gonewildstories Archives — Page 4397 of 5640 — NSFW story

Younger girl from work [MF][Open]

As mentioned before my girlfriend Ivy and I decided to try an open relationship. Ivy is out of town for work. And according to the do’s and don’ts we agreed on I decided to go for it. It is a lot easier for women to find a man to be with than the other way round. Maybe that is part of why I went for low hanging fruit. Though to my shame, I have to confess I broke some of the agreed upon rules.

Cassandra, or Cassie as everyone calls her, is in her early twenties and works at the front desk of my office building. She is much younger than me. I don’t know if it is daddy issues or something else, but she is hitting on me in regular intervals. I am guilty of flirting back before, but it never went further than that. I did take advantage of the fact. It is a good stroke for one’s ego though when a pretty young girl is flirting with you. And not just for tips or something like that. Read more »

[MF] A hot blowjob in the back of my car. (long)

I wrote a comment about this earlier and I wanted to write more about it because I enjoyed it so much. This is pretty tame compared to most of the posts I have read on here, but oh well, it was fun ;)

This happened back in my senior year, we were two 18 year olds who had been together for a little while and were each others first time. To keep things simple, I’ll call her Zoe.

Zoe and I would regularly meet up at a beach between our houses. It was right in the middle, so it was the perfect place to meet. We’d usually just meet there for a bit when we wanted to talk or just hangout after work. It wasn’t a very private spot, it was a small parking lot with maybe 6 spaces, just off the side of a fairly busy road. It was winter at this point, so we would just sit in my car under a blanket to chat. But this night was different, she suggested that we have a movie date in the back of my car. I had an SUV, so with the back seats folded down flat, it was basically a full size bed back there. So she brought blankets, pillows and her laptop, we set up in the back of my car and got comfortable. It was a cold night and we could have just gone to my bedroom to watch a movie, but she thought this was cute. We were both wearing sweatpants and hoodies, plus we were cuddling under the blankets and the car warmed up quite a bit throughout the movie. Read more »

[MF] transcendent sex

If you read some of the subs like /r/sex, you know there are frequent questions that are thinly vailed requests for fap stories. Rather than spam any of those subs, I thought I’d write something up for here. It was prompted from thinking about if there was one particular experience where you started as a child and left a man. It’s been almost 20 years now, but I remember it like it was yesterday.

Me: Post-college, not a ton of confidence or experience. Living the dream.
Her: Post-college. Beautiful, confident, yet self-destructive. My dream girl for years.

It’s the afternoon on a leisurely early fall weekend. After waking up late, we’ve spent most of the day in bed. It started out just lounging, but only being a couple for a month or so, this inevitably led to things turning sexual. I’m sitting upright in bed, leaning against the flat backboard. We’re both naked. She has her head on my chest and is lightly, ever so slowly running her fingers over my stiffening cock. Across from us, I can see our reflection in her dresser mirror.

Humming dreamily, she says, “I’m going to have to get myself a new dildo. Mine doesn’t do anything now.” Read more »

Nude Night Walk [M]

This is a story about a dare I did in 2011

Okay this one starts with chatting to this girl on another site, I left hints about my exhibitionism and then one night I said how I was gonna get naked and after and a little longer talking, I say that maybe I should go for a walk to the shop as i am (it was about 11pm or so). She thought it was crazy and didn’t believe I would do it and at this point I didn’t either wasn’t even being half serious.

At this stage though I wanted to prove her and possibly myself wrong and do it. So I had it planned for the next night and I also planned to do a couple of clothed test runs. The next night comes and i’m sitting downstairs. I wasn’t really up for it and it was also windy and i think it was rainy too. I think I just wanted an excuse to not do it and that fitted perfect. The next day I was annoyed that I didn’t do it and felt I let myself down. Read more »

How I Learned to Stop Worrying and Love (er…Tolerate) Rimming [FM]

About me, because you want a mental image I’m sure: I’m Brooke, I’m 24, 5’3″, 135 lbs. I’m all ass, no tit, and I look vaguely Lebanese but am actually Cuban.

So as I discussed in the last thread I made, I went through a bit of a period between the time I was 18 until I was about 20. I was doing risky things with people I didn’t know on a semi-regular basis, probably once a month or so. It was like I was in heat; the combination of attention and the ability to finally fulfill certain fantasies or cravings combined together to make me do things that, in retrospect, were not really very well thought out.

I had started by meeting men in hotels. Strangers. I’d troll Craigslist and find guys looking for women who either had pictures I like or a way about them (you can get a sense of how someone is from how they write, usually). I tried mostly to stick to men who were in town for work, but it wasn’t like I was background checking them or anything, I just assumed if they said they were they were and went with it. Read more »

[MF] Dressed in my sisters clothes.

When I was younger I had a babysitter who would dress me in my sisters clothes. It started off as a joke but eventually every time my sister would leave for tennis or piano lessons she would dress me up. I’m talking head to toe. Tights, panties, dresses etc. my sister was 2 years older then me so her things fit well at the time. At first I didn’t enjoy it but after a while I started to look forward to it. It went on for a couple years then my sister got old enough to watch me. After she stopped babysitting I continued to dress up even to this day. Is it weird that I like looking back on it and get aroused thinking about it?

Every Guys Fantasy [MFF]

New to posting but your welcome to let me know your thoughts.

I think it’s safe to say every guy dreams of having a 3way with 2 smoking hot girls, so here is my experience.

Backstory:
So I had just been through a few short term relationships and I decided if girls can be heartless so can i. I would be the jerk and play the game that is dating now days. Not chasing the girl, not spending money on fancy dates, the bare minimum to have sex with them. (Suprisingly little in college)

I dont think I’m bad looking, I hold a more muscular build. I’m about 6ft tall and am pretty quick witted with my words. Longer brown hair, clean beard lines.
Pretty much your normal college guy.

Girls:
So to give you a mental picture of this girl and her friend.
We will call her “Sarah” for animinitys sake.

Sarah is a 5’3 long black hair Hispanic and white mix.
In her free time she enjoys going to the gym, alot.
Her figure is better than anyone I’ve seen by far. Read more »

[FM] His first multiple!

My paramour met my friend and I for some drinks downtown. There had been a home football game, so there were crowds everywhere, except one of my favorite dive bars. My friend sat at the bar awaiting our drinks while I offered to show my beau where the restrooms and back exit were at the bar. The restrooms are quickly passed on the way to the exit, but then there is a long dark hallway lit only by the exit sign leading to a back alley. I led him to the door and showed him the alley, but it was well lit this night due to all the trash collection after the game. “Remember this for next time,” I told him as I grinned devilishly. We then walked back inside the dark hallway, and I grasped at his belt to pull him to me just as his hand was stroking the side of my face as he kissed me against the wall. I didn’t want my friend to feel like a third wheel, so I knew this would be the only time we could feel each other’s tongues for awhile. I moaned softly as he pulled away, my lips still parted, but we had to get back to the bar. Read more »

It happened again. [MF]

Haven’t had much to mention [since my last post](https://www.reddit.com/r/gonewildstories/comments/9l87mm/fucking_the_ex_mf/). She hadn’t been interested in doing anything, and my attempts to get things going were met with a firm “Go find another lady to play with”. Well, I already have, but that’s none of her business at this point. We’ll come back to that.

That changed today. She came downstairs to get ready for work wearing a sleeveless dress which I initially assumed didn’t have a bra on under it. I offered to play with her tits for a bit before work, and she informed me that she was wearing a strapless bra. I confirmed that by reaching around from behind her and giving her breasts a firm squeeze, rubbing over her already-hard nipples, which were poking through the material. She let out a groan of pleasure and I knew that I had her again. I played with her breasts with one hand while I used the other to reach under her dress to check out the panty situation.

She typically wears your bog-standard cotton mom panties when she goes to work, but as I had already suspected she was wearing one of her lacy thongs. I gave her ass a squeeze, then a smack, before grabbing the back of her undies, pulling the material tight over her pussy. That got a “fuck” and another groan out of her. Read more »