Tom Joins Harem of Mature Woman

In Chapter 1 Tom was recruited by SweetCheeks to join her harem of live-in men and he experienced his first group sex encounter in her residence. You may wish to read Chapter 1 before continuing.

Once again, many thanks to my muse for this story, SweetCheeks. The character was inspired by her pics and writings on Fetlife. All of the actions in the story are fantasy and from my imagination. I did receive her permission to write and submit stories inspired by her.

As the four of them exited the swimming pool, Tom's mind was rehashing everything he had experienced in the last few days. Reading the sexy, 71 year old SweetCheeks' advertisement, the interview, going over the contract, moving in, and the introductory session of eroticism.

This last 30 minutes had been a time of post-sex sensual relaxation as they had enjoyed the water. Of course there had been some sexy contact even as they recovered in the water. He had enjoyed many different touches. SweetCheeks coming up behind him and pressing her large tits against his back. Coming up behind her and running his hands over her more than ample ass cheeks and wide thighs. Enjoying the feeling of weightlessness in the water as he hugged her to him. She had similar exchanges with Luis and Mike.

Tom had also enjoyed admiring middle aged Luis' magnificent cock and Mike's young hard muscular body. There were enough times that their cocks brushed against him as they swam by that he knew it could not be entirely accidental. He found himself enjoying those touches along with SweetCheeks' body.

After toweling off and laying in the sun for a bit, the subject of going in and showering was brought up. SweetCheeks looked pointedly at Mike and said, "You remember your next job, don't you?"

Mike looked my way and said, "Sure do, Miss SweetCheeks. Looking forward to it. C'mon, Tom, Let's head upstairs."

Tom followed him, curious as to what was in store for him.

As Mike led him up the stairs, Tom admired the trim build and tight ass at eye level ahead of him. The muscles in Mike's ass flexed on each step up. They went into Mike's bathroom. Mike told him to rinse off in the shower. After a minute or so, Mike reached in, shut off the water, and opened the shower curtain. "Stay right there."

Tom realized what was happening when he saw the can of shaving cream in Mike's hand. "I hope you are okay with this?"

Tom answered, "When in Rome..."

Mike pulled over a stool and sat in front of Tom. He lifted Tom's balls and began spreading the shaving cream around them. Then around the base of his cock and the hairy area above it. Tom felt his cock becoming harder. "Sorry about that."

"It's okay by me," Mike answered and gave the tip a squeeze with his other, free of suds, hand. "Turn around and bend over."

Tom did so saying, "I don't think you'll find much more hair. I'm not a very hairy guy." He knew he had no chest and back hair.

"Hate to break it to you, but your ass crack definitely needs clearing." Tom felt the razor begin to scrape over the sides of his crack. "See." Mike held up the razor to show Tom that it was full of hairs. He rinsed it in the sink of hot water and proceeded down to shave Tom's perineal area. "Now turn back to me." Tom did.

Holding cock and balls to one side, Mike shaved one upper thigh and then the other. He lifted the balls. "You have nice, big, hanging balls!"

"Oh, yes. As I get older my balls hang lower and my cock gets smaller!"

Mike laughed. He ran the razor over the underside a few strokes and then released them. He then released Tom's balls and held his cock up while he finished shaving the scrotum and the underside of the cock itself. By this time, Tom's cock was erect. Mike maneuvered it back and forth as he shaved the rest of the area clean. He squeezed out a warm washcloth and soothed Tom's newly shaved areas with it.

Mike then gripped the shaft of Tom's cock and began to pump it. He took the tip into his mouth and sucked that while running his tongue around it. Tom felt his balls tighten and a climax building. When he was about to shoot, Mike pinched the base hard and took his mouth off. Tom groaned in frustration. Mike grinned at him.

"You know we are not allowed to cum without permission. You don't want to break the rules on day one, do you?"

"I guess not. You got me going though."

"Anyway, it's time we started preparing dinner. Let's finish showering off and head down. Luis will be waiting." They stepped into the shower together and rinsed off. Then they toweled dry.

Tom commented, "That's the first time I've showered with another guy since school locker rooms."

"Just wait until all three of us join Miss SweetCheeks in her shower!"

"That sounds fun! Do we put on any clothes before going down?"

"Nope. There are aprons in the kitchen if you want to protect yourself while at the stove. Miss SweetCheeks enjoys watching us work in the buff."

They finished up and headed downstairs.

A stir fry was on the menu for dinner. A naked Luis was getting things organized in the kitchen. SweetCheeks was sitting at the head of the table farthest from the kitchen and facing it, drinking a glass of wine. As Tom approached, he saw that she was wearing a short, black t-shirt with a bare midriff and a pair of black panties below. As he got closer Tom was amused to see "FUCK" in large print where the t-shirt stretched over her tits. Underneath in smaller letters, each with a checkbox, were the words "You," "me," and "off." Tom realized he was staring.

"See something you like?" said Sweetcheeks.

Flustered, Tom answered, "No...sorry...Miss SweetCheek..."

"No?"

"I mean to say 'yes' and that you look wonderful. I see much to like. Sorry for staring. Miss SweetCheeks."

SweetCheeks laughed at his discomfort. "That's okay. I like your new look!" She nodded down to his crotch.

"Thanks, Miss SweetCheeks."

Tom joined Luis and Mike in the kitchen area. Together they prepared the meal. Luis had Tom man the frying, suggesting that he don an apron. Tom did so. The apron choices were all feminine and frilly.

SweetCheeks giggled, "I like the look! Your butt looks cute and sexy sticking out the back of that sexy apron. What do you think, boys?" Luis and Mike agreed.

Tom divided the dinner onto four plates. Mike whispered, "One of us waits to eat. We take turns waiting on her. As the newby, your first tonight. In a bit I'll take your place and you can sit and eat. In the meantime, stand to the side and be ready to serve her."

Mike and Luis each grabbed a plate and sat at the table. Tom took a plate and placed it in front of SweetCheeks. She said "Thank you" as she reached around his waist and gave his ass a squeeze.

"You are welcome, Miss SweetCheeks."

"May I please get a glass of ice water and a refill of my wine?"

"Yes, Miss." Tom followed her orders.

After a time Mike took his place and Tom sat and ate.

The rest of the meal and the cleaning up went smoothly as did the evening. They sat and watched a movie on TV. Luis sat between Sweetcheeks' feet on the floor, her legs spread wide around him. Occasionally she would lift a foot onto his lap and he would massage it. Tom noticed that Luis tended to guide her foot onto his cock, stimulating himself as he massaged. SweetCheeks seemed to enjoy both parts of that.

Tom and Mike sat on either side of her. Every so often she would turn to one of them for a hug and a long kiss or lift her T-shirt and guide one or both of their mouths to a nipple. The whole situations was very sensual though not overtly sexual.

All in all, Tom decided it was an enjoyable way to watch TV.

At the end SweetCheeks announced she was heading to bed. She gave no other instruction so Tom headed up to his room. The others were doing the same. When Tom shut the door to his room his phone dinged. Text from SweetCheeks. "Come to my bed."

Tom stepped into the hallway and Luis was also on his way. They had received identical texts.

The bedroom door was open and they entered. SweetCheeks was on her back in the center of the bed. Tom immediately noticed a large ceiling mirror above the bed. The room was dimly lit with a few electric "candles."

"Hello, boys. I want to feel sandwiched in by male flesh as I sleep tonight. Luis, you on this side and, Tom, you over here." They climbed in. She was naked under the sheet. She rolled onto her side facing Tom. "Luis, snuggle up against my backside." She reached around Tom's waist and pulled him back into her. "Oh, yes. This is what I want. Man flesh all around me!"

Tom felt her magnificent breasts pressing his back, her hips against his ass, and her thick thighs along the back of his own. Her warm breath on his neck made his whole body tingle and gave him goosebumps. Tom pictured Luis spooning her behind them, his cock pressed between his abdomen and her ass. Tom felt SweetCheeks reach around his waist and cup his cock and balls. When he started to get hard she pumped him a few times, getting his hopes up. But she whispered, "Sorry, I'm saving this for a little excursion tomorrow. Nothing for you tonight."

Tom felt her body relax into sleep. He could hear from Luis' breathing that he also slept. Soon Tom joined them.

Hours later, Tom felt himself slowly waking due to motion around him and the absence of covers. As he gained consciousness he heard SweetCheeks softly exclaiming, "Yes. Luis...Yes...Yes." Tom decided to pretend to stay asleep and see where things went. He realized that she had rolled a bit away from him so that she was more on her back. He turned his head to look up at the mirror. Luis had two fingers in her pussy and was finger fucking her. A few minutes later, Luis pulled them out. They glistened with her juices. He spread her natural lubricants on her swollen clit and gently massaged it and she purred with pleasure.

Tom continued to feign sleep as he watched. Luis alternated between finger fucking and clit stimulation for a while. SweetCheeks was twitching in her enjoyment and obviously approaching a climax. Luis, keeping his fingers in her pussy, rearranged himself so as to take her clit into his mouth. Now the action was mostly hidden from the mirror and Tom, blocked by Luis' head. It was not hard to imagine though as SweetCheeks jerked in orgasm letting out screams of pleasure.

Realizing that no one could even pretend to sleep through this, Tom "woke up" and turned to the action.

SweetCheeks told him, "You missed all the fun." Tom nodded sleepily. She turned to Luis. "And my poor Luis is now all excited. Luis, I want to watch you cum. Jack off for me and cum on my tits."

Luis eagerly straddled her stomach with his knees on either side of her and began pumping his cock. Tom and SweetCheeks were both mesmerized watching the thick seven inch erection get worked over. Luis mostly gripped the shaft and jerked himself. Occasionally he stopped to rub his cock head with his precum, cupping the head with his palm. A thick vein stood out along the length of his cock.

"Here I cum," he gasped as his body shook with his climax. Ropes of his cum shot over SweetCheeks tits and neck. Some even reached the corner of her mouth. She licked it with her tongue and smiled. Luis was still pumping and the shots were smaller and less forceful. He slowed to a stop. "Oh, yes," he said.

"Oh, yes," echoed SweetCheeks. "I love watching a guy masterbate. Seeing that burst of cum erupting knowing he was watching me as he came is so sexy! Tom, go to the bathroom and get us some washcloths to clean up."

Tom did so- a couple of warm wet ones and a couple of dry ones. Luis took one of each to clean himself. Tom used the others to clean up SweetCheeks as she fondled his hard cock. He ran the wet washcloth over her tits and neck gathering up Luis' large deposits of cum. He then used the dry one to finish the job.

SweetCheeks gave his cock a hard flick with her finger. "We'll take care of this tomorrow. Let's get some more sleep."

They settled in, this time on their other sides. Tom's hard-on was nestled along SweetCheeks' ass crack. He reached one hand around her and cupped a breast. His nose was near her hair and he breathed in her womanly scents mixed with the aromas of cum and sexual activity wafting up from below. Despite all the sensory stimulation and the mystery of what awaited him tomorrow he eventually slept.

The morning sunlight and SweetCheeks getting out of bed woke Tom. She headed to her bathroom saying, "Go up and get cleaned up and head for breakfast."

"Yes, Miss SweetCheeks." Tom headed out. As he headed across the main living area to the stairs, he saw Luis and Mike, naked as usual, starting work on breakfast. After exchanging good mornings, he headed upstairs, showered, and shaved. Then he returned to the kitchen. They cooked and served breakfast in the same way as they had managed dinner.

SweetCheeks was actually dressed. She had on a red loose top, a pair of tight black pants that went to below her knees, and tennis shoes. She looked at Tom. "You and I are going hiking this morning. Get dressed and we'll head out."

Tom eagerly headed back upstairs. He decided to wear a T-shirt and loose shorts- commando of course- along with socks and tennis shoes. When he returned downstairs SweetCheeks told him to grab the day pack that was waiting and they headed to his car. When he asked where to go she gave him the name of a state park that was about 30 miles away. Tom was familiar with the park.

As they drove Tom made some quick glances at her. The obvious shape of her nipples showing through the fabric made it clear that she wore no bra. She lowered her left hand to his crotch and gave his equipment a squeeze. Then she slipped her hand under the waistband.

"Going commando are you?"

"Yes, Miss SweetCheeks. I thought that would be your preference."

"Good call." She massaged his cock to an erection and then cupped his balls. She cycled between rubbing his cockhead, gripping his shaft, and playing with his balls. "Save your cum. Don't let me push you over."

"Yes, Miss SweetCheeks." Tom concentrated on driving and enjoying the wonderful sensations she was subjecting him to.

As they approached the park she withdrew her hand. "Park in the hiking trail lot- the upper lot." Now she was fiddling with her phone. Tom pulled into the lot and parked. "Grab the day pack. I have some water bottles and granola bars in there." The pack was stuffed more than that. Tom wondered what else was in it.

They headed into the woods from the lot and within 50 feet got to a wide, well used trail. SweetCheeks said, "Turn left." They hiked along the trail passing other hikers and dog walkers going the opposite way. About 10 minutes in, SweetCheeks pointed out a less used trail to the right. Tom knew that the main trail made a big loop back to the lot and this smaller trail cut through the loop and rejoined it. Tom followed her down the trail.

As they hiked he admired her wide, curvy backside, her shape curving in at her waist. Then widening out at her hips and butt. When her shirt pulled up a bit he could see the tattoo on her lower back: "Sweet Cheeks" surrounded by a looping rope and flowers. The tight pants hugged her thighs. He almost stumbled a few times from not watching the path. His cock was still semi-hard from the drive.

Suddenly she stopped. His momentum carried him against her back. She pushed back against his cock with her ass and wiggled it. He murmured his approval. She then turned off the path through the underbrush about 25 feet where there was a small clearing. She took the pack off his back and removed a ground cloth.

"Help me spread this out."

"This is pretty close to the path."

"Hardly anyone ever hikes this path. We'll be fine. Besides, part of the fun is the chance of being seen." They spread out the cloth. "Lay on your back."

Tom did so. He watched as SweetCheeks peeled off her pants and her beautiful pussy came into view. She stepped over his torso. He was now looking straight up at her pussy, the red ribbon in a bow tattooed above it. She lowered herself over his face, feet below his arms and knees above and on either side of his head. Her thick thighs encased his face. She maneuvered herself so that her slit was right over his face. When he managed to tear his eyes off her pussy and look upward he could see up her loose shirt- the bottom of her breasts above him. He had tantalizing views everywhere.

SweetCheeks' pussy approached his lips. "Gently, please," she said. Tom lightly licked the outer lips from button to top. "Oh, yes!" He kissed and licked her perineum, then swiped his tongue into her slit. "Just be still with your tongue extended." She took over for a time, fucking herself with his tongue and grinding her pussy over his face. His nose took in her sexy aromas. "Now kiss and suck my clit. Not too rough though." Tom kissed it and took it into his mouth, gently sucking on it. Then he began to lick over and around it. She moaned her approval.

Suddenly Tom heard a sound. Whistling. Someone was coming up the path whistling Danny Boy. "I think someone's coming," he said.

She joked, "Yes, me!" Then, "Don't worry. I have a couple of online fans who live near here. They are voyeurs and like to watch when they get a chance. Hope you don't mind company. I texted them from the car. Whistling Danny Boy tells me it's them coming. Get back to it." She ground herself into his face harder and he resumed his attention on her clit. "Reach up and use a couple of fingers on my G-spot."

She lifted her left leg and Tom worked his right hand and arm into position and plunged two fingers into her. He pressed them forward and stimulated the front side of her vagina.

"Oh, yes... keep rubbing...right there...keep licking my clit...yes...yes." Tom felt an increase in wetness over his chin as SweetCheeks climaxed. He felt her body relax over him. He licked more of her wetness into his mouth, savoring the flavorful liquid.

SweetCheeks moved her body down his, reaching for his cock. She pulled at his shorts. "Lift your hips." He arched and felt his shorts yanked to his thighs.

Despite how turned on he was, his cock was now only semi-hard. She sat back, her pussy on his cock, and started to grind on him. He looked up at her big, cloth covered tits sagging down towards him and took one in each hand. She leaned forward and he released them as they enveloped his face. He pressed them into his face, enjoying the feeling of them through the shirt. He felt himself becoming erect again.

SweetCheeks leaned back and guided his cock into her. Her pussy felt luxuriously warm and wet. She leaned back and sat still. She gave a wave. Tom turned his head in that direction. At the edge of the clearing stood two middle-aged men, all smiles and waving back to SweetCheeks. She responded by grabbing the hem of her top and lifting it off over her head. Her tits bounced as they were freed. The two men clapped and grinned. She smiled back and began to fuck Tom in earnest. She leaned forward, placing her hands on either side of his head. Now her breasts hung down, brushing his face, their motion matching the motion of her hips.

Tom interchanged holding her tits and grabbing her wonderful ass as she screwed him. The two guys had dropped their shorts and were pumping their cocks. After all the teasing since he last came Tom was worried he might not last long, but he was doing fine so far. He felt SweetCheeks building again. Her eyes were on the two men. Tom glanced over. One definitely was ready and they both watched as he shot out a stream of cum. At that SweetCheeks whole body vibrated as she also came.

She relaxed into a slower cadence- for a short time. She soon started ramping up again. Tom felt his balls tighten and knew he was past the point of no return. "Can I cum, Miss SweetCheeks? Please?"