When I was a little boy my mom would drop me at the library downtown. I posted previously about meeting Jack in the basement men’s room of the public library downtown where I grew up after seeing a note in the graffiti on the stalls. Being 9 or 10, I was fascinated by the drawings of cocks, invitations for blowjobs, and that “Be here at 2pm” was too enticing for me to resist. He discovered me waiting, a very tall stocky (almost) handsome man in his late 30s/early 40s. I helped him to piss at his invitation, by unzipping his pants and pulling them down, and then holding his cock to aim the piss stream into the toilet. It was very exciting, but I knew my mom would be there to pick me up soon and had to go. He asked me to meet him earlier the next day, and also to keep what we did a secret – I agreed.
Jack met me almost every day after that. It always started with me helping him to piss, and my getting his pants down around his ankles was part of the ritual. Meeting him every day and helping him piss, followed by helping him cum escalated fairly quickly. By the end of the week I was sucking his cock for him fairly vigorously, and I took his load in my mouth willingly, with him giving me whispered directions in his deep voice.
We were also interrupted several times, and Jack having me sit in his lap to hide my presence from other visitors while he pretended to be taking a dump. I’d be sitting in his lap with my legs wrapped around his waste, my small torso laying on his chest and belly…my face buried in his neck while we waited for whoever to leave so we could continue. I didn’t mind this at all, appreciating being wrapped up in his masculine scent.
He spent time with me after he got off, too – which I looked forward to as much or more than helping him with his horny cock. We often walked downtown and chatted, sometimes having a snack or lunch before walking me back to the library in plenty of time for mom to pick me up. After several days of nearly being discovered, though, he told me it worried him that eventually someone would discover us because that bathroom was used by men regularly to hook up. He asked me if I’d be ok with him driving me to his house to spend time. I agreed as long as he promised to always have me back in time before mom missed me and I got into trouble. He was happy and said we’d be more comfortable there, and have more time to “play.”
The following Monday my mom dropped me off in front of the library as usual, but Jack whistled at me before I could either go into the library entrance, or walk around to the side basement entrance that led to the public bathrooms. He must have been watching for me to be dropped off. I hopped into his truck and we drove away, stopping at a drive through to get shakes before heading to his house. He asked me about my weekend and other small talk until we arrived at his house – it was only a few minutes from downtown.
His house was small but had a large yard and an attached garage – he parked inside, saying he’d prefer the neighbors didn’t notice that he had company, especially since I was so young and small. We entered into the kitchen and sat at a small table to finish our shakes and talk, and then he asked me if I wanted to go play on his bed where it was comfortable. I said that I did, so we walked back with his arm around my shoulders.
I was accustomed to the ritual now, and I unzipped his jeans and unbuttoned them without being asked. He sighed and smiled down at me while I did, but things changed a little with the new environment. He also asked me to unlace his work boots and lifted his feet one at a time for me to removed them and his socks. He stepped out of his jeans and hugged me, massaging my back and squeezing me into his belly. He pushed me away after a minute and asked me to unbutton his shirt for him, too – new. I complied in silence though – very excited to see more of his body. His cock stood up on its own while I struggled with his buttons, and he was fully erect with his cock pressed into my upper chest as I helped him shrug out of his shirt.
It was the first time I’d seen him completely naked and I was enthralled. He was so tall he towered over me – muscular, but stocky. He just looked like superman to me, but a little pudgy, especially with his oil slicked hair and cocky grin. He pulled me into him again picking me up off the floor and laughed…asked if I liked what I saw. I of course said yes. He put me back onto the floor and told me I could undress too if I wanted.
I was nervous and embarrassed but complied. I was so small and skinny compared to him, and I was especially ashamed of my small penis and barely descended balls. After I was completely naked before him he said I was beautiful and soon I’d develop into a handsome young man. His cock was throbbing and he said he would like some help again but on the bed this time. He picked me up and tossed me easily onto the bed and we wrestled some, him tickling and teasing me before settling down. He lay back on the bed in the middle and spread his legs. He said I knew what to do now so he’d let me take over.
I settled between his legs and began to stroke his cock, very familiar with it by now. I also began to suck the head and it startled me when he moaned loudly – he snickered at the expression on my face and said we weren’t in the library anymore and so didn’t have to be quiet. I laughed to and went back to work, sucking and stroking him while fondling his balls. His grunts and moans spurred me to try harder to get more and more of his cock into my mouth, and I gagged a few times. He asked me to slow down also, saying he wanted it to last a long time.
He also held my head in place and pumped his cock in and out of my mouth several times. After getting close a few times and pulling me off of his cock to recover he asked me if I wanted to try something new. I said sure and he lifted his legs, exposing his asshole to me for the first time. He asked me to lick it for him, so I kneeled in beneath his hanging balls and licked…I was a little nervous it would be dirty and small, but he was very clean – it just smelled iike him. He moaned very loudly at the first lick, almost like a cry…I knew it felt good to him, and i wanted badly to please him…so I kept licking, kissing, with him enouraging me to press against his asshole hard with my tongue and face.
This continued for some time, with him telling me to sometimes lick his balls or cock again for a few minutes and then back to his asshole. He stopped me altogether at one point, saying he was getting too close and he would need to cum soon. Again, he asked me if I wanted to try something new and I said yes, again, intoxicated with what we were doing. He asked me to lie on his chest with my ass near his face so I could relax while I sucked his cock and finished him.
I settled over him and lay all of my weight on him since he was so big I couldn’t really put my legs down anyway, and I began to suck his cock again – his big arms wrapped around my waist to hold me in place. While I sucked he began to massage my ass cheeks with his large hands, kneading them in time with my sucking. He asked me if I wanted to see what it felt like to have a tongue on my asshole and I “mmhmm’d” around his cock, feeling him spread my cheeks wide. I squealed involuntarily when his hot tongue connected with my asshole and he laughed.
We continued this way, my mouth vigorously sucking his cock while he licked, kissed, and sucked on my asshole. He was overstimulated soon, and told me to just hold still. He began to pump his cock in and out of my asshole and I relaxed…realizing the angle was easier to take his thick cock, as more and more pumped into my mouth and down my throat – all the while he was enjoying my ass. He warned me that he was going to cum and asked me to remain still…he pumped slowly and I felt his cock thicken even more before spurting jets of cum into my mouth. I was used to the consistency and taste by now so I just swallowed reflexively as his cock pulsed and spurted. I felt his cries and moans more than heard it, since his face was still buried firmly against my asshole.
Once his tremors stopped and his cock softened he scooted me off of him and turned me, then held me against his side. We chatted awhile, with him asking me about how I felt after, since we’d done some new things. I told him it was great, of course, so pleased that he seemed happy too. We drifted off a little and I was still snuggled up tightly against him when he nudged me so he could get up. I heard him pissing in the bathroom and was a little hurt he didn’t invite me to help him. He came back to the bed and snuggled up against me again, though and I quickly forgot.
He massaged me all over, which was glorious…giggling as I grunted and moaned. He spread my cheeks again while I was on my belly and licked and sucked on the hole more, then felt him massaging my hole with his finger. He asked me if I minded if he checked to see how tight my asshole was, and I told him it was ok. He licked and sucked more, pausing to massage it with his finger…eventually I felt him push into me slightly. I squeaked a little at the penetration but didn’t ask him to stop. He continued to lick and suck and the sounds grew wetter, until I felt his finger finally slide into me and he held it in place.
He asked me how it felt and I told him it felt weird, like I had to poop. He asked if there was pain, and I told him it kind of burned – he slowly withdrew his finger and apologized for hurting me before crawling back up to lie beside me. I told him it didn’t really hurt much and it was ok. He squeezed me and smiled, saying I was a good boy and he was so glad I’d met him in the men’s room. He explained that there were many things he’d like to do, but he was concerned about me being so young and small. I told him that I was having a good time and loved what we were doing, then asked what else he wanted to do.
He explained to me about fucking, but he was afraid his cock was too big for me right now and we might have to wait until I was older. I protested and said that I wanted to but only if he did. He just patted my back while I lay against him and looked up at the ceiling, saying he would think about a way for us to try. But for now, what we had done so far was fun enough…and that he would continue to check my asshole for tightness.
Since it was getting late, we finally got dressed and he drove me back to the library, but dropped me off in the back parking lot just in case mom had beaten me there. He hugged me again, and told me to be a good boy – saying he’d pick me up the next day around the same time. If he didn’t catch me when mom dropped me off, then he’d meet me in the men’s room in the basement.