Brewing at the office [MF]

I’m a guy in his early twenties who works with a small team. I’ve always had a preference towards older women, whether that be teachers, friends mom’s, or celebrities. So, when on my first day, I met the woman I was starting with, Marie, a pretty blonde, single 48 year old year old, my head immediately began drifting off onto the possibilities.

Marie and I have developed a very open friendship, talking about sex, porn, and relationships. Lately, things have begun to feel a bit different. Yesterday, she asked about how my sex life has been and I said nonexistent, which leads to today’s event.

Upon walking into the office this morning, I greeted Marie. She immediately groaned a bit so I asked what was wrong. She complained of a painful knot in her neck. After talking for a few more minutes, the groaning continued until I volunteered to help her out.

I stood above her and began massaging her bare shoulders and neck. The groaning turned into moaning. She kept whispering how good it felt and asking for me to go deeper and then mix it up with slowly scratching or tracing my fingers along her smooth skin.

How I Actually Lost My Virginity [FM]

The day after [my encounter with Joe](https://www.reddit.com/r/eroticliterature/comments/b3t5ua/how_i_almost_lost_my_virginity_fm_repost_blowjob/) was among the most nerve wracking days of school I’d ever had. Not finals, not pop quizzes, just a simple day of practicing to march in for graduation. Simple, right? The problem was, even though Joe was there, he wouldn’t look at me. When I met up with my usual group of friends that morning, he just mumbled a hello and focused on his breakfast. When the bell rang, he was the first to shoot off to wherever he had to be. When all the graduating seniors met up for marching practice, he just took his place in line and kept quiet, instead of joining the rest of us off to the side, joking about how stupid it was to build two days into the schedule to learn how to walk properly. I really, truly thought I had messed up our friendship forever. To my eighteen year old mind, it was the end of the world.

How I Almost Lost My Virginity [FM] (Repost) (Blowjob)

I was a good girl all the way up through high school. Straight A’s, I never got into trouble, I always did as I was told, but, unknown to my parents, I’d gotten pretty heavily into watching porn. Watching the women sucking and fucking on the screen in my bedroom was the height of sexiness to me, and I, a virgin, knew beyond the shadow of a doubt that I 100% needed to get fucked.

Unfortunately, I hung out with a bunch of hopeless virgins like me, and I knew that the only way they managed to talk to me at all was to not view me as a sexual figure at all. Baggy clothes and no makeup only helped/hurt, I know, but I liked their company. Had I just whipped my tits out and announced my pussy open for business, I knew they would all run for the hills, so I did what I had to do to keep the friends I wanted. Graduation was only days away, though, and while I could have just walked into school with a tight top on and batted my eyes at some jock, I wanted something a little more personal.

Big sex with a below average cock [MF]

My wife and I have been married for 23 years. About 10 years ago we started going to a nude beach in NJ and I commented to her that I always thought I had an average cock. After looking at the guys there, I realized that my cock was pretty small. I realize that you can’t really tell unless they are erect, but it still was apparent that I was definitely below average.

I never really thought about it much and she never seemed to care, so it was never a big deal. As part of the conversation, she disclosed that I was, in fact, the smallest partner that she had ever been with and that she actually had dated three or four guys that were very well hung. She also said not to worry and that my cock feels fine and our sex is great – but it still left me wondering and a bit worried about it.

Tapping Shoulder Tappers [red ink welcomed] [mff] [pot] [ws] [enema]

Shoulder Tappers 

As  I walked into the liquor store I spied two fresh barely legal females, a slender late teen, and her  stocky friend,they were approaching random people , clearly they were shoulder tapping. I went and got my four pack, a pint of rum, and rolling papers.

   As I exited the store the two moved into an area were they would intersect my path.

  “Mister?”

“Yes young lady.”

” We’ve just about given up on finding someone generous enough to get us some supplies to take to a back country party.” 

“You need a booze buyer?”

“Yes we do, beer, schnapps, wine cooler,  and Jagermeister.”

“Well I just might be your broker today young  ladies. Just what’s in it for me?”

“You could keep any change… ”

“I’m fine for money Miss. So I’m willing to put myself into a position to get arrested, and fined for buying booze for minors.”

 ” Hmm Um… ” The strawberry blonde started . ” Well what would be sufficient to persuade you to help us Mister?”

” First, my name is Earl. Second… just how bad do you want supplies?”

Me and my grandma

I admit it. I once was in love with my grandma. Or better said, hard for her. It was quite some years ago. I was barely out of school, she around sixty. And a widow for the better part of a decade. And yes, she liked it hard. And yes, there was a certain period in our lives when we fucked each other like some animals. At every possibility. For a while. No, we are not together any more. But what happened is still our little dirty secret.

Back to that point in time were it all began. I was a fresh high school drop out. On the hunt for job. Something with a perspective. With the chance of building up a career. But in the area I lived in, nothing. Just minimum wage jobs. So I had to look elsewhere. Everywhere. And I found something. An office job. In a really big and well established company. Far away from home. So I needed some accommodation.

But the payday wasn’t that great. So renting my own place was not doable. For the moment. Luckily my grandma was living near my future workplace. Alone, in a big empty house. Grandpa was already gone for good. Her offspring, my mom is one of them, already out of the house. So plenty of empty room for me to occupy.

Me and my grandma

I admit it. I once was in love with my grandma. Or better said, hard for her. It was quite some years ago. I was barely out of school, she around sixty. And a widow for the better part of a decade. And yes, she liked it hard. And yes, there was a certain period in our lives when we fucked each other like some animals. At every possibility. For a while. No, we are not together any more. But what happened is still our little dirty secret.

Back to that point in time were it all began. I was a fresh high school drop out. On the hunt for job. Something with a perspective. With the chance of building up a career. But in the area I lived in, nothing. Just minimum wage jobs. So I had to look elsewhere. Everywhere. And I found something. An office job. In a really big and well established company. Far away from home. So I needed some accommodation.

But the payday wasn’t that great. So renting my own place was not doable. For the moment. Luckily my grandma was living near my future workplace. Alone, in a big empty house. Grandpa was already gone for good. Her offspring, my mom is one of them, already out of the house. So plenty of empty room for me to occupy.

[M]y [F]irst Coworker—and Boss’ sister—Fuck: Part I

I’m fit, blonde hair, blue eyes, late twenties, well-spoken, about 6’2″ with shoes, and a proud nerd. I switched jobs like 2 years ago and immediately was thunderstruck by a coworker who emailed me some introductory information about the company. We worked though in different offices. It didn’t take long for me to realize it was my boss’ younger sister and that we would be training together in my second week a couple of items.

I’ll call her Jade. Jade was mid-twenties, strawberry blonde thick long hair, porcelain complexion with sharp eeyebrows, big brown eyes, and full lips. And curves for days. Busty, thick hipped, and lovely thighs, but not heavy at all. I couldn’t keep my eyes off her profile pic in the emails she would send to me. And in-person after training together, sitting next to one another, I kep looking at her lips. Her voice was a little deeper than I expected, but I liked that. An alto not a soprano. It was hot. I kept my distance for weeks. She was in a relationship I learned and I was too. But that didn’t stop her from emailing me in times when I honestly probably didn’t need to hop in and help her digitally. I would analyze her playful unnecessary use of an emoji or exclamation point. And since Social Media was a part of our work for marketing and learning about competitors, naturally her profiles starting getting recommended to me.

The Sissy Journal Vol 001

Day : 03/13/2019

Time : 1:30 PM

How : Gr****r

Where : His Place – House

Name : ? 001 ?

He hit me up on gr****r. We chatted and swapped pics. Sent girly pics first, then boy pics. He wanted to meet up right away.

I went over to his house in boy clothes. He lives only a few blocks away. I walk in…

As tall as me. Olive / white skin. Chubby Hairy Daddy Bear. Glasses. Cute.

We sit in the front room and I light a joint. We puff it once before clothes start coming off. I show him my freshly shaved legs and asked if I shaved all the way to my ass. Of course I do and he wanted to see. I strip completely and turn my ass in front of his face while he sits on the couch. He touches and spanks my ass. Then he stands up and takes his pants off. OH MY GOD, HE IS UNCUT!!! I have never sucked an uncut cock, so I quickly get on my knees to give it a try. LOVE IT!!! He likes deep head. He wanted to fuck me, and tried a few times, but I wasn’t “ready” ( I explained it to him after ) for anal. He stood over me and worked my mouth and throat till he was ready to cum. Asking where I wanted him to cum, I opened my mouth and stuck out my tongue. I let him cum in my mouth and kept in in for a little bit after. I spit it into a tissue that was in my jacket pocket. HOT ONE, HAVE TO DO IT AGAIN!

What arouses me

I’ve grown up in a conservative home. Meeting girls was impossible. Early on I resorted to masturbating and watching porn. All this is so unnatural.

Later on I discovered that I’m a submissive. My most powerful erotic experiences are related to shame.

One of my friends had a possesive attitude towards me. I always imagined kneeling before him and licking his feet.

My boss was a woman with a nasty steak. She quickly found out about my being submissive. She browbeat me into doing extra work. Everytime she scolded me, I felt aroused. More I try to hide my erection, more she’d mock me. Once she casually flicked me. I ejaculated. As I stood helpless before her with wetness spreading on my pants, she mocked me for being an inefficient sissy. I had two more ejaculations, making her more and more derisive.

More than actual physical act, it’s mental embarrassment, guilt, shame, submission, taboo, and mocking that triggers me.