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So, here I sit, 40 years old and just now realizing that while I am not attracted to men, I love pricks. I love mine, and I love looking at others. Hard or flaccid, black, white, or brown. The thought of a hard cock makes my dick twitch. I guess I have always felt this way, but I guess I never really got it because the men attached to the pricks I have seen inspire no sexual feelings at all.
It was the damned internet. Shemale porn everywhere. and while the majority of the images inspire no lascivious thoughts in me, I cannot help myself from seeking them out. And every once in a while I am rewarded by the image of a gorgeous woman with lovely tits, gorgeous ass, and a big hard prick.
So I fantasize, and jack my dick to thoughts of one of these gorgeous lady/boys dominating me and making me suck her prick. I have even bought dildos and fucked myself in my virgin ass to thoughts of being taken by a beautiful shemale.
I have at times thought to act on my obsession, but porn, the occasional 1-900 number, and chat rooms are as far as I was able to take it.
That is until I met Jamie.
Okay, about me. I am 6’ tall and weigh about 240lbs. Because of my height, I carry the weight well. I am not ripped, but neither am I a slob. I work in construction, and am in pretty good shape considering my eating habits. I am average looking. The kind of man some women think is handsome, and some wouldn’t spit on me if my head was on fire. As far as my “manhood”. I guess it is right for my size. I don’t know how long it is exactly, but I have never been embarrassed to take my clothes off in front of others. And if what I have seen in changing rooms is any indication, I’m pretty well off.
My job takes me out of town a lot, hence the poor eating habits. But the travel affords me the opportunity to experience a lot that I would never have the opportunity to otherwise. I am divorced, with no children, so I am not really tied to anyone or anything, so I am able to “play” when I am out of town.
I have got the art of seducing younger women down to a science almost. And I have enjoyed the company of more than a few during my travels. Sex isn’t always, or even usually the result of these indulgences, but it happens often enough to keep me happy.
Now the story.
I was working in New York. About an hour away from Manhattan. I was going to be there for about four months. Being that close to the city, I had the opportunity to go there on the weekends once or twice. I considered going to a club where I might actually meet a real shemale, or even hiring a tranny escort, just to have the experience. But I chickened out each time. I had fun in New York though, even got laid once.
So I’m working in this little town and spending my weekends playing golf, or going to the movies. I wasn’t planning on going back into the city anymore, so my dreams of finding me a real shemale slowly faded.
One night, about two weeks from the end of the job, I decided to go out to a pub down the street. It was within walking distance, and I had kept telling myself I would check it out before I went home for good.
The food was good, the beer was cold, and they had live entertainment after 10. It was just before midnight, and I was finishing my fifth and what I swore would be my last beer. As I was turning to leave, this young woman sat down beside me.
I guessed her to be about 25 or so, with long blonde hair and a really nice figure. She was about 5’9”, tall for a woman, and slim, with what appeared to be a nice full set of tits. She had a narrow waist and her hips flared in a way that made me do a doubletake. She was wearing a tight multi-coloured dress, cut low in front and with a hem line that was threatening to climb above her thighs as she slid onto the stool next to me.
I sat back down and turned towards her.
“Can I buy you a drink?” I asked. An oldie but a consistently successful ice breaker.
“Sure she said, if you sit and have one with me”
Now there was no way I was walking out with that kind of invitation handed to me by this hot little number.
I sat back down and she ordered for both of us.
“Two shots and two drafts, barman” she said, smiling mischievously.
The barman didn’t ask shots of what, or what kind of beer, so I figured her for a regular.
“I’m Jamie” she said, holding out her hand.
“Hi, my name is Tim” I reply, taking her hand. It was warm and delicate, with long tapering fingers and well manicured nails.
The shots,(whiskey), and the beers( draft lager), arrived and we moved to a table.
We chatted for awhile about nothing in particular. The band was playing and announced they were going to “slow it down” a little.
Jamie asked me to dance, and being semi inebriated and increasingly horny, I agreed. The thought of this lovely young woman in my arms was arousing carnal thoughts in me.
She fit perfectly in my arms, and as we swayed to the music, she whispered in my ear, “wanna get out of here?”
I leaned back and just grinned at her. Her green eyes sparkled with delight as she took my hand and led me off the dance floor and towards the door.
We both made a detour to the lavatories, and then were outside.
“Where do you want to go?” I asked.
“Where are you staying?” Jamie responded.
“I am staying at the Hampton Inn just down there” I told her, pointing vaguely in the direction of my hotel.
“Sounds good to me”
We walked hand-in-hand down the brightly-lit block. Just before getting to the hotel, we passed an off-license where Jamie insisted we pick up a bottle of wine.
We got back to my room, and I realized that I had no wine glasses, and no corkscrew. I got two hotel glasses that were clean, and I opened the wine with my pocket-knife.
We were both giggling and laughing at the situation.
After a couple glasses of wine, and more small talk. Jamie looked into my eyes and said, “are you going to kiss me?, or what?”
I broke out laughing, it was just funny for some reason.
Jamie joined in and somehow during the laughter, I wound up closer to her. Her beautiful, almond-shaped eyes looked into mine as I leaned in for a kiss.
Her full and sensuous lips found mine. They were so soft and wet I almost came in my pants.
I have always liked kissing, and we spent a long time doing just that. Kissing like lovers who have known each other for a long time. There was some touching and caressing, all over the clothes though.
Sometime during this necking marathon, Jamie’s hand ended up on my thigh. High up and close to my straining penis.
While we kissed, she let her hand slide up and over the outline of my manhood, caressing it through my khakis.
I began to fondle her full breasts through her dress, and eventually was able to manoeuvre her so that I could slide her dress off her shoulders and expose two of the most beautiful tits I have ever seen. The were so round and firm. But soft at the same time. Her areola’s where dark brown and large with nipples that were hard and long, just the way I like them.
I tried to get her to let me slide the dress under her hips so I could see the rest of her body, but she had other plans.
“Just lay back, cowboy, its time to play” she said grinning like the Cheshire cat.
Lay back I did, and she leaned over me, planting first one nipple, and then the other in my mouth. She left each there for only a few seconds, then repeated this. The second time, I heard her began to purr, yes purr.
Then she said “Bite Them!!”
“what?”
“BITE THEM GODDAMMIT!!!, BITE MY NIPPLES, HARD!!!!”
So I did.
She began to squirm and moan like no woman had ever done with me before. Jamie reached behind herself and took my stem in a vise-like grip.
“If you want me to take care of this, you better bite me harder.”
I wanted her to take care of me in the worst way, so I applied yet more pressure with my teeth.
“Yes, yes, yes YES!!” she screamed. And I swear I think she orgasmed right then.
My nipples are sensitive, so I could relate, but I had never shot my wad just from nipple play. WOW
As soon as her breathing began to come back to normal, she slid back off my lap and knelt between my legs.
Jamie undid my belt and unzipped my fly, then began sliding my pants down. I raised my hips to facilitate this action and as my pants were fairly ripped off my legs, my swollen prick sprang to attention and waved in the air merely inches from this sexy woman’s panting mouth.
“AHH” she said, more of a yell than a whisper.
She opened her mouth and swallowed my length in what seemed like one motion. I shave my nether regions and she was licking my shorn balls and taking them in her mouth in a way that was making me vibrate.
Then she moved back to my rod. Licking and slathering it with her tongue. She held the base of the shaft with one hand, and my balls with the other.
As she began to slide my trembling member over her tongue and down her throat, she started squeezing my nuts with every down stroke.
I never would have believed something that hurt like that could feel so good. Damn, I was in heaven.
As I began to feel my impending orgasm build inside me, I was torn between letting her take me over the edge, and wanting to take her clothes the rest of the way off and fuck her good and hard.
As this decision was being weighed in my fevered brain, Jamie took the reins and relieved me of the responsibility of making the choice.
She pulled back, my incredibly swollen prick bobbing just in front of her beautiful face.
“You like?”
“Oh god, YES!”
“You want more?”
“Yes yes yesss”
“You want to cum in my mouth don’t you?” she asked quietly.
“Yes, but I want to treat you right too Jamie, I do. Please take off your dress and let me taste you” I pleaded.
“Are you sure that’s what you want?”
“YES”
“Are you positive?”
“YES, YES, YES”
“Okay, but remember, you wanted it”
All I could think of was how badly I wanted to see this seductress naked. How I wanted to run my tongue all over her body and taste every inch of her skin.
Jamie stood, and for the first time all night looked a little unsure of herself.
She turned her back to me and slid her skirt down over her hips, hooking her thumbs in her G string and taking that down as well.
She stood with her legs together as she bent over to disrobe, and in the limited light, I couldn’t see her pussy but her arse was incredible.
I have always been an arse man, and hers was first rate. Two gorgeous cheeks, full and plump, just as a woman's should be.
Slowly she began to turn towards me. As she turned completely around to face me I looked at her eyes, then her lips, her shoulders, her beautiful big breasts, her narrow waist, her flaring hips..... her big, hard prick…
Big hard prick? Yes, it was fully erect jutting out proudly by its own powerful tumescence. It was amazing!
I did a classic double-take, then realized that all my dreams and fantasies were standing right in front of me. I stared in shocked disbelief, then glanced back up at her breasts and face, then back at that enormity transfixed...almost hypnotised.
The concerned look on Jamie’s face disappeared as she saw the smile on mine.
She stepped close to me and murmured sexily: “Still wanna taste me?” As she spoke she reached down to draw the foreskin back to fully reveal the pink-mauve dome in all its glory.
In response, I reached for her hips and urged her to me. With her standing, that beautiful male organ was right at face level. It was about the same size as mine, but not as fat. I smelt the glorious odor of her fabulous genitals. I took a deep breath stuck my tongue out and began to taste her. Touching the dome with the tip of my tongue. I didn't care about whether she was a male. To me she was all female...a beautiful girl with a lovely penis, and down there, below its base I could see her bulging testicles...simply delicious balls.
Jamie shaved completely like I did, and I spent a long time teasing and tasting her.
Finally, I opened my mouth and slid down over her beautiful flesh.
Within minutes she was pumping my face like it was her job. I fondled her balls gently as she had mine, and she began to shake and moan like she did when I sucked and bit her nipples.
I had never tasted spunk from another prick before, but I was ready to do it now! I wanted her to come in my mouth, down my throat. I needed it.
Once again, Jamie had other ideas. She began to talk to me again. Her voice rough and stern like when he told me to bite her harder.
“Oh, you are a good little cock-sucker aren’t you?” she grunted forcibly.
“Mmmmm...Mmmmm..” I moaned around her solid column as she continued to fuck my face.
“You want to taste my spunk, don’t you?” she growled.
Again “Mmmm...Mmmmm...” was all I could manage.
“Well, you will, slave, but not yet!” Something in her voice scared and excited me like I had not thought possible.
She pulled herself from my sucking lips and I actually whimpered. I wanted to suck her so badly.
She turned and picked up her bag. She rummaged inside and came out with a tube of lubricant.
Now as I said, I am an arse man, but really only to gaze at and perhaps being subjected to, but all I wanted then was her penis in my mouth at that moment.
I began to tell her this, when she cut me off.
“I know what you are thinking, you little cock-sucker! But it's not for me!”
With this she got on her knees again and roughly lifted my legs back towards my shoulders. As she took my penis in one hand I felt something cold on my anus.
She began to lubricate my tight hole and then slid one, and then two fingers up inside as she continued to grip my prick. I then started to feel afraid thinking about that monster of hers pushing its way up my tight rectum.
When a girl sticks a finger up my ass it always makes me cum bigger. I don’t know why. And as much as I wanted to suck Jamie’s cock until she came down my throat, the way she was making me feel made me lie back....somewhat docilely.
All of a sudden, she pulled her mouth from my penis and assumed a more upright position.
As I realized what was about to happen, I opened my mouth to protest, but it was too late.
“Here, slave, we both know what you really need,” she said through gritted teeth.
With those words, she rammed her rock-hard rod into my tight ass. The generous lube and some finger excercises had loosened me sufficiently but still didn't prepare me for that huge insertion up my rectum.
The pain was intense and all my sexual passion subsided. It took some time but then the initial pain faded to a dull ache, and then a delightful tingle. As she began to thrust, the tingle turned to the most intensely hot sexual pleasure I have ever known.
That lovely, sexy Jamie gazed down into my eyes as she pounded her prick into me, and as she continued to fuck me, she swore at me calling me names all the while. I had already figured out that this was how she expressed herself when she was really into the sex, and honestly it just turned me on more, especially hearing her using such foul expressions. After all, wasn’t my fantasy to be dominated by a gorgeous-looking shemale? Well it was happening, and it was both exciting and yet I had a feeling of being used against my will. It must have been my sub-conscience or my natural masculinity, so I kept gazing up at her...admiring her superb features and her lovely jerking breasts which all seemed to quell my misgivings. I began to actually feel like a sex-slave and felt glad being "raped" by a sensuous she-male.
As her pace quickened, I knew she was close to coming, yet I couldn't feel any sexual excitement. only a sense of being dominated...humiliated.
Just when I thought I couldn’t take any more, Jamie pulled out of my anus, leaving me feeling empty.
“but..but” I stammered.
“Shut up and get down on the floor” she commanded.
I did as I was told, and she climbed on top of me in the classic 69 position.
She took my flaccid member and ordered: “Swallow my prick, you little spunk-loving slave, and you'd better not come until I do!”
With that, she swooped down on my penis taking it into her mouth and began bobbing her head up and down like a piston.
I wasted no time. I opened my mouth to take that beautiful piece of meat between my lips.It was that sexual combination that caused my member to harden. Her weight on me, her hugeness in my mouth, her heavy balls resting on my eyes, her breasts pressing on my torso and my penis being sucked so skilfully.
I soon came close to coming many times. A beautiful woman sucking my penis, and a beautiful she-male's penis in my mouth. I was in a kind of sublime mix of heaven and euphoria.
After a very few minutes, I felt her tense up, and sure enough she began to release warm, thick globules of semen down my throat. As soon as the first shot hit my tongue I started to shoot my own load in Jamie’s mouth.
We spent some time licking each other clean and then we cuddled next to each other on the floor, pulling a blanket across our bodies.
“Did you mind about the way I talked to you, I cant help it when I get that turned on,” she murmured softly.
“Don’t you dare apologize” I replied, “you are everything I have ever wanted in a woman, and more. I wouldn’t want you to change a thing”
She smiled and said, “You never had a prick in your arse before, did you?”
I admitted that I had not, but that I might not want to experience it again. "Somehow," I said, "thinking about it, fantasising and all that is entirely different to actually doing it; but at least," I assured her, "I was glad to have had such a lovely, beautiful girl like you to seduce me."
She then shocked me by saying that I was now her permanent slave...not just a sex-slave but a body-slave...to cater for every bodily function and to tend to her every need as well as the apartment she owned, the cleaning, dusting and to wash her smalls. And then I began to question and face the reality of fantasies. So far, everything, even the acute pain and shame of being penetrated by a fearsome she-male penis, was bearable, and sucking her member, licking her full and heavy testicles was exciting. I didn't even mind so much knowing I was to be her sex-slave, until, that is, she forced me to undergo far more intimate services - that of submitting myself to her bodily functions... something I carelessly overlooked when she spoke of it.
The first act began when, after about half an hour, she told me that she needed a pee. Okay, I thought, go along, I'll lie here and await her return from the w.c., but she shocked me by murmuring that I must lie on my back. What for? I asked myself. I soon found out. She moved and knelt astride my chest. She looked down at me unsmiling taking her flaccid penis in her hand. "Come on, then," she said. I immediately realised her intention and my senses rose up in protest. I couldn't believe she was really going to piss in my mouth and make me drink it! I started to grunt my protestations but her expression changed. Her lovely eyes flashed and her lips curled into a kind of sneer: "Open your mouth, slave!" she growled. She gave me no option. I prepared myself for something I might have fantasised once...yes, and found exciting; but in reality I found it distasteful and profoundly degrading. I steeled myself against the resistance, the unpleasantness as I gulped the successive mouthfuls and reopened my mouth for the next. Fortunately, I found very little disagreeable taste, not giving my tastebuds time to register the flavour, but I felt utterly humiliated and yet, to my surprise, rather pleased that I had successfully accomplished another of her desires (she later told me that she loves pissing in a man's mouth, especially if he's unwilling) but then, after a few days under her demanding command, she virtually shattered me by revealing that I am to be subjected to a further intimate service - "The most immaculate..." she informed, and she introduced that awful ordeal by first bidding me to attend her in the w.c. where, to my horror, I saw that there was the shocking absence of toilet-paper!
It has been a long two months now since becoming Jamie's body-slave. All my erstwhile fantasies have now been fully realised - for the good or otherwise I cannot decide, but I know that soon I should escape her clutches which I readily threw myself into. Jamie might be aware of this, that's why she is exacting every possible immoral, bizarre "services" from me. On her part, she tries to convince me to stay with her, she even threatens to kill me if I try and leave her. So I'm in a dilemma. If I decide to get my own life back, could I lose it altogether by realising yet another of my fantasies...of being killed by a beautiful, sensuous she-male?
So let this be a warning - whether it's better to dream
Are you out there?
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