College Freshman Adventures Part 1: Janis

I’ve always had a thing for legs. When I was around fourteen, I distinctly remember reading a copy of my dad’s Sports Illustrated Swimsuit Edition and gawking at the smooth, tanned legs of the woman on the cover; her body brightened by her orange swimsuit, her feet curling together in the foreground of the picture on the sand of the beach where she sat. She looked at you with the coy, jaded look women are meant to have in these photos. I wondered, at that time, if I would ever be this close to a stunning female’s legs in real life and if she would ever look at me like so.

Let’s fast-forward five years.

My buddy Jason and I sat on the porch outside a house party in November, watching the partygoers exit. We were drinking scotch on ice and I was numerous sheets to the wind. Jason burped. “I’m gonna flunk that test tomorrow,” he said. I watched the legs of the girls wandering outside. A few of them stumbled on the doorstep like drunken high-schoolers (which was basically what we still were, as freshmen ages 18 to 19), some of them were helped out by their equally smashed, wonky boyfriends (or guys who wished they were their boyfriends), and others exited smoothly and without any help, thank you. Many wore those tight black silk pants that is a continuing fad among the hip middle class female set. But a surprising number wore skirts—short skirts—although it was a cold night.

[F/M] Black Friday Deals

So over the summer I went to my very first gloryhole after a lot of hunting and loved it. I really wanted to go again but found that I didn't really have the time until my Thanksgiving break. Yesterday I was able to go back again for the first time and it was absolutely amazing.

Around noon of yesterday I had to make sure that my parents were fine with me being out for the night. I told them I'd be out with friends and at the latest I'd be home around three. They trust me so there was no issue and they said to be careful but that was about it. Flash forward to 9:00, I've already taken a shower, done my hair, my makeup, and gotten dressed. I tell my parents I'm leaving and head out. The hole is around 30 minutes away so I made a quick pit stop at CVS for some condoms and a bottle of water. I got back in my car and around twenty minutes later I was pared at the location and ready to go. I went through a quick mental checklist making sure to bring my phone, the bottle of water, and the condoms. I walked in and since I knew where I was going headed straight for the back. I walked into the booth, locked the door behind me and got settled in. I set all my things down and stripped naked putting my things on the small bench the ran along one wall. I sat and played with my pussy while I looked at my phone waiting for my first cock to appear.

[m/f] (pt2) Casually sexing Miss Vanilla

The second time I saw her, I knew it wasn't going to be wild. But I already had a room booked in L.A., to meet with this asian girl I'd been skyping with, who posted an ad in raomd. She cancelled at the last minute over "morality" issues, so I called Miss Vanilla because she lives nearby where I was staying.

[m/f] (pt1) Casually sexing Miss Vanilla

As the title states, I've been having some casual sex with a very "vanilla" type girl. She's sweet and nice, and way into having sex with me, but she's just not quite the kinky little freak that I am. Anyway… here's some stories that some of you might enjoy..

Our Jack and Rose Moment

One night after driving home from a date I pulled into my girlfriend's driveway to drop her off. I didn't plan on going inside as it was well after midnight and we were going to see each other the next day. However, we wanted to chat about the movie we saw so I shut the car off to chat. As we discussed the movie, both of us began to get a little chilly with the heat no longer running. Finally, she told me she was too cold and ready to go inside, leaning in for a goodnight kiss. As a total shot in the dark, maybe just to tease her, I said 'if you're so cold, let's heat things up' before leaning in to kiss her back. After the quick, innocent goodnight kiss she didn't pull away but just smirked at me. Neither of us were big dirty talkers, so we developed a habit of using subtle hints and body language to imply when we wanted it. I looked at the back seat and she said let's go.

My first time swinging: eating my favorite thing! [f/f, mentions of group]

Notes: This is probably rather mild compared to this subreddit's standard posts! Pretty normal lesbian sex lies within. Also, a little lengthy and not too graphic, but wanted to share nonetheless :)

This all began when I met my boyfriend's buddies for the first time. They are fantastic people, a delightful married couple in their 30s. My partner and I are twenty-somethings and horny as all hell. We have fantasies of all sorts, including cuckolding and the like. I have previously been in a lesbian relationship that lasted over a year and a half, so boobies are still something I like. When I met the wife of this couple, I saw a beautiful woman with a fantastic sense of humor, refreshing perspective, and, okay, massive titties and an ass that filled out some jeans so right. I was in polite company and couldn't fathom that this couple was into swinging, so I dropped the thought of getting my hands on those tits and went home.

Daddy(43m) Finally Catches Babygirl(23f) Part II

In Part I (https://www.reddit.com/r/gonewildstories/comments/3u153i/daddy43m_finally_catches_babygirl23f/) I introduced my new submissive, Sara and described our first face-to-face meeting. I will continue providing updates on the progress of her training in subsequent stories. At this point in time we are about two months in – so I have some catching up to do. The time between our first and second meeting was perhaps two weeks. Sara was having some reservations. It was unclear if it was genuine pangs of conscience or just fear of getting caught – probably both. One thing I have learned about training a sub who is in an otherwise committed relationship, you have to teach them to compartmentalize. You can't equate a Dom-sub relationship with something that is traditionally romantic. I hold no prospect of living together, falling in love, getting married, or otherwise sharing a life. Rather, we have one purpose which is to engage in training and teach her to submit and serve. Sure, there can be kindness, friendship, and small talk, but make no mistake it is a power relationship. Once the sub accepts this, and places our relationship in the proper context, then they find it easier to move forward. I never encourage them to break up, or abandon their significant other. Thus the next phase of Sara's training involved having her internalize these ideas. She continued to check in, follow rules, and one thing I noticed, is that she required very little correction. Sara learns fast and is an eager student. She enjoys turning our motel parking lot encounter over and over in her mind. It is clear she is hungry for the next lesson. As the day approaches for our second encounter, she is excited and wants to know the details of what I have planned. I never divulge too much, only saying we will begin to cover the rules and boundaries in more detail. Time permitting there may be some playtime, and I will introduce her to roleplay. Sara likes this and I have her read a few erotic stories to set the mood. She is a natural babygirl, and loves the idea of the taboo. In fact, I am not sure I have ever met a sub who enjoys discussing Daddy-Daughter roleplay as much as she does. Apparently it has been a dark fantasy of hers for several years, and she has never been able to share it with anyone. I wonder to myself what I have done to deserve such a gift – a young woman, with stunning looks, who is not only a natural submissive, but likes all the dirty kinky things I do. Sara does not appear to be aware of the power of her own sexuality, at least she doesn't flaunt it, or abuse it the way many sexy women do. There is a sort of sexual humility to her.

Finally, anal isn’t hurting anymore! [F/M]

I read this sub all the time and I have an amazing sex life, so I wanted to contribute something! I'm no writer though, so please keep that in mind.

I guess I'll start with descriptions and get that out of the way. I'm about 5'7" and pretty thin. I have small tits but I've always been told I have an incredible ass; it's pretty big and firm. My boyfriend is 6'3", with an incredible body. He's muscular and really cut.

So anyway, that's us. One ordinary day, we were sexting all day throughout work, so I was feeling really horny by the time I got home. He got off later than me, so I am home and super turned on playing with my clit. I decide to out on a sexy little g-string, a matching bra, and a pair of thigh high socks. I send him pics and tell him to come over and come straight to my room when he gets off.

My first experience with a transgendered woman (M/T)

It was a late night, I was 18 and very horny in my parent's house, and I was on craigslist looking to experiment a little. I've known for a while that I'm bisexual, but at the time I had only been with cisgender women before. I was trying to find a transwoman to mess around with and get to know, as I had developed a bit of a fetish for them.

I posted an ad, and after sifting through a lot of scammers and old guys, I connected with a very beautiful woman with an enormous cock. I was nervous because I assumed that her pictures were fake, but she agreed to come pick me up as she lived in the next town over. When she arrived, she was just as sexy as in the pictures, and she was very dominant. She was tall, with an hour glass frame, and long, straight blonde hair.

"Nice to meet you boy," she said in a very feminine voice, as she grabbed my ass and rubbed my cock in her car.
She then proceeded to guide my hand towards her cock, and I was amazed to feel that it was quite big even soft. As I started rubbing it, she began to get hard and it was evident that she was much larger than my modest 6.5 inches.

Initiating her in to our club [M/f/m]

This was back when I was 19 and in college. I had a best friend Jim, and we spent most of our time hanging out. One of us would get our hands on a bottle of booze, and we would stay up all night drinking and playing video games. Basically, your typical nerds. We knew we were geeks and we didn't really care; we were having the time of our lives in college staying up late, eating pizza three times a day, drinking lots of liquor, and trying to meet girls. We weren't so good at that last part, though. Both of us were virgins when we got to college and didn't really know much about flirting, dating, or sex. We both eventually met some understanding girls and got the first time out of the way, though. We also decided to make a "secret society" after reading about Skulls and Crossbones because we thought it was cool. We never wound up doing anything with it but for a while we thought it was really bad ass that we started a secret club, even if it only had two members and never did anything. Like I said, nerds. However, we had a few things going for us. For one, we were both in decent shape. We didn't work out or anything, but we were both tall and blessed with fast metabolisms so the pizza and laziness hadn't done any damage yet. We also both happened to be really good at talking to people. Jim had actually studied social engineering through a book or a website or something. So nerds, yes, but not your stereotypical "neckbeards".