tagTranssexuals & CrossdressersI Owe It All To Jimmy

I Owe It All To Jimmy

byLisa Fallon©

It all started innocently enough. My friend Jimmy and I had been down at the river horsing around and both of us wound up soaked from head to toe. His house was only a short distance so we hopped on our bikes and sped off.

When we arrived there wasn't anyone home. He handed me a towel and told me to take my shower first. Jimmy said he would grab some clothes for me and leave them in the guest room. I cleaned off the muck of the river and after turning off the water and wrapping the towel around my waist I padded off to the guest room.

There were clothes on the bed as promised but not quite what I had expected. I thought it was a joke so I picked up the pretty lace panties and bra, short skirt and top and went looking for Jimmy. His room was just down the hall so with the pretty garments in hand I knocked on his door.

"Hey Jimmy, what gives here, I'm not wearing this stuff!"

"I thought it would be fun if we both dressed in girly stuff Eddie", he said. "Haven't you ever done it?"

"Uh, no I haven't, and I'm not about to start", I answered.

"Come on Eddie, it really is a lot of fun, just try it this once, I promise you will really enjoy it."

He explained that often when no one was home he would put on his mom's or sister's clothes and masturbated in them. He said it felt really good and that we should do it together. I figured what the hell and slid on the panties.

I must admit that the tight panties felt very sexy and the whole idea was making me very hard. I struggled with the bra trying to hook it around my back. He showed me how to hook the bra first and twist it around my torso, then slip my arms into the straps. I pulled on the top and zipped on the skirt. Jimmy just smiled at me and told me to wait for him to grab a quick shower.

I laid back on his bed and rubbed my cock through his mother's panties while I waited for him. In no time he had showered and appeared in the doorway wearing a pretty black lace panty, bra, and garter set. He showed me how he put on the stockings and attach the garters. My cock stirred when I felt his silky clad legs. I told him that I wanted stockings too, so he went down the hall and got a pair of tan thi-highs from his mother's lingerie drawer. I slid them on and got light headed from how sexy I felt.

"Eddie, have you ever had you cock sucked?", Jimmy asked.

"Uh, well, y'know I...um..", I stammered.

"You are gonna love it!", he smiled.

And love it I did. He proceeded to get on his knees and take my hard cock into his mouth. In only a few strokes I shot a hot load into his throat. He gulped it down and gently pushed me down to my knees.

The first time he came in my mouth I was shocked at how hot his cum tasted. The textue of his smooth cock as it slid in and out of my mouth was amazing.

That afternoon and many afterward Jimmy and I explored the world of sex together. He sucked my cock and I sucked his. After a couple of months we were fucking each other almost every day.

One afternoon his mother came home and found us dressed up in her lingerie with Jimmy pounding his cock into my ass.

"O my God!, what is going on here?", she screamed. "Oh my God!, my son is a faggot!"

I had not considered that I was gay until I heard her say that. Well I guess I was bi anyway. I still liked girls and so did Jimmy.

He was firing his hot load in my ass when she ran from the room. He didn't pull out until he was spent and my ass was gleefully full of his hot cum.

"Wait here", he said, and without taking off her lingerie he went down to his mother's room.

She was laying on her bed sobbing and wouldn't open her door. Jimmy came back to the room and told me I had better get dressed and leave. I did so quickly.

The next day at school Jimmy told me that his mom wanted to talk to both of us that afternoon. I was sick to my stomach all day in fear of what might happen.

When we got to his house I was shaking as we entered the kitchen. Mrs. Lowen, to my complete surprise, was very sweet and had made a batch of cookies for us. We sat at the table and very calmly discussed what had been going on between us.

"Well", she said, "from now on you may not use my clothes. I will get you boys some things in your own sizes and I can give you some tips on makeup. Just promise me that you will practice safe sex."

Jimmy and I continued our relationship through the rest of senior year. We even double dated to the prom. After taking the girls home we had our own prom at his parents summer cottage.

We would hook up on breaks from college and continued our affair into our mid twenties.

His mother never betrayed our secret. We run into each other from time to time, and although I still slip into a sexy pair of my wife's panties now and then, it just isn't quite the same.

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byLisa Fallon© 0 comments/ 107611 views/ 3 favorites

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