Tom Joins Harem of Mature Woman Ch. 01

Author's note: Many thanks to my muse for this story, SweetCheeks. The character was inspired by her pics and her writings. All of the actions in the story are fantasy and from my imagination. I did receive her permission to write a story inspired by her. She and I have never actually physically met. That is not to say that she does not lead a sexually exciting life. Her profile indicates that she does. However, this story is my fantasy inspired by her.

Tom was 69 years old when his wife passed. Since retirement she had been most of his social life. He had spent his time either home with her or doing solitary things like hiking and kayaking. Of course, hiking and kayaking can be done socially, but he had always preferred to go solo. They had been married for 45 years. They had an excellent relationship and enjoyed doing things together.

But on her passing he was alone in the world. No real friends. No sex or romance of any sort. He felt like depression was on his horizon.

Speaking of sex, he and his wife had led a very vanilla sex life. Of course his sexual stamina at 69 was not what it had once been, but the two of them had made things work. They enjoyed each other in a variety of sexual and romantic ways. It had just been very vanilla.

In private, however, Tom had been obsessed with some more kinky thoughts. He had never acted on them in the real physical world, but he had spent time looking at online porn, reading erotic stories online, checking out various fetish blogs, and fantasizing about a less vanilla sex life. Which he knew his wife would not be into.

Tom was particularly drawn to fantasies and videos where the male was subservient to the female. He liked CFNM (Clothed Female, Nude Male), femdom, and other fetishes in that line. Obviously, with much more free time on his hands and no wife to surprise him, he started spending even more time on this little hobby- meaning a lot of time on the internet.

And he continued to feel more lonely and in need of human interaction and touch.

One day he was on the personals section of a fetish blog and ran across the following listing:

"71 year old BBW looking for a male house "boy" to move in and serve her in a variety of ways. Do not answer this if you are not okay with large women and older women. Do not answer this if you are only interested in a short stay. I am looking for a man for an extended period of service. In addition, he must not be the jealous type as I like to enjoy the company and service of many partners. You will be joining others on my staff. Age is not an issue. Room and board provided. If interested contact me to set up a time that we can interview each other. Obviously compatibility is needed on both sides." A gmail address was at the end of the listing.

Also in the listing were her city and a face pic. A pretty woman looked out at him with a friendly smile and sparkly greenish eyes. Her shoulder length hair was dark with a reddish tint. Tom assumed that at 71 it was dyed. Bangs covered her forehead. Prominent cheekbones defined her face. Tom decided that she looked friendly, nice, and definitely lovely. He knew some men would consider her too big, but he preferred larger, curvy women over skinny ones.

Tom read the listing about 10 times. The city listed was only an hour away. Was this something he was interested in? Yes. But was it something he wanted to do? He wasn't sure.

He had trouble sleeping that night. His mind was dwelling on the listing. By morning he had decided to at least follow up. He could always back out later. He sent an email to the address listed.

"I came across your house boy listing and I am interested. I am a 69 year old retired widower. I think I am interested in the position. What should I do next? I live about an hour from you." He listed where he lived.

Within an hour he received a response. "Since you are so close, how would you like to meet today? Say around two this afternoon?" It was signed "Karen."

Over a few more emails they agreed to meet at a bar near where she lived.

The rest of the morning Tom was restless and had trouble concentrating on anything. A few times he almost emailed her and canceled. Other times he was very excited about the meeting. He forced himself to eat a small lunch before leaving his house around noon.

After he had driven there, parked, and entered the bar he looked around as his eyes got used to the dim light. There were a couple of guys sitting at the bar. He spotted Karen sitting at a table in the rear. She was a large woman who exuded sexuality. Her face was even prettier than in her picture. She wore a patterned skirt that came to below her knees. It hugged her ample thighs and hips. Her left calf was covered in a large tattoo dominated by roses. On top she wore a green, tight, short sleeve sweater that showed her large breasts to advantage. Her forearms sported more nice tattoos.

She saw him focus on her and gave a wave. He headed back.

"Hi, I'm Tom."

"I'm Karen. Have a seat." Tom sat across from her. She went on, "But I prefer to go by 'SweetCheeks- in honor of this." She smiled as she leaned to the side and gave her own rump a slap.

He said, "I've never done anything like this before. I'm a bit nervous."

"Relax. I'll be gentle. Let's get to know each other a bit. If at any time you decide this isn't for you, just say so and head off. No hard feelings. I will be honest if I don't think things will work out from my perspective."

"Fair enough. Can I get you a drink?"

"A beer would be good."

Tom went to the bar and brought back a beer for each of them. He set them on the table and sat back down.

"Thank you, Tom. I may as well start. If at any point you don't like what you hear, just say so and we can part as friends. My first impressions of you are good, but I will want to know more about you in a bit. So I'll try to give you a picture of what I want."

"Sounds good."

"Well, as the listing said, I am looking for live-in males to join my-- um, let's say harem. That's probably the most honest description. I am not ashamed to say it- I like sex. I like sex a lot and I like a lot of sex. I am married and do live with my husband, Alex. He is fine with my satisfying my sexual needs with others. There are two other men living in the house. Luis is a middle aged Latino and Mike is a 25 year old young man. So you would be one of four. A lot of guys cannot accept that. Give it serious thought."

"I will."

"By the way, Mike and Luis address me as 'Miss SweetCheeks'." She stopped and grinned. Tom nodded. "We have a big house. You will have your own room, but I could visit at any time. Or I could summon you to come to me at any time. The three of you will keep the house, do the grocery shopping, and do the cooking. How are your cooking skills?"

"Actually I am a pretty good cook."

"Great. How are you feeling at this point? Still interested?"

"I am. I need to ask a question though."

"Shoot."

Tom started by briefly describing the vanilla history of his sex life. He went on, "What makes me a bit nervous, Kar- I mean SweetCheeks- is that I definitely do not perform as well now as when I was young. If anything, you seem to be sexually functioning at a super high level. It makes me wonder if I can really add anything to what you have going on."

SweetCheeks answered him. "Until about ten years ago my sex life was limited and unfulfilling. Reading the Twilight trilogy and 50 Shades of Gray turned me on and inspired me to remake myself. I spent time on line and pushed my way into a new lifestyle that emphasized erotic and stimulating sex. I have been a sub, been a Domme, and been gang banged- among other things. I have played with young men and older ones. I have learned that men of all ages have varying advantages. I find that many older men can be enthusiastic, sensitive, responsive, willing to take their time, and willing to substitute other activities if their cock doesn't perform. They can be selfless and generous. I have some nice cocks at my disposal already. I am seeking other skills to supplement my harem. What do you think? Am I asking for something you feel comfortable offering?"

"Sounds exciting. I hope it is okay to tell you that my cock is twitching just hearing you say all that."

"That's good to hear," SweetCheeks replied. "Excuse me. I need the lady's room." She stood and headed back. As she walked away, Tom admired her lovely curves. Her tight sweater accented the curves of her waist. Her skirt was tight over her big sexy ass and thighs. Below the hem her calves were magnificently accented by tattoos. As he watched her ass sway, Tom imagined massaging it.

As she returned she flashed her delightful smile at him. Tom knew he was hooked and had to see more of her. Before sitting she turned her chair sideways, sat, and said, "Test number one. My feet are sore. Can you massage them for a few minutes?"

Tom was surprised. "Right here?"

"Yes, right here. There are only a few other people around."

Tom stood up, moved into the aisle, and knelt on the floor. SweetCheeks lifted her left foot and Tom slid her shoe off. As he rubbed the bare foot he admired the rose pattern tattoo that covered her calf. He glanced toward the bar. Most of the other patrons' eyes were on the two of them, wide smiles on their faces. He wondered if SweetCheeks had played this game here before.

"Oh, yes," SweetCheeks moaned. "That feels great. Feel free to rub my leg also." Tom, keeping one hand on each side of her calf, kneaded her leg from her ankle to her knee. She moved her right leg to the side to make his job easier. His eyes traveled upwards between her chubby thighs and he realized he was seeing her bare pussy. "Enjoying the view?"

Tom blushed and nodded.

"That's far enough for now. Slip that shoe back on and do the other." He repeated the foot and leg rub on her right leg. It had a smaller fleur-de-lis tattoo on the outside of her lower calf and ankle. Again she rewarded him with a nice view of her sexy pussy.

On a whim, Tom said, "May I?" And he raised her foot to his mouth and sucked in her big toe.

"Oh, please," SweetCheeks replied. Tom licked and sucked her toes for a bit and kissed and licked her whole foot as he rubbed it. The other bar patrons were really watching now. He spent some time with his mouth around her toes as he used his tongue to explore each one.

"You know you have to go back and do the left one now, don't you?"

"Yes, Ma'am. I'd love to." Tom put on her right shoe and took the left off a second time. He gave that foot the same attention.

After a time SweetCheeks said to replace her shoe. Tom did so saying, "You know, I'm not generally that much into feet and toes, but yours are so sexy I wanted to explore them. I admit that doing it here in public was a turn on also."

He sat back in his chair. SweetCheeks said, "Thank you. That was nice."

He said, "It was worth the drive just for that!"

They talked more about themselves and answered each other's questions for a while. Tom became more and more comfortable and enamored of SweetCheeks.

Finally she said, "I think you would make a wonderful addition to our household. Take a few days to consider things and let me know whether you wish to join us. I have a contract for you. Take it with you and read through it and complete the questions. Doing this may also influence your decision of whether to join us. Should you decide to do so we can discuss it before you move in and each sign it."

"My tendency is to say 'yes' right now, but you are probably right that I should give it some thought. And look over this contract. It's hard to make an objective decision with you sitting there so enticing and erotic."

They stood to go. SweetCheeks held out her arms for a hug. They embraced. Tom felt her hands grip his ass. He returned the gesture loving the feeling of her ass in his hands. She pushed her hips into his groin and pressed her tits against him. He gasped, "Oh my God!"

She said, "This is to remember me while you decide." She finished with a firm kiss on his lips. "Let me know what you decide."

The whole drive home Tom thought about the feeling of SweetCheeks' curvy, welcoming body against his own. It was all he could do not to pull over and study the contract.

At home he sat down with the contract. He read the purpose statement. It explained the purpose was to establish consent to the relationship, to define the duties and responsibilities of each of them, to establish limits, to establish a safe word system, to define possible punishments, and to promote communication. He read on.

Section 2 gave a place to fill in his name and declare that he was offering himself to Miss SweetCheeks (she had her sections filled in) as a consensual slave. He would be free to end the relationship, but he would not ever be eligible to return. With SweetCheeks permission he could leave the house for other business on a limited basis. No sexual activities were allowed in these cases. Sexual activities in the presence of Miss SweetCheeks would be allowed at her discretion. Masturbation was only allowed at her discretion.

Section 3 explained the responsibilities of Miss SweetCheeks: supplying room and board, physical and emotional safety and stability, etc.

Section 4 listed the expectations of him: to be clean, to be dressed or not dressed as instructed, to make his body available for her pleasure, to honestly answer her questions, to do his part to cook meals and keep the house clean. He would willingly submit to reasonable punishment for disobeying or displeasing Miss SweetCheeks.

Tom found Section 5 to be the most interesting. It was a list of things asking him to define his limits. He marked as off limits: play that involved feces, drinking urine, burns and tattoos, suffocation, extreme pain. He marked as okay most other things such as orally pleasing including rimming, nudity around the house, being spanked or whipped, ass play, water sports on body, and male to male contact including oral sex.

Section 6 informed him that the safe word used in the house was "red light" to stop immediately and "yellow light" if an activity was nearing his limit.

By the end of reading it he decided to give it a try and to start as soon as possible. Why not? He had nothing to lose. Reading the contract and filling it in had him worked up sexually. He realized he had been fondling himself as he read. He pulled down his pants, gripped his cock, and started jerking off. He spit on his fingers and massaged the head of his cock with the wet fingers of one hand while he jerked with the other. He was starting to reach a climax when he realized that he might wish he had waited if certain things were to occur the next day. He forced himself to stop and allow his cock to relax.

He emailed SweetCheeks in the morning. He spent the day running errands and making arrangements for his absence. SweetCheeks replied to him that he could move in the following day. She included other relevant information. He spent a restless night due to being excited- in more than one way- about his upcoming experience.

***************************************

Tom walked up to the front door of the large house. It was fairly new construction. He would almost say mansion. When he rang the bell, SweetCheeks answered and welcomed him in.

The main living area was a large open concept space. Two good sized couches and several comfortable looking armchairs were arranged around the area along with a number of tables. At the back there was a kitchen area to his left and a dining area to his right. Windows lined the back wall. There was a door into the backyard. There was also a doorway to the immediate left and a stairway going up along the right wall.

SweetCheeks motioned him to a chair and he sat down. He handed her the contract, completed and signed. She sat down and read through his notes. "Yes, I think you will fit in quite nicely. Time for the tour. You can see most of the general living area from here. We'll save the basement for later as a surprise." She gave him a wink. She pointed to the door to the left. "That is the master suite for me and Alex, my husband. He is out of town for a few days. By the way, Luis and Mike are out back doing some weeding in the flower garden by the pool. You'll meet them when we get there. Bring your bag and let's go upstairs to your room."

They headed upstairs and walked past several bedrooms. SweetCheeks continued, "This is my husband's second room if I have something special going on in our master suite. This is Luis's room. This one is empty. The last one down there is Mike's." She had stopped at the fourth door. "And this is yours. We designed the house so each room has a bathroom."

They stepped into his new room. SweetCheeks pulled him into her and initiated a long, deep kiss. She squeezed his ass as they kissed. He rubbed his hands up and down her back and ass, enjoying the feeling of her full ass cheeks.

"Welcome home," SweetCheeks said with her infectious grin. "Take a few minutes to unpack. I'll wait out back and introduce you to the others when you join us."

Tom unpacked and got his stuff organized. Then he went down and headed through the door into the backyard. The yard was enclosed with a solid rock wall eight feet high.

The first thing he noticed was SweetCheeks. There she was- laying on her back on a wooden chaise without a stitch of clothing left on her. She had a big grin on her face which was framed by her dark hair. Her hands were crossed over her pussy area, her tattooed arms helping to support her large breasts. Her inviting and chubby legs were extended towards him.

The next thing he noticed were the two nude males working at the flower garden, their asses facing him. SweetCheeks said, "Luis and Mike, come meet our new housemate."

They stood up and came over, exchanged hellos, and shook hands. Luis was middle aged and Latino. Average height and weight. But what Tom could not help but notice was his uncut cock. Though it was flaccid it looked to be about six inches long and very thick. Tom mentally compared it to his own cock which was about half as long when soft. Luis had tight smaller balls where Tom's balls hung down and were quite large. Mike was a handsome young man with more average assets. Like Tom he was cut. Unlike Tom, both men were shaved bare in the pubic area.

Mike said, "Well, are you going to join us? You seem to have us at a disadvantage."

Realizing what he meant, Tom stepped to the side where there was a table and chairs. He stripped off his clothes. He walked back to the group enjoying the feeling of the sun on his body but not enjoying the feeling of self-consciousness that the others were checking him out.

Mike said, "Relax. You look good for someone close to seventy."

"Thanks."

SweetCheeks spoke up. "I think it is only right that I welcome our new partner with a nice blowjob! Tom, come stand over here next to me." Tom walked over and she fondled his cock and cupped his balls with one hand. With the other she pointed to Luis and towards her pussy. As he approached she spread her legs. Tom got a good look at her waxed pussy. Above it was a tattoo of a ribbon tied into a bow as if to announce the nice gift below. Luis got to his knees and began licking her pussy lips gently. She pointed at Mike and then her chest. He went to her side across from Tom, got down on his knees, and began sucking on her nipple and rubbing her breast. Her nipple and Tom's cock began to grow hard together. Tom reached down and rubbed her other breast before pinching the excited nipple.

SweetCheeks licked the precum from the tip of Tom's cock. "Mmm. I love the sweet taste of precum." He watched as she licked his shaft from his balls to the tip- the bottom, the sides, the top. She used her tongue all over his cock head with extra time at his frenulum before she took him into her warm wet mouth. She slowly bobbed her head fucking him with her mouth, looking up at him with her sexy green eyes. Tom stole glances at the others. Mike continued to excite her nipple. Luis's face was buried in her pussy. Tom could see her wetness covering his face. SweetCheeks' nipple was large and firm between his thumb and finger. SweetCheeks was squirming and moaning with pleasure as she sucked Tom's cock.