1. Alone At Last! My First Sissygasm.

    Date: 9/18/2017, Categories: True Stories Author: MirandaGreen, Source: LushStories

    I had been planning this night for weeks. Ordering clothes online and getting ready for my ultimate fantasy. My girlfriend was about to leave town to stay with her family for the weekend and I was so excited I'd finally get a chance to explore my sissy side. I'd been watching sissy hypno videos for days in the build-up and had everything ready in a box in the attic. As soon as I saw her car drive off I rushed to get ready. I grabbed a quick shower and shaved, applied some makeup as best I could, put on my wig, stuffed my bra with breast forms and tucked my cock back into my panties. I felt a rush of excitement as I stood in front of the mirror. Admiring myself and dancing a little shaking my hips and sticking my bum out. I slid on some fishnet stockings and my new high heels and began loading sissy instruction videos on my laptop. I came across the perfect one, a woman called mistress Minxie who was also wearing stockings and high heels. She had a laptop with a slideshow of huge cocks. She began by telling me to stare at the screen. I felt so sexy watching myself in the mirror dressed like a slut, following her every direction. She then ordered me to dress like a girl and I felt a shiver as I slipped on a sexy sheer mesh lace bustier with a suspender belt. Fastening the suspender clips to my fishnet stockings and tucking in my breast forms, I put on my new wig and admired myself in the mirror. I was completely lost in a trance and grabbed my girlfriend's dildo which she kept next to the bed along with some tingly sex lube. This was the first time I'd ever done this and my heart was pounding as I listened to my new mistress instruct me. I could no longer control myself. I poured lube onto the dildo, set it to vibrate and slowly eased the tip into my ass. It felt so good as I stroked my hand up and down my legs and over my bustier feeling the soft stockings and fake boobs. I lifted my ass in the air and watched as the vibrator disappeared inside me. I began to moan like a girl and wriggle, pushing the dildo into me further and further. Minxie was calling me a sissy and I loved it! She was right, I felt like the dirtiest slut ever! If only my girlfriend could see me now, dressed like this, she would probably call me names too. As I fondled my ass with the vibrator I realized I'd stopped looking at the sexy mistress girl and was now transfixed on the cocks. Imagining I was being fucked in my virgin sissy ass. I caught another glimpse of myself in the mirror as I moaned with pleasure. I began trying out different positions and finally found the perfect one. I sat on top of a pillow with a vibrator deep in my ass as I bounced up and down, my fake tits jiggling in my bustier. Suddenly I began to feel something I'd never before experienced, my first sissygasm. I grabbed my cock and jerked off hard and fast as the vibrations teased my anal clit. My mistress was telling me to fuck my sissy ass and I was. I could feel myself begin to climax and began ...