My First Sissygasm

This is a true story about the first time I felt the sensation of cumming like a girl.  I don’t mean a prostate orgasm, where you ejaculate through anal penetration, but my first time feeling what I can only describe as a full body sissygasm. 

It was another night alone, dressing up in my apartment.  I was feeling really girly and really horny.  I took my time getting myself dressed up.  After a nice long shower, I shaved my legs and any other annoying body hair.  I got out, dried myself off, and lotioned my skin.  My lingerie was already laid out from before my shower.  Slowly, I slipped my bra on and clasped the back, then placed my breast forms inside to give myself a nice C cup.  Then, I pulled on my garterbelt, followed by sliding a pair of sheer black stockings up my silky legs.  After they were clipped in place, I pulled on a French cut Victoria’s Secret thong, loving the feeling of it sliding up between my cheeks. 


Next, I went to my closet and pulled out a black dress with sheer sleeves and pulled it on.  It was above the knee, but not short enough to be considered a mini-dress.  Then, I slipped on a sexy pair of 5” high heels, followed by my favorite necklace, bracelet and earrings. 

I took some time to put on some sexy makeup with a nice smokey eye look, and red lipstick.  My nails (hands and toes) were already painted a pretty red from the night before. 

And there I was, all dressed up with nowhere to go.  I decided to put on some porn and maybe chat with some online friends.  I always loved watching trans porn, imagining it was me getting fucked by some hot guy but also enjoying how sexy the girls in the videos were.  It was a really slow night in the chats, but I was getting so turned on by the videos, I just needed to get fucked.  It’s like this ache in my body that I get and the only thing that will help it is getting penetrated. 

I got out my favorite dildo, and just relaxed on the bed.  I decided to give a call to my favorite phone mistress for a session.  She was always so good to me knowing just how rough or gentle I needed her to be.  Tonight she said she would walk me through a fantasy of the two of us going out and picking up a guy to take home to fuck me.  It was so sexy hearing her talk me through the process of her dressing me, and getting ready to pimp me out to a guy at a bar.  Once she got to a point where we found someone to take home, she told me to get my dildo lubed up and ready.  She started describing to me how he would lay me on the bed and push my dress up, licking my smooth legs and stomach.  Then he would pull my thong off and lick my tight little hole getting me ready for him.  She finally had me tease my hole with my dildo as she described his hard cock playing with me before slowly pushing into me. 

At this I began fucking myself with the dildo as she described him fucking me with his big cock.  Slowly I slid it in and out of my asspussy feeling every inch of it as she talked me through having this sexy guy on top of me working his cock into me.  My clit was half hard, but she told me not to touch it at all.  I was only to use the dildo for now.  This was how a woman got fucked, so that’s what I did.  As I kept sliding it in and out, she told me to go faster and slower, harder and softer, all the while describing this guy’s body on top of me, kissing me while his big, hard dick filled my tight hole. 

After maybe 20 minutes of getting fucked, and not touching my clitty, it was like my sexual focus completely shifted.  It was like I wasn’t even interested in my clitty being stimulated anymore.  I just felt how hungry my pussy was and it wanted to be filled.  So fill it I did.  I kept fucking myself with the dildo feeling so feminine and girly.  After a few more minutes of this my mind just allowed my body to feel all of the sensations that this cock in my pussy was experiencing along with the narration I was getting from my mistress. 

Then it happened.  I started to feel a tingling sensation in my pussy and I thought I was going to just have a regular orgasm.  But that didn’t happen.  The tingling continued, but then it started to spread through my whole body until finally I felt this feeling that I can only describe as a full body orgasm.  My pussy pulsated as I continued to fuck myself with my dildo, but I also was squirming around feeling this amazing feeling all over my body.  My mistress told me to keep going as she described how this guy was making love to me and kissing me.  When the sensation finally stopped, she talked me through how he would start going harder and then finally shoot his hot cum inside of me.  This got me so hot, but I was still just so amazed by what I just experienced. 

When we were done, she told me how happy she was that I had my first sissygasm.  It was an orgasm that happened through anal penetration only and did not involve me ejaculating.  I came like a woman, and it felt so incredible to take one more step towards womanhood.  After we hung up, I thought about masturbating some more but decided not to.  I wanted to just enjoy this feeling that I just had and enjoy feeling like a slutty girl who just came from getting fucked by a hot guy.  I got changed into my nightie and drifted off to sleep feeling almost like a new woman.

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Updated: July 31, 2021 — 3:14 pm
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