"I don't know how I let you talk me into this," I said as Henry drove the car into the hotel parking lot. I nervously looked up at the tall building, the lights from the windows shining out into the night. I realized my hands were trembling slightly, and tried to calm them.
"Because this will be awesome, that's why," Henry said. I looked at him and he grinned. I had seen that grin a lot in my life. Henry and I had been friends since we were kids. We had been through a lot, but never anything like this.
"I don't know, man," I said, "A gang bang, though? With some hooker?"
"I mean I don't know if I'd use the term 'gang bang'," Henry said, waving a hand dismissively as he parked the car, "It's literally just the five of us. And don't call her a hooker, Dirk said she's a really high-price escort. She's a professional." He turned off the car and we both stepped out. I was shaking a little more now, and my heart was absolutely pounding, but my body seemed to be on autopilot.
"OK fine, but what if..." I said, quietly. I looked around the empty parking lot. I'm not sure who I was looking for or who I would have been nervous about seeing. I did clock Josh, Tad, and Dirk's cars already parked.
"She won't find out!" Henry said, louder than I would have liked, "Listen, you know I love your fiance, but this is a once in a lifetime opportunity! Plus, wouldn't you rather do something like this when you're just engaged and not fucking married? That's way worse!"
"I guess," I said. I didn't really see the difference. I knew what I was doing was wrong, but my fiance had been out of town on work a lot lately and it didn't look like that was going to change anytime soon. As a result, we hadn't had sex in a while. A long while. The thought of fucking some hot chick, whether or not four of my friends watched, turned me on so much it kind of clouded my thoughts to everything else. Plus Henry, along with my other friends, have been really supportive about it. They really helped me feel like what I was doing wasn't that bad. I knew it was that bad, deep down, but they helped.
I looked over at Henry, who was confidently striding next to me through the parking lot. Henry was tall, like me, but in a little better shape. He didn't have a six pack or anything, but he worked out way more than I did. I noticed that he had combed and smoothed his short blonde hair in preparation, which I admit looked good. His face was also freshly shaven and he had thrown on what looked like a new polo shirt and jeans.
We walked into the hotel and continued past the front desk, where the pretty brown-haired clerk smiled at us but did not inquire further. My pulse slammed in my ears as I found myself wondering if the girl waiting for us was going to be as good-looking as that girl had been. As we rounded the corner, Henry said in a low voice, "Dirk already texted me and told me they're in room 312."
I checked my phone. No messages from Dirk or in our group chat. I found it a little odd he had messaged only Henry and not me, but I brushed it off as jitters. We reached the elevators and, once the doors had slid open, stepped inside. Henry pressed the button for the third floor. The doors closed and the elevator started to slowly make its way up.
"Listen," Henry said, after a quiet moment, "if we're going to do this..."
"Yeah?"
"Just," Henry paused, clearly trying to think of a good way to word whatever he was about to say, "Just try to be cool about everything."
"What is that supposed to mean?" I asked, taken aback.
"It's just that you can be a little weird about stuff sometimes," Henry explained, "Which usually isn't a problem, it's not like you're not fun to hang out with or anything. But like, let's call a spade a spade here, the five of us are about to fuck some chick together."
"Yeah, I'm aware."
"No, what I'm saying is we're all about to do something we've never done before. It's probably going to be great, but let's be real, none of us really know what to expect. We're all in this together."
"Huh, I hadn't really looked at it that way."
"Yeah, so whatever happens in there, just try to go with the flow. Be cool. Just let it happen."
I nodded to him, but also to myself as the doors opened and we stepped out. We followed the signs to room 312 and I thought about this more. My nerves were calmed, slightly, by the thought that my friends were probably just as nervous about this as I was. However, we finally reached room 312 and my heart felt like it was going to pound out of my chest. Henry knocked, and very quickly the door opened. Josh smiled at us both and raised his eyebrows, then gestured for us to come in.
Josh was a college friend of mine. He was asain, and shorter than Henry and me, but way stockier and clearly worked out. He kept is jet black hair cut very short and was also wearing nicer clothes than I was used to seeing him in.
The room was simple, but nice. A single bed sat in the middle next to a few bedside tables. A chair was in the corner next to the desk with a television. I saw Henry drop his backpack into the empty chair. Tad and Dirk were already there, and so was the woman.
Dirk was a long-time co-worker of mine. We had worked at the same company for almost six years and were pretty good friends by this point. Dirk was tall and skinny, but with a square jaw. He had short, dark hair and dark skin. Tad was as white as Henry and I. Shorter than Dirk but taller than Josh, he had shaggy black hair that even now looked unkempt. I had also met Tad in college, where we had actually been roommates with Josh in our last two years. I nodded to both of them. As we entered, they both straightened to attention and smiled, obviously eager to get going.
My heart leapt into my throat as I looked at the bed, where the woman sat. She was already undressed, wearing only a lacey black bra and panties. Even with her lounging on the bed, I could tell she was petite - shorter than probably all of us - with wide hips but a slender waist. She had long blonde hair that she wore down and had wide blue eyes, which were currently looking down at the phone in her hands. The blonde hair fell down over her amazing tits. They were bigger than my fiance's, but not huge. As soon as we walked in, she perked up. Her eyes shot to Henry, and then to me, and then to Dirk. I saw Dirk give her a small nod, to which she responded with a smile and put her phone down on a bedside table.
"You boys ready to get started?" She asked, leaning back against the headboard and spreading her arms out to the side. As she did, she arched her back, making her amazing breasts pop even more. I felt myself start to get hard through my jeans.
The room was quiet for a brief moment before Henry said, "Fuck yeah."
"Alright, let's get to it then," she said, still smiling, "Why don't y'all whip those cocks out for me. I want to see five naked men in front of me."
My heart threatened to burst through my rib cage now. This was it, do or die. I had, of course, seen Josh, Tad, and Henry naked before, but never anything more than a glance. As for Dirk, I couldn't even remember a time when we were in the bathroom together at the same time. I hesitated, but then saw all four of my friends start to undress. While the others started with their shirts, Henry, next to me, unbuttoned his jeans and dropped them. He hadn't worn any underwear and his hardening cock flopped out. I had forgotten how hung he was. I tried not to stare as he kicked off his jeans and pulled off his shirt.
"Not bad," the girl said, eyeing Henry's cock. I found myself thinking she wasn't wrong.
As I began to pull my shirt off with trembling hands, the three others had already begun disrobing from the waist down. I couldn't help but look as I tossed my shirt aside. My heart dropped as I glanced at all three now exposed dicks. My penis was definitely the smallest here. I hadn't even thought about this. Tad already had a full erection, his dick sticking straight out from him like a metal rod.
As I pulled my pants off, I saw the other four begin to slowly stroke their cocks as they approached the bed. I had definitely never seen any of my friends masturbate before. This made me realize how deep I was already in this. This both terrified me, but also calmed me, oddly. I dropped my underwear and my own modestly sized erection bounced against the cool air of the room. I had never before been so aware of my own nakedness. No turning back now, I thought to myself. I tossed my clothes into a small pile and looked over at the bed. My heart leapt and my erection throbbed when I saw the girl, her eyes locked on mine, beckoning me over with a single finger.
I approached the side of the bed, standing next to Henry and Tad. Our shoulders were touching, and I felt them move as they continued to stroke their own cocks. I followed suit, trying to focus on the girl's tits and not Dirk's cock, which I could see just past her.
"You're first, cutie," the girl said to me. I sucked in a small breath as she reached for me. Me? Why me? I had hoped to maybe just watch at first, get a feel for what we're doing. I looked at Henry, who smiled and jerked his head towards the bed in an encouraging way. I took in a deep breath and remembered to go with the flow.
As she pulled me onto the bed, my heart began to beat even faster against my chest. She pushed me onto my back, where I lay with my upper torso propped up against the headboard. She smiled and slowly crawled backwards, walking her hands down my bare chest and stomach. I was trying to keep my attention on her, but I was always aware of the looming, naked figures of my four friends, all of them now slowly stroking their hard cocks.
She reached my own erect penis and firmly grasped it with her hand. My erection pulsed excitedly against her fingers as she squeezed. She parted her red lips and, with a sly smile, took my cock into her mouth. At once, my eyes closed and my head fell back as she ran her mouth up and down the length of her shaft. I felt her slide her tongue up and down and around my cock as it slid in and out of her mouth. She was a true master. My fiance gave me plenty of blowjobs, but what this girl was doing was on a whole other level. She began to bob faster on my dick, spit dribbling down the sides of my cock. I looked back down at her, watching her push a lock of her blonde hair behind her ear. I wished she would take off her bra and panties, it would have been so much hotter with her naked too. In my ecstasy, I failed to notice my four friends moving slowly closer around the edge of the bed.
Suddenly, I felt someone grab my wrist and start lifting my hand. I snapped my head around and saw Henry guiding my hand towards his own erect cock. I looked up at him, shocked, but he just smiled, raised his eyebrows, and said softly, "Come on, man."
Before I could respond, Dirk spoke up too, "Yeah dude, you're hogging all the action." At this, he grabbed my other hand and started forcing it towards his own dick.
"What the hell, no way," I said. I tried to pull my hands away, but Henry and Dirk tightened their grips. I didn't want to make too much of a scene, so I didn't try any harder. Before I could say something else, the girl pulled herself away from my cock and took in what she saw. She smiled in a mischievous grin.
"Oh my god," she said, "That's so fucking hot, I love guy-on-guy. Jerk them off, that's going to get me so wet so fast." She bent down again and took my cock back into her mouth, but kept her wide, blue eyes looking up at me expectantly.
