My Online Hoo-Up

All participants are well over 18. There are some gay and sexual slurs used playfully between characters in the story. If this disturbs you, please do not read this story.

*****

I stepped out of a shower for the second time in two hours.

I had washed myself from the top of my head to the tip of my toes, sparing no hidden spot or orifice, when I woke up this morning. Then, walking with my backpack over to the hotel on an unseasonably warm November day, I found myself perspiring, so that I felt I needed another shower to freshen me up. The person I was meeting would expect no less.

I based that opinion on some of our chats on an online hookup app. King and I had been talking for a week.

DRMWeaver705: I am d&d free, checked and confirmed.

PantyKing999: Me too. I shower before meeting and expect the same.

Naturally, I made a point of honouring his concern. Even my fresh sweat was washed away and our meeting was set to take place in fifteen minutes in this very room. I worried a little that if King was too clean, I might not smell some of the natural musk that so aroused me in a man. If I had my way, I might have asked him to shower the night before and not wear deodorant; I had a slight armpit fetish which was not helped by the taste of aluminum zirconium. A clean man can still produce a natural and attractive odour in my opinion, but I know that tastes differ.

I towel-dried in front of the slightly-steamed bathroom mirror, assessing what I had to offer. I was a little under six feet, a bit on the chubby side with hairy man-tits, a middle-aged man's belly and strong legs. My penis was currently shrivelled and withdrawn, a fraction of its full size. That reminded me that I wanted to take a Viagra before my friend arrived.

Still naked, I went around the room, preparing it. I reached into my backpack and produced two bottles of water, thinking it would be a courtesy to supply my guest with a refreshing drink. I set one bottle on each of the bedside tables. I also put a couple of condoms on each table; I doubted we'd collectively get off four times or more, but safe is better than sorry. I left a tube of lube within easy reach. I pulled out my supply of Viagra, briefly considered taking two of the little blue pills and settled on just having one. I downed the caplet and chased it with some of the water out of one of the bottles.

From our chats, I understood that my partner was into undressing his playmates, so I applied deodorant and put my clothes back on, omitting only socks as they were pointless. I went into the bathroom and wiped the steamy residue off the mirror before discarding the wet towel in the bathtub. Then I returned to the main hotel room and took a seat in a strong chair with no arms.

This was a morning rendezvous. I was a married man, currently out of work due to the COVID-19 shutdown, while my wife was deemed essential in her work. Her work hours were my free time, so I had nine to five today to meet with my online lover.

I did not start out looking to cheat on my wife, but I have always been bi-curious and as I neared my fifty-first birthday, I felt that I owed myself an experience that was just for me. I had put it off at twenty, at thirty and at forty; now fifty, I wanted to try this while I still could. My waistline was expanding annually and I was not likely going to grow more attractive as the years accumulated. I was already experiencing erectile dysfunction at times, hence, the Viagra. Moreover, things between my wife and me in the bedroom were stale. I never previously had a problem with premature ejaculation, but with my meds for various conditions, I now either came too quickly or I outlasted my own stamina, unable to finish. It was frustrating for both my wife and me. The character of my sexual performance had changed. I often expelled a lot of pre-cum, sometimes a load almost in itself, and comparatively little semen.

Over the years, I started watching more porn as my problems set in, and inevitably I switched from viewing women online to men. My curiosity was decades old but I had experimented to only the slightest degree, viewing gay porn and chatting with men online for cybersex mostly. I found myself turned on by gay stories in online forums.

Finally, I began to see a recurring ad on porn sites for a gay online hook-up app that promised to connect men for satisfying sexual encounters. I may have been slightly drunk or too horny the night I clicked on the ad. I boldly reviewed the site for profiles of other men looking for gay sex in my area. There was a cruising bulletin board, in which people live-messaged where they were looking for sex: parking lots, rest stops, public washrooms, parks, trails and so on. While that intrigued me, cruising seemed to leave much to chance and the risk of discovery.

Before I selected any profiles to view, I noticed that almost everyone had profile pictures. I had never done anything like this in my life, but now I found myself holding my phone at awkward angles to capture pictures of my hairy naked torso, my arse and for the private pics gallery, my cock, both in its erect and flaccid states. I uploaded the pictures to the app, then quickly deleted the pictures from my phone and updated my profile.

What was I looking for: fucking, sucking and jerking off.

What were my turn-ons: I selected several types of men from a checklist, including bi-men, married men, tops, chubs, bears, etc. I was not looking for a perfect physical specimen. As I noted in my preferences, I was looking for a mentor, a teacher, someone with patience. Race unimportant, body type unimportant, age unimportant.

What were my turn-offs: people pushy for private pics and pic collectors (I'd seen that on someone else's profile), rudeness, pointless chat, lack of hygiene, pain, scat.

As it happened, I had a number of chat requests right away. I ignored those whose profiles had no pictures; that very lack of photographs made me feel they were not committed to what they were doing here. One or two fellows had fetishes I had no wish to explore. Another was a top looking to break in a new slave; that wasn't what I was looking for. I thought I needed a top, but I actually received a message from a versatile male that caught my interest.

It was PantyKing999, whom I refer to as King. He was interested in stripping for me, blowing me and letting me fuck him, but he also wanted to be blown in return. Was I interested?

I looked over King's profile, starting with the pictures. He was a thin, well-hung man with a tight-looking, almost bony ass. In several of his pictures he wore panties and nylons, which was not really much of a thing for me. His stats said that he was almost a decade older than me, but he gave good chat. We discussed the details of what we would do with each other.

Was I interested?

Hell, yes. He had seen my less than trim, athletic figure and accepted me and my potential. He was willing to teach me. And more important, he was willing to fuck.

I notified him that I was indeed interested. The hard part was finding a time and place to meet as neither of us could host for our various reasons. Nothing he said made me think he was attached, but I could not blame anyone for not wanting to invite a complete stranger to their home, however intimate the planned activities. We settled on a local hotel we both knew about; King had stayed there before and advised they were flexible about check-in and check-out hours, making it an ideal hook-up location.

I offered to get the room on my credit card, and King would pay me back half the rate in cash. So, it was agreed. Because of my wife's schedule, we needed to book for a weekday, but the night before, my wife announced she was taking a mental health day and staying home with me. How could I describe my feelings? I love the woman but she has a natural way of frustrating me sometimes. I furtively went on my phone, tapped the app and left a message for King that I had to cancel for the next day. It wasn't prudent to keep that app open on my phone with my wife around, so I didn't wait for a response. In fact, I didn't visit the chat room for a couple of days; only when my wife resumed work did I go back in to reconnect.

I was sorry to see that King thought I called the whole thing off due to last-minute nerves.

PantyKing999: Maybe you're not really serious about trying it with a man. Maybe you're just not ready.

I reflected on that. I felt like I was ready to try sex with a man, but I was not willing to throw away my marriage, especially on what was essentially a mere experiment. I knew I was taking risks, but I felt my caution would compensate. I clearly couldn't have disappeared for parts unknown while my wife wondered what I was up to on her day off.

I explained this to King and he was mature about it, but playful too.

PantyKing999: Suppose I give you another chance. If we meet, what will you do for me?

We had already discussed blowjobs and me fucking him, but we hadn't broached the use of my ass. I daringly offered him my anal cherry.

PantyKing999: More than that, lover. You're going to give me a head-to-toe tongue bath before I plough your ass.

I agreed to these terms, finding myself turned on by the idea. We set a new date, and here I was at the hotel waiting for King to make his appearance. As the clock neared the hour, I became very nervous. What if he didn't show? What if he did show? What if I couldn't go through with it? And again, what if I could? Would this be a one-time experiment as intended or would it become a regular thing for me?

Finally, there was a rap at the door. I had texted King the room number as soon as I checked in. I left the chair and crossed the room to open the door.

King was as tall as I was, but he was much thinner. His eyes sparkled with wit and intelligence from behind thick-rimmed glasses. His thin, wispy hair had turned to silver and was neatly combed straight back. His hands were large and he extended one toward me to shake. I was sure that he was about to introduce himself by his real name, but then he remembered that part of my fantasy of our meeting was that we should remain anonymous. I would call him "King" and he would call me "D".

I overcame my hesitancy and with my hand still in his, I pulled him inside as he had asked me to in one of our chats. I closed the door with my other hand. I walked him a little further in, past the bathroom door and in front of the closet and its mirrored doors. I let go of his hand, took off his coat and hung it in the closet. I stood behind him then, looking over his shoulder at his face in the mirror. Then, still watching myself work, I began to hold him from behind, letting my hands wander over the front of his shirt, squeezing and kneading his muscles and his man-boobs. I could feel his hardening nipples through the fabric. I leaned in and kissed his neck; I had to push up on my tiptoes to make up the height to lick and bite his earlobe.

King was enjoying watching himself be ravished by a virtual stranger in the mirror and I felt my own business end stirring. I wondered if it was just the Viagra or the experience itself that was giving me a hard-on. Probably, it was both. My stiffening penis pressed against King's ass hungrily. He sighed appreciatively.

"You could let a man get in the door and get his boots off," he said with a chuckle.

I smiled, knowing this was my cue to go sit down and watch the show. He was getting ready to strip down for me. Once more I was on that sturdy, comfortable chair.

"Can you take a video for me, please?" King asked, walking over and handing me his phone. I knew that model of phone and didn't need the crash-course on how to use it. I had been clear with my boundaries when he had suggested pictures and videos. I would be happy to record him in the act, but I was not willing to be recognized in media myself. We compromised by agreeing that I might appear from the neck down. But that was for later.

I held up the phone and hit the record button, capturing King's denim-clad ass as he bent over and untied his boots. When he turned around and kicked the boots off, I confess I zoomed in on his pocket rocket. I knew from King's profile and photos that he was a nine-incher and it seemed coiled inside his pants. I wondered if King took Viagra before coming here too; probably not, if his boasts of a high sex drive were true.

I raised the cellphone so that I had his face and torso in view as he unbuttoned his shirt and removed it.

"Undress for me slowly," I said and King seemed to approve. He had an undershirt on and he made a meal of removing it. Then, his hands dropped to his belt, unbuckling it and sliding it out of its loops. He swung it around a couple of times before tossing it on the floor by his boots. He opened his button and slowly lowered his zipper. He turned around and ground his ass at me while I zoomed the phone in on his gyrating buttocks. Then he straightened up and pulled his pants down hard on one side and then the other, revealing his panties.

What followed wasn't quite a dance, but King did show himself off rather nicely with some surprisingly graceful turns as he crossed the room. He was soon towering over me and I looked up at him from the chair. He had mentioned that he liked his lovers clothed a while longer than he was; it made his feeling of exposure that much more acute.

We had discussed his striptease in our chat, and it was agreed that I would remove his panties when I was ready.

I stood up well within King's personal space, which was difficult for me; I was the original social distancer even before COVID-19. Heat rose in my ears and cheeks. I put my arms around King's naked shoulders and leaned in to kiss him on the lips. It was my first kiss man-to-man, and the principles were the same as with any heterosexual kiss. Once I realized this, I was able to give myself over and our tongues twisted and wriggled in each other's mouths pleasurably. Our freshly-shaved chins and cheeks scrubbed each other slightly. I felt hot, and I tried to will myself not to sweat.

When King broke the kiss after a couple of long minutes, he laughed and said, "You're new at this?"

I grinned. "But eager."

"Yes, you are," King said, giving my erection a squeeze in my pants. I cupped his panty-covered buttocks in return.

He led me over to the bed before centring himself on the mattress, supporting himself with his knees and elbows. His head was in the pillows, so I still had room to kneel behind him at the foot of the bed.

"I believe you mentioned something about a tongue-bath?"

"I believe I did."

"Start with my feet."

I took his naked feet in my hands and found myself appreciating their rough texture. I didn't know what King did for a living or if he was retired, but these were a working man's feet. Still, there was no acrid foot odour; his feet were scrubbed clean. I massaged the feet and calves, taking my time getting started. I wanted to enjoy every moment. My hands reached his thighs and kneaded them while I began to work with my tongue.

I started at the bottom, lapped at the soles of his feet each in turn. I sucked his toes and licked between them. I dragged my tongue up his Achilles tendons and over the calves. His legs, like the rest of his body, were fully shaved and smooth. After a minute or two working on the calves and behind the knees, I licked and nipped at his thighs until I reached his buttocks, but I was going to make him wait that out while I washed the rest of his back, his shoulders and his arms. Only then did I lick my way back down to his arse.

I slowly and deliberately hooked my fingers around the waistband of the panties. Then I pulled them down to his knees. He lifted first one knee and then the other off the bed so I could pull the panties off. Holding them in my hands, I couldn't resist smelling them, but they were very fresh and were little infused with their owner's scent. I tossed them aside with King's other clothes. He was completely naked for me now and it was time to lick his ass.

I kissed my way across his buttocks and stroked the crack of his ass with my tongue. Even here, King was fresh and clean, and my nose found only the slightest tantalizing wisp of man-scent from his asshole. I hadn't expected to put my tongue in his hole, but here I was lapping away at the little bud between his cheeks. I was leaning with my lips and nose deep in a man's asshole and not repulsed. I was hard as a rock.

"Do you like my ass?"

My yes was muffled by his buttocks, but he understood.

"Do you want to fuck it?"

I was a little surprised by the timing. Of course, that was one of the things we met up for, but I had also explained in chat that I was usually not able to perform again very soon after having sex; I was a one-hit wonder. It would usually take me a day or two to build up enough spunk to fuck again. If I fucked him now, he might have to entertain himself for the rest of this session. I started to remind him, but I had the taste of his ass on my tongue and a boner in my pants, a combination that was not best-suited to selfless, good judgement.

"Yes, I want to fuck you." I truly did.

"In that case," King said, pulling his ass out of my face and hopping off the bed. "It's time to undress you."

I set my feet on the floor and stood at the foot of the bed while he walked his naked body around to face mine. His nine-inch cock pointed at me like the arrow of a compass. I let his hands do their work as he efficiently stripped me. He pulled my shirt over my head before taking my watch off.

"Forget about the time," he said, tossing the watch on top of my discarded shirt.

He pulled me close with one arm and drew me into a hot kiss while his other hand worked on unbuckling my belt. My cock was squirming in my pants by the time he freed the belt from its loops. It dropped to the carpeted floor with a soft thunk, but by that time, King was already lowering my fly. He popped the button and stepped back so he could use both hands to pull down my pants. He let go of my trousers and I stepped out of the pantlegs.

"Now to see this for myself," King said as he hooked his thumbs around the waistband of my underwear and began to tug.

I didn't want him to get his hopes up about my package; I'm just not that big, but I'd prepared him for that in chat and with my private pics on the app.

"Beautiful," King said as he pulled down my briefs. I was gratified and utterly naked.

"Just a taste..."

King put his lips on my cock and kissed teasingly. His tongue darted between the tiny slit at the tip of my penis.

"Salty," King said. "I think your cock is hard enough to take my ass."

I pulled myself away, hungry for his ass, and stepped over to the edge of the bed so I could reach one of the condoms.

"You know you don't need that," King said, moving back onto the bed, this time laying face up.

"Thanks. It's, uh, just for safety," I answered clumsily. I knew that King said he was disease-free, and I believed him or I wouldn't be here, but I felt I owed it to my wife to take all precautions to keep her safe. King shrugged, a little disappointed I think; he had told me in chat that he liked the feeling of someone coming inside him.

I tore the foil of the condom and stretched the prophylactic over my small, stone-hard cock as King watched me. I was hoping that King would feel me when I was inside him. I lubed up my cock before rubbing some more of the jelly into King's hole. When I knelt between his legs again, I matched my dick to his asshole while he reached around behind and pulled his cheeks wide apart for me. I braced myself by putting my hands on the bed on either side of King's body, then I slowly pressed my prick into the space between his buttocks. For a few seconds, the ring of his sphincter resisted my entrance and I was stumped; I was new to this and I didn't want to hurt King.