As I looked up the steps to the front door of the Hawkwood family home, I was filled with dread and anxiety. I started up the first step and I could hear my mother pull away in her car behind me. I could hear the sound of rubber on the wet asphalt fade out as it made its way down the the circle of the drop off area to the black ribbon of the long driveway that led to the front gate, passing the lush grass and trees that lined it. I wasn’t entirely sure why I was there.
Just two days before, I had returned from a disastrous date with the school slut. It’s harsh to say, I know, but that’s what I have to call a woman who ditches her date at a party to go off and get high and fuck another guy. Granted, I was pretty hopeless with women. I was despondent. I had graduated from high school just the week before. It was 2009, and no one was hiring for summer jobs. I couldn’t even get laid or find someone to love. When I unloaded my feelings on my mother, she was quiet but sympathetic.
My mother is one of my heroes. At 18 and a senior, she got pregnant. What makes that especially surprising for her is she was one of the smartest girls in school. Nevertheless, she fell for a bad boy and got knocked up with me. Her Catholic mother insisted she keep me, although I think my mother readily agreed. My grandmother, Sue, was a widower and a hospital administrator. I was born in July just after my mother graduated from high school. Grandma Sue was in her late fifties by that point. My mom, Laura, was a late in life child and her only child. To keep mom on the college track, she was willing to raise me. While I was still a baby, my father, who never did marry my mom, overdosed. My mom — Kate is her name — went on to finish college and then after a few years of work, got her MBA in finance. By the time I had graduated from high school, she was the youngest female CFO at a major corporation.
On the board of the company for which my mother works sat Jane Hawkwood, the 40-something matriarch of one of the oldest and richest families in Central City. Just the evening before that fateful morning in the summer of 2009, my mother informed me that she had obtained a summer job for me. I was going to be a personal assistant to Ms. Hawkwood.
After I rang the bell, I watched through the thick glass of the door as Jane Hawkwood exited one of the rooms along the hallway of the main floor and started walking down the wide front hall. I could write an epic poem about her appearance but I’ll spare you the torture. Her skin was alabaster white, her hair long and red, her figure statuesque. In short, especially to a virgin, like me, she was a mesmerizing vision.
The click of the tumblers in the door lock woke me from my revery.
“You must be Trevor Brooks?”
“Well, come in,” she said as she opened the door wide. “Follow me, Trevor.”
We walked back to the room she had exited a moment before. It was a surprisingly modern office for a 120-year-old mansion. The clutter was minimal, exhibiting instead all the elements of sleek design.
“Have a seat,” she said, gesturing toward a chair. “Tell me about yourself.”
I skipped over the family history. Mom probably had told her about it or preferred her not to know. I talked about school, my interests, and even touched on my recent problems with girls. She smiled at that.
“OK, well, Kate probably told you that I’m looking for a personal assistant. I’ll pay you $100 a day, and I can guarantee you at least this first week. We’ll talk like this again on Friday and assess whether we like the situation enough to continue it through the summer. Does that sound good?”
It sounded great. I could earn as much as $6,000 by the end of the summer.
Ms. Hawkwood even gave me use of an old Jaguar in the six-car garage out back for errands around town. Basically, I was a go-fer. I picked up and dropped off dry cleaning. I picked up lunch, I made reservations, I made appointments for her. When she didn’t have anything for me, she had me on “on call” status. That meant I was given ample time to read in the large family library. Friday rolled around sooner than expected. Most of the day was full of chores. I didn’t get much library time, but the activity kept me from being nervous about the end of the week assessment. A little after four o’clock, Ms. Hawkwood entered library, where I had been for the first time that day.
She sat down opposite me in the other overstuffed, leather reading chair.
“I’ll get straight to it, Trevor,” she said. “You’ve been an excellent personal assistant. I have no complaints. You’re a fast learner.”
I beamed with pride and relief.
“You have only one more test to pass. I know you can fill the ordinary, every day role. The question is can you handle special duties.”
I’m sure I looked crestfallen and disappointed.
“Let me explain, Trevor. I need a house boy, not just a personal assistant,” she said. Now, I even was more confused. “House boy has a special meaning among my circle of female friends. You see, Trevor, I’m an especially busy woman. You know that now as well as anybody. Time is precious to me, which is why you are here. But, I need more than a personal assistant. I’m a highly sexual person, and I need someone who will serve those needs, too.”
Ms. Hawkwood laughed. “Don’t be so petrified. Tell me what you think. Take a minute to gather your thoughts.” I did. I took more than one.
A thousand thoughts crossed my mind, but they settled on one immutable truth: I was a virgin without any immediate hopes of that changing. I probably should explain here what some of my disadvantages were. I was and am 5 feet 6 inches and of slender build. My head was crowned by an unruly mop of curly black hair, and I have a weak chin. To top it all off, I ordinarily was petrified before a beautiful woman. Although still intimidating, Ms. Hawkwood already had become familiar enough that I had lost most of my nervousness around her. She was super smart, sexy as hell and I could learn a lot from her about sex and more.
In my reply, I more or less told her this. At the end, she smiled and stood up.
“You’re a wiser young man than I expected,” she said. “Please follow me and we will begin your training.”
To say I was taken aback when we talked into a hall closet would be an understatement. Next, she accessed an app on her smart phone, appeared to enter a passcode and then spoke a voice command, “Open seasame.” I almost laughed.
An audible click came from within the inside wall of the closet and the panel swung open an inch. Ms. Hawkwood pushed it further open and stepped forward onto a small landing. Wordlessly, I followed her down a narrow flight of stairs to a basement. Motion-activated lights came on along the walls, providing ample but soft, indirect light. I had been all over the house and had no idea this large room was even here. There was no doorway out to the rest of the basement, which only housed the heart of the HVAC system, a washer dryer and storage. The room was so large it must have taken up half or more of the footprint.
In one corner was a very ordinary setting — a king size bed, two bedside tables with lamps, a table a few feet from the foot of the bed with a large, flat screen TV. However, the rest of the basement was probably the best equipped and designed sex dungeon in America. There were sawhorses, three Sybian machines, peg board walls replete with sex toys. I could go on, but you at least have the general picture.
When we got to the foot of the stairs, Ms. Hawkwood ordered me to disrobe and hang my clothes on the clothes rack that stood there. Now, I was beginning to get the jitters, but I complied. She looked me up and down like a farm animal she was assessing for purchase.
“You’re not in bad shape,” she said. Her eyes had traveled over my cock, but now returned for a closer look.
“Now, that is a surprise.” I blushed. “How big are you, Trevor?”
“Uh, a little under 5 inches flaccid, and almost eight inches when very hard.”
“Very nice,” she said. “I didn’t tell you this, Trevor, but whenever we are down in this room, you are to refer to me as Mistress Jane or Miss J. Understood?”
“Yes, Miss J.” She smiled again.
As we walked to the far end of the room, navigating around various large toys and bizarre machines, Miss J continued to talk.
“I have to say it’s unusual in my experience for a man of your size to be so well endowed. Your cock also looks to have a lovely shape, Trevor.” I blushed again.
“Just as I am Miss J in this room, I think I will give you a special name. You will be ‘Teapot.'”
I laughed. “Why’s that, Miss J?”
“Because, Trevor, you’re short, but you have a big spout.”
We both laughed, and that put me at ease.
Still fully dressed in simple black dress shoes with two inch heels and a simple, black dress, Miss J stopped before what I only can describe as a throne. She sat down on it.
“Bring that mat over and kneel before me, Teapot. Pick out some lube from the shelf over there,” she said pointing to a spot along the wall.
I complied. There I was — a naked and well-endowed virgin kneeling before a fully clothed, beautiful goddess. My cock was as hard as stone.
“Now, Trevor. I want you to give me seven edges. That’s masturbating just short of orgasm and stopping. You can use the lube.”
I squirted some KY into my hand and started stroking.
“When you are close say, “Edge, Miss J. Thank you, Miss J.'”
I nodded in the affirmative and said I would obey.
“Good, I’m going to explain some things while you do that. … First, don’t assume I think your virginity is a problem. I know you’re disease free, and I like a blank slate.” She gave me a kind smile.
“If you take my discipline and guidance, then you’ll learn a lot from me and become a confident and skilled lover.”
Then, her demeanor became more severe.
“However, I regard men as beneath women in most instances,” she explained. “That doesn’t mean you don’t have value. I love a good dick as much as the next girl, but they should be submissive and obedient to women. I will teach you this truth. Fortunately, you don’t appear to have become too polluted by patriarchy. You’re still young.”
I don’t know why, but her words were exciting to me.
“Edge, Miss J. Thank you, Miss J.”
“Stop! Hands at your side.”
I let my arms and hands hang loosely while I rest on my haunches.
“One of the chief sources of the world’s troubles is patriarchy,” Miss J explained. “War, inequality, hierarchy, many of these evils stem from the out-of-balance psychology and social structures that flow from patriarchy. I’m part of a network of women working to change that, a quiet revolution, and we need knights. Would you like to be my knight, Teapot?”
“Yes, Miss J.”
Her smile returned. “I’d like that, too. Time will tell if we both can make that happen. … You may resume your edging, Teapot.”
I was so hard. I found her commanding presence, erotic and arousing. My lack of experience made it even more appealing. I could relax and follow her lead.
I hit an edge in about two minutes, her silent staring only turned me on more. She laughed, and then I blushed and complied with her second command to cease and desist.
“You see, Teapot. Most men, and many women, are betas. That doesn’t mean they are stupid or incompetent. It just means they’re more suitable as followers. Women are more empathetic. They understand feelings and people more quickly than men. That’s why they are more suited to lead. Patriarchy has brainwashed them and directed them away from realizing that truth.”
I hit my third edge. It almost felt as though my semen was a wave crashing at a seawall. I felt it surge and then fall back as I took my hand away. My cock was purple and bone hard.
“You are a beta, Teapot. You’re smart. Despite your size, you may even be an excellent knight, but I can tell from our week together that you are a natural servant. You want to be led, you want to be taught, don’t you, Teapot?”
“Yes, Miss J.”
“Keep stroking. I like watching you play with your big dick.”
Her words were turning me on, even the philosophical ones. I hit the fourth just as quickly as the third. This time I gasped and moaned as I fought back the Big O.
“So, tell me, Teapot, have you fantasized about dominant women? About an older woman taking control of you and teaching you about sex?”
“Yes, Miss J.”
I fantasized about a lot of things but dominant women was among them, especially one who would teach me about sex.
I started working on my fifth edge.
“Well, I’m going to teach you how to make drinks, how to wait on a group of women and how to entertain,” she said. “I may even have you get completely naked in front of them. Would you do that for me, Teapot?”
“Oh, yes, Miss J,” I nearly came at the thought.
I put my hands at my sides again.
“I have to say I am impressed and a little sorry for you,” Miss J. said. “Your cock looks painful. For a virgin, you’ve shown remarkable self discipline. That’s good. You’ll need that character trait. So, Teapot, if I had you serve at a cocktail party and I ordered you to lick the pussy of a guest, would you?”
I replied in the affirmative.
“Would you lick ass, if it was clean?” Again, the answer was yes.
“Would you suck cock for me, Teapot?”
I hesitated just a second or two before agreeing.
“A little bit inhibited there, but at least you’re willing to explore.”
At her command, I started climbing toward the sixth edge.
“You are such a horny, little puppy, aren’t you, Teapot? … Why don’t you whimper for me like a little puppy? Beg for me.”
Mewling sounds started coming from my throat despite myself. I turned beet-red from the humiliation.
I almost came, but Miss J caught me in time.
“Bad dog!,” she sauntered over and slapped me lightly on the face. I whimpered again and she smiled. Next, she walked over and picked out a small collection of joined bands, stretchy bands.
“Now, do you want to give me a seventh edge? Will you honor me with another sacrificed orgasm or should I send you home?”
I whimpered like a puppy and shook my head.
“Then get down and lick my shoes, Teapot.”
I crawled to her and kissed the tops of her shoes. I licked at her feet and whimpered.
“Good, boy.” She patted me on the head. “Now, give me that seventh edge.”
I sat back on my haunches again and started stroking in earnest, after applying more lube.
“That’s it. Stroke it, you pervert. You’d do anything to touch me, wouldn’t you, Teapot? You can speak again.”
“Yes, Miss J, anything.”
“If I let you come tonight, will you lick it up? Oh, I still want that seventh edge, of course. I’ll tell you when.”
“Yes, Miss J. I’ll eat it for you.”
“That’s a good boy. Tell me what you think of what’s happening and what you think of your Mistress. Let me hear you fawn.”
I told her how beautiful she is, how glad I am to be taken under her tutelage, how happy I was to be her house boy.
“Edge, Miss J. Thank you, Miss J!”
I was ordered one last time to stop.
“Stand and come here, Teapot.”
I approached her on her throne. She leaned forward, and using both hands, she placed the collection of bands on my cock and balls. It was a cock strap and separator. There was no way I would lose my erection any time soon.
“That looks good. So purple. Now, kneel here.”
She pointed to a spot very close to the base of the throne.
With a whimper of overwhelming helplessness and desire, I fell to my knees. Somehow, it felt heavy with meaning, like I was falling forward into a future that was destined but not completely of my choosing. The choice itself was destined.
Miss J gently took my head in her hands and guided my face and mouth to her warm, wet pussy. Its musk and moist heat was intoxicating. My virgin hunger was sharp and compelling.
“It’s time for communion my new knight,” she said. “Drink from my holy cup.”
She must have needed this release as much as I did because she gasped loudly at the first contact of my lips with hers. I licked at the pink softness, tasted her salty sweetness and dove in with eagerness.
“Oh, that’s it but more slowly. I’ll teach you.”
For the next several minutes, I followed her instructions and struggled to pay attention, and it was a struggle not to lose myself in my oral worship of her. Miss J guided my pace and direction. I licked from the entrance to her quim along the lips and inside them, up and around her clit and down again. I kissed, I gently sucked when told to. After some time, the two of us reached an unspoken understanding. I began to get an idea of when to lick and where, how hard and for how long. Her words of guidance became more infrequent and her breathing more labored. Finally, with a shudder, a jerk and a loud cry, Miss J orgasmed, splashing my face with a small squirt of her juice. She pushed me away.
I too was panting for air.
We looked each other in the eyes and she smiled.
“That was excellent, especially for your very first time. I can’t imagine how good you will be in a few weeks.”
She stood and removed all of her clothes. Miss J ordered me to rise and hang them on the rack near the stairs. While I was doing this, she had retrieved a toy from the wall that prompted me to stop and stare. My teacher was holding the next implement to be used in my education, a harnessed dildo.
“Don’t be afraid, Teapot. Learning how to be fucked is the first important lesson in learning how to fuck. If you take this cock, then I’ll take your virginity tonight, not that I need to bargain with you, but fair is fair.”
I nodded with some hesitancy.
She smiled and ordered me over to a low table that was topped by a padded wedge. Once I was there, she bent me over it. Miss J made some adjustments — a bar pushed my legs forward and underneath my torso, opening my ass up wide. The wedge was perfectly shaped to accommodate my abdomen and relax my back downward, providing that extra bit of stretching to open my anus and butt cleft to their maximum. Miss J cuffed my hands to the sides of the table. I felt a motor kick in and raise the table an inch or two. My ass hung just over its edge.
“There, that’s perfect,” she said as I felt her squirt lube into the crack of my ass. I could tell she now was wearing disposable, surgical type gloves.
Walking to my front, she showed me a small, tapered butt plug made of silicone.
“To really, do the anal right, you need to be warmed up first. It’s not like in the pornos, Teapot. Learning about sex from pornos is like learning how to drive from a car chase movie. Just relax and let me do the work for now.”
Gently, Miss J circled the ring of my asshole with the tip of the plug. With almost imperceptible slowness, I felt her insert it, pushing at my sphincter as her thrust moved its wider base further inside. I exhaled. I was so full. It wasn’t comfortable, but it didn’t hurt.
“What does it feel like, Teapot?”
“It feels so big, Miss J. … It’s OK.”
“You see, Teapot. Women come more from licking than from penetration, but by mastering the right techniques, it can be pleasurable. I think this will help you learn that lesson, even if the ass is vastly different from the pussy.”
“Do you feel captive, Teapot? Do you feel vulnerable to my mercy and my strength?”
“Yes, Miss J.”
“Good, that’s how most girls feel their first time, too. I want you to feel that. Don’t worry. I don’t like so-called feminization. I like to feel a man submit to me as a man.”
Both of us were quiet for the next several minutes as she worked the plug back and forth and even rotated it some. I felt my sphincter relax and loosen some. Occasionally, I uttered quiet and involuntary whimpers. Miss J removed the plug.
Next, from somewhere else in the play room, she retrieved another toy and showed it to me.
“This is a prostate massager, Teapot. You’re going to like this.”
It had a curved shape, wide and cylindrical for half, then thinner and finally bulbous at the tip. More lube was applied, and I felt it go in much more easily than the butt plug. It began to vibrate at a low oscillation.
Miss J spent a minute or two working it around my ass, stimulating everything, but then concentrating at a spot on the inside of anterior, behind my cock and genitals. I gasped.
Suddenly, my ass came alive. I can only describe it as a new sensation that was somehow a pleasurable itch. I even started to hump the massager a bit.
“That’s a good, little bitch,” Miss J praised. “Moan for me.”
My moans were real but I upped the volume for her enjoyment. Her magic had turn fear into hungry desire.
Mistress walked over for another visual demonstration. The flesh colored dildo was six to seven inches in length with a peculiar bump midway down the shaft. I watched in fascination as she lubed it up.
Next, she returned to my ass and slowly withdrew the massager, which she had left securely embedded and vibrating in my ass. Miss J slowly removed it, but quickly pushed the strap on in. I yelped more in surprise at her speed than in pain. Her initial insertion was rapid but the remainder of her penetration was slow. My ass stretched and widened to accommodate, and then I felt the bump on my prostate and moaned.
Miss J laughed a low throaty laugh.
“You like that, pet?”
“Ohhh, yes, Mis J. Thank you, Miss J.”
For the first time since she had put the cock strap on me, I felt her reach around and grab my cock.
“My, that little boy clit is desperate to be let out, but I think it will have to wait. I really want to feel that cock now. Before I knew how big you are, that really wasn’t a priority.”
As she spoke, Miss J slowly was thrusting in and out of my ass. Each time the bump hit my prostate and my arousal rose just another little bit. My cock was painful in its tumescence and confinement. My moans were loud and constant.
“I like noisy bitches. That’s one reason I have a sound-proofed dungeon. It allows us to get as loud as we want. Do you like my cock in your ass, Teapot?”
“Yes, Miss J. Thank you, Miss J.”
“That’s a good boy. You want to be a good boy, don’t you, Teapot?”
“Yes, Miss J.”
“Of course, you do. You are such a horny little slut.”
Her thrusting increased in tempo but every minute or so she would stop with the dildo all the way in my ass with the fronts of her thighs touching mine. From her motions, she was rubbing herself against the base of the dildo, which I later learned was equipped with clit stimulator. Finally, Miss J was humping my ass and the dildo for the last time. I felt her jerk and shudder in another orgasm. She collapsed and bent over my ass. Her upper body rested on my back and felt her nipples tease my skin there.
“Oh! God! That was great! I love pegging,” she gasped. “You’re a good fuck, Teapot.”
“Thank you, Miss J.”
Miss J stood, removed her dildo and harness and tossed them into a basket she set aside for toys that would need cleaning later. Incidentally, this became one of my duties.
Next, she undid the cuffs and helped me up. Miss J finally removed the cock strap and tossed it into the basket as well.
I ordinarily would expect my cock would have been ready to explode, but it was in a weird state — still hard as steel but almost numb. With her hand around my cock, she led me to the large bed in the showroom-like set up I had seen on entering the dungeon.
Miss J pushed me down on to it face up.
“We’re going to see just how much self control you have. I expect you to come in seconds, being a horny virgin who has been teased mercilessly. This one time, I will not punish you for coming quickly, but if you want to impress me, then you’ll hold off as long as you can.”
With that said, and without any to do at all, Miss J straddle my midsection, aimed my cock at her pussy and descended on it.
That first penetration was exquisite, and I somehow managed to savor it. Miss J’s pussy was hot, wet, smooth and all encompassing. I was panting for breath and trying to hold off. Miss J kept me inside her. I felt her muscles flexing around my cock, squeezing and milking me. Her smile was a little cruel.
“This is the only way you ever will enter me, Teapot. I will ALWAYS be on top.”
Miss J rose up, the nether reaches of her pussy lips embracing the tip.
“Your cock feels great inside me, by the way. It’s hitting spots long neglected.”
Her quim swallowed me again. Again, I resisted.
“Tell me what you want to be, what you’ll do if I let you come inside me, Teapot?”
“Oh, Miss J, I’ll do anything. I’m yours. I’m your slut, your slave, your property. I’ll serve you and anyone else you tell me to.”
“Good,” she said as she drove my sword back into her scabbard.
Miss J picked up the pace. Both of us were silent except for heavy breathing and low moans. It was less than a dozen thrusts before I could no longer hold back. My cum jetted from my cock in one long, amazing spurt. It filled her and coated my dick. The release was fantastic.
Miss J shuddered at the sensation of my seed splashing inside her.
Quickly, she moved up to my head and straddled it. I looked up at the wet, dark, matted hair of pussy.
“Lick,” was all she said. I dove in with my tongue again, scooping out and swallowing my own seed. “Yes, that’s a good little cementer. Miss J enjoys her Teapot. You learn so fast. Remember to kiss the spot near my clot, the one I showed you earlier. Do it when I tell you, Teapot.”
I slowly licked and swallowed, enjoying the mix of her juice and my seed. After a minute or two, she said, “Now, Teapot.”
I kissed and licked the spot.
Her orgasm seemed like a little but pleasurable orgasm that was shutting off her libido, like the rattling of a door on a bar closing for the night. In its quiet way, it seemed powerful though.
With a somewhat wistful sigh, she dismounted.
“That’ll do, Teapot. That’ll do.”
Miss J picked up a robe from the rack near the door and said, “Clean up here and pick up your check on the front table near the door. I’ll see you on Monday, Trevor?”
“Have a great weekend.”
“You, too, ma’am.”
I spent the next 10 minutes cleaning and righting the room. I dressed, followed her instructions and went home.
Next week was another story.