working my way up to a complete sissy tramp

The party.

I met Liam at a party. One of the guys I worked with invited me. He did warn me that there would be a few gay couples. That didn't bother me. I've been around gay people before. Turns out there were only gay couples at the party. And a few guys there by themselves, like me. I was a little uncomfortable at first. Liam sat right down and introduced himself. He was a little older and didn't seem gay at all. He made me feel better. I relaxed and we chatted.

"Your friend from work told me about you."

I wasn't sure what that meant. But he was nice. After a while, Liam admitted he was interested in 'pretty' guys like me.

Liam told me "I've been gay all my life, but only recently began to pursue meeting, and going out with other guys."

I didn't know I was pretty. He said I could be.

I've only had limited success with girls or guys. Now in my late 30's, I haven't had a real relationship. Or much of a sex life either. Liam wanted to show me his new car. It was parked next to the house. It was dark now and I could barely see walking out to the car. He said it was a BMW 5 series. Whatever that is. As soon as we were in, he leaned in and kissed me. I've never been kissed by a guy before. I let it happen. I'm not sure why. Surprise? Or, no surprise at all? When I didn't resist, he came back for more.

"This is nice. You are a very attractive young man. I liked you as soon as I saw you. Let me know if you want me to stop. Just tell me."

Back to some kissing. Before I knew it, his hand was in my pants. The kissing was nice. His hand felt good rubbing my crotch. Quickly my pants were unzipped. He was pulling and stroking my hard-on.  We sat there kissing until I came. I let out a girly squeal then made a gasping sound. I came in his hand and all over his new car's seat. He smiled, handed me a soft cloth, and told me it was okay.

"This was a nice way to break in my new car. Thank you for letting me do that. I hope I didn't embarrass you. We can go back to the party. Or... I just live a few miles from here." His car was already running.

I was looking down at my crotch, covered with the cloth. Then I looked back at him. I didn't say a word. I was still in shock. The car began to move. And that was it. Off to a stranger's house for a night of forbidden gay sex?

The house.

"We will take it slow", he assured me. "I've got a new bottle of Scotch I'd love for you to try."

I was on the couch waiting for my drink when he walked in completely naked, holding two glasses of whiskey. He was tall and was sporting a fully erect penis. His chest and pubic hair were thick and dark. I shyly took a glass, trying not to look right at his manly cock. He politely took my hand and pulled me to my feet. Down the hall, through the doorway, onto his bed. We sat there, sipping the Scotch while he was undressing me. He gently laid me on my back, rubbing and kissing me all over, This time he put his mouth on my dick and worked it until I was hard again. We were both breathing deeply. He moved his body around, taking my hand and wrapping my fingers around his cock.

"Just give it a good squeeze. Everything will be just fine after that."

I started stroking his cock. It was another first for me already! His hands were on my head and shoulder, guiding me down. A couple of inches of his cock were sticking above my hand. I wrapped my lips around it and sucked. I know what a guy wants. Right? He wanted me to give it a good suck. Didn't he? His hand was working my cock as well. This was great!

"It seems you want that. I'm glad. You seem to be a natural. I knew it when I met you. Don't stop until I tell you. Okay?"

I nodded as I continued to squeeze and suck his long, fat cock.

I didn't handle his wet, sticky load quite as smoothly. It was another mess. I choked. I was coughing and trying to breathe without swallowing any of it. I blurted out something like "Oh, what the fuck?" I was so embarrassed. But he had a bathroom towel right there for me. He did his best to calm me down.

"Take your time, baby. It's all okay. You were awesome. I'm so glad we explored this for you together. I've got so many more plans for you. I hope you enjoy being here with me."

Gee, he was being so nice! After I caught my breath and cleaned the cum off my face, I remember looking up at him and saying:

"I'm not sure why I'm telling you this. I should be going and never coming back. But I am enjoying being here. With you. What sort of other plans do you have for me?"

The girlfriend.

We showered together. He dropped to his knees and blew me in there. He soaped me up and began to shave me all over. I leaned back in a daze, relaxed from the sweet, satisfying blow job.

As we were drying off, I asked why he had shaved me.

"I want a girlfriend." He said. "We will get your hair styled tomorrow." 

A girlfriend? I remembered he told me I was pretty earlier. Am I going to be a girl now? I was still floating like I was in a dream. All of this was so new. But, I liked it. I was nervous as I realized I liked it a lot. So, I just went with it. He had been nice. Polite and respectful. And, do I have a boyfriend now? This is all very strange and confusing.

Back in the bedroom, I was given a lacey pink bra, matching panties, a tight girly teddy, and some other things to wear. I hesitated each time he handed me another girly item. I kept looking back at him, with a questioning look. Each time he simply gave me a little head nod, and a smile. Once I was dressed, I posed in front of the full-length bedroom mirror, looking myself over. He had brushed my wet hair straight back, giving me a clean, fresh look. He stood close, taking pictures of us with his phone. His hand was on my ass, giving my cheek a good firm squeeze.

"How fucking sexy I am." I thought.

The image I was seeing in the mirror wasn't me anymore. There was a tall female model in a pink one-piece corset-style teddy. The outfit fit me perfectly. It showed off the round of my ass. Under it was a tight lace padded bra with cute little shoulder straps. The bra and panties were barely showing. Just a slightly different shade of pink. My long slender legs were covered in soft, silky nylon stockings. They came almost all the way up to the teddy's bottom. There were no garters so the stocking he picked had tight elastic bands in the tops. Everything looked sexy and felt really nice against my warm, freshly shaved skin. My little cock and balls were locked in a pink plastic chastity cage. I've never seen one before. But I felt even sexier with it on. I liked it. I liked it a lot.

"Now that you're presentable as a girl you need to understand your place here. I'll satisfy your little dick from time to time, but we will keep it caged for most of the time. Our focus will be for you to suck me off as many times a day as I want. At least 3 times a day. But probably more like 4 or 5. Having a sweet little girlfriend like you around makes me really horny. What do you think? Can you live with that?"

His hand felt nice on my butt. I did like the taste of his cock" I'd slipped in and out of my mouth. But, what does he mean about me living with this? 

Before I could ask any questions, he put his hands on my shoulders and gently pushed me to my knees. I found myself looking up at him, shyly holding his cock. I suppose we both realized I was answering his question. I looked over at the mirror. Again I was amazed at what I saw. This pretty girl in sexy underwear sucking off her man. I fell into a daze. All I could think of was his cock. I squeezed it and popped the tip of it into my mouth. I felt myself giving in to some crazy, new obsession. I was sucking as if my life depended on it. I loved it! I couldn't wait for him to cum again! I wanted to taste his cum. I wanted to do a better job swallowing it. Every bit of it! I wanted to please him. I wanted to show him I could be a good girlfriend. What has he done to me? What have I done to myself?

Coming out.

The next day we went shopping. He didn't have anything I could wear out as his girlfriend, so I wore my boy clothes. The department store was bright and full of people. I was nervous and really embarrassed. But the lady clerk in the women's department didn't seem surprised when Geoff asked for some clothes for me. She quickly looked me over and went around the store pulling all sorts of things off hangers and shelves. Back in the changing room, I was surprised by how well everything fit. She had picked out a few knee-high skirts and a couple of tight, low-cut girl's blouses. There was a nice pink party dress and a dark grey women's suit, like a secretary or a librarian, would wear. Very classy! 

Geoff wanted to join me in the dressing room, but I wasn't ready for that. So I muddled through the unfamiliar clothes, trying on different combinations. 

Under the pile of clothes was an assortment of underwear. She had chosen some simple lace bras and panties. On the packages, the bras noted they were padded push-up styles. 38 B cups. I guess that's my size? The panties were all thong back. I wasn't sure about them pulling up my ass crack, but I tried them anyway. White, pink, red and black. I was really self-conscious that she had thought about what underwear I should be wearing. I didn't want to try any of them on. But I had to wear something other than my boxer shorts under the party dress, didn't I?

When I did come out, I was in the party dress. I wasn't sure it worked for me. Geoff stood up and stared. His mouth was open. I think he liked it. 

I went back in and then showed off the skirts and tops. He liked them all. When I thought I was done he had one more item for me to try on. It looked like a wedding dress. He said it was a bride's maid's dress. It was light pink with some ruffles and a split side open all the way up to my hips. I pulled on the white thigh-high lace top stockings and stepped out carefully for his approval. It fit me perfectly. It looked awesome with the padded bra filling out the sexy little breast area. The clerk had done a good job. But she must have moved on to some other customer or duty. 

Geoff pushed me back into the dressing room. His hands were all over me. He loved the feeling of the dress on me. When I tried to tell him to back off he kissed me. He held his mouth over mine, hushing me, as he felt me up, groping me everywhere. He pushed my hands into his crotch. Was I going to suck him off in here? What the fuck?

Geoff backed up against the door, holding it closed. I was pushed down to my new full-time position. He rubbed the dress, grabbing my tits under it as I pulled out his cock and went to work. Fortunately, he came really fast. I didn't like being exposed like this. But he didn't seem to give a fuck. As I swallowed, I gasped for air. He was moaning a lot. 

A knock on the door. "Is everything ok in there, boys?"

"Yep. We are on our way out right now."

I quickly dressed back in my regular clothes. But Geoff wasn't having it. When we came out I was in a short blue pleated schoolgirl skirt and tight tank top. I was barefoot but still wearing the thigh-high stockings. My hair was a mess. Yep, I looked like I'd just blown a guy in the dressing room. I was even more embarrassed when I noticed the lines and the color from my red padded bra showing from under my white tank top. We stacked up the remaining clothes, slowly made it through check out, and finally out to his car. 

We sat there for a moment. I was looking down at the floor with my hands pressed between my knees. I felt myself shaking and about to cry. He looked over at me, trying to comfort me. But he did a poor job.

'"That was really fun, wasn't it? You seemed to take it all in stride. I didn't think you'd actually let me dress you in all those clothes. But when you did, and you look so fucking pretty, I couldn't help myself. And, I might add, that was a GREAT blowjob!"

Wife.

He asked me to quit my job. Every day I wear one of the dozens of outfits he buys for me. I've learned to cook much better. I don't mind keeping the house clean and making dinner every night. But most of all, I dream of when I'll be sucking his big, beautiful cock again. 

Maybe he will come home for lunch like he did yesterday? Maybe he will bring his buddy Carl home for dinner again. Carl has a real nice cock too. Geoff tells me doing his friends is what a good wife does for her husband. I really can't argue. Because I don't know. 

But if these panties don't loosen up and stop squeezing my dick, and my panties don't stop pulling my butt cheeks apart, tickling my hole, I'm going to cum, right here in my apron!

Billy