Giving a creampie to a curvy MILF stranger [MF]

Before my wife and I found each other and started having our own adventures, I spent a few years exploring the swinger scene as a single guy in my early 30s. This was in the heyday of Craigslist personals, and I had some great luck finding folks to play with. One of the biggest turn-ons for me was the anonymity of it all. There was nothing quite like meeting someone for the explicit purpose of sex, knowing that within a few minutes the clothes would all be off and you’d be deep inside this person that you’d literally just met. It focuses the mind on the urgency of fucking…no thoughts about relationships, consequences, personality…all that mattered was the act.

Most of my hookups during this period were with hotwife/cuckold couples that were looking [for a guy to come in, act the role they wanted, and hit the road](https://www.reddit.com/r/Cuckold/comments/yma1l4/dominating_and_creampieing_a_submissive_hotwife/), which suited what I was looking for perfectly. I did have a few experiences with single women, however, and one really still stands out to this day. She was a short, curvy MILF named Tina, in her early 40s, divorced, with a teenage son who she shared custody of (so she often had her house to herself). I met her on a swinger personals site (as opposed to my usual haunt of Craigslist). Her profile pictures were some boudoir shots and they were absolutely stunning…she had red hair, huge (but firm) breasts, and a big curvy ass that I just needed to see her throwing back on my cock.

Dominating and creampieing a submissive hotwife and humiliating her cuck [MF]

About a decade ago I spent a few years serving as a bull for hotwife and cuckold couples. I got started in the swinging scene with more standard mfm/mmf threesomes, but over the years my dominant side had started to come to the fore and I realized I really enjoyed taking an alpha role and having the woman entirely to myself while her husband just sat there and watched. The more anonymous the better, as it let me get out of my head and be someone completely different than I was in my day to day life.

At the time the best way to meet people was Craigslist personals (RIP). It took work, but a well written ad would get responses (and a lot of spam and scammers, but they were usually easy to sort out). I opened my e-mail one afternoon and saw a response to my most recent ad from a man named Dave. His tone was very submissive, and I could literally feel his nervousness through the screen. He said that he and his wife Jane were staying at the local casino this weekend (Turning Stone in upstate NY, if anyone is curious – although I no longer live in that area), and they were looking for a guy to come and fuck her the way she really wanted to be fucked, hard and deep, and rough, before filling her with a thick load of cum.

[MMF] Two bi guys & a gal walked into a bar…

…and walked out a little tipsy, flirty, and ready to fuck. My wife Mary (at the time, 33) and I (then 36) had met John on Craigslist personals, right before they shut down. He was a hipster biker type, muscular but not cut, about 5’10”, with brown eyes, mutton chops and a slightly tamed shock of dark, almost black hair. I’m 6′ tall, brown hair, blue eyes, with a tendency towards a dad bod but in decent shape from a running hobby. Mary is 5’8″, with curves in all the right places, greenish brown eyes, and long auburn hair.

We headed back to our place, which was only a few minutes away. I grabbed us another round of drinks and we all sat down on the couch, Mary in the middle. We chatted a little more, nervous tension in the air – this wasn’t a first time for any of us, but it was our first time together, and there’s always that long moment before someone makes the first move. As I took another sip of my beer I saw John’s hard cock stretching his pants, and I knew I had to get my hands on it. I leaned in and kissed Mary, and as I did so I reached across her and started to rub him through his pants. Tension broken. John started to kiss Mary’s neck and rub her breasts through her top, and we were a pile of hands and mouths, kissing, touching, stroking, rubbing.