Tranny Tina’s Sex Secret

My name is Jordan Conrad. If you’ve never read them, I guess I should give you a quick summary, so you’re not in the dark about what’s been going on in the past few months of my life. Bear with me during the slow parts. I promise this is all going to be a lot more interesting as you keep reading.

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Last summer, I came home after finishing the second semester of my sophomore year at the University of Connecticut. Once I was home, I fell into my old routines, hanging out with the usual crowd who were also home for the summer from their various schools. Through a friend, I “met” a girl named Rebecca, and there was an instant attraction between us. I say “met” because I did know her vaguely in high school, but we had never been close friends. Within days, she and I were a couple, and I fell in love with her before I even knew it.

Later that same summer, Rebecca and I went to Vermont with a group of friends to stay in a timeshare condo owned by my friend’s parents. Since we were a couple, we got a bedroom all to ourselves, one with a king-sized bed and its own bathroom. You can imagine what was going through my head when I thought of the two of us together, alone at night with no one to disturb us. I don’t want to come off like a horn dog or anything, but young men have needs. I was also a virgin at the time, as was Rebecca, and I was eager to lose my virginity to a girl who meant so much to me.

I could never have predicted the surprise that was in store for me.

As I had hoped, things got hot and heavy between us, almost as soon as we were in bed. I knew this was the moment. But then something went wrong. Rebecca became upset and afraid that I wouldn’t love her anymore if we had sex. That wasn’t true, of course, but I still wanted to do it REALLY badly. That’s when she revealed the biggest shocker of my life: Rebecca had a penis. She had been born a boy and had chosen, before I ever knew her, to become a girl as she believed she was meant to be. For many years, she had been living as a girl, though hidden in her panties was a six inch penis and a pair of testicles.

At first, I didn’t know how to react, until I came to the slow realization that I didn’t care. I loved her and the fact that she didn’t have a vagina did nothing to change that. In fact, as our love-making began, I discovered that a penis could actually be a lot more fun than I had ever imagined a vagina would be. I mean, with a vagina, you can lick it or you can put your penis into it. Her butt was a more than adequate substitute for that and, in addition, her penis could be licked, sucked, stroked, jerked, or put my own ass. Not to mention the fact that a penis gives you a little reward at the end. I mean, pussies are OK but it’s nice to have something solid and warm to hold in your hand. But I digress. If you want to read about our first night, check out “Rebecca’s Secret”.

Sadly, that perfect, transcendant summer had to come to an end. Rebecca had to go back to California for school while I remained relatively close to home - meaning, the other side of the country. We talked about our relationship for a long time and decided the best solution was to put it on hold while we were apart. We could date other people as long as we remained true to one another in our hearts. That was obvious, though. It didn’t really need to be said. I could never love anyone but her and I knew she felt the same way. So, after a night of sex that made our first time seem like a cuddling contest, we said goodbye.

When I got back to school, I had no interest in finding another girl. I was still too hung up on Rebecca. But, as the weeks went by, I began to think more seriously about finding someone. Rebecca didn’t want me to be alone all year and, to be perfectly honest, I didn’t want to be alone either. I began to date other girls, some only once or twice, some more seriously. No one really made me feel the way Rebecca did, though. There was no spark between us.

That wasn’t the only problem. I had come to discover that, once you go tranny, you never go back. The sex was decent, when I could get it, but it simply didn’t compare to the kind of experience I had with Rebecca. A pussy simply wasn’t enough anymore. I needed a girl with balls, if you know what I mean.

On Halloween night, I found the girl I was looking for, right under my nose.

Tina and me

On a whim, I decided to take a Creative Writing course during the Fall semester. I had enjoyed writing “Rebecca’s Secret” and I seemed to have some talent for the written word, plus I needed the English credit, so I figured it was a good idea. The course was actually fairly popular so I was lucky to get in. My first day of class, I walked into the door of a packed classroom and quickly scanned for the only free desk, which was in the back. I moved towards it and sat down. To my right was a goth-looking dude dressed in black.

To my left was a sinewey blonde girl wearing a long, flower-print skirt and a Rainbow Brite t-shirt that wasn’t faded enough to actually be from the 1980’s, but which I assumed was reprinted as retro fashion. She also wore open-toed sandals on her feet, a hemp necklace, and several hemp bracelets. She was your typical modern hippie, not the kind of person I had too much in common with, but she had an open, friendly face and luminous blue eyes.

“Hi,” I said, smiling to her.

“Hey,” she replied, blushing, and then turning away. She was shy, I guess.

“I’m Jordan,” I told her.

“I’m Tina.”

“Are you an English major?” I asked her.

“Yeah,” she said, “but this isn’t a required course.”

“I need the English credit,” I explained, “but I like to write short stories so I figured it was a good fit.”

“Cool,” she said, finally meeting my eyes.

Things went on like that between Tina and me over the next few weeks. Every day, I would walk into the classroom to find Tina already sitting at her usual desk. I would smile at her, she would smile back, and we would exchange idle pleasantries until the professor arrived. Sometimes we would talk after class while she waited for the bus, but not every time.

The process was beginning to frustrate me. I really liked her. Despite the fact that she was so shy, I was able to learn a few things about her. She was 18, a freshman, and she was from New Hampshire where she lived with her parents, two brothers, and one sister. She also also very bright, funny when she worked up the courage to make a joke, and an excellent writer. Her specialty was poetry. Her stuff was amazing, much better than mine. She hated to read in front of the class but, when she did, everyone was blown away. Especially me.

Meanwhile, my talent for writing short fiction was growing, and the professor was impressed. Tina always gave me positive feedback on my writing and encouraged me whenever she could. There wasn’t much positive feedback to give on my poetry, though. I stank. Tina, on the other hand, had the opposite problem. She was great with language and images, but had trouble with things like plot and characterization. On Friday, a week before Halloween, our professor assigned everyone in the class to bring one poem and one story to class the following Friday, then dismissed us.

“Hey Tina,” I said, catching up to her as she walked towards the bus.

“Hey,” she said. “What’s up?”

“I was thinking and I wanted to ask you something.”

“OK?”

“Do you want to come over to my place on Thursday and read each other’s stuff? I’ve been struggling with my poems and I was hoping maybe you could give me some pointers. I could try to give you some pointers too.”

“Uh, yeah, that sounds alright.”

“Awesome. We’ll work out the details later. I think that’s your bus coming.”

“Oh yeah. Umm, see ya.”

“Bye.”

The next Thursday, as we had planned, Tina came over at 7:00 PM with her new poem and her new story. My roommate was gone so we had the place to ourselves to read and talk about our work. It was an unseasonably warm night so Tina had showed up in a pair of cut-off jean shorts and a peach-colored tanktop which showed off her lithe body, pleasantly round butt, and c-cup breasts. I actually found it a little hard to concentrate since every time she leaned over, I got a nice view of her cleavage.

She read my poem and I read hers. Then she read my story and I read hers. The subject matter was shocking, but something I knew a lot about. It was about a girl whose dating a boy but feels unable to express her desire for him because she knows that they can’t have sex without her revealing her darkest secret - she’s a pre-op transsexual.

The gears in my mind started to turn and I began to look at Tina in a new way. Sure it was possible that the story was truly just a piece of fiction or perhaps even intended as symbolic metaphor. That’s probably what she expected me to think. But was it possible that her story was based on a true experience? Was it possible that Tina had her own secret as well? I looked at her closely. She had a feminine face and body, but she was tall for a girl, nearly six feet. Not only that, the way she wrote about the transsexual lifestyle was so accurate, even down to the subtleties of emotion, which I had picked up on from Rebecca.

I knew there was only one way to proceed. I would tell her the truth about myself and see if she responded in kind. I wasn’t ashamed of Rebecca, but it wasn’t something I wanted to broadcast to the world, either. Tina, however, I felt I could trust.

“This is a very realistic story,” I told her. “You really captured what it’s like to be a transsexual.”

“I did?” she asked hesistantly.

“Yeah,” I told her. “If I tell you a secret, will you keep it?”

“Of course.”

“You know my girlfriend Rebecca that I’ve mentioned to you a few times?”

“Yeah . . .”

“She’s a transsexual. She was born male but now lives as a woman.”

“Is she a post-op?”

“No. Pre-op. She’s still got all her parts.”

“Have you two . . . had sex?”

“Many times,” I said, grinning a little despite myself. “I didn’t know she was a transsexual when we started dating. She only told me later. I was a little weirded out at first, but it didn’t last long. The way I figured - just because she had been born a man didn’t mean she was any less of a woman now. At first, I thought the whole penis thing would be too much, but I actually liked . . . I’m probably getting too graphic.”

“That’s OK,” she said with a laugh. “Thank you for trusting me. I won’t tell anyone.”

“You know,” I said, “you can tell me anything you want too.”

Tina looked into my eyes and opened her mouth to speak. Then she closed it again. I felt something pass between us but it was gone in the blink of an eye. Tina looked at the clock on my desk and told me that it was time for her to go. She had an 8 AM class. I thanked her for coming over and for her help with my poem. I opened the door for her and, as she walked past me, I put my hand on her elbow. She turned to face me and I suddenly realized how class we were. Well, there was only one thing to do now. I leaned in and closed my eyes. Our lips brushed together softly, then parted.

“Goodnight,” I told her.

“Goodnight,” she said in a whisper, and then she was gone.

It will be continied…




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