The story of how I started cheating on my wife with my Cougar Neighbor

Hello people, I hesitated to share my story but everyone is doing it, so why not? This happened some years ago, I married my girlfriend when we were pretty young (around 22) maybe we rushed things since we knew each for about 2 years before we got married, we moved together into a new apartment since she used to live with her parents and where I was living is a shit hole.

3 months post marriage I started to have some teenage thoughts, remember when we were 14 and imagined that any woman in the street is a horny slut who’s ready to have sex like pornos? Yeah, I started to have these weird ideas about this mid age lady who’s living with her 9 years old son, honestly she’s a prefect 10 for a woman in her age, even my wife used to get jealous of her, she’s that type of a woman that resisted aging as hard as possible (even thou you can tell she ain’t in her 20’s no more) she has a dark blonde hair, perfect body and curves, she clearly likes sun bathing because her bronze skin is just amazing.

Sex and the telescope…

Sex and the telescope….

September in Chicago. Normally a very nice month, but this particular Friday the wind and rain were vicious.

It had been a tough week. This was my third sales call to this company, and it had been tough. I'm 46 years old, and I think the oldest person in this upstart company was 26. The youngest was Chad, the IT guy, who just turned 21 on that day. But, the contract was finally signed!

There was a short after-work celebration at the local pub for Chad, who had just turned 21. There was a lot of good natured kidding about finally being able to have a drink. Chad, for his part, was mesmerized with Kristen as he always was. Aged 23, she had a body that you would almost not believe was real – her photo could be on any magazine cover; she was simply beautiful. She also paid virtually no attention to Chad – almost to the point of being rude. You know the type. After about an hour everyone broke up to head home.

I am going to perform again at private Vegas sex club

In early September I performed in a live sex show at a private Vegas sex club. I needed money for college and I have to admit, I was curious and cautiously excited about the sex.

You can read about my experience here. https://www.reddit.com/r/gonewildstories/comments/3mwaty/performed_live_porn_at_a_vegas_sex_club_for/

I've been invited back and here was the invite I received from one of the owners at the club. This is happening at the end of the month.


We have an opening for you if you want it. Saturday October 31 $5000 plus tips. We pay for airfare and expenses like before.

Situation: This is in the small room. Father daughter show. You and two men. One is 51, the other is 48. Both fit. You met Joe according to him. He was in the after care room and talked to you about your show. Remember? Mike is the other guy. He's a nice guy. You will like him. Hung like a horse if that matters to you. Internal cum shots required. Anal and DP required. Blow jobs required. Light spanking and hair pulling required. Daddy talk and name calling required. Light bondage possible. Toys possible. We can talk about limits when you get here. Duration 60 – 75 minutes.

Accidental anal (m/f)

I've been with my girl for more than ten years and had always been disappointed at her unwillingness to take my cock in her ass. I've always been an ass enthusiast and hers is a particularly lovely, big round firm one with a cute rosebud so you can imagine my disappointment. It was an ass that needed my cock in it.

The most I was allowed to do was rub my cock against her rosebud a little to get myself excited before fucking her pussy.

One night we were playing with massages and I was enjoying the view of her on her stomach with that amazing ass tempting me. As I applied more and more massage oil, I cheekily let some ooze between her ass cheeks each time. I saw her move her ass a little as the oil dribbled onto her rosebud but she said nothing; obviously enjoying having her back, neck and shoulders massaged.

I alternated between rubbing oil into her back, and massaging her neck and shoulders while cheekily also rubbing my cock between her ass cheeks. I'd been sneakily oiling my cock as well while oiling my hands so it was gliding between her cheeks nicely.

35M36F 9am First order of business. Fuck Jennys throat!?!

I have posted before about how I hooked up with an old work friend Jenny and although we have had a few quickies I havent written much else.

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https://www.reddit.com/r/gonewildstories/comments/3n4pjb/35m36f_i_cannot_believe_i_got_laid_this_way/

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The sex is good with her when we get a chance to do something but with my wife and fwb and her dating from time to time we keep it sweet and infrequent.

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I came into the office this morning and introduced the staff to their trainer for the day. I couldn't wait. Most of the company in safety training all day means I have a blissful day of not being interrupted while I get my stuff done. I settled down with a coffee knowing the only other people in our corner of the site was Jenny sorting out Patent requests and our receptionist Maggie. About half 9 Jenny burst in.

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Jen: "Quick I'm stressed as fuck and Mags is out to the post office".

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[F]emale white rapper/hippy/sex worker is pretty awesome. Part 1 of 2

This story is kind of hard to write because its 2 different days but the girl is the same so I'll do my best to sound coherent.

So a couple months ago I met this girl at my favorite bar. We made eye contact across the room and I knew it was on. So I went over made my move, danced, kissed, blah blah blah until closing time came around. It was interesting because her older sister was actually hosting that specific night at the bar and her older brother (who is deaf), I rarely even meet the family of women I date so this was weird. Especially meeting her brother who was dressed more conservatively than this particular spot entails. Its especially weired for me because I have a little sister coming of age and I realized that i definitely do not want to party with her because I don't want to see her running into guys like me chatting her up, the thought boils my blood. Anyways, when we decided to go to my home together she eventually lied to him saying she was going over another friend's house and I was a friend of that friend, her sister was more liberal and didn't care either way. Funny little side story was that we shared an Uber with a group of random girls going the same way because she mistakenly jumped into the wrong car and the girls that actually ordered it said fuck it and road with us. This drive was funny because the topic of her being a rapper came up and she got compared to Iggy Azalia and these were a group of black girls so the tease was real.

4 MILFs, 12 Holes (Part. 2) [Str8, mFF, anal, cuck, oral]

I walked out of my hotel room holding Mrs. Done's room key. The comfort level in my pants were dropping the more and more I thought about the things I was going to do with her. Her room was the same one that all of the MILfs met me in, so I already knew where I was headed. The keypad lit up green as the door un-locked and I let myself in. I was greeted to the beautiful sight of Mrs. Done with her legs spread apart and completely naked; she must have fallen asleep like this. A purple dildo laid near the bed, it probably fell off. Mrs. Done shifted around on her bed, spreading her legs even further apart making her pose look like a frog ready to jump. I walked over to her and stood over her sleeping body. She writhed in a little pleasure after I poked her left breast. Her suitcase that was across the room suddenly fell over. As I picked it up, I noticed rope in her suitcase. Mrs. Done must have really wanted to get freaky on this fuckcation. I grabbed the ropes and began to tie Mrs. Done's wrists and ankles to the bed frame pillars. Mrs. Done woke up after I was done tying her up.

[M/F] The one that got away

First proper wall of text so go easy on me.

This was a while back but one of the best experiences of my life, hence why i am trying to put this into words.

This goes back to the days of college for me, a chance to reinvent myself after being a fairly "normal" guy in secondary school. Being known as a funny guy, the class clown and a guy that everyone knew but didn't quite fit in.

In college i decided the best way forward for me was to embrace the tough guy persona when in reality, i wasn't. I was from a notoriously rough area but i had always kept myself out of trouble and generally consider myself to be a nice guy.

Others however, did not see it this way. Especially as i was now going to a college that others saw as upper class. Things started out fairly normal for the first few weeks but eventually i was getting too fed up of the girls and how posh and stuck up they seemed.

I [M] found an old erotic letter to a college girlfriend on my computer, thought I’d share it with you

I don't know if this would be liked here, but figure I'd share it all the same since it was written with passion.

We start by slowly making out, standing up. I pull you close and gently hold your face in my hands as we kiss. I can still taste the sweetness from our drinks from the party we just left, even though you put a mint your mouth on the walk over to your apartment. I slowly start to let my hands explore your sexy body over your clothes, making sure to touch near but not directly on your pleasure centers, making you want it that much more. I see that and know that this will be no quickie.

Ricardo

I knew what I was getting myself into with Ricardo from the beginning. There was never a time where I didn’t know exactly where we were headed, and I always had the opportunity to stop. Perhaps that’s why I didn’t. I smiled and twirled a lock of hair around my finger as Ricardo looked me up and down, taking in my dress and heels. “You look nice. Where are you going?” I smiled and shrugged, flipping my hair over my shoulder. “That depends on who I’m going with.” Ricardo shook his head slowly, his jaw tensing. “Oh, the things I wish I could do right now.” I grinned wider at him and bit my lip, watching the blood rush to his face. He slammed me into the wall so fast I didn’t see it happen, hands on my shoulders, pinning me against . “You’re playing with fire, little girl.” I laughed and leaned in, letting my lips graze his ear. “Mm, yeah, it’s getting hot in here.” He seemed to agree as he leaned forward to nibble on my collar bone, a low groan working its way out of him. I ran my hands through his hair, gently tugging and pulling until he finally looked up “What?” I grinned for a long moment, drawing it out. Then I took his bottom lip between my teeth. “Come and get it, tiger.”

Published
Categorized as Erotica