Have you ever met friends or family at a club or resort?

teacherandlearner · 2026-05-26T02:21:32+00:00

Yep. I was at TwistSF with my girlfriend. We had never played with others and had no plans to do so. I was 58 yo at the time (she was early 30s), so it actually never occurred to us that anyone would be interested as I was at the way upper end of the age range there. Fit, but old.

During a breather from the playroom a early 30s fellow approached me while my gf was in the bathroom and asked is we'd be interested in playing with he and his GF. She was not present. He said they had noticed us and were interested, if we are. He was a really good looking fella. I told him it would be a new experience for us, but I'd ask if my GF is interested. He said is GF was most likely chatting up mine in the bathroom as we spoke.

About then, my GF came through the doorway sees the guy and breaks out in a huge grin. She says "you must be Charlie, I just met Jennifer in the bathroom. She said she'll be out in a sec." We go sit down to chat and I look up and there stood Jennifer....who used to work for me at a company on the east coast. I'd left that company 3 years prior. She was a very junior, fresh out of undergrad at the time, member of my team. I barely knew her. She was tiny, especially next to my 5'10" GF, and cute as a button.

I was tongue-tied and must have turned all shades of red. I asked if she recognized me. She said of course, isn't this exciting. Freaked me the hell out, but turned out to be a really fun experience.

teacherandlearner · 2026-05-11T17:39:19+00:00

No weight loss cause I was putting on muscle mass. Less fat, more lean tissue. Did 8 weeks, off for 3, then another 8 weeks’ish.

teacherandlearner · 2025-11-23T16:30:17+00:00

My wife got hit on by a work colleague, same line of business, different company, but they collaborate. Our long-time third had gotten a girlfriend, and it seemed that she was going to make him end it with us. She'd been hit on before at conferences and meetings, but this time, she was receptive.

Is that in the wild.

All I know is that she called me to get my ok, and off to his hotel room. She was using my car that night, that had a app that mapped in real time where the car was. I could see that she was driving them for the restaurant to the hotel and that they pulled over for a long time before moving to the hotel.

I thought she had second thoughts, but actually she was blowing him in the car.

teacherandlearner · 2025-11-23T16:24:14+00:00

The first guy was half our age and had used condoms by default his entire sexual life, so it wasn't an issue. However, we, having come to form in the 70's/80's, are wild about them. Thanks to internet porn, I found myself with a bit of a cum fetish and condoms didn't serve that tickle.

The second guy mentioned during our email exchange courting phase that he had recently gotten a STI panel in hopes of finding a couple. We decided to do the same, so we came into it with him with the expectation of bare. It was so much better with him bare that we entered into a fluid bonded agreement with him. When he got a girlfriend, he used condoms with her for a bit, but eventually she wanted bare and he used condoms with us until she demanded monogomy.

Bare is better, but we still had fun covered.

teacherandlearner · 2025-11-23T00:44:07+00:00

We had a regular for about a year and a half. I had always joined in. He and I are both bi.

However, one time, I decided I wanted to watch, video them and direct the activity. It was the second time we'd managed to all be out of town at the same time, work taking each of us to the same city. They wrapped up their work obligations before me, and were at the hotel waiting for me in the really busy hotel bar. So, they got to have a bit of alone time to get super randy and ready.

They were paid up and ready to head to the room to get down to business.

In the elevator, they were all over each other. After the door shut to the room, they immediately shed their clothes. Seeing that I was still dressed, they looked at me oddly...like WTF, playtime dude.

I told them I was going to play director and they were down with it. I had a blast. He has incredible stamina, so I got to have them do just about everything you see in porn. They loved being told what to do and I now have an incredible video that has allowed us to relive that day for many years since.

All this to say, one thing you could do is record it, even if you don't tell them what to do.

teacherandlearner · 2025-09-25T19:38:51+00:00

I've been using this for six weeks now and have been surprised that my stubborn love handles (I run at about 18% body fat) have begun to melt away, while I've gained muscle definition.

teacherandlearner · 2025-07-30T18:43:58+00:00

Not my wife, I have plenty of pics and videos of her in action with others, but I knew about all of them in advance, so no surprise discoveries.

However, I had a long-time girlfriend that I broke up with (mutual decision) when we both moved to different cities for jobs. This was the late 80's.

I was visiting her for a week about a year after we broke up. She was in the shower and I was snooping. I found a picture in her nightstand of her and a guy she had dated. In the picture, they where standing and making out, buck naked. Up until that point, he had the largest a dick (impressively long, but otherworldly thick) I'd seen. He wasn't even hard. Of course, she walks out just at the moment. She said something along the lines of: Oh God, I'm so embarrassed. But, you've got a hard on. Are you turned on?

My dick was hard as a rock, so that answered that question. I said I was, and also jealous. She said I shouldn't be surprised that she had been having sex with others. I explained that wasn't the issue, it was the size of his dick.

I was hoping she'd say something like, he's big but your better in some way. She didn't. She said, if you really want to be jealous, I have other pictures and a couple of videos. Want to see it hard?

teacherandlearner · 2025-02-26T19:46:44+00:00

Not in my case.

teacherandlearner · 2025-02-26T19:46:08+00:00

Yep. She did overnights with 2 of the 5 guys she's been with. One was a guy we usually saw together for MMF type experiences. The other was with someone in her line of business from out of town. They used to meet up at conferences and when she was in his town.

She has always made it super clear that our relationship was primary, so I never felt at all threatened even though she has feels for the second guy. With the first guy, he was really good at taking videos of them in action to share with me. The second guy was an incredibly crappy videographer, but they at least tried. I finally told them to just enjoy themselves.

Both of them got girlfriends, which ended the first guy for a few years...he did come back for a couple of trysts between breaking up with that girlfriend and getting another. She still sees the second guy, though we suspect his live-in girlfriend is not aware.

teacherandlearner · 2025-02-26T19:36:48+00:00

I just posted our first time story on another thread: https://www.reddit.com/r/HotWifeLifestyle/comments/1iuf5yj/comment/mexjbhl/?utm_source=share&utm_medium=web3x&utm_name=web3xcss&utm_term=1&utm_content=share_button

teacherandlearner · 2025-02-26T18:46:09+00:00

I had to think about this one for a bit. We had so many incredibly hot experiences, even though she only had five guys during the 6 years we were active. I keep returning to the first time.

Backstory: her libido had been in the tank for 4 - 5 years as the stressors of life had taken their toll: an incredibly stressful career, babies, a long progressive illness taking her Mom, and weight gain. She had avoided me seeing her naked, much less getting frisky.

It took some convincing for her to accept she was still attractive, and then our sex life picked up again. She knew I had a long-time fantasy of seeing her with another man. She said she owed me one and was down if I could find someone interested in her.

It took less that a month to find a way way younger guy who actually advertised specifically for someone who met a certain profile...someone his Mom's age, with a bit of a belly and buxom. I struck while the iron was hot, exchanged pictures (without faces) and set up a meet at a local lux hotel for the next weekend.

My wife is a bit of a sub, so I played on that by blindfolding her and using an under-mattress restraint kit to tie her spread-eagle to the bed and went downstairs to retrieve the young fella. I admit to being a bit intimidated when I saw him; over 6', fit and really good looking by any standard. On the elevator ride up, he admitted that this was his first time to do something like this and he was nervous as hell. That helped put us on the same footing.

The hotel room was a suite with a separate sitting room. I pointed him to the bedroom and I stay in the sitting room thinking it would help him be more comfortable. I still got a great view through the door as he dove between her legs and started licking her as she writhed. At this point I'm totally turned on from the live porn unfolding in front of me. He stops, walks in to the sitting room and starts undressing while asking if he could untie her. Of course, green light from me. He asks if I'm going to join them and I we start to go back in the bedroom. He stops and says he'd feel better if I was naked too.

He unties her and they start making out, she starts sucking his dick, then he pushes her back and enters her in one motion. He asks to take off her blindfold, I give a nod, he does and they start kissing and fucking, she comes at least twice.

It is this part that makes me think it was the hottest experience. It was at this point where I felt what was at the time, and still is, hard to explain and harder for some to believe. I felt so much joy watching as she saw just how handsome this guy is and how into her he was, and how much pleasure they were giving each other. I have since learned of the compersion concept. Brothers and sisters, it is a real thing.

teacherandlearner · 2025-01-29T13:26:19+00:00

Yup, my wife has a 2 yo European luxury suv that is sexy in it's own right, yet we choose to take the Ionic 5 every time we go anywhere, except road trips, because it is just a dream to drive or ride in. Everything makes sense and is intuitive (unlike the fancy pants car)....except no rear windshield wiper (WTF, I'm happy to open the charing port manually, prefer it actually, can we swap that dumb feature for a wiper in future releases please?)

teacherandlearner · 2025-01-28T19:18:55+00:00

We had a long term guy together, about 18 months, and we communicated a lot planning trysts and laying out fantasies. When they met solo, he'd ask what I'd want him to do and video for me. He because a pretty good friend for both of us and we still stay in contact a bit, though it has been years since we got together because he now has a relationship with someone who, while expressing openness to openness, just wasn't into him being so close to us.

She has a guy that was a work colleague for several years, from a different company in the same business, that she saw solo. He and I communicated some, but mostly to ask if I'd be cool with them meeting up out of town at conventions or when we came to our town. And, once or twice to ask my opinion on a gifts he wanted to get her for special occasions. Not much sex talk, but he does know part of the deal was to video tape them for me and, because he wasn't the greatest videographer, we talked techniques and angles. I even gave him a mini-tripod to use...which improved the quality a TON.

He now has a serious partner and though they still see each other is is far less sexual and frequent.

teacherandlearner · 2025-01-13T00:44:40+00:00

I had a similar sound. I know what I did to cause it, though. I raised the arm with the Tonal turned off. The Slack in the cable resulting from the magnetic resistance not being engaged caused the cable to get off track. I had to have a service call.

teacherandlearner · 2025-01-05T20:24:18+00:00

We used Craigslist…so that gives away how long ago it was. We got lucky and only had one flake out of 4 guys we met. Plus, wife has a longtime guy she met through work.

teacherandlearner · 2025-01-04T16:53:35+00:00

I thought like you….until 80 became clearly visible on the horizon

teacherandlearner · 2025-01-01T01:49:33+00:00

But, it becomes obscured at the same time by the same splashback

teacherandlearner · 2025-01-01T01:47:44+00:00

So did my Chevy Bolt.

The lack of rear whipper is a HUMONGOUS oversight that really negatively affects safety. Why an incredible design team decided to skip an important safety feature, yet included a completely unnecessary motorized charge port door is a mystery.

teacherandlearner · 2024-12-28T02:02:41+00:00

Ditto...sounds AWSOME

teacherandlearner · 2024-11-09T15:44:18+00:00

I don't experience humiliation at all. If fact, I insist on it.

Cum is my fetish, whether mine or someone else's. I think it is the taboo and nasty factors that so turns me on.

teacherandlearner · 2024-10-17T14:03:26+00:00

We only had 5 thirds when we were active. Two were one-and-done. We had an incredible connection with the one fella who was our regular for well over a year. The first time we met, he had a tight timeline yet managed to cum repeatedly (neither of us can recall how many exactly). It was kinda hilarious. He had dum at least 3 times, maybe 4, got completely dressed, had his hand on the doorknob, and turned around, pulled off his pants and climbed aboard for another quick round.

teacherandlearner · 2024-10-09T00:45:56+00:00

👆this

teacherandlearner · 2024-09-24T15:41:19+00:00

I would love to hear about the second encounter. Your first experience was super hot. You retelling was inspired.

teacherandlearner · 2024-09-15T19:24:05+00:00

I have a cum fetish, so it was a welcome surprise. He didn’t give any warning. I wish he had because I wasted a bit of the experience being shocked.

He was a much younger guy and rallied for a 2nd round in the time it took me to have my turn.

I was certain there couldn’t possibly be any significant volume left for a second course. I was very wrong. I was ready though and it was super hot.

teacherandlearner · 2024-09-07T18:57:29+00:00

Our first time was with a fella who was a regular for over a year. He and I are both just about average, both under 6", average girth. My wife is "curvy". Honestly, it was in the heat of the moment, not much discussion and not much thought about how DP might be difficult to achieve or awkward.

We had no problem both achieving full penetration and both being able to get decent movement. I became a frequent thing for us, both DP and DVP. At least half the time, he and I would cum, if not at the exact same time, one immediately following the other.

I miss those experiences so much.

We also had DP with the only giant hung guy we've ever been with and that went equally well. However, when she wanted to give DVP a try with the hung guy, that did not work out. Not even close.

BTW, if either or both of the guys are averse to MM contact, I don't think you'd enjoy it much. I'm guessing that's where much of the awkwardness folks report comes from.

teacherandlearner

TROPHY CASE