I’ll never forget my first sissy orgasm.
It was the first day I moved out my parent’s house. I was 19 and up
until then I had only come close to achieving a full on sissy anal
orgasm. Even though I had been playing with dildos and butt plugs for
a year I just hadn’t been able to reach that point of sissy bliss.
Now however, I was alone. COMPLETELY alone.
I still hadn’t unpacked everything from the move but I knew exactly
which box had all my panties, toys, and lubes. I opened it up and
dug through the contents pulling out my favorite pink thong with
matching bra and a bottle of KY Jelly, as well as my 6 inch dildo
and of course my butt plug.
I undressed, and slipped into my lingerie feeling giddy and girlie
smiling the whole time. I was so excited that I was talking to
myself in my high pitched sissy voice. I remember talking to my
dildo, telling it that we were all alone now and nothing was going
to stop us from getting to that special place of an anal orgasm.
I kissed my dildo, licked it, sucked on it. Thinking of how good it
was going to feel to finally let lose, to go the distance and
fuck myself like the filthy little whore I’d always wanted to be. I
remember my clitty dripping as I sucked and licked my dildo. I
remember how wet and sticky my panties were. I remember looking into
my mirror and seeing how my stiff clitty looked in my panties. What
I’ll never forget though, was how slutty I looked back at myself.
I took a deep breath and relaxed myself enough to put the dildo down
and lubed up my butt plug. I wanted to make it last as long as
possible. I slid my thong strap to the side and slid the the cool
slippery plug up inside me. I felt it pop in as my sissy pussie
wrapped it’s lips around the tapered curve, then put my thing back
between my cheeks helping it stay in place.
I can still feel just how fem i felt walking around my apartment.
The way I walked with my ass stuffed was different. I took light
girly steps and arched my back so my butt stuck out. I knew it was
time for a cigarette.
I found my pack after some digging a round and walked to the window
to open it and lit up. I smoked very differently that day, my lips
were puckered out and sucking down the warm smoke filled me with a
rush of endorphins that gaze me goose bumps all over my freshly
shaved body.I held the cig with a limp wrist and made my motions of
smoking as women-like as possible. I was loving every moment of it.
I was on the third floor so i could look out and down my open window
without the fear of anyone seeing me. I leaned on the window ledge
and bent at the waist sticking my ass out with my elbows resting. I
was free.
After finishing my smoke, I knew that it was time to get to
business. I opened up some sissy hypno vids on my computer and set a
playlist on repeat. I turned the volume up and loved the sound of
sex filling my room. It was so nice not to have to use headphones.
I got down onto the floor and lied on my side to slip my butt plug
out and slide my panties down to my ankles. I grabbed the dildo and
started sucking again desperately as if I was trying to get a mouth
full of cum. After getting it wet with a nice sloppy blowjob that
left my chin wet and dripping I stood the dildo upright on the floor
and mounted it.
I lowered myself slowly onto it feel all 6 inches penetrate me. I
felt it push into me and I gladly welcomed it in balls deep. I then
sat there on it. My clitty stiff and leaking while i was stuffed and
on my knees. I let out a long and loud girlish moan knowing no one
would hear me. I was in heaven.
It wasn’t long before i started slowly riding the rubber cock. I
remember pretending to be a sissy hooker in a whore house, and my
dildo was a client that had paid me to pleasure him. Or that I was
stripper in the back of club giving a man a good time. I was going
through fantasy after fantasy, and I was picking up the pace as
well.
Soon I was bouncing on the dick. Breathing as if this was work out,
panting like slut, moaning out loud and begging for more. I was
calling myself every dirty name in the book. Slut, sissy bitch, anal
whore, cum guzzler, cock magnet. I grabbed my ankles for leverage
and started slamming myself onto the cock ramming it hard and fast
inside me.
With each thrust my clitty twitched and leaked more stings of sissy
pre cum onto the floor. My ass cheeks pressed into the floor each
time I went down and I could feel a wet sloppy mess beneath me.
Again and again I fucked that cock. Over and over I cried out in
pleasure, pushing myself further and further as I felt orgasm in the
distance.
I knew I had to keep going, I told myself not to stop. I had to beg
out loud to please don’t stop, please let me cum, keep going please.
My mind had gone to a place i didn’t know existed. I was fucking
myself mindless and raw. I was sweating and gasping for breath, my
muscles ached and my sissy cunt was sore, but I forced myself to
keep going. I forced myself to accept that I could cum from this. I
told myself I had no other choice and that this was a sissie’s
destiny.
Then I felt it. It started small at first like tiny little ping in
my ass and behind my balls. I had untapped something deep inside me.
I knew I was close and as much as I wanted to stop and have another
smoke I wanted to cum even more. I fucked that cock as hard as I
could slamming myself onto it like a desperate bitch in heat. I
needed it.
Then The feeling inside my cunt grew stronger and I felt my whole
body start to shudder and my knees went weak. It took every bit of
strength i had to keep riding that cock as I felt a shock wave blast
through me. My ass hole tightened and I fought it’s clenching to
keep riding through the orgasm. I cried actual tears that ran down
my cheeks as I cried out that I was cumming.
My body felt like it was being pumped full of electricity with each
pump of the full length of that cock. I grunted, moaned and my body
trembled in response. All I could do was grit my teeth between gasps
of breath and begging for more while my eyes were clenched shut. I
could only focus on the intensity of pleasure I was feeling in my
ass.
It was in the moment I realized I had gotten there. I had achieved
the sissygasm, and I will never forget how good it was. I fell to
the floor after it was done. Panting, sweaty, and spent. The cock
was still buried in my ass and I didn’t yet have the strength to
reach down and pull it out.
I did however notice the globs of cum on the floor that I must have released during the orgasm. I hadn’t even realized. lol.
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