Pretty in Pin

As sixty seven year old Everett Horton sat on the edge of the motel room bed waiting for his new acquaintance to emerge from the bathroom, his mind kept going back a half a century to a motel room even more dingy that this one in Colonie, New York was.

Back then Everett wasn't the old geezer waiting at the bed. He was the lad in the bathroom getting dressed the way that the man wanted him, and while it disturbed him back then when he was the one putting on the panties he had been given, Everett feared that the reason it had bothered him was that he had liked it. A lot, and while it was the only homosexual experience in his life, he had been tempted many times since then but had resisted.

The young fellow in the bathroom wasn't much like he had been. Tommy - what he had given as his name - was a 19 year old college student and was nowhere near as naive and ignorant as Everett had been back there decades ago in that motel in Malone, New York.

This effort to recreate the past on Everett's part had been on his bucket list for decades, and now with his wife passed for a few years and his time running out he had used social media and technology to find a young fellow willing to help him.

Everett explained what he was interested in doing and said that it would involve a bit of role playing, part of it with him being the seducer like that other man had been, but in the end Everett wanted to play the himself in the role he had played half a century ago. At that point Tommy would begin playing the part of the man that took Everett the boy that night.

Everett knew it was risky to have a casual meeting with a stranger like this but he realized it was a bigger risk for young Tommy who had a lot more to lose. They had both been cautious in meeting but in the end Tommy agreed to go along with it, even the panties.

The pink panties. Everett had been made to put a similar pair on back then, and while he hadn't have them on all that long he had enjoyed the feel of the satiny fabric on his skin and the way that man's hand felt as he rubbed him. This time though, Everett wanted to be in that other man's place, the one rubbing the panties and having Everett do things to him. After that, they would swap roles.

The bathroom door opened, effectively interrupting his reminiscing, and then Tommy entered the room slowly and shyly like he himself had. Unlike Everett Tommy was a big strapping lad, his 5'11" frame nicely proportioned, and his hairy legs showed that he was a natural redhead.

It wasn't Tommy's legs that Everett fixated on but the bulge in the panties that seemed to be throbbing in the snug confinement, and that was another instance where the two differed greatly.

"Tight?" Everett asked.

"A little," Tommy admitted and he grinned sheepishly, making him look a lot like Alfred E. Newman of the old Mad magazine days.

"Come here son. You look wonderful," Everett beckoned, and as Tommy came over to face him he could feel the heat from his body.

Everett reached out and ran his hands up and down the crinkly fur that covered the boy's lower torso, enjoying the feel while looking at what looked like a snake crammed into the tight pink undies.

"You're very well-endowed," Everett finally said when he couldn't ignore the elephant in the room any longer, and as he brought a shaky hand up to the bulge he added, "You're very well endowed indeed."

"Yes, I guess am," Tommy said as Everett's wrinkled hand made contact with the satin, and the boy let out a sigh that Everett echoed as the old timer ran his hand along the length of the bulge.

"You aren't even fully hard yet," Everett noted as his hand ran up the semi-spongy tube which was stiffening under his stroking, and as it grew longer and threatened to explode out of the satin Everett wheezed, "Oh my."

"We don't have to - you know," Tommy said of what the old man had told him he wanted done to him, but Everett shook his head no.

"No. I mean I can understand why you wouldn't want to, but I still do," Everett said before leaning forward and kissing the bulge, nibbling his way over towards Tommy's hip where the the tip was.

"Good, because I want to,' Tommy said as he cradled the old skull in his hands. "I want to fuck you in the ass so bad."

Everett's heart skipped a beat when he heard those words in the last sentence, because that was what that man had said to him 50 years ago.

"I like the way these panties feel on my dick," Tommy said as Everett gently bit the satin. "Don't know if it's the panties or what you're doing but either way, it's making me really hard."

"I know," Everett agreed as he rubbed the flat of his hand along the length of Tommy before wrapping his arms around him and hugging him, his hand squeezing the tight buttocks while exhaling loudly.

"I want to see you," Everett said as he leaned back, but Tommy's freckled hands grabbed his when he brought them up to the elastic of the undies.

"Get your clothes off first sir," Tommy told him, and reluctantly Everett got up and shed his shirt and trousers, but when he started to sit back down Tommy stopped him.

"The boxers too sir," Tommy said.

"In a while."

"Now sir," Tommy said, and as he reached down and grabbed the base of his own cock through the satin he squeezed it and added, "If you want this get them off. They're coming off anyway."

Everett shrugged and very reluctantly let his baggy boxers drop to the carpet, half expecting the boy to laugh at the sad little wrinkled tube that was barely visible in the silver bush around it.

"Love hairy chests," Tommy said as he ran his hand over the silver cloud on Everett's chest and looked down at the senior's tiny organ without comment while letting his hand go down to take it. "Relax. You're supposed to be enjoying this."

"I am, believe it or not," Everett said as he felt his dick begin to get hard as the lad pulled and stretched it out to something halfway respectable.

"That's it - I can tell you are," Tommy said with a smile as he let go and put his hand on the old man's shoulder and eased him down to the perch at the end of the bed.

Everett exhaled when he saw that not only had the bulge gotten bigger, making the panties arch out from the force of his arching organ, but there was a wet spot over by the young man's hip.

"I'm excited too," Tommy declared as Everett took the elastic in his hands and tried to coax the satin panties down, not an easy task because they were even more cramped than they were when they went on.

Everett finally got them down a ways, enough to expose the head of Tommy's uncircumcised manhood, and as more and more of the vein-riddled underside of the shaft was exposed Everett's heart beat faster and faster until at last it came free.

The old man ducked away as the long arching prong swayed upwards majestically, the ghostly pale organ bobbing as Everett struggled to get the panties off Tommy's hairy legs.

"There," Everett said as he got them off, inhaling them briefly before tossing them on his own clothes for a souvenier, and then turned to the business at hand.

"Damn," Everett whispered to himself as he brought his right hand up to the base of the shaft where the massive organ emerged from the burnt orange curls, and when his left hand grabbed above his other hand he couldn't help to see that the shrouded glans was still uncovered. "You should be in the movies."

"I was once," Tommy said, looking down and obviously proud of himself. "A man wanted me to have sex with his wife while he watched and filmed it."

"You like girls too?" Everett asked.

"Guilty," Tommy said, and while they would have never done anything like that, the thought of his late wife getting a look at what he was holding amused him.

"Been a while," Everett said as he leaned forward and prepared to take the second cock he had ever held into his mouth, the foreskin inching backwards to expose the tip of the head which was a ruddy pink and stood out against the creamy white below it.

"That's it, skin it back and suck it hard," Tommy sighed as he watched the old fellow open wide to take it the knob. "Don't be shy."

"Ahh!" Tommy exclaimed as Everett moved his lips back and forth over the puffy ridge, and Tommy lifted his left leg and put it on the mattress next to the senior's hip. "You're doing fine sir. Is it big enough for you mister?""

Everett's jaws were already aching as he struggled to get his lips down further, taking his upper hand off so he could fondle the dangling nuts underneath, the somewhat normal sized moist orbs fitting nicely in his palm.

This allowed Everett to use the hand still wrapped around Tommy's cock to go up and down the throbbing shaft, something that Tommy seemed to appreciate.

"That's it man, jerk that cock," Tommy exclaimed. "Imagine what this big dick will feel like in your ass. That man who did you when you were young - you said he was big too right?"

"Yes," Everett wheezed as he came up for air for a second, and as he looked at what he was sucking he added. "At least I thought he was until now. This is..."

"You're doing fine sir," Tommy said as he took his cock from the old timer and raised it upright and suggested, "Give my balls some love if you want."

Everett nodded and ducked under to get at the furry sac, and when he started sucking on the bigger one hard he got a delighted yelp from the lad.

"Oh yeah - fantastic!" Tommy declared while leaning his lower torso forward to make it easy on the old man. "Suck them nuts good."

Everett heard the snorting and grunting but didn't realize at first that it was him making the noise, and he was a bit sad when Tommy had him go back to his cock.

"You're good - no lie," Tommy exclaimed after watching the senior valiantly try to get his mouth farther down the shaft, and then he reached down and lifted Everett up to his feet.

Even though Tommy was only a couple of inches taller than he was, Everett felt like a child as Tommy hugged him to his well toned upper torso, and that feeling was compounded as their genitals ground together down below.

"Feels nice doesn't it?" Tommy asked as he leaned back a little so they could watch their cocks duel, and Everett laughed when Tommy made his cock twitch and slap his boner.

"I'm not going to win this battle," Everett mused as the two pale organs rubbed and tapped against each other.

"There isn't a loser, is there?" Tommy suggested, and the old man was forced to admit he was right because the feel of the boy's hot throbbing organ against his was magical. "Here. Let's..."

Tommy had Everett hold his dick out straight so Tommy could rub the tender tips together, pushing them into each other making the gooey openings leak even more.

"Nice?" Tommy asked, and Everett nodded even though seeing the two dicks together like that was a little embarrassing, especially since the senior citizen's early assessment of the lad's cock being twice the size of his own might have actually been an understatement.

Together, the two hands clamped themselves together tightly, and for a moment it felt so good Everett was afraid he was going to cum. Luckily Tommy let go and eased the old timer down onto the bed before going over to the little bag he had brought with him.

"Please be gentle," Everett heard himself whimpering as he watched Tommy snapping open the tube of gel while returning to face him.

"Here, why don't you do the honors mister?" Tommy suggested, handing over the lube to the senior whose hands were visibly shaking as he took it. "Still time if you don't want to you know. We can just talk and stuff."

"No, I'm fine," Everett replied as he filled his palm with lube. "They shake a little bit even when I'm not nervous."

"That's it. Lube that big boy up good," Tommy encouraged as Everett rubbed the gel up and down the length of the organ, even the base where it wouldn't be needed. "Now get on up so I can grease your anus."

Everett felt light-headed as he stood up and climbed onto the bed, getting on all fours for the second time in his life, and Tommy playfully smacked his pale bony butt as he took in the view from behind.

"Damn mister, you got a pair of nuts on you don't you?" Tommy said as he reached down and grabbed the low hanging balls that had been swaying between his spindly legs, and as the lad kneaded and twisted them the moan his got in return made him ask, "That hurt?"

"No," Everett grunted, and as a result the lad began to rough them up even harder, almost twisting them in a knot as he leaned around him to looked down at the old man's reaction.

"Yes, you like your balls played with rough don't you?" Tommy cackled as Everett nodded with his eyes screwed shut and him biting his lower lips. "Makes your little dick hard doesn't it?"

Everett nodded, stunned at how the words Tommy used were so similar to the way that man had mocked him years ago, and just like it had done that time, the ridicule only made him harder.

"I should have said that," Tommy said as he milked his aging nut sack. "That wasn't nice. I'm sorry."

"No need. After all, I am rather small, and if I somehow had forgotten that, being with a man built like you would have reminded me," Everett explained.

"It's time," Tommy whispered in his ear, the very words that Everett had asked him to use, and the chill that went down his spine made him shudder even more that the greased finger did... - or the second finger... or the third, until finally the digits were removed.

Tommy then assumed the position behind Everett, rubbing the plump knob against his anus and up and down his ass crack as Everett waited for the second man to take him anally, and since this lad was even larger than that man had been back then he braced for the pain.

"Uhhh!" Everett moaned as the tip of the lad's monster poked into the puckered ring, and the old man's arms buckled briefly when the fat head popped inside of him.

Tommy stopped there, allowing the elderly man to recover before easing a little bit of the shaft inside him before retracting, stopping before pulling the ridge of the knob out.

"You okay man," Tommy asked, and after Everett grunted in the affirmative the kid reached under and found the old-timer was still fairly hard. "I guess you are okay. You like my cock in your ass don't you? Have some more."

"OHHH!" Everett groaned when after Tommy slipped a little bit of his massive meat in again, he kept going until most of his greased tool was in the hot cavern.

"Oh man, you are so tight," Tommy hissed as he held the old man's pale bony hips and began to move in and out in rhythm, nudging a little more in with each stroke until Everett was fully impaled with the lad in right down to his nuts. "You got it all. Want me to stop? I can cum any time you want."

"No. I want it," Everett managed to say as the grip on his hips got more firm and their bodies began to slap together,

"And you're going to get it," Tommy cackled as he began to thrust harder and faster, and the moans the old man was making along with the creaking bed inspired him more.

Tommy reached around again as he leaned into the senior, and when his fingers found the slim shaft he jerked it hard.

"Gonna cum aren't you?" Tommy asked as he kept humping and jerking, and the answer came in groans.

A minute later the old man's face was in the bedding and his spent dick became too gooey and little for Tommy to hold onto, so the lad concentrated on business.

"You want me to cum yet?" Tommy asked, and although he couldn't hear what Everett said he saw the nod of his head, so he stopped holding back and let out a bellow and he erupted into the old fella, filling his aged bowels with his hot seed until he had nothing else to give.

As Tommy began to go flaccid he slowly pulled out of Everett, wincing and looking away when he saw the gaping orifice that took its time retracting and going down to the bedding.

"You alright Everett?" Tommy asked as he put his hand on the ashen back when he thought he heard sobbing, but while the senior looked disheveled he was okay.

"I'm fine. Thank you," Everett replied with a weak smile, and after the lad rubbed the old man's back for a while he said he had to go.

"Classes in the morning," Tommy said as he ran into the motel room bathroom for a quick shower before drying and getting dressed while Everett watched.

"Look, I know we discussed something and I respect your feelings about that, but I would still like to at least take you to dinner sometime as a token of my appreciation for doing this," Everett told the boy before he left. "No strings attached of course."

"Oh, I wouldn't mind the strings," Tommy replied with a smile. "Having been eating campus food for months I would like that though. You know how to get a hold of me"

As Tommy put on his pants Everett felt a shiver run down his spine as the lad's flaccid penis disappeared from view, the size of the organ even in repose making him shudder when he realized all of that had been inside of him.

"You were marvelous," Everett told his young friend before he left. "You can tell your drama teacher that you were in a play where you played two parts involved totally different people, and the crowd loved it."

You might not be able to relive history completely, Everett concluded when after Tommy left he struggled to sit up on the bed, the feel of the lad's seed leaking out not unpleasant, but this had been plenty close.

"Maybe I'll do this once every 50 years," Everett chuckled aloud as he waddled to the bathroom. "Should be recovered by then."

*****

Thank you for reading.