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My First Experience With A Man

"My first experience with a man and he made me crossdress"

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Famous Story

It happen when I was 18 years old. I was working for a clothing company at the time and it was a slow Tuesday morning. As I was folding clothes, a tall (I’m 5’5 he was 6’2) light skinned black man approached me. He introduced himself as Sam. He looked like he was well into his forties but was really fit. He inquire about several clothing articles in our store and slowly the conversation became more about me. How old was I? Did I like working there. Innocent questions that raised no alarms in my head. 

He began flirting with me and getting close as he talked more about how he and a roommate of his just got a place down the street.  He asked if I had a lunch yet, which made me look at my watch to check the time. I told him my lunch wasn’t until another twenty minutes and he looked at me and asked to see my watch. He held my hand, and lifted my wrist and turned it back and forward. I noticed he pressed himself against my arm, and that’s  how I knew he had an insterest in me.

I had never been with a man before. I exclusively always went out with girls, but always was curious how it would be like to be with a guy. The flirting became more physical. As he laughed he would gently place his hands on me. This made me nervous but in a good way. Guys at the store would always hit on me, but I never wanted to get involved with anyone at work. But with him, I felt in my head that if I did pursue this, no one would know. 

I agreeed to meet him for lunch. We chatted. He explained what he worked in and how he was new to the area. He shifted the conversation and was very straight forward, “Have you ever been with a guy?” he asked. I got nervous and giggly like a girl. I’m sure I blushed but I was really turned on by the way he was talking and flirting. I told him I had never had an experience with a guy, but often fantasized about being with one. I explained that every so often, I would lay in bed, and finger myself imagining I was being penetrates by a friend. 

He looked at my while grabbing my hand and said to meet him after work. If I was insterest for me to come over and we could hang out. He promised it would just be us two and nothing would happen as it would just be a way for us to get together. I became really nervous. I didn’t know anything about this guy and ever been with one, and here it is an opportunity, but with a complete stranger. 

I accepted.

He smiled and told me to just relax. He was curious as to my waist size was and told me put no mind to it.

Later that afternoon, he texted me and told me he would wait outside the store for me. I met up with him and we walked back to his place. Once we arrived we walked down a white hallway to the living room. We sat on his couch and began making conversation. He put a movie on for background noise. He asked me if I was okay with taking ecstasy and I accept it. After taking the pill we chatted for about another twenty mins. 

Once the pill began to take effect, he began to rub my shoulders. He began to whisper in my ear to relax and after each whisper, his lips got closer to my neck until he eventually began kissing me and dragging his lips up and down my neck. He turned me around and said. Go to the restroom. There’s a surprise for you in there. You don’t have to accept it, but if you do come outside with it. 

I went to the restroom down the hall. I closed the door behind me and notice there was a box with a bow. A card it read “Freshen up and come enjoy yourself” I open the box and inside was a set of tigh high stockings, garter belt, a tight white  skirt and black long sleeve blouse and a black thong. My hands began to shake. I knew I wanted to experience being with a guy, but this was different. It gave me a rush. I felt really horny just thinking about wearing it. I showered. Cleaned my anal cavities. Shaved my thighs. And put on the gift.

I was amazed how good the lingerie looked on me. My bubble butt and wide hips gave out a real feminine look.

I put a towel around me to cover myself as I made my way out to living room. Once I got there, Sam was in his boxers looking at me. He smiled. Reached out his hand and said, “My god you look sexy, take that towel off” I took off towel slowly and turned around so my ass would be the first thing he saw. 

The ecstasy was rushing. My hands felt cold but warm at the same time. I slowly slid my hands up and down my body slowly moving it in a snake motion for him. He stood up and put his arms around me. I felt him. He moved his hands on my hips and said, “Your mine now.” He kissed my neck from behind. The background R&B music set the mood. I slowly griended my ass on him. He turned me around and we began making out. I lifted a leg put it around him and he held it in placed while grabbing and caressing my ass. He let go and got me behind me once again.

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He slowly pushed me towards the couch, and told me out my hands on the arm rest and stick my ass out a bit. He got in his knees. He started hissing the back of my legs while grabbing my ass with both hands. My skirt was in place, and I felt his tongue slowly making his way up my ass. He pushed the skirt out the way with his face and I felt his tongue in between by cheeks. He used his hands to spread my ass open and moved my thong to the side. He began eating me out slowly. His lips and tongue were in sync. It felt amazing.  Even if wasn’t on ecstasy, I’m sure it would be felt just as great, but the ecstasy enhanced it. He layed me on my back. Held my legs together in the air and licked my ass using the tip of his tongue to go inside me. He pressed his lips against  my hole and felt his tongue move around in circles. 

He turned me around and forced me on my knees. He took out his cock. It was thick and black. No less than 7 inches. I was beyond turned on. I stuck my tongue out and began licking his shaft. He mouth fucked me for 5 minutes. I’m sure I didn’t need do that great of a job, but I tried my best. 

He moved me to the couch. Put me on my knees lifted my skirt up and slid my thong off. He spanked me twice. I could hear him moaning. Still, he made sure I was okay with everything thus far. “Are you sure you want this?” he asked.

I told him, "Yes baby. Fuck me. Fuck me hard."

He got the lube. Covered my asshole with it and his dick. He teased me for several minutes. Rubbing the head around my ass and slapping me with it. Then, the pressure began. He slid inside me as he moaned. “You’re so tight!” He yelled and grabbed my ass. He slowly began going in and out and got faster and faster. 

It felt amazing. I always heard about it hurting. It didn’t with me. Sure there were moments were I felt pain. But this was good pain. I was in heaven. Suddenly, the front door down the hall opened. 

I panicked, but he held me in placed. “That’s my roommate, he’s okay don’t worry. I’ll tell him to go away if you want me to.” He proceeded to fuck me. I kept moaning even if tried hard not to. His roommate came in and saw us. 

“Oh wow. What do we have here? She’s sexy Sam.” He came around and high fived Sam and stood there looking at him fuck me.

Sam, while fucking me told him, “She’s yours after if you want her, isn’t that right baby?” I stood up and felt his cock sliding out. I was beyond horny. I put my arms around the new guy and asked him his name.

Eric he said, while putting his finger inside my ass. “Come see me after you’re done with him” 

Eric left to his room. Sam smiled and told me if this works out, this could be a regular thing. That I would belong to him and Eric and I would want for nothing. He pushed me on the couch and spread my legs. He put his dick inside me while holding my leg against his chest. He put one of his fingers in my mouth and I began to suck on it. He grabbed my other leg and pressed both of my legs against my chest. The angle his cock was going in and out felt amazing. He drilled me in that position. 

A scene from a porn I had watch came into my head. I push him off me and felt his cock slide out. I had Sam lay on the floor and I stood above him facing the opposite way. I squatted and grabbed his dick and guided it inside. I bounce on his cock putting as much inside of me as I could. His hands held my ass and spanked me and told me to keep riding it. 

I felt his hands lift me. He stood up and held me down with his hand on my shoulder. “Open your mouth,” he said. He began jacking off. I got underneath his shaft to lick his balls when suddenly - his cum splashed all around my face and dropped into my mouth. He shoved his cock and told me to suck on it and not take it out. His hands held my head in place. His cum dripping from the side of my face. He pushed off and slapped my face with his cock. “You’re amazing,” he said while caressing my face. “Go clean up and see Eric. He’ll be your second daddy. Treat him as good as you did me.” 

I got up and gave him a quick kiss. I went to the restroom and cleaned myself. I showered and put on my lingerie and outfit on. I felt fresh and ready for Eric. I was nervous but the ecstasy made me loose. I tip toed to eric’s room. The door was closed. I gently knocked. Waiting outside I adjusted the height of my skirt and made sure everything looked okay. Eric open the door, looked me up and down and smiled. “Come on baby... let’s have some fun.” The door closed behind me. 

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Written by Sexybottom4u
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