gonewildstories Archives — Page 4100 of 5640 — NSFW story

(Sissy) Hooked up with a guy for the first time today! [TM]

So, I met him in a bar around a week ago, and we talked a bit. We organised for me to go to his (today).

I dressed up in my best slutty clothes and my hottest high heels, a lot of freshly shaven skin on show.

He greeted me at the door with a smile and a warm hug, made me a coffee and chatted for a bit in his lounge, during which he showed me his good Sti check . After a while, he told me to put my cup down, and he put himself on top of me and kissed me so hard I don’t think I’ll ever forget the feeling of his tongue on mine.

Then he peeled himself off me and I swear I was heartbroken, but then he held out his hand for me, I took it, and he kissed it so gently! It was better than my dreams! Then, he led me upstairs to his room… ;) Read more »

Sleeping with a married co-worker in her own bed [MF], cheating

You can read my other stuff for some context but it’s not 100% needed.

A quick summary of my life at this time. I was in my late 20s and had a mess of an affair with an employee. It led to a stressful work life and a trial separation from my wife.

The woman I slept with was turning out to be crazy, she is Mia in this story and not that important.

Another division head in my company, Lisa, had started to come around more often. We would chat and just bullshit. Often bitch about life.

I recognized all the signs that it was getting more flirty. I wasn’t totally clueless this time.

She was not like Mia. Mia was a 10/10 redhead with legs and an ass to die for.

Lisa was more a mom type. Short. Curvy. Dirty blond hair. Her face was average. Her body was…normal. She wasn’t turning anyone’s head.

I wasn’t that attracted to her. And stupid me was full of myself since I had been fucking Mia. Why I thought I deserved better since Mia was using me (see last stories) I have no clue. Ego is weird. Read more »

Best Ride Home Ever Part Two [MF]

So if you want this to make more sense, read the first part otherwise as I used to say as a wee lad, you are being a silly goose. Youthful insults laid down, if you are still with me, on with the regularly scheduled naughty story.

So I woke up Friday morning on top of the world. Thursday had been such a thrill and it was honestly great too not just from the taboo of cheating on my gf. I love those floodgate moments where you finaly get what you want after a long time of holding back. The first thing I did after that first stretch in bed was reach for my phone and immeadiatly text Brie telling her how amazing last night was and how fucking hot it was. I was already thinking about her and I wasn’t even out of bed yet.

Within a couple minutes she had replied, “I know right, I was so turned on in the back when I felt you against me knowing it was me that made you that way.” Followed with, “And then when we kissed outside I knew I was going to be a very bad girl. So umm, what are you thinking about in bed about me. I bet I have an idea.” Before I could respond she sent me a topless selfie from her bed where she was still too. Read more »

Wi[f]es sister made fa[m]ily vacation one to remember.

Every year my wife’s family rents a fancy lake house at a popular lake. Her dad, grandparents, sisters and their families go as well as my wife and I so it is a house full but has plenty of room for everyone. Us younger people hang out by the pool and hot tub a lot of the time. One time will stand out in my mind forever.

Her sister and husband recently moved to California which was 5 months before our trip. We had been drinking most of the day and was upstairs watching football. My wife’s sister, we will call her Erin said she was going to the hot tub and asked if anyone wanted to go. There was not a reply so on her way downstairs she asked me if I wanted to go. I said “what the hell” let me change and grab some beer and I will head down. “Ok” she replied.

Erin was a nice looking girl, c cup breasts, wide hips, and an ass for days. When I got down there, Erin was already in the hot tub. She was wearing a little bikini that barely covered her tits, and showed off her amazing ass. I took off my shirt and climbed in the hot tub with her. Read more »

I [M]45 gave the sister[F]43 in law a pubic haircut and we both masturbated

TLDR : Wife can’t have sex so lets me play with her divorced sister.

My wife Jane, 45, has a condition that not only prevents her from having penetrative sex but also has removed all of her sexual desire. I still love her but I do miss a bit on nooky. She still occasionally helps out with a bit of hand or mouth release but I know she is not enjoying it so it kind of takes the edge off of it.

Her sister Kate, 43, separated from her husband a couple of years ago and is now officially divorced. Having a full time job and two kids she doesn’t get to meet many people so has been single since he left. She finally struck up a close friendship with a colleague from work which she was telling us about one night when she was over our house. She explained she was due to go out on their first proper date together and was hoping for more than a kiss and cuddle at the end of the night.

My wife joked that she hope Kate had tidied up her lady garden, suspecting a few years of neglect. Read more »

Sex at a 4th of July Party [MF]

It was 4th of July and one of the first hot days of the year. One of my friends called me up about going to a party at his girlfriends parents place and with nothing else to do, I ask my roomie and my girlfriend if they wanted to go.

Before I get into it, let me tell you a little about my girlfriend Morgan. She was 5’6”, long thick black hair, thick with 36DD boobs and a booty to match. Morgan was a bigger girl but she had the confidence of Tommy Lee and the libido to match, or at least sometimes it felt like it. At this time we had been dating 4 years but we had never felt more distant. Little did I know, she was cheating on me but I wouldn’t find that out for another few months.

Me and my roomie go to pick Morgan up and she comes running out in her token summer outfit: Black tank top, cut off denim shorts, flip flops, with sunglasses on her head and her thong showing. Morgan loved to show off and I think part of the reason she did it was to make me jealous, which it did. Read more »

Choke [M]e and stop holding back. [F] Aka last Tuesday

This actually is my alt account’s alt. Because ya know, cheating. I really get a kick out of writing my stories. Maybe it’s an extension of my exhibitionism. Either way, I’m not taking the risk. These stories will all have been recent. Many years of a relationship have left me a bit out of shape. My plan was to pick up a few sexting partners to get off with in the meantime. I’ve been running, have a HIIT regimen lined up, and by summer look for some regular partners on the side. That timeline got sped up a bit. It was one of the anonymous chat apps. Honestly, don’t even want to write the name, hate for my gf to see it on my phone and possibly figure it out if she ever saw this. If this kind of thing gets your dick hard, my girlfriend is laying on the couch right next to me. Read more »

Fooling around while the sisters slept beside us [mf]

One of my bestfriends in highschool was this girl Jane. I was in love with her, but she had a boyfriend and I was completely friend zone.

When we were 20, I was over at their house and we were watching a movie on this big couch. We had pulled it out into the bed so we could lay out. Jane’s younger sister and her friend, both 18, came to watch the movie with us.

It was typical as we all lay there watching the movie. It ended and soon we fell asleep. I was sandwiched in the middle beside her sisters friend Jenny. Jenny has huge tits and I wanted to see them. So, we started making out. I quickly had her shirt up to see them. Amazing, of course.
I started sucking them and fingering her. We were being as quiet as possible as the sister were on either side of us. Soon Jenny was cumming as holding her breathe to be quiet.

As soon as she finished cumming, she slid down the bed and took my cock in her mouth. She hid under the covers and sucked my cock until I emptied into her mouth.
We both went to the bathroom to clean-up a bit. Then back to bed in between the sisters. Read more »

My new partner [M] has me [F] wearing sex toys at work and speaking events

I actually considered making a throwaway for this…however, I have decided that I didnt want to hide the sexual side of me with anonymity which in turn makes me feel shame for them.

I met my most recent partner actually through a subreddit which in a strange turn of events has been the best relationship I have encountered in my dating history. He’s funny, dynamic, smart, and everything I desire and am attracted to in a guy. My sexual history has been fairly “Laissez-faire” and I have done a fair amount of submissive play including shibori, tying, etc. but nothing of high magnitude.

As I have aged, I have stopped concerning/worrying myself what my partner wants to what *I* want and trying to vocalize that. He has been extremely receptive and tender in that regard as we build our sexual compatibility.

I like to be shamed into tapping into that core “sluttiness” that I have burning inside me…that feeling of being controlled and shamed…all in my head…the outside audience not knowing what is truely running through my mind as we I work, socialize, and blend into the the background. I work in an office and field environment so theres opportunities to branch into a bit of public play at the place where you are most serious. Read more »