[MF] The Day Before We Met

I met Elena on Ashley Madison, where I was — predictably — looking to find
someone as bad as I am to flirt with, hoping all along that it would turn into
something more intimate as it went. We started off with pretty good chemistry,
if I do say so myself, and determined that we were, if not neighbors, close
enough that we would be able to make it to the same hotel room at the same time
soon.

Flirting progressed to some pretty serious dirty talk. Elena has a delightfully
dirty mind, and a killer body. Sexy curves, long straight blonde hair, a
mischievous smile and an endlessly dirty mind. Neither of us pretended we were
each other’s one and only affair even from the start, and I can tell you…
knowing that the woman you’re going to be sleeping with is seeing other guys is
a special kind of *hot*.

We made plans to meet for lunch to see if our solid online chemistry was going
to turn into something physical. The day before that, she had a date with
another potential affair that hadn’t net managed to close the deal with her, and
I … well, I got impatient. I started texting her dirty thoughts in the morning
and didn’t let up, telling her how much I was looking forward to all of the
illicit fun we’d be having really soon.

Teasing my old high school friend [FM]

This is a LONG confession so I apologize in advance!

In the past, I never noticed, but my friends were always telling me that I naturally teased guys with the stark contrast between my sexy figure and my genuine innocent personality. My figure made regular clothes very sexual, and I wasn’t really aware of it until recent. I would be happily sucking away and deepthroating on popsicles with happy sighs without realizing what I looked like (don’t laugh!). I’d bite my lips and moan in frustration when working on problems. I’d even get down on the floor (face down ass up) to grab things with no consideration as to how my ass looked. I was really naive. Like so naive that if you didn’t know me, you’d think I’m just messing with you.

Despite all this, I thought they were full of shit. I still had major body confidence and self esteem issues, and I thought they were saying that to just make me feel better. Me, sexy? A tease? HA! I wished. I did continue to wonder though. That’s why this past summer, I came to the conclusion that I needed to go a little outside my comfort zone. I decided that I was going to take a baby step and try some simple intentional teasing. Maybe my friends were right. I just needed to put things to the test.

[MT] My first experience with a trans woman

I had been browsing sites like CL, OKCupid, POF, etc. for years trying to strike up a conversation with a legitimate trans woman. Most would end up being either professionals, or bad CD’s in wigs (nothing wrong with CD’s it just wasn’t what I was attracted to). I am a straight guy in terms of my dating past and sexual experiences, but the thought of being with a woman who also posses a penis is something I have been drawn to. I am 5’9″, in shape with a decently defined 6 pack, and oblique muscles, clean, and a working professional so I thought finding someone through these sites would be easy and we could go on a date and feel each other out.

Unfortunately, this was not the case and for years I would message girls only to have things fall through at the last second. Sometimes this was my fault since I was new and nervous. I had no experience and would also end up worrying that I was going to be chopped up by some axe murdered via Craigslist. Years had gone by, and after a long term relationship ended I decided I was serious about exploring this new side of things. In reading online I noticed that a popular app seemed to be a good place for linking up and actually connecting. So I downloaded it, and spend a few weeks messaging and looking around to no real success.

Making her cum on a train journey [MF]

The story of what happened when me and my ex-gf/sub found ourselves on a quiet train home after a day out…

——

We sat by each other on the train, the light gradually dimming as the sun set. We hadn’t been able to keep our hands off each other all day as we walked through the city with our fingers intertwined, lips locked and bodies pressed against each other almost constantly.

She was sat a little on my lap, her body resting against mine as we kissed. Her soft, supple lips felt divine. My right hand slipped up her back and started to lightly pull at her blonde hair.

I was growing hard and she could feel me through my jeans. She smirked and started to stroke me through the fabric. Her fingers wrapped around the width, sliding up and down, drawing a soft moan out of my lips.

She smiled and began to kiss my neck. Softly. Sending shivers through my body. I pulled her closer to whisper in her ear. “Naughty girl,” I said with a soft growl, she gasped slightly as the syllables left my lips. “But two can play at that game.”

My [F] trainer [F]

I’ve been working out with the same trainer for about six months. We switched to virtual trainings a few weeks ago for obvious reasons. Maybe it’s because I get to see her from different angles than when we are together at her house or maybe it’s because I’m constantly fucking horny from looking at porn, reading stories, and getting dirty DMs on Reddit but, for whatever reason, I was so turned on today.

She is cut but in a very feminine way. She has fake tits which are a little smaller than I prefer but she wears tanks that show them off. Her ass is insanely high and tight. I doubt it’s intentional because she seems super straight (although she did compliment me on my “great high, round ass”) but when she leans into the camera, my pussy tingles.

My home gym is in a room in the basement. We finished up a hard workout and when I knew we were completely disconnected, I laid on the floor and played with my clit until I exploded.

I’m starting to see a pattern ?

That Time I Got Jerked Off in a Sleazy Porno Theater [MM]

None of my friends know this story, none of my ex’s, or even my wife, but it’s absolutely true.

I found my first porno in my Dad’s sock drawer when I was a teenager and it was one of the classics, Taboo, on VHS. This movie was a classic, Kay Parker and her fantastic huge tits, was such an eye-opening experience for me at that age and molded me into the horny guy that I became. I’d watch it whenever I had some time to myself and since this was before the internet, I really had to enjoy what I had since I couldn’t go and get any other films. Other than a few Playboy’s and Penthouse magazines, that was the only adult entertainment I could find. A few of my friends and I would trade movies that they also got, from their Dad’s or from an older brother or something.

A Friendly Night Out (MMMMFFF)

They had all be friends for years now. They met at work and after meeting each other they started going out to concerts, bars, and just about everywhere else together. The seven of them were almost more like family than friends. Amber and Rus were housesitting for a friend with a large studio apartment downtown. They had invited everyone out the bar hop and then crash at the apartment.

Only Amber and Rus were a couple. Amber was average height, brunette with blue eyes, tanned skin, and a skinny build. She had small perky breasts and liked to dress in revealing and fashionable clothing. Rus was tall with dark hair, and athletic build. Despite his size, he had a pretty low tolerance for liquor.

Rex, Brent, and Mike were in a band together. Rex was the singer and guitarist; he was slender with slicked back auburn hair and pierced ears. Brent, the bassist, was also of slender build with blonde hair, blue eyes, and tattoos covering both arms. Mike was the drummer. He had dark hair, a ripped body, and tattoos covering most of his skin below the neck. They hung out together and rehearsed almost every night. They were all single, but usually found a girl by the end of the night.

Sleepy morning memories

My eyes open and I awake from my sleep. I’m lying on my left side facing into the middle of the bed. Between me and the light coming in through the early morning window is you. You’re facing the same way as me, so all I see is your exposed back that’s not covered by the duvet. You’re completely still. My eyeline follows the curve of your outline from your neck over your shoulder and down to your waist and the small of your back where your two Venus dimples frame an inviting scene. After that you’re covered up with blanket, but already I know I need to get closer to you.

I wiggle in towards you to be your big spoon. You let out a comforting sigh the instant our skin
touches and wiggle your hips into me so that there’s maximum body contact. My hands instinctively wrap around and envelop you, starting on your left shoulder and moving diagonally across your chest, in between your breasts, on to your right hip and down your thigh towards the knee as far down as I can reach. Your breathing continues to be relaxed, consistent and comforting. My hand
moves back the opposite way, but before it reaches your shoulder you dip your head slightly and catch my thumb in your mouth. Very tenderly you start working it around your tongue, caressing and kissing it with your lips whilst continuing to quietly moan. All the blood in my body floods towards my crotch. I’m instantly hard; throbbing in anticipation of what’s to come. I’ve no idea how I’m managing to be so cool and restrained.

[FM] deep throating and finger fucking in a Bed Bath and Beyond parking lot

A couple years ago I hooked up a man whose dick had a slight curve. I dont know if it hit my g-spot but it was the first time I squirted when I came. From that moment I became his complete cockslut. Anytime he called I’d come running eagerly my panties already soaked in anticipaton by the time I arrived

Once we only had 15 minutes so we met in a Bed Bath and Beyond parking lot because it was nearby and in a parking structure so a bit private. I got into his car that only had slightly tinted windows but I didnt care. I had slipped off my panties in my car and was wearing a dress. He unzipped his trousers and i knew exactly what to do. I swallowed his warm thick cock trying hard not to choke. He was leaned over towards me and slipped his fingers between my legs. I lifted my dress to my hips so be would have better access. While my head bobbed up and down on his stiff cock his fingers tugged on my pussy hairs then parted my folds before he plunged them in deep and started finger fucking me with no mercy. I bucked my hips against his palm as his cock eased further down my throat.

The Eternal Convention[fantasy][non-con][sloppy kiss][anime][sailor moon]

Alex woke up in his hotel room with a smile and a feeling of excitement. He had travelled from city to city to follow the Sailor Moon convention, and was at the final stop before returning home. He was looking forward to enjoying his last weekend of pretty girls in cosplay, and he ate a quick breakfast and hurriedly dressed and made his way down to the convention hall.

The sun was shining, and the world was right. Alex skipped down to the hotel lobby and walked down the long hallway toward the convention hall, whistling a joyful tune all the while. He made it to the double doors, and as they swung open, he was greeted with a familiar, yet exhilarating sight.

Hundreds of women of all races, sizes and ages, all dressed in Sailor Moon cosplay. A tall, leggy woman with milky white skin was dressed as Sailor Moon. Her tight white dress with short blue skirt and big red bow hugged her petite frame, and the long pigtails hung down from her blond wig. A small asian girl dressed as Sailor Mercury walked by with a sly smirk, her short blue wig shimmering in the fluorescent lights. Her blue thigh-high boots made her legs look longer than they were, and Alex followed her slim frame across the room.