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olddenverguy
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@confessions
01 Dec 2017 1:01PM
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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!

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Anonymous
@confessions
09 Mar 2008 3:47PM
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My gf's best friend is the biggest bitch I have ever met. Pretty much everyone that knows her is in agreement with me. We absolutely hate each other and I find it hard to be civil anytime she is around. The problem is that her bitchiness makes her smoking hot to me and I fantasized about her when I was with my gf. This girl owns a restaurant with her husband, so one night I went there and sat at the bar till closing and it ended up just being me and her alone with the doors locked. She was really annoyed with me and kept hinting it was time to leave. I was alittle drunk by now and told her if we could do a shot together I would tell her my reason for being there. Well we did several shots as I confessed my attraction and my fantasies. She was not impressed at all and promptly showed me the door. As i was just about to walk out I grabbed her and tried to kiss and as she pushed me away we both tripped on a stool and fell. While on the floor I tried to kiss her again and this time she kissed me back. That was the hottest kiss ever! After dreaming of this and finally feeling her tongue, that was fucking heaven! We went upstairs to her office and ripped each others clothes off and she practicly shoved my face between the sexiest legs I've evr seen. I have to say when I would fantasize about her it was always a hard grudge type fuck, but this was not the case. After i licked her to orgasm I climbed on top made slow and sensual love to her. The kind where you kiss passionately and stare into each others eyes. It was so amazing and passionate that I came inside her without either of us saying a word. Afterwards we layed there kissing and touching before we went at it again. The girl I hated last week with every fiber of my being is now the girl that I love and lust for more than any woman on the planet. This is my true confession and it feels damn good to get it off my chest.

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Anonymous
@confessions
22 Dec 2016 11:55AM
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I confess, I fucked a secretary in our company. Sylvia is a smoking hot cougar. She has an incredible body for a woman her age and takes very good care of herself. She never had any kids, so I guess that makes it easier. She also has a very classy yet sexy way of dressing for work everyday.

She is as sweet as can be. Always smiling, eager to be helpful in any way she can. One of those positive spirits that, coupled with her stunning looks, makes you want to fuck her. And yes, I have masturbated in the men's room a time or two because looking at Sylvia got me so horny.

We have worked in the same company for 10 years, so we know each other pretty well and are quite comfortable with each other. Our interactions were always professional. I said "were".

I heard from other guys in the office that Sylvia is a crazy flirt. She was never flirtatious with me, maybe because I am one of the big bosses. And because sexual harassment lawsuits are so common, I have never wanted to cross the line into unprofessionalism.

Well, I decided I'd experiment a little. I started to compliment Sylvia whenever she came into my office with something. I had to sign expense accounts and she often prepared them for the sales guys, so her visits to my office were almost daily, though very brief.

I'd say things like, "You look amazing today.", or "That is a stunning blouse you are wearing." or "I love those glasses." and "That hair style looks great on you."

She loved the compliments so much she started walking in and asking, "How do you like this shirt?" or "What do you think of this neckless?" Eventually, her questions got to "Do you think this is sexy?" and "Do you think this is hot looking?"

Then one day she took those daily exchanges to a whole new level. As she was walking out of my office, she turns her head, looking over her shoulder at me with her hand on her hip and asks, "Does my ass look good in these pants? I'm not wearing any panties." I just about dropped my teeth. She walked out with a devilish grin on her face.

From that day forward, she started to get more bold in her approach to me. A few days later she is wearing a white, button down shirt that is sheer enough that you can see she is wearing a lacy bra. She walks into my office, puts the expense reports in front of me on my desk and asks if I can sign them right away, as she waits. I, of course, comply.

As I'm looking over them, she leans over placing her hands on my desk and asks, "Do you like my neckless?"

I look up, and her neckless is hanging perfectly in front of the cleavage between her breasts and I can see right down her blouse at those magnificent tits. I smile ear to ear and nod gleefully. She asks, "Do you like anything else that you see?" All I can say is, "Oh yes." She then says, "I wore this shirt just for you today. The lacy bra is a little extra I threw in for your viewing pleasure." I can't stop smiling. I can feel my face getting beet red. She then turns and walks out with that devilish grin on her face again.

Later that day, I have to leave the building for a meeting. As I step out of my office she says, "Are you leaving for the day?" I tell her yes and she follows me to the elevator. When the elevator door opens, it is empty and the two of us step in. When the doors close, she turns and plants a passionate, lingering kiss on my lips. The door to the elevator opens and she exits saying, "Have a nice day." with that devilish grin again. I am blown away and she is all I can think about for the rest of the day and night.

I'm an early bird and always get to the office by 6 am, way before anyone else does. It's my most productive time of the day before others start arriving by 7:30 am and fills up by 9:00 am. Everybody in the office knows my routine.

The morning after the elevator kiss, I'm in by 6 am as usual. About 6:15, I hear the unusual sound of another person entering the office. I hear the elevator bell. I hear the sound of footsteps on the hard lobby floor. I could hear some shuffling at a cubicle common to one arriving for work. I note that it is unusual so early but keep working at my computer that faces away from my door.

The next thing I hear is "Good Morning" in the sweetest, seductive tone. It is Sylvia at my office door. I turn around in utter shock. There she stands in my doorway wearing one of those wrap around dresses that is propped open by her hand on her hip as she leans on the doorway with her opposite shoulder. It was the most seductive, sexy pose. She is wearing the sexiest lace bra and panties. Her tits are huge. I am speechless.

Without saying a word, she walks in, closes my door, turns off the light, walks behind my desk, spins me around in my office chair, kneels down in front of me and starts undoing my belt and pants. By this time, my cock is rock hard. As soon as she pulls it out of my pants, she goes down on me. Once soaked in her spit, she draws back, unsnaps her bra at the clip between her tits, and starts giving me a titty fuck while looking up at me.

No words have been spoken. The only sound is heavy breathing and moans. Once done with the titty fuck, she stands, turns around facing away from me, lifts her dress to expose her ass, reaches around to pull her panties to the side, and lowers herself down on to my cock.

The sensation of her pussy fucking my cock was amazing. I've never seen a woman get so wet. My cock is quickly covered with her creamy wetness. I can't believe this is happening to me.

I whisper, "I'm going to cum, I'm going to cum." She quickly stands up, turns around, drops to her knees in front of me, looks into my eyes and says, "Cum in my mouth." Down she goes and boom, I explode in her mouth.

She took every drop of cum and kept sucking until I was drained. When it was clear I was finished and my cock already starting to soften, she stands up, straightens up her panties and bra, quickly closes the wrap around dress as if nothing had just happened, looks at me and says, "I like a certain kind of cream in my coffee. Now that I've had it, can I bring you a cup?" I nod in agreement, she turns to walk out, blowing me a kiss.

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@confessions
11 Sep 2012 11:32PM
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This morning I picked up a 10 pack of rolls, and after eating one, I called up a hooker from Backpage. I sort of told her I was rolling and she said that I should've gotten her one, too. I said I might have 2 with me if you got a friend that wants to join in. Hot damn - she had a friend with her at the motel. I popped a viagra and drove straight there. After we got settled in, we each popped one (that's 2 for me)and started smoking some chronic. Next thing you know, the 2 girls are all over each other. I wound up with one of them riding me reverse cowgirl and bareback on the edge of the bed while the other one got on her knees and licked/fingered my ass, sucking my cock, and eating the other girls pussy. I shot the most enormous load into her cunt while the other girl had 2 fingers up my ass on my prostate. After I pulled out, the girl on the bottom sucked my cum out of the girls cunt and then we had a 3 way kiss with snowball.

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