Adventures of Shemale Sandra Ch. 01

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The Story of Sandra.
3.6k words
4.35
68.7k
18

Part 1 of the 2 part series

Updated 10/24/2022
Created 06/01/2004
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Elyquent
Elyquent
12 Followers

His name was Phillip. Or at least it had been. Honestly, he wasn't sure who he was; all he knew was that what he had done two years ago was what he thought was right. This was the lifestyle he wanted.

It should be said that Phillip has always had strong female influences throughout his life. He and his three sisters were raised in a single parent home by their mother. She cared for them, did her best to support them and because of this his childhood was for the most part pleasant. But there was always one thing missing. Phillip never could fit in with the other boys. He often spent days alone in his room wondering why this was, but the only conclusion he could ever come to was that it was his sisters' fault. Oh, how they had subjected him to the colorful side of life -- flowers, dress-up, dolls, giggling, you name it and he was put through it. And a lot of DID rub off on him, he reasoned.

But he loved them, and he enjoyed their company no matter the consequences. Even when he outgrew their antics(and underwent other necessary separations from them -- puberty and all) he still longed for female companionship. This he sought in his classmates, but the slightly pudgy Phillip never met with much luck in that regard either. He was chronically shy. His attempts at forming bonds of friendship with the opposite sex were always turned down with frightening sincerity. He couldn't bring himself to demonstrate all of the characteristics his sisters had instilled in him as a kid because he didn't want to be branded a "fag", and so everyone thought of him as weird and repressed.

So he mostly stuck to himself. It wasn't too bad he thought. He was still picked on occasionally, but he reasoned that he didn't care. He worked a part-time job, made good grades and had plans to go into the computer field when he went to college. What did he need friends for? Everything was working out quite well. In fact, there was only one problem as he saw it. Just one thing holding him back from a life of utter profressionalism. Just one especially little thing.

His penis.

What a curse he thought this was! It was always distracting him from what he knew was important. Worse yet, no one cared or even seemed to acknowledge that he had one. Especially not girls. For so long he had wanted to see a girl naked. His sisters were one thing, but he wanted to see a real girl's body. He didn't even have to put his penis in her; he would be content to rub it against her naked leg gently. Then he would cum, and he could put it away. That was all he wanted, but he couldn't have it. Girls were freaked out by him for some reason. And guys, well, at least he could talk to them normally. Even though most thought of him as a pudgy nerd.

His sexual tensions began to perpetuate when he eventually moved out of his mother's home and began going to college. He found himself almost alway sporting an erection. At times he would even skip class to go and jerk off. He was already a sexual maniac, and he hadn't even had sex!

That's when he started to subscribe to the Internet. It soon became his best friend. He would spend all night on it, finding pictures and studying them closely while he stroked his attentive member to a gooey orgasm. Hardcore, lesbian, masturbation, bondage, cumshots -- he was into it all. But one fetish in particular had caught his interest. This was that of the T-girl or the shemale. He was infatuated with the idea of being a woman. It would mean he could for once be accepted sexually and that he could easily go into bars and pick and choose which guy he wanted to take home with him. Sure, he still wouldn't have much luck with girls, but at least this way people wouldn't call him a "fag", or at least he hoped not.

And he had the money to try it out, so he began to do research.

Two years passed.

Now, he was no longer a he. He was a she, and her name was Sandra. Sweet, 5'9, slightly plump at 150lbs Sandra. Her hair was long and brown with slight bangs peeking over the edge of her eyes, her skin was a luscious shade of tan and, oh, her breasts, they were coming along beautifully. Large, rounded and topped with two puffy brown nipples, slightly droopy but big enough to easily call a man's cock to attention. She was stunning, she thought as she laid there on the bed, her own cock standing at attention. She had been holding it in her hand and stroking it wildly for a while.

Her plans to go out that night didn't involve getting a hard-on, and so she endeavored to make her girly-dick more compact. Up and down her hand went, over and over. She briefly imagined what she might look like to others right now, a full-figured woman laying on the bed trying to get rid of a raging hard-on. The idea was actually a big turn-on to her and after latching onto it in her mind she began to stroke faster. "Oh God," she cried out in a cracked voice. Her speech wasn't entirely feminine, but neither was having a big, bulging cock, and so she had comes to grips with the fact that everything wasn't going to be picture-perfect.

But she sure looked it right then as her cock began to tremble of its own accord. The first spurt shot onto her stomach, but the second was like a fountain as it erupted all the way up to her flowing brown hair. And then there were two more. The last simply dribbling down her now-shrinking girly-cock. Sandra lay there on the bed, breathing heavily. It was some moments before she actually regained the energy to stand up, and when she did her words were briefly, "Shit!" She had made a mess just before she was going to go out.

She walked to the bathroom, her cum-spattered breasts jiggling with every step. Looking in the mirror, she began to pick the gobs of salty liquid from both her hair and body. She dropped all of them in the toilet and flushed. Her last task in the bathroom was to wipe herself down with a towel. Then she went back to the living room. Her outfit for the first big night out was laid out on a nearby chair. She reached over to a nearby desk and grabbed a roll of tape. Pulling her testicles and flacid penis back, she taped them off just before the hole that was her girly-pussy. Three strips should do it, she thought.

Next, she stepped into the panties laid out before her. They were white, silky and, she decided, a comfortable fit. After that came some very short shorts and then a low-cut tank top which didn't leave much to the imagination. Her outfit was complete. Something suitably slutty for a very slutty night out on the town, she thought. Her plans didn't include leaving the bar without a partner.

She climbed into her car and began driving down the street. Her taped penis was cooperating nicely and she hoped that it would continue to do so throughout the night. The last thing she wanted was to pop a boner right in the middle of the bar. She crossed several more streets and eventually the raunchy bar was in her sights. This was the best place to start out at, Sandra figured. The men here had a legacy of desperation, and just last week a regular was caught having sex with none other than his pet dog. If they'd go for a dog, they'd certainly be thrilled to have her, she reasoned. Even if she did have a little surprise for them.

But those thoughts were quickly pushed away as she threw wide the door of the smokey bar and entered. She swayed her hips alluringly during her approach to the bar and eventually took a seat on an empty stool.. There were three other guys near her. She didn't like to drink too much as a rule because it was harder to control her voice after a few cold ones. Besides, she was a lady and wanted to remain respectable.

But it was hard to resist when, not long after entering, one of the relatively skinny men seated at the bar scooted over to the stool next to her. "Hey, do you want something to drink?" he said quietly. Sandra turned to face the man and looked him over briefly before smiling. "Sure," she said. Before long there was a Milwaukee's Best sitting in front of her. The guy spoke again, "I-I've never seen you here before, a..are you new?" He was obviously a little shy. Sandra felt especially confident after noting this. "Ya, I'm from out of town," she explained after a lengthy gulp of beer. The guy didn't say anything.

She took another sip from her beer and took the liberty of browsing around the bar. It wasn't terribly crowded at this hour and besides the men seated at the bar, there was only one other group here. And they were off in their own world playing pool. She did, however, see that the other guys at the bar seemed hesitant to approach because of the man next to her. Sandra silently wished her beer-buyer would just break the silence and say something; she wanted to move on to another man if not.

Eventually, he stammered, "You're pretty, nice hair." A pause. "I mean, you have pretty nice hair," he corrected with an awkward smile. Sandra returned the expression but could tell this guy wasn't going to make the first move. She decided that she would have to. Daringly, she placed her hand on his thigh. He almost seemed to jump when she did, but he then put his hand on her thigh as well. Sandra started to rub, and the guy reciprocated. It was her turn to speak. "You're pretty cute yourself," she stated, along with a more mischievous and confident smile than he had shown. "Thanks."

By this time, she had finished her beer. The guy immediately offered her another, but she declined. She was doing her best to keep her voice feminine and didn't want to mess up, as she had already caught herself slipping once or twice. Luckily the guy didn't catch on. "So wha...what's your name?" he stuttered.

"Sandra, you?"

"Jeff," he announced with slightly more confidence.

"Cool," Sandra said idly.

She was still rubbing his leg and began to notice that it was having an effect on him. His blue jeans were bulging at the front, and Sandra had caught the bulge several times with her passing fingers. She grinned about it, and Jeff noticed, smiling. Sandra mused, "I'm happy we got to meet, and you seem to be too!" Her voice had cracked a bit, and she cursed herself, vowing not to talk in such big sentences. But again, he didn't seem to pick up on it, as his reply was a chuckle.

He elaborated, "Yeah, I-I guess I'm having a good day since I met you." Sandra was both charmed and confident. She was going to make a move. "This bar is smokey," she spoke, "My place?"

She continued, "I have more than beer!"

Jeff seemed sold. "Sure," he said and stood up with Sandra. He quickly turned his back to the rest of the bar, futilely trying to hide the elevated crotch of his pants. They walked out together. After a drive and a little bit of touching, they arrived at Sandra's house. Jeff seemed excited, and Sandra definitely was. This was it, she knew; the night she would lose her virginity. They got in the door and Sandra sat down on the couch, motioning for Jeff to sit beside her. He clumbsily did, his pants still bulging from their touching in the car. Sandra couldn't help but smile.

Jeff, however, was visibly nervous. In a way, Sandra felt sorry for him. She knew that, were she in his position, she would be the same way but, somehow, she derived confidence from her female form. She felt on top of the world mostly. But there was one thing bothering her at this moment too, and that was how she was going to break the news to him. Before she could think further on the subject though, Jeff hastily interrupted, "Uh... so you have drinks?"

"Actually, I'm all out," Sandra replied with a big smile, "I just said that so you would come here." She could tell Jeff was starting to sweat a little bit so she once again put her hand on his thigh. He did the same to her. They started rubbing again. Sandra trembled a little and started to worry as she felt the tape pop off of her formerly trapped girly-cock. She was getting a hard-on and fast. Her testicles were once again hanging down too, and she could only imagine what the front of her shorts would look like soon. Hastily, she made a move.

Her fingers went to Jeff's zipper, and she began to unzip his jeans. Jeff looked shocked and only managed a, "Oh baby," before visibly tensing up. Sandra figured in this position that she could conceal her secret by laying on her stomach, and so she did just that. He was wearing tight briefs. It took a bit of a struggle to yank them off, and when she finally did, what she noticed the most was that they had a rather large wet spot on the front. Pre-cum was already seeping from the slit at the end of Jeff's rod.

By this time, her hand had encircled that rod and was giving it a vigorous work-out. She felt like a pro when it came to handjobs after so many years of beating her own pud. Jeff began to get more comfortable, and he reached over and grabbed clumbsily at Sandra's swinging hooters. She hadn't bought any bras yet. They were just kind of dangling down, barely encased in her loose tank top. She liked the feeling of a man groping them very much. In fact she liked it so much that when Jeff tried in vain to pull her top over her head but instead ripped it straight down the middle, she only laughed.

He uttered a thousand apologies, but she just ignored him, not really caring. Her focus was on tending to that big, hard rod in between his legs, and her hand was doing just that. Meanwhile, Jeff had begun to suck on her large mounds tenderly. He really seemed to be interested in them, and that made her happy. But it was only a matter of time before she had to explain something else, she realized. Jeff's hand had been rubbing her thigh this whole time and was gradually beginning to gravitate towards her crotch. She winced as Jeff touched her cock.

At first he didn't seem to believe it, and Sandra felt him giving it extra attention momentarily to make sure it was what he thought. Then his hand left it, and his mouth opened, "Damn, are you one of them Hermpahodites or whatever?" Sandra responded, "No, honey, I'm a shemale" Jeff seemed to consider this for a second. Sandra began to masturbate him full-force in reponse. Maybe this swayed his judgment a little bit, as the next thing to come out of his mouth was, "You won't tell anyone, will you?" Sandra quietly sighed with relief and promised secrecy. Before long Jeff was pulling at her daisy dukes.

They soon came off along with the panties underneath, and there Sandra lay, entirely naked in front of this man. Admittedly, she felt more than a little un-lady-like as her five-inch boner throbbed and pulsed between her thoroughly tanned thighs, but Jeff didn't seem to particularly care. He was obviously quite excited, and even a little more confident now that he knew he wasn't the only one who was a little different. For a while they just sat there, staring at each other's naked bodies. Jeff was mostly looking at Sandra's she-cock.

Sandra wrapped her fist about her massively erect girly-dick at this point and began to tug on it while she looked at Jeff's own. "Jeffy, would you like to be my first?" she asked softly in her best impression of a whimpering female voice. She reached down and parted the entrance to her tight she-pussy, awaiting his response. Jeff seemed eager, and after a brief pause reached for her legs and lifted them up in the air. He positioned his throbbing meat at the dark entrance to her love tunnel and began to push forward.

It felt uncomfortable to Sandra at first and even hurt a little bit. But after a while she began to get used to it, and wow, was it turning her on. Jeff was kneeling on the couch in front of her, inserting his bare cock into her virgin asshole, while her legs were high up in the air, and her own cock rested against her tan stomach, leaving a trail of pre-cum as it slid around with every thrust of Jeff's member. This was heaven, Sandra thought. She tugged on her little girly-cock some more and whimpered. He was really going at it now. Sandra began to cry out, "Yes!" and, "Harder!" Jeff complied.

She was enjoying having this guy's big dick in her girly-pussy, and the fact that he was pretty much a stranger was even more exciting. She loved the idea of a strange guy fucking her in the ass and man-handling her sweet breasts. And Jeff was doing just that, his hands squeezing the sensitive orbs of flesh to the point that they almost hurt. Sandra started to buck back and forth on his cock and yank even harder on her girly-rod.

Her strange lover began to work her over even harder, his hands molesting her rounded breasts with no remorse. He pulled his member out briefly and lifted up Sandra, who has still tugging on her manly hard-on, and placed her on his lap. He reinserted his dick and went to work. Sandra just thought this was the greatest thrill. She loosened her grip on the rod between her legs and tried to steady herself. She was bouncing up and down frantically now, her cock slapping from her stomach to her penetrated ass and back again. How much longer could she hold out?

"Oh, Jeff!" she moaned, "Fuck my pussy baby!" Jeff was ramming her furiously. His fingers were digging into her thick thighs as his butt thrusted up and down, propelling his rock hard man-cock out of her puckered, little pussy. He was kneading her massive tits in his hands while at least making some attempt to balance her. It was a little hard to do with how much she was bucking though, and a few times Sandra slipped off to the side, but he fucked and grabbed her back into an upright position. He had a dead sexy shemale riding his dick like a little cowgirl, and he wasn't going to let her go for anything. At least until he shot his load.

Now crying out in a desperate and cracked voice, Sandra literally began to throw herself onto Jeff's tool with every bounce. Her cock and titties were slapping against her body so rapidly that they were leaving large red marks. "Oh Goddddd," cried Sandra, and suddenly shot a geyser of cum straight up into the air. It plummeted back onto her cock and all over the couch. Her irritated cock spurted for at least a minute before finally going to rest, at which point the vicinity was soaked with her thick lady jizz. She began to fondle her nipples and continue riding, although a little slower now.

Seeing the amazing site of a grown she-woman blowing such a massive load, Jeff was compelled to do the same and promptly shot a similarly massive load into the depths of her ravaged hole. His highly excited dick trembled and trembled inside the foreign girly-pussy for what seemed like minutes before finally ceasing its fire. They both lay there for about 5 minutes afterwards, Sandra's limp cock draped across her cum-soaked thigh and Jeff's resting in her rosey red asshole amidst more oozing cum.

Jeff said, "Are all shemales this fucking sexy?" Sandra stood up now, and smiled tenderly at him. A small stream of hot jizz was dribbling from her used fuck-hole. "Yes, baby," she responded through short breaths, "We love to fuck!" As if to accentuate this, she tugged on her shriveled girly-cock some more. Jeff almost felt like having another go, but both of their cocks were still sore from the experience, and so he told her he had to go but asked when they could meet again. "I'm sure we'll see each other again sometime, honey", was her reply. He nodded contently and left after cleaning up and putting his clothes on. Sandra looked on the couch at the mess of cum-stains and could do nothing but smile.

This was only the beginning, Sandra thought. What a beautiful new life this was!

Elyquent
Elyquent
12 Followers
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2 Comments
AnonymousAnonymousalmost 20 years ago
what a way to start writing

elyquent,

Your story is very, very hot and is exactly what I would like to do once in my life: live as a shemale, get picked up and fucked. I have loved and fucked many shemales, but secretly I would have liked more to be one of them. Please write more and more about this super sexy gender, the shemales whom we love sooo much, mmm

Diano

ps write me directly to diano_69@yahoo.com if you want me to share with you my experiences with shemales.

di

AnonymousAnonymousalmost 20 years ago
HOT

Very sexy start. I hope Sandra has many more stories to tell. Thanks for the great story.

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