After I finally got to touch and suck James cock for the first time, we hung out more than ever. He would come over to my house or I would go to his. Whoever had the house to themselves we would try to plan something. We tried jerking each other off at the same time while watching porn. Sitting on the couch side by side, awkwardly bumping arms into each other. James was finally touching my cock too.

Him being taller than me, it felt like his hands felt huge compared to mine. His hands weren’t just bigger, but his fingers were thicker too. I definitely take after my mom’s side of the family because my fingers are thin and girly like hers. For example my ring size is only a seven compared to the average male being a size ten.

For me it felt weird to have another person touch my cock. It felt good but it just wasn’t the same. Nobody knows how to touch my dick like I do. I know how to hit the right spot, or the right motion, or rhythm. Him touching me still felt good, but I was enjoying it mostly because I got to touch him at the same time. 

Not knowing the right motion with our hands, we found it hard to finish with just our hands jerking each other. So he would end up asking if I could help him finish with my mouth. He would encourage me saying, “You know you want to,” and even joked about pulling out his wallet. Which made me feel like a whore even though I wasn't taking the money.

As soon as I started to get up and change position to help him out, he would smirk at me. Maybe I seemed a little too eager to help him out. He would just lean back and wait for me to get to work. This happened several times over a couple weeks. I didn't mind taking on the girly role cause thats what I had been fantasizing about.

Finally one of the days we were in his room about to do our usual. We both sat on his bed and pulled our pants half way down and started to jerk off and get hard. James spoke up and ended up asking me if he could try sucking my cock. I think he was feeling guilty that I was always the one sucking his cock, or maybe he was curious too. But so far he hadn't really shown much interest in returning the favor. I was caught by surprise by this but of course I wasn’t going to turn down my very first blowjob. I replied, agreeing to it and tried to not sound too excited.

James had one of those metal bunk beds with the bottom bed that folds into a couch. At the time he had it in the bed position and I lay back, staring up at the bottom rungs of the upper bunk. 

He actually had some porn magazines that he stole from his dad’s collection and had his favorites stuck into the rungs of the upper bunk facing down so he had something to look at hands free while jerking off. It was kind of nice to have something to stare at while lying back and trying to let him do the work. 

He reached out and I felt his hand grasp my cock. His hands felt a little cold but got warmer as he slowly started to stroke me. He sat beside me as I lay there with my eyes closed. I heard him shift his position and peeked my eyes open as his head went down on me. I could feel his warm breath just before he wrapped his lips around the tip of my cock. He didn’t kiss or lick or do any of the things I usually did for him. He just got straight to business, wrapping his lips around the tip. He wet it with his spit and started bobbing his head more and more.

It felt slippery and warmer than his hands did, but his saliva also felt cold when he would come off and the air would blow over my cock. The sensation was odd being my first time. It obviously felt like nothing I had experienced before. His mouth didn’t really have the same pressure or friction that a hand does. It didn’t feel as tight around my cock. But it was so warm and slippery I didnt care, it felt amazing.

He sucked around the head of my cock for maybe a minute or two before working his way further down. He managed to end up touching his lips to the base of my cock with his nose pressing into my hip. I’m not going to lie, I was a little jealous he was able to go all the way down on me without gagging, something I had tried many times to do on him.

The fact he was able to not gag on me coupled with the fact his lips didn’t feel tight around my cock kind of made me second guess if I really was average sized. The only reference I had for size at the time was his cock and all the porn-star-sized cocks I had seen on the internet. So it made me feel small.

I began to stare at the porn pictures above me looking at the girls showing themselves off and posing. Maybe it was because there were no action shots of them sucking a guy or getting fucked, but I just couldn’t imagine any of them being the girl sucking on me. The bad thing about internet porn is it makes it harder to use the imagination in the moment when you are used to seeing exactly what your want on the screen in front of you.

Maybe it was because it was my first blowjob and I felt awkward not knowing what to do with my hands, but it was hard for me to cum. James sucking me felt amazing, but I just couldn't concentrate enough to finish.

All I could do was admire the pictures above me trying to focus on their bodies while trying to concentrate on the feeling of James sucking me. I started thinking about what they were wearing. Looking at their lingerie and how it hugged their curves. This led to me thinking how my ass would look wearing what they were. 

One of the models I liked in particular was this brunette that had similar color hair to me. She was tan, wearing these little white lacey undies and bra. It was a double page spread with a picture of her in white three or four inch heels standing up against a wall and sticking her butt out while slightly bent over, staring back at the camera. The other picture of her was her bent over and kneeling in the seat of an arm chair with her legs crossed at the ankles still with the heels on, pointing towards the camera. 

Her legs looked amazing and smooth and made a nice heart shape with her ass. The way her lacey panties hugged her ass cheeks just right and really hot. I thought to myself, I’d love to have a pair of such frilly/lacey panties in my collection. I closed my eyes, pretending I was wearing what she was. Pretending James was sucking me while wearing them with my cock poking out the top of the lace.

My shorts were still only pulled down just enough where my cock and balls were out, so my waistband was under my balls holding them up and putting pressure on them. This helped me imagine that I was wearing a pair of lacey panties and that my cock and balls were being supported by them, reminiscing about the times I lay in bed at home wearing panties and the same feeling I had then. 

While remembering images of other gurls I’d seen with their sissy cocks sticking out of their underwear getting sucked on by their lovers, I continued picturing James sucking my cock while I wore the same white frilly panties that this porn star was wearing. And man did that do the trick. The thought of this started to make my cock twitch in his mouth as I squeaked out in my labored breath that I was getting close to cumming. 

I was trying to be courteous and not just surprise him with it. But he surprised me and he continued to suck me just like I did for him. As I felt myself tense up and start to cum in his mouth, he stayed still with his lips wrapped around the tip and his hand grasping my shaft jerking up and down. 

It felt amazing, nothing like cumming in my hand. It was way more intense and was hard not to move too much as I bucked my hips and my body convulsed. He kept jerking me off with his mouth wrapped around me until cum had stopped coming out of me. He popped his mouth off the head of my cock, lips sealed holding my cum in his mouth and swallowed. I just lay there relaxed, and exhausted, melting into the mattress. 

He let me lie and enjoy it for a minute before he broke the silence and asked me how it was and I could only respond with an "awesome". He just chuckled and told me he was glad before reminding me it was his turn and i was to return to my girly duties.

His words sparked my interest and gave me a bit of energy to sit up as he proceeded to lie back like I just had. I changed my position so I was knelt beside him. Again maybe being a little bit too eager but I returned the favor with a bit more enthusiasm still imagining I was wearing the lingerie while sucking him.

So that’s how my first blowjob went. Thanks for continuing to read. The next story I'll post I’ll tell how dressing like a girl for James all started. I will talk about what sparked the idea and how he found out I was willing to dress for him.