Halloween is a Night to Let Go

Jaimie was my college room-mate, during my sophomore year. He was a theater major, fairly thin but a little soft-bodied, and almost a foot shorter than me. He hadn't even started to shave every day yet so she really looked too young for college.

We got along very well, but we traveled in different circles, as they say -- I was a business major (my name, by the way, is Bob.) Sometimes on weekends, when I wasn't going out with my buddies, Jaimie and I would hang out (especially if the weather was brutal -- this was Vermont and it could get cold) and we'd listen to music and just talk.

I was really looking forward to Halloween -- there were going to be a lot of parties, on campus and around town, and I wanted to hit as many of them as possible. Or stay at one if I found a hot girl. Also, Halloween brought out the wild animal in people -- must be the dressing up, pretending to be someone else, and getting drunk. And as Halloween was going to be on a Friday, I was looking forward to a weekend of collegiate debauchery.

My costume was nothing original -- some people built elaborate costumes made out of cardboard and chicken wire, and couldn't move through the crowd or even sit down. ("I'm the Arc de Triumphe!"). I was Frankenstein's Monster, based on Herman Munster. Big boots, old suit, green face make-up, glue-on bolts, and done.

I spent much of the afternoon drinking beer, and getting my costume ready. Friends would drop by and stick their head in the room; wed make plans to run into each other later that night at this place or that party. I didn't pay much attention to Jaimie, who was traveling back and forth from our room to the bathroom, hauling bags of clothing and I don't know what. He was out more than in.

It was 8 o'clock that night, and I was about ready to go out when a girl just walked right into my room. Red hair, kind of curly, spike heels with open toes (red painted toenails) and a bathrobe. What the hell?

Before I can say anything, she looks, up takes off the road, and grins from ear to ear. "Think it'll work?" asks Jaimie.

My roommate had transformed himself completely into a girl -- a woman, really. You could recognize him, especially if you knew him -- and I think from his face, which was not masculine but not really feminine, many people would guess he was male, but his make-up, hair, dress -- a red satiny sheath with skinny shoulder straps -- would not give it away. Neither would his body -- trim legs but nice legs, the dress came to above his knees -- and god-damn! He had hips and an ass, and he wasn't big-breasted by any means but he had something in there -- he had to have had something in there, but it didn't show. The tight red dress really gave him curves. And he had stockings on.

"Holy shit," I said. My jaw was actually dropped. "Yeah, I think you'll pass. But you won't pick up any girls in that outfit -- unless they're into girls!"

Jaimie laughed at that and I could tell he was pleased with my reaction -- he'd put a lot of work into his outfit and paid a lot of attention to detail. Maybe it was because he was in theater, but his make-up was flawless. Bright red lipstick, eye shadow, long lashes...amazing. But his hair -- it wasn't a wig. He'd dyed his dirty-blond hair red and curled it.

Jaimie said, "Well, I'm off -- see you later," and walked out the door. Damn, he looked like a sexy woman just walking away -- just a little sway, and -- was that a little jiggle? I even heard a couple of guys in the build holler something at him, and one of our friends on the floor stuck his head in the door and asked, "Bob, who was that!?"

It was a wild night, I went to a bar, then a couple house parties, and around 11:30 a couple friends and I drove a little way out of town to another house party -- in Vermont, you don't have to drive far outside of a town to be 'in the sticks.' It was a small house, very crowded. We looked at some of the costumes, grabbed a beer, hung out with friends, had a good time. Eventually I worked my way to the front of the house. The Rolling Stones were playing -- loud -- and in the dining room/living room area, people were dancing. Well, you couldn't call it dancing, really, the place was jammed with people, so they were just squeezed in, and kind of jumping up and down or bobbing to the music. Many had shed pieces of their costume, or all of it, and we in 'regular' clothes. It was just a mob of mean and women having a good time.

A hand grabbed my arm, it was Wendy, a friend of mine and she hollered "Come on!" and dragged me into the fray. Pushed along without any plan, I ended up almost in the middle of the mob, and we were just kinds of dancing, our arms around the waists and shoulders of people near us. I really got into it.

Soon I noticed, though, that some people were bobbing, but kind of rubbing on each other. Rubbing groin and copping feels, grinding on each other. Wendy kind of popped out of the crowd right in front of me and right into my arms, we started bobbing and grinding without missing a beat. Wendy had long blond hair, had a few extra pounds, and was very nice to crush my body into. She and I were just friends, we'd never been intimate, but the moment, the alcohol -- we were really rubbing on each other.

Just as suddenly, Jaimie appeared next to us. Wendy shrieked happily and grabbed him and pulled him into us and yelled in my ear, "This is Jaimie. I just met her tonight. She's really neat." ('Really neat' was Wendy's highest compliment.)

Wendy pulled Jaime right into us, and Jaimie was smiling and raising his (her?) arms over her head and grinding into Wendy's thigh -- and then mine. The mob went on bobbing around us, no one noticing anything, the music was blasting, and the tribal sorta-dancing continued for quite a while. Jaimie kept rubbing on, and growing bolder, caressing Wendy -- and Wendy kept rubbing on me. At one point she was just straddling my thigh, grinding almost circles and whispered in my ear, "Isn't she cute? She's so hot."

So Wendy thought Jaimie was a girl -- and hot. I thought Wendy was hot -- and the booze and her rubbing her large breasts and thighs against me had nothing to do with it -- and Jaimie was high on the thrills he was getting 'passing' and rubbing on Wendy -- and me, once in a while -- or high on I don't know what.

Finally Wendy stopped and said, "I need air." We were crushed in there, it was hot, Wendy was perspiring a bit...and Jaimie was a little bit disheveled but amazing still intact. How he could be in that mob on pike heels, I didn't know.

Wendy grabbed my hand and whispered in my ear again, "Bring Jaimie." I grabbed Jaimie's hand and we worked our way out of the mob.

Wendy led us upstairs, down a hall, and she went into the bathroom. She automatically looked at Jaimie -- all women go to the bathroom together -- and Jaimie went in with her. They were in there for more than a few minutes, and I wondered how Jaimie was going to pass that particular test -- and hen they emerged Wendy still looked overheated and Jaimie's lipstick was smeared.

I went into the bathroom and Jaimie told Wendy, "I have to touch up my face," and followed me in. I held myself up on the wall while peeing and Jaimie re-did his lipstick -- I hadn't noticed his tiny silver purse before.

"She thinks you're hot," I told him.

"So do I," said Jaimie, smiling.

"No, man, she thinks you're a girl!" I said, laughing.

"Jaimie finished his lipstick, looked in the mirror a moment and then looked at me, standing their with my cock in my hand, and said, "Tonight, so do I." He spun on a heel and walked out of the bathroom. I splashed water on my face and went out, Wendy and Jaimie weren't in the hall but I found them in a bedroom across the way, sitting on a bed piled high with coats.

I sat on the other side of Wendy and she immediately wrapped an arm around my shoulders and pulled me in for a kiss. It was a big, sloppy kiss, lots of tongue -- my favorite. Within a moment I noticed her other hand was on Jaimie's thigh. Jaimie just sat there. Wendy and I continued kissing, Wendy's hand started moving on Jaimie's thigh and Jaimie pulled his dress up and bit and Wendy's hand hit the lace at the top of Jaimie's stocking. She moaned at that, and spun around and kissed Jaimie. I started shoving coats off the bed.

I moved next to Wendy, on my knees on the bed, and she turned and looked up; we kissed. I leaned her back and kept kissing her, and Jaimie semi-straddled one of her thighs and was caressing her breasts. Wendy's eyes were closed and she was really enjoying the feeling of my mouth on hers, and Jaimie's body on hers and her breasts being caressed through her sweater. Wendy and I shed our tops and and resumed kissing, Jaimie caressing and sucking her breasts. I started rubbing her left breast while Jaimie was sucking her right breast and stroking her body -- occasionally our hands bumps into each other.

Wendy broke our kiss and raised her head to see Jaimie sucking one tit and me caressing the other. Jaimie locked eyes with Wendy, moved over to the breast I was caressing, and started tonguing the nipple between my fingers, and then took my hand in his, and eyes still locked on Wendy's, slid my finger into his mouth and sucked it like a little cock.

I had never had sex with a guy, let alone a guy in a dress, but at this point I was horny to the point of bursting and no longer cared. I didn't have plans to go down on him but if Jaimie was sending a signal I wasn't arguing.

Wendy just moaned, Oh, god," and stripped off her jeans. I got naked and fell back onto Wendy, and Jaimie got up off the bed, reached around behind him (her?) as woman do and dropped the dress. Spike heals, thigh-high stockings, red satin panties with ruffles, and a red satin bra. Jaimie didn't have large breasts be he had something there...because his body was soft, the shape of the bra cup gave him small breasts. She looked hot.

I rolled off Wendy, and let Jaimie slowly crawl his way up her body. She lay full out on top of Wendy and they began seriously kissing. I was rock hard watching this.

Wendy reached and pulled me to her, so that we could kiss, and my body rolled into hers -- and Jaimie's. My cock was pressed against a soft thigh, no stocking so it was Wendy's -- but whose hand was squeezing my cock?

Jaimie slid down Wendy's body, and nibbled her way down...down...Wendy gasped and Jaimie buried her head between Wendy's thighs. I moved up and put my throbbing hard-on on Wendy's face and she attacked it with her mouth.

Wendy had a quick orgasm from Jaimie's tongue, and pulled him up -- she released my cock to kiss her and taste herself on Jaimie's lips. She looked up at me and I moved down and she and I kissed -- I could taste her juices on her lips and tongue. Wendy turned to Jaimie and kissed her again, then me, and soon we were in a three-way kiss.

A redhead and a blond were fucking their tongues into my mouth. That the redhead was a guy, my roommate, gave me a sense of unease but...more than that, I didn't care.

I moved back up to my knees and my cock was in front of Wendy's face again -- and below Jaimie's. Wendy licked the underside of the shaft ad Jaimie took the head into his mouth. Wendy's eyes blazed, watching a hot redhead share a cock with her.

I reluctantly pulled away but slid down and between Wendy's thighs and slid right into her. Jaimie was all over her tits and face, kissing, sucking, caressing, as I fucked Wendy as hard as I could. Wendy's tits were each almost the size of Jaimie's head, so I had to rise up to give him room.

"Fuck me-fuck me-fuck-me," Wendy moaned. She was very tight and felt so good wrapped around my cock. She grabbed Jaimie by the hair, mashed their mouths together, and trembled beneath me -- her second orgasm.

As Wendy panted, catching her breath, I slid out of her and Jaimie slid down, and sucked my cock, licking Wendy's juices from it. He slid back up and moved into the kiss me, her tongue sticking out. Jaimie was a great kisser; tickling the roof of my mouth with her tongue, sealing out mouths together and sucking hard.

Jaimie then kissed Wendy just as deeply, and then stood up off the bed, turning as she stood up so that her back was to us. She had a great little body -- better than most other girls I'd been with. She stretched and tried to arrange her hair.

Wendy whispered to me: "I want to watch you fuck her," and before I could answer, Jaimie slid her panties down -- nice ass -- and turned around, facing us. Red satin bra over little tits, lace-top thigh-high stockings -- and a short (five inches?) but hard cock, sticking straight out with a slight upward curve.

"Oh, god!" said Wendy, "she's got a dick!" I thought Wendy might be shocked or perturbed but when Jaimie climbed back on her she positively wrapped herself around Jaimie and pulled her in...Jaimie's cock slid right into Wendy and they began fucking. Wendy caressed Jaimie's back and ass. I moved and put my cock back in Wendy's face, and she sucked me -- hard.

Jaimie was too short to reach my cock -- or Wendy's mouth -- but she kissed my thigh.

Wendy really started to buck, almost screaming, "fuck me-fuck me" again.

Wendy came again -- I love multi-orgasmic women -- and Jaimie pulled out, his cock glistening and hard. Wendy pawed at Jaimie and pulled him up, sucking both our cocks. First one, then the other, then rubbing my cock on Jaimie's, then stuffing both cockheads into her mouth.

Jaimie dropped down the wrap around Wendy and share my cock. With both of them licking, sucking, stroking, I began to lose control -- "Oh, yes, I'm gonna cum" -- and they just began sucking harder. I rocked my hips harder and faster and I came in Wendy's mouth, and Jaimie's. As much as possible they shared my explosions. I moved down and we had another three-way kiss -- sticky.

Wendy moved Jaimie up and her cock was sliding along our lips and tongues. I opened my mouth and sucked it in -- hard. Wendy's eyes were on fire, watching me suck this cock. My left hand was wrapped around Jaimie, caressing her very sexy thighs and ass. Except for the hard cock in my mouth, yes, Jaimie could 'pass.'

Unlike and Wendy and I, Jaime came very quietly -- no moaning or bucking, just shot a blast into my mouth. I backed off and a rope of cum shot between Wendy's face and mine, then she grabbed Jaimie's cock and let the rest flow into her mouth.

Another sticky three-way kiss...I was actively, hungrily sucking Jaimie's tongue. While Wendy and Jaimie continued to kiss, I moved between Wendy's thighs and flicked my tongue -- fast -- across her clit and her thighs clenched and she shuddered one last time.

We caught our breath, and with a little laughter, found our clothes, and left the room, and the party. Wendy kissed us both good bye.

Jaime looked at me and asked, "Now what?" (And that is a different story, for a different time.)

To finish this one, Wendy and I didn't see each other for a couple of weeks after that Halloween night. We did get together several times in the spring for sex; Wendy developed a taste for being spanked. She said she could almost come from having her ass slapped. By her junior year she was only dating women -- 'lipstick lesbians' -- but she was always very friendly to me when we ran into each other.

I always found Wendy -- usually dressed in jeans and bulky sweaters, and more than a few pounds overweight -- to be more sexually attractive than a lot of the Hollywood and TV stars. Maybe that's because of an attachment to her participation in my first bi-sex, maybe it was the thrill we shared of spanking her and then taking her...maybe it was that she knew I had a thing for short red-heads, with tight boobs and a cock.

But as I said, that's another story.