Getting fucked by a client while on a business trip…again! (M/F) NSFW

You may recall my earlier story about being fucked by my client Dave at a business dinner:
https://www.reddit.com/r/gonewildstories/comments/3e5bbz/fucking_my_client_at_a_business_dinner/

Here is what happened after…

I woke up to the obnoxious sound of a cell phone alarm. Without opening my eyes, I could feel that I was in my hotel room (quite a normal feeling since I stayed in that hotel a few times a month for business). I rolled over to grab my phone while simultaneously realizing that it wasn’t MY phone going off and that I was quite a bit hungover. That’s when the events of the prior night came flooding back to me. The business dinner…the drinks…running into Dave near the restrooms…how he had smiled at me…how he had forcefully grabbed me and kissed me…oh god did anybody see us? Then I remembered how he had come up behind me in the dark bar and slid his hand up my dress…I recalled the sheer ecstasy of his finger sliding beneath my underwear…… and the fear of being caught in that position. Oh right, and then the amazing sex we had had in this very hotel room and then again just a few hours ago. I started to worry if this morning was going to be awkward, when I heard him switch off his alarm and felt him roll up behind me. He moved my hair out of the way, kissing my neck and said “Wow, that was an incredible night, I am seriously dreading going to work today.” I smiled and said “Me too, at least I just have a couple meetings and then I’m on a train back to NY.” He said “Oh right, well I better get going.” He dressed quickly and came over to sit by me in the bed. He leaned in, kissed me, and told me that he had a great time and that I should let him know when I was back in Boston next. I agreed.

Kiki

This is the story about how I met the most important woman in my sexual history. If Kiki is reading this, I hope she remembers who I am, and sends me a PM.

I was a shy kid with few friends all through high school. I went to college having gone to prom without a date, and not having dated anyone all 4 years. I tried dating once I got to college, but after having my heart broken a couple of times, and being friend zoned by a woman I pined over for 2 years, I was still a virgin at 22, and frustration was setting in.

By that point, I had discovered that the Internet was a good way to kill some of the frustration I was feeling. I discovered cam models, who would pay attention to my needs, and then get naked for me. I  remember accidentally spending over $70 on a session once because we got to chatting about other stuff than sex, and the minutes just kept ticking by.

Our First Night at “The Club”

Where to start, this outing had been a long time coming. Cindy and I had wanted to explore non-monogamy including swinging for a while, but living in a small town, we had limited opportunities to do so, that all changed with a recent trip to the “big city”.

As we’re planning to move out of the small town we’ve called home for years, Cindy and I had a chance to go to the city we’re moving to and check it out. One of the things we desperately wanted to do was go to the club. Finding a place wasn’t hard, in fact for a beginner the choice is mind boggling, with no less than four clubs in the city to choose from. After sending out an email to the hosts of the club we chose, introducing ourselves, we very promptly received the appropriate information and we were going to the club!

The entire day leading up to that night was very charged between Cindy and I. I was nearly constantly hard, and C wasn’t helping the situation exactly ;). Our first stop was an adult store because why not? Cindy found a gorgeous purple and black bustier/corset and fishnet stocks that made her look like a million bucks. She wore the corset to the club that night with a light fluffy blue dress over it that totally said “girl next door”.

A good day off

This happened just this morning, so it’s still fresh in my memory.

We made plans for me to come over about 10. All her kids would be at school and her husband was out of town.

As soon as I got in the door we were all over each other. Hands exploring, tongues in each other mouths. Clothes were getting stripped off with every step.

As she led me towards her bedroom, my hands grabbed her perfect tits. Just a little larger than a handful, with hard nipples I could feel in my palms.

We made it to her bed and continued making out. As we continued kissing and nibbling, my hand slid between her legs.

I found her nice and smooth with her the hood of her clit just barely peaking out between her lips. As I grazed it, she shivered.

I chuckled to myself looking forward to backing up my claims to her of loving to go down on women.

I broke our kiss, sucked on one of those perfect nipples, then slid my tongue down her stomach.

I could feel the heat radiating from her already.

College Orientation [M/F]

I’ve browsed this sub for a while and figured I would finally contribute some material. I’m graduating from college in May and was thinking about some of the times I have had over the course of my career and thought others might like to hear them. The first memory is about my time as an Orientation Leader at my school. It was an easy gig that paid decent money to essentially just walk kids around campus. Most of these sessions were just day sessions but there were always 2 overnight sessions. This mean kids would stay over on campus and have time to sort of feel out what it’s like to stay there. Luckily for us, we were really only responsible for the kids until 9pm then we could do whatever we wanted. This summer in particular, I had just recently broken up with my GF and she had given me a pretty dumb reason for the breakup so I was on the hunt.

Hotel Sex After A Six Month Dry Spell. [m22/f20]

It’s been a while, so I thought I’d make another contribution. This one is about the time Rey and I fucked all night after not having sex for six months.

This is what Rey looks like, btw: http://i.imgur.com/D7RDLn0.jpg
(Not her, but really close)

As I’ve shown in my previous posts, Rey was a bit of a freak. Just before we started dating, she got out of a long term relationship that involved not having sex for the last several months, and having boring sex with only her ex’s kinks more or less forced on her. Terrible sport. By the time she met me, not only was she dying to try some of her own fantasies, she was desperate for sex in general. So naturally we had a lot of it.

Not long after that though, Rey got accepted to her first pick college. After calling in most of senior year and being too depressed about her past relationship to do anything in her first (and only) semester at community college, getting accepted to a private university was a huge opportunity for her. I might not have explained this with all of the fuckery before, but Rey was incredibly smart, and for the entire time I’ve known her incredibly driven. She said that my drive made her want to be better, so I guess we made each other more driven (?), but she was relentless in her pursuit of education. Again, big deal.

Alone in the Dark (His perspective) [MF][bd][Mdom]

This is a companion piece to ‘Alone in the Dark’

You’re alone in the dark until I enter.

I open the door as little as possible, so not enough light falls on you for me to see you, and I close it quickly.

I stand there silently, giving my eyes time to adjust, until I can see the discreet glowing stickers placed on the frame you are strapped to. There are just enough of them that I can orient myself and find you, but you have no idea they are there.

My feet bare, I softly pad toward you, and silently place some of the items I’m holding near your feet, then move around to your left side. I can smell your delicate, floral perfume. I wonder what you look like. What colour is your hair, your skin, your eyes? I’ll never know.

I gently place my hand on you head. You start in surprise. You weren’t even sure anyone had come in, were you? I stroke your hair, thick and lush, and bend to smell it. Clean and fresh.

Alone in the Dark [MF][bd][fsub]

I’m alone in the dark.

I’m bent over a wooden frame, a padded leather block supporting my hips, another under my shoulders and upper chest. My arms are stretched out ahead of me, my wrists secured to a post. My legs are spread, and my ankles shackled to the frame. I’m wearing just a plain white bra and panties.

I’m not sure how long I’ve been here. Two, maybe three hours. Plenty of time to think about what might happen, who might use me. A man or a woman, men or women. Would they use me gently or cruelly? Caress me or whip me? Call me ‘sweet thing’ or curse me as a filthy whore? And when?

I’ve run though numerous fantasies in my head, sometimes thrilling, sometimes frightening, but always ending in damp panties.

It’s pitch black, not the slightest hint of light, and completely silent.

Abruptly, a click from behind me, and a shaft of light as the door opens, then darkness again as it closes.

Did someone come in? No matter how hard I strain, I can hear nothing but my own heartbeat.

In the middle [Bi] [FMM] [Anal] [Reluc] [Fdom] [Msub] [Mdom] [first person]

I’m in a room, I don’t know where it is, could be a hotel, could be somebody’s house, all I know is that it isn’t my place. There’s a bed against one wall and an armchair facing it but there’s also a mat on the floor and I realise that the room is very much used for one thing only, and that thing isn’t sleeping. The door opens behind me but I’m not allowed to turn to see who it is because She’d punish me if I did.Her voice both puts me at ease and inspires fear in me simultaneously.

“Jazz, I’m glad you’re more with it now. I’ve brought a friend here to help me to teach you a lesson because you’re such a quick study.” Her hands run between my legs from behind as I remain as still as possible on all fours. My cock starts to stiffen due to a combination of the tone of her voice and her touch and it’s then that I feel her slip something over the head and fasten it behind my balls. She obviously needs me hard for something. She walks into view and I see another pair of legs beside hers they could be anybody’s legs, but I know they’re not female from the way he stands.

[M]y [F]irst Tinder Hookup After Moving to Orange County

Long time lurker, first time poster to r/gonewildstories. If I’m being completely honest, this is my favorite subreddit, so I thought I should probably stop freeloading and contribute! This story comes from a few months back, but it was a good time. Here is a small window into my life, my personality, and some of the interesting parts of online dating that kind of contextualize this story in my mind. I hope you enjoy!

So fade in: It is August, and I just moved to Orange County in July for a new job as at a small startup company. I’m excited for many reasons, but if I’m being honest, one that was pretty high up there was getting my own room. For months I had been living in my own living room because my best friend (female, lesbian ex-gf, now completely platonic sister from another mister; long story) had needed a place to stay while figuring out her new direction and going back to school, and so at my old place, I had offered her my bedroom since I only had a 1bd. Now, having moved to Orange County into a 2 bedroom (she needed a change, and I didn’t really know anybody in OC, so I invited her to go with), I was pretty jazzed to be in a two bedroom since it would allow me some of the privacy I really needed to…have guests.