Jackson [MFM?]

Jackson

I had lost two stupid cases in as many preceding days. I wasted time after I got home from work because a girl that works in my office, that I have had sex with, said in her emailed invitation to happy hour that it went until 7. So I changed into my finest lumberjack/hipster/skater attire, drank two medium-sized glasses of rye whiskey alone, and ambled down the sidewalk to the designated bar which is five blocks from my house.

Arrival at 7:15 and nobody was there with the exception of a young woman from my office who was still attired in her somewhat ill-fitting suit from doing her own trial that day. She informed me that the others had been there, but had left prior to 7pm, babies.

So anyway, we started drinking a few beers, coworker was not interested in staying out late, she graciously paid for my beers when I went to the bathroom. I struck up a conversation with ‘Johnny’ who was, for whatever reason, editing ski photos on his macbook, at the bar. Trying to get some visibility. I asked him where he had been skiing, just as this googley-eyed, but very cute, brunette that is sitting on the other side of Johnny starts to flirt with both of us, with what I can only describe as strong body language. She is alone. Being the suspicious type, I ask her whether she is working in some capacity and she revealed that, indeed, she works for Jagermeister. ‘Heidi’ then explained the medicinal benefits of Jagermeister as a digestif and its other various medicinal qualities, of course I was slightly teasing her about her product and the fact that nobody expects, nor yearns for, Jagermeister as a substitute for virtually any other liquor in a cocktail. To prove her point I suppose Heidi ordered a round of Jager-Manhattans (Johnny was able to slyly order a tequila-based drink from the bartender on the same tab). We drank our drinks. Heidi had unnecessarily slipped into conversation that she had a boyfriend. I talked about skiing with Johnny and we got psyched about skiing in Jackson, which for the purposes of the drunken excitement I promised free accommodations with my uncle who lives in the area. He scribbled down his phone number the old fashioned way and we three almost simultaneously headed for the front door.

I was pretty tuned up. So of course, I was whistling at the top of my range, Johnny Cash “Jackson” (which is actually about Jackson Mississippi) as I walked uphill. From across the street, a woman’s voice yells “Have you ever whistled like that into a vagina?” Of course, I was intrigued. I crossed the street with some lame response. It was one attractive blondish girl in boots and two guys, who toted a case of beer and a large bottle of cheap tequila. We stood around and talked for a minute, they suggested that I get in their car with them (the girl’s Mini). They reassured me it wouldn’t be too far down Federal.

The car ride had indicated to me the following social structure: all three worked together at XXXX apparently in the corporate side (I didn’t ask), David was hyper sexual and gay and wanted everybody to know it, Charlie was his enormous straight friend from work, Cassandra seemed happy to be the only girl, they all had the day off tomorrow (which was Friday) and wanted to drink.

The house was suspiciously nice on the inside. Well-decorated and understated with low-profile furniture, nothing was out of place. David’s pride and joy. He showed us around, including the basement, his room/closet, and quarters for his two roommates (another had been banished recently). We drank beers rapidly and chattered about god knows what. Two more coworkers showed up. I was the random guy who’d gotten picked up in the street.

Hot tub time! The two extraneous coworkers disappeared, I peeled off my clothes inside the house, cradled my dick/balls in my hand and tiptoed outside into the freezing cold outside.

Cassandra was already partway submerged, and made no efforts to hide her perky tits and small nipples. She’s 41 but my guess was in her mid-thirties, she didn’t strike me as an athlete but thin and healthy in that effortless kind of way. She giggled and kept an eye on me as I splashed my way into the tub. We grazed legs and got in close to each other. She was into it.

The two other boys arrived in half a moment, wearing boxer-briefs surprisingly. Everyone was getting a little drunk/loud right from the start, but David pushed the envelope further by declaring a game of truth or dare. (A side-note, it appears to this author that David had a paraphilia for ‘turning’ straight men, or even to performing sexual acts on straight men without their consent He stated that his first sexual experience had been forced on him by a man, possibly at a young age). David was choosing the dares, first for Charlie and myself to kiss on the mouth, which we protested and refused then settled on a standing naked hug and congratulating ourselves on our straightness. Charlie had to get out and run around the house, naked. Cassandra was asked the truth of who she wanted to fuck the most of present company, and looked my way. Charlie and me had a kissing competition with Cassandra as the judge of both our techniques. Dicks were simultaneously extracted and compared.

Oh shit. Dare. Our hyper-sexual T&D dictator, dares me to teabag Cassandra in front of the group.. I protest stating that my dick wasn’t hard, but I was made to stand up while my semi-hard cock was inspected by Cassandra and David at less than arm’s length away (‘nice’), and Charlie not much further. I stood on the bench as Cassandra licked her lips, got underneath me, and started sucking on my balls one after the other as my cock immediately swelled to life across her face and forehead, to proud full-size. David was cheering her on, and I know Charlie was watching.

That was not the peak. Soon we were taking turns licking Cassandra’s titties held up above the jets (again, scored on technique); she was sampling Charlie’s cock, then mine, taking turns, arching her hips to display her rear-pussy to the opposite party. David could not restrain his arousal, and kept reaching hands and feet under the hot tub to fuck with Charlie and me, and we would yell and tell him to fuck off. Charlie eventually resigned to the fact that he had a girlfriend, as he said, and that Cassandra really wanted to fuck me anyway. He made steps to leave. We all got cold and went inside.

David’s roommate Alex came home, we all talked, he seemed to be internally raising his eyebrows a little bit at the level of raunchiness and intoxication he was observing in the kitchen. Alex has a beautiful NSDTR, which however was not as intelligent as my own. We played with the dog, walked in size 10 high heel shoes across the kitchen, and just talked about bullshit for probably an hour, steadily drinking even more. Sensing the weirdness creeping in as David was suggesting we all get into his bed, I prepared to hail an Uber to spirit me away from this situation. I was trying to make my escape but they weren’t having it.

On the front porch, at David’s suggestion, Cassandra pulled my dick out of my pants and started tugging on it as I waited for my ride. She told me she wanted me to eat her right there, so I did. I think the first Uber driver came past, saw what was happening, and changed his mind about stopping. I got notification the ride was cancelled. I was unbelievably horny and it looked like Cassandra wanted to have a little fun with me as a random stranger. She led me into the master bedroom, I stripped her little remaining clothing off and leaned back for a moment to take in the landscape. Her tight body obviously had not borne children, and she looked at me like she was really hungry. We didn’t waste too much time in locking lips, hands roaming all over each other’s bodies, me lifting her up and parting her ass with both hands. I started to touch her vagina with my right hand fingers, parting it slightly, and feeling the sticky wetness on the pads as I oriented myself and took a swipe at her clit. She was into it. The light was dim, I think the TV was on, cable. I heard the door open and click behind me and to my right. I knew it was David. At that point I didn’t really care because I was pleasuring this really hot blonde chick who was moaning and having a great time. But at one point I peeked back, and this fucker was filming us. Filming his co-worker getting her pussy worked over by me, a complete stranger. I smacked the camera out of his hand. Cassandra didn’t seem to care that her co-worker was making porn of her. I continued my duty, putting fingers inside of her, she was very vocal. David starts doing things like holding her legs back, grabbing one of her tits, then I feel him grabbing my ass. I turn and smack his hand away, saying I’m straight and to fuck off. I’m drunk. I’m enjoying what I am doing with Cassandra. But David is getting closer to my ass, trying to stick a finger in me, I have my legs crossed to prevent him, he tries to stick his tongue into the clenched thigh/ass area. I’m pushing him away, but he’s persistent. He may have had some near-successes. (Who can remember?) I don’t want it to interrupt what I’m doing to Cassandra’s pussy and ass with my fingers and mouth, but it’s distracting to say the least.

At one point I get up, push David out by the shoulders, (both of us are completely naked with hard-ons, his is smaller), he tries to tell me that nothing is wrong, I lock me and Cassandra into the room using the skeleton key. We make out and fool around for another twenty minutes or more. We don’t fuck and I don’t come. She rolls over as if to sleep, and I give her a perfunctory cuddle for a few seconds but I know that I must leave. I can’t really believe what just happened, with the three of us in that bed, but I grab for my jeans and hoist them up over my legs and hastily button my flannel. I open the door, David jumps into bed with Cassandra. We have a brief conversation where I assure David that me and Cassandra already exchanged numbers (we had not).

Beam Me Up, Scotty! The Uber picked me up, and I did not indulge in small-talk but chuckled while I softly whistled the Johnny Cash song.

Source: reddit.com/r/gonewildstories/comments/4abotk/jackson_mfm