Going to my prom

After college I started crossdressing for real. Not going out or anything, but I worked hard on getting in better shape and trying different outfits and make up and the like. My hair wasn't very long but I let it go until I could just pull it back into a tiny ponytail. I noticed with my hair all pulled back and little make up I could, maybe, on a dark night, pull off being a real girl. This made me very happy as I would experiment with the make-up and dress in different outfits and have very good jerk off sessions.

Of course, I got bored being alone all the time, so I started dressing and posting ads and pictures on some gay websites. Most gay guys it turns out aren't interested in a crossdresser. Finally, after several attempts I met a guy who liked sissy boys and liked me and would agree to fulfil my fantasy. 

My fantasy was to be picked up for a date and taken to my high school senior prom as a girl. He was nice and said he would do most anything to impress a sweet little sissy girl like me. he sent me a picture of him in a black tux and told me he knows of a place where they play all kinds of classic rock music, including plenty of slow songs, making it great for dancing.

His picture was a little blurry, but he looked to about 40 and in decent shape. He said he is hairy and has a little bit of a beer belly, like a dad bod. I told him I was OK with that. 

After I sent him some pictures of me in a couple of different prom dresses, he picked the pink one and things began to move quickly. The bar was having rock night tomorrow and I needed to be ready. 

I was so nervous! I felt like a silly schoolgirl. I was also very excited. Then the reality of it all began to set in. I've never even kissed another guy, let alone anything else. As I slipped on my lace undergarments, A white camisole and silk slip, I felt my skin was cold and I was actually shaking. I'd forgotten to put the bra on first. I can't find my panties. I was going to be late getting ready. Fuck!

I quickly removed the camisole and pulled on the small 'A' cup white lace and satin training bra I'd purchased just for this occasion. I'd ordered two medium size silicone breast forms made to fit in small slits in the bra, filling the small bra cups to perfection. I took a minute I didn't have to admire my new curvy shape around my chest. My hands couldn't help but slide over the bra, enjoying the feeling of the soft lace and my new sexy tits.

The panties of choice were rather heavy rather than a tiny thong back. I needed something to hold my package in check for at least most of the time. Although after feeling myself up, I could tell this might be a chore. The full coverage satin and lace panties, like mom might have worn back in the day, seemed to do the trick. 

I was gazing in the bedroom mirror admiring this pretty little flower in her sexy bra and panties when my phone buzzed and startled me back into reality. He was fucking out front!

In a rush I pulled on the camisole and slip and flung the dress over my head. I raced to the front room, quickly positioning the dress around my body, grabbing my pink 4-inch heels, purse and jacket, and out the door I went. 

I felt flushed and disheveled as I stumbled out the door and down the walk to the street. It was late evening by now and the street was dark and silent. I barely even noticed the minivan he was driving. More of a work van actually. Small, like a delivery thing. I grabbed the door handle and fell into the front seat. "Oh my gosh, I'm so sorry to make you wait!"

A deep older man's voice replied: "It's OK, babe. We have all night." The doors locked, and off we went.

I've heard if a girl is ever assaulted by men wanting to kidnap her, getting into their car means you are in real trouble. Do everything you can to not let that happen. I just realized I'd jumped right into a man's van. A man I've never met and know nothing about. It's dark in the van too. His silhouette is much as I expected from his photo. And he was in a suit jacket. Black, I think. I carefully pull the seatbelt around my chest and buckle it. Looking shyly and nervously at the man in the driver's seat. "Hi."

"You look cute. Thank you for dressing up so nice. The bar is downtown, as you know, but I wanted to take one detour before we get there. Is that OK?"

:I suppose. What do you have in mind?"

He didn't answer. Again, suddenly, the reality of where I was hit me. Fuck.

We drove silently toward downtown. He took a turn back into a warehouse area. It's dark and cold here. I was looking away from him out the window into the dark night. I was shivering. 

"I have an office here. This will just take a minute. We pull into a parking area and stop. He takes the keys and quickly goes into the building and returns. He has a small package in his hand. The hairy old guy looks me in the eyes. " This is for you. Then I'd like to get a taste of what I'm doing this for."

In the bag was a nice silver necklace. It had a large red glass heart pendant on it. I held it up to see it better in the dim night light. He took it from me and placed it around my neck. While he was snaping it in behind my neck his face was right in front of mine. He gave me a little kiss on my cheek. His beard was a little scratchy. But his lips were smooth. 'A taste' is what he had said.

I didn't move. His hands were resting on my shoulders. Our eyes met in the dim light. "Get in the back of the van, sweetie."

"What?"

I quickly glanced back between the seats. In the rear area was a pile of blankets and a thick comforter sort of thing. There were some throw pillows tossed around. 

"What? You want to go back there?"

"Yes. I told you I want a taste. I want it now. You said you'd be a good date. Don't be a liar. Let's get to it."

His hand was holding my arm and the other was pulling me from the back of my neck. He led me into the dark back cargo area and pulled me on top of him. My legs spread out with one knee on each side of him. His hands grabbed my ass cheeks and pulled me in further. Before I knew what hit me, he was kissing and groping me like a drunk... well, prom date. 

Every time I would try to speak, he would shove his tongue in my mouth and hold us there kissing with a hand to the back of my head. My dress was half pulled off, pulled up nearly over my head from behind. He had fun with his other hand working my ass in my pretty panties and my tits in my cute little bra. I tried to get into it. But this was all so new. But I didn't hate it either, I realized.

I took a breath and gave in. I kissed him deeply, sucking on his tongue and moaning like a horny little slut. We kissed for a long time. Somehow, I was only dressed in my bra and panties now. My pretty prom dress, camisole and slip were somewhere else in the van. But I didn't care. His warm hairy skin was all over me. His clothes were mostly gone too. I sucked on his hairy chest and ran my fingers through it. "You're a good girl. A good girl and a good slut. So now you'll suck my cock like a slut." This wasn't a question or a request. More like a demand.

Pressure on my shoulders and him moving his waist around to meet my face happened quickly. I had to get back up on my knees a bit to be in position. He must have had a nice view of my ass in the tight white panties. "You have a fine ass, my new friend. I'm looking forward to having it for desert later as well."

If I was wondering if I really had much of a choice in the matter, I was wrong. A strong hand on the back of my neck and the other guiding his hairy cock into my mouth was making this happen no matter what. Well, shit. I'd kissed the guy. Why not?

He wouldn't stop telling what to do. He said I suck at sucking. I tried to tell him this was my first and I was doing my best. But it's hard to communicate with a big hairy cock stuffed in your mouth. 

After a few minutes he pulled my hair, jerking my head back away from his wet, spit dripping cock. He started jerking off right in front of my face. I tried to move but he held my head firmly by the hair on the back of my head. "We're going to have to work on this, you little cunt. Oh fuck!"

And he came.

His cock was immediately shoved back into my mouth. "Swallow it, swallow all of it, you fucking bitch!"

I choked and spit and gagged and then, finally, I actually swallowed some of it. Cum was all over my face, all over my chest, my bra, everywhere. He held his cum dripping cock in my face expecting me to finish him by licking and eating the remaining cum still running out of it. "Eat it bitch."

I guess I went from 'sweetie' to 'bitch' in just a half hour. 

We cleaned up with some of the blankets and I did my best to regain some composure. We rummaged through the van for our clothes and tried to dress as if nothing had happened. Looking in the mirror I knew I was fucked. My face was a mess. I did seem to get my dress back on in a suitable fashion. But I couldn't find my slip or my camisole. I said fuck it and off to the bar we went.