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 c****, 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 c*** 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.

We met every day that week to repeat the same thing, but after being interrupted several times he asked to play at his house. He’d pick me up as soon as my mom dropped me off and drive to his house a few minutes away. It was very different at his house because we played on his bed, and we both got completely naked. By then I was able to s*** his c*** pretty well and we explored more – having me eat rim his a** while I sucked and him r****** me. I loved laying on top of him so he could f*** my mouth with his c*** while he licked and sucked on my hole.

We talked about f******, but he was worried my a****** was too small for his large c***. He even inserted a finger into my hole to confirm – it was uncomfortable and burned a little. We met every day for him to pick me up and carry me to his house to play, and he continued to test my a****** with a finger…he loved inserting it into me while I sucked on his c***. After a few days he was able to f*** it in and out of me. pretty easily, and graduated to two. I noticed that he was f****** it in and out of me using the same rhythm I used on his c***, and it was pretty pleasant. Near end of the week I was easily able to take two fingers and he was pretty pleased. Even after he had gotten off a few times, he’d slide two fingers into my hole while we snuggled and napped. He was still talking about f******, but despite me being able to take two fingers he was concerned his c*** was still too big. As he was driving me back to the library he told me he had a friend that he’d like for me to meet if I was interested, and that he might be able to help us with f******. I was nervous about it but agreed.

The next day when we walked into his house, a man was sitting at the kitchen table having a beer. He was older than Jack, and shorter when he stood to meet us, but still much taller than me. I guess that that he was in his late 40s/early 50s…bald, and had a goatee that was mostly white with a little black here and there. Jack introduced him as his friend Robert and they sad down at the table…Jack pulled me onto his lap. Robert commented on how cute I was and said that Jack talked about me all the time. His smile reminded me of Jack a lot but I never knew if they were related. He asked me all kinds of questions about me, and if I was having fun with Jack, etc. He seemed a little nervous about my age, but I guess seeing me so comfortable with Jack he relaxed. Robert finished his beer and said he was ready to have some fun if we were.

We all went to Jack’s bedroom and they began to take their clothes off. With the ritual interrupted I just watched them. I loved seeing Jack completely n***, his large frame muscular and stocky – Robert was very different, even beyond his bald hair and salt/pepper goatee. When he undressed he was very hairy. He was also shorter, but still very muscular with a larger belly. Some of the hair on his chest was also going white, but from his chest down the hair was black like Jack’s. Jack’s large thick c*** still hadn’t gotten hard yet, but Robert was hard before he took his underwear off. The difference between their c**** was noticeable. Robert’s c*** was much smaller and thinner.

Robert stood by Jack and they both looked at me smiling, and Robert asked if I was ok – I said that I was. Then he asked if it was ok if he helped me get undressed, and I automatically just held my arms up. They both laughed and proceeded to strip me naked before squishing me between them in a hug. I felt intoxicated in their presence, my face buried in Jack’s belly and Roberts fur tickling me on my back. I was hyper aware of Robert’s hard c*** pressed into my back, and I felt Jack’s c*** twitching against my chest. They both hopped on the bed to lie side by side, and Jack asked me to help Robert with his c*** first.

I crawled between Roberts legs to kneel between them and took the opportunity to explore his furry legs and belly. I stroked Robert’s c*** and fondled his c***, easily getting my fingers around his shaft. I leaned down to begin to lick and s*** on his c*** and fondle his balls, aware that Jack was watching carefully and stroking his c*** to hardness. Robert hissed and moaned,telling Jack that he wasn’t kidding…that I did know how to s*** c*** really well. Jack reached over to stroke my head while I sucked Robert’s c***, telling Robert that I was a great boy and always did a good job. Robert’s c*** was much easier to s*** so I was going a little crazy on it, easily taking in to the base.

After a few minutes, Robert patted my head and asked me to stop before I made him c**, laughing at how eager I was for the c***. He told me to work on Jack for awhile and he was have a different kind of fun. Jack scooted to the center of the bed when Robert rolled out of the bed. I immediately began to s*** on Jack’s larger c***, feeling Robert’s weight on the bed again behind me. I squealed when his hairy goatee suddenly connected with my a**, causing them both to laugh. Soon we we all grunting and moaning, and I was electrified having a mouthful of Jack’s c*** and my a** being scrubbed with Robert’s goatee.

Robert patted my a** after eating it for a few minutes, saying he’d be right back. I watched him go into the bathroom and returning a moment later holding a small tube of something. He watched me s*** Jack’s c*** for awhile, and Jack reached over to stroke Robert’s still rock hard c***. Robert said he coudn’t believe how well I was sucking Jack’s large c***, before getting behind me again. I gasped when I heard a wet sounding squirt and felt cold liquid flowing onto my crack. Jack patted my head and said it was ok, that Robert was going to finger my a****** like he had been doing.

I relaxed as Robert massaged my a******, enjoying the sensation of his fingers warming the liquid. I protested a little when his finger finally slid in. He held it in place while massaging one of my a** cheeks…remarking to Jack that he wasn’t sure about this because I was so tight. Jack encouraged him to keep going, because I would loosen up some and telling him to finger f*** me in time with how I was sucking his c***. Pretty soon I was drifting down Jack’s shaft with my mouth in time with Robert’s fingers slipping in and out of my hole and the rhythm and sensations were amazing. I protested a little more when Robert added a second finger, but adjusted soon with the new method. Robert also began twisting his fingers around in my hole, causing me to shudder. The feeling was bizarre but nice. Robert also massaged my small balls and c*** underneath me, causing my legs to quiver and I couldn’t help but moan.

Robert’s weight shifted and I felt him scoot further onto the bed, kneeling behind me…his c*** lay against my crack and the fur of his legs and groin tickling my a**. “I’m going to try to put my c*** inside your hole, but just a little. Tell me right away if it hurts, ok?” He asked. I didn’t answer but nodded, unwilling to take my mouth of Jack’s c***. I looked up into Jack’s face and he looked at me and smiled. I felt the head of Robert’s c*** pressed against my a******, nervous but excited. I felt Robert h****** against my hole for several minutes while I sucked, and suddenly it slipped inside me, just the head.

Robert massaged my hips, but held himself still, asking me if I was ok. I’d let Jack’s c*** slip out of my mouth. I answered that it didn’t hurt but it of burned a little. He told me to try to squeeze it with my a****** as hard as I could, then relax. He kept repeating it over and over, and I complied. After a few minutes it stopped hurting and I began to s*** Jack again. Robert continued to hump gently, not really moving his c*** just getting into a short gentle pace, sometimes pulling the head of his c*** out and popping it back it, and he kept squirting more liquid onto my hole. It was a strange sensation, the feeling of his c*** inside me, and I was very aware of each time his c*** would slide in a little deeper into me.

After a few minutes, Robert’s bush was against my a******, and he told Jack that I had all of his c*** inside me now. Jack told me he wanted to see and scooted off the bed. I moaned as Robert pulled his c*** out to the head to show Jack and immediately pushed it back inside. Jack patted my back while watching Robert’s c*** slowly slide and out of me. Robert said I was extremely tight but taking it better than he expected since I was so small. Jack told him to keep f****** me and returned to my mouth so that I could continue to s***. I was being fucked at both ends, with them grunting and moaning – so was high, being filled at both ends with thrusting c****. The wet sounds of my sucking and slobbering on Jack’s d*** was joined with the wet sounds of Robert’s c*** – my hole was making squelching and farting sounds.

After several minutes of this Robert told me he was going to f*** harder and to tell him if it became painful. He increased the speed of his pumping, and also began to pull his c*** out and slide it back in, moaning about how wet and tight it was but loosening up. Jack pulled away again to reposition himself under me, his head between my legs, and scooted I could reach his c***. I realized he was watching Robert f*** my hole from underneath. I also felt his mouth begin to lick my balls and c*** and I squealed, but didn’t struggle at the stimulation. Jack began to f*** my mouth in time with Robert’s strokes and I soon didn’t have to move at all…just enjoy being fucked at both ends.

Robert’s f****** had become pretty hard now, and the slapping sounds quicker when he said he was going to c** and whether he could c** inside my a**. Jack told him to fill me up and Robert buried his c*** deeply into me, causing me to moan. I felt his c*** thicken inside me, then begin to pulse. I realized he was squirting c** into my a******. Jack wriggled out from under me while Robert held tightly against my a******. Once he’d joined Robert behind me, Robert began to pull his c*** out, causing me to hiss and moan. Suddenly I was empty and Robert collapsed beside me, grinning and laughing. He kissed my forehead and told me that Jack was right – I was an amazing boy.

Jack slid a couple of fingers into me easily, rubbing my asscheeck, and asked if he could try his c*** inside my a** now. I said ok, and felt his large cockhead press against my hole. Robert stroked my head while Jack humped against me, and I moaned loudly when it suddenly popped in. Robert told me it was ok, and said to squeeze with my a** and relax, over and over, as I’d done with his smaller c***. After a few moments Jack pumped a little more, then pulled out of me…and then pushed into me again, a little deeper. I was very wet but it still took a lot of effort for Jack to push into me.

After a few minutes, slowly f****** in and out of my hole, Jack’s bush was against my a******. I was much fuller now, and I could feel a heartbeat but couldn’t tell if it was mine in my hole or his c***. Slowly he pulled out until just the head remained, then pushing back in. I couldn’t move and wasn’t aware of much except Jack’s c*** – I felt stretched to the limit though he was gentle and slow. I was aware of his c*** flexing in my hole, used to it doing the same but in my mouth while I sucked. Soon he was pulling it completely out of me and sliding it back in, and my arms and legs were quivering. Robert was stroking my hair and told me to just lie down on the bed to relax.

Jack lowered himself onto me completely, nearly covering me entirely. He was such a large man that my head was under his chin when he was fully lying his entire weight on me. I watched Robert while he watch Jack f*** me. Jack was grunting as he pushed and pulled his thick c*** in and out of my a******, sometimes pulling it out completely then pushing it back in…I was aware of the wet sucking sounds my hole was making as he fucked it.

He whispered that he was getting close but he wanted to see my face while he came, so he pulled out of me and rolled me over onto my back. Robert sat up to hold my legs up to my check while Jack pushed his c*** back inside my a****** and began to f*** again. Robert was watching his c*** slide in and out of me and told him that I was a natural at taking c***. Then he lowered himself onto me again and told me to hold on, so I wrapped by arms around his neck.

Jack told me how amazing I made him feel and how great I was doing learning something new to please him. I was beyond doing anything except nodding and moaning by then. He began to pick up the pace, f****** me faster, although he would still pull his thick c*** out of me now and then, inviting Robert to look at my a******. After several minutes he commented that my a****** wasn’t closing anymore, and seemed happy about it. Jack announced he was about to c** and lowered his weight onto me again, now pounding my a****** before tensing up all over and bury himself as deep as he could. I felt his c*** thicken inside me, and I felt him shooting his thick ropes of c** into my a******.

He stayed on top of my, heaving and moaning, before finally kissing my forehead and pulling his c*** out of me and rolling off onto the other side of me, leaving me between the two of them. I was vaguely aware of a need to get to the bathroom and told Jack, but my arms and legs would not work well…I was too shakey and weak. Jack finally picked up me and carried me to the bathroom to sit me on the toilet, where I almost immediately began farting their two loads of c** out of my hole.

After awhile I was finally able to stand on my own. Jack led me to the shower and we both cleaned up, Jack doing most of it…lathering me up and hosing me off with a handheld sprayer. We dried off and returned to his bedroom where Robert was still laying. We got dressed while Jack told him he needed to get me back to the library – this was the longest he’d kept me and he was afraid my mom would beat me back there to pick me up. Robert got up to hug me and tell me how glad he was to finally meet me. I agreed and returned the hug as tightly as I could.

On the drive back, Jack asked me if I was ok – whether I was terribly sore after being fucked for the first time. I told him I was sore, but it didn’t hurt too much. He said it would probably be worse the next day or two. Since it was the weekend I wouldn’t be able to see him, but that I needed to be careful not to let my mom and dad know that I was sore because it might come out that is was from f******. He told me to soak in warm water if I needed to and also to watch for blood when I went to the bathroom, saying if I did bleed any I should probably stuff some toilet paper into my crack – promising me that if I did bleed any it wouldn’t last long and was nothing to worry over.

Luckily we did beat mom back, so I just waited on the steps for her – other than running down to the basement public restrooms once to fart out some more c**. Jack was right that I’d be more sore the next day. When I woke up I was immediately aware of my sore hole, and had to force myself even to fart while sitting on the toilet. While I was bathing later, I explored my hole and it felt hot and sore, but not too bad. I never noticed any blood, which relieved me. By the next day the soreness had almost completely subsided, and I was looking forward to Jack f****** me again.

Robert was there at Jack’s now and then, but not terribly often, over the summer. I liked him, but now as well as I did Jack. I do credit him, though, for taking my a*** cherry and making it possible for me to be able to handle Jack’s much bigger and thicker c***.

More soon.

• Share on Facebook