Kinky Boat Ride
I was an extremely lucky guy. While I am not a nerd, I have a knack for developing innovative software. While I was in high school, I developed an unique program that I was able to sell to Microsoft for about $10 million. In college, I developed another application that netted me $150 million after a bidding war between Apple & Motorola. So now, at the tender age of 23, I was semi-retired. I bought a beautiful home on 5 acres right in the Chesapeake Bay and a nice 40 foot sailboat and set about enjoying myself.
To make things better, my beautiful and sexy mom came to stay with me. She is a wet dream come to life! She had my older sister when she was 17 and she had me at 18; so she is only 41 now. And she looks 10 years younger; she is fanatical about working out and keeping her luscious body in perfect shape. And what a body! She is fairly tall at 5 feet, 9 inches weighing in at 130 pounds. She has wavy auburn hair, beautiful green eyes, full, pouty lips and freckles across the bridge of her nose (as well as on her arms and chest). She has the classic hourglass figure with huge tits (40 DD), a thin waist, flaring hip, a tight, full ass and long shapely legs.
We settled into a great routine, taking the boat out each morning to a deserted cove where she sunbathed in a sexy string bikini while I fished leisurely. On this particular day I decided to shake things up. I invited my friend Kristen to join us. She is a Dominatrix I met online who is training me to be a Dom. She was a beautiful, petite blonde. She wore a tiny bikini which showed off her tanned body and carried a big leather satchel.
"Mom, this is Kristen. She is a Dominatrix who is training me to be a Dom."
My mother stood up to meet Kristen. Kristen spent several moments looking my mother up and down and appraising her body.
"Nice to meet you Mrs. Jones," Kristen said looking my mother in the eye.
My mother looked down and said, "Nice to meet you too."
She laid back down on her front and Kristen laid down right next to her.
"So Kristen, do you have slaves?" my mom asked totally surprising me.
"I have one. She is totally submissive and a pain slut. She cums multiple times when I punish her."
They were quiet for a while until we pulled into the cove. Then things began to get interesting.
"You have an incredible body, Mrs. J." Kristen said as she ran a finger up the back of my mother's leg. "This is a very spankable ass.
"Have you ever been spanked Mrs. J.?"
"Um yes. My father used to spank me when I was younger," my mother replied.
"When was the last time he spanked you?"
"On the morning of my wedding."
"And that was the last time you were spanked?"
"Um no. I was spanked a few years later."
"Who spanked you then?" Kristen asked as she continued to caress my mom's leg.
"My daughters' second grade teacher, Ms. Simpson."
"Oh sweet! Tell me all the details; how old was she, what did she look like, how did it come about?"
"I guess she was around 40 at the time. She was very pretty but very strict. She started to criticize my sweet Nicole and I guess I lost my temper a bit and told her what I thought of her. Before I knew what happened, she had me laying over her desk and she was spanking me fast and hard. Before I could catch my breath, she had my dress up over my back and my panties down and she was spanking my bare bottom with a hairbrush. She spanked me until my bottom was hot and very red before she stopped."
"That is an incredibly hot story Mrs. J." Kristen stated. "It got my juices flowing. Based on the wet spot I see on your suit, it did the same for you. Spread your legs Mrs. J. so Brad can see how aroused you are."
My mother moaned but obeyed, opening her legs. Kristen had gone from touching my mom's leg to caressing her ass.
"Mrs. J., it looks like you enjoy having your naughty bottom spanked? Isn't that right?"
Another moan followed by a muffled word.
"What was that Mrs. J.? I didn't hear you."
Yes," replied my mother.
"Yes I like having my naughty bottom spanked."
"Would you like to be spanked now?" Kristen asked as she continued to feel her ass.
A louder moan! "Yes!
"Okay! Just raise up on your knees and present that sexy ass!"
"Oh no, please don't spank me in front of Brad."
"Don't worry Mrs. J., I am not going to spank you in front of Brad; he is going to help me spank you!"
"Get" SLAP "your" SLAP "ass" SLAP "up" SLAP SLAP SLAP.
My mother got on her knees while her head was still on the deck, pushing her ass into the air.
"Brad, come over here. It is time to practice your spanking technique," Kristen said as she got on her knees next to my mother.
I moved quickly and knelt down on the other side of my mother.
"This will be perfect," Kristen said cheerfully. "This will allow us to thoroughly cover her entire ass."
With that, she yanked the bottom on her bikini up pulling it deep into her ass and baring both cheeks. They were strikingly white relative to the rest of her tanned legs (well, they were now slightly pink from the initial spanking she had received).
"Nooo..." cried my mother as she tried to get up and brought her right hand back in an attempt to pull down her bikini bottom. However, Kristen caught her hand and pushed it up her back. In the process, someone's fingers got tangled in the strap of her top and it came undone.
"Oh no...please let me up!" my beautiful mom said as she started to struggle to get to her feet. Her struggling caused her heavy breasts to pop out completely. They were lily white like her ass and her nipples were long and hard.
"Oh no you don't," Kristen yelled as she held my mother down. "You are not getting up until you have been thoroughly spanked."
Kristen gave her a few more hard swats which surprisingly settle her down. Kristen moved my mother's arm back and put it back on the deck by her head. While she was there, Kristen released the strap around my mother's neck and pulled her top right off. She did it so quickly, my mother had no time to react.
"Let's get started!" Kristen said and laid a hard smack on the cheek closest to her. I duplicated it on the other cheek. Soon we were in a nice rhythm alternating swats like clockwork. After 10 minutes like this, we had covered every inch her ass as well as the tops of her thighs. Mom was moaning steadily now but kept pushing her ass up higher to give us better access. There was a huge wet spot on her bikini bottom (there was one just as big on Kristen's suit as well) while I had a raging hardon.
"I think we should try something different," Kristen said. She reached into her satchel and pulled out two large, heavy, wooden hairbrushes and handed one to me. My mother was trying to catch her breath and whether consciously or subconsciously wiggling her butt.
"Mrs. J. I think it is time to remove this sopping wet bottom," Kristen said as she pulled on the ties at my mothers hips that held the suit together. Quickly, Kristen grabbed the bathing suit and pulled it off. She literally had to pry it out of her ass and pussy. Suddenly, we were both looking at mom's very wet and very aroused pussy.
"Spread your knees apart Mrs. J. so we can see just how excited you got when your son spanked you like a naughty little girl," Kristen commanded.
"No please don't make me do that," mom pleaded.
Kristen took the hairbrush, turned it around and slid the handle down mom's slit getting it slick then positioned it at her anus.
"Spread those knee slut or I will ram this up your ass."
Quick as a flash, mom spread her knees. Now I could see her engorged clit standing up proudly.Needless to say, I was rock hard.
Kristen moved the brush handle to mom's face. "Mrs. J., you got my hairbrush all wet. Lick it clean so I can use it to continue spanking your naughty ass."
I leaned over to see what my mother was going to do and saw her demurely licking her own juices off the handle. When Kristen was satisfied the handle of her brush was clean, she said, "I think that naughty bottom needs more punishment."
She reversed the hairbrush and brought it down hard on my mother's now naked ass. I followed suit on the other side. Again, we got into a rhythm of alternating spanks as my mother moaned and kept sticking her ass up further and wiggling it. After another 10 minutes of this, her ass was very red and very hot to the touch! (I couldn't resist the occasional caress in between swats).
Kristen stopped paddling my mother and said, "Alright, Mrs. J., I think you have had enough pain for today. Now I think it is time for the pleasure. Get up on your hands and knees."
As my mother quickly did as she was told, Kristen reached in her satchel and retrieved a huge dildo. She leaned over and whispered in my ear, "Go forward and play with her big tits while I pleasure her with this."
I didn't need to be told twice! Since I was ten years old, I had lusted after those huge knockers and now I was finally going to get to play with them. I scooted up front and sat by my mom's head. I waited momentarily until Kristen began. When mom began to moan loudly, I knew she had. I reached forward with both hands and cupped her heavy tits. Her moaning increased as I caressed her. I leaned down and kissed her sweet lips as I grabbed her engorged nipples between thumb and forefinger and pinched hard. As my tongue dipped into her mouth and I twisted her nipples, she came hard. As she gasp and convulsed, I continued to maul her tits and kiss her deeply. Then I saw Kristen slip the dildo out of her pussy and push it slowly into her anus. By the time the dildo was half way in, my mother was cumming again, hard. For the next several minutes, she had a series of mind-blowing orgasms as Kristen fucked her ass. By the time Kristen removed the dildo, my mother's eyes had rolled back in her head and she lay on the deck in a fetal position, completely exhausted by the ordeal.
I returned to the helm and headed back home. I dropped Kristen off and told her we should do this again tomorrow. She agreed, kissed me deeply and left. I returned home and carried my mother into the house wrapped in a towel and put her in her bed.Then I went to my own room and sought long overdue relief by masturbating furiously.