From the court to the couch [MM]

I recently became a member of a local gym and started playing in a weekly basketball group. Lots of older guys but fairly competitive. After a few weeks I had gotten to know most of the guys pretty well. Most were there just to get some cardio in every week. I was the same.

This past week I went at the usual time but there weren’t enough to play so myself and a stranger just spent the time practicing. When that was over we both headed to the showers to get ready for work. He is an older black guy, 48, tall and in really good shape considering his age. The real bonus is that he is a lawyer and is very well put together. Being my typical self I made sure to check to see what he was working with and I was pleasantly surprised at how clean he kept his manscaping.

We finished showering and headed to work. It wasn’t until after he had left and I was packing my bag that I saw he left me a note. Very simple, saying he had a good time and would like it if I text him sometime. I didn’t get a gay vibe out of him so I was cautiously optimistic. Most straight men wouldn’t leave a note. I text him within minutes of getting in my car.

[FM] I (31F) pegged a beautiful young Airman (20M) after we took turns on my sybian

Napsturbate

God bless the motherfucking Air Force. I’d been killing my entire day off alternating between riding my knock-off Sybian and napping- a 20 year old Airman on Tinder hits me up and wants to spend some quality time with me. I told him I was busy napping. He asks to join, and I clarify I’m actually interested in said napping activity- after 30, those naps become increasingly valuable. I’m not saying I wouldn’t cum on his face when I woke up, but god damn it I was exhausted after another successful ride and I need a power-nap to go round 4, 5, 82- whatever. He says that’s fine, he’d like to nap with me. Yeah yeah, I know how this goes- you’re gonna crawl into my bed and those wandering hands are just going to oops their way into my naughty bits. I’ve already prepared my litany of No’s leading to the inevitable GTFO. Whatever, come test my patience adorable baby-faced man. Now that I’ve lost 50lbs I might just fuckin’ eat you– I’m hangry. The drive from base to my house is a solid 30 minutes so I dozed back off by the time I hear the knock on my door.

[M]y first time anal experience with toy [Elaborated]

[Short version](https://www.reddit.com/r/gonewildstories/comments/617lby/my_first_time_anal_experience_with_toy_short/)

I [24M] bought my first anal toy few months ago, it is a wired vibrating prostate massager, it is beginner type, about an inch in diameter at its thickest part & insertable length is about 4 inches. While the toy is on its way of shipping, I decided to try using my finger using glove, it is my first time insert something into, TBH, I feel gross, it didn’t end up good, my penis became flaccid right away & I didn’t masturbate for more than a week until the toy is delivered.

When the toy finally arrived, I can’t wait to play with it, I didn’t pick the color, it send out randomly out of 3 colors, I am good with all 3 colors, but I didn’t expecting a [pink](https://www.reddit.com/r/SexToysCollection/comments/5us7j1/my_humble_collection/) one sent to me, it is so hot, turn me on right away. I didn’t use the toy right away, instead I waited until weekend (still didn’t masturbate since last time, 1 week+). I already read something about prostate orgasm from /r/prostateplay before I decided want to explore anal, that is mainly why I got into anal play & my first anal toy. Watched some anal genre porn & browse some photos subreddit, my favorite one being /r/buttplug, prepare myself into the mood. The mood is very important, I don’t want to end up like last time.

[M]y first time anal experience with toy [Short]

If you never have any backdoor experience, the first time is incredible, at least for me. I start cumming involuntarily once I have the prostate massager first inserted, and I haven’t turn on the vibration yet. The load is huge and long, it just keep slowly dripping out and I can’t control it. This is my longest orgasm yet, it is a whole body experience, my mind is like frozen/paused for a while, and my whole body muscle is like shaken & exhausted. Also I never experience any refactory period after that, I am still in harden state and horny mood, I jerk off right away by stimulating my penis, this time the small load shoot out further rather than dripping out. The deep breathe after that is like I have taken a intense exercise session.

Reese Becomes P.C.; [mT][huml][sissy][anal][gang][buk][inc][prost][exh][mast][Tdom][Msub]

It’s an excellent Sunday morning for a cum shower. A good day to get down on your knees for Sky Daddy, and let him rain his love down all over you~
Fuck, my mouth is watering now… Anyway, I hope you enjoy.

-Starla

****

My name is Reese [redacted], and I am a student at [redacted] High. I’m writing to you, today, because I fucked up, and immediately after fucking up, the world decided to fuck me over on top of it.

See, this city used to be a good, wholesome place. There were no queers, or lgbts; everyone did it the right way by waiting until they were 19 to get married, and then having children during college. We all loved Jesus, voted Republican, and knew deep down that Obama was a Muslim.

Everything changed when we got our first tranny student. He was a nasty boy named Pete (he wants us to call him Shannon, now), who started wearing eyeliner one day, and it seemed like the next, he came in wearing all women’s clothes and makeup. He even had his hair done up, too. I say he was nasty because we used to hang out a lot. He wasn’t my best friend, or anything, but we were in Scouts together, and we’ve slept in tents together before, and he didn’t tell me.

My Weekend in Philadelphia Pt II [MF] [Bondage] [Femdom]

I was under the impression a blindfold was simply deployed to steal my vision and keep me on edge, to anticipate what was coming next, or where Miss Janet was in regards to me, or what toys she had at her disposal. It did all of that, of course, but it absolutely heightened my senses elsewhere with my sight gone.

They bit hungrily, craving the thin flesh of my hard cock and bound balls. All told, Miss Janet informed me that she placed 18 total clothespins on my head, shaft and balls. Her praise kept me focused, not wanting to complain verbally or groan in anguish.

She flicked the clothespins with her forefinger and giggled when I would moan or try to wiggle my cock and balls away from her strikes. The second I settled into a pain on one specific pin, another would get flicked or pulled. I didn’t care to use either safeword, even with the current pain, I feared it might get worse. Still, as if Miss Janet could read my mind, when something really started to burn, she would place a vibrator of some sort on my adorned cock and make me forget all about the decorations.

[MF] Wife keeps me awake for just a little longer… she wanted to play!

About a week ago, my wife and I were getting ready to go to bed. As we laid down, I was very tired but it was clear that she was not. She tried talking to me, nudging me and everything else but I was really ready for sleep.

She stopped, got real quiet and said “I bet you’d turn over for a blowjob…”.

I thought about it, and I guess I wasn’t that tired and rolled over. She smirked at me and began to tie her hair up into a bun. Then, she got on top of me and started to grind. She was really rubbing her pussy up and down on my cock, which was getting harder by the second. I could feel the wetness starting to coat her panties. She took them off and let me feel, and she was already getting real wet. She made her way down and kisses my cock as she took it out of my underwear. Finally, she took it into her mouth and began to blow me. Looking up, she took my cock out of her mouth and stroked it while she sucked my balls.

How A Game of Call Of Duty And A Bet Cause Me My Virginity [MM] [First Time] ‘NSFW’

I’m going to start this story by saying I apologize ahead of time for my grammar and writing errors this is my first time ever writing a story and my first time posting on here so I hope you enjoy my story and please bear with me the story may start out slow but it will get interesting. Everybody names has been changed in this story for privacy reason and everything in this story is true.
I’m Apologize for the long post as well.

First a little description of me. I’m Ciel, 20 years old, 5’10, Asian, Bisexual, Black Hair, between 190lbs-200lbs so I’m not fat but at the same time I’m not skinny so I guess you can say I’m Slim (Currently working on losing more weight and trying to get a 6 pack), Sophomore in College, Goth/Alternative Style (I had snake eyes tongue piercings and a smiley piercing but they fell out so now all I have now is a septum nose piercing…I’m thinking of getting more I just don’t know yet).

This Description is about…..We’ll call him “D”, So “D” is 19 years old, 5’8, He considers himself “Straight” but deep down I think he’s Bisexual…I don’t know, Black, between 170lbs-180lbs, Slim but muscular with a 6 pack, 2 tattoos.

[MF] Wife and I get into Anal for the first time… with explosive results!

I just wanted to say thanks for reading my stories everybody! Always seems to get a good response here so, I wanted to post one of my more… interesting stories. This story is about anal on me so, if you aren’t into anal on men then you might want to move along.

———————–

One night, my wife and I were talking sexual taboos. We were discussing what we think is things that would be “weird” to most people but something that we would like to try. I finally built up the courage to tell her that I want to maybe try anal on me. I have always been a bit curious but, now I wanted to try it for real. She told me that she loves me and that if it’s something that I want to try, she would help me. That night, while we were having sex, she brought it up again and I told her I wanted to try it. So, she stopped and made me sit on the bed. She pulled her hair back and began to slowly give me a blowjob. She was sucking it full force when she slowly began to message my thigh area. It felt good and the blowjob was pretty intense so I didn’t stop her. Before long, she began to move her hand closer and closer to my asshole. I pulled back a bit at first, just shocked that my wife’s hand was down near my hole, but that it just felt… different. She told me to relax and that she wasn’t going to go any more than what I wanted. Then, she continued to blow me and slowly rub a finger around my asshole. The feeling was amazing and really describable to somebody who hasn’t had it done to them. She rubbed it along with my taint and blew me until I came right in her mouth.

[MFFF] Sex Cruise pt 2B [long] [group] [pegging] [anal]

[sex cruise pt 2a](https://www.reddit.com/r/gonewildstories/comments/5tyl6t/mfff_sex_cruise_pt_2a_long_group/)

Basking in the glow of having just fucked Katie and watching Jenny get fucked by Gabriella, I didn’t think things could get hotter. That was when I remembered Gabby’s hand on my ass and the promise she had made. She reminded me that she hadn’t cum yet and neither had I. As we looked at Jenny and Katie embracing and kissing, I could feel Gabby start massaging my left butt cheek. I turned to her and she had the sexiest grin on her face. This was the first time I really took in Gabby’s looks. She was gorgeous. Full sexy lips, dark brown eyes, nice pert breasts, flat stomach, muscular legs and ass. She was a sexy dominant woman. The type you take home and let her choke you a little bit just so she would take charge.