My Four Friends

"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.

I sighed and looked back at both Dirk and Henry. Josh and Tad were both nodding, smiling encouragingly, and continuing to stroke their cocks. Henry gave me a knowing look, not letting go of my hand. I knew what he meant. This is the kind of thing he had been talking about when he said I should "go with the flow".

I relented, allowing Dirk and Henry to both place my hands around their cocks. Their members were warm and stiff in my hand, and honestly didn't feel terrible. I had probably jerked off so many times that feeling a hard cock in my hand was nothing new to me.

"Go on," Henry said quietly.

Keeping my eyes firmly on the girl between my legs, I began to stroke both of their cocks. As I did, Dirk let out a loud sigh and put his hands on his waist. Henry smiled, closed his eyes, and said, "Fuck yeah man, that's so good."

The girl paused my blowjob once again, smiled, and moaned, "Oh my fucking god, that's so fucking hot. Keep going."

We continued for a small while like this, the girl taking my dick into and out of her mouth while I ran my hands up and down Dirk and Henry's cocks. The room was quiet save for the wet noises coming from her mouth and Dirk and Henry's soft moans. I felt my friends' erections grow harder in my hands.

"Fuck yeah, stroke their cocks," Tad said, quietly but suddenly. I was surprised and looked at him. I was expecting him and Josh to be watching the girl do her work, but both of them had their eyes locked on what I was doing.

"Do you like it?" Josh asked, working his own cock.

"What?" I said. For a moment, I stopped working Henry's cock out of surprise, but he reached down and moved my hand, indicating for me to continue. I obliged but continued to look at Josh.

"Do you like it?" He asked again, "Stroking their cocks?"

"Um, I guess it's not bad," I responded.

"He fucking loves it," the girl chimed in, lifting her head up, "Look how fucking hard he is." She pointed to my cock, and Josh, Tad, and Henry laughed softly. I felt a rush of embarrassment. I mean, of course I was hard because of the blowjob. Right? She looked over at Dirk.

"And look, he's loving it, too. Oh my god, you know what would be so hot?" She looked at me, an eager smile on her face. She reached over and pulled me to her. I dropped both penises, but neither Henry or Dirk seemed to mind. She positioned me on my knees on the bed, right in front of Dirk. I was looking at her, but I could see the outline of his throbbing, hard cock out of the corner of my eye. She raised her eyebrows and gently placed her hand on the back of my head.

"You should suck his cock," she said quietly.

"Oh fuck yeah, you should man!" Josh said eagerly.

"Do it, dude," Tad said.

"You might like it," Henry offered from behind me.

I looked around, bewildered. I was ready to go with the flow, but not ready for anything like this. I had never considered myself gay, bi, or anything close. I had never even messed around with a guy before. Especially someone like Dirk, a guy I had known and worked with for years. I looked up at him. He stood over me, naked and erect, with an odd smile on his face. It wasn't the warm, encouraging smile he had had when he told me to jerk him off.

I started to object, to say no, to do anything, but as soon as my lips parted, Dirk thrust his warm and eager cock into my mouth. A musty, somewhat sweaty taste filled my mouth as his dick did the same. He slid it as far back as he could, over my tongue and dangerously close to my throat, moaning as he did. I tried to pull away, but the girl firmly pressed the back of my head, keeping his cock in my mouth. Dirk began to slide his dick back out, but before it left completely, he thrust it back in again.

"Oh fuck, that's so fucking good," he said, putting his own hand on the back of my head. The girl pulled hers away, but then used it to grab my hand and guide it towards Josh's awaiting cock.

"Do him too," she commanded, "Oh fuck, suck that one and jerk off that one. It's so fucking hot, you're going to get me nice and warmed up for later."

I complied, wrapping the hand around Josh's cock and beginning to work it up and down. At the same time, though, I looked up and gave Dirk a pleading glance. He kept his hand firmly on the back of my head, pushing my mouth onto his cock with every thrust.

"Be cool, man," he said quietly, sliding his cock into my mouth again, "Take one for the team. Oh, and watch those teeth."

This hardly seemed like taking one for the team, but Josh then added, "Yeah dude, it's called foreplay. Gotta take care of the lady before she takes care of us. Be respectful. And stroke faster."

The reality of the situation hit me at that moment. There I was, completely naked, kneeling on a hotel bed, sucking one dude's cock and stroking another while two others guys watched and jerked themselves off. The humiliation shot through me like electricity, setting alight every nerve in my body. However, it wasn't a terrible feeling. As Dirk thrust his hard cock into my mouth once more, I felt a string of drool fall from my lips and onto my fully erect penis. As I stroked Josh's dick harder and faster, I felt it pulse with excitement almost in time with my own. Every time Tad or Henry whispered encouragement behind me, or when I heard the sound of their continued masturbation, my heart raced a little faster. Did I like this?

"Let's switch, yeah?" I heard Henry say. I snapped out of my thoughts as Dirk pulled his cock from my mouth. I let go of Josh's cock and wiped my lips. I noted my still throbbing erection, but was excited to switch with someone else and maybe take a break.

However, I felt hands grab me from behind and spin me around. I was suddenly kneeling before Henry, who touched the tip of his cock to my mouth and gave me a small smile.

"My turn," he said gently.

He pushed his cock against my lips and, to my surprise, they parted without resistance. Henry slid his dick all the way in, over my tongue and into my throat. Henry looked down at me, still smiling.

"Yeah, just like that," he said softly, "Good boy, just like that."

My heart pounded. I had never been called a "good boy" by anyone, much less my best friend of over fifteen years. But when he said it, I couldn't help but get even more turned on. I wanted him to do it again, so I began to bob my head up and down on his cock. I remembered what the girl had done with her tongue, so I tried sliding my tongue up and down his shaft as I sucked. It seemed to work, as Henry closed his eyes and rolled his head back.

"Look, he's loving it," I heard Dirk say from behind me.

"I'm loving it," Tad said from next to Henry. He was still stroking his own cock. When I saw this, I reached over and pulled it from his hands. Without really thinking about it, I began to stroke. Tad did not stop me, and said, "Oh man, looks like he knows what to do."

"I know what I want to do," Dirk said. I then felt Dirk's rough hands grab me around the waist. He pulled, positioning me on my one free hand and knees. I kept sucking Henry's cock and stroking Tad's, but it was a little harder now in this position. I tried my best to keep up. Henry thrust his dick deeper into my mouth, placing one of his hands on the back of my head and moaning softly.

Dirk's hands slowly drifted from my waist to my ass. I felt him caress my cheeks, and then without warning he spanked me. Not very hard, but hard enough to make me pull my mouth from Henry's cock and let out a noise similar to both a small scream and a moan. Tad, Dirk, and Henry laughed at my outburst. Henry pushed my head back towards his cock.

"Ah ah ah," he tutted, "Don't think you're getting out of this that easy, keep going." I followed his order, resuming my bobbing up and down on his cock. To my confusion, I saw Henry and Tad both look over at something behind me.

"Do you have enough, Josh?" Henry asked, looking away but not stopping his pelvic thrusting into and out of my mouth.

"Yeah," I heard Josh respond from behind me, "Yeah it was enough, thanks."

I pondered this for a moment, but then the truth was revealed to me. Walking by behind Tad, towards the door of the room and fully dressed, was the girl. She was counting a large wad of money. Seemingly satisfied, she shoved the money into her purse and saw me looking at her. She smiled and winked, and then disappeared out of the hotel room door.