All right everyone, let me tell you about the time I lost my anal virginity. This happened just over 24 hours ago with my [22/F] boyfriend [29/M] of a few months. For some background, he has had anal sex before but I hadn’t ever – only some light anal play, maybe a finger on occasion, that sort of thing. For some of the cute background on our relationship because I’m sappy and have an emotional approach towards sex, we’ve both said one of the main things that attracted us to the other is that we’re both equally goofy and silly. We joke around a lot and have a lot of fun teasing each other. I have a tendency to be a tad bit high strung while he’s very mellow, so we balance each other out nicely. All in all, he’s fantastic and last night only proved this more.
Tag: Anal
Seconds, please?[M]
Out for lunch walking to our destination.
I can’t help myself but to playfully grab and lightly slap at your ass.
You tell me to stop but your facial expression says otherwise.
As we seat for lunch I place my hand in your thigh softly rubbing my fingertips up and down your inner thigh, grazing your pussy each time.
I can tell you’re starting to get horny the longer I do it time after time again.
You tell me that we are leaving in a stern voice “going back to yours now” you murmur just at an audible volume.
We head to the car, you don’t hesitate to throw your hand into my pants grasping at my dick fondling as I become harder from the recent attention.
Before you start the car you let go of me and undo my jeans and pull out my stiff, hard cock me continue to fondle me, this time with an in time up down stroking.
Before long we arrive at my house cock still in hand.
I pull from your hand to put myself away as we head inside, heading straight for the bedroom.
The moment we hit the boundary of the room we collide like a magnet to a fridge, roughing each other up as we strip the other while exchanging deep kisses.
[M]y Girl [F]riend? Or her best [F]riend? Part 4 [Conclusion] [LONG] [Threesome]
[Part 1] (https://www.reddit.com/r/gonewildstories/comments/64ny5f/my_girl_friend_or_her_best_friend_decisions/)
[Part 2] (https://www.reddit.com/r/gonewildstories/comments/66fvi7/my_girl_friend_or_her_best_friend_part_2/)
[Part 3] (https://www.reddit.com/r/gonewildstories/comments/66t57l/my_girl_friend_or_her_best_friend_part_3/)
So lets fast forward a few weeks. Liz and I were still dating and she was getting more daring sexually on every date. Jacqueline and I had stepped up our game and began having sex on an every day basis either before or after school. Ever since I had found out Jacqueline’s secret, I had been dropping subtle hints to Liz about possibly having a threesome, or even just trying new things. She had never gone this far sexually with anyone so she was timid about things, but at the same time, she was hungry for more of the things she liked. One evening, Liz and I were on a date. We went out to eat, and Jacqueline “happened” to be there. Liz immediately asked Jacqueline to join us. Little did Liz know, it had been planned for a week. The whole time during dinner, Jacqueline kept talking about how sad she was about breaking up with her last boyfriend and even made a comment about possibly wanting to see what dating a woman was like. Liz laughed a bit, but didn’t react negatively to the comment. I had snuck in some whiskey to mix with our drinks. Liz accepted and after a glass of whiskey and coke, she was being very flirtatious and handsy with me. Jacqueline and I knew we were on the right track. A couple more drinks in Liz and we could bring up the idea.
An unusual end to my Friday night [MF]
I lurk on reddit, and I’m kind of in a relationship so this is a throwaway and I have regrets about what happened. It was unusual and not at all like me, so I feel like writing about it. The alcohol content was high, so some of the details are hazy for me.
This started on Friday night at a cheesy club night in London (if you are local then you might be able to guess where I’m talking about). The kind of place where the crowd is a bit older (I’m 30) and we “ironically” sing along and wallow in nostalgia. I very rarely go clubbing now but was with 3 male friends (and one of their wives), had had quite a lot to drink and was generally having a good time. The place was busy, we were up at the front and strutting our stuff. At one point we started dancing with a group of three girls, took a selfie with them and I jokingly called them our groupies.
[MF] [MMF] [Cheating wife] turns me into her husbands bicurious use
I had met Tim and Sammy through work. Tim was a few years younger than me, athletic, and full of self confidence. Sammy was his slightly younger wife. She was Filipino and had an alluring body and face. I had a reputation for sleeping with people’s wives at works that was, well, deserved. Sammy found out about the reputation through some of the other spouses.
It was not shocking really when she messaged me on FB one night. Her hubs was at work and I had the night off. Her boredom was apparent in how she was talking as we kept messaging. I was a bit tanked so me leaving my place was a no go. I got tired of her round about suggestive messages so point blank asked her if she wanted to come over and have some fun. She agreed. I was stoked. Then got to wondering as I waited for her to drive over why she was ‘bored’. Her hubs was a good looking guy. They seemed lovey dovey whenever we were hanging out outside of work as a group.
My [F]irst Experience, Part Three
I do seem to be committed to explaining how I went from late-blooming “never-been-kissed” to, well, been-kissed-and-then-some but still a virgin, and some people have enjoyed [part one]( https://www.reddit.com/r/gonewildstories/comments/643txs/my_first_experience/) and [part two](https://www.reddit.com/r/gonewildstories/comments/65kugl/my_first_experience_part_two/). So I suppose I should, to the extent that tales are ever complete, tell the end of this one.
I set out to write this as one story: some background and then a single particularly memorable event. That became cumbersomely long, however, and perhaps the background itself is interesting as an exploration, and so this has become two stories, the next to be posted later.
As I said last time, at first I was slightly-reluctantly dragged along into sexual experimentation with Gordon, but the incorporation of ejaculatory delights in to the scheme changed my attitude toward that. And so once I was giving Gordon handjobs on a regular basis, it would be pointlessly restrictive for him to keep his pants on but his penis exposed, so usually his pants came off. And so although there’d been a rule that my top could come off but not my jeans, well, that just left me overdressed, right? I doubt that was actually my logic, but somewhere along the line (I actually don’t remember how or when) I became willing to be naked with him.
[M]y Girl [F]riend? Or her best [F]riend? Part 3
[Part 1] (https://www.reddit.com/r/gonewildstories/comments/64ny5f/my_girl_friend_or_her_best_friend_decisions/)
[Part 2] (https://www.reddit.com/r/gonewildstories/comments/66fvi7/my_girl_friend_or_her_best_friend_part_2/)
The next morning, I got ready for school totally anticipating the surprise Jacqueline had to tell me. We all went to a private school so I was typically dressed in slacks and a polo shirt, and the girls usually wore skirts with polos. I pulled on my uniform faster than normal, grabbed my bag and left 30 minutes earlier than usual. My parents had already left for work so I didn’t even have to come up with an excuse for leaving so early. I hopped in my truck and headed on down to the park near school.
I remember it was gloomy overhead as I pulled up, the spring rain was constantly rolling in. Jacqueline was already there waiting for me. I climbed down from my truck just as it started to sprinkle. I got into the passenger seat of Jacqueline’s car and she immediately gave me a kiss and hug. She told me she missed me so much and that she couldn’t wait to see me. I kissed her back but felt strange that she was so happy to see me knowing that the day before I licked and fingered the hell out of her best friend. She could tell I was perplexed and ran with it. Instead of jumping right in to telling me her secret, she started small talk. She asked about my classes and homework, my truck… I couldn’t handle it. Finally I cut her off, and flat out asked her what her big secret was. She smirked at me with a devilish grin.
First Time in a Gay Bar [MT][anal][exh]
Looking for feedback, hoping the fine folks at Erotica can let me know if I’ve struck a good balance between story and fap material. Language selections were made with a male audience in mind but I’d love to hear your thoughts.
And, of course, descriptive accounts of how this story made you feel and what you did about it are always welcome!
—-
I did consider myself a straight guy once. I dated women, enjoyed the sex, and didn’t feel like there was anything missing.
But still, every once in awhile I’d wonder what it was like to be with another man. Pretty soon, that idle curiosity became something more… But in the town I was from, you just didn’t admit to that kind of thinking. One of my long time friends, Bobby, had actually moved away shortly after “coming out of the closet” because people were so weird about it around here. It was only after he’d moved that I kind of thought it would have been interesting to experiment those few times he’d made passes at me, rather than just politely turning him down.
[FM] First time anal with me on top.
My Reddit man makes me crazy in a way I’ve never been. I do what he says in bed without questioning, and I like it.
He was working out of town last week, so I flew to meet him. We had wonderful, crazy sex at night and he left for work the next day. I lounged by the hotel pool and had a spa day. I was relaxed and ready to see him.
I got the simple text “I’ll be back to the room in twenty minutes” and began to scramble. I showered and put on my thigh length black socks, his favorite, and nothing else. When he opened the door I stood there smiling.
We hugged and kissed as he backed me to the edge of the bed. He pushed my thighs to my chest and ran his tongue along the tender skin inside my thighs.
I was already wet and prepared for him to lick my pussy when I felt his hands grip my thighs. He dipped his head lower and began to lick my asshole. My head spun and I grabbed the back of his head, pulling him tighter.
First Time in a Gay Bar [MT][exh] (long)
I did consider myself a straight guy once. I dated women, enjoyed the sex, and didn’t feel like there was anything missing.
But still, every once in awhile I’d wonder what it was like to be with another man. Pretty soon, that idle curiosity became something more… But in the town I was from, you just didn’t admit to that kind of thinking. One of my long time friends, Bobby, had actually moved away shortly after “coming out of the closet” because people were so weird about it around here. It was only after he’d moved that I kind of thought it would have been interesting to experiment those few times he’d made passes at me, rather than just politely turning him down.
The real tipping point I think came one night when my computer died and I had a huge project due. I begged a friend to borrow his laptop, took it home, and got to work. I finished late that night, and figured I’d have myself a good fap before bed.