My 1st Time

I have always been a crossdresser, ever since I was really young I wore panties and dresses. Then as I got older I began wearing panties , bras , and stockings. Then fully dressing like a girl. When I was younger I was passable.. not so much anymore. But I remember when I was 16 I was in a corner store and there was an older guy there. He noticed I was wearing panties so he began to talk to me. He mentioned that he wanted me to go with him and be a girl for him or he would tell everyone I was wearing panties. Well I was really nervous but I went along with it. ( I wanted to experience the whole girl thing) but I was really nervous cause I wasn't with a man before. I met him at his car and we drove off. On the ride he took my hand and placed it on his ****. I began to rub it and I felt it grow bigger and harder in my hand. I was very excited and I rubbed it more intensely. It wasn't long before I had it out of his pants and was stroking it. He pulled my head down to his lap and I had his **** inches from my mouth as I stroked it.. He pushed my head down on his **** and I opened my mouth and let him in. I began sucking him the way I had girls suck me in the past. I must have been doing good cause in minutes he was moaning and holdin my head on his **** as he shot gobs of goo in my mouth. He held me on his **** till I swallowed every drop.. He pulled into a motel and got a room. We went into the room and he put on a **** movie. He told me I was going to do everything that the girl in the movie did. He was firm but very gentle and let me be the girl I always wanted to be. I sucked him hard again and he laid me down on the bed. He started to kiss me and caress me and it got me tinlgy everywhere. It wasn't long before he was lubing me up and sliding his **** in me. It was a little painful at first but he went very slow and let me adapt to having him in me. He put my legs over his shoulders and continued to work his **** in my manpussy. As he thrust in and out of me I actually started to enjoy it. THe thrill of wearing my girlie clothes and being taken as a girl by a man was so intense, I couldn't have stopped this from happenning. My inner girl had taken over. I was his girl and I wanted to make him happy. He pump in and out of me and continued to kiss me, soon he was pumping harder and deeper and I felt him pussh all the way in and he seeded me with another load of ***. I was a girl at that moment. Taking a hot load from my guy. The feeling of him inside me and knowing that I fully satisfied him with my mouth and my manpussy is what led me to a life of being a crossdressing ****. I never let a guy wear a rubber. If you're going to **** me then I want it bareback and I want your *** inside me. I love the way it feels when it drains out of me and gets my panties cumsoaked..
crossdresserkaren crossdresserkaren
41-45, M
3 Responses Dec 16, 2012

Wow loved that story. I'll bet you were hooked for the rest of your life. I know I have been.

Bareback is stoopid and irresposible. End of story.

bareback is the only way to go. i feel the same way if uare going to **** me then do it bareback and let me feel u shoot in me.

Thank you Allison... I'm glad to hear that someone feels the same way

Agree with you girl, I am not really ****** without the *** in me and I love being really ******.