Sissy Biography - VI

It wasn’t long after that last foray before the relationship started going south (for a number of reasons), and the sex dried up.  It wasn’t surprising, the two of us had a lot going against us (being in our early 20’s would probably be at the top of the list), and we ultimate just weren’t right for each other (panties notwithstanding).  

Unfortunately, I was still sharing a lease with her, and forced to share living space as our interactions became steadily colder and colder. 

After such an explosively amazing episode, I had hoped we could continue pushing each other sexually, but we didn’t.  This left me sexually frustrated, and with the worst goddamn itch to keep up the panty-play as much as I possibly could, but my girlfriend had let me know that no sexual activity was going to occur in the near future. 

So, there I was with the only girl I’d ever told the breadth of my sexual fantasies, and she refused to engage in even the most vanilla of sex, let alone indulging my weird fetishes.  I was stuck, I wasn’t willing to leave the relationship, and I wasn’t willing to cheat.  The only consolation I had was that I had access to my girlfriend’s wardrobe. 

As a lot of people with pent up sexual frustration will tell you, the longer the frustration goes on, the further out a person will go to satiate it.  In the months between our panty-stravaganza and our inevitable break-up, I went from being a panty-waisted, panty-wearer to a damn-near full-on closeted sissy.  I started digging deep into her closet, pulling out old skirts and dresses, stuffing her bras under sexy tops, and wearing her high heels.  I would say, however, that this was the time period where I started engaging in the real sissy behavior. 

 

I remember watching myself in the full-length mirror, red-top, black heels, black skirt pulled-over my waist, my cock pulled through the leg of the black panties (the same from our last entry), pumping myself for all I was worth.
 

I felt my climax approaching closer and closer, my orgasm all but erupting.   This time, though, something was missing…I needed something…extra.   I couldn’t put words on it (especially while I was masturbating in the middle of my bedroom dressed like a girl, when my girlfriend could have decided to skip class and return home), but I knew that I had to take things an extra step further.  The skirt and panties were a nice start, but something else needed to happen.  I need something to put an edge on this orgasm.  I needed something to make the act more depraved somehow—I needed to degrade myself.  I needed for the little sissy in the mirror to learn her place.  I needed that smug little tart to learn what happened when she kept dressing like some goddamn slut.  That fucking cock-tease had a lesson to learn: if she was going to keep sneaking around behind her girlfriend’s back and dress up in panties like a little whore, then she was going to pay the price!  She was going to learn what happened to little sissies who thought they were entitled their sissy clothes and their sissy orgasms.

My climax was building to its apex, so I did the only thing that made sense:  I roll onto my back, draped my legs over my head and pumped my cock at my face.  After about three strokes, I came—oh, god, how I came. Jet after jet of white hot sticky cum plastered my face, my chin, and an eye I closed just-in-time, gluing it shut.  I never knew I could cum so much, its sticky warmth creating a trail down my face as gravity took hold over my cumshots.  I just kept cumming and cumming, and, while I came and stroked and came, I was taking deep, climaxing breaths.  At first I barely noticed, but I felt the second shot enough to snap myself into it: I was cumming in my mouth…I could taste it, warm, gooey, salty.  I was in such a frenzy that, even with this realization, I couldn’t stop myself; I kept stroking, getting every last bit of semen out of my cock, while I got my first true taste of cum.

 
Eventually, the orgasm ended, and I ease myself back to the floor.  I felt the cum trails on my face already beginning to dry and tried to puzzle out how I could stand up without dripping cum all over the apartment.
 

 What the fuck had I just done?!  What the fuck was wrong with me?!  I was laying in the floor, dressed like a fucking sorority girl, wearing my girlfriend’s panties, covered in cum!  This was not normal!

The sissy-shame that accompanies those few early releases hit me full force.  I began to question what the hell was going on, and what I needed to do.  I needed to hit the breaks on this fetish shit.  I needed to try to figure out what to do about my relationship.  I needed to clean up without making a mess before my girlfriend, or our other (lady) roommate got home.  But, there was one thing I needed to do, before all that, that became quite evident.  Something I needed to do immediately, and so I set about the task like any dutiful sissy would.

I swallowed.