Some of my stories are true, some have elements of truth, and some are pure fiction. This one falls into the true category and I haven't decided how much to admit yet.
I keep a couple of the hookup sites on my hidden web browser. The thoughts of hooking up ebb and flow and occasionally I use the mail feature to communicate to all the guys who send smiles, winks, and dick pics. I used it once to have my first experience (First) losing both my oral and anal virginity and later for a hookup that fits into the elements of truth category. Some of it has been changed to protect the guilty.
It had been a while. Almost six years since I last had sex with a man. I still remember the smell of cock, the tug of flesh and the burn, ache, pain, pleasure of accepting the penetration and the little thrill of being taken. It had either been too hard to get away or the timing hadn't been right. But I kept looking out of habit. Wondering if the stars would align or even if I could still do it.
You get all sorts on gay hookup sites but most are about the moment. A fast and furtive emptying of balls and then anonymity. Bi guys like me on the downlow. The divorced guys. The players. Most looking for a fast hookup.
And I get a lot of attention. For one thing there were a lot of good pictures. A hobby of mine. And I wrote a pretty good profile too explaining what I wanted. And without getting too full of myself I have a good body and my face is never in a profile image. Lean and tall at 6-3, long muscular legs with a very round ass and very smooth ivory skin. One guy asked if I was of mixed race because of the skin but I am not. My cock is a very fat 2 inches and a quarter wide with elegant pink/brown skin and proportions. It's only six and half inches long but in my very biased estimation it looked good. Once in drunken teenage moment friends had seen it and proclaimed it a "horsecock" because they all had skinny inch and half wide cocks. The bottoms ignored my profile settings and I had lots of offers to suck it and more even though I had no interest. With men I was mostly a bottom are at least a versatile bottom.
Even with that attention it was difficult to get anything going. They'd want to do it right then or want me to host. Neither of which could easily happen but I'd engage just to see who was out there. The funny thing was that my first hookup was relatively fast and easy but there were all sorts of issues with reengaging. He wanted a boyfriend, tried to fuck me without a condom, and was pretty small. I could live with one but not all three.
Then there was the guy who couldn't host but wanted me to blow him at parks and the like. I was an oral beginner for one and it wasn't my primary thing. He was persistent but it didn't work out. There was one that stood out though but he was from down south. Richard from downstate. His message started out.
"I love your body. That beautiful ass I could worship. That thick cock I could suck. That soft skin I could stroke as I made love to your body." He was six hours away but I shared my private pictures anyway. It felt good to be so desired.
He reciprocated and what I saw made my mouth water even though I don't consider myself a connoisseur of dick. Thick, long, and veiny with an upcurve. It was oiled probably from jacking off and I looked at the pictures several times. He was too far away and honestly he looked way bigger than I had taken or could take. Especially now that I was out of practice for so long.
For whatever reason we kept talking over the year. The feeling of being that desired was heady. Way beyond the normal "want to fuck today? Can you host?" messages I got. He'd always say how much he liked my body and how he'd like to worship it. I'd send him select pictures too that weren't out there otherwise.
Then there was the message. "Going to be up your way on business in two weeks. Staying at the XYZ lodge in your town." I knew exactly where it was and it turned out to be one of my rare alone weekends where the wife and kids were going out of town. I had to stay in town to work.
I felt my mouth get dry and my pulse pounded. Was I willing to do it again? It had all been abstract with Robert the past year and here now it was suddenly a possibility. I looked at his profile again. That oily thick cock and I could imagine it in me. Could I get it in me? I paused before caution was pushed aside.
"I'm free that weekend and I'm ten minutes from your hotel" I typed and the response came immediately.
"Would you like to meet at 8 am at my hotel? I'll send you my room number when I check in."
I hesitated at the commitment. Was I going to go through with it. I could bail now but if I said I'd be there then I didn't want to be a flake.
"Yeah, I'd like that."
"Don't feel like you have to. I've been hoping to meet for months now to see if you're as delicious in person as you are in pictures. If you are then I'm going to want to ravage, worship, and make love to you. Is that something you want? I promise you'll never feel more desired."
I stopped. The blood in my head pounded with every heartbeat. It was a moment of truth. And I really wanted to feel desired as offered.
"I want it. 8 am Saturday."
"Great, I'll see you then. BTW, attached is my latest test. I haven't been with anyone in a year but if it helps put your mind at ease."
I sat back heart pounding and wondered what I had just gotten into. The test result were clear and I could see Robert's full name and address on there.
Friday afternoon I checked the site and Robert had messaged. "Room 402, south side. See you tomorrow."
My guts clenched but not in a bad way. I looked at the pictures of his cock again and could feel my mouth water. I was going to do it.
The next morning I was up at six and had coffee early to help clean out. The long unused enema kit hung full of warm water from the hangar on door handle as I threaded the lubed nozzle through my sphincter. The release of water made me shiver as I felt my bowels fill.
Expel, repeat until nothing but clear water and I shaved and showered. I stood looking in the mirror afterwards and then bent over. I was lightly furred with pale hairs but no zits. My anus was pink and tight and I lubed and fingered it briefly trying to imagine taking a cock into it again. A shred of doubt crept in at the tightness but Robert showed every sign of being experienced in the ways of breaking in holes for cocks.
Dressing was odd. I was dressing to seduce a man which is something I hadn't done before and the image of a giggly schoolgirl went through my head. He desired me and I wanted to be desired. The G-string was too flimsy. The jock seemed to much of a cliche. The regular boxer briefs said not really trying. White or black thong? White I decided. It was more virginal and I felt a little like a virgin at that point.
It cupped my package and the band rode up between my bare cheeks as I pulled the tight jeans on. Short sleeved open neck shirt and barefoot in deck shoes. I looked in the mirror and tried to decide whether I looked like a guy on his way to get fucked.
I was early and puttered around unsuccessfully. I could feel the strap rubbing my anus and I was highly distracted. Time to go. I grabbed a small go bag that had lube, condoms and wet wipes and drove over with my stomach doing flip-flops.
It was a suites style hotel and these rooms were the executive versions. 402 was on the top floor and was easy to find. I stood there a second before knocking and the door was opened almost immediately.
