Jill the Best Secretary Ch. 06

Old age was making me soft. I finished my drink and felt a little guilty looking in at Jill. She looked pitiful, her leash still hooked to the couch. My cum drying on that beautiful face. I almost felt bad knowing I had broken her once cheerful outlook on life.

My problem was, eventually, I would grow tired of her. Then, what to do for fun. Maybe make her available for gang bangs. There was no shortage of men wanting her. And would be willing to pay for the privilege.

I gave her an hour more chained to the couch. I walked into the room; she was trembling from fear and not being able to move. She hung her head, not able to look me in the face. I unhooked her restraints and told her to go wash up. I gave her a quick hug, and she started to smile.

After showering, she walked into my study naked, cupping those perfect tits. Her pink nipples pointing straight out. She whispered.

"What do you want me to wear, Master?"

"You can wear sweats now, but I want you to dress for dinner. We're going out to eat. And I want everyone looking at you."

She nodded but kept her head down.

I had broken her, but I couldn't ruin her completely. I wanted a little fight left in her.

Jill came back in almost transparent black yoga pants and a crop top. She had put her hair up and walked over to me in black high heels.

She snuggled up to me, nuzzling my neck, saying.

"I'm so comfortable; I didn't feel sexy in sweatpants. Are these all right? I really do love you, Master; why are you so good to me? Am I talking too much?"

"If you are, I'll slip something in your mouth," I said, looking into those round blue eyes.

Pursing her pink lips, she whispered

"You can do anything you want. I'm yours forever."

I reached over and pinched her nipples. She cried out but didn't stop me. We wrestled around. I pinned her down, grinding on top of her. She was a dream come true.

I decided we would go for a walk; the weather was nice, and I wanted to show her off. We drove a few blocks to the center of town and then walked for a while window shopping. I was enjoying the stares Jill was getting. I'm sure she realized her yoga pants were transparent when the sunlight hit them. To her credit and fear of a spanking, she ignored their stares. But I couldn't blame them; her top was little more than a bra, exposing most of her tits except her nipples.

We entered a small coffee shop and sat next to the front window. She knew I wanted her on display and leaned forward, her firm boobs practically on the table. I sent her up to get the drinks. Of course, all the men followed Jill's progress in her four-inch spike heels. It was an ego boost for me, all these guys knowing I could tap her whenever I wanted.

We spent a good hour talking. Jill seemed relaxed, I guess, hoping her discipline was over. Think again, Jill. As I followed her out, I realized her ass was in full view with those see-through black pants, and in the front, the smallest of thongs covered her pussy. I made plans for that rear.

Jill asked if it was all right to do a little shopping. I am not the type of man to follow a woman around a store holding her purse; come to think of it, that was not something any man should do.

We got to the door of a lingerie shop.

"I'll give you half an hour, then I will be leaving, so unless you want to walk home in those heels, you better be ready."

She smiled and kissed me on the cheek. As she turned to go into the store, I couldn't resist that smooth ass in those pants. I slapped her with a good open-handed shot on the ass. She wasn't expecting it and yelped loudly as she rubbed her rear, hurrying into the store. A middle-aged woman looked on in disgust. I found out later that the woman approached her in the store and wanted to know if Jill was trapped in an abusive relationship.

Jill hit her with that dazzling smile and said with a little laugh.

"I sure hope so. I need it."

Jill couldn't wait to get into the car and tell me what had happened. She was so proud of herself. I kissed her and told her to do something for me. She sat up in her seat,

"Anything you want, Master."

"Play with your tits on the way home."

"Aren't you afraid someone will see me?"

"If they do, they'll know how lucky I 'am. Now get squeezing."

I could see how embarrassed she was. We had to stop at a red light. Several people were standing by a bus stop; I looked at her and said.

"What are you waiting for?" Her hands were trembling as she cupped her boobs rolling her nipples between her fingers. I waited for a few minutes, giving the people a show. Her boobs were super sensitive, and it wasn't long before she was moaning, letting her head fall back with her mouth partially open.

Finally, she gasped. "Are we almost home? I am going to explode."

"We are almost there."

I lied; I had purposely gone out of my way while she was working frantically on her swollen tits. Two men in a truck alongside were watching us; I slowed down and stopped. They couldn't believe their eyes, yelling something I couldn't understand and waving. Driving off slowly, I looked back, and both were giving the thumbs-up sign.

Jill was oblivious, her eyes shut tight. Thank god the traffic was light. I kept one eye on the road and laid my hand on her thigh. She squeezed her legs together and groaned, then let them fall open to my touch. Her pants were so thin I could push her thong aside and ease my finger in slightly. She placed her hand on mine and tried to force my finger deeper. The pants were preventing any penetration.

"Slow down, Jill. We'll be home soon."

"Oh please don't tell me to stop I'm sooo close."

We pulled into our driveway. I looked over at my beauty, her top pulled down, one hand torturing her nipples and the other hand in her lap, moving gently.

"Let's go inside and finish this."

As she turned, I unsnapped her skimpy top, pulling it off. She gasped.

"What if someone sees me?"

"Then we will invite them in for some fun."

"That's not funny; you're not serious, are you?"

"Oh, Jill, I'm just kidding, but it might be fun," I said as I dreamed of different scenarios to put her in.

She looked both ways; seeing no one, she opened the car door and stepped out. I pinched her rear to get her started.

She ran as fast as her heels would allow while cupping her bouncing tits. It was still light out, the sun setting. I hoped the college boys from down the street would be out, but no luck. Jill made it to the door, which was locked, of course. I stayed in the car for a few minutes. Finally, I walked to her.

"Hurry up, Master. I'm afraid someone will see me.

'I'll open the door if you stop covering your tits." Which was a joke. Her hands barely covered her nipples. Her boobs bulged obscenely behind her hands.

"I'm begging you, PLEASE don't make me do that."

"Turn around, face me, and cup those tits and shake them a little."

A tear rolled down her cheek as she closed her eyes and bit her lower lip. She complied, her nipples hard as rocks. Just then, the automatic lights came on, bathing the porch in a soft glow. She cried out involuntarily.

"For that, put your hands behind your back and stand straight up."

She looked at me with pleading eyes.

"The longer you take to do it, the longer I'll make you stay that way."

Jill blushed furiously and complied. Her tits protruded on her petite frame, making them look bigger than they were. She was shivering in the night air, her beautiful boobs covered with "goosebumps."

I couldn't resist. I cupped them together and sucked on her nipples, carefully nipping them until she was moaning.

"Take me in the house. Do anything you want to me. Treat me like a whore."

I stepped back,

"Ok, you want to be my whore, pull your pants down and finger yourself."

Tugging her pants down, she slipped her finger in her wet pussy with one hand while squeezing her tits with the other. She couldn't stand up straight. Her fingers glistened in the light.

"Lick your fingers clean."

She practically swallowed her hand as she licked and sucked her juice from her fingers, softly moaning.

I opened the door, and once inside, I reached down, grabbed her around the waist, and threw her over my shoulder. I could feel her tits rubbing against my back. She squealed as I smacked her ass and carried her into our bedroom, dumping her on the bed. I pulled her yoga pants off, snapping her thong in the process. Jill lay there panting, looking up at me, trembling, she whispered,

"What are you going to do to me."

I didn't say anything; I just stood over her, holding my cock, rubbing against her already wet cunt, then lifting her and hooking her legs over my shoulders. I found her puckered asshole—her eyes were wide in fear. "Not in my ass, please use my pussy. I want you inside me."

"Don't worry, I'll be inside you; it will just be your ass."

"Ohhh, nooo." She groaned as I poured some lube on my finger and slowly pushed it inside her tight hole.

"Please stop; it's going to hurt."

She looked up at me, her blue eyes filled with tears.

"Can't we just have regular sex? You can finish in my mouth if you want, please?"

I smacked her tits and said.

"Get on your hands and knees."

She immediately got on all fours with her ass in the air. I poured the lube on my finger and gently probed her ass. I could feel her tense up and move away a little.

"You're only making it worse for yourself, Jill; just relax."

I knew she couldn't. I had fucked her ass before, and she hated it. All she remembered was the pain and some bleeding, and she didn't want to go through it again.

She couldn't relax; she was starting to cry as I was trying to get my finger in. She was moaning and groaning, telling me it made her feel like a tramp. I reached into the nightstand and pulled a slender dildo out, just for situations like this.

Her voice quivered.

"What are you going to do with that?"

"What do you think? I'm going to fuck your sweet ass."

I said as I lubed it up and eased it into her puckered asshole. She was gasping and trying to move away. I got it in about two inches and said.

"Hang on."

I switched it on. She let out a low moaning sound and wiggled her ass. I probed her cunt with my dick, and she dropped the front half of her body, putting her head on her folded arms, pushing her rear in the air.

"Please take that thing out of my ass. I don't like it."

I ignored her. She was still tensed up. I slid my rock-hard cock in her snatch. I could feel the vibrations from the dildo in her ass. I increased the setting to medium, and she thrust herself backward to meet my attack on her cunt.

I was enjoying myself. Between her tight pussy and the vibrations, I knew I wouldn't last long.

I started gently moving the dildo in and out.

She was grunting quietly, finally saying she was finished. The dildo hurt her, and she couldn't enjoy herself. I pulled it out, slick with lube, making a wet popping noise.

I was far from over and rolled her over on her back.

I plunged into her dripping snatch, eliciting a moan telling me to take it easy. I battered away at her, enjoying her discomfort. I couldn't last much longer.

Her cunt was so tight, and looking down at her beautiful face, I let loose, filling her up. She wrapped her long legs around me and kissed me hard on the lips.

She whispered. "I never thought I would love someone as much as I love you and how you treat me."

We both collapsed, falling asleep with my arms around her.

We slept until nine the next day. I laid back, looking at her as she slept; she was beautiful, her delicate nose and unblemished skin, but the best was her tits. Even lying on her back, they hardly sagged. I never thought I could have snagged a beautiful woman like her. So why did I want to exploit her?

I got up without waking her. Walking into the kitchen, I toyed with the thought of a little party with Jill as the entertainment. I didn't know if I would tell her beforehand or surprise her. And should she be the only woman with three guys or maybe a few couples? But it might crush her beyond repair. And I didn't have the time or energy to break someone new in.

My thoughts were interrupted when Jill walked in with black bikini briefs on and nothing else. Her ripe tits bounced with every step she took in her heels.

"May I make you breakfast, darling?"

"Sure, eggs would be fine."

As she walked by, I cracked her tight ass, she squealed!

"STOP IT!"

At the same time, bending over, shaking her ass, "Maybe one more, please? I feel naughty."

She smiled that same smile that got her hired.

After we ate, I heard the guys shooting baskets and thought I'd walk over.

"Jill, what would you think about inviting the guys from down the street to watch the playoffs?"

Jill frowned.

"Just us and them and no one else?"

"That's what I was thinking."

"I would feel funny being the only girl."

Her mind raced back to her eighteenth birthday.

A girl she hardly knew told her there was a party at a house where the parents were away. There would be free food and booze. But she chickened out, afraid of not knowing anyone. It turned out there were three girls and at least fifteen guys. They spiked the girl's drinks and gang-raped them. One girl had to be hospitalized. And three months later, another girl turned out to be pregnant. When she first told me the story, she admitted feeling a tingling in her pussy. The thought of being surrounded by a gang of men, free to do whatever they wanted, had turned her on.

"What are you afraid of, Jill? I would protect you."

Jill snapped back to reality.

"I know you would. I just don't see how it would be fun."

I knew then it would have to be a surprise. Now, I would have to figure this out.

I told Jill I was just going down to talk with them. She had a worried look and said she would shower and get dressed.

I walked down and introduced myself. Bill and Todd were staying with Frank, whose parents owned the house. They were seniors at State University. They readily accepted an invitation to watch a playoff game this Saturday night. I know they were dying to ask if Jill would be there. Finally, Frank got up the courage,

"Ask your wife if we can bring anything?"

"Oh, Jill's not my wife. We are just living together."

The look that came over their faces was priceless. I'm sure they believed they had a shot at her. After all, they thought I was a harmless old man who couldn't satisfy a girl like Jill. This was going to be fun.

Jill greeted me at the front door wearing a dark brown demi-cup bra, matching panties, garter belt, and coffee stockings, teetering on her four-inch red-sole heels. Her blonde hair was in a loose bun with strands framing her flawless face.

"What can I make you for lunch?" She purred.

"I'm not hungry yet. Let's sit by the fire."

I sat on the couch while Jill started a fire, bending over more than necessary. After ensuring I had a pillow and was comfortable, she snuggled up to me, her perfume filling the air. I looked down at her bra, barely containing her full tits.

How was I going to break the news? Then I thought, screw her. Her divorce was almost final. She had settled for cash, about enough to last a year. So, in reality, the way she spent money, she had enough for six months; then, she would depend on me. So she had more to lose than me; Jill needed me, not the other way around.

"I invited the guys to watch the playoff game this Saturday night."

She had been running her hand down my leg, but she stopped, and I felt her body tense up.

"Just guys?"

"Yes, all I need you to do is get drinks and food and, of course, look beautiful."

"I'll do whatever you ask, darling. What do you want me to wear?"

She said, her voice void of emotion.

"We have all week to think about it; let's enjoy today."

With that, I put my hand on the back of her head; she took the hint and moved down, unzipping my pants. Her hot velvet mouth swirled around my cock. I kept pushing her head down, making her deep-throat me. I enjoyed hearing her gag, but I wanted to fuck her. I pushed her on her back and pulled her panties off, noticing they were wet in the crotch. I took off my pants and shirt and lay on top of her, my dick finding her wet split and slid in. She gasped."

"Give me a minute to get ready, darling; you're too big."

That did wonders for my ego. With renewed energy, I pounded her without mercy; her nylon-covered legs wrapped around my back. I didn't last too long. I came, filling her up. I should have cum on her face, but her cunt was too tight. But I wasn't worried; there would be plenty of cum on her face soon enough.

We spent the day in front of the fire.

The rest of the week was routine, with Jill cleaning the house in her underwear. She did not mention the party once.

Saturday morning, I told her I was going to the liquor store.

"What do you want me to wear tonight?"

she whispered.

"I'm going to surprise you."

She smiled, but it was her phony smile.

The day dragged by. The game was at seven so at six o'clock we went to our bedroom. I sat in my chair, and Jill stood before me. I started to unbutton her top and noticed she was crying softly.

"I'm scared. I don't know these guys; all I want is you."

"And all I want is you, Jill. Since you've been so good about this, I've got a surprise for you. I'll tell you later."

I finished the buttons and spread the two halves of her blouse, exposing an overflowing white lace bra. I opened the front hook, and her pear-shaped tits leaped free, wobbling slightly.

"We're just going to watch the game; nobody will touch you."

I unzipped her skirt, letting it fall as she stepped out.

I unhooked her garter clasps, rolling her stockings down. Her garter belt and panties followed.

I motioned toward a bag on the bed containing her underwear for the night. She slipped into a black waist cincher and a half cup bra, creating deep cleavage. She slowly turned her back to me so I could pull the laces to the cincher tight. She groaned,

"Not too tight. I have to breathe."

That made me pull it tighter.

She stood still for a minute, then put on her sheer black stockings, pulling them tight. The cincher was so tight she couldn't twist far enough to fasten her rear garters. Asking me to help her. I pulled her stockings tighter, fully expanding her stocking tops. I then handed her a black hobble skirt. It was high-waisted and reached below her knees with a zipper in the back.

She stepped into it, struggling to pull it up over her hips.

"Are you sure you want me to wear this? I am barely going to be able to walk."

"That's the idea."

I smiled as I pulled the zipper to tighten the skirt.

Jill stepped into her four-inch black heels and a skin-tight, sleeveless white stretch top.

She took a few tentative steps, almost falling.

It's like my ankles are tied together."

"The idea is you take small steps," I laughed.

Which she did awkwardly, mincing across the room, her boobs bouncing.

"I don't think this is a good idea in front of young guys."

"You'll be fine now; let's get the food out."

I had a raging hard-on watching her struggle to walk.

They came over at seven, and I told them to sit anywhere.

"Jill, our guests are here."

She walked carefully, taking tiny steps, and came out of the kitchen with some beers, blushing furiously as her tits bounced with every step. Their eyes bulging out of their heads. They were captivated by her body. They just stood there looking at her without saying a word.

"Guys, this is my fiancé, Jill."

I had no intention of marrying her; I just liked screwing with her head.

I hoped they were too busy looking at her tits to see the shocked look on her face. I thought she was going to pass out. She motioned me to the kitchen. She had tears in her eyes as she hugged me tightly.