I had searched all my life, all my adult life that is. Since I was 18 my dream, my fantasy was to find and fall in love with a shemale. To anyone who had known all my long term boyfriends, that admission might have been obvious. The list was a pathetic hint of my secret wish. There was Mike, the bisexual swinger. Troy, the Latino with a decidedly feminine demeanor. Allen, the long haired adonis with rock hard man boobs. And finally George, who I'd met by chance in a chat room and who shared my transgender fantasy.
George had taken advantage of his anonymity and posed as a transsexual while we courted online and once the time came for us to meet at that hotel room in North Phoenix, I was too worked up to be disappointed that he was merely a cosmetically enhanced cross dresser.
George was supportive of me. He often complimented me, ignored the fact that I was a very small breasted woman with a skinny body and slightly oversized behind. My face had always been beautiful, my legs-perfect and my vagina was as fresh as a twenty seven mother of none could be. I almost married George. Almost uprooted and moved from my home in Tucson to be with him in Palm Springs. I guess though, in the end, the move was too much and George was probably the first man who lost his heart to me. But he left me with just enough computer savvy to revisit my dream.
I spent a sad month learning how to please myself with shemale dreams and a small vibrator. I might have been satisfied with that for a long time had I not stumbled onto a site in one of my rare internet porn searches. I found a particularly natural looking blonde model who had a moderately sized penis and natural looking, generously sized breasts. She was my fantasy for weeks, and what a fantasy she was.
About the tenth time viewing her, I was deep into a multi-orgasm in front of my computer screen when an urge to see her toying herself with a dildo struck. As I moaned aloud and my pussy dripped onto my fake leather chair, I manipulated the mouse erroneously and clicked onto a chat room for shemales.
I had already came four or five times which is probably the only reason I would have forsaken my favorite pictures and stayed on. I didn’t trust chat rooms after the George incident. But I humored myself, talked to a few patrons who were also, probably just posing men. Then I met Kerri.
She seemed honest enough, and unlike others, did not balk when I admitted that I was neither shemale-nor male and even said that she usually prefers female company. We discussed sex and soon began some dirty talk and since I was still nude, her conversation had me masturbating before I knew it.
I soon admitted having an orgasm to her and agreed to exchange photos. Hers was a picture taken next to a pool. She was topless, her breasts were fairly large and supremely natural. No circular silicone jigglers that you could bounce a quarter off of, Kerri had well formed parts, and her rosy nipples were erect and in perfect compliment. Her bikini bottoms barely concealed what appeared to be about six inches of semi-hard cock between her fabulously tanned legs. Her hair was blonde, her body, although not quite perfect, was a stunning site, and her face stared from the computer screen and reflected the 22 years she claimed to be.
I laughed, only a few flaws. I remember thinking-why would this girl be chatting? She could easily be playing in person.
I sent a photo anyway. Me in a long blue dress I had worn to a friends wedding. And Kerri complained that she had sent a semi-nude so I should as well. I didn’t have naked pictures but promised to take one and be back in a few minutes.
I almost knocked over a table trying to ready for the picture. She had said to either hurry or she was going to leave. Being nude, and my pussy being my best sexual attribute, I decided a slut pose would be best. I laid out on my side, set the timer, snapped the shot and rushed back to upload and send. In my haste I failed to notice that the picture was a complete failure. My breasts, as tiny as pears, seemed to sag like little balloons filled with coins. The little tuft a fur above my clit looked like a 1977 style big black bush. My usually exotic-long black hair was behind my back and what little could be seen looked as if it had just been slept on.
As I looked, after the photo was sent, I cringed, then laughed aloud probably just another George anyway.
Two full minutes passed without comment before she typed one word-Beautiful. I denied it, claimed I looked better in person and she asked me if that was an invitation to meet. Before I could answer she told me to click on a link that would allow me to view her camera. I willingly clicked and was so happy to see the same girl from the picture appear on my screen. She stripped off a tee shirt as soon as I was watching and held up a printout of my picture. There I was-naked and willing-a perfect six on a scale of one to ten.
Suddenly her camera moved and focused on the photo of me which she sat on a desk right next to her keyboard. Before I could ask-answer-or reply, her hard cock came into the camera view and her hand stroking like mad.
I almost had another orgasm. Probably the only thing to stop me was the fact that I was way beyond my quota. Kerri kept stroking though and as I joined her, it was obvious that I would soon have what I describe as a massive one.
It was all over too quickly. Her cock blasted a massive load that covered the picture and streamed a shot or two onto her keyboard. And for the first time in my life, I squirted.
The computer encounter dwelled in my mind for weeks as I visited, and revisited the site but never encountered Kerri. I tried with a few other shemales and shemale posers but never found one I liked. I had given up and even abandoned the site for three or four days when I again got on the computer and a blast of excitement, when a window popped up with her name attached and Kerri said, /> We chatted again, this time like infatuated high schoolers. We discussed music and movies, likes and dislikes, food and drink. We became fast friends and she soon told me that she lived in the LA area and asked if I would like to come and visit.
I wanted to wait, didn’t want to seem overeager, but we soon realized that an immediate meeting would be best. She volunteered a semi-public place to meet-a shemale club that allowed only feminine patrons-no men or cross-dressers. I told her that I thought shemales preferred men but she laughed and said, “The porn sites would make you believe that but it’s not true.”
The nine hour drive felt like ninety. I had taken a couple days off and drove to LA in mid-week planning to return to my job next Monday. I was too tired to think once I reached LA but as I made way through the massive city and came up to the address and the sign that read Candy’s Club, my senses renewed and my pussy was in danger of staining my jeans.
It was near three when I entered the dark bar-like club and only two people were there. The bartender was hidden in the back busily preparing for a rush, and a liquored up waitress who had way too many male hormones was sweeping up. I ordered a drink and found out that the rush was about two hours away, ordered a sandwich, and took a seat at a table.
The sandwich and drink were served within minutes, the manly waitress brought it and began to casually reveal the type of place I had entered. The sandwich sat on a plate, and was held waist high-a hoagie style bun that was supposed to contain ham and veggis. The drunk waitress signaled for me to take the sandwich but held onto the plate when I tried. She signaled again and this time I simply grabbed the hoagie.
Imagine my surprise when I found that no ham wascinside that bun. The veggis and bread slid off and a nice looking four inch-mayonnaise covered cock was left on the plate.
I giggled, expecting a joke to follow but the waitress didn’t budge.
She said. I was unsure if it was a question or accusation.
I nodded and she immediately removed her shirt. Her naked body was appealing, but her face, except for the longish brown hair, looked more man than woman.
I objected. “I’m meeting /> The voice erupted behind me, a mans voice.
I turned to look, and the bartender had shown herself. She too was a very masculine shemale, completely naked, but her wide load body had to be pushing two hundred.Her hard cock was eight inches long, and looked about as wide as an f-ing soup can.
I looked forward, not at either one, and said. “I’m meeting Kerri. She said this was a nice place.”
The bartender laughed, the drunk waitress joined in. They both blurted between guffaws. And the waitress. the biggest slut that comes here and she does not sleep with /> I moved to get up but as expected, the bartender wrapped her powerful arms under mine and held me fast. The waitress unbuttoned my jeans before I could object and pulled them down to my knees. I kicked madly but the pants ruined the impact and my effort simply made the waitress angry. She grabbed my panties and instead of pulling them off she pulled them up with all her might. The fabric wedged into my vagina and ass so forcefully that I assumed both were bleeding. Then, with one violent jerk, she ripped the fabric from my holes causing a rug-burn effect and I screamed.
My fight had been stolen, I was afraid, my body was now a limp playtoy for their pleasure, and they had some unappealing wants.
As they laid me out I gathered that the waitress was named Donna, the bartender was Sharon an although Sharon was larger and stronger, Donna was clearly in charge.
Sharon controlled me by sitting backward on my face, her knees on my arms. Her large balls rested on my chin and her asshole covered my nose and mouth. I would have suffocated but as I became oxygen deprived, she lifted her weight just enough to allow my face to turn to the side, then she sat back down, my hair wedged in her crack.
Donna was already going down on me, her tongue slid in and out of my pussy and two fingers jammed painfully into my virgin ass. I fought the urge but soon my juices began to boil and mostly because I could now see neither one, I was in eminent danger of orgasm. Thankfully she stopped just before I started moaning.
For a moment I thought it was over, but the manly tramp was simply repositioning. Her smallish cock slid easily into my pussy and she began fucking as if she were trying to kill me with each forceful thrust. Her dick slipped out at one point and I tried to close my legs. Mistake-she grabbed the small triangle of hair above my pussy and ripped about half of it out. I screamed, but my legs spread wider than the state of Nebraska.
Donna fucked me another five minutes or so and again worked me to near orgasm then she pulled out, Sharon arose, and that little dick shot sperm all over my face.
All the disgust disappeared when something deep inside me realized that I had just pleasured my first shemale. My hands were now free, one grabbed and stroked the last few drops from her tiny cock, the other hand massaged my pussy in haste. I came aloud, moaning like a schoolgirl whore, not believing the repulsion that had so quickly subsided.
My pleasure was short lived. Sharon positioned herself atop me. Her strong arms held mine, her wide body kept my legs wide. Her face was something like a freak-fat, twisted, looking like a rabid animal about to devour a t-bone steak. Her eyebrows were thick, her shoulders too wide, her center was flabby and fat and her crotch was hairy all the way to her belly button. Worst of all, she had small breasts that sagged a bit and reminded me of leather sacks of sand. Her nipples were large, like pinky finger tips and her thick cock needed no help finding my poor little pussy.
The first thrust seemed like it ripped me open. The second was thankfully a bit more lubed and although painful, went in a bit easier. She grunted and even drooled but thankfully she guided that fat thing with long gentle thrusts. I began to think I’d survive.
A couple minutes in she laid her entire weight flat atop me and began kissing my neck. She worked her way to my lips and extended her tongue but I resisted, remaining tight lipped, moaning in pain as she resized my pussy.
She tried to coerce my lips apart for a few minutes but seemed to give up. “I think you don’t want to kiss me… I’ll come much quicker is we kiss.”
Her breath was a bit off-not terrible-but certainly not fresh, and was just another thing that repulsed me and steered me far from the orgasm forced on me minutes before. I kissed her passionately and this seemed to slow her rate of thrust which also may have been a good thing.
Several times I felt that ramrod tense up, and each time she fought the urge to come and continued thrusting. Fifteen, twenty, thirty minutes of constant rhythm made my pussy feel like a chewed up dog toy. I was sore, and as far from turned on as humanly possible. My pussy was getting dryer and dryer and I began talking dirty in an attempt to hurry her up, and end the torture.
“Fuck me baby.” I called out. “Come for me.” I begged over and over.
Soon she joined in on the verbal assault. “I’m going to come in your pussy. I’m going to fill you up.”
And I was sure she would carry out just that until she pulled violently out and slapped me hard across the face. My chest looked like a small boys when I was stretched out on my back. My small breasts flattened out and my nipples sat like lonely points on a clean level map.
She pinched one nipple very hard. “I don’t turn you on bitch?” She said spitting in my face with each word.
I called out in pain and claimed she had gone too long. She slapped me again, licked her hand, stroked her cock and forced it harshly into my ass.
The only anal sex I’d ever had prior to this caustic battering was the two fingers Donna had liberally inserted a half hour before. I screamed and cried and begged but she continued to thrust like a big fat animal and for the first time, I considered that I’d be killed after they were through.
“Want me to stop?” She growled.
I whimpered. /> “Then I want you to suck me till I come and you’d better swallow every drop.”
I pleaded, imagining the taste of my ass among other things.
She thrust harder and deeper. I thought the pain would make me pass out for a second but unfortunately I remained conscious.
She sensed the pain. “Going to suck me off?” She growled, a stream of saliva dripped from her mouth onto my face.
I whispered, seeking to end the pain at whatever cost. Another mistake, because when she pulled that fat cork out, the pain was the worst yet, and again, I barely remained attentive.
By the time I realized my dream like state, her cock was shoved into my open mouth. The taste was too much, I gagged, spat out her cock and vomited. She allowed me a few seconds to recover then promised that if I did it again, she’d lock me in a dungeon and fuck me everyday.
I was sucking that fat cock in an instant. She jammed all eight inches in and the only thing that saved me from throwing up again was that nothing was left to throw.
Her cock tensed, I tasted pre-come, and she pulled out. I thought she would shoot on my face but instead she lumbered into 69 position and shoved her cock right back in Her tongue began working my pussy but there was no feeling left. She continued to lick me, although my pussy was like the Sahara.
A half hour later I began to wonder if she’d ever come. Donna had even called out to her that customers would soon show up, and she would soon have to unlock the door.
Sharons tongue slipped from my pussy and licked the area before my anus. She licked a few times and a rush of ecstasy shot through me. She must have sensed it because her tongue slid deep inside my rear and worked with impressive strength. My orgasms began within a few seconds. One orgasm, sixty seconds later, another, a minute and a half, number three hit hard. For the first time I was screaming for joy, I released her cock and when the forth orgasm erupted, I squirted what seemed to be a gallon all over her.
All went still, I lay there moaning for minutes, my body quivering with injured pleasure. When I came to my senses, she was positioned above me straddling my face. Like a slut in lust, I returned the favor. My tongue slid past a tangle of pubic hair and into her ass. I went as deep as I could and though she clearly enjoyed, she could not wait to force that fat cock back into my mouth. I sucked like a vacuum and she moaned like one. Within seconds that cock shot what seemed to be a gallon into my mouth, and down my throat.
She moaned a minute, then climbed off me. I saw all those features that repulsed me before and was willing to excuse each one. I dreamed she would kiss me and tell me how special I was but she dressed quickly and dashed back to the kitchen.
I was still spread eagle when Donna came out and told me. “If you report us, we’ll have our story straight. It’ll be two against one and we’ll make sure your family hears about this… You gonna cause /> I sat up. “No problems.” I said.
She threw a wet towel at me. “Clean up the mess. If you want to stay you’ll have to take a shower in the back room.”
I checked my hair-come-vomit and who know what else. I was more of a mess than either one of these ladies, I thought. And I did exactly as she said.

story by: auliianlit

Tags: reluctance transsexual diary sex story

Author: auliianlit

Related sex stories: