30 in 30 Challenge

(Photos are from 2023)


When I was younger, I was very competitive. 


The challenge:

Fuck 30 New Cocks in 30 Days.


The challenger: b.

The challenged: Shorty (me) (in my mid 20s)


This challenge would have been very easy. 

IF I didn't work a full time job plus a part time job. Plus I had a family.


It was more challenging to find time than it was to find available cocks to please me. Oral and/or vaginal sex counted.


30 new cocks in 30 days? I'd have to get creative.


To be honest, years later I don't remember each of the 30 cocks I played with. There were a few that stuck out and one that I still keep in touch with. 


Did I win this challenge?

Fuck yeah I did. It was a mind blowing adventure.


The first gentleman that sticks out is one I still chat with today. I found guys to fuck in Yahoo chatrooms and met them somewhere for a little naughty time. I knocked on his hotel door, a little nervous. In the early 2000’s my self-esteem was low. I didn't find myself attractive at all and I definitely didn't think of myself as the object of anyone's sexual desires. 


I pushed my nerves to the side, took a deep breath, and knocked on the door. 


A good looking man in his late 20s answered and invited me in. I think he was more nervous than me, which immediately calmed me knowing that I was not the only one.


We both got undressed. There was no sexy all over each other, tearing clothes off like you see in the movies. We got naked in our individual corners of the room and then met naked in the bed.


What started out as a mix of awkwardness and nerves quickly turned into a late afternoon of great sex. I took control and kissed him. Kissing is not something I do often with strangers. I don't know why or what prompts me to kiss someone. Maybe someday I'll try to figure that out. 


From kissing to licking to sucking to fucking, we spent over an hour exploring each other's bodies. 


When we were finished, we freshened up, kissed goodbye and went our separate ways. Over the years we have stayed in touch and occasionally got together to fuck. 


Another man I fucked was even more memorable because of the extra risk factor involved; we went parking. We were being naughty in the front passenger seat of his truck, then the tailgate, then bent over the front seat, getting railed from behind. 


I had to be at work by 8am, so we met early. It was before the summer heat hit so I could spend a ½ hour getting fucked then pull my dress back down and go to work. 


To win this challenge I'd need more than one cock at a time. Of course, that meant a trip to Fritz the Cat, a bookstore just outside of Wheeling, West Virginia. 


(This bookstore has been sold and is currently under new ownership and much, much better than Fritz was. I 100% recommend checking it out, it IS worth the drive.)


b. always accompanis me to the bookstore. We arrived and made our way to the glory hole section and entered a booth. This was pre-remodeled Fritz, with the old booths made of plywood or something similar with holes that were too small cut in the walls.


I wrapped up a few cocks and sucked them one at a time, through the glory hole while b. watched and handed me condoms. 


We exited the glory-hole area and went into the theater. Back in those days the theater floor was sticky. You definitely didn't want to get too comfortable in the theater without first inspecting your seat. 


They always gave us free theater access because not many couples visited, likely due to the lack of cleanliness. When a couple went into the theater, many of the lurkers would pay to go into the theater to watch or hope they got chosen to fuck. 


b. took a seat in the front row and I sat on his knee. I was not touching the chair. Guys would get closer, but not close enough to touch. I let my eyes adjust to the darkness of the theater with only one big screen in the front of the room. 


After my eyes adjusted enough I looked around at the guys. I was looking for both cleanliness next to hardness. 


I could see through their pants if they had the right kind of cock to fuck me in the theater. The only position I felt comfortable with was standing facing the old theater style seats with my hands on the back of the seat and Mt play partner behind me, sliding his cock in and out until I decided he was finished, or he came…whichever came first. (Pun intended lol)


I located the cock I wanted. He was big enough, but not too big. Too big and it hurts me to get fucked from behind. Too small and we risk losing the condom in that position. I needed a cock that was just right. 


Not too big. 

Not too small.

Goldicocks (me) found the cock that was just right. 


I motioned him to come closer and whispered in his ear “do you wanna fuck me?” Of course he did. He was hard at my mere presence…he was ready to fuck. 


I wiped down the back of the seat with rubbing alcohol pads, those little ones that diabetics use to prick their finger before testing their blood sugar. The alcohol was sure to kill most anything that may have had contact with the back of the seat where my hands went. 


After putting a condom on my new play partner I tuned around so he could fuck me. It didn't take long before he fucked himself to orgasm. 


I stood up and straightened out my dress and sat on b.’s lap while my play partner pulled up his pants, condom still dangling from his penis, before exiting the theater. 


It was almost time to go. Before I left I wanted to check out the small toy sales section of the bookstore. I wasn't looking for toys, I was eyeing up the guy behind the counter. I saw the way he looked at me when we first walked in the door, well over an hour ago. 


He watched me as I browsed. He asked me if I needed any help. I couldn't resist. “Wanna help me cum?” 


And started the saga of the summer I fucked the Fritz the Cat employee. He had a big dick too… and was young, well young for me, in his late 20s. But that's a story for another time. 


If you enjoyed this trip down memory lane, let me know! I'll be sure to write about more of my fun fucking adventures.


I hope you enjoyed reading my sexy adventures. 


Kisses 💋 

Shorty 


Can you share with your kinky friends? 


Join my group on FetLife

https://fetlife.com/groups/288472