First Time Being Watched by a Woman 37[FF]

It’s been about three weeks since I posted on dirtyr4r asking for a woman to watch me. A few of those who messaged me asked me to post a success story, so here it is!

One woman, let’s call her Josie, emailed with a good explanation of why she was into this as well and explained some of her own history. (Also, I asked and Josie is cool with me posting this.) She’d been divorced as well, so we clicked on that front and really hit it off. She was also cool with not talking on Kik. Seriously, please stop asking me to Kik you.

We met for drinks first just to see if there’d be enough of a connection and comfort to get through the initial jitters of stripping in front of someone. We also laid down some ground rules, like no touching, and had a great evening talking. We actually talked too long and made it back to my place late. I had no idea where to start, but she said, just tell me where you want me. I pointed to a chair opposite of my sofa and she sat. She could tell I was nervous so she said I should just start slow.

My [F]irst Time in Ropes

Hello,

So lately I’ve been playing around with writing down some of my stories. I was recently gifted a copy of “50 Shades of Grey,” by a well-meaning friend. Pleasant intentions, but I doubt she has any idea that I’ve out-performed the acts in that book and done them in a more safe, sane, and fun way. Maybe other young women could use a better example as well.

To set the stage, several years back I was finishing up my doctoral work which involved a good deal of travel around the country. Prior to finishing up at one of my test sites and before heading to the next one, I figured: I’m moving to a new city, this is the one time in my life where I might get the chance to try out a completely new identity. I was passingly familiar with BDSM through online stories and I had a bit more of a fascination. I had read just enough to know that it intrigued me; but not enough to know what I was doing. But, I had decided, this was my chance, this was my shot to give it a try.

The time I [ F ] fucked my friend’s fiancé behind her back. [FM]

Back in the fall of 2015 , I had been fucking my friend’s fiance behind her back. They had an arranged marriage and shortly after the engagement, their families started encouraging them to spend time together to get to know each other. My friend used to be my subordinate at work but she quit after the match was made. She said she wanted to be a mom, while working part time for her fiancés family business. Both of their families were very wealthy.

A few days before she quit, she introduced me to the guy. We’ll call him S (his first name initial). He was tall, around 6 feet, well spoken, polite and very handsome. As we chatted I knew I wanted him in my bed. In order to make this happen I’d have to get close to the girl. We’ll call her C.

I fucked three sisters, part one [MF]

Elaine and I were too big of rivals to ever be anything deeper than we were. Hell, we were probably too big of rivals to even be calling ourselves best friends. But that didn’t stop the 7 AM snaps of her holding up a Starbucks cop, closing her pretty hazel eyes, biting her tongue, and flashing a peace sign with “good morning, bestie <3” splatted across the pic.

Curiously, courageously, or maybe just lackadaisically, I’d occasionally snap back a photo of me right after a shower (chest-up, obviously, also, she was way more of a morning person) under some subliminal photo-communication posturing to take our attractive snap relationship a bit more revealing.

And until a fateful day last May the closest we ever got was a similar post-shower pic from her (chest-up, but sadly with a towel covering what I had deemed as truly incredible breasts), flipping me off as she held up a towel. Like I said, rivals. Who argued, and fought, and argued some more, and frequently typed paragraph after paragraph towards each other about passions that got very intense when those passions didn’t align with each other.

[MF] Covering her in cum

I’ve posted a few times to mixed results…first time was solid, next time not so much. So, third time is the charm right. :)

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I’d been fucking Molly for a few months now and each time we were together our encounters seemed to go up a level. We started talking more about exploring things we’d never thought of before, playing a kinky version of truth or dare with each other. “Would you let me fuck you in the ass?” “No way, your cock is way to big.” “Would you let me stick a finger up your ass and rub your prostrate while I blew you?” “Ummm, hell yes, I’ve heard the orgasim is amazing so, why not…but I may have to have a bottle of wine in me first!” Maybe it is tame for some, but not me. I can talk it, but walking it is different.

To recap, Molly: 5’8″ or so, size zero, 105 lbs., smooth all over, b-cup tits and an ass to die for. Me: 6’4″, 220 lbs, shaved smooth with a small patch of hair above my cock which is probably above average (though I think it’s average even though I’m told differently), close to 9″ long and thick.

I lost my virginity to a 50 year old [MF]

I grew up super prude and when I was 18, almost 19, I decided I needed to just get it over with. Virginity had been holding something over my head for so long.

I made such a bad choice. I met a man who was super kinky. And for some reason, I let him play me. I went along with it for some reason? Part of me is like YOLO and it’s not that deep. Part of me feels hella guilty.

I agreed to meet him in person. Made sure to tell a friend where I was. I gave him a two hour blowjob. My first one ever. I actually liked it. We ended up having sex. Remember this is the first time I had met him in person. It was so so stupid but I wasn’t really in my head. So yeah. Was 18 and lost it to a 50 year old.

I feel super guilty about it now, but I figured that it’s a “gone wild” story if I’ve ever heard one. Just needed to put it out there!

Ta[M]ing the ice princess (hot [F] bartender) (NSFW)

Nicky was 28 at the time and a bartender at a well known restaurant with all female hot waitresses where I was a young manager at 24 years of age.  She was aging out of the restaurant biz and moving to a professional career in nursing, but held on to the occasional night weekend bar tending shift (read: moneymaker) like a crocodile holds on to prey. 

She was an east coast Italian girl with a toned athletic frame, about 5-7, naturally tan but even more so during summer beach season. She also had a healthy amount of attitude.  Regular customers loved her and took good care of her.  Her attractive face and body paired well with her smart ass vibe.  I’m such a smart ass too (guess that’s how I end up with these type of chicks) so our banter could get pretty heated and we certainly played it up to customers at times which was always good for a laugh and some more bucks in her tip jar. 

She was sassy enough to earn the nickname ice princess and I think that was a play off of the fact she was a figure skater when she was younger and still had some shapely legs and curves on her butt to prove it.

My crush [F] knows me better than I [M] know myself

Disclaimer: Due to privacy and security reasons, I am not disclosing my name or my crush’s name.

For my entire time in high school, I’ve always been looking at this girl who to me, was the perfect person. She was really smart, athletic, confident, and great in almost every way imaginable. She was a part-time tutor, in student council, founded the Physics, Psychology, Neurology, Microscopy, Forensics clibs and was on the board of the Politics, Finance, and the Debate clubs. On top of that, her softball and swimming team always win, she ranks in the top 1% of students academically, and has already been admitted into the world-renown Oxford University in England. Always, she knew what to say, what was about to be said, and knew what to do in any given situation. I personally couldn’t imagine wanting anyone other than her, though she does feel way out of my league. She was the pinnacle of perfection and I couldn’t imagine looking up to anyone but her. She was my mentor, my senpai, my queen, my goddess, my everything. I feel eternally grateful for her mere existence, for she was everything I imagined the ideal person would be, even before I entered elementary.

I got into a [F]ight during sex

So last weekend i met that hot tough biker looking guy in bar. After a wild night partying and drinking, i invited him to my place. We first kissed and i wrapped my hand around his neck and he was grabbing my butt. We got naked and started fucking. During the whole thing he was calling me names and talking to me dirty. I asked him to tuned it a little bit down cuz he’s really using very nasty humiliating word and I didn’t like it. So when i was giving him head he pulls my hair and slap my face and said ” yeah suck that cock your filthy cocksucking slut”. From there i lost it and got furious. I snapped and screamed at his face and kick him on the balls. Then kicked him out of my place ?.

For me i don’t mind dirty talk but there was something in his tune and voice that I didn’t like plus I’m such a moody person so maybe I wasn’t feeling it

[M] [F]ucked this hot Asian chick from the Airport

(You can skip straight to her getting fucked at the bottom)

Been flying across the country for the last 6 years for my job. I fly at least once a month and I have sat never once got a hot girl to sit with. This time wasn’t any different because in my row the hot girl was sitting in the window seat and I was sitting in the aisle seat.

Between us was a guy who looked more or less her age and of course they got to talking. I just sat minding my own business until she was on her phone and I saw her scroll her photos and unintentional or not I caught the nudes. I am not into BDSM but she is deep in it apparently with those kinds of pictures.

I now think she was doing it to tease the guy next to her and he was much slower than I in realizing what was visible on her phone every few minutes of her scrolling around. She isn’t shocked or embarrassed when the guy actually says something to her about what he saw and they fall into a conversation that made me jealous to not be apart of. She and the guy next to me both have a layover in my city and I am thinking of joining in on their conversation but I felt like this guy was putting in tons of work and I have some booty waiting for me later that night anyways.