How I [F]19 got into a sexual relationship with my boss [M] and why my hubby doesn’t mind.

So I started college last year and was looking for a job near campus to earn a bit of extra money. When I saw that a medium sized local law firm was looking for someone part time as office assistant I was super excited and applied. A few days later I got a call that I should come in for an Interview. That is where I first saw James. He is the old bosses son and soon co-owner of the firm. James is just about 6 feet tall, 29 years old but looks younger in my opinion, athletic and a very charismatic, charming guy. The type of man who can get you to say yes to almost everything…

I was getting interviewed by someone else when he stopped by to say hello and introduce himself. I instantly felt an attraction but was not sure if he did too because altho very nice he seemed in a rush and left quickly.

Down & Dirty Hotel Hookup, [Roleplay], [MF]

This story is for a reader who contacted me privately with a suggestion. I hope that you enjoy!

*For readers who are unfamiliar, my wife Jade and I are average suburbanites, with a fairly active and recently rejuvenated sex life. We’re both in our mid-thirties; I’m white, average build and about six feet tall. Jade is mixed Asian/Native American with an average build (thick ass, small breasts), radiant green eyes and long black hair.*

*****

It was a cold and rainy Saturday night. I’d been talking to a woman throughout the week who wanted to meet up for a drink (and more, for a price, she’d implied) at a local hotel. After getting my room key, I quickly found her, sitting at the middle of the hotel bar. She wasn’t hard to miss. She was already flirting with the bartender, who looked eager to be talking to her. In her mid-thirties and with long black hair, she was dressed in tight jeans, black stiletto heels and a flowing, sparkly top, complete with a lot of makeup and big jewelry. She was definitely curvy, which I didn’t mind at all, and her hips were highlighted by her tight jeans. I felt a pang I’d jealousy and excitement, as the bartender was clearly into her. I walked right up to her and said “Hi, Jade.” Her eyes lit up and she gave me a kiss on the cheek. She wore bright red lipstick and some dark eyeliner that drew out her eyes. “Hey guy, are you going to buy me a drink or what?”

[MF] The perks of dating a pro triathlete: tight body, awesome tan, and fully shaved

In my 20s, I was an aspiring pro male cyclist. To pursue my racing dreams, I moved to Colorado and would race and train 3-5 hours a day. While it’s a lot of working out, it’s a lot of down time, and being a 20 something fit guy, you’re constantly looking for good trouble and better pussy. I’d hang out at the bike shop, coffee shop, the park, the pool, wherever people were at. At the pool was where I met Jenna (not her real name).

Jenna was already a pro triathlete. She had long blonde hair, lean and toned, 5’7”, 130lbs and you could see her thigh, shoulder, abdominal muscles. Not a 6 pack or overly muscular. She was at the pool a lot doing laps and as an athlete, I wouldn’t hit on her there. I noted her backpack had some sponsor patches and figured out she must be a triathlete. I made note of which bike and clothing sponsors she had cause I’m a bike nerd.

Selena’s Family Reunion (Incest | Cousins | Taboo | MF | Oral )

Finally I had made it to Texas for the annual family reunion that our older relatives always hosted. I had just gotten back from filming a movie about spring break. After filming I was kind of glad that I had done the movie, because I had worked on getting this great bikini body. My body was in perfect shape and my tan was golden without any pesky lines around the bikini areas. We reached the family house where we were all unpacking our bags from the car, when my grandmother came out to hug and kiss everyone. She quickly told me that I needed to put on a shirt, because I was only wearing my blue bikini top from the movie with a pair of denim shorts. I promised her I would as soon as I got to my room to unpack.

That’s when she told me that I would be sharing a room with my sisters and cousins this year. This was the new housing conditions since my aunt had to have her own room with the baby. I told her that I could stay in the hotel downtown, but she insisted that the family needed to stay together. I tried to argue that we was too old to be staying in the same room as our cousin Brandon and his sisters. The debate was hopeless. Grandma demanded that it would be just fine. So my sister and I headed up to our room to unpack.

[MF] I (M36) Went from teaching her (F23) English, to teaching her sex (Part 2)

A couple of months passed since my last “lesson” with Hina. I thought about her from time to time, but she was dating some other guy, not to mention our age gap and the fact that I used to be her teacher back when she was still a young teen. I decided I was lucky to have gotten her to blow me twice and swallow my load once, and move on keeping the hot memory. One day Hina messaged me out of the blue and we texted for a bit, which lead to a meetup. While there I asked about her and her new boyfriend and if our lessons were any help.

“Yeah, everything went okay I guess.” She said not sounding all that excited.

“Just okay?”

“We made out, got naked, I gave him a blowjob and I think he liked it. Then we had sex. It was a little painful and uncomfortable at first but I got used to it, and it wasn’t bad.”

“You still don’t sound that jazzed about the whole thing.”

“Yeah, I guess I was just expecting more. SEX! Everyone’s so crazy about it. But he put it in, in and out for a few minutes, and then he was done.”

Got a free blowjob from a hooker [MF]

I was about 19 or 20 I went through a phase of trawling through dating websites (pre tinder) for older women who were down to fuck.

I had some free time and saw a profile online for a 30 something blonde bbw. We starting chatting and she mentioned she was in town today. I lived with flat mates so she wasn’t keen to come to mine and she was travelling in a caravan so that was out. I got the feeling she was travelling with her husband or kids or something.

As any horny teenager does when they get a hint that they might get some, I sent a dick pic to her. She said she loved sucking cock and that it looked tasty. She told me she was staying near a beach across town but maybe we could have some fun in the car. So I got my ass in the car and drove down to the beach.

I should mention that this was the middle of the day during the holidays so this beach area was really busy. I parked in a car park near the beach and messaged her so she new where I was.

My engaged friend is getting sluttier and cockier (part 3) [MF]

Acquaint yourself with Sarah and I. [Part 1](https://www.reddit.com/r/gonewildstories/comments/hrluth/my_first_time_with_my_friend_who_had_a_fiance_mf/?utm_source=share&utm_medium=web2x) and [Part 2](https://www.reddit.com/r/gonewildstories/comments/huivv9/my_adventures_with_an_engaged_friend_part_2_mf/?utm_source=share&utm_medium=web2x). I also write about Sam and I, [My adventures with Sam](https://www.reddit.com/r/sexstories/comments/hm6ifj/the_first_time_i_fucked_my_longterm_friend/?utm_source=share&utm_medium=web2x)

~~Long post~~

Halfway through the trip Sarah had given me a blowjob and we had fucked twice. I was very single at the time, so I was constantly in a flirty mood. I had some chemistry with two other girls who came on this trip with us. But, something happened at the halfway mark which turned it into a more exciting vacation.

Midpoint of vacation: I got my cereal and beer, walked out to the deck and sat in peace. Sarah and I had not done anything in the past day or two. No change in her behavior, just for the past two days, she didn’t come to my room, I didn’t find her downstairs at night or anything (I lurked a bit). But like every morning, this day too she came and sat beside me with her breakfast. Only today it wasn’t as peaceful. We heard a lot of commotion and yelling and laughter. I got annoyed and got up ready to ask someone to shut the fuck up, but as soon as I saw who was causing the noise, I just came back smiling and sat in my chair. Sarah asked who it was and I just said, “Its fine…” she got up and looked around. Came back towards me and slapped my shoulder. “I hate you…” she said sarcastically. About 6-7 sorority girls had arrived in the villa right next to ours. One of our friends happened to be in the same sorority as the girls next door (different chapter). The rest of the morning I had a smile on me, Sarah at one point asked, “Can you not be this happy?”

Gavelstock Manor

Their caravan had split from the main highway 45 minutes ago, and each new road had less pavement and more rocks. They had slowed to a crawl, but were still making good time – they’d make it to the rental before the sun was down, and would be able to enjoy a swim at the lake. Xtel was in the back of a six seater van with a man she didn’t really know other than it was, in fact, his rental, asleep in the corner hugging his duffel bag having come straight from a ‘night shoot’. Driving was their mutual friend Dexter, who was gabbing up a storm with Becky in shotgun.

Watching with side eyed pride, Xtel watched her girl spend the four hour trip feeling out Dexter the way a lioness stalked it’s prey – it was her M.O. Becky and Xtel were best friends since they dormed together in college, roommates for 4 more after that, and sworn-to-secrecy partners in exploring each other in the bicurious phase. She knew ALL her tricks. Their love was deep and intimate but beyond that now, so there was no jealousy in watching Becky use her words to savor the man driving her. Enthusiastically, she found out about Dexter’s connections with the man in the back seat and how he was able to score an impossibly balling lakeside ‘rental’…as well as if he was single, physical, friendly, and hot-to-trot.

My [28F] holiday to Europe which ended in a [Group] ? ✈️

This is my first story. Don’t be too harsh please! Haha. And it’s looong!

I’m a highly stung primary school teacher and team leader ?‍? Middle of 2019 I took 4 weeks off to head to Europe and do a tour with one of those group tour things organised through the travel agent.

I got it on with a couple of guys on the trip, a foreign guy or two but they were nothing compared to this night!

Our group went out for dinner with the tour guide. All had some drinks afterwards and such and started splitting off. Myself [F28, pasty white and half sunburnt with average height, big booty and thighs that touch thanks to mum and C cup boobs] and a few others including my roommate Sophie [F26, not pasty white but still white, taller than me with a tight bubble butt and slightly smaller boobs] went on and ran in to another tour group. Sophie and I were chatting with a couple of cute guy next door types [both mid to late 20s, our sort of age, I didn’t even know exactly, neither were super fit and built but they weren’t fat either, just a good average guy next door] who didn’t seem to cocky and were a good laugh. Few drinks. Some flirting. All harmless fun. It got to about midnight and Sophie and I were calling it a night, we were drunk, but not plastered, just buzzed and feeling great you know? Haha. We started walking back and the guys followed us as there hotel was further past ours. During the walk there’s plenty of flirting, butt squeezing and such.

My girlfriend’s cock is bigger than mine (MTS | anal | bj | exhibitionism )

My girlfriend’s cock is bigger than mine.

I met my girlfriend on the beach, of all places. I had come out of a bad relationship a few months prior, unsurprisingly related to my tiny cock. My then girl just got bored of it I guess, but it might have been my constant bitching and self inflicted deprecation, who knows. In any case I met Cassandra at the beach.

She was on a lazy chair sunbathing and I was playing with my dog. I threw his ball but the wind caught it and fell next to her. She was startled when a huge hyperenergetic golden retriever jumped at her searching for it. I ran to apologize and had to grab Mr Woofer by the collar.

“Sorry miss,” I said, she was shockingly beautiful, long dark hair, big puffy lips with a smile waiting to shine, dark green-brown eyes, a huge pair of tits that she showcased to all to see on a tied two part bikini, and between her legs, the largest bulge I had seen on a girl outside of the internet.

“Don’t worry pretty boy,” she said winking and started to pet my dog, “whose a nice boi? eh? whose a nice boi?” She said while petting him.