Trying on a few new things

The party

My sister Jill left a lot of clothes when she moved away from home. I've been dressing in her underwear and outfits for years. I was always confused about how I felt wearing them. Did I want to be her, or did I want to be closer to her? I know she has more than one boyfriend. My mind wanders to where she is doing things for them in her sexy bra and panties. I almost always start thinking about being forced to my knees sucking a big fat cock every time I pull on one of her garments. Whatever it was, my naughtiest thoughts always surfaced when I was in them. 

Last Halloween I met a guy at Jill's party while I was dressed in an old prom dress. He tried to get me into the bathroom where he could lock the door and grab me. He wanted to kiss me and who knows what else. I wish now I had let him. I wonder all the time what that would have been like. I still can feel his hands on me and the taste of his lips. Jill invited me again this year. She had warned me there may be a few gay guys at the party last year. And she reminded me of it again for this time. I said I wasn't bothered by that. She told me after last year's party how silly I looked in her old dress. But this year she said I should dress like a girl again. Like she knew someone might like me that way? I was really excited. And nervous.

This time I spent a lot more time with my hair and make-up. I watched some YouTube videos on how to do it. I pulled my hair back and put it in a ponytail. It was just long enough for that. Then I used some extensions to fill it out. It looked pretty cute hanging down to my shoulders. I tried to keep the make-up simple. A little eyeliner, shadow, and pink lipstick. I wore a tight little white lace pushup bra and matching thong panty. I'd picked out a couple of party dresses but then I noticed a nurse's outfit in the back of her closet. It had the cute little nurse's hat and everything! I had to buy new white seam-back stockings because I've ruined all the other nylons she left behind. I picked up a pair of white pumps at the discount store for $24 and I was in!

The white one-piece nurse dress fit a lot tighter than the prom dress did last year. I'm still in pretty good shape for a guy in his mid-20s, But it probably could have used more curves. My ass is only so round and I didn't want to stuff the bra cups. I wasn't very happy with it until I put up my hair and attached the hair extensions. Wow! What a difference a simple change with the hair makes! I looked pretty fucking good!

I guess I never really thought ahead about what might happen. I was hoping I'd meet another guy like the last time, or maybe someone I've met before. Has my sister set me up? I know a lot of the same people she knows. Could it be someone I know? No one really stuck in my mind as a candidate. I've never felt anticipation like that before. I was feeling shy, excited, and scared shitless to the point where I almost decided not to go, all at the same time. 

I put on mom's long London Fog coat and drove across town to Jill's house. I had to park 2 blocks away. She and a girlfriend had rented a huge old house. There was plenty of room for a big party. And there was a big one tonight! I had to walk a long way in the 4-inch heels. I didn't like that. But I couldn't take them off or I'd ruin the stockings. I stumbled down the walk past all the parked cars, finally making it to the house. The party was going on in the back yard so I walked around the side of the house and went through the gate. Shit! More walking in these impossible heels!

This year the party was all gay. Turns out my sis and her girlfriend were really girlfriends. There were a few other dyke couples and the rest were all guys. 25 or 30 of them. I was the only guy in a dress. I felt like everyone was staring through me. I didn't know anyone. I was about to spin around to leave when someone pulled at my coat offering to take it for me. It wasn't a chilly night. I didn't wear it to keep me warm. I was hiding my outfit until felt ready to show it off. And I wasn't ready.

My sister appeared to save me. Or so I thought. She said she should introduce me to everyone. But she whispered for my dresser's name. I started to get dizzy. All these guys looking at me. I told her to just use my real name, Bill. But she came up with her own name for me instead. She introduced me, as my coat was pulled back over my shoulders, as her bi-curious brother, Barbie.

Everyone clapped and hooted! "What the fuck, Jill?" My coat disappeared. I was handed a tallboy bottle of Bud. I was standing in the middle of the yard in this skimpy short dress with everyone pointing, laughing, and staring at me. I could feel my face flushing. I'm sure it was bright red with embarrassment. Two guys who seemed to be a couple came over to humiliate me. "Hey, Barbie! Do you want to join us? We need a little cream center for our Oreo. Hahaha!"

I spent the next few minutes looking for my sister so I could yell at her again, and for mom's coat, so I could leave. I think I was even crying a little. What a shitty party! I ended up in the house looking around aimlessly. 

A firm hand slipped up onto my shoulder. Jeff was a foot taller than me. He was older too. Probably too old for me, I thought. But, what was I thinking? I'm not in the mood for any sort of conversation or encounter. I just wanted to cover up my outfit and get out of here. But Jeff had my coat. He kindly offered it to me. He helped me with it. He was nice. After he told me his name he asked if I'd do just one thing for him before I left. I laughed, rolled my eyes, and looked at him with suspicion. He quickly attempted to explain. "It's just a simple thing really. When your coat opened up and showed your sexy outfit under it, I almost dropped my beer. I'd love it if you'd do that again for me. Would you, please?"

Suddenly the memories of last year's party rushed into my head. The guy grabbed me, forced himself on me. I wasn't sure if I liked that even after all this time. Maybe I was ready? But maybe not!

I held the coat tightly closed. I'd only been there a few minutes. it was still very early. What would I do if I left this party? I'm not going anywhere else dressed like this. The beer tasted really good. I wanted another one. "Get me a beer and we will see."

Jeff was gone then back in a flash. He opened the cap asked if we could not do it here in front of all these weird people. With the long neck of the bottle sliding into my mouth and keeping the coat tucked closed, I slowly nodded. Jeff talked to my sister for a moment then took my hand and off we went. 

These old houses have really cool staircases going up to the bedrooms and bathrooms, he said. I guess he was some sort of architecture expert. There was something going on in the first 2 bedrooms. And even the one at the end of the hall was busy. Not to be denied, he pulled me into the bathroom and locked the door. This was the same bathroom I'd been groped in last year. But Jeff didn't care. I was against the back wall with him leaning against the door, securing it closed. And blocking my escape, I feared.  But I mustered up some courage sparked from the feeling of his hands on me, pulling me up the stairs and in here. I think I liked being led around like a captive or a slave or something like that. I straightened my back, threw my shoulders back a bit, and posed as well as I could in the classy, full-length coat. He took out his phone, pointed it at me, and started clicking away. 

I moved one foot forward, then the other. I turned my head to the side, then back again, looking right at him. I noticed he was rubbing his crotch. "Please take it off. Please!" I'd never had a guy beg me for anything. This was pretty fun! He was giving me all the attention. And he was loving it. 

I slowly moved my hands to the front of the coat where the belt was. I carefully unbuckled the clasp. The two ends of the belt fell to my sides. I felt like a model doing a striptease. He was rubbing himself a lot harder. I gently took the lapels of the coat and opened them just a bit. Before I spread the coat out completely, like a beautiful bird spreading its wings, I reached underneath, pulling the zipper in the front of the dress all the way down. I felt it open, relaxing its tight grip around my nervous, shaking body. "You're really going to like this," I said.

I was so excited and in such a hurry to show off the sexy lace bra and panties I was wearing under the dress, I forgot I was with a complete stranger, locked in a small, private room. But, what the fuck? Right? I took the corners of the coat and opened it completely. My arms spread wide out,  exposing my fallen down dress, my warm smooth skin, and the awesome panties and bra. 

Jeff's phone hit the floor. I think he cracked the screen. But instead of going down for it, he moved right in on me. Deja Vu? Maybe. He led with a warm wet kiss. And he wouldn't stop. His hands slipped back around me, hugging me close. Suddenly I realized his shirt was unbuttoned and his pants were on the floor. I was shaking but really having a good time too. he hesitated, whispering to me. "Stand right like this. Please let me do this. Please let me!"

Jeff's hands cupped my perky, lace-covered breasts. His face slipped down over my tummy as he dropped to his knees. He was licking and kissing everywhere as he went down. His head and shoulders wedged between my thighs, moving them apart. My legs were spread out really far. I was leaning back against the wall, propped up on my tippy toes. His mouth opened as he engulfed my whole package in his mouth. It felt nice having my dick and balls suckled while they were still tightly wrapped in the soft sexy lace panties. I could hear him moaning with pleasure. He gave my tits a good hard squeeze. Then one hand dropped down under him. Before I knew it he had managed to get my dick out from inside the panties, sucking it into his mouth. I was pretty hard by now. He was jerking off while he sucked me. He squeezed my tit again, really hard. I looked down at him. He was looking up at me. I froze in horror. What the fuck was going on? But it was much too late to stop now.

I took a huge, deep breath. My eyes rolled back in my head and I came. He was choking and slobbering cum everywhere. My hand was on the back of his head, holding it close as I unloaded. I didn't remember moving it there. I didn't remember anything. I was caught in the moment. That was it. 

Jeff had one of the bathroom towels. He was wiping his face and cleaning up the mess from my panties. Some of it was running onto my stockings. He kept muttering: "Oh my God!" Down on the tile floor was another long stream of jizz. Jeff had cum too. I slid down, sitting on the toilet seat. Jeff collapsed on the floor, leaning back on the tub. We didn't say anything. He was catching his breath and trying to button his shirt. I looked across the bathroom, catching a glimpse of myself in the mirror.  Shit, I still looked pretty good. My hair and make-up were still in good shape. Jeff hadn't ravaged me too badly. I wiggled a little pulling at the dress so I could zip it back up. Then I hear the door unlock. Jeff is leaving. Well, if that isn't just like a man? 

He surprises me by reaching to help me to my feet. I wobble in the heels on shaky legs. He takes me downstairs and we have another beer. He is rubbing the small of my back while we sit and chat. He tells me what he does for a living and I try to explain that I'm still in college. Sort of. It's complicated. His hand slipped under my butt a little. I stop talking and look right at him. He silently stares back at me. Then, with loads of confidence, he says: "My car is right out front. I've been waiting here for you since 6."

Well, I guess that will be another conversation for another time. He has a nice car. Again he asks a direct question. "I want you to suck my cock right here. Will you do that for me, please?"

I mumble and stumble and try to get it out. "I've never really done... you know? That."

"It's ok, Barbie. I've never done that before either. That was my first. And I'm so glad I let myself try it. You will too."

Jeff is slowly pulling the zipper on the front of my dress down again. "Why don't you just take this all the way off?'

I didn't even hesitate! What the fuck? Off it came. Over the center console. Down I go. This guy is already hard as a rock again. Once you've got a cock in your mouth you kind of get into it. Anyway, I sure did! I didn't even notice his hand up between my butt cheeks. Well, I barely noticed. He was pulling my hair and grunting while I did my best to shove his cock down my throat. He was groaning and talking dirty to me when he came. I had two fingers up my ass and one big wet salami choking me. I almost puked from his cum filling my mouth and shoving the tip of his cock as far in there as he could. When I finally broke free, sitting up to get away from that fat fucking cock, there was cum drooling and running everywhere. "Oh Fuck!"

Before I could get all the way back to my side of the car, he grabbed me, pulling me back over. He pulled me close and kissed me.  "Give me more of you, Barbie!" We had a really long, really wet, really sloppy kiss. There was plenty of cum in my mouth. There was plenty all over my face too. There was cum everywhere. We just kept kissing. Fuck!

With our faces dripping with cum, he looked at me and said:" I want to take you home tonight. I want you to stay. I want to fuck you, Barbie. I want to fuck you like you're my girl. Will you let me do that, Barbie?"

One of his hands was squeezing my nipple. One of my hands was squeezing his cock again. I wanted to go down and suck it some more. Him playing with my tits felt nice. I quickly remembered his fingers in my butt a minute ago. I liked that too. Did I? Fuck yes, I did. I swallowed a glob of cum and said: "Sure."

Chapter 2. Becoming Barbie.

Second chapter coming soon.