Category: gonewildstories

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. Read more »

Why is it such a Tabboo to goto Pleasure workers? This is more of a confession [M]

For the past 6+ months, I have been having unprotected sex with prostitutes. What started on a drunked night as a dare, became a secret habit. I was was depressed the first time, once I got sober and regained my senses. Feeling bad for myself did not help me. I tried confiding about this with a dear friend of mine. But after a few days, she said it was spoiling her peace of mind. After days of feeling sorry for myself, I realised the we only live once. As I was not sure if I got infected or not, I went on a spree. Any available prostitute I come across, who was willing to go without, I had sex with. At times, in the most unexpected places. Lost count after 25.

Not really proud of what I am doing but not remorseful either. It sometimes feels like its not wrong, as they too are people like us who are trying to earn a living and I am helping them in their business. And I am not comitting any crime as I am not forcing nor hurting nor robbing anyone and it was always consensual. Read more »

Watching our mate break in the new girl Megan. [MF]

Megan was pretty and petite. Very early 20s. Barely 5 foot tall, she had an incredible tight body. Fridays at work were casual and she would often wear gym leggings. You could see every curve on her lower body: two gym-tight cheeks and a lovely mound at the front.

When they learned she was single, some of the lads at work (me included) were desperate to see who could fuck her. She was only seconded to us for a couple of months: this added a further challenge. We got to work. After work drinks always had a flirty vibe. It wasn’t that unusual for colleagues to hook up or fool around a little. It was that kind of place. Good fun, no judgement.

I’ll be honest here, I took an early swing and had a big miss. We’d been out drinking for a good few hours and she was touching my arm a lot, flashing me the eyes and we’d spent a lot of time laughing. I leaned in for a kiss and received the last-minute head turn, allowing me to make only a cringe-worthy peck on her cheek. Someone obviously saw and the lads ribbed me for a few weeks. Gradually, a couple of the keener ones had tried and failed in much the same way I had and the inevitable rejection became something of a badge of honour. Megan seemed to be thriving off the attention. Read more »

sucked off a stranger on his birthday [FM]

About 2 months ago, I was out grocery shopping and a guy helped me with the groceries, he carried them to the car. We chatted a bit and got to know each other, he said it’s his birthday and he actually asked me out. I kindly let him down, because I wasn’t ready for dating atm, but I offered him a new deal :)

We got into his car which was parked near to mine, 5 minutes in and he came in my mouth, I had my lips around the tip of his cock and sucking it with my tongue, his cock throbbing and exploding cum in my mouth was so hot. I then wished him a happy birthday with his cum in my mouth and swallowed.

I had my husband record him cumming on a hotel mirror. I then proceeded to masturbate to it. [F][M]

This past week, my husband had to go out of town for work for a couple of days. Due to our work schedule and life in general, we didn’t have time to have sex for a couple of days leading up to his departure so I knew he would probably be horny. Throughout the first day of him being gone, I was sexting him and sent him a couple of naughty photos. Things like me bent over with a message saying, “I wish you were behind me right now.”

Later that day, I sent him a message saying I wanted to see him cumming. He asked me what I wanted him to do and where I wanted him to shoot his cum. I gave him a couple of porn categories to use to tease himself and said I wanted him to shoot his cum all over one of the mirrors in the hotel room. He was so excited and said he would do it that evening once he was back in the hotel room. Read more »

[FMF] Threesome last week

So I have been hooking up with a guy I met on tinder.. and we hook up a few times, big stud man, playboy, massive flirt, great in bed. You know the hunk fuckboy kind. So last week, friday night, we were laid down on my bed, naked and sweaty from our hot sex, and we were chatting. The talk turned towards what kind of stuff we had done, as we were very sexual and wild, so we kept asking questions and I told him some of my hot stories… Until I told him about the time in my college when me and my roommate decided to explore if we were bi.. and we kissed.. kissed some more.. and half an hour later we were both on bed sweaty and happy from the orgasm we each got. So he was surprised I was bi, obviously as I didn’t tell him before that. Read more »

walked in a library to study, walked out with my pussy leaking cum [FM]

I went to a library nearby where I live to study after I procrastinated for a long time lol. But as I was sat , there was a guy sitting opposite to me and he’s very clearly hard and his bulge us visible through his shorts. I would be lying if I said it didn’t make me so wet, I asked Reddit for advice and I mostly got something like “grab his cock” which is absurd lol but one amazing redditor told me to flash him. I literally took off my bra Infront of him and flashed him. We looked at each other for long a time and sexual tension was very high. He approached me and said he’ll reverse a private room to “study”. Read more »

I 32[m] had anal for the first time with my wife 31[f]

So the past year or so my wife and I have been exploring anal. I love to eat, play with her asshole. We got a starter 3 size plug set. I’d use the little and medium size a lot on her. She loves it. She goes crazy when I eat her ass and finger her ass while in doggy.

The other night after a full week of being away and a lot of sexual build up, we had some intimate sex. I had her positioned in doggy and did my normal eatting her ass and fingering her ass. She was extra relaxed with it and loving it. I got the medium size plug and plugged her and fucked in doggy. She told me she wanted bigger. I took out the plug and put a condom on one of our glass dildos and started to place it into her ass. She was going nuts with orgasms. At one point she was begging for my cock to go in her ass. Holy hell I thought! It’s gonna happen! Read more »

What’s a little [F]ucking between good [F]riends?

This is my first time sharing an experience like this online but I was just SO high off it that I had to share it with the sub I enjoy so much.

❤️❤️ let me know what you think!

Last night I went to visit my friend because her and her boyfriend got in a fight and I thought she could use some support. After catching up, we started getting ready together. She loves it when I do her makeup.

We are both pan, and have always talked about our pan-ness, but surprisingly never done anything with each other. As long as I’ve known her I’ve been with my husband, and she’s been with her boyfriend for most of the time.

Since I arrived at 2pm, we started drinking a little early and ended up bar hopping until 12am. Before we left, we put on outfits that made us feel feminine and sexy. It was hot out, so I wanted to wear the least amount possible. I wore a white little crop top with no bra and a straight plaid mini skirt with black low top converse. I knew everyone would be able to see not only my nipples, but the curve of my full breasts against the thin, tight fabric of my top. It made me feel confident. Read more »

Cock Worship – I had a threesome with my best friend [FFM]

If I’m being completely honest, I wouldn’t really label myself as Bi-Sexual and never really thought of myself as being overly attracted to other women.. I mean YES like most girls I have been frisky with my friends on a night out drinking alcohol, making out at a club, grabbing their boobs and ass although never really took it any further than drunken, playful foreplay.

Anyway one of my friends [Jess] is an absolute stunner, she is busty I am so obsessed with her boobs and every time we are together I can’t help but feel and play with them.

Recently on a night out she confessed to me that she would get very turned on every time I touched her boobs or gave her any sexual attention and at that moment, I felt a sigh of relief and excitement as now I could potentially satisfy my bi-curious urges.

That night at the bar, we had a few cocktails, feeling tipsy and giggly amongst each other. There was a guy who was staring at us from across the room and after locking eyes with him I couldn’t help but give him a big cheeky smile. Read more »