Late 40’s [F] and the college boy [M]: A first for both of us Pt. 2

Thanks for all the positive notes on my first post–really glad everyone liked it. I’ll definitely get to the PMs soon. That post is [here](gonewildstories/comments/598ol8/late_40s_f_and_the_college_boy_m_a_first_for_both).

I actually was about halfway through writing about getting my a previous gf off under the covers with her dad in the room (and how she paid me back w/ a quickie just as he walked out), but really do appreciate the asks for me to finish telling about my first night with Kim–so I’m sharing that instead.

As a refresher, I was a tall, gawky kid growing up, with glasses and an overbite. Then I wrestled throughout high school, got contacts, and dental work fixed my alignment to where I’m actually a pretty good looking guy (I’m told I look like the senior in Sixteen Candles), but I still have the perception of myself as a gawky kid with glasses and can still be somewhat shy until engaged and alternate between overconfidence and no confidence.

[MF] Pornstar Penis after work

Yesterday I went out costume shopping for a Halloween party. I wanted to buy something that I could dress up in again throughout the year (to justify those +$50 costumes). I ended up getting a Wonder Woman sequin corset and matching tutu skirt (http://imgur.com/gallery/z3MFY). When I got home, I tried it on. Loving the costume, I sent some pictures to people I tease on kik, Pornstar Penis being one of them.

He flipped out and wanted to drive to my place to fuck me right away. Since it was pretty late, I told him that I couldn’t, and we rescheduled for today.

He came over to my place after work. I greeted him in my costume, with my hands on my hips. He quickly took his shoes off and pulled me closer to kiss me. We shortly discussed the cleavage that the costume provided. Then he walked behind me and lifted the tutu, revealing my naked ass. He groaned and bent down, kissing my ass cheeks while he grazed my legs with his fingernails, starting from my ankles and gliding up to my thighs. I took my skirt off, now only in my red sequin corset. He wanted to leave it on longer but was afraid of breaking it before I could wear it for Halloween. So off it went. When I put it aside, I turned around and walked back to him, tits exposed. He groaned again, staring at my breasts.

[F] Flashing on the bus

I was going to work today by bus since my car is out of gas and can’t afford it as of today with rent coming up etc etc.

I notice these guys pointing at me and they weren’t quiet about there comments. Instead of being mad or upset which I waited maybe 10 minutes until the stop before I should get off.

I lifted my skirt and gave them a good look at my ass for the entire time it took the bus to make the slow right turn and smiled and stuck my tongue out at them, ignored the comments from the other people and fixed my skirt on the steps of the bus and saw one of the two guys with a thumbs up lol.

I feel fun today lol

Blow & Go [F]rom [M]y Mistress

Story starts next in the paragraph. This is all background information. I’m married. My girlfriend knows that. She lives too far away to hook up regularly and my wife doesn’t want any details or anyone coming over. So, we text a lot. We only got to mess around 4 times before calling it quits; the first and last times were fun but don’t make for an interesting story. First time, I go to her house, go down on her, she cums, goes down on me, I cum, leave, blah, blah, blah. The last time, I go to her old place to help her load up some stuff in her car and she sucks me off as a thank you. Wonderful, knowledgeable blowjob, but not much of a story. Anyway, the other 2 I just need to put the story out there, especially the second one!

The first thing to know is that she is a kinky girl. I’m in a very vanilla relationship at home and she is anything but vanilla! She accepted that my interests are much more tame than her’s and we would often text about the kinky stuff she was into. I loved talking to her about these fantasies but wouldn’t act them out myself. She would, however, find some other boy to go play with and have him do all the fucked up things I would say to her in our messages, then she’d text me back the details and sometimes send pics.

Grinding on him in Busch Gardens and jacuzzi tub sex [MF]

Last week my boyfriend and I went to Busch Garden’s Howl-O-Scream in Williamsburg, Va. We had been talking about this trip for weeks, because it is one of my favorite things about the halloween season. We’ve been together for over a year now, but we’re still all over each other like we’re still anticipating the first time. He’s a redhead and the hottest looking nerdy kid imaginable. He’s about 7 inches and uncut. I have light brown hair and green eyes, as for my body I have a small waist, thick hips and thighs, and size DD breasts.

We got in line for a roller coaster which is both of our favorites, but had an hour and a half wait. We were obviously surrounded by people but I was already stupidly horny. His favorite part of my body is my ass, which I will say is pretty great, and I know when I grind my ass on him he’s always super into it. Every time we stopped in line I would stand in front of him and press my ass against his hips. I tried to make it look like we were just cuddling, not sure if it worked though. Every time I pulled away he pulled me back to his hips. If I was feeling brave, I would twerk my ass cheeks a little bit. Every so often he would whisper for me that I was driving him crazy. A few times I discretely rubbing him through his pants with my hand. After at least an hour of me teasing him, we got on the ride and things calmed down a bit. The sexual tension was still ridiculous though.

[FM] Partying With Jane [Oral] [Anal]

After reading a story in this sub recently that featured shotgunning beers, it jogged my memory of an encounter that I had ten years or so ago.

Jane and I grew up in the same town together, attending all of the same schools and graduating in the same class. We had always been friendly, and had a chemistry that I’m not sure either of us knew how to act on. Admittedly, she was no ten. In fact, she was probably closer to a five. She was around five feet tall and was on the bigger end of curvy. She had a decent set of DD tits though, with a big butt to much.

A couple years after graduation we found ourselves at the same small party, which more or less consisted of ten people hanging out and playing drinking games. We immediately gravitated toward each other, partnering up in beer pong and more or less never being outside of an arm’s reach of each other. As the night wore on people started to leave, with the two couples that lived in the apartment heading to their rooms to screw and go to bed.

[FM] A welcome gift from my 25yo ‘boss’

I’m just an 18 years old idiot who just found a dream job at this mall in Sydney as a sales assistant. The first day I was working there I was introduced to this beautiful sexy lady called Claire. She is actually the manager of sales but she also one of the interns’ guides around the entire mall. 5’9″, cute, long brunette hair, slim figure, 25 years old last but not least, hot. I think she’s a bit too seductive, always want to be the center of attention, wears incredibly sexy outfits once in a while. But hey, she has the face to complete the rest of her body, in my eyes at least.

So for a few days I did quite good for an intern. Punctual, obey the orders and also always offer some help for the workers there. To be honest, I did those things just to catch her Claire’s attention, also not gonna lie, to check out her amazing rocking body as well. Just this one evening around 10pm, I was relaxing in the staff lounge waitinflg for my shift to end early. As I was scrolling my Facebook feed, Claire or Miss Johansen, what I call her, came into the lounge heading to the pantry. I replied her smile with nod along with a “Miss Jo..”.

How I Learned To Love The Gym [fm]

I’ve always been meaning to get more in shape. I have a gym membership but I only end up going once or twice a month. Lately I’ve been trying to be better about it, and that turned to being a regular after meeting James. He was tall (6’8), muscular, black, sexy as fuck. Always weight training with his shorts and tight shirts. I loved watching him as I worked out, imagining what he looked like naked.

Eventually I got the nerve to introduce myself. I made some excuse, said I wanted to learn more about the weights and asked him to tell me about it. Turned out he was a really charming guy, we hit it off. The next few times I visited the gym we worked out together and I caught him checking me out. This last time, he asked if I wanted to go back to his place when we were done. I smiled, coyly asking him what we’d do there. He winked and said I should use my imagination. I did, so to his place we went.
We started out talking, having a drink.

Roommate [F] caught me [M] masturbating [college] [inexperienced]

Resubmitting because I didn’t see the the new account rules. —

Hello /r/gonewildstories. I’ve lurked for a while now and have been thinking about contributing – time to finally do it! This story took place almost a decade ago when I was a sophomore in a college in the deep south. It’s not a story of crazy kinks or giant orgies, but it remains one of the hottest experiences of my life. Fair warning – the [inexperienced] tag means that this story involves a lot of five finger shuffles, priming the pump, taming the one-eyed snake, whatever.

I was 19, just under 6′ tall, normal build at about 180lbs, not super athletic, but not a couch potato either. And I was a little awkward and very sexually inexperienced. I’d only had a few dishes from the classic sampler of experiences that nerdy kids got in high school and freshman year – some awkward grinding at school dances, a bit of over-the-pants rubbing from equally nervous and inexperienced classmates, and the small collection of handjobs and toothy blowjobs that I still jerked it to a couple years later. To put it mildly, most days it felt like my balls were fit to burst, I noticed tits and ass on college girls every time I went to class, and I was constantly thinking with the wrong head. That being said, freshman year was great. I’d learned a lot about confidence and getting out of my shell, and I had met a lot of great friends that stuck with me through college, and even to the current day.

After a week away from my fiance [mf]

My fiance’s groomsmen took him on a camping trip for his bachelor party a few months before the wedding. While they were gone, he and I were talking about sex a lot via text. The subject of fantasy came up, and we started talking about all of the things we’d like to try. The whole week he was gone, we drove each other wild with stories of threesomes, sex in public, orgasm denial, restraint and more. I was also posting pictures and videos of myself on Reddit, and he was going insane over the messages I shared with him from my inbox.

I’m pretty sure I was dripping wet the entire week he was gone. I bought a new dildo about three days in and fucked myself with it over and over, while wearing the butt plug I had also purchased. This was the week I discovered my ability to squirt.

Finally it was the night he was coming home. We had decided that from the time I picked him up until the time we got home (about an hour), he would be in command and I would do whatever he said.