Thread: Shemale Stories
View Single Post
  #112  
Old 02-17-2009
smc's Avatar
smc smc is offline
Senior Ladyboy Lover
 
Join Date: Nov 2008
Location: Boston area, U.S.A.
Posts: 18,085
smc has a reputation beyond reputesmc has a reputation beyond reputesmc has a reputation beyond reputesmc has a reputation beyond reputesmc has a reputation beyond reputesmc has a reputation beyond reputesmc has a reputation beyond reputesmc has a reputation beyond reputesmc has a reputation beyond reputesmc has a reputation beyond reputesmc has a reputation beyond repute
Send a message via Yahoo to smc
Default Be My Valentine? (part 2)

(part 2)

Heading out from the men's room, Steven ran into a guy he knew from high school, hanging at the bar with some woman he's never seen.

"Hey, Steve, since when do they have costume parties on Valentine's Day?" the guy asked, mockingly.

"I beg your pardon?"

"What's with you and Miss Chuck Sweetlea over there, all dolled up?"

It suddenly hit him. It's wasn't an accident that he felt so comfortable. His mind was probably working overtime to suppressed the thought, but he was on a date with Chuck.

In his freshman and sophomore years of high school, the Sweetlea's nephew Chuck had come to live with them while his parents went away on some kind of church mission. Back then, Steven lived across the street in his parent's house, the very one his sister now owned.

Chuck was the only kid in the neighborhood Steven's age. They became good friends. They did everything together. They shared the same hobbies, listened to the same music, and talked about asking out the same girls, which they never got around to doing. They got drunk together, stealing wine from his aunt and uncle and whiskey from the liquor cabinet at Steven's house. And one night, when they went camping at the state park nearby, they drank a little too much and jerked each other off. Chuck had even touched Steven's cock with his tongue, for about five seconds, before they both recoiled in shock.

In some ways, Steven considered that night to have been the loss of his virginity. Sure, he hadn't penetrated anyone, but he let someone touch him and he had an orgasm.

Chuck moved away just before junior year to join his parents somewhere in Asia. Eventually, they just lost touch.

Now, Steven was confused and even a bit angry. He collected himself as best he can and heads over to the table. Sitting down, he looked Charlene right in the eyes and says, "You're Chuck."

Charlene was completely non-plussed. "No, Steven," she calmly replied, "I was Chuck."

"What the fuck?" Steven stammered. "What have you done with yourself?"

Charlene was silent.

"Do you really expect me to go to that dance with you?" Steven asked, trying not to shout.

Charlene was silent.

"Say something, damn it!" Steven shouts this time, and a few heads turn.

Charlene's lower lip quivered just a bit, and it seemed that she might start crying at any moment. Then, suddenly, she straightened up in her chair, pushed out her pert breasts, took a deep breath, and said, "We are friends, and you shouldn't speak to me that way. If you want to know about me, you have to take me to the dance. I promise not to embarrass you."

Now it was Steven's turn to be silent.

"Remember how close we were?" asked Charlene. "Do you trust me?"

Steven sits for several minutes, conflicted. He looked Charlene up and down. To her, he seemed to be having a silent debate with an angel and a devil sitting on his respective shoulders. Finally, he relented.

"Okay, but you have to tell me everything. And no dancing!"

They put on their coats to leave. They hurried to the country club, found a table away from others, and sat down as dinner was served. Steven was now anxious to hear Charlene's story.

She tells him about moving to Thailand, where her parents were doing church work. They were so busy traveling around the country that they pretty much left her to fend for herself alone. Chuck went to an American school in Bangkok and befriended one of the young teachers there who instructed students in the Thai language. Her name was Lee, and she was only a couple of years older than Chuck. They stayed friends when he graduated and decided to enroll at the Mahidol University. He saw Lee often.

One weekend, during Chuck's third year at the university, Lee asked whether he would like to go on a real "date." Always in the past, their time together had felt like friends hanging out. She said tonight would be different.

They had dinner at a nice restaurant, went to a nightclub in Bangkok and danced for hours, and then went to an all-night bar where they sat in a quiet booth and laughed and talked and, for the first time ever, started to make out. Chuck was very excited; he hadn't had a girlfriend since the last year of high school in Thailand, and that had only lasted for a few weeks, although he did to have intercourse with her twice. Lee whispered into his ear that it was time to go to her apartment. They rode in a taxi, and Lee began to do everything she could, short of stripping off her clothes, to get Chuck aroused in the back seat. She licked his ear, kissed him, and stroked his cock through his pants. She took one of his hands and put it under her shirt and on her tits. Chuck thought he would cum before they even got to her place. But he managed to hold it in.

Once at her apartment, Lee quickly stripped Chuck's clothes off and took off hers, except for her silky boy shorts. She had small tits, with very hard little nipples. As she climbed atop and Chuck and rubbed herself against him, he began to lose his mind. She smelled so delicious. He loved the feeling of her hair across his chest. His cock was so hard, and he felt like he would cum at any moment. Lee sensed this and slowed him down. Then she got off of him and sat at the edge of the bed.

"I like you so much," said Lee, "that I am afraid. I am sorry I have gotten you so aroused. I do not want to disappoint you."

Chuck was hearing nothing about turning back. "Why would you disappoint me? You're beautiful."

Lee stood up suddenly, turned away from Chuck, and pulled down her shorts. Slowly turning back to face Chuck, she revealed her secret: a small, brown, smooth, slightly erect cock, with a tiny drop of dew at the very end.

Looking Chuck right in his eyes, Lee smiled sheepishly.

"I want that!" Chuck said, in a loud voice that surprised Lee. He reached out and touched it gently, the dewy precum wetting the tips of his fingers.

At this point in Charlene's story, Steven was in a state of shock. He barely heard her as she recounted the incredible sex with Lee that night, or how they stayed in bed for the rest of the weekend, or any of it. He excused himself for a moment and went outside for a bit of air.

"Your date," some older guy outside told him as he passed Steven to reenter the building, "she sure is a looker."

As Steven walked back into the ballroom, he looked across at Charlene, sitting alone at their table. She really is pretty, he thought. But it's Chuck, he also thought. He makes his way back.

"Are you okay?" asked Charlene.

Steven spoke with bewilderment tinged with just a hint of anger. "Okay, I get it, you had sex with some kind of freak. But how did you end up like this?"

Charlene was visibly hurt by the word he used, but she remained strong. She told him that after a few months in the new relationship with Lee, Chuck began to realize that what he really meant by "I want that" when he saw Lee's cock. He wanted to be like Lee. It made sense. It explained everything he had always felt about himself that he had shared with no one, even Lee. It took several years, and Lee was with him all along the way as he transformed from Chuck to Charlene. That was a good thing, because Chuck's parents disowned him.

As Charlene, he lived a decent enough life in Thailand. Lee remained very close, although as the transformation went on she was less and less interested in sex with Chuck/Charlene. After a few more years, Charlene began to miss the United States, and decided to return. But to where?

Throughout all this, "Chuck" had stayed in touch with his aunt and uncle. They knew about his transformation, and were supportive. They tried, unsuccessfully, to get Charlene's parents to let her back into their lives. Auntie even visited Charlene in Thailand. So, Charlene decided to return to the Sweetlea's home across the way from where Steven used to live. That was three weeks ago, in late January. She holed herself up, hardly going outside except for a couple of times to the grocery store with her aunt. That's where she ran into Steven's sister, for just a moment.
Reply With Quote