Something New: Three's a Party

I had a few more sessions with my new girl, and we got to be something like friends. She helped me bring my makeup game to the next level, and we even had one normal non-kinky sex date, but as hot as she was, the rubber dick just wasn't the same. Around the time I was about to break it off with her, she actually met someone she kind of liked on a personal level, and our sexual relationship was over, leaving me to continue my escapades as Sheila.

I was content with my life. New men in my life on the regular, and I still made it down to the glory hole on occasion when I just wanted to guzzle down a lot of cum without all the hassle. I'd found my something new, and I was loving it. I didn't see any need for another change any time soon. Life, however, had other plans.

I was working on arranging a date when another guy I'd reached out to responded back. I was looking forward to a busy week, but it turned out that he wanted to get together the same night as my other date. When I told him I was busy that night, his response caught me off guard.

"I don't mind sharing," he messaged back. "See if your other guy wants to tag team you."

I'd been double-teamed before, most notably that first time in the gloryhole, but a couple times since then. It was super fun, but it usually ended up being a gay couple who wanted a NSA 'gurl' to service them for a night. These were two guys who were 'straight' (which in TrapFinder lingo meant that I wouldn't be receiving any reciprocation, which I was fine with), which meant that their whole entertainment for the night would be me; I wouldn't have to share their attentions with anyone else. I immediately messaged back, and then sent one on to my original date.

"You interested in sharing me with another guy?" I asked. "Got another guy on the hook who doesn't want to wait his turn." His reply was almost immediate.

"You really are a dirty girl, aren't you? If I'd have known you were into that, I'd have asked this sooner. I have a friend who's always been curious about traps. Do you think you could handle three at once?" I replied yes without even thinking about it, and the date was set.

When the night came, I made sure I was at my slutty best. Fishnet stockings over smooth legs, and a satiny open-ass gaff, topped off with a corset and my best looking breastforms under a sheer black babydoll dress, and a gothic red wig of curls. Then I headed out to the hotel where we'd agreed to meet.

My guys had agreed to spring for a fairly high end suite; we wanted to make sure that there was plenty of room for our escapades. Even though I had a fairly conservative woman's coat over my lingerie, I think the dark red wig made me look like a hooker; the only part that bothered me was the idea that I'd have to be paid to do this, when I loved it so much. Still, when the clerk gave me the eye, I winked at him and blew him a kiss before going in to the elevator.

The suite was everything I'd hoped for, and my gentlemen were all waiting for me. They'd cracked open some champagne and were getting to know each other when I arrived, so I joined them on the large sofa for a glass myself, after removing the coat to reveal my feminine charms. I sat down between the two men who obviously knew each other, and we had our bit of small talk; one of them was obviously nervous, but equally excited; the other two had obviously been on TrapFinder for a while and ogled me openly; the closest put his hand on my thigh as soon as I sat down.

After my glass of champagne was empty, I turned to my shy guy, and put my hand on his chest, which his friend took as a cue to start groping my hips and ass. I leaned in to kiss him, holding off just the last little bit until he leaned in for it, and his lips met mine. It was obvious that, while he was nervous, he wasn't exactly inexperienced and he quickly got into the kiss in a way that made me feel very excited. It didn't hurt that his friend had pulled my hips around to expose my butt, and was now kneading my ass cheeks in anticipation.

My third lover was less patient. I caught his approach out of the corner of my eye, and glanced over as he dropped his trousers, and a large, uncut cock sprung to attention a foot from my face. I reached out with one hand and started stroking it, then gave the shy guy a smile and a wink before turning my attention to the cock in my hand. He watched as if transfixed as I kissed the head, then ran my tongue down from the slit along the shaft to the base, then back up again, pressing my tongue underneath as I rose. I gave shy guy one teasing glance before slipping the head between my lips with a pop, and began descending again, feeling the thick shaft and soft skin filling my mouth with its musky warm taste. I heard him exhale slowly as I did, thrusting lightly as I enveloped him as fully as I could, pushing deep enough into my mouth that I would have gagged if I'd had less experience. Instead I just kept working my mouth slowly up and down his cock, while my hands fumbled at shy guy's fly until I got it open and another cock filled my hands.

His cock was nice sized, uncut with an upward curve that I knew would hit my P-spot like a dream, and I moaned appreciatively around the cock in my mouth at the thought of it up my ass. I stroked my hand gently over the surface, paying especial attention to the sensitive edges of the head. He responded, groaning and beginning to thrust lightly in my hand. Meanwhile, the hands on my ass changed position and spread my cheeks, exposing my tight asshole to a warm probing tongue. I loved it when they did that; I pulled the cock as deeply into my throat as I could and held it as sensations radiated out from my ass, then when I couldn't hold it any longer, I pulled off and switched my attention to the cock in my hand, slipping it between my lips and stroking the other, still slick with my spit.

This continued for a minute, one tongue in my puckered asshole while I swapped back and forth on two cocks, drawing them deep into my mouth and humming in the back of my throat while stroking the other, before switching and doing the same to the other cock. Then the tongue in my ass withdrew and I felt something firm replace it, pushing insistently between my cheeks. I had shy guy's cock in my mouth, so I looked up at him with my lipsticked mouth around the base of his shaft as the pressure at my ass slowly pushed in, and I felt my eyes rolling back at the sweet sensation of a throbbing cock filling me up. He looked down at me and suddenly jerked, and I felt a splash of hot cum hit the back of my throat, followed by another, and another.

"Oh," he exclaimed in surprise, "I'm sorry, I should have warned you."

"I'm not at all sorry," I purred, before milking the last of the cum out of his softening cock. Teasingly I showed him the cum on my tongue, then stood up to offer him a kiss. To my surprise, he took the opportunity, leaning in and kissing me, full-tongue, exploring my mouth and tasting his own cum. Meanwhile, the guy in my ass was starting to really get into it, long slow withdrawals with hard thrusts that rocked me forward. My newbie finally seemed satisfied that there was no more cum in my mouth as he drew back, letting me bring his friend to my lips and give him the attention he deserved. He was eager and started face-fucking me as soon as my lips were around his cock, and I caught the new guy watching avidly.

Normally I'd be completely lost in the two cocks pistoning into my mouth and ass, but something about the look in his eyes seemed familiar, so after a moment of enjoying being spit-roasted, I winked at him and crooked a finger to gesture him closer. He didn't hesitate, but leaned in close, until his face was right next to mine. I reached up and gently guided the cock out of my mouth and turned it toward him. New guy looked up shyly at his friend, then opened his mouth and took the cock in; I could see the satisfaction as the thick shaft slipped between his lips, and felt a moment's jealousy before the pounding in my ass got harder and it was all I could do to remember my name. I could feel my cock leaking from the amazing feeling of the assfucking I was receiving, as well as the beautiful sight of a fledgling cocksucker enjoying his first cock.

I let my mind drift as the cock hammering in and out of my ass increased its pace, back to that first fateful night in the men's room. So much time had passed since then, and I'd come to love the cock more and more, both the taste of it and the hot gush of cum down my throat and the delicious sensation of one splitting my cheeks as I felt now. I envied this young man the discovery ahead. The cock in my ass started slamming erratically, harder, and I heard his drawn-out groan as he painted my asshole with his cum. He stroked in and out a few more times and I felt the ever-present disappointment when he finally withdrew, leaving my ass empty but for an oozing puddle of cum that dripped out of my hungry hole.

Speaking of hungry, my new cocksucking friend had found his rhythm, and was really going to town on his friend, whose cock glistened with saliva each time it slipped out, almost all the way, before it vanished once again. I started to feel a little left out; My ass-fucker would probably be a few minutes, so I crawled forward and positioned myself on my back to take the novice cocksucker's bulging head into my mouth. He gasped as I swallowed his cock, and gave a little thrust. I reached up and grabbed his hips to encourage him to continue moving, since I wasn't in a great position to move my head. He caught on quickly enough and began fucking my mouth while sucking his friend's cock. That was when his friend groaned, and I knew what was coming; my fledgling cocksucker was getting his first load of cum.

He gagged for a second, and I thought he was going to spit, but then he unexpectedly rallied and started bobbing on the twitching cock slowly, and I could see his throat working as he swallowed it down. Silly boy didn't know that you're supposed to show it off before you swallowed, but he'd learn. I decided this was my chance, and turned myself around, pushing my ass up against the newbie cocksucker's stiff cock. I reached around and using the lube of my last lover's cum, slipped it into my asshole with a lustful shiver. I was right; his bulbous head and curvature hit my prostate just right, and he soon obliged me by rocking his hips back and forth, sliding his cock out and back into my eager hole.

After a minute, my other two guys came around to the front, and I reached out and took their cocks in my hands, stroking them gently back to life. I brought both cocks together and rubbed them between my hands, before pulling them in and slurping both heads into my mouth. It wasn't easy to work both cocks at the same time, but I was a professional cocksucker at this point, and I worked my head back and forth, letting the two dicks rub against each other as they stretched my cheeks and I worked my tongue on the underside. I probably wouldn't get either of them to cum like this, but by the twitching and the moans, you know they liked what I was doing. Meanwhile my cocksucking lover pounded his curved cock in and out of my asshole until I could barely focus on the pair of cocks stretching my lips.

I knew I wasn't going to last. He was hitting the spot just right, so I stopped playing with my other two lovers, and focused on one cock at a time, stroking one with my hand as I did my best to swallow the other one entirely, then switching. I heard the quickening gasp from the man whose cock was in my hand, so I switched and wrapped my lips around the head just as it spasmed and I felt the hot load spatter the roof of my mouth and drip onto my tongue, before being followed by another burst, then another. I milked the last few drops out then pulled back to show his load puddled on my tongue. As I did so, the other cock jerked in my hand, and a splash of hot cum hit me in the face. I pulled it to my open mouth and heard him grunt as three more surges sent the rest to mix with the pool of jizz already filling my mouth. Before I could clean the last drop of sweet cum off his twitching cock, my third lover thrust just right, and I threw my head back as waves of delight shivered through my body as my own cum spurted out to fill my panties and drip down my inner thighs. This didn't slow him down at all though, and his pounding kept hitting the spot, pushing me further over the edge than I've ever been, until finally I lost track of time or anything else but the rhythms of pleasure washing through my body.

When I came back to myself, I was huddled on the ground, sweaty, sticky with cum dribbling out of my mouth, panties and ass, and my three lovers were getting dressed. My new cocksucker saw me stirring and gave me a shy smile before he left. Sometimes they stayed the night, but it looked like I'd have this luxurious suite to myself for the rest of the night; maybe when my legs stopped shaking I might go down and flirt with the cute clerk a little bit, and see where the night went from there.