Slut Series: Massaged

*Disclaimer: The following is based on true events. Names, locations, etc have been updated for anonymity and privacy. Some details have been embellished to make a more compelling story and to reflect my personal preferences.

Hi, I'm Rob. Welcome to another chapter of a series I like to think of as journal entries, or confessions, based on my prior life as a total slut. None of these are intended to be read in any sort of numerical order.

After any breakup, I tend to have a series of sexy fun flings to take my mind off the heartache. I was 26, single, and ready to mingle. This story takes place probably four months after a breakup, so I was well involved with all the apps available, getting my lure back out there.

I'll start with a brief description of myself to help in your visualizations. As I mentioned, at the time I was 26. I have dark brown hair, green eyes hidden behind glasses, gauged ears -- though not too large, and probably about a dozen tattoos scattered about my person including two half sleeves. I'm 5'9", about 150lbs, slim from biking and inner-city walking. I'm a gaymer and fairly nerdy, yet athletic.

I lived and worked in the downtown area of a small city. It had a big enough gay scene that plenty of new faces popped up every day. One such new face was Curt. Curt had all the features I was interested in: tall -- probably 6'3", close-cropped hair, well-kept beard, and strong muscles. Curt also happened to be 53 years old. He was twice my age. To some, that may be a turn-off. To me, it was novelty and exciting. I liked his silver hair and beard. It was mature, distinguished, and sexy.

As was usually the case, I pretended to play hard to get. I guess I just loved the thrill of the chase. Or rather, being chased. Don't worry, I'm very active in the chase. I love the flirting and the build-up. It always makes the physical activities that much more passionate.

We had several days of back and forth messaging through one of the apps. There were two reasons he had me very intrigued: his leather fetish and his strong desire to give me a massage. Oh, he also had a beautiful, cut, thick 8" dick. I suppose that actually makes three reasons. Three very good reasons. I'd never really had much of a leather fetish, but I did appreciate how it accentuated a man's masculine nature. And Curt looked damn good in his leather vest and chaps. To be honest, it was the promise of a sensual, erotic massage that got my juices flowing. Plus, I'm a millennial, and I've been tense for most of my life.

We agreed to meet up one humid August afternoon. I thoroughly showered, scrubbing every crack and crevice. I'd only signed up for a massage, but I was counting on things to escalate. I put on a tank top and a pair of tight shorts that came up mid-thigh. He lived about half a mile from my apartment so I decided to walk. This probably wasn't a good idea, as I was sweat-soaked within five minutes. Fifteen minutes later, I was knocking on Curt's front door. I barely had to wait before the door opened and he stood towering in front of me.

"Rob! Hello! Come on in," he said in a deep voice.

Curt greeted me with a warm smile and moved back, allowing me to step inside. His condo was dimly lit and all the shades were drawn. I imagine this was to set the mood. Blessedly he had air conditioning, which wasn't always common in the Northeast. Soft jazz music played and the smell of aroma therapy candles wafted through the air.

"Make yourself at home," said Curt. "Can I get you anything? Water?"

"Iced water would be great," I replied. "It's wicked hot out there today."

"I hear ya," he said, hustling to the kitchen.

I took this time to look around. It was a tidy spot, a really great living space. Artwork and photography lined the walls. There was a brown leather couch in front of a large flat screen tv. Underneath that was an impressive collection of records. In what I imagine was the dining room, a long table had been pushed to the wall. A massage table was set up overlayed with a white sheet. He sure meant business.

Curt returned with the glass of water. The cold glass helped to cool my warm hands. Curt's smile was infectious and I immediately felt at ease around him. He wore shorts made of gray sweat-pant material and a simple white undershirt. His smooth arms belayed strength. I admired his shapely calves and thick quads. I especially enjoyed how pronounced his bulge looked in those shorts.

"Come and sit, please," he said, putting one hand on my back and directing me to the couch.

He sat with one leg crossed underneath him so he could turn towards me. I sat next to him and took a big gulp of water. He had one arm up on the couch cushions, his hand close to my shoulders. His long pointer finger reached out to trace the lines of my vine-tattooed arm. We chatted idly about the weather, work, and the annoyance over increased tourist traffic, but nothing of real substance.

"Yeah, work has been super stressful lately," I said, setting down the glass on a coaster and resting my hand on his thigh. "Plus with grad school, I never get much chance to relax."

I knew what I was doing, and so did he. I was not so subtly giving my cue that I was interested in staying. Interested in getting naked. Interested in feeling his big hands all over my body. He scooted in closer and put both his hands on my shoulders working his thumbs into my back muscles.

"I hope you'll allow me to help you with that," he said, flashing his smile again.

"Absolutely," I said, leaning in closer.

Feeling brazen, I planted my lips on his. He pulled me tight to his chest and returned my kiss, sucking on my tongue. Curt rose from the couch his shorts tented, pulling my arm to get me on my feet. He led me to the massage table and turned to kiss me again.

"You make yourself as comfortable as you want," he said, patting the massage table. "Strip to your underwear at least, then go ahead and lay on your stomach. Put this sheet over you when you're ready. I'm just going to get the oil ready."

He left for the kitchen. I pulled off my tank top and dropped my shorts. I'd worn a black jockstrap underneath, the straps lifted my perky cheeks. I decided to keep it on and let Curt decide when it should come off. I heard the microwave turn on, which confused me, but I shrugged it off. I slipped underneath the top sheet on the massage table, putting my face through the hole in the headrest.

I heard his footsteps approaching and then felt his hand on my lower back.

"Did I hear the microwave going?" I asked.

"Yes, sir, you did. I like to use coconut oil. It melts to a liquid in the microwave. It's incredibly hydrating for the skin and super slick. It can also be used in more sensitive areas."

He didn't see me raise an eyebrow, but I'm sure he knew I was following along. Curt folded the top sheet several times until it was a thin rectangle of cloth that barely covered my butt.

"Please feel free to let me know if anything feels uncomfortable or painful," he said.

Curt scooped some of the oil into his hands and rubbed his palms together. He started at my lower back, applying firm pressure with both hands along either side of my spine, pushing up towards my shoulder blades. His fingers gently grazed my skin on their travel back to my waist. He repeated this movement, hands not stopping until he reached my neck.

He continued up and down my back, stopping to work on knots in the shoulders and traps with his elbows. I grunted through the pain, but his touch was magic to my muscles. I felt the stress and tension melt away beneath his attentive hands.

"How's everything feeling so far?"

"So good," I mumbled, barely audible.

Curt smiled and gathered more oil. He went to the far end of the table and drizzled the warm liquid up my calves and hamstrings. I could feel it drip down to the inside of my thighs. His thumbs attacked my calves, and I quivered as he further released tight muscles. Through his movements, I could feel the strength and power in his muscular arms.

With fingers outstretched, he palmed the back of my thighs. Each time his hands traveled upwards, he got closer and closer to my ass. With one more sweep upwards, his hands went under the top sheet, under the straps of my underwear, and kneaded my glutes.

"Is it alright if I take off this sheet?" he asked politely.

I nodded in the headrest and reached back to pull the sheet off for him. He didn't comment on the black jockstrap but I hope he liked it.

"It would make it even easier if I took these off," he said, snapping one of the straps.

I lifted my hips up and he pulled them down by the thick waistband. My hard dick got caught in the movement and came to rest between my thighs and pointing towards my feet. He stood at the end of the table again, surveying my bare ass and erect cock. He made another pass upwards over my hamstrings, this time squeezing and pulling apart my cheeks to reveal my smooth, pink hole. His hands went down into my crevice, running his fingertips over my hole. He continued down and thumbed my cock, rubbing my precum around the tip. I was loving every minute of this.

He walked to the front of the table, taking his shirt off. He leaned over my head, running his hands down the length of my back. I could feel his hard cock rubbing against my head. I couldn't wait to see it, but I didn't want him to stop just yet. Instead, I reached my hands up and found his thick quads. I continued my search upwards, into the legs of his loose shorts. My right hand found his throbbing 8" cock and my left found his heavy ball sack. I could feel the wetness of his precum, and I yearned to taste him.

I retracted my hands enough to escape the legs of the shorts, but quickly reached up and yanked down on the drawstring and waistband. Curt didn't stop me and continued working the muscles of my shoulders and neck. I found his freed cock again, stroking it in my right hand. I could just barely touch my thumb to my middle finger around his veiny girth.

I lifted my head up and pulled at the back of his thigh with my left hand, using my right hand to guide his prick into my eager mouth. Curt's hands left my shoulders. With one hand, he supported me at the chin, the other wrapped around the back of my head. He took control here, pushing his dick into my mouth as far as I could manage, retreating when he met resistance.

"Ah fuck, Rob," he whispered. "Your mouth feels amazing."

I wanted to release my dick out from under me, but Curt kept me in this position for another five minutes or so. He fucked my mouth at a steady pace. I was getting more comfortable taking it down my throat. I was able to swallow him until my nose was nestled in his trim, gray pubic hair. His thickness made my jaw sore but I wanted so bad just to please him. He pulled his dick out from between my lips, setting my head down gently.

"I'm not quite done with you yet," he said.

Curt stepped away momentarily. Underneath the headrest, he showed me what he brought back. It was a slender rod of clear glass, with a slightly curved tip that kind of resembled a dick head.

"I'm going to use this on you now, is that okay?"

I nodded in silent approval. I've never actually had anyone use a dildo or prostate stimulator on me. This made the experience even more unique and exciting. He slowly walked alongside the table, drawing a line down my back with the glass toy. His long dick equally dragged across my arm and side. He stopped to stand next to my ass, his dick poking into my outer hip.

Curt set the toy down between my legs. With one big hand, he spread my cheeks while the other dribbled more of the hot oil onto my hole. He set the bowl down, keeping my cheeks spread wide. With his free hand, he used his long middle finger to work the oil into my hole. The warmth of the oil and the pressure of his finger made more precum leak from my dick. From the sticky wetness I could feel on my hip, Curt was getting equal pleasure. I arched my back and pushed my hips up into his touch, encouraging his fingers to delve further.

Ever so slowly Curt pushed the bulbous tip of the glass rod against my hole. I squeezed and relaxed my pucker in response. The glass felt almost cool in stark contrast to the warmth of the oil and Curt's skin. He pushed firmly and the end penetrated my sphincter. The mix of cool and warm inside my hole gave me an entirely new feeling of pleasure. I writhed on the table, grinding my dick into the padding and my hips pushed up, trying to take more of the glass inside me. Curt removed the toy and walked to the front of the table.

"Get on your hands and knees," he whispered into my ear.

I scurried into the position.

"Come down to your forearms," he said, pushing firmly in-between my shoulders.

I did as he asked, resting on my forearms and arching my back, presenting my ass. He leaned over me, toy in one hand and the other guiding his cock towards my face. I opened my mouth to happily take his dick again. I slurped on his head, taking half his length along my tongue. He pushed the glass rod into my hole and I moaned around his dick. I absolutely loved the feeling of being filled at both ends. I tried to take more and more of his cock, gagging and choking myself.

Curt started a steady rhythm of pushing the toy in and out of my hole. Each time he pulled it out, he pushed his hips forward to shove his cock further down my throat. In and out he went with the toy and his dick, essentially fucking both my holes. If I had my hands anywhere near my dick, I would've been cumming all over the massage table.

"I think you're loose enough for me," he said, taking the glass dildo out of my hole. "Are you ready for this dick in your hole?"

I nodded while slobbering his meat.

"Tell me you want it, boy."

"Please fuck me, sir. Fuck me with your big dick!"

He walked to the back of the table and pulled at my feet so I was once again lying flat on my stomach.

"Show me your hole, boy."

I reached back to spread my cheeks, winking my pucker at him. He growled in response and slathered oil onto his dick. He got up onto the table, sort of in a push-up position over me. His cockhead was pointed directly over my hole. He lowered himself down and I helped guide his dick. He had indeed worked my hole loose enough, and with the oil, his greased-up pole easily slid inside me. His dick, however, was much thicker than the toy had been. I kept my cheeks spread as he stretched me out even more.

"Oh fuck," I gasped, "It's so big, I can feel you stretching me out."

"That's right boy, open up for me," he growled back.

He kept himself propped up with his arms, but his hips and legs lowered onto mine. He drove his hips down until he had fully penetrated me. I could feel his heavy balls resting on my taint. He gently thrust up and down with his hips, taking it slow to help me acclimate to his girth. I moaned into the sheet with each downward moment, feeling my hole open more and more. I got to a point I could squeeze around his dick while he trusted in and out.

"Ah fuck, that's right boy, grip my cock."

Curt fully lowered himself onto me, his full weight pressing down onto my body. He wrapped one muscled arm around my neck. With his free hand, he pulled on my hair, angling my face so he could shove his tongue into my mouth. His hips began deep, deliberate thrusts that jostled the massage table each time his pelvis slammed into my ass.

"You like this dick, boy?" he asked.

I nodded and whimpered.

"Tell me how much you like it, boy," he demanded.

"I love your big cock, sir. I love you stretching my hole. I want you to fuck me all night, sir!"

After fifteen minutes of his powerful thrusts, Curt climbed off me and the table. He rolled me onto my back and spun me around perpendicular to the table. He lifted my legs and took an ankle in each hand.

"Look at that beautiful gaping hole," he whispered. "You want me to fill it back up?"

"Please, sir," I said while nodding. "I need your dick, sir."

He pushed the tip of his dick against my pucker. I pushed my hole out to take the head in. Gently he pushed forward with his hips, inserting his meat inch by inch until his balls bounced on my taint. He pulled all the way out, making me feel empty. Again, he slowly pushed in, taking his sweet time. It was amazing how this beefy, masculine man was so caring, gentle, and attentive, yet I wanted to obey every word he said.

He pulled me by the hips, resting both my legs against his chest, my ankles on his shoulders. He leaned forward, practically bending me in half, and kissed me. His beard tickled my chin. Our tongues wrestled as he continued his deliberate thrusts. He broke our kiss and stood up tall. He took both my ankles in one hand, his other arm wrapped around my thighs, keeping my legs tight together. He started thrusting into me faster and faster, his balls slapping my ass cheeks. He looked down to watch his dick slide in and out of my loose, wet hole.

He pushed my legs down, turning me onto my side in the process, my shaped like an L. Curt hammered into me. One hand held me tightly by the hips, the other he reached to my mouth. I sucked on his first two fingers, staring into his eyes, moaning wildly. Curt's chiseled chest was glistening with sweat. He looked like almighty Zeus, pounding his godly seed into me, a mere mortal. The table beneath me shook and shuddered during this welcomed dick assault.

He paused thrusting briefly to pull me close to him, spinning me on his dick so I was bent over the table. By now, he'd been fucking me for almost an hour. It was as if he wanted to cover every position imaginable. His stamina was incredible. He lifted my left leg from under my thigh so one knee was up on the table. He held on tightly to my hips and resumed pounding my gaping hole. The table was rocking from him fucking me so fast and aggressively. I held onto the sides for dear life, my throbbing dick continuing to leak precum. We were both dripping sweat and Curt was panting from his exertions.

"Are you ready for your prize? You want my cum, boy?" he asked.

"Fuck yeah, daddy, give me your load!"

He pulled out of my ass, spun me around, and pushed down hard on my shoulders. I collapsed to my knees and he started jerking his pole in my face. I opened my eager mouth, sticking out my tongue. I watched the display of orgasmic pleasure painted on his grizzled face.

"Fuck! Here it comes, boy. Eat my fucking load!"

Curt grunted as his dick spasmed, shooting hot jets of his man juice onto my face. Some landed on my cheeks and lips. Most of his load landed on my tongue and I greedily swallowed it all. I had my fist, wrapped around my dick, pumping furiously. In a flash, he had me back on my feet. He picked me up and laid me on the table on my back, with my head hanging off the end.

"Clean my dick off, boy," he said while straddling my face.

I took his cock in my mouth, tasting his cum and my ass juices. His sweaty balls rested on my nose. Curt bent at the waist, shoving two thick fingers into my well-used hole. His other hand took over jerking off my cock. He stroked me with a tight grip while finger fucking my hole. I reached back and held onto his ass while taking quick breaths through my nose. I thrust into Curt's hand. He leaned over more and took my cock into his mouth, swallowing my 6.5" inches down to the base. I erupted in his mouth, and he swallowed every drop. Curt pulled his now soft dick from my mouth. He lifted my head and we shared one last kiss. I was still trembling and panting from the tumultuous orgasm.

Curt offered up a shower to get cleaned off, and I gladly accepted. We took turns washing each other in between heavy make-out sessions. After drying off and getting dressed, he made us each an old-fashioned. We sipped the bourbon arm-in-arm and casually talked about the art and photographs on the wall. Afterward, he showed me some pieces from his leather collection. I was particularly drawn to the cuffs and collars. He even let me borrow them for an upcoming black party I was going to attend during Montreal Pride, but that's a chapter for another day.