HOA King
This was written and edited with Grammarly. Hopefully, the flow works. Thanks for reading.
Caroline shook her head as she prepared to be with her benefactor. She knew him to be the oddest man she'd met. He was a well-to-do businessman, 20 years or more her senior, well-groomed, and fit from being an avid tennis player. Yet he was also, effeminate, with a higher voice, and oddly carried himself from a lifetime of being alone. Also, a misogynist who bickered with men and women over petty things. Yet, he had local weight as the head of the neighborhood HOA. He also had bizarre sexual fetishes. Caroline figured that he was impotent in any form of sexual situation outside of what he was able to get her to do. She relied on him because she was always in dire need of financial assistance for her kids. And she and her two kids lived in one of his houses a few streets over.
This summer evening she was alone in Kevin's spare room in nothing but a red teddy and a tight black harness. She was attaching the straps to her thighs when Kevin walked into the room. He spoke and moved like he was conducting a meeting, demanding to know why she was late and moving slowly.
She told him to shut up. He stopped abruptly and shook his head then looked off. Then changed his tune, asking how long she had tonight.
"Look, Wimbledon boy, you and your cutesy all-white tennis outfit should keep quiet. Once I start I might just wear that ass out." Kevin smiled like it was his birthday.
Caroline snapped a 7" dildo into the front of the harness and felt the weight as it dropped from her hand. It bobbed about for a second until she pulled on it a few times, and let it go so it bobbed again. As Kevin got on the bed he dropped his shorts leaving him his polo and shoes. She scolded him about shoes in the house., and in the bed. He mumbled something back. Caroline reached into a dresser drawer and pulled a tube of lube to show him. She then squirted some on her hand to rub on the fake penis. Before him she masturbated on the plastic unit, stroking in slowly as she artfully twisted her hand. Kevin propped up on an elbow like he was watching a movie. He then remarked that she looked fabulous in the fading evening light.
With her fake penis bobbling about her Caroline pulled on a wig of straight, long blonde hair. Her outfit is now complete: barefoot, blonde wig, red teddy with no material covering her backside, a black leather harness about her waist, and a sizable fake penis. She tossed the lube to Kevin who was propped up on an elbow as he caught it. He proceeded to smear a handful up his rectum. When he went to say something she preemptively held a finger up to shush him.
Crawling on the bed she moved his leg so he was flat on his back. His eyes moved back and forth from her emotionless face to her plastic cock. Her cock had a life of its own now, bobbing and weaving as she moved about. Kevin lifted his legs to his chest as she moved in close. He made some odd throaty noise when she the head pressed against his rear opening. Over the last year, she had fucked him enough that there was little resistance when she entered him. Allowing the muscles to time to accept the violator she stopped moving once the entire head was inside. A sparkle in his eyes told her he was ready for more. She walked forward on one knee, followed by the other, until the dildo was half in. Both remained silent as they waited for his body to relax. Once Kevin nodded she slammed her hips forward until she smacked into him. He exhaled loudly. She then withdrew until the head nearly popped out. Then slammed into him again. Once, twice, and a third time until she met no resistance to her thrusts.
Kevin's head dropped back into the pillow as Caroline picked up the pace. In decent shape, she could easily maintain her activity for a good bit before needing any respite. She now leaned over him so they were face to face. Her hips hammed the fake cock from the tip to the hilt and back as she studied his face. He showed no emotion at all. His eyes were closed and his mouth was closed except for the corners. His breath was completely quiet.
After several minutes his legs started to drop so she snapped at him to raise them. Hands went behind his knees and he immediately did as ordered. She spoke now in mocking tones at him. Asking if he wrote enough fines to homeowners. Did he win at tennis? Men's or women's teams? Did he correct the staff at the club? Did he let all the other HOA members know who was in charge?
Caroline felt sweat on her forehead and a trickle from her lower back run between her rear cheeks. Her breath was easy, but, she began to sweat. A droplet fell on his forehead and his eyes flew open. A stern look came up to her from below. She blew the sweat off her lips onto his face. That set him off as he tried to lower his legs to get up. Caroline widened her stance and leaned into him before pinning his hands to the pillow. She warned him she might not continue if he acted up. Her hips barely missed a stroke.
" Women sweat too." She spoke to him like a fussy child. They both were 5'6" but she carried an additional 20 pounds. She was younger and stronger than Kevin. And she had spent time in the Marines grappling with proficient ground fighters. Kevin had no such skills. She could easily control him, and that made their meeting all the more exciting for him.
Caroline stopped suddenly as her hips needed a break. Standing up and reaching down, she spun Kevin over by his waist. She then lifted his hips while kicking his knees apart. Standing feet shoulder width apart she reentered him. It took her a few strokes to find her rhythm before pounding him to her hilt. Now she smacked his ass as she returned to asking him questions like, did he run down the cleaning crew for a dusty picture? Did he berate the yardmen for cutting glass slowly? Though she found this type of sexual activity odd, a smile crept across her face. He loved to bully anyone he could and cried foul when he didn't get his way. It is pure joy to punish cry bullies like Kevin. He yelped as each smack struck his tiny little ass. In her odd manner, she felt she was retribution for everyone who dealt with his male Karen.
The sun had set and the deck off the room was dark. This prompted an idea. She grabbed Kevin's collar and walked him out to the deck. He stood in his polo shirt, naked from his waist to his shoes. After bending him over the rail Caroline told him to wait. Walking back to the desk in the room, she used a tissue to remove the 7" penis and replace it with an 8", thicker penis. This bigger, thicker penis had a more pronounced bob to it. Walking up behind him she felt herself drip from sweat and female excitement. Kevin stood motionless waiting for her. She whispered in his ear not to make a sound as his neighbors might see what he was doing. Adjusting her height to line herself up, she then slammed the new unit deep into him. He yelped under his breath. For 10 minutes he held in any sound as Caroline slammed up his rectum with an 8" fake phallus. With machine-like repetition Caroline fucked him. She treated this exercise like a run; focusing on the scenery of the houses before her and not the road below. And just like a run, she began to sweat heavily. Her breathing was quick and quiet as sweat lathered across her shoulders. Only when her hip muscles began to tire some that she tell him to turn about. After he did, she lifted him so his lower back rested on the railing. She then sodomized him face to face for another several minutes.
Tired and lathered, she told Kevin to go back and get on the bed. Kevin's dick has been limp the entire session. And now, Caroline looked down at it, it just flopped about, lifelessly. Inside she told him to fly flat on his front. She mounted his hips, inserted the penis, and returned to thrusting into him. The contact of the womanly body above him, the fake phallus in him, and the soft sheets below finally gave him an erection. Yet it still took several minutes of effort before he made a series of squealing sounds. He finally came.
Relieved that her task was over, a drenched Caroline hopped off the bed and began the clean-up. Kevin lay face down and motionless with his face buried in a pillow. In an adjacent bathroom, she washed the toys before putting them in a desk drawer. As she dressed she reminded Kevin that she had to tuck her kids in, then left. He told her to come back next week.
As she walked home Caroline remembered that in two days she had to visit Mrs Smith for the groceries.
Caroline, in a surprising twist, revealed her knowledge of Kevin's unusual sexual preferences. She mentioned his affinity for pegging, a practice involving a strapon, saying, "Once I start I might just wear that ass out." Later, she donned a blonde wig, red teddy, black harness, and a sizable fake penis, also known as a strapon, to carry out their unconventional activity.
