Liz and I going out for coffee became a regular event. We usually went to the same coffee shop and spent hours talking about things feminine. Liz worked hard to make my female side come out.

Usually, people left us alone in the back of the shop to talk. Every now and then a man or men would try to strike up a conversation. Liz would politely get them to leave us alone. I didn’t trust my voice and never said a word.

That all changed on one of our excursions. I was wearing a denim skirt and a white top and was really feeling my feminine side. Liz was talking to me about men and their needs. My feminine side was really kicking in and I was enjoying the conversation. This was the point where my life took another turn.

A man stopped at the table and started talking to Liz. He was attractive and had a wonderful presence. I felt drawn to him. Liz introduced him as Dan. He was about six feet tall, blond, and well-proportioned. He was friendly and exhibited all the things that Liz had taught the feminine me to look for in a man. I found myself drawn to him and Liz encouraged him to stay with us.

I didn’t say much during the conversation. I did notice Dan looking over and looking at my legs a lot. I asked him if he liked my legs or if he was just trying to figure out how to get between them. With no shame, he said, “Both!” I was flustered at this point but was really getting to like him.

We were at the coffee shop longer than usual. Suddenly, Liz looked at her watch and announced she had to be somewhere else. She asked Dan to take care of me and bolted out the door.

We were left alone. Dan asked if he should walk me home or if I would like to go to his place for a glass of wine. I accepted and felt a thrill as I tucked my hand under his elbow to leave the shop.

Dan lived close by in a two-story townhouse. We went into the living room, and I sat in the corner of a lovely L-shaped sofa. I kicked my shoes off and tucked my legs up on the couch as he brought two glasses of wine. Our conversation bounced around and he did his best to keep me comfortable.

After a while, I felt flushed, and it seemed like the distance between us on the couch was getting closer. I was really getting excited at being so close to him and was wondering what would happen next. Liz had never coached me past this point. Maybe it was the wine, but I made a decision that I have never regretted since.

I leaned over and straddled his lap. I threw my arms around his neck and shoved my tongue in his mouth. He responded eagerly, and we made out for a while. Suddenly, I realized that his hands were no longer around my waist. He had moved lower and was sliding them up and down my thighs. He was completely under my skirt as he ran his hands around. I was really hot.

At this point, I decided two could play. I unbuttoned his shirt all the way to the waist and began playing with his chest. I was really getting into it.

At that point, I made a decision. I slid down onto my knees and began unbuckling his belt. He lifted slightly and I pulled his pants and underwear down to his ankles with one pull. His manhood was there in front of me. I had never done this before but knew what I liked a woman to do.

I slowly started licking his shaft from bottom to top, eventually taking the shaft into my mouth. As I went up and down on the shaft, he began moaning. I did my best. I felt a twitch and suddenly he exploded in my mouth. I swallowed what seemed to be a never-ending stream of semen. When he was done. I licked up everything and then jammed my tongue into his mouth again in a really passionate kiss.

I didn’t know where to go from there. I was still horny and really wanted to be fucked. I stood up and wiggled out of my skirt. I asked him which way the bedroom was and told him that he needed to fuck me silly.

Dan led me to the bedroom playing with my ass the whole way. I crawled onto the bed, dropped my panties, and got on my hands and knees. I told him that I expected to finish with my legs around his neck. He just smiled. He quickly grabbed some lube and began massaging my hole. He popped two fingers in, and I moaned, anticipating what was coming next. He removed his fingers and got behind me. I felt a little pressure and he popped his dick into my ass. It felt different than the dildos that I was used to. It felt better, a lot better.

Dan quickly established a pace and I pushed back in time with him. It burned but felt great. After a bit, he pulled out and asked me to get on my back. I obliged and he pulled my legs up around his neck and re-entered my ass.

I guess it was the excitement and the rubbing on my cock. I felt great! Suddenly, He exploded in my ass, and I came at the same time. I blacked out.

I came to in an unfamiliar place and position. My head was on Dan’s chest and my arm across him. I could feel the dried cum cracking on my belly and my hip was in a wet puddle on the bed. I remembered what happened. I felt great, just a little sore from the fucking that I had taken.

I looked down and saw the tool that had given me the thrill of a lifetime. I slowly slid down and took the object of my desire into my mouth. Dan woke and said that it would be a while before he was ready again. He pulled me up and kissed me.

I eventually got up and cleaned myself in the bathroom while redoing my make-up. Dan had brought all my things to the bedroom. I realized what time it was and told him that I needed to go home.

He offered to walk me, but I declined as it was already morning. He let me out the door and I began walking home. My mind was racing. I had a ton of thoughts:

How and when should I contact Dan again?

What should I do next? I really needed to talk to Joan and tell her what happened as well as confess about Ellen.

Why did I fall so hard for him? Was I actually learning my female role?

With my mind racing, I walked past a construction crew and wondered what it would be like to have all of them at once. The comments they made as I walked by told me that they would do it.

As I neared the house, my phone rang. It was Liz asking how things went. I told her the story and hung up as I walked into the house. Ellen was there and asked me why I had a “just been fucked” look with a smile on her face. It was like she already knew.

More to follow, I promise.