Paying Rent Ch. 03

Story Info
The deal is coming together.
3.7k words
4.38
24.3k
1

Part 3 of the 6 part series

Updated 09/29/2022
Created 07/08/2006
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It Begins

"Dean, give me a hand moving this coffee table." Both men moved and each took an end, and then slid the table across the front room floor and out of the way. Both were slow to straighten up. Troy moved over toward his friend Dean and placed his hand on his shoulder, just as dean reached his full height, of 5'8", he turned and looked troy in the eye.

"Are you really sure that this is what you want?" Troy questioned, as he looked down into his long time friends face.

"More than anything that I have ever wanted in my life, old friend." Dean smiled.

Troy moved back over to his armchair, and took a seat. Dean joined his wife Sherry, in the middle of the room. Taking her hand they both faced Troy. They were all three ready to begin down this road, into a new and somewhat scary world. Silent for a moment, they all knew that this was the point of no return. They all smiled at each other, but it was clear that Dean and Sherry were not going to move without a word from Troy.

"Alright." Troy smiled. "Lets see what I just bought." He rubbed his hands together. "I want you two to strip, and put your clothes over there on the coffee table and then return to your present positions."

Sherry untied her robe, let it slide down her arms, and then threw it at the coffee table. Smiling she turned back to Troy and, with palms out, stood straight and gave him a kind of wide eyed, "ta-da" look.

Troy smirked and smiled in return. "Very nice young lady, but I'd like you to go pickup your robe and gently fold it on the table."

"Sorry Sir." Sherry said quickly, as she moved over to retrieve her robe, and do as commanded.

Dean had walked back over to the coffee table and was in the process of undressing. He had heard the exchange between Sherry and Troy and was folding his clothes as he took them off. Once naked, he rejoined his lovely naked wife, in the middle of the living room floor, facing his long time friend, he took her hand again.

"You two aren't a bad looking couple." Troy offered.

Dean looked his wife up and down and then looking a Troy, smiled and nodded.

"I don't want ether one of you to speak unless I ask you direct question. Is that understood?"

Both nodded. Dean said a quiet "Yes."

Sherry offered a bolder, "Yes Sir."

"Dean, how is it that you don't have a hard-on? I'm about to bust my pants open."

"Well," Dean hesitated, "You know that I've had some problems." Troy nodded. "And, well this is one of the 'complications'."

"What do you mean? Can you get a hard-on? Or is this permanent?"

"Oh." Smiled Dean. "I can get an erection. It just needs a little help sometimes." Now looking at the floor again, he went silent.

"Don't just leave me hanging." Troy ask, sitting up. His sarcasm was not lost on his friends. They all giggled a little and then returned to their solemn tone.

"As we have tried to prepare ourselves for 'you', we have actually found a couple of things that work." Troy nodded and Dean continued. "Of coarse there is some drugs, like Viagra, but my Doctor doesn't like me using them. He says that it can really mess with my bad blood pressure."

"So has he got another prescription, or what does he suggest?"

"He has given me some samples to try, but warned us not to use them more than once a week, and he would prefer less often."

"So does that mean that this whole thing is just going to be me having sex with your wife?"

"No." They both answered in unison, and then smiled at each other.

"We have found that there are other things that will work, at least on a temporary basis." Troy could see Sherry squeezing Deans hands and smiling supportively, and he gestured for Dean to continue. "For example, Sherry loves to be spanked." Troy smiled and raised an eyebrow to Sherry, who grinned and nodded her head up and down quickly.

"She likes to be spanked until she is crying, and then I usually stop anyway, because I don't like to make her cry."

"I would love more and harder." Sherry butted in.

"I ask you not to interrupted." Troy stated sternly.

"Sorry Sir." Sherry whispered.

Troy looked at Dean and nodded.

Dean knowingly continued. "Well, anyway, trying to prepare for anything that you might want us to do, I ask Sherry to spank me."

"How did that turn out?" Troy interjected.

"Not good for Sherry, she just doesn't have it in her."

Troy looked at Sherry and they both nodded, as Dean pressed on.

"She ended up bawling hysterically and couldn't continue." Sherry started to tear up and Dean put his arm around her. "She just doesn't have the dominant gene."

"So where are we going with this?" Troy ask.

"Oh, sorry Sir." That was the first time that Dean had addressed Troy as Sir. "I didn't mean to drag this story out, but out of the experience, we learned that a spanking will give me a hard-on. We don't know how long it will last, because we were cut short."

"I'm so sorry." Sherry whimpered into Dean shoulder.

"It's alright baby. We learn and we move on." Dean comforted.

"So, what else have you got?" Troy pressed.

"Oh, yes, sorry. We have also done quite a bit of anal play. Both on Sherry, she loves it by the way, and on me."

"So, what all do you think that I'm into?" Troy questioned sternly. "What have I ever done to make you think that I'm the least bit interested in any kind of sex with you?"

"Sorry Sir." There it was again. "It's not that, but we mean to serve you fully, and we mean in any way that we possibly can. We just tried to think of any possible scenario, and any possible act that you might wish us to do, whether as a couple or individually."

"O.K. I'll buy into that." Troy responded. "Thank you, by the way. As for poking you up the ass, I'm not ready for that. Let's just take that a little slow for now."

"Anything you wish." Dean looked down, embarrassed. "Anyway, getting my ass licked and fingered will get me hard. We have also learned that a dildo, or a vibrator will keep me hard for awhile longer."

"Well, buddy, don't hold your breath waiting for me to lick your ass. Cause it ain't gonna happen." Troy smiled sarcastically. "How long can you keep it up? You know, with something stuck up your but I mean?"

"We don't know. We haven't tried a lot of things, and the ones that we have tried we only tried for a little while."

"Gees, the more we talk, the more we learn." Troy sat quietly for a moment, collecting his thoughts.

"I need to be getting home." Pausing a moment to see his friends reaction, Sherry and Dean looked and each other, and then back to Troy. The dejected look on their faces spoke volumes. "Don't worry. We're going to do this." Troy added with a smile.

"Thank you so much." Said Dean, as they both let out a sigh of relief.

"We're going to play for a minute and then I've got some things for you two to do, then I'll go home and talk to Joan about you two moving in." Troy stood up and removed his clothes. He was only six years younger than Dean, but he looked fifteen years younger. Also, standing 6'3", he over shadowed his friends by quite a margin. Then taking one step closer to Sherry, she smiled up into his eyes. He reached down and ran a finger through her pussy lips. Smiling, as he returned to his seat, he rubbed his fingers together, slick with her moisture.

"Alright Sherry. I want you on your hands and knees in front of me. Give me a good blowjob. Dean I want you on your hands and knees behind her. I want you to lick out her asshole. And Dean, I mean I want to see that little asshole literally shine! Do you understand me?"

"Yes Sir!" Piped Dean, with a smile, as they both quickly moved into their assigned positions. Sherry quickly engulfed Troy's erection. First licking the head and then the shaft before trying to swallow it whole.

Troy placed a hand on her shoulder and one on her head as he watched his two friends begin to work for his approval. Dean had moved in behind Sherry and the way she was moaning over his dick, he figured that Dean was doing his part. He had to give her high marks for her effort and technique. His own wife didn't like to give head and only indulged him on occasion.

He was no expert, but this felt pretty damn good! Troy enjoyed watching the scene that was playing out before him, and let it continue for a while, but he didn't want to cum in her mouth. He realized that this was their first sexual act as slaves to him as thier master. Before too much time had passed, and he got any closer to climax, he tightened his fingers into Sherry's hair and pulled her reluctant lips up and off of his dick.

"Dean, stop for a minute. Sherry, I want you to crawl up here and straddle me." Sherry smiled and began to move into position. As she slid a knee onto each side of Troy's legs, he reached up and cupped her tits. She leaned in and began kissing him. Troy broke the kiss off with, "You have nice tits baby."

Sherry smiled and said, "No, now 'YOU' have nice tits." She giggled and then added, "But thank you."

Her hand trailed down his chest, finally grasping his firm penis. She shifted and aimed it for her slit.

"Stop!" Troy said forcefully.

Sherry froze, wondering what she had done wrong.

Troy smiled evilly. "Dean, 'You' put my dick into your wife's cunt." Sherry smiled back into his eyes. Dean placed one hand on the small of Sherry's back and with the other on Troy's penis; he gently pushed his wife down onto his friends' dick.

"That was very good Dean." Troy said with clear condescension. "Your wife has a nice, soft, wet, pussy."

To Troy's surprise, Dean's answer came without any sign of jealousy or spite. "You know it, buddy. She is the best sex in this town, or any other."

Sherry leaned in and kissed Troy again, this time tonguing him for quite some time. She was well versed and creative as she bathed him in kisses and sucked his neck.

"Dean, I want you to continue licking her asshole."

"As you wish, Sir."

And almost immediately, Troy could feel Dean's beard rubbing in between his legs and his tongue working on her asshole. Sherry began to slowly slide up and off of his shaft, then reaching the top, she would slowly descend, and as she slide down the length of his dick she would kind of twist and swirl her hips. The feeling was magnificent.

Then Troy got a new shock. As Sherry would rise up off of him, he could feel Dean licking his balls and lower shaft. Then as she lowered back down, he could feel Dean's tongue slide back up Sherry's lower slit and up to her asshole, where he would shove it inside her, and twirl it around.

Sherry and Dean were falling into a wonderful rhythm, but Troy couldn't hold back much longer. "Shit!" Troy said. "I hate to say this, but I need you to stop." Looking at Sherry.

She looked back blankly, "Did I do something wrong? Sir? I'm very Sorry."

"Hell! No!" Troy laughed. "You two are so damn good, that I'm about to blow my load in the first couple of seconds we're together." With his hands now resting on her thighs, and looking her directly in the eye, Troy took a breath. "Need you to slide off of me baby."

Sherry moved gently, but followed her orders even as Troy was giving them. "I want you to turn around and spread your ass cheeks and put my dick up your ass." Sherry smiled and gave a little giggle as she stood and turned around.

Dean remained on the floor, and as she lowered herself back down, without being prompted, he took Troy's penis and guided it into his wife's descending asshole. She had a hand on each ass cheek and her hole was quite wet with Dean's slobber.

Even with his dick greased up from her twat, they met with a little resistance, but soon were sliding in. Both Troy and Sherry let out a collective sigh, as she hit bottom, and rested her soft ass on his lap.

Troy reached around from the back and took one of her breast in each hand. Then he eagle claw gripped each tit firmly and pulled her back into his chest. She let out a little gasp again, at the pain, but said nothing. "Don't move. I want to just feel this for a second." A moment passed, and he could feel her asshole involuntarily contracting around his dick. "God, that feels great! Dean, don't you have something to do?"

"Yes Sir."

And immediately Troy felt whiskers brushing his inner thighs and then a tongue on his balls. Dean's tongue moved up to Sherry's wet pussy lips and then slid inside. Troy could feel his friends tongue swirling around inside of Sherry.

"Damn!" Troy whispered into Sherry's ear. Sherry bucked her hips and tightened her muscles, both her ass, around Troy's cock, and her pussy around her husbands tongue. He could hold back no longer, and let his cum flow into her tight ass.

Resting a minute and catching his breath, Troy rubbed Sherry's chest and nipples. Then once recovered, he started slowly, "That was fantastic!" He almost whispered. "You two will be the death of me." Sherry leaned forward and started to rise up. Troy, still holding her tits, tightened his grip and pulled her back onto his lap.

"Not yet baby." Looking over her shoulder and down at Dean. "Back up buddy, but stay down there." Dean complied. Whispering into Sherry's ear, "Honey, I want you to get up, spin around and clean my cock off."

Troy loosened his grip, on her tits and let go as she rose up and turned around. She quickly knelt down and began licking his cock.

Looking passed her, toward Dean, Troy said, "Guess what your job is buddy?"

Without any hesitation, Dean almost leaped forward and began licking and sucking on his wife's asshole. Troy, once again rested a hand on Sherry's shoulder and one on her head.

"I've never had anal sex before." Troy mumbled, more to himself than to his companions. "That was truly fantastic!" Then he just quietly watched his two friends continue to follow his orders. There would clearly be physical limitations, but setting those a side, this would be better than any fantasy he had ever concocted on his own.

"Alright, you two get up and stand in front of me again."

Sherry pushed off of Troy's lap and stood, then turned and help Dean to rise to his feet. They kiss quickly, turned to face Troy, and held each other's hands.

"Well how do you two feel?"

"Fantastic!" Sherry yelped, as she jumped in place.

"Wonderful, truly wonderful." Dean said looking directly into Troy's eyes.

"So this is what you two have in mind?"

"Yes! Most enthusiastically Yes, this is exactly what we want to do." Dean responded, while squeezing Sherry's hand and pointing to each other. "Please, Please dear friend, is there anything else that we can do for you? Anything to make you feel better? Anything to bring you pleasure?"

"No. I'm really good right now. But thank you for asking. You two are really amazing. It's no wonder that I love you both so much." Troy stood up and reached for his clothes. Sherry and Dean both also reached for Troy's clothes, in an attempt to help him dress. "I didn't tell ether one of you to move. Now get back over there."

"Sorry Sir."

"Apologies, Sir."

"Don't worry about it. We will formalize some rules as we get into this." They both nodded and Troy began to dress. "O.K. I have some stuff for the two of you to do."

"Yes Sir. Anything at all." Dean responded smartly.

"First and foremost, Sherry."

She looked up brightly into Troy's eyes and said, "Yes dear, anything all."

"I can't stand a hairy pussy. It has been a sore point between my wife and I for many years. You will happily keep your entire body shaved."

Sherry smiled and nodded, "Yes sir, happy to do it sir," and then she giggled like a schoolgirl.

"I'm serious about this Sherry. I want you happy about it, and I want you completely bare. Is that understood?"

"Yes sir, that won't be any problem at all. Anything that pleases you will please me even more my love."

"Dean, I want you to shave your crotch too." Troy paused a second to watch Dean's face. But to his surprise, there was no anger, discomfort, or animosity of any kind. "I don't have any specific plans for you right now, but be sure that your crotch and asshole are shaved and stubble free."

Troy was pulling his pants on now and started to look for his socks. "The two of you will never again wear clothing. Of coarse there will be some obvious exceptions. When any of your kids come over, when my wife is around, when we are working, or any other time that I specify, I will expect you two to dress quickly and correctly. But the second that you step in that door, the clothes are off, do you understand?"

"Yes sir." The two said in almost unison, then smiled at each other.

"What?" Troy questioned.

"Well," Dean began, "we expected this much."

"Don't get to sure of your selves, I have more." Troy smiled, as he sat down to pull on his shoes.

"Sherry, my love." She looked up from her husband and over at Troy. "I want you to let your hair grow longer. I don't care for it this short. I know that it's easier to take care of, but I want it longer. Let it grow and I'll decide just how long to let it go. I'm thinking down to your shoulders."

"Yes sir, it will be my pleasure."

"Dean, I want you to keep you beard in better shape."

Dean raised a questioning eyebrow.

"You let it get pretty rough and scraggly between trips to the barber. Keep it trimmed nicely or I'll have you shave it off. That's not such a bad idea anyway, I've never seen you without a beard."

Dean looked a little alarmed, but also resigned.

"For now just keep it trimmed buddy."

"Yes, I will, thank you, Troy" Dean said while still looking down.

"O.K. those are the main things." Troy stood up and approached the couple.

"You two are in bad shape and I want you to be around a while." Now circling the pair as they kept facing the chair he had just vacated. "Starting tonight, the two of you will start walking. Tonight you will dress comfortably and you will walk around this subdivision. Tonight make one loop. That will be about half a mile. Every corner that you come to, I want you to stop and kiss each other. I want a good kiss that people will remember."

The pair smiled at Troy. "We can do that sir." Dean said smiling.

"I will increase the length of your walk every day. You will be sore and tired every night. You will both loose some weight and over all be in better shape."

"Thank you sir." Sherry smiled, at Dean. "I've been trying to get him to exercise for years."

"You need it too baby." Troy jibed. "I want you two to be around for awhile. And if I'm going to own you, then I want it to be good looking property." They all laughed.

"I'm going home. I want the two of you to go clean up, shower, shave each other, and then go for your walk. Remember, when you return home you are to be naked at all times. Carry a little towel with you, I don't want ether one of you leaking on the furniture." They all laughed again.

"Tomorrow I will be by after work. I need you to have all of your bills, and anything else concerning your money, all together, so that we can go over it and see where we are." Troy had worked his way toward the door, and then turned back.

"I need to see any paperwork that you have on your work also, when your final days are, any benefits coming our way, and anything else that you can think of, does that sound alright?"

"Yes, I will have everything ready for you sir." Dean smiled. "Thank you again for doing this for us. This really is very, very, important to us. We love you very much. Thank you so very much."

Troy put out his hand and took Dean's. They shook hands and looked into one another's eyes. "I really do love you and your wife. We will make this work. I know that I will make some mistakes, but if you are willing, we will build a life together."

Dean's eye's teared up. "Thank you so very much. You are truly the most important and best man in my life." Letting go of Troy's hand, Dean reached back and took Sherry's hand. "Without you we would have nothing, but with you we have everything. Thank you."

12