The Making of a Middle-Aged Cumslut

It was almost three o'clock in the afternoon and I had just checked in at a hotel on the edge of town. I took a good look around the room to ensure it was as bland and impersonal as the rest of this franchise hotel. I stowed my luggage bags in the closet. I closed the blinds and drew the curtains, rendering the room quite dark. I turned on the bathroom light, letting the glare cast one spear of light but overall, the room was heavy in shadow.

I received a text notification. I swiped my phone open and read the message. It was one simple word: "Here."

My nerves twisted my guts. My hand shook and my lip trembled. A desperate thought surfaced. The man didn't know where I was. I could still chicken out. I was tempted to turn off notifications, call up room service and pretend for the next few hours I was here on a holiday. But I was tired of being 'curious', so instead, I tapped out a reply on my phone: "2nd floor, room 208. Card key is under the door. Let yourself in."

It was done then. I stripped off everything I was wearing except for a flimsy pair of boxers. I didn't want to be totally naked. This visitor considered himself straight; in chat he told me he wasn't gay but he was interested in my offer because "sissies give better head than women". This guy doesn't want to see my cock and to be honest, I had no desire to show off my organ. As I had gotten older—I had just turned fifty—and put on weight, my cock seemed to shrink and hide more in its nest of pubic hair. It made me feel slightly inadequate.

All that remained was to place the pillow on the floor, kneel, face the door and wait. I set the pillow between the bed and the door, and just out of the direct light streaming into the room from the bathroom. I interlaced the fingers of both hands on the top of my head like a man awaiting arrest. I didn't know if my visitor would be nervous and I thought he might be comforted if he saw me in a completely non-threatening pose. I was posed away from the light so my face was in shadow. I didn't mind appearing anonymous in this endeavour and from some of my research, the men who would visit me under these circumstances might also want to go unremarked.

What kind of men, you may ask? They were the kind that answered an ad like mine of course.

I posted a very straight-forward greeting on several dating websites: "Hello. I want you to put me on my knees." I filled in the 'about me' section as well. "Now that I have your attention, I am a chubby, somewhat hairy bi-curious male looking to play. I am new at this and need a good teacher who will instruct me while I'm on my knees before him. I will suck him to completion, and if he wants, I will suck him again. I want to meet discreet, married and mature males for oral sex only. Reciprocation would be nice but is not essential." I added a picture of my somewhat doughy dad-bod in a light that showed off my body hair. I understood some guys really liked that.

I had multiple responses to my ads. Most were time-wasters from distant cities or even out of the country. Others just wanted to chat with someone of like mind. I did participate eagerly in such chats many times, often tugging myself off to a powerful orgasm. It wasn't the real thing though and I was craving a real man's cock in my mouth.

There were sounds at the door. A card key beeped and "John" entered. Everyone meeting on these websites provides what is likely a false name for convenience. The hallway illumination backlit him and my first view of him was his silhouette. He was a stout lad, but he had said he carried "a few extra pounds" in his profile so I was expecting that. He closed the door and turned around to face the room. It took a few moments for his eyes to adjust. He threw the card key on a nearby desk.

I was still kneeling on the pillow. His vision adjusted and he looked around the room, perhaps satisfied that I hadn't set up a camera in a corner. He walked over to me and popped the button of his pants. He pulled down his fly. When he saw me reaching out to help, he stepped back. When he turned, I thought he was leaving, but instead he just walked into the washroom and pointed his tool at the toilet. He left the door open. I remained kneeling with my mouth watering while he urinated. You could tell by the way the piss sounded in the toilet water that it was expelled powerfully. When he was finished, he made no more effort to clean his penis than to shake the organ. He left the toilet unflushed but at least he washed his hands.

I could more easily see him under the bathroom lights. He had a slight gut, but otherwise he looked to be in shape for a man who claimed to be nearly fifty. He had dark curly hair and a well-trimmed beard. He felt like a man who made his living with his hands, perhaps a tradesman or mechanic. He wore a wedding ring.

He stalked his way back over to me with his dick hanging out. It swung like a pendulum. When he stopped in front of me, I could just barely see his hairy balls in the dim light. I reached up and tried to expose more of John's genitals, but he pushed me back and grabbed his swelling erection at the root. He wasn't interested in making my first cocksucking experience comprehensive; he only wanted to get off.

That was okay with me. With his dick in his hand, he started feeding it to me. My lips touched the head of his cock, kissing and nuzzling.

I was surprised at myself. Whenever I had dreamed of the moment of sucking my first cock, I always imagined I'd be hard during the experience. God knew I had been walking behind a boner the whole week since this day was arranged. When aroused, I normally drool copious amounts of pre-seminal fluid as well. Instead, I was shriveled and dry. I knew the reason. I was scared; scared I wouldn't be able to do this, scared I wouldn't be able to bring him to a finish and scared that I would be sick if my lover ejaculated in my mouth.

The fear seemed to fall off a little as I began to get into my very first blowjob. I began exploring the head of John's cock and tasted another man's salty pre-cum for the first time. I massaged his shaft with my hand while I concentrated my oral efforts on the glans of his penis. John was not oblivious to my actions. A minute after my tongue touched him, he was already groaning. I didn't want to seem overconfident and I didn't want to get him off too quickly.

I dragged my tongue down his rod and began to feather it with kisses. He seemed to like this for a few moments, but then he reached down with both hands and repositioned my head so that my mouth was once more at the tip. As I leaned in to resume my efforts on his cock-helmet, it became clear my feeder had other ideas.

He thrust his hips forward and his five-inch dick penetrated my face to the depth of my tonsils. I gagged and my eyes snapped wide open, issuing tears. He seemed to sense he had exceeded my current skills and he backed off a little, almost pulling out. Without even thinking, my tongue resumed its massage of the sensitive tip of his cock. Again, he pushed himself to the back of my mouth, but this time more slowly and not as deep. I ran my tongue along the underside of his meat. He sawed in and out of my mouth, slowly picking up speed as I tried to suppress my gag reflex. We came to a compromise in which he was face-fucking me as far as I could manage while I began to apply suction to my efforts. My cheeks hollowed as my mouth pleasured John's dick.

Up until this point, I had no time to think. I had just been dealing with the situation one moment at a time. Now I was getting the hang of this and my confidence was increasing. I was adapting and I began to realize that I liked the feeling of my tongue smoothing the wrinkled edges on the underside of John's cock. I enjoyed the taste of pre-seminal fluid in my mouth. I liked having my mouth treated like a pussy.

My dick was no longer disinterested. As I envisioned, I was sufficiently aroused to have a full-on erection as I sucked the cock of another man. I felt the occasional twitch in my penis as I thought about what I was doing.

I had taken some classes teaching Cognitive Behavioural Therapy. There I learned about mindfulness. Some people call it a fad, but it's been around for thousands of years. You can mindfully wash dishes, feeling the water and its temperature on your hands, experiencing the scent of the detergent, immersing yourself in the moment. You can eat mindfully too, inhaling the scent of your food, experiencing its flavour and texture in your mouth. The key is to live in the moment and not only will you worry less about past and future, you enrich your present. At least, that's what I got out of it.

I was living in the moment now. I had no thought of being embarrassed or discovered and exposed. I had no thought of the needs that drove me to meet this man in this room. Instead, I was immersed in the feeling of it: the spicy male scent of his pubic hair; the slurping sounds I was making over his dick; the taste of his clear, slippery pre-cum; the sight, seen through the top of my eyes, of my lover's face drawing a map of lust and ecstasy. I had discovered a technique and a rhythm. Everything seemed perfect.

And then it got better.

John pulled his dick out of my mouth. His knees were slightly bent and every muscle taut. He threw his head back and gave a mighty groan. He ejaculated great ropes of semen over my face and hair; some landed on my chest. The semen was hot on my skin. His jizz smelled vaguely earthy, a little like the smell that hangs in the air after you mow the lawn. I heard my own voice groan, "Yessss, God... yes."

When he was done, John remained standing in front of me and I quickly realized he wanted me to lick the saliva and semen off of his dick. I rose to the occasion, licking until I thought he might go hard and feed me again, but no such luck.

John took a step back, perhaps a little frightened by my eagerness, gently pulling his cock from my mouth's grasp. He tucked his tool back into his pants. I was horny as Hell and wished for a hole to put my cock in, but I knew it was not to be. John was quite clear that he was a feeder, not a cocksucker.

Cocksucker! I thought with a thrill. Now the next time someone calls me that, and in my town someone will, it will be true for the first time. I was ecstatic. I had sucked cock without chickening out, choking or getting sick. It was a long-time ambition fulfilled.

I had left water bottles on the desk in case my sperm-donor or I felt dry. John cracked one open and downed it in one. He said "Thanks" before he walked out of the room and out of my life. As all of our previous chats were online, this was the only time I ever heard John's voice.

After John was gone, I got up, practically giddy. Surprisingly, my knees were not too bad; I walked off the stiffness after a minute or so. I looked down at the tent in my boxers and smiled. My wood showed no sign of softening as I walked over to the washroom. I looked at myself in the mirror. Looking back at me was a smiling, cum-covered, newly-minted cockslut with a boner. I was a proud disgrace. Thanks to my erection it was with difficulty that I added my urine to John's in the bowl and flushed. I licked around my lips to taste as much of his cum as I could, but then I wiped off the rest with a towel. As I knew from my experience of eating my own cum, it's just not as good when its cold.

I still felt incredibly horny from my experience. My cock strained against the fabric of my underwear, demanding attention, but I was determined to hold off on my release just in case one of my feeders decided to return the favour after they got off.

I went back out into my room and looked at the time. Five to four. I had been sucking John for at least forty minutes. I didn't really know if that spoke favourably of my stamina or John's. I did know that I needed a shower, a drink of water and a rest before my next caller visited at six o'clock.

Another one, you say? Well, if I was renting a nightly-rate hotel room for a brief encounter anyway, it made the most sense to book more than one feeder too. I preferred to think that was confidence, not hubris. I made "dates" with three men in all. "John" was the supposedly straight, silent type looking for anyone to blow him.

Next up was "Dean". In our correspondence, Dean mentioned that he was bi, but he was still hiding in the closet from his conservatively religious family. He had no hang-ups about men giving him blowjobs. He was the youngest of my dates if he was telling the truth about his age. He was twenty-three, which was not quite half my age. That interested me.

In the meantime, I had to get myself ready and get some rest. I took a long hot shower and scrubbed myself fresh and clean. When I dried myself off, I put on a fresh pair of boxers. The old ones were stained by some of John's cum. I brushed my teeth as well, so my breath was minty fresh. I wanted to approach each encounter as fresh as possible for my feeders.

I had allowed each encounter a minimum of three hours in case of the unexpected. So, the next appointment was for six o'clock and the last one for nine. Right now, I could afford a half-hour for a nap. I set an alarm to make sure I didn't oversleep. To my surprise, despite my excitement from my last encounter and my anticipation for the next, I did manage to sleep for over an hour. I downed a whole bottle of water. It wouldn't do to get dehydrated when you're drooling from mouth and cock.

I quickly restored order in the room. I opted to give myself two pillows this time and stacked them accordingly. I carefully pushed the card key back under the door for my next visitor. The next few minutes seemed terribly long as measured by the hotel room alarm clock. At four minutes to six o'clock, a text notification came through on my phone and my dick spasmed in my boxers.

I read the message: "@ hotel u here?"

I was feeling more playful this time than last. "I'm on my knees waiting. Room 208, 2nd floor. Card key is under the door. Let yourself in."

His response: "b right there."

He would be here in moments. I resumed kneeling on the pillows and once more I interlaced the fingers of both hands over my head. A few seconds later, there was a half-hearted knock at the door before my visitor remembered the card key was right in front of him. He unlocked the door and entered the room with a swagger, tossing the card key on the desk across from the bed. He closed the door behind him and looked at me. When his eyes adjusted, he ogled me kneeling in my boxers waiting to be arrested. My dick was fully erect, putting a point in my underpants.

"Holy fuck," he said. "You really are eager."

"I hope you are too." By this time, I had a whiff of him. He was wearing a popular cologne and he had been drinking. Not necessarily a problem.

Dean pointed at the bathroom. "Mind?"

I shrugged. "Please do."

"You into watersports? You know, golden showers?"

"No." I definitely was not. Dean shrugged.

Unlike my previous visitor, Dean closed the door, leaving me in darkness. I heard him pissing and once more marveled at the force with which some men can urinate. It seemed when I hit my late forties, my own powerful streams turned into trickles. After a minute or two, I heard Dean flush and wash his hands. He emerged to find me still on my knees. I was initially disappointed to see he had fastened and zipped up his pants.

Dean was lanky and close to six feet tall. He had straight blond hair and a fashionable length of stubble on his jaw. He looked lean and hard in his jeans and t-shirt.

"Okay, you little bitch," Dean said, getting down to business. "Good to see you know your place. On your knees before a big, fat, juicy cock."

I was not too startled to be spoken to this way. I had included dirty talk as one of my likes in the profile that attracted Dean. My erection did not abate in the slightest.

"Today, you're going to work for it, sissy."

"Okay."

"Not 'okay', cocksucker. How do you address me?"

"Sir?"

"Yes, 'sir' will do." Dean grabbed his package in his right hand and squeezed it provocatively. "You want this, don't you?"

"Yes, sir." It felt ridiculous to call a man less than half my age 'sir'.

"How bad do you want it, cumsleeve?"

"Very badly, sir."

"Tell me."

"I want your cock, sir. I want it in my mouth."

"What will you do to get it?"

"I'll crawl and beg if I have to, sir." I didn't get off on the crawling and begging really, but I did want his cock very badly. My mouth watered for it.

"Lean forward. I want you to put your hand on my trouser snake."

I reached out tentatively and he grabbed my hand and put it on his crotch. I could feel the pulsating organ inside. It was hard to be sure, but it seemed like he was carrying a few inches there. I was still playing the game patiently, but as Dean's penis hardened, his need grew.

"Take it out, sissy," he commanded. There was a note of desperation in his voice.

My hands were already there so it was easy to unbutton and unzip him. I began pulling his pants and underwear down, hoping I would not be cheated of the chance to play with his balls as I had been with John. Dean let me pull his pants down to his knees. I looked up at his cock, but it was hard to make out in the darkness. I had to straighten up to face it head on. I was aroused by his pungent man-scent.

"Get to work, fag," Dean said.

I needed no further urging. After my experience earlier today, my cock-shyness had worn off. My own dick was still rock hard and throbbing. My cock and mouth drooled. I jumped on that cock like a man in the desert leaps at water.

My mouth closed over the head of his cock. I followed the advice of a gay writer and quickly traced out the alphabet with my tongue over the sensitive cock helmet. I had reached 'q' when Dean grabbed my head and thrust his seven inches as far in as I was able to take it. He gave a cry that was half misery and half ecstasy and, after less than a minute, he blasted his semen down my throat. There was so much cum that I couldn't contain it all; it poured out the sides of my mouth and I swear a little came out my nose.

The taste of his semen was intoxicating! Viscous and potent, the fluid was sweet with a salty aftertaste. It filled my mouth and I leaned back and opened my mouth to show him what a cum whore I was. My face and chest were covered in his splooge.

But Dean was on another track altogether. It was immediately apparent that he was ashamed of his premature ejaculation.

I swallowed the sperm in two large gulps and looked up at the young man. His anguish affected me even in my ecstasy. In a way, it was flattering to have inspired a premature orgasm; it suggested I had some skills. Still, I tried to think of any words of consolation. In the end, action carried the day. I took the softening cock back in my mouth and repeated my alphabetic exercise. Before I got to the twenty-sixth letter, Dean was hard again. As I inhaled more of his prick, tongue-massaging it as I'd learned to do only three hours earlier, Dean began taking a real interest and his despair seemed to lift. After a few minutes, Dean tangled his fingers in my hair as I sucked his cock with gusto, and he began to control my rhythm. His confidence was restored as we passed the five-minute mark and approached ten.

"That's it, cocksucker," Dean said. "You liked that cum I gave you? You're going to get some more soon."

That was fine by me. I couldn't keep this pace up forever and my jaw was beginning to ache. I began massaging his balls gently, thinking that might make him come sooner. I would have done anything at just that moment for another taste of his cum.

"Keep sucking, you little cum queen," Dean said. "You'll get a reward soon..."