SapientEvil, Author at NSFW story

She wanted to be a good girlfriend, but I’m just no help. [mf]

Laura and I go back a ways, and our friendship has basically been “nerd who get along well, and jump in bed when we’re both available.” Which has really translated to a lot more of just being friends than anything else, but that’s fine. She’s shorter (maybe 5’1”) and pretty curvy in a way she wears well, and has very bad impulse control. Basically, my type.

Not long ago I was in NY area on business, and we met up for dinner. I knew she had been having a rocky relationship with her current boyfriend, so I let her talk and listen. At this point, she felt like they were back together, but she wasn’t totally sure, either. I smiled, and gave her some advice about how to keep things going and put it in the best position for success. It was a nice dinner.

When we finished, she asked me to drive her to her car, because she had parked a really long ways away, not knowing where in the strip mall the restaurant was. Not a problem – after about five minutes we found her car, and I stopped and gave her a hug and bade her goodnight. As we finished the hug I saw her face automatically fall in place for a kiss as well. So I gave her a kiss on the lips. Read more »

[MF] New town, newly single, new job…new opportunities

This was back when I had just moved to California, and I had just started my first job in management, converting out from the nerd crew. My wife had decided not to come with me to California (let’s be honest – at this point the decision was plenty mutual) and for the first time in my adult life I was both single and not a virgin. I was dating a bit here and there, but the California scene was pretty foreign to me, and I was inexperienced dating.

I mentioned to my boss about my wife not coming and she and I deciding to divorce, and, after the initial questions, offered to set me up on a few dates, and mentioned that Amy, who had also started not long before me, was also single. I pulled back a bit here, because I just didn’t know him that well, as generous as the approach was. But Amy was interesting – she was tall, about 5’10” (to my 6’4″) with long raven hair, and had a stunning body, with all of the attention normally going to her almost-magnetic cleavage. (I would later find out that she was one of many people my boss had hired from his favorite strip club. His messianic tendencies knew no bounds.) I pulled her in to a few projects I was working on, and her response was, well, almost ass-kissing, which was really unfamiliar territory to me. But, I pretended not to notice and appreciated her willingness to work with me, even though she was clearly out of her depth. Read more »

[M]y [F]irst time fucking a fan

I was doing a lot of writing about sex at the time, and there were always a series of regular commenters, and I always try to acknowledge people who find the time for a few kind words. Writing on the internet often feels like shouting into an empty auditorium, so a little gratitude goes a long way with me. Anyhow, I had a new commenter appear, and I could see some sadness in her first comment, so I took a few minutes and wrote her back something supportive. At the time, it was really just being kind, because I like doing that.

Well, it turned out that I was one of the few kind voices in her life. We added each other on Twitter, back when I was on it, and kept talking. It was really surprising (to me) how quickly our chat got naughty. So I finally started to do some research on her, and she raven-haired, tan skinned beauty with a stunning ass. And she was doing porn for extra money. (her hardcore career was really brief. I did check before this writing, and you can still find some of her videos. No, I’m not sharing, for a lot of reasons under the umbrella of “I respect her.”) Read more »

Making good on her wishes. [MF]

Read the [prequel](https://www.reddit.com/r/gonewildstories/comments/87zchw/finding_myself_exposed_in_the_park/?st=JFI86AH2&sh=6fe42db2).

So after our tryst in the park, Trish was texting me nearly constantly (and I was happily texting her back) about what she wanted on our date. Years of poor fulfillment had given her a considerable wish list, and it wasn’t going to be easy to fulfill them. But we planned a night for her to come to my house. Normally I would cook dinner and we would enjoy it together, but this time she wanted more and didn’t want to waste any time.

I saw her car pull up and opened the door as she walked on my porch. She was wearing heels that made her only a few inches shorter than my 6’4” frame, and I welcomed her a kiss on the lips, which she answered by parting hers. Almost instantly we were making out in the doorway with my hand sliding down to her ass pulling her inside. As she came in I closed the door behind her, and kept kissing. She was wearing a wraparound sun dress, that complemented her long, gray-streaked hair, which was pulled back in a ponytail. Read more »

[F]inding [M]yself exposed in the park

So, while I was living in New York, I decided to poke around on OKCupid, advertising myself as married and in an open relationship. I wasn’t really looking to make myself emotionally available, and we were far enough from the city that it quickly proved hard to find people who really could engage. I got a few supportive messages here and there of the “it’s not for me, but happy for you” type, but it just wasn’t what most people were looking for. Which didn’t really bother me, after all I’m not looking to hurt anyone, but it did get frustrating. Then a new person popped up, in her mid-40’s fresh of her divorce and first dipping her toes. I sent her a note, and while her response was hardly a sign of interest, she wasn’t closed off. So we chatted for a bit, and I got to know more about her and her situation, and I could see her starting to think that maybe I could be a nice first fling. Read more »

Making her naughty wish come true [MF] (cheating, really cheating)

So, this is the follow-on to this post: https://www.reddit.com/r/gonewildstories/comments/82mi2g/mf_the_best_head_i_ever_got/?st=JEJOL1WU&sh=ddb578e6

After our first meeting, and her orgasms at my hands and my orgasm in her mouth, the flirtation on our phones found another gear. One thing about me and many of my experiences is that there tends to be a LOT of play over text messages before. It’s fun to get the other person really turned on, and also fun to really explore what each of us want. And over the next few months we were really working each other over. I did come back to her breathy request at the end about wanting to feel my cum inside her. This one really curled my mental toes, even though I’m super militant about safe sex. (How do I know I’m clean? Because I don’t make fucking exceptions!)

But then she revealed she had condoms in her purse with her that day. So maybe we could have gone that next step that day after all. I hadn’t brought any, so I had put that thought out of my mind. The image of her swinging her leg over me and guiding me in, however, was definitely attractive. But she also wanted to insist on a bed next time, and I couldn’t blame her. Read more »

[MF] The best head I ever got

It was a couple years ago. I had connected with another Redditor who liked my stories online and we had been exchanging messages. She lived in Germany, a few hours from me, so we both knew it would only be a matter of time before we met. She was married, but frustrated, and our texting grew more flirtatious the infidelity became part of the kink. It wasn’t just that she wanted some more, the fact it was a secret made it better.

The day did come when we first met, in a village a safe distance from her home. We walked around a bit, talking, feeling each other out. Eventually I found a quiet corner behind a church where there wasn’t really anyone else, and she realized where we were, too. She leaned against the wall and I stood in front of her, kissing her. The first kiss was great, and began gaining momentum, our tongues sliding over each other. I slid my hand under her shirt, and she helpfully unclasped her bra, so I could feel her bare breasts in my hands. we were still both standing, kissing like teenagers, my hands groping her as she rubbed the bulge in my trousers (I was still wearing a suit and tie). Read more »

Playing with things that are not mine [MF]

I first came to know Lily through Twitter. (It’s one of my weird abilities in life to convert “online interaction” into “woke up next to her.”) In her case, she was friends with another play partner of mine that I had spent a marvelous weekend in the Reeperbahn district. Although my history with her friend was never REALLY made explicit, we kind of knew what was up. Lily, however, was married, and in a very conservative religious community. While I was trying to be circumspect about who I chose as partners at the time, and avoid the drama of an angry spouse hunting me down, there was a chemistry there I couldn’t ignore. Especially after seeing her get involved with a second-rate character in an online-only thing, I kind of felt that stupid male competitiveness thing kick in.

So I finally decided to parlay the online chemistry into a date, which turned out to be a very easy proposition, as she was even more interested than me. We picked a weekend her husband would be away, which he was on a regular basis, and I booked a hotel room in her city but a different neighborhood. Although traffic wasn’t my friend, I made it there within a reasonable time of my target, and she was waiting in the lobby, her hair neatly tucked under her hat, dressed conservatively. She was short, about 5’2, with dark hair and pale skin. I’m about 6’4”, so the difference in height was really noticeable. Read more »