One night when i was 14 i had a friend spend the night, we talked about sex as most guys our age did, and the fact than neither one of us had ever had sex. We talked about the typ of porn we liked as we had found our parents porn stashes and would watch them every chance we got. Then it came up that he had seen a bi vid that his mom had, it was mm/mmf, with one sean involving a guy dressed like a girl and it had realy turned him on. He said that the guy looked hot as a girl, and that he was getting a hard on just thinking about it. I could see it getting hard in his shorts and i was starting t... Continue»
After splitting from my wife a few years ago, and having the house to myself, I decided I would take the opportunity to indulge my bi-sexual side and have as much hot fun as I could with men rather than finding another woman immediately. I have always been quite a dominant guy and I have never played the submissive, over the course of several months I met up with a few guys who on the whole wanted to either be dominated or give as much as they took. That was until one day I got chatting via a gay dating website with Brian a 58yr old guy who as it turned out wanted to purely pleasure me, he wanted to be sucked and wanked but he did not want me to fuck him. This seemed reasonable to me, and after a few more chats we agreed to meet, we arranged for him to come to my place and fuck me there. It was during one of our chats that brian asked me something that no one else had ever asked before, he requested that I crossdress for him if would be comfortable with it. Now personally I had never contemplated crossdressing before, yes I had fucked cd's on occasions and have very much enjoyed the experience but to do it myself felt daunting.
After some consideration I decided that I would indulge brians fantasy, but not go the whole distance, I settled on wearing some sexy knickers a bra and some hold up stockings and heels, but not getting fully dressed up with wig and all that.
I had three weeks to prepare myself for the arranged meeting, so during that time I went out and purchased a black lace padded bra, matching hipster style lace knickers and some black hold ups. Heels on the other hand were a different issue, I finally tracked down a pair of stilletos from an adult catalogue designed for crossdressers and tv's. When the day finally arrived I decided to tease brian a little by texting him and giving him a brief idea of what I was gonna be wearing for him and what I wanted him to do to me as I wear them. 7'o'clock that evening I prepared myself for his arrival by slipping into the sexy underwear and sat tentatively awaiting his arrival, I can honestly say even with the glamorous sexy underwear it did not make me feel remotely feminine and seemed to drain any dominance that I would usually feel from my body,
As the door knocked I peered through the peep hole to check it was brian and proceeded to open the door wearing only my underwear and greeted him with a sensuous kiss, I already knew that brian from his description was a large built guy, although quite short he looked rugged and stocky, full of strength and domineering, during our chats he had told me that he was quite well hung (which I like), what he failed to say was JUST HOW WELL HUNG!
As we moved into the lounge we began kissing again and as we stood there he reached around and began to caress my arse over my panties before moving his hand around to the front and rubbing his hand over my flaccid cock and balls. To me he did not seem to want to be too f***eful and it began to make me feel like he wanted me to be too feminine and womanly, so as he leant in to kiss my neck I whispered in his ear that I wanted him to treat me like the dirty little slut that I was feeling dressed this way, I urged him to use me for his own benefit, to do what he wants to me, because if I was going to be a sub for a change I wanted him to to make me feel that way.
With that he placed his hands on my shoulders and f***ed me to my knees in front of him, barking at me that he wanted to fuck my face and make me gag on his hard cock. As I knelt there he began to unbutton his shirt and as I glanced up I could see his hairy chest and erect nipples, I then proceeded to undo his jeans and slip my hand in the front of them, immediately I hit a tell tale bulge concealed beneath his shorts, to my surprise it must have been a good 7inchs long but more surprisingly was the fact it was that size whilst still flaccid. my mind began to race trying to imagine how big this fucking monster cock was going to be when erect, tentatively i slowly began to ease his thick veiny shaft from his shorts, as i did so it literally just flopped out and hung there inchs from my face, it was massive, easily as thick as a can of aerosol. Nervously i leant forward and began to lick around the head of it, lifting it up as i did so so that i could run my tongue down the length of the underside of his cock all the way down to his balls which were equally as large and hung heavy between his thighs. Slowly i began to ease my mouth around his shaft, gradually taking it deeper with every suck, slowly it started to stiffen in my mouth stretching it wider than it already was. As i sucked it i began to realise that his cock although huge, was also one of those cocks that are so big they never truly get fully erect, just stiffening enough to give the pleasure i really desired. As i sucked his cock i could feel every vein that bulged on this monster my lips bumping over them as they slid up and down his shaft, suddenly brian clasped one hand onto the back of my head and wrapped the other around the base of his cock pulling his foreskin right back to expose his bulging cock head, he then proceeded to f***efully fuck my mouth, thrusting violently his cock to the back of my throat, it was all i could do to stop myself gagging, the faster he fucked my mouth the more vocal he became, calling me his "bitch" and his "dirty whore", all the time he abused my mouth like that i rubbed my own cock getting it harder with every stroke, sensing that he was going to cum, brian pulled away and proceeded to slap his wet cock onto my mouth and face until his impending climax sub-sided.
Now as he pulled me up by my hair he thrust me towards the sofa and as he pushed me onto all fours he tore open the arse of my panties, before bending over and rimming my arse, getting it nice and wet in anticipation of feeling his slab of meat penetrate my tight hole. As he rimmed me pulled my cock and balls out through the torn panties and began to wank me quite roughly, pulling at my balls as his tongue explored my hole, After a few minutes he sat on the sofa and pulled me towards him and astride his lap facing him, slowly i rubbed some lube up and down the length of his cock and as i did so i began to lower myself onto his thick shaft, inch by painful inch my tight hole gradually took his cock deep inside, after a few minutes of gentle persuasion i was fully impaled on his 9ins of cock, i then proceeded to ride his cock, savouring the feel of this giant penis stretching my arse to breaking point, as i was riding him he slipped down the straps of my bra off my shoulders and began to suck and lick at my nipples, gradually beginning to bite and chew them harder the more aroused he became, i was now running my hands through the thick mat of his chest hair, periodically pulling at his big nipples and leaning forward to lick and suck them. after a good 20 minutes of riding him he lifted me off his cock and pushed me to the floor where he then proceeded to rub my penis and finally take into his mouth, as he sucked greedily on my cock i could feel his fingers probing my now loose hole, firstly pushing one finger inside he then followed that with a second, then a third. After a few minutes of sucking me he pushed me onto my side and positioned himself behind me so he could fuck in the spoons position, as i raised my stocking clad leg i looked at my legs and thought how good stockings felt to wear and also how sexy it felt to wear stilletos with them for another man. As he got into position comfortably he eased his thick prick back inside my burning arsehole, and as he held my leg in the air he caressed my thigh at my stocking tops and proceeded to fuck me again, as he thrust his cock in and out of my hole i rubbed and wanked my own cock furiously, every thrust he made he was hitting the spot and within a few minutes i felt my cum rising and knew it was only a matter of time before i shot my load, a few strokes later and it happened my body stiffened as i spurted load after load of hot cum firstly all over my stockinged leg then all over the floor. Feeling my own orgasm pass brian then started to pick up the pace as his own approached, as i laid there being used i concentrated on the feel of his veiny shaft filling my arse, until finally with an almost primeval grunt and shudder brian flooded my hole with his hot thick cum, i could feel every pulse of his cock as it pumped his semen deep inside my hole.
That was my one and only time to date where i had played the slutty submissive and is still the only time i had crossdressed for anyone, although given the right opportunity i would now definately do it again.