Accidentally fucking an ex prostitute [MF], anal, rough

This is a one off story. The time period doesn’t matter.

I’m six feet or so, normal build, not super athletic but in shape. Your average white guy in my 30s (when this occurred).

I met Jill through an online site. It was geared towards kink and sex. Not so much dating. I had zero success before talking to Jill and after. It was a massive sausage fest of a site with more bots probably than women.

Jill was a good 10 years older than me. She was maybe 5’5” and 130 lbs if I was guessing. She didn’t have much of a chest but nice legs and ass. Her profile was pure sex showing off just about everything. She had massive nipples that I assume needed a padded bra to hide.

She was still cute for her age but it was her wild side that seemed interesting.

I contacted her, expecting nothing in return. I was shocked that not only get a response but one without a link to go to or broken English.

We chatted for a couple weeks off and on. She was almost too good to be true. She was super sexual and into anything.

Mealtime with Jordan [M/M][Anal][Snuff][Blood]

As I hunt around the city for a good meal I’m given plenty of opportunities. So many men around the clubs, dancing, drinking, having a good time. I could easily reach out, grab a man and take him to my lair for a feast.

    But, I’m feeling adventurous, so I continue hunting, occasionally stopping to admire men I see in the clubs, writhing their firm bodies together, their virile semen calling out to me to be drained, or their rich blood coursing through their bodies.

    I can feel when the focus is on me, I listen to the conversation while I stand casually against the bar, drinking from a beer the bartender gave me.

    “Dude, just to talk to him. If you’re trying to get laid, you have to make a move,” someone I assume is his friend states.

    I’m approached by a man and he smiles at me.

    “Hi, I’m Jordan,” he says. He’s average height, decently handsome with a thin body. I can smell his potent semen in his virile male body and smell his blood in his veins.

    “I’m Gavin,” I reply and look over at the bartender. “Would you like a drink?”

[M]ore wild [f]irsts

Sooooo, the second time we met up.

First time is [here](https://www.reddit.com/r/gonewildstories/comments/c1dqdy/i_had_four_firsts_in_the_same_night/). (Pun intended)

This time, it was quite late. We just hugged when we saw each other, it didn’t feel right to kiss him right away even though he certainly would have been up.

He sorted his stuff out, since he had just gotten home from training. He asked me how the traffic was (I live 2,5 hours away) and if I was hungry. We sat outside for a while, basically catching up, because we don’t like texting very much, which always gives us something to talk about. Then went to his kitchen, I sat down and he got to cooking, giving me stuff to chop in the meantime. He made cocktails again, but only two.

After some talking and joking around, he put a hand on my chair and finally leaned in for a kiss. I immediately complied, I was longing for him and felt my lower abdomen contract full of desire. I touched his face with my left hand and kissed him slowly and sensually, while he started using his tongue and touching me all over. My breathing got louder and I whispered ” I thought you wanted to cook”, with no intention to stop kissing him whatsoever. He stopped suddenly, frustrating me.

Master May I [MF] [First Post]

“Kana, I asked you here to discuss our status…” Spoke a tall brunette man, his gaze fixed on the girl kneeling at his feet. She was dressed like an absolute slut, her round breasts fully visible through the sheer material of her pink crop top, save for heart-shaped patches covering her nipples. Her shorts just barely fit over her fat ass, and did nothing to conceal her thong.

“I see you’ve worn the outfit I picked out. Did you get any stares on your way over?” he inquired, raising an eyebrow.

“I got a few… And one lady looked at me like I was possessed.” Kana scoffed, shaking her head a bit.“Well, get used to it, pet. I’ll be picking out your clothing from now on.” He sighed softly, reaching over to ruffle Kana’s hair as a smile broke out on her face.

“You mean… You want to be my Master?” She grinned up at him, receiving a mild smirk in return.

“Yes, sweetheart. I’ve decided to make you my property. I’ll be making your decisions from now on, so don’t worry about thinking too hard about anything.” His hand slid from her hair to her chin, cupping her face and making sure her gaze was fixed on him.

10/10 Tinder Date [FM][anal]

We matched 6 months ago before Christmas. His work with an airline and my limited availability have kept us from being able to meet up sooner, but we have enjoyed the months of texting and sharing pictures. This past Friday, our availability finally lined up, and he invited me to spend the evening with him.

Filled with nervousness and a little apprehension, I drove an hour into Atlanta to his midtown highrise complex. We met somewhat awkwardly on the street as he hopped into my car to direct me to the proper parking level and spot. We shared a mutually nervous hug after we parked and made awkward small talk as we rode the elevator to his floor. His voice was soft, his embrace was warm and firm, and I began to let myself relax and take in the experience and his presence.

[M]y sexual experimentation with anal play (true story, etc.)

Yeah this probably sounds gay but I’m not (yes I’ve experimented in real life, no it didn’t turn me on). About 9 months ago I quit watching porn, hence why I don’t really try anal play anymore.

However, when I was watching, I saw videos of straight guys trying dildos or wearing butt plugs in their day to day life which I thought was SOO hot, like just walking down the street with a fist size plug all up in your booty? That sounded so hot. So naturally, curiosity got the best of me. Girls (and guys) have – without fail – always mentioned that my ass is my best feature so I was like yeah I’ve gotta try this.

I went on a sex toy shop and bought a few things. I bought a 9” white, suction cup dildo, a large butt plug and I was about to check out. Then my feelings kinda surprised me. If you look at me, I’m a masculine man. I work out (a lot), I’m currently a military reservist and I’m not a bitch in the slightest. Yet before I checked out, I found myself browsing lingerie. I knew exactly what to look for as well because I knew what I liked on girls. I browsed for what was probably an hour before I settled on some things: a couple of pairs of high denier (like opaque) black hold up stockings, a few black thongs and a little black dress.

[M]y attempt at a “per[F]ect week”.

For those not in the loop of what a perfect week is, its sleeping with a different girl every night of the week. So, 7 girls in 7 days. This is my story at taking a shot at the perfect week. TL;DR at bottom.

This was about 4 years ago now. I was in college, my roommate had just moved out and I was having a fun time using Tinder to its fullest. Now as you know it is kinda difficult as a guy to get girls to match, much less get them to agree to meet, and even less likely to end up sleeping with them. So my prep work was about 3 months of chatting up girls, setting up times, going on dates, etc. etc.

Quick bio: I am pretty much the definition of Average Joe. I’m 5’7″, 170lbs , brown hair, brown eyes, 6″ dick. I had built my tinder profile to be extremely open to what I wanted, and it seemed to work. I was taking a semester off from school to work so that I could pay for the next semester, which meant working the afternoon/night shift. I usually got off around midnight or so. Pretty good time to get off and meet up with girls in a college town, or get up early and do something in the morning.

My [F]irst time with my now husband was a threesome with anal [MFM]

It was few months after I met Chris (see last post) and we’d been fuck buddies for a few months when he said he had a buddy who’d be interested in a threesome. I’d had one threesome before with some college guys but we were all been drunk and it was just shit. This time though I knew Chris turned me on all on his own so another guy would just be a fucking bonus.

On the night, at Chris’ suggestion I wore a short tight dress with no bra so that it hinted at my nipples. The other guy, Steve soon turned up and we had a drink and chatted on the couch. Steve has a slim body with short dark hair and a cute smile. After some talking both of the guys’ hands started to wander to my bare thighs and waist and soon Chris suggested that me and Steve go ahead to the bedroom to ‘get to know each other’.

[MF] RAOBJ stranger turned to BDSM friend with benefits

Last week, I was itching to suck some cock and needed something that night, so I made a post on r/randomactsofblowjob. It was short and blunt; my mood was overwhelmingly horny. After being stood up at a cafe – probably prompted by some fuckhead on my post accusing me of being a man – I texted a friend about it and he chastised me for using Reddit. “Reddit is too dangerous,” he chided. “Just come home and play League with me.” But I was pissed at the fuckhead on my post, the German guy who stood me up, and my friend for chastising me. As a big “fuck you” to the world, I picked someone at random from my PMs that night, and here I am today with a summer fuckbuddy who is more than willing to engage with my kinks. We’ll call him C.

About me: 19 years old, 5’1, half Asian and half white, 130lb. Moderately attractive if I may say so myself. 80% lesbian and that 20% straightness is addicted to dick.

I’m going to talk about our encounter last night because C asked me to, and at this point we’ve only met three times and I’m not ballsy enough to be bratty and defy him.

I had four [f]irsts in the sa[m]e night

* five

It’s also my first here and I hope you’ll enjoy!

We met up shortly after texting for a week.

Before that, we spoke on the phone. He made me laugh and I felt like I could talk to him forever, it just never gets boring. I was almost completely over someone else and thought it’d be good to get to know someone new. He knew I was a virgin (although I had a dildo, so not much hymen left).

Upon meeting up he was very nice and authentic. I’ve never met someone like him. We talked for a few hours and I was adjusting/trying to relax.

Anyways, we went out along with a bottle of white wine to a historical building surrounded by fields. This place had a balcony and we were completely alone. We were making jokes, teasing each other and drinking. Both started to get tipsy and he started putting his arm around my waist while I leaned on the balcony. After some more talking, he put our wine glasses away, looked at me, ran his hands over my neck, breasts and waist, said he liked me and kissed me. I am super sensitive and kissing is enough to make me wet. I started moaning almost immediately, he said he liked how I kiss.