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Hairy Bear & his new Sissy

I had enjoyed the casual company of a sissy boy for a few years but he recently moved to another city. So here I was seeking a replacement. I placed an add online searching for a sissy boy. The add read “Hairy masculine bear seeks sissy boy to service his cock & ass. Must have a high level of depravity, must enjoy piss play & be willing to try almost anything”.

Within 2 days I had several applications but one stood out. He called himself Sissyboy, he was only 18yo, 5’7 tall & according to his application, he had a skinny hairless body & he was looking for a new daddy. What struck me was that he had extensive previous experience servicing another bear & loved drinking his piss & eating out his dirty shithole. I replied to Sissyboy’s message telling him to come to my house the following night with a full bladder.

Later the following afternoon I sat in the sun on the back deck, naked, a 8” butt plug inserted in my hairy ass with the gentle breeze blowing across my hairy body. There’s no skin on my body that isn’t covered in hair. I love it, it feels sexy. Sitting there in the sun drinking several bottles of beer was a nice way to spend an afternoon. Drinking beer was always my prelude to piss play. I found I can drink quite a bit without feeling like I have to piss, it fills up my bladder & I can retain it for a few hours, but once I start to piss there’s no stopping it. So there I was, enjoying the sun whilst occasionally slipping the butt plug in & out of my hairy ass.

Sissyboy knocked on my door at about 7. Still naked, I opened it & in he walked. He was perfect, quite feminine in appearance, short in height with a shaved head. He had a long overcoat on which I found strange given it was the middle of summer, however when he took it off I understood why, he had purple coloured stockings & a suspender belt on, & a pair of black high heels & nothing else. His small cock hung down to his suspender belt, he looked very sexy indeed. He immediately dropped to his knees & put his nose in the thick pubes above my cock, showing obvious delight in the masculine smell. I stepped back, telling him to wait until he was told what to do while secretly enjoying his eagerness. We walked into the kitchen where I grabbed him a beer, I wanted to ensure his bladder was full. He drank it down quickly while looking at me with sheer delight in his eyes.

Once Sissyboy had finished the beer we walked out onto my deck. The night was still warm & I had big plans for my new sissy. We both lay down on the lounge together, his head resting on my hairy chest with my big arms around him, holding him tight against me. He was playing with the hairs on my belly & occasionally running his hand down to touch my cock, which by this time was rock hard. I told Sissyboy that he could have a taste of my cock so he reached down & ran his lips over my helmut. As he did I reached around & started playing with his ass crack, inserting a few fingers into his asshole & bringing them up to my mouth to taste his ass juice. He was an expert cocksucker, I had to tell him to slow down before I came. So he started licking my hairy balls instead.

Sissy told me that he would need to piss soon & wanting some action for myself I told sissy to lie on his back & I then climbed on top of him & sat my hairy ass on his face. He parted my hairy ass cheeks with his fingers & instinctively started eating out my hole. I hadn’t washed since the night before & I must have tasted quite bitter, the strong musky smell just turned sissyboy on even more. He was quite the dirty slut. While sissy was eating me out I bent down & sucked on his little cock. I told him that it was time to give his new daddy a drink so he started pissing into my mouth. I couldn’t swallow it all, what I missed ran down over my hairy chest onto sissyboy’s belly. His piss tasted really nice, quite warm & salty. By the time he had finished my face, head & most of my hairy chest was wet with Sissyboy’s piss. I really do love being pissed on, my hairy body looks great when its wet.

Sissyboy was lying down on the lounge & I was standing over the little slut. He sat up & started sucking on my dick & nutsac. After a little while of cocksucking I turned around so he could resume servicing my asshole. I love being rimmed, it must be one of life’s great pleasures. He was feverishly rimming me, darting his tongue in & out of my ass, inserting it as deep up my ass as he could while running his hands thropugh the hair on my back. I turned around & kissed him deeply, tasting my own ass juices as I’d done so often in the past.

I lay Sissyboy down on his back & pulled his legs up on to my hairy shoulders & pushed my cock into his asshole. I slowely started fucking my little sissy, my cock going in & out of his mancunt. He felt good. Really good. I started getting faster & I could feel the cum rising from my balls. It got to a point, rather quickly, where I couldn’t hold back anymore. I was fucking his mancunt quite hard & fast now & within about 2 minutes I started cumming, I felt my cock shooting hot cum into the ass of my sissyboy. Once I’d finished I crouched down & licked at Sissyboy’s ass, sucking my cum from his shithole. I love eating my cum from a guys ass, the taste of the cum mixed with ass juice is delicious.

With my balls now empty it was time to piss. I love a good piss after cumming. I lay down on my back on the lounge where the sissy had just been laying. Sissyboy lay next to me with his head on my hairy chest & I told him it was time to drink from daddy’s cock. Holding my cock in my left hand I started pissing, I directed the stream of piss from Sissyboy’s mouth to my own & back again, all the while covering my hairy chest in more urine. We both swallowed as much of my piss as we could. I was now thankful I’d d***k so much beer earlier, I had quite a large volume of piss to release. By the time I’d emptied my bladder we were both pretty wet. Sissyboy lay next to me & we both fell asl**p.

I was awoken by my good mate Bill calling my name. I’ve known Bill for years, we met at the local gay sauna & we often catch up for a fuck & suck session. Bill, like me, is extremely hairy & also a lover of piss play. Bill had been horny so he went to the sauna but didn’t find anything to fuck so he came to see me. I woke Sissyboy up & introduced the pair. Bill looked quite interested in my new sissy & promptly undressed himself. I told sissy to look after Bill while I went inside & prepared some beers, my bladder needed refilling. I looked out the kitchen window & saw my sissy, still dressed in stockings & suspenders, sucking off my hairy bear man Bill, sissy’s hands reaching around & fingering Bill’s hairy ass at the same time.

As I came out the house my sissy stopped sucking off Bill & we all sat back & had a few beers each. By now the time was just after midnight & I was feeling awake & horny again. I’d d***k half of my 3rd beer when I had a thought. I told sissy to lie face down on the lounge & I inserted the beer bottle into his ass, empyting about half a litre of beer into Sissyboy’s lower bowel, giving him a beer enema. I told him to hold it in for a while. Bill & I sat down on the ground next to each other & I told Sissyboy to bend over in front of us. I wanted the sissy to spray us with his mixture of ass juice & beer. Bill got the idea & we both moved closer to sissy’s ass. Sissyboy couldn’t hold the enema any longer & out came this mix of beer & ass juice, covering our faces & hairy bodies. I looked quite a sight, I was already covered in piss from earlier, now that was mixed with beer & the remnants of Sissyboy’s ass contents. Bill pushed me over & started running his tongue through my hairy chest, lapping up the ass juice from Sissyboy.

I leant over & started sucking Bill’s hairy cock. He was very well endowed, probably a touch over 10” & very thick. He had a mass of thick pubes too that ran all the way around his balls & covered his asshole. I pushed his legs back raising his asshole up & started eating him out. Sissyboy came up around Bill & started sucking his cock as I licked his out his shitter. This went on for a while, Bill could last a long time, often we would fuck for over an hour. I wished I could last that long. After a while I wanted Bill’s cock in my ass so I got Sissy to lube Bill up. Sissy sucked on Bill’s cock, leaving plenty of spit on it. With Bill still lying on his back I squated down on to Bill’s shaft, lowering myself on to his weapon. It slid up my ass easily & I started fucking him, riding him like I was on a horse. Sissyboy lay down behind me & licked Bill’s cock as it slid out of my asshole, giving me plenty of lube. Bill’s cock felt great, he was a big guy & I was fucking his cock as fast & deep as I could. Bill started grunting & I knew this was a sign he was ready to blow. A few more pumps into my ass & he exploded, I felt his warm cum enter my ass cavity & he came & came. Sissyboy was still licking his cock which by now was also covered in my ass juice & his cum. Once Bill had finished cumming I climbed off him & while Sissyboy cleaned up Bill’s cock, I sat my hairy wet ass on Bill’s face & he sucked his own cum from my asshole.

Just like me, Bill usually needs a piss after cumming & as I was sitting on his face I knew a piss was imminent. As his cock grew flacid Sissyboy was still licking & nuzzling it, Bill started urinating on himself. I leaned forward & grabbed his cock, directing the stream of piss over my face & into my mouth, occasionally giving Sissyboy a taste. By the time Bill’s bladder was empty he was as wet as Sissyboy & myself. The beers that Sissyboy & I had consumed when Bill had arrived were now ready to exit our bladder’s. I instructed my sissy to stand next to me & with Bill lying on his back on the deck, we both gave him a piss bath. He has a wonderful body, like me he’s really hairy & now he was covered in piss, all the body hair was matted with our urine. Sissyboy & I lay down next to Bill & we all fell asl**p.

Updated: October 21, 2016 — 1:28 pm

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