Would you play with a former school mate from years gone by?

[sunbuckus 3,567]

When I was in elementary/middle/high school, I liked quite a lot of boys. For the most part, I can still recall their names. Well, last night, I had a dream about a former crush coming on to me sexually--as adults. Oddly enough, I was aware enough at the end of my dream that I said to myself, "Gosh, this would be a great question to pose to the SB forum!"

 

So, now that you're a swinger, if you had permission from your partner to play with a former crush that you had when you were school-age and they were interested in playing with you (assuming they are single/widowed/divorced/also a swinger with permission), would you?

 

Or, if you were attending a school reunion or came upon a former schoolmate that you now find attractive, would you pursue them (if everything was kosher--everyone involved is in the loop)?

[Mbgdallas 203]

Without a doubt yes!

[wearetheone1967 40]

I had a crush on anything with boobs, back then. I doubt my wife would go for that now. The funny part, is the only girl I dated in high school besides my wife... had no boobs. LOL.

[enhancer 1,585]

Sure why not! At this point so many years later and with my tastes on what I like changing so much over the years I would have to wonder though if I would still find them attractive.

[GuyInMD79 1,500]

Yes! I can think of one person, who I dated in high school and then in college...

 

Also, my main high-school crush is my wife!

[Guest]

We kind of did this. Went to reunion, the best friend of my high school boyfriend was there. We had all double dated a lot, I’m sure he had seen us fucking in the front seat while he and my best girlfriend were doing the same in the back seat and so forth. His wife was also there. I was a widow. A few weeks later, he calls me, has come to Chicago where I live and wanted to meet for dinner. We did, he tries to hustle me off to bed but I say no, you are married. Five years later, another reunion. I’m with my new BF, we have started swinging, done several MFM and a few swaps. Same guy is at the reunion, now divorced. I had told BF story of the prior reunion and his visit, and intent. The guy starts hitting on me, BF tells me to go for it, I’m flirtatious and seductive all evening long. At the end, I ask if he would like to join us for drinks afterwards and we go to the hotel bar where BF and I are staying, and the three of us end up in bed. No regrets.

[GoldCoCouple 4,065]

HELL YEAH! (as long as the Ms. was okay with it, that is). With how screwed up I was in high school (and even into college) I had dated lots of girls, but the strict Christian upbringing kept me from having sex with most of those girls. There are several that I would love to rectify that with now (even better, with the Ms. playing with us as well). Sign me up!

[Alura 2,774]

I was fortunate enough to spend an afternoon, during a class reunion, in a motel room with my high school sweetheart and a "Tryst Kit" (wine, glasses, lubricant, etc.) prepared and named by the late Mrs. Alura. We tried to return the favor on Laura's behalf at her reunion, but her high school sweetheart, who was even single, just didn't seem to get the idea of what was being offered to him. (Terry, if you're out there, you missed something special!) Laura got only a kiss.

[econobiker 165]

Good topic!

And interesting in that I've just been friended on that professional social network (rhymes with inked bin) recently by a woman who was a former high school classmate and who I had a crush on. But my crush never worked out as she and I maintained a friendship only back then, never more than friends. She seems to be single and lives near where i grew up and where i still have relatives. I missed my 25th high school reunion but, when Red and I visit there again, maybe Red would allow a visit with this woman, with whom I would be upfront and truthful about swinging. And see where it goes from there...

[asncpl 729]

Definitely YES! It'd satisfy my curiosity in so many ways. Ever since Facebook, I had reconnected with many of my schoolmates. Some have gained more than a few pounds, but some I still found very attractive.

[J&Wu 408]

I would treat them like anyone else if they showed up at our swing club.

[twohots4u2 188]

The first high school reunion I went to was the 30th.  I had been married and divorced, and lived about 500 miles away. Several of the women I had dated in high school were there and some of them were flirting with me.  There was one woman I had dated the summer before I went off to college, and while we did not have sex we did some very hot and heavy petting that summer.  

 

We traded phone numbers and she told me to give her a ring the next time I was going to be in town.  Several weeks later I was in the area on business and gave her a ring.  She suggested that we meet for lunch in town about half-way to the city I was working in.  We did, and she let me know that she was free for the rest of the afternoon.  After lunch we went to my hotel and had several sessions of fantastic sex before she said she had to go home and fix dinner for her husband.  

 

That started a three year affair of get togethers about once a month.  We were both in our early 50s and so she did not have to worry about getting pregnant.  Every time we parted she left with her pussy full of my cum.  Several times we arranged things so we could spend several days together and they were like honeymoon period, all we did was fuck, eat, and sleep.

 

Her husband got sick and she felt guilty about our affair.  So, by mutual agreement we stopped.  Never expected to have so much fun at 50!

[PSULioness 847]

We play primarily with my old school friends from college. I can say that my whole life changed because of being introduced to this lifestyle. 

 

I say playing with people you already know and have something in common with is so much better than chancing it with strangers. 

 

Cheating with an old classmate is just that, cheating. Cheating is not swinging. I don’t know your situation, I couldn’t cheat and live with it. I needed to tell the person I cared that I had sex with someone else. That is me and I don’t condemn others for their choices. 

[cplnuswing 4,713]

Absolutely! In fact, just seeing this thread brought several minutes of pleasant fantasizing about who all exactly would be on that list

[njbm 2,871]

We met a couple for drinks and the wife formerly worked for another business in my office building. I didn’t recognize her from her online pictures. We knew each other well, told that to our partners. Her partner said this is so taboo, we have to do it. We did and it was a memorable session for us. No encore, though the other boyfriend and I stay in touch. 

[Partyboobs 3]

I have lol. Ran into an old school friend at an event. Was only wearing a see thru thong bikini... I sucked his dick and we fucked after lol

[couplers 4,640]

My regrets aren't the guys I didn't have sex with, it is the girls.  

[GoldCoCouple 4,065]

I just WISH that we would have a high school reunion so that the opportunity could at least be there. Coming from a VERY SMALL high school, it just doesn't seem to happen. I even tried to suggest that we combine several years into one bigger reunion (even as many as 5 years into one) but it just never got any traction. Tough when your graduating class was 52 people (hey, I graduated in the top 50 of my class!). 40th has already passed...

[Funmom 45]

My husband and I do not live in the town nor state that we grew up in. So just last year after not being around a long time I went back to visit while my husband stayed and worked. I got invited to one of my old BFFs birthday partys. I told my husband and he said if something comes up to go ahead and play if I wanted to. At the party I was drinking and alot of old classmates where talking to me. By the later hours I was feeling good and horny and a few of the guys kept flirting. I ended up having sex with three of them at different times throughout the party

[barefoot_so_goo 46]

Yes, I actively pursued this before and after my divorce. Just realizing time moves on and I missed a lot of opportunities when younger.

 

The first was a woman who pursued me in high school, but I didn't think was a good idea. (I had many other serious issues going on as well.) As I was going through my divorce, we talked through Facebook, leading to phone calls. We live across the country, but when my divorce was done and I had some free time, we met and things moved right where I'd hoped. She was still married but he had moved out (he was abusive). She'd put on a lot of weight, but still had the same beautiful eyes. Several great hours together, all over her house.

 

Second woman is a year older than me, so a year ahead in school. Very outspoken and intimidating to me then. But we connected on Facebook as I was at last getting the divorce. She'd been divorced twice and had lots of great advice, and was a great support. Hours-long phone calls. Also across country, but she flew up to see me. One thing led to another and we didn't leave her hotel room for a day. The next day we went to a LS club; she'd been a nudist but hadn't ever been swinging. She loved the experience, even though she stayed with me. She went home happy. Over the next two years, when I traveled to her, we had some great afternoons.

 

One intensely emotional point came up with both women: why didn't we get together? Look, pointing to pictures hanging, these could have been our kids. We'd still be making them. Crying, mostly about they'd made bad choices and kept ending up with abusive men, which was why they stopped at two kids. Just a lot of emotion all coming out at once. I'm grateful for all the therapy I had, as we were able to talk through it all. Still on good terms with them both.

 

There's something amazingly satisfying about curling the toes of a girl you'd stupidly missed out on twenty-five years before. Double thrill if it's on her husband's side of the bed!

[J&Wu 408]

On 6/15/2021 at 9:43 AM, GoldCoCouple said:

I just WISH that we would have a high school reunion so that the opportunity could at least be there. Coming from a VERY SMALL high school, it just doesn't seem to happen. I even tried to suggest that we combine several years into one bigger reunion (even as many as 5 years into one) but it just never got any traction. Tough when your graduating class was 52 people (hey, I graduated in the top 50 of my class!). 40th has already passed...

Only 8 in mine, we were having yearly reunions since 2015'ish and in 2019 all graduating classes for the school at the local Indian Casino. Then COVID intervened😢. I was in the top 25% of the class! Actually both of us went on to medical schools and we had one RN, one school teacher and a financially successful farmer.

[Anon321 522]

My GF has!  A few summers back she met a guy at a party who she went to high school with and he fucked her brains out.  She absolutely loved the experience and saw him a few times after that.  I believe there was at least 1 or 2 others as well.

[discreetplay 235]

On 6/14/2021 at 12:47 PM, cplnuswing said:

Absolutely! In fact, just seeing this thread brought several minutes of pleasant fantasizing about who all exactly would be on that list

 

You and us both. Now that "school mates" are a bit older and likely more open-minded about things, I'd love to meet up with a few crushes I had. I'm thinking of one right now that I'd be quite interested in. 

[Rock n Tits 186]

We have a good friend that Tits first jr high school boy friend. At the time they kissed and felt her small tits but we got together after his second marriage fell apart and had a long relationship found out then that he and she and his first wife had threesome. We are still good friends and see each other but he has remarried and the wives do not get along but it was fun while it lasted.

[Sophy 569]

Unfortunately, I live in a different country now, but given the opportunity yes absolutely.

Edited November 17, 2021 by Sophy

[let's do it again 414]

I have, twice. Both times the women were back in town visiting relatives and looked me up. After talking for a while about high school, we moved to the bedroom. It was fun, but reminded me of why we didn't go further in high school!