Category: gonewildstories

That time I [M] gave one of my best friends [F] her first orgasm ever! :)

For some backstory: me and a friend of mine met in college when I was 19 and we’ve been close ever since. About two or three months after we met she invited me to her apartment and we ended up making out and eventually having sex three times before the night was over. Her roommate probably wasn’t pleased lol.

Anyway, the next time I was over at hers she confided in me that she’d never had an orgasm. She said that sex and masturbation always felt amazing to her, but she’d never experienced the explosive “wow” feeling, that bursting release of pleasure that everyone talked about. In fact, she’d only ever felt a “buildup,” (what she called the mounting sensation she felt was rushing towards…something) once with an one night stand and once when she was fingering herself. She didn’t want us to focus on it when we had sex, but wanted to be honest. So for years we’ve had a good friendship, great sex, and a fun time learning each other’s likes, dislikes, kinks, and everything else. But as much as we’ve grown and experimented, both with each other and with other people, she still never had an orgasm. Read more »

[M]y [F]irst Affair – She blew me again, this time husband was eating breakfast upstairs

After the daring episode with the phone, dinner at their house that night was fairly uneventful. She had changed into suburban mom wear for dinner with the family, a mid-length skirt and matching blouse. But several times through the evening, when the rest of the family was out of eyesight, she would flash me, either spreading her legs open while sitting across from me, or once pulling the waistband of her skirt down to show me the ‘whale tail’ of the thong I had picked out for her while we were shopping. She knew the effect she was having on me and was having a great time teasing me, knowing there was nothing I could do about it.

Finally dinner was over and the three of us moved to the outside patio while the kids went to their rooms for the night. Michael (her husband) had had several beers during dinner, and now was pounding them down even faster, either through discomfort or in order to show he was the man of the house. In either case, he became louder and more belligerent, and began to berate her for trivial things about dinner as well as other pre-existing issues. She kept trying to mollify him, playing up to his ego, finally sitting on his lap in front of me, to ‘show me’ how manly and powerful he was. Of course, as she did so, to talk to me she had to turn away from him, and she would roll her eyes or make suggestive faces to me, even licking her lips, while he couldn’t see. Read more »

A league of her own – how I [M] started this long affair with an instagram model [F]

This happened six years ago, when I was installing some hardware project for a business. It was a huge project, a new building for an IT business, and they decided to hire me as a consultant. It took about 3 months to plan it, with a ton of back and forth, and I had to travel several times to a different city.

She was always present in the meetings – I wasn’t sure what exactly was her role, until I understood that she was the boss’ pet. She never said much during the meetings – from time to time she asked some questions, never out of place, but my feeling was that she was in these meetings mostly to learn or to make sure that things don’t go out of plan. We had a few discussions – I think that it took a month of weekly meetings to actually talk to each other, at the coffee machine, while waiting for the coffee to get made. Her name was Anna (let’s say) and she was indeed beautiful. The sort that takes your breath away when you’re in your 20s. The sort that steals you from your wife with just a „hello”. Baby blue eyes, strawberry blonde, perfect skin, and definitely one that visited the gym often. Read more »

[MF] how an accident became a blessing

After a little while of me and my ex dating we obviously found out about what gets us going and what doesn’t in the bedroom. One of the things on her list of no no’s was anal. As I stated in my last post with another ex, I’m an ass man so needless to say I was wounded by this haha. I tried to talk her into it but she was not interested, so i decide to respect that. I never questioned her about it again and basically in my head i set it in stone that it was never gonna happen.
One particular afternoon we had a free day and we both decided to have a date night, nothing special, just go out to have a meal and a few drinks then head home and do what we were doing all morning and afternoon, watch tv. Everything went great we got home and we kissed once we took our coats and shoes off. Her kiss wanted much more and I could tell by the way she kissed me. It was a really soft but well pressed kiss which lasted longer than a normal kiss should, so I did the same thing. Within a minute we were taking our clothes off, she was undoing my trousers and put her hand on my cock and started stroking me. I on the other hand was kissing her neck and down on to her boobs.
We headed for the living room and I moved her towards the arm off the chair, grabbed her hair, scrunched it up and made her bend over the arm with her ass nicely presented and told her sternly to part her legs, she did so with this amazing smile. I scrunched her hair tighter which made her moan and middle and ring finger on her pussy rubbing up and down slowly. She was incredibly wet. I didn’t put my fingers in like she thought i would and instead went straight for it. In one smooth thrusting motion my cock was inside her which made her gasp and moan but not loudly…more in surprise and relief, she wanted to skip the foreplay as much as i did.
After a few minutes of pounding her on the arm of the chair I had her lay on the sofa on her front. I love this position. I can kneel and fuck her, grabbing as much ass as i want or i can also lay myself on top of her and wrap my whole arm around her neck and maybe nibble on her ear which she loves or moan into her ear which she also loves, win win for me.
I chose the second way, body on top and arm around her neck. This is where the accident came in. I was on top but my cock wasn’t inside her, I was grinding it between her ass cheeks. As I took my cock in my hand ready to guide it into her pussy I misjudged ort maybe it was the alcohol but i guided it straight in her ass. She yelped and tensed up but wasn’t in too much pain. I realised she couldn’t move to push me out because my weight was on her, she had nowhere to go.
I didn’t want to move out of fear of hurting her so i said i was gonna pull out slowly. Now this is what she said which is probably the most incredible thing I’ve heard just because of the shock of realising what she said. “no don’t, just fuck me slowly”. Yep. The surprise on my face must of been a picture because she moved her head which was still locked in my arm, looked at me and laughed a little at my surprise. She put her head back which i took as the signal to do what I have wanted for so long and slowly fucked her ass. She winced at the pain while simultaneously moaning in pleasure. We stayed in this position fucking. She managed to loosen up after a few minutes and she told me to go faster.
I was getting close after what felt like an eternity and she could tell. My grunts were getting louder and my grip around her neck got tighter. Barely able to make a breath she choked out “cum in me ” and i did. I loosened my arm and took it from her neck. I was still on her with my cock in her ass twitching, to which she cheekily started tensing her ass and smiling and laughing at me while i moaned from how tender and sensitive my cock felt. We had a chuckle, i asked her “what the fuck just happened” she replied “my ass fuck just happened. We talked and lay there for a while and she said it was the most intense orgasm she has ever had. Same goes for me. Nothing since then has made me feel that good. The blessing was she was wanting anal from that night on.
As always my dm’s are open for conversations and questions. Thank you for reading.

2nd date with 26[F] and 36[M]. Hot stuff

2nd Date:
This is about a week after our first date. We’ve made last minute plans to hang out. I get to his place and I forgot how cute he is. I get all shy again. He gives me a huge hug and kiss on the cheek and we go up to his place. When I’m around him, I don’t get embarrassed by my body or anything. We sit on his carpet and he can’t keep his hands off me. He’s touching my legs and caressing my face. We move to go in his bed. (Still no furniture). We are laying on his bed and he begins to kiss me. He’s not wasting any time. We were supposed to watch our show but he has other plans. He moves on top of me. His kisses are fucking amazing and he gives lots of attention to the neck. He takes off my shirt and pulls down my bralette and begins to give lot of attention to my tits. He again says it’s getting too hot and takes off his shirt. He goes back to sucking, licking, and blowing my tits. He also grabs both tits and squeezes them together starts sucking each so fast. He pushes my tits together and motorboats them. I’m getting so wet. When he finishes with my tits. He asks if he can lay back. I nod. He takes of his shorts and lays back on the headrest and asks me to lay between his legs. Read more »

[M]y first time handling a cock [M] was in front of my best friends wife [F]

So you can say that I have an… interesting relationship with my best friend. We didn’t wear a lot of clothes when we were roommates in college, we would get handsy with each other’s girlfriends (consensually of course, they were into it) and fucked in front of each other on occasion. After college he went into the the military, and moved away with his fiancée.
I had the opportunity to visit them at his various posting a few times as I’d travel for work quite a bit, and sometimes I’d find myself close by. I had a meeting about an hour away from where he was stationed, so I drove down for an evening with them. We were drinking pretty heavily on their couch, and the three of us started stripping down (as would often happen.)
Before we knew it, we were all pretty drunk, and very naked. I was sitting in the Mideast of the couch, between the two of them.
“You know” I drunkenly philosophized to my friend, “I Jack off all the time, but I have no idea how other people do it. Do I do it normally? Am I weird? I have no idea!”
My friend started stroking his cock right next to me. “This is how I usually do it, with my left hand and I give it a little twist.” He went from soft to fully erect VERY quickly. He is also rather well endowed. I’ve seen his cock more times than I can count, but only erect a time or two. And never up close like this.
“Huh. I just go straight up and down, like this.” I showed off my fairly normal technique, and pretty soon we were both jerking off next to each other while his wife laughed at the ridiculousness of the situation. She rolled her eyes and excused herself to go pee. “Guys are so obsessed with their dicks.”
As soon as she left the room, he reached over and started stroking my cock with that twisty motion he was showing off earlier.
“Whoa, what are you doing?” I asked with shock.
“Just playing with your dick. No big deal.”
I’ve had plenty of handjobs before, but never from another dude. And he knew exactly what he was doing. It was awesome. He must have felt my cock pulsing because he said to me “don’t cum.”
Do I told him to slow down, and I calmed down a little, and he continued to stroke my cock with that weird twisty motion that felt so good. “I said don’t cum. Yet.”
“Then knock it off for a second.” It was my turn to stroke his dick. I had only handled my own cock before, and I was shocked by how soft it was. His penis was much larger than mine, but mine was at least harder.
“Remember don’t cum yet”
We were stroking each other dicks still when his wife came back into the room.
“What are you doing?” She asked with visible confusion on her face.
“Just playing around. If it’s weird, just tell us to stop.”
“Do what you want.” She said with shrug. Her naked form sat back down next to us. I reached out at caressed her breasts while her husband stroked my cock.
“Now it’s getting weird. Put those away.” Read more »

[M]y g[F] public exposure ideas

26 [M4R] gf public exposure ideas

Hi there. Looking for ideas on how to show off my gf. I know the obvious sending pictures but ideas in the past have been setting my phone on the counter with a nude displayed so the guy at the counter can get a look. Have my gf flash a truck driver. Changing room with the door open. Etc. we’re trying to find more ideas like that to expose her another man. She’s 23 and quite sexy. Message me with your ideas!

Also really looking for ideas on how to show off pics to strangers in person! Like showing a random guy. Leaving my phone out. Etc

I [M] fucked a cop with the most perfect boobs in her bikini

Years ago, I met a woman on a dating website and we clicked almost immediately. And when she started sending pictures – clean ones at this point – I couldn’t believe me eyes. She had an incredible figure. Like hourglass perfect.

Then came the NSFW pictures. Her boobs were absolutely perfect. Probably still the best I’ve ever seen. Full, round, big, perky. I’m getting hard again just writing this.

We got dirty pretty quickly and we talked about meeting at a wedding she was going to so we could fuck in the pasture next to it but it didn’t work out.

Finally, around Memorial Day Weekend that year, we made plans. I was coming back from a weekend out of town and she was at a pool all day. She showed up at my door in a black string bikini and a coverup with a hat on. She wasn’t made up and smelled like sunscreen and rum but, fuck, she was sexy.

It took us about four seconds to start making out and we ended up knocking
Into every wall en route to my bed. I got her on all fours and pulled her luscious tits out and began playing with them from behind her back. Read more »

Once upon in Enfield Conn [FMF], the conclusion.

Pretty exhusted, like held the second girl in my arms. I had just closed my eyes when the room telephone rang. It was my wake up call. I moved as fast as I could to answer it before it rang again.

My quick movement had awoken the girl was with. I took her hand and head to shower. For some reason I locked the bathroom door. We washed each other. She paid special attention to my dick and it rose to the challenge. Soon she had her legs wrapped around my hips. As hot water slashed against my chest then on to nipples I maneuvered to enter her. She slid downward as I pushed upwards. I was barely inside of her when she grabbed me tight, she shivered throwing her body into spasms when she came. I trust upward often and hard trying to extend her pleasure.

We were still fucking when the pther girl began banging on the door, yelling ” What’s going on in there “. She continued banging and yelling and we continued fucking. Until the girl in the shower came 3 times and I busted my load deep inside her.We cleaned up. Read more »

My [F] First CNC experience

A few summers ago, when I was 25, I was really struggling with a fantasy of mine and how to play it out, and honestly if I wanted to play it out at all. I was talking to this guy online for a while, we were sharing fantasies, experiences, and honestly just having some decent conversation. He was in his early 40s, married, quite handsome, and fun to talk to. At the start of our conversation, I found that he traveled often for work, and would love to meet up with me at some point. I welcomed the possibility in the future.

One night we were talking about some pretty deep shit, past sexual abuse, and how I felt about it. I told him things I never told anyone before. I actually came to a few realizations as I talked to him. I’m not going to get into it all, but in a nutshell, we came out of the conversation with me yearning for something I struggled with in the past.

He told me he could make it happen. Safely. Read more »