How I [M]21 lost my virginity to a [F]30 redditor I met on my local r4r subreddit [Long]

So lately I’ve been reading this sub and It kind of inspired me to write the story of how I lost my virginity to a redditor some months ago. Idk if I’m the best writer but I did my best, I really just wanted to get this down and share it. I did my best to provide as much detail and at times the story might be a bit cringey or awkward, but I wanted to tell the story how it happened through my eyes.

At the time of this story not only was I a virgin but really inexperienced in general. Out of high school and in college I’ve never had a girlfriend, much less a kiss or done really anything, so I was looking to potentially try and do something about it. I had been browsing my local r4r subreddit when I saw a woman’s post saying she hadn’t gotten laid in a while. I sent her a message and I explained my situation. She started weeding out the other applicants and after chatting for a bit and exchanging some pictures she chose me. We talked and decided on a date to meet up. As the date got closer I was a bit nervous and tried to plan out exactly what we were going to do, messaging things like Are we going to do doggy, missionary, would you like me to eat you out? etc…Knowing I was nervous she humored me and kind of explained we should probably take things by ear.

[M]y [F]orbidden fling in college

I had been a late bloomer as far as sex and with other things too. I didn’t even play on my varsity football team until I was a senior in high school. By then I was “man sized”. So that was why I ended up playing at a junior college before I couldn’t play anymore. Fortunately I had good enough grades and got an academic scholarship to a major university.

The university I attended has a lot of foreign students from all over the world. In one of my classes a girl caught my eye, but almost all semester she ignored me like I wasn’t alive. I had found out she was from a very conservative country that frowned upon guys like me, seeing us as inferior. But I had a plan. We got assigned at “random” to an assignment and wouldn’t you know, we were in the same group. After 2 weeks she finally agreed to meet up for coffee. Honestly I didn’t expect much but wanted to see how far this could go.

How I found out my friend is a secret slut like me [FFM]

One of my old work friends, Daniela, hit me up last week because she was back in my city temporarily. I hadn’t seen her for a few years after she moved out of state, so I was looking forward to seeing her so much. We both love a good party, so we made plans to go to the club on Saturday 30th for Halloween. She is super pretty, she’s Cuban, similar height to me, curly brunette hair, big brown eyes and she has an amazing figure. She’s a few years younger than me so I’m sort of like a big sister to her, but I’ve always had a bit of a girl crush on her. We talked about guys and stuff in the past, but she had no idea about the full extent of my sluttiness, and I never knew hers…

Saturday 30th rolled around and we were having a great time in the club. Daniela looked gorgeous in her all red devil outfit and honestly, she was hotter than any of the guys there. We danced with a guy who invited us over to his table, and we ended up chatting to him and his younger brother, who unfortunately wasn’t as smooth, tall, muscular or good-looking as big bro. After a few drinks, they dared us to make out with each other.

Fucked [M]y ex [F]rom high school years later while her BF/Ex BF was at work

I had met Kate in our senior year of high school (both of us were 18) and we had hit it off. By that I mean she was jerking me off on our first date when we went to see a movie. Not long after I ended up being her first, which went on for a while until we broke up. Periodically we would find each other and hook up though. She had joined the military and the night before she left, we had another fling.

Well after she got kicked out of the military, no surprise there, she got knocked up and married some guy. I’d lost touch with her by then. But like always she resurfaced and came to hang out at a popular bar with me, while I was still drinking a lot. She admitted to me her dad had never liked or approved of me, he wasn’t a fan of interracial couples I guess. She had just gotten divorced or separated, hard to tell with her sometimes. One night at the bar we snuck off and she gave me a nice BJ in the bathroom. Truthfully I would have fucked her but due to the circumstances we couldn’t. She had brought some guy with her and one of her friends too, so she had to hurry back to them. Found out later that guy was some guy she’d been seeing. Shocker.

[FT] My Girlfriend and I – Date Night

[I’ve shared some of my stories, but never about my best friend and girlfriend and our own adventures in kink and bondage and the many stories it’s brought us, so I wanted to begin to write about them and share here! Hope you all enjoy!]

“You didn’t tell me my wardrobe options would be limited when you put this…cage…on me…”

“Locked it on you. You look amazing, I love the sundress. Did you know I’m a sucker for high heels, too?”

I wore my own pair of black stilettos. I didn’t wear heels outside of the bedroom much at all, but I wanted to give off a classy but powerful vibe. Like a seductive boss. But as Meg called it weeks later I looked like a high-end call girl in my leather pencil skirt and plunging top. I took that as a compliment.

Meg was in a flowery and flirty dress – a mix of cocktail and summer day – stockings, and her own pair of heels in a black chunkie bootie style. It was a good thing I wore heels, she would have been towering over me, and that isn’t useful when you’re trying to give off a vibe.

[MF] Giving my friend her “firsts” (part 3 – final)

-NIGHT 4-

Mary came back the following weekend. This time she seemed a lot more confident and relaxed. I guess she felt like she was getting the hang of this whole thing after getting each other off the weekend before. She seemed like her regular old self, no sign of nervousness as we hung out through the afternoon and into the early evening. I wonder if she knew what this night would entail. I had one more night planned before finally taking her virginity. So far she had no reluctance or hesitation with anything we’ve done, but I was always nervous about asking a girl to suck me dick for the first time. I guess it was my turn to be nervous for a change.

Eventually we were making out on the couch again and Mary had taken her shirt and bra off quite early, eager for me to play with her breasts again. Of course I obliged. Soon our pants were loosed and hands roamed in and out to touch and tease each other. It was easy to tell that she was a lot more comfortable with the situation now and it was much easier for her to get into it.

[MF] Giving my friend her “firsts” (part 3 – final)

[PART ONE](https://old.reddit.com/r/gonewildstories/comments/q7b1bc/mf_giving_my_friend_her_firsts_part_1/) link to GWStories post.

[PART TWO](https://old.reddit.com/r/gonewildstories/comments/q7nfrk/mf_giving_my_friend_her_firsts_part_2/) link to GWStories post.

-NIGHT 4-

Mary came back the following weekend. This time she seemed a lot more confident and relaxed. I guess she felt like she was getting the hang of this whole thing after getting each other off the weekend before. She seemed like her regular old self, no sign of nervousness as we hung out through the afternoon and into the early evening. I wonder if she knew what this night would entail. I had one more night planned before finally taking her virginity. So far she had no reluctance or hesitation with anything we’ve done, but I was always nervous about asking a girl to suck me dick for the first time. I guess it was my turn to be nervous for a change.

Eventually we were making out on the couch again and Mary had taken her shirt and bra off quite early, eager for me to play with her breasts again. Of course I obliged. Soon our pants were loosed and hands roamed in and out to touch and tease each other. It was easy to tell that she was a lot more comfortable with the situation now and it was much easier for her to get into it.

[MF] FWB Introduces a Kink that Pays Off With Wife 10 Years Later

My kink was introduced to me in the Summer of 2011. It was a wild and sex filled season for me. It was filled with pool parties, late night parties, and an entry level finance job that was no more than a way to pay for my fun times as 23yr old. I had the most sex I had ever had that summer with too many partners looking back but it was fun and I managed to escape without an STD or a kid. I managed to juggle 3 FWB but one stood out the most. She introduced me to a lot new experiences and ideas, and she had sex drive that was even higher than mine. After the first time we met in May and going through September there wasn’t one time that we hung out where one of us wasn’t cumming. Her name was Tiffany.

my vixens unexpected gift [MF]

Last weekend, my gf went to a house party in her own place (which is a medieval town between Antwerp and Brussels in Belgium). It was actually a drink organised by friends of her dad and the invitation included also her. She and I were easy, had no horny plans, though she knew she had a permanent free pass (or carte blanche). Yet, it would be a quiet Saturday night, so I thought.

At the party, there was this interesting older guy, early 50’s, a curator of a small filmfestival, so plenty to talk about, seen my girls wide cultural and intellectual interests. She is a stunning beauty, so she always attracts new attention, so nothing new there. The drinks were plenty, it became later and later, and the atmosphere became looser, merrier, more flirtatious. The perfect setting for my girl to let any reserve go and transform into this flirting yolo vixen, with those typical tantalizing eyes. So the subject changed towards (open) relations, liberal sex, sexuality, and she seduced him to leave the party and to go to his place, a few streets further.

Amnesia Was The Best Thing To Happen To My GF [M/F/F/F] Part 33

[Previous](https://www.reddit.com/r/eroticliterature/comments/qly3ss/amnesia_was_the_best_thing_to_happen_to_my_gf/)

*** ***Chris*** ***

It’s been about a week since New Years. While fun, we decided to give Raissa and Victor a chance to come to terms with what they want with each other. I think me being in a polyamorous relationship gave Raissa the idea, but I don’t think Victor is into that kind of a relationship.

My vacation is over, and I have to go back to the office.

Lanie is a great boss. She is, but she has a tendency of hiring on a bias. The office is filled with very attractive women and men. They are all young but they are also fully capable of doing the things thats needed to be done. I don’t have a say on who gets hire, but I’m starting to think she has some sort of evil plan or something.

“Oh, I just like looking at attractive people,” she said when I confronted her. She and I have a great working relationship, and it’s kind of like a sibling relationship, “what? Don’t you like looking at people with nice, plump asses and thick breast? I do. Don’t you dare tell HR that or I’ll fire everyone!”