gonewildstories Archives — Page 3077 of 5640 — NSFW story

[M]arried [M]an’s First Naughty Craigslist Encounter

# This will be the first installment of my confessions on my erotic deeds / misdeeds. I offer these not to brag, though there was often joy and exhilaration, or with a sense of conquest. And I offer them without moralizing, though there was also at times degradation. I tell them because we are all storytellers and where else but on an anonymous board like this one can I tell these stories? You can judge them and me if you want, but I can promise you that they are all true. So read on.

About me — I am now in my mid-to-late 60s, well liked and respected in my profession, a ‘success’ I suppose in that sense, and also have grown children and a few grandchildren who hold me in esteem. And I have been married to the same woman for several decades, the only woman I have ever been married to … unless you count that period of my great affair, when I loved and was loved by two women and somehow managed to get through it with everything more-less intact. But that is not the story for your ears, no offense, as I hold my experience with the other *her*, may she rest in peace, as sacred. But I digress. Read more »

I [M] felt obligated to prove my lack of refractory period to random internet stranger [F]

I’ve posted occasionally and responded to the posts of others and it usually doesn’t go very far. One time however I had been messaging back and forth with another Reddit user for several days and had revealed my lack of a refractory period. I had never had one and honestly thought it wasn’t real. I would always masturbate before a date or other close interaction with girls that I find attractive to minimize the chance of random boners popping up. My teenage awkward years never left me even decades later I’ve never had to worry about getting it up even when I don’t really want it to happen.

This person was upset over a previous date of hers not being able to perform in the bedroom on their first meeting and she was blamed as the reason for their lack of enthusiasm. It had turned her off to dating ever since and she was convinced that she would never find someone who could find her attractive enough to become excited. When I told her that some people had to get themselves off right before dates just to avoid the tenting of pants that can occur, she sent a pic of herself and said she had the cure to boners with her ugly face. Her face was anything but ugly and eventually I was able to convince her to try dating again. Read more »

[MFM]Life Lessons [Long]

A thing I have noticed on this board recently is that people are pretty much only talking about victories and successes. They are always about the hottest things that happen and never the fairly normal stuff that happens to. Maybe there’s a reason for it, but personally I miss the stories that were sweet, funny, or sometimes just outright embarrassing.

So for the sake of bringing some of those stories without pissing off too many of you, I’m going to warn you ahead of time: This story is about a crushing and embarrassing failure on my part that makes me laugh thinking about it now. Wasn’t so funny at the time. Unless I am told otherwise, future stories will not give this warning. They may be about success or failure… but considering my sex life they will probably still be hilariously awkward.

A long time ago I took a girl I was dating on summer vacation with me and some friends after we graduated high school. Near the end of the trip there were just three of us left in the cabin. Being a bunch of teenagers left alone in the woods obviously we got up to some stuff that will fit on this sub. Maybe I’ll go into those stories too later. Read more »

[MF] Our Last Day of Vacation Was an Interesting One.

My girlfriend and I have been together 3 years now. She 40 and got out of a 15yr marriage when I met her. The last 6 years or so of her marriage was nearly sexless. I’m 34 and can’t say I had much better luck with relationships. For most of the time we been together she did not want to talk about desire and sex, but would still want sex constantly. We have a great sex life, but there was always this communication block and it was a bit of enigma for me. After a time we explored, learned, and even started talking about sex. One of the things I learned, and a relevant tidbit for this story, is that she is really turned on by the idea of showing a 18yr guy how to eat pussy and showing him what a blowjob is like, especially if it’s before his first date. Another is being watched. She wants to see men’s erections caused by wanting her, but being unable to have her. I’m 100% on board with these fantasies. Partially, because I want her see her loose her damn mind living them out, but there is also this good house wife going naughty thing she has going on. Read more »

[MFF] Wife seduces Co-Worker.

The time was way back in 2011 while I worked at Target. My wife was popular with my co-workers because she would always bring me breakfast, lunch, or dinner if I was working late. She was especially popular with a co-worker of mine, let’s call her “Kim”. Kim was a tall, busty Puerto Rican with huge tits and an ass to pair. My wife and Kim would always casually flirt together, a wink here a nod there but nothing ever came of it. One Saturday night, Kim and I are getting off at the same time so my wife decides to invite her out to drinks with us. We head to a local dive bar and I watch as Kim and my Wife enjoy some drinks, flirt and laugh with each other. Pretty soon my Wife insists Kin accompanies us back to our apartment. At the apartment we sit down, talk, laugh it up and enjoy each other. While we’re siting down out of the corner of my eye I see my wife and Kim begin to make out. As soon as Kim notices I’m making Eye contact with her she begins to blush. I join in and begin to relish in the experience of getting to shag a co-worker (a three some rule my wife had set). Fairly quickly my Wife strips the clothes off of Kim and herself. Eager to join I stand up and my wife unbuckles my jeans and drops my pants where my now rock hard cock flops out. Hard, I’m 7.75 x 6 inches and I always thought I was “average”. I wish I could describe to you the reaction on Kim’s face. Her eyes and mouth were wide open and she could only bite her tongue and muster the words “wow, ok than”. We move into the bedroom where I quickly begin to plow away at my wife. I was hoping to give Kim the same treatment but sadly she wasn’t willing to “try”. The night mostly went with me fucking my wife while Kim made out with her, sucked on her titties and allowing me to finger her. Kim was very much turned on when I came inside my wife (IUD’s are awesome). The night ended and we parted ways. Work was a lot more fun after that night. Every time Kim saw my wife or myself she couldn’t help but giggle and blush. What was most exciting about this was after I left for Basic Training, my Wife and Kim continued having a sexual relationship(I allowed my wife to do this with women and still encourage it today) Read more »

[F] Question about masturbation and depression.

I won’t go into it too much so as not to bore you all, but I have a question about your experiences with masturbation and depression that’s been needling me for awhile.

Like a lot of people, depression dampens my sex drive. It dampens just about everything. I cry more, I’m empty more, insomnia sets in because of depression and also anxiety, anhedonia can set in, waves of grief hit me (sometimes at semi-random times, other times sparked by triggers or stress), etc. There are a lot of reasons I deal with depression, so these manifestations vary.

Sometimes, though, I feel like the only way I can feel anything is by masturbating. Has anyone else experienced this?

Sorry for the more dour topic, again. Y’all’s thoughts are appreciated.

Coffee and cunt [MF]

I met a woman at a coffee shop off of Craigslist back when the social and personals were a thing a couple of years ago. I was in my late 40s and she was 29. My office was close by, the woman in question asked if there was somewhere we could be alone before we had coffee. If we went across the road. As soon as the door closed behind us, we were all over each other, I pushed her up against the door and her cunt was already so wet I could smell her, my hands were everywhere, she dropped to her knees and took my thick hard cock in her mouth and sucked me off like her life depended on it, she couldn’t get me inside her quickly enough, she even has condoms on her. I held her down and fucked her hard on a work colleagues desk. I pounded her tight cunt with one hand around her throat and the other pushing her legs back, watching my hard cock slide in and out of her very wet cunt was so hot. I lost count of how many times she came. When I was ready to unload, I pulled out and she finished me off in her mouth, I fucked her mouth and unloaded a big warm sticky load from my balls, she let a little drip out and onto her amply sized tits. I went down on her afterwards and licked her wet cunt while I roughly fingerfucked her while she came over and over again. We left my office and went to have coffee, half an hour later she was back on her back being pounded senseless on the same desk. What a way to spend a Saturday afternoon. I was inside her 15 mins after first meeting her, that was a record. Read more »

[MF] The Saga of Sally – Analville, Population: Sally and I

(Welcome to the Saga of Sally! This is the story of my relationship with a girl called Sally. This is **Part 3**. I recommend you start from the [start](https://old.reddit.com/r/gonewildstories/comments/hsqikr/mf_the_saga_of_sally_cumstained_jeans/) – each piece will link you to next part at the end.

A brief reminder what Sally looks like (there’s a reference photo in the first part): she’s a pocket rocket, thick, redhead tomboyish girl, with an hourglass figure and the thickest ass this side of the Equator according to the Guinness Book of Records inside my head.)

For the next month or so, Sally and I fucked like rabbits. We had said we wouldn’t be exclusive, that we would just be friends with benefits, but when your booty call is also your best friend, you end up spending most of your time with them. There was no time for anyone else. I left my cold dorm room behind and spent my days either in class or at Sally’s house. If her parents were around, we were just friends hanging out. If we were home alone, we spent afternoons fucking each other to countless moaning orgasms. We learned a lot about our sexual tastes in that first month (and Sally fortunately got on the pill). My favorite position was doggy style and Sally’s was cowgirl, but both of us also fucking loved each other’s favorites. Sally liked to be spanked. I liked to cum on her skin. We both found that we got off on the risk of being caught. One afternoon I pressed her against the french doors of her dining room and fucked her from behind, her naked breasts pushed against the glass. We both knew inside that none of her neighbors could see from the angle, but we both came faster than ever before. Read more »

[MF] The makings of a slut

I’ve experienced a lot of different women in my life and this is one that I got to know particularly well…

I answered an advert on Craigslist, a woman went by the name of Leonora, she was looking for an older experienced man who knew what he was doing but a man who was also dominant and definitely erring on the side of kinky. A man of the world who knew how to hold himself and was a gentleman on the outside but behind closed doors, let the animal part of himself out to play.

We chatted for a few days about the kind of thing Leonora was looking for and what I enjoyed, we arranged to meet at a pub in the back streets of a fashionable well heeled area of London and agreed to exchange pictures that day. Being a teacher, she was very cautious about showing me what she looked like although her description was pretty damn accurate as it turned out.

I remember feeling nervous, i didn’t know a lot about Leonora except she was 31, 5’5, a natural blonde, long shoulder length hair, she said she was in great shape, smallish tits but a nice round arse. Read more »