TL;DR I “dated” Linda and Dan for a year, and, at least in the short term, satiated their thirst for Dan enjoying his role as a cuckold (I didn’t know it was called cuckolding at the time). This story is about how we became “really good” friends about a month into our relationship.
I was early to mid 20s when this took place. Linda and Dan (names changed) excited me greatly. Hope you enjoy this sordid tale of lust.
My second job in the Boston tech market was, frankly, my dream job. I was young, and yet I got to contribute to this up and coming company, and nobody questioned my age; for my really friendly co-workers, it was about ability and mentoring a young person like myself. People would frequently drop by my office and kibitz about work and life, and even when they didn’t like my work, they would still mentor me so that I wouldn’t make the same mistake twice.
Linda was a lot like that, but she’d appear in my office, leaned against the doorframe (that’s before cubicles became this shitty thing, and you could actually close your office door), and would crack jokes and play with her necklace as she talked about path forward and “how to sell software,” or whatever it was that we talked about. I admit that I took notice of Linda right away. She was easily mid-50s, but had this youthful enthusiasm about her. She’d wear these tight jeans, bulky sweaters with turtleneck collars, and clogs. And at the end of any chat, she’d stop playing with her necklace and would visibly shove it down the front of her sweater. At least once I could swear that I saw her nipples poking through the chain-link pattern on the sweater.
One of my other co-workers dropped by and warned me about Linda and her husband, Dan. “They’re swingers,” they said. I played dumb and suggested that swinging was something from the 1970s, and I think I persuaded my co-worker to knock it off about this topic, so it was never mentioned again.
Thing changed that year during a company Christmas party. I finally met Dan that night, and Linda looked ravishing in this floor-length, green, velvety, dress, and her heels were visible as she cut the rug with Dan during the dance hour. She was the only woman at the company who was sporting cleavage, and I admit that I was enthralled. It wasn’t until Dan started talking to me at a urinal later on that things got real, as they say.
He wrote down their phone number on a disposable hand towel, and then both he and Linda headed out. I left about an hour later, stopping on my way to use a pay phone (after I bought condoms at a mini mart), to call them to say that I was on my way.
Linda and Dan lived in an affluent Boston suburb called Lexington. I arrived on their doorstep about 90 minutes after they left the party. Dan welcomed me in, he poured us a couple of stiff drinks, and we sat in front of this hanging fireplace (the room was adorn with a furry rug and hardwood floors and all of these crazy stereotypes that I won’t get into now). Linda showed up in lingerie about half hour after that, and I almost ran the hell out of there. My bisexuality and sense of adventure were things I definitely kept to myself, and in particular in a professional environment.
And yet they calmed me down, Linda disrobed, and I had my way with her while Dan watched — then he started jerking off while I split my attention between fucking Linda and Dan’s masturbating. We went on like this for at least an hour. Then we repeated for the next couple of weeks in basically the same pattern. Then Christmas hit, New Years hit, Linda was aloof at work, and I thought it was over. It’s not like I had regrets. It’s just that I wanted more.
They invited me to this well-known restaurant/pub in Harvard Square one night after work. That’s when they laid it on me. They wanted us to be better friends, and I asked what that meant. They slid a set of papers across the table to me, and asked if I would get tested as well. They were both negative, and wanted to go raw — and were hoping that I was the same. Hell. Yeah. I love raw still! So I said that I would and said that they had other things in mind, which they whispered to me even with the loudening music.
We had a date the following Friday night, so I brought my (negative) papers along. I went down on Linda then started fucking her.
“Nut up in her! C’mon, boy! Nut up in her!!!” Dan egged me on from the sideline.
I couldn’t hold it much longer and absolutely filled Linda with my cum.
Dan got up off the couch, came around me, and tapped my right butt cheek. “Well, don’t keep a guy waiting!” He unzipped his fly, and pulled his pants down. Then he got in between Linda’s legs and ate my creampie. The he started fucking her, didn’t last long, and finished inside of her as well.
“Want to go again?” he asked me, and I nodded. “Well, you know what to do,” he said, so I positioned myself between her legs and was about to start fucking his wife again.
“No, not that!” he slapped his forehead. “This!” he exclaimed, while visibly sticking his tongue between his index and middle finger and sliding it in and out.
I ate the creampie out of Linda, and started fucking her. I admit that I was having trouble getting started again. Linda suggested that Dan give me head and that he was very good at it. So, I sat on their sectional sofa and her husband fluffed the shit out of me.
Then I fucked Linda again to completion, and Dan returned the favor. So at the end of it I enjoyed sloppy seconds… and thirds.
Linda and I would fuck, alone, in their marital bed, periodically — when she’d call in sick. Dan and I would have a rendezvous in the Alewife “T” parking garage where we’d share some head. Ultimately though, it came to an end. They were super nice about it, and really, I couldn’t complain, but they found a younger model, I think. But what a year it was.
Source: reddit.com/r/gonewildstories/comments/jakiih/mfmmf_the_year_of_linda_and_dan
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