I briefly had this friend Wes when I was in junior high school that I knew from church so he and I were friends even though he was pretty nerdy and all the kids at school made fun of him. Wes was a year older than me and I was flattered he wanted to hang out with me, although I realize now thinking back that he wanted something else and that's why he always invited me over for sleepovers.
Wes only had a single bed and I slept on a cot on the floor, and we'd usually stay up late talking about video games or TV shows we watched. We both slept in our tighty whities and T-shirts, although I usually took off my t-shirt because it got so hot in his room.
One night out of nowhere he asked me, 'How long are you?' He meant my penis and I hadn't previously considered the question, so I honestly didn't know. 'I dunno, a few inches, I guess.' 'You have to make it hard to find out,' he said, and he pulled out a worn porno mag from under his bed. I was sort of bewildered, this older boy looking at porn in front of me, but curious too and we sat next to one another on his bed looking at the pictures. It was a hardcore mag that showed men and women together and I was riveted and tenting out my undies within a few minutes.
'Wow,' he said. 'That's something there.' He meant my erection. There wasn't any way to hide it but I didn't plan to take it out. 'Look at mine,' he said. I didn't want to, that seemed really gay, but actually Wesley's dick was hard to miss. I think the extra year was the reason why, but he was so much thicker and longer than me and the head of his cock was actually protruding from the blue and yellow waistband of his undies. I looked away quickly. 'Dude,' I said. 'That's gross.'
'I'm longer than you,' he said. In retrospect: what a preposterous approach. But at the time, he got what he wanted because I took the challenge. 'No, you're not,' I said, fearing it was true he was. My boner was throbbing hard and wetting all over and I pulled my undies down to let it out. Wes took a ruler out of his desk and walked over to me. 'Let me do it,' I said. I didn't want him touching my dick (yet). 'You don't know how,' he told me. He took the ruler and pressed it into my lower abdomen and flat against the head of my arched cock. I started throbbing even though I didn't mean to. I started to feel like I was going to need to jack off, even if Wes was there.
'It's six inches,' he told me. His fingertips grazed me a little bit and I shuddered involuntarily. 'It's more, cause it's curved,' I said.
Wes pulled down his underwear and his huge dick sprang out. 'I'm seven and a quarter even with the curve,' he showed me. I didn't look away. It was true, Wes had a huge cock. Again, if the girls in school knew that he might not have been so much of an outcast. He also had huge, low-hanging balls that were almost lemon-sized.
I realized it was turning me on to be sitting naked on Wes's bed next to him. We were probably only five inches apart and he was only wearing the t-shirt. 'You're pretty close to cumming, aren't you?' Wes asked me. 'I guess so, yeah.' 'Want to do each other?' he asked.
I would have said no, I didn't think I was bi or gay at the time (I am now happily bi-sexual, although married) but I also had never been jacked off by anybody and my only big cums with other people happened when I was making out with girls, unprecipitated.
So I said: 'Sure.' 'You do me first,' he said. I tentatively let my fingers graze his cock and it jerked around a little. He took my hand and gripped my fingers around him. 'I know what to do,' I said, although that wasn't true, exactly. I started to loosely slide my fist up and down his dick, taking my thumb to coax some of his precum out, and I felt him begin to spasm. My first time making somebody else cum, wow, what a turn on.
'Are you going to do it?' I asked him. He nodded and squinted his eyes shut. That big dick and balls started spewing in loose arcs out over the floor between the bed and my cot. I just fanned my hand as fast as I could and kept going, and he just kept cumming, four of five big spurts and then a couple of little gobs and then a few more spasms. His balls shrank up against him, I loved watching his balls shrink (one of my big turn ons to this day, makes me feel so in control) as I emptied Wes out all over his room and he started to get a little smaller in my hand (although still hard).
I was wicked hard and needed to come, pulsing and oozing like crazy. I stood up across from him and put my hands on his shoulders and said, 'You do me, now.' I was practically begging him. Compared to his meat, I only had a skinny little banana dick, but I was rigid and sticky and Wes used both hands to rub me like a piece of play dough. I shot off immediately, I think sooner than either of us expected, and I gushed really thin, high-pressure jets right onto his chest and neck, soaking his t-shirt through. He cried out and wriggled out of the cum-soaked shirt. 'Ew,' he exclaimed.
The room stank of our cum. I was glad his parents didn't come in to check on us, even with our clothes back on, it would have been unmistakeably musky in there. The smell got me hard again and again for the rest of the sleep over and even though Wes wasn't interested any more because my cumming on him had freaked him out, I jacked off anyway, knowing he could hear me and sure that he was watching.
Wes and I didn't have any more sleepovers but I still fantasize about his huge meaty dick poking out of those tighty-whities with the yellow and blue stripe and me soaking him with my juices. I wish it could have worked out, but I don't think he was ready to acknowledge that part of himself.