u/ts2054

With my new account, I decided to restart my stories and tell my sissy story in order. I started out much like every other sissy. I would snag some panties from the dirty clothes here and there. Eventually the rabbit hole just kept going to make me the slut I am today. This is the story of the very first cock I ever sucked.

I was 22 or so, and at this point I had been dressing for 10ish years, but I had never met up with anyone. I’d thought about it but never made the leap. I’d just gone through a bad breakup, and I decided there was no time like now. So one day I did what every cock hungry slut did back then and posted on Craigslist.

I didn’t get many replies, but there was a post that I saw from a guy named Kevin. He was looking for a jerk bud and said that if other things happened he wouldn’t be upset. I sent him a message asking if he’d be okay with me dressing up when I came over. He said he’d never been with a crossdresser but he’s not against it. We agreed on a time later that evening and I started picking out my outfit.

It was just after dark when I left my apartment. Kevin only lived a couple blocks from me. I decided to drive over in my guy clothes and change once I got there. I was insanely nervous. My hands were shaking and my heart was beating out of my chest. Finally, I pulled into Kevin’s driveway. As soon as I parked, the porch light turned on and the door cracked.

I grabbed my bag and walked towards the door. Kevin let me in and introduced himself. I set my bag down and we had small talk. He even showed me around the house to show me the things he had remodeled. After 15 minutes or so I felt more relaxed. He looked at me and said “so you wanna change?” I nodded and walked to his bedroom. I closed the door behind me and started to change.

Back then I was a dainty 135lbs at 6’ tall. I picked out a black and white polka dot blouse, black leather skirt, black tights, and a pair of 4” pumps…they were also black to complete the look. Underneath my tiny sissy cock was tucked tightly in my lace panties and I had a black lace bra crudely stuffed with socks. I hadn’t started with makeup and wigs yet, but when I walked out Kevin told me how hot I looked.

We both went and laid on his bed. He turned on some sissy porn and we both started watching. I could see the big bulge in his gym shorts. “Do you mind if I pull it out?” He asked. I told him to go ahead. I’d love to watch. My little cock was still soft and tucked away as he whipped out his 10” cock. It was thick and to this day the biggest cock I’ve seen in person.

He started stroking it slowly and moaning. I watched in amazement. I must’ve watched him rub his dick for 3-4 minutes before I stood up. I don’t even remember this part but next thing I know I was standing on his side of the bed starring at his cock. His hands were off of it now and it just stood straight up. Throbbing hard. I slowly reached up and wrapped my fingers around it. “Holy shit” I whispered as I felt just how big it was in my hand.

I told him how I’d never touched another cock before and how it felt different than I imagined but i liked it. I stroked his big cock for a few minutes. Then again, without even realizing what I was doing, his cock was in my mouth. It stretched my mouth and slammed the back of my throat but I was loving every second of it.

I had no clue what I was doing but I’d suck for a few minutes then suck his balls as I stroked his cock. His moans were loud and deliberate as his breathing was heavy. He kept telling me how good my mouth felt and I gave the best head he’d ever had.

I paused briefly and watched the porn as I stroked his dick. “Can we do that?” I asked nodding to the porn. The man had the sissy in the video bent over railing her. “Are you sure? Have you ever had anything in there? I don’t want to hurt you.” I told him how I had a dildo that was 7” and I rode it everyday.

He agreed to fuck me after some more head. As I was crawling on the bed and bending over for him, my phone went off. I stepped over to grab it. As I did, I saw him standing there with his massive cock and panic set in. I had all the PNC thoughts before even cumming. I sadly panicked and made up an excuse to leave. I didn’t even change. I just went to my car and went home.

Kevin if you’re still out there, please let me finish the job!!!