Weekend Vacation – Part 2 [MF][MFF][Group][CUCKOLDING][Long]

I hope you can forgive bad formulations and mistakes, English is not my native language.

How I was cucked by my buddy Karl for the first time after losing a bet to him you can read [here](https://old.reddit.com/r/cuckoldstories/comments/9b97nw/wager_with_an_old_army_buddy_mffcuckoldinglong/).

And how my wife arranged for me to be cucked a second time on our wedding anniversary, I posted [here](https://old.reddit.com/r/gonewildstories/comments/9bvyiw/anniversary_surprise_mfcuckoldinglong/).

Part 1 of this weekend can be found [here]
(https://old.reddit.com/r/cuckoldstories/comments/9ecv2w/weekend_vacation_part_1_mmfcuckoldinglong/?)

So after the events of Friday the four of us, my buddy Karl, his girl Christine, my wife Clarissa and me, still had Saturday and part of Sunday in the city before driving home. We filled the days with some more sightseeing, doing some fine dining and other vacation stuff in the city. Nothing out of the ordinary. Saturday night however was more memorable. The plan was for us to go to a casino.

And that is what we did. We dressed up, went to dinner and did some gambling. What I did not know at the time was, that the others had planned a setup to continue the cuckolding that had started mildly the night before.

[FM] Really Real Estate

Let me start this off by giving you folks some background on me. I’m doing this for a couple of reasons, one – because I think you need to know this stuff in order to understand the magnitude of why this was such an atypical situation to happen to a guy like me, two – because I’ve been an active Redditor for over eight years and I have a strong belief in giving *something* back to the community, and three – you can decide in the next minute or so if you feel like wasting your time reading this wall of text. Oh yeah, four – If you did read this, I’d like your input and opinions on things, after all, that’s what we are here for.

Neglected Husband Craigslist Lotto Winner Part II [FM] (yes there’s a few pics calm the fuck down no more pms please)

This is part two of how I became the one in a million guy searching on Craigslist to find the nearly perfect dream. Part one is right [here.](https://www.reddit.com/r/gonewildstories/comments/9egwra/neglected_husband_cruises_craigslist_and_hit_the/?st=JLW0PNO0&sh=c250a323)

Also please don’t send me PMs that just tell me she’s hot or asking for pics. Digging up these pics is a lot of work and I’ll share what I can. I am also sad to say that too much of what I have has my dick in it. Don’t nobody wanna see my dick.

On with the story.

Over the next 3 days we texted almost nonstop. A lot of it was sexual in nature but most of it was not. I spilled my guts to a senior in high school as pathetic as that sounds and she spilled her guts to me. Mary had a very successful mom who worked 60 hours a week and an equally successful stepdad for the last 5 years who she said was super creepy. Her real dad could take the cake for one of the worst possible pieces of dog shit to ever resemble human form. He left when she was 5 and she had occasional contact with him over the years. During this 3 day time frame she told me her bio dad was coming to her high school graduation which was in 2 weeks. I asked her when his flight landed and she said he had not bought the ticket yet. I knew then this piece of shit wasn’t coming.

Neglected husband cruises Craigslist and hit the lottery. [MF]

Save the hate please. I’m not trying to brag I’m just sharing. I’ll happily delete if it ends up triggering uncontrollable emotional responses.

I never thought I would be a cheater let alone a married one. That all changed last year. Until a few months ago I had an 18 year old girlfriend, eventually 19, and I was 38 when we started. I’m not proud of it but I don’t regret it at all.

My wife and I have been having problems for several years and like most relationship problems it crept into the bedroom. Before I knew it our sex life was non-existent. I have a very high libido and she did too when we got married. In the last 12 months before I cheated I had sex with her maybe 5 times and none of them were satisfying.

Last year around April when craigslist personals still existed I found an ad with a shockingly beautiful 18 year old blonde looking for someone to chat with online. I sent her a message and she sent me her KIK back. We ended up talking for a few hours when she suggested we meet up and smoke a joint. I still can’t believe I went and met her.

[MF] Drunk cheating with my wife’s best friend

This happened about a year ago, and for awhile I felt pretty bad about it, but I also can’t help but get super hard when I think about it. My wife hasn’t been totally faithful either – not that that’s an excuse, but we’re not perfect. Here’s how it happened:

My wife and I went out with a group of friends last year, and after dinner and a few drinks, we got rides back to our couple friend’s apartment. We’ve been friends with Kate and Mark for probably three years or so, and have gone on several vacations with them and spent lots of time together, but nothing sexual has ever happened between the four of us.

Just so you can picture everyone, Mark is a bigger guy, a few inches over 6 feet tall and about 230 pounds, somewhat muscular with brown hair. Kate is a bit tall as well, about 5’5″ and thin at around 120 pounds. She’s got light blonde hair halfway down her back, a relatively thin waist, and large C cups that fill out her frame really well. Her ass isn’t huge, but it’s round and pretty perky.

Not just another Tuesday,[MFF]

I’ve always hated Tuesday’s, the most depressing day of the week if you ask me, you didn’t, well I better get on with the story then.

First a little background because it’s very important, as I feel like the luckiest man alive. I am 50, I don’t feel it and thank god,(and also because I workout and run) don’t look it. I am married to a wonderful and very sexy 42 year old, she is from a wonderful group of islands somewhere in the Pacific which is where we live. We met 12 years ago while both working in the U.S. (I am British). Our first date ended up in a strip club in San Francisco where she got me to pay for her to have a private dance with a stripper, whom she got very handsy with. Straight away I realised she was a keeper.

Weekend Vacation – Part 1 [MMF][CUCKOLDING][LONG]

I hope you can forgive bad formulations and mistakes, English is not my native language.

How I was cucked by my buddy Karl for the first time after losing a bet to him you can read [here](https://old.reddit.com/r/cuckoldstories/comments/9b97nw/wager_with_an_old_army_buddy_mffcuckoldinglong/).

And how my wife arranged for me to be cucked a second time on our wedding anniversary, I posted [here](https://old.reddit.com/r/gonewildstories/comments/9bvyiw/anniversary_surprise_mfcuckoldinglong/).

After those two stories happened, I was cucked a few more times by Karl, after losing other wagers to him, and once or twice my wife arranged for me to be cucked. While those sessions were just as enjoyable it was nothing new. I have one cuckold experience left though, which is interesting enough to post it. So here goes:

So my buddy Karl, his long time girlfriend Christine, my wife Clarissa and I arranged for a little vacation. So we booked some rooms at a hotel in a big city for a weekend, from Friday to Sunday. We checked in and unpacked. After that we went out, shopping, sightseeing, drinking and whatever else you do on vacation in a big city.

[FMF] Manipulating a friend to fuck my husband

My husband and I opened our marriage over a decade ago. We are both just on the plus side of 40, with a kid in middle school. THings have never been the same after opening our relationship. As it’s the case with most open relationships, it is easy to find men who want to be with woman than the other way round.

My husband works with a guy, Sam. He’s 8 years younger than us and married to a knockout looking woman, Aditi, a striking brunette with shoulder length hair and a body to die for. They too have one child, a daughter. An year has passed from the last time my husband was with another woman. He likes younger ones and it is hard to find given our ages. Sam confessed to having hotwife fantasies to my husband while discussing their sex lives. Over the next few months, all four of us got together for dinner at either their home or ours. There was one problem, Sam has brought up the fantasy with his wife only recently.

[MF] Honeymoon sex and a ruined orgasm

I wrap my towel around my waist and open the bathroom door. She is waiting for me, in a sexy black lacy outfit. My new wife isn’t particularly body confident (though she definitely should be) but I can see wearing this outfit has made her feel sexy as hell.

I feel my cock literally spring to attention and I drop my towel and walk over to her. I cup her face in my hands and kiss her, gently at first but then more greedily.

She moans softly and I can feel the heat coming off her body as she takes my cock in her hand.

We stand there for a while just making out before she leads me over to the bed and pushes me down on it. I make myself comfortable  and lie back with my hands behind my head.

She laughs at my relaxed pose and then starts kissing me gently all over my body, pausing to occasionally gently bite one of my nipples which she knows drives me crazy.

She flirts around  my cock, getting close enough for me to feel her warm breath and then I watch in awe as her tongue flicks out and slides tantalisingly up my shaft.

Andi’s Date (FF)

Every time my wife gets ready for a date with me, she spends time on her hair, makeup and the clothes that best flatter her curves. That night was no different, with one exception: I was not her date. This particular night she was prettying herself up for her first date with another woman. She was nervous. She changed her mind back and forth at least twice on backing out of the whole thing. No matter how many times I told her I thought she was sexy and that I was OK with it, she naturally had reservations.
How we both got to this place is a story in itself. Like many others, Andi has always been curious about “what it would be like” with other women, and appreciates a good set of proportioned curves, sometimes sharing her own appraisals of women we see on TV or around town. However, her journey to making love with another woman proceeded slowly. We are kinky, open-minded, curious and –until that night– monogamous. Like many couples, we shared our sexy dreams and enjoyed porn together, but we’d kept it all in the realm of fantasy.
About a month before this night something changed. Andi came home with something she had to tell me. It seems a switch flipped in her and she decided she wanted to take the next step and actually meet another woman and see if they clicked. She explored the safest option and found someone from one of the hookup apps who was also curious and willing to meet up for the safe lunch.
I admit I was a little shocked she’d gone that far without telling me beforehand. I was also more than a little turned on, to be honest. I was not hurt or mad. To that point, we’d discussed hypothetical rules and what-ifs while in bed together, but nothing concrete. Anyway, Andi had lunch with the woman I will call Michelle and they hit it off pretty well, feeling the next step would be the three of us to meet for coffee before she and my wife went out on a real date, solo. Both of them were surprised when I didn’t balk at the idea or try to invite myself, turning it into my own male fantasy.
That’s when I reminded my wife how many times I’d told her that I didn’t necessarily want to be a third and supported her explorations one-on-one if that’s what she wanted. In my mind, two women making love is a beautiful thing; a work of human art I don’t need to mix my brush in. On the flip-side I know that if I take the plunge of sleeping with another guy, I will want her there with us and involved in some way. The hottest thing I can think of is having him balls-deep inside me while I am balls-deep inside her. I want to be able to look her in the eyes when I feel a cock slip into me the first time, but this story isn’t about me.
Fast-forwarding to the big date night, with all the logistics and protocol out of the way, all that was left was for the evening to begin. I had to get her out the door without trying to take her right on the spot and remind myself that for that night at least, she didn’t belong to me. We’d agreed that the two women should go out, have drinks, dinner and more if the mood was right. I was OK with Andi not coming home until the next morning if that’s what fate had in store.
So, at this point, I was alone in the house with my thoughts, wondering what was going to happen and hoping they didn’t back out early or worry about what I needed. A couple of hours went by before I got my first text from Andi. While we’d agreed texts and calls weren’t really necessary or expected, I was happy to find out she and Michelle were having a good time. The second text I received made it clear just how well the evening was going. They sent me a short “selfie” video of the two of them kissing rather passionately and Andi ending the clip by mouthing “thank you.” My body reacted immediately and with an intensity I hadn’t felt since my early 20s and I mouthed back “you’re welcome.”
Another couple of hours went by before I got what turned out to be the final text of the evening. It said “See you tomorrow morning. OK?” It was accompanied by a photo of a hotel room key. I responded with, “Yes, darlin’ have fun. See you tomorrow morning.”