Masturbation Archives — Page 453 of 468 — NSFW story

The Start of [M]y Sexual Li[F]e

I've bee lurking GWS for awhile now and I think it's time I catalog my experiences here as well. All you need to know about me is that I'm currently middle aged and while I'm not an Adonis, I'm attractive enough to have gotten all the pussy (and occasionally dick) that I've had. I've seen many a story here about girls losing their virginity, but hardly any about a guy's first time. So that's where I'm going to start.

I was what you might call a late bloomer (at least by today's standards). I had my first girlfriend, let's call her Amanda, at 18. She was my age as well, but vastly more experienced as I would come to discover. She was a very petite girl, standing only 4' 11" and probably 100 lbs soaking wet. She had no chest to speak of, but she did have a nice, tight little butt. She had a slender face and long raven black hair. But what really got me were her eyes. Big, blue and round just like any Pixar character you'be ever seen. I could get lost looking into them. Read more »

Shawna: Roma Revenge – Part I – The Metamorphosis [nc, MF, mast]

My name is Shawna. At least, according to my license it is. I used to be Shawn Milner, a relatively successful businessman with a bit of a drinking habit. I had lived as Shawn for twenty-seven very satisfied years, taking what I wanted from life and giving it my charming company in return. Even when that company was unwanted.
I was handsome, bold, strong… I really had it all. Not that I didn’t work hard at some of it; it takes more than wishful thinking and good genes to earn a square chest and a six-pack. But the art of communication, the gift of manipulating people? That came naturally to me, and I had no problem reaping its benefits.
I still remember the party that changed my life. It was a business function, after-hours drinking in the office. I suggested to Maria, one of our younger interns, that she should stick by me for the evening. Didn’t really give her a choice, to be honest. A strong personality can be like that.
Maria was smoking hot. She reminded me of that slutty-looking girl in that Disney movie, the one with the hunchback, but with more clothes on. I’d set my sights on her, but she was playing hard to get, acting like she just wanted to be friends. I’d have been fine with that, except that I wanted a piece of her. So I spent the party nursing one drink in a red plastic cup while making sure she had considerably more than that. Granted, there’s nothing wrong with fetching a lady a drink when she’s thirsty. Not at all.
Crushing up a few allergy pills into the drink, on the other hand, is more of a gray area.
At the time I didn’t see anything wrong with what I was doing. Or at least I didn’t let myself see. I justified what I was doing, telling myself that she was obviously drinking like a fish, and she’d get wasted eventually, so there was nothing too bad about giving her a little nudge in the right direction. And besides, there was like a fifty-fifty chance that she’d wake up, remember nothing, and thank me for taking care of her. So I felt no guilt – consciously, at least – when I dragged her down to the parking lot and into my car. And I felt even less guilt when I pulled the car over, leaned back her seat, pushed up her skirt and shoved myself inside of her.
The really hilarious thing is, it wasn’t even that good. I barely lasted a minute, pumping into her at an awkward angle, and I came before I was ready to. I had planned to shoot it over her chest or face or something, but instead I exploded mid-thrust inside her. That was probably my real mistake.
I took her home and laid her on my couch, then went up to bed. The next morning, she was gone, and I had a hangover so bad I wasn’t even sure what had happened wasn’t some weird dream. It couldn’t be, though, because I found Maria’s panties in the pocket of my slacks when I went to toss them in the laundry bin.
Maria didn’t show up to work the next week, but nobody said anything to me. I was starting to think that I’d gotten away with my little indiscretion and had pretty much put it out of my mind by Friday night.
Saturday morning proved how hasty that had been. Read more »

Im 42 years old, married with 3 kids and i fucked my sons friend.

This is the story of how I had sex with my sons best friend (Cameron). However before i begin i should first give you a little backstory, i am 42 years old and married to a wonderful man, however, as cliche' as it sounds he works a lot. He is a Nurse and does 12 hour shifts, most of these shifts are at night so when he gets home he sleeps during the day and then gets back up and goes to work so we don't have sex as often as i would like. I have blonde shoulder length hair, c cup breasts and a fairly decent ass (i think its my best quality). I work out a lot and eat well so i am fairly fit. Read more »

The end to 4 years of no sex. (Part 2)

Now I don't know what made me do it exactly. Maybe it was my anger from being rejected by a couple female interests earlier in the year, the testosterone boost from working out 3-4x per week (as a result of that anger), or the fact that I had not been on a single date in years. Then again, maybe it was a combination of all these things. All I knew was that I needed to get laid.

The closest I achieved to penetrating pussy in the last few years was by proxy of a video-calling service to an eagerly sexual Indonesian girl half-way around the globe. We engaged in several sessions of mutual masturbation. I recall her placing her pussy in full view of the webcam as she laid back, fingering herself as I broadcast my own stroking routine with pleasure. On an earlier occasion when we were chatting, she asked "What size your dick." "5 inches," was my response, to which she followed with neither disappointment nor glee, but went on with her persuit of other questions, as though we were moving into a more serious relationship with each other. When pressed, she let me know that size wasn't that important a matter to her. She was a bit funny though. On one of our video sessions, she had gotten herself off and was then watching me intently as she was typing out messages to "help" me get myself off. "Making a baby" is one of the things she would say, which was probably one of the least sexy things I could think of. Then when I did cum all over myself she said "that's it?" I suppose my ejaculation via webcam was not as explosive and momentous as the porn she had been watching. Read more »

Hilly and Ben – Their First Date 4 [mf][Str8][oral][mast]

Click on my name for the previous story called The Choir Trip or the first three parts of this story.

"Oh look," Kaylee snarled. "It's Ashley and her mini-me."

Bailey laughed like the joke was funny. The two of them sat at the center of attention in the soprano section surrounded by their venue of vultures. Hilly had been similarly insulted by the pair when she arrived but chose to ignore them to get her music together for rehearsal.

Looking up, she did notice something different with Ashley and Madison. Hilly remembered that Ashley had driven Madison home after the student council meeting. Thinking of her own study session with Ben, she smirked and wondered if they made use of their time together as well.

Ashley looked over to gave Kaylee a snort and look of pity. "Is that all you got, Bi-Bitch?"

It made Hilly chuckle that she dropped their new name for the duo in front of the whole choir room.

"Bi-Bitch?" Bailey sputtered.

"Two bitches in one," Ashley explained as she passed them by.

"The only thing bi I see around here is you," Kaylee said with a wicked grin, like she was telling a deep, dark secret. Read more »

Mixing pleasure and business [m/m]

This is the sequel to http://www.reddit.com/r/gonewildstories/comments/1zclih/mixing_business_and_pleasure_mm/

tl;dr – I met someone at a business conference in another state and we found out that we were both curious about other guys, so we blew each other in my hotel room (as one does, I suppose).

After we both came into each other's mouths that night, we didn't end up doing anything else (yes I know I hinted at it at the end of the first story), as we were both quite spent and I had to leave the next morning on an early flight. We parted with a nice long kiss and made a promise to catch up again when I was back in town. This was six months ago.

As it so happened, work sent me back for another conference, but this time my one night stand (let's call him Jacob) wasn't required to attend this time. We exchanged numbers after our encounter last time, and so the week before I sent him a text to let him know I would be back. The reply was quick from Jacob – he still thought about that night, thanks to my 'amazing cock-sucking skills' (yay!), and that he would meet me after the conference to have 'dinner and more ;)' Read more »

Things I’ve literally f*cked myself with | Or why I should always travel with a cucumber [F40 Masturbation]

In the last several months I've gone on a few trips without any sex toys. Once because I rented a holiday property and it was going to be my Mom, son, a close friend and her kids, and it just seemed weird to pack a vibrator. Another time I was travelling just with my Mom and we were sharing a room. Recently I went to a family member's house and the walls are super thin.

I've subsequently learned that not having a toy is a big mistake. It leads to some pretty raunchy behaviour on my part.

I guess I should clarify that I need assistance to cum through masturbation. Not sure why but my own hands just don't do it for me. Perhaps I could find a lover who could educate me. But until that happens and I'm master of my own domain, I need a toy.

So… at the holiday property one day I found myself alone and desperately horny. I'd been on the naughty online dating site and having some great sexting exchanges and was all worked up. I rummaged around the kitchen, as it held the most promise. One washed cucumber later, I was fixing myself up quite nicely. Except the cucumber was cold. Microwaving it seemed wrong and potentially could end badly. Do they explode in the microwave? I didn't want to have to explain that one. Read more »

25[F] [Str8] Bus encounter with a perv [voy] [huml] [mast]

[Fiction]

I'll let you in on a little secret. I have what I assume is a rather unusual fetish for a woman. I love flashers. I love perverts. And I love the idea of non consensual surprise penis. Let me give you an example.

So as you can probably surmise at this point, I'm quite the voyeur. I love the thrill of seeing a penis in the wild. At first, I had to make do with the occasional cock outline in a swim trunk, an underwear-clad bulge showing through the leg of a pair of shorts, perhaps if I got lucky, the swaying of a cock behind a loose pair of sweatpants. But on one special day taking the train, my wildest dreams came true.

I was taking a long train, about an hour and a half. Being a Monday afternoon, the car was fairly empty. I settled in by a window seat with my bag on the floor. I spread out, and enjoyed some window-gazing. A few stops into my trip, I notice a guy walking down the aisle. I don't think much of it at first. The car is still very empty, so I did not anticipate him taking a seat next to me. Except that's exactly what he did. "Excuse me, is this seat taken?" I make note that it's a man in dress pants and a coat. Brown hair. Otherwise nondescript. In the moment, all I can think to say is "sure, no prob." Read more »