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Anonymous
@confessions
02 Apr 2024 5:10AM
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I have this long term connection with a woman, that finally gave some results.

She is a friend, from a larger group of friends that used to go out together, when we were younger. After some time, the group broke up, everyone got married etc (except me), and we would see each other, not so frequently. In her 20s, she was this tall, cute blonde, slim, but with huge tits, and one of my friends from that era, dated her at the time, so she was off limits. After they broke up, while the group was still all together, we started occasional flirting, and she was a real tease, but it never lead to anything. She then got married, got three kids, got fat, and all that is left of her were her huge boobs, who got even bigger.

We all, or most of us, meet up from time to time, for old time sake, and in one of these occasions, when piss drunk, I told her that I was so into her, that I jerked off to her fb almost daily. I bit my tongue as soon as I said it, but she just let it pass, with a smile, and before leaving, when saying goodbye, she made a little tap on my croch, and whispered "something to think about tonight".

When ratio came back, the next morning, I called to apologize, and she accepted it, and that was it. We were both drunk, I said a stupid thing, she did something stupid either, and that is it. She is not hot now, so some male attention, I guess, felt good, and that was it.

Few weeks back, we were out and about, again, after more than a year, and I immediately saw that she was trying to be close to me, talk to me, since the begining of the night. Never in her life has she worn cleavage, but that night, it was so big, that everyone was staring at it.

I didnt drink, excused myself because I came with a car, and had to work in the morning, and she said "yay, I have a designated driver".

When we were coming back, she was drunk as hell, and she started teasing me, licking my ear, touching my chest, and asked me what am I gonna think about when I get back home (bare in mind, I told her that thing some two years ago). At this point, I was hard as hell, and I replied that I will imagine her sucking me off.

"Pull over".

It wasnt the best, it was a drunken blow job, but she was into it, and I came pretty fast. She swallowed every last drop.

That night, when I left her in front of her building, she was all giggly and cheeky. Tomorrow, I woke up to realize, that she blocked me on all social media, and even on the phone.

Makes me kind a sad. She is a fun person to be around, but I guess we both made a mistake with this one.

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Anonymous
@confessions
03 Dec 2023 4:19AM
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I fucked a married woman.

So I am 30, single, and havent had sex for quite some time. She is ten years my senior, a bit chubby, not the most beautifull woman in the world, but not ugly, short hair, but with a pair of nice tits. We work together, in a restaurant, and before or after work (since we have uniforms), I have noticed she dresses poorly for a woman her age - yoga pants, and tight shirts. Man, did I gawk at that fat ass, and juicy tits every time I could.

Since I am single, and a walking hormonal bomb, I started flirting, not because I thought anything would come out of it, it was just a way for me to play, and get a bit of mental material for later jerk off sessions, dedicated to her.

She started responding to it, but I still thought it is a dead end. She is just having fun, messing around.

But, I have noticed she has been brushing against me, smiling at my stupid jokes, and well, I responded by trying to find myself in situations in which we would be close, and in which we would touch our bodies.

That went on for quite some time, until, one night our manager asked her to lock up, since she had to be somewhere. So I decided to stick around, until it is only two of us. We have this back room, where we change our uniforms, and I waited for her to go there, and when I approached the door, I asked "are you decent", after knocking, because I needed the place too.

"I am, you should have come earlier"

That gave me wings. I entered, saying something like, I am in a rush, and proceeded to undress, to my underwear, to change, to my "civilian" clothes. I was intentionally turned her way, in baggy boxers, with a full on hard on. Still thinking nothing will happened, I just wanted her to see how excited I am to be near her, and use that thought as wank material, after I run off home. But then, while putting my hoodie on, still turned to her, I felt her hand on my cock. As I tossed my hoodie to the side, there she was, sitting on that couch, rubbing me through my boxers. I lunged at her, started kissing her, while peeling the jeans off of her. Hairy pussy, I mean, really hairy, havent seen that in ages. She was wet as a rain forest, so I was inside of her, very fast.

In while I was undressing her bellow waist, she took everything off north of it. Huge tits!!! She wanted it. she kissed me back, holding my shoulders, my forearms, while I was fucking her. I wanted to enjoy the sight of her tits, so I put her legs on my shoulders, and started fucking her hard. They were bouncing all over the place, so she grabbed them in her hands, while looking at me.

I got her shins in my hands, and pulled them back, so I can pull a bit back, and look how I enter her, while not losing pace.

Oh, she loved it!!!! And I was ready to bust...

Guess she saw that too, so she pulled me close, and started getting for under me. She wants to be on top, I thought.

As I lie on my back, you can imagine my delight, when I saw her stepping over my face. Oh, what a huge ass!!! Her wet, hairy cunt was on my face and I just started devouring her. She started sucking me, all the way, but I had no time to think about it, as she was wiggling her ass, rubbing her cunt all over me. Her pubes were so wet, her moans with a cock in her mouth...

And then I remembered a "trick" I used in such situations before. Anus stimulation, ok, that could do the trick, but I pulled her ass cheeks apart, while looking straight into her brown eye. She starts working harder. I try to position myself as close to there, while not reaching for a lick, acting all casual, it is just there. My nose touches the inside of her cheeks, then her asshole, and then she starts moving so violently, up and down, that her asshole presses hard against my nose and upper lip, and starts shaking. I press her down with right hand, while with the left I push her head down on my cock.

As she started cumming, she almost broke my nose, but didnt push her head back. I came so hard, that she was not able to consume it, she pulled back, gasping for air, while my cum was running down my croch.

I smelled like cunt for three days.

It was fun, and it felt ok. We were laughing and joking afterwards, and I felt good things are about to happend.

The next day, nor the day after that, she didnt come to work. On the third day, manager told me she quit, out of the blue.

That is my luck. I have this feeling that anyone else would turn this into a fuck - buddy situation, but not me.

It has been over a year since, and I still cant stop thinking about it.

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