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Jack and Tom

I had finished my uni work for the day quite early and I sat at my desk at home, idly browsing porn and hookup sites looking for something to tickle my fancy. I’d been exploring my bi side a bit more lately, moving from “letting” guys blow me to meeting guys for some mutual wanking and oral. I was enjoying practicing sucking cock and obviously loved when guys returned the favour. I’d still occasionally meet a guy or trans girl and fuck them but most of my meets would be sitting watching porn with a guy; kissing, wanking and sucking each other.

I got chatting to an older guy called Jack. He was 46, looked in good shape and had a nice thick looking cock. He told me it was 8 inches but I’d learned by now that I’d believe that when I saw it. He was visiting my town for the night for work and asked if I’d be free later and wanted to come round to his hotel room for a session of mutual head and wanking. I said I would and once we’d exchanged phone numbers he said he’d pick me up around half 5 that evening.

I got a little worried that I was already so excited about meeting later so I decided I’d just relax, wank to some porn and recharge before I met up with Jack. I shot a load to some bi porn as was my tastes at the time. I took a long shower and tried to relax and stop thinking about my meet later but I couldn’t stop opening up the hookup site and looking at Jack’s cock and body. I left my apartment just after 5 and headed towards where I’d asked Jack to pick me up; I wasn’t out as bi to my flatmates so I didn’t want to meet him too close in case they saw me get in his car. I was halfway to the meeting place when Jack texted me. As soon as I felt my phone vibrate my heart sank. It must be Jack cancelling, he wasn’t real, he was just wanting to get my pictures, he’s had a better offer. It turned out the last guess was half right.

“Hey D, just picked up a friend that’s going to join us, hope that’s OK. He’s about your age too”. I re-read the message a few times and was trying to decide if I was OK with it. I’d always avoided guys my own age in case I bumped into them in university or through friends. Before I’d had a chance to construct my reply, Jack’s car pulled up and I got in. He looked amazing and I loved the smell of his aftershave. He introduced me to Tom who was sitting in the back and then drove off towards the hotel. Tom seemed nice and friendly, but he wasn’t really my type. I thought about telling Jack I really wasn’t feeling it but then he rested his hand on my knee and a rush of arousal came over me. I felt the warmth rush to my cheeks and when he grabbed my hand and placed it on his bulge I knew there was no turning back.

We got to the hotel and Jack lead us to his room. I was so glad we didn’t have to pass reception. Jack started to undress and Tom and I followed his lead. When we were down to our underwear Jack beckoned us to come closer to him. I got there first and was rewarded with a deep passionate kiss, Jack’s tongue exploring my mouth as we both moaned deeply. He turned his attention to Tom and they shared a long kiss too. Jack looked amazing! He had a tall muscular frame with a little hair on his broad chest. He’d undressed to reveal he was wearing a jock that just about contained his impressive bulge. Tom looked great too; he was slimmer than me and mostly hairless, and rubbed at the bulge in his briefs as they both kissed. I watched them make out in front of me, my boxers tented up by my hard cock. Jack pulled me in closer and asked that me and Tom kiss. I enjoyed being watched even more than watching and me and Tom put on a show for Jack, we felt like two boys trying to show off who was best for Daddy. Jack joined in and for a while we all swapped kisses and rubbed each other’s cocks. When I wasn’t involved in the kiss my mind raced. Would two of us suck the other? Would one suck both? Would we lie down and all suck each other? I hoped if we did that I got to suck Jack’s thick cock, it looked huge in his jock.

“Come here and suck us” Jack told me. I needed no second telling and dropped to my knees. I pulled out both their cock and they slipped out of their underwear. Jack was every bit as big as he looked in his pictures, easily 8 inches and a nice thickness. Tom turned out to have a very nice cock too, maybe 6.5 inches but thick and meaty whereas Jack’s felt like a bone with no meat, just absolutely rock hard. It was such a turn on to suck them and hear them moan through the kissing. I took my time and gave nice slow head to them both, wanting to savour this moment and not wanting anyone to cum too quickly. I really loved sucking Tom’s cock, his girth stretched my mouth wide open and I enjoyed seeing him moan and react with every lick and stroke.

Jack pulled me to my feet and Tom took my place on his knees. Tom started by sucking my cock while I kissed Jack and rubbed his cock. When Tom moved to Jack’s cock, Jack told me to pinch and rub his nipples. Tom was taking his cock deep in his throat as I was pinching Jack’s nipples and kissing his neck. It felt amazing to see him writhe and squirm while two young guys pleasured him.

For a while we went on like this, switching positions and taking turns on our knees. It was a sensory delight, going from having two cocks in your mouth to having yours sucked while you made out with the other guy to sharing a cock and making out on your knees while a cock pushed between your lips or licking the balls while the other guy sucked the shaft. I was standing with Jack while Tom worked between our cocks, wanking one while he sucked the other. Jack looked down at him and asked “Do you want me to fuck you?”

Tom was pretty taken aback. “I don’t do that. I’m top” he said. I said I was the same and it became clear there’d been a mix up somewhere. 3 top guys here blowing each other and Jack really wanted to fuck some ass. I could tell he was disappointed but we went back to taking turns blowing each other and making out. I was on my knees sucking both their cocks and I couldn’t escape wondering how it would feel to take them in my ass. I’d never had anything bigger than my finger in my ass and as I sucked Jack’s big thick cock I wondered just how hard it would be to take it. I started to think how hot it would be to be the meat in their sandwich. Would they take turns fucking me? Would Jack’s long hard cock feel better or would I like Tom’s thickness. I’d made up my mind; I was getting fucked.

Once again I found myself standing with Jack while Tom sucked our cocks. I kissed Jack’s neck and worked up to nibbling his ear. “Do you want to fuck me?” I whispered to him. He raised an eyebrow and asked me if I was sure. I said I was but he’d have to be gentle as I’d never been fucked before. He assured me he’d make sure it felt good and we all moved to the bed. Tom said he just wanted to be blown and watch Jack work me open so he lay back on the bed propped up against the headboard.Jack positioned me bent over on my knees with my face in Tom’s crotch and my ass up in the air to the edge of the bed. The tension was getting too much for me and I slipped Tom’s cock into my mouth to distract me.
I felt Jack’s hands spread my ass and half expected a lube finger to slide into my hole. I was pleasantly surprised to feel him tonguing my ass, starting with gentle licks but then probing my hole with his tongue. It felt amazing and I moaned loudly while sucking Tom’s cock. Once I was relaxed, Jack started to rub my ass with his finger. I really wanted it inside and when he spat on my hole and worked his finger in I knew I was going to love his cock in there too. He gently worked my hole until he was knuckle deep and slowly fucking me with his finger. He started to slip a second in but had to stop and lube up his fingers and my ass. In what felt like no time he was deeply working me with two fingers while I sucked on Tom’s cock and occasionaly turned back to Jack to join the filthy talk of how he was going to fuck my virgin ass. He asked if I was ready and when I said I was he rolled on a condom and lubed up the full length of his cock.

I thought since I’d been fucked quite roughly with two fingers that a cock wouldn’t be that much harder to take. I couldn’t believe how big it felt as he pressed the tip into my lubed ass. I groaned through a mouthful of cock and Jack slowed down and held still. He told me to relax, that he didn’t want it to hurt and that if I relaxed he’d be able to gently stretch me out. The next few minutes were mostly painful, but I did get some enjoyment from knowing I was managing to take his big cock in me. “Guess what” Jack asked, before telling me that he was balls deep. My virgin hole (I couldn’t call it that anymore) had taken every bit of his thick 8 inches and I felt an amazing rush when I realised that. He held me still for a second and then began to gently fuck me. His short slow thrusts felt amazing. I knew his cock was deep in me but it felt like it was ready to burst out of my chest. He worked up to longer strokes, still slowly and once he pulled all the way back, lubed his cock up and slid balls deep again, all the pain was gone and I could fully enjoy him fucking my hole.

“I’m getting close” Tom said. I’d been sucking his cock this entire time and he was clearly enjoying watching Jack open me up. In hindsight I maybe should have slowed down but Tom wanted to cum and a switch had flipped in my brain and I was hungry for as much cock and cum as I could get. I started taking his cock deeper in my throat while Jack picked up the pace behind me. I bucked back as I pulled off Tom’s cock, then pulled my hips forward as I throated him, making sure that my ass was working the entire length of Jack’s cock. I only stopped working both cocks when Tom started to unload in my mouth. I swallowed every drop while Jack pushed and held his cock deep in me. Tom was spent, he lay back on the bed and watched the rest of our fuck session.

Jack wanted to change position and he lay down on the bed and had me sit on his cock. I couldn’t believe how easily he slipped back in my ass, I was totally stretched open. I alternated between bouncing up and down the full length of his cock and rolling my hips while taking him deep in me to grind his cock in my ass. The grinding felt so good I was worried I’d finish before him if I kept doing it so I went back to riding him. Jack told me to pinch his nipples while I did this and I did as I was told. I started to really get into my role as the sub bottom looking after daddy. “You like that, Daddy?” “Is my ass tight enough for you, Daddy?”, “Fuck me deeper, Daddy”. This drove Jack wild, and we made out passionately while he fucked me from the bottom. I could feel his balls slapping against my ass as he hammered his cock into me.

Jack told me he was getting close and wanted to cum while fucking me on my back. Again, I did as he told me and lay on my back with my legs wrapped around him while he slipped his cock into me once again. After how easily I’d ridden his cock I didn’t expect just how much I’d feel while he fucked me on my back. His cock felt absolutely huge and it felt like it rubbed against something inside me that sent tingles to my cock. Jack started to really fuck me deep now, he lifted my legs over his shoulders and pinned me to the mattress, pounding his cock balls-deep in me with every stroke. He asked if I wanted it harder and of course I replied “yes, Daddy”. As he picked up the pace I could hear his breathing get deeper and louder. He grunted with every stroke and I could tell he was getting close to cumming. I reached down and started wanking my own cock in rhythm with each thrust. I held myself right at the edge of cumming until Jack started fucking faster. This sent me over the edge and my cock started shooting long ropes of cum all over my chest and stomach. Jack let out a huge grunt and I felt his cock erupt inside me. I’d forgotten Tom was even in the room but at this sight he wanked himself to another orgasm, it felt hot that he’d gotten off just watching us.

We kissed while Jack’s cock twitched and pulsed inside me for what felt like a lifetime. When he pulled out I could see a huge load had filled the tip of the condom. We all showered there and freshened up to go home. The entire trip home I felt like my ass was gaping wide open and worried it wouldn’t return to normal, a feeling I’m now very used to and can identify as just having a well-fucked hole.