Virgin [f]riend becomes a friend with benefits [MF] [long]

There is a fair amount of backstory and set up to this story. I hope you’ll read it but if you want to skip to the naughty part scroll down until you see ##########.

When I was 25 I went through a really tough break up. I had been with my ex for about 8 months and I was head over heels in love when out of the blue (to me at least) she dumped me. Her name was Natalie. She was very religious and I am not. She was very fit and a vegan and I am a bit of a chubby nerd with self esteem issues who at the time didn’t even know how to cook. Now that I type it out… I probably should’ve seen it coming.

The love that I felt probably had more to do with the fact that sex with Natalie was the best sex I’d ever had. We met through a dating app and she was the most conventionally physically attractive girlfriend I’d probably ever had except for maybe my high school girlfriend. She was really fit with short blonde hair and perky little A cup titties and a round athletic ass.

[MFM] Anal Threesome Part 1

This particular sexual adventure with Susan and Greg happened on a hot Summer day while we were in Susan’s livingroom with the fan on and all of the windows open. We needed to cool off, so we kept pouring drinks and clothes started coming off. We were pretty comfortable around eachother by this point so seeing Susan strip down to her bra and panties was normal but still sexy. Greg sat on the couch shirtless with his shorts on, while I relaxed in my boxers and tank top.

Susan sat on the couch between Greg and I, but she wanted to lay down, so she lifted her feet off the floor and swung her body around so that her legs landed over top of mine while her upper body and head rested against Greg. 
“Much better,” Susan said as she smiled while looking up at Greg, and then she kissed him. Greg kissed her back and put his hand on her bra which quickly slid down her supple cleavage as he groped her breast. Susan giggled as they continued kissing so I placed my left hand on one of her legs and traced my way from her knee up to her inner thigh and Susan spread her legs open. I rubbed her pussy mound through her panties and she moaned in reaction, so I pulled her panties to the side exposing her welcoming pussy.

She taught me oral [MF]

So I was DM’ing with a follower who has been chatting with me for a while. She was complimenting the retelling of my adventures with Beth many years ago, and she remarked on my particular success with oral sex with Beth. Frankly, I’ve always thought oral was a skill set in which I excel, and it’s because of the experience I had early on, thanks to one particular girl, Stephanie. So I thought I’d share that experience. This is the story of how Steph taught me to eat pussy.

So I was 18, just started my senior year in high school. I’d lost my virginity a couple years before that but didn’t exactly have a line of girls outside my door. I was a bit of a nerd and somewhat introverted, but I was fairly self-confident.

Steph was the older sister of my friend Troy. She was 19 going on 20 and in her sophomore year of college. I’d known her for a long time, since we had grown up in the same town. We had gone to the same elementary and middle schools, although I had moved away for my first two years of high school and then moved back – since she was two years ahead of me in school, we never went to the same high school together.

I F19 have been a dom in a lot of sexual experiances – I decided to change it up a bit

My entire sexual life, I have always been quiet dominant, unusually for a girl.. And I love it. I won’t give it up. But I really want to be absolutely dominated once in a while. I got a new dorm mate last month. And he was a player, one of those types. Lets call him Ben..

He noticed that I had quite an adventurous room, sex toys all over the place etc, so he always asks me questions about my sex life. He knocks on my door one night, and comes in and sits on my bed. I had been watching porn before this, so I was really horny when I looked into his eyes. I decided to interrupt what he was saying and kiss him, and he didn’t look back. He pinned me down and fucked my lights out, and he kept doing this every night, my moans being muffled by a gag that he stuffed in my mouth

He’s fucked me with my favorite dildo several times. My juices have been splattered all over my room. This is amazing

Published
Categorized as Erotica Tagged

Helping Out A Neighbor Part III [M34/F39] [Hand Job] [Flesh Light] [Edging]

*I really advice you to read the previous parts first.* [*They are over ther*](https://www.reddit.com/r/dirty_boy96/comments/xuvm0t/helping_out_a_neighbor/?utm_source=share&utm_medium=web2x&context=3)*e. Enjoy your read.*

Three days after my first video shooting I got a text. It was from my upside neighbor, the woman I shot porn with. No, not as an actor, just being her camera guy. She asked me how I was doing, we texted back and forth for some time, then she asked me the following: “Are you still using your new toy, your new flesh light, made after my pussy?”

No need to deny anything from my side. I told her that I was dumping at least one load into it in the past three days. That it felt nothing but good when my rock hard dick was sliding in and out of it, and that it was one of the best gifts I ever got. She texted me back a few happy smileys. Then she asked me a live changing question: “You wanna show it off on camera? You wanna show, you wanna let the whole world hear how good it feels? You want me to use the toy on you, to hold it in my hands while I slide it up and down your rock hard dick?”

Published
Categorized as Erotica Tagged

[FM] Fucking Our Dealer

In hindsight, we should have known it was a bad idea. It’s almost laughable now to think this was going to end any other way. My boyfriend and I were short on cash, so offering Damon, our hook up, a blowjob for a sack of weed didn’t seem like a terrible idea. After all, I had blown guys before, so one more wouldn’t really matter. Right?

I stopped by Damon’s after work, and he had no idea what I was about to propose. We thought that would be best to surprise him. We had also hoped that maybe the tips I made from my shift that evening would pay for the weed instead. It wasn’t enough, so it was back to plan A.

Damon opened the door to his apartment and looked me up and down. He usually did this anyway, whether my boyfriend was with me or not. He could tell it made me a little uncomfortable, but he apparently didn’t care. Of course, considering what was about to happen, a slight glance was the least of my worries.

How I Turned Myself Into A Perfect Sissy Part IV [M23/F26] [Anal] [Deep Throat] [Pussy Licking]

*I advice you to read the previous parts first.* [*They are over there*](https://www.reddit.com/r/dirty_boy96/comments/xuwfq0/how_i_turned_myself_into_a_perfect_sissy/?utm_source=share&utm_medium=web2x&context=3)*. Enjoy your read.*

A few months later it was time for the next step. Not the biggest step out there, but it was an important one for me. My roommate and I went to a barber shop. It was time to get my first female haircut. At least the first one done by a professional, because my roommate has done her best to make my hair look as good, as female as possible since I began my journey.

Once the hairdresser was done she showed me myself in the mirror. I just felt pretty. I felt gorgeous. Maybe for the first time ever. I took more than just one selfie, the all went online, and my viewers, my fans, they loved them too. Nothing but uplifting comments on that day. I just felt nothing but happy.

On the following day it was time for a very painful appointment. It was time to burn away more of my body and facial hair. It was time to make me even smoother. The progress so far was good. My beard was only half as thick as before, my chest hair was more or less a thing of the past, my followers had spoken many uplifting words to me. To keep me going. And yes they were paying for it all too. I just love them all.

30 [M4F] – the cuckold partner, what would you do to get that promotion?

Hey there DPPs, I’ve always been curious, and I guess now it’s the time to finally find my RP player who have similar interests into what I like.

First a little about me; I am [M30] mixed Arab/Latin.

Kinks: cuckolding, pegging, sph, BBC worship, cumplay, humiliation, femdom, forced-bi, creampie cleaning, pregnancy, risky creampie, breeding, sissfication, chastity, bull & wife & hubby dynamics, lingerie, cuckold pregnancy, bull fluffing, butt plug, skin and body build contrast,raceplay, BNWO, black cock superiority,submission.

I do have a kink for weight gaining for me, I do understand not so many like it, but it’s something I would love to experiment with and we can discuss it further if you are interested.

Now here is the scenario I am thinking:

We are a couple in a happy, loving relationship. We could either be BF/GF or husband/wife, I’m ok with both.

Our relationship is going great in our busy city life, we are both working in the same place, and this could be where our relationship started, and we are known in the workplace as the love birds.

[MF] I accidently picked up a hooker and ended up sucking on her tits

**Context:** I am a 21 y/o virgin living at college right now. I have always had issues socially because I have high-functioning autism. Then I went to an all-boys high school. This taught me how to make friends with guys, but it left me even more socially inept when it comes to women. I have never even asked a girl out, let alone date one, and the only two times I kissed a girl were both truth-or-dare games when I was in elementary school. So basically, I have no game whatsoever. This also made me a very straight-laced kid, waiting until I was 21 to smoke weed and drink so it would be legal.

Last night, I went to a party a frat was hosting at their house near campus. I smoked weed and drank, then left the party at 2am when I was sobered enough to drive. I stopped at a Speedway on the way back to my dorm for some Monsters. As I got back into my truck, a black woman (Late 20’s to early 30’s) walked up and asked for a ride home to a really ghetto area a ways away. Just wanting to help her out (and still being autistic) I let her get in and I drove for a long while as she directed me further into a real ghetto part of the city. We made some idle conversation along the way: What I had been doing “I was at a party”, what I did “I go to the University nearby”, how old I am “I’m 21”.

Life Lessons: Chapter One: 21+ [F30/M34] [Straight Sex] [Busty] [Huge Boobs] [Implants] [Sex Worker] [Cheating]

Chapter One: Introductions

For as long as I can remember, I have always liked cocks. It started on my seventeenth birthday when I caught my older sister April bobbing her head up and down in the back of her boyfriend’s car.

I didn’t see anything other than her head going up and down repeatedly because the moment I started getting closer, she spotted me and shooed me away.

April is eight years older than me, and between her and my older brother Clive, they raised me. My parents died in a car accident when I was nine. Clive had to step up and be the so-called man of the house at twenty-two.

The two of them raised me to be different than they were. They always told me our parents were reckless and parented by the seat of their pants.

It was why Clive dropped out of high school, and April had so many after-school activities. Neither of them wanted to be around our parents.

I learned quickly that my parents died the way they lived, doing things they weren’t supposed to, namely drinking and driving. A tree stopped them both from doing that ever again.