I had just gotten divorced from my first wife and was at the bar when I met this nice young lady. We chatted for a bit and agreed to met for lunch the next day. We met up and hit it off. Now I have been dressing and bi since the 80s and normally I tell a person right off the bat but I did not tell Tina about it for some reason.
She invited me over to have dinner on the upcoming friday night. We both loved football just different teams and they happened to be playing each other. Tina says lets put a bet on this. I asked whats the bet. She smiled and said if I win you have to dress up as a girl all weekend. Every where we go you have to be dressed. Hell I thought not a bad thing. And if I win I said, she sat there for a moment and said I've always wanted to be submissive so if you win you get to lead me around all weekend no matter where we go on a leash. We made the bet. There was just one part she left out of my payment.
I lost. And Tina and I happened to be the same size so she picked out an outfit for me to wear on Sat. A nice blue bra and panty set. A white blouse, black poodle skirt. Black nylons and little black 2inch heel boots. Got up the next morning and got dressed. I already had long hair and back then I was skinny and kinda fem anyway. She did my make up and off we went.
Where we lived there was a park that there was some nice hiding spots to do things in and she led me to one of them. She had a smirk on her face and said oh I forgot to tell you as a girl this weekend that means all things girl. This is my friend Tony and you are gonna give him a blow job right here. I thought to myself well hell if this is how this relationship is going to start it is gonna be a wild ride. I walked over and got on my knees and pulled his shorts down. Just as I started to slide my mouth on his dick we heard someone yell "JUST WHAT THE HELL ARE YOU DOING"
We jumped and Tony pulled up his shorts and we all ran the hell out of there. We got back to the car and I suggested lets go back to Tina's house. They agreed...
As we were headed to Tina's place I said let's stop and get something to eat. Tina asked are you sure you want to be in out dressed like that in full view. I answered the bet was a girl for the weekend where ever we went so yes.
We stopped at a Chili's and went inside. I got a few stares but nothing to bad. The server came over and commented I looked cute and where did I get the blouse. I said it was hers and pointed to Tina. I explained I lost a bet and the server said oh that's to bad you make a very cute girl. I blushed.
After about 10 mins Tina needed to go to the bathroom and in the girls way she said come on let's go. I've never used a ladies room before, but the bet was girl for a weekend. Tina went in to make sure no other ladies were in there. She stuck her head out and said come on and remember you have to sit to pee.
We finished and ate lunch and headed out. We got back to Tina's and it was my turn to shock them. I pushed Tony down on the couch and said where were we I never got to finish that blow job. I got on my knees and started giving him the blow job I owed him, I noticed Tina had slipped out of the room for a moment.
As I was busy with Tony I felt my skirt being pushed up and my panties pushed to the side. Then I felt Tina's finger slide into me. She said just getting you ready for the strap on. Girl for a weekend I thought.
As I gave Tony the blowjob Tina continued to finger my ass. I had never had a dick in my mouth and one even a fake one in my ass at the same time but I had always wanted to try it. But my first wife wouldn't allow it.
I felt Tina get inbetween my legs and start to slowly push the strap on into me. I moaned loudly around Tony's dick. It wasn't a large strap on maybe 6-7 inches big but with one in both holes it felt fantastic. Tina went slow at first and as she picked up speed fucking me I picked up speed sucking Tony. I felt Tony start to spasm and slid him all the way in and felt his hot cum in my mouth. As a good girl I swallowed it all.
Tina picked up speed and reached inbetween my legs and started jacking me off. It didn't take long for me to cum all over her hand. Which she then said turn around and made me clean her fingers off.
Tony left after about an hour of us just hanging out and Tina suggested I stay the night. I said yes right away. She found me a nightie to sleep in and we crawled into bed. We made out a bit and then fell asleep(boring I know).
In the morning she was willing to let me out of the Sunday part of the bet but I said no, a bet is a bet. She had a red sun dress that fit me perfect and did my make up.
We decided to go shopping for some of my own stuff. She made a comment of can't have my girlfriend wearing my shit all the time.
At this time I was skinny and able to shop at non-plus size stores so we went to the local fredricks in town to get some panties and other things. As we were shopping she whispers to me.....seems like you are buying for more then a weekend huh? I whispered back Kinda. I'll explain later.
We then went to a few stores and got a couple skirts and dresses for me. And some heels.
When we got to the car I said ok confession time. I already dress up and my ex wife threw all my stuff away when we split up so this was to replace some of it. She said well confession time I know your ex wife and knew this and thought we could have the fun she didn't like.
We went back to Tina's and sat down on the couch and talked about things. She said if you want you can stay here and stay dressed in the apt all the time if you desire that. I said that sounded like fun but I wanted to go out in public as well at times.
We stayed together for about 9 months til Tina's job transfered her out of state and my job I had to stay where we lived at the time. The whole time I was more then Girl for a weekend. I was Girl for 9 months.
The end
