[Fiction] Dare initiation

[messyalan]

CHAPTER 1
I have known for a long time that my husband cross dressed and it hasn't really bothered me. However, about a year ago I found out he had gone outside dressed as a woman. When I asked him why he explained it was originally a dare but he'd got a tremendous thrill getting up the courage and then actually doing it. I couldn't really understand it and this is the story of how my husband got me into dares or, more specifically, exhibitionist dares.
Now I am a fairly shy girl but I do relax among friends. I have a good body, I'm told, but rarely show much of it outside the house. It was while we were out shopping that Steve started me on my conversion. He saw a dress in a store and asked me to try it on. I took it into the changing room and put it on. The dress was not designed for a bra as it had a plunging neckline but I am a big girl in that department and very rarely go without a bra. Not because my boobs sag but it can get uncomfortable and I suppose I also feel people looking.
I went out of the changing room to show Steve and he looked me up and down before saying, “Lose the bra, it looks ridiculous.”
Straight away I felt myself blush as the female assistant looked straight at my chest.
“It's not my kind of dress” I hissed back acutely embarrassed.
“Humour me, please” he replied and I went back to the cubicle.
Feeling very self conscious I loosened the dress, took of the bra and zipped the dress back up. With more than a little trepidation I went back out.
“That looks fantastic” said Steve and again I felt the gaze of the assistant but she was at least smiling. “It could do with being a lot shorter but I like it. Lets buy it.”
“When would I wear it?” I asked, genuinely trying to think of a time I would wear a dress like this.
“How about now?”
“You are joking. It's hardly a shopping dress.” I replied wondering what he was doing.
Turning to the assistant Steve asked, “Can I just pay for it and she can keep it on?”
The assistant explained the dress needed to have the security tag removed so she would need to take it to the till but she would bring it straight back.
“That's settled then. Get the dress off and I'll pay for it.” and I walked back into the cubicle slightly dazed. I slipped the dress off and passed it to the assistant around the curtain then sat there in my knickers whilst Steve paid for it.
A few minutes later she returned and passed me the dress along with a bag for my jeans, bra and jumper. It took a few moments for me to pluck up the courage to step out but I kept thinking how ridiculous it was. After all it was just a dress and its not as if I was naked.
I took Steves arm for security as we walked out of the store and I felt as if everyone was looking at my chest.
“I think I've done enough shopping for one day, can we go home now?”
“Don't be silly. How often do we get a day out together. Let's have some lunch.” replied Steve stepping out down the street.
Gradually I started to lose my nervousness as everyone in the street was just going about their business. We got to a restaurant and were shown to a table by a very handsome Italian who left us some menus. I busied myself choosing the food only to realise the waiter was back and standing at my side. Goosebumps ran through me as he must have a good view down my cleavage and the feeling I had now was flirty rather than embarrassed. I demurely leant back and gave him my order before excusing myself and heading to the ladies. Once in the empty room I spent a little time adjusting my breasts so they were pushed up a little more and slightly apart.
I returned to the table and sat down carefully not breathing too hard. When the waiter returned with our food I really enjoyed watching his eyes undress me.
As the waiter left Steve said, “So now you like the dress?”
Was I that obvious?
“I guess you won't want to return it then?”
“I'll keep it for now.” I said matter of factly and smiled inwardly.
That was the start of my transformation.
Actually I think the start was an hour later when we got home and Steve grabbed me as we walked through the door. To be fair I was as horny as him and he only removed my knickers and pushed my dress up before taking me on the hall carpet. Definitely my best shopping trip yet!

CHAPTER 2
The next time was a weekend trip out for a walk and a pub lunch. I had put on a thin white cotton blouse and long shorts along with white trainers.
When Steve saw me he said, “How about taking off you bra today?”
At first I wasn't sure but eventually plucked up courage to go back to the bedroom, take off the blouse and bra and put back on the blouse. I looked in the mirror and you could vaguely see my breasts but you could definitely see my nipples. Still unsure I compromised by putting on a thin white cardigan which I could pull round me and I shoved my bra in my bag.
When I went downstairs Steve gave me a kiss and a feel making my nipples stick up again.
We walked for about an hour and saw very few people and in the warm sun I took off my cardigan and enjoyed the thin cotton playing on my breasts.
When we got back to the car parked near the pub I put on the cardigan again on the pretext it was cooler in the pub. In fact it was quite a bit warmer but I couldn't bring myself to take off the cardigan as I felt I would be too exposed although I did leave it unbuttoned. After about 20 minutes I went to the bathroom and splashed some water on my face to cool down. As I walked back into the bar I noticed one or two men looking fairly obviously at my chest. I looked down and was mortified to see I had inadvertently splashed water down my blouse which was now stuck to my left breast hiding very little. My first instinct was to pull the cardigan round but realised this would just highlight it even more so I just sat down and turned to hide as much as possible.
Steve saw and said, “Now that is a great improvement.” then he leant over and whispered, “I think I might rip that blouse off you later.”
I felt myself go bright red but also got a tingle knowing what happened the last time we got home.
After only ten minutes my blouse had dried off and I felt more respectable. That was when Steve said, “Do you want another drink?”
I had already had two drinks and didn't want any more so said, “No I've had enough thanks.”
“How about your blouse, it looks very thirsty?”
I couldn't believe what he was inferring but something made me tingle again so in a loud voice I replied, “Maybe just a glass of water before we go.”
Steve smiled and went to the bar before returning with a glass of water and I noticed lots of ice. I wondered whether that was his idea?
With my back to the majority of people I put the glass to my lips and tipped but made sure a quantity ran round the edge of the glass and down my front. It really was freezing but I managed to get over half down my front. Apart from my blouse my shorts were also wet and I put the glass down and headed outside.
Steve followed and we walked the short distance to the car. I went round to my side but Steve followed and asked me to show him the wet parts. Looking around I saw no one nearby so I opened my cardigan to show the blouse plastered to my breasts. He smiled and walked over and leant forward to kiss me. I too leant forward and our lips met. However at the same moment he grasped the top of my blouse in both hands and ripped it open right down the front.
I was shocked and aroused at the same time. I pulled the cardigan round me but he coaxed my arms open again then opened the car door to let me in. Apart from one moment at the traffic lights I managed to keep the cardigan open as I knew Steve wanted it and it was starting to turn me on as well.
This time we made it to bed before sex but it was a close thing.

CHAPTER 3
After some discussion Steve wanted to move the dares up a level. I agreed in principal but needed two thing I didn't own. An A line denim skirt and a thong. I don't wear thongs as I prefer the feel of shorts but Steve assured me men would find a thong sexier. I got a pink satin one along with a mid thigh skirt and we were ready. Well Steve was, I wasn't so sure. However the dare was there.
One other thing I had to do for the dare was shave. I keep myself trim but don't bother with shaving as I don't like the prickly feeling of it growing back. However Steve volunteered and he made a very good job, especially rubbing in the moisturiser afterwards!
We agreed to go to a shoe shop. He would go in first so people would not know we were together then I would follow. I had practised bending in front of the mirror and was surprised how far I had to bend before the thong was visible.
When I walked in I was surprised how many people were there but it was too late to back out and I wandered round getting a number of glances probably because of the length of the skirt. Eventually I plucked up courage to bend straight legged to select a shoe from the floor knowing what was on view. As I stood I was desperate to turn round but knew I couldn't let on. I replaced that shoe and selected another before finally picking a high heeled strappy shoe and asking the young male assistant if I could try the pair on. I sat in the chair whilst he went to the stockroom to get the matching shoe and I sat slightly open legged but not too blatant. I noticed one or two men congregating in my line of sight and I guessed they were hoping for more. The assistant returned and asked if I wanted him to help. I looked at him demurely and answered yes. As planned he knelt down and slipped off my shoe before offering up the new one. As he put the shoe on my foot he put his other hand on the back of my calf and it sent a tingling sensation up my leg. So much so that it was almost involuntary as I let my legs part revealing the underwear. I could see he was looking but he made a good pretence of not seeing. Once he had tightened the straps on one shoe he repeated the routine with the other before offering me a hand to get to my feet. I don't normally wear a high heel so I found it slightly awkward as I tottered down across the shop and back again watched by an increasing number of the men.
I sat back down and let him remove the shoes making sure I gave him a good view before thanking him and leaving the shop.
When Steve and I reached the car I was feeling very hot and flustered.
“Was that OK?” Steve asked as he started the car.
“Better than OK, I thought I was going to cum as his hand touched my leg.”
“Really? Why didn't you?” was all he asked.
“Not really appropriate is it.”
Steve laughed, “Maybe not. So, head home then?” as he drove off.
It didn't take me more than a second to say, “Oh no, I want to try that again but this time with a bit more risk.”
“How are you going to do that then?”
I didn't say anything but reached under my skirt and slid my thong down and off my legs. As Steve gasped I lowered the window and tossed them out. “Now find me another shoe store.”
I must admit that as I entered the next store my bravado was disappearing fast. However I was on a dare so to speak so I repeated the routine not knowing who might be watching. Eventually I selected a pair of knee boots with a spike heel and asked the assistant for the pair. Unfortunately when he returned he just gave me the box and went off to serve someone else. Not part of the plan. Still I would still try them on and slipped off my shoes. As I tried to get my foot into the boot I realised it was very tight. At that moment a young female assistant came and asked if I needed help which I did.
She knelt down and put one hand on the sole of the boot and the other behind my leg just above the knee. Again this wonderful feeling ran through me and as I bent my leg to help I was obviously showing her everything.
The assistant suggested trying a half size bigger and I agreed. She went off and quickly returned with a new pair. She repeated the process and this time both boots went on with a lot less effort. I stood and walked up and won and felt really good in them. So much so that I decided to buy them although it was much more than I had ever spent on footwear.
I told the assistant and asked her to help me get them off. I sat down and she helped me take them off then she said something I was surprised to hear, “We have some nice thigh boots you might like to try. No obligation.”
Something in her voice made me agree and I sat there smiling as she went off only to return with the most ridiculous boot I have ever seen. It was black patent and the heel must have been at least six inches. I laughed but she insisted I try so she helped me on with both boots leaving the top rolled down to my knees. Then she helped me to my feet and helped me steady. There was no way I was walking anywhere in these.
Then something happened I really wasn't expecting as the assistant knelt down and started to roll the boots up to their proper place. As she did so her hand moved up until it touched my pussy. It wasn't an accident and I was shocked and excited at the same time. She kept it there for a few seconds before repeating the process with the second boot. This time her finger slipped just inside and I trembled and nearly fell off the heels.
I sat back down and she helped me off with the boots before I put on my ordinary shoes and we went to the till to pay.
As we got to the till I turned to the assistant and said, “Thanks.”
“Thank you,” she replied and blew the tiniest kiss.
God I was horny.
This time I took the initiative and we stopped in a lay-by and fucked on the back seat.

CHAPTER 4
Steve wanted public nudity. Now I wasn't going to walk through the shopping centre stark naked but I gave it some thought.
Eventually I came up with an idea that Steve approved of. I put on a suspender belt and stockings along with a pair of heels. Over that went a knee length coat.
We started off walking through a park and I just let the coat hang open. I kept my hands in the pockets so I could just pull it closed at a moments notice. We stopped for a time and sat on a bench where I enjoyed the feeling of fresh air on my body as I let the coat lie open at my sides.
We continued our walk through the town and I pulled the coat shut as people approached. Even I was unsure how to progress this dare until I saw the workmen repairing a section of roadway. Allowing someone to see you partially naked from a distance feels far more controlled than up close and personal so I told Steve to hang back and I walked along on the opposite side of the road with the coat hanging open. None of them seemed to be looking my way so I stopped and turned back and forth as if looking for something. Suddenly one of them saw me and did a double take as he realised what he could see. A few nudges and they were all looking my way.
“Lost something, luv?” one of them shouted.
“I'm looking for the post office.” I shouted back.
“Can't hear you luv. You'll have to come closer.”
My heart started racing but I took the first steps towards them. Everything in my body told me to close the coat but I didn't and eventually stood a few feet from them.
I repeated my question and my voice sounded so shaky. By now all three men were staring at my naked body and one of them pointed down the road.
Thanking them I turned and slowly walked away resisting the urge to run. I was so charged up.
Steve caught up with me at the car park and I was so hyper I actually took my coat off and carried it as we climbed up to our floor and crossed the parking area to our car.
Needless to say sex was hot and passionate but in our own house this time.

CHAPTER 5
The final dare, to date, was actually based on one seen on a website. Although Steve wouldn't tell me what he had planned I insisted Steve accompany me dressed as a woman and do the same as me, whatever that was. Eventually he agreed but said he would need to do some planning.
It was a few days later when he told me everything was ready and we both got dressed. I had seen a few pictures of Steve dressed but never seen him in person. When he appeared I was quite impressed. He was reasonably passable and his make up was good. The blonde wig looked natural and he hadn't gone overtly sexy with a knee length skirt, blouse and mid height heels.
Steve volunteered to drive and we set off into the countryside. He said he was already charged up driving dressed as he was. Only when we had driven quite some distance did Steve explain what he had planned. He had hidden a set of clothes for each of us a secret location. He was going to enter that into our sat nav without letting me know where it was. Then we would divide the number of miles to the destination by the number of clothes we were wearing. I would then drive and exactly at each designated mile marker we would both throw an item of our clothing out the window. Once we got to the end location we would both get out, find our clothes and get dressed.
I actually got excited by this dare but then questioned Steve about the clothes we were throwing out as I didn't want to lose any of mine as they were quite new.
“Another part of the excitement as we won't know what happens until we come back later today. In fact I'm even more concerned about my clothes as they are my special dressing up clothes.”
Feeling more relaxed I finally agreed and we swapped places. Steve put the final location in our sat nav and we counted our clothes. Counting the shoes as one we both had six item of clothing and twenty miles to go so we agreed we would stop every three miles leaving two miles to go naked.
I set off and wished I had worn lower heels as these were difficult to drive in. We decided we would start at the bottom so when we got to the first stop we both discarded our shoes. I threw mine some way as I wanted them hidden from view. The second stop saw our stockings and suspenders go out but the stockings were so light neither of us expected to find them again. The third stop was actually right outside a pub and we quickly removed our skirts and threw them out as far away from the road as we could. Fourth stop saw us again on a country road and the knickers went out. Again fairly light so they landed only a few feet from the car. The fifth stop was on a village lane and I was getting concerned about our final destination. Throwing our blouses out I felt very naked for the first time. Finally we stopped at the edge of an industrial estate and out went the bras and Steve removed his wig. Only then did I realise the slight advantage Steve had as he didn't have boobs. I drove on very conscious of our state of undress but I was relieved when we turned into a car park for a large DIY chain. Steve then pointed to the recycling bank at the far side of the car park. He explained the clothes were in a bag behind the large bin.
Thankfully there was only one car there as we drove up and that drove off as we arrived. I stopped the car and was just about to get out when we saw a lorry coming towards us. I suggested we wait but Steve pointed out it was the lorry coming to collect the bin. If he saw the bag behind he would almost certainly take that as well. Now we were in trouble. Get out naked to get the clothes or risk losing them all together and have to try and find the ones we threw away. We both looked at each other and without a word being said we both got out and walked as calmly as we could to the bin knowing the driver of the lorry which had now stopped would see everything. Retrieving the bag we walked back to the car and then I decided to add another level so I flicked the remote and locked the car door. When Steve looked at me I upturned the bag and emptied out our clothes. Seeing my plan Steve then walked over and we got dressed without any rush before we got in the car and drove off.
Unfortunately the sun was shining on the windscreen of the lorry so I couldn't see the drivers face but I assume his mouth was hanging open.
The final thing was to retrace our route and recover our clothes. The bras were still where we'd left them as it had only bee a few minutes. Neither of our blouses were to be found. I assume tidied away by some litter conscious person. Surprising both sets of knickers were still where we'd left them although both of them had got muddy from being blown across the grass. When we got to the pub we saw someone picking up our skirts and walking towards the pub with them. I wonder whether any of the people would work out what really happened? As I suspected no trace of the stockings although the suspenders were still there as were the shoes at the final stop. Unfortunately I had thrown mine so far they had landed in a drainage ditch and were soaking wet.
What an end to my daring journey. Except it probably isn't the end as I will want to do more.

[chicken mafia]

Nice story so far and I'm looking forward to reading more.