*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."
