Sex with People from My Past

tagGroup SexSex with People from My Past

In Dec of 2020, I ran into an a girl a used to know.
We went to the same highschool but she was a few years younger and I didn't really know her then. After highschool I was having a sexual relationship with her father. I didn't realize he was her father or that he was married until I ran into him and his family one day and he introduced me as "the Starbucks' girl" cause I worked there and that's where we had meet. Leslie, his daughter, recognized me from school and she began chatting with me. I felt weird being so friendly seeing as I was fucking her dad but she is genuinely a sweet girl. I broke things off with her father after that but Leslie stayed in touch with me for a few months until she came out to me as gay, and wanted her first lesbian experience to be with me. Have to admit, it was tempting, she is really cute blonde but at that time was still 16 plus the recent sexual relationship with her father had me feeling a bit uneasy, so I felt like I had to turn her down.
Anyways, when we saw each other the other day and we chatted a bit. I learned her father passed away 2 years ago of a heart attack, that's kind of unnerving, knowing someone I've had sex with has died like that. She confessed to having a huge crush on me all through highschool and after. I told her she was always very pretty and if I had known about her crush on me in highschool, I definitely would have taken the opportunity. As we chatted, she flirted and asked me out. I told her about me and Jason, that we swing and some about our swinger experiences.
So, as Leslie and I chatted with each other, she asked about our swinger situation. I explained about our past and how our relationship had evolved and some of the sexual activities we enjoy. She didn't seem doubt anything I told her, she knew my sexual reputation in highschool. She said she was always very interested in being more sexually adventurous but with people she could trust and fell safe with. She was actually bi now and had never had a threesum and asked if she could meet Jason. She admitted to wanting a threesum, and that we could be her first threesum. I was excited at the idea of being able to bring home a cute girl for Jason, so we arranged a "date night" for them to meet. I was Jason would think she's as pretty as I do. I'm just not sure what would happen if she found out about my past with her father.
For out date with Leslie, we had some takeout and then a few drinks to relax. There was plenty of flirting and then some kissing. We didn't want to overwhelm her with anything to "kinky" for her first time, we did not want to make her feel uncomfortable. She and I started, kissing, helping each other strip out of our clothing. Jason made himself comfortable too, and wrapped one arm around each of us, groping our tits as we stripped each other from our bras. I grabbed her hand and guided it onto Jason's hard cock. Kissing each other deep, we worked together stroking his cock, feeling it throb between our fingers.
As we caressed one another, we stripped till we were all completely naked. Jason moved behind Leslie and wrapped his arms around her, kissing her neck, letting his hand slide down over her wet pussy, feeling her wetness. I kissed my way down her neck and chest to her nipples. I suckled her hard nipples, feeling melting into Jason's arms. Together we focused on pleasuring her, Jason gently grinding her clit, my mouth taking her nipples. She slowly gave into our seduction. We could feel her body tremble as she gave into the pleasure and let herself cum for us.
As she came we continued pleasuring her, prolonging her intense orgasm, feeding off her unleashed sexuality. We delighted in the reaction her body had to us. She melted into the moment letting us guide her into an orgasmic euphoria. I moved up to kiss her, my hands now over her tits, pinching her nipples, making her moan. Jason pushing two fingers into her waiting pussy, now soaking from her orgasm. Curling his fingers inside her, gliding in and out, still massaging her clit, made her juices trickle down his hand. Her body under our control, her orgasms building more and more, we felt she almost as though she was our puppet completely under our control. Something she didn't seem to mind at all.
After several intense minutes, she seemed to almost collapse on us, her breathing heavy and eyes glazed over. She stared intently on me, pushed me onto the couch, got down on all fours, pushed my legs apart, and eagerly began licking my hot pussy. Her ass up in the air, she reached under herself to spread her wet pussy, an open invitation for Jason's cock. She licked me hard and steady at first, lapping up any juices that had already dripped from me, then used her tongue to find more of my juices inside my soaked pussy. Jason didn't miss his cue, he happily stuffed her hot pussy with his pulsating cock. I could see the look of bliss on his face as he took long slow strokes to fuck her. I imagine I must have had almost the same look on my face.
Leslie was very skilled with her tongue, and enthusiastic too. As horny as I had gotten making her cum, now her mouth on my pussy, and able to see Jason fucking her, I was cumming so hard. I grabbed her long hair in my hands, and pushed her head harder down, she didn't resist, she was giving into me, letting her use, letting me control. As I controlled her head, Jason controlled her hips, grabbing them in both hands, holding her still, plunging his cock into her as he willed. He used hard fast thrusts to make her cum, then slow long ones to make her writhe and moan into my pussy. Again she was a puppet to us. We controlled her to maximize our pleasure and she was more than willing, she wanted it that way.
Finally I could sense Jason erupt, he came hard and long inside her, and I had cum several times feeding Leslie my juices each time. She sat up with a blissful smile, licking her lips. We could tell she was thoroughly fulfilled. What she didn't realize though, we weren't quite done yet. I could tell she didn't expect anything more as I moved her to my previous spot and spread her legs as she had done to me. It was time for me to indulge in one of my delights. With her legs spread, Jason's thick cum was now oozing from her opened juicy pussy. I slurped up the glob of cum before it trailed down between her ass then, using my tongue, scooped any more I could find from inside her. Jason watched, stroking his cock, watching his filthy cumslut eat his cum from a freshly fucked pussy. Leslie was a bit surprised that I was doing this, even though I had told her how much I did enjoy it. But she eased up and let me finish lapping up all that I could. Just as I thought there was no more cum, Jason came once more by jerking off all over my tits.
Leslie just looked at my tits, and the cum splattered all over. She meekfully leaned in to lick up my messy tits. She ran her tongue thoroughly across my skin, making sure not to miss a spot. Once I determined she had done a good job, I pulled her to me and kissed her, tasting the mixtures of pussy and cum on her lips and tongue. Several more minutes of kissing and naked bodies rubbing together had passed before we realized how late it was and how thick the fog had gotten. We asked Leslie if she just wanted to spend the night, our bed is big enough to accommodate her. She was happy to accept our offer. This was mine and Jason's first sleep over threesum date. It was actually pretty nice.
So last Christmas and NYE, we had involved our new friend Angela into our swinger circle. At that time, she was taking back her sexuality after being under the influence of her drug dealer bf for such a long time. She was more than excited to help participate in filling a few sexual fantasies for Jason and for Jerrod, and began dating again. Ironically, she ended up dating an ex of mine, Mark. He was my first bf from highschool and my first sexual experience. But he was an asshole back then, he broke it off with me after getting what he wanted. It seems he's matured a lot since then though. Jason and I even went on a double date with Angela and Mark at her request to show us that he had changed since then (it was 13 years ago).
Once the quarantines were placed, they moved in together quickly. Seems things have been going really good for them. But Angela did want to continue swinging with us and the group we have made. But I felt weird about it, wasn't sure I wanted to have sex again with an ex, especially this one. But Angela and I kept in touch through the lock downs. No matter what happens, we still want her as a friend.
For this NYE, Angela invited the group from last year over to Mark's house for a party, pretty sure we all knew what kind of party they we hoping for. Stephanie and Steven couldn't make the trip that far, but Lexi and Jerrod were excited about going and so was Jason. For some reason he doesn't have any problems with me and an ex being together as long as it's in the swinger fun context. So I agreed to go, but Jason and I asked to bring a date, Leslie, almost just like Angela was our date to last year's party. Of course it was ok, the more the merrier.
The party started very typically, some drinks and finger foods. Then some smoke and more food. The relaxed atmosphere lead to a lot of flirting, Jerrod never misses an opportunity to flirt with me. Angela and Mark seemed like they wanted to broaden their relationship boundaries and flirted with everyone, Leslie explored her options, Jason just flirted with all the girls of course. Slowly but surely, we were all kissing someone other than our significant others and half-naked, and the kissing lead to the girls performing oral sex.
Jerrod was more than thrilled for me to suck his cock again. I wasn't sure how the others paired off initially, but Jerrod wanted me to snowball Angela after he came, so with my mouth full of cum, I looked around for her but made eye contact with Leslie instead and thought I'd delight her with a warm cum-kiss. I gave her a big sloppy kiss and she happily slopped it up as she stroked a hard cock with on hand and grabbed my ass with the other. Then she pulled the cock between us, we took turns sucking it in a way to see who could make it cum first. She won as it started to blow streams of cum in her mouth, and we shared another cum-kiss.
Then wondering which cock we were sharing, I looked up to see it was my ex, Mark. I guess I was caught in the moment and hadn't noticed. Being caught off guard, it made me swallow what I had of his load. I knelt there in front of Leslie, looking up at Mark, and back at Leslie. Then around the room to see Jason face-fucking Lexi and Angela deep-throating Jerrod. So as not to ruin the mood of the party, I simply slide to the floor and pulled Leslie between my legs and to eat my pussy and watched as Mark ate her pussy. The rest of the night went pretty much the same, a few more swaps of partners before we matched back up together and causally got dressed. A few hours into the new year, we called it night, we invited Leslie to stay with us again, but she chose to be dropped off at home. I told Jason what happened between me, Leslie and Mark, he said he saw the whole thing and just thought I was over my issue about it. I think I am.
So with the recent fun we've been having, it's got me thinking about what's next. Ever since my gangbang in July, I've been contemplating a bukkake and what it would take to make one happen. We know we could probably get the guys from the gangbang again and that would be nice I guess. But Jason says since it's my 27th birthday, we should attempt to get 27 guys to cum on my face.
I wasn't sure we'd be able to get that many men without just accepting random men off the street or off the internet, which isn't something I'm thrilled about. But Jason is undeterred. Apparently, he asked Lexi about the total number of trustful "massage" clients she has and if she thought if any of them would "tip" for an opportunity to participate in a bukkake. She says she may be able to get up to 15 guys depending on how much of a tip we request. Since it's more a party, the tip would only be nominal to help pay for party supplies or decorations. So as of now, Jason and Lexi think they can get at least 21 guys together. They say it could possible be $10.00 to participate "manually" or $20.00 for assistance from Lexi. With almost three months left to plan, I think they may actually be able to pull this off. I'm gonna wait and see.

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