tagTranssexuals & CrossdressersEnd of the Beginning

End of the Beginning


Note-Ian was kind enough to let me use a character he created for a story of my own. Read "Retrained in Basic" first; this will make more sense.

Jamie stood there with her mouth hung open for a moment. She was utterly shocked. How could it be true? Chloe and Josh met at basic, how could they be engaged? It had only been a month since Jamie left. Tears stood in her eyes but refused to fall. This was not at all what she had envisioned. “Maybe it wasn’t love after all. Perhaps it was part of some left over confusion. It was natural to love your first though. Or at least believe that you do” she thought.

Unsure of what to do next she started for her car, but was stopped by a large handsome man. “Are you ok Miss? You seem a little lost,” said the man. Jamie looked up and found herself staring into the clear blue eyes of PV2 Matthew Bruce. Private Bruce was 6 feet 2 inches of beautiful. He was a blonde (though at the moment his head was shaved), built, and well tanned. The term ’gym bunny’ flittered across Jamie’s mind.

She shook her head in response to his question. “I am ok I think.”

Bruce nodded. “Hey, you look familiar. Do I know you from somewhere?”

Jamie gasped inwardly. She had been in basic with this man! Although she had told her mom, she had not started talking to people she had known with the exception of Chloe and Josh. This was different. “Might as well tell him,” she thought. “What have I got to lose?”

She took a deep breath and said, “It is nice to see you again Private Bruce.”

A look of confusion came over Matthew. He studied the girl and his eyes widened in realization. “James Newberry!” he exclaimed. Jamie nodded.

“I am having my name changed. Call me Jamie. Jamie Newcherry.” She stuck her hand out to shake his. She was not sure if he would take it, but she had to try. Matthew smiled in response. He slowly reached out and took her hand.

“It is a pleasure to meet you Ms. Newcherry. You can call me Matthew.”

Jamie beamed. She was afraid no one would accept her. It was a relief that Matthew did. She had liked him in basic. They had been friends. However, after that night with Chloe and Josh, Jamie had not been able to look anyone in the eye. “Thanks Matthew” she said. “How did you know it was me though?”

It was Matthew’s turn to look embarrassed. “Well, it is kinda hard to explain. I know, let’s go have dinner and we can talk about it.”

Jamie smiled. “Ok, I would love to. Do you want to go change first?”

Matthew was still wearing his full dress uniform from the ceremony. He shook his head. “I like the uniform. I think it makes me look good. But I should change in case anyone were to recognize me.”

“Indeed it does look good,” thought Jamie. She nodded. “I think I am dressed ok for dinner. Let’s go!” She was wearing a little red sundress with white flowers and little yellow stamens. She had a white handbag and white flats to match. The shoulder length auburn wig blew slightly in the wind. It was a rather convincing wig and Jamie had chosen it because it was her natural color.

“I just bought a new truck. Wanna take mine?” asked Matthew. He had been anxious to show it off to someone. It was a black F150 with a gray interior and a cd changer. He offered Jamie his arm with a grin. She swooned as she grasped it, hoping that what she felt was shared by her new companion. “Look, would you mind if we went somewhere out of the way? I don’t want to look at anyone from basic. Eight weeks was plenty.”

Jamie knew there was more to it. He did not want anyone in the military to call him out. She nodded. “I understand.” She was getting suspicious though. By this time, she was sure that Matthew was gay.

They climbed into his truck “I am going to check into a room, you don’t mind riding along do you?” Matthew asked.

“Not at all. As I recall I was supposed to be doing this too.” Jaime replied.

“You know, it is funny. We all thought you just wanted out.” began Matthew. “I never thought… you know. Look, you asked how I knew it was you. I know that must have been a surprise to you. Not many people would recognize you. I…well… I have a confession. I knew who you were so easily because I liked you. I have been interested in you since I first saw you. But you know how it is in the Army. I couldn’t just come on to you. But seeing you tonight, well, I like the new you.”

Jamie had no idea what to say. She sat there trying to sort out her emotions as the truck came to a stop in front of an out of the way hotel. It was nicer than most of the others in the area while being out of the way. It was the perfect place for Matthew to spend the week. “Let me run in and see if there are any rooms available.”

After a few minutes, Matthew returned. “Ok, I got a room. Do you want to come in with me while I change?”

“Sure, I mean if you think it will be ok.”

“Jamie it will be fine. None of the others will be out here. And there is only a small chance anyone would recognize you anyway.”

Matthew had gotten a room on the first floor. He opened the door and clicked on the light, throwing his suitcase and duffel bag on the floor. He started to open the suitcase when Jamie stopped him. “Maybe dinner can wait,” she cooed. Jamie looked into Matthew’s eyes to see his reaction. Matthew stood up slowly. He placed one hand around Jamie’s small waist and the other under her chin. He slowly lifted her chin, looked into her eyes and kissed her. She felt as though she were being swept away. Matthew felt himself getting hard almost immediately. It had been three months since he had sex. He move his hand around to the back of her neck as the kiss got more heated. Both felt the tension rising. Their bodies were responding to each other, and need took over.

Jamie suddenly broke the kiss, getting to her knees. She wasted no time unzipping Matthew’s slacks. She smiled as she freed his elongated member from his boxers. He was a full seven inches with a wide girth. Her tongue traced circles around his circumcised head, teasing him. Matthew moaned in frustration. Her heart started to race as she heard the pleading tone of his moan. She quickly slipped her lips over his cock, bobbing back and forth as though she were an expert. She could feel the head of his throbbing member hitting the back of her throat. Matthew placed his hands on her head, exaggerating her movements.

Suddenly Matthew pulled Jamie back. “I will cum if you don’t stop now. It has been awhile.” Jamie nodded and stood up, but not before pausing to admire his glistening penis.

“I want you,” she whispered.

Matthew led her to the bed, undressing as he went. He had no desire to ruin his uniform. Jamie sat on the bed, but made no move to undress. She was curious to see what he would do next. Plus it gave her the chance to admire his body. The only flaw was a three-inch scar just to the right of his belly button. He approached the bed and stood directly in front of her. She traced a finger over the scar. “What’s this from?” she inquired.

“Later” he replied.

Matthew pulled her to her feet, and turned her around. He kissed her slender neck as he bent her over and lifted the skirt of her dress. Jamie had chosen a pair of thongs for the day. Suddenly she was glad she had. They were a little red pair that matched her dress. Matthew smiled. He had entertained fantasies of a transsexual, but had never before experienced one. He found it to be an enjoyable experience. The feminine softness of Jamie mixed with the musky male scent drove him wild. He slid her thongs to her ankles, revealing a rather well formed ass.

Making sure he was still slick from the blowjob he started slow into her tight little hole. Matthew was very much a gentleman. Nevertheless, Jamie was not up for the nonsense. Without a word she pushed back, burying his cock in her ass. A moan escaped from them both. Matthew was a bit surprised, but took no time pondering the move. He started pushing in and out and fell into rhythm with ease. Jamie met each thrust pushing him farther in. “Harder, please!” Jamie pleaded. He obliged at once, pumping in and out of her ass, releasing his pent up frustration. Jamie felt an odd pleasure and pain; this was different from her first encounter. There was more passion and feeling here, more need.

“I am going to cum!” Matthew exclaimed. Jamie moaned louder and louder, sounding more feminine now than ever. Such ecstasy! She had never felt so filled, so complete before as she did with Matthew’s throbbing cock insider her. Matthew came, spurting his juice into her ass.

She sighed, content for the moment. “I think I need a shower” she joked and slid from her dress.

Matthew snickered as he slid out of her. “We can arrange that” he said, admiring her body. He noticed that she was wearing a red padded bra. He looked at her and asked, “Um, I hate to ask, but have you gotten smaller?”

Jamie looked puzzled and then realized what he meant. “Oh, you mean my clit. Yes, the hormones I am taking are shrinking it. It’s ok though, I don’t mind. I was around five inches, now I am down to about four. The doctor warned me that it may happen.”

Matthew smiled at her. “I think it’s perfect,” he said, stroking her. “Now how about we go for that shower?”

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