I was 32 years old when it all started, my name is Tony. My wife Jane was 25, we had been married 5 years and our sex life was virtually non-existent. I'm 5'8" tall, with a slim build, blond hair and blue eyes. I'm quite fit at 150 lbs. Jane is a stunner blond blue eyes 120lbs 35c very sexy.
I guess part of our sex problem is my cock, or lack of it, it only reaches 4" when really hard, its cut quite thin and I also have small balls. To make things worse on the times we did have sex I used to cum virtually as soon as I put it in her. After the first few months in order to reduce her frustration I agreed to go down on her after I came, even though I found it repulsive at first, I got used to sucking my cum from her, and at least she used to reach orgasm, it reached the stage when we never had sex without me using my mouth on her.
The number of occurrences reduced to once a month then once every 2 or 3 months, I reverted to jerking off a lot, using a hidden pile of porno magazines and videos, as well as Internet. I found myself drifting more and more into perversion. I had a fantasy of wearing girls clothes, being tied, ass whipped, and used by men. It was of course just my fantasy. More and more my mind was filled with such fantasy as I jerked off until I couldn't cum without being used.
I live in Melbourne, Australia, and travelled regularly interstate to Sydney. Sydney is Australia's gay capital, has lots of porno and video shops, which I began visiting regularly when I went there. I started using shops with glory holes, although I couldn't bring myself to suck another cock, I was sucked a few times myself. I also went to sex cinemas where I masturbated not just myself but sometimes other men's cocks as well. Mine was always smaller which I constantly found to be embarrassing, even had guys laugh now and then.
I hadn't had sex for months and was in Sydney more and more, and I decided to try and act out my fantasy. One thing I knew was that I always chickened out of anything serious at the last minute, and once I came, I found the whole idea disgusting and wanted nothing further of it. Anyway, this visit I had planned it all. Our sex was such that we no longer saw each other naked at all, sex was always in the dark, and she never touched me at all.
I was in Sydney for the week, so on the first day I purchased a dilapidating cream, I didn't really have much body hair anyway, but I removed it all and used it on my face, I hadn't shaved for four days, so when I was finished I was smooth as baby the only hair being on my head. I planned to stay away from the gym I used for a few weeks so that colleagues wouldn't see my hairless state.
Then came the next level of my fantasy, I put on track suit pants and top with runners jocks and socks, I took my wallet and some Velcro cuffs that I had made. I designed the cuffs so that using some pieces of string I was able to tie my wrists behind me, pull out the string and then be helpless, requiring someone else to release me. Then I visited a lingerie shop, the shop assistant was quite young, barely 20 I would have guessed. I was extremely nervous and embarrassed.
As soon as I went in, she asked if she could help, and I told her I needed panties, matching bra and suspenders and some stockings. She asked what size, I took a deep breath and a gulp and told her they were for me. She grinned and asked what colour I'd prefer, and I said that I'd leave it up to her. She came back with bright red lace thong panties and bra and suspenders with some black nylons.
She suggested that I remove all my clothing and try them on and give a call when I was ready so she could check it for me. I could hardly remove my clothes I was trembling that much. Somehow, I managed, and it felt incredible on my smooth skin. Whilst I am fit, I also have smallish breasts that are quite feminine, not requiring a bra of course but with feminine thick nipples.
I had it all on, and with trembling voice, I called the assistant. She opened the door with that same grin on her face and told me to step out as the light was better. I nearly passed out when I did as there was a sophisticated looking lady with probably her daughter staring at me. The girl giggled the lady looked at me in disgust and turned the girl away.
The assistant told me the fit was good, but I needed padding and she left me standing there in the aisle while she found a couple of pads. She stuffed them in my bra and adjusted my panties, pushing her fingers under the gusset. She giggled and told me she thought I had had the sex change at first. I had a raging erection, but it was so small that even with the skimpy panties it wasn't obvious.
I told the assistant I would take it all and to throw out my jocks and socks - I was determined to go through with my fantasy and didn't want the chance of changing my mind. They were quite expensive, but I felt really sexy. My next stop was a hardware store, where I purchased some bamboo canes, and my final preparation was to buy some makeup.