Masturbation Archives — Page 394 of 468 — NSFW story

Fucking Kristy in her Bed – Pt.2 [MF] [affair] [cum] [piss] [anal] [oral] [mast]

A week after Derek cheated on his long term girlfriend, Heather, with his gym friend, Kristy, he felt horrible angst. Would she tell? Would he be able to live with himself?

Derek and Heather frequently ran into Kristy at the gym and they continued to run into her for weeks and weeks. Kristy and Heather always got along and his worse fear is they’d bond and Kristy wouldn’t be able to hide the truth from her new friend a moment longer.

Eventually, Derek caved and texted Kristy.

“I’m such a hot mess,” he wrote. “I am so nervous that you will tell Heather. I believe you when you say you won’t, but I just need to hear it again.”

“Why don’t you come over and I’ll tell you to your face,” Kristy responded.

Derek knew what this meant — they were going to fuck again. And honestly, he couldn’t wait. He’d been thinking about fucking Kristy for almost a month. He’d become a little obsessed with her, jerking off to those slightly revealing Facebook photos of Kristy in bikinis or low cut dresses. Read more »

Fucking Kristy on her roof deck [MF] [cheat] [anal] [mast] [oral] [creampie] [voy]

Derek wasn’t the type to cheat, but when he saw Kristy’s instagram post, he knew he couldn’t fight the urge much longer. He needed to be inside of her. There she was, the girl from the gym, topless on the beach, her left hand covering her gigantic breasts, her right hand over her mouth giving a little “shush” expression.

He yanked his pants off, jerked off to the photo and then clicked on the little heart.

How could he pull this off? She knew his girlfriend, they all worked out at the same time every evening. He’d have to be careful.

“Love the photo,” he said in a DM.

An hour later, she responded with a “thanks.”

Well, this wasn’t going well. He was hoping for a little rope, something to keep the conversation going.

“Do you have a pool?” He asked.

“Roof deck,” she responded.

Kristy wasn’t bending. He imagined she knew what he was after and she wasn’t the cheating type, so he gave up after writing back with one word: “Nice.” Read more »

Thanksgiving Shenanigans [MFF] [Voyeur]

It was the weekend of Thanksgiving. Sarah, Nina, Jessica and Todd arrived at the Flemming residence for thanksgiving the Thursday prior. Introductions to the family members: Sarah and Nina are twin sister about 5’6 and a curvy 160ish lbs and 35 years old. Jessica is 6’1” and a skinny 140 lbs and 30 years old . Jessica is married to Todd who is 6’3” and a muscular 170 lbs and 32 years old. Sarah, Nina and Jessica are all sisters and their parents are Michael and Elizabeth in their late 60s early 70s. Thanksgiving dinner had gone as planned and now the weekend was for the 4 kids to enjoy as Michael and Elizabeth were going to Dallas to spend time with cousins. As the 4 of them started to make plans Nina received an emergency call in from works so she had to leave immediately back to Philadelphia. So it was just Sarah, Jessica and Todd left at the house. They all three decided to watch a movie. The three of them got sheets and got into sweats to get comfortable. Todd and Jessica cuddled on one couch covered by one comforter while Sarah got comfortable on another one. About ten minutes into the movie there was a pretty sexy scene. As they watched, Todd placed his hand on Jessica’s leg. He began stroking the inside of her thigh and she responded by opening her legs slightly. He glanced over to be sure that Sarah wasn’t watching him. Todd slid his hand from her knee up her inner thigh until he found her sweet wetness. Judging from the soaked condition of her sweats, panties and her pussy, this whole scene was making her wild with want. His middle and forefingers glided into her hole and pressed against her G Spot as his thumb resumed circling and stroking her clit. Jessica’s eye closed and she inhaled sharply, her breath hitching several times. Todd moved her panties aside, and sank three of his fingers inside her. For well over half the movie, her fucked her pussy with his fingers. She surprisingly kept quiet the whole time only because she was pulling his hair and biting his shoulder…hard. After a while she noticed his erection pressing into her thigh, and Todd felt Jessica’s hand begin to stroke his crotch, only a few inches away from Sarah’s hand. She began to stroke it lightly, caressing his cock, touching his glans through his trousers. Todd looked at Jessica, but she looked straight ahead. He was afraid that Sarah would see. By now Jessica was stroking his cock with rhythmic slow motions and when he looked at her, he gave her the signal that it was time to go upstairs and finish with the business. So they both used the excuse that they were tired and were going to go to bed, and let Sarah know that she could finish the movie without them. Little did Todd and Jessica know the first sexy scene also turned on Sarah and she was also horny from the movie as well. She decided to end the movie and make her way up to her room. Per her horny habits she took off her sweat pants and sweatshirt so that she was just in her Tshirt and panties. She pulled up fanfiction on her phone and got into bed. She found a new Sailor Moon fanfic (Rated M) She then decided she wanted to play in the tub. So she got up and got her towel and proceeded to the bathroom closest to her end of the hallway. As she stepped out of the hallway she heard a slight moan. She saw that Jessica and Josh’s bedroom light was still on so she walks quietly over to their room to see what is going on. There on the bed sat Jessica, braless, and panty-clad giving a completely naked Todd a blowjob. Sarah was mesmerized by the scene in front of her and her pussy started to get wet. Todd had his hands on his hips as he thrust his cock in and out of Jessica’s mouth. Jessica’s lipstick coated lips were firmly wrapped around his cock as she massaged his balls with one hand and stroked his long hard dick with the other. He then entwined Jessica’s long black hair in his fist and used it like a horse rein to force her further down onto his shaft. Jessica moaned groaned and using her hands pulled his ass towards her trying to force that cock right down her throat. Sarah was so excited as she watched she could feel her pussy getting wet and slid a hand into her panties and started rubbing her slick slit and the nub which was already sticking out from under its hood. Sarah’s fingers of her right hand were fingering herself frantically. She had released her tits from her t-shirt to allow her to twist and flick at her nipples. She was biting my bottom lip to stop her moans from being heard. Meanwhile Jessica was being face fucked, that’s the only way to describe what Todd was doing to her sister. Sarah, by now had decided she needed something bigger, other than my fingers to satisfy the feelings she was having in her pussy. Looking around quickly she saw Jessica’s hairbrush. Grabbing it she quickly used it to good effect. Rubbing the handle all over her slick lips and dripping pussy, before inserting it into her hungry pussy. She could feel it banging against her clit, and knew that would soon bring her off. “I want you so bad Josh. Come on fill me up with your cock, I want to feel that cunt stretcher inside me!” Moaned Jessica. Read more »

Moving Away: An Encounter With an Ex Before I Left Town [MF]

_Reposting this because it randomly got deleted? Taking the opportunity to edit my writing from 5 years ago. The second part is still up here: [Moving Away Again](https://www.reddit.com/r/gonewildstories/comments/w35lu/moving_away_again_mf/)_

It was a hot day at the end of July and my apartment had no air conditioning. I could feel the sweat running down my neck as I heaved my mattress out into the hallway. I was 22, in about as good of shape as I’ll ever be, but a day’s worth of moving everything I owned out of my apartment, down six flights of stairs and into a UHaul really started to take it out of me. I stripped off my drenched t-shirt and grabbed an ice cold beer from the fridge. As I took the first swig, my phone rang.

“I heard you’re moving away.” The voice on the other end belonged to Jana, the first girl I had ever truly loved. After dating for most of college, our relationship had imploded in spectacular fashion. Tearful fights, intense makeup/hate sex, late night texts, the whole nine yards. Exactly the type of thing you’d expect from two high-intensity kids barely out of their teens who had a whole hell of a lot more living to do. Read more »

Sisterly Secret [ff][inc][anal][mast]

SISTERLY SECRET

The night crept outside; its shadowy veil sharply punctured at regular intervals by the lights on the street. Moonlight broke at the glass window and faintly showered the room with its sheen. The place, however, remained mostly pitch-dark. Two beds occupied most of it, and two girls were inside. A couple of bags lay sprawled on the floor next to the big wardrobe, and two nightstands adorned the side of each bed.

Sidney and Emma, sisters, eighteen and twenty-one, had been reunited by Christmas tradition. The family had come together, as per yearly custom, to celebrate the merriest time of the year. The parents slept heavily at the end of the hall, in the biggest of the rooms. One door before that a single bed remained unoccupied while the elder brother was out partying. And finally, to the left, the girls’ bedroom sheltered the two siblings from the cold outside.

It was around 2am when she felt it; it was the younger of the two, unable to sleep, who this time felt that tingling, that urge. She had been thinking about it all week, waiting, dreaming, and now had appetite for it… her sister’s ass. Christmas night would mark two years since the first accident. The girls had discovered a new taste of fun and pleasure, and it had changed them forever. Read more »

Hawaii hotness with [m]y (kind of) cousin [f]

*I’m on a trip in Hawaii right now, and all I can think about is what happened the last time I was here on a family vacation when I was 19. All the reminiscing inspired me to share this little story about me and my cousin.*

First, some background. I’ve always known my cousin (we’ll call her Sammy) is cute. Even before I knew what it was to be attracted to a girl, her freckles and tomboy attitude drove me crazy. And as we grew up, her just one year behind me in school and age, that feeling grew too. She changed from an adorable little redhead with a big gap between her front teeth to a total knockout by the time she graduated high school. And I was enamored the entire time. We didn’t see each other that often, so every time our family got together it seemed like she had developed some new enrapturing feature. Her braces came off and she had a beautiful, lily-white smile. Her bright red hair began taking all sorts of interesting and enticing shapes as she got involved in cosmetology. Her shirts started getting lower as she developed a pair of perfectly perky and squeezable boobs. And her jeans got tighter as her volleyball-playing butt got ever rounder and firmer. Read more »

Cheating her way out of a bad situation [MF]

I had just started college and was trying to get settled on campus. I thought a good way to get involved and meet people was to join a fraternity and get involved with the Jewish community on campus. This story focuses on the latter.

I started to spend a fair amount of time at the campus Jewish center meeting some fun people and to my surprise, some beautiful women. I was a confident, good looking 18 year old guy and like any one my age, thought I was pretty hot shit. So I was not shy talking to girls. This was especially easy because most of the other Jewish dudes on campus were kind of dorky. Anyways.

I met Lauren one Friday night in the fall. She was blonde about 5’3”, and the reason I first noticed her were her enormous tits. I went up to her and sat down and we started to chat. She was very charming and pretty and frankly seemed out of place being from California at my midwestern school. She almost immediately called me for being interested in her because of her boobs. I steered into the skid and admitted that was the case. She smiled and told me she appreciated the honesty. After this we talked on the phone a few times, chatted online and continued to see each other at events. There was definitely some chemistry between her and I. There was only one problem, she had a boyfriend. That problem was exacerbated by the fact that they lived together on campus. This, however, would soon change. Read more »

Sexy Doctor [MF] [oral] [mast] [cum]

Friday: 11am, I walk in to the gym and I see her, a striking short haired brunette, petit, muscular (but not in a gross way), dark brown eyes. She was stunning.

Saturday: 10pm, my friend got a little too drunk and fell down the stairs. Broke his foot. We go to the hospital and check in and while he’s waiting to be seen, I went to grab a drink from a vending machine and that’s when I saw her, or at least a photo of her. The brunette from the gym — she was a surgeon and part of the hospitals “get to know the staff” campaign.

I returned to the gym on Monday, hoping she’d be there. She wasn’t. I went back every day at the same time until I saw her at 11am. Friday. I went over and introduced myself, said I saw her photo in the hospital, explained why I was there, blah blah blah.

We got to talking and I told her I was in advertising. She said she’d always been interested in the world of advertising and wanted me to teach her everything there was. Read more »