Tag: Oral

The Sissy Journal Vol 001

Day : 03/13/2019

Time : 1:30 PM

How : Gr****r

Where : His Place – House

Name : ? 001 ?

He hit me up on gr****r. We chatted and swapped pics. Sent girly pics first, then boy pics. He wanted to meet up right away.

I went over to his house in boy clothes. He lives only a few blocks away. I walk in…

As tall as me. Olive / white skin. Chubby Hairy Daddy Bear. Glasses. Cute.

We sit in the front room and I light a joint. We puff it once before clothes start coming off. I show him my freshly shaved legs and asked if I shaved all the way to my ass. Of course I do and he wanted to see. I strip completely and turn my ass in front of his face while he sits on the couch. He touches and spanks my ass. Then he stands up and takes his pants off. OH MY GOD, HE IS UNCUT!!! I have never sucked an uncut cock, so I quickly get on my knees to give it a try. LOVE IT!!! He likes deep head. He wanted to fuck me, and tried a few times, but I wasn’t “ready” ( I explained it to him after ) for anal. He stood over me and worked my mouth and throat till he was ready to cum. Asking where I wanted him to cum, I opened my mouth and stuck out my tongue. I let him cum in my mouth and kept in in for a little bit after. I spit it into a tissue that was in my jacket pocket. HOT ONE, HAVE TO DO IT AGAIN! Read more »

[True Story] Fucking two redditors in one day (Part two!) [Oral] [Mf] [fsub]

Me: 24, brown hair, baby blue eyes, lip and nipple piercings, curvy/plus sized.

Ty: 30s, fit and broad shouldered, brown hair and blue eyes, CEO suit type.

So I had a bit of time to kill between Keegan and Ty. Ty lived in a high rise condo which had a coffee shop at the bottom floor. We planned to meet there either way, so I arrived a bit early and ordered breakfast. There ended up being plastic in my food (yuck) so I got it for free, opa!

He was running a bit late, so I stepped outside to wait for him. It was freezing balls outside and I was underdressed, so as soon as I saw him, I said “let’s go straight to your place”. He and I had been talking for a few weeks at this point, and I was super excited for my playdate with him.

We get upstairs and into his apartment. He gave me a quick tour, and I kicked off my shoes and dropped my bag. He grabbed a handful of my hair and dragged me in for a kiss, aggressive and powerful and dominant and just how I like it. He growled into my ear, “You’re going to be a good girl now and suck Daddy’s cock”. Read more »

[True Story] Fucking two redditors in one day (Part one!) [Oral] [Mf]

After my first trip down /r/randomactsofblowjob, I was super happy and felt more confident. Lane was such a sweetie and I had such a nice experience with him that I decided to try for another one. I threw up an ad for a bigger city and was promptly drowned in messages. (I’ve learned since that I usually get anywhere from 20-50+ responses per ad, depending on the size of the city.)

There were so many nice guys to choose from! I honestly couldn’t decide. It came down between two guys and they were both honestly perfect. My inner ho said, “why not both?!” So I scheduled Michael for the morning and Ty for the afternoon.

Michael, a random guy in his 20s, ended up cancelling the day before. Boo! Ty was still on though. I had already felt pretty committed to being a slutty girl that day, so I threw up another ad looking for a last minute fill in for Michael. I went to bed with minimal responses, and figured it just wasn’t meant to be. Read more »

Please Dadddddddyyyyyy. Pleaseeeeee will you? [M] [f] [inc] [oral] [voy]

It had been a long trip and I am so glad to be home. The jet stream was good to us today and made our trip an hour and a half shorter then it should have been so instead of getting in at 2 pm we got here at half past noon. The drive home was quick, no traffic at all, what a pleasant surprise. I think of calling the house but pass on it thinking that there would be no-one there anyway. The cab pulls in to our street and I stop him and tell him that I will get out here , it’s too nice of a day no to walk the last few hundred yards. The cabby gives me a funny look as he gives me my change and pops his trunk. I get out of the cab and the warm spring breeze caresses my face. I get my bag and start the walk down the street taking in all flowering trees and shrubs. Their aroma is intoxicating and my mind wonders of to Kelly, my 17 year old daughter. Just before I left on my trip I walked in on her in the bath. It was a honest mistake, she had left the door to the bathroom unlocked and I did not realize that she was in there. She was laying in the tub with her legs up on the edge and her eyes closed with one hand on her rather large soft breasts while the other one was in-between her spread legs. Read more »

[MF] Don’t fuck your coworkers (unless they’re hot)

It’s a bad idea to try to fuck your coworkers. But sometimes your coworkers have a nice ass, great tits and a sexy smile. So this started with a truly bad decision.

I met her a few years ago, and immediately was friendly to her. This was a lot because she was talented, and a lot because she was attractive. I promise that I don’t befriend my coworkers just because I want to fuck them. But I will absolutely picture what it’s like to fuck a coworker that’s attractive.

With her, she had spent time modelling. Going through her Facebook photos was definitely interesting. I did my best not to be a perv, but she was stunning. And she kept posting about open relationships. It was something that she was curious about. Eventually, I took this as an “in,” to strike up a non-professional conversation with her.

Each message I sent, I was fully prepared to shut it down, take a cold shower, and move on. But every one of replies tugged out more and more details about my private life. Read more »

Covert Seduction [MF]

Her second drink arrives as she perches on her barstool and patiently observes her target, Victor Lancaster. Victor may not know that his company manages investment accounts for sex traffickers, contract killers, and other unsavory groups. He is a rainmaker, a moneymaker, and the company lets him do his magic. He’s the weakest spot in the company’s security armor.

Victor is good looking, better than many of Taylor’s assignments. He’s already got some gray, a bit early for a 35 year old man. He’s just over six feet tall, and fit. He’s wearing a perfectly tailored suit, stylish and sleek, with a slightly loosened tie. He’s got a roguish smile, the easy confidence of a man who has won at life repeatedly, and expects the world to continue to lay down at his feet. Taylor is ready to make her move, to reel in Victor like the arrogant fish that he is, but there is an obstacle. Read more »

I Fucked [M]y Brother’s Date [F]

This is my first story C&C is welcome, DMs are too!

Within 24 hours of breaking up with my now ex-girlfriend I had a rebound and fucked my brother’s date.

I’m a 22 and this happened a few months ago. I had moved to a much larger city for graduate school and I was in a relationship that wasn’t going anywhere, was long distance and had serious issues.

I ended it and within minutes had a Tinder, bumble and a few other apps set up. I was ready to move on and see what a city had to offer me. After swiping away I decided to head to sleep and see what would happen.

The next day I woke up to my brother in the other room getting a call, he darted into the shower and went out the door in a rush. I didn’t care for it and went about Looking at my matches I had a few matches one of them had an usual message: “Peter (fake name)? Is this you?” She had confused me with my twin brother. I explained that we were Twins and that it’s an understandable mistake. She then revealed to me that she was on her way to meet up with him on a coffee date. We chatted a bit and jokes around before their date. Then silence for about an hour or two until I got a message asking to become Facebook Friends. Read more »

My First Bisexual [MMF] Experience

We had a super cute guy who lived next door to us a few years back. He was about 25, I was 32 and my husband was 40. There was a ton of sexual tension between he and I from the day we met and I was always flirting. Since we were swingers, my husband has always always been cool with any advances I make, in fact he encoraged it and still does. I always made a point to sunbathe on my deck where he could easily watch. Although I never went nude, I came very close and enjoyed wearing as little as possible when I knew he was around. I knew he loves looking.

One afternoon he joined us for drinks on our deck and things got very friendly. We decided to move indoors and a game of strip poker broke out. Since there was only three of us, we were naked pretty quick. He was every bit as yummy nude as I had hoped – great body, nice legs and a beautifully shaped penis with a nice trimmed bush and perfect set of tight balls. His cock looked good and I couldn’t help but wonder how big he would be when erect. Read more »

Well Endowed; A detailed sexual history of how I came to realize [M]y cock is huge.

I didn’t have the slightest clue or idea that I was well endowed until age 28. I have had a fair amount of partners, many of which dropped hints or made it abundantly clear, but thanks to porn and associated conditioning, it took me a very long time to finally recognize, understand and overcome a serious insecurity that my cock isn’t small, isn’t average, but actually is unusually large. Below is a brief account of my sexual history and all of the “hints” I received (and flew well over my head) over the years, leading to eventually overcoming this insecurity. Fair warning that this will read as a humble-brag, and to be honest, it more-or-less is exactly that. I’m writing this with clear eyes in hindsight. This is almost even therapeutic for me as at the time I was going through literally all of these experiences, I was seriously and shamefully in denial that I was large, assumed I was small and inadequate (thanks to porn’s misconceptions and a few select partners), thought every girl was just being nice & lying when complimenting me, and was constantly trying every thing possible sexually to be bigger and better to live up to the pornographic expectations from the clips I watched through my adolescence. I hope you either enjoy reading purely as a sexual experience or it helps you to overcome your own insecurity and that your cock is perfect, no matter what may you think or feel otherwise. Read more »

Swapping Fuckbuddies [FM]

Amy is my best friend, and has been since we met my freshman year of college. Starting sophomore year, we roomed together, and we were usually connected at the hip. There wasn’t a hardship we didn’t share, a joy we didn’t celebrate together, or a guy we didn’t tell each other about in total, juicy detail. By junior year, we had gotten a bit of a reputation on campus, and by senior year, we were officially the girls your parents warned you about. We heard rumors about girls specifically requesting on their housing forms to not be roomed next to us, but we never figured out if that was true, or just ego stroking. Regardless, our senior year, we found ourselves in a huge basement room for three people, but our third roommate, a sweet girl named Karen, spent most of her time at her boyfriend’s, so Amy and I had pretty free run of the room. We’d set it up, with a little bit of help from some duly compensated frat boys, with makeshift curtains (sheets) that allowed a measure of privacy while changing and, more importantly, while fucking. The room was split into quarters, a common area, my bed, Amy’s bed, and Karen’s bed, which we sometimes used, with her permission (I think), as a bit of a catchall. It mainly became used as a coat room, very handy when patience is not in the cards. Read more »