First Multiple Sissygasm Today

I had my very first multiple sissygasm.

I own a fucking machine. It has been the source of much pleasure since I bought it. I decided recently to try for a really great sissygasm. For those of you that don't know, a sissygasm is having an orgasm with a soft cock from ass/prostate stimulation. Well, I decided that I was going to prep myself to have a nice large sissygasm. This meant no jacking off for a week. I was so horny by the end of the week I was waking up to hard painful erections.

I prepared myself for my adventure by cleaning myself out completely. After that I went to my special room and set things up. The computer was turned on and porn, mostly creampie gangbang, crossdresser's cumming while being fucked, and sissygasms, was setup to play. I then set up the Sneaky Pete. It is a fuck machine that has adjustable front and rear supports so it can be positioned in several ways. I had it set up to pound my ass as I was lying face down. The toy attached was the vac-u-lock wave, one of my all-time favorites. It has two nice bumps, one front and one about mid-way, that really do a number on my prostate.

Getting my basket of clothing I started to sort what I wanted to wear. I thought to myself, yes, the red stockings and garter belt will feel nice. Shoes next, some 3 inch healed back straps with bows on the toes. Then I grabbed a red short satin robe and a corset, black with red accents. I was unsure of the corset as it had not fit me very well a few month ago.

First I pulled on the shear red stockings and attached them to the stretchy red lace garter belt. I was pleasantly surprised when the corset went on and was so loose it almost fell off! I've been working at losing weight and it seems I've been successful. I pulled the satin laces tighter on the corset and loved the feeling of tightness. Next were a pair of panties that I had recently purchased. Full cut red satin with black trim. I pulled them up over the stockings and garter because I knew they would be coming off first. The robe felt so smooth and soft flowing over my shoulders as I put it on. Last came a short blonde bob-cut wig and then the shoes adorned my body.

There's something about putting on the shoes that just completes the transformation in my mind. Once they go on I'm absolutely keen on getting my ass fucked! I may not look like a horny slutty lady but I sure feel like one when those shoes complete the outfit.

For a while I sat back and watched the porn I had on the screen. There were four windows open on the big screen TV so I could switch my view to whatever caught my eye. It's kind of strange that my cock doesn't really get hard when I'm watching while dressed waiting for my ass fucking. I get hard easily enough, dressed or not, but something in me just stops that from happening when I am trying for a sissygasm.

My head was swimming from the porn and being dressed fully in lingerie. The feeling is almost like being high. My cock was leaking so much pre-cum into my panties that I could feel my balls getting wet. After watching several scenes of sissygasms (one of which is of a sissy cumming 3 times in the same session from just a dildo in the ass!) I knew I was ready.

I took off the robe and the panties and positioned myself face down with the toy at my ass. I had pumped a bunch of lube into my fuck hole earlier so the toy slid in with ease. The moment the toy hit my prostate it immediately forced out some cum! Just one squirt but it felt good. I turned the machine on and started it slowly fucking me. I was so full of cum from waiting that each thrust forced a bit out for the next four or so thrusts. Not orgasms but a really nice feeling all the same.

I settled in to a nice rhythm of pushing my ass back as the dildo pushed into me. Slowly my body started to acclimate and the dildo warmed up. Each time I thrust back against the toy that was penetrating my slick asshole it would push on my prostate and increase the feelings of being a slut that wanted nothing but to fuck and be fucked. Have any of you ever noticed that? After a certain point of sexual stimulation the mind kind of blanks out and all you can think of is sex. Well, at least that is what happens to me.

After a while I turned my head towards the screen and watched as cocks on sissies pumped out cum or cunts were being filled over and over again with cocks and cum. My arousal ebbed and flowed at this point, peaking and then slowly diminishing. I would pump my ass back at the toy a bit and the arousal would ramp back up. Or I would focus on a particularly nasty scene on the screen and imagine I was that girl or sissy being fucked. After about twenty minutes of this, you have to be patient when trying to have a sissygasm, the feelings in my prostate started to signal to me that an orgasm was imminent.

As the toy bumped and pushed at my fuck gland, the tip of my cock, which I had not touched this entire time, started to tingle. This told me that a sissygasm was possible and might happen soon. Soon is a relative term when trying for a sissygasm and this time was no different. My arousal started to ebb a bit and I thought that I might have to touch myself to put me over the edge. Just as I was getting ready to do just that the tingling came back hard!

I sped up the machine so that it had close to the same frequency as my prostate does when I have a regular orgasm which is about eighty five strokes/pulses per minute. My body tensed, my legs went stiff and a huge blast of cum shot out of my cock! Just one though, and I was slightly disappointed but only for about ten seconds. I had had that happen before and then my arousal dropped to nothing. Not this time! The toy kept banging at my ass and suddenly three more massive squirts of cum shot out of me with my prostate spasming and throbbing away. I could feel all the wet warm cum around my cock slowly seeping into the towel under me.

I was extremely happy with what had happened but it wasn't over. Everything felt so damned good that I just let the fake cock slam in and out of me. My mind was pretty much switched off by this point and all I could focus on were the feelings in my body. The intense joy of my ass and prostate being stimulated to the point of orgasm was intoxicating. Then, out of nowhere, my ass started to spasm and my love gland was doing the same. My prostate and ass just throbbed and throbbed and throbbed over and over again for at least two minutes. They were both twitching at least twice the rate of a normal orgasm. My entire body started twitching form the feelings.

The sissygasm started to slow to a stop so I stuffed my mouth with a soft dildo and started to suck on it. This only made my ass clench down even harder and set off an entire new round of convulsions. Have you ever noticed that when you suck on something your ass tightens up? I have and it made that last sissygasm a pleasure to remember. I was yet again wracked with a burst of twitching, convulsing muscles all over my body centered and focused into my cock, ass, prostate and balls. My mind was so overwhelmed that I couldn't even think. The only thing that mattered was that plastic cock going in and out of my ass and to try and make the feelings last.

Slowly the feelings faded and I slowed down the machine until it was at a stop. I languished in the afterglow of the massive endorphin rush that I had just received. My mind was filled with thoughts of what it would be like with a real cock. Maybe it's strange or maybe it isn't but I have absolutely no attraction to men. Seeing a man does nothing for my arousal at all but when I am dressed up I love the idea of being fucked by cock or sucking cock or both!

I was in that mind blanked state after the massive multiple sissygasm I had just experienced. I slowly brought the machine up to a slow rate and relaxed while the toy again slid in and out of me. I thought that I would see if I could touch myself to yet another orgasm. I snuck my hand underneath myself and gently started to play with the head of my soft cock. I started to rub at the frenulum on the underside of my penis. That is an intense feeling even if you are not hard. The sensation built in me until I was right on the verge cumming yet again.

I snuck my free hand over to the control by my head and pushed up the speed from a gentle thrusting to a determined pounding. Just a few strokes in and cum was flooding my hand in a more standard and less intense orgasm.

I slowed the machine to a stop and just laid there reveling in the feelings. All this time my cock hadn't become even a bit hard but that didn't matter in the least. I laid there for a few more minutes just taking in the fact that I had just cum several times in a row. A low level vibration of pleasure infused my body. I pulled my cum covered hand from underneath me and looked at the gooey mess in my palm. I couldn't help myself, my tongue reached out and licked it all up. I swallowed with a contented sigh.

My head dropped to the pillow and a smile was on my face. I stayed that way with the fake cock in my ass for about ten minutes or so before I decided it was time to go get cleaned up. During that time I decided I would write down the experience to share with all of you.

Thanks for taking the time to read this story. It's all true. I hope you enjoyed reading it, I know I enjoyed living it.