A Sissy Slut's Diary Ch. 03

"You like taking cock, you fucking sissy bitch?" he asked and I moaned in response, knowing the answer was evident.

Every thrust into me made me feel so full, not in a satisfying comforting way but intensely so, like I was sure each time he wouldn't fit himself all into me, that I felt the pressure of him inside me, never quite comfortable with it but enjoying it nonetheless. I was practically limp, much drunker than I'd meant to be, forgetting to put in the usual effort to make my voice higher pitched and more feminine, just softly moaning into the bed lost in the moment.

When he lifted my waist up and pulled me up onto the bed I fell like a rag-doll, letting him move me onto my back and pull my legs up against his shoulders as he slid back inside of me, staring down into my eyes as I kept crying out. I jumped a little as I felt his hand on my cock, startled to look down and see him stroking me. I wasn't hard, too overwhelmed from the feeling of him inside me, but I felt myself getting there as he squeezed the bottle of lube over my dick, oiling me up as he kept stroking. I leant my head back and closed my eyes, no idea what to do with all these sensations, of his cock inside me, of someone else stroking my own cock for the first time, of my feet up in the air and his other hand stroking my chest.

I felt him lean down, his pace inside me slowing as he stroked me harder, asking if I was going to cum. I didn't opened my eyes but nodded, feeling that I wasn't even fully hard but was already so close to my limit, feeling sure I wouldn't last more than a few more seconds.

"Stop," I breathed, knowing as soon as I came I'd feel that familiar shame of when I would jerk off with a dildo inside of me, only this time with a cock in my ass that I knew wouldn't just stop.

My plea didn't stop him though, and I felt my whole body shake, my neck bending back as he milked my cock. I could feel it spray across my stomach and chest, and looked down to see David wiping his hand clean on the bed and then gripping my waist again, fucking my harder. Suddenly I was back to feeling like I had the first time, the pleasure from being fucked fading, realising that I was lying here looking at my stocking-clad legs resting on the shoulders of a man I didn't even find that attractive, who I'd invited purely to stick his big cock into me as I lay here with lipstick and a wig on. Still his cock kept sliding in and out of my hole though, and I closed my eyes, not wanting to look at him as he kept going.

What I didn't expect though was that as I lay there feeling ashamed I actually started to like it, not just being fucked but being ashamed of it, feeling pathetic and embarrassed lying here with a stranger getting ready to cum from fucking my asshole. I felt filthy, and it made my heart race. Within the space of a minute I'd gone from regretting everything to feeling thrilled by it all, and as David pulled out of me and ripped off the condom, spraying my torso now with his own cum as well as mine, I was actually disappointed he didn't keep going. He was stood over me catching his breath so I reached down, swiped across the smooth skin of my stomach with two fingers, swiping up hot cum that I raised up to my lips, smiling at him as I licked myself clean of what was probably both of our cum.

By the time he'd sat on the edge of the bed dressing himself I had wiped up most of the cum off of myself, savouring it as I licked my fingers clean, feeling more than ever like a real sissy slut as I swallowed it down.

"Let me know if you want to do this again," David said as he stroked my leg, watching me clean myself off before heading out of the door, so much calmer now than when he had walked in. I felt calmer too, I realised, satisfied, confident, sure of myself. If there was ever a test of my conviction this weekend had been it, and as I curled up in bed I didn't even bother showering, didn't remove the wig, just lay there feeling warm and proud and content in the knowledge that I'd been fucked three times in two days, by two different guys at that, feeling my ass ache and knowing that this was absolutely the best weekend of my life.