Adventures of Shemale Sandra Ch. 01
Keywords: Ch., of, 01, Shemale, Sandra, Adventures,
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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.
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Keywords: Ch., of, 01, Shemale, Sandra, Adventures,