After 17 long years, I lost my virginity [M/F]

After reading people’s posts here for years, I’m really excited to finally have a story of my own. Thanks!
(I omitted the times I accidently poked her in the asshole with my dick, it was awkward)

Guys, I recently achieved my boyhood dream, I lost my virginity. Not only that, but I was fortunate enough to lose it to my amazing girlfriend, who I will refer to as Amber. To describe her, she has a crooked smile, really cute cheeks (face and butt) and her breasts are perfect handfuls. Also she wears glasses. (She asked me to say they’re ray bands but they’re not) But I digress, the first time we did it, I was inside of her for 10 seconds, the fact I didn’t finish right then and there is a miracle. The reason it only lasted 10 seconds is due to a fear of getting caught. So yeah, that was how I lost my virginity. It was dorky but hey, I finally did it…

The End of Susan Brown [FFMM][snuff][bdsm]

When I first met Danna I never really had a chance. I was a young first year engineering student enjoying finally being free of the moral authority of a small town in Northern Ontario. She was my Calculus TA, daughter of a Toronto Dominitrix and heir to a small fortune from her dad (mom’s client), just giving lesbianism for a try before settling down. Perhaps because of her upbringing there was this sexual predator aura around her. I’ll tell you this, there wasn’t a single guy in the class who missed her tutorials.

I guess because I was the only girl in the class she took a notice of me, and placed me under her spell. I always knew I liked girls, but where I came from that unspeakable. I am not sure if I was lucky or cursed that as soon as I found a place where I could be free, I immediately found someone who could oppress me.

Best orgasm of my life!

I weote this on another board, but just found this place and thought it would be more appropriate here.

So the other night I was finally able to be home alone and was feeling incredibly horny. I recently heard about a site where you can go on, and your webcam would be connect with others. I never dared to do it before, but I dunno, the thought just really turned me on tonight. I made sure only my body and nothing else about me could be seen or noticed. Oh by the way, I’m a guy, pretty skinny, but pretty toned as well (to give you a picture). The ladies just haven’t been going my way lately and really wanted some human contact sexually.

So I’m on going through cams, cock in hand, not seeing very many women, when some guy writes me a message saying my technique could be better. I asked him what he meant and he started telling me to do things. Like rub my balls, switch up my stroking speed, get lube, just rub the head…..it went on and on for about 20 mins. By the time we got to the end, my cock was as hard as it has ever been, and I blasted so hard i actually let out a moan. It was one of the most incredible orgasms I ever had.

Had my first real [M/M/F] experience the other night and I’m still trying to process it.

So it’s been a while since I’ve posted here, but that doesn’t mean I haven’t been having fun. I just haven’t done anything that quite lives up to my previous stories. Until last weekend…

Before I begin, let me say two things. First, [in one of my previous posts](https://www.reddit.com/r/gonewildstories/comments/2int6y/fun_and_frustration_at_a_party_then_release_mfm/) I told the only MMF experience I’ve had. It was fun, but I’ve never really counted it as a threesome because we never really did anything as a trio. And two, I consider myself straight. It’s not that cocks or gay sex bothers me, it’s just that neither of them have ever turned me on. And I think that’s part of why this experience a couple of days ago has been so crazy for me.

Anyway, on to the story!

Daddy gives me a punishment. [Gay] [Mm] [bdsm] [Mdom] [oral] Daddy gives me a punishment.

It was a Friday afternoon in the summer. I had been invited over to my friend Riley’s house for the first time to stay the night. I headed over to his house around 3 PM. It was nice a nice and warm day and we went outside and walked to the park, hung out and came back around dark. When we came back his mother had made us dinner.

She had cooked some hamburger helper and had the table set. Me and Riley sat down and ate with her. We ate for probably about 30 minutes and then decided we would go play some Halo in the living room because that’s where the biggest TV in the house was. We played Halo until about 2 in the morning and then his mom walked in.

“Time to go to bed boys.” She said in a hushed voice. We complied and headed to Riley’s room where there was a bed big enough for 2 people to sleep. I laid down on the left side of the bed and then he got in the bed and turned the lights out.

My outfit got me laid! Yaaay! [f/m], or [m,m] (depending on perspective – explanation within)

http://i.imgur.com/a/DSTZp

He told me I look “super adorable” in this outfit and politely asked me to wear it to meet him. So I did, and… we had liftoff! Yay!

Confession for the sake of this story: I possess unusual anatomy. I’d rather not delve too into it, and you’re better off not thinking too hard about it, but suffice it to say I was raised male, most parts are male, and I usually (but increasingly don’t) present in my day-to-day life as male. Strictly physically speaking, however, I’m not quite one or the other, but the more I say, the more curious you’ll be, and I’m not taking pics. Sorry, but that’s not the point of this story. :)

I only bring it up because this dude was so cute about it. I told him from the beginning that I’m (mostly) biological male, and he was so wrapped up about “gay” insecurities , until I decided to open up to him about me a little more, and then all of a sudden his eyes lit up and he was suddenly all crazy about me again, because in his mind he was now justifiably fucking a girl. Obviously that was great because I was going to fuck him as a girl anyway, so it was nice that he loosened up and seemed to understand his role as penetrator. I suspect my choice of [panties](http://imgur.com/yF0PoKE) didn’t hurt him either. ?

Straight sex stupor. [MM] [M/uglyF/M]

I thought I was straight until I met Doug. The first time I looked him in the eye it seemed he was high on some wild drugs because his eyes looked so crazy blue, and as his gaze pierced through me I felt my cock start to twitch. He kinda had eyes like a pure-bred husky dog. Soon I realized he wasn’t high on anything; Doug was just very confident and relaxed, always in control, and crazy good looking. He was a pure-bred Bohemian from a Czech family that farmed close to a neighboring town. I was at a beer keg party when I first met him, and I was excited to find out he was fast becoming a friend of one of my regular party buddies, Richard.

Afternoon Run [M/GRP/GAY]

It was a bit of a blur how we ended up here or how, but after making eye contact during our run it was inevitable. Not surprising considering we happened to run into him again and he happened to follow us home. Not surprising given you could see my running shorts strain at the thought and as we three sat idle in the elevator his shorts were under the same strain.

All the same there we were with you lying below us. Your eyes locked on mine as he pulled my shorts down and I moved to free my legs. You reached to the side of the bed and pulled out massage oil and handed it to him along with a thin, ribbed, condom. As he dripped the oil onto my bare ass, you bit into the foil wrapper and handed him a freshly unraveled condom. Your hand helped him guide it on to this now throbbingly large dick.

A young boy discovers he is gay [MM]

A RIVER RUNS THROUGH ME

By: Peter Venlig

It was 1970, and I was in highschool when my body went through some funky hormonal changes that had me questioning whether I was sane. I was a good kid; I got along well with my family, and I had a group of friends that I loved to hang out with, but I always felt awkward like something was missing. I needed some excitement in my life, but I didn’t know where to find it. Then a new kid came to our school, and I caught him looking my way a lot. That was when my life changed in ways I could never imagine.

Jimmy was 2 years older than me, and his family moved to our little town after giving up the city life. Jim was immediately popular with all the cool kids just because he was from somewhere else, but it didn’t take long before he got friendly with my dorky crowd instead. He obviously didn’t think being cool was all that much fun. Soon we became friends, and he often came looking for me between classes. It was always a thrill to see him because I thought he was incredibly good looking with his bright smile, and he always made me laugh.