A pure fantasy about a young man changing his life by becoming a woman.
I pulled up to the valet parking of the hotel. As I got out I saw the young attendant look down my dress and then look at my legs as I swung them out to stand up. I smiled to myself. I was really going to do this. I was going into the bar in this hotel and pick up a nice guy. If I liked him enough I was going to have sex with him as a woman. My new equipment was ready and I had to try it out.
I felt very sexy in my dress. My legs were tanned and toned so I wasn't wearing hose, just a small lacy thong. My new pussy was getting wet from the excitement. I had a new lacy push up bra and I loved the feeling of how much my boobs weighed as I walked into the lobby. They were heavy and this gold lame dress showed them off. I had my hair and makeup done at the salon and from the stares I was getting it was worth it.
I entered the bar. I had been here before. I had picked up a good looking guy and we had gone up to his room. He was pretty drunk and I let him fuck me in the ass. He thought it was my pussy and I didn't tell him any different. Now that I had gone through with the surgery I had a real pussy. The doctor had done a great job and I wasn't worried about it not working like a real one. I even had a cervix way up inside me. It would bleed every now and then but he said that this was normal.
I made my way to the bar and took a seat. I ordered a drink and looked around. Most of the men were stealing looks my way. I guess they were waiting to see if I was meeting someone. The women looked at me with some jealousy. I was obviously taking attention from them. As I looked around the bar I saw a man. Our eyes met and I saw his recognition. He smiled at me and I smiled back. It was the same guy I had been with before from here.
He slowly walked over to where I was seated. He took my hand and raised it to his lips and kissed it. He led me over to a table in the corner. As we sat there he laughed and said he thought he would never see me again. I had caused quite an impression on him and he said I had ruined him since no other woman could come close to me. I smiled at the compliment and we made small talk over drinks.
After awhile he got serious and said that he really had missed me. I was all he could think about at times and he had been back here over and over trying to find me. As he said this I was getting hot. I remembered his cock. It was large, maybe 9 inches, and very thick. The head on it was enormous. I wanted him badly but I was concerned it would fit in me. I had been able to get a pretty big dildo in me but it took some work and I think he was bigger.
He really was a very sweet guy and he was being sincere with me. He asked me if I ever thought about being with him again. I honestly answered yes, because I had. He wasn't drunk like the last time and I could tell he was nervous. I took his hand and squeezed it to give him some reassurance. He swallowed hard and asked me if I wanted to leave the bar and go up to his room to be alone. I looked down and smiled demurely and accepted his offer.
When we got in the elevator we were alone and he pulled me close and kissed me. It was very passionate and I could tell he was worked up some. As the doors opened we parted and I straightened my dress. There was an older couple standing there and it was obvious to them what we had been doing. Smiling we made our way down the hall to his room.
It was an executive suite and was very plush. He fixed us some drinks and we sat together on a couch. He complimented my dress and how sexy it was. I smiled and stood up. I asked him to help me with the zipper. I turned my back to him as he slowly unzipped me. I turned back around and let the dress fall to the floor. He looked he up and down and I saw a big bulge in his pants. Standing up he pulled me close and kissed me again. Reaching behind me he unclasped my bra. Gently he slid the straps off my shoulders and let my boobs free of their confinement. Dropping my bra he bent down cupping my breast and raising the nipple to his mouth. It felt so good I moaned out loud. After giving them both some good attention he released my big nipple and stood back to look at me. I turned and slowly walked to the bedroom wearing nothing but my thong and heels. His eyes were burning my ass as I swayed it back and forth.
I climbed up on the bed and used a long finger to beckon him to join me. He stood in front of the bed and got undressed. He had a trim body with some salt and pepper hair on his chest leading down to a narrow waist. His brief were the last to come off and there it was. His big cock was at attention. It was too heavy to stick straight up. I think I let out an audible gasp and I felt nervous fluttering in my lower stomach. Could I make this work? Would that fit in me?
He joined me on the bed and this time left the light on. He slowly pulled my panties down and off exposing my new intimate areas. I had worked out a lot and my thighs and belly were tight. My legs were spread a little and he looked me up and down, from my big heaving breasts to my trimmed and now open pussy. All he could say was beautiful.
He crawled up next to me and started kissing my body slowly working his way down. He paused at my breasts and squeezed and kneaded them as he sucked on my nipples. Moving down he gave my belly little soft kisses until he reached what he was really after. I was shaking some as I opened my legs to him and awaited his touch. He was the first man to explore me down there. I prayed it would past the test.
His kisses got closer and closer to my core. Finally he licked my wet folds and I moaned. He took his time and after pulling on my inner lips he flicked his tongue on my clit. It was like a lightening bolt. I think my hips came up off the bed. He got down to business and sucked my big clit into his mouth. I wonder what he would think if he knew that had once been the tip of my cock? It was very sensitive and I felt an orgasm building. He let go of it for only a moment to tell me how big my clit was and how much he loved it. I could only say don't stop. He had two fingers shoved way up inside me as he chewed on my clit. I wonder if he could feel my cervix? The dam broke and I shuddered and came. I flooded his face with my juice which he licked up greedily.
He gave my legs little kisses as I recovered. I pulled him back up to me to hug and thank him. I reached between us and found his throbbing member. He moaned as I stroked it. I worked my way down to it and could not get my hands all the way around it. I licked the huge head which was leaking. I opened my mouth wide and got the head and a few inches in. Somehow his cock seemed a lot bigger then I remembered. Maybe it was because he wasn't drunk this time. As I sucked on it I was getting my nerve up to try it. I decided now or never and I rolled on my back and told him I was ready for him.
As he climbed on top of me he asked me if I was using protection so I wouldn't get pregnant. I smiled at him and said there were no worries. Given the green light he guided his big head to my entrance. My pussy this time not my ass. There was plenty of natural lubrication between us. As he pressed forward my pussy lips split apart stretching to take him in. I asked him to go slow since he was so big. Guys love to hear this and he responded how he loved my tight pussy. I leaned my head back and gritted my teeth as he pushed some more. Slowly but as nature intended my pussy opened up more and his glans slipped in. Now that was done he let go of his cock and adjusted our hips for better alignment. Pushing forward with his hips more of his fat cock went up inside me. I couldn't believe it, I was able to take him. At least this far because the was a lot more cock left to go in. I was sweating and cooing to him urging him on. With little in and out motions he worked more and more in me. We were making wet sucking sounds as the lining of my pussy didn't want to let go as he pulled out before plunging back in.
I wrapped my legs around his butt and pushed him deeper. I had to have it all. He was picking up the pace as my cunt walls stretched to accommodate his cock. Finally after one strong thrust I felt his pubic bone against mine and I knew he was all the way in, I had done it. He knew it too and began giving me all he had. He was hitting bottom with each stroke smashing my cervix. It was like we were made for each other. My clit was so swollen it felt like it would burst. It was getting rubbed by the tight fit and pounded as he bottomed out.
I told him I was close and I wanted him to come with me. I felt his cock swell even larger and I knew he was ready. His butt muscled clenched and he shuddered as his cock went off inside me. I came hard as my pussy clamped down. I flooded him again as well as the sheets. His sperm was like hot lava and I knew I would always want more. He filled me to overflowing since there was not much room in my packed pussy. Finally slowing down it was like neither of us wanted it to end. Even as he started to withdraw his semi hard cock it was a tight fit and hesitated to come out of me. As it popped out I felt so empty.
I made my way to the bathroom to clean up some and he did the same. We climbed back into bed and held each other. He told me he had recently divorced his wife. They had been in a loveless marriage for years. His kid was in college now and he made the decision to find a new life. He said he knew that this might shock me but he wanted me in his life. He knew we had just met but he had to take the chance that I would be interested in him. I smiled at this handsome man and stroked his face. I said of course I am interested in him. He kissed me and held me close. I could tell he was getting ready for round 2 because of the large growth between us.
I rolled him over on his back and took the lead. Climbing on top of him with my back to his face I started to guide him into me. We had done it in this position before but this time it was my pussy. A pussy he now owned. I had to use my weight to help with his entry. As he eased inside me I slowly lowered myself down and down. He moaned as he watched his big cock disappear up inside my tight pussy. After a few strokes I had him all in. It was such a different feeling in this position. I was impaled on his large pole. I ground my clit on his balls. I could take some short strokes but it was hard. He grabbed my hips pulling me all the way down on his cock and rolled off the bed taking me with him, his cock still buried in me.
We stood near the bed and bending over I gave him full access to ram me from behind. And that is just what he did. This was animal sex. I was sweating from the pounding I was getting and he was sweating from the effort. His hips would bang against my ass making slapping sounds. We were both crying out and talking dirty. I wonder if we could be heard next door. He was lasting a long time and my legs were getting shaky. My pussy was on fire and was clamping on his cock with each stroke. He reached around and grabbed my breasts for leverage. As he kept plunging deep into me he started to pull on my big nipples. This sent me over the edge and I orgasmed. He came too flooding me with hot sperm. He had deposited another big load in me and I loved the feeling. Lucky I couldn't get pregnant because I had taken enough sperm tonight to get any genetic female knocked up.
We collapsed forward on the bed. He was careful not to crush me. His cock was still firmly planted in me. Finally after a few minutes he stood up and withdrew from me. We took a shower together climbed in bed and fell asleep. In the morning we made sweet gentle love before we both had to go. I was a little embarrassed to leave in the same dress I arrived last night in. There was no doubt to anyone what I had been doing. We exchanged numbers and he said there was no way he was not going to have me in his life now that he had found me. Could I love this man? I think I could.
We saw each other again over the next few months. He made plans to move to my city. I think I was falling for him. Luckily the spotting and occasional bleeding had stopped. I was glad for this but lately I wasn't feeling well especially in the mornings. I had made an appointment to go see that female ob/gyn friend of mine to see if everything was still as it should be.
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<a href="https://www.lushstories.com/stories/trans/crossroads-ch5.aspx">Crossroads Ch.5</a>