I've been single for a few weeks now. I left a toxic relationship that was fun but definitely had no love for the last few months. It's my fault for not putting an end to it sooner but I really enjoyed the sexual aspect of it.
It all started when I got caught on video sneaking my ex's sister's panties from her dirty laundry. I was looking for socks and convinced myself at that point, I might as well go for gold. Unfortunately her sister had a camera set up in her room and saw me take her used panties to the bathroom - and it's the fastest I've ever cum.
Well that led into more or less blackmail and I became a sub for my dom of an ex. I learned and appreciated so many new kinks and the biggest one I enjoyed was crossdressing and being used. She used to call me a sissy and would peg me, make me worship her, do humiliating things like be her toilet. Eventually she got bored and left and I was torn between relief and sorrow.
That crossdressing kink stayed and I had plenty of toys, outfits and wigs as well as a decent collection of makeup now. I also have a cage I use when I'm feeling naughty and it's becoming more frequent. I tried really hard to get a prostate orgasm but I get too frustrated and end up taking off the cage and finishing the old fashioned way.
I decided I wanted to achieve the "sissygasm" and after a lot of research I figured if someone was fucking me who was big, then I'd cum in no time. I was scared to do something too gay and I didn't want to cross a line but I convinced myself it was worth it. The first step I took was I froze my chastity key in a block of ice. This helped so much because I would ride and ride my toys but want to touch my dick, but I couldn't quick thaw the key in time so I just kept fucking my ass to get any relief. When I fuck my ass I'm usually really hard when I start and it strains against the cage but after a bit I go limp and just ride for the anal pleasure.
The next step was to find someone game. Now that I was super horny I needed release. I got a few DMs on reddit and exchanged a few photos and vids until I found someone interested. He was a bartender, 6'3 and muscled up. His cock was massive and after some more exchanges he said he wanted to use my ass. I tell him about my key and he says to bring it over this weekend. The whole week I was edging to my toys nonstop but couldn't get the release I craved. I would send more videos to the guy and he would encourage me to behave and keep the key frozen. As it approached Friday evening I got excited and nervous.
I got ready for the night. Made sure I was completely shaved, and I wore my one piece fishnet lingerie. I painted my nails purple and put on my pink wig. I put on some short shorts that really made my ass look good and a white top. I have some open toed heels that really pulled the look together. I spent a long hour trying to follow an egirl makeup tutorial. After I was ready I grabbed my chastity key from the pot I was thawing it in and headed over to their place.
When I arrived I got real nervous and thought about leaving. Some people outside were staring as I headed up to his apartment but before I could second guess myself and leave he opened the door and greeted me with a kiss on the cheek. He told me to come in and I did. He saw the key in my hand and took it. His apartment was well kept and the lighting was dimmed low. He had some sort of electronic music playing. As he closed the door he hugged me around the waist and whispered in my ear.
"You ready for your world to change?".
I shuttered and got chills down my neck as he came in to suck on my neck. I started to moan and I was immediately hard against my cage. My nervousness disappeared as he led me to his bedroom. His strong body guiding me quickly.
He pushed me down on the edge of the bed and whipped out his cock. It was as big as my forearm and thick! It was happening so fast but I was so horny from all week that I reached out and felt his balls. So heavy and full and that's when I dived in. I started slurping on his balls like crazy. It tasted freshly clean like soap and I moved up his shaft. I started kissing his length and head started deep throating. I was so horny for cock that I tried my best but could only get halfway down.
He said "Damn baby, you are a good sissy slut."
This made me moan more and I started making the most embarrassing slurping noises. I was gagging and tried to go down even deeper. I had a lot of practice with my ex and her strap on, but that couldn't compare to this. I was feeling so naughty, and I was holding my breath longer each time. I then came up for air but he held my head down and started fucking my throat. I tried to push away from his thighs but he was too strong. I was trying to breathe through my nose but I couldn't and I started to black out a bit, but then he pulled out and slapped me across the face with his heavy cock.
