JJ and I have been friends since 5th grade. He's always flirted with me, and he's fun to hang out with, but I've never really been romantically interested in him.
We decided to hang out and watch a silly movie on Valentine's Day as we were both dateless and think the holiday is kinda dumb anyway. He came over with a couple of movies. We kept making fun of the movie's sex scenes, and he joked about not knowing what sex is like since his experiences with girls are few. Then I admitted to him that I've never gone to home plate either. This shocked him cause he knew I dated frequently and have had my share of fun.
"So what mostly have you done?" He asked. I told him, "A lot of handjobs, some oral, and being naked making out." He then just blurted out, "Maybe we should get naked and make out." I looked at him sternly, playfully, yet sternly. He let out a nervous laugh, "Yeah, I know, but worth a shot." He then looked back at the movie and softly asked, "Do you think...maybe...possibly...you would be willing to...um...give me...a handjob?" He looked back at me to gauge my reaction. I got a bit serious on him and asked, "Are you sure you want to cross that line in our friendship?" He said, "I had one once before from a girlfriend a few years ago and it wasn't very good, she didn't make me cum, and, well, I trust you, plus you have experience."
I agreed to give him one but made it very clear that this does not mean we're going to date. He nodded his head. I sat closer to him, facing him. I noticed he already had a bulge in his shorts. I lightly tapped my fingers on his bulge and said, "But you need to take it out for me if you want a handjob." I positioned myself kinda on my knees a bit facing him which put my chest near his face. He looked up at me and asked, "Can I see your tits?" I pulled down the straps of my tank top and blue bra, exposing my tits to him. I told him that he could only look, keeping his arms at his side as I gave him the handjob.
He unzipped and out sprang his cock, uncut and average size and very beautiful and smooth-looking. My left hand wrapped around it, starting with a soft squeeze and simple massages. I then started to stroke his cock, up and down while gently massaging it, occassionally rubbing my thumb over the tip. I began to work him faster as I felt his hard breathing against my tits, just inches away from his face (he just kept staring at them). "Wow, your nipples are getting so hard!" he said. I said, "Of course, I'm doing something sexual! Handjobs are fun!"
Then, after only a couple of minutes, he just exploded all over himself and my hand, even on my arm, and some on my shirt. As he relaxed to catch his breath, I got up to the bathroom to wash off. I completely stripped my shirt and bra off and came back to sit with him, handing him a towel to wipe off with, and enjoy the rest of the movie. He looked at me kinda puzzled, his dick still hanging out of his shorts, and glancing at my tits. I looked at him and said, "What? You've seen them now, and I like to be topless in my apartment. You'll get used to it."
As he wiped off and zipped up, he told me the handjob felt amazing! He was still kinda in shock of what just happened. The rest of the night, he eventually got used to me being topless even though he couldn't stop staring for most of it. I eventually went to my bedroom to sleep, and he slept on the couch. Then morning showed up and...well... to be continued...