This is a continuation of the first part of the story:
After our first date with Jim I felt kind of frightened with this whole thing tormented with questions like "Am I gay now?" or "What if someone finds it out?". I was confused, scared and ashamed. I liked it so much that I was sure I would never do it again. I had the same feeling after some of my previous encounters, but this one was just brighter and bigger.
At 11am next morning I sent a message to Jim saying I want to see him again, and Jim agreed. One of the things we talked about the previous night was my experimentation with cross-dressing and all those fantasies when I was picturing myself to be a girl. I asked Jim if he would mind if I came in women’s dress and he actually did not.
On my way to Jim I went to a store and bought everything I needed:
- Short and sexy black dress
- Wide black belt with big round buckle
- Beautiful lace black bras with push-up pads
- Black lace thongs that matched the bras
- Sexy black stockings
- Elegant high-heels with leather lacing wrapping up ankles almost up to the knees
- Black collar necklace and matching bracelet
- Brown glossy lipstick and little make-up kit
The buying process was a bit uncomfortable especially when I got to the register. It all looked like an all-in-one cross-dressing kit, which exactly what it was.
It also cost a bit more than I initially expected, but other than getting through the register I enjoyed the processes having hard-on through the most of it.
Once Jim let me in, I passionately kissed him on the lips and went to the bathroom to clean up and change. I took a shower, purged my ass with an enema, and shaved my face once again for better smoothness. Then I put on my stockings and shoes, put on my bras, put on my thongs squeezing my dick towards my ass to look more like a girl on the front, and finally put on my dress and jewelry. I spent two hours in that store for a reason - everything fitted me perfectly. I put on my make-up and finally look into the mirror. I saw a slender beautiful girl there, with big breasts, narrow waist and long legs.
The face looked girly too. I did not have a hair cut for a while and my hair looked like girly boy-cut style. Add juicy wide lips, long eyelashes and colored eyelids. Thanks to tonal cream there were no signs of any facial hair on my cheeks or upper lip either.
Finally I got out and came over to Jim. His eye got wider in amazement when he saw my transformation. I asked him to dim the lights in the room to find some slow music to dance. He uncorked a bottle of champagne and poured it into elegant champagne flutes.
We started dancing. I out my head on Jim's shoulder and started to kiss me in my neck and bare shoulders. Jim hand slipped down from my waist to my ass. He teased it for some time and then put it under my short dress and thongs. He got his hand back and put his two fingers against my mouth. I sucked them to moisture them a little bit. Then he got back under my thong and started massaging my ass crack and asshole. Pretty soon both of his fingers slipped inside. What a pleasure it was dancing with my man, while French-kissing him and having his fingers massaging my rear pussy!
We drank some more champagne followed by another long kiss. I could not wait anymore and got down and unzipped Jim's pants. I got his dick out and started to kiss and lick it like crazy. My mouth was full of saliva. I lowered my head and his dick easily slipped into my throat. It felt tight but much better than the previous day. I almost did not gag at all. Jim started to moan, fucking me into my throat faster and deeper.
Then Jim led me to his kitchen and bent me over the table. He raised my dress exposing my round ass, and took off my thongs. He started to brush his big now fully-erect dick across my ass. In a couple of moments his dickhead slid inside my ass. I asked him not to do it and put on a condom, but he told me he was not going too deep and this was perfectly safe. He also told me he did his STD exam just the previous weeks and the results papers were still on his desk in the living room. I did not know whether to believe him or not.
My protests were too weak anyways. I wanted him to fuck me so so badly! I wanted him to fuck me without a condom and cum inside my ass. I wanted to feel his cum pour out of my gapped ass and flow down along my inner thighs, when he gets his dick out. I wanted it to be like in those porn image galleries and movies, when the asshole is wide-open and white sticky cum is dripping down from it.
Jim did not fully proceed with bareback fucking respecting my feelings. He just put me down on the floor, got my legs up, put on a condom, and shove his entire dick into my asshole with a single swing of his hips. Then he got his dick out and inserted it into me again. He did it several more times. I was enjoying the feeling of it immensely. The Jim started to move inside of me, pumping his dick in my ass faster and harder. He was fucking me and kissing me on the lips like that for quite a while.
Then he got his dick out and told me to get on my knees. I did so, and he immediately squeezed his big dick into my ass and started to fuck me doggy-style. I was still wearing my dress and everything and it made me feel very hot.
Jim took me to the bedroom. I was on my back again, legs up on Jim's shoulders. Jim kept fucking my butt and I kept moaning and pleading him to fuck me more, to fuck me harder, to fuck me deeper.
Jim asked me who owns my ass now, whom it belong to. Sure enough I answered it belong to him and moaned again, squeezing his big upper body with my arms and French-kissing.