A Fresh Start

2005 24-25 yrs. Old

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 three 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 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 convinced Walt to brutally fuck me. She hoped 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. I was more upset with him not calling!

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 in love with a transsexual woman. Oh….I was a lot of fun…..and great in bed. Even interesting! But a life partner?

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. Mostly, he’d drop me back at my 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.

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 an 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!

I’d gone out with Fred 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 of 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. Most of the men I fucked preferred doggy style, or me face down flat on the bed. (I actually preferred it face down. The sensations of a cock against my ass walls feels different.)

Since this was still early in our relationship, he still hurt a lot entering me. Walt watched for the signs of distress and slowed his thrusts, even stopping, so I could adjust to the pain. I wrapped my legs around his waist and pulled myself further onto his cock. As I relaxed, Walt slowly picked up the pace until he found his rhythm. He can fuck me thoroughly at this pace, and fuck for a long time. I pulled his face to mine and ran my tongue into his mouth. He kissed and nibbled my neck. (I have a persistent hickey on my neck, and am proud of it!)

I felt my cock stiffen between us. It rubbed against his stomach as he thrust into me. When I came, it startled him, but he soon resumed his pace. About five minutes later, he groaned as her thrust one last time and filled my ass.

He wanted to roll off, but I held him close. I clenched my ass and writhed beneath him. I felt him stiffening inside me. (Walt is amazed at how often I can coax his cock back to life!) We lay on our sides, my back to him as he fucked me again. He reached around me and played with my cock as he thrust into me. With my legs together, he can’t go as deep, but my channel fells tighter. He soon came again.

He held me a few minutes, then I cleaned up and fixed breakfast. Our eyes never left each other’s over the meal. My foot caressed his leg under the table. I could tell he was uncomfortable, but I enjoyed teasing him. My eyes told him I wasn’t teasing, but was ready again.

“Aren’t you tired??” he asked incredulously.

“Nope!” I replied. “You did all the work!”

Then I grinned wickedly. “I’ll do all the work this time!”

As he lay back on the bed, I worked at taking as much of his cock into my mouth as possible. When he was hard, I used both hands to lube and play with his cock. I made all the suitable noises showing how awed I was with his size. I straddled him and guided his cock into my asshole. Since he’d already fucked me several times last night, and again this morning, entry wasn’t nearly as painful, although my ass walls were a little sore.

I rode him like a rocking horse, just shallow movements in my ass. I’d raise myself then slam myself back down on him. I had him grab my waist and help lift and pull me back. I leaned back and stroked my cock. I waited for him to come before I creamed into my hand. I licked it all up.

“Why do you do that?” he asked.

“Because I like the taste,” I replied with a smile. “And I like the taste of yours. And…..as long as you’ll have me……as long as you want me…..I will do my best to learn to take more of you into my mouth. To suck you so I can get more of your delicious cum!”

Then, more quietly, and a little fearfully, “I’m yours. As long as you want me…….Hopefully for a long, long time.”

We ended up making out much of the day. That night, when he thought I was sleeping, he told me he loved me.

I loved him, too, but it would be many weeks before I had the courage to tell him. 

------ To be continued ------