gonewildstories Archives — Page 5590 of 5640 — NSFW story

Lesbian sucks two loads from me

I've mentioned in previous stories that I've had great luck with Craigslist platonic ads. Recently while preparing for an extended business trip to a new town, I replied to an W4M ad that basically said "Looking for a chat friend". Turned out to be a mid 40's lesbian who was in a long-term relationship. "Lesbian" may not be the correct term but that's how she identifies, even though she had a boyfriend when she was younger and still is very attracted to men. But she had not touched a cock in nearly 20 years. Said she kissed a guy once at a party a few years back but nothing more.

We exchanged a few emails about random life things and also exchanged pictures. She wasn't really my type but she seemed nice and I've had a fling with another bi-girl that before was in a long-term "lesbian" relationship. So I Figured it was worth pursuing either way. Shortly after exchanging pics, she started calling me "sexy man" or "hot stuff" so I knew what was going on. It didn't take much prodding to find out she was craving a cock really bad. Her girlfriend was butch and found men absolutely disgusting. Because of that, a threesome wasn't a possibility at all so she knew she had to do something on her own if she needed a man fix. She told me that she remembered sucking her boyfriends dick all the time and she really missed that. I didn't want to come off as being pushy so I just told her that it sounded hot and he was a lucky guy. Read more »

Cynthia’s beginning part 2 – M/f – d/s

I want to inventory each step along the path. But, to be fair, it was a slow one at first. Each day seemed to add a new small step of perversion and sexual discovery for Cynthia. It would take too long to detail it all.

We moved very slowly. Tieing her legs and her hands. Having her beg to cum. Having her call me sir. For the most part it was all the same though. I’d tie her up on the bed and fuck her. We added layers each time. This time I spanked her as we fucked. This time she begged to cum. This time I threatened to fuck her ass. This time I tied her kneeling and that time laying. Hands up, hands down, etc. Then we started to incorporate pain. A bit of spanking. Nipple biting. Some smacks to the face.

The first night I spanked her, we were both taken back by how much she loved it. We were naked. Her across my knee. I demanded she count each spank and by 20 she was begging me to fuck her. Begging to have my cock inside her. I made her wait to 50. She came so hard I thought she would pass out. Read more »

I’ll be there for you [m+f]

It’s been a long year. Since last we spoke (see Sorry and Gotta make hay for examples) and a lot has changed. Medical issues, biopsies, tears, hugs, shit. Not to go all Debbie Downer on your collective asses womp womp … This is /r/Gonewildstories afterall… Life goes on and we do the best we can.

It’s times like these that make you realize, one way or the other, what sort of relationship you have. I would say ours is just great.

When we first found out she was sick it was quite a shock. We had been busy raising our young boys, working, and squeezing in as much fun times as we could. You never expect something like this, especially in your 30’s, which is probably why it was so devastating. There was an awful lot of soul searching and talking that took place during all this. Inexplicably this whole thing managed to bond us even more rather than tear us apart. Read more »

The First Time (or why you don’t leave two sexually frustrated and emotional virgins alone in an empty house) [M/F]

     The rain tapped lightly on the roof, filling the silence that enveloped my bedroom. We sat at either end of my bed in the corner of my room, soaking in the aftermath of the chilled phone call from the boy’s mother. His brows knitted as he looked to the floor.
     "I…I don't know what…" He trailed off, covering his face with his hands.
     "Hey," I started, trying to find the words. "It's ok-"
     "No, it's not!" He exploded, turning to me with pain in his eyes. I sat back, startled. "I'm sorry," he said quietly, pinching the bridge of his nose with eyes squeezed shut. "I don't know what's wrong with me. I can't get any of this right. No matter what I do, someone is always going to be pissed at me!"
     “Nothing is wrong with you,” I said, shifting on the burgundy comforter, “Not a single thing.”
     “I can’t appease them without hurting you, and I can’t make you happy without starting a war with them,” he muttered. “I can’t win.”
     I didn't know what to do- I'd never seen someone in a state like that. Looking at him then, watching him wrestle his demons with his eyes squeezed shut and head against the wall, I knew I couldn't fully comprehend what he was going through. I hated his parents for making such a big deal over something so small, but I knew that his entire future depended on them so he couldn't afford to argue. I didn’t know what to do. Read more »

The most tempted I’ve ever been, I’ve cheated and it felt great [m/f]

My ego really wants to post this with my real account, but I won't. Also, there are some people in my life that could figure this out if they ever read this.

I used to be proud of saying that I had never cheated in my life, but that all changed a bit over a month ago. The universe put me in a very difficult position, my relationship was hellish, my girlfriend played so many games and was so insecure (I ended it things 2 weeks ago). All the signs were there indicating that the relationship was coming to an end. We could no longer agree or meet in the middle on certain principles. The only thing that worked was sex, she let me do whatever I wanted.

This is what happened- Read more »

Craigslist True Story

Put an ad on CL recently looking for a F or CPL for a BJ.

Had a couple respond and arrange a meeting. I drove to an empty parking lot along a busy road as instructed and waited. I was nervous and excited at the same time and even considered leaving once I saw they were 10 minutes late, but boy I am glad I didn't!

They pulled up in a large White pickup truck with a crew cab. I got out of my car and walked towards them. The wife opened her door and jumped out. She was about 5'5" with shoulder length blond hair. She had very short tight Jean shorts on and a large loose white T shirt that barely concealed her large tits. She smiled, gave me a quick hub and told me to climb in back.

The husband moved her front seat as far forward as it would go to give us room. They asked me to sit in the middle and pull out my cock.

The husband adjusted his mirror so he could see my cock and told me how nice it was, even though at 7 1/2" I feel I am fairly average. Read more »

It was just supposed to be a standard three Some…[MMF, Reluctant bi]

Hey everyone, I had the craziest sexual experience of my life so far last week and just need to share it!

So I've got a couple married friends, Kyle and Brittany. I've known them forever and we're really close. We're quite open with each other and talk about our sex lives all the time, meaning mine as a single guy and theirs as a couple. Frankly I think they get off hearing about my experiences and live vicariously through them.

Anyways, after many drinks one night they confess that they've been discussing the possibility of inviting a third into bed with them. They danced around the topic a bit before admitting that, yes, they were asking if I would be that third. Now, Brittany isn't a girl that would necessarily turn your head on the street. Don't get me wrong, she's a good looking woman but fairly average and has a few extra pounds on her. Not that I mind, that's exactly the type of body I like. Thick and curvy. Those two words definitely describe Brittany. She has this incredible rack that just sits on her chest like a shelf (38DD's I found out), but they are all natural. Any shirt she wears just strains to contain them. She has a soft mid section with a bit of a belly, which again I like. But when you get to her hips…oh my god. The widest, swaying hips you've ever seen, attached to two impossibly thick thighs and a huge, round, shaking ass. Read more »

The Complete Date (MF)

Amy was a girl I dated early on in college. She was just a bit over 5', black hair, little on the side, full C breasts, a nice small ass that popped in her tight jeans. Classic handfuls of ass. We were taking it slow, going out on a few dates, hanging out with friends. Our 3rd date came around, we decided for dinner and a movie.

I go to pick up Amy, meet her and the door and I'm greeted with that hug and passonate kiss you experience when things are heating up. She was wearing a tight red top and jeans. We drive to dinner, small talk about our classes. She's being more hands on tonight with the hand holding, footsie. I tell her I hope she enjoys the movie, said said we will either way. We then head over to the movie. Read more »

Secret Slut Adventures

I am a 31 year old Secretary in a nice office. I dress very nice, but as unsexy as possible for work. My co-workers, friends and family all think I am a total prude. Most likely even think I am a virgin, but that ship sailed long ago.

I now schedule weekend trips out of town and away from anyone I know to go on my slutty adventures. I have gotten sluttier over time to the point where I feel like I have done almost everything…and loved most of it.

I had a few boyfriends over the years, but most barely tried to kiss me. They all "knew" I was a good girl, mostly because of my family and the friends I kept. Things improved in college (I only finished two years). I was still proper and demure, but I spent a semester in Europe and really got my first real education.

I traveled Europe as much as possible that year, which is where I started the whole, slip away for a dirty weekend. I would go to new and exciting places and reinvent myself. I started buying slutty dresses and going to clubs to drink and dance which lead to a few one night stands. Read more »