First Time Sissy - The Bike Path

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to while I got ready. I could already feel my manhood slipping away from me.

I started by going to the bathroom, and shaving my body. It felt so good to know that my pussy was completely smooth if a man were to ever come and take me from behind. I could hear the sissy hypno from the shower, and repeated every phrase that I was told to. "I want to suck cock." "I love cum." I would say aloud for the first time. It felt so hot to say the words. They got more and more intense as the video continued. "I want to find a daddy to make me a whore." "I want to walk the streets dressed like a slut." I was completely smooth at this point and felt so sexy getting out of the shower.

I then went over to my bed of toys and pulled out my chastity cage. I had never actually put it on before, only ordered it online earlier that week knowing I would be alone. I squeezed my sissy clitty into the tiny pink device. It barely fit, but made me feel so hot. I decided I wouldn't be taking it off until my roommates came back from their trip. I went and took my jeweled anal plug, and slowly slid it into my tight freshly shaved pussy. Being plugged and caged made me feel so depraved and horny. I put on a corset to immediately start training my waist to look more feminine. I put a double padded bra on, to feel like I had some real tits that men could play with. I then slipped on a garter belt, and some thigh high stockings. I slipped a tight pink thong over my chastity cage. I looked at myself in the mirror and had never felt so hot in my life. I then sat down at my desk to put on makeup. I put some dark eyeshadow, some black winged eyeliner, fake eyelashes, some matte pink lipstick. I was starting to look like a real girl! I found a sexy red top and slipped it over my corset. I took my pleated mini skirt and pulled it up over my waist. I put on a short black wig with pigtails, and some black platform heels. I looked like the real deal. I couldn't help but taking pics of myself to send to real men online. I had never actually met with a man before, but maybe that would change.

Every night I would pull out my jeweled anal plug, and break out my realistic 8" pink dildo for anal training. I would watch anal training videos, and follow the motions exactly. First, I would practice getting it as far down my throat as I could, getting it further and further without gagging every night. Then I would get on all fours and slowly enter it into my sissy pussy. At first it barely fit, and hurt so bad to get it in, but a few days later I was able to follow along with the anal training videos no problem. It felt so good having a dildo shoved up my tight pussy. I kept wishing it was the real thing.

After a few nights of dressing alone and watching sissy hypno videos, one video came up that kept encouraging me to go outside dressed as a girl. It turned me on so much that I decided I would drive down to the local bike path and walk outside as a girl. It was late enough and there shouldn't be anyone around. I packed some toys into my purse, and plugged up my sissy pussy. I walked out of my house completely dressed and in heels. It felt so liberating. I quickly walked to my car and drove to the bike path. I parked my car, and started walking around. It felt so hot being outside in heels and a tight dress. Then I saw a man walking his dog. I got scared but continued walking past him.

He made eye contact with me and said "Hey cutie!" I couldn't believe it. "Hey Daddy." I replied with a smile. He said "Why don't you follow me back to my place, where I can put this leash on you instead?" This was it, my first real opportunity with a man. "Yes, sir!" I blurted without thinking, and began following him back to his place off the trail.

I followed him in the back door. He sat down on the couch, leash in hand, and told me to crawl over to him. I obeyed and crawled, spreading in front of him on all fours, presenting my plugged pussy and locked clitty for him. "Good girl" he said. He stands up and puts the leash around my neck. He began inspecting me head to toe, then sat back down on the couch and pulled my leash toward his cock. I pulled down his pants and immediately shoved his cock in my throat. It was huge, and tasted so good. I gave such a messy blowjob and felt so hot.

Daddy pulled my leash up and said "Bend over the couch." "Yes, daddy." I replied. I bent over the arm of the couch and daddy pulled the plug out of my pussy. He said "Tell me how bad you want my dick, baby." I screamed out " Daddy please fuck me as hard as you can. Cum all over my sissy face." He pressed his big cock against my pussy. I could feel him entering me, my pussy slowly opening up to his huge cock. He started going in and out, gaining speed and getting deeper with each thrust. "Oh my god, your cock is so big daddy! Please fuck me harder!" I couldn't believe what I was saying. Daddy pulled back on the leash and started tensing up. I could feel him getting close. "Please cum on my face daddy!" I yelled. He pulled out of my pussy, pushed my face aginst the couch and came all over my face/hair. "You like that you little slut?" I was moaning in pure ecstacy. "Yes daddy!" I gargled through the cum. He pushed the plug back into my pussy, then lifted me up by the leash, brought me to the back door, took off the collar, and said "Meet me in the same place, same time tomorrow night, you little whore." Gave me a $20 bill, then sent me on my way with cum still dripping off of me.

I walked back to my car, knees still shaking from being fucked. My sissy pussy was so sore from being destroyed for the first time. Cum was dripping off of my face. I felt so hot, I couldn't believe it. I felt like such a good little street whore, getting paid to be fucked by a stranger. I drove home and passed out, still plugged, dressed, and covered in cum. I couldn't wait for the next night to come any sooner.

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