Tag: Group

How a vacation with fa[m]ily [f]riend’s turned into me hooking up with a 30 year old mother as an 18 year old.

All right, this is actually a true story. It’s one that’s been imprinted into my minds sexual history gallery because when it happened, it was completely unexpected. (first post – a little long)

I was 18 on a family vacation to a summer cabin on the West Coast. My family was meeting our closest friends, including my best friend and my sister’s best friend at the time. This family’s name is the Henderson’s and they were also bringing along the Henderson’s father’s brother (around 35) his fiancé (early 30’s) and the fiancé’s younger sister (around 30) who had a son who was around 7 at the time. So as it goes it was my family in one cabin, the Henderson’s in another, and the Uncle and his fiancé and her sister’s in another.

My parent’s are liberal people, and having just graduated high school, my best friend and myself were considered adults throughout the trip. The older adult’s on this trip loved to party, and wine and beer flowed from the porches to the beach all throughout the early afternoons and into the nights of perfect weather. My best friend and I had access to beer and wine whenever we wanted, and often spent the evenings after the large group dinners lugging hidden beers in our pockets down to the beach. We met a bunch of other young vacationers our age and partied on the beach early into the morning’s aiming to meet girls at the various fires that littered the coastal beach. Read more »

Ladies Night (M/F Cheat)

It's feels strange writing about this, but I feel like I need to acknowledge how the whole situation really makes me feel. It took place almost 2 years ago. I (26) and my fiancee Jill (25) had been together since grade 11 of high school. We were each others first serious relationship, stayed together through university in separate cities, got a house together in our home community, and had been engaged for about 6 months…6 months away from our wedding.

Neither one of us had ever been much of a partier. I can admit that I was always a little overprotective of her, and I think she was with me as well. During our university years, I wasn't very comfortable with her going out, so neither did I…she did the same. There was never any agreement between us, just kind of a mutual understanding between the two of us that carried on after our school years. Read more »

Used by unknown men (f/m/group)

I'm a 19 year old bisexual girl in my freshman year of college. I met my Mistress at a party shortly after arriving. She's a freshman as well. Normally I wouldn't have mentioned my interest in submission to someone I had just met, but I had been drinking, and we were talking. The next day, when we were both sober, she offered to explore my submissiveness with me. I've been her's ever since and our relationship has slowly grown deeper.

One night, my Mistress told me to meet her in one of the classrooms on campus. I was to disrobe upon arriving, and wait for her there. This was late at night on a weekend, so there was little chance of getting caught by anyone. When I got to the room, I stripped, and placed my folded clothes on one of the desks. My Mistress usually requires me to fold my clothes neatly when I remove them, so I knew she would want me to do so here as well. I sat down to wait for her on a towel I had brought for the purpose since I didn't want to sit directly on the chairs in the classroom. Who knows what's all over them. Read more »

The Night I Played a Game Called Cluster(f)uck

Here’s a story that happened a few years ago when I was single and child free. It happened one weekend when I was visiting my friend at college in New York. I had been friends with Jessica since high school and I hadn’t seen her in the six months since she had swapped cities. She was living in a dorm and had a new boyfriend that she met there. At the time we were all 19 or 20, Jessica is around 5’5 with blonde hair and blue eyes but her greatest asset had always been her large tits that measured in at 32DD. Her boyfriend was called Marcus, I had never met him before but found him to be very attractive and charming. He was a native New Yorker, around 6’2 with dark hair and a well-developed body due to his weightlifting regime.

I arrived on Saturday morning at JFK and got the train to Jamaica Station where Jess and Marcus were waiting to meet me. I was immediately attracted to Marcus and it was great to see my friend again after so long. We got the train to Manhattan and spent the day being tourists and catching up. We had our dinner downtown before it was time to head home, Jessica told me that we were going to get drunk that evening and have some fun. Little did I know! Read more »

Bondage play at the club, group, [FFM]

I'm Tom and in a non-monogamous relationship. Other than that a normal guy with a normal job. I like writing about my experiences so (a) people know that a normal guy can have crazy sex and (b) because it turns me on knowing that you are reading this ;-)

For more about me see my previous stories: https://redd.it/1euujl https://redd.it/1glu4c https://redd.it/1goejp

Anyway, this event took place at another one of the parties I described in a previous story. It's a great venue with lots of friendly sexy people. This time I was there with Leah. We had been dating for about 4 months at that point. She's super sexy. About 5'8, pale skin, and lots of freckles. Slender build with small firm breasts and pink, perky nipples. Quiet personality but always a big smile. Leah is also in an open relationship and married to a friend of mine, but that's another story.

The evening got started perfectly. We drove to the city, had a delicious dinner at a Thai restaurant and then spent some time relaxing at a Russian Bath House. It's clothing optional with lots of hot pools (although no sexual activity allowed). Feeling clean and calm we headed over to the club. We had both been there before and first made the rounds greeting friends but it didn't take us long at all to find our way to the dungeon room. Read more »

My First Time Having Sex in Public. (m/f)

I've never considered myself much of a writer, but I figured I should contribute to this sub since I visit it so often. My sex life has been waning in recent years, but it was pretty exciting for the majority of my adult life. Maybe I'll post more if this goes well. Feel free to comment, I'm genuinely interested in what people think.

Background: All through high school, and Bailey and I were close friends. She was about 5'5”, pale as can be, and though I dont know the specific size, she had the largest breasts I have ever had the pleasure of pleasuring. Her face always reminded me of Kate Winslet, but with a deep purple bob cut. She definitely played to the 20's flapper girl type of fashion, which I loved. All of that being said, my intense attraction to her was by far more mental. We were both huge geeks, and aside from obvious nerdy fair, we would spend hours and hours talking about religions, politics, philosophy. It was clear that there was a mutual attraction from day one, but being young in high school, we never pursued it beyond friendship. Read more »

[m/f+f] My NYE: Sex toys, Skype and Champagne

Ahh New Years! Drinking, singing old Scots language songs, balls dropping, what isn't to love?

Typically, the wife and I shun anything having to do with being social on NYE. Sometimes we'll have a few friends over, or host a dinner party for a small group, but more often than not, we settle in, drink a bottle of good champagne and fall asleep before 11:00. This year, that's what was supposed to be the plan, and it started out that way.

As usually, this involves my wife, Amy, and our dear friend, and sorta fuck-buddy, Carrie. Amy is 5’2”, very thick and curvy, with substantial breasts, typically a DD bra size, I think. She just died her hair almost black, and it's now cut short, almost a pixy cut. Carrie is at least 5" taller than my wife. She's very active in the roller derby scene in our town, and works out almost every day. I've known her forever, and growing up she was very much a tom boy. Her hair is naturally red, and she always has some kind of "flair" in it, either dyed streaks, or highlights or whatever. Her breasts are smaller, but a nice handful, topped with small pink pierced nipples. Her ass is fantastic, full, round, and firm. She's strong, without being masculine, and now that derby season is in full swing, she's straight up cut. Read more »

Fucking my cousins [m]arried best [f]riend..

Before I get a bunch if flak, she's in the process of getting a divorce.

Anyway, been while since I've submitted here, and have a few stories to tell. This was a few months ago.

My cousin, Danni, was having her birthday. As we are both relatively close, she invites me to come out to get some drinks with her and some friends. We all meet downtown at some fancy jazz bar, and get some very very overpriced drinks. I decide on only have two, so by the time we leave, I'm not even tipsy. We decide to hit the strip, which has tons of bars downtown. While we had a group at the bar initially, my cousin brought her best friend, who I had barely noticed. She's the same age as my cousin (23) and actually pretty cute. She's about 5'6, with what looked like DD's, a nice thin waist, and a nice round ass. The more I looked at her, and the more shots I pounded with them, the more I wanted to pound her instead. Read more »

(M)y first time with a (T)rans girl

(This is a true story and also my first attempt at writing. Hope you enjoy)

This happened back in college at the 21st birthday of an acquaintance of mine. My friend Josh was a pretty cool guy, lived in a decent sized house off campus, and loved to throw parties. Josh also happened to be gay as were most of the attendees at the party. I had hung out with him before and knew what his party scene was like. Although I was straight none of his antics never bothered me or made me feel uncomfortable. The same cannot be said about his roommate.

The party got started about 9 o'clock and there were probably 30 to 40 people in the house. Josh's roommate was there and was already drunk by the time I got there. His normal aggressive manners were on full force thanks to the alcohol. I had come in from the patio to get another drink and the roommate corners me by the drink table. He basically pushes me into the table, grabbing at my crotch, and tries to kiss me. Now, I'm not homophobic in any way, but I can't stand this type of aggressive behavior from people. Read more »

Lost my virginity to my best friend (mf) (Cheating)

So to start this off, I'm here to turn people on, not start a moral debate, if you don't like what I've done, don't read it.

In my last year in high school I was a bit of a late bloomer. I had a handful of girlfriends but nothing past second base. I started getting close to Erika and Anna both at the end of the year. Anna was in a long term relationship, but we had grown extremely close to the point that I considered her my closest friend. Anna was about 5'2'', blonde, blue eyes, with curvy hips and D cups. Erika, while on the less attractive end of the scale, had a great personality, with red hair and freckles. She never wore makeup and was a tom-boy.

Erika and I entered a highschool type, hands holding, light peck kisses only type of relationship a couple months before prom. We never had sex, she'd barely touch me for the most part. We had next to zero chemistry, but I wanted to give it a go anyways, since I had gotten desperate. As the partying picked up, Anna and I would flirt more and more. Grinding, arm on the leg when laughing ect. The sexual tension between us became palpable when we were alone. Read more »