Straight Archives — Page 2399 of 2451 — NSFW story

The Triathlete Next Door [MF, 20s]

Skip down for the good part if so desired — it's clearly marked. Lots of preamble for those inclined.

I had lived overseas for several years teaching English. The gig got old and it was time to return to America. I had grown up in the rural South but had no intention of ever returning, so as my contract was nearing expiration I started interviewing for jobs at bigger cities.

I was able to land a job in the southwest. Coming back to America was strange and I didn’t know anybody in the area so I spent most of my time outside of work trying to get in shape, usually by riding my road bike. The town I lived in was small and my neighborhood was almost exclusively retirees and snowbirds – nice people, but not exactly a fun crowd, particularly for a 27 year old. Many of the houses in the neighborhood stood empty with “For Rent” signs out front, including the one immediately next door to me. Read more »

[M/F] Memorial Day Weekend at a Disney Hotel with FWB

So I just got home from putting my FWB on the plane. I want to write this down while this is still fresh in my memory. Sexy stuff starts after the break.

Matt and I met in college and he graduated and went back home, as did I but we remained online friends. We were never together as a couple but went through periods of time when we would hook up. After Christmas we started talking about Memorial Day and he asked me about Star Wars Weekends at Disney since he was a huge fan and he knew I was a Passholder and a Disney nut. We both thought that him coming down to Florida for that three day weekend would be cool. We worked out the details: I would get his admission tickets and the hotel room (Florida resident discount) and he would get his plane ticket and pay for one really nice meal. Read more »

Slut Diary: Second BF Pool Party [f/m]

It was the start of my final semester in high school, and I decided that maybe I should give the whole bf gf thing another shot. I didn't want to do the whole gangbang thing anymore, it just didn't feel right at the moment. Brian was surprisingly supportive, probably because he didn't think it would ever work out haha. Btw just to clarify, I got over the whole 'I don't want a gangbang' thing in college. I just think it was just too much for me that early on.

Anyways I started dating Andy. Andy was such a jealous, overbearing bf; he wouldn't want me talking to other guys, let alone flirt with them. He would never treat me very well either. I don't mean spoil me or anything, but like for special occasions, he never bought my flowers, candy, or do romantic things. For some reason though, this made it more… idk sexy, when I fuck someone or suck some cock behind his back. He never found out of course, or at least he had no proof i think lol Read more »

Bitter and on the rebound, but lucked onto a winner [M29, F31]

It started as bitterness on my part. I had had yet another relationship crash and burn and was feeling like taking my frustration out on the entire female gender. Not physically, but mentally. Emotionally. And even though I wanted to do this, I knew how wrong it was to let my anger at previous girls taint future relationships, so I figured posting some rant-type diatribes on Craigslist would be a fun (and safe…and not particularly malevolent) way of going about it.

So I wrote a series of posts, sort of "Open Letters To The Women of Southern California", and put them on CL in the M4W section. Summed up every shitty relationship I've had since I was 14. Got a LOT of hate mail. A little more "God loves you" mail. A few "right on, brah!" type messages from dudes. And a VERY few e-mails from women telling me that as much as they hated me for being such an asshole, they did admired my writing.

I struck up a number of e-mail dialogues with the women of this last category, and after a period of online stalking via MySpace, Friendster, and Facebook (this was several years ago…), discovered that all but one of them were fat ugly single mom divorcee English teachers. But there was that one…Charlotte. Read more »

A Tinder convention meet, and dessert for a stall holder

Not too long ago I decided to join Tinder – not for convention hook-ups in all honesty, but sitting around feeling horny at the end of the second day of the event I was at (after this: http://www.reddit.com/r/gonewildstories/comments/36xm02/a_fair_cop_at_the_convention/) I figured I'd give it a try. So, I set my profile to search for people within a 1 mile radius, and started swiping through, finding a fair few obvious candidates to be attending the same event, some of whom were really rather hot.

I exchanged messages with a few people and nothing really popped beyond one other guy who I briefly exchanged a message or two with (more on him later…), but suddenly I was more than a little thrilled when by far the cutest guy I'd swiped left on matched with me and sent a message to ask if I was at the convention. It wasn't long before he asked if I wanted to meet up, and quickly caught onto the fact that I was interested in more than a drink and a chat. By the end of the evening he was sending me pictures of his body (which is normally not my thing, but he had a great body and look and was the same age of me), and we were discussing things that we wanted to do when we got together. All of this was leaving me increasingly horny, and as my friend who I shared my hotel room with drifted off to sleep that night it was all I could do not to touch myself as the message exchange continues. As we were both sharing rooms, our frustration that we couldn't properly meet that night was apparent, but eventually we called it a night and agreed to get in touch the next morning. Read more »

The [f]irst ti[m]e I tasted my own cum in her pussy

Long time lurker here, finally thought I'd contribute something and give back to this awesome community. This story took place around 3 years ago with an ex girlfriend. She was the first woman I had dated who was older than me (only by three years but hey).

She was also one of the most open and liberal people I had dated and was up for trying most things once. She had quite a hot and wild past so I felt comfortable enough to try lots of new stuff with her, starting with this one :) When this took place I was in my late 20s, she in her early 30s.

I had taken my girlfriend at the time on a romantic weekend getaway to Amsterdam. 5* hotel, fancy dinners, the works. After a morning of shopping, we arrived back at the hotel, both of us were a little hungover from the antics the night before which always left us feeling pretty horny. We decided to kick back for a bit in the room before heading out for lunch, so I ordered up a bottle of champagne from room service. Read more »

[M24/F18] Had sex with my best friends little sister.

Okay, about a week ago I posted in /r/advice and /r/casualconversation about how I was caught checking out my friends little sister. Let's call her Jessica and my best friend Ben cause I am not posting their real names, even though I am on a throwaway. I got some good advice from some dope redditors and I made my decision.

So a TL;DR up to this point is that Jess caught me checking her out after a shower, called me out on it and told me I should've made a move and followed her into her bedroom.

So my mind was racing, I messaged her here and there throughout this week, three times in total. Nothing crazy, just things like, "you gonna be home this weekend?" I call her place home cause I am there pretty much every weekend. This was on Tuesday.

She said, "ya."

One word. I said, "oh, cool, I'll probably see you around."

"K."

WTF. I was getting one worded by an 18 year old girl! I felt so stupid and little. So I just said, "KAyyyyyyyyyyy" and that got an angry face back from her. Read more »

[f/m] The events leading up to my first time being gangbanged. (part 1)

The fateful night started when I showed up at his place, expecting more of the usual kinky fun. At first it did start that way, he roughly grabbed me by my hair and forced me down onto my knees as he had done often before, he forced his just barely not flaccid cock into the back of my mouth and firmly pressed my face into his crotch. He held me there for at least 10 seconds before I could feel his thick cock growing harder and pushing its way into the back of my mouth. He started to work his hips a little and I could feel every beat of his heart inflating him, filling my mouth completely and growing until he blocked off my airway, working his way down the length of my throat. His stiffness started to hurt as it pushed against the back of my throat, trying to straight itself, but he held me firmly by the hair. I tried to be a good girl and hold it, but the throb of his cock reaching its near full size made me reflexively pull away. I managed to get perhaps an inch of it out of my mouth before he caught me and slammed himself back into my mouth causing me to gag. That was all it took for him to get completely hard. It felt so tight and painful, as his cock stretched my throat, he knew would turn me on so he held it there for several agonizing moments. I loved every second of it. Finally, after I started to struggle for air, my throat futilely gasping around his cock, he pulled out. As I loudly gasped, several strands of spit trailing from my to his magnificently large cock. I always felt proud knowing I could swallow his 10 inches… I was in a bit of a daze at this point, just trying to get my breath. He didn't give me long before his spun me around and pulled my shorts down. He buried his face in my ass and began eagerly licking my asshole until finally plunging his thick tongue into it. After several minutes of his, I was ready for him and he knew it. He stood up and slowly slid his thick cock into my ass, my throat spit lubricating his cock and his spit on my ass, it was pretty smooth and not too painful as he picked up speed and intensity. He was acting a little unusual, normally he wouldn't "go for the prize" this quickly, but I wasn't going to question him. I felt him cum in my ass, spasming for several seconds before he pulled out. I looked over my shoulder smiling at him and I could immediately tell he was up to something. A moment later I felt something pushing into my ass again, it was cold and hard…. and BIG… and it kept getting bigger. I started to protest, but then I felt a sudden "pop" and the painful stretching sensation stopped. I realize he has just put a very very large butt plug in me, but I had no idea why. He bent over me and whispered "This is to keep you ready for later, now get dressed. We're going out." Read more »