tagTranssexuals & CrossdressersMy First Shemale Sex

My First Shemale Sex

byavailable269©

I had developed a strong desire to be with a hot looking shemale for a long time. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our firm in Las Vegas had experienced a server failure, and I was to leave that afternoon on a flight to Vegas to rebuild the server on an emergency basis.

After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous during a flight, so I needed a drink to calm my nerves. I sat at the bar and ordered my meal and drink. After a few drinks were gone, I noticed this stunningly beautiful lady enter the bar. She sat a few stools away from me at the bar, and I couldn't take my eyes off of her. She was a raving beauty, with long dark hair, and perfectly shaped breasts, and a nice, sexy low cut dress that showed a lot of cleavage. Her face was as striking as any fashion model; In short, she was a living goddess. I could not keep my eyes off of her, she was as fine a looking a woman as I had ever seen, and I could feel my cock stirring in my pants. She was one foxy looking lady.

During one of my many glances, almost staring at her beauty, she looked directly at me and smiled. I almost choked on my drink as our eyes made contact. My first reaction was that she was just being friendly, but I was very mistaken. Suddenly, she got up and moved to the chair directly beside me, and I was suddenly as nervous as a schoolboy on a first date. She introduced herself, and I found her name to be extremely enchanting. She said her name was Raven, and that was very fitting given her long and flowing jet-black hair. We talked the small talk for a time, all the while I stammered over my words. Feeling my nervousness, she reached out and touched my hand, trying to calm my kid nerves. My cock immediately shot to its full length, and I was suddenly extremely hot for sex with this beautiful specimen of a woman.

With that thought in mind, and a couple of more drinks later, the conversation-changed direction drastically. I started dropping compliments about her beauty. I told her how stunningly beautiful and sexy she was, and looked into her dark eyes while saying it. I immediately felt her hand on my leg, very near my now extremely hard dick. Her touch felt electric as she very slowly caressed my leg. Her hands wandered ever closer to my now throbbing cock, and then I felt it. She used her right thumb to gently stroke my swollen cock head as we sat at the bar. The electricity of the moment felt like a bolt of lightning as it shot through my body, and the risk of doing this in public added an additional thrill to the element.

I was in ecstasy for a moment, as she asked me if I wanted to go someplace and have some fun. I asked what kind of fun did she have in mind, and with a big beautiful smile and a wink, she replied, " What ever feels good". My cock was harder than it had ever been as thoughts of this woman naked on my bed went racing through my mind. I told her I had a room upstairs, and asked her to come up with me. She almost screamed the word yes as I took her hand and led her to the elevator.

When the doors closed, we found ourselves locked in embrace, hands exploring each other's bodies. The feel of her warmth, the scent of her hair, and fragrance of her perfume drove me wild with desire. She was one extremely sexy lady, and she was with ME!! We were kissing passionately as the elevator stopped and the doors opened up to a middle aged couple standing there. Only slightly embarrassed, and a little proud as we passed the couple, the woman gave me a wink as if to give her approval. With Raven's hand in mine, we entered the hotel room. Since the company was footing the bill, it was a very nice room, with a hot tub, and all the comforts.

I turned to her and looked at her ravishing beauty and thought how wonderful this night will be making love to this exotic lady that has fallen into my hands. I stroked her gleaming hair as our lips met in a warm, soft kiss. Her taste was fantastic as our kiss became more passionate. She was very different in her manner than most women I had been with. She had a very special knowledge of the ways of pleasing a man, and I found it intoxicating, and very erotic just to kiss this sexy beauty, much less the exciting thoughts of what was to come. She led me into the bedroom and she looked at me with kitten eyes, and started to unbutton her blouse. I stopped her, for I wanted to do this myself, and she looked at me and smiled enticingly as her arms relaxed at her sides.

I found the first button and opened it, slowly revealing more of her golden silky smooth skin. I lightly stroked the newly exposed skin, and then slowly ran my moist tongue across the now glistening flesh. She rocked her head back as moans now escaped her parted red lips. What a sight to see her so turned on by this meager gesture to her sexuality. I could only imagine what was to left to come. I repeated this little ritual on every button, licking and caressing the newly exposed flesh, as she moaned her approval on each one.

I could now see the beautiful valley of cleavage, and her silky sheer red bra, and her hard nipples just begging to be sucked, but that would have to wait, as she reached for my buttons, and repeated the ritual again for me. Her lips and tongue danced on my nipples like feathers, and the feeling was so sexy, and erotic. I could feel the electricity between us as her mouth did it's magic.

She worked each button as if it were a treasure being exposed, using her hot smooth tongue to kiss and lick the newly exposed flesh. She eventually arrived at the last button, and pulled my shirttail from its tucked position, gently letting it fall to the floor. She started kissing my chest, and sucked each extremely hard nipple as if it were her favorite candy.

She kissed and licked her way down to my belt, and then reached for the buckle to release it. I stopped her briefly and led her to the bed. We lay down onto the satin sheets that were a deep red color, and she continued to unbuckle my belt. She popped open the button and slowly pulled my pants completely off and dropped them on the floor. She gently caressed my hard cock through the material of my underwear, and then slowly slid her hand under the fabric to touch my raging hot dick.

Waves of ecstasy roared through my body as she expertly massaged my throbbing hot cock. She slowly removed the briefs and the hardest cock I had ever seen slowly peeked out from beneath the material. Her eyes widened as the hard 6-inch cock came into view. She had the look of pure sexuality in her eyes as she complimented me on how beautiful my hard shaved dick looked to her.

She suddenly, but softly softly spoke " I love a smaller cock on a man, it is easier to deep throat it for long periods of time". I was in heaven as her words worked their magic on my imagination. I could visualize my dick buried deep inside this stunningly beautiful woman's hot sucking mouth.

It was now my turn to remove a portion of her clothing, and I reached out to stroke her perfect breasts. I slid one shoulder strap of the sexy red lace bra, and kissed and licked the smooth flesh of her shoulder. Shivers must have overtaken her as she embraced me and seemed to tremble with excitement. I ran hot, wet kisses all over her neck and shoulders and she responded by reaching for, and stroking my dick as I kissed her body passionately. I laid her back onto the bed with intentions of getting her completely naked. I removed her bra completely to expose the most perfect pair of breasts I had ever seen. They were the ones I had dreamed of many times before. They were not overly large, with small, but long hard nipples just waiting to be sucked by my hot, wanting mouth. I caressed the hard pointy nipples, and then sucked one of them into my mouth. I could see the passion on her face as I sucked the hard rose buds; first one, and then the other in rotation.

I paused shortly and then slowly removed her red tinted stockings, stroking the velvety smooth skin of her legs as I removed them. She now lay almost naked before me except for her matching red panties, and garter belt. Man what a sexy beauty I had before me, and the sexual passion was growing stronger by the second. I reached to remove the garter, and slid it off and onto the floor with all of the others clothes now lying there. I stroked the smooth flesh of her stomach, and planted kisses along its length, while she moaned in ecstasy, and deep passion. Her moans grew louder with every flick of the tongue, and I wanted very badly to get her completely naked. I started to remove the red silky panties, but she stopped me, and told me to lay back and she would make me feel like I was in heaven.

I replied to her request and lay back on the satin sheets to let her do her magic once more. She stroked and caressed every inch of my hot, naked body. Something about her mannerisms were far different than any woman I had ever been with. She seemed to have a magic touch, and knew and used every trick possible to bring extreme pleasure to me. She just seemed to know what I liked, and what I needed to feel the ultimate in sexual pleasure. Her next conquest was to make hot oral love to my aching cock. She moved her silky wet lips along its length while cupping my balls in her delicate hand. I opened my eyes to her engulfing my entire dick deep into her wet mouth. I have never been more aroused by oral sex in my life. I was in sexual heaven. She then sucked my smooth balls into her talented mouth, and swirled her tongue around the pearly hot globes of flesh. They plopped out of her mouth with a hot sucking sound that had me now moaning in pleasure as never before.

I had the strong urge to kiss the mouth that had just released my cock from it. It tasted wonderful as our tongues danced with each other in an erotic, sensual deep kiss. My hands now roamed the sexy curves of her delicious silky flesh, trying to bring her the pleasure she was arousing in me. I stroked the hot mound of her pussy, but found it to be hard and stiff like a cock. Oh my lord I thought, she has a cock!! I was startled, for a short while, but my fantasy of having sex with a hot tranny popped quickly into my mind. I stroked the hot mound under the silky panties, as it grew even hotter and harder.

She must have known that I figured it all out, as I started to remove her silky panties, but then paused to look at the erotic site before me; a beautiful shemale in hot red silky panties with a hot and hard cock about to be exposed to my eager gaze. I stroked the hot cock through the silky material as she had done for me. I could see the outline of a small, but extremely hard cut dick underneath the sheer material of the red panties. Sexual passion engulfed my being as I reached under the hot red panties to feel the source of all the heat radiating from them. I slowly grasped the waistband of her silky sheer panties, and slid them over her hot smooth legs to reveal the nicest 7-inch hard cock I had ever seen. The swollen purple head glistened with sexual excitement, as several drops of delicious pre-come peeked out from the slit. I could not resist, I licked the drops from the swollen cock head and tasted the golden nectar of this hot sexual beauty before me. Her beautiful small tranny cock was hot as fire, as I again kissed the swollen purple head and took it into my wet mouth, swirling my tongue around it like a snake after it's prey.

The heat of her hot cock was overwhelming, as I then took the entire 7 inch length of this hot dick deep into my now dripping mouth. The silky texture of this hot beautiful cock in my mouth sent waves of ecstasy across my body as I sucked her hot shemale tool in and out, deeper and deeper until she screamed with pleasure. She moved to gain access to my dripping hot dick, and we sucked each other with a never before known passion, with me on top and her underneath. As I slowly fucked her wet mouth, I was becoming insane with desire and I screamed out in passion as both of our cocks received the ultimate in mutual pleasure. She suddenly stopped sucking the hot dick before her, and turned her attention to my hot manhole. Her expert tongue found it's target, and I almost blacked out from the pleasure as she worked oral magic on my butt hole. She inserted a finger into the hot, wet hole and fucked it in and out as I screamed in ecstasy from her expert fucking and licking. I could feel the cream starting to rise and I screamed that I was about to come. She returned her dripping mouth to my aching hot dick and swallowed it to the base in one big gulp. The hot man cream spurted out in long spasms that must have fulfilled her want for hot silky man juice, as she swallowed every precious drop as the spasms continued for some time, and my balls ached like never before. It seemed, as they would soon follow the spurts of hot cream as it flowed down her sucking hot throat.

Even as this progressed, I never lost mouth contact with her beautifully raging hard cock. I blew the hottest load of my life with a hot shemale cock deep in my mouth. I could not have asked for a hotter sexual experience then with this very sexy, and erotic shemale. It was a fantasy come true when it was the least expected. After we recovered from the earlier hot oral session, we continued the night with my first hot cock inside my manhole. She magically produced a small 5 inch jelly cock and lube from her purse, and slowly, and gently prepared my virgin love hole for what was to be another erotic episode in our already pleasure filled night. She first lubed up my hot puckered hole, and then inserted a slim finger into my virgin love box. This feeling was not completely new, as I had done this to myself a few times in the past. She slowly pumped the silky finger in and out of my hole until it disappeared completely inside the hot cavern. She then added a second finger to the mix, and worked in slowly inside my depths. Now came time for the jelly cock to prepare me for the ultimate pleasure. I felt it's initial touch, and it seemed to be so big I wondered if it would even fit. It really did not matter much though, as her finger manipulations had brought me to a sexual plateau I had never experienced before tonight.

She worked the jelly cock into me very slowly as my anal muscles seemed to relax and allow this new sensation to continue. A few inches at a time, and she would only pump it that far on each stroke. I then felt a little pressure as she stroked it even deeper now, but I begged her to continue. The cock went past the resistance, and slid all the way in to its full depth. I felt pleasure that has never been known to me before as she now increased the speed at which the rubber cock plunged in and out of my well lubricated, and burning hot love hole. It now plunged to its full depth on each stroke, as I arched my ass up to meet it's new welcomed intruder. I could now feel the fake balls bumping my ass cheeks with every stroke.

Suddenly she pulled the rubber cock out of my hole with a popping sound, and I looked at her as if I were a scolded puppy that had done something wrong. This feeling was short lived as she laid the cock down and rose up on her knees to show me the hottest, hardest cock I had ever seen. It was deep purple all the way to her tightly hung hairless balls, the swollen purple head now dripping clear nectar onto the bed. I moved to lick the precious clear fluid from her steaming hot shemale cock. It was a beautiful sight to see as this hot, hard she-cock was then directed towards my now open, and waiting manhole. I felt the heat as the swollen purple head touched me for the first time. She inserted just a few beautiful inches into my wanting tunnel, and teased me for a short time before giving me just a little more of her glistening, hard fuck tool. Now, she finally plunged the hot she-cock deep into my waiting depths, as wave of ecstasy coursed through my being. She pumped her beautiful hot she-tool in and out until I was drunk with sexual spasms that were totally alien to me.

I could feel her hot being taking control of me as her hot shemale fuck tool plunged in and out in frantic rhythm. The waves of ecstasy continued in rhythm with the plunging hot dick that was now deep inside me. The heat between us was intense, as she suddenly screamed with passion as the time of ultimate sexual pleasure was now upon her. She clenched large amounts of my flesh as the waves of ecstasy overcame her being, and the pearly nectar pumped deep inside my smoking hot butt hole, while my own hard cock erupted hot streams of pearly nectar onto the sheets in unison with hers. She screamed with pleasure as the hot cream filled my deep cavern, and then she collapsed on top of me from near exhaustion.

She fucked my virgin manhole two times that night and each time was as intense as the other. My hole was virgin to a hard, hot dick, and she showed me the pleasures of having a hot stiff cock buried deep into my love hole. She was very gentle, loving, and patient, yet very sensual and erotic with my introduction to anal fucking by a hot shemale dick. I gained a new respect for sensual anal sex on that very hot, erotic night. She treated me as a fragile child while she showed me how erotic getting slowly, and sensually fucked into ultimate ecstasy can be.

I returned the favor, and got to feel my hard cock buried deep into her hot, sexy shemale fuck hole. That was another first, but most definitely not the last time I would fuck a hot butt hole. It was the sexual adventure of a lifetime, and the hottest night of sexual pleasure I have ever experienced. Hot sexy shemales rule!!!

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by Anonymous

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by sxad_24707/11/14

Awesome

No sweet she male ever has to worry about me seeing her sweet prick...I want it.....it does not scare me off.....love cds or she males........just not enough around.........

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by Anonymous06/21/14

You are hot!

I never became so hard.I`m throbbing and ready to explode!

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by Anonymous05/26/14

curious

U want to be fuck by a shemale so bad just can't find one

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by Anonymous03/13/14

There is nothing better than being fucked by an attractive shemale mmmmmm.
I love it

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by Anonymous01/01/14

my fantasy

For over 10 years I have fantasized for that ooportunity,my wife's and I sex life is zero which fuels my fantasy more. I have been masterbating with a 7 in glass dildo for years because the orgasms aremore...

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