My most recent time fucking a crossdresser [M28, T19]

I’ve always had a voracious sexual appetite that has led me into the rabbit hole on more than a few occasions. For my first story, I’m going to retell my most recent night with a crossdresser. This happened in February 2016 and is as accurate as my memory will allow.

I’m 29, tall, a fraction overweight, but I would imagine reasonably attractive. I am single, live alone and have no dependants. I did well at school and at university, and have found success in the financial sector. I am not objectively rich, but do make a six figure salary and have the toys to go with it. I only mention that as for the purpose of some other stories, I have managed to use it to my advantage to sleep with women very much out of my league. Sexually I am very much of a hedonist, but in my day to day life I am boringly ordinary. I do not drink, do drugs or smoke. My cock is just a hair over 7 1/2 inches, although it’s not particularly thick. It’s perfectly straight, something that has been commented on by lovers a few times.

Paying for it: Volume 1- Helping a friend [m/f]

So I decided to chronicle a series of adventures in my life that I’ve had that had something in common, I paid for them. Yes look at the loser who paid to get laid. Well I didn’t set out looking to hire a woman for companionship. The first time fell into my lap if you’ll forgive the pun and from there it progressed.

Now a few things to get out of the way.: yes I know this is dangerous: stds, arrests, getting robbed or worse are all potential liabilities. I have always worked to minimize these risks so please let’s leave the lectures out of the comments and PM’s.

Well on to the first instance…

I was in college and the Internet was just getting mainstream. Using telnet to connect to other university computers and chatting with other students there was something only a few people were really doing but it was going on. I got to know a student Anne, from a nearby college and we hit it off well enough to have a meeting for dinner and a drink to see if there was any potential. We hung out for a day and though there was some attraction it wasn’t enough of a spark for either of us to parlay it into a full dating situation. However we remained friends and chatted regularly. Over the months ahead. Even though we didn’t even kiss at our hangout meeting we eventually got to discussing sexual topics, because that’s what you do when you’re in college, especially if you’re going through a dry spell.

Story from my old job/ My manager who became my domme (M/F, bdsm/femdom, long)

This is the part 2 of this story. You can find part one in my submitted posts.
After what had happened between us, there wasn’t much sexual intimacy for a while. I stayed with her now and then, we’d cuddle, laugh, play Mario kart. But regardless of that, she still considered me to be her sub and considered herself to be my domme. I was totally fine with that, it was honestly really nice and stable. I was always curious why she never wanted to do anything sexual afterwards, but I soon figured out why.

She would control me in nearly every way during the week, sometimes taking two weeks, and would let all of that raw sexual power out on me afterwards for a few days. Close to a week after the first story, I noticed Dylan becomming much more assertive with me when it came to everything. She wanted things done, and done right then. When she asked for a massage or a neck rub, after a while she stopped using my name, but would call me slave, or something to that nature. She’d remind me how disposable I was, that she could replace me with a thousand others, but that would just be a hassle. If she or I needed something and she sent me to go get it, she would put me against the wall and leave a hickey on my neck to let the world know I belong to her. She would tell me what I should do in the gym to get myself fit for her. It might sound like too much for some, but I was on top of the world being her sub. Then when the weekend came around, she would completely dominate me for 3-4 days straight.

<Still Guilty> Hot gf’s roommate

I think it is finally time to tell this story anonymously to an audience. I’m still working through the feelings associated, etc. It kind of fucked me up because it was the first step in an eventual very emotional breakup with my gf. I wasn’t very attracted to her although she is good looking and a lovely person. I mostly just really liked and admired her. We’re still working on being friends a few years later. Anyway, this experience helped me see that I needed to end it, but also made me feel really fucking guilty. I have only really talked about it with my fiance (who is the absolute best), and she gets it, but I need to share more.

My gf and I used to sleep over at each others’ places sometimes, especially on weekends after partying. We were both sophomores in uni at the time, so both had to share our rooms with a roommate (which as anyone who’s been to uni knows is both a blessing and a curse – my roommate from that year is still a great friend, but there were a lot of close calls on him walking in on me and my gf). Anyway, this story is about several of those nights sleeping over at my gf’s place.

Lechomancer Curses 10: Banishment [mf][ff][bondage][toys][oral][anal][paranormal]

“Hi Michael,” Brittney sighed into the voicemail. “Listen, I’m really sorry, and I really need to talk to you. I screwed up, big time, and I don’t want things to end like this. Sorry about leaving so many messages. Please call me back. Sorry.” She hung up the phone and tossed it on the bed.

This was so fucked up. She had never been the sort to cheat before, and then, out of nowhere, this charming, well-dressed man starts flirting with her. She didn’t know him, never even heard his name, and before she knew it, she was inviting him home and luring him into her bed. It had to happen on the one day Michael was home from work early, and then her stupid temper had made her so defensive. He had every right to be mad, but because he yelled at her, she screamed back at him, and kicked him out, and now everything was a mess. Brittney just really needed to make things right.

Her fiancé had stormed off hours earlier, running back home to his family, probably telling them every horrible thing they were happy to believe about her. Brittney was certain the Meyers were vilifying her, ready to crucify her. Fuck, she just needed a chance to talk to him, to make him understand that is was a mistake, a one-time thing.

That first fall [FF][Voyeurish]

It was a few years back as fall started to approach in her first semester at college. She was one of those motivated types, though she was a freshman she was enrolled in a lot of the same classes as me when and I was a sophomore. I was bothered by it because for me I viewed college as an opportunity to break away from the strict rules of the house-hold I had grown up in; later I would learn and come to appreciate her drive, ambition, and tenacity.
It was that first fall where she started to grown on me, we became friends, and even a little more. Her name was Nadia, I don’t know if she was 100% Irish because she lacked the stereotype personality of a feisty redhead, but she sure looked the part. Shoulder length orange-red hair, light cream colored skin with freckles covering her arms and face. She was slender since she ran Track in high school, though you’d never guess that since she was practically always buried in books and wore leopard print glasses over her sparkling emerald green eyes. For the school that we went to she always dressed kind of conservative, I almost spit out my iced Bhakti chai the first time we went to the new pool and saw she wore a one-piece. Despite all of this, Nadia had an amazing girl next door vibe. She was always classy with her clothes and didn’t dump on heavy foundation or liners.

Shawna: Roma Revenge – Part XVII – Many Happy Returns [MF] [END!]

I woke up the next morning to the familiar call of nature. Yawning, I stumbled into the bathroom to relieve the pressure. I stood in front of the toilet, dropped my shorts to the floor, and promptly pissed all over myself.
I’m pretty sure the neighbors downstairs heard my relieved laughter as I threw myself clumsily into the shower.

Ladies After Tequila [FFF]

Jackie’s keys slipped out of her fingers while she giggled and braced her hand on the trim around the doorway.

Kate, a whimsical brunette, laughed and spanked Jackie on the ass while she was bent over to retrieve her keys. “Spank that sexy lesbian ass!” She glanced over at Jade but the motion put her off balance and she teetered back and forth.

Jade laughed at her two ridiculously drunk friends and put her finger up to her lips while stumbling forward. “Ssshhh. You guys, we definitely don’t want to wake up Jackie’s neighbor.”

Jackie finally picked up her keys and was pushed inside her apartment by two giggling and off-balance friends. She leaned against the wall to take her shoes off and said, “You two should stay here a bit until you’re more sober. I’ll,” she hiccoughed, “I’ll make popcorn.”

Jackie fumbled in the cupboard for the popcorn while her friends dumped their shoes and purses on the floor. Kate and Jade plopped onto the bar stools on the other side of the kitchen pass through.

Jade slapped her hand on the counter, tossed her blond hair behind her, and winked a smoky, blue eye at Jackie. “Bartender, a drink, please!”

Journalist Solo in Napa [M] (Jamie & Penny Part 1)

Drunkenly kicking off his expensive loafers, Jamie shuffles across the hotel suite and heaves his six foot frame into a deep leather wing chair. With a sigh he flips open his laptop and stares at the screen. Writing is the last thing he wants to do right now, but he hasn’t written a single word all day, and he just can’t afford not to.
The SFGate generously offered to sponsor his attendance at the journalistic conference in Napa, but when they offered to put him up in a dive hotel off of the highway he declined and booked himself a more luxuriously appointed room not far from his favorite winery. When he booked the suite he thought he’d have company, but now he’s alone.
After a long day of reviewing grammar, corporate guidelines, and journalistic integrity he’d hit the hotel bar with a few colleagues and now his thoughts are warm and slow after one glass too many of a spectacular california red. With a sigh he begins typing and hesitantly picks his way through a piece he’s working on, gradually immersing himself into the story. The amber California sun has long set and the room is dark when Jamie halfheartedly types out a few final sentences and shuts the laptop with a heavy sigh. He’d done what needed to be done and not a word more – tonight his heart isn’t in it.
He pushes himself away from the desk to flick on the lights and grab a beer from the mini-fridge. After a long pull of the cold drink he puts down the bottle and sits at the end of the king bed to undo his tie and unbutton his crisp white shirt. He feels a pang of sadness as he looks around the tastefully decorated room. The room was made for romance, and the stone fireplace across from the white-clothed king bed demands an offering of sex. “Not tonight,” he says out loud as he pulls back the sheets and sinks into the bed. The white linens scratches against his skin as he pulls off the rest of his clothes and slides under the covers, clad only in a tight pair of tight black boxer briefs.
It doesn’t take him long to drain the first bottle of beer twist the top off of a second, which he’d left waiting for him on the beside table – dripping cool condensation onto the expensive dark wood. He heaves another sigh and turns on the tv. The news drones on for under a minute before he flicks his way to the pay per view channel. He ticks past the New Releases section before arriving at the Adult options. The videos available are the same low quality garbage available in any hotel in America – heavy on the “teenage” girls element, with a generous bent on bukkake and angry, but very chesty, moms.
Jamie didn’t care much about the content. He was lonely and seeking solace in the guilty pleasure of hotel porn. He relaxes as the bulge stirring in his black boxer shorts seemingly comes into control – worked up partly by the selection of movies in front of him, and partly by thoughts of the blond woman who should have been enjoying this beautiful Napa Valley suite with him.
He chooses a video for $8.99 that promises a to be full of youthful football players and their sophomoric cheerleading counterparts. Taking another long pull of beer, he’s momentarily distracted by the ridiculous storyline before it leads, shockingly quickly, to a scene with two muscled college jocks circling three cheerleaders, who smile up at them from their place on their knees on the floor of the locker room. The cheerleaders are clearly old enough to have their own kids in college, but he didn’t care. The movie was nonsense, but it satisfied a baser instinct. He pulls the band of his black underwear under his heavy balls and massages his thickened cock in his fist. On the TV a coach comes into the room and takes charge of the younger gang – forcibly deciding which athlete gets to enjoy the pleasures of which cheerleader. It’s only when the coach helpfully coaxes the jock’s oversized cocks into the the girls that Jamie’s brain truly checks out. The room is filled with the sounds of sex on tv, and the rhythmic thwapping of his fist sliding up and down over this rock hard cock. His ass presses deeply into the bed just as the coach is showing unexpected cum over the students writing on the locker room floor. Jamie tenses up and shoots a milky spray of cum onto his smooth, lightly furred stomach and chest.
Before long his thoughts are slowing down again and he’s sleeping soundly under the covers, and the room is lit only by the flickering of the muted tv cycling through endless images of the hotel and local attractions.

Last time with Ashley [m/ff]

I almost didn’t write this but it’s in the timeline of events with me and my step-dad but I know you horny pervs will like it :) I don’t consider this one of my 6 times I did anything **that** sexual with him.

About a week later from the swinger adventure, my step-dad comes to me and wants to know if I’ve been keeping on his demands. He changed somethings around. He took away my dildo because I was getting too loose. He gave me a finger clit vibrator. He also took away my starter butt plug, no replacement. He said both my holes were too large for him and needed to be shrunk. At night time, I was to use the finger vibrator until I got off while squeezing my left nipple during orgasm.