First real Sissygasm

True story of my first Sissygasm and learning I was a cock loving sissy.

My first story ever about my first Sissygasm. I have always lived straight but found myself drawn to the other side. I still remember the picture on the internet from the first time I saw a guy with a big cock coming out of his mouth. I went to exit the page as fast as possible but before I hit it I felt something I had never felt. Like a good throbbing feeling but not just in my dick. I felt it all through my body and I needed more.
Over the next few years I tried different things from my finger to a hairbrush handle to a cucumber. I eventually tried a real dildo and loved it. Anal always felt so good.
Later on I got in a relationship with a woman. We will call her Lee for the story. Lee was beautiful and way out of my league. She was tall and slim but not too small. Tits were not big but very nice and she only got better going down. Her legs were long and sexy. Beautiful ass and she knew how to use her body. The way her back arched while in doggy was a work of art! She even had beautiful feet and toes! Especially in heels. Lee loved to ride and could ride better in heels than most women can barefoot. Lee had loved black cock before me so I am sure I didn’t pleasure her near as much as she did me. It was so hot to think about her sliding up and down on a big black cock. I could get a few stories out of her but that was it. I never told her how much I would like to watch or better yet dress up with her and join them. I never told her about my love for anal or how I was really attracted to gay porn. Especially BBC!

One day we had drinks and some “other things.” I had a great buzz and was more open to things than normal. She had me lay down and started blowing me. She moved down and licked my balls then down to my ass. I exploded instantly. She took notice of how excited I was and continued to lick from my cock to my ass. Then she took her small toy and eased it into me. I blew instantly. By the time we finished I had came 9 times that day. After that I was more open to letting her do things. She would lick and finger me often. Sometimes using a small dildo on me. This went on for several years. I always wanted more but never told her.
One day Lee text calls me from the car and tells me to get a bath and be smooth cause she is on her way and has a surprise. She would often go get some black cock in a sexy dress with nothing underneath. Lee never would admit it. I didn’t care. I understood. I just wanted her to tell me about it but she always denied it.
She would come home used and messy then give me the best fuck. Letting me lick her whole body then riding till I was completely drained. So on this day I do all I need to be ready. When she arrives she grabbed my cock and lead me to the bed. Telling me to lay down as she dropped her short strapless dress to her waist. Now revealing she had no bra and no panties. My mouth watered to eat her pussy! Lee may not admit where she had been but she knew I knew and she knew what I wanted. She reached under her short dress and pressed 2 fingers into her used pussy then brings them to my mouth. I am happy for the taste But this is different today.
Instead of 69 or riding me she did something new.
She put her hands under my knees and pushed them to my armpits and began licking me like there was a prize at the end. At this point it’s important to know I didn’t know a prostate orgasm was real. I loved a finger or toy inside of me but that alone never made me cum.
Back to the story…
I look down and I am covered in clear precum. It’s running off my stomach.
After 5-10 minutes of basically fucking my ass with her tongue Lee tells me to get on my knees with my face down. I do so and she starts licking. She pulls my cock between my legs and starts sucking as she slips a finger into me. Then 2 and then 3. It feels so great.
I am about to blow and she lets my cock slip from her mouth while keeping her fingers in me. She says she got us a new toy and pulls it out of her bag by the bed. I wanted to run when I saw it. 12 inches and almost the size of a soda can. I try to tell her no it’s too big but I only moan. With 3 fingers still inside of me she puts more lube on and in my now open hungry hole. Taking her fingers out she gets the giant and starts to lube it. I watch and imagine it being a real huge black cock in her sexy hands. At this point I feel like I am in a constant orgasm. A buzzing rolling through my body. I feel the cold tip touch my hole. Then I start to feel the pressure. It’s all I can do to bare it. As the head pops inside I make a sound I never heard myself make. A moan mixed with a squeal. That buzzing feeling gets stronger and stronger as I come to terms with the fact I am a sissy. A cock loving cum craving sissy. I want to spin around and dive into lee’s used pussy just hoping to taste a drop of black cum but the huge cock at my entrance controls me right now!
I’m shaking and It’s unbelievable but hurting at the same time. I start to feel it pushing in again and it feels like there is broken glass on one side. It’s cutting me I think. There is no lube on one whole side. I feel like I am tearing as I yell STOP! It’s not wet on one side.
As those words leave my mouth I instantly feel the huge dildo slam all the way in, then out leaving only the head in then all the way back in at a speed I didn’t know Lee’s hand could move. It was going all the way in. I wish I knew how to describe its speed as I screamed. Maybe a jackhammer speed. At the moment I screamed I was on my hands and knees with my head leaned back, basically a 12 inch soda can jackhammering away on my ass and a faint taste of lee’s pussy and her black lovers cock on my lips. I wanted to leap forward and get away but I felt something I had never felt. I looked down and I see more cum than I had ever seen. It was all over me, the bed, and still shooting ropes of white cum as far as my face. I am pretty sure I blacked out.
It was a half second of sharp pain instantly replaced by the strongest most intense feeling I have ever had! Since that moment I knew I was going to need to cum this way a lot more and I knew I could never please Lee. She likes a huge black cock shoved in like that. I can’t give her that but I completely understand why she wants it. I want it too.

I hope you enjoy my true story. I apologize if any grammar or spelling is wrong.