My start (little slow story)

[subDanni]

In my previous living arrangement I was always able to live out some of my secret fetish fantasies online, as I was living alone in my apartment. My fetishes was the main reason I didn't want to rent out my spare bedroom to any of my friends, or strangers, obviously. But after a close female friend of mine was kicked out of her boyfriends apartment after they broke up, all this was about to change. She was a student and didn't have a job, and therefore had very little money. We had been friends for many years. I considered her to be one of my closest female friends. Not that I had many female friends, but I felt she was a person I could trust. When she told me about her situation I quickly considered the option of letting her live at my place, for a while at least. Her only options was to live on the couch at some of her student friends, so after a little consideration I offered her to stay at my place. In my spare bedroom, until she figured out what to do. I knew she wasn't able to pay, but I didn't mind. Since I'd never rented out my spare bedroom, it wasn't like I was losing money. The only problem was that now I couldn't do all the perverted things I usually did with my dominating friends I had online. I would also have to hide all my fetish equipment a little better. Another concern was that I thought she was really hot. She was the kind of girl I sometimes fantasized about and also the kind of girl that have a lot of sexy clothes. Having her live at my place would give me the opportunity to go through her stuff. Particularly her underwear. Maybe she had sex-toys, like for example a dildo. This was something I never should do, but it would be hard to resist. Nevertheless, since this was just a temporary solution I would have to manage and don't do anything stupid.

She started living at my place in the beginning of the week, but since I was gone on a work related trip we wasn't able to catch up before Friday, in the afternoon. And not for long as she was going out for drinks with some of her friends. After she'd left I went to the living room to watch TV. I didn't have any plans and it didn't take long before I wanted to go into her room and poke around. I tried to resist, but it was hard. I wanted to sniff her underwear, and also wear them. I decided to invite some friends over to get my mind on other things. We watched movies for a few hours until I got a message from my new roommate. It was late and she had lost the last bus back home and could not afford a taxi. She asked if I could pick her up. I said yes, pretending that I didn't wanted to, but I actually didn't mind. My friends went home and I went to pick her up with my car. On the car ride home she apologized several times for having me pick her up. It was noticeable that she'd had some drinks, but she wasn't drunk. When we got back to my apartment I asked her if she wanted something to eat and drink: “You should eat something and drink some water so you don't get a hangover. I can make you something”, I said. “Oh, thank you. You are so kind”, she answered and sat down on the sofa in my living room. I brought her a glass of water and sat down in the sofa. “You don't want to sit next to me?”, she asked with a little laugh in her voice. “Yes of course”, I said and sat down next to her. “I think it will take me some time to find an affordable place I can live for myself. Right now I'm almost broke”, she said. “That's ok, take the time you need. It's no rush. Besides, it's nice to have some company”, I replied. “You are too kind to let me live her for free. I wish it was something I could do to repay you”, she said as she touched my thigh with her left hand and gave me a sexy look. “I don't know where you are going with this. It feels wrong to take advantage of your situation. I just want to help a friend out”, I said. “Oh, I just think you deserve a reward for all the things you do for me”, she said and moved her hand up to my crotch, and continued, “at least let me give you a little lap dance, that's harmful”. I got very excited, but managed to answer that it was OK. She stood up, she was wearing black and tight leather pants, sexy high heels and a sexy white top. She started to dance a little for me. With her ass in my direction. It was very sexy. I could see that she was wearing a black bra. I figured she wore a sexy black thong under her pants. She then turned around and sat down on my lap with her breasts very close to my face. I got very excited and my penis became erect. She grabbed my hands and put them on her breasts and smiled at me. “I noticed that you are getting excited down there”, she said. “Yes it's hard not to. You are very hot”, I answered. As I sat there, I didn't thought about fucking her. I thought about how much I wanted her to dominate me. I wanted to be her submissive. “You know. I could take care of that”, she said as she smiled and put her tongue out in a sexy way, implying she could give me a blow job. “You really don't have to. I feel that I take advantage of you”, I answered, even though I wouldn't mind her taking care of my boner. “Well, isn't there anything I can do to repay you?”, she asked. I started thinking. She was a person I trusted and she was very open minded. She once told me she'd had a boyfriend who had a feet fetish. When she told me about it she said it wasn't a big deal for her. Having this in mind I really considered asking her if she wanted to hold the key to my chastity device. In my horny state of mind that was a harmful request, but regardless, it was hard to ask. “Well, there is one thing I want to ask, but I'm not sure if I dare”, I answered as I moved my hands from her breasts to her legs. “Oh, just ask, I wont tell anyone. But I can say right now that I don't do anal”, she answered. “No it's nothing like that. I just have a strange fetish”, I said. “Oh...Well, what is it? Now you get me curious”, she replied. I paused, but decided to ask,“Well, I like to wear a chastity on my penis. Have you heard about that fetish before?”, I said. “Yes I've heard a little about that, why do you want that?”, she asked. “Well, I get turned on by not being able to masturbate, especially if a sexy girl like you have the key. I think it's the giving up control part that turns me on. I've worn it before, but never longer than one week. That's about how long I want you to have the key.”, I said. “So I just hold the key to the thing?”, she asked. “Yes, and no matter how much I ask you for it back you must not give it back before”, I answered. “Well, this could be interesting, but doesn't it hurt?”, she asked. “Only when I get really turned on and my penis try to get erect, but that's a part of what turns me on about it”, I answered. I was really excited now and said;”But promise you wont tell anyone. Is it ok if I put it on know?”. “Yes, I want you to. And I wont tell anybody. Maybe I can make the food and you can get your device on”, she replied and stood up and went to the kitchen. “Yes”, I said with an exciting voice. I went to my storage room and got the chastity device. When I got back to my apartment I went to the bathroom to take it on. Suddenly she knocked on the door, “the food is ready”, she said. “I'm coming, just give me a minute”, I answered as I put the lock on the device. I got out of the bathroom. “Here is the key”, I said and gave her the two keys to the chastity. “Well, I want to see it”, she answered. “Really? It's a little embarrassing”, I said. “Come on, I want to see my locked up penis”, she said with a smile on her face. I noticed she called it her penis. I liked that. I pulled my pants and boxers down. She gently touched the cage with her finger tips, and then my balls. I gasped as she gently stroked my balls. “Hehe, I think this will be a hard week for you”, she said. “Yes, but it's important that you are strict and don't give me the key too early”, I answered. “As you wish”, she answered. We went to the kitchen. “So, let me ask you. You said you've worn it for a week before. Where did you leave the key then?”, she asked. “I used a numeric plastic lock for someone to control it online. I had to send photos every day to show that the number on the lock was the same. I could just take it off if I wanted, though. Which I eventually did.”, I answered and continued. “But now we use a real lock and I can't get out before you want me to”. “I see, so you have a little experience. Was it planned one week with this online friend of yours?”, she asked. “No, but I cracked after one week. And it wasn't that exciting when I knew I could take it off when I wanted”, I replied. “It seems to me that you don't want to know when I'll let you out”, she said with a smile on her face. “You're right, but I want it to last more than just a few days”, I replied. “Oh, it will”, she said. I got a little suspicious, but I figured she was joking around. The way I knew her she would let me out next Friday. I thought about the situation I was in. Even though this was a really small part of all the things I'm into it was nice to for the first time involve a real person in my submissive fetishes. Someone I didn't met online.

[subDanni]

The first days was a little difficult. Especially sleeping with the cage, but it got adjusted and became easier as the days went by. I'd learned from the last time that the first days was the hardest. And also if I became really horny it was hard to sleep with the chastity. When I was at work it was fine wearing the cage, unless I saw some of my sexy colleagues. When I saw them I began to fantasize and the cage became uncomfortable to wear. Luckily for me, there weren't many sexy women at my department at work. My keyholder had just started in a part time job after the weekend so she wasn't home so much this week, which was also lucky for me. Her presence made me very horny. She didn't tease me, though. She just kindly asked if I was doing ok. Other than that we didn't talk about the fact that I was wearing a chastity on my penis.

On Thursday I lost control, in a way. She wasn't home, so I decided to poke around in her laundry. I found her sexy thongs and bras. I started to sniff them. It felt amazing and I became really horny. I was doing very good until this point, but one could say I'd cracked. I pulled my pants down and rubbed her panties on my chastity and balls. At this point I was extremely horny so I sent her a text message and asked when she was coming home. “In a few hours, why do you ask?”, she replied. I knew I shouldn't ask, but I did, “Is it possible to be released today? It's just one day before”, I asked. “Haha, I don't think so, you told me not to”, she replied. “Please reconsider, it's becoming too hard”, I replied. “I don't have time to send more text messages now, we'll talk later”, she answered. Somehow my mind had a little hope that she would release me today. I was in a state of horny and stupid. I took off all my clothes. There were several sexy thongs and bras in her laundry, but I found a really slutty and pink set. I put them on and went into her room. I took my normal clothes on as well. There was a lot of sexy clothes in her closet. Skirts, tops, underwear etc. I wanted to try on a sexy outfit. Even though I'm a skinny guy her clothes would get stretched out, but hopefully not too much. Before I managed to decide what to wear and messing up her closet, as I was until this moment just watching into the closet, I could hear someone unlocking the main door. I quickly turned off the lights in her room and went out, shutting the door behind me. It was her. She was home already. “I thought you said a few hours”, I told her. “Well, I was just getting off the bus when you texted me and I found the text message strange so I decided to lie and see what you were up to”, she answered with a grinning smile. “I'm not up to anything special. Just a little horny”, I answered, knowing I was wearing a pink thong and bra under my clothes. Her pink thong and bra. “Oh, really”, she said, as she went into the laundry room. “What happened her? The laundry is all over the floor”, she acknowledged . “I dropped the laundry basket, I'll clean that up”, I answered. I was really nervous and was not sure what she was thinking. “Oh, thats ok, I can fix it myself later”, she said and continued. “I've thought about your request and I want to see my locked cock before I decide if I'm letting you out early”. “Oh, that, well I changed my mind. I want to go the whole week”, I answered. “That's ok, but I still want to see how my penis and balls are doing”, she said. This was turning me on a lot, but I was also scared, since I was wearing her underwear and I didn't know how she would react. “You want to see it now?”, I asked. “Yes, now. Drop the pants, boy.” she said. Her voice were getting a little strict now. “I just have to apologize. Please don't tell anyone about this”, I said as I took my pants down. “Oh my god, is that my underwear? Why are you wearing my panties?”, she asked. “I just poked around and got really horny”, I answered. “Is this one of your fetishes? To wear female underwear”, she asked. “Yes, especially if they belong to a sexy woman”, I admitted, looking down, ashamed. “Well you're a real pervert. But since you're kind enough to let me stay here for free I'll let you keep that thong. Don't worry, I won't tell anyone”, she said. “Thank you so much, but I have to admit something else”, I answered. “Omg, what is it?”, she replied. “I'm wearing your bra as well”, I said. “Take of your shirt so I can see. You know what. I'll let you keep that too, and I'll let you take all my dirty underwear. I have a task for you”, she answered. I became really horny and also kind of nervous, “you'll let me get all your used underwear? That's ok with you?”, I asked. “You don't want it?”, she asked. “Yes of course I want them, but I'm a little curious and nervous about this task you mentioned”, I said with humility in my voice. “Well you should be. I want to do something fun. I want you in chastity for one extra week.” she said with a grinning smile on her face. “Really? That will be hard for me. I'm really horny now.”, I answered. “Yes, but not only that. I want you to wear a different bra and thong everyday to work”, she said. “I have to wear your used underwear to work?”, I answered, as I became kind of shocked. “Yes, you're not allowed to wash them either. To prove you really do it I want to see you wearing them when you leave in the morning and I'm also gonna send you a message were I ask for a picture of you only wearing a thong and bra. You'll have five minutes to reply with the proof”, she said. “What happens if I don't manage to do it?”, I asked. “Well, for every picture you don't send or you respond too late we will add one day to your chastity. Think you can handle more than one week more week?”, she replied. “That will be hard I think”, I said. “Yes it will. But you will just have to manage if you don't follow my rules”, she said with a cruel voice and continued. “Also, I want you to buy me new underwear. Don't you think that's fair?”, she said. “Yes, I agree. I'll give you money for new underwear”, I replied. “No, I want you to buy it. On Monday after work. Five bras and five panties. I hope it will be humiliating for you. Wearing my used underwear and a chastity while buying me new underwear. If I don't like what you've bought me you will have to buy new ones the next day.”, she answered in a strict tone. “Yes, I'll do what you say. You've become kind of cruel”, I said. “I know you like it you little slut, and it also benefits me”, she answered and continued, “Now put your clothes back on. And yes, you will leave my used underwear on”. I did as instructed.

I really liked the task she gave me. It made me really horny, but I was also a little scared, because someone at work could notice that I was wearing female underwear. I was also afraid that I would end up with even more days in chastity. I was already starting to lose control and was becoming really frustrated.

[Bdeups1]

This story is really good

[subDanni]

Going to the lingerie store that Monday after work was really humiliating. The ladies who worked there was really sexy. It was hard not to think about my humiliating situation. It made me horny and also a bit ashamed. My face became red when I walked around in the store. I tried to be very quick and picked out thong and bra sets I thought was sexy. I also picked out a little expensive underwear. I didn't want to risk having to go back. It was hard to tell if the sexy lady at the store selling me the underwear was thinking that I was a pervert who liked to wear female underwear since my face was red and I was a little nervous, but I didn't care. I just had to get it over with. On the car ride home I was relieved that the day had gone sort of well. I'd bought her new underwear and replied to her messages within time, although it was humiliating to stand in the toilet at work in just a used thong and bra, and of course the chastity on my penis. When I got home I laid the underwear I'd bought for her in the living room. She was working so I would not see her before Tuesday morning. Before I went to bed I sniffed all the used panties and bras she'd let me have and decided which ones to wear the next day. The days went by and I completed her picture tasks in time. She only messaged me twice a day asking for a picture. Due to her working situation we did not see each other much the first days of the week, but on Thursday she sent me very many messages requiring pictures of me. I became nervous and frustrated. I wasn't able to answer everyone in time. She instructed me to do different things in all of them so I couldn't use the same picture twice. It would also be noticeable if I did. I managed to fail four times. That meant four more days in chastity. I replied on her last message with a question: “Why do I have to send you so many pictures today? You know I'm wearing female underwear.”. “I'm bored and just want to have a little fun. By the way, you have four more days in your cage*”, she replied. “Can you please reconsider? It's impossible to reply so many times”, I asked. “Maybe. I'll give you the days back if you give me the password to your computer”, she answered. I just remembered that she was home that day. She didn't have to go to work again before next week and was studying from home. I wasn't sure if I wanted to give her my password. Even though all my porn was stored on an external hard drive and I deleted my browser history every evening, there might be a way to find out of about more of my fetishes besides the ones she already knew about. “Why do you want to go on my computer?”, I asked. “Don't worry, I won't go through your porn stash. I forgot my computer at school and need one to study. I'll let you off the hook if you let me use your computer*”, she replied. I wasn't sure, but I thought I'd done all the precautions I needed so I sent her my password. I didn't receive any more messages that day and could go home knowing I would most likely be let out of chastity the next day. It'd been a difficult but exciting week. Having to wear a chastity while knowing a sexy girl were holding the key and giving me humiliating tasks was like a dream come true. The fact that I was wearing her used underwear made it even more frustrating for me. Which turned me on a lot.


When I got home she'd made us dinner. “Hi, I hope you're hungry”, she said as I entered the kitchen. “Hi, yes I am. Nice of you to have dinner ready when I come home”, I said. I didn't want to mention anything about the chastity just yet, so we just spoke about normal things while we ate dinner. After a little while she mentioned my trip to the lingerie store: “I forgot to thank you for the new underwear you bought me. It's all really sexy, you have good taste”. “Thank you, I just picked out what I thought was most sexy. And what I would want to see you wearing”, I replied. “Really, well I don't know about that. Maybe you will, if I'm feeling particularly nice one day ”, she answered with a smile and continued “are you excited for tomorrow?”. “Yes, two weeks without masturbating is really hard, especially when I have to do humiliating tasks for you”, I answered. “Hehe, I can imagine that you're quite frustrated. I hope you enjoyed that I've been a little cruel”, she said. “Yes, it turns me on”, I answered. It seemed that there was something she wasn't telling me. I got nervous that she'd might found something on my computer. “Bye the way, you're Skype logged in automatically, sissyslave_24, that's what you call yourself online?”, she said with a little laugh in her voice. It felt like my heart stopped. I hadn't thought about my Skype. I'd done a lot of things in front of different masters and mistresses on Skype. “Eeh, eehm”, was all I managed to reply before she continued, “well I didn't think much about it at first, but suddenly a guy called master_for_sissies started chatting with you. Or should I say me”. It still felt like my heart wasn't pumping. He was one of the people I'd done a lot of dirty and humiliating things for on cam. He was also living in this city, but we'd never met in real life because I didn't dare taking it that far. And I'd never shown him my face, even though he was really eager to both meet and see my face. “What did he say?”, I asked with a nervous voice. “Well first he told me to get my cam on and take off my clothes. I told him that he wasn't chatting with you. I even got the cam on for a few seconds to prove it.”, she answered. “OK, that was it, you logged off after that?”, I asked. “Hehe, far from it. He told me quite a few interesting things about you. He said that even though you two had played a lot online you didn't want to meet him in real life and not show him your face”, she said. “That's because we have an online, sort of relationship”, I said, still frightened of what she was going to tell me next. “Don't you want him to dominate you in real life? He showed me some of your chat logs and it seemed to me that you really want someone to dominate you”, she said. “I'm not sure”, I answered. “Well, I took the liberty to send him one of the pictures you sent me today so he could see your face. I told him that the underwear you were wearing was stolen from my dirty laundry. I also told him I had control over your chastity”, she said. It was hard to wrap my mind around this situation. She continued, “he is really eager to meet you. He told me all about the power I have over you due to your cock being locked in chastity and he gave me a very tempting offer”, she said, smiling. “What do you mean?”, I asked. I was shaking more now. “Oh, you look so scared. He just said that he could book a trip for me with hotel and all included this weekend. He just wanted me to leave you here”, she said and continued, “so basically I gave him our address and he want you to be his slave or whatever this weekend. Isn't this what you've dreamed of?”, she asked. She seemed to be really happy about all this. “I'm not sure what to say. What happens if I deny?”, I asked. “Well my trip is already booked, so I don't really care, but he might get upset. I should warn you that I did send him all the pictures you sent me this week. Maybe he'll post them online, I don't know. He told me all about the stuff you've done for him on cam. It seems about time you two play for real”, she said. “What happens after the weekend, then? This is all going very quickly”, I asked. “Well, as far as I'm considered you're off the hook, unless you want me to lock you in chastity again. Which, by the way, your master said would be very easy for me to do.”, she answered and continued, “you seem like a completely different person in the chat logs he showed me. I've learned the last two weeks that you're really kinky, but that is nothing compared to what I've read about you now”. “Yes, I'm ashamed of myself now”, I said while I looked down. “Don't be. I don't care. I just care about this trip of mine. And I want you and your master to have fun. I don't judge”, she said. “Well, maybe it isn't so bad”, I said. “Come with me”, she said. We went to the laundry room. “Take off your clothes except the thong and bra you're wearing and get down on your knees”, she said. This got me horny and I thought maybe she would let me out of the chastity, so I did as she said. She pulled out a dirty thong from her laundry basket. One of her new ones, which I'd bought her. “Do you want this?”, she asked. “Yes I do”, I answered. “Well, according to your Skype friend you have a lot of slutty clothes, so why do you want this thong, then?”, she asked and leaned back on the sink. I was on my knees in front of her. “Because it's been worn by a sexy lady”, I answered. “Open your mouth”, she said. I did, and she stuffed the thong in my mouth and continued, “I'll be honest. Your Skype friend told me that I would only get the trip from him if I could convince you to be his slave this weekend. I really want to go on this trip. Won't you do me this little favor?”, she asked as she tapped my chastity with her feet. My mind was spinning. I was so horny and in a way I really wanted to be dominated by my online master in real life. She stood up and got really close to me. I had her crotch right in front of me. “Grab my ass with both your hands”, she instructed. I did. It felt amazing. The chastity became painful to wear as my cock pushed hard against it. She pushed my head into her crotch. “Take a deep breath”, she said. My mouth was gagged with her thong so I took a good sniff with my nose. She pulled my head back and looked down at me. “Won't you just do this little thing for me? Just nod your head”, she said. I looked her in the eyes. She made it sound so harmless and after a few seconds, I nodded. She got two more used thongs and stuffed one more in my mouth and made me wear the other one over my head. “Do you like how I'm treating you?”, she asked. I nodded again. “You look so ridicules. Well, you can keep them, but you need to pay me. I need some extra cash for my trip”, she said. “Yes”, I said as I pulled the panties out off my mouth. She left the bathroom and I went to my bedroom to get my wallet.

Later that evening she told me that my Skype master wanted to chat with me so he could give me some instructions. He would arrive the next day, in the evening and expected me to be dressed up slutty and ready to be his slave. I was instructed to have a clean ass and luckily for me I had equipment for just that purpose. I was also instructed to have a lot of ropes and duct tape ready, and my cock was to be locked in chastity. Receiving these instructions made me nervous for what he had planned, but I figured at least I would get to masturbate before he arrived. When I was done chatting with him I went to the living room, where my new roommate was watching TV. She would leave early the next day on her trip so I was hopping for a chance to masturbate Thursday evening. “Will you give me back the keys to the chastity tonight or tomorrow?”, I asked. “Well, about that. Your master told me to put the keys in a lock box with a combination on it. He told me you have one of those”, she answered. I did have one of those boxes. “Won't you just let me masturbate one time tonight? He won't notice”, I begged. “No. It's more funny to deny you”, she said smiling and continued, “there is an upside though. He wanted me to text you the combination to the lock box before he arrives. He will tell me when. So if you're bold enough you'll unlock yourself and masturbate before he arrives and lock yourself up again”. “So I'm allowed to masturbate tomorrow?”, I asked. “Well, he told me to warn you that if you wasn't locked when he arrived you would be sorry. He didn't say what he would do. Only that it would be painful for you”, she answered. I figured this meant I wouldn't be able to jerk off tomorrow either. Although having the keys in my hands could change my mind and make me do something risky.

While I tried to sleep I thought about what I would wear for master. I knew what he enjoyed seeing me in. Even though I wasn't a very hairy guy I would have to shave my body as well. I wanted to be perfect for master. Because I wanted to please him, but also so he wouldn't punish me. While thinking about this I licked and sniffed the bra and panties I just received from my new roommate. She gave me the ones she'd worn today. I loved licking the crotch of the panties. I was really horny and frustrated, and thought about what might happened to me this weekend. I assumed I would get tied up by another person for the first time and fucked in the ass by a real cock for the first time. After a while I eventually fell asleep.

[redtiger]

Please break your story into paragraphs of a reasonable length. The unending blocks of text are extremely intimidating and very difficult to read.

You do not need to worry about tabs, alignment, that kind of crap. Just do a double space between paragraphs.

[subDanni]

Originally Posted by redtiger

Please break your story into paragraphs of a reasonable length. The unending blocks of text are extremely intimidating and very difficult to read.

You do not need to worry about tabs, alignment, that kind of crap. Just do a double space between paragraphs.

I didn't thought about that when I wrote this. I'll keep it in mind next time I write something here.

[DanB258]

Please tell us more of the story

[vance810]

Lovely! Hope to see a continuous of this story. Sounds like an amazing and exciting experience!

[SissyJess121]

Yes, please continue this story, I love it! It is almost cruel if you would stop at this point.