With the house all to myself from Thursday through Sunday night, I suggested to Robby (our gang bang guru) that it would be great for him to arrange a fuck session where we could take advantage of an empty house for a change, rather than renting a hotel room for our activities. He came through within the first couple of hours, which just shows what an amazing track record he has of snagging seriously fuckable women.
He'd connected with Jamie via a Craigslist ad. She's 30, 5-5 120, with blonde-highlighted light brown hair and 32B tits. The photo posted here is the one she sent along with her request to meet. Because it was midday Thursday, Robby was only able to arrange a threesome, since the rest of the guys in our over-50 GB group couldn't make it on such short notice. Jamie was apparently OK with that, though, since this was to be her first multi-guy sex encounter and she wasn't too sure how overwhelmed she might be with more participants. And if her claims could be believed, it would prove the first time in more than a month that she'd had any kind of sex at all.
While waiting for them to show up, I gave Robby some shit via text because, after picking Jamie up from her place in North Denver, he had trouble finding my house on the southeast side. He claimed his GPS was all fucked up, but I was more certain it was operator error. Also on the way over, he "warned" me that Jamie was a bit on the skanky side, but I replied that, given our plans for the afternoon, that was a benefit rather than a flaw.
They showed up at my place just before 1:00 p.m., around 20 minutes late. I'd prepared our guest room in advance by stripping the queen-size bed and putting on a new bottom sheet plus clean pillow cases, setting out a brand-new tube of lube, and adjusting the shades so the room wouldn't be quite so bright. Meeting them at the front door, I saw that Jamie was dressed in a pleasantly slutty outfit: Short green cloth jacket over a black lace sleeveless top with a purple bra showing underneath, a denim micro-mini skirt that barely covered her ass, and over-the-knee high-heeled leather boots. She had her hair tied back in a ponytail and spun around after coming through the door so I could apply the green silk scarf I was using as a blindfold. She'd asked for this as one of the conditions of the afternoon's activities, and I was happy to oblige.
Given the lateness of their arrival and the fact Robby had to leave in an hour to pick up his kids from school, we immediately headed upstairs and got down to business. I helped Jamie off with her jacket and unzipped her skirt so she could slip it off. She quickly removed her lacy top and I unhooked her bra. We all agreed she could leave her boots on for the duration. Meanwhile, Robby was stripping down to bare skin, tossing his clothes haphazardly onto the floor in his haste to start in on Jamie. She asked us to leave her undershorts on -- they were leopard-print boy-shorts -- which was fine because they'd been altered by having two carefully placed holes cut out of the crotch. One showed off her smoothly shaved pussy while the other exposed her tight little asshole. I ran my hand down over her buttocks and slipped my middle finger into her tight, wet pussy while removing my clothes at a pace considerably slower than Robby had achieved. He put his hands on her small, firm tits and began to suck on her nipples, which stood up nicely to the attention. She used one of her hands to tug on his fully erect cock - it was hard even before he took off his trousers -- and meanwhile I disengaged so I could remove the rest of my clothes as well.
Robby suggested she lie on her back, which she did, and he stuck his face in between her thighs to taste some of that sweet, sweet pussy. I thought he might be down there a while, but after only about a minute of some serious licking he stood up, pulled her hips closer to the edge of the mattress, and jammed his seven-inch dick into her wet slit. She had her legs up in the air with Robby pressing his hands against the backs of her thighs to keep them there as he pounded her hard. I'd stroked myself from a semi-hard to a fully erect state and climbed onto the bed so she could take my dick in her mouth. By changing my angle of approach, I was able to slide my entire member into her mouth. Of course I'm less than six inches, so it's not a huge challenge, but I could still sense the tip of my cock hit the back of her throat with every downward thrust, which was a great feeling.
After a few minutes of fucking her while standing alongside the bed, Robby suggested it was my turn to squeeze my dick into that pussy. We helped flip her over -- her equilibrium was compromised somewhat by the blindfold -- and I entered her from behind, doggie-style. It had been a couple of months since I'd had sex, so this was a welcome opportunity and I made the most of it, thrusting enthusiastically as Jamie reached down with her right hand and rubbed it briskly across her clit. Meanwhile, Robby had opened up the small bottle of Astroglide he'd brought with him and suggested we DP the girl. She was definitely on board with that idea, so we maneuvered ourselves into position with me on my back and her on top, facing me. She reached down and re-inserted my cock into her pussy and leaned forward so I could suck on her tantalizingly erect nipples. I moved my legs together and Jamie did the same with hers, which allowed Robby to climb aboard and straddle the two of us. He squirted some lube onto his index finger and worked it into Jamie's rear hole, removed it quickly, and leaned forward while pressing his cock's head against her anus. She balanced on one hand above me while reaching back with her other hand and pulling her butt cheek aside to provide him greater access. A deep grunt from her, plus added pressure on my dick inside her pussy, told me he was in her ass. I lay still with my hands on Jamie's hips while Robby did all the work. He pounded her ass with enthusiasm and some deep penetration while she ground my pussy against my lower body. I saw Jamie's chest flushing red and moved my hands from her hips to her tits, tugging insistently on her nipples to match the rhythm the two of them were playing out above me. After a couple of minutes, Jamie let out a big groan and announced she was cumming.
By this point Robby was starting to run out of gas, so he pulled out of her ass and stepped across the hall into the bathroom so he could find a towel for wiping off his dick. Jamie rolled off me and onto her back, but she was clearly far from done. Neither was I -- so I climbed off at the foot of the bed and pulled Jamie toward the edge, pushed her legs up into the air and told her to hold them there (which she did by looping her arms around the backs of her knees), and then I sank my cock into her ass. It was the first time I'd done anal in probably 20 years, and it felt terrific. I was soon pounding her with balls-deep thrusts, and she let go of one leg so she could reach down and mash her fingers against her clit in a rapid-fire manner. Meanwhile, Robby crouched next to her face and stuck his newly cleaned-off dick into her mouth. She sucked him enthusiastically while I fucked her ass; then her butt muscles clenched and she was suddenly in the midst of her second orgasm.
Once it passed I withdrew, especially since my legs were shaky from all the thrusting that I was hardly used to anymore. Robby decided he wanted some more of Jamie's asshole, so we switched positions and he stood at the foot of the bed with his dick inserted all the way into her poop-chute. After about eight or ten thrusts he announced he was ready to cum, so he pulled out and shot a nice thick glob of white goo all over her pussy lips, with some coming to rest on her shorts. I was positioned behind her, with her head cradled in my lap, so I reached down and used two of my fingers to scoop up some of Robby's ejaculate. Then I popped my fingers into Jamie's mouth and she sucked them dry.
By now it was time for Robby to split, but I wasn't quite ready to call it quits and Jamie agreed to let me take her home. As Robby dug around on the floor for his discarded clothes and started to put them on, I finally pulled off Jamie's blindfold -- it was simply too much in the way after all this time -- and convinced her to get on top of me, 69-style. Robby said a quick goodbye, to which Jamie was only able to reply with a muffled grunt, since at that moment she had my entire cock in her mouth. I licked her pussy, sucked on her clit and slipped a finger into her ass, hoping to induce a third orgasm, but she came off my cock long enough to explain we'd made her pretty sore down there, so instead I pulled my face and hands away from her crotch and simply let her do her work. About three minutes into this latest activity I said, "OK, finish me off." Jamie took that as a cue to get me to cum, so she wrapped her hand around the base of my cock, sucked harder on the head, and shortly thereafter I was pumping my jizz down her throat.
She wanted to smoke a cigarette (Marlboro!), so she slipped on her black lace top and I led her toward the deck that's just outside our back door. She also wanted something alcoholic to drink, so I unscrewed the top off a tiny bottle of Barefoot Moscato and poured it into a juice glass. Classy presentation, eh? By now it was nearly 2:30, so rather than begin another fuck session -- we were both pretty sore at this point -- I suggested I drive her home. We got dressed and hit the road. On the way there, we enjoyed an interesting conversation about local politics, the police -- she was on probation for her 2nd DUI, thus a suspended drivers' license and the inability to drive -- and other non-sexual elements. As she exited my car she stuck her head back inside and gave me a warm kiss on the lips. "Tell Robby I'll be in touch again soon, OK? And next time, a couple additional guys would be all right." She'd obviously enjoyed herself!
My girlfriend and I already when to Haulover Beach together and loved it. When her two girl friends came to Miami she insisted that we all go together. Of course I said I was down but I played it cool and said only if you're okay with them seeing me naked and me seeing them naked. She said, "Of course I'm okay with it! You're all my best friends!" Her friends said, "Okay but we need to pregame and get a little drunk first" 
All 3 of them were shaved or waxed smooth. They said they always look "presentable". The shorter one had her clit hood pierced and I told my girlfriend she should get one of those too! She actually did eventually get it pierced. The shorter one complimented me back and said, "We can see why (my girlfriend) talks about your cock" as they got to see it go from small to fully hard. I apologized but my girl said, "Don't apologize!" and gave it a squeeze in front of them.
