Hello Blanda, well the second time I was all dressed up and met with a man he invited me to his house and when I rang the door bell and the door opened I was surprised, pleasantly, but surprised. He was standing there all dressed up in a nice frilly dress I could see his nylons and his breasts firmly under his dress.
I came in dressed with shirt and pants over my dress. He invited me in to his living room and I said that I needed to join the party so I took off my shirt and pants and was standing there in my dress with my breasts perky. My dress was a little black dress clinging tightly to me. He offered me some wine and we sat and talked for awhile about what we liked to do and found out that we had similar likes. It was a great pleasure to relax in my dress with another man also all dressed up and talk about our feelings being men who liked to dress up in women's clothing and some of the experiences that we had with other men.
We finished our wine and went to his/ her bedroom. I reached to pull my dress up and over my head and he helped me with that. There I stood, no dress on, just my bra with inserts and panties and nylons and garter belt. I then helped him out of his dress and he was also then in only bra and panties, no nylons. Both of our cocks were big, hard and bulging through our panties and we reached out for each other's cock to stroke them.
I reached into his panties and pulled out his cock, it was as clean shaved as my own. He reached down and took off his panties and I did the same. We were naked except for our bras and me in my garter belt and nylons, both hard erect. We reached for each other's cock and started stroking. He then went to his knees and licked my shaved cock and played with my balls and then took his finger and moved it around my butt. Well, my legs moved apart all by themselves and then he put his finger in his mouth and then he went back to my butt and slipped it inside of me. That's when I moaned.
He asked if I wanted him to butt fuck me. Well I had certainty played with my own ass before but other than toys, I was virgin there and said that I was not sure if I (his cock) would fit in there without it hurting. He said that all it would take was to start slowly using a small dildo and then morning to a larger one and then to a larger one.
Well at this point I was so very gamed to try and said so. He brought out three different sized dildos and some k-y jelly. He was very gentle and started with the smallest and slowly moved to the largest one. All of this time I was bent over and he was sitting behind me and I could see in my mind just how I looked. Bent over with my arms on the night table my ass stuck out and my breasts hanging down and my cock rock hard with this man in his bra gently widening my butt hole. He finally said that when he takes the largest dildo out of me that the hole stays open and that he could penetrate me now easily and asked if I wanted him to do me doggie style or as a slut? After a moment's thought I said that I would like to try it both ways.
Well he stood up and grabbed me on either side of my butt and then stuck his cock into me slowly but by this time I was so lubricated inside and out that it didn't hurt at all. After a few short strokes he went in deep and then he started thrusting in and out. Then he reached around and started to stroke my cock. Well the feeling was outstanding and I wanted to cum and have him cum right then.
But I told him not to cum because I still wanted to try like a slut with my legs in the air and my breasts laying there on my chest. So we moved to the bed and I lay there on my back, he moves to kneel by my open crotch and takes my legs and puts them on his shoulders and I lift my hole up to him. He grabs hold of his cock and slips it once again into my ass. This time he goes slower to prolong it.
While he is moving in and out I'm watching his breasts bounce around and I can also see my breasts move around which was such a big turn on for me. He started to move faster and I started to stroke my cock in time with him. Not to long after we both came within moments of each other.
After that he invited me to take a shower with him and I said yes, I was sweating and had a lot of lubrication to remove. There wasn't much in the way of sex in the shower but we both cleaned each other's crotch and he toweled me so I did the same for him.
It was years ago and I haven't done it again, however I do think about it often. Maybe I'll get a chance to do so again.
By the way, when I was getting ready to go I first thought that I would just pick up my girlie clothes but decided that I wanted to drive back home wearing them and so I did. I put my shirt on but left the pants off. The bottom of my dress looked like a skirt.
Good memory!