Double Date With My Sister.

I was 14 when my oldest sister who was 20 asked me to double date with her. She was seeing this guy she liked alot and one day he asked if my other older sister who is 16 would go out with his brother on a double date. Well my sister Linda said no way the kid's a nerd and he's dead to the world. Even trying to bribe her wouldn't work. Then oldestest sister Lisa aked me and I said i wouldn't know what to do on a date. She told me you don't have to do anything we're going to a movie you hold his hand sit next to him. He's shy quiet guy, I've met him. Night of the date was like a royal affair my mother, 2 sisters all helping me dress making sure everything was just right,Hair just right, makeup not over done, nice floral paisley design dress that was very comfortable to wear, nails done a little perfume and I was ready. My sister Linda was dressed to the 9s. Our dates arrived and off we went to the movies. This kid Joey was so shy his brother had to tell him to talk. And then tell him to hold my hand. I realized my sister Linda was right and that I was safe with Joey. I started to flirt with him, something I had never experienced before or done. It just seemed to come natural. I asked him if he liked my dress, my hair, smell of my perfume. I had to drag every answer out of him. I asked what school he went, classes he was taking, music he liked etc. I was giving it everything I had. At the movies we held hands sitting down and I put my head on his shoulder. I even rubbed his thigh a couple of times. After the movie we stopped and got a soda and a snack and home we went. He walked me to my door while my sister was still in the car. He thanked me for going out with him. We stared and finally I made the move and gave him a nice kiss and he left.

Now you would think this was not a successful date. Even I was a little disappointed about it. Me and my sisters discussed it several times. But as time when on I realized what a confidence booster this was to my crossdressing. Not the fact that I had dated, that I had kissed. But one big step in my achieveing a new level in becoming a woman. When I went out now I no longer thought do people notice if a i'm a guy. I look at everyone as just people.
femboy4u femboy4u
12 Responses Apr 20, 2011

Over the years, we double dated as few times when we were younger, with in our group of couples.

I had or we had this one friend whom I took diving class with that we both knew prefer to go out with other girls, and we had no issues with that my GF / wife even set them up with boys to go to school dances as a double date. they could not dance with each other but they could be with each other.

Many times over our high school years we would have study sessions up at our boss's cabin.

This one weekend 6 of us was going up to study, and we had been talking about it at school when the girl as if she could join us and we looked at the other couples going and we all said sure why not see if so and so wanted to join us too.

Understand we were not like other kids if you have read any of the Roberta story's, I have written you will understand it was a great weekend,
and I think or know it broke a lot of ice with the four others that weekend.

I think that was a wonderful story, Im so glad for you.. and to have had such good sisters to help you. I didnt get as much support from my family when i came out.. XXX Diane

nice story glad it went well!

Have been out several timessince then. Nothing sexual yet. Everytime is an experience to enjoy and boost my confidence. I guess like any girl I'm waiting for the right guy.

What a lovely story about your evening out on a date. Very fortunate to have dreams come true.

enjoyed the story fun and enjoyment experience is the best teacher

Very nice one, just a suggestion if u dont mind, <br />
Could have added the step-by-step makeover dressing makeup & inbetween conversations ete,. that would have added more spice. <br />
this is just an opinion so dont take it otherwise.<br />
<br />
wish u good luck

I was too young for confidence at the time. But did realize later it was a great experience.

Your Welcome.

A beautiful story, femboy. thank you for sharing.

I really enjoyed this story.....LPB likes this!

Thank You.