NSFW story — Page 10119 of 11466 — collection of stories you shouldn't read at work

[M]Had a fun time with a [t]rans escort

So ive been having a rough few weeks and I looked up escorts in my area. Found a bbw blonde thick ass transwoman. She was at a hotel 10 mons from my job so I couldn’t say no.

I called her, we set up a time and I go to her hotel room. She was wearing a cute right dress and gave me a hug.

We chatted a bit, she had just flown in from out of town like an hour earlier. I lay down the agreed amount and we both undressed. She gave me a blow job with a condom. I am a striaght male but I couldn’t resist asking her to put one on so I could. She is very fem, and is on hormones so erections arent easy for her but I kept going until felt her swell up in my mouth.

I got to eat her ass, watch her twerk, fuck her, and cum while kissing her.

I womt forget this experience and glad it happened

[m][bi][inc] How I became a sissy

It all started when I was in school, I was a skinny, quiet boy still waiting for puberty to hit. I had just discovered masturbation when I would take a day off school to watch porn and play with myself until my parents came home. At first I was normal enough, playing Hentai games and watching videos and climaxing over and over and over until one day I saw a pair of my Mothers panties on the landing out for the wash. I only noticed them because the night before she had been fucked by my Dad, I know this because I was listening in and playing with myself. I kept the panties. I would rub them on my cock and sniff the creamy spot and it would send me into a frenzy until one day I decided that I would try them on, The feeling of my mums panties against my cock was like nothing id felt before, I went week and just lost myself. on my knees in my room leaning back and stroking my cock until I came all over myself. At that moment I think was when I became Melissa. I would wear them to school with the lace pulled up into my ass and my skin pulled back so every movement could be felt. Fast forward to when I was older, I had already started photographing myself and playing with older men on Omegle and just being a lewd teenage sissy when I decided I would complete the image. I would play in my mothers panties often so why not her bras and heels as well? I was truly a sissy and it only got worse from there. When I was 18 I started roaming the streets at night looking for trash bags that people would throw out with clothes in, the ones with Lingerie and underwear in I would take and the rest I would leave. I found skips and lingerie sets most of which you can see in my albums on imgur. It wasn’t until I turned 20 that I started posting them places. I got my first job and with my first pay check I bought a wig and some anal trainers which turned out to be way to big for my tight little hole but they were fun none the less. Every day I become Melissa more and more and I just need to serve someone, A sissy, another woman, anyone I have so much exploration to do and I hope I can find someone to finish the transformation which started all those years ago.

Fucking my college professor. [FM]

I posted on here a while ago and ended up deleting my account/posts because I suspected somebody had outed my professor, but turns out it was unrelated to my Reddit content. SO I’m back!

Back when I was 18 and a freshman at a major public university, I was taking a gen ed course (can’t say subject for privacy). My professor was insanely handsome (for writing purposes I’m just going to refer to him as Professor/my professor) and I crushed on him throughout the whole semester. Turns out that my thing for him wasn’t as discrete as I had hoped, because the day after the semester ended, I got an email from Professor. REALLY wanted to attach the email for y’all but I just looked back and alas, since it was to my university account from many semesters ago, it was automatically cleared away. Anyhow, in summary, this is what it said:

“Hey Student, I really enjoyed having you in class this past semester and I hope you enjoyed me as your professor. Tell me I’m not crazy and that you might be interested in me beyond just discussing (subject)?” Read more »

[MF] A fond travelling memory

This story took place in May while I was backpacking through south east Asia. I left out all the details that could lead to her identity. Scroll down if you want to get to the action right away (:

One day I was scrolling through my tumblr dashboard, when I stumbled upon a picture showing this beautiful girl. I noticed that it was a submission to a blog that is all about pierced nipples and this girl wanted to show hers to the world. The caption said something like that she did them without anyone knowing and that they deserved some lovin’. And she was right. I’ve always been a sucker for pierced nipples, but hers looked especially good. Together with her petite frame and the tan skin, the picture was mesmerizing.

I decided to give it a try and shoot her a message. I know these things come off as creepy quite fast, so gave it some effort to be as polite as possible. Judging from her tumblr, she seemed to be a very talented artist, so I complimented her on that… and of course her beautiful submission. She was flattered and we started chatting. Let’s call her Janice. Read more »

[MF] Making use of a rest stop…

A little goofy and maybe a questionable location, but thought I’d share especially since my wife can be a bit reserved at times, it’s always wild when she finally lets loose.
My wife and I are fairly young, and often have taken trips to Cincinnati, which is only a few hours away. Recently on the way up, I reached over (while driving) with one hand and started rubbing her bare legs (she was wearing a skirt). Long story short, my finger eventually ended up inside of her for a few moments, sort of teasing her. Before long, I took ahold of the wheel with both hands for a few moments, and notice she was not only starting to finger herself, but was recording herself doing it for me to enjoy later, which is definitely not like her! She likes to make me happy, but is pretty self conscious for some reason, and can be pretty conservative at times.
I ended up reaching over and taking her to an orgasm. That wasn’t quite enough though.
Shortly after we pulled into a rest stop that looked like no one was at anyway (fairly early morning). We both went into the family restroom and I pulled my shorts down as she took off her skirt. She sat slightly up on the front of the sink (her panties still partially covering her butt), we wrapped our arms around each other, and then I went in her as deep as I could. We were a little worried it may be uncomfortable the way we were angled, but with her slightly raised up, it felt amazing for us both. We went hard and fast, making it difficult for us to be queit. It didn’t take long for us to both orgasm.
We then snuck out of there as queit as we could so no one would notice (despite no one else ever pulling up seemingly).

[MFF] Two people on the rebound is intense. (part 2)

Part 1 is [here](https://www.reddit.com/r/gonewildstories/comments/6wk2fj/mff_two_people_on_the_rebound_is_intense_part_1/)

Where was I? Oh yeah, So my Blonde friend and I had started to perform having sex over Skype in front of a pixie looking redhead friend from one of my previous jobs. We had invited her round to watch and she agreed.

Remember how nervous you get when you are about to have sex with somone for the first time. Imagine the same only you are going to have an audience of another attractive girl. Performance anxiety can creep in and ruin it for everyone.

Wine helps.

It helped me.

So the day arrived and the doorbell rang. I was a strange experience standing in a room with both of them, knowing what we about to do.

So we all had some drinks and then moved to the bedroom. Before long I was on the bed with our blonde friend and our pixie friend was curled up on a chair watching us.

We performed anything she asked us to do, apart from anal, our blonde friend wasn’t keen. So for two hours our little pixie friend got to watch and instruct us on what she wanted to see. Read more »

[MFF] Two people on the rebound is intense. (part 1)

So I was dumped, and she had just dumped somone. We were work colleges and were both young and single.

She was a petite blonde with the kind of ass that would make some men hate themselves for knowing they would never even get close to an ass that perfect.

One night with the work colleges was all it took before we were fucking each other. It was a fun causal affair.

But then one night when we were messing around we tried doing something on chatturbate. Was just a simple blowjob but she wore a mask… but she wasn’t keen on being seen by somone she knew.

So the thrill-ride was over.

Then I bumped into an old friend from an on older job.

She was a little cute pixie looking redhead who was a bad girl with an innocent face. Nothing happened other than we spoke about the old place and how it sucked. The usual.

So a few days later I was over at our blonde friends place, we are just watching TV and getting in the mood. Then it hit me. Read more »

[MF] the banker(23f) and I(33m)

So this happened several years back and still one of my fondest memories. Her name was Clara and she worked at a local bank I frequented a lot for obvious reasons. Kay was a petite little girl about 5’1″,105lbs, dark slightly longer then shoulder length hair dark hair, mesmerizing eyes (almost disneyesque), 32a/b chest and a cute bubble butt for a white girl. She had a great warm personality that seemed like she was just geniuinely nice to everyone. Now me I was 5’11 190lbs red short hair.

Every time I saw her we’d chat about common interests and things started to progress towards flirting. One day I mentioned her nail and how I loved what she did with them ( I have a bit of a thing for well done nails) she smiled and presented then all playfully saying how she’s running out of ideas on what to do. I mentioned a starry night theme (I just watched the Doctor Who episode with Van Gogh and she knew what I was talking about) later that night I get a message on FB from her asking for my number bc she wanted to show me something. I give her my number and a few min later it’s a picture of her new starry night nails. Of course now I’m inteigued. One thing leads to another and the flirty becomes x-rated over texts. Read more »