The Dungeon [Dark][Pleasure][Helpless]

Awoken by a pounding headache, a cold chill travels down your spine. The realization of not knowing where you are sets in. Fear begins to overcome the headache pounding at your skull.

A metallic door grinds open. Candlelight begins dancing around the room. A shadow appears as the light begins to fade, the door slams shut with a bang.

A slight pressure on your right arm followed shortly by a prick. A tingling sensation burns through your veins. All blur of a moment. Talking, a deep male voice.. Are there two people? “Get ahold of yourself..” You think.

“I know you can hear me. I have wrapped your head in some gaze, you were bleeding from the wreck. You may feel a bit dizzy, I gave you a sedative. It should last another few hours. Try to relax, my plaything”

..darkness..

You wake up once more, pounding headache gone. Your eyes open as you scan your surroundings. You can make out a wall made of black bricks. A strange smell divides your attention for a moment. “How.. did I get here” you mumble in silence.

From A Prompt: A Virgin Wakes Up in the Body of a Pornstar [mf]

Jennifer never really cared about sex, and it shouldn’t have been surprising. The Puberty Fairy had pretty much passed her by. Short, thin, and mousy, nearly to the point of vanishing into the furniture, people kind of ignored her. She was used to it, and she hadn’t expected anything to change when she came to college. She still wasn’t sure how her roommate, Samantha, had found the confidence to go out and hook up with a boy during the first week of classes. In the darkness of their room, Jennifer’s long mop of wavy brown hair shifted on her pillow, as she tilted her head to peer toward the door, her ears vainly searching for footsteps coming down the hall.

Jennifer sighed and reached for her phone. “Going to sleep. Class all day tomorrow. Please be quiet if you get back in the middle of the night,” she texted, setting her phone aside to charge and resting her head on her pillow. She was going to mentally review her notes to put herself to sleep, but sleep found her before she could even start.

The Hot Tub [MFF]

It was a Tuesday afternoon, the summer of my high school graduation. I was going about my usual day woke up late, cooked an over medium egg and coffee with light cream. Suddenly I feel my phone start to blow up, I check the messages and its my childhood friend Kayla. She only lives about 2 hours away from me now, after my parents moved us in middle school. She states her regret in not being able to help me ring in my 18th birthday the “proper way” what ever that means. She also said she will be coming to visit a friend of hers tomorrow and wants to come over for a few to catch up. I have not seen her in almost a year so I’m very excited by the idea. I gladly accept her offer and tell her she more than welcome over for dinner. Truth be told I have no right inviting her over, my parents are currently out of town on a friends week at the cabin, and my sister stayed at college over the summer. Never the less I invite them over. Seeing as the only thing I can actually cook well is a fried egg and toast, it’s looking more like pizza is on the menu for tomorrow. The day finally arrived I truthfully had no real expectations of that night just some pizza, catching up, and I guess making a new friend. Kayla texted me saying shed be here at 6:00 PM. As per our usual agreement Kayla and her friend pulled up around 6:35 PM casually late as always. Kayla was a light skinned girl, stranding about 5’2” thick curly black hair, light brown eyes, she had some great curves too, and medium sized breasts. Her friend was the polar opposite. Pale as the driven snow, long straight blonde hair, standing easily 5’10” pushing 5’11”, slender, with maybe a B cup to boot. Kayla walks in and throws her arms around me squeezing me tightly. ‘Bro!” she exclaims “I’ve missed you, how have you been?” Before I can get a word in edge wise she introduces her friend. Her name is Alison, I couldn’t help but notice her shorts being a little too tight on her. Giving me a slight view of the outline of her plump pussy, I look away quickly as to not raise any flags. To answer Kayla’s earlier question, I fill her in on the details of the past few months. I’ve graduated high school, and I have my sights set on starting at a community college before applying to State. We catch up for about an hour before Kayla asked if my parents still have that hot tub. They did in fact still have it, I asked if they brought swimming suits and they both smirked saying no. Alison chimed in “ we do have on something close though… if your ok with that?” she grins knowing my response already. “Of course, that’s fine!” my response sounds almost desperate and the two girls giggle as we walk to the hot tub. I grabbed some towels and drinks for us, whatever beer dad had left in the downstairs fridge.

The Monet [MF][Cheating][holdthemoan]

Part One

Chapter one

It was over a year prior to the events of the [The Stake-Out](https://www.reddit.com/r/eroticliterature/comments/grd4f1/the_stakeout_mfvoyeurcum/?utm_source=share&utm_medium=web2x). Sean Fleming’s target was a late Monet; his mark, Katherine, the unsated trophy wife of “Duke”, an aging baseball player turned philanthropist.

Sean’s play was simple. Seduce the wife and obtain the security code for the couple’s ritzy colonial in Queens. His crew specialized in undetected theft. Their M.O. involved swapping the target work for a high-quality forgery before anyone grew the wiser. That said, Sean would have to locate the work and study its mounting.

Sean planted himself as a temporary server at an upcoming charity banquet that Katherine and her husband had attended for the last five years. Sean was charming and a chameleon. His ivy education found him comfortable in bespoke suits while his rough upbringing left him equally comfortable in the rags of a pauper.

In a white shirt and black tie, Sean approached Katherine’s table. He took the parties’ orders while making light conversation. Sean positioned himself directly across from Katherine and caught a glimpse of her eyes looking up and down his athletic build. Nonetheless, he was deliberately over-attentive to the young brunette sitting at his left. He subtly shunned Katherine leaving her uneasy in her seat.

The longest time [MF]

For months we’d both been fighting pent up sexual frustration and enjoyed teasing the other. It was a game we’d become very good at over 4 years time. It had been a long awaited experience for us both. We’d talked about what we’d do to one another at first glance for months leading up to this.

As I pulled up, I was fully aware of my lingerie under my clothes, riding up into my wet pussy from anticipation. And my butt plug applying the perfect amount of pressure which only amplified things for me. Would we instantly rip each others clothes off? I’d hoped he would push me against the wall and tear my yoga pants down to reveal my sexy lingerie I’d bought especially for him. I’d been imagining biting his lip and looking into his deep sexy eyes as I licked my way to his delicious cock. All these sexual memories of the two of us come rushing back to me as I sit there preparing myself for what’s to come. Eventually I am feeling more turned on than nervous and go knock on the door.

The Stake-Out (MF)(Voyeur)(Cum)

After fourteen days, the interior of the cargo van started to feel like a coffin. Stake-outs were normally insufferable but this one was particularly bad.

For starters, we were parked off Park Avenue on an upscale Manhattan street. The nearest coffee shop or bodega was an avenue west or 13 streets south. This made pissing more than an inconvenience. My male counterparts had it easy. I can’t count the number of times I found a piss-filled Gatorade bottle left in the van at change over.

The second thing that made this particular assignment insufferable was the arrogant son of a bitch we had as a mark, Sean Fleming. He was under surveillance for his suspected involvement in an art theft/forging ring. We believed he served as the group’s honeypot. He would seduce NY’s waspy housewives to locate targets and secure access for the rip crew.

He was just over 6ft tall and had the body of an Ivy League rower. He was traditionally handsome; a few loose curls above his right eyebrow routinely rebelled against his otherwise polished appearance.

Inappropriate People

He was her work buddy. They rode the elevator together and sometimes had lunch together. Ken was tall, with a baseball player type build. Nice arms, a goatee, and working man’s hands.
She was pretty. Short but not stumpy. Big, perky tits yet to be ruined by children. Straight, honey-colored blonde hair and piercing blue eyes.

Over the years they developed a friendly relationship and banter. Never anything inappropriate, they both seemed to be happily married. They’d meet in the cafeteria at lunch and talk about their favorites on Netflix and the things their spouses had done to annoy them the night before. Amelia had always found him attractive and she had caught him sneaking a look at her tits every so often.
She enjoyed their time together but they had never hung out outside of work.

It was Christmas and the annual company party was at a beautiful hotel. All the years before they’d both brought their spouses to the party but this year they were both flying solo. Since most others were there with their dates, they had sort of paired up for the night. Laughing and drinking way too much, they spent the night getting closer and closer to each other physically. And enjoying the emotional connection they had already begun to build at work.

[M]y [F]irst time with my ex wife

My relationship with Kristina had been an interesting one.  We met in college when some mutual friends were actually trying to set us up with other people at a party.  We spent the evening talking and found that, at that time, we had some common interests and goals, and eventually made our way back to my house.  Since I was one of the older guys in my house I had the privilege of having my own room. That had some great benefits on this night and a few others.  When we arrived to my room I opened a few beers and we carried on talking for a while on the couch, and eventually things progressed to us kissing, and pawing at each other like teenagers.  We continued the fondling in a slow escalation with our hands over our clothes, but soon I had a hand under her sweater and felt the softness of the skin on her back, and as that happened we turned so that my back was against the back of the couch so that she was all but laying on me.  She in turn, reached down to stroke my length over my jeans, then began to fuss with my belt buckle.  Ultimately, things progressed to the point to where she started to slide off of my lap and to her feet, but not before she took hold of my shirt and pulled it over my head.  Once standing, she walked over and locked the door, turned and walked back toward the couch grabbing her beer.  She steadied herself, took a big drink, looked back at me and winked.

[FM] I finally pegged my boyfriend

My first post here described the first time I rimmed and fingered my boyfriend, Henry. After that incredible evening, we occasionally incorporated anal play into our rotation of sexual fun, but it was not an everyday occurrence. I think we kind of wanted it to remain special – something rare for when we wanted to switch around our usual power dynamics. I didn’t post this story immediately after my first story because I didn’t want to give you all the wrong impression. Nine times out of ten, Henry takes the lead in the bedroom. Whether he is bending me over my desk or pushing me to my knees, we are both usually happiest when I am submissive and he is dominant. So, when I’m pegging him or fingering him, it’s a fun and rare change of pace.

A FantASStic Gamble [MF][Anal]

I’m not sure if this is against any rules. I loved [u/filthhunter69](https://www.reddit.com/user/filthhunter69/) ‘s story below and wanted to expand on it. [https://www.reddit.com/r/eroticliterature/comments/gpjtkj/i_fucked_my_moms_best_friends_daughter_in_the_ass/](https://www.reddit.com/r/eroticliterature/comments/gpjtkj/i_fucked_my_moms_best_friends_daughter_in_the_ass/)

******

“Oh my. That was fantastic,” my mom sighed as she set her paperback novel on the table. We were sitting on the back deck of our home on a warm May afternoon. I had just graduated college and had no idea what I was going to do with my life. The job market wasn’t exactly hopping with opportunities as it is. And I’m a political science major, for fuck’s sake. I just choose to not think about the decisions I have to make until I have to.

My mom picked up her phone. I knew she was calling her friend Carol.

“Yes, I just finished it. It’s so good!” Her eyes brightened as she listened to Carol gush over the same trashy novel.

“Oh sure! She can come pick it up this afternoon. I may not be home but Jeremy will be here. I’m sure he’d love to see her. Okay. Bye.”

“That was Carol. Kathleen is going to come by this afternoon and pick up this book.”