First time with a cougar

First time with a cougar

This all happened before my wife and I started dating, about 10-12 years ago, I was just about to turn 22, and I was involved in a lot of chat rooms at the time, it was between that, video games with my friends, and racing at the tracks.

I started talking to one woman on the chats, getting to know her, surprisingly she actually kept talking to me cause online I’m a total perv and never really got lucky with most girls on there. She told me she was 30 and single, taking care of her mom and going back to school while working as a bar tender. I thought sounds pretty cool, and kept her as a friend for a while. Things did get sexual and I showed her photos of me, clothed and cock, and she never complained about it. We never got into cyber, she didn't like that, but I finally got her to meet me one night after a race at the track.

[M/F] My Affair: The Rules

This is the second in what is likely to be quite a lengthy series. You can read the first part here.

Rachel was naked, kneeling in front of me, her skin a creamy white in the pale light of the streetlamps coming through the sheer curtains. Her eyes were a little glassy from the booze and her lips were glazed. I was sitting on her couch, my own clothes in a pile on the floor near the front door. It was late in the evening and we had been out at a club with friends. My wife was away at a conference and Rachel's husband was out of town for work.

My cock was hard and still wet with her saliva. It had been seven months since that first night.

She crawled into my lap and wrapped her arms around my neck, pulling me close. She smelled so good. Our bodies pressed together, I could feel her trembling. We kissed deeply. She straddled me, her pussy achingly close to the tip of my now throbbing cock. She rubbed it there for a moment, riding the shaft against her clit. I could feel her warmth and wetness and I was getting lost in desire for her.

Part o(f) (m)y misspent youth.

Most of you would probably consider me an old fart because I’m nearly 50. As a old coach I had once said “I may be old but I still get morning wood” so there’s that. This story is from the early 90’s when I was a young hunk of a man who didn’t know how good he had it, and didn’t take advantage of his assets as much as he should have.

I’ll try to describe myself as I was for the ladies. Young looking white guy with medium length wavy brown hair decent chin and large but not crazy large nose, a relatively ordinary face all in all but nice blue eyes for you to stare into… At the time I was riding my bicycle 25 miles from my house downtown to my job in the suburbs so I was told I had a world class ass. Bike riding wasn’t and still isn’t that cool so I’d say I was could be considered somewhat in the geek spectrum. I’d played division 1 baseball in college and I lifted weights so my upper body was decent as well but I was no adonis. I was fairly evenly proportioned so from a distance I didn’t look tall but I was 6’1”.

My Affair: The Beginning

I’ve known Rachel for quite some time. We met via a group of social media enthusiasts back in 2007 when Tweet-Ups were still a thing. She and my wife hit it off pretty well and soon we were hanging out with Rachel and her husband quite a bit. They’re about our age, a little younger. Rachel is a grad student. Her husband works in IT. She’s very cute, in fact she looks a bit like my ex-girlfriend Laura (see my previous stories for some info on her).

Rachel has smaller breasts, but they’re perkier than Laura’s. Her skin is pale, her hair a lighter brown and her eyes a wistful blue. She’s not as curvy through the hips, but her legs are longer.

She’s one of those people who has very little in the way of a filter on her brain. No subject is taboo. She talks openly about just about everything from her bathroom habits to how many times she’s been caught masturbating by her parents, her brothers, her college roommates and a neighbor. I find it refreshing. My wife, on the other hand, isn’t quite so open. She thinks Rachel is a little weird. She likes her, but sometimes the conversations make her blush.

[F]licking it [F]or him [Oral]

I can feel the ropes tightening around my wrists as I move my hands to get the blood flowing back; they have been numb for…I really can’t say how long. I don’t know how long I have been here. My ankles are tied too but not as painful. As the blood travels back in my extremities, pain resumes. I shouldn’t have done that. Numb was better. He warned me it would happen if I fought the restraints too much.

[M]y Wedding Night with my Wi[f]e.

The other night things got out of hand.

My Wedding had just been a few days before. I was sitting on my honeymoon bed with my dearly beloved wife and she leaned over and kissed me on the lips. My Gosh! You won't believe what happened next!!! She put her flippen tongue in my mouth and began to lick mine.

I sprang back like a mad cat, hissing at her, "What the flip are you doing my dear."

She looked at me with sad eyes, "It's French."

"O I see."

"Did you like it," she asked with those soft pussy cat eyes.

"I suppose it was okay, you can try again I guess… but next time warn a fella before you throw a slug down his tonsils."

So she came back over to me and put her mouth over mine. She stuck her tongue in and it was rather interesting. It felt gross yet nice. Usually I can't stand the thought of another's saliva, but the germs became irrelevant as I also swirled my wet woolly through her mouth. I even touched her slippery teeth a few times. I felt something inside me change in this very moment. We went for ages, it must have been like at least 30 seconds by the time we finished. And that tingling hung around.

Taking advantage of my wife’s acceptance [m/f/m]

My wife and I have been more open sexually lately and I have been taking advantage of her opening up more. She has gotten to explore so far having oral sex with a couple of friends as well as being fucked by a friend and myself.

This time I told her to test the waters and see how bad strangers want her. I posted some pics of her and it got some good reviews. She loves the comments but wouldn't go as far as meeting up with someone or doing anything with them. More so because she's afraid of STDs. I don't blame her and share the same feelings.

We had gone out before to clubs, but I don't dance. She went out on her own or with other friends onto the dance floor to dance and have a good time. Guys have approached her to dance and some got a little fresh. She would come back to me telling me that she could feel their dicks getting hard or that they tried to feel on her tits. One guy even asked her to go out to his car for a quickie.

(M)aking of a Hotwi(f)e

Preface: My wife and I have discussed her being with another man. I don’t see this as cheating. We did have some ground rules, no getting attached, no anal (her tight ass is mine). We have since made more rules, but this was our first experience (and when I say our, I mean her). It’s also worthy of noting we married young and we were early to mid-20s when this happened.

So it was my birthday. It all started out with a friends and family get together at a private function center, the manager of the function center is a close friend (whom we will call David). I had a fair bit to drink. The night itself was pretty normal for a night out (the girls didn't come out after the function center), with the exception of our last port of call was a strip joint. Nothing overly excited happened at the strip joint, just the normal ogling.

In the Early AM I called the wife, asked if she was up, and if she’d come pick me up and give me a lift home (and drop a few of the boys off on the way) – she did, what a good wife.

The Concubine 28 Fsub

Good evening /r/sexystories, I am a fairly regular, albeit new poster over at /r/dirtypenpals and it was recommended I post here. Always love to hear what my stories for you or to you.


I loved the way his hand felt between my legs as he rubbed me outside my panties. He would kiss me deeply, his tongue wet and strong, invading my mouth as I struggled to breathe. White panties, that’s what he wanted. He liked the way they looked when they got wet and sticky, and he would slide them between my lips when I started to get worked up. He would rub me like this until they were soaked and then peel them off of me to slide his cock inside, bringing them to his face and breathing my scent as he drove in and out, and then taking the wet crotch and folding the fabric, he would place them in my mouth and tell me to suck. Watching me taste myself would drive him into a frenzy, and my pussy was sure to be sore by the time we were done. I loved it.

I [27M] did it again…sucked my new friend [40M] while he looked at my wife’s nudes (LONG)

For those who haven't already, I suggest checking out my previous story here: http://www.reddit.com/337ain. It gives some backstory I'm going to skip here and will add at least a little sense to my admittedly strange new kink.

Just as the last story began, I had no plans for a face to face encounter. It was a rush to share with you all and more so to read all your comments and messages (thank you for that). That week I couldn't stop thinking about sharing the story and revisiting the encounter itself. It ended up being a light work week and come Thursday we decided to have a spontaneous date night since my wife was having a girl's night in on Friday at her friend's house. After wine with dinner and more back home after, I worked up my best shit-eating grin and told the wife I was dying to get her in front of my camera again. She put on her best shocked and disinterested act, but I knew from the naughty sparkle in her eye and the subtle lip-bite that she wanted to pose.