Clothing Optional Weekend with Friends – Part 3 [Mf] [MF]

After our fun in the shower and bathtub, we all ended up in the master bedroom cuddling on the king sized bed. Me and Tom on the ends and our wives in the middle. Nat and I were naked except for a pair of towels lightly draped around our bodies. She had her head resting on my chest while her fingers lightly traced up and down my torso. Much the same scene was on the other side of the bed, but I was too engaged in the moment to pay much attention.

Tomorrow morning we were heading back home and I think all four of us had the same thought in mind: making the most of tonight. It was still early and we had the energy for a couple more hours of play. I just needed a few more minutes to get myself ready to go again.

In the meantime I let my hand caress Nat’s breasts. So full and different from my wife’s. It was silent and the only movement on the bed was the gentle movements and touches of hands all over the place. As I focused in on Nat’s nipple, I could hear her breathing get shallower. She leaned her neck back a bit and brought her lips to mine. A long, slow, passionate kiss as I played with her nipple.

Sneaking around with a college coworker [MF]

Back in college I had one of those great low-effort on campus jobs in the student union. Basically all I had to do was walk around the building every couple hours and make sure it’s still there. Every now and then we’d set up or take down some AV stuff. Tons of downtime. My coworker Annie and I often worked overlapping shifts and we got along pretty well.

Like most college kids, we had hormones. Those hormones would often spur us to talk and tease about sexual things. She’d brag to me about whatever sexual conquest she had last weekend, I would (jokingly) brag about my size, etc. We’re both very sarcastic and could play off each other for hours with that style of humor. One time we were walking down a hallway and she abruptly stopped in front of me and her hand swung backwards right into my crotch. I joked that if she wanted to get her hands on it, she can just ask. That kind of teasing.

My wife shares me with her sister [MF]

A few years back my wife’s older sister came to stay with us for a few weeks. She was moving across the country and her lease ended a month before her new job opened up, so she crashed at our place for a bit. She’s similar to my wife, physically. Both petite, slim, with a bit of curves. But personality-wise, they couldn’t be more different. My sister in law Nina could be somewhat combative. She’s definitely got a soft center but she puts up a tough outer shell. At times she lets down her guard and comes to us for help, advice, whatever, and the real her comes through. More often than not, though, it’s masked under layers of sarcasm and dry wit, which makes her a fun sparring partner to joke around with, but can be somewhat exhausting at times.

In any case, her and I never really had much of a relationship outside her sister. So having her around at first was a bit awkward. At times my wife would be at work and it would just be the two of us sitting around watching tv or scrolling mindlessly on our phones with no words spoken for hours. My wife noticed the silence between us and one day on her way out whispered to me, “Try to talk a bit with Nina. You know she has trouble opening up with people, maybe just go out for dessert or something together?”

Our first time swapping with friends [MF] [MF]

My wife and I have another couple that we’re pretty close with. We’ve been friends for about a decade and have always had a good time being ourselves and very relaxed around them. There’s been many nights where it’s just the four of us hanging out into the AM hours at one of our houses enjoying each others company. I’d always been attracted to my friend’s wife, Nat. She’s pretty different from my wife, both physically and her personality. She’s taller, and a bit curvier, but still pretty fit. My wife is on the shorter side and slim. In any case, other than the occasional suggestive joke here and there in the group, my attraction to her was always just a fantasy and there was never really any sexual tension between us all.

One night we were hanging out at their house playing board and video games. A combination of things like taboo, pictionary, Mario Kart, etc. As usual, we were all being super competitive and trash talking throughout. Adding fun stakes to our games has always been part of the deal. Usually silly dares like drinking a shot of hot sauce or telling an embarrassing secret.

Reuniting with my high school sweetheart [fm]

Kelly and I “dated” for like a week in high school. We were both awkward but cared a lot for each other. For a lot of reasons we couldn’t really be together despite having this very cute on again off again thing.

I was a year older than her so when I started college we gradually lost touch. The emails became less frequent and eventually stopped altogether. Until a few years later she emailed me and told me she was coming to town to visit some places for grad school and asked if I wanted to meet up.

We met up for dinner at a sandwich shop near by her hotel. It was great seeing her again. We caught up, talked about how much of a missed opportunity we had in high school, etc. When it was time for her to head back, I walked her back to her hotel and up to her room. I hugged her and told her I had a great time.

She said if I’ve got nothing else to do I may as well hang out a bit longer. I genuinely enjoyed her company so I accepted.

Meeting up with my high school sweetheart years later [MF]

In high school I had a semi-girlfriend named Kelly who I was crazy about. Puppy love. We never really went out technically. I was too shy and timid and kind of chickened out of formally going out with her. We both knew we liked each other a ton, and flirted all the time, but other than one week of walking around school holding hands, we never went anywhere with it, but we were always very good friends.

She was a year younger than me, so when I went to college we slowly drifted apart. An email here or there, but we mostly lost contact as the years went by. After having not seen each other for 4 years, she emailed me telling me she was coming into town to visit a university she was considering for her masters. She was staying at a hotel nearby and asked if I wanted to meet up for dinner. I jumped at the opportunity.

I’d be lying if I said I didn’t still have feelings for her. In my mind she was always my high school puppy love that was a big “what if?” in my head. But we were just meeting up as old friends, so I never let my hopes get up.

[M]utual masturbation with a work [F]riend

This happened in college when I worked in the student union. There was a dedicated building car that student employees could use to drive around campus for whatever errands we needed to run. We always got our job done but were never above wasting time, especially on late night shifts when the workload was light.

One night I needed to drive across campus to deliver some form that probably could have waited until the next day, but I was bored at work and had nothing better to do. I asked my two coworkers on shift, Annie and Lisa, if they wanted to come. They were always down to take the building car because we usually stopped at McDonalds for a snack afterwards.

Anyways, I was driving with Annie next to me and Lisa in the back. As they tended to do, they were teasing me about the fact that they both got laid regularly and I didn’t. Lisa especially had a tendency to brag that her boyfriend takes care of her regularly. Annie was a bit more reserved, and while she was sexually experienced, rarely talked about it. After a few minutes of teasing, I decided to start shooting back.

[MF] My sister-in-law and I get friendly

My wife’s sister has always been attractive to me. Shes a couple years older than my wife (I think she’s around 32 or something) and has never been married. She’s actually pretty shit luck in general with guys. Ever since I met her something about her has struck me as being a bit wild. Maybe it’s because my wife’s family is relatively conservative anyways, so she is a bit of a black sheep. She’s more willing to wear tighter clothes, lower cut shirts, etc. I’ve always appreciated that of course and wouldn’t mind sneaking peeks whenever I could, but obviously never thought of doing anything about it.

Anyways, last year she came to visit. She lives in Oregon, so she was flying into town and I went to pick her up from the airport. I’ve done it before and we chat a bit, but for the most part we don’t have a ton in common and the ride will tend to be quiet. This time I asked if she’s been meeting any guys she’s interested in. She told me a few, but none of them ever pan out. I kind of felt bad for her. She’s picky, but she’s also got horrible luck.

[MF] A Snap to the Wrong Person

This all started with me trying something new with my wife. I’ve been traveling and being away from her is hard. Both because I miss her and because she can do things to me my hands just can’t. We’ve never really been the sexting type (at least not since we were still new to each other), but my hormones were raging and I decided to take a risk.

I wrote out a snap post, no image, just a black background with the text “FYI, I’m really horny, especially when I’m away from you. Prepare yourself, or you can do something to help me out right now.” I figured that was suggestive enough without being too blunt. I sent it off and went about doing some work in the hotel room.

An hour later I got a notification from Snapchat that my snap was screenshotted. But not by my wife. Her sister. My mind raced. I must have sent it to my sister in law accidentally. Holy crap. I hadn’t sent a dick pic or anything, but that’s still embarassing. Plus why did she screenshot it?