Play Date [*/M] [Edging] [Anal] [Handjob] [Medical] [D/s]

Adam was 25 years old, muscular, blond, and quite the specimen. We had met online and discussed our shared fantasies for weeks. Well, one thing led to another, and I found myself setting up my playroom in anticipation of his arrival.

I own an exam table, as I am quite fond of playing doctor. This, I positioned for how I envisioned my playmate upon it. The back was raised nearly vertical, and I extended the metal stirrups–nothing thrilled me like a man in stirrups. 

Adam arrived right on time, and after a few pleasantries, we got down to business. Showing him my playroom, I could tell he was impressed with my level of dedication. Playing doctor was a kink of his, too, but today we had something different planned. I wanted to build Adam up to an exhilarating orgasm. This session would be all about him and his pleasure; however, it was clear that I was in charge. Naturally submissive, the young man was excited to play by my rules.

Adam inspected the exam table excitedly. Honestly, I couldn’t wait to see him atop it! Once we had become comfortable with one another, our play date began. I told him it was time to remove his clothes, and the young man was soon undressing before me.

My new friend played sports, and his training was obvious. Nicely developed muscles greeted me as he disrobed, and soon he was standing in only his boxer shorts. His chest and legs were hairless, and when the underwear came off, I saw that he kept everything well-shaved.

I patted the exam table and told him to hop up. Taking a deep breath, he took a seat, and awkwardly placed his bare feet in the stirrups. I adjusted him back a bit and spread his legs further apart. Finally, drawing his knees closer to his chest, his bottom was left perfectly exposed at the edge of the table. 

“Are we ready for this?” I asked, looking over the man.

“For sure,” Adam smiled, obviously a bit nervous.

“We’re going to go nice and slow,” I told him, pulling a pair of exam gloves from my pocket. “Remember, the key is to bask in the present moment; try not to focus on the climax. It’ll be difficult your first time, but I think you’re going to really enjoy this. We’ll start firat with a little anal massage. Sound good?”

“Sounds good,” he answered.

“Well then,” I grinned, snapping on the gloves, “here we go.”

Taking a bottle of my favorite lube, I stepped between Adam’s spread legs. My new friend looked amazing, his genitals so soft and smooth. His impressive penis lay flaccid against his hip, but I was confident that would soon change.

Squirting a generous amount of lube on my gloved finger, I took in his little pink starfish. Not a hair was to be seen, as I set my finger to his tight round muscle. Starting with little circles, I spread the lube about the sensitive area. Nice and slow, I rubbed him.

“How’s that?” I asked, knowing that he had never experimented down there before.

“It’s good,” he breathed. “Feels really nice, actually.”

Round and round I went, before applying another glob of gel. It had only been a few moments, and already I noticed his scrotum was retracting. That wonderful penis was plumping up as well. It had been two weeks since Adam’s last orgasm, as I wanted him quickly on edge.

“You like this, hmm?” I asked.

“I do,” he whispered.

“You have a lovely bottom,” I observed. “Most guys are so hesitant about being touched here, but it’s a fantastic erogenous zone. Tell me what you’re feeling.”

“I feel exposed,” he said. “It feels…almost wrong? But, I really like it at the same time.”

I continued the slow massage, extending out to the perimeter, then returning back to the middle of his anus. The pink skin glistened in lube, and his member continued to steadily stiffen.

“That’s a good boy,” I said, watching as he grew. “Let your body react. There’s nothing to be ashamed of. Remember, take long, deep breaths.”

Adam inhaled deeply and blew out his nervous air. Hands were at his sides, and his eyes were shut. As I worked him, that beautiful penis began angling toward his tummy.

Placing the pad of my middle finger directly against his hole, I gently rubbed. Softly, I applied a bit of pressure.

“Mmm,” came a cute little moan.

“How’s that?” I asked.

“Different,” he sighed. “But good.”

Pushing gently, the tip of my finger started to squeeze past his ring. I retracted as he caught his breath, and resumed massaging his entrance. Once he relaxed a bit, I pressed again. Slowly, my finger began sliding into the man.

“Ughh!” he grunted, his toes scrunching up in the stirrups. 

“My goodness, you’re tight,” I smiled. His strong ring of muscle gave way to a cavernous depth, warm and wonderful. Gently, I probed about, locating his sweet gland.

“Oh, my god,” he sighed, breathlessly.

As if pushing a button, his penis became fully erect, and his testes cinched up close to his body. The sight of this stud, spread wide and fingered, was amazing.

“That’s your prostate,” I informed, softly tapping. “Nice and healthy.”

“That feels so…weird,” he groaned.

Slowly, I withdrew my finger from his body, and he stifled another moan. Reaching over, I picked up a small metal butt plug from the nearby table. 

“What do you think?” I asked, holding it up. “It’s a little bigger than my finger, but I think you can take it.”

“I’ll try,” he answered, watching as I generously drizzled the toy with lube.

Touching the metal bulb to him, I slowly circled it around. 

“It’s cold,” Adam said, resting back his head.

“It’ll be warm soon,” I smiled. “Deep breaths. Relax your sphincter.”

I watched his chest rise and fall as he calmed himself. Placing the tip of the plug to his center, I applied some slight pressure, watching it peek in.

“It feels,” he breathed, “a lot different than…your finger.”

“Indeed,” I said. “But this is going to slip right on in.”

Easing up, I circled his anus a few more times, getting him used to the sensation. Already, his glistening muscle seemed less tense.

“Mmm,” he moaned. “I like that.”

“When it enters you,” I told him, “I want a nice, long moan. Can you do that for me?”

“Yes,” he panted.

I gently, steadily, pressed the bulb against his hole. Slowly, stretching him open, it reached the widest circumference of the plug. Then, his anus closed around the tapered end, sucking it into his virgin rectum.

“Ohhh!” he moaned, taking it. A decorative red gem remained at his entrance.

“How’s that?” I asked, running my fingers over his bottom, brushing across the jewel.

“It’s so good,” he whimpered.

“Good,” I smiled. “You’re doing so well. Now, we’re gonna lube up the rest.” 

Grabbing the lubrication, I began squeezing a generous amount over his privates. Starting at the tip of his penis, I drizzled along the shaft to the scrotum. 

I placed my fingers on his pouch and slowly started to spread the lube. My gloved digits slid wonderfully along his orbs, and his smooth skin soon glistened. Down I went, distributing the slippery substance under the scrotum and slathering it across his perineum. The pubococcygeus muscle bulged, hard and swollen with arousal.

“Fuck…” Adam sighed.

The man’s penis stood tall and straight, and a glob of lube made its way down the thick shaft. Moving to his member, I distributed the gel, being careful not to overstimulate. Adam closed his eyes in pleasure, and I soon had him shining. Taking a step back, I appreciated the wonderful sight before me.

“You look amazing,” I said.

Adam smiled and blushed, averting his eyes in self-consciousness. Those muscles were phenomenal under his smooth skin. It was his vulnerability that excited me most–the way he was fully displayed: Those feet cradled in the stirrups; his pink, glistening genitals engorged with excitement; that round red gem sparkling at his man-hole. What a vision!

“There’s nothing to be embarrassed about,” I told him, as he turned red. “You look fucking amazing.”

“Thank you,” he whispered, his eyes going to what I was taking from a nearby table.

“This is a little vibrator,” I said, flipping on the device to its lowest setting. “I think you’ll enjoy.”

“Oh!” he gasped, as I touched it to his perineum. “Ohh…”

I moved it about his underside in slow, steady swirls. The device hummed against his slippery skin, and I watched his penis flex, fattening up even more. A single bead of clear fluid escaped from the tip.

“Uhh,” he continued. “Hmmm…”

“That’s right,” I smiled.

Sliding the bullet slowly up, I ran it along his scrotum with a light touch. 

“Ooh, fuck…” Adam squirmed in the stirrups.

“Try and keep still,” I reminded him, gliding the device along his testes.

The young man restrained himself while I teased his gonads. Over the top, underneath, around the sides–I covered every bit of his sack. By now, his balls had cinched up so very close to his body.

“Feel nice?” I asked.

“It’s so good,” he nearly whined.

Sliding the vibrator downward, it set it rattling against the red gem of the butt plug.

“HMMmmm,” Adam moaned, as the plug vibrated against his innards.

“That’ll stimulate your P-spot, as some call it.” I informed him.

“Ahh!” he gasped, trying to steady himself. 

“I love how you moan,” I cooed, cupping his balls. Softly, I caressed them, as the plug tickled his gland. 

By now, his erection was raging. The shaft, thick and webbed with veins, throbbed with his pulse. The swollen head shined in a mixture of leaking fluids and lube. How he must have yearned to bury it into something deep and tight. Three pumps, and it would probably have given up his load.

I turned off the bullet, and crouched between his spread legs. Placing my thumbs upon each side of his PC muscles, I massaged up and down, side to side. My gloved thumbs circled over the sweet spot between the testes and anus. Every time he tightened up, the plug was sucked in a little deeper.

“Oohh, that’s good,” he breathed. 

Sliding down, I circled the butt plug, enjoying how it looked against his tanned, smooth skin. Gripping the ruby, I have a little tug; it didn’t budge, held tight by his sphincter. 

“How does the plug feel?” I wondered.

“I feel…so full,” he could barely think. “And it’s so…so deep.”

“Go on,” I prompted.

“I, I want to push it out, but,” he panted for a moment, “but I can’t.

“And these beautiful balls of yours?” I asked. “Are they full?”

“They’re so full!” he nearly sobbed.

“I know,” I sympathized, moving my hand toward the base of his penis. Taking it between my thumb and forefinger, I gave it a little squeeze. “My goodness, you’re so hard.”

“I’m so hard,” he repeated, whimpering.

With only a thumb and finger touching the sides, I slid up his shaft.

“Mmm,” Adam let out, as I went.

Reaching the plump head, I touched a finger to his urethra. Swirling over it, I slid in his slick emissions. Soon, I was running my finger around the whole of his helmet, mixing his self-made lubrication in with the artificial.

“Huh-uhhg,” Adam pathetically moaned, as my finger went round his rim. 

Gliding my finger down the underside of his shaft, his penis did its best to press up against me.

I formed a hole with my fingers, and placed my hand above the head of his member. Slowly, in a loose grip, I lowered my hand over him.

“Mmm-hm,” he breathed.

“Show me how you thrust that big penis,” I demanded.

Adam started pumping his hips as best he could in his position upon the table. Up and down his penis moved, though I kept my fist so that it just skimmed his shaft. 

“A-huh-mm,” he whimpered, apparently unsatisfied with the looseness of my grip. “Please, let me…”

“I am letting you,” I said. “Im letting you show me how you fuck.”

“I’m so desperate!” he groaned. 

I squeezed my fist a bit tighter, watching as the poor man thrust. Up and down went his thick shaft, the plump head poking out past my ring of fingers. My god, he was big! I could feel the warmth of his manhood through the glove, and the texture of his engorged flesh.

“Slower,” I ordered, as he got a bit carried away. “Good boy. Nice and easy, just like that. Up… Down… Up… Down…”

“Uh…uh…uh!” He moaned, each time his tip poked through my ring of fingers. 

I knew he was getting close, and I released him just in time.

“No, no!” the man begged, thrusting into empty space. A nice stream of clear fluid trickled from his tip. “Ah-huh…”

“Shh,” I comforted, softly patting his testes. “Just relax. Breathe. Stay still.”

Adam stopped pumping his hips in vain and inhaled deeply. Another clear bead oozed forth as he flexed involuntarily, followed by a desperate moan of frustration. And there he throbbed, longing, his eyes silently begging for relief. 

I let him calm down a moment, before again setting the vibrator to his little gem. Immediately, he started panting as the sensations titillated his insides.  

“I can’t take anymore,” he cried. “I-I can’t take it.”

“Would you like me to milk you?” I asked.

“Yes!” he wept. “Please.”

“Tell me,” I commanded, pressing the vibrator harder into the plug.  

“I want you to milk me,” he whined.

“Keep still, now,” I said, again taking him in a loose grip. 

Up and down I slowly pumped, barely making contact. I swear, I could feel him expanding into my hand, ballooning to fill my grasp.

“Ohh, god,” he moaned. “Oh, I want it so bad…”

“Relax all your muscles,” I told him. “Breathe. Feel the pleasure in your loins; your prostate; your testes. Think about your rectum, packed for the first time–your anus, hugging the metal stem of the plug.”

Adam was calming himself, breathing nice and deep as I talked. Opening his eyes, he looked from me to his genitals, watching as I stroked.

“Oh, it’s so good,” he sighed. “Please, don’t stop.”

“What am I doing to you, Adam?” I asked.

“You’re milking me,” he answered. “Y-you’re milking me.”

The vibrator hummed against the plug. Up and down I slid my hand, slow and steady. The PC muscles twitched, and I knew he was peaking.

“Oh god,” he breathed, fighting to stay still. “Please don’t stop.”

I continued on, as the young man moaned beautifully. His eyes were on my hand, watching as it stroked up and down. He twitched some more down below, his body attempting to initiate an orgasm. A wad of white emerged from his head–semen that couldn’t wait for a strong contraction.

“Ooohh,” let out Adam, watching as it dripped.

“That’s a boy,” I said, slowing my pace. “Moan it out. You’re doing just fine.”

“MMMmm,” he purred, as his premature cum flowed thickly between my glove and his penis. 

“Very nice,” I said, releasing him.

“Noo…” he nearly sobbed, looking at me pathetically. ” Please!”

I clicked the bullet to a higher setting. Holding it against the plug, his eyes almost rolled to the back of his head. The young man positively sang. Never had I heard such beautiful, sexy sounds coming from a male.

“Ohh,” he moaned with each breath. “Oooh, God. Yes… Yes.”

“That’s it, Adam,” I spoke softly. “Just ride it out.”

Placing my finger at the very base of his penis–right where the underside of the shaft meets the scrotum–I softly rubbed in circles.

“Ohh, yeeaah,” he positively moaned, almost in a feminine tone.

Gone was his self-consciousness. The young man was in the moment of ecstasy, and he had lost himself in pleasure. The base of his manhood bulged under my finger as I gently massaged. Semen again started oozing forth, running down his straining shaft.  Poor Adam was so close, straddling the brink of orgasm.

“Stay still,” I coached. “Feel it rising in your penis. That’s a good boy.”

“Oh yes,” he wailed, his head thrown back.

Cum dribbled in a stream to his tummy. The PC muscles began to spasm, and I knew it was about to happen. His legs wide, heels cradled, the man could only sit there, moaning in bliss.

“Oh!” he gasped, as the head of his penis swelled. Toes splayed in the stirrups as he peaked. “Oh. OH. OH!”

A jet of hot cum shot from the man, landing high upon his chest. Another followed, and another. I continued rubbing, watching as his member jerked and spit in ecstasy.

“Hmmm!” he nearly cried, spraying himself in spurts of semen. “Oohmm…”

At last, his wad was spent, dripping down his torso as he panted. After recovery, I popped out the plug, and we got him all cleaned up. Discussing the session, he obviously wanted to come back. I told him we’d give it a month for buildup this time, and while we wait, we can devise the next setup in the playroom.

The end

Source: reddit.com/r/eroticliterature/comments/urkt97/play_date_m_edging_anal_handjob_medical_ds