[27M] Went on my first cruise last month, met a woman [37F] that made me question how I view sex, as a topic and activity. [MF]

To preface, I posted this story on another sub two months ago. Someone suggested I post it here as well, Hope you enjoy! the original post is here: [https://www.reddit.com/r/sexstories/comments/u5ecdf/27m_went_on_my_first_cruise_last_month_met_a/](https://www.reddit.com/r/sexstories/comments/u5ecdf/27m_went_on_my_first_cruise_last_month_met_a/) for context on any unanswered questions you may have. If you still have any, I’ll answer them here too.

This is my first time telling a story. Be easy on me, lol. It’s a little long as well, sorry if that’s not your thing.

A few details before starting, I am getting out of a stressful ,DB marriage situation (It was mutual.) our divorce finalized 3 weeks before the cruise. we hadn’t had sex in over a year. I’d forgotten what a woman could do to me and I began thinking I might not find women sexually attractive due to the negative connotations that my now ex-wife had created on behalf of women in my head. Of course, this is a terrible train of thought. I was NOT in a good headspace. (I’m fine now, but if you find yourself in a similar situation, PLEASE do yourself a favor and talk to someone. if not a therapist, I’ve found complete strangers give pretty good, unbiased opinions.) :)

Sorostitute Surpries [M]e On Our First Date

It was August of 2019 (which was a very good year for me) and I had matched with Rose. A 5’3” slim-thick asian girl with light brown skin, dark hair, and big brown eyes. If memory serves me, she was about 23 or 24. She showed up in a simple black dress that went down to her lower thigh.

We had an interesting phone date (I usually like to have a phone date to make sure there’s some sort of conversation chemistry) before meeting in person; the phone date was interesting because she engaged me quite a bit, but I didn’t get the impression she was particularly interested. She also made it a point to say that I wasn’t typically the kind of guy she went for, but neither was her last boyfriend and they really hit it off. She was “trying new things this summer.”

We decided to meet at the Chicago River for drinks and I remember her being somewhat late. A bad uber driver apparently taking her to the wrong location for the bar we were going to. She said that happened to her a fair amount, and that she got hit on a lot. I believed her; between the way she looked and the thirst of uber drives, yeah…

Gone wild doctor visit [MF]

Me and my wife are in fertility treatments. Our road to get pregnant went through so many doctors between her legs. 🙈

All this made us imagining cases were doctors are taking things farther… Even one of the treatments was a doctors that had to dig deep inside her with his hands, while an intern and me are looking at him. TBH it was super hot.😎

This week we had a treatment that is called IUI which basicly means that I have to cum into a cup , and then a doctor is injecting it into her. Since I had back pain, I asked for a room when I can lay instead of sitting while I jerk off, so I have got a genicologist room with the bed where ladies can put their leg in the air 😆

I fucked a guy I just met on my couch [FM]

You would never guess, but I am actually extremely shy around people I don’t know. Especially when the topic of sex comes up.

I was 18 and just moved into my roommate Stacey’s apartment. We had met a few times before, but she was more a friend of a friend rather than a “friend”. I met her boyfriend Ron early on and you can read more about the fun night the three of us had in my other posts. Long story short, we get along great. That’s good for many reasons, but a big one is that I moved a little way away from home so most of my current friend group is hers.

Ron, Stacey and I had just got done smoking when someone knocked on the door and then walked in on their own. The guy was tall and black and, he looked around Ron’s age. I noticed right away that he was a good dresser. He had a beautiful smile, but the first thing I noticed was his arms threatening to burst his shirt sleeves. It actually startled me a bit because I wasn’t expecting anyone to be coming over, but I quickly realized it was Ron’s friend. I smiled and waved awkwardly from my big chair with too many pillows when they introduced me.

Fulfilling a friends fantasy [MF]

I was having an intense fling with a work colleague who had, like me, recently separated from her partner.
She was 33, around 5’1, blonde hair,32DD breasts and a tight arse.
We had shared a lot of fantasy’s one of which she kept coming back to.
I booked a hotel for us in Edinburgh, and we went for a meal before heading back to our room.
I had laid out on the bed what I wanted her to wear, black peephole bra and a pair of stockings. She went to get changed and when she returned I laid her on the bed. I then tied her hands to each corner of the bed and her legs likewise. She was spread wide and exposed, her slit was alreadyk glistening. I got the wand vibrator and turned it on low and started to press against her pussy, angling it up and pressing on her clit for a few seconds before removing it and starting again. I was taking to her asking her if she felt like a good slut and if she wanted a treat. She said she did so I sent a text message of our room number and instructions to text me when at door.
The man I text I had been chatting to via a popular swingers site, he was in his 50s, stocky and had a thick 6” cock. He had agreed to come and help fulfill my friends fantasy and had been briefed on the script.
As I waited in him to text me back I went down on my friend slowly teasing her clit with my tounge, getting her close to edge , I felt my phone buzz so I stopped , and went to open the door quietly.
I allowed our helper into the room, I asked her if she was ready for her present and she said she was so I sat on edge of bed as our guest went I over to her and took one of her nipples in his mouth.
He unbuckled his trousers, stepped out of them, all the time his hands were exploring her body, pinching her nipples, he slipped 2 fingers into her and then took his hand out of her cunt and straight into her mouth…
He stroked his cock till he was hard, rolled on a condom , knelt between her legs, he looked at me , I nodded and he then pushed his fat cock into her. The way her back arched and her mouth opened ha stayed with me to this day.
He started with two slow strokes and then he began to fuck her hard, he was lying on top of her, his hands under her arse pulling her onto him
As he fucked her hard. The noises she made were incredible and after a few minutes of fucking he made a loud noise signalling that he had came.
He climbed off, got dressed, left the room. I then undid the ties, Removed the blindfold, and cuddled her as asked her how it felt to be fucked by a stranger she didn’t see and didn’t know their name…..

Still slutty at 61. [FM]

I’m a 61 year old woman. My husband is the same age as I am. We have been together for 26 years, 17 as a married couple.

I’m happy to report that I’m still his slut. The same slut whom he took to his bed 26 years ago. I still love sucking his cock, licking his balls and getting pounded by him like nobody’s business.

Over the years our sex life had only gotten better. He and I have been through so much together. Our bond has taken our sexual chemistry to a level I didn’t think was possible.

Today we are a lot less busy that we were a decade ago. We travel together, work out together, foster fogs and cats together. We are best friends. But we also give each other a lot of space. I have my interests and goals, he has his. Spending some time apart just makes our desire burn brighter.

Meant to just meet up for lunch with a guy who’s not my husband & ended up fucking him. [FM]

***Disclaimer – all names have been changed of course. & no I won’t tell you my other account or share my nudes on here, you will just have to use your imagination.***

If you don’t want to read the beginning skip this paragraph ****

I had been speaking online to this guy for a little while before the constant sexting and video calls were driving us both wild & decided to just meet up and talk in person.
A little bit about me –
I’m 5”11 with long brown hair, big f cup boobs, big hips and a big ass. Chad who I was to meet up with ( also married ) stood just above me at 6ft 1 and has a nice average sized body, And a great big cock we will get to soon.
I thought about the logistics of working out how to meet him as he lived about 50 miles away & needed to pay a babysitter without my husband knowing I’d left the children for the day. The guilt was also there but this wasn’t my first time cheating and remembered how fun it had previously been.
I drove to him as he planned on meeting up with me on his hour lunch break and I met up with him at the local mall.
We awkwardly hugged hello and we started walking together. He just quickly steered us towards the toilets and we went into one of those baby rooms that have private cubicles moms can breastfeed in.

Wanna Improve Your Grades? [Mature] [MF]

It all happened years ago. Back when I was 21 years young and still a college student. Life was great back then. I was studying, I was partying hard, I was fucking around a lot, I had a blast. But there was one thing that stood out, one thing that I will never forget.

There was one professor, she was around 55 years old, she was nothing but hot. A good looking woman. With next to perfect curves and a beautiful face. She always dressed the same way: A shirt, always buttoned up and an extra long skirt. Her hair always pinned up. Wearing some age old glasses. Conservative as fuck.

But she gave me the hardest boners ever. I just had to look at her, and I was rock solid. So instead of listening to her lecture, I always fantasized about being with her. About pulling up her skirt, spreading her legs and licking her pussy. I was as distracted as someone could be. She was talking, she was writing stuff on the blackboard, it all just went past me. A very big problem. Because it was an essential subject.

a quick trip across state lines [MF]

This is going to be a long one! But wirth it!

I am not going to mention where I live for privacy reasons, but I can say I do not live is a state where gambling is legal. I have always been a fan of some fun at the casino. The closest town with gambling to me is about an hour an fifteen minutes from where i live. I know it’s not a long trip but I dont make it very often.

I tried to get some friends together to join me in a quick trip over state lines for a night of drinking and fun .but all I got was excuses… “I can’t afford the extra money ” or “my wife doesn’t want me to go.” I figure what ever 🤷‍♂️ I’ll make the trip myself. I pack up an overnight bag, gas up the car at the station and head out on the road. I’m just jamming to some music, eating some junk food and enjoying my drive.

The not-so-happy end of my threesome [MMF]

*Once upon a time I posted and then quickly deleted this. Considering one of these men wrote about our sex life in his dissertation and the other recently wrote a memoir I played a role in, enjoy…*

I had a threesome with two dudes and it was fun. After it happened, both of them worried a little too much about my feelings.

In the end theyre the ones who got a little weird.

I once came home from work to find my boyfriend belligerently drunk. This wasn’t a huge surprise as his best friend was about to leave us the following day and he wasn’t good with feelings.

*Also, the three of us had been hooking up all week.*

After a huge fight ensued, his best friend and I managed to put him to bed.

“Come here,” he said. I

“I’m not going to bed at 8:00pm,” I answered as I tucked him in.

“I didn’t mean you, you presumptuous ass.”

“Go to bed, damn it!” His best friend said.

We left him like that.