Tag: Straight

Wedding Date [f/m]

I've known Jason for almost 10 years now. We've always considered ourselves as very close friends, where if I drank too much and stayed over with him in his bed, we might cuddle a bit and pass out innocently. Until that one time a few years ago when we went to a wedding together.

We partied all night at the wedding, which spilled over into an after party at a local bar. Shots were ordered along with mixed drinks, and the next thing we knew, we were in my best friends bed completely naked. He had my legs spread wide and was sliding two fingers in and out of my wet pussy slowly, making me moan. The booze-fueled night had forced us to throw our inhibitions out the window. So, when he grabbed my legs at the ankles and brought my legs up over his shoulders, I was more than ready to feel his big dick in my tight hole. Read more »

[M]y night of [F]un with Iris

It’s Saturday night and here I was at a party with my girlfriend, Iris. We barely knew anybody there as it was a friend of a friend of a friend’s party that Iris got invited to. I’m not really into the party scene; I mostly like to hang out in smaller groups, and am mostly a fan of one on one time with friends, and especially Iris. How I landed her I’ll never know. She’s about 5 foot nothing and packed full of energy and fun, always coming up with creative date ideas and different things to do. Nevermind the fact that she is an absolute babe. Iris has long flowing blonde hair with a little streak of purple through it, rocks a sweet pair of B-cups and has quite the nice round ass, which of course is always fun to grab a squeeze of real quick. On this night in particular she was wearing her nicest red top with thin black vertical stripes running up it, along with some blue jeans. Me being the slob that I am came dressed in my nicest Iron Maiden shirt and some older black jeans. I basically looked like a Maiden roadie. Fuck you, Maiden is awesome. Plus on this night I was DD, so I basically cared about as much as the writers of Heroes did after the first season. Read more »

Good sa[m]aritan, helping the secretary [f]ile.

Im a Warehouse Supervisor for a start up (kind of?) corporation. I have been there for about four years and in general, I think I am pretty well-received. I have made lots of friends and gained several raises since I started.

I had a good friend in payroll, her name is Kim. I knew her prior to this job and I am good friends with her boyfriend. We'd often smoke weed together or go get lunch. She would always fill me in on the rumors and gossip and general happenings at work.

One day she spilled the beans on our secretary, Shobna. Shobna is in her mid thirties and recently divorced. Kim filled me in on Shobna's husband, how they basically have had a dead bedroom and married out of convenience since they had children.

Apparently, Shobna confided to Kim about her recent sexual conquests and hooked up with two guys within the same night. A friend's party and then a bar. Two thoughts came to my head, 1) did she use protection? and 2) how can this happen to me? Read more »

Replaced by her sister [MF] [cheat]

So, my girlfriend was out of town. In fact she was out of the entire country. She had been gone six weeks at the time and wasn’t going to be back for another six. She had been accepted for an Erasmus term which meant she got to spend twelve weeks studying in Italy. I was delighted for her. The only issue I had with the plan was that it meant there would be no sex for almost three months. I tried to keep busy so my mind would be occupied and I had been ‘sorting myself out’ but the longer time went on the more difficult it got and things that would make me horny seemed to be seeking me out.

A couple of the lads had arrived back in town. We had planned our holidays so that we could have the time off together to catch up. Since college finished last year we had been growing steadily apart so when we had an opportunity to get together we went all out. We met back in our local and sat in our usual spot. The conversation of turned from work to sport to absent friends and family to women and memories from school. The lights flashed and before we knew it last call was to be ordered. We all decided that the night was still young so we moved on to a club. It was a student night which meant the place was crawling with people but after a few years going through those doors we had gotten to know the door man who just waved us through. Read more »

“My best friend who is straight just made me cum.” That’s interesting I thought to myself [f/f] Part Two

If you haven’t read part one read it here http://www.reddit.com/r/gonewildstories/comments/3bcwh8/my_best_friend_who_is_straight_just_made_me_cum/

Sorry for being a tease! And here we go

As Chloe went to her room I went into the bathroom and gave myself a pep talk in the mirror. I’m confident in my vagina pleasuring abilities but I was still nervous as fuck. I took a deep breath and put my game face on.

I walked into the bedroom and there was Chloe standing just as I had instructed her to. “You are stunning Chloe” I told her breathing her in. “It’s taking everything I have right now not to put my hands all over you.” Seeming to come out of the trance I had her in she rushed out the words “No, No that’s good you should do that.” I lifted my finger to her lips “ Shhh there will be plenty of that but 1st I’m going to tell you exactly what I’m going to do to you.” “You see,” bringing my forehead to hers so that our lips were so close that when I made certain sounds they would touch, “the real trick to foreplay is the moment before you kiss for that first time.” Moving up to her ear I ask her “I’m going to tell you now how I’m going to make you cum first.” She sighs deeply “Yes “ Read more »

Mixing pleasure and business [m/m]

This is the sequel to http://www.reddit.com/r/gonewildstories/comments/1zclih/mixing_business_and_pleasure_mm/

tl;dr – I met someone at a business conference in another state and we found out that we were both curious about other guys, so we blew each other in my hotel room (as one does, I suppose).

After we both came into each other's mouths that night, we didn't end up doing anything else (yes I know I hinted at it at the end of the first story), as we were both quite spent and I had to leave the next morning on an early flight. We parted with a nice long kiss and made a promise to catch up again when I was back in town. This was six months ago.

As it so happened, work sent me back for another conference, but this time my one night stand (let's call him Jacob) wasn't required to attend this time. We exchanged numbers after our encounter last time, and so the week before I sent him a text to let him know I would be back. The reply was quick from Jacob – he still thought about that night, thanks to my 'amazing cock-sucking skills' (yay!), and that he would meet me after the conference to have 'dinner and more ;)' Read more »

“My best friend who is straight just made me cum.” That’s interesting I thought to myself [f/f]

-Holy wall of text batman. I added a **** if you want to skip forward to the sexy times. There is some backstory here and those are the type of stories I enjoy reading so I wrote mine that way. The jist of it my best friend since high school, whom I came out too, who had been in the straight girl box got very forward on her 21st birthday….

Edited cause I can't spell for shit

I've known I was a lesbian since I saw Lindsey Lohan in Mean Girs for the first time. I mindless uttered "wow she's hot." The group of friends I was with joined in with "Yeah she's so pretty, oh my gosh I love that top etc.." I realized I meant hot not in an envious way, but in a holy I want to play with her tits and make her cum kinda way. (Probs more pg13 though in real time because I was in 7th grade) Read more »

Worst prostitute ever! Part III [m/f]

Oral sex can at times be a fairly complicated process, whether it’s a man or woman you’re performing it on. It’s made harder if you were in a situation like I was, where I had a large butt plug sitting rather uncomfortably inside me.

As a prostitute there are a few key points to consider when you’ve got a client’s cock in your mouth. The key one is when to put the condom on him. It was entirely up to me when to put the condom on during oral sex. With my first few clients, I’d always put it on immediately but then quickly discovered that caused all sorts of problems. It was hard to get guys to cum, they’d lose their erection and decide they wanted to fuck you vaginally or anally instead. It was easier just to leave the condom off and either put it on towards the end, or let them finish by masturbating and ejaculating onto me.

The second point was whether to let a guy put his hands on your head to guide you. With some men (not just clients) this could be seen as an invitation to try and jam their cock down my throat. However by letting him guide me, they often ended up finishing a lot faster, and provided I kept both hands on the base of his cock I could usually stop men from getting carried away. Read more »

Risky sex with the Japanese student teacher

Skip ahead to SEXY TIMES if so inclined.

Midori

When I was in my 20s, I moved to Japan to work as an English teacher in the north. I worked in many different settings but spent most of my time in a sort of community college. Every year at our school, we would hire 6 college education majors in their senior year for some hands-on experience. They worked with us for a year at a time, learning English and American-style education while assisting us with our duties.

The Japanese academic year starts in April and essentially goes year-round. In July and August of every year, a new set of Japanese recruits would rotate through our school for one week at a time as part of the interviewing process to start working at our school the next spring. Some of the applicants were older, more experienced teachers, but most of them were juniors and seniors in college. Read more »

When hiring two prostitutes to have a threesome, there are some points to consider. [MFF]

The absolute key thing to remember is to try and make sure that the prostitutes you hire don't hate each other. There are other factors as well, but that one is pretty key.

Let's call our big spending customer Alex. For the 6 months I'd been working as a prostitute he'd been a regular of mine, for the most of it.

He was a bit weird, and a lot of the other women at the agency didn't like him, but I got on with him pretty well. With me at least he directed a lot of his energies towards role play and light humiliation, rather than the more extreme stuff he often wanted with other women.

He was that key thing, a regular. Someone that would adjust his booking around your timings. He'd book me for two hours twice a month on whatever time was convenient to me, so it spared me having to fight for bookings with the agency.

Let's call my colleague Alice. Straight off Alice called herself an escort rather than prostitute. Despite the fact that like the majority of the women at the agency rarely actually did anything that included the social aspect of escorting with the clients. Rather than a descriptive term, I felt she used it as a kind of euphemism, for how she earned a living. Read more »