Tom Joins Harem of Mature Woman

In Chapters 1 and 2, Tom was recruited by SweetCheeks to join her harem of live-in men, he experienced his first group sex encounter in her residence, and he and SweetCheeks had some sex in public on an outdoor hike. You may wish to read Chapters 1 and 2 before continuing with Chapter 3.

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.

Tom woke up the morning following his hike in the woods with SweetCheeks. His mind was still rehashing the experience of sex out in the woods with the other hikers as voyeurs and the memories of SweetCheeks' thick body looming over him, blue sky above her form. He rose from bed and shaved and showered. Then he headed down to the kitchen, nude as expected.

He, Mike, and Luis- all in the buff- prepared breakfast and served SweetCheeks hers, waiting on her needs and wants. She was anything but nude. Black leather dominated her look- a tight black leather corset over a black leather skirt that came to midthigh. Black fishnet stockings and black leather boots. Tom thought she looked sexy and dominating.

When the three boys finished the kitchen clean-up she announced, "I am in a dominating mood today! We will be heading to the basement in a bit." Tom had been curious about the basement ever since she had referred to it when he first arrived.

She held up a paper bag. "But first you will each draw a slip of paper from this bag."

Luis drew first, then Mike, and Tom last. He took the last slip. SweetCheeks said, "Let's see what we have." Luis' slip had a "D" on it. Tom and Mike each had an "S" on theirs. She continued, "Luis, you will join me in a Dom role. Mike and Tom will be our subs in this morning's activities. Luis, go to my room. There is an outfit for you on the bed. Mike and Tom will remain naked, of course."

When Luis returned he was wearing a pair of black shorts of stretchy material that showed off the bulge of his large cock underneath, a black leather vest, and black boots. The four of them headed to the basement.

The basement was one large size room with a number of wooden structures- benches and scaffoldings and other items. There was an open shower in one corner. The light was dim but the area seemed clean and organized.

SweetCheeks ordered, "Slaves. Down on your hands and knees!" Mike and Tom obeyed. Several seconds passed. Luis stepped over and gave each of them a slap on their ass. SweetCheeks said, "That was for not verbally acknowledging the order. For today I am Mistress S. 'Yes, Mistress S'. Got it?"

"Yes, Mistress S." Both Mike and Tom answered.

"And this is Master L for today. He is second in command to me."

"Yes, Mistress S."

SweetCheeks went over to a cabinet and returned carrying two sets of leash and collar. She handed one to Luis. She proceeded to buckle the collar around Tom's neck. Luis did the same to Mike.

"Time for our slaves to get a little walk. Heel, slaves."

She and Luis started walking around the perimeter of the room. Tom followed her and could sense Mike following Luis behind him.

"Luis, aren't they good little slave pets?"

"Oh yes, Mistress. They are doing fine."

After a few circuits they stopped in the corner by the shower.

"I think it's time for a shower. Roll over, slaves, onto your backs. Next to each other." She then stepped towards Mike and Tom, one foot between each of their legs, nudging their legs apart as she stepped. When her feet were between their thighs, she stopped. Luis positioned himself above their heads. Both were still holding the leashes. SweetCheeks hiked up her skirt. Underneath her pussy was bare. Mike and Tom took in the view. Luis had undone a flap in the front of his pants and pulled out his big cock. He began to piss on their chests and faces. She slightly crouched and released a stream alternating between dousing Tom's cock and balls and Mike's.

Tom found the feeling of their warm piss luxurious- especially on his cock and balls. When Luis was aiming at Mike, Tom could open his eyes and watch the urine gushing out of her. When Luis was aimed at Tom, he shut his eyes and enjoyed the warmth as it covered his face and chest. Eventually their streams came to an end.

Luis asked, "What do you say, Slaves?"

"Thank you, Master L and Mistress S," said Mike.

"Yes, Thank you, Master L and Mistress S, for that pleasurable shower," added Tom.

They were ordered to rinse off under the shower and then dry off. They did so. They were also told they were to be silent unless told otherwise- not even any "Yes, Mistress S" or such. SweetCheeks then held up two blindfolds and handed one to Luis. She blindfolded Mike and Luis blindfolded Tom. They were ordered back to their knees and led by leash about 20 feet away.

"In front of you is a bench. Feel for it." Tom touched the bench in front of him. "Now move forward and place your chest on the bench with your hands on the floor on the far side." As Tom got into position he bumped elbows with Mike and knew that they were next to each other on the bench.

The next thing Tom felt was a cold, moist finger rubbing round his asshole. He realized it was wet with lube.

"We are preparing you two for a later activity." The finger entered his rectum, spreading the lube around inside. He jerked when it rubbed his prostate. Then it was withdrawn. It left an empty feeling behind. But not for long. Something cold was now pushing at his rectum. He wondered if it was a dildo, but soon realized it was a butt plug. It was slowly being pushed into him, twisting back and forth to work it in. He felt his sphincter being expanded out. When he gave a small yelp of pain, it was pulled back. Then it was worked back in and out for a bit, each time entering a bit farther, the pain a bit less. Then he felt the widest part pop past his anal ring, almost sucked into his ass. His ass felt stuffed full- now more of a good feeling without any pain.

He assumed- correctly-that Mike had been getting the same treatment.

"Stand up," commanded SweetCheeks. Mike and Tom were guided to a nearby wall. Tom felt himself pushed up facing the wall. His hands were spread above his head and secured to the wall. He felt a stick tapping his knees apart and he widened his stance. The stick tapped back and forth between his knees, then his thighs, then ended tapping his balls a few times. At the same time he felt his ankles secured in place. He was left that way for a few minutes and assumed from the sounds that Mike was undergoing the same process.

Suddenly Tom felt a sharp spank of a bare hand on his ass. A matching sound came from beside him. He wondered if Luis or SweetCheeks was spanking him.

SweetCheeks said, "I understand both of you enjoy a bit of pain and abuse. Well, we are in the mood to supply that."

Mike said, "Yes, Mistress S." Tom echoed him. They braced for more.

And more came. Tom felt much harder bare handed slaps on both butt cheeks and both thighs.

"You were told to be silent!"

An occasional carefully aimed slap caught the back of his balls. Any time that he grunted in response the next one was a bit harder.

Then the slaps stopped and he heard some rustling around. He felt leather fronds brushing his back and he figured out that he was feeling a flogger. He felt it between his thighs and then pushing up into his crotch, tickling his cock and balls. Then he felt it across his already sore ass. For several minutes he was flogged on his ass, back, and thighs. It was oddly stimulating as well as painful.

Then the flogging stopped and he was left alone to listen to the activity next to him. He could not make out exactly what was happening to Mike. He heard some sounds of velcro. He heard some gasps that he assumed were Mike's. There were a few slapping noises now and then. At one point he heard Mike gasp, "Please Mistress. Please let me." This was followed by another slapping noise.

There was no other verbal interaction until he heard SweetCheeks say, "Let's take off slave Mike's blindfold while we work on slave Tom."

Tom then felt a couple of slaps on his rump. A hand reached up between his legs and gave his cock and balls a hard squeeze. He gritted his teeth to stay quiet. Then he heard the sound of velcro as his wrists and ankles were released. Four hands guided and rotated him around so the wall was behind him and the wrist and ankle restraints were replaced leaving him bound to the wall, spread-eagle and facing the room. A body pressed into him. He could feel that it was SweetCheeks, her corseted tits pressing into his own chest. Her hands on his ass held him against her and he felt a sensual kiss on his lips.

She broke off the kiss and he felt her body slide downwards as she dropped to her knees. Her mouth enveloped his cock and brought him back to full hardness. When he moved his cock a bit he got a hard slap on the thigh and her mouth released it. She jerked him by hand for a few minutes. He felt her lips back around his cock head and her tongue playing at the tip as she pumped harder. He felt himself building to a climax. He forced himself to stay mute and still. Just when he was about to explode, her mouth released him again, the pumping stopped, and she squeezed the base of his cock, stopping his cumming. He couldn't help groaning. "Please, Mistress S, let me cum. Please let me." Instead he received more spanks on his thighs and cock.

She then tightly grabbed his balls with one hand. Tom grunted and received another slap. He felt his stiff cock roughly slapped back and forth. He felt small but intense pinches all over his balls. Then on his nipples. Then along his shaft. The blindfold loosened and came off. He blinked his eyes even though the room was only dimly lit. He looked down. His nipples were clamped, the two clamps had a connecting chain. There were clothespins clamped on the skin of his cock shaft and all over his balls.

Tom glanced at Mike. He was done up the same way. SweetCheeks stepped in front of Mike as Luis did in front of Tom. In fact, Luis started mirroring her. Whatever she did to Mike he did to Tom. With his left hand he took the nipple chain and pulled it taut. Tom felt his pinched nipples more intensively. Luis' right hand slapped Tom's cock back and forth a few times. Then he removed the clothes pins on Tom's shaft and began to jerk it. SweetCheeks was pumping Mike's cock. Tom could feel the cum building again. And again, just when he was about to burst, Luis stopped pumping and pinched him off. Tom groaned and could hear Mike doing the same.

Luis and SweetCheeks backed away and she said, "I am so turned on! I am so wet! Luis, I want your nice, big cock! Let's make these two blue balled boys watch." She bent over a table right in front of them, hiking up her leather skirt as she did. Tom looked with jealousy at her wonderful, thick ass and thighs. Luis moved up behind her, dropping his shorts. His cock popping free and slapping against her ass. Then he slid it into her easily and they began to rock back and forth as he fucked her from behind. She pulled down the top of her corset, releasing her tits. The large, soft breasts bounced around below her as Luis slammed in and out.

Tom was mesmerized by the sexiness of them. But despite being so aroused and despite being edged and cut off twice, his erection was softening. The price of getting old he thought to himself. He peeked down at Mike. And of course Mike's cock stood straight as a flagpole. Tom went back to watching SweetCheek and her swinging breasts. She was now reaching climax.

"Yes...Yes...Luis....Slam it in...Right there....God you fill me up...Don't stop...Hard...Yes...Here I cum!" Her whole body shook as she came. Luis simultaneously let out a loud grunt and obviously climaxed with her. He continued to push in and out at a slow pace as they came down from their orgasms.

"Oh, yes. Luis, that is what I needed right now. And you two-" She looked at Mike and Tom. "-I hope you enjoyed the show as much as I enjoyed showing off." She pulled her corset back into place and straightened her skirt. Tom could only think about the juicy state her pussy must be in. Luis did not bother to replace his shorts. SweetCheeks motioned towards Tom and Mike. She began removing the clothespins from Tom's balls. Luis did the same on Mike. They then undid the ankle and wrist ties. Tom was relieved to get feeling returning to his arms and hands.

Next Tom was led to a bench and told to sit and once again be blindfolded. He spent the next 20 minutes fondling himself and listening and trying to figure out what was happening. At one point SweetCheeks called over to him that he shouldn't worry about missing out. That he was next in line for similar treatment. She added that he better not make himself cum.

When his turn came the blindfold was removed and Mike was gone. Tom was led to a low table padded on top. But the first thing he noticed was that SweetCheeks had lost her skirt. She leaned back and sat on the edge of the table. She spread her feet apart.

"Before we go on, I really need a cleanup." She pointed down to her pussy. Tom dropped to his knees and moved in.

"Start with the drips down my thighs." Most of those drips were semi-dry. Tom had to use his own saliva to wet them down so that he could lick and suck them up. He could taste both her juices and Luis' cum. He wondered if Mike had added to it. He worked his way up to her pussy. He ran his tongue through her slit collecting globs of cum. Again, a mixture of female and male cum. He could tell she was working her muscles to force more down to him. He sucked in the wet globs, enjoying the tastes as he did so. He did a final licking around her pussy lips. "Very good, slave Tom. I feel much cleaner. Lay here on your back. Leave your ass hanging off the table."

Tom laid as directed as SweetCheeks put on a strap-on dildo. He watched as she spread lube all over it. She lifted his legs up, indicating he should keep them there. She grabbed his butt plug and pulled it. It popped right out. She rubbed some lube on and into his asshole. Tom thought to himself that he had never seen a sexier sight than SweetCheeks approaching him in her black leather corset, her amazing cleavage, the strap-on sticking out ahead of her, and her sexy face grinning mischievously.

Then the tip of the dildo touched his ass. It actually slid in easier than the butt plug had. SweetCheeks slowly pushed her wide, sexy hips forward, driving the dildo into his ass. Then she began to steadily fuck him. He relaxed to take in the feeling. He knew that some guys really got off when their ass was penetrated. He was not one. He had played with dildos, butt plugs, and had been pegged. The anal penetration was not orgasm causing for him, much as he wanted it to be. He enjoyed the experiences, especially getting pegged, but they were not enough to make him cum. What he did like about getting pegged was the feeling of submission, of being the one getting fucked, of the woman's hips driving into him.

So he concentrated on watching and feeling his sexy Mistress slam into him. When he started jerking himself his hand was immediately removed from his cock. He did not cum, but he knew that she came at least once from the base of the dildo slamming her clit. After that she pulled out leaving him feeling very empty.

SweetCheeks removed her strap-on and produced a similar looking item. She walked to the end where Tom's head was and he realized what she had. This harness went onto his head. It held a ball gag in his mouth. Extending forward from the ball gag was another cock shaped dildo. After securing it on his head she climbed onto the table and straddled his face. Tom watched her pussy come down onto his face. The tip of the dildo disappeared into her slit. Then her pussy and thighs enveloped his face. She bobbed up and down over him. He watched her pussy swallow and release the dildo over and over. It was intriguing to see the action from below. As she continued, occasionally drops of her pussy juice dripped down on and around the harness. He was inundated with the aromas of her pussy.

But suddenly there was a change. He felt his legs lifted again and something against his asshole. As it worked its way in he realized that it must be Luis' big cock. Could he take that? Yes. It worked its way in. It was way different than a butt plug or dildo. Hard and erect as it was, it was still pliable enough to fill every corner of his rectum and touch everything. At least everything that mattered. Luis began actively fucking him. It was amazing. Tom felt his own cock harden. He felt his prostate stimulated. Luis continued to push in and out. In minutes Tom felt himself ejaculating all over his stomach without any direct stimulation of his cock. That must have excited Luis because Tom felt Luis' cock pulse and shoot his load into Tom's ass. Luis slowed his action as he pulsed more cum into Tom. Then SweetCheeks whole body shook and Tom could feel her climaxing above him. They all relaxed as they came down from their orgasmic highs.

When they had recovered, SweetCheeks climbed off and Luis backed away. She helped take the harness off of Tom's face. He could feel Luis' cum leaking out of his ass.

SweetCheeks said, "Well, that was great fun!"

Luis agreed and asked, "How about you, Slave Tom?"

Tom answered, "Oh yes, Mistress and Master. It was an exhilarating morning."

SweetCheeks and Luis gathered up their articles of clothing. SweetCheeks told Tom that they were heading upstairs and that he should clean up the dungeon.

"Yes, Miss SweetCheeks."

She and Luis headed upstairs leaving Tom to his own thoughts.