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What I Had Been Missing

"An older male has his first gay encounter."

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2.6k words 2.6k words

I rose up on my elbows and looked down at my groin area. A terrycloth hand towel was draped demurely across my cock and balls. I sighed deeply and considered what had transpired over the last hour.

First, some background:

I had been a rudderless ship for almost three years. I was only fifty-five when my wife of twenty-seven years was killed by a drunk driver. I went through the usual stages of grief and returned to my job as a marketing executive for a medium-sized Chicago brewery after three weeks.

My job performance really didn’t suffer all that much. I didn’t self-medicate with my wife’s bottle of Xanax or the complimentary six-packs from work. On the other hand, I realized I was functioning on auto drive. It obviously helped that I had a more than capable staff.

Rumors began to circulate that we were a take-over candidate. These rumors crystallized into reality when “suits” began materializing at the brewery. We were a no-tie, rolled-up-sleeves kind of shop. They wore dark suits, rep ties, cap-toed oxfords, and chartreuse visitor hard hats,

I rapped my knuckles on the door jamb of my boss’ (the CMO) office. He kept his phone to his ear; but motioned me in, pointing to a desk-side leather chair.

David lowered the receiver to its cradle.

“Is it true?” I asked.

“Yep and it’s bad,” he answered.

“How bad?”

He rubbed his bald head. “Real bad, the evil empire from Belgium is buying us out. Speaking of out, we’re all canned.” He shuffled through a stack of sealed envelopes and handed me mine.

The near present:

I didn’t mope around after being let go. The very same day, I hired a headhunter to start an employment search. Surprisingly and despite being almost sixty, I received five employment offers. The good? I was flattered. All proffered jobs were at the VP or CMO level. The bad? Every single offer involved pulling up stakes and moving to LA or New York City.

It took me ten days and five bottles of California Cabernet to decide my future.

I decided I’d rather stick a fork in my eye, than leave Chicago. I just couldn’t see selling our house in Evanston; the house in which Mary and I had raised the kids.

I sat in the den, the room Mary called my man-cave, looking at the single banker’s box on the floor in front of me. This one box contained the entire contents of my old office at the brewery. I had been putting off opening it. I took a sip of wine. My plan was to sort things into three groups. Paper would be tossed into the fireplace, my keepsakes would be displayed on the bookshelves or tables and the rest would feed the dumpster. By the time I finished the first of my self-allotted two glasses of wine, I had kept only a single family picture. We were standing atop Vail mountain, smiling with ski poles held high overhead.

Then and there I decided I was officially retired.

My early day routine was pretty simple. Each morning I’d arise at around 6:30 am, rub my eyes and scratch my nuts. I’d don sweats and my favorite New Balances. After stretching and doing a hundred pushups and crunches each, I’d hit the sidewalk. My five-mile route took me past the university and its half-dozen coffee shops. My usual was Common Ground, a place where the baristas knew my name and drink.

I developed a few friendships, mainly fellow runners or university staff. We all had in common a need for early-morning caffeine.

Chad was working the head of the order line one morning. He was a good-looking twenty-something with a surfer vibe: blond mop, maybe 5’ 11” and 165#. He smiled, “The usual, Rick?” He grabbed a Sharpie and wrote on a large paper cup.

I nodded, paid, and thanked him.

I walked to the pickup counter and checked the orders visually (touching others’ cups bugs me). All were mediums or plastic. Meg walked up and handed me my latte. She grinned and handed me my beverage. “Something special today, Rick?”

“Nope, thanks.” I walked out the door and took a sip. That’s when I saw it. Chad had drawn a tiny heart over the “i” of Rick.

I felt a twitch in my cock and balls, but thought nothing of it. I knew I wasn’t gay, but I was flattered that a handsome young man was in some fashion interested.

The present:

Out of the blue, an old friend called. He asked whether I had any interest in a free charter flight down to and back from Albert Whitted Airport in St. Petersburg. He was taking his wife and kids on vacation for ten days and there was an open seat.

I thought, what the hell? My social calendar is open.

I booked a ten-day stay at the Turtle Beach Resort near Siesta Key, opting for a cottage with a boat dock. My final job was to find a boat. After a fifteen-minute Google search and a twenty-minute call, I was all set.

The Embraer Praetor would land at around 11:15 am. I’d grab my small backpack and walk over to The Teak for lunch. The boat was being dropped off next door at the yacht basin.

I reserved a Mako 114 CC, small enough that the liability insurance wasn’t a nonstarter (particularly since I had a recently renewed captain’s license); but big enough to handle the swell of Tampa Bay.

Thirteen days later, I was sitting in my personal jacuzzi, glass of Shiraz in hand.

I had turned up the heat of the jacuzzi to warp to try to alleviate an aching low back. Thinking I was thirty again, I’d stayed out on the water for almost six hours. The chop on the way back from Sarasota was a killer, also.

I eased out of the spa and toweled off. My intent was to ring the front desk of the resort and query as to whether there were massage therapists on site.

I was disappointed to hear the answer was “no”, but the staff suggested I talk with the concierge for perhaps alternative arrangements.

The concierge was both pleasant and efficient. She suggested the resort had a relationship with a nearby hotel. All I needed to do was pick a day and time. The therapist would show up at my cottage within a ten-minute window. The fee (other than tips) would go on my tab.

The therapist was scheduled to arrive around 8:30 pm, give or take. I had a half hour to blow. I rinsed off in the shower, sprayed on some Sure and donned my sweats. I poured a glass of Cab and settled into a wicker chair. I casually wondered whether my masseuse would be hot.

Almost on the dot, the doorbell chimed. When I opened the door, I was briefly set back. There standing before me was an athletic-looking young gentleman with his hand stuck out.

We exchanged pleasantries as he entered the cottage and proceeded to set up his table. His name was Dirk. I asked if he’d like a drink. He looked at my glass, suggesting “I’ll have what you’re having.”

“I’ve got to take a quick call. Why don’t you get comfortable? Let’s start with you face down.”

I figured when in Rome, do as the Romans do. I stripped down to my birthday suit, crawled onto the padded table, and positioned a towel across my butt.

Dirk made contact by lightly placing one hand on my back. He asked if I wanted to use the horseshoe face rest. I passed: claustrophobia. He asked if there were any areas on which he should focus. I suggested my low back and upper traps. I volunteered that I typically preferred a light to medium-pressure Swedish technique.

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Dirk retrieved a plastic squirt bottle of oil from the kitchen microwave. After re-establishing contact, he liberally applied oil to my torso and shoulders. The oil was warm, almost body-fluids-warm.

He thoroughly worked my low back, rib areas and shoulders. His technique was smooth, almost fluid in nature. He rarely lost contact.

Dirk, repositioned my right arm down the table, my hand and fingers at the very edge. He started at the shoulder and worked down to the fingertips. After massaging the palm, he replaced my hand; but now with the fingers dangling freely over the side.

Dirk leaned across my torso to position my left arm much like the right. His basketball-style shorts brushed my fingers. I felt the unmistakable prominence of an erection.

I opened my eyes as Dirk rounded the top on the table to massage my left upper extremity. There was no mistaking his boner.

Dirk finished my other arm and once again left my hand dangling over the table edge. He removed the towel and liberally oiled my buttocks and legs.

He ran his fingernails lightly up my left leg, across my buttocks, and then down the right. I broke into goosebumps.

Dirk began kneading my buttocks, his thumbs toward the midline, fingers pointing outward. He paused and added more oil. I sighed as the warm fluid ran past my anus and on to the taint. Dirk followed the path of the oil down my crack with his thumb. Involuntarily my thighs parted. The sensation of his thumbs teasing across my pucker sent a message to my cock, “Rise and shine.”

I raised my pelvis up and down slowly to match the rubbing of his thumbs. I felt him making contact with my ballsack and on to my cockhead. With one digit, he circled the very tip of my prick, lubricating the head with both his oil and my dripping precum. Dirk shifted his other thumb up to my greasy anus. I wanted him to finger-fuck my virgin ass. As he applied pressure, I rose upward and backward on my hands and knees to signal my readiness. His thick thumb popped into my hole.

I growled out an almost unintelligible, “Oh yeah. Fuck me.”

Dirk pistoned his right thumb in and out of my rosebud, while simultaneously circling the base of my scrotum with his other thumb and index. I gritted my teeth as he pulled my cajones toward the mattress. I had to either collapse onto the table or lose my nuts.

He released my screaming balls and withdrew his thumb from my ass. I felt cheated. Dirk slapped my ass. “It’s time to turn over.”

As I was rolling over and getting comfortable, Dirk was reheating the oil and washing his hands. When he returned, he asked, “Would you mind if I got rid of these shorts?”

I was struck dumb. I simply looked at the tented fabric and the obvious spot of precum. I nodded and closed my eyes. I thought of barista Chad.

Dirk oiled my chest and belly. I could feel the liquid pooling in my navel. I could also feel my nipples hardening, despite no stimulation from Dirk. He took his time massaging my chest from the side. His cock touched my left hand. I could feel his precum dripping onto my palm. I circled my fingers around his organ.

I rolled slightly toward Dirk so that I had an unobstructed view of his dick and balls. His velvety schlong was a thing of beauty, at least two inches longer than my six and a half, plus proportionately thicker. I dropped my hand down to cup his lemon-sized testicles and added my right to his meat. As I slowly jacked him, he closed his eyes and moved his hands under his shirt and up to his pecs. I surmised he was pinching his nipples.

Dirk withdrew slightly, announcing it was time to get back to the massage. Disappointment number two.

He ran his fingers across my left nipple as he walked to the head of the table. Dirk started on my pecs, making progressively smaller circles until he teased, then pinched my BB-sized nipples. He worked his way down my chest and abdomen, leaning over my head as he did so. I could feel his meat make contact with my forehead.

I shifted my hands up and around his torso. I encouraged him to move downward. Dirk rose up slightly and moved another two or three inches toward my groin. His dripping dick, then balls touched my lips. I tilted my chin up and licked the base of his swollen sex organ, then sucked his left nut into my mouth. I could both smell and taste his musky man scent. I let it pop out. I really wanted Dirk’s prick in mouth, but the angle was terrible.

Dirk sensed my need. He rose up from his leaning position and shifted over to the right side of the table. He instructed me to scoot down the table somewhat. I flexed my hips and knees; plus rotated toward him. My face was now just inches from his beautiful man-meat. The head was glistening with a droplet of precum dangling toward the white table cover.

Without thinking, I leaned forward and caught the drop with the tip of my tongue. I painted my lips, then savored the salty sweetness. Dirk directed my head toward his cock with his left hand. He fisted his thick sausage and plunged the plum-sized head into my hungry mouth.

Dirk removed his hands from both my head and his sausage. While keeping his pelvis affixed to my face, he leaned down and across my torso. He balanced his left hand on the table, leaving his right free for play.

He didn’t disappoint me. He lifted my stiff prick off my belly and licked what I surmised was precum from my belly. He slid my dick into his warm mouth. He began a slow and light-touch jack of my shaft.

I had zero experience giving head, but figured I’d just wing it, giving my lover what always felt good to me.

I worked my tongue in circles on the bottom of his cockhead and the first inch of shaft. I jacked his shaft from his balls to my lips, adding rotation. I hoped to wring out a huge volume of his hot jizz into my hungry mouth. For the third time, I thought of Chad.

Dirk had a PhD in cock sucking.

I felt him adding both speed and pressure to his technique. He was bringing me close to ejaculation. Instinctively, I did the same to his organ.

I felt Dirk stop sucking. He rose slightly and growled, “I’m gonna cum. Want it in your mouth?”

My response was nonverbal. I pulled more of his breeder into my mouth and jacked him even harder.

I felt Dirk’s body, hand and mouth pause. He held his breath momentarily, then bucked his pelvis and shuddered violently. He uttered something unintelligible, trying to speak with my cock in his mouth. He filled my mouth with four or five or maybe six ropes. I swallowed his warm seed to keep from drowning.

Dirk commanded, “Shoot, Baby. Give me your load. Cum in my mouth.”

While keeping his luscious semi-hard dick in my mouth and mine in his, he gave my spewer a vicious work-over. I shot within seconds. I heard Dirk making satisfied slurping sounds. This made me beyond delirious. My taint spasmed as I pumped out the forth and final rope.

Published 
Written by Delbert6776
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