I was married right out of high school, and to no one's surprise, by the time I was 22 I was separated. She had cheated on me within the first year, and by the time I discovered it, she was already on affair number 3. I moved back in with my parents and she moved to Iowa to be with her "dream man".
I was working as a cook at an upscale chain restaurant. If you've ever worked in that type of place, you know it's pretty much a d***ken and d**g-addled porn production lot that cranks out food. It was not unusual for employees to draw straws as to whom went home with who.
I had been "dating" a server named Diane, which is to say we were pretty much just steady fuckbuddies. Every night was capped off by drinks and pool at the local bar. Most of the employees went to the same place, and it was frequented by other restaurants employees too. Most towns have a couple of bars like this that cater almost exclusively to hospitality employees after about midninght on weekdays. Diane and I would usually drop about 50 bucks each on drinks and then find somewhere to fuck our brains out.
Diane wasn't exactly a vision of perfection. She was about 5'2" and thick. She was a 38D and had a bit of a belly to go along with it, but the girl was a freak. There is NOTHING she wouldn't try once, and she actually enjoyed surprising her lovers with ass-to-mouth. Our first time together was on the hallway floor in front of her parents open door. If it was risky, she'd try it. Dangerous? It made her cum harder. It shouldn't surprise anyone to learn she was also very bi.
A typical Wednesday night found us at our favorite pub, her drinking cosmos and me double fisting pints of Newcastle. I would buy two pints at the bar and drink one on the way back to the table. One of the other servers, Justin, had joined us as most of our crew was giving way to the steakhouse crowd that tended to get rowdier. I usually stayed on as there were a few hot pieces of ass that worked there, particularly the married girl. I may be a hypocrite, but I liked the way she jacked me with her 6 month old wedding ring on.
Making my way through the crowd, half lit and chugging my pint as I walked, I saw Diane's foot working her way up Justin's leg. Feeling like I was going home with a dry dick, I turned around and downed the second pint on the way back to the bar. If I didn't have a woman to ride, I was going to make sure I at least needed a cab ride home. Two more pints and I worked my way to our table. Justin announced he needed to break the seal, and when he left, Diane asked if I was cool with her flirting with Justin.
"It's what it is, D. I know you like to fuck."
"Yea, but honestly, I'm wondering what it would be like to fuck both of you. You up for that?"
By this point, I'd had about 6 or 8 pints and wasn't giving a fuck about anything but getting fucked.
"As long as he doesn't try to put it in the wrong ass."
The waitress walked by and it was my "regular" server. I tipped well, and most of the girls took care of me well if my glass was empty, but this one in particular always brought me two without me asking or explaining. I nodded to her and within a few minutes two more Newcastles had magic-poofed there way to the table. (Obviously I was pretty well recognized at this bar, I don't know if that's good or bad!)
Justin came back and Diane looked at him and said,"You're not set on leaving alone are you?"
Justin looked at me and was obviously more than a little uncomfortable.
"You cool with this man? I mean, I know you guys are sorta......"
"We're not anything," interrupted D,"but two people who fuck when we need it."
I took another sip (read:gulp) of my beer. "Justin, you're not getting what she's saying. She wants us to run a train on her, and right now you're the only thing she's waiting on."
"FUCK!" Justin yelled,"Hell yea, I'm in."
We finished our drinks without saying much more. At this point in my life, I was pretty cynical and brooding. When I was drinking, I wasn't much of a talker. I can imagine Justin was quiet because he had just been hit with a proposition that he might have been rethinking. D was just fucking smug.
D and I loaded up in her car and drove to the hotel we had decided on, Justin was hitting the liquor store for beer and meeting us there. We got the room, and when Justin knocked on the door, D was riding me on the edge of the bed. He cracked open a fresh beer and D took one while she rode me. I can't imagine what a fly on the wall would have thought, D and I both drinking beers while she's rocking her pussy on my cock, and Justin laying next to us stroking his cock and drinking. D came quickly as usual and then got on her knees for the traditional first nut facial between us. My cum shot across her lips nose and tits and when she started licking it off, it put Justin over the top. Cum slut that she was, D scrambled over to his cock and put her lips just over the tip. Just as he shot off, she was catching every drop.
I hadn't paid much attention to Justin til then, but it was obvious he was bigger than me. I'm a little over 8, but he was easily 10 inches and just as thick as me. D slurped on his cock, taking every drop and doing her best to help him recover. Her ass was way up in the air, and I was not going to miss an invitation. Knowing she was soaked, I lined up my cock and buried it to the balls in one stroke. D groaned, and lifted her head off Justin's rapidly hardening tool.
"Fuck this is awesome," she said,"Pound me onto his cock."
I did too. She didn't move at all, just let me fuck her pussy hard enough to give Justin good head from the pounding. I stuck my thumb in her ass and soon I was about to burst. Ordinarily, I would have shot on D's back, but considering Justin was as likely to get hit with it as her, I grabbed her hips and shoved my cock as deep into her as I could before unloading what felt like an oil tanker worth of jizz.
Having a guy cum in her always made D cum too, and she gasped as her wetness started seeping past my cock and onto my balls. At this point, Justin was hard again and when I pulled out, she crawled on top of him. She started riding him, and I finished the beer I was drinking while she was riding me and he watched. When I was done, I got on my knees next to her head, grabbed her by the hair and stuck my half limp cock in her face. She opened her mouth and it was my turn to have another man's thrusts push my dick down D's throat. When I was hard again, I pulled away from her and went around behind them. I grabbed her hips and steadied her motions, then lined me dickhead up with her asshole. I'd never fucked her ass without lube, but at that point I was too d***k to think about that. I pushed hard and her experienced ass allowed half of my length to disappear into her asshole.
"Want me to pull out?"
"No, just remember it's a fucking dry asshole"
"Good, I wouldn't have anyway."
I waited for her asshole to loosen up and then started pushing the rest of my cock into her. I knew this was what she really wanted. DP was on her list of things to try before she died. I reached up and grabbed her hair. I pulled like I knew she loved it, and that's when it got surreal.
"Justin, choke me."
"What?" he asked, looking shocked.
"Choke me while his cock is in my ass and he pulls my hair."
Justin wrapped his hands around her neck as it was arched from my using her hair as a handle. I had never choked her, and I'm sure Justin had never done it to anyone, but she was obviously enjoying it. He would squeeze for a few seconds then let go so she could gasp for air. When she could breathe, it was in gasps followed by guttural words like,"Oh fuck" and "damn good."
I felt that tingle in my balls and knew I would be soon be shooting her ass full of another load of cum, and Justin's breathing told me we'd be pretty close. I let loose first and I think the throbbing of my cock carried through the membrane between D's ass and pussy and sent Justin off too. D began screaming, her ass tightened on my cock and I'm sure her pussy clenched Justin's too. When I was done, I pulled out my cock with a pop, and D rolled off Justin's rapidly deflating dick. He immediately got up and went to the bathroom, then quietly put on his clothes and left. His last sight for the evening was D rolled on her side dutifully sucking my cock fresh from cumming in her ass.
"Damn." Justin shook his head, I guess after what he had just done it was still shocking to see a woman that sucked a man's cock after he had fucked her ass.
D sucked me clean and hard again, and we finished the night with me pinning her arms behind her back while I relentlessly drilled her to my completion.
After I had cum that last time, she curled up in my arms and kissed my cheek before dropping off to a deep satisfied sl**p. While we had all enjoyed a tremendous fucking, I knew it wouldn't have happened without liquid courage and the don't-give-a-fuck attitude that comes with it. It was my first threesome with D, and the only one with another man, but those stories will be for another time.