How I Got Started (Fiction) Please Rate It After You Read It
From the begininng when Kerry and I started dating it was ALL about SEX. We could be anywhere at anytime and she would jump me. It would start with the question "Do you trust me ?". Then in elevators, department store dressing rooms, movie theaters, airplane restrooms, just about anywhere, we'd be having great sex. She would try any type of sex or any position in any place, nothing was off limits it seemed. I knew once she asked me that question I was about to have sex in some place or in some way that I never had before. It got to the point that I never even thought about it and would just say "Of course !!".
She was also very into lingerie and sexy outfits. She liked them a lot so I sarted buying her more and more. She would tease me with the lingerie. She would rub the silk, satin, lycra, spandex, lace or whatever, over my cock, my nipples, my ass, anything that she thought would turn me on. It got to the point that the slightest touch of any of it would get me hard. One day I had to leave Victoria's Secret because just the sight of all of it made me too hard to stick around and shop. I was in bad shape.
One night we were back at her place having an all night session. Kerry had a talent for keeping me hard and excited for hours on end without letting me cum. It sounds bad and in some ways it was but, when she would finally let me cum it was the BEST. So we had been going at it for quite a while and she was rubbing me all over with her full length satin night gown. She was giving me a blow job but I kept squirming because I NEEDED to cum. So she looked up from her position between my legs and said "Do you trust me ?" and I said "Of course !!". She got up off the bed and told me to stay lying there naked. First she came back with 2 wrist restraints and hooked me to the bed. She returned to the task at hand and after only a couple of minutes stopped and said "I have another idea !!". She got up and went to a drawer in her dresser and returned with a pair of pink lycra panties !!! I had no idea what she was about to do but my cock was purple I needed to cum so bad. I never asked her anything.
She smiled this hot smile and said "Here, let me slip these on you" and she did. She kept saying that she had never seen me so hard, that it must be how much I enjoyed wearing her underwear. All I could do was moan and pray that I'd get some relief soon. Kerry got back between my legs and started massaging me through the lycra. My cock must have grown another few inches. I was so hard and so desperate to cum that you could see every single veign in my cock. Hell you could even see it through the panties !!! She began licking my cock through the panties. I couldn't believe how sexy that looked and felt. Then she freed my shaft from the pink prison but kept my balls wrapped in the panties. before I knew it she was deep throating me but squeezing my dick at the base to keep me from cumming.
I voiced a complaint about not getting any relief. My girl asked me if I liked when she sucked my cock. I answered with a resounding YES !!! Then I was told that we had a problem because she liked sucking my cock and if she let me cum she would have nothing to suck on. Basically I was told to wait and enjoy it. What seemed like hours later after all her sucking and licking and rubbing her gown on me while being wrapped in her panties Kerry decided it was time to give me what I'd been waiting for. She mounted me while still dressed in her night gown and my balls still encased in lycra and rode me hard. She tweaked my nipples with one hand while reaching behind her with the other hand and massaging my balls in the panties. When I came it was so hard I thought I would launch her off me. I was exhausted as well as utterly and completely satisfied.
I lay there catching my breath while my love got up and returned with a baby doll nighty for me to sleep in. Right then it seemed like a great idea so I let her dress me in it after removing the restraints. I slept very deeply that night while my girl rubbed me all over all night. I was HARD ALL night long. I had some wild dreams that night for sure. I woke up because I dreamed someone was giving me head in my sleep. When I opened my eyes I realized someone was giving me head as I lay there in my nighty. Kerry asked me if I enjoyed last night and I told her it was the most amazing night of sex I'd ever had. Panties and nightys became a regular part of our lovemaking from then on. The very next day my girl started making purchases for my wardrobe. We would play dress up every weekend (not during the week because it was too draining and I needed my strength if I was working the next day).
As time went on my outfits grew. I was soon wearing garters and at first fishnet stockings. I was told the hair on my legs was ok with fishnets but it would ruin the sexy stockings with the seams my girl wanted to see me in. So we were going to shave just my legs but then it only made sense to shave everywhere. I was told it would be OK to keep some pubic hair as long as I kept it trimmed. Each time that I got deeper into dressing it only seemed like a tiny step from where I was and it kept my girl happy so I never thought anything was a problem. Next up was shoes. Heels had to go with my outfits so I started small and kept practing and practicing till I could glide in 5 inch heels and even walk in higher ones if I needed to.
Then came the next major milestone. One night in September Kerry had played with my nipples so hard that when I dressed for work Monday morning they were raw under my dress shirt and hurt like hell. She had a solution. I was handed a silk camisole that protected my nipples and soothed them under my shirt. I went to put my boxers on and was stopped before I even got my first foot in. I was told there was no way I could wear boxers with that camisole, so on went the matching thong and off I went to work. This was the first time I ever wandered out of the house with womens clothing on. I was more turned on than I ever thought possible. I was so distracted at work that I had to say I was sick and leave at lunch. When I got home and explained it to my girl she threw me down and fucked me right there in the living room keeping me in my camisole and thong the whole time.
The end of next month came the holiday custom made for guys that wear womens clothes HALLOWEEN. Kerry asked me if I still remebered how hot I was the day I wore my camisole and thong to work. I told her I would never ever forget that. Then she asked "Do you trust me ?". My usual response followed and then I was told about her idea for our Halloween costumes. She wanted us to go out as school girls, plaid mini skirts and all !!! I was nervous but she said she had everything covered. First of all we live in New York so we would go to the parade in the village so that on the off chance anyone could tell I was a guy after her make over, I would just be one of many. I do proffesional voice overs,all kinds of characters and could make my voice pass for a womans so we would be fine.
That night I was even more excited than the day I went dressed in womens underwear to work. I was given an addition to my wardrobe to help make sure nothing unwanted popped up. I was given a gaff to keep my cock out of the way. I was already hard so I had to get my cock sucked till completion before dressing. I was so excited and Kerry wanted me dressed quickly so I think it took 10 seconds LOL. Then it was a matching virginal white satin bra, panties, garter belt and seamed stockings. Next was the plaid skirt 5 inch fuck me pumps, blouse and Blonde wig.
The parade was great I was hard as steel the whole night. Nobody seemed to figure out I was a guy, they all thought we were 2 lesbians LOL !!! I figured it was all gay people where we were and they were just being nice. My girl told me she'd prove nobody could tell and took me to a bar in Penn Station called Charlie O's. It is probably the straightest bar in all of Manhattan. So many guys tried to pick me up and/or grab my ass I had to believe her.
We took the Long Island Rail Road home. On the trip she made me go into the bathroom and bring her my panties and gaff (she wanted unfettered access to my cock on the way home). We fucked in our seat and then she got on her knees and sucked me off too. We only got interupted once by a conducter collecting tickets. I never figured out how MUCH or how little he saw. It was the HOTTEST experience ever. She dressed me in a very sexy nighty when we got home and we fucked and sucked, and sucked and fucked until well after the sun came up !!!!!
After that I would go anywhere and do anything while dressed in womens clothes. No matter what I'm doing while dressed I am always excited beyond belief !!!!
