Fun Times at Halloween Ch. 02

Story Info
After the Halloween Bash, he gets asked to the formal.
2.6k words
4.61
115.7k
75

Part 2 of the 2 part series

Updated 10/29/2022
Created 01/10/2008
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It was the following Monday and I got a call from Kathy to come over to her room. After class, I headed over there and she let me know that she ran into Red. He said he had a great time at the party and wanted to take me out sometime. I was both excited and very nervous because even though I had sucked him off last saturday night at the Annual DK Halloween Bash, he didn't know that underneath that maid outfit I had worn, I was really a guy.

"Well, what if he did know," Kathy said.

"You told him?" I replied, both shocked and scared.

"Yeah, he won't know who you are anyway, so I figured if he really wanted another date, he should know the truth that he had a guy suck him off."

"How did he take it?" I asked.

"Not as well as you did," she said with a wink. "He just stood there for a minute after I told him, then told me that you sucked his cock so good that it might be worth it. With the work I did dressing you up and making you look so much like a girl, he wouldn't mind living the charade another night. Then he asked if I'd see if you would go to the winter DK Formal with him in a few weeks."

"What? He wants me as a formal date?" I said surprised.

"Yeah, and I told him you'd totally go with him since Shooter had asked me earlier in the day and I couldn't go to a DK party without one of my girlfriends. A girl could get taken advantage of," she said with another wink.

The rest of that week, Kathy and I began preparations for the formal. Kathy had me talk to her in my softer girly voice all week and helped me groom myself to look more feminine. By the end of the week, I was also very good at doing my own makeup so I looked the part. She dressed me up the following weekend and we went up to the local mall to shop for a formal dress. She had me wear a black mini skirt and white button up men's shirt, with a sweater hung over the shoulders. I also had on a white thong and matching lace white bra. It was a very pretty look and she said it would also be easier to have a button up shirt when having to try on dresses.

At the mall, we went to a few stores and she had me try on a few dresses before finally finding a long sleeve black v-neck number with matching black choker. The v-neck didn't go down too far to be too exposing, and the hem was nice and loose, so that when I twirled it came up a bit like you see in movies. I loved it.

After that, we went to the lingerie store and picked up a nice black lacey bra and matching thong and garter belt set. The shoes I had already matched the outfit, so I was all set there.

The anticipation the next week made the time go by so slow. I would stay up late thinking about a few weeks ago when I was under the bar with Red's nice seven inch cock moving in a out of my mouth and how good his cum had tasted when he came. I had to masturbate every night because it got me so hot.

The day had arrived and Kathy and I showered together just like we had before the DK Bash. She helped me get cleaned up and surprised me when she wanted to give me an enema to make sure my ass was nice and empty for Red. It was a strange feeling, and the thought of fucking Red started a new chain of tinglings in my crotch. We got dressed, me with my brown wig, breast forms she had gotten me, black dress, bra, thong, and matching garter set. We went outside at 6:30pm to meet the guys.

A nice stretch limo pulled up and the Red and Shooter got out in their suits. Red had on a nice dark blue number with light blue shirt and tie. He looked quite handsome. He came up and I gave him a big hug, then before letting go of me, he kissed me on the lips once. We just stood there for a minute, looking into each others eyes when Kathy told us we were going to miss dinner.

"So, where's dinner?" Kathy asked.

It's a place about twenty minutes away, in the next town over. Shooter popped open a bottle of champagne and we all started drinking and I started to feel more relaxed, like I had at the party when I realized I was passing for a hot girl. Sitting across from Shooter and Kathy in the big limo, I actually caught shooter trying to sneak a peak up my dress. I made sure to cross my legs, but did allow my dress to come up enough so he could see the back of my legs where the stockings were attached to my garter belt. I could tell it was getting him excited.

Dinner was pretty nice, Kathy sat on one side with Shooter and Red and I were on the other. I couldn't help myself any longer and used the time at dinner to reach down and start playing with Red's cock under the table. It got hard immediately when I unzipped his pants and reached into his boxers to stroke it.

His seven inches felt great in my hand. I had the feeling Kathy was doing the same thing, and confirmed this fact when we made a 'girls' trip to the restroom.

Around 8pm, we had finished dinner and got into the limo to head over to the banquet hall the guys had rented back in town. As soon as we were in the limo, Kathy had sat on Shooters lap and they started making out. Red leaned over to me and we also started kissing. I immediately pulled his cock out again so I could play with it. He started massaging my ass and it got me really hot. I slid down and set myself right between Red's legs and started licking up and down his shaft. Then I stuck his cock in my mouth and started taking him in and out at a nice pace.

At this point, Kathy looked back over her shoulder and told me what a slut I was. I showed her the thumbs up sign and heard her tell Shooter that she was sure I wanted to really get fucked tonight. Then I heard her say to shooter, "you've been checking out that hot slut all night, you want to fuck her?"

"Red, you ok with that?" he said.

"Sure, it's not like she hasn't been with any of my brothers before," Red replied.

I felt Shooter get back behind me, then lift up the back of my dress. I felt Kathy's evil hand pull my thong to the side, then her hair on my ass as I imagined she was lubricating Shooter with some of her saliva. Then I felt her hand guide shooter into my ass. It felt so hot to have Red in my mouth and Shooter's eight inch cock being buried in my ass. After a few minutes, he had his cock all the way in and started a nice rhythm, pounding long strokes in and out of my ass. I meanwhile looked up into Red's eyes as I sucked his cock, working in time with Shooter. As he pounded in, I moved forward and took Red all the way into my throat, then out when Shooter pulled out. After about ten minutes, I felt the pace from behind quicken and started really going to work on Red. A few minutes later, I felt Shooter shoot his huge load into my ass as Red groaned and dumped a load into my mouth, which I hungrily swallowed down, expertly. I felt Kathy move my thong back in place and tell me that it should be nice and soaked by the end of the night from his cum dripping out of me. I kissed Red's cock and put it back in his pants as we pulled up to the banquet hall.

I felt so dirty as we walked in, filled with two loads of cum and headed straight for the bar with the group to get a chaser. We started out with a round of shots, then had another glass of wine each. Thankfully we had dinner, so I was just pretty buzzed at this point and not totally wasted. We danced for a while together to some hip-hop. Thankfully, Kathy and I had practiced some dance moves during the week and I tried to look as sexy as the other girls, moving my hips and shaking my ass to the tunes. At one point, the lanky black guy whose cock I also sucked at the Halloween Bash asked if he could have a dance and I agreed. It ended up being a slow one and he made sure to keep both hands on the lower part of my back, just enough to rub my ass when we turned away from Red. He made sure to tell me how much he had enjoyed fucking my mouth at the party a few weeks ago. I told him his was the first cock I had ever deepthroated and felt his ten inches start to get hard.

He peered over to see Red, his date, Kathy, and shooter at the bar doing a round of shots and took the opportunity to french kiss me right there on the dance floor. Then he grabbed my hand and led me off the dance floor and towards the bathrooms down the back hallway. He pulled me into the men's room and into a stall. He ordered me to sit down on the toilet while he unzipped his pants. He pulled out his half erect cock and shoved it right into my open, waiting mouth. I couldn't believe how hungry I had become for cock. Just like at the party, he held my head and began fucking my mouth roughly, burying his cock down my throat and then pulling out so the tip was just inside my mouth. Each time, his balls would come to rest on my chin. One time, he pulled on of those dispoable cameras and snapped off a shot with his cock all the way in and his tiny pubes covering my mouth. A few minutes later, he started to buck at the knees and then shot his load into my mouth. There was so much, some dribbled out my mouth, but I caught it with my fingers before it hit my dress. He snapped another shot of me licking it off and then made sure the bathroom was clear before he headed out. I took a moment to pull some makeup out of my purse and touch up my smeared lipsick, then headed back out to the bar for another cum chaser of alcohol.

Red asked me where I had been and I told him I had to use the rest room for a minute. He led me out to the dance floor for another slow dance and started whispering in my ear how much he was looking forward to fucking me. That turned me on so much and I peered over to Kathy and nodded my head that we should leave. She was grinding up on Shooter and I could see she was ready to go too. Red called the limo driver and told him we were ready to head to the hotel that they had booked rooms at. The guys were pretty happy and decided to roll back the ceiling window and stand up and ride in the cool air for a bit.

Kathy gave me that evil grin of hers and went over to Red and unzip his fly. She told me that I had already sucked him off tonight, so it was her turn. I got in front of shooter and pulled out his cock in turn. It took a little more time to get them hard, the boys were a little drunk. But we accomplished the task and then Kathy pulled out a five and said, "first one to finish off her guy, gets it." I quickly picked up my pace and kept an eye on her to see about her progress. She worked Red's cock and I saw him looking down at her. She reach up and pulled down her strapless dress and bra and that's when he pulled out and dumped his load right onto her exposed tits. Damn her and her unfair advantages. I felt Shooter start to moan and then felt him dump a smallish load into my mouth. His bigger load still reside in my ass, and some down my inner thigh at this point.

The driver pulled up to the hotel and we all got out. The guys checked us into a suite that had a set of rooms. The guys fixed us drinks and then I saw Kathy grab shooter and pull him into the bedroom on the right of the living area. Red came over to me, set the drinks down on the coffee table, then wrapped his big arms around me, put his hands on my ass, and picked me up. I wrapped my legs around his hips, arms around his shoulders and we began to kiss as he pushed us up against the wall. I reached down and undid his fly and pulled his cock out. I moved my thong out of the way and he pressed his cock against my ass. He slowly eased his way in and then started to fuck me. He moved his hips down and back and then would slam into me as I used his shoulders to brace my weight so that I stayed elevated. He fucked me hard and good. After a few minutes, he walked us over to the couch and layed us down, me on my back length wise. He was on top and moved my legs up to his shoulders and then got completely on top of me and started pounding me. My ass was in such a position that it was behind arced upwards to meet his cock as he made each thrust. His balls would slam into my ass every time he pounded down. I just looked down past my soaking wet thong and watched his cock move in and out of my stretched out asshole.

A few minutes later he got off and went over to sit down in a chair and I ran over and sat in his lap and guided his cock back into my longing ass pussy. I rode him for what seemed an eternity, him with one hand on my ass, one on my breast forms. Kathy really did good work as I imagine he visualized fucking a hot chick's pussy in his mind. I heard his breathing get faster as mine did as well and then he grabbed onto me tight and slammed into me deep and shot his load in. I felt his hot spunk and also started to come and soak my thong. I turned around to see Kathy and Shooter peaking out of the bedroom, Shooter pounding her pussy from behind and sticking a finger in her mouth and holding one of her tits. I just lay up against Red's chest, head turned watching my good friend get nailed. Shooter came a few minutes later and they both collapsed in the doorway.

Red picked me up and carried me into the bedroom, stripped off my dress and we layed together the rest of the night, me in my lingerie, him naked with my hand around his cock. I couldn't help think of how much of a cum whore I had become...

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
13 Comments
ThegentlesoldierThegentlesoldier6 months ago

Very sexy story. I loved it, both parts. So much cum, I bet next time there will be more men.

robin48robin48over 2 years ago

nice story...believable

Riki1942Riki1942over 8 years ago
I Love The Whole Scene!

I love stories on this subject! I'm gay, a Transvestite and I love sucking cock and getting fucked! I have a special friend who is the only one that I let fuck me bareback and know well that thrill of knowing I have my partners load deep in my ass when he cums. I think it would be a real turn on to have a girl like that watching me getting fucked.

Riki

Tootight1Tootight1almost 9 years ago
good story

liked the story a lot. a good friend, I would think so. not having any background on the people leads to some serious questions. the first one being, should they get checked for STD? the second, being, when do you sit back and re-evaluate the situation, with Kathy. what are his feelings about her, and her feelings about him. how much further are they wanting to take this, and to what end? great story, could make a good porn, or full length movie.

ChrisissyChrisissyover 9 years ago
Love it!

Love the story line! Would love to have had this type of fun in college!

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Hallowe'en Party After losing bet, gets lots of attention.in Transgender & Crossdressers
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
Billy Is Billie on Halloween He is invited to a costume party as a schoolgirl.in Transgender & Crossdressers
The Barbeque A lost bet leads to a day as one of the girls.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
More Stories