** This is the next story and stage in my life. The first story is titled, "From Handjobs to Orgies" and is published and I recommend reading first. As with my other true story, I love to get feedback to know what you thought and if it got you going! Enjoy **
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Now that Ashley and I had broken up, I found myself graduated from college with a full time job in finance and working through the grind. I spent my nights and weekends doing the usual things, hanging with friends and going to bars. Of course, I now also had experience in the ways of swinging and playing with others so everything wasn't exactly the same...
I used various apps and websites to find other people in the "lifestyle". At this point though I was a single male so not exactly your typical couple. My first hit was a couple who messaged me out of nowhere.
They introduced themselves as Dan and Jess. They were mid 40s, professional looking couple from what I could see and read on their profile. Dan was about 5'11", in average shape, white and looked like an average guy. Jess was 5'5", blonde, in shape but not too fit, nice looking ass and maybe some C or D boobs based on the pictures I had received. She was attractive but not a super MILF or model.
We chatted online for a while, got to know each other. They lived about 20 minutes away, he worked and she was a stay at home mom. They were looking for males and couples to play with, and after some further deep diving in conversation, they were after hung males who had their lives together. Well, fortunately, I could check those boxes.
They had played with two guys in the past with her giving the first guy a handjob and then a blowjob a week later in a hot tub at their house. The 2nd guy they actually took the plunge and had a mfm 3some and he got to fuck her. The experience was good, but he left a lot to be desired after only lasting a few minutes. Dan loved it and was revving to see it again, especially from a hung guy who could perform. Jess certainly was not putting up much resistance.
We eventually determined a time and place to meet and say hello, just a quick coffee and chat. The day came and I showed up and shortly after they arrived. She was wearing some tight jeans and a nice top that showed her boobs were probably closer to Ds than Cs. We chatted and talked about nothing for a while before finally the conversation turned a little seductive. I could see the fire in her eyes and knew we would be connecting again in a more private place.
On the way out to the cars she leaned in and gave me a little cheek kiss as we hugged and gently did a quick glide over my cock as she let go. Two days later they messaged me seeing if I could come over that evening to watch a game. Of course I could. I showed up right on time and ready to go. A few hours prior I had a long stroke session to make sure I wouldn't be too eager if the occasion came.
They let me into their house, it was a nice upper middle class residence. Their two kids were at friends places that evening so they had the house alone. They offered me a drink and had some snacks as we settled in. Jess was wearing a dress that was just a little too formal and tight for a night of watching football on the couch. It rounded her ass perfectly and showed those boobs again.
We once again chatted about nothing until Dan left the room to go take a call. Whether the call was fake or not I am not sure but she took the opportunity to join my couch. She cuddled up next to me and I put my hand on her exposed thigh. A moment later she leaned in and we started kissing getting closer and closer. I wasted no time and slid my hand under her dress to find nothing but a wet, shaved pussy. She returned the favor and slid her hand on top of my shorts.
From there she pulled down my zipper and slowly worked my cock out. I was already fully hard, a very thick 7.5" of cock with a little upwards curve and a big head. She started working it as I was exploring her pussy with my fingers. She had a surprisingly tight pussy despite having big pussy lips and she had a seductive moan.
After a few minutes of this she lowered her head onto my cock and began sucking me. She was an absolute star at sucking cock and was one of the best BJs I had ever had. At some points it felt so good I couldn't concentrate on fingering her tight pussy. Fortunately she slowed down just enough for me to regain my senses and slid her dress up exposing her beautiful pussy. I was able to slide three fingers inside and she was moaning hard as I finger fucked her.
Then she stopped, pulled down my shorts all the way and pushed me long ways across the couch and got into 69, her dress still on. I began eating her pussy, shoving my tongue deep inside as she was swallowing my big cock.
At some point Dan walked back into the room. Can you imagine walking into a room to find your wife hanging over a guy, her dress up to her waist and her mouth full of big, thick cock? Well, I could actually and I knew how awesome it is. I first caught notice of him on the recliner, his cock out as he had started to stroke. He had a very average cock, maybe 5.5" or 6" and a normal girth. Nothing to write home about but not bad either.
We kept going at it for a few minutes before Jess decide to unmount and get down. As she got down she waved at her husband who returned a big thumbs up. She then turned back to me, swung her leg across me and mounted back up, still in 69 position. Only this time she positioned her pussy right above my cock and gently started lowering herself.
The head of my cock slowly started to slip inside as she let out a gasp. She tried to continue to lower herself but had to keep pulling up, the fit was extremely tight.
She turned to me and said "Fuck you are so thick, I'm not sure it will fit!"
I replied "Oh it will fit in time, just need a new position."
Dan was furiously working his cock now, thoroughly enjoying watching his wife struggle to fit my dick. I pulled her off and then put her back down on the couch with her legs spread in the air as I lowered myself to her.
Once again my cock head slowly entered as she muttered something about a big cock. This time with the slight upwards angle of my cock going the other direction inside her I was able to have a bit more room. Still it was slow going with every inch taking a few minutes, but before long I was balls deep and she was out of breath.
I began the slow rhythmic pumping at that point with her wet, tight pussy swallowing my cock. Before I knew it she started cumming, her pussy squeezing my cock urging it to fill with cum. A moment later I heard Dan moan and he blew his load, shooting it a couple feet. But I had held strong, my cock was still rock hard and filled her pussy.
I slowly slid my cock out, still hard, and helped her stand up. I got behind her, smacked her ass and squeezed it before pulling her dress up and over her head. I unclipped her bra and her now obvious D titties fell out, beautiful and plump. Grabbing them in my hands from behind I squeezed them in full view of Dan. Then I moved my hands to her waist, gave her ass a big smack and moved her to the coffee table.
I had her bend over the coffee table on her knees, and positioned myself behind her. At this point she was facing Dan, her face about three feet from his chair where his cock was getting hard again. I was less gentle this time as I plunged my cock deep inside her and she squealed as I began pumping her with long strokes. For five, ten minutes I hit her pussy from all positions as he worked his cock and she moaned.
Dan eventually stood up, walked over to Jess and presented his cock to her. She grabbed it at first and then pulled it into her mouth, giving him her amazing BJ. So there she was, taking my cock and sucking her husbands, finally experiencing a good 3some. A few minutes later I filled her with my huge load and Dan blew his second load in her mouth.
We all went back to the couches, naked and worn out. We chatted some more, actually watched some of the game and hung out. Later in the evening we all ended up on the same couch with Jess in the middle and she was kind enough to give us a double handjob, with both of us cumming on her tits at the conclusion. I left that evening with both of them begging to meet again.
And we did. Over the next six months we got together seven or eight times, always pretty predictable. She became sluttier and sluttier, by the end greeting me completely nude or fucking in their backyard pool.
While I was still fucking Jess, I met another couple. He was a 53 year old marketing exec and his wife was a 41 year old smokeshow little MILF. She was about 5ft tall, brown hair, a runner type with small boobs but a great tight athletic ass. She was always wearing yoga pants or even those little volleyball shorts and an athletic top. She looked ten years younger than her age and was obviously well taken care of.
He was the typical wealthy executive, a little overweight, somewhat aloof and perpetually busy. Not a real attractive man and likely had little time to satisfy his very fit younger wife.
We had a few outings together, a meal, some drinks and whatnot. One day she texted me and asked if I wanted to go for a jog with her. I loved to run and why not go running with her, she was sexy and I was hoping to add them to my friends list.
I got to the trail and she was in these skin tight lycra volleyball shorts with an orange top that ended at her waist. Her ass was in perfect view for everyone to see. We chatted and stretched and that is where I noticed when she bent over that she had on a little thong. I got slightly hard at the sight but held it together and we went running. A few miles later we stopped and sat down on the trail. We were both sweating nicely and feeling good.
