My first time story

When I was 18 I knew I wanted to be sissy, at least half of the time. I didn’t have any clothes or dildos yet, so I would just pull my boxers up as high as I could so they would get tight and roll up waist band down to my ass crack. I also had a plain red t-shirt that I would fold and knot in between my bitch titties to make a bra kind of thing. And then from there I would post my body on Craigslist or shake around on cam sites. I posted ads all the time and would get flooded with emails but obviously I was brand new to this and talked on every single guy. But one day I decided that this was the day I was doing it. I’m not sure why that day was the day, I guess I had enough of the thoughts of it and of course I was probably horny as a motherfucker.

As I sorted through all the responses to my ad, I responded to a few older daddy types and settled on one man named Sammy. Sammy sent over a couple of body and cock pics, all looking good enough for me. He wasn’t big, maybe just under average. I sent him a few more body and ass pics and chatted for a bit. I let him know it would be my first time and to please be gentle. I know we all want to be super experienced but I was wise enough to admit that I needed help. After some more small talk he sent his address and I told him I’ll be there in an hour.

I hoped in the shower and cleaned myself the best I could and shaved my body head to toe. I naturally don’t have much body hair so it wasn’t that time consuming. Throughout this process I’m pretty much on auto pilot due to the nerves. I don’t know why, it’s like, I want to do this so bad but in the moment I just want to stop, and yet I put the ‘stop’ thoughts aside and push myself through it. Anyways I pulled my boxers way up high like I had mentioned and put on normal boy clothes and ordered my uber.

My cock was rock hard throughout the short car ride but all at the same time my hands were sweaty and shaky and my foot kept tapping on the floor. When I arrived at his apartment building I rang his bell and took a deep breath…

Sammy greeted me with a smile. He was wearing a white tank top and big basketball shorts.

“ please come on in” he said guiding with his hand. I awkwardly crept in and stood in in the living waiting for him.

“How you doin?” He asked as he approached me. He squeezed my butt cheek and had me sit on the couch. He sat down next to me but left one seat cushion in between us. I sat facing forward and he sat positioned towards me.

“Wow you are cute”

“Thanks” I replied with a slight smile.

“Wow this really is your first time… if at any point you want to stop you just let me know, ok?” He said. I know he felt like he had to say that but it did make me feel a little better.

“ have you ever given a blowjob?” He asked.

“No… first time for everything I guess.” I replied.

“Oh, that’s ok. We’ll go slow. Can I show it to you?”

“Sure” I replied again. Sammy jumped up from the couch and pulled down his shorts and underwear exposing his little soft cock to me. He began to play with it. I stared emotionless at it for moment. Then I guess my second nature just reached out for it with my hand. When I made first contact with it Sammy let out a big and deep ‘oh yeahhhhh’. I pulled on it and twirled it around my fingers. I felt hit getting hard in my hand. He took a step closer to me and now his cock, balls and belly were a few inches from ny face. All I had to do was lean forward…

And so I did. I opened my mouth and went for it. I was surprised by cock just tasting like skin for some reason. I sat still with it in my mouth for moment and my eyes squeezing shut. Another few moments went by and then I began to slightly bop.

“Your not to bad at this” Sammy said. I just kept doing what I was doing. He began rubbing my head which was ok but then he started pushing my head down. I withdrew from the discomfort.

“Sorry baby” he said

“It’s ok, I’m just not used to it” I said as I went back to it. He put his hand back on my head but didn’t push me anymore. I began to work up some rhythm but then he stopped me. I think I was giving a bit of a toothy bj. I could feel some teeth touching his cock. But I was learning why it’s a blowJOB. It’s a bit hard at first to get it down.

“That was good baby. Now let me see your ass” he demanded. I stood up and dropped my pants to the floor. He reached for my rock hard cock and played with it. Then he turned me around and admired my ass.

“ ok what you are gonna do now is get in doggy right here. Can you bend over like in doggy?”

“Ok” and I did what was asked. Sammy put on a condom and lubed up his fingers before inserting them into me. Nothing I hadn’t felt before, but it felt so violating having someone else do it. He used one finger for about a minute then added a second. He told me he loved how tight I was. After another minute he pulled his fingers out and lubed up his cock. My mind was racing. I was quiet as a mouse. I buried my face in a pillow and just waited. I felt his cock head press up against my hole. It definitely felt bigger than his fingers. He pushed in and sharp pain made me squeal.

“Oowwiee” I shouted out. He continued to push in without saying anything. The pain felt excruciating but I held my ground. My legs were shaky and I could feel my face becoming red hot. I felt him sliding in more than felt his belly pressed up against my ass. I knew he was all in. He stayed still for moment.

“You good, baby?” He asked.

“Yeah” I whimpered back.

Then I felt the pull back and the pain returned. He picked up pace slightly. All I could do was squeal into the pillow. I could hear him moaning but I could tell it was awkward for him. He pulled out and applied more lube. A lot more. The reinsertion was less painful but still present. I felt he was able to slide in and out better. We fucked quietly for about 5 minutes before he pulled out again. I let my body fall to the side and I looked at up at him.

“Get on your knees and suck my balls” he demanded. I took a moment to catch my breath before getting on my knees before him. I began to lick and suck his balls gently as he removed his condom.

“You’re gonna try this cum” he said as he began to jerk off ferociously.

I anxiously waited for him to cum. Even my ball licking probably sucked because all I could think about was hating tasting cum. I had no idea what to expect. I’ve only tried my in small doses and it was always in post nut clarity so I never liked it.

“Open up, boy”

I opened my mouth and squeezed my eyes shut so tight. Then I felt it hit my tongue. I immediately closed my mouth and turned my face away. The rest of it got all over the left side of my face. I sat there stiff as a board not having a clue on what to do next.

“You weren’t bad at all” he said as he went to grab me paper towels. I cleaned my self off and left without saying much else.