Our Junior Year

Harry leans over and Kisses my back.

We rest quite a while in total silence, I know I’m wondering what thoughts are traveling through Harry’s mind right now, I finally separate from Josh, as he rolls over and Harry just says how hot that was unconsciously still stroking his semi hard dick. Josh then asks if Harry would like to try fucking me or him, with hesitation Harry responds with a question “Yes….?” Josh flips me to my back and holds my legs up as Harry instinctively kneels behind me, Josh bends me over exposing my hole upward, and he pours a sufficient glob of lube into my crack , his fingers caress my hole, as I glance at Josh’s face and he stares into Harry’s eyes. Harry’s dick now rock solid again, like an endless desire of young adolescent hormones touches the lubed crack with its head. Josh still holding my ankles close to my head with one hand now, he touches Harry’s shaft with his free hand, and rubs it in between my cheeks. Now I’m not a lover of bottoming, but I do it for Josh’s pleasure, and I love him, but Harry is also much smaller than Josh and a lot slender. Harry begins to push in, all while Josh is tenderly speaking, almost in a whisper “that’s it”, you can apply pressure” push a bit harder” you can do this”. Josh didn’t know it, but it’s those words he uses when he does me that sooth my mind, as we both listened intently. Soon Harry breached the ring and Josh moved his hand from his shaft to Harry’s tight little ass, and he ever so gently guided Harry s manhood into my ass, I didn’t even wince, and thought he still had further to go when I felt his nut sack on my ass. He’s in I thought. Harry tried to lay on top of me between my spread legs squashing my nuts between us as I gently pushed him up and off and grabbed my nuts to help protect them and jerk myself at the same time. Harry began slowly pumping, it felt great with no pain, shit I thought maybe Josh banging my ass might be stretching me out because this was a breeze, it usually took me forever to get used to Josh being in there. Harry was pumping away almost uncontrollably and was deaf to Josh’s voice telling him to slow down and enjoy it at this point. It was no use, Harry was spewing cum in my hole almost as soon as he started, but hell it was his first, then it dawned on me I was his first ass. I didn’t know it at the time but Josh revealed later he took his lubed up fingers, and played with Harry’s hole all the while he was fucking me.

After a short nap, Josh asked Harry if he was ok and if he enjoyed it, but warned him once more this should be thought of as “training” if you will, and he needed to get out there and test those waters for himself, and when he was ready he would eventually want to come out. He stressed he didn’t mind fooling around with him, but wanted to make sure it didn’t become a regular thing. After Harry dressed and left, I began to wonder if we went too far, or too fast, and felt guilty that we may have used Harry. Josh later said it reminded him of his one night stands and although it was hot he still wanted me to be sure that I was still and always will be the one for him, I felt so reassured by his words.

The next day we got a call from Tommy and things were moving along at his Ranch, he told me he hired his ex girlfriend Maryann, which both Josh and I once again got very concerned with, as she was OK but her new boyfriend (Billy Prescott) was a dick and really could mean trouble. Immediately the Devin concerns took a back burner in my mind, as now I was more concerned with Maryann and if she was using him.

Then he told us about this guy Kevin that he hired, and how huge he was and the town board meetings and how he’s been fighting the locals, who even though the farm has been operating for years as his parents, that now expanding it and Gay prejudice was spreading amongst the towns people. Tommy had a great opportunity to expand into a neighbors land and turn part of the riding stables into a dude ranch. All in all we thought it was too much too fast. Josh and I wished we could help but weren’t quite sure what we could do.

Later that night my dad called and told me of the woes that Tommy was suffering, and how local suppliers were cutting him off, some of it was because the property and money issues weren’t settled yet from his parent’s death, inheritance, and insurance, and he had a huge cash flow problem, but we all suspected a bit of discrimination going on as well. With that Josh was scrolling through his phone and soon took over the conversation he found a gay pride flag on Amazon and told my dad he was sending it to him, he agreed to place it in the window for all locals to see. My dad has been in business for almost 35 years and was well respected in the town, he survived the big corporate giants who tried to undercut him and take his business away. He felt he could show his support for Tommy and suffer little consequences. I had my doubts, as I expressed, after all I grew up in that town, and wasn’t comfortable at all until Josh brought me home to come out. Josh then found small desk or table top flags on sticks and ordered up 150 or so for my dad to place on the counter, Josh was all in as was my dad, but I was concerned.

Tommy called again the very next day all excited, and said my dad had put an LGBT flag in his center display window facing out onto Main Street, we told him we knew and it was all Josh’s idea. Tommy couldn’t be more thankful for all the help dad had provided for him during his time of need as well as Josh and me, he also said Devin, Kevin and Maryann were all so very supportive, they could see a gold mine was on the cusp of being discovered and all wanted a piece of it, but the town board was still against any variances to set the Dude Ranch in motion.

The next day Josh and I were off to classes and I got a call from dad about 9am our time (8am in the Midwest) his store was vandalized, window was broken, flag torn down and burned inside luckily the fire didn’t spread. My concern for mom and dad was genuine I quick called Tommy and told him what happened and Tommy and his crew all went down to town to help my dad. I called Josh crying that we had done a bad thing, Josh immediately ran across campus to me and offered to fly out to help or aid, I told him about Tommy and Devin and Josh calmed me down and suggested we wait a few days first, reluctantly I agreed.

Tommy called later and said the most of the other merchants chipped in and helped my dad, clean up, board up and got him up and running and the stick flags arrived he told me my dad was handing them out like lollipops and almost all were gone before the end of the day, and how almost every store had a small little LGBT flag somewhere prominently displayed.

Maryann had asked if Tommy could hire Billy Prescott, oh shit I thought another dumb move, but Devin convinced him to do it and it turned out Billy’s dad was the town supervisor and was a driving force in the decisions made on the town board. I guess it paid off because after the vandalism and the town outcry, then Tommy hiring that loser who couldn’t keep his fast food job and Maryann dumping him, I guess it all worked out so apparently Billy was working out better than expected and was making money that his dad insisted he begin doing or he was out. Damn things were looking up for Tommy. Josh and I thought this guy Devin might be a good fit for Tommy, he seems to be working out well,

No sooner was that discussed and within a few days we were hearing stories about Devin this, and Devin that, and Tommy even got a little descriptive about their personal time, in fact he got us all hot and bothered one night when he told us a story about he, Devin and Kevin who they were calling Hulk and the threesome they had in Tommy’s living room. Hot Damn Josh and I had to meet this guy, and almost couldn’t wait till our Christmas visit back home.

That night in bed Josh and I were talking, and all we could picture was this big green monster having his way with us, Josh told me he thought Tommy was exaggerating, after all Tommy was a “Novice Gay” and Josh bet me he could take Hulks dick up his ass in a heartbeat, I laughed and pulled out our “toy box” and said oh yeah and pulled out the huge hollow dildo we only used once, I slid it on over my hard dick, I fit in the hollowed out part, which somehow seemed tighter fit this time, and began lubing it up. Damn that rubber sleeve made me at least 3 times bigger all the way around, well I recall the last time I used it Josh couldn’t walk for at least a day or so. I got Josh naked and began working his ass with various lubed up but plugs and even had some anal beads while I sucked that massive member of his down my throat, I was proud these days that I could take him without gagging and the “cum like” saliva it produced from the back of my throat made me slip and slide up and down like a pro, as I deposited it on his shaft and it dripped to his balls even down to the butt plugs I was playing with.

Then whether he was ready or not , I certainly was, I rolled him over on his stomach and lined up that rubber appendage I was wearing complete with oversized balls that mine fit nicely into, I began by sliding up and down, Josh carefully poked his ass upward and I located his hole with my fingers and began to apply pressure. At first it was like he was clamping shut, he wouldn’t let me in., I know he was scared because of all his talk, but then I reached under his raised off the mattress abdomen, and ran my fingers in his thigh joints between his balls and he liked the tickle and he lost his concentration and I was able to slide the tip in and hold it. Then I reached with my right hand and began stroking him as my left caressed his ball sack, and I pushed in a bit more . I didn’t hear any noise from him and I bent over to see his face, his mouth was clamped hard onto his pillow and his eyes were shut so freaking tight the crows feet stretched almost to his ears. I couldn’t make him suffer anymore and I began to pull out when he yelled, “no keep going don’t stop your almost there”, of course I had no feeling in that rubber sleeve so I couldn’t really tell, and so I pursued, and in I went slow but sure, till I was all the way in the rubber balls squished into his ass and my balls into the rubber lining. I began to stroke in and out very slowly at first as Josh yelled” Fuck You Yeah” over and over, he said he loved it but he was in pain I could tell. Then it happened, like the first time I was fucking him with this dildo, my lubed dick began sliding around inside this sleeve, so the huge rubber dildo was fucking Josh, and I was fucking the rubber dildo inside of him, till we both came almost together, his dick still being jerked by my hand and mine filling the dildo as the squishing suction noises of dick and cum and rubber were squirming around in Josh’s ass. We collapsed in exhaustion and fell asleep

About 3am Josh began tickling my tummy and it felt weird as I still was inside this dildo and my dick was hardening at his touch and this heavy rubber appendage began trying to move as I grew harder and harder, then Josh reached down saying he’s been watching me sleep with that fucking toy on for a few moments, as he grabbed it and pulled it off of me I was actually stuck to it as he stretched my shaft, we laughed and Josh tried to put the head of it in his mouth but there was no way he could even fit it. Then he said I still bet you this thing is bigger than Hulk.