Tag: Anal

Oh John! [anal, Gay, Best Friends] First Post

This is how I remember the events that evening. We had too much drinks and started to talk about sex. Me, John and 4 or 5 other guys talked for what seemed a long time. I made some stories up but admitted I was a virgin. John surprised me by saying the same and Paul too. That made me happy – I wasn't the only one.

I kept listening to those guys barging about banging some girls imagining me instead – those small shorts showing off hot hairy muscled legs, those strong arms… all that time I was hiding my bonner.

Eventually we went to bed. We were enjoying holidays at Paul’s beach house – no parents allowed. Three rooms – a large one for Paul, Richard was sleeping on the living room, Joshua (?) and Matt were sharing a bed and me and John another one. Old friends, old habits.

John brought some bears to the bedroom – “hey wanna talk some more?”

“Sure!” I was fucking drunk to say no.

Let me introduce you to John (or just skip this part if you’re horny). Read more »

(M)aking of a Hotwi(f)e

Preface: My wife and I have discussed her being with another man. I don’t see this as cheating. We did have some ground rules, no getting attached, no anal (her tight ass is mine). We have since made more rules, but this was our first experience (and when I say our, I mean her). It’s also worthy of noting we married young and we were early to mid-20s when this happened.

So it was my birthday. It all started out with a friends and family get together at a private function center, the manager of the function center is a close friend (whom we will call David). I had a fair bit to drink. The night itself was pretty normal for a night out (the girls didn't come out after the function center), with the exception of our last port of call was a strip joint. Nothing overly excited happened at the strip joint, just the normal ogling.

In the Early AM I called the wife, asked if she was up, and if she’d come pick me up and give me a lift home (and drop a few of the boys off on the way) – she did, what a good wife. Read more »

Late-night Tinder meetup [m/f]

I was rebounding from a recent breakup so had been meeting up with guys on Tinder. Although I don't mind casual sex, I enjoy flirting and intelligent conversation over a drink beforehand and tend to be drawn to other well-educated, clean-cut types even on dating apps.

Jack and I had been messaging most of the day on Thursday and I could tell he was forward and assertive — traits I hoped would carry over into the bedroom. Although both of us had evening plans, I encouraged him to stop by my apartment around midnight once he was free.

When he knocked on the door, I wasn't immediately attracted to him — he had a little more of a beer belly than I would have liked, whereas I am very fit. I'm petite, a size 2 with 32Cs but a round, perky ass that barely fits into my jeans. I tend to like guys who are bit more ripped, but J. immediately made eye contact with me and I could tell he was experienced with women (and in bed). Read more »

My (25f) tinder date (pictures)

I live on the east coast and work in Software marketing. I am very attractive and dated half a dozen guys so far. I have 36C breasts and 35 ass. I am currently seeing a guy for one month but we are not serious yet.

I have used tinder but never met a guy. I visited California on a work visit last week. I met a couple of friends from college whom I usually meet during my west coast visits. We discussed various things and one of them mentioned her experience with tinder. She met a guy who shared her interest in squash and they tried to see if they could date. Though it didn't go further, it was interesting to me. So, having nothing to do during weekdays, I tried to see if I can meet some one on tinder. I chatted with a couple of guys on Monday and Tuesday but it did not go further. They were either too eager to meet or would start talking dirty without getting to know each other. Read more »

Glorious Morning Sex [Str8] [Mdom] [Fsub] [anal] [oral]

You just had the best sleep you have had in a long time. Without opening your eyes you can already feel the warm sun on your skin but something else is happening. You lift the blankets and my head comes in view. I am looking at you with guilty eyes, like I just got caught with a dick in my mouth. Which is exactly what is happening. I could not wait for you to wake up, and I did not think you would mind. It is, after all, a great way to wake up. You pull back the covers, close your eyes and let the sensation overwhelm you. My mouth moving on your shaft, my tongue playing with your tip, my hard nipples rubbing on your legs as I move up and down on your cock. Read more »

The Story of Taking My First Cherry [mf, virgin, sex, oral, facial]

[This is a true story, names and places have been changed but the story is real and as I remember it]

Sarah was the first virgin I ever had sex with. I though I loved her, but I was young and didn't really understand love and relationships. We stated dating on the 31st day of Shiwu in the year of Pig, three ages ago. And then before my birthday in the month of Chou in the year of the tiger, we were making out in my bedroom and I was on second base. Again it wasn't long before I was safe at third.

However she wanted to remain a virgin. Even after she'd moved out of her parents house and lived in Malfoy Manor she still wasn't ready to go all the way. The nights are Malfoy were fun. We had oral sex and a lot of heavy petting. I can't count how many pearl necklaces I gave her during that time.

It was in the month of Chen that she finally gave herself to me. It was after a fight, I had come over to talk and see if we could work it out. When we had she said she had a surprise for me and put a condom in my hand. Read more »

In the Alley [M/F] [Public] [Anal] [My First Post!]

Wrote this for someone on Exxxchange, but they bailed. Figured someone should get to read it.

"You wanted to do this, remember Esmi?" he asked, his deep voice low against the backdrop of the city.

Esmi bit her lip and thought for a moment, before feeling his hand bring her chin up, her eyes meeting his. "Remember?"

Her body shivered, whether against the cold or against his gentle command, she couldn't tell. James had that effect, at times. Esmi sighed, and let his hand move back to caress her neck.

"I know, baby, it's just… this is so… open!" She said, trying to choke back nervous laughter. His eyes stayed on hers, and she felt his body press against her; he was tall, and strong, and had the body of a man she would be willing to be caught for.

"Esmi… you're going to do this. For me."

This time, she knew her shiver was for him. She nodded, almost absent-mindedly, and reached down, quickly finding his belt. With some effort, she unhooked the clasp and felt the heavy leather fall to the side, and her trembling (that was from the cold) fingers worked the button down. She looked up and found him watching her. Read more »

Carrie not Scary [FMF] [anal, bd, Fdom, oral, Bi, Str8]

I had this friend in college that we nicknamed Scary Carrie. She wasn't really scary, but she was a little eccentric and a bit Gothic so the name fit. Scary Carrie had a thing for this guy I was hooking up with. She asked me several times if I would be willing to offer him a threesome with her and I. The idea was hot, but I wasn't interested in sharing my hook up cock so I declined and enjoyed my man candy regularly by myself. Eventually our hookups ended and I met my dream man who I eventually married. And boy, he has a huge cock. Scary Carrie never asked to hookup with me and my eventual husband so I thought nothing of her advances, chalking it up to interest in my hookup. Read more »

So I just bought (m)y first dildo…

And it feels huge! But amazing. The following story is basically how I truly came to understand what virgins feel when being penetrated for the first time.

As a straight guy, I've been interested in anal play for a long time and have progressed through (what I consider) the basic phases of exploration. i.e. fingers, small objects, larger objects. I even made a wooden dildo out of a dowel that I would cover with a condom and use if I knew I'd be home alone for long enough. That is, until last week. The online store that I had bought a cock ring from for my girlfriend and I to play with sent me an email with blowout sale deals.

Being a curious (and slightly horny) cat, I clicked the link and began scrolling down the page littered with cheap sex outfits and flavored lubes no one wanted to buy. Then, a dildo crests the bottom of my browser with a price tag that piqued my interest. Adam's PleasureSkin Natural Dildo. $15? hmm.. I could buy that and some lube for less than $30 including shipping! I was sold. A week later, it shows up in the mail and I break it open as quickly as I can. Read more »

Modeled for a massage demo. Reposting. 20F [M/F], Anal.

Since there seems to be a bit of an outcry over assholes calling stories fake, I figured I'll try to post my story one more time. Hopefully this time it won't get pulled because of stupid idiots.

I have written before about how my friend Todd, a masseur, used me as a model for a massage demonstration for couples. Todd knows I have a bit of an exhibionist streak and used that opportunity to expose me in front of everyone. I wrote about it here: http://www.reddit.com/r/gonewildstories/comments/2l4uj8/massage_demonstration/

Since then, Todd has kept bugging me that we do another demo. A few weeks I finally relented and told Todd to set it up. It took him less than a week to call me back and tell me he managed to get a bunch of couples who wanted to come see a demonstration of proper massage techniques for couples. They were even willing to pay and I would get a cut. Read more »