Hi this is a true story about my first time having sex with a man wearing panties
So I had been crossdressing since I was 10. I had experimented with other boys just jerking them off until one night I got drunk and stoned when I was 16. A buddy of mine who we had jerked each other off was there in the bed room with me. He jokingly asked if I had any panties around. Not knowing I was a crossdresser. I got up and grabbed my 2 favorite pair, a pair of black lacy silk ones for him and my purple lace ones for me. He said turn the light off and lets put them on. So i shut the lights off and we quickly stripped and put on the panties. We were both excited and I thought it would just be a jerk each other off session. Boy was I wrong.
I turned the light on and his cock was already hard and poking out the top of the panties when I looked. My cock got hard instantly and I knew right then we were going to do more then just jerk each other off. At least I wanted to. I wanted to feel him inside me all of a sudden. We drank a couple more beers sitting there with hard ons. Waiting on the other to make the first move. I finally decided to make that move and slide over to where he was sitting on bed and told him his dick looked sexy in the panties. I reached down and slowly played with it. He looked at me and said why don't we go farther this time. I shook my head yes. What do you want i asked. He said suck me for a bit. So I went down on him and licked the head of his cock sticking out of the panties. He moaned loudly, i moved the panties over so i could get at his dick. he wasnt very big about 6 inchs but it was my first time giving a blowjob. I licked his shaft like the girls in the movies do. Then I went back to the top and opened my mouth and slide his dick inside it. I was able to take all of him with no problem. I loved the taste of him. I played with his balls a little when he suddenly pushed me off him and on my back. Put my legs on his shoulders and faked like he was going to stick is cock in my ass.
I looked at him and said do it. I grabbed the ky i kept by the bed for when i dressed and used a dildo. Moved my panties aside and lubed him up. He looked at me and said really? you want me to fuck you? I said yes please do it. He put the head of his dick at my hole and started to push in. I resisted a little since i hadnt really used the dildo to much so i wasnt used to being fucked yet. I said just push it in. He pushed harder and slide all the way inside my ass. It hurt a little but felt good. I was in heaven. He asked me if i wanted it slow or fast. I told him to go slow at first i wanted to enjoy this. so he took his time at first. We fucked slowly for about 20 mins and he started to pick up speed. I told him we needed to switch ways of doing it as my legs were cramping on his shoulders. I got on my hands and knees and he got behind me. We both still had the panties on. He moved mine out of the way and since i was loose from his good fucking he slide right back into me. I told him to fuck me hard now i wanted it fast hard and deep. So he started going hard. It wasnt long before he said he was going to cum and did i want him to cum in me. I moaned yes deep in me. He grabbed my hips and slammed as deep as he could and i felt his hot sperm shot into my ass.
I was rock hard and horny as hell by the time he finished. So i laid on my back and he got on top of me. I slide right into his ass with no resistence. I asked if he had done this before and he told me yes. He rode me for about 15 mins before i got close to cumming. I asked him if he wanted it in his ass he said yes. I grabbed him as he slammed down on my cock shoving into him and shot my load deep in his ass.
we laid there with cum dripping out of our asses for about 20 mins or so. Got up and got another couple beers and he asked if i wore panties a lot. I told him thats not all i wore and got out my bra, garter and nylons. I got dressed for him in those and his cock got hard again. I said I also have a skirt and blouse that i wear want me to put those on too? He shook his head yes and I got fully dressed in front of someone for the first time ever. I put a little lipstick on and he stood up and looked at me and said i made a sexy woman. He kissed me. I told him i wanted to taste his cum. So i got on my knees like a good little slut and started sucking his cock. I played with his ass as i sucked him and it didnt take him long to start to cum. I slide him half way into my mouth so i could taste his cum. He shot in my mouth and I swallowed it all as fast as i could. I missed some and licked it off him.
This is what started me out on a sexual awaking that has seen me do random things with people and led me to being a total crossdressing slut when dressed up. I will do it anywhere anytime when I am dressed up.
I don't get out much dressed anymore sadly. But if you like this true story I have more to share with people. Like my first time with a real tranny. Or how I met my new tgirl girlfriend. Or how roommates found out i was bi and a cder