Category: sexystories

Back Room Fights 2.2: Michael vs. Maggie (Mixed Boxing) [Str8] [mf]

“All right everyone, this upcoming match is a mixed boxing bout between two returning fighters. The bout will take place in three minute rounds until a fighter is knocked out. The winner will receive a $2000 bonus and receive oral from the loser. Now introducing our fighter in the blue corner. He has a record of 0 wins and 1 loss. He is 5’11’’, 159 lbs, and is a 22 year old college student. Please welcome Michael back to the ring!”

Michael removed his robe revealing his cute, lean body. Today he was wearing a tight fitting pair of briefs that clearly outlined his large dick. His eyes were playfully determined as he stared across the ring at his still hooded opponent. He moved his brown hair out of the way of his eyes and bounced back and forth on his feet in anticipation of the fight. He didn’t like to be in the losing column but the hard fought match against Brooke last month had not been embarrassing. He had enjoyed eating her juicy pussy but hoped to get sucked off instead this week. Read more »

A Mentor [Part 3] [MMF]

As Jayne disappeared through the sliding door Tom turned his attention to me and asked how a dumb fuck like me ended up with a girl like that? He made fun of me all the time like that at work, it was just us guys being guys. I laughed and said honestly I have no idea. He told me a girl like her deserved a real man and I was going to have to figure it out pretty quick. I laughed again and toed the leg of my BBQ. Tom started to explain to me the difference between a gas and charcoal grill and why charcoal was better. It actually did make sense.

Jayne came back out with a beer for me and she had a bottle of whiskey as well.
I don’t like whiskey so trying to avoid it I asked about the girls. She said they’d had a long day and she’d just tucked them in bed for the night. Tom inspected the whiskey and apparently approved. But playfully Jayne grabbed it back, pulled the cork and started chugging it! I cringed watching and even Tom’s eyes widened. When she finally tilted it back down her cute facial features screwed up in a look that let us know the taste had finally hit her. Tom congratulated her and stepped forward to pat her on the back. He told her he’d never seen anything like it, while he was rubbing her shoulder. She was blushing and said something about getting the job done quick and easy. I was feeling sick again watching Tom Read more »

An Improbable Stream of Sexual Consciousness [F/M] [Str8]

The hotel bar is dark, but busy.  You walked in, trying to act nonchalant.  Reminding yourself to look confident, un-self-aware, as if you were here for business, just one of the guests.  You haven’t felt the cold outside, thanks to the warm, buzzing feeling inside.  The fabric of your black dress, thin, pressing against your skin, slides smoothly against your overcoat.  You can feel the goosebumps all over your body.  The anticipation is intense, and so is the second-guessing.  Should you have come?  This is insane.  He won’t show.  Your mind is racing.  It was one thing to exchange glances, but now…  Read more »

A fantasy fulfilled [fMMmm]

She always had fantasies that made her feel different than any of her friends. Admittedly, she never thought she would be able to enjoy most of them, but her fantasies gave her drive. She poured her energy into her school work, determined to create a lifestyle for herself that would give her the flexibility that being an independent woman would afford her.

 

She wasn’t looking for love, but the moment she met Dean she had a crush on him. He wasn’t her first crush, but he sure made her feel like he was. He was an adjunct professor at her college, so their relationship had to remain a secret to the rest of the world, but between the two of them no secrets were ever kept. Over time their relationship grew deeper and she began trusting him with some of her tamer fantasies until one day, after much discussion, they found themselves in an open relationship.

 

Like all relationships theirs had certain routines, too, so she saw nothing unusual in his text inviting her over for the weekend. She looked forward to being invited over and dolling herself up in the manner of his choosing. Today’s request was for her to wear the black silky dress he enjoyed that highlighted her curvy ass, and tight enough on top that it showed off her voluptuous breasts. Read more »

My first ever sissygasm.

I was staying with family in a camper on their property. I would bust my ass on the property every day. Then at night I could go to my camper.

While in my camper I was able to dress up in a variety of women’s clothes. I dressed up in matching bra and panties, and silky pink dress that I had just bought a few days before. I had also purchased a new silicone chastity device. I had my toys out, condoms and lube. I took my “realistic dildo” that had balls at the base and zip tied it to the leg of the table. I was able to to then put the condom on it with my mouth, then turn around and proceed to ride the dildo until I lost control shot a stream of cum, and was shaking so much that I collapsed. It took an hour before I could move again.

It was so strong and intense that I am careful about how often it happens.

Private College Cock Rating

The girls and I set up another contest. The 5 invitations were sent to the guys in our college classes on facebook. They were told to arrive showered and clean shaven. They would be rated on three categories, length, girth and overall aesthetic.

We had already had a couple of these contests. The winner always got to do what ever he wanted with us afterwards. Last time, the winner was in bed blindfolded, and we all gave him blowjobs, having to guess who each mouth was.

We re-invited the winner from last time, he was near perfect and hot as fuck. The men arrived as scheduled, they were given towels to cover up and blindfolds. They were told to get nude, put the towel and blindfold on and line up.

The candidates lined up, and were told to drop their towels. They looked good besides #3. He hadn’t followed instructions, he had a substantial amount of pubic hair, and had a weird amount of foreskin. “Candidate #3 sorry, you must go.”

The girls took turns inspecting the others. They all had decent erections at this point, #1 and #2 both looked shy of 6” erect, and also in my opinion didn’t meet aesthetic requirements. Alison rudely said, “1 & 2 leave.” Read more »

A Mothers Work is Never Done! Chapter One

“GLURK GLURK HURK-Ahhh!” The loud wet suction noises followed by a deep breath for air filled the room. Margery gasped for breath, and brushed a strand of light brunette hair to the side. Her short cut hair was seldom in the way, but when things got hectic and she worked up a sweat she missed when it was long enough to put into a proper bun.

“Come on Mom, I’m so close!” Her son’s voice had that whining tone that both annoyed and oddly endeared her. He’d always been a momma’s boy, and even now he relied on her for so much. But it wasn’t his fault that the only woman that could take care of his needs was his own mother. She smiled up at her son, her red lipstick smeared around her mouth but somehow not managing to make a dent in the mother love of her smile as she looked past her son’s massive cock and met his eyes. Read more »

Success or Failure – A Cautionary Tale

Yes, of course as an adult I realize I should know better. Given that I faced being “dumped” versus finding some adult company, I chose fun. I miss being sexual, I miss sharing that with a man. Of course I would have preferred to spend all my time with just one guy, not try to craft the perfect man from a bunch of different ones. If a man can sleep around, why can’t I? All of these encounters were safe, we used condoms, and a few men even left wearing masks!

I am writing this up as sort of a memoir, as well as to recount the events of the last two weeks. This is WORDY, so grab a cook drink, settle in, and buckle up. A bit of backstory: I was planning to travel for personal reasons, and about a month before my trip I met two men online who were both very interesting, very nice, sexual… men I would normally be attracted to. However, one of these men seemed much more my type, and as we got to know each other over the next few weeks I started to wonder if the connection would translate to real life. Both of these men lived in the place I was visiting, but I made the crazy decision to ask one of them if he was interested in us staying together during my visit to see if anything real happened between us. Read more »