[Fiction] Gardener/Handyman Wanted

[MasterBilly]

Gardener/Handyman Wanted
Leaving school was easy, the hard bit was trying to get a job. I never really excelled in anything at school, so I did not exactly have a stack of GCSE’s under my belt. Life was tough at home, dad had long since done a runner and mum either couldn’t or wouldn’t work. So there wasn’t a lot of money to throw around and all the local job opportunities were aimed at people with experience. As a 16 year old virgin with no money and fewer friends life seemed pretty bleak, but that life was about to change by a chance visit to a local newsagent. The note in the window read:

GARDENER/HANDYMAN
WANTED

ENTHUSIASM MORE IMPORTANT
THAN EXPERIENCE
REASONABLE RATES OF PAY
TEL 01234 567890



It was a couple of miles from home, on the edge of a fairly wealthy area, being borderline desperate and with nothing to lose I duly noted the number and that afternoon I gave it a call.

The phone was answered by an obviously refined lady who, after a brief discussion, invited me to an interview the following Monday at 9 am.

The interview went well, Mrs Jordan lived in a large house on a posh estate and was a ‘city widow’, she saw her husband for an hour each evening before bed and at weekends, the work involved mainly gardening or weeding and any general cleaning jobs that she needed doing, the pay was not brilliant, but was as much as I could expect as a 16 year old school leaver. She seemed particularly interested in my girlfriends and my experience with girls. I had none but obviously could not admit it. I stumbled through the question claiming that I had a bit of experience but not much and was currently between girlfriends.

“How much experience,” she asked.

“Oh the usual,” I replied going red.

She smiled at me with raised eyebrows and the conversation stopped as I went brighter red and shrivelled up in my seat. Eventually and to my relief she moved onto another subject.

I was offered the job on a temporary basis, to start immediately and cash in hand. Mrs Jordan led me into a spare downstairs room and told me to change into shorts, t-shirt and flip-flops so that I didn’t dirty my own clothes.

My first job was some general tidying in the garden and after about an hour I sat down with Mrs Jordan for a cup of tea and a chat. I say a chat, I did very little talking, mainly ‘yes’ and ‘no’, but she did seem to want to talk about sex a lot, which I found strange.

After my tea break I went back to work until dinner time, we had chicken sandwiches and I noticed that the bread was a lot nicer than we had at home, Mrs Jordan talked more and more about herself and sex in general. By now the sun had come out so after dinner I was tasked with weeding the garden whilst my boss lay on a sun bed, sunbathing in the middle of the lawn. She came out wearing a red bikini, but very quickly the top came off as she lay there soaking up the rays.

I tried concentrating on the weeding but it was difficult, I was trying to garden only feet away from an attractive woman wearing nothing but a skimpy red bikini bottom, my erection was massive. She was about 27 or 28, her husband was about 10 years older and was a big shot in the city. I could believe it, this was a 6 bedroomed detached house with a large secluded garden. A Mercedes Benz and a BMW were both parked on the drive and the inside of the house just stank of money.

“Ahem,” I heard a slight cough from behind me, I looked around at Mrs Jordan. “Tony dear, would you be a saint and rub some sun cream on my back for me?” she smiled and rolled onto her front.

I got up and self consciously made my way towards her. I was wearing cheap baggy boxers and a pair of baggy shorts. I wasn’t exactly ‘tenting’ but there was a clear bulge in front of me. Lingering slowly I rubbed the cream into her back, enjoying every second, this was as intimate as I had ever been with a female. I stopped when I felt that I could not spend any more time without being labelled a pervert and watched as she pushed her red waistband down slightly revealing about an inch of the crack of her bum.

“Just rub a little more cream on that bit please, I hate an obvious bikini line.”

‘Wow’ I thought to myself ‘this really is not happening’ as I covered the area required with more cream.

“Why don’t you join me on the other sunbed, you’ve been working too hard today,” Mrs Jordan said after I had finished.

“Er no,” I stumbled, confused.”Er ... I’m here to garden ... if your husband ... I mean ...” I got up and started to make my way back to the gardening.

“Stop,” she looked at me from her side on position, this was the first time that she had spoken sharply to me all day.

“I’m paying your wages so you will do as I say, my husband will not be back until 9 O’clock tonight, I enjoy your company so take your top off, lie on the next sunbed and sunbathe,” she scolded.

Not really knowing how to get out of this possibly embarrassing situation I hesitated before removing my top, stepping out of my flip-flops and laying down on the next sunbed. Mrs Jordan told me to put some suncream on, which I did and then laid back and tried to relax. After about 15 minutes I started to enjoy my new job, to think that I was actually getting paid for this, when Mrs Jordan started talking again.

“So when did you actually finish with your last girlfriend then Tony?”

“Er ... erm ... er ... about ... about 3 months ago,” I lied.

“So you’ve gone 3 months without sex?”

“Er ... yes Mrs Jordan,” I felt uncomfortable calling her Mrs Jordan in this environment, but she had not said that I could use her Christian name, I did not even know what it was. To be honest, despite her being overfriendly towards me I think that she enjoyed watching me squirm a little as I addressed her as Mrs Jordan.

“So you have had no casual relationships in the last 3 months,” she enquired.

“No.”

“Oh, you poor boy, that’s without any form of sex whatsoever, oral or vaginal.”

“Yes Mrs Jordan.”

“You have had oral sex then?” she asked.

“Er ...,” I thought about lying but decided to come clean. “No, Mrs Jordan.”

“You poor boy, 16 years old and you’ve never had a blow job.”

She got up and knelt down beside my sunbed, her boobs looked beautiful, especially her nipples; my cock was rock solid, she placed her hand on my bared lower leg.

“Would you like a blow job now?” she asked softly.

I might have been sexually naive, backward you might say. But even I couldn’t get this question wrong.

I nodded my head. “Yes,” I whispered, before remembering my manners. “Please.”

She smiled at me before unfastening my shorts and tugging them to mid thigh. She hooked her fingers into the waistband of my red and white stripped boxers and started pulling those down as well, my bottom naturally raised itself to assist her. She took hold of my erect knob and kissed the end, before looking me in the eyes and smiling. Opening her mouth she went about half way down before sucking her way back up.

I was overjoyed, at last it had happened; at long, long last my sex life had started. Alright it wasn’t vaginal sex, but it was a blow job and it was happening to me!

It was wonderful, she was sucking so hard, I didn’t know it then but my cock was in the mouth of an expert, her teeth combined with her saliva were doing magical things, especially around the tip. Wanking usually took me about 5 or 6 minutes, but Mrs Jordan’s mouth had me cumming in less than half that time. She sucked every last drop out of me before yanking my pants and shorts off my legs, picking up my t-shirt she marched off to the house with her mouth closed.

So she wanted me naked did she, well after what I had been through that was fair enough. I lay there enjoying the sun, contemplating life, staring at Mrs Jordan’s bikini top. I picked it up and inspected it, suddenly feeling like a pervert I quickly put it back down, looking around nobody had seen me.

Presently Mrs Jordan came out with a tray of two cups of coffee and some biscuits, still topless she placed it on the patio table, came across to me and disappointingly put her bikini top back on and invited me to join her for coffee on the patio.

“Er, can I have my shorts back,” I asked.

She raised her eyebrows and starred at me with a half smile.

“Please,” I asked again.

“Come on Tony, coffee,” she ruffled my hair and walked towards the patio.

I looked at the flip-flops, thought about putting them on and the decided that it would be pointless and made my way across to the patio.

Feeling completely self-conscious I sat there naked, listening to Mrs Jordan ramble on. I kept making furtive glances towards the house, wondering where exactly my clothes were, I wanted to ask but didn’t. Mrs Jordan was obviously getting some sick pleasure out of having an embarrassed naked boy in her garden.

She kept talking until the coffee was finished and then she got up, stretched off her legs, picked up the tray and turned to me.

“I’m just going to tidy this lot up Tony, I’d like you to go back to gardening please.”

“I’ll need some clothes,” I said trying to sound forceful.

“No Tony,” she replied shaking her head and smiling. “Naked is good.”

“No!” I said emphatically, enough was enough. “I am not going to do anymore work for you without clothes. You must give me my clothes back now.” I felt that I had good reason to get angry, okay she was my boss, she had given me extended tea and lunch breaks, allowed me to sit around on the lounger, not to mention the trifling matter of a blow job. But forcing me to work naked was still a form of sexual abuse.

Disappointingly Mrs Jordan did not seem to take my anger seriously, she simply raised her eyebrows and smiled at me.

“Mrs Jordan give me my clothes back now,” I said standing up and raising my voice.

Her eyes dropped to my cock, eyebrows still raised, smile still on her face, I moved my hands in front of me, blocking her view.

“Tony go back to gardening now,” she said quietly.

“No Mrs Jordan, I will not do any more work for you until you return my clothes.” I was nearly shouting now, anybody in the nearby gardens must have heard, but I didn’t ever have to come back here, if the neighbours knew that there was a naked boy in Mrs Jordan’s garden then it surely must be more embarrassing for her.

“Really,” she replied. “So how do you intend to get home without any clothing?”

She had a point, there was no way that I could run 2 miles home stark naked. I realised that I had overplayed my aggressive stance, she really could leave me naked in her garden for as long as she wanted. I tried another approach.

“Please,” I asked calmly.

“Put your hands on your head Tony,” she instructed.

I did as I was told and she studied my nether regions for a short while.

“Would you like another blow job this afternoon Tony?” she asked. Silly question, it may be wrong to make me work naked, but I was not going to refuse another blow job was I.

“Yes,” I replied softly.

“Then return to your gardening,” she told me before walking back to the house with the tray.

With the depressing feeling that comes with losing an argument I turned and walked naked back to the flowerbed and returned to my weeding, trying to console myself that I had been promised another blow job. It is the way the human brain works I suppose, but after a short while I had convinced myself that my stance had forced Mrs Jordan to either return my clothes or give me another blow job, she could not return my clothes because she would lose face, her only way out was to agree to give me another blow job. In other words I had forced Mrs Jordan into giving me another blow job; well maybe, at least that train of thought made me feel better. It was about 4:30 when I was told to tidy up and then come into the house for a shower. The Jordan’s had a big house and actually had a shower downstairs, next to their utility room; there was, however, no towel to dry myself.

“You go ahead and take your shower, I will go and fetch a bath towel from upstairs,” Mrs Jordan informed me. Again I had nothing to protect my modesty and I noticed that there was no lock on the door to the shower room, Mrs Jordan or anybody else for that matter could just walk in and see me naked. It seemed to be a recurring theme in working for Mrs Jordan. I showered off and dripping wet cracked the door open slightly.

“Mrs Jordan I’ve finished, could you bring me the towel please,” I called out.

“It’s here in the parlour, I’m a little busy could you come and get it yourself.”

“I’m dripping wet, I’ll get water on all your carpets,” I replied, desperate not to have to do a streak though her house.

“It doesn’t matter, they will soon dry,” she answered.

So she wanted me to parade naked around her house did she. With a sigh I opened the door and walked towards where her voice had come from, avoiding the temptation to run, trying not to give the impression that I was totally humiliated.

Predictably she wasn’t busy at all, when I found her she was just sitting down with a large towel draped over the side of her armchair.

“Stand there with your legs apart and I will dry you off,” indicating a spot just in front of her.

Hell fire this woman really was a pervert, I knew that there was no point in arguing, so I did as she wanted. She did dry me off as well, starting with my head she worked her way down my body, she even dried under my foreskin, though she didn’t spend any more time down there than she needed to. When she had finished she sat back down with her knees very much together, patted her lap and spoke.

“Right Tony, bend over my knees,” she commanded.

“Why?” I asked, suspiciously.

“Because I told you to, now do it,” she growled sternly.

With a shrug and knowing that I was unlikely to win any argument with Mrs Jordan I bent over her knee displaying my fresh bottom to her. She took hold of my right arm forcing it up my back.

“Right, don’t you dare move a muscle young man or I will rip your arm right off,” she shouted at me, putting the fear of God into me.

With that she proceeded to spank my bottom, a 16 year old teenager and I was being spanked like a young child! For what? I hadn’t actually done anything wrong. In fairness the spanking didn’t really hurt, it was light, the humiliation was the worst. Though when I got up I did feel a rosy glow about my face, more than on my bum. I also had a semi, it was strange, impossible to describe, but this attractive woman had spanked my bare bottom and I think that I actually enjoyed it.

“That was for arguing with me when I told you to garden naked Tony. From now on if you are going to work for me you are to do what I say, when I say it, no questions asked, do you understand?”

“Yes Mrs Jordan.”

With that she knelt before me and put my semi erect cock in her mouth, true to her word she gave me another blow job. Daringly I put my hand on her head and stroked her, looking up she seemed to smile with her eyes before returning to the job in hand, or job in mouth.

I lasted a little longer this time, but again when I blew my load into her mouth she sucked every drop out of me before disappearing to the kitchen, presumably to spit it out.

Returning she sat down on the sofa and invited me to sit next to her, as I did she placed her hand on my knee.

“How many times have you really had sex Tony, honestly?” she asked me.

I looked at my feet shyly, biting my bottom lip I looked at Mrs Jordan before speaking.

“None,” I whispered.

“So you are a virgin?” she asked in confirmation.

“Yes,” whispering again.

“Yes what?” she asked sternly demanding an answer.

“Yes I am,” I replied looking down at my feet.

“Yes you are what?” her voice demanded.

“Yes I am a ..... a vir ..... yes I am a virgin,” I stuttered looking her in the eye again with tears of humiliation starting to form in the corner of my own eyes.

She reached across and cradled my scrotum. “Tony dear there is nothing wrong with being a virgin, we were all virgins once, by the end of this week I intend to claim your virginity, is that okay?”

“Yes Mrs Jordan,” I murmured.

“And if you carry on working for me this summer I will see if I can get a couple of girls more your own age for you to fuck. Would you like that?” Mrs Jordan had a very refined accent, but when she said ‘fuck’ it sounded really dirty. I could feel my eyes sparkling as I replied.

“Yes Mrs Jordan.”

“Good boy, now here are you wages for today, now go home and I will see you at 9 o’clock sharp tomorrow morning, do not be late Tony, I will not tolerate tardiness,” with that she let go of my scrotum, handed me £65 in cash before leading me out of the room towards the front door, I began to panic.

“Er, Mrs Jordan please can I have some clothes to walk home, please?”

“It’s alright Tony, your clothes are in the porch,” she replied laughing, holding the door open for me she deliberately watched me as I got dressed into my own clothes that I had arrived in that morning. I finished tying my shoelaces, nodded a quick goodbye to my new boss and grabbed the outside door handle to leave.

“Just one last thing Tony,” I turned and faced her. “Remember from now on I expect you to obey my exact word instantly and without question, there was far too much backchat from you today, I don’t want to have to smack your bottom, but I am prepared to and can do it a lot harder. You are to obey my every word instantly and without question, is that clear?”

“Yes Mrs Jordan,” I replied before heading out into the street. That evening I thought a lot, had I been abused? Well yes I had, being made to work naked in her garden was abuse, alright, there were mitigating circumstances, but she still took all my clothes, hid them and told me, as my employer, that I had to work naked in her garden, that was sexual abuse! Before giving me my clothes back she told me to bend over her knee, she smacked my bottom and told me it was a punishment, that was sexual abuse! Alright, it wasn’t very hard and it did give me a semi, but that is not the point, it was sexual abuse.

That said, was I going to do anything; if I did then I would have to do it now. I could hardly work naked in her house for 3 weeks when I was being paid cash-in-hand every day and happily going back the day after, and the day after that; then suddenly complain of abuse after 3 weeks. I would be laughed out of court. I looked at the £65 at the side of my bed, I thought about Mrs Jordan’s promise to let me shag her this week and the promise to shag other girls in the future. No, I convinced myself, being made to garden naked was not really sexual abuse, it was just a bit of adult fun that was all, I was becoming an adult now. I thought more about Mrs Jordan making me work naked in her garden, I was getting another semi just thinking about it.

[MasterBilly]

I rang Mrs Jordan’s doorbell the following morning at 10 minutes to 9, conscious of her promise ‘not to tolerate tardiness.’ Mrs Jordan showed me into the front room where I had received my spanking the previous day. Judging by the size of the house there would be two further reception rooms. On the table there was a pair of shorts and a t-shirt, both clean and pressed along with a pair of flip-flops. Without being told to I stripped down to my boxer shorts.

“Do you want me to wear my underpants underneath the shorts Mrs Jordan or would you prefer me to go commando,” I asked submissively. I had clearly worked out the best way to keep on her good side.

“I think commando would be better,” she replied smiling. “Then when I decide to spank your bum I only have one item to pull down.”

Noting that she said when and not if, I slipped out of my boxers before asking her permission to put on the shorts and t-shirt. There was a long pause as Mrs Jordan inspected my body.

“I think not, I have a little job for you upstairs first Tony.”

I followed her upstairs and into the master bedroom, by the time that we had got in there my knob was almost erect as I was by now expecting another blowjob, my hopes were to be dashed though as she instructed me to climb into bed as she stripped down to her bra and knickers with her back to me. Both items were red lace and she looked as erotic as fuck as she climbed into bed with me. Was this it, I asked myself, was I about to lose my virginity?

Again I was about to be disappointed as she told me to roll away from her, wrapped her arms around me and proceeded to spoon me. I know that it should have been the other way around, but with Mrs Jordan it just seemed natural.

“So Tony did you masturbate last night?” I was getting used to Mrs Jordan’s intimate questions and they no longer shocked me.

“No Mrs Jordan.”

“When did you last masturbate?”

“Er ... Saturday evening Mrs Jordan.”

“What did you think about when you were doing it?”

“I can’t remember.”

“What did you think about Tony,” she repeated raising her voice and squeezing my balls at the same time.

“I can’t remember Mrs Jordan,” I squealed. “Honestly I can’t remember.”

“Okay, I will believe you. But you must have some sexual fantasies that you think about when you are playing with yourself. Describe them to me and make sure that you go into detail.”

I did, I currently had three favourite fantasies but there was no way in the world that I wanted to tell them to another person, I’d die in shame. That said Mrs Jordan still had a firm hold of ‘those that were most dear to me’ even though she had now relaxed her tight squeeze. As I hesitated I could feel her grip tighten slightly, I quickly began.

My three favourite fantasies were all kinky, one involved two girls that I used to go to school with having a lesbian orgy, for some reason it always took place in my bedroom even though I wasn’t there. The second one involved me finding a woman tied spread-eagled to a bed naked but with a blindfold on, I proceeded to have my wicked way with her and she never found out who I was. The third fantasy involved me secretly watching a girl masturbate in the woods, I recorded it on my mobile phone and then threatened to expose her unless she had sex with me.

I was forced to go into detail about all three fantasies. Mrs Jordan enjoyed watching me squirm as I told her, finally after lots of questions she seemed happy and rolled me onto my back and lowered her head under the sheets and started sucking on my limp manhood. I felt a wet finger push its way up my cheeks and start rubbing my bumhole; what on earth was she doing down there? I was disturbed and wanted to pull her hand away, but I also feared Mrs Jordan and was scared of stopping her from doing something that she obviously wanted to do.

Nobody had ever touched me there, well not since I had learned to wipe my own bum. It was a strange light tickling that was doing something to me and yet it was wrong. To touch that most private of places was both wrong and dirty, I don’t mean ‘fun dirty’ I mean ‘disgusting dirty.’ To actually play with and rub that spot was wrong and dirty 10 times over. But to do it to another person uninvited, those sort of people should be in prison.

I tried to put the disgust to the back of my mind as I concentrated on the vacuum pump that seemed to be attached to my penis. Mrs Jordan had me rock hard within seconds and her sucking combined with her teeth running up and down me as well as her tongue; I was in paradise! That tickling on my bumhole was doing the trick as well, no matter how dirty and wrong it was.

I was getting close, building right up to the edge, almost there, about to shoot; when Mrs Jordan did something that I would remember for the rest of my days. Just as I was about to ejaculate she shoved her finger right up my bum, all the way! I wanted to shout no and protest, but just as it went in I exploded in the most amazing fashion. Shooting stream after stream into Mrs Jordan’s mouth and calling out in pleasure at the same time. It was fantastic, awesome, totally and utterly brilliant.

As I came down Mrs Jordan still had her finger all the way in me, but was resting her head on my stomach, presently she climbed out of bed and made her way into the en-suite returning a few minutes later to cuddle me. She rolled me over so that I was facing her and wrapped her arms around me, I wrapped my arms around her too as I felt the forefinger of her right hand slide down the crack of my bum as it sought out the entrance to my brown tunnel. I thought about resisting as it pushed into me, then thought better of it, I felt the finger slide all the way into me, it still felt very wrong and very weird, but I knew not to complain.

An idea came to me, could I get my finger into her bum? Why not, she didn't ask permission from me! I lowered my hand down her back and into the waistband of her knickers.

"What are you doing Tony?" Mrs Jordan asked with only a hint of protest.

I pushed a single finger down further into the crack of her bum.

"Don't even think about it," she warned, but not aggressively, I decided to chance it, she would only smack my bum again and to be honest I partly wanted her to! I pushed my finger further and touched her sphincter. Suddenly she let go of me, sat up and aggressively pushed me onto my back, I looked up just in time to see her right hand come flying into my face.

"I said no Tony, when I say no you do as you are told, now get downstairs and wait for me there," she furiously shouted at me.

The slap across the face had caused tears to form in my eyes, but I could still see how angry she was, I had really upset her. I slipped out of her bedroom naked and waited for her at the bottom of the steps. I wondered at that point if I should just go into the front room, put my clothes back on and get out of that house for the rest of my life, this Mrs Jordan woman was a fucking psycho.

I didn't leave, Mrs Jordan did come down the steps in time with a very serious, unimpressed expression on her face. She grabbed me be by the arm and physically dragged me down into the cellar with her fingernails digging painfully into my arm. The cellar was very large and very empty except for a bucket with a stick and paint brush and four large bags of whatever in the corner.

"Right young man, in the fullness of time you will be punished for your disgraceful behaviour in the bedroom, but in the meantime you will whitewash the cellar. The whitewash is in those bags, you mix the powder with the water from the tap in that bucket and then you whitewash the walls, any questions?" Mrs Jordan was smiling forcefully as she spoke, I was too scared to ask her any questions even if I could think of any.

"No Mrs Jordan."

“Now I suggest you work hard and quickly, there will be another punishment if it isn't finished by lunchtime,” with that she walked back up the steps and out of the cellar, disturbingly locking the cellar door as she left, I was locked in! Naked!

I now really wished that I had left the house with my clothes when I had the opportunity, this was getting scary, if I ever got out of this house alive then I was never coming back ever.

In the meantime my chances of survival were going to be increased if I did the work and did it well. I don't know if anyone has ever whitewashed cellar whilst naked before, but it was certainly a novel experience for me. I worked non-stop for two and a half hours, the walls were completely covered, so was I and I spilt a lot on the floor as well, I hoped Mrs Jordan was not going to react too badly to that, but she was one unpredictable lady. When she came down to inspect she seemed fairly pleased, she even laughed at the sight of me plastered in the stuff, she nodded at me when I apologise for the whitewash spilt on the floor.

“Turn around Tony, spread your legs and touch your toes."

I did as I was told, keeping my legs well spread, despite the humiliation I knew that it would cause I was desperate to get back into her good books, even if it was just so that I could get out of there. She reached over and prised one of my cheeks apart and inspected my hole.

"Tony dear, I am paying your wages, does that mean that I can ask you to whitewash my cellar?"

"Yes Mrs Jordan."

"Does that mean that I now have to go around to your house and whitewash your cellar?"

"No Mrs Jordan," I replied rather than, 'we haven't got a cellar you psycho bitch' which was what I was actually thinking.

"So if we are in bed together is it all right if I decide, as your boss, to stick my finger up your bum?"

"Yes Mrs Jordan that is perfectly alright."

"And does that give you the right to stick your finger into me?"

"No Mrs Jordan."

She gave me six more smacks, a lot harder than the ones I received yesterday. This time I did not get a semi erection and there was no warm glow about my face, these smacks hurt, especially they last few.

"Right you can stand up now Tony," Mrs Jordan said after the sixth smack.

I stood up straight, shaking with nerves.

"Six smacks were for getting whitewash on my lovely cellar floor, you will get your punishment for your behaviour in the bedroom later, do you understand?"

"Yes Mrs Jordan."

"Right then follow me," Mrs Jordan lead me to the downstairs shower room and told me to have a shower and then report to her in the conservatory, this time though there was a large towel for me to dry out in private.

I was really caked in whitewash and it took some time for me to clean myself properly. I had also had enough though, as soon as I was dry I would head for her front room, get my clothes and leave, by the window if all the doors were locked. If she tried to stop me I would run into the front garden naked if necessary and get dressed there, if she came after me I would even run into the street naked and dress in the middle of the road. Nobody knew me in this part of town and the way that I felt at the moment I couldn't give a fuck.

I made my way into the front room and my clothes were nowhere to be seen, I had a quick look around but she had obviously hidden them.

"Tony dear, where are you?"

Shit, I thought decisions, decisions. I could run out of the door in just a towel, that would mean a 2 mile walk across town in a towel and barefoot, not tempting! I could carry on searching for my clothes, but knowing Mrs Jordan she would have hidden them well. In not finding them I would, no doubt, suffer her wrath again. The only other option was to drop the towel and report to Mrs Jordan in the conservatory. The towel hit my ankles and I made my way to the sun trap of Mrs Jordan's conservatory.

There was ground coffee, some bananas and smoked salmon sandwiches, I had never eaten smoked salmon sandwiches before, what a different life the wealthy lived. Mrs Jordan rambled on for a while before she suddenly, and for no apparent reason, asked me another intimate question.

"How often do you masturbate Tony?"

"Usually about once every 5 or 6 days."

"Is that all, you really should be ejaculating more often than that," she told me.

"Well ... er ... isn't it dirty to do it a lot."

"Not for a boy, your testicles are continuously producing sperm, it is perfectly healthy to get rid of the excess, your mouth is continuously producing saliva but you wouldn’t go a week without spitting or swallowing would you?”

“No Mrs Jordan,” I replied becoming confused, surely there was no connection with those two principles was there.

“And I notice that you didn’t object when I gave you two blow jobs yesterday. You did not say to me in the afternoon, ‘oh no, I’ve already cum once today, you must leave it another 5 or 6 days before you give me another blow job.’ You didn’t say that did you?” she asked.

“No Mrs Jordan,” I replied, sort of seeing her point.

“So are you going to make sure that you ejaculate at least once a day from now on?”

“Yes Mrs Jordan.”

[m55uk4younger]

I wonder where this story is going but please continue.

[MasterBilly]

m55uk4younger, many thanks for your positive comments.

Though I have to say that it will be some time (6 - 18 months) before I continue with this story, for various reasons.

It will continue eventually though.

[MasterBilly]

We finished our meal with me basically listening to Mrs Jordan ramble on about trivia. As she finished she stood up and led me to the bottom of the garden where there were a few basic gardening tools, mostly what I had used before.

“Right then Tony I would like you to go back to gardening now, I’ll leave you to get on with it.”

“Yes Mrs Jordan.”

I knelt down to start gardening but looked quickly over my shoulder at her walking back to the house. I still did not know whether or not I should carry on working for her or never come back after today.

After about 20 minutes she came back out dressed in a blue bikini with a cool drink and sat on one of the sun lounges in the middle of the garden, the bikini top came off very quickly and she laid back on the lounger to sunbathe. Another few minutes went past and I heard the soft tones of Mrs Jordan’s voice.

“Tony dear, could you come here a second please.”

I got up and walked across, as I approached her I started to think of the surreality of the situation. Here we were, in this lady's back garden in the early afternoon, I was starkers and she was in just a bikini bottom.

“Could you rub some sun cream over my stomach and chest please.”

“Er, can’t you do that?” I asked thinking it was a bit of a ridiculous request.

“Tony love, I pay your wages and I would like you to do it,” there was a slightly dangerous edge to her voice, only slight but I could not miss it.

I took the tube offered and squeezed a large amount onto her stomach, working it in all over, I went under her bikini bottom, but only by a fraction of an inch, I enjoyed working it into her navel and had covered every inch of skin up to her bosom when I ran out of cream. I picked up the tube again and for some reason this time squeezed it onto the palm of my hand, rubbing my hands together I had cream on both hands and I placed a hand on each boob at the same time, shitting myself because I could never work out what her reaction to anything would be, I slowly massaged her breasts, not daring to look at the expression on her face.

“Don’t forget the nipples Tony,” Mrs Jordan told me as I was moving onto the upper chest.

“Er, I thought that I had done them Mrs Jordan,” I said nervously, of course I had creamed her nipples and she knew it.

“Tony the nipples are very sensitive to sunburn, I suggest that you do them again,” as she said it she gave my penis a quick playful flick which was of course was by now a solid, rock hard shaft.

I squeezed some more cream onto my fingertips and gently massaged her nipples, feeling horny as hell I discreetly looked down at my cock, not only was it rock solid but it was generating precum as well and I hadn’t even touched it. I was desperate to jack off, but I could hardly do that!

The thought did cross my mind, there was no way on this planet that Mrs Jordan thought that she needed some more sun cream on her nipples, for whatever reason she wanted me to rub them again. As I finished doing around her shoulders Mrs Jordan finally seemed happy.

“Thank you Tony, that’s very good of you, you can go back to gardening now.”

“Yes Mrs Jordan,” I walked back to where I had got to a few minutes ago with my erection swinging back and forth and my bell end completely covered in shiny precum. All that I could think of was that this simply cannot be right.

A short while later and Mrs Jordan got up and went back into the house, returning moments later with a single stiletto in her hand. She walked right up to where I was working.

“Tony can you leave that please and come and lie down on the grass, face down.”

“Er, why Mrs Jordan.”

“Because I am telling you to.”

I did not really expect a better answer, suppressing a sigh I put down the hand fork and laid down on the grass in front of her. She immediately knelt down over my upper back facing my legs, she then placed each of my arms over her calves, squatting down completely my arms were now trapped between her thighs and calves, I tried pulling on them but I could not move an inch, I was well and truly pinned down.

“Don’t struggle Tony, this is when you get your punishment for your behaviour in the bedroom this morning,” Mrs Jordan informed me.

She picked up the stiletto and started spanking my arse with the flat sole, it hurt like fuck and trapped as I was I started screaming, after only two she paused.

“I don’t mind you crying, in fact I quite like it, but if you continue to scream like that I will give you double,” Mrs Jordan said.

This was getting fucking incredible, I was not even allowed to scream in pain. I bit my lip and cried into the grass as ‘the fucking psycho’ gave me four more. As she finished she got off me and told me to get to my feet, taking me by the hand she led me up to the house just outside the French Windows. She peeled her bikini bottom down and turned to look me in the eye.

“We are now going inside and I am going to claim your virginity, you are going to fuck for the first time Tony, alright.”

“Yes Mrs Jordan,” I replied, staring at her through tear stained eyes.

We entered the house hand in hand as she led me to the foot of the stairs before slapping me lightly on my sore bottom.

“Up you go, I’ll follow you, you know where the bedroom is,” she said.

I headed up to the master bedroom and made my way in, Mrs Jordan followed and immediately laid on the bed and looked up at me, unsure what to do I just stared at her, I had never been in this position before. After a few moments of nothing happening she spread her legs, bent her knees slightly and pushed them out wider adopting the classic missionary position, I still was unsure what to do next.

“Tony, why don’t you come down here and rub my pussy for me,” Mrs Jordan clearly realised how useless I was and was gently trying to get the best out of me; I realised how lucky I was, most women would have given up on me already, left me and gone to join their mates, ridiculing me behind my back.

I went across and sat on the bed next to her, stared at her pussy, then her face, then her pussy again and nervously reached out and stroked the hair at the side of her vagina, feeling braver I started to stroke the slit itself. Several strokes later and not really knowing how to advance this I heard Mrs Jordan’s gentle tones again.

“Tony dear, start fingering me.” Whilst I accept that I was being extremely naive and slow, I ask you, the reader, to bear in mind that for sticking my finger up her bum earlier in the day I was made to whitewash her cellar naked and got a sound spanking on the garden lawn with a stiletto, this was a seriously fucked up lady and I for one was shit scared of her.

I started rubbing harder against the top of the slit, trying to force my finger in there.

“Er, what are you doing Tony?” I stopped instantly out of fear.

“Trying to finger you ,” I replied nervously, looking her in the eye.

“The entrance to the vagina isn’t up there, it’s further down,” she told me softly and patiently.

Feeling a berk I rubbed further down until I got to the middle of the slit, I concentrated on that area my rubbing becoming more insistent.

“Lower down than that Tony,” Mrs Jordan said giggling, I was obviously making a prat of myself here.

I worked my way down near the bottom of the slit and rubbed harder and deeper, the ground just seemed to open up, my finger just seemed to slip into her body, I was fingering her! Fuck me, I was actually fingering somebody for the first time in my life! But who on earth put the vagina all the way down there, it was literally between her legs, I thought that the vagina was meant to be at the front? For fuck’s sake it was only an inch or two from her sphincter! Anyway, back to the fingering, I forced two fingers into her hard.

“Ouch, take them out now Tony!” She shouted. Fearful of another spanking I quickly removed my fingers and looked up to her, she beckoned me up to her with her finger, closing her legs she patted the bed at the side of her for me to join her, she had a friendly half smile on her face. I laid down alongside her and she placed an arm around me.

“Tony, can you remember when I pushed my finger up your bum?” Could I remember? What a stupid fucking question, it was a life changing event, I would remember it for the rest of my life. And it only happened a few hours ago!

“Yes Mrs Jordan,” going for tact rather than sarcasm in my reply.

“Did I stick it up forcefully or gently?”

I thought back, it all happened at once, her finger rubbing my hole, her finger going in, me ejaculating, her finger being all the way in. But as I thought about it while she did push her finger in fairly quickly, her finger did actually enter me gently.

“Gently Mrs Jordan.”

“Of course Tony, the anus and the vagina are very sensitive areas, to be enjoyed you have to handle them gently. When you finger the vagina, go in gently, be gentle when you are there and then withdraw gently. Remember, you are trying to turn the lady on not hurt her. If you hurt her then she will never go near you again, if you turn her on then she will follow you everywhere, do you understand?”

“Yes Mrs Jordan.”

“Alright then, let’s give it another go; go back down and try again,” she told me, bending and spreading her legs back into the missionary position.

Wondering if it was like this for every bloke on his first time I went back to her crotch and started fingering her again. Slowly and gently I worked two fingers into her right up to the knuckle.

“Gently, feel around the inside Tony, I will tell you when you have reached the right spot.”

So I had a feel around, not really knowing what I was looking for, there were several things up there, all of them slimy, up against the outer wall, just below the pubic mound, were some ripples, as my fingers roamed over them I got a definite moan out of Mrs Jordan. I ran my fingers over the top edge of the ripples.

“That’s it, that’s the spot, keep working there,” Mrs Jordan voice was suddenly high pitched as I kept my fingers around that area, stroking and rubbing.

At one point I started rubbing too aggressively and received a sharp scolding from my boss. I did notice that her vagina was getting wetter, despite my lack of knowledge I did know this to be a good thing. I also notice her hips moving slightly and the tuts and moans coming from her lips were definitely not critical.

“Okay Tony, stop there,” she told me and after a brief pause I was also told to remove my fingers. I could not stop staring at her pussy, Mrs Jordan for her part reached down to my cock and gave it a quick slap, it bounced from side to side.

“Time to put that to work Tony, lay on top and slide it in slowly,” she made it sound so simple, I knew where to put it, surely it should slide in naturally, right?

I laid on top of her in an undignified fashion, supporting myself with one arm and trying to feed my cock in with the other, where had that bastard hole gone? After much wriggling around Mrs Jordan decided to take over and feed it into her vagina herself. I slid it in and out a few times when my teacher felt the need to address me again.

“Tony, just try swinging your hips rather than sliding your whole body.” In many ways I was glad that I was going through this with Mrs Jordan, somebody who obviously needed to keep quiet about the whole thing, if this had been with a girl from school who knew all my mates and then the stories of how useless I was had got around, well I would be the laughing stock for years.

“That’s better Tony but try swing your hips in more of an arc.”

So I tried, it was harder and towards the end it started to pull on my abdominals, I was going to have to work on those, but Mrs Jordan still had one final bit of advice to give.

“At the end of each stroke try and push my body up the bed, don’t push it all the way in.”

With that last instruction Mrs Jordan genuinely seemed to be enjoying it, I on the other hand was not going to last much longer and was soon emptying my seed where nature intended, for the first time in my life.

“Was that okay,” I asked rolling onto my back, not really knowing what to say.

“Not really Tony, but it was your first time, you will only get better.”

“Oh,” I said feeling crestfallen, was I really that bad. Mrs Jordan sensed that I had taken a blow and attempted to restore my confidence a little.

“Tony dear, look how much that you have learned today, you now know where the entrance to the vagina is, you know how to finger a woman properly, you now know where a lot of her buttons are and you now know how to fuck properly. You have learned so much Tony and with a little more practice you will be a good fuck, I promise. In the meantime feel proud about how much you have learned, alright.”

“Yes Mrs Jordan,” I said to her, smiling into her face, she really had made me feel better.

“Roll over onto your stomach,” she told me, I did and straight away.

She knelt over my bum and started tracing her fingers over it, at first I thought that she was going to spank me again, she didn’t but she did prise apart my cheeks, I felt her inspecting my brown starfish before she placed a wet finger on the centre. I was suddenly very uncomfortable, but if I wanted sex rather than a spanking tomorrow then I would have to live with this. Her finger pushed slightly at first, but I got the message, I was going to be finger fucked up the bum, again.

As her finger pushed harder I relaxed my muscles and it slipped in naturally. She frigged away in a sawing action for a few minutes and, I have to say, I enjoyed it. Then she curled her finger around and started massaging an area at the back of my cock, it felt amazing.

“Ahhhh ..... ooooh ..... oh my gawd ..... yeahhhhh ..... ooo,” moans of absolute pleasure came out of my mouth.

“Enjoying this Tony?”

“Oh yes, it’s wonderful, thank you Mrs Jordan.”

“That area that I am touching is called your prostate, this is a prostate massage,” she told me, continuing the massage for a short while before removing her finger.

“You can roll onto your back now Tony,” she told me, slapping my bottom playfully as she said it.

I did as I was told and she flicked my rock hard cock a few times with her fingers. How on earth had it become so hard so quickly, I only ejaculated about 5 minutes ago.

“How did you give me a lob on so soon after I ..... er ...” I did not know how to ask her, did she have special powers or something. In the past when I shot my load I could not get another erection for up to an hour later, no matter how much that I played with it.

“Ha ha,” she laughed at me. “It was the prostate massage. You’ve never been touched there before have you?”

“No Mrs Jordan,” I replied.

“You really enjoyed it though didn’t you?”

“Well it was strange ..... at first ..... but then ..... yes, I enjoyed it Mrs Jordan,” I admitted sheepishly.

“Well, maybe if you are a good boy I will do it again tomorrow,” she suggested with an electric glint in her eyes.

“Would you like me to massage your prostate Mrs Jordan?” I ventured.

She just laughed at me, long and hard. There was no need for that, it was a fair enough offer in my mind, she even wiped her eyes at one point. She did calm down enough to voice her opinion, eventually.

“Tony you will not be massaging my prostate, for one thing your fingers are never to stray anywhere near my back passage, is that fully understood?” Her voice started in a jovial fashion, but she said the last four words very firmly and forcibly.

“Yes Mrs Jordan.”

“Secondly the prostate is well let’s say ..... in fact I think I will let you go online tonight and research the female prostate,” she giggled, clearly I had said something wrong.

Mrs Jordan got up and placed a chair in the middle of the bedroom and told me to sit on it, sitting on the backs of my hands. I did as I was told placing each hand palm down under my bum, she grabbed a pink silk dressing gown and put it on, lying back on the bed and looking at me I suddenly felt very exposed. This was becoming something of a ritual with Mrs Jordan, she would embarrass me and then take me up to the heavens, then embarrass me again. The same question went through my brain. ‘Should I stay or should I go’.

“Tony tell me about your three masturbation fantasies again, go into detail and miss nothing out.”

So I did, I went into more detail than I did that morning, explaining all the things that she questioned me on, it was embarrassing, but not as bad as that morning, after all she knew it all now anyway.

Afterwards she seemed happy and gave me a large, soft, white bath towel and then invited me to shower in her en suite. I left the door open thinking that she would want to watch me, but that was not her motive.

“No, close the door Tony, I don’t want the steam coming into the bedroom.”

So I had a shower in private and what a shower, it had jets coming in from the side, a vast array of shower jets. On the rack there were several shampoos, some scented, some not. I spent about ten minutes in there, at home a shower usually took me about three minutes.

After I had dried off I went back into the bedroom with my towel wrapped around me. Mrs Jordan was lying on her bed in the pink silk dressing gown reading a book, as I entered she smiled at me, put the book down and stood up. Untying the dressing gown it naturally opened up at the front before she allowed it to slip off her shoulders and fall to the floor. She looked stunning, I still could not believe that this was happening to me. Her body curved in all the right places, her boobs and nipples were just perfect, her bush was ..., I quickly looked up, not wanting to be caught staring at Mrs Jordan’s pussy for too long.

“It’s alright, there’s no reason to look away, you can look at my nether regions if you wish,” Mrs Jordan said softly.

We held eye contact for a few moments before I worked my eyes slowly down her body towards her pussy. It looked perfect, neatly trimmed and you could just see her slit through the hair, I could feel the stirring in my own loins. She dropped to her knees in front of me, undid my towel so that it fell down to the carpet and started sucking. I naturally started stroking her hair, I was about halfway there when she suddenly stopped. Standing up she took me by the hand and led me downstairs to the porch, on the small table in the porch were all my clothes in a neat pile, all pressed.

“Thank you for all your work today Tony, if you will just sort yourself out here I will get your wages,” with that Mrs Jordan disappeared back into the house and I started to get dressed, I was just pulling my jeans up when she reappeared, still naked with my £65 for the day. I thanked her and finished dressing with Mrs Jordan watching me. Once fully clothed I said goodbye to her, opened the door, stepped outside and tried to close it behind me. Mrs Jordan however, kept a firm grip on the door handle holding it open. Okay, I thought to myself, not really knowing what to do I repeated my goodbye to her and started walking down the garden path.

“Goodbye Tony, see you tomorrow.”

I turned around to see a stark naked Mrs Jordan stood in her own doorway waving goodbye to me as though it was the most natural thing in the world.

“Oh bloody hell,” I said under my breath, embarrassed as fuck, I kept my eyes to the ground and walked away as fast as I could.

[WedgieSlaveKyle]

Its back, let's gooo

[MasterBilly]

Wednesday morning and I was shown into the front room, on the table were the usual clothes, t-shirt, shorts and flip flops in addition there was a small butt plug and a bottle of lubricant. I looked at the butt plug, it was about four inches long, thin but with a sphere about halfway down it. Whether I liked it or not, this was going up my bum at some point today. I accepted it, Mrs Jordan had fingered my bum hole several times yesterday and I currently had £130 in my wallet, in a few hours time that would be £195, riches beyond dreams to me! What was the difference between a butt plug and a rich ladies finger anyway? I was not looking forward to the plug, but I accepted it.

I undressed leaving my clothes in a pile on the floor, naked I asked Mrs Jordan what she would like me to wear. Wordlessly she picked up my grubby underpants and looked inside, turning them inside out she showed the inside to me. I could feel myself getting smaller and smaller in utter shame. There was a light skid mark down the back, to the front there was a visible piss stain as well as a small cum stain. I was so incredibly embarrassed, it would have been bad enough in any environment, but here, in the spotless, sumptuous arena of Mrs Jordan’s house it just looked worse.

“These are disgusting Tony.”

“Yes Mrs Jordan,” I replied, not knowing what to say.

“Why are you wearing disgusting underwear?”

I thought about replying with, ‘I’m not, I have taken them off’, but quickly dismissed it, even if a cocky answer did not incur her wrath it was unlikely to do me many favours.

“Mum didn’t do any washing this week,” it was true, mum used to wash every Monday, but of late she started washing every second Monday, none of my clothes had been washed in over a week.

“Then why didn’t you put a clean pair on out of the drawer?”

“I haven’t got any, I only have four pairs of undies,” my eyes were welling up in the shame of it all. But it was true, I only had four pairs of underpants and by now they were all dirty, though I admit that I could have found a cleaner pair, but I did not know that Mrs Jordan would be inspecting them and I certainly did not know that she would put me through this.

“So what is to stop you washing them by hand?” She asked.

“Er I didn’t know, er, can you do that?” I had never even heard of washing clothes by hand, that was what washing machines were for. I did not have a clue how they worked, but somehow they did.

“Oh Tony, Tony,” Mrs Jordan sighed. “You should at least wash your socks and underpants, it’s hygienic. I will show you how later. In the meantime just put the flip flops on, I would like you to tidy the garage this morning.”

Still feeling humiliated about the underpants I put on the flip flops as Mrs Jordan picked up the butt plug and squeezed some lubricant on it, smearing it over the length of the plug with her fingers. She handed it to me and I held it by the base as she wiped her fingers dry on my dirty underpants. She then told me to come with her and I followed her into the garage. You could of course access the garage from the house, what else in a house this size.

The garage was a mess, things piled up untidily, shelves empty, spanners and screwdrivers left on the floor. There was also a chair by the wall that Mrs Jordan pulled into the middle of the garage. Sitting on it she pushed her knees apart and called me over, I stood a couple of feet in front of her.

“Closer Tony, come right up to the chair, stand between my knees,” Mrs Jordan told me.

Conscious that my limp cock was only inches away from her face I stood there as she admired my bits for a few moments.

“Now Tony, I would like you to put that plug into your bottom,” she told me with a casual look on her face.

I tried, it felt strange, but when it got to the ball it hurt too much. Mrs Jordan gave me advice like ‘try squatting down’, ‘lean forwards’, ‘push out like you are having a poo’. It did eventually slip in and as the sphere went up through my sphincter it was the strangest feeling in the world.

“Now stand up straight between my knees again Tony,” Mrs Jordan loved calling the shots.

I complied and watched happily as Mrs Jordan took my penis into her mouth, unlike yesterday afternoon though, this was the full monty. She slowly worked me up to a full erection and then as I started to get close she reached around and grabbed hold of the base of the plug and slowly pumped my arse with it. I had never even considered ‘anal’ before, yes there were a few schoolboy jokes about homosexuality and taking it up the bum, but I had never seriously considered it. But it was great, I actually enjoyed it. So many things were going through my mind, anal is wrong, this is so right, I am getting paid to receive blow jobs. All these things came together in my brain at the point of explosion, I fired several streams into Mrs Jordan’s mouth and she continued to suck me dry before pushing the plug all the way in, getting out of the chair and leaving me alone in the garage.

What was I supposed to do now, I was naked apart from flip flops, I had a butt plug up my bum, the lady of the house had just given me a blow job and then wordlessly got up and left me, presumably to spit my load out. Was I supposed to start tidying things up, just like that!

I looked inside a couple of boxes, nothing of interest lay within. I was browsing around when Mrs Jordan came back in, she told me roughly where she wanted things putting and that she would be back in an hour, she did not expect it to be finished but she did expect progress.

About an hour later she came to get me and led me into the drawing room (what the hell was a drawing room?), insisting that I removed the flip flops before going into the house. There was an upright chair with its back to an empty fireplace which I was told to sit on, Mrs Jordan insisted that I sat on my hands. I sat on the backs of my hands as I did in the bedroom yesterday.

“Now you are to remain sat there Tony, I will be about half an hour, when I return I may have somebody with me. If I do then we may ask you some questions. In the past Tony you have told me some white lies.”

“I haven’t, I’ve told you the truth,” I blurted out, how could she accuse me of lying.

“Like on Monday when you said you had experience of sex and were currently between girlfriends,” she said with raised eyebrows. I went red, bright red, I could feel my face burning. The fact that I was sat stark naked in her drawing room was irrelevant, I had been caught lying and I could not handle it.

“Whatever, you will not tell lies in front of my guest, if you do then I will spank your arse until it is red raw and then humiliate you to the very core, do you understand?”

“Yes Mrs Jordan.”

With that she left, I sat there and literally watched the clock, relieved that she had not pressed me anymore over the lying incident.

I heard several people arrive at the house over the course of the next 20 minutes or so and they all had female voices. It was about half an hour after Mrs Jordan had left me when she re-entered the room, she had said that she may bring a guest in with her, she brought them all in. I sat there in a state of shock as I counted 8 females as well as Mrs Jordan enter the drawing room and sit down in the various lounge chairs. I had not really noticed before but all the lounge chairs were in a semi circle facing me. Sitting on my hands, which were now getting numb, I had no way of covering my bits up. They examined me at their leisure. Most of them seemed happy, not surprising as they had a naked 16 year old boy to stare at, though a couple did seem very serious. The ladies themselves were all in the 25-35 year old bracket and all appeared refined, elegant and rich; similar to Mrs Jordan, who herself was probably one of the youngest of all 9 ladies.

“Right then ladies, this is Tony,” Mrs Jordan told the assembled group. Murmurs of greetings spread around the room.

“Tony, tell the ladies about each of your sexual fantasies, you have three of them. Go into detail and leave nothing out.” I stared at Mrs Jordan in shock, those fantasies were private, I would never even tell my closest friends. Mrs Jordan had coaxed them out of me in a moment of passion, now she wanted me to tell eight female strangers about my most private thoughts and if I did not do it then she would punish me. How could she, how could she treat me like this. I was aware of her promise to spank my arse red raw, I looked up at her with my eyes pleading for mercy.

“Tell the ladies your fantasies, don’t keep them waiting,” Mrs Jordan said with a hard edge to her voice.

“Please Mrs Jordan,” I whimpered.

“Tony, you know what will happen,” this time Mrs Jordan was virtually growling.

Crestfallen I let my eyes drop to my bare feet, taking a deep breath I began with my fantasy about finding a girl masturbating in the woods, it seemed the least embarrassing until got to the point where I got my phone out and started recording it, I suddenly found myself extremely humiliated telling this part of the tale.

“Tony, look up when you are telling this story, you are speaking to an audience, not your feet,” Mrs Jordan said forcibly. I looked up and saw all the female faces in front of me, they seemed to be eating into me, this was just awful.

As the fantasy went on I talked about me blackmailing the girl, tears of shame started to form in my eyes. I was stuttering and shrivelling up in my seat as I slowly got to the end of the story.

“Well done Tony, now move on to your second fantasy, remember,” Mrs Jordan snarled. “Leave nothing out, tell the whole truth and face your audience when you speak.”

I moved on to the two girls that I knew from school having lesbian sex in my bedroom. I found it slightly easier, it was still fucking embarrassing, but it did not seem as bad as before. At the end, without waiting for Mrs Jordan to tell me I went straight onto my final fantasy about finding a woman tied spread-eagled to the bed, this story I did find embarrassing to tell and by the time that I had finished I was in tears yet again.

“Now Tony, tell the ladies what you do when you are thinking about these fantasies,” said Mrs Jordan.

“Er, I don’t do anything,” I said confused.

“Tell the truth Tony, you play with yourself don’t you?”

Hell fire, surely she did not want me to admit that in front of all these did she?

“Well Tony, tell them all what you do, tell the truth,” Mrs Jordan said.

“I touch my pe ..... penis,” I said, I was completely in tears now, tears of pure shame were streaming out of my eyes and down my face.

“Do you just touch it or do you stroke it?” Mrs Jordan asked, again there was force in her words.

“I stroke my penis,” I replied looking up at her through bright red eyes, thinking how could you put me through this, how could anyone put another person through this.

“Is it called a penis or a cock Tony?”

“It’s called a cock,” I knew that is what she wanted me to say, though I could not understand why she wanted me to call it a cock.

“Then tell your audience what you do and when you do it.”

I looked around at them, about half of them were smiling, thoroughly enjoying my humiliating predicament, the other half seemed to have curious expressions on their faces, I suppose they were wondering if I would actually say something as humiliating as that, but what choice did I have, I was in a deep pit with Mrs Jordan staring down at me.

“I str ... stro ... stroke my cock,” I stuttered.

“When do you do it Tony?”

“When I’m thinking about my fantasies,” I sobbed.

“Then tell the ladies what you do and when you do it.”

“When I’m thinking about my fantasies I stroke my cock,” I blurted out now crying out loud.

“How long do you do it for?” Mrs Jordan asked again.

“Until I cum,” I whispered, looking down at my feet.

“No Tony, say it out loud and look at your audience, how long do you do it for Tony?”

I looked up at the ladies, unable to see them clearly through my tear soaked eyes.

“I stroke until I cum,” I repeated loudly.

“Now Tony, I want you to tell everybody what you do, when you do it and how long you do it for,” Mrs Jordan said cruelly.

“I str ... stroke my co ..... cock ... when I’m ... when I’m thinking about my fantasies,” I stuttered through tears before continuing. “And I do it until I cum.”

“Moving on Tony, I would like you to tell everybody what state your underpants are in,” Mrs Jordan said to my utter horror, I could never do that, ever.

I just sat there with my mouth open, shaking my head, this was unthinkable. Mrs Jordan repeated her instruction, but I couldn’t, I just couldn’t.

“No please,” I whispered out loud.
“For the last time Tony, tell my guests what state your underpants are in.”

I just sat there silently with tears streaming down my face, I could never, ever bring myself to openly discuss that.

“Very well, there will be consequences Tony, but if that is what you want, so be it!” With that Mrs Jordan went across to a chest of drawers, opened the second one down and using a single finger and thumb extracted my underpants, I felt sick as she passed them around.

“Have a good look at these ladies, I suggest that you pay particular attention to the inside, quite gruesome actually. But these are the underpants that Tony turned up for work in today.”

I sat staring at my feet as my undies were passed around the group of women, despite repeated instructions from Mrs Jordan to look them in the eye, my body simply would not do it.

“They are disgusting!”

“What a dirty little boy, he needs a good spanking.”

“Tony, you are disgusting.”

“I want to be sick, I do not know how anybody could be that dirty. Tony, do you actually know how to wipe your own bottom?”

“Oh my God!”

“They are truly disgusting, how can anybody allow their underwear to become so dirty, let alone put them on at the start of the day. I have never, in all my years, seen anything as disgusting as that, he has actually cum in them as well and still put them on the next day.”

I do not know who said what, I was staring at my feet throughout, but all those comments bit very deep.

“Tony stand up and turn around,” Mrs Jordan told me. It took a few seconds to register what she had said, but I complied, just happy not to be looking at the throng of female faces.

“Now touch your toes,” again I complied, in this bent over position I fully expected to receive another spanking but Mrs Jordan actually wanted to humiliate me more, not cause physical pain. She pulled on the butt plug, pulling it part way out so that the sphere was caught in the tight muscle of my sphincter.

“Look ladies, he enjoys wearing a butt plug as well, Tony tell the ladies why you enjoy wearing a butt plug.”

“I just like it,” I said whilst still crying my eyes out, not knowing what to say, but scared of going against Mrs Jordan.

“Okay Tony, you can go and wait for me in the conservatory,” Mrs Jordan said, pushing the plug all the way up me.

I got out of there as quickly as I could and headed for the conservatory, I sat down in one of the chairs and looked out over the garden, shaking like a leaf.

[MasterBilly]

A short while later I was joined by Mrs Jordan, she produced a case which she opened and pulled out a chrome butt plug with a long brown foxtail, the plug itself was wider than the one that I currently had in me.

“Now Tony it’s a nice warm day, so I would like you to do some gardening and I would like you to wear this while you do it. Now come and bend over my knee and I will swap your plugs for you.”

“I don’t want to work for you anymore Mrs Jordan,” I blurted out.

“Oh, okay, I understand you Tony, that is your choice. But you will see today out and I will pay your wages for today. Now bend over my knee so that I can swap over your plugs.”

“No!” I said hoarsely before looking away. “I don’t want to work for you anymore Mrs Jordan.”

“Tony, bend over my knee now,” I did not move, I just kept staring out of the window.

“NOW!” She shouted, but still I did not move. She leaned across and put her hand on my thigh, I could feel her staring at my face. Suddenly she grabbed hold of my testicles, I quickly put my hands over them but I was too late, her hand was on my balls, my hands were over her hands. She squeezed hard and then released the pressure.

“Would you like to reconsider?” She asked with a hint of sarcasm in her voice.

“I’ll bend over your knee,” I gasped, recovering from the recent pain inflicted on me.

“And will you work for me for the rest of the day?”

“Yes Mrs Jordan.”

She gave my balls another quick squeeze and I yelped out in pain before she let go completely, after allowing me to recover she patted her knee in indication for me to bend over.

I found my face only inches from the floor as Mrs Jordan prised my cheeks apart and removed the first butt plug, I felt the cold metal of the new one push up until it started hurting and I cried out in pain.

“Remember to push out like you are having a poo, Tony.”

I did and it slipped into me, though with a fair degree of pain. Why in the world people willingly did this was beyond comprehension to me. I stood up straight when requested/ordered and Mrs Jordan peeled back my foreskin and gave me a quick kiss on the end of my cock. With the first plug I never really noticed once that it was in me, this was different, there was definitely something up my bum and it felt strange, not uncomfortable but it was just strange.

“Right then Tony, go out and start gardening, everything you need is at the bottom of the garden,” Mrs Jordan told me after she had pecked me on the end of my knob.”

Feeling ridiculous with the end of my tail about 8 inches off the ground I went out and did my job, trying to forget the horror of the drawing room incident. A short while later Mrs Jordan and one of the ladies from the ‘drawing room’ came outside wearing bikinis and carrying a sun lounger each, they started sunbathing only feet from where I was working. I gathered that the other 7 had now left. The conversation of the two ladies covered many subjects but frequently kept coming back to me, they were never derogatory, in fact Mrs Jordan was occasionally nice about me, but it still felt uncomfortable hearing people talk about you as though you were not there.

By lunch time Mrs Jordan’s guest had left and she invited me to join her for sandwiches in the conservatory, once seated, which itself was uncomfortable with that bloody thing up my bum, Mrs Jordan peeled off her bikini top before slipping out of the bottom half. She positioned her chair well back to the side of the table giving me a superb view of her entire body. If this was meant to entice me to stay then she was wrong, nothing in the world would keep me in this fucking house after what I had to go through that morning in the drawing room.

After lunch I resumed gardening and I saw very little of Mrs Jordan for some time, it would be approaching 3 pm when she called me from the house and told me to join her. I was handed a large bath towel upon entering the house and was invited to take the plug out, I did and wrapped the towel around me before following Mrs Jordan into the main reception room. I was shocked by the sight in front of me as I entered.

In the centre of the room there were two blond girls in their early 20’s, both attractive, stark naked and stood with their hands on their heads. The nearest girl had her pubic hair shaved down to a well trimmed landing strip, the second girl was completely shaven, Mrs Jordan sat on a sofa and invited me to sit down, I chose a single armchair.

“Now sluts this is Tony, he doesn’t need to know your real names, ‘sluts’ will do for the moment. Sadly though, Tony has never seen a girl masturbate, well not in real life anyway. So you two sluts are going to rectify that now. Start masturbating and do not stop until you orgasm,” Mrs Jordan told the two girls.

I was unsure whether they would or not, just looking at two naked girls was giving me a massive lob on and the thought that they may actually play with themselves was only making me hornier, but part of me still did not think that they would actually do it. However, that part of me was 100% wrong, slowly the girls dropped their hands and started touching their fanny areas.

Their techniques were totally different. The nearest girl with the landing strip inserted two fingers into her vagina and stroked away with regular strokes, occasionally reaching right up and doing something inside herself, I could only assume rubbing her g-spot. Her left hand moved between caressing the area at the top of her slit and moving up to rub her left nipple, before moving back down to her slit again.

The other girl simply prised her lips apart with one hand and rubbed the exposed skin with the other. I was staring at her glistening fanny lips exposed for me to watch, I remember thinking how it looked like slices of processed ham. I vowed never to eat a ham sandwich again.

I could not understand why they had such different techniques, surely there was only one way to masturbate, after all there was only one way for boys to masturbate. I looked at their faces, both girls were developing flushed faces, though the girl nearest was redder. I looked down at their vaginas, again more seemed to be happening to the nearest girl, the two fingers of her frigging hand, in fact most of her hand was covered in slime, pussy juice. I was fascinated with how much she was producing.

I was in my element, I never thought that I would witness anything like this in my life. Two beautiful girls touching themselves purely and simply for my pleasure, why were they doing it? Who cares? My prick was forcing a tent pole in the loose covering of the dressing gown. Strangely I felt no need to attempt to cover it up.

The girls carried on and even started moaning, were they moaning for my amusement or was it genuine, I liked to think that it was genuine. The girl closest reached an orgasm first and emitted a few ooh’s and ahh’s as she climaxed. The other girl carried on rubbing her pussy lips but was clearly getting close. As she reached an orgasm she called out loudly, almost screaming and my eyes were diverted to her face, looking back down at her pussy moments later I saw that juice was actually running down her leg.

“Well done sluts, now for the fun part, we are now going to play Musical Fannies, I want you two sluts around the back of the sofa now.”

Both girls made their way around the back of the sofa and under Mrs Jordan’s instruction they leaned right over the sofa, spreading their legs out wide and pushing their bums in the air.

Mrs Jordan then indicated for me to join her behind the two girls, patting the first girl on the small of the back she gave me my instructions.

“Right then Tony, I would like you to stick your cock into this sluts vagina and start fucking her, now please!”

‘Oh Lord this is fantastic,’ I thought to myself. I am going to fuck at least one, possibly both of these attractive girls, me, somebody who has only recently lost their virginity. After a little effort my rock hard cock entered her and I started fucking. Mrs Jordan put some classical music on, but I did not have a clue what it was.

“When the music stops you are to pull your cock out and start fucking the other slut, okay Tony.”

“Yes Mrs Jordan.”

After about a minute the music stopped and I withdrew and moved to the other girl, there was a short struggle as I entered her but when I got all the way in she grunted in pain I felt like a right stud, every time I pushed in she grunted in the same way, I told myself it was because I had such a large cock, the thought only made me hornier and more aggressive. I also noticed that her twat was tighter than the first girl, that made me feel better too, the fact that I was now able to compare girls fannies, I was becoming a veteran!

The music stopped and I moved back to the first girl, old slack fanny. The music was lasting for about 40 – 60 seconds before it stopped and I noticed that I was entering the girls easier and easier every time.

I was on my eighth fuck, i.e. the second girl who could not handle my size, when I shot my load. I had not cum in several hours and I rammed my cock right into her, ignoring her cries of pain as I fired my semen deep into her body.

I pulled out slowly as Mrs Jordan stopped the music and walked up to the first girl and slapped her hard on the bum.

“Okay, your friend has taken his seed so you can suck him clean, get on your knees in front of him now.”

She complied instantly, dropping to her knees in front of me she took my gooey member in her mouth and proceeded to suck and lick it clean, I had to pinch myself to make sure that I was not dreaming.

Once Mrs Jordan was satisfied she sent me to the conservatory with a glass of wine whilst she had a ‘quiet word’ with the two sluts.

I sat there stark naked looking out over her garden wondering how much better this day was getting. Presently Mrs Jordan joined me and sat down next to me with our knees touching.

“Now Tony, when you got your cock all the way into slut number two, did you notice any reaction from her?”

“Yes Mrs Jordan, she grunted.”

“Why?”

“In pain, because of the size of my cock.”

Mrs Jordan laughed long and loudly at this, before offering me her views on the subject.

“Tony, believe me, your cock is no longer than anyone else’s; it is not the size, it is what you do with it. Some girls, like slut number two, do not have deep vaginas, which means that men should show more care and not push their cocks all the way in, you will only hurt the poor girl. Do you want to be regarded as a good fuck or a bad one Tony?”

“A good fuck Mrs Jordan.”

“Of course you do, they are the ones that get the most sex and give the most pleasure. So are you going to be more considerate when you fuck from now on,” it still sounded strangely filthy when Mrs Jordan said the word ‘fuck’.

“Yes Mrs Jordan.”

We rejoined the two girls and Mrs Jordan instructed them to perform a girl on girl 69 for our entertainment. The girls exchanged glances before slowly getting down into position. It was the first time that I really noticed it but the two girls were clearly not there for their own pleasure, but I did not know why they were there, as they started performing lesbian sex in front of me I cared even less.

They started eating each other out and I was encouraged to get up and walk around them, inspecting closely what they were doing. I could actually see the anus of the girl on top, to see that most private of places lewdly displayed was a massive turn on. The girl on her back orgasmed first, as her orgasm died down Mrs Jordan produced a small thin butt plug and liberally lubricated it before inserting it slowly into the girl on top.

I felt really sorry for her, she had done her job and brought off the other girl and now she was being made to orgasm on her own in front of an audience whilst having toys inserted up her displayed bum.

“Tony why don’t you fuck her bum with the butt plug a few times,” Mrs Jordan asked me with her eyebrows raised.

Was she inviting me or telling me, either way it was too good an opportunity to miss, I reached around the back and gently withdrew the plug nearly all the way, acutely aware of Mrs Jordan’s instruction not to be forceful. I slid it all the way in before repeating my action. I had by now totally forgotten about any sympathy that I had for the girl in question, this was simply fantastic, fucking a girl up the bum using a plastic toy. I briefly wondered if I would ever get the chance to fuck her up the bum with my cock.

The third time I took the plug out completely and watched as the hole sealed itself up, she was by now getting close and it was only a matter of time before she came to orgasm, after which I probably would not be allowed to carry on. Making the most of it I slowly fucked her two more times just as she came, I watched in amazement as her juices covered the face of the poor girl licking her out.

I removed the plug completely and offered it to Mrs Jordan who for some reason refused to accept it, so I stood there like a lemon holding the plug by the base. I was naked, the towel and dressing gown that I had earlier was lying discarded on the floor; the two sluts were obviously naked, only Mrs Jordan was clothed. Again I had one of those surreal ‘is this really happening’ moments.

The two sluts were ordered by Mrs Jordan to take the plug from me and go and clean up themselves and the plug and then to report back.

As they left Mrs Jordan grabbed the towel off the floor and threw it at me, I wrapped it around myself instinctively feeling grateful for the covering, before thinking what difference does it make anyway. Mrs Jordan had seen every little private part of my body and I had just witnessed the two sluts performing the most humiliating tasks imaginable.

They came back in together and as me and Mrs Jordan sat in front of them they were ordered to stand with their hand on their heads and in turn describe the first time that they had ever had sex.

The first girl clearly did not want to describe the event and initially glanced around the room in bewilderment before taking a deep breath and starting to talk about it. She spoke in a flat monotone voice but it was still a massive turn on for me, listening to a girl talk about sex obviously was to a 16 year old with virtually no experience, but when that girl is blatantly forced into it then it is ten times more erotic. She clearly wanted to get it over with and paused very little going into as little detail as she thought that she could get away with. At the conclusion of her tail Mrs Jordan seemed quite satisfied and told the second girl to describe her experience.

If the first slut found the experience difficult then the second one found it immense. Her eyes filled up with shame as she stuttered and stammered through her story, in a way it reminded me of my experience in the drawing room that morning, the big difference of course, was that I hated every second of my time in the drawing room; this on the other hand was the most erotic thing that I had witnessed during my 16 years on the planet. A naked girl talking about her own sexual experiences whilst being totally humiliated, I would be having ‘memory wanks’ over this for the next 10 years.

At the conclusion of the second girls story Mrs Jordan allowed them both to get dressed and depart the premises. She turned to address me using her patient and understanding voice.

“Tony, do you see how hard it was for those girls to talk about sex?”

“Yes Mrs Jordan.”

“The fact that they found it difficult increased their own sense of humiliation, if they had ‘owned’ the stories, talked about them with confidence then it would have been much less embarrassing for them, after all we have all had sex at some point, why should it be embarrassing talking about it. It was the same for you this morning. Everybody masturbates at some point, girls included. Talking about it should not be embarrassing. The next time that I ask you to talk about sex do it with confidence and authority, it will be far less humiliating. Do you understand?”

“Yes Mrs Jordan,” I replied, seeing her point. I also liked the fact that she openly admitted that girls masturbated.

With that she took me into the utility room and showed me how to hand wash my underpants before hanging them over a radiator and telling me that they would be dry by tomorrow morning, inferring that I was to walk home commando. I briefly wondered what her husband would think when he came home and found a strange pair of men’s underpants hanging on the radiator, before dismissing the thought. Mrs Jordan was far too shrewd to be caught out like that.

Finally Mrs Jordan watched me get dressed, minus my undies of course, then paid me my wages for the day and then bid me goodbye.

As I walked away from the house I thought about everything that had happened, it had been one hell of a day, at lunch time I was determined never to go near that house ever again, but now I was unsure, would I go back? Did I want to go back? Was the money actually worth it?

I passed the house next door just as the lady of the house was walking out of her garage.

“Can I have a word please,” she beckoned me over using three fingers of her right hand.

“Why?” I asked suspiciously.

“Please, just a quiet word,” she reiterated.

There was something about her that was curiously inviting and I walked across to where she stood, she looked me in the eye as she started to speak.

“I am Patricia Johnston and I live here, I know exactly what is happening to you next door and it is illegal,” she said calmly staring me in the face.