Crossdressing [M] – The Time I got Caught

This story is real and happened a while ago, also while 21+

So I’m finally living in my 1st apartment while in college. It was honestly the best feeling: freedom, fantasy and self discovery.

I had been wearing panties for sometime and had amassed a great collection, some purchased, some borrowed buy all commingled in my top drawer because I lived alone. At the time, some of the panties I owned had the matching bra so there were quiet nights I would get all dolled up and just transform into my sissy self.

Well one afternoon I get in a cute thong with matching bra, sadly purchased, and loved the fact that I’m able to lounge around my place acting all girly and slutty. The blinds are kind of open but it’s the day so you cannot see in really. As day turns to dusk and dusk to night I’ve decided it was time to play. Now I could have played anywhere but seeing myself dressed up, I wanted to see myself play.

I went into my bedroom, turned on the light, sat up against my bed on the floor and faced the mirrored closet doors and started to lube up and play. I have to admit, it looked very sexy.

[MF] Amanda – My roommate Part 3

Longer build. If you don’t like it, find another story! This is one of my favorites.

We rested there a while, with Amanda draped on and nuzzled against me in my lap, her long soft hair’s sweet scent tickling my nose. I bent my neck to rub my nose against the top of her head, breathing in her scent and the warm air that arose from between us. As if in a steam room, we soon went from comfortably numb to uncomfortably sticky, and as her body expelled my quickly softening cock as the cool air invaded we both sighed, sharing a deep kiss before standing and stretching.

After a quick shower we found ourselves in our towels getting water in the kitchen and heading to bed, but we both paused when we stepped towards the bedrooms.

“… which one?” asked Amanda, turning her petite but trained body against mine.

I wondered what hers was like, “Can it be yours? Looks… soft”, at which Amanda nodded and led me in, moving her large mattress’ sheets back and dropping her towel. I followed suit and slipped under the covers, turning to spoon her.

Finally hooking up with my stepmother. [Pt.2][taboo][light cuckold][jealousy]

It was my sophomore year of high school, and I still thought way too often about back when I was in 8th grade and saw Amy step out of the shower. It still stung every day that I didn’t see her fucking tits. All this time I hadn’t seen much more than my stepmother in a one piece swimsuit, which only made me imagine what I saw underneath that one day even more. It wouldn’t be until this year that I saw more of Amy.

I was housesitting the neighbor’s 2 story house next door on a Friday night, and I was sitting up in the family room at about 9 pm. I was not allowed to have any guests over, so I just sat there watching movies, eating snacks and texting friends like I usually do in my house anyways. It hit me when I saw the “Low Battery” notification that I left the charger for my phone at my house. I had a weird feeling about using someone else’s things when it was unnecessary so I walked back over to my house to get my charger.

Reopening Old Wounds (part three) [loving sex] [friends] [cheating]

He pushed me back, “Hey, hey, what’s wrong?” He asked as he looked me over.

I wiped my eyes and looked at him, “I fucked up. I…I…didn’t think you’d ever…and we only have a few more days together. Why do I fuck things up so horribly, B?” I asked through my tears.

“You didn’t think I’d ever what?” He asked.

I motioned down to us, still connected and tilted my head, “Fuck me,” I said, “I…need to…I have to try and prevent a pregnancy and you just made me not want to.”

“You’d want to…”

I nodded and he pulled me to him in a tight hug, “And you can’t because of Nat and Grady?”

“Yeah.”

“For what it’s worth, I don’t want you to have a kid by them either,” he said.

“Why not? It has no bearing on you. We have a few days together at best. What would it matter?” I asked.

“If you go home pregnant, your husband is going to assume it’s mine and might tell my wife,” he said.

Car sex in front of friends house [F]

I was on a date and my date had this fantasy where we would get naughty in front of his friends house but obviously he wouldn’t know, well we had been making out and kissing and teasing each other in the car it was an suv decent enough for a girl to ride. My date took me to his house where he tied my hands with his tie as he fucked my throat laughing as I started to gag a little, he said I know you like it rough and I know you love being a tease. He knew how kinky and open minded I was so he said why don’t you ride me in front of my friends house in the car we drove up to his house on the way there I was rubbing and teasing his big cock.

[F(playing M)4F] The Burden of Fame in a World Unlike Our Own (character/story driven, romance, breastfeeding, size play)

Firstly, to clarify, I am a woman but for this story I am only interested in playing the male role. I am open to male partners but only those willing to play female characters. This is a story that I created with one of my favorite roleplay partners who is now unfortunately among the [deleted]. If you’re out there and are reading this I would love to continue. Otherwise, I’m open to anyone interested.

This is an idea that is a combination and culmination of many of my previous prompts and interests. The premise may be quite silly on the surface, I admit that, but that playful absurdity combined with deep, well developed characters is part of what I love most about roleplaying.

The story is set in a modern world very much like our own except with one key difference. The spectrum of size for men’s and women’s endowments (male genitalia and women’s breasts) far surpasses anything which is considered normally achievable here. (I could go on about exact sizes but I’m open to discussing that with you to find something enjoyable for us both.) Not only that but that aspect of exaggerated sizes is at the crux of their society. Those sizes are not only the central aspect of their concept of beauty but carry enormous cultural, social, even spiritual significance.

Teacher’s Golden Rule [FF, Fetish, Water sports, Teacher, Student] (Part 2 of 2)

—-

“Why don’t we leave,” Mrs. Oliver suggested. “I think the lovely aroma we’ve created may give us away.”

My skirt and knee socks were soaked and spotted. I didn’t care.

“My god Janet, the front of my skirt… look at it,” Nancy cried. What are people going to think.”

“Just walk out… quickly. Don’t worry about it. We don’t know anybody here. C’mon, lets go.”

We followed her, walking quickly. I stared straight ahead… Curiously, I was wondering whether any of the men were looking at me, wishing they could fuck me… If my dad were here, would he want to fuck me too? I shuddered at what my virgin mind could conjure up since falling prey to Mrs. Oliver’s sick and twisted idea of pleasure.

Professor Drew’s car was parked at the farthest end of the lot. Once there, I felt relieved. I didn’t know Mrs. Oliver had something else in mind.

Professor Drew wasn’t handling the nights events well. Sobbing uncontrollably, she was having difficulty finding her car keys in her purse.

This is my confession as a priest (38M) who gave into the temptation of a beautiful nun (19F)

Note: This confession is completely fictional. It is a fantasy that I wanted to write down.

I’ve been a priest for 10 years and I don’t regret it. I came into the priesthood at a dark time in my life. The only woman I’ve ever loved had died and I was lost. I was seeking comfort. I was seeking faith. And I found it in the church. For 10 years I have devoted myself to God and to speaking his word. But at the same time I am human. And I am reminded of this every morning when I wake up with a hard on. I don’t even masturbate. I can’t bring myself to it. It’s a sin, I know it. I would hate myself for it afterwards. But what I do enjoy doing is edging myself. I grip my hard cock and stroke it until the point of climax and then stop. I’ve been doing this for

The Sluts of Wollenham: Chapter 2 [fantasy, beastfolk, satyrs, freeuse, anal]

**Chapter 2: Between Two Rivers**

(*[Read Chapter One here](https://www.reddit.com/r/eroticliterature/comments/hukjlq/the_sluts_of_wollenham_pt1_fantasy_beastfolk_anal/)*)

The wodewose is now making his final thrusts into Miss Blossom. Desiring a closer look, Miss Boo crawls forward – any concern she had for her friend has now given way to prurient curiosity and even titillation. Without thinking, she unbuttons her breaches and slips her hand inside. A moment later the beastman raises his head and his triumphant roar echoes throughout the glade. Boo shivers with excitement. It’s clear he’s ejaculating – even under his thick hairy pelt Boo sees his whole body convulse. After twelve more firm thrusts he relaxes, then withdraws his cock. He’s now finished with Blossom, and no longer having any interest in her, he strides off into the woods. Boo feels she should say something after him as he goes, but nothing comes to mind. She looks at her friend again. Breathing deeply, Blossom rests her forehead on the grass. Cum seeping from her rear end glistens in the sunlight. Turning her head a little, she looks at Boo. Embarrassed, Boo takes her hand out of her breaches, then says in a quiet voice “Very ill-mannered that fellow, walking off like that without a word.”

She told me to fuck her in her Halloween makeup and costume — after finding out why, I couldn’t say no. [FM]

Prior adventures that are somewhat related:

I [M] got to watch a long-term flirt have passionate sex after not seeing her for a few years. [FF] [FM] from gonewildstories

I [25/M] fucked the hot bartender [27/F] after she demanded it (not that I was complaining) [FM] (long-ish) from gonewildstories

I got a blowjob from a bottle service girl in the back room of a nightclub. [FM] from gonewildstories

(skip to &&&& for the naughty stuff)

I’ll set the scene: I was DJing a bottle service nightclub on a Friday of Halloween Weekend in 2014, and it’s a wild night. Sparklers, glowing bottles, CO2 cannons, it’s great. The club was packed with bachelor and bachelorette parties, there was a dozen and a half other tables going crazy — and with it being Halloween Weekend, it was even more debaucherous than usual. Holidays always bring out the nutters (St Pats, Halloween, NYE, Thanksgiving Eve are the terrible foursome).