Where it happened: motel
Langauge: English
Sex: Male
Rating: 2
Category: Straight
Well at 49 and recently divorced after many years I started having these weird feelings. One night when I was having sex my girlfriend was on top and riding me and playing with my nipples. That’s when it happened. I found myself wondering what it would be like to be the one being made love to. To know how she feels sucking a cock and having it inside her. These thoughts and desires kept growing and I found myself fantasing what it would be like to be a woman. I started wearing panties instead of mens briefs. They felt so good. Next I started tucking my dick in my crotch so my tummy would be flat. I learned to walk and sit down in a femine manner. I’ve never crossed dressed. Not yet anyway. But I started wearing tight pants and tight pullover shirts in public. I really started feeling like a woman or so I thought. One evening on the internet I was going through some of those personal ads. There was a photo of a really nice looking man who had recently divorced and was looking for a friend and companion. I wrote to him and I guess at first he thought I was a woman. After a few emails back and forth he told me that he wanted to meet with me.He was coming to a city close to where I lived. He would be there for a few days on business and it would be a great time to meet he said. We agreed to meet at a restaurant in a town close to where I lived. He still didn’t know I was a man. We had talked about having sex and how I wanted to suck on him and such. I started to worry as the day approached and was going to back out but my desires won out.
He was shocked at first. But we shook hands and sat down and started talking and he started laughing at how this all was going. Golly he was gorgeous. He said he was straight and never had a m/m affair and wasn’t sure if he could have one or not. I told him that I’d never done this before either but I didn’t understand why I feel so giddy and feminine. Well the conversation and dinner went off ok. He paid for the meal and I figured that was it, all over and still not satisified sexually.
He opened the door as we left and asked if I would like to talk some more, it would be a long lonesome evening and what the heck we could still be friends. I agreed as he walked me to his car, he even opened the door for me as I got in. We drove around for a while making small talk. He saw an x rated movie theater and asked if I wanted to go. Of course I said yes. While watching the fuck flick I noticed his bulge. I wispered to him that I wished I was the one up there sucking on that huge dick. He didn’t say anything back. I felt kind of dissapointed. I started rubbing my flat tummy and circling my fingers in and out of my crotch. He didn’t seem interested in me at all. After the movie we stopped at a pub and he bought us a few drinks. It was getting late and I told him I should be getting back home. It would be almost a 2 hour drive for me. As we were driving back to the restaurant he said that I shouldn’t be driving that far after drinking and such. He said his room had two beds and that I could stay with him. I quickly agreed.
When we got to the room he pulled the covers down and told me I could have that bed. He got down to his shorts and got into the other bed. I was still standing there fully clothed. I had never been seen in my lace undies by another man and was embarrased to undress in front of him. I guess he sensed my selfconciousness and turned to the other side. I got undressed and as I was getting into the bed I noticed him looking at my butt. We laid there talking about the movie and I noticed his hard on through the covers. I guess I started wimpering something to the fact that I just needed someone to love me for a change and to just make me feel good. Next thing I knew he was sitting on the side of my bed and rubbing my neck. I looked up at him and asked him if I was a bad person for the way I felt. He said no and pulled me to him. He started touching me all over. Soft and gentle. When he started rubbing my tummy and crotch I knew I was in heaven. He took his cock out and asked if I would please him with my mouth. He slid it in as I licked it all around. It was beautiful not really fat but about 8″ or longer. He layed down with me and I started sucking him some more. Soon he couldn’t hold back anymore and held my head as he let his manhood unload in my mouth. I swallowed it all for him. After that we fell a sleep together. Sometime during the night I awoke to him rubbing and fingering my cunny hole as he now calls it. I just laid there as he pleasured us both. He got up and went to the bathroom. I rolled over on my back wondering why he stopped. Worried that he was having second thoughts. That all ended when he came back with some lotion from his bag. He smiled at me as he knelt between my legs. I pulled my knees back to my shoulders spreading my cunny wide for him. I was now about to know what it like to be fucked. He tucked a pillow beneath my ass and rubbed the lotion in and out of me. It felt so good and didn’t hurt at all. Then he put the head of his dick to my cunny. He looked down at me and I smiled knowingly that I was ready for him. He pushed the head in a little and it only hurt a tiny bit. I felt confident and told him to go ahead and fuck me. With that he pushed with all his weight and drove it all the way to his balls. I screamed in agony it was ripping me in two. God it hurt! My body was shaking and hurting like all hell. Tears were rolling down my face as I begged him to stop but he wouldn’t he just kept pounding away like a pile driver. I told him it hurt and he said I’d get used to it. He told me to shut up and fuck him like the whore I was supposed to be. He fucked me brutilly for the next 15 to 20 minutes. I hated it, it hurt and burned the whole time. Finally he came and fell exhaused on top of me. I layed there with him still in me for what seemed an eternity. After a while he got soft and slid out and rolled over. He hugged me and said I gave him the best fuck he ever had. I layed there crying and regretting what I had done. I got up and went into the bathroom. When I sat on the pot his juices flowed out of me. My cunny was wide open. I wiped myself and noticed that I was bleeding as well. I took a hot shower and next thing I knew he was in there with me. I couldn’t believe him. He was horny again. He told me he was going to make love to me from now on and that he would never hurt me like that again. When we got back in bed he did as he promised and has made me his lover. After a few days the pain and the bleeding subsided and we now have the greatest sex you can imagine.
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