The Masked Woman and the Mistress

Warning: This story contains graphic scenes depicting humiliation and pain.

This is a work of fiction. Names, characters, businesses, places, merchandise, companies, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters are 18 years or older when in sexual situations.

This is Boxwood's and Mistress SWP's shared fantasy.

This story is another prequel to Jennifer's Road to Submission.

Troy appears in that story and is described as a tall, muscular football player who had discovered his submissive tendencies.

Laney appears in that story and in The Vortex and is described as an All-American girl, blond, attractive, tall and lean whose innocent appearance conceals a submissive streak and a very dark side. This story begins in the summer after Troy's first year of junior college and his first year of junior college football.

Mistress Claire appears in The Vortex and is described as an attractive woman, a scientist in her early 40's, always impeccably dressed. She has chestnut brown hair, blue eyes, and a curvy figure and shapely toned legs.

*****

Prologue

I'd finally found what I wanted. I had no idea that this world existed or that I would want to be a part of it. But I discovered that it provided the perfect counterbalance to my vanilla life.

If anyone in my vanilla life discovered me in this position my football career would be over. I was willing to take that risk, in fact compelled to take that risk, since there was no way I could ever give up this way of life.

I was sitting, hugging the back of a tall-backed chair in her bedroom. I could feel the cold leather of the chair's seating surface against my bare bottom and the soft fine wool of the Oriental carpet on the balls of my feet. A nude woman with a black leather mask covering her head was kneeling next to me with her hands clasped behind her back, silent and still as a statue.

A woman's voice, calm but forceful, called out, "Troy, have you decided on how you wanted to be punished?"

I was certain of my choice. "The signal whip, Mistress."

"And how many strokes for cumming without permission?"

"Ten ma'am."

"Very well."

I could hear her feet padding on the plush Oriental rug as she retrieved my favorite whip. My skin started to tingle in anticipation of my punishment. I put my fingers on my wrist. My heart rate was 160 beats per minute. I really wanted this, needed it. Sweat was already forming on my brow.

Moments later I heard footfalls in the hallway and could then sense Mistress Claire standing behind me.

"Are you ready to receive your punishment?"

"Yes ma'am."

"Count for me you worthless piece of shit."

The air sizzled as my Mistress expertly flicked the signal whip. The popper's five tassels exploded on their impact with my back, causing me to arch my back and exhale loudly. Even though I wanted to issue a blood curdling scream I relied on my training to stay silent. My back was now crackling with pain as I felt the rush of endorphins surge through my body.

"One . . . may I have another?"

Chapter One

I'd played football all my life. From midget to junior college. I was hoping to make a name for myself as a hard hitting free safety and transfer after my sophomore year from junior college to a Division 1A school, preferably in the Big East conference where I would get maximum exposure for the professional draft.

I was always good at football but it wasn't ingrained in my DNA. My friends knew I was easy going, even shy. But on the field I was expected to be a tiger and I'd trained to deliver on that expectation. I've laid flat many a wide receiver that dared venture into the middle of the field, which belonged to me and me alone. I didn't particularly enjoy this aspect of the game although many of my teammates relished these gladiator elements, and in my free time I would have rather read a good book than caroused in a bar and chased eager and willing women.

Money was always tight for me. My parents helped me some, but with three brothers and sisters I shouldered most of the burden of my junior college tuition and living expenses. And living in Los Angeles was expensive. I was always looking for odd jobs to make money. Given my size, 6'2", 185 pounds, I was good at being a handyman and also performing construction and yard work. My dad was a journeyman bricklayer so I had spent a number of summers on construction crews.

In the summer between my freshman and sophomore years a teammate's mother knew a woman through the East Side golf club that needed a significant amount of yard renovation at her house. I was given the address and told to be there on Saturday at 9 a.m. to meet the owner and find out if I could help her. I made the fifteen minute drive to a fashionable neighborhood in Brentwood and arrived at a Tudor style house at the end of the street. It was a beautiful home so I expected to see a beautiful woman answer the door. I wasn't disappointed.

Claire was beautiful. The thing about Claire's beauty was that she was striking and not some over the top former beauty queen. She had well-cut brunette hair and light makeup that highlighted her eyes. She was wearing a casual dress, but well-fitted and short, so yes, I noticed her well-proportioned breasts and her tanned smooth and supple legs. My first impression of her was more the grace and ease with which she carried herself. I'd had my share of women, and women who had thrown themselves at me, but I knew she was different. She wasn't fazed in the least by my build or what I've been told are my youthful good looks. She was all business. I was more interested in the work than any thoughts of an entanglement with her, romantic or otherwise.

I shared with her my considerable experience with construction and landscaping work. I also gave her my hourly rate. As I was talking to her I could feel her cold calculating assessment of me as her eyes wandered during my recitation. What was she thinking? Her cool and collected manner revealed nothing. She seemed satisfied with the recitation of my experience and my rate and told me the biggest part of her project was a retaining wall to be built of railroad ties forming a series of planter boxes up the slope in her back yard. Someone else had already started it, so I could see how it would work, and all the pieces were already there.

I set about continuing the project although there was no expectation I would complete it that day. Late in the afternoon, when she checked on my progress, I was exhausted from moving the heavy timbers and hammering in the anchoring spikes. I was in prime condition, pretty much, and I sort of bulked up and posed a bit as she walked across the lawn. I couldn't help but notice the elegance in the way she carried herself, so different from the young women that I associated with, and that triggered pangs of longing that were unexpected to me.

Claire sounded upbeat in her assessment of my work. "Troy, this wall is beginning to look very good, but it looks like really tiring work. Come in, I need to show you the garden plan, and you can have some hot tea - - it's actually much better for you on a hot day than iced tea."

I didn't think there was anything behind her invitation to go into her house and I welcomed the break and the refreshment. "Thank you Ms. Henley, that would be great, even better than the cold beer I was thinking about."

At the door, she turned to me. "This may sound odd, but I lived in China for a while and picked up some customs; take off your boots when you go in. In China wearing street shoes inside is very rude." Inside the door, she slipped off her shoes and into sandals that were on a mat. I had to unlace my boots, and then take off my heavy socks which were dusty. It did feel odd to be barefoot in her house.

"Go ahead and use the restroom to wash up. I've put out a fresh towel for you next to the sink. Don't worry about getting it dirty. The bathroom is the second door on the right. I'll be in the kitchen making tea. Just make yourself at home in the living room after you've cleaned up."

I was still studying Claire and trying to understand why an older woman would arouse me. I wasn't really paying attention to what she was saying and walked down the hallway and opened the first door on the right. I flicked on the light expecting to be in the bathroom. Instead I was in a guest bedroom. There was a woman wearing a leather mask that covered everything except her mouth. She was nude and kneeling next to the bed. She turned her head quickly in my direction upon hearing the opening of the door. I was momentarily stunned, then stared at her for a moment, and then quickly turned off the light and shut the door. I went to the next door and found the bathroom. I was shaking from what I had just seen and probably wasn't supposed to have seen. I took plenty of time to splash my face with cold water until I could regain my composure. I was only 20 at the time, so my experience with sex was limited to women my age who were relatively inexperienced. I wasn't sure what I had just seen but I was highly aroused by this startling discovery.

I returned to the living room and sat on the carpet awaiting Claire, still shaking from the indelible image of the nude woman in the mask. Claire brought in the hot tea and the landscaping plans. I politely drank the tea and feigned interest in the plans, but the whole time my mind was trying to process the scene in the guest bedroom.

" . . . and after finishing the planter boxes what is your recommendation on the irrigation system?"

Claire looked at me. I gave her a blank stare. I had no idea what she had been saying.

"Troy, have you been listening to me?"

I hadn't been. The image of the nude woman's perfectly shaped breasts was capturing all of my conscious thought. "I'm sorry Ms. Henley, it's been a long day and I think my mind wandered when you were explaining your landscaping plans."

"I understand," she told me, but I'm sure she didn't. "You've been working hard in the sun for the last four hours. Why don't you go home and come back tomorrow to see if you can finish up with the planter boxes? We can discuss the irrigation system tomorrow at 9 when you're a bit fresher. And please call me Claire."

"Yes ma'am, Claire."

I couldn't get out of the house quick enough. I wanted to be by myself in my apartment. I got to my apartment about 15 minutes later, took a quick shower, and then in my underwear popped a beer. I settled into my living room chair I started to recreate exactly what I had seen. I remembered it was a guest bedroom with a double bed and dresser. There was an Oriental rug next to the bed. The woman was wearing a black leather mask that zipped up in the back. It had a large hole in the front through which I could see her lips. Her blond hair was protruding from the back of the mask. She was kneeling. She was nude, but she was wearing a brown leather collar that looked like a dog collar but was wider. When I opened the door and turned on the light she turned towards the sound. I could see her pale white skin and small but shapely breasts. I guessed she was about the same age as me.

I was moved by that scene. As I was recreating it in my mind my cock was rising in my underwear. The pleasant buzz from the beer and the erotic scene I had recreated in my mind had me stroking my cock and dreaming about the girl and her submissive position. I was confused by my feelings but clearly aroused. I had a pit in my stomach. An empty feeling. Did I want to be like her? Kneeling and waiting for my Mistress? Or taking this woman in the mask? Fucking her? Making her mine? Within minutes I was spurting cum up my chest. Too many thoughts to process and too tired to process them. I fell asleep in the chair and didn't wake until the middle of the night, with my underwear still down around my ankles and my cum now dried on my chest and matted in my pubic hair. I cleaned up and went to bed.

I woke up the next morning already in a state of nervous excitement. I arrived at Claire's house promptly at 9 the next morning. She answered the door, this time in a short white tennis dress and in her white tennis socks. I decided that she was beautiful no matter what she was wearing. My longing was turning into outright lust.

"Right on time. Why don't you come in and we can discuss the irrigation plan. I've got to get to a tennis match at the club."

We went into the living room and Claire quickly recapped where she wanted the irrigation lines buried on the landscape plan she had laid out on a low rise table. As she was explaining the plan she leaned over to point, and I was focused on my clear view of her sports bra, encasing two well rounded breasts, and not on the landscape plan. I think she saw my eyes straying to her breasts. She told me she should be back around noon. She left me in the house with the plans and told me to help myself to any food and drink in the kitchen while she was away. She bid me goodbye and left through the front door.

Of course I couldn't resist. As soon as I could hear Claire's car start up and then drive down the street I went to the guest bedroom door. It was closed. This time I carefully opened the door, trying not to make any sound. Instead of turning on the light I relied on the ambient light from outside the room to see what was inside. Like yesterday, the woman was kneeling next to the bed with her head facing perpendicular to me and this time not turning towards me. She was wearing the same black leather mask. I was practically shaking as I studied her. She had fine wavy blond hair peeking out from the back of the mask. Her breasts were small but sexy. Her nipples were erect. She had tanned arms and legs. I wanted so badly to touch her. I spent about five minutes in the room, memorizing every detail, and slowly stroking my cock inside my pants. I was breathing heavily and hoping the woman wouldn't hear me. I then quietly left and shut the door.

It was hard for me to focus on the tasks Claire had assigned to me, but once I got started I worked steadily until the timbers were all pounded into place and the irrigation lines were laid in the beds and connected to the stubs previously installed. As I was finishing up Claire came into the backyard, looking comely in her short tennis dress.

Claire was beaming. "Outstanding Troy. The planter boxes look great and you really understood what I wanted with the irrigation lines. Why don't you come in and wash up and we'll discuss the next phase of the project and I'll also pay you for what you've done so far?"

I went into the house, took off my shoes and socks, and washed up in the bathroom. I looked longingly at the closed guest bedroom door. Claire was waiting for me in the living room. She was sitting in the tall back leather chair with her tanned and shapely legs fully exposed, barely covered by her short tennis dress. There weren't any seating options other than the carpet so I sat on the floor. I wasn't sure how it was going to happen but now I wanted Claire in the worst way. Hopefully my body language wasn't giving this away.

"As far as the landscaping goes, the next phase will be filling the planter boxes with a soil mixture. I'll have the soil delivered later today and you can come back tomorrow to fill the boxes. Can you come tomorrow to handle that?"

"Yes ma'am . . . I mean Claire."

"And here's a check for your work yesterday and today." She held the check in front of her. I got up and stood in front of her. I reached forward for the check. As I was reaching for it she pulled it back.

In a commanding voice Claire said, "Kneel."

"Excuse me?" I wasn't sure I heard her correctly. I thought I heard her say "Kneel."

In a stern voice, Claire repeated, "Troy, if you want this check I want you to kneel."

My ears weren't deceiving me. I wasn't sure why she wanted me to do it but I knelt in front of her. She leaned over and held the check in front of me. As I reached for it she grabbed my wrist. I was surprised at the strength of her grip. I looked up at her and our eyes met. She had the bluest eyes I could recall seeing. I couldn't explain why, but I wasn't afraid. I could have easily overpowered her, but it felt right to be kneeling at her feet and under her control. As right as I've ever felt in my life.

But then the inquisition began. In a stern voice worthy of a prosecutor, Claire asked "You went someplace yesterday that you didn't belong, didn't you?"

I was taken aback by the bluntness of the question and its embarrassing subject matter. I'd been caught with my hand in the proverbial cookie jar. "It . . . It . . . It was an honest mistake. I thought it was the bathroom door."

"And you went back in today, didn't you? Was that an honest mistake?"

"I . . .I . . .I did. But how did you know?"

"Laney told me yesterday that someone came into her room while she was waiting for me. And she didn't have to tell me about today. I knew when I left the house this morning that you wouldn't be able to resist visiting her again."

"I'm . . . I'm so sorry." I was both sorry and ashamed. Now I could feel Claire's true power and dominance over me. It was as if I was a pane of glass and she could see through me and into my soul. She let go of my wrist and leaned back in her chair. I had red indentations in my wrist from her fingers.

"Did you masturbate last night?"

She said it so matter of factly. I sheepishly answered, "I did."

"Tell me why."

"Because I was excited by what I saw."

"Do you know why you were excited?"

"I don't. I don't understand my feelings. I've never seen anything like this."

"Did you want to ask me about Laney, the woman in the guest bedroom?"

"I do. Is Laney here under her own free will?"

"Yes, in fact she has asked, no begged to be controlled by me."

"But why?"

"This may sound nonsensical, but she feels empowered by her surrendering control to me."

"And why is that?"

"Because Laney has been told what to do her entire life. I control her life in a way where she can explore and discover who she really is."

Claire leaned forward and looked me in the eyes. Those shimmering pools of blue again. "Did you want me to show you the power of submission?"

I wasn't sure what I was agreeing to, but I couldn't get the vision of Laney and her submission out of my head. "Yes, I would."

"Wait here." Claire walked away. I stayed on my knees and eagerly awaited her return. A few minutes later she walked into the living room holding Laney's hand. Laney was still masked and nude.

"Kneel slut." Laney knelt on the carpeting next to me.

"Tell your Mistress your purpose here."

"To please you, Mistress Claire."

"And what are you?"

"I'm a worthless slut. A fuck hole for my Mistress's pleasure."

"Laney, I have Troy here. It would please me if you would suck his cock. Would that please you?"

"Yes Mistress, this worthless whore would like nothing more than to suck Troy's cock if it pleases you."

I was highly aroused by this salacious talk. My cock was already tenting in my pants.

"Troy, take off your pants and stand in front of Laney."

I couldn't get my pants and underwear off fast enough. Laney was so seductive, kneeling with the black mask on, waiting with her lips parted and her legs spread apart.

"Troy, your first step to submission is to recognize that I'm your superior. You'll call me Mistress or Mistress Claire. Is that clear?"

I tried to keep my voice from shaking. "YYYYes Mistress Claire."