I suppose I’ve always been Bi curious or maybe gay. Late in my teens, I rented a room in which was the landlady’s wardrobe. In those days I was a lot slimmer and quite pretty if the photos are to be believed. When the couple went out, I would try on her dresses. I remember a long pale blue one which tied nicely around the waist. I hadn’t the breasts to carry it off but it sure felt naughty to me.
It must have been a year later when I was waiting for the bus home from Tech college in Chelmsford that I had my first sexual contact with another person. It was probably near payday as I had gone to the pub and had a couple of bottles of strong beer before setting off to the bus station. Plenty enough for a newly turned eighteen year old to feel the effects but now I needed a toilet. The stall I chose had a hole in the wall and I fantasised about whatever could happen through it.
A man was just visible through the hole and he was wanking. After a few seconds I placed a finger tip through the hole and withdrew it. He put his cock through the wall and uninhibited for once I dropped to the floor and began to suck it. After a couple of minutes, he was hard and I stopped fellating him; he withdrew his cock I put mine in its place. Having my cock sucked felt nice but I was a little too shy to let it go so I pulled away, letting him put his cock through the hole again. This time I kept going and a minute later he came in my mouth. I hoped I’d get the same treatment but I heard the flush and the door open and he was gone. I had a stranger’s spunk in my mouth and I spat it down the bowl and full of confusion went to wait for the bus.
I never did that again but a few months later I did meet another young man who led me out to the urinals where we stood side by side and wanked each other. I came almost immediately but was always fearful of being discovered so as soon as it happened, I scarpered.
I thought about women pretty constantly but had come to realise that there was more than one sort of sex and that I didn’t really mind how I got my jollies.
I was twenty, in Maidstone and that hot Saturday afternoon I again needed the conveniences. I was bursting and joined the queue of men at the bus station. I really hadn’t twigged but when I arrived and drained down, I understood why. Another hole! I put my cock through it. I didn’t pull away. Keeping silent, (as if those outside didn’t have a better idea of what was going on than I did), my knees actually went weak as I had the most intense orgasm I had ever had losing any consciousness of anything other than the spasms of extreme pleasure I was feeling all over my body.
And that was it for years. Women came and went, my fantasies became more detailed and experimental and I tried every sort of sex toy I could make. Rubber bands on my cock and balls and tying them up with shoelaces were common for getting off but I was starting to know what turned me on. I had a curiousity to try anal sex. What did it feel like to get one up the bum? I experimented with smooth screwdriver handles and a cigar tube which I later filled with lead shot to make it feel more solid.
I wanted to wear knickers but was too afraid to buy them. I found a pantygirdle in some discarded jumble one day and cut a small hole in it that would just allow my cock through. The tightness around my waist, bum and thighs turned me on and it was my sex toy of choice for a couple of months in my flat. I knew I would have to try rubber. It was becoming an obsessive kink. but it wasn’t sex with somebody else.
Around my early thirties, I was with a woman who adored sex but I wasn’t quite fulfilled. One day I went to the public conveniences in Romsey where there was what I now know as a glory hole. I passed the man who came in a little later and looked through the hole at my erection, a note. “Meet outside, blue Saab.” I drove him back to mine and we wanked each other perfunctorily until he asked me if I took it. I was only too ready but I insisted that it was safe. He wasn’t happy about it but it was the only way so duly sheathed, he wiped his spit around my entrance and plunged the whole length of his cock straight into me in one great thrust. The pain was pretty acute and I gasped before asking him to fuck me good and hard as although he didn’t know it, thirty seconds before I had been a virgin and I didn’t mind it hurting this once because I really wanted to feel it. Besides, I didn’t want to reveal my lack of experience.
He came, seemed disappointed and I drove him back to his car. So far it hasn’t happened again.
From time to time, I’d buy bodystockings and control tights and on my first visit to Amsterdam I went into a sex shop and bought a pair of black rubber panties. The tightness on my body was nice and I thought of how it must feel to be tied to the bed and fucked. I was starting to feel sensations in my nipples and found that stimulating them was pretty wonderful. A porn magazine with a pair of shemales as they were called then giving each other a 69 was one of the most erotic things I had ever seen. Having your cock sucked as you were making another man shoot his load in your mouth must be amazing and next time, I would definitely swallow the lot.
I bought a very small house out in the French countryside. I kept a pair of panties and a nightie there but I really wanted to have a collection of sex toys. A double ended dong made for a woman to work both of her holes was my next experiment. The slim end went into me easily and within three days I managed to get not just the big end inside but the whole twelve inches. If I’m ever fucked again, I’ll know that as long as my partner takes his time, I’ll be able to take it all.
I have tried every sort of anal vibrator but none of them give me any sort of stimulation so I gave up on them. An anal douche connected in place of the shower head gives me a bit more fun so I use that instead.
I’d like to buy some sexy undies and some toys to work my nipples but most of all I want a fuck buddy who will safely fuck my bum again and let me do the same to him. If he dressed me up as a woman, I’d enjoy it and if he dressed as one himself, I’d enjoy that too and I still haven’t done that 69. These days I live in Dorset and could be found where the guys are fab under the name of pansexual. Let me know if you would like to give me an adventure for the next chapter.