My Brother Made Me Do It

Many people ask me how I started dressing in woman's clothes. The short answer is my older brother. He was in high school and I was in grade school. My parents would go out sometimes at night and have my brother watch me. We would watch TV and play some games until one night my brother Todd said let's play a new game. I said what is it. Let's play dress-up, I'll dress in dad's clothes and you dress in mom's clothes. I said why do I dress in mom's clothes? He said because you are much thinner and will fit in mom's stuff. I said I didn't want to play but he kept saying come on please it won't hurt just this once. I finally said ok. Off to the bed room we went. He said we'll do you first. He went through my mom's drawers and pulled out a pair of panties (he said what are you waiting for takeoff all your clothes.), a bra, girdle, panty hoses, skirt and top.
I put them on and was standing there, Todd said here put these socks in your bra. You don't look anything like mom but you look like a little girl. Here put some lip stick on. He walked me over to the mirror and said see. I did look very different and then he put his hands on my **** and said these make you look so sexy. And nice legs.
He said don't you feel good, you look good. I said, I guess so now you dress in dad's clothes. He went over to dad's drawer got a pair of underwear out and put them on. They were boxer shorts. As he put them on I could see his **** was starting to get bigger. I could feel myself getting bigger as well. Not sure if was the clothes I was wearing or the fact that I was staring at his ****. I really felt different. He looked at me and said look what you are doing to me. I said how. He said you are so sexy.
Todd said want to see what girls do to guys when they have a hard-on. He went over to the VCR and truned it on. It was pre-set to a pacific place in the movie. What was playing was a x-rated movie. A woman was on her knees in front of a guy with his **** in her mouth. She was licking and sucking and licking until he climaxed in her mouth and the two of them were so satisfied. He said see come on you try that on me. I said no way. He said you know you want too you haven't taken your eyes off my **** since you put on those clothes. With that he took off the shorts and he was naked. He was sitting on the edge of the bed with his legs spread and a very hard ****. He said I'll make a deal with you, I bet your little **** is hard and if it is you'll suck my ****. I said it's not he said let me see and walked over to me and pulled the girdle down. He found my little **** at attention. See you are a little girl and want to suck me there is the proof. .
Come over here now or I will tell mom and dad that you were wearing mom's clothes and here is the underwear you ripped putting them on. He had another pair of panties that had a hole in them. I said you wouldn't, he said I won't if you come over and act like that woman in the movie.
I walked over to the bed and got down on my knees. As I got closer he said go ahead I will help you through it. Just put your lips on the tip for now. I put my lips to the tip of his **** and now just suck on the head a little. Very good he said. A little bit of pre-*** came out. Tatse it it doesn't taste bad does it. He was right it didn't I continued sucking a little and then remembered what the woman was doing in the movie. I started licking his balls and his **** until I got to the top of his **** again and tired to put his whole **** on my mouth. I was really getting into it. I could feel my **** getting harder and harder.

As I stared down his **** with my mouth I started to cough. He was too big for me. He said ok we'll go slowly. For now let's just have you suck as far as you can and use your hands. I started moving my head up and down with my hand covering the part of his **** I couldn't fit in my mouth.
I could tell he liked it when all of a sudden he said don't stop, keep going I am going to ***. I thought, I know what that means and just as I was going to pull away he put his hands behind my head and push his **** in my mouth. The next think I knew I had a mouth full of ***. When he let my head go *** was dripping from my mouth. He had a ton of *** he must have been saving that for weeks. I was about to spit it out when he said, no don't, it will stain the carpet you have to swallow it won't hurt you. He said you saw the woman in the movie please it looks so sexy to watch you do that. So I did. He said see that wasn't so bad. He was right it actually tasted different and as time went on I learned to love the tatse of ***.
With that I reached down and felt my panties to find to my surprise they were soaking wet. I have climaxed in my mom's panties. Todd said no problem give them to me. I took off all her clothes and put them back the way they were. I looked over at Todd and said did you wash out the panties? We can dry them with the hair dryer. He said, well I don't think so, because now if you don't do this again for me I have something to show dad. What do you think dad will do to you if he knew you were playing with mom's panties and climaxed in them? You know how bad he talks about ****. I said so what do you want. When mom and dad go out I want you to dress up like a woman and suck my **** whenever I want it. You have no choice and you'll get to like it. He was right so over the next couple of years I did learn to like it and even look forward to dressing and servicing him. Now sure where he got them but Todd brought me sexy dresses and even a wig. I found when I dressed I got a hugh hard on and as he climaxed I did also. I think it was the rush of *** hitting the back of my throat or feeling him *** all over my face. And at the end I could take his whole **** in my mouth and swallow every drop of his ***. However what he did to me just before leaving for college would really make me the way I am today.
Litemike Litemike
61-65, M
2 Responses Sep 15, 2012

Wow... wish it had been me

Oh, you got me hard too!