Brother and Sister roleplay

I created this the other day thinking about if I had a sister. Sadly I only have brothers, I think the taboo is beyond hot! If you like it I have the other half of the story that I would love to pass on to you. Anyways, take a read:

Being home blew. So. Fucking. Hard.

Okay, I couldn’t blame my parents, honestly, they helped put me through college and in the process lost their gorgeous, three bedroom, three story country house and now live in a slummy two bedroom house in town. Since my sister is just now in her senior year of high school she still lives at home, so she’s afforded the second bedroom as my parents have the other.

Which means I’m relegated to the living room couch. Which, again, isn’t terrible, and most of this is the thesis of a first world problem, but sometimes I hate the loss of privacy.

In the old home during my late, sleepless nights I’d splay out on my king sized bed, basking in the light of my laptop screen with my basement bedroom door closed, away from everyone, fervently jacking off to whatever erotic videos I could find on the internet. Sometimes I’d even get daring and hope on cam and let some lucky lady see my youthful stomach clench up as I softly moan and spray cum all over my happy trail, and chest.

Cute Babysitter: Part 1 [MF]

As a 28 year-old single father, I was incredibly busy. I was lucky to have Dani around to help with my 2 year old daughter, Lilly. Dani was 15, but she wasn’t the terribly angsty type of teenager. It helped me when things got stressful. She had helped me for the past two years and I paid her well. Being a successful banker made that possible.

She was incredibly cute. She was about 4’10” with long, dark brown hair, hazel eyes and beautiful, full lips. Over the past year I noticed her grow into a woman. She started working out and started sporting a round ass. Her tits came in rather quickly. They grew so fast I noticed she was wearing new bra’s every month. They were incredibly large, especially for her small, slim figure, but they definitely added sex appeal to her. She was 15, though, so I’d never imagine doing anything with her.

Published
Categorized as Erotica

[voy] [str8] [MF] I followed you home

My sweet,
I hope you enjoyed last night as much as I did. I can still smell your pussy on my fingers, I can taste your saliva on my tongue. The feeling of your body shaking as my cock penetrated you is still fresh on my mind. Your sweat still drips down my chest as I write this. I’m stroking my cock thinking about you. Thinking about the way you guided my fingers inside of, how you sucked on my balls, how you ran your perfect tits up my crotch and chest, how you told me to fuck you as hard as I could.

I want to give you props for how you rode me, how you were able to roll your lower body and move my cock around inside of your pussy. I bounced you up and down and heard the wetness of our sex collide. I was so turned on when you came and screamed out my name. When you bent over the bed and pulled your legs apart and told me to fuck your tight ass. I did, and I shot my cum inside of you, and again you screamed in pleasure. However I have something to confess.

head to a random Craigslist guy in Vegas. 50MWM

About me. Im 50 married with grown kids. I did give head a few times when i was growing up but nothing in literally decades. so a couple of months ago i find myself in vegas for a few days. i put an ad in CL, asking if anyone wanted to allow a rookie to suck their cock. i got a few responses, and one guy seemed very nice, and happened to be in the same hotel. we went back and forth a bit, and i got up the nerve to head to his room (was a bit buzzed so that helped). we were emailing and i said i was outside so he came out. very very awkward moment but he was nice. we headed in, and trying to be quiet i guess almost no chit chat. admitted i was nervous as fuck, and just asked how he wanted to be positioned. he dropped his pants, and laid on the bed. i will admit he did have huge balls, but was only abotu 6″ hard. i got down on the bed. one hand on his cock and other on his leg. played with it till he got hard and slipped on the condom. i started to do my thing. sucking his balls, licking the shaft and then slide it in my mouth. started to bob on it. i tried to take my time and let him enjoy it. i guess we went for about 15-20 minutes and he said hes close. so i just slide it all the way down (not too hard to deep throat 6″) and he arched his back and came hard. After he was done. i just held his cock in my hand and was licking his cock head, and playing with the bubble of fresh cum in the condom. He was willing to suck my cock but that was enough for a first time so we parted ways. We emailed a few times and he said i gave good head so i was pleased about that. I will be out of town for work again this week and will admit i have already posted an ad, and im down to one 48 year old guy, or a 46 year old black guy for my next cock.

My First Tinder Experience [m/f]

I’m not sure how I learned about Tinder, but eventually I heard about this new app used for hooking up. Tinder would like us to believe it’s a dating app, hell some of the women on Tinder want to believe it’s a dating app, but we all know Tinder is used for hooking up.

So I joined Tinder and started my profile. I was living in North Jersey at the time about 15 miles from New York City so I had tons of profiles to swipe right on. This was a couple years ago so there was no daily limit on the number of likes you had, and I spent the better part of three days swiping right. I had a number of matches and began chatting with them and feeling them out.

One girl in particular was from Rockaway, New York. She did shift work at a hospital, which was perfect for me. I had never been to New York at this time and really had no idea where it was. I pulled it up on a map and it was only 18 miles or so, the drive seemed doable to me. The conversation turned sexual eventually and we chatted about what kind of things we were both into and our likes. She lived at home and her parents were out of town for the week so we made plans to meet up after she got off of work one day.

Fantasy becomes reality. Fucking my friends 18 y/o sister.

Brief overview, my childhood friend Bryan since kindergarten has a sister Danielle who is 8 years younger then us (shes 18 were 26). I’ve watched her grow up but around the time she turned 16 she got crazy hot and has only gotten gotter since. I would be lying if I said I hadn’t fantasized about her before but the fact that she’s my best friends sister and (mainly) ger being underage I never dared to go beyond that but that all changed the week before she set off for college.

About a month ago Danielle was having a big going away party before leaving for college and of course I attended. Because of her birthday she graduated highschool before turning 18 so being that she had just turned it was also a birthday party for her as well. Nothing that night went out of the ordinary and being that we were all drinking I decided to crash at B’s place for the night on his downstairs couch. Sometime in the early morning however I was woken up from the feeling of being touched.

(M)y (f)irst anal experience with Meghan and her fat ass

A year after I’d graduated from college I was back in my college town to visit some old friends. Of course we all got drunk and went out to the townie bars. My college town was more like a village that tripled in size during the school year, so everybody knows almost everybody.

Late in the night when I’m good and hammered I end up randomly grinding with a cute, lightly freckled redhead. We grind for a bit and she’s not a big girl but she’s definitely thicker than the athletic, fit type I usually go for. She’s about 5’5 with a meaty ass for a white girl and every time she rubs it into my crotch, my cock is begging for a bite of her. She knows exactly what she’s doing and isn’t shy at all with her booty. Her skirt is way too small showing almost every inch of her thighs, but all I want to do is hike it up a bit more and have my way with her.

My First (and incredibly rough) MFM

My first ever threesome happened at a frat party in college. I was a freshman. It was my second ever time going out that semester; I went home a lot because I was dating my high school sweetheart.

I was on the dance floor with some friends all evening. I danced and flirted with a few guys throughout the night and must have felt at least 10 guys grab my butt cheeks in the dance floor.

At some point, a really hot guy (Dave) asked me if I had ever been to a frat party before, and when I said no he offered to show me around. He smiled at me and extended his hand, leading me upstairs.

He did give me an excellent tour, which conveniently ended in his room. His roommate (Tom) was already there, just out of the shower, shirtless. ‘Well hell’, he quipped as I looked at the ground. We all sat down next to each other on his couch, me in the middle. After some small talk, in which Dave learned I had a boyfriend, he asked me what I missed. I was unable to answer.

[20M] After months of flirting, I finally had sex with my [39F] university teacher!

Pictures of her (with her permission)

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She first started working at my university back in November, and she was in charge of one of my units and had us for class every Wednesday. When I first met her, we really hit it off, not in a sexual way, but we got on and had a lot of things in common. I saw her every Wednesday and we really formed a good teacher and student friendship. However, shortly after Christmas, our student teacher friendship went a little further because of my growing confidence.

One day, while she was helping me with my work, I got confident and decided to flirt with her. I was telling her that she looked wonderful and started to compliment her body and her breasts. At first, I thought I went too far, the teacher student bond is broken and now it’s going to be awkward between us. But surprising…she fell for it and started to flirt back with me, she had to be quiet as she did not want anyone else to hear that we were flirting with each other. She was telling me how attractive I am and she loved our conversations that we had at the end of her lessons.

[M]arried [F]antasy

I hear the car pull up. Two quick honks slip out from its underbelly. The first honk was to turn on the alarm, the second lets me know it’s driver is my curvy wife. She comes inside and heads for the room. She enters the room, spinning behind the door as she shuts it, that feeling of exhaustion after a long day of work written on her face yet glowing through it, is her beauty. I offer her a bowl and a hug. She raises her finger up to me in protest. She holds the green and blue glass to her soft naturally puffy lips. I use my torch to light her way. The green turns to an ashy gray. She holds her arms open to me. My arms wrap around her, I feel her chest press against my ribs. Her scent even after work, is enchanting. I lean in closer towards her neck. Her hair sways to the side, parting its way for me. I kiss her neck gently. she paints the room with clouds. My lust grows further for her. I kiss her shoulder, she responds with a light moan. I peel myself off of her, like a sticker on beautiful plastic; shine. I step away from her and explain that I’m busy with work tonight, I rub my head lightly with my left hand while staring into her deep dark brown eyes. I can always see myself in the reflection, How I disappoint myself in her presence. I hold her side with my right hand. She holds her hand over mine. She slides it downward, past her side and to her hips. I feel her curves between her smooth skin and perfect warmth. I take a step closer, she takes a step away from me, but towards the bed. I step with her, I rest my lips back onto hers. I grip her curvy hips and lay her onto the bed. I get on top of her and kiss her neck again for a moment and then find myself between her cleavage. Her skin is silk on my face, my beard tickles her gently. I slide my hands down her pants, feeling her legs; her pants drop to the floor. Her nipples harden behind her bra. I unlatch her it and pull it off her. Her wonderful large chest is revealed to me in such a way that I can hardly contain myself. I slide my right leg between her legs and gently press it against her warm panties. She moans at the pressure. I gently grind on her, rubbing her pussy through her panties. I slide my hand in her panties and spread her lips and gently press my leg against her again, slightly harder now, her pussy throbs. I lick her nipples just before giving them a light suck. My cock throbs in my boxers. She reaches into my boxers and feels my hard cock in her hand. I throb in her tight grip. She rubs on me while I grind on her. Her large tits bouncing lightly while I suck on her nipple. She squeezes my cock and looks in my eyes “I need you inside of me.” My cock throbs hard. I get on top of her and I spread her pussy lips. I grab my big dick and rub the head on her clit, rubbing it up and down we both moan. I send her tingles as i rub the head of my cock around her pussy lips. I push my cock slightly into her pussy, the wet plungling feeling takes over me. My cock slips deeper into her, the warmth, the wet slick grip threatens to make me cum before even getting started, a truly melting feeling over comes me. My balls hit against her ass, I’m deep now. So deep. I pull out slowly to avoid hurting her since I can tell by her eyes that I’m already too deep inside. She lets out a heavy moan as I slowly slide out of her, I push back down. Her eyes go wide and her pussy throbs, her mouth gaping open, her tits bouncing with every heavy slam of my cock hitting deep within her tight moist pussy. My cock throbs, she moans. I start fucking her faster, she gets wetter as I slam my cock in and out of her. She stops me and pulls my cock out. She crawls over to me and slides my cock into her mouth, she sucks on me like she means it. My cock throbs like crazy in her mouth she feels my excitement and perks her tits up for me, I feel myself getting close, I throb in her hot mouth, her puffy lips wrap around my thick dick. I moan deeply and just before I cum, she stops. She turns around and raises her ass to me. “Please hubby, fill my cunt” I jump to her and grab her hips, my cock stiff as a rock slides into her with ease, I slam my cock into her as hard and as fast as I can. Her wet pussy makes the sexiest sounds as my thick dick slides in and out her tight box. I grab her tits from behind and slam her pussy as hard as I possibly can “CUM! CUM INSIDE MY PUSSY HUBBY!” My cock pours days and days worth of built up cum into her tight pussy. as I pull my cock out it pours out as well, a pool of hot white cum sits between her legs. She takes two fingers and scoops some up, she drinks it from her fingers. “Perfect.”