Written by Nylon_pylon

14 Jul 2012

I can honestly say despite still feeling mentally young, I was in my prime at the age of 25 way back in 1986. I was boxing for yorkshire and aiming for a place on the England squad. No point denying it my skills let me down and I never made the grade. However as a result of all that training I lost so much weight I went down to 10st. There wasnt an ounce of fat on me, I am naturally tanned with black hair and the younger kids in my gym used to call me Rocky.

At that time I used to work behind a bar and never had any tracting the ladies.

The girl I was living with at the time chatted me up in that bar the year before. Her name was Debbie, and I dont think there was a man in that bar that didnt want to put his cock in her. Debbie was tall and blonde, definitely not skinny. nice round arse and perfect tits, she was an outreageous flirt, loved attention and at 20 years of age stood 6ft 1 inch tall. Being only 5ft 9 inch tall myself I loved her height, part of the reason being Debbie always wore stockings and enjoyed the feel of her long legs wrapped around me whilst fucking.

I was very shallow in those days, Debbie was arm candy, she was hot and fun, but I doubt we ever had a decent conversation. All we seemed to do was fuck. It was whilst living with Debbie that my bi side surfaced more than ever, her height and body size were ideal when it came to my crossdressing. Whenever I was alone in our flat, I would raid her wardrobe, slip into a tight short dress, choose from a selection of suspender belts and stockings and wear her shoes, which were just right for my feet. I never bothered with her undies as I wanked myself into a frenzy and didnt want them staining.

Debbie was quite kinky herself, a great believer in vibrators, when a man wasnt handy, so she kept a nice long white one in her bedside drawer. She often insisted I snog her after giving me a blow job, so she could pass the spunk back into my mouth for me to swallow. She always said that if my cum was good enough for her to swallow it was good enough for me.

Debbie was special looking back as she racked up a number of firsts for me. She was the first girl ever to finger my arse, which I adored. She was the first girl ever to suggest I also should wear stockings and suspenders when we made love. Of course I played the macho guy pretending it was crazy and I looked foolish, but all the time secretly loving it as our nylon legs became entangled. It was during one of our heated sessions she pulled out her vibrator. Thank God I was younger and more in control as my arsehole was literally puckering up at the thought, and just recalling that moment has my cock leaking today. Sadly, depending on your perspective, she began to use it on herself. We ended up in a 69 position with me ontop, cock deep in her mouth as I fucked her with the vibrator. When she felt the time was right she removed the vibrator and sat op on the bed. She pointed the tip of the vibrator at my face and with a wicked look on her face told me to suck it. This I did for a good five minutes, before she stopped me and sat on my aching cock. Gutted no bum fun.

A few weeks later I was working in the bar, the landlord and his good lady were in their late 30's and had their own group of friends (usually couples) who all managed to go out once a month. One couple in particular Alan and his wife Debbie both in their 50's invited my Debbie along with them. As she was only in the pub out of boredom waiting for me to finish, I suggested she go enjoy herself. Apparently a great night was had by all, new friendships formed etc.

We shared the taxi home with Alan and Debbie, and when we dropped them off first my Debbie went inside with them, moments later returning with a plastic shopping bag, when I asked what was inside it Debbie told me it was a dress that the older Debbie had given her. Even the taxi driver looked surprised, as the older Debbie was a big breasted chubby woman who looked good for her age, but unless it was a dress she had bought 30 years ago, was never going to fit her.

No sooner had we got home than our sexual athletics started. Debbie had a hot black basque on and black patterned stockings, she was eager for me to dress in stockings and suspenders. As she made her way out of the bedroom to nip to the toilet she tossed me a little black nylon nighties she often wore. "Put that on too" she winked.

I made my half-hearted protest, but as soon as she left I couldnt wait to get into it.

I lay on the bed with my throbbing cock standing up. When Debbie entered I almost emptied my cock on the ceiling. Still looking red hot in the basque and stockings Debbie was now wearing a black rubber strap on.

She walked over to me like a woman on a mission took hold of my head and told me to suck it. This may sound odd, maybe I'm a selfish sod, but this was 1986 it wasnt cock shaped like these modern designs that look realistic it was just a piece of black rubber on a leather belt that reminded me of a small policemans truncheon, and l really couldnt work out what possible satisfaction she got out of me sucking on it. After all it wasnt real, not part of her body, but sure enough when I looked up at her, she had a face full of lust and her hips were actually fucking my face.

We were not destined to stay a couple long. When Debbie finally got around to fucking my arse with the strap on I dont think either of us were thinking of the other. She seemed to relish the role of being the dominant arse fucker, slapping my butt and calling me her bitch. As for me, with my slim fit body dressed like her bitch I gave up the pretence and whimpered like a real cock slut. She even fingered herself to orgasm as she humped me. We enjoyed several more months together before we sadly just drifted apart.

On the day she packed her belongings to leave the flat, she handed me the plastic bag the older Debbie had handed to her that night. Inside was the strap on, which she asked me to return to the couple. I was gobsmacked and asked how they even came to such an arrangement, what she had told them she needed it for (Not I the macho boxer surely) Debbie just laughed and said the older Debbie thought I might enjoy it, besides her husband Alan had his eye on me. But thats another story!