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.
I gasped and coughed for a bit and then he pushed me on my back. I thought to myself that I needed to get out of here. It was really hot but also I was getting kind of scared. I thought if I could make him cum quickly then I could go home ASAP.
He lifted my leg and took of my heel. I could see my painted purple toes through the mesh and he seemed to appreciate it as he started kissing my heels, my soles and went up to my toes. He started taking deep breathes and then he ripped my fishnets to expose my bare toes and foot. I was a little mad at first as my Ex had bought me this lingerie but soon that was forgotten as he was really worshipping my foot now. It felt so good as he was kissing my ankle. I was incredibly hard at this point but I didn't realize it until now. My dick was straining against the cage and I needed release. He spent a long time on my foot and I think it was mostly for him than for me. He didn't even mention he liked feet.
He then put my leg down and took of my other heel. Swiftly, he ripped my shorts down and I felt so exposed. You could see my caged dick and I saw that I had a lot of precum.
"Nice, you're a good sissy. Your clitty is all caged up. Good." he said in a lustful voice.
The praise made me even hornier. I took of my shirt to expose more of myself and I realized I liked feeling vulnerable like this. He grabbed a hold of my cage and it all fit in his large hand. He took some precum that leaked through my cage and rubbed it on my nipple. He went to start on my other foot and ripped that side too. At this point I didn't care and was rubbing my own nipples. I was moaning lost in the moment.
After maybe ten minutes of him worshiping me and I was needing to cum. I didn't care how. I reached for his massive cock and I barely touched it before he slapped me away and that's when he flipped me over with such force that I was scared again. He then ripped my fishnet suit at my ass. Freeing not only my ass but my caged "clitty". He then dove in and started eating out my ass.
"I have to get this bussy ready baby" he said before diving back in.
