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Disclaimer: If you don't like stories with explicit and kinky male on male sex... you shouldn't read this one.
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Chapter 1 - connecting with Jay
37 degrees Celsius, that's what I woke up to. I hate air conditioning so I used the ceiling fan for all it was worth, which wasn't much. At least the hot air was being pushed around a bit.
The thin white sheet was clinging to my naked body, the thin sheen of sweat and the damp heat made me horny as always.
With my left hand I traced a line over my pecs, pinched my nipple, stroked my dad belly and finally grabbed my 19cm cut cock. I was alone , on holiday and woke up to my third day of being horny as hell.
I fired up growlr and picked up my search from where I left off.
I'm a 48 year old dad, with a bull type dadbod. Smooth, 182cm tall and a tight 103kg on the scales. I lost my virginity to a bear daddy when I was 16 and I've been a sucker for bears, daddies and pigs ever since.
Growlr is an okay app to find a partner but I had been at it for two days and hadn't had any luck yet, just the usual talk and no action. I didn't expect much when I dove back in on this sweaty steamy morning.
The message icon had a blue dot which wasn't uncommon but this time I noticed I received a message from a user called #n•1. His user name didn't make sense to me but his pictures were of a sexy as hell bear body. Big tits, nice round belly, lovely ass and a good amount of fur. I didn't expect him to reply to my woof but he did.
Instead of the usual "hi" or "private media has been unlocked", this guy came out with: "you look hot daddy but I'm bottom too :("
I had forgotten to update my profile, I prefer to be bottom and submissive but I can be a dominant (sadistic) top as well. Based on the pictures from this guy I'd do whatever it took to play with him.
"I can be top. What do you like?" I replied and I didn't have to wait long for an answer.
He seemed excited, his name was Jay and he told me he loved the kinky part of my profile. A lot of people say that but then when it comes to action they'd rather stay vanilla, or they chicken out altogether.
Despite my misgivings due to earlier experiences with praise like this, my dick gave a little twitch and I allowed myself some hope that Jay might actually be a doer.
As a test I asked him what kinky things he dreamt of.
"I've always fantasised about being raped"
What a perfect answer! Forward yet vulnerable and a clear indicator that he might actually be serious.
His fantasy was also something I empathised with wholeheartedly. Both on the receiving and giving end.
We continued to chat and eventually decided to meet at 9pm that evening in my hotel room. Jay was a bit worried about his husband catching him but he was also horny as fuck. He told me he'd be there.
Damn. 10 hours to kill. I grabbed my gear, went to the nude beach and edged whilst dirty old daddies ogled me from the bushes. Two came up to play, I let them touch and put on a bit of a show, but stopped them before getting off, I wanted to give Jay the full load.
At 9:10pm I was getting frustrated, he seemed so genuine and right as I was about to fire up my app again, the door opened (I love leaving my hotel room door unlocked so a strange horny man can simply walk in) and in walked a gorgeous, short bear.
His pictures were accurate. His shirt stretched nice and tight over his belly. His shorts were short, I could see he was hairy and he had nice calves.
I got up, pushed him against the wall and kissed him deeply, hungrily, exploring his body with my hands whilst pinning him. He was a good kisser and so submissive, it was clear he was there to please me.
Pushing his hands up I grabbed his shirt and pulled it off. I took a step back and grabbed his shorts, pulling them to his ankles and saw his package in a jockstrap, just like I had ordered him.
I pushed him down to his knees positioning his eager mouth where it belonged and told him to take my cock out. He obeyed and held me with both hands, licking the pre-cum gingerly from the tip of my cock then, admiringly, he slowly swallowed me whole.
Pushing his head to the wall I gently fucked his face whilst telling him that I was going to fuck his arse next. His feelings were unimportant to me, he was here to serve me and I was going to do what I wanted.
His eyes reacted like I expected, eagerness with a tinge of fear. So fucking hot.
Pulling out slowly I ordered him on all fours on the bed. Face down, arse up. As he positioned himself I grabbed a condom from the night stand. I hate these things but we said we'd go safe.
Jay asked for lube but I denied him. "My spit is all you're getting boy" I growled as I separated his cheeks and spat on his hole. Then I thrusted in without holding back.
Jay's body spasmed in pain and I loved it. I told him I don't care. His ass is mine, his body is mine, he has no will. His reaction was a gasping " yes daddy" as I ram my cock into him.
I pull out and take off the condom. "I'm going to fuck you raw" I warn him before actually doing it. Rape play is fun, the real thing is not.
His response is exactly what I hoped for, pleading eyes with resistant words. "Are you going to rape me raw daddy?"
It's clear he wants me to and I'm so hot, I need to concentrate not to cum as soon as the tip of my dick touches his hole.
Breathing in I line up my cock again and drive down hard, going balls deep instantly. The slap of my thighs against his ass cheeks is making loud echoing claps in the room whilst the pillow muffles Jay's screams of agony and delight.
Sweat is starting to run and I realise I want to look this slut in his eyes as I orgasm. Instead of fucking him more, I pull out and grab a 22cm dildo from the night stand and place it on the floor next to the bed.
"Ride that cock boy" I order Jay and he eagerly positions himself crouching next to the bed. He slowly sinks his body on the big dildo. It's hurting him and he's going slowly so I climb on top of him and lean my body weight into him, forcing him down.
"Does that hurt boy?"
"Aaah yes daddy" and my dick just loves the pleasing tone of his voice.
I put my hands on his hips and my thighs on my hands, leaning in I push Jay even deeper on the dildo. He screams and the extacy in his eyes is intoxicating.
His open mouth is just begging to be kissed so I lean into him more and stick my tongue in aggressively, probing, demanding as I jerk off and push the massive fake dick even deeper into my boy.
His full weight is on it, my full weight is on him and I explode onto his stomach whilst kissing this wonderfully slutty bear.
We lean into each other and I keep him pinned, my cum sticking between our bellies. I don't let him up but grind his body, knowing the dildo is filling him.
After staring at him intently I softly whisper in his ear.
"It's time to talk about fulfilling your fantasies boy"
To be continued....