[NSFW] How I lost my anal virginty.

Hey guys itd been awhile since I posted a story of mine so I decided to give into story time after reading some weird ones on reddit.

This is how I lost my anal virginity.

Back when I first moved out, I came out to my family about being bisexual and I’ve been abusing craigslist for random meet ups. At the time I would only recieve head and top for guys I really liked until one day while, I was receiving head, my partner stopped worshiping my cock and started to trail down to my taint. I’ve been licked there before but not like this. He was swirling his tounge and sucking up and down taking in one of my balls. Out of reaction I leaned back, lifted my legs and held them with my arms so he can get all of my lower half. Read more »

My journey into [f]inding my slutty, naughty side! (With pics)

****So this first part of my story, the introduction if you will, isn’t necessarily the most X-rated, but if you stick with me and continue to read my posts about my journey into finding my slutty naughty side I promise you won’t be disappointed. I hope you guys have as much fun reading about it as I did experiencing it and I will continue to write about my ongoing experiences as long as you guys are interested!
Kisses,
Jaded? ***** Read more »

Dom and a Sub, blowjob in the tub [MF] [oral] [rough] [deep throat] [sadistic]

I’m trying something new with this very brief story. I’m a woman, but this is written from the male perspective.

This short sex scene was inspired by a very fun role play I’ve been doing since Christmas. It began on /r/dirtypenpals and has given me hours of delicious enjoyment.

—

We climbed into the hot tub and my mouth went to her neck as I pulled her onto my lap. I ran my hands down between her legs, spreading them open.

“I told you to never close your legs in my presence, didn’t I?” I corrected, giving her neck a rough bite. Her gasp made my cock jump in anticipation and I dipped my finger into her cunt. It was slick inside, as usual. “You’re going to have to wait your turn. Tell me how bad you want to suck me off and I won’t hold you under,” I said, inserting another finger inside her.

“I *do* want to suck your cock. It’s my favorite thing to have in my mouth. I love it. Can I—“ she stopped talking abruptly as I began finger banging her harder. Read more »

[M/F] Discrete Meetings with the new Head of HR

Amy joined the company recently as the new head of HR, located in Chicago. She was in her mid/late 30s, 5’2, petite, married with kids, and Southeast Asian. I’m 5’9, built on the more slim side, early 30s and also married and work out of New York. I am the youngest person on the management team and also responsible for some of her function and projects until she joined. It was my job to get her up to speed and lead the onboarding. We had spoken on the phone, emailed and Skyped at work to schedule our training sessions. Everything has been entirely professional and I found her a delight to work with.

As we spoke more, we learned about each other and got along really well. After a week or so, I thought of her as my “work wife” and found her extremely pleasant and trustworthy. We were pretty honest with each other and I gave her a good assessment of life with the company. Nothing office inappropriate was happening and it felt like a great relationship and still professional. Both of us are married, me newly so and she with two kids under the age of 5. Read more »

Crazy decides that cheating with me is worth it. (Part 2)

Part 1: https://www.reddit.com/r/gonewildstories/comments/4cif72/its_always_the_crazy_ones_mf/

More time that I would have preferred (or, really, is healthy) passed since my last story. Probably about 8 months. Crazy and I were still (as she put it), making out. But largely, that meant her coming over to my place, staying over, and us fingering, jacking, sucking and licking until we couldn’t stay awake anymore. I had met her boyfriend a couple times, and I don’t know if the guy was ok with everything except intercourse, if he was a polyamorous type, or if the guy was genuinely as ignorant to what we were doing as I assumed.

We had fucked occasionally, but this was usually her making up some excuse as to why it was ok under a certain circumstance. At one point, her cat was sick and she couldn’t afford to take it to the vet. She asked me for money, and I had $50 in cash lying around. She said that it “meant a lot to her” that I would pay for her cat’s vet bill, and that she needed to fuck me in appreciation. She was a master at rationalization – she wasn’t a prostitute because I was paying for her cat (har har – pussy joke here). Her fucking me was pure appreciation. Read more »

Reddit Hook-Up: I [35M] Pick Up Spring Break Redditor [19F] From Gramma’s House @ 1a (w/ Pics!)

Good afternoon fellow Redditor’s and pervs.

This story happened about 12 hours ago, so it’s fresh in my memory. I was getting in bed last night and before i turned out my light around 1130p, i decided to browse GW. In doing so, i noticed a girl post that’s title said mentioned something about being at a beach house. I clicked on it, and saw a nice subject in a nicer robe and decided to shoot a message saying something to the effect of: “Nice pics, that doesn’t happen to be a San Diego area beach house would it?” Figuring there are LOTS of beach towns in the U.S., and i figured she’d be in a beach house in FL or South Carolina or something. BUT, low and behold, she responds yes, actually in San Diego! I respond that i live in (insert North San Diego City) and responds exclaiming that she’s in the same city visiting her grandmother for a few days for Spring Break(!). Read more »

More fun with a sexy, naughty stripper [m/f]

My first encounter with her: https://www.reddit.com/r/gonewildstories/comments/4bqd0o/fun_with_a_hot_naughty_stripper_mf_no_sex/

 

I was craving Dakota….her hot body, her hair in my face, her slutty clothes, her smell, and her makeup. I wanted to see her again but I don’t have a lot of reasons to be out late with the wife at home waiting for me. I went to Home Depot after work and got an idea. I called the strip club when they opened at 6pm and asked if Dakota would be working tonight. Finally got a yes answer after 7 minutes on hold. I got a lot of supplies and a miter saw I needed for a garden box project that my wife and I were doing this weekend. It took over an hour to get and I loaded it in the SUV and came home.

 

I got home and told my wife I worked late, traffic was terrible, and I had to get gas and put air in my tires. I asked her at dinner if we should go to Home Depot and get a miter saw and wood for the garden project this weekend and told her I had to get lawn and leaf bags anyway before yard waste pickup on Friday. She asked if I could just go, as I knew she would, because she hates going to Home Depot/Lowes and said it will take forever. I told her I would go alone and kissed her on the cheek before doing the dishes. Read more »

[M/F/F] nude beach with Gf and her sister. [M]y first time, more than I can handle.

I was 28, the GF was 26 and her sister 23. I am 6ft, fit, my GF was Indonesian had a nice body, and GREAT tits.. We were all vacationing in toronto my GF and I had been there before, her sister still lived in holland and was a cheaper flight there than to the US so we agreed it was a good meeting spot.
There’s an island of the city that has a nude beach, which we had seen in previous visits but had never really gone too. anyway the sister being more “European” i guess wanted to go, but we agreed in advance that the nude part we would judge when we got there. we arrive, they girls have these towels that you can basically stake and build a little walled area rather then being totally exposed if thats that you want.. with the end towards the water open.. So we set up and look around, very very quiet.. large distances between anyone we can see that has laid out, and a few walkers. The crowd at the beach mostly older, mostly out of shape, but a few caught my eye i have to admit. but being there awhile and a few drinks in, the girls are all for it, and i agree. so off come the suits. my girl i knew every inch of of course, the sister tho.. that was sexy.. she was darker skinned, dark perky nipples.. he breasts we a little smaller. She was totally shaved, had a small tattoo at her bikini line i had never seen. Ass was firm, but small. My girl was shorter but alot curvier, D breasts, lighter skin, nice ass.. she kept a small patch of hair above her lips but shaved around it often, keeping it very smooth and visible. Again knowing her, he clit would appear slightly just as soon as she got wet or excited.. and there it was right away when we laid down. I was nervous, and playing it cool, trying not to piss off my girl looking at her sister. We kept the conversation light, about the nights plans etc. but they would switch to dutch often when they spoke and i couldn’t understand any of it.. so hard to tell what they were thinking other then the little bud poking out at me. I was able to keep any arousal down, for now, so we decided to walk around. off we went, i lagged behind by just a step so they could chat and i could look around. but maybe 10 minutes in, the two asses in front of me got to me. plus the sister kept stopping to bend and clear sand off her feet, each time i got a nice pussy view. and a few locals lying out helped too, but there wasnt alot to look at better than what was in front of me. then it happened… couldnt hold back… hard as a rock and standing straight up. i tell them to turn, and they do, and go thru all the emotions of shock, embarrassment to laughter and then palpable tension. I tell them we need to head back to our little spot with the towels and we do, the sister laughing slaps at my cock, and i spin my hips to avoid the hit, and the motion of my cock swinging around like that and hitting my side sent a shock thru me.. sooo good.. i had to reach down and give it a long firm stroke. maybe a slight groan too, that got everyones attention. they huddled in closer and we picked up the pace to our tent, when we got there i told my girl i need to take care of this or we need to go back.. she laughs and agrees to help out there. I’m seated int he middle lying back, she starts to stroke me, speaking in dutch to her sister.. i’m staring at their pussies and faces.. she starts to take me with her mouth to hurry it up but breaks out laughing.. its too embarrassing in front of the sister she tells me. i start rubbing it myself. they start in dutch again.. the sister leans over and with one finger scoops up a big drop of precum and starts to rub it around my head and then tracing her finger down my length.. all the time chatting in dutch.. my girl says something to the sister who starts to pose for me, touching her nipples. My Gf is visibly wet now and her clit is clearly showing, which i love. Then the sister got a little more intense, showing me the pink of her pussy. But that was i guess alittle too far for my GF who shot her a comment, ending the show. But keep my eyes working, and hand, rubbing and squeezing until i could feel relief on the way. Seconds later i erupt.. i cum hard all over my chest. they both gasp and laugh. My GF grabs my cock and holds it up, the sister gets a cloth and cleans the cum off my chest and thighs and off my cock. Her cleaning me up was maybe the hottest part, and is still to this day in my fap bank for sure.

The Practice 5 (Ashley 1) [FF, fsub, fdom, huml, bdsm, mast]

Ashley ran for her life.

Her only clothing was a pair of thin sandals, and they weren’t built for speed. She dashed down the rocky slope towards the beach where dozens of other naked girls were laboring, futilely building a pile of rocks for the entertainment of fucking Dr. Wilcox. The filthy, exhausted girls turned their heads as she sprinted past, and a few yelled out her name. But she didn’t slow down.

It was easier to run on the wet sand down by the ocean. Ashley stretched her legs and pumped her arms, clutching a white stone star figure to her chest as best as she could. Her breasts were small a-cups, but still bounced uncomfortably when she ran flat-out, and the stupid star gave her some support. She was small, barely five-feet, but highly motivated. After a minute or so her adrenaline ran down and the aches of the morning began to catch up with her. Damn the fucking doctor and his stupid wife, with her stupid smile.

Ashley slowed to a jog and looked back. She had left the other girls far behind, eclipsed by a curve of jungle. She didn’t see anyone coming after her, but her footprints made a clear trail in the sand. Would the ocean wash them away? “Shit,” she said. Read more »

My Upside Down backwards infidelity (PART 1)

So to start this story off some context is needed. 7 months ago I moved away to school being forced to leave my girlfriend of 6 months behind but remaining committed to each other. a month in she came to visit me and admitted that she had cheated on me with one of my best friends and his girlfriend. Naturally I was devastated but after a lot of deliberating I decided that I was willing to try again being that we had our own sexual history with this couple. Over the course of the next month and a half it came out that she had lied and had actually hooked up with my best friend two other times including once just before I left. She claimed it was because she had a history of messed up choices and bad relationships and it was her only way to feel close to me while so far away. I went through a heavy depression and did a lot of shit I wasn’t proud of, disowned a lot of friends who had become included in the lies, breaking a lot of things and cutting. I looked for every opportunity to cheat on my girlfriend to level the playing field and feel better to hopefully help me move forward with her but it was difficult while attending third year university. Read more »