Homeless man invited to a friend's house for a shower. He is given the chance to to cross dress. He finds that he was meant to be a woman. This is pure fantasy but I wished it would have happened to me.
My story begins a few years back on a hot August morning. I was homeless at the time and struggling to get by today. I was standing on a corner trying to panhandle some money however I wasn't having much luck. I was just about to leave when Carol showed up. I love it when she comes by. We would chat for a while and then she would give me some money or take me to lunch. It was lunch. To my surprise, we were going to her place to eat. She was going to make a special lunch. While she was cooking, I could take a shower. I really needed one bad. On the way over to her place, I wondered why she was doing this.
When we arrive at Carol's place, she showed me to the bathroom. I quickly undressed and jumped into the shower. Before long, there was a knock on the door and she entered. Carol left a razor and a towel. On the way out, she grabbed my clothes.
“These things are filthy. I am going to clean them” said Carol.
“I don't have a change of clothes. I'm not comfortable wearing just a towel.”
“I will find clothes that will fit you. I should have a pair of pants your size.”
After I climb out of the shower, I notice a a pile of clothes and pink razor. The shaving cream had flowery smell to it but that didn't bother me. I kind of like the way it smelled. After I shaved, I went into the bedroom. I unfolded the clothes and found a short skirt and a low cut blouse that would have shown cleavage. I wasn't sure about putting them on but I didn't like the idea of running around in just a towel. So I put them on. The clothes seem to fit me except for the blouse. It was loose on me but then again, I didn't have any tits to fill it out.
I walked to the living room. She sitting on the sofa waiting for me. I sat down in a chair across from her. She was sorry that she could not a pair a pants that would fit me. Then I noticed her staring at me and smiling. I realized that I was exposing myself. I am not used to sitting lady like.
“You wouldn't happen to have a pair of panties that would fit me?”
“Let's go see what I have in your size.” I followed Carol into the bedroom and she went to drawer. “Here's a pretty pair and a lacy bra to go with it. Now hurry up and change.”
I unbuttoned my blouse and hoped she got the the hint to leave. However she just stood there waiting for me to finish. I quickly pulled up the panties under my skirt. When I put the bra on, Carol stood behind me and fastened the hooks.
Carol said “We have one thing to do.” She took my and led me to her dressing table.
On the table was a vast assortment of makeup. Carol began working on me. She hummed a tune with a big smile on her face. I sat there as Carol worked and began to wonder why she doing this to me. In the past there were times I wished I was a women. But I pushed it out of my mind. Now those feelings were returning. Was I meant to be a women? Before I knew it, Carol was done. I looked in the mirror and saw the face of a women. I wasn't the most beautiful women but I looked good.
“Carol, why did you go to all trouble to make me into a woman.”
Carol said “I could tell from our conversations that I seemed more feminine than masculine. I decided to give you the opportunity to explore my feminine side. To further help you, I invited a friend Tom over for lunch. You might like him. It will give you a good opportunity to practice being a woman. I told him all about you and he really wants to meet you.”
Carol left me and I sat there gazing at the mirror. I couldn't believe what was seeing. I was looking at my chest and wondering what it would be like to fill out those cups. I traced my fingers over the lace and stopped at my nipples. I ran my fingers around them They started to get erect. I had to stop because I was becoming excited. I quickly finished dressing and left the room.
While Carol was in the finishing lunch there was a knock on the the door. I answer it. There in the door was a handsome man. I invited him in and we went to sofa and sat down. He introduced himself as Tom and I as Allison. We talked about all sorts of things and found we had a lot in common. We were having a good time when Carol brought in lunch. After we finishing our meal, all of us sat in the living room talking. Carol rose and said “We were out of wine and I need to go to store to buy more.
After she left,Tom came over to couch and sat next to me. I felt a little uncomfortable but at the same time a little curious. Was this part of Carols plan to complete me becoming a woman. Then he placed his hand on my leg. I turned to look at him. Without any warning Tom gave me a long and tender kiss. He leaned back and gazed into my eyes. Tom asked “Did it bother you when I kissed you?”
“No not at all. I have never kissed a man. In the past, I would never have considered kissing a man, but I like the idea. Especially since it was you.”
Tom reached over and put his arm around me. He pulled in close and gave me passionate kiss. Those old feelings of wanting to be a woman came flooding back to me. Tom slid his hand under my skirt. Something in me awoke and I started to swell. He could tell I was excited. I took the hint and slid my hand down his pants. The more we stroked each other, the more we wanted wanted each other. I couldn't wait any more. I took my hand out of his pants and started to undo them. Tom stopped me and stood. He took my hand and led me to Carol's spare bedroom.
We stood in the room and Tom began to slowly undress me. First, he undid my blouse and slipped it off. Next, he pulled down my skirt and I stepped out of it. I stood there in my bra and panties with my erection poking out of my panties. Tom reached down and stroked my member once. He pulled down my panties down to release my swollen cock. When he took of my bra, we faced each other and kissed. I reached around him and squeezed his checks. I desired to pull him close to me because I really wanted to make him cum.
I sat Tom down on the edge of the bed and then I pulled his shirt over his head. I stopped for a moment. I reached down and ran my fingers through his chest hairs. I pinched his erect nipples. I quickly got on my knees and removed his shoes and socks. I reached up and undid Tom's pants. I slid his pants while keeping my eye on his crouch. I couldn't wait to see what was attached to large head sticking out of his shorts. I pulled down his shorts to reveal his thick and veined cock.
I was so excited that I couldn't wait to please him. We kissed and this time our tongues danced together in a pulse of what was to come. When we broke the kiss, I slowly slid my tongue down his chest. I paused briefly and licked each nipple. I continued on down his chest and down his shaft and stopped when I reached his balls. I took each one and gave them gentile little suck. I moved back to the head. I put my lips around it. As I swirled my tongue around the head. I could taste the precum. I began to move my mouth down his cock. I didn't think I could swallow the whole thing but I did. I moved back to the head of his cock and Tom gave out a moan of pleasure. Again I went down his shaft and felt the veins on my tongue. I did this a few more times and then I stopped. I looked up at his faced and gave a big grin. Then I went back to sucking his cock. I loved the feeling of him sliding in and out of my mouth. After several minutes of enjoying taking him in my mouth, Tom stopped me. I thought was I doing it wrong but then I found out why we stopped. He told me to get on my hands and knees.
Tom got up and went to the night stand drawer. Tom got a tube of lube and put on some lube. He then came back to bed and put a big blob on my asshole. He used his finger to push it in. Tom gently pushed his finger in and out. Now, I was ready for him to enter me.
The sensation of him sliding his shaft into me was quite pleasurable. At first he pumped slowly, he gradually went faster. I was getting really excite. I could feel his balls slapping against my body. I felt that this must be like it is give yourself to a man. I loved the idea of having a man inside of me. I wished I had a clit so I could orgasm. Instead I played with my member. With every forward and backward thrust, I would rub the head of my cock. Tom stopped again.
This time he had me lay on my back. He got between my legs and pulled my legs onto his legs. Now, I know what it is like for a woman to spread her legs for man. Again he entered me. I loved seeing his shaft and bushy pubs moving toward me. I watched them move back and forth. I could see the excitement and pleasure in his eyes. I couldn't help it, I started to stroke my shaft. I realized now that I meant to be a woman and some day, I would have to get the surgery to become a woman.
Tom stopped to put some lube on me. As he pumped me, he began to stroke me. As his cock went in, he would slid his hand down my shaft. When he pulled out, he would slid up my cock. I couldn't help myself. I started breathe heavy. I began to move with him. When he pushed in and I move toward him. When he pilled out I moved away. When I got the movement down, Tom stopped and concentrated on pleasing me. Our strokes were in perfect harmony.
After several minutes of our sexual dance, Tom and I were breathing hard. I knew he was close to coming. I felt like I was going to explode and explode I did. I shot cum onto my chest. And then Tom let out a huge moan and shot his load of hot cum into me. Tom was truly satisfied and so was I. I felt like the woman that was inside me wanting to get out.
We lay on the bed. He rolled onto his side and we began to kiss again. I wished we lay here forever. Finally we got up and went to the bathroom. Tom washed my chest, cock and back side. I gently stroked his cock with water to remove the lube. I really wanted go back to the bedroom and do it again. Instead we got dressed. I watched him pull up his shorts. I wanted to see his member one last time. Before we walked into the living room, Tom and I embraced. After a long kiss, we left the room.
There sitting on the couch was Carol with a big smile on her face. I blushed and sat down. Carol asked how was it? I said that I loved it and have never experienced any thing like it. After all these years I have never had great sex like this. Tom agree with me. Tom said it was great and would like to meet with me again.
We talked together for awhile and made plans for this coming weekend. This time I was going to spend the night. This time Carol was going to teach me how to put on makeup. She promised get me clothes of my own and a pair of shoes. Carol had the perfect nightgown for me to wear. It was getting late and I had to leave. Tom got up to leave. Before he left, Tom gave me a kiss and that he said would see me on Friday. I went into Carol's bedroom. Carol called out and said to keep the bra and panties because they were mine to keep. I got dressed in my regular clothes except I wore my two gifts. After I washed my face, I was ready to go. I hated to leave but at least I have next weekend. She drove me back to corner and we said our goodbyes. She said she would meet me here next Friday at 2:00. I went home content that I get to dress and be a woman again. I wondered what Friday will bring.