The following is an account of a true encounter between consenting adults. The names and places have been altered to protect the individuals. Any resemblance to actual persons is purely coincidental. It is not intended for minors. If you are offended by sexually explicit material or have received this document by mistake, please close the document now. If not, read on and enjoy yourself.
I met Barry originally through an ad in a regional swinger's magazine. He was an advertising executive from a major southeastern city and, like myself, had been married for a number of years. We got together about a dozen times over a three year period at motels both in his city and in my home town. He was especially attracted to my crossdressing interests, and always insisted that I meet him dressed up and play the role of Mona with him, something which I was more than happy to do. I normally went to the motel first to wait and get ready for our discreet meeting. Following is an account of one of those meetings.
As usual, I selected one of those cheap, out-of-the-way motels with short-stay rates. You know the kind - small dark rooms, bedspreads with cigarette burns, and stale, pine-cleaner smell. .After checking in to the room, I undressed and prepared for my lover with eager anticipation. I shaved my ass and balls smooth and used a lower enema to get squeaky clean inside. I showered and massaged myself with some body lotion that smelled very nice and feminine. I then put on my black lingerie outfit - bra, camisole, short slip, stockings, garter, thong, heels, and wig. I admired myself in the mirror, thinking that I looked pretty good. I was trim and tanned, my legs were long and well shaped, my ass was firm, and my stomach was flat - not bad for a middle-aged crossdresser.
To pass the time while I waited, I put a hot transexual video in the portable VCR I brought with me. I love to see beautiful shemales being totally ravished by well-endowed, hard, virile studs, and I always imagine myself participating in place of the shemale actors.
In order to be ready (stretched) for Barry, I took my large male dildo, lubricated it, and gently worked it into my shaved male pussy as I watched the action on the video. It is at least 8" long and 2" in diameter and feels really good. I can eventually take it all the way inside until the ballsack at the end of the dildo is pressed against my asscrack. I am very anal erotic and always use one or more dildos in my private masturbation sessions, which can sometimes last several hours. I really had to resist the temptation to ride the dildo and masturbate while fantasizing over the sucking and fucking on the TV screen.
My friend finally arrived, and I greeted him at the door with a long, passionate kiss. I then went over to the bed and began to display my body to him, playfully caressing myself in an erotic manner. I pulled up my slip, removed my black thong, and unashamedly revealed my arousal to him, massaging my hard, 6-inch clit. Barry watched me intently and slowly began to remove his clothes. As I pleasured myself before him, gradually the woman in me began to come out and I was gradually transformed into Mona. I was filled with desire to please him in every way that a woman can satisfy a man, and then some. I turned over on my knees and elbows and exposed my smooth, shaved ass to him. I licked my index finger, reached back between my legs, and began to tease my puckered rosebud. I slipped the end of my finger past the tight sphincter and into my warm chute, moaning softly. I slipped it out, then back in, deeper this time. I gazed at Barry as I fingered myself, showing him exactly what I wanted him to do to me. I rolled over on my back and spread my legs widely, plunging my finger all the way inside. I closed my eyes groaned as I massaged my sensitive prostate G-spot and my hard drooling clit at the same time. When I opened my eyes, Barry was standing next to the bed with only his briefs on, the prominent outline of his male hardness was clearly visible on the front. I pulled my finger out of my pussy and licked it off erotically, then plunged it back inside as I admired Barry's body.
He was in his late 40's, about 6'-1", medium build, with salt and pepper hair. His body was firm, not flabby, and he had very little body hair. I went over to him and traced the outline of the bulge in his briefs with my fingers, then leaned down and nibbled it gently through the stretched fabric. A wet spot appeared at the end of the bulge as I did so. I slipped my fingers under the elastic waistband and slipped his briefs down to his thighs. His rigid cock sprang forth and pointed upward at a 45 degree angle. Clear threads of pre-cum were already oozing out of his cock-slit and running down his shaft. Barry's cock was just over 7" long and straight rather than curved (like mine). He was circumcised, and the flanged head was flared and quite pronounced, looking much like a swollen pink mushroom. Most of all, he was very hard and long lasting, something which I appreciated very much.
I looked intently into his eyes as I took his erection in my hand and began to lick up the bottom side of his veined shaft, pausing to suck on his ball sack. I moved up and circled the prominent flange with my tongue, then ran it across and into his drooling cock-slit. He threw his head back and gasped as I did so. This was my signal. I sucked his engorged mushroom head into my mouth and swirled my tongue over and around it caressing his sensitive flesh. He groaned loudly, and I quickly consumed the entire shaft. I began to take his rock-hard dick with long, powerful sucking motions. I am quite good at this, and I can usually bring a guy off in a few minutes if I don't stop. I took Barry to the verge of orgasm, and kept him there for some time, pausing as necessary to prevent him from going past the point of no return.
During one of the pauses I got up and lay on the table on my back with my head hanging down over the edge. Barry approached and leaned over me and slipped his cock into my hungry mouth. This way my throat was straight in line with his cock, and I could take him all the way deep throat style. I had to resist the gag reflex as his cockhead eased past the back of my mouth and slid down into my throat. Inch-by-inch I swallowed more of him until he was all the way in and his ballsack was pressed firmly against my nose. He knew to move gently, and after a little while, I was able to accommodate his full length thrusts. Fortunately, he also knew to pull out occasionally so I could breathe. As he enjoyed face-fucking me in this way, he focused intently on my neck so he could watch the lump made by his cockhead moving up and down my throat. I loved taking him like this and pleasing him. But, what I really wanted was for him to make love to me like a woman. That part of me that was Mona desperately wanted to be overpowered by his strength and animal passion and to feel his wonderful male organ penetrating my hot, tight mancunt.
I crawled on the bed and got on my back with a pillow under my hips. I spread my legs wide and lifted them to welcome him to my pleasure center. He crawled up between my legs and smeared some slippery lubricant onto his bare dick, then squeezed some inside my puckered hole. He moved forward until his cockhead was poised right at my willing orifice. Our eyes locked together as he pushed, sliding the engorged, flanged knob past my outer ring of muscles. I groaned as my sphincter muscles clamped sown on his shaft behind the head and he continued to slowly impale me with his manhood. Just over half way in, his plum-knob encountered my second, inner ring of muscles which separates my rectum from my lower bowel. The muscles guarding the last orifice resisted briefly, then yielded to his entry, causing me to close my eyes and moan with pleasure as I was fully penetrated. I locked my stocking- covered legs behind him and gave my body to him completely.
He then began to move, slowly at first, then somewhat faster. I really like to be fucked in long, slow, deeply penetrating thrusts so that I can savor the full sensation of my lover's dick moving in and out. Barry knew just how to move. He especially knew how to angle his movements so that his dickhead drove into and along my sensitive prostate with each thrust. His motions sent me into a semi-conscious state of pure sexual ecstasy that only another man can give. He leaned down and kiss me passionately as he made love to me, our mouths locked and our tongues dancing together. I expressed myself in deep groanings of unspeakable erotic pleasure: "Yesss...pleezzeeee... Barry! Oohhhh ...fuuuuck meeeee!"
His lovemaking soon brought me to my first prostate orgasm, and I cried out loudly as seminal fluid gushed from my semi-hard dick, forming a puddle on my heaving stomach and running down my sides. Barry stopped briefly as my anal muscles gripped his hard shaft in orgasmic spasms. Sometimes I have cum twice while being fucked by Barry. He really knew how to make deep, passionate love to a man-woman, and I was fortunate to have him as my lover.
When my spasms subsided, he resumed his wonderful hip motions. This went on for some time, and he would occasionally pause if he was getting too close. I could tell when he was approaching his own orgasm. He would start to grunt and his thrusts would quicken. I urged him on, "Ohhhhh yesssss... Barry, pleeezzzeee cummmm in meeee!" Suddenly, his back bowed and he thrust into me as deeply as he could go. He groaned loudly as he exploded inside me, pumping his pent-up load of hot semen deep into my bowels. I could feel the warmth of his cum and jerking of his cock as it recoiled from each spurt. I loved it! There is nothing like being fully consummated with my lover's seed deposited deep inside me. He rolled over on his back to recover. I rolled with him and stayed impaled on his cock until it softened and slid out. We cuddled and held each other on the bed for some time, then got up. He dressed, kissed me goodby, and left.