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My (29m) first time with another man (40s) involved being put into bondage
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I met him on the local reddit page back in late 2021. Both of us single, but he was well off and had a large collection of bdsm items - including some he didn't show originally. After a week or so he offered to get a hotel room for us to meet and have fun for a night...

He laid out how he would treat me. What to expect. Some safe practices. He made it feel comfortable so I agreed ti the meet for the next weekend. He teased me all week, making me swear to not cum until he could force me to with his own actions. Mostly had me prepare my ass for lots of fucking.

I was nervous as hell Saturday and almost quit on the walk there - but this is what I wanted. And I was promised and shown the potential for an amazing experience. So I got to the hotel And went the room he texted me.

He opens the door he asks for to come in. So enter the room and closes and locks the door behind him. We exchange some small talk before he gestures to the center of the room where I can now see the bed to rigged for my binding.

He steps in front of me and lays out of the ground rules nice and clearly while he undoes my tie (he requested done business attire and a butt plug so I happy obliged). As he finished and I agreed to continue he sat down on edge of the bed and told me stop naked. I quickly undressed, turned around and showed my butt plug. He chuckled and popped it out before handing be a pair of leather underwear (same ones he was wearing) and told me put them on - they were open backed but had a buttoned flap for cock and ball access.

First bondage: he told me to lay down on the bed where he proceedes to lay next me, talking me though how I'm about to tied up. First he puts the cuffs on my ankles and artists. Next he grabs the spreader bar and extends it out - forcing my legs wide open and exposing my asshole to the cool air. Then the wrists, but he fumbled for one more rope - the one for the bar. The next moment my knees are touching my chest and my ass is sticking straight up for him now - I can feel a pool of precum building in my new underwear...

He spits on my hole. Rubs his fingers over it and feels me shaking in anticipation. He goes to the dresser and pulls out a bottle of lube. Pours some into one hand and proceeds to finger my hole - pressing more fingers to get my hole ready. The one thing he told me is he won't his cock but a series of strapons that will be more than enough for me to handle - I get his cum later though.

So he fucks me with the first one - a standard dildo boring special, similar to my toys. But he goes for an hour. My legs completely numb at this point. He releases me and let's me recover while he tells me how good I was and how turned on he was while m he stuck his hand inside to feel his wet I was - and I was drenched.

After a little bit I told him I wanted to make him cum but he said not yet - he wanted to one more bondage session. So he went into the bathroom and walked out with a straight jacket...black leather...with a gag and a face mask. I said yes and he strapped me in them bound me on my knees on the bed.

It felt like 5 hours but he went on and on and on. Moving from the first dildo to the secobd one then the third one. I never saw them but I definitely felt them as they opened me up more with each one. It was 2 hours of my hole being used - with some breaks, but I was left on pace.

I begged for a break. To please let me focus on his cock for a while. He agreed and took everything off me but he put me plugged my ass as he instructed me to my knees in front of the couch in the room. He took off his underwear and sat down as I moved in to get to work.

I worked his shaft and his balls. Being him hard while using the excess amount of precum I made as lube. Nice and sticky as his and mine started to mix together. I stroked his cock until he slowly took a handful of my hair and slowly pressed my head forward and down until his cock entered my mouth and my warm wet tongue went to work. He pull me off of I got close to the edge and then stick me back on it like a human fleshlight. Until he waited to long and blew his load in my mouth. I pulled away a bit surprised...and undid my flap, exposing my cock and with a mouth of a cum I looked at him and then my cock and he muttered a soft "yes".

So I let his cum fall from my mouth and drop down until my cock and balls where I proceed to lay back on the floor and slowly stroke my cock as he watched. After a couple minutes he said stop and get on the bed in the same position. So I did and he and grabbed the final dildo size. He said I have to at least get the tip in in order to be allowed to cum tonight. So he spread my legs and watched as he lubed up this cock, pressed it against my hole and fold me to relax.

It took a bit but he got it in and I was breathing heavily as my the feeling of being stretched was intense. He slowly rocked his hips a bit and started to squeeze my balls. He told me to play and never stop playing with my nipples. I complied and and he moved to my cock.

I quickly admitted I would cum very easily right now and he said good, now play with your nipples or I push this couch deeper.

I blacked out from pleasure and he forced me to cum all over my chest. Using my cum and his spit for lube.

I was drained. Completely and it was now 7am the next day. We took a shower where I blew him one more time and then he went out separate ways. Never to speak again sadly.

But now I wished he actually dumped a load in my ass...

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1 year ago