Prom night for a sissy crossdresser

The restaurants and bars were packed. Cute high school kids all dressed up. Must be prom weekend or something. I couldn't get into my favorite place to eat, so I further wandered downtown looking for plan B. Boise has changed a lot in the past few years. I remember when there were just a couple of gay bars downtown. It seems like they all gave some sort of gay theme now. 

I finally found a seat at the bar and ordered an appetizer. I noticed a group of young people at a table past the end of the bar. A couple of guys in shirts and ties, and a couple of girls in pretty prom dresses. How are high school kids getting drinks in here? 

One of the young men shyly walked over to me.

"Excuse me. I'm here asking for a friend. My friend, down there in the pink chiffon dress, would like to buy you a drink, and maybe get a picture with you. Would that be OK?"

Surprised, I look down the bar at the girl. Well, a boy in a girl's dress it turns out. 

"Really? You all seem to be having a good time on your own."

I'm 50, but I look pretty good for my age. I'm very tall, 6 foot 4. And I did dress in grey slacks and a nice dress shirt tonight. I was caught off guard. 

"She would really appreciate it."

"Ahhhh...sure."

Before he motioned to his 'friend', he whispered to me that she was really a boy. I whispered back that I already figured that out.

It took the other two kids a minute to convince her to actually come down to meet me. They pushed her, actually. She was flushed with embarrassment. That was cute. The closer she got, the prettier she was. Tall, 6 foot ish. The pink dress had ruffles along the top and bottom. It was the type with no straps holding it up. Just elastic above her perky breasts, falling smoothly down to just above her knees. She was wearing tan nylons and some cute little pink flats with those straps that wrap up around the ankles. I've always loved those. Her hair was shiny blonde with long curls and some pink ribbons falling over her bare shoulders. 'Fitting nicely in that tight little chiffon dress,' I thought to myself. 

She musters up some courage and walks up to me. I ask "How are you all in here drinking? Isn't it prom night?"

She hesitates, but finally gulps and answeres "Oh, yes. But I'm a few years out of school. We all are. I never had a chance to go to dances, so we thought it might be fun to do this tonight. I always wanted to go out for prom."

She is looking up at me with those beautiful blue 'puppy dog' eyes. This is fun but I'm ready to eat my appetizer. "All right. Let's get a picture."

She hands her phone to one of her friends and steps right in, close to me. She takes my arm and pulls it around behind her. Another 'puppy dog' look. "Is this OK?" I nod. 

Her arm slides behind, hugging me tightly. Looking up, she says "Thank you. I really appreciate this."

Her friend starts taking pictures. Her head falls against my shoulder. I pull her a little closer. She lets out a sigh. Her hand squeezes my side. I feel like I'm back in high school. It's like a ... special moment. 

My hand wanders a little bit. Just up and down the side of her. I can feel a wide sexy strapless bra under her dress. She lets another sigh slip out. I feel her warm, wet lips touch my cheek. Her hand is up in the middle of my chest. I turn to look at her. She steals one right on my lips. I'm not sure how to respond. I just smile. 

"Hey! It looks like Jesse is in love! Haha!" She blushes and looks down at the floor. 

More pictures. Another round of drinks. We end up sitting at their table with her arm around me. In the bar, there is a small dance floor. She asks me for another favor. A smooth song is playing. Her arms are up around my neck, she is gently nibbling my neck. My hands are moving up and down her back. The dress is soft, slippery, and tight. 

"Do you like my dress?"

"I do. Where did you get it?

"My sister loaned it to me. And pretty much everything else I'm wearing. Those are her hair extensions."

"I like them. I like your whole outfit. You're very pretty as a girl. But, you know that."

My hand is on the back of her dress, feeling the outline of the strapless bra. MY other hand slides down just above her nice little butt. There is an outline of a thong back panty. She looks up at me again. 

"My sister gave me those too. Do you approve?"

I feel myself flush a little. That was embarrassing. "Sure. Of what I can tell. I like them very much."

She leans up and kisses me on the mouth. Her hands pull my head down as she opens, inviting my tongue to enter. I slip it in a little. Her mouth feels nice. Her lips taste like cherries. I like it. Her friends are gone. It's almost midnight. She says she might need a ride home. 

In my car, she jumps me. She can't get enough kissing me. Her hands are all over me. Opening my shirt, down inside my slacks. My shirt is unbuttoned. My fly is open. Her fingers are in my hair and wrapped around my cock. I've got her dress pulled halfway down and halfway up. One of my hands is down the top of it. Grabbing at her perky little nipples under the sexy strapless bra. I slide my other hand down her back, down the top of the thong panty, and between her cheeks. Very nice!

"If I suck your cock, it will be my first one. Can you help me if I'm doing it wrong?"

I'm pretty hot and horny right now. I'm mostly hard. I look down into those darling eyes. "Sure. I'll let you know."

She sucks as her life depends on it. When she comes up for air I can see she is crying. 

"Are you all right? You don't have to do this."

She looks back into my eyes. "Fuck, I've been waiting for this my whole life. I couldn't be happier."