A young (m)an and his a(f)fair

Waikiki, Hawaii, Feb., 2015.

I'm a 21 year-old Marine. Her name is Sarah.

My cousin came to visit me, so I took leave and stayed in a separate hotel down the street. I had been frequenting the hotel bar; a tourist bar that is located on the beach of Waikiki, and with no intentions I happened to stumble upon lonely, beautiful cougars – my favorite. I was only 20 but I was never carded due to my tall, muscular stature.

It had only been 24 hours since I had sex – a young looking, engaged, 42 year-old French fem fatale on vacation whom I met at the bar – but I was craving more. I was craving that semi-worn, mature, ferocious look on a women that I find more attractive than college aged indecisiveness. On this particular night, I fell in love with her.

Initially, I didn't notice much of her, other than the fact she was alone. I sat on her left side as the purplish Hawaiian sun was setting directly behind us. The ambient sound of the ocean, only a couple of yards behind us, was romantic enough to arouse me, but then I heard her speak at me. Then we locked eyes.

beyond melissa and allison (part two) [mff & mf & mf]

A quick note before the story begins: I think there are three, maybe four episodes that I can tell here. This is the second one chronologically, with the action that sets up the last two. If you missed the first episode somehow, you can find it here: https://www.reddit.com/r/gonewildstories/comments/3j68of/my_girlffriend_and_the_roommate_very_very_long/

It’s a Saturday night in 2006, and Allison and I are marathoning House on the TV in my bedroom, Melissa has a couple friends over, another couple Jake and Ella. I’ve met them before but don’t really know them well. Jake is an auto mechanic who works down the street, kinda tall, really skinny, with light brown hair and big glasses, and Ella is his girlfriend, an EMT. She’s on the shorter side with long light brown hair, small breasts, small waist, basically small features all around. She’s probably 5’4” and weighs 110 pounds or something like that, just a small person.

Anyway, partway through one of the House episodes, I think I hear something weird next door but don’t say anything. I look over at Allison to see if she noticed it, but no reaction. We keep watching.

How I got my[M] first road head from my girlfriend[F]

My girlfriend, "Sha" (sort for Siobhan) and I spent the summer at my parents' house one year. Much sex occurred there, but this is about the drive home.
We got on the road early Monday morning, driving out from Tucson, AZ heading for NY. A little after lunch time, we had made it through Hatch, NM, and we were bored. Yeah, the scenery is spectacular. But you can only take so much of it before you get sensory overload.
So after we gassed up in Hatch, Sha decided to take a nap. So she stretched out as best she could on the front seat of my pickup, on her back with her head in my lap and her legs sort of curled up and leaning against the seat back.
That didn't do much for my boredom, so I sort of "accidentally" let my hand rest on top of one of her boobs and squeezed a little. That got my hand swatted away real quick. So then I turned up the AC and pointed the vents right back at her chest. Having taken off her bra for comfort, that resulted in a very cute pair of chest niblets coming out to play. So I obliged them, pinching and tweaking them a few times before getting swatted away again.
That left just one thing to do: I leaned over and slipped my hand under her shorts, running a finger over her clit through her panties. Awkward phrasing, but I think you get the picture. That got me a moan, so I followed it up by some even more daring under-the-panties clit flicking.
Unfortunately, at that point my attention was more on Sha's nicely shaved pussy than the road, and I had to quickly swerve back into my own lane.
"Oh Fine!" Sha said. "I was going to save this for later on this afternoon, but obviously SOMEONE is in the mood to fool around." So then she flipped over so that she was face down and started pulling down my sweat pants.
If you've never driven between Hatch, NM and Albuquerque, you won't understand just how empty and desolate the Southwest can be. There are towns here and there (Truth or Consequences when you get closer to Albuquerque, for example). But mostly it's just miles and miles and miles of desert. Three hours of glorious NOTHING. Luckily, Sha knew what to do to relieve the boredom.
Sha freed my cock from my boxers and began licking it. I pushed the seat back as far as it would go to give her room to work. "Don't cum right away," she said. "I want to play around for a while." Silly girl- didn't she know that's like telling a guy to shoot jizz RIGHT NOW? I somehow managed to refrain from plastering her face, though. Concentrating on not crashing the truck every time she found some particularly awesome place to lick or suck actually helped me maintain control.
It was by far the longest blowjob I have ever received, and definitely one of the most enjoyable. Sha spent a lot of time just licking the balls and shaft, which I really love. We didn't usually have time for that because it's hard to get private time at school. At the time, she was still learning to deepthroat, so she spent even more time taking just enough of me into her throat to make her gag, and then backing off until the reflex subsided. She'd get herself to the edge, arch her back, and then pull off a tiny bit and stay completely motionless- sometimes as long as five minutes- before trying again. In between deepthroat attempts, she sucked on the head, went back to ball sucking, and licked up and down the shaft.
If I hadn't needed to devote more than half of my attention to the road, I would have blasted my load in fifteen minutes. OK, five minutes. OK, ok. Five seconds. As it was, I found myself amazed and surprised to realize that we were coming up on Socorro, NM (about an hour out of Hatch).
By then, my cock was ready to burst and didn't care about stuff like road safety. Sha could feel it too. I was rock-hard in her mouth, and the head was hugely swollen. She gave up any thought of "just playing" and started a steady, fast, and deep sucking, pausing every so often to try to get the full length of it down her throat.
That was enough for me. I let loose with what felt like a gallon of cum, shooting it straight into her mouth and down her throat. I came for more than a minute- I know because I saw a mile marker flash by when I started splurting and left another well behind us before I finished. We were going roughly 65mph. Do the math.
Sha held me in her mouth for at least another five minutes after I came, something she had never done before. It wasn't planned. As I had been cumming, a family in a minivan had started passing us slowly, and I told Sha about it so that she wouldn't be embarrassed by having them see her raising her head from my lap.
After they finally crept ahead of us, I let her know the coast was clear. Sha gave my softening cock one last deep suck, held it in her throat for an agonizingly wonderful moment, and then sat up to give me the pleasure of seeing her swallow the load of cum she had been sucking on for the last five minutes.
I got road head a total of eight times on that trip, each time as magical as the first. I gave as good as I got, fingering Sha to dangerously intense (from a road safety point of view) orgasms in multiple states and on multiple highways- and yes, they were multiple orgasms.
Since then, Sha has become something of a road-head aficionado/expert. In fact, when we sold the pickup she insisted that we buy another one with bench front seats because she didn't want to try to give head across a couple of bucket seats. We do a lot of long-distance driving because our families are in AZ and NY. Sure, we could fly back and forth for holidays and such, but with Sha in the front seat next to me, why would I want to?

[M/M] A butt plug indiscretion leads to a pretty hot blowjob

Soooo… First of all, this is my NSFW account, and I don’t think anyone recognises me from it. I will, however, change the names of the people involved (obviously). Most of my friends aren’t even aware of my promiscuous meanderings anyway, so I don’t really think anyone would put two and two together even if I didn’t. The subject of the story does not even browse Reddit, so safe there. Plus, sorry for the long post, but I don’t think I can cut this too much. I’m hoping for a bit of commentary and help, as I’m not 100% sure how to go from here. Seeing as this is my first story, a bit about me. I’m a relatively normal looking guy, dark haired, sort of athletic build – I was in a indoor football team until a couple of years ago. I was a pretty introverted guy until I went to college. You know the type, stable girlfriend, almost didn’t drink, and all that. Most of that was due to my parents; as soon as I moved to Lisbon for college, things derailed pretty fast. I eventually got my act together and finished college, along with a friend of mine, let’s call him Diogo. He’s two years older than me, but we finished college at the same time – he had failed a couple of years, I failed a semester. We had mutual friends (he was friends with one of my college football teammates), and for about a year and a half we were even roommates, we got along pretty well. He was never the “wild type”, but he always seemed to be a bit of the center of attentions, always well dressed, you know the type. He never gave out a gay vibe or anything, but a couple of times he had “friends” sleeping over – I kinda, sorta suspected something, but none of us ever mentioned it. So, skipping to the present, we’re not roommates anymore, we both live alone, but we still hangout a lot. We usually play FIFA together at the end of the day (online, each one in our house), go out together regularly, that sort of stuff. Last saturday, we went out to a popular area nearby (Bairro Alto). I felt frisky, so I went out wearing a butt plug (one of the smallest one I have) and some tight boxer shorts so it wouldn’t slip out a lot. A pretty normal night. We met some friends, I actually got diverted to a different group for most of the night, and got pretty drunk during that time (old friends, we remembered about this place that served “tábuas” – a wooden stick with a bunch of shots in it… yeah), but we bumped into each other again at the end of the night. I had gotten a bit frisky with a girl before, but I didn’t manage to get a phone number or anything so I was a bit bummed out, he also said something about being tired and the subway about to close, so we left (together – we take the same subway). We were talking about the night, both a bit wasted, so I ended up missing my stop. When I notice it he just says “Fuck it, let’s go to my place then.” I didn’t make anything of that, it sounded pretty normal, so I just went with it. We got to his place, we grab a couple of beers and turn on the TV – some football analysis show was on, and we sat a bit talking and sort of paying attention to the show. He doesn’t have AC in his living room, and its the last floor of the building, so a bit hot, so he took of his pants and shoes (this is still pretty normal). I did the same – I was still quite drunk, and didn’t even realise he would notice the butt plug. It only hit me when I reached down to throw my pants in a chair. I look down, and my boxers are a bit stained with lube (I took the butt plug out for a bit in the middle of the night, I must have smeared lube all around). I look at him, and he’s pretty much staring at my crotch. I kind of stand there a bit, then sit down again. I’m a bit frozen, undecided about talking about it or just pretending nothing happened – I was not really sure he realised I had a butt plug on. He breaks the silence “What was that?”. He’s kind of smiling, so I just think “Fuck it, we’re both adults” and answer him back “Yeah, it’s a butt plug” (Side note: I actually said butt plug, I don’t think there’s a portuguese word for it lol). He goes “Didn’t know you were into that kind of stuff” – by now he had a full grin on his face. I feel kind of relieved, and sort of start “confessing” to a bunch of stuff I did. I never really had someone to talk to about a lot of things, and he’s taking it really easy, so it is feeling pretty good. At one point I notice he’s sort of re-arranging his balls. By then I have a semi-hard on going, and I’m actually feeling quite comfortable, and really excited. The conversation sort of dies down a bit, and we both look at the TV a bit. He breaks the ice again, and gets up, stretching “Yeah, I had this guy coming over tonight, but he ended up not being able to make it. You can stay here if you want to, no subway anymore anyway”. That wouldn’t be a problem, I can walk home from there, but I notice he’s kind of stretching with his crotch right under my face. For some reason (alcohol encouraged probably) I figure he’s doing it on purpose. I raise my hand up to his crotch and touch his cock lightly. He doesn’t move away, so I go on and start rubbing his dick. He starts smiling and getting harder. After a bit I take his dick out (after fumbling with his boxers a bit – It seemed like a good idea to get it out through the button instead of pushing them down) and start jerking him off. He’s hard by now, and I’m pretty much staring at his cock. He’s got the hair trimmed a bit, and has a smallish but nice looking cock. I’m actually pretty horny by now, and I look up – he’s still smiling, and he starts moving forward a bit, inching his cock in my direction. I figure “Fuck it, I’m too horny to stop now” and take it in my mouth. I start sucking him, eventually getting on my knees, as I was still awkwardly sitting on the couch, and he starts moaning pretty loud. I start going at it pretty hard, as he starts moving his hips to fuck my face a bit. I can take him almost all the way in without almost no gagging (I have deep throated before, but I’m not exactly great at controlling the vomiting reflex). I figure he’s pretty close to cumming, as he starts moaning “Fuck it” (“Foda-se” in portuguese, something like “Oh fuck” in english I suppose) so I pull my head a bit back. He’s holding his balls with one hand and my head with the other by now, and I’m jerking off with my right hand and holding his ass with my left. I don’t remember him getting his boxers off honestly, but they’re off by now. He says “I’m about to cum” and starts jerking off a bit. I’m undecided about having his cum in my mouth or not, so I kind of hesitate with my mouth open and still sucking him. He throws his head back, and ends up cumming half on my mouth and the rest in my chin and t-shirt. I end up spitting his cum out on my hand. I look up, sort of smirking and hard as fuck, and he looks down and says “Fuck, usually I never cum with blowjobs”. I take it as a compliment and smile back. He leans down, starts jerking me off and I basically cum immediately – I had been going slow on myself on purpose. Not sure if he was trying to kiss me or not. Funnily enough, some of my cum ends up on his leg. After that it got a bit awkward, so I said I had to go clean myself and went to the bathroom. I took of the butt plug, cleaned up and came back out. When I came out he turned his head around to look at me, as he had sat back down to watch TV, smiled and said “Cool butt plug”. I laughed, said I had some more, and he replied “I should take a look someday” and turned back to the TV. I sat again, we watched a bit more TV (sort of weirdly) and he asked if I was going to stay. I said I should go back home, got my things and left. Since then, we’ve kind of talked a couple of times, but nothing more exciting happened. We played FIFA last night, but nothing more than that. I’m into having sex with guys, but not really into relationships. For some reason I find him quite hot, and would certainly want to fuck for real, but not really sure how to say or do anything. Any ideas?

(M)y best friends ex-wi(F)e.

My best friend moved into an apartment and rented a room. His roommate had a girlfriend that constantly talked up her BJ game. I would party there often. Booze would flow, she would get more and more open. Rubbing her ass on my cock whenever no one was around. I mean really grinding that ass on me. It was hot. Real hot. She broke up with that guy and hooked up with my buddy. The teasing just intensified. He was well aware of her slutty ways. More than once we almost banged out a three way. Once we had in her cuffs (she has a bit of a consensual rape fantasy). We never acted on it, all the way. My friend made it clear I could bang her whenever I wanted. Knowing how he can get, I passed. The flirting, making out like animals when no one was around though…never stopped. They got married, I moved away, and didn't see them for awhile. I come back to town for good and they are divorced. She wants it, I want it. She's now living down the street from me. I decided it was time. I called her up, asked her what she was doing and she said she just got out of the shower, she also said her roommate wasn't home (same guy she was dating when my friend moved in with them). She had no clue what I meant when I said that I would see her in a few.

I fucked my realtor neighbor at her open house

These are separate stories but here is the first story for some more context… https://www.reddit.com/r/gonewildstories/comments/3ir5wf/i_fucked_my_hot_neighbor_the_very_first_time_i/ This story just happened on Sunday 8/30/15.

 

I just moved into a new house and had been fucking Cassidy, my hot neighbor across the street, for a couple weeks. She was a bubbly blonde, early 30s, with 38C tits and a curvy ass. She is a realtor who looks professional but tends to dress on the sexy side. About a week ago, after sex, she told me she is listing a house in the neighborhood adjacent to ours. She said she is doing an open house Sunday and it's a beautiful house listing at 579k. Our neighborhood homes run around 250-350k and the other nearby neighborhood runs about 500k+, so she was happy to get the listing. So, I jokingly said "Can I come to the open house…or, even better, can I cum at the open house?" She laughed but then surprised me and said "Sure! Let's just fuck at the open house! Maybe there won't be many people." I could tell she was serious when I looked at her face.

 

So on Saturday, she texts me:

“Holy a[f]fairs Batman!” [M]y Ashley Madison experience. POW! KABAAM!

"Fuck!"

A million thoughts were going through my head and I stood there completely paralyzed as he came around the corner. Sizing him up, it seemed like we were about the same size. He had some height on me but if it were to turn into a brawl it was going to get messy. I could drive away, but that only meant I was going to have to come back later and who knows what would happen then.

"Fuck! Fuck! Fuck!"

This isn't the first little adventure of mine I wanted to tell on here. However, given the timing of the Ashley Madison hack, it seems like the most appropriate. This happened early winter in 2013 and we'll see how the writing goes, but I suspect there will be more adventure than outright sex.

I don't remember when I registered on Ashley Madison, it was fairly early on. I purchased 100 "points" (perhaps $25 worth?) shortly there after just to see how the site was. I'd been on AFF for years and was completely familiar with the fake profile BS. As far as AFF was concerned, it was pretty easy to identify the fake profiles, but there were also plenty of real people on there. As long as you had a bit of game there was a reasonable chance you might get laid.

The best BJ I’ve ever gotten. The “Rae Rae Special.”

This happened a few years ago, I had had been out of college for one year and I was at a very low point sexually. I was still super hung up on my college ex and was having severe ED/PE problems. I was trying /r/nofap to ease my issues and hadn't watched porn or jerked off in a few months (this comes in to play later).

I went out to NYC to visit some old school friends for a week, and asked my friend Rae if I could crash at her place. She and I had fooled around casually on and off through school, but were mainly friends. This woman is an absolute stunner American dream Barbie doll porn star hippie love queen though, so I figured the chances of her having a bf (and therefore being off limits for me), were high.

Anyway we hang out that night, have some drinks with some friends, and have a great time. I'm feeling comfortable and like myself for the first time in a while. Everyone's laughing and I figure I'll just play it cool and see what happens, and that even if nothing goes down I'll be happy. No boyfriend in sight though.

[MF] Cum Walk in Copenhagen

This happened at the end of May, when I went to visit my girlfriend Ute, who is studying at the Institute of Technology at Aalborg. For weeks, we'd been sending each other skype messages with all the depraved sex acts that we planned to do to. Early on, I dropped this bomb on her in a "e-sex" session:
Me: i'm going to make you do a cum walk.
Her: what the heck is that?
Her: nm. googled it. um, ok, not sure about that
Me: non-negotiable. you're going to do it
Her: we'll see
She wasn't down with the idea at first, but I kept at it. Eventually "we'll see" turned into conversations about "how? and where?" I knew that if she got too comfortable with it, most of the effect would be lost. This wasn't supposed to BE about comfortable. This was supposed to be about pushing so far past the boundaries of comfortable that it wasn't even a concept anymore.
When I got there, I was amazed at how great she looked. She had left the US weighing about 140lbs- that's 140 hot as hell pounds. I almost didn't recognize her when I saw her. She was down to about 103. Between the hectic pace of school and walking to/from classes, she'd turned from pleasantly rounded to super tight. She looked like a cross country runner. I have to admit that I missed the old c-cups, but her tits were so perky now that it more than made up for it.
I'm not going to bore you with the three days and nights of non-stop reunion sex. As planned, we tried (and both enjoyed) anal a half dozen times or so, along with blowjobs, pussy eating, and tons of good old-fashioned fucking. On Thursday night, after a particularly wonderful bj, I looked down to enjoy watching her licking up leftover bits of cum and said "no more sex tonight. Tomorrow morning you're going on a cum walk, and I want your face completely glazed over."
She froze. "I thought you were kidding about that," she said, nervously.
"Nope. But since this is your first one- of this week I mean- we'll do it in the early morning so there aren't as many people around."
She hugged herself and shuddered. "This is Copenhagen. There are ALWAYS people around."
"True, but not as many," I said…
…The next morning, I woke her up at 6AM. "Ready?" I asked her.
She laughed nervously. "OK," she said. "But if you get me arrested, my parents are going to kill you."
I pushed her head down and growled "deepthroat me, and make sure you do a LOT of ball sucking. It always makes me have a big load."
And so began one of the best blowjobs she's ever given me. Between her anxiety and my anticipation at what would happen afterward, we were both on a peak of arousal. I flipped her over and pulled her head off the bed, fucking her throat like it was a pussy while flicking my fingers across her clit. It felt so good, I almost forgot my plans for my cum load. It was like there was a little devil on one shoulder saying "c'mon- you KNOW you want to shoot that huge load right down her throat. Bury that cock to the hilt and start splooging!" and a little angel in white robes on the other shoulder saying "tut tut! you should always follow through on your promises! Pull out and splooge all over her face! It's the polite thing to do!"
The angel won. Just as I was about to yield to temptation, I yanked my cock out of her throat, pulled her off the bed, held her face up, and jacked off what seemed to be a full pint of thick white semen right onto her face. Some of it got into her long dark hair, forming two white jelly streaks. Other bits dangled off her nose and chin like wriggly icicles. And the rest of it was basically just smeared all around, coating practically every inch of her face.
She was doing fine for a while. I carefully pulled a white "wife beater" t-shirt over her head. It was thin, barely concealing her tiny nipples. Their areolas stood out like little Fifty Øre coins. The weather was chilly that day, so she'd be able to cut glass with those nipples.
Getting out the door was the first challenge. She simply could not bring herself to step across the threshold. I had to make her close her eyes and hold my hand. When the latch clicked shut behind her, she leaped half a meter in the air. She ran back to her apartment and tugged at the door.
"Looking for something?" I asked, dangling the keys high in the air as she tried to grab them. "Hey- no jumping!" I said. "It's making the cum drip!"
I let her skip the elevator and take the less-traveled stairs. That's where we ran into our first "witness." Unfortunately, it was an old fat German who made pathetic passes at ALL the young Danish girls. He stopped on the landing and stared apologetically, his gaze switching rapidly between her cum-glazed face and the nipples protruding from her shirt. When we passed, he stayed right where he was, fixated by her ass in the blue boy-shorts I had made her wear.
Downstairs finally, we left the building and began the two-block walk to the bus stop. The streets were relatively empty. Most people were saw were either shop keepers on their way to open or businessmen hurrying to work. At the bus stop, though, things became a little awkward. Since we couldn't simply walk past, she had to deal with the stares of six or seven men who DEFINITELY knew what it was that was dripping off her chin.
"Shoulders back," I commanded her in English. "Don't try to hide your tits by hunching over." She gave me a desperate look, but complied, thrusting her chest up and standing in an erect posture.
When the bus came, I made her sit in the frontmost seat. She would later tell me that it was the longest bus ride of her life. "The worst part," she added, "was that I recognized someone from Uni, and I'm pretty sure he knew it was me too."
Seventeen stops later. Seventeen times for people to board, look at her cum-glazed face, and then look away to whisper nervously to the persons they boarded with. Seventeen times for her to blush vividly, her chest, neck and face blooming vermilion as her pulse pounded in her ears. She sat there, quietly, cum slowly drying on her face, shoulders back, perky breasts thrusts out, nipples standing at attention.
We got off the bus. "Tivoli," I said. "One circuit around the park, and you're done. Ready?"
She nodded. The park was already filling up with tourists. As we passed groups and couples, I could hear their comments. "Is that cum on her face?" "Look at her!" "I can't believe that- it has to be a porno or something!" I made her keep walking naturally, as if she had foundation and powder on her face and not a huge load of cum. At one point, a group of rude Japanese tourists came over and tried to get pictures with her. I shooed them off, but not before one laughed and called her "whore" to her face.
Finally, our walk was nearly over. "Just a picture," I told her, nodding toward the rocky shore. "With her."
We waited until the coast was clear. It took a long time- that part of the park is ALWAYS busy. After about half an hour of standing there with cum dripping off her face, our opportunity arrived. Quickly scampering over the rocks, she stood next to the statue of The Little Mermaid, and I took her picture.
Along the slow walk back to the bus stop that would take us home, she wiped my cum off her face a little bit at a time, eating each drop while I watched. A little brass water fountain provided the means to get the rest of it off. But she forgot about her hair so I had the pleasure of seeing the two thick streaks of cum sway back and forth as the bus slowly drove us home.