Jill the Best Secretary

Jill five

I woke up wondering if what happened last night was just a dream. I carefully rolled over, and she was, sound asleep on the floor. She was in the fetal position, still dressed in her underwear, consisting of her garter belt, stockings, and bikini briefs. When I got up to take a piss, I saw her face and was amazed at her beauty, even first thing in the morning. When I came back from the bathroom, she was starting to wake up. She pulled herself up on one elbow and smiled at me.

"Good morning, Sir," she giggled.

"You think that's funny," I tried to sound stern.

"Oh no, but after last night, I can't call you Mr. Bennet or Bob; I want to show you respect; you're not mad at me, are you?" My bottom is sore now; I don't want you to get mad."

"You don't deserve a spanking yet, but you're on thin ice. Now get going, and make me breakfast, NOW!"

Jill hurried out of the bedroom, moving as quickly as she could in heels. As she was getting things ready, I told her I needed a paper from the car and to get it. The car was in my driveway, a good thirty feet away.

"Sir, may I put a jacket on, please?"

"No, absolutely not; now get going." I snapped her ass with a towel, and she yelped and rubbed her cheeks. I could see her trembling as she opened the front door and moved quickly to the car; she unlocked the door using the remote as I watched her thru the kitchen window. I was holding the spare remote. I promptly locked it again; I did this several times, enjoying her stamping her feet in frustration. Finally, I let her open the door and get the paper. As she locked the door, I set the alarm off. Some guys were playing basketball in their yard. Hearing the warning, they saw Jill gamely trying to run in her underwear, stockings, and heels. I thought about locking the front door but was too lazy to go in there. I could hear the guys clapping and shouting, wanting her to come out. Maybe someday, when I'm tired of her, I'll invite them in, but not today.

During breakfast, her phone rang; it was her mother. I held up my hand; no phones while we were eating. Jill cast her eyes down and tried to speed up her eating; I finished and told her she had to clean up the kitchen before she could call her mom back. While she was cleaning, I got out a little present for her.

"I'm going to call her now, ok?"

"Just a minute, I've got something for you. Let's go in the den."

Jill walked into the den; I had put one of the bar stools in the center of the room.

"Now, come over here and bend over."

Jill had a killer butt, round and firm. "What are you going to do?" she whispered as I ran my hand over her butt.

"I bought you a little gift, now relax.

Her eyes widened, and the color drained from her face as I showed her a "u" shaped vibrator. "Are you going to put that thing in me?" she gasped.

"Why not? It will be fun."

Jill wisely kept her mouth shut. Using the gel that came with it, I slipped it into her slick cunt, with the largest part centered on her swollen clit. I adjusted her panties and motioned to the stool.

"Hop up," I said and get comfortable," sitting in her underwear and stockings. She looked at me, holding the remote before her worried face, and I almost felt sorry for her.

"Now call mom, and put it on speaker."

She blushed beet red as she picked up her phone, as I settled on the couch directly in front of her. Tears streamed down her face as she placed the phone on the table.

Just as I thought, her husband had called her mother, begging for help. What a wimp. Jill was starting to explain that she didn't love her husband anymore. I felt it was time. I flipped the switch to on and set it at one; Jill's face froze, and she mouthed, "Please stop."

So I set it at two, and she pressed her thighs together, squirming on the small stool. She was starting to gasp and pant. I could hear her mother say,

"What's wrong, Jill?" As Jill dropped the phone and grabbed her crotch, moaning. I gave her a break and switched it off; she regained her composure and told her mother she was sick and would call back later.

Jill fell onto the couch, "Where did you get that, and can you do it some more."

Maybe sometime if you're good. But you'll have to earn it."

Jill rolled over and withered on the couch, her legs clenched together. Finally she stood up and hung her head down, and whispered.

"I'm yours, do as you want with me."

I had some ideas of what to do to her,

But at my age, I couldn't keep this pace up indefinitely. I decided to wait for the weekends unless I changed my mind.

When we arrived at the office, there was a message to call Jim at the main office.

Everything changed rapidly; that sleazy boss of mine called to say there was nothing he could do; I had a week to close the office. I was pissed, but they would give me benefits for a year and six months' pay so it could have been worse.

I called Jill into my office and told her she would get a month's pay, but she was happy just to be with me. We boxed everything up for the movers in two days and took the rest of the week off to relax.

That night we were watching a movie in the den when one of the actresses bent over, her top rode up, exposing her "Tramp Stamp." I told Jill, "That would look good on you; let's get you one tomorrow. I'll call Lynn now."

Jill curled up next to me and whispered.

"I'm scared. I want you with me. Do you think Lynn could knock me out?"

My hand dropped to her ripe tits,

"I thought you liked pain."

"Only if you're the one hurting me, sir."

At the same time, I rolled her nipples between my fingers, pinching harder. She moaned and tried to move my hands; Please stop; I don't feel like it now."

I saw red.

"Don't ever say that again, now, stand up."

Jill stood up, hanging her head, avoiding my eyes. I pulled out a set of fur-lined handcuffs and swiftly fastened her hands behind her back. She let out a soft squeal as I pulled her back down.

"Please be gentle; I'm scared."

"I hope I can control myself, but you need to know who's in charge."

With that, I pulled her lacy cups down, her tits popping up. I roughly pinched and rolled her nipples, squeezing harder all the time. She was gasping and moaning; as I reached down and stroked her cunt; I thought she would explode. I slapped her tits from side to side, enjoying her yelps of pain.

I continued abusing her tits; she just sat there, hardly making a sound except for a low groan from time to time. I picked her up and put her on the arm of the couch. I removed my belt and laid it across her butt, letting her feel the cold leather.

"I deserve it, don't be gentle, Sir."

Her heels put her rear at the right height; that ass was a beautiful sight, framed by her garter straps and silver clasps, pulling her stockings tight.

I doubled my belt and gently touched her skin; she shuddered, knowing what was coming. I took a full swing, and the smack sounded like a gunshot in the small room. She let out a healthy scream, and I followed with two more. She didn't try to get away. Just wiggled her butt, side to side,

"I need more," she groaned. I didn't disappoint her. I paused hits to give her time to prepare for the next one. I continued until her ass was bright red. I was careful not to break her smooth skin, not this time.

"Did you learn your lesson, Jill?

"Yes, Master,"

Well, that was something new. I knew Jill well enough that calling me Master was something she had given some thought, not a spur-of-the-moment thing.

"Get on your knees, Jill. I'm ready for a blowjob."

She struggled to get off the couch,

"Please help me. I can't do it by myself."

After watching my beautiful blond struggle for a few minutes, I pulled her up by her ponytail and rolled her onto the floor. She got on her knees and took her position before me. I pulled my dick out and slapped her face, smearing her delicate features with pre cum. I pressed my cock to her lips; she quickly sucked me in, looking up at me with wide eyes. To say Jill's tongue was talented is an understatement; she attacked the end of my cock, licking and sucking and deep-throating my dick with little grunts of pleasure. I held the sides of her head and fucked her mouth until she was spitting pre cum mixed with spit. She took hold of my dick and pulled it out of her mouth, saying,

"Cum all over my face, Master. I'm your whore."

I took hold of my dick, jerking off, inches from her face; my first shot hit her between her eyes; she flinched but knew not to move. The next was in her right eye, and the rest dripped on her tits. She didn't move; kneeling on the floor before me, she cast her eyes down, knowing her place. She was still handcuffed but didn't say a word.

I pulled her up, but she kept looking down and whispered,

"Was I good? Did I please you, Master?"

"Yes, for your reward, you may call your mother, with a five-minute time limit."

"But first, I have something for you." I handed her a small black bag; she gasped when she took it out; it was a narrow black leather collar with jewels and a small silver padlock fastener. I opened it, putting the key in my pocket. I then fit it around her neck, snapping the lock,

"You're mine now."

I unhooked one hand and gestured toward the couch,

"Put a towel down so you don't drip cum."

It was clear I wouldn't let her clean up before her call. I sat on a chair across the room with my cell, taking pictures of her with my cum drying on her face. She wiped some cum from her eye and quickly sucked it off, afraid to look at me. The call was sad, I had put her phone on speaker, and her mother couldn't understand why she would leave such a good husband. I stood up and walked over to her; there was a large drop of cum on her nose. I scooped it up and held it in front of her face, and then I smeared my cum on her cheek.

Jill's eyes were welling up, and she could barely speak, so she cut it short, telling her mother she had to go.

I patted her on the top of her head and said,

"Good girl; now clean up, and let's get some sleep."

Lynn returned my call in the morning; in talking with her, a "Tramp stamp" was out for now; it seems a garter belt would be right on top of the tattoo and interfere with healing. I wasn't going without seeing her in her sexy underwear for a couple of weeks, so I decided on something for her neck.

She got out of the shower with a small towel barely covering her; she coyly asked me to approve her outfit. Jill slipped into a pale-yellow mesh bra with a matching thong, garter belt, and suntan stockings. She went to her closet, wobbling on her white stiletto heels, and picked out a short white skater's skirt and white wool sweater that molded to her tits. She slipped into her heels and laughed, "I hope it's not windy today; this skirt will never stay down." Giving me that pouty look, she did so well. Pete was right; I had lucked out.

We ate at a small coffee shop. I was walking in with a blonde beauty dressed like Jill was, which did wonders for my ego. Most of the women had on jeans and flat shoes, making me the envy of all the men. I noticed a woman and man paying close attention to us. Jill recognized the man. He worked with her husband. I told Jill to move her legs from under the table and pull her skirt to her garter clasps. She looked at me with pleading eyes, but she knew better than to object and slowly pulled up her skirt and displayed her stockings, her cheeks turning red. The woman came over and forced a smile, introducing herself and asking,

"What an unusual choker; it almost looks like leather," Jill remained silent, looking to me for permission to answer.

"Jill answer the nice lady,"

Jill cast her eyes down and mumbled, "Thanks; it is leather."

The nosy old broad frowned at me and walked away without saying a word.

After we finished, I sent her up to pay the bill, watching all the men follow her with their eyes, her white four-inch heels making that great clicking sound. I had told Jill to get me a pack of gum from the bottom shelf, and she knew what I wanted. Her cheeks flushed, but she obeyed and bent over at the waist, her skirt flaring up, exposing her stocking tops. She stood up and smiled that smile that first sold me.

She took my arm and put her head on my shoulder as we walked out.

I called Lynn, and she met us at the door. Jill was shaking as I looked at the samples, and Lynn and I settled on a design.

Jill wanted to know what it was, and I said she would see it when it was done. I kissed her as Lynn took her arm and said to give her at least two hours, maybe more; I had no idea how long these things took, so I told her to call me.

Lynn was looking forward to seeing Jill again, and they sat down to have a cup of tea and relax before starting.

Jill was nervous and gulped her tea down. Almost immediately, she felt woozy and staggered when she stood up. Lynn helped her to the recliner, saying.

"That's such a pretty outfit you have on, and I don't want it to get wrinkled; let me help you off with it here." Jill felt she should complain, but no words came out as the room started to spin.

Lynn deftly unzipped the skirt, pulled it off, and unbuttoned her top. She got a hand full of tit as she helped her into the chair. Lynn stood back and admired Jill's beauty as Jill slipped into a fog.

She was finished in two hours and called me saying to give her another hour. She had covered Jill with a sheet so that she could concentrate on the tattoo. As she took the sheet off and looked at Jill in her underwear.

What a pity it was; for her to be wasted on a man. Carefully, she moved Jill's thong down to her stocking tops and massaged her soft pussy. Jill began to moan and moved her legs apart so Lynn's tongue could get into her moist pussy. Jill was waking up and realized what was going on; she half-heartily said,

"Stop it right now; this isn't right; you're taking advantage of me. I will tell my Master what you are doing to me?"

Lynn was not fazed; she attacked Jill's warm cunt with her tongue and fingers. Jill tried to resist but ultimately gave up.

It didn't take long for her to have a decent orgasm, pinning Lynn's head between her nylon-covered legs. As Jill relaxed, Lynn moved up, laying on top of Jill, and gave her a wet kiss, tasting of pussy juice. Then she moved up, straddling Jill's face, and lowered her aching cunt onto her. Jill wasn't quite awake when Lynn started rubbing her pussy on her mouth, smearing her face with wetness.

Jill woke up mad, "Get off of me, I don't like this!" as she pushed her off.

"I can satisfy you in ways a man can't. Just give me a chance."

Jill shook free of Lynn's probing fingers,

"Just get away from me."

Lynn left the room quickly as Jill reached for her phone and called me to come to get her. As she was getting dressed, she wondered what she would say. Lynn was stoned-faced when she explained how to care for the tattoo.

On the drive home, Jill seemed distant, but I was sure it was whatever was in the tea. Her neck and wrists were bandaged, so I had to wait to see them.

Jill took off her skirt and top as soon as we got home. She made me lunch, saying she wasn't hungry. We then sat on the couch in front of a fire. She snuggled up against me and said,

"I never want to leave your side again."

"Ok, but what's wrong?"

She then told me everything that happened with Lynn, finally breaking down crying.

I held her close, reminding her she had some blame for what happened.

But my mind was racing with the possibilities of Jill enduring forced encounters with lesbians while I watched.

I slept well and woke up to a beautiful young woman in stockings lying next to me; I nudged her awake.

"Good morning, Master. What's up for today?"

"I'm going to take you shopping, but first, let me remove your collar so you can shower."

As Jill got up, I told her to wait a minute. I pulled out a short leather leash that I had hidden.

"Get on all fours, now," there was no question in my voice. Jill dropped to her knees and then her hands, "What are you going to do, Master?"

"Teach you how to crawl, my beautiful whore."

I hooked the leash to a ring on her collar and pulled her a few steps; I looked back at her,

"What are you waiting for, I said CRAWL!"

She hung her head, and with her full tits swinging, Jill crawled to where I was standing.

I jerked the leash up, telling her to sit up and beg.

"I don't like this, Master; can we stop now."

I sat on the couch, pulling her leash until she was at my feet. Jill was not enjoying this.

"I want you to sit at my feet until I decide what to do with you for asking me to stop."

She just sat on her knees, her butt resting on her calves, the stockings pulled tight. Holding her hands up in the traditional begging stance, her head hung low. Jill's phone rang in the next room, and it was her father. I thought it was time for some fun.

"Let's go, Jill; time for you to learn to fetch."

I stood up, pulling her leash, as she dropped down and crawled into the den. I spotted her phone on the desk. I picked it up, held it before her face, and slid it across the floor. I walked her over to the phone and told her to pick it up with her mouth. With tears streaming down her face, she was able to get it into her mouth.

"Good girl, now come to me,"

Jill crawled back and sat at my feet, her tits nearly out of her bra. With the phone still in her mouth, I took it gently from her, patting her on the head, saying,

"Good girl, now call dad and tell him about your tattoos."

Jill was trembling. She was ashamed to talk to her father on a leash, especially with me beside her.

She told me once that she was very close to her father, and he, in turn, treated her like a princess. As she was getting ready to call, I stood up and took my pants off, my semi-hard dick inches from her face.

"What are you doing? Please, not while I'm talking to him."

I sneered,

"Suck me till I'm hard, and then I'll let you jerk me off while you talk with him."

She slowly nodded yes and took my cock in her hot mouth, and began going up and down, softly moaning.

If you try and make me cum before your done talking, I'll cum all over you and put you on "Face time" with him."

I was rock-hard, but I wanted to watch her giving me a hand job while talking to her dad.

I heard him pick up, and tears started running down her face at the sound of his voice. He couldn't understand why she left her husband and even offered to come to get her and take her home.

"You don't understand, "daddy." I'm much happier now. I'll call you; I have to go."

"Look at me, Jill," As she turned toward me, I unloaded all over her face.

"Don't clean up till I tell you."

"Yes, Master," she mumbled. I hooked her leash to the couch and went to get a drink.

To be cont.