I [F] had a Spring Break to remember

I posted this on r/stupidslutsclub. There’s not a lot of activity over there. Didn’t see anything in the rules about ceossposting so hope this is okay :). I’ve been documenting my adventures for awhile, check on my post history of you’re curious.

So this week was Spring Break, and what a break it has been! I get the week off at my job. My birthday has been earlier in the week and I was taking care of some obligations, but I knew I would have 2 1/2 days to be a big slut, and that’s exactly what I did.

So from where I left off last time, I continued fucking Dean and Gabriel, when I could. I’ve probably been averaging 1-2 times a week, not nearly enough than what I usually want.

So, let’s begin.

[MF] My best buddy’s widow. Part 4

Part 3 here:

https://redd.it/b1ewjh

Last weekend was the longest time that Addie and I spent together. A couple of things contributed to that. First, I think Addie was happy that we basically got her daughter’s blessing for us to see each other. Addie was not sure how her children would take to the news of the two of us seeing each other and having her daughter’s approval was a big relief to her. She was not really worried about her son since she felt that her daughter had her back.

The second was the fact that I will be gone for the next two weeks for work and I will be on the West Coast and Hawaii. Calling each other will be more limited because of the time difference, especially when I am in Hawaii.

I’ve already talked about what happened on Thursday on part 3, so I will start with Friday.

It was a busy day for me since I was leaving on Monday. I made my appointments, made sure I had everything I needed for my trip, etc. I was getting ready to make another pot of coffee when Addie walked in. I was surprised since it was only 12:15. I asked if everything was okay and she came up to me, threw her arms around me and we kissed.

Had [M]y way with a virgin sissy in a Dallas hotel room

Playing with people on Reddit is damn near impossible. If you find someone near you or just willing to play virtually there is a higher than they flake out than on any other platform. Fetlife or Tinder are much easier. But there are less people on Fetlife and less kinksters on Tinder. So I end up here.

Lena was posting pics when she first caught my eye. This wasn’t the normal guy in panties stuff. These were full blown photo sets from the lips down. Skirts. Blouses. Dressed. Heels Stockings. Lingerie sets with matching garter belts. It showed dedication. I noticed we were in the same city. And so I messaged and we started chatting.

Some elements of her story were typical. She liked to dress up. She was curious about men, but had never been with one in any capacity aside from a little oral exploration, but that was way back in college before she started dressing up.

I was more fascinated by the atypical things about Lena. That she’d first started crossdressing when a girlfriend has requested it. That the woman had taught her how to dress and do makeup. That she’d been fucked with a strap on regularly.

Big sex with a below average cock [MF]

My wife and I have been married for 23 years. About 10 years ago we started going to a nude beach in NJ and I commented to her that I always thought I had an average cock. After looking at the guys there, I realized that my cock was pretty small. I realize that you can’t really tell unless they are erect, but it still was apparent that I was definitely below average.

I never really thought about it much and she never seemed to care, so it was never a big deal. As part of the conversation, she disclosed that I was, in fact, the smallest partner that she had ever been with and that she actually had dated three or four guys that were very well hung. She also said not to worry and that my cock feels fine and our sex is great – but it still left me wondering and a bit worried about it.

Up Against The Wall [MF]

“So long, first apartment. I’ll miss you,” said Tyler Avery in a distant, but resigned tone.

“Technically, it’s a dorm room, Ty,” said Lindsey Bailey, his bemused girlfriend of the past two years.

“Call it whatever you want. It’ll always have a special place in my heart.”

“Despite the moldy showers and lousy heating?”

“Especially because of the moldy showers and lousy heating.”

It might have been a strange sentiment to have, holding an undersized and unremarkable apartment in such high regard. Tyler certainly didn’t blame his girlfriend for being eager to move out the day after they graduated college. However, he couldn’t help but have some personal attachment to his first ever home away from home.

“This is where I finally grew into who I wanted to be,” Tyler said to himself. “I got to reinvent myself within these walls. I became someone I could never have been anywhere else.”

[M]y [F]irst Coworker—and Boss’ sister—Fuck: Part I

I’m fit, blonde hair, blue eyes, late twenties, well-spoken, about 6’2″ with shoes, and a proud nerd. I switched jobs like 2 years ago and immediately was thunderstruck by a coworker who emailed me some introductory information about the company. We worked though in different offices. It didn’t take long for me to realize it was my boss’ younger sister and that we would be training together in my second week a couple of items.

I’ll call her Jade. Jade was mid-twenties, strawberry blonde thick long hair, porcelain complexion with sharp eeyebrows, big brown eyes, and full lips. And curves for days. Busty, thick hipped, and lovely thighs, but not heavy at all. I couldn’t keep my eyes off her profile pic in the emails she would send to me. And in-person after training together, sitting next to one another, I kep looking at her lips. Her voice was a little deeper than I expected, but I liked that. An alto not a soprano. It was hot. I kept my distance for weeks. She was in a relationship I learned and I was too. But that didn’t stop her from emailing me in times when I honestly probably didn’t need to hop in and help her digitally. I would analyze her playful unnecessary use of an emoji or exclamation point. And since Social Media was a part of our work for marketing and learning about competitors, naturally her profiles starting getting recommended to me.

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!

[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”.

[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.

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.