2005 24-25 yrs. Old
Ch. 1 - The first Date
I enjoyed being fucked hard, and occasionally, roughly. I even enjoyed mild 'discipline'. I could handle someone using a riding crop or belt on my ass for short periods. I was pretty freewheeling when it came to sex. I wanted it frequently. I experimented my new found gender freedom with as varied a group of sex partners as possible. I fell in love often. At least I thought it was love. But what I really wanted acceptance.
By the time my relationship with Silve and Miguel neared its end, I was looking for more. I just didn't know what!
Enter Walt.
I wanted Walt the first time I saw him. He was tall, rugged, and very good looking. And totally uninterested in me! He saw me as a spoiled teenager. He also knew I was Miguel's mistress. Miguel and Silve were secretly amused at my attempts to seduce Walt. Both were hoping I'd be suitably humbled, and more submissive, with his rejection. What neither expected was that I might succeed. Or that he would fall in love with me. With ME...of all people. Or that I would fall in love with him.
When Walt finally took me, it was rough! He had the biggest cock I'd ever taken: over eleven inches long, and over two inches thick, with a bulbous, baseball like head. He hadn't been with anyone since his wife left him several years earlier. I'd come onto him so hard, he couldn't help but take me. And take me he did. Hard. Very Hard. He was unleashing several years of pent up sexual frustration. At this point he didn't care that he was fucking a transsexual. He used me several times that first night.
He moved in with me while he was doing the work in Miguel's apartment. Once he grew comfortable with the idea I was just a different type of woman, he opened up to me. Our frantic sex became gentle lovemaking, with him considerate of my desires and feelings. He was interested in me as a person. He listened to me, laughed with me instead of at me. He was disappointed when our time together ended. And so was I.
Silve was no fool. She saw the burgeoning romance and did what she could to quash it. She and Miguel had other plans for me. Dark plans. She convinced Walt to brutally fuck me, hoping I would think he was just like all the others; using me, then discarding me.
I actually enjoyed him taking me that hard, but hated being left tied when he went away. I was more upset with him not calling!
I later found out he felt he had brutally raped me. He'd unleashed a side of him he never knew existed: a side he didn't like. He was afraid for me. He didn't understand the games I played with Silve. I had a hard time convincing him he hadn't hurt me: but he wasn't sure he wanted to be involved with me if that was how I wanted to play!
Neither of us were really sure we wanted to pick up where we left off. I was angry with both of us. He was ashamed of himself. I believed he was bothered at being attracted to a transsexual woman. Oh...I was a lot of fun...and great in bed. Even interesting! But someone who can share your life?? And being as immature as I was, I wouldn't see I was just as much a part of the problem.
But, sometimes, absence does make the heart grow fonder. And we were fond of each other. So much so, that we decided to pick up the pieces and start over. We started out like other couples, getting to know one another.
Walt took me to dinner a few times. Afterwards, he'd drop me back at my old apartment. A few times I stayed at his, though we weren't back sleeping together. We danced around the issue of my gender a little. He came to terms with it long before I really did. I was still having trouble accepting people could like me as I was!
Walt's opinion? I was his girlfriend. End of statement!!
Our first real date was burgers and a movie. He let me choose the movie. I remember it quite well: we went to a film festival and saw Forbidden Planet, an old Sci-Fi adventure. He did all the right things: popcorn, a soda, letting me pick our seats.
Part of the way into the movie, he put his arm around my shoulders. I smiled inwardly at what I thought was a clumsy attempt to cop a feel of my small breast. I guided his hand to it, but he quickly pulled away! I guided it again, and again he pulled away. I tried a third time and he pulled his arm off my shoulder.
What gives??? I thought guys copping a feel at a movie was normal. I decided to snuggle against him. Not long after that, he placed his arm on my shoulders. I gave him a few minutes, then pulled it between my breasts and held onto it. This time, he left it. I felt content.
Back at his place I kissed him and thanked him for the wonderful evening. I started to undress, but he stopped me. Now, I was really confused. He'd wined and dined me, so to speak, now it was time to spread my legs.
He sat on the sofa and I sat next to him. He was holding me as I reclined facing him.
"I can't remember the last time I saw the whole movie!" I said. "That was nice! Thank you!"
When he looked at me strangely, I explained, "I was usually giving head partway through the movie. That's what my dates seemed to expect!"
"Haven't you ever gone on a date, and just have fun? No strings attached?"
"But sex is fun!" I retorted. But I knew what he meant.
He was surprised I'd never gone out on just a date. Never had a great time with the girl or, later, boy. He was flabbergasted I'd never just spent an evening making out. Or just going for a walk! Or holding hands!
I'd gone out with Fred, my first boyfriend's roommate, a few times, but they weren't real dates. We were friends keeping in touch, occasionally having sex. My other so-called dates were just me turning tricks. Walt took me on my first real date! (And many, many more!) I was 25.
It was nice feeling like I didn't owe anyone sexual favors in return for a nice time out.
We made out on the couch for a couple of hours then went to our rooms. (We'd already started having sex again, but we didn't always sleep together.)
Sometime early the next morning, I found Walt drinking coffee on his sofa. I pulled off my sleep tee and crawled onto his lap. I took his face in my hands, kissing him and smiling.
"Walt, thank you for last night. It was nice not feeling I had to provide sex in return. But, when I do have a good time, I want to be fucked. It feels right to me."
I took his coffee and pulled him up.
"Take me to bed, please?" I asked.
He took me literally. He picked me up and carried me to the bedroom. I didn't recognize the symbolism in his act at the time, but I later came to understand this was one of the subtle ways he told me he loved me, and would always take care of me.
Walt was still dressed. I knelt before him and freed his cock from his pants. I have a small mouth and struggled taking his cock into it. But I tried, anyway. At first, I could barely take more than the head and maybe another inch into my mouth. Most the time, I held my lips snugly against skin and licked the head. I bobbed a few times then licked and kissed his shaft. When he came, my lips encircled his slit and I accepted his load into my mouth and swallowed it all.
I lay back on the bed as he finished undressing. I watched in anticipation as he lubed his cock. His cock looks large even in his big hands. I pulled my legs back to allow him greater ease in entering me. Walt prefers fucking me face to face. Another expression of his love and respect for me. Most of the men I fucked preferred doggy style, or taking me face down flat on the bed. (I actually preferred it face down. The sensations of a cock against my ass walls feels different.)