A league of her own – how I [M] started this long affair with an instagram model [F]

This happened six years ago, when I was installing some hardware project for a business. It was a huge project, a new building for an IT business, and they decided to hire me as a consultant. It took about 3 months to plan it, with a ton of back and forth, and I had to travel several times to a different city.

She was always present in the meetings – I wasn’t sure what exactly was her role, until I understood that she was the boss’ pet. She never said much during the meetings – from time to time she asked some questions, never out of place, but my feeling was that she was in these meetings mostly to learn or to make sure that things don’t go out of plan. We had a few discussions – I think that it took a month of weekly meetings to actually talk to each other, at the coffee machine, while waiting for the coffee to get made. Her name was Anna (let’s say) and she was indeed beautiful. The sort that takes your breath away when you’re in your 20s. The sort that steals you from your wife with just a „hello”. Baby blue eyes, strawberry blonde, perfect skin, and definitely one that visited the gym often.

Our second conversation was a bit longer. In the mean time I found out she was the main account holder – her presence was not needed in the meetings, but she wanted to get more involved, perhaps to prove that her presence there was not only due to being the boss’ girlfriend. Our second talk was not a private one – we had a long dialogue during a business dinner, where I understood what was her role in the project, as well as I drawn some lines regarding her involvement in the project. The next day we continued what seemed like a growing animosity, but during the breaks we had friendly chats. I also have a semi-public persona in my country, and she read some of my stuff, and she liked it – we had a nice, relaxed conversation where I think that I went ahead and almost jokingly suggested I wouldn’t say no to her even if I was married. It was a bit of a touchy topic; the boss was married. But I calmed her down, explaining that luckily I’m not married, nor will I ever be – I’m not that kind of guy.

I came back every two weeks, and her involvement in the project was thinner – she made sure that things were on the budget, as planned, and she participated to some discussions, but as summer hit nobody was really interested in working too much on the project. The implementation started, and I, together with a team of 3 of their firm, started doing the work. But there were some budget issues, and I had to call her – but she was out of office, and someone gave me her number. I talked to her over the phone, then she contacted me over Facebook – it was easier that way. She was in Dubai, and she was pumping her Facebook feed with her instagram pictures.

One week later, as the project was under way, she came back. We had a lengthy discussion, that was professional but went a bit off track. I was joking about her instagram photo shoot, and she started saying that it’s a good thing that liking stuff on instagram can be done with one hand. „Well,” I said, „I never jerk off while liking stuff, I like stuff first and then just go through pictures. But in your case, my tinder date last night took care of me”.

We started going deep off-topic here, one-upping each other. She opened her Tinder, and asked me to open mine, and we matched. I went back to the hotel, and at 1AM I heard the chat. I woke up (it was a tiring day), and it was her, asking me if I felt like dancing.

It was a huge concert after-party, with some minor local stars, and she got me in. It was the usual, full of druggies, arrogant pricks and overpriced escorts. I guess she got bored, and needed some company. The club was dimly lit, the bathrooms were full with what felt like it was bad porn movies filming simultaneously, and she was quite horny. I got myself a few drinks to catch up to the mood, and we started dancing on the dance floor – well, it was more like grinding each other rather than dancing. I was behind her, her ass grinding against my hard cock in the middle of the dance floor, and I just gave in – I let my left hand over her chest, my right hand under her short skirt, and she started begging me to do her. My hand went up her skirt, and she wore nothing under; my finger entered her with ease, while she started breathing heavily, trying hard to breathe in the semi-dark, hot air of the dance floor. I fingered her fast until I saw a woman looking strange at us, and I drove her to the side of the dance floor, in a more secluded place.

I leaned her towards the wall, and she pushed her ass back, griding against my cock. I started fucking her with two fingers until her body jerked incontrollably, and I slowed down until the tremors subsided. I then put my fingers in her mouth and she licked them thoroughly, then I took her hand and went out towards the exit. „Let’s go to my hotel”, and she nodded, then went to the woman that was eyeing us minutes earlier, kissed her passionately on the mouth, and came back while a cab was already waiting for us outside. The hotel ride took about ten minutes, but she was just too horny, and in the back of the car she started a handjob. After two minutes she was down on me, sucking my cock, while I was reaching under her skirt, trying to finger her.

I stopped her just short of our hotel arrival. I paid, then took her up. I threw her on the bed and fucked her raw – my pants down to my knees, her skirt only raised a bit to her waist. She asked me to fuck her raw – she begged me to cum inside her, and her loud orgasm told me she loved knowing she’s being filled with cum.

I fell with all my weight on her afterwards, barely able to move, unable to even get out of her pussy. She started flexing her muscles, somehow, and while I barely felt anything, her movements definitely invited more. She was breathing heavily under my weight, but her griding already turned me on for a second round when her phone rang. I got up, and she took a few seconds to gain her composure, while she answered the phone. „I will be back on the 15th” she said (it was the 10th). „Yes, it’s not a problem, but it’s late and I’m tired. I need my beauty sleep”.

But her conversation went on awkwardly, despite her efforts to dismiss it, and I was drunk enough to think that it’s a good idea to finger her while she talks. She welcomed it, and she started responding almost instantly. She turned around and took my hand and started to lick my cum-filled fingers while she was „uhum” and „yes”-ing at the phone. She then showed me that I should offer her my cock.

She kept quiet while entered her, she muffled a gasp as I started entering the rhythm, and she said what sounded like a tired „’night”. She dropped the phone and I put my hand around her neck – she told me before she loved being joked. She finished in a matter of seconds, in a long audible pleasure discharge, her body exploding uncontrollably.

Minutes later, on the balcony, she told me that was her fiancee. The boss’ son. And he was off with business, and she was „out of town”. That meant she was at the disposal of her soon to be father in law.

She was a busy woman. I haven’t seen her for days afterwards, but in the last day of that week, we had a meeting. She reserved a meeting room, and the moment I got there, she pulled down her skirt and bent over the table. I fucked her again, raw, then she asked me to fill her ass.

I entered her ass with a bare minimum of resistance – my cock was wet from her pussy, but even so, it was obvious she was not taking her first cock up her ass. She took it in without flinching, and she came when she realized I was cumming. Or she just faked it a bit for my pleasure.

She was noisy – so noisy in fact that I was afraid someone heard us. They very well might have, but we had the room for an hour, enough time for two people to get out as if they had a normal business chat in a meeting room.

The adventure didn’t stop there. It was, as I said, just the beginning. She was definitely out of my league, but she later confessed to me that what attracted her was that I didn’t try to hook up with her with stupid phrases – she loved talking to me, even flirting with me, and she appreciated that I was sure of myself, and not trying to parrot some PUA idiots. It was the advent of PUAs, and everyone came with techniques to pick her up, and she was tired, and felt that most of the guys following those techniques were stupid.

We never lost contact – we still talk from time to time. Three pregnancies stole a bit of her thunder, but she’s now a single mother with a lot of money from the ex and she has her needs. I’m not even her only affair. And, yes, her girlfriend? from the dancefloor? We fucked too. But these are different stories.

Source: reddit.com/r/gonewildstories/comments/o822m2/a_league_of_her_own_how_i_m_started_this_long