Jill the Best Secretary Ch. 03

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Jill has a surprise of her own.
4k words
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Part 3 of the 6 part series

Updated 01/28/2024
Created 07/28/2022
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hoover789
hoover789
307 Followers

I was pleased with Jill, she did what I wanted with only a minimum of complaining, like I said, we were getting along like an old married couple, but that was going to change, and I had no idea it was coming so fast.

Jill continued to wear stockings and garter belts, most of her dresses were tight enough to show her garter clasps thru the thin material. Between her legs and tits and her choice of underwear she was a dream come true

She enjoyed going to the post office every day; loving the looks she got, walking to get the mail in her spike heels. Wednesday while she was gone, her husband called.

He had been trying to reach her, but to no avail. He wanted her to stop by the dry cleaners on the way home, he needed his suits for this weekend's trip. We talked for a few minutes, he said he was tired of going away , but this was an important client, and he could not get out of it. while he was talking, I was planning what I was going to do to his busty wife, I got a raging hard on, picturing her asleep on their bed with my cum dripping off that beautiful face.

Soon Jill returned with the mail, feeling fairly good,

"Well Mr. Bennet what's up for lunch?"

"Let's get something from the deli." I said looking at her perfect butt, as she bent over to pick something up, she always made sure to wiggle when she stood up.

"Sounds good, I'll get it when its ready,"

She didn't think I knew that the young guys in the deli fawned all over her, if they only knew what I was getting.

Later after we had finished eating, I casually said,

"So your husbands going away this weekend, and you didn't see the need to tell me?"

Her face lost color and she looked down at the table,

"I'm really sorry, it's just for Friday night, I forgot about it till now."

" lying to me is worse, you definitely need to be punished, now come over here."

"What are you going to do?" "I promise to make it up to you, I'll do anything you want this weekend, just not now."

"What if I don't want to wait?"

"Please, Mr. Bennet, not in the office, I want to relax, and I can't here."

What an interesting thing to say. She came close to saying she enjoyed it, one thing for certain she wasn't happy now. Her eyes were welling up, and she was visibly shaking.

"Now strip, you know you need this, I can't believe your husband doesn't spank you regularly."

"You can't be serious; I wouldn't let him spank me." "Then that's his fault, a man should be able to discipline his wife, with a good spanking when she needs it."

Jill got a sick look on her face; she knew what was coming.

"Mr. Bennet you know the door is unlocked; anybody could walk in."

" You can lock it if it makes you feel safer, but only if you take your clothes off first."

"Why are you doing this to me, somebody could just be walking by and look in."

"Hurry up or I'll make you work the rest of the day in your underwear."

"I never thought you'd be like this," she murmured.

Jill turned beet red and reluctantly unzipped her skirt and let it fall to the floor, then she unbuttoned her blouse and hung it on the chair. She was gorgeous, standing before me in her underwear ,she had on a pale purple demi cup bra, matching silk panties, garter belt and sheer off black stockings.

"If you want you can lock the front door, but you better hurry, remember we're due a delivery of copier paper, you might have to answer the door dressed like you are."

She stifled a groan and walked slowly to the door of my office and carefully looked out, bending over as she hurried to the door and locked it. Then she ran as fast as she could in her heels, back into my office, tits bouncing like crazy.

"I can't believe you made me do that; can I get dressed now?"

"No way young lady it's time for your punishment for not telling me about your husband, now come over here."

She walked over to me, mindful of the way her tits were jiggling, trying to overflow the lacey bra.

"She bent over at the waist, adjusting her stockings, she looked up at me, do you think this bra is too skimpy?"

I knew she was trying to distract me and maybe get out of a spanking, and it almost worked, like most beautiful women she knew how to use her body.

"What do you want me to do, I said I was sorry for not telling you."

"Jill, the cute act isn't going to work, I'm going to warm up your butt."

With that I grabbed her arm pinning it behind her back and forcing her over my knee, her sheer panties stretched across that round butt, she started kicking her legs and begging me not to spank her.

I rained four quick blows to her upturned ass; she was squealing like a stuck pig.

"Please stop, it hurts, I'll be good I promise, please let me up."

"Not just yet, I want to take the sting away." I stroked her ass gently, after a minute my fingers strayed near her cunt, she spread her legs slightly and moved her ass up a little, making it easier for me to trace her mound carefully. She was moaning and trying get her slit closer to my probing fingers. I moved her silken panties and gently slid my finger into her hot wet cunt, I swear she had an orgasm, she squeezed her legs tightly around my hand trapping it. She begged me to stop, saying she couldn't enjoy it and wanted to wait, but she continued to grind her pelvis against me.

I pushed her down to her knees, she looked up at me with tears running down her face from the spanking, her tits nearly out of her lacey bra.

"I want you to remember you said I could do whatever I wanted this weekend, I'm going to hold you to that, now get dressed."

" You know if your husband spanked you when you needed it, you'd be more truthful and a happier wife."

Jill looked down at the floor and nodded yes, she got up, adjusted her bra, and got dressed, careful not to look at me or say anything, I know she didn't like me talking about her husband, but she never complained. She wasn't broken yet, but she was close.

The rest of the day was uneventful with Jill speaking only if necessary, so it surprised me when at the end of the day, she came in to say goodbye, she bent over and kissed me on the cheek and whispered in my ear,

"I want you to stay at my place Friday night, he won't be home till late Saturday, and I just want to have time together with you."

I said I would think about it, Jill looked at me with those blue eyes and said, " You won't be sorry." She got to the door, turned, and looked at me, then rubbing her rear end, she winked and left.

I had thought her being married would rule out her falling in love with me, maybe I'm wrong, but it sure seemed that it was happening. The way I looked at it, was a woman in love will let you do anything you want to her, for a while anyway.

Since Jill had started working, I noticed a lot more men paid their premiums in person rather than by mail, and Jill never disappointed them, with that smile and body. She always made sure to give them a little leg show, but always acting innocent.

One day a man in his late sixties, came in with a chip on his shoulder about some payment that hadn't been credited, she brought him to her desk and resolved his problem all while distracting him by exposing her stocking tops and garters, he left flying high, from her little show, saying how good she was.

Friday came and I was like a kid at Christmas, thinking of ways I could dominate, poor Jill.

I was at my favorite spot, waiting to see her get out of her car, and I wasn't disappointed. When she parked and swung her legs out, her skirt was up to her crotch, displaying sheer black stockings, she quickly stood up and pulled her pencil skirt down, but it was so tight she had trouble getting it down to her knees.

It was almost painful, watching her walk, between the skirt and her heels she could barely move, the sweater top trying in vain to control her perfect tits. Sitting down at her desk, she said,

"I know you like me in heels Mr. Bennet, but these four-inch stilettos are real killers."

"Get used to them, you'll be wearing them to bed Friday night."

She just smiled and shook her head, "men," she was always amazed at what turned them on.

We settled down to work, the morning went quickly; at lunch Jill seemed to have something on her mind.

Wondering what drama she had thought up now. Finally I broke the ice,

"What's bothering you Jill?"

She wouldn't look me in the eye,

"Mr. Bennet, I know it was my idea, but I don't think you should sleep over, I'm scared we'll get caught. I'll do whatever you want tonight, but I don't think it's safe you staying in my house."

She sounded sad, but I couldn't let her change plans, I was supposed to be in control.

"You asked me to stay over and I'm going to hold you to it."

"I know I've not been a good wife, but I feel bad for my husband, it's not his fault, please don't make me do this."

I wasn't going to let her off the hook, but I also couldn't force her into a corner,

"Alright, I won't stay over, but it's going to cost you, and you know how creative I can be."

Jill grimaced,

"Thank you, I promise you'll have a good time, just please don't get too creative."

Quitting time came and we locked up, Jill telling me to come over at six o'clock, she said she wanted to look special. I got there just at six, and of course she wasn't ready. She had a terrycloth robe on and had just started fixing her hair, she told me to get something to drink and make her a martini.

I made the drinks, with a little more liquor in hers, and headed for her bedroom, she stood in the doorway blocking me from going in,

"Let me get dressed, go sit in the den, I won't be long."

"No," I said firmly, "I'm going to watch."

"At least let me put on my bra and panties in the bathroom?"

"I guess, just don't be long."

While she was gone, I took a look around, I noticed on her bureau there was two pictures, face down, I put them up, one was her husband and her on their honeymoon, the other was her parents, she didn't want to see their faces while she was screwing me, that could be the only answer.

I sat back on her bed, and prepared for the show. Jill didn't disappoint me, she fastened her garter belt and pulled on sheer black stockings up those flawless legs, her tits almost bubbling over her half bra, as she twisted to fasten her garter clasps.

"Do you want me, to put on a dress or this robe?" she said holding a black lace robe, that barely came down to her butt.

"The robe is good."

"Thanks I didn't feel like a dress tonight," as she slipped on black heels.

If I were married to Jill, I would be fucking her as much as I could, I didn't know what could be wrong with her husband.

We went into the den, I made sure to stay one step behind her, taking in the sight of those nylon covered legs with her heels forcing her round butt out.

"Let's order Chinese I'm starving." Jill said, getting out a menu.

We had a half hour wait for the food, I sat on the couch and pulled her down next to me, putting my arm around her, cupping her soft tit with my other hand. Her eyes closed as I started kissing her neck and at the same time placing her hand on my growing cock. Jill was moaning as I freed her tits and began lightly biting and sucking her swollen nipples. She was holding my head against her chest and at the same time telling me to stop, the food would be here soon. We were sitting there kissing lightly and holding each other, her fingers wrapped around my dick gently stroking me, when the doorbell rang. I got some money out and handed it to her.

"You're crazy, I can't go to the door dressed like this." As she nestled her tits back into her bra.

"Well I can't either, he probably knows your husband, just stay behind the door,"

as she got up, I cracked her on the ass, she yelped and went to the door clutching her robe around her, wobbling on her heels. She tried to hide behind the door, but to no avail, her legs were in full view as she took the food with one hand and pushed the money at the startled delivery man, exposing her barely covered tits and then slamming the door shut. I was laughing, but she didn't see the humor, glaring at me as she made another drink.

I was finding out Jill was the type of woman that liked sex, and was willing to try different things, but first she had to be drunk, to give herself an excuse, which was fine with me. The food was good, we finished and sat close to each other talking and getting drunk.

Jill was definitely high, she was starting to slur her words, and more than once asked if she could take off her heels, of course I said no.

We sat on the couch, she turned toward me and whispered, "Kiss me." Our lips met, her mouth opened, her tongue searching for mine. Her eyes were closed, and her moaning was becoming ragged as my hand strayed to her cunt; she stiffened at first, then moved a little, granting me access to her warm slit. She gasped.

"Don't stop, it feels so damn good; he never does this anymore," as my fingers found her clit, massaging it. I had two fingers in her, her head laid back and was lolling side to side.

"I'm close, for god's sake don't stop, I'm gonna cum!"

And cum she did, shuddering and squeezing her legs together grinding her cunt against my hand.

"I want more;" she hissed, "Now make me a drink, and lets go to the bedroom." She sat on the edge of the bed drinking her martini, I pulled her back onto the bed, taking her bra off, while licking her super sensitive nipples.

"Time to suck some cock Jill," I said moving my dick close to her open mouth, I rubbed my hard on over her lips and she greedily sucked it down, moaning and slobbering over it. I noticed her hand had strayed to her cunt, she was rapidly fingering herself , I pulled my cock out of her mouth and rolled her over,

"Stick your butt up, I'm going to fuck you from behind."

I moved up behind her and slipped my raging dick in her hot slick cunt, it felt like paradise, I tried to pace myself, taking short thrusts. She adjusted to me and started meeting my full assault on her hot pussy, she started to tremble and had another violent orgasm, wiggling her butt against me. She started to slow down some and gasped "Don't cum in me, I'm still not on anything, I can't believe you didn't bring a rubber."

I'll be damned if I was going to wear a condom or cum on the sheets. I grabbed a bottle of hand lotion from her nightstand and dribbled some on her puckered asshole.

"What the hell are you doing?" she sounded scared.

"If I can't cum in your cunt, I'm going to fuck your ass."

"No way, now get off of me, and I'm not kidding!"

She started struggling trying to get up, but I was too strong for her, and she finally gave up and started to babble, begging me to stop.

"Relax, I'll take it slow."

I said as I slipped a greasy finger into her puckered ass, I gave her a minute then eased my cockhead in, there was resistance, but her tight hole finally gave way, as I slid in her hot tight little ass. She let out a groan amid her crying,

"You're tearing me apart, TAKE IT OUT !, TAKE IT OUT! , I'LL DO ANYTHING YOU WANT !... I'll do anything you want, just take it out," she lapsed into sobbing, as I pounded her virgin ass, enjoying her discomfort, after a couple of minutes, I couldn't hold back anymore, I let loose, cumming in her tight ass. I finally relaxed pulling my dick out and she collapsed on the bed, crying, cum dripping out of her.

"I can't believe what a pig you are." She groaned

I was exhausted; but satisfied, I was going to give her a few minutes before talking with her. She finally pulled herself into the fetal position, and wouldn't look at me.

"I'm getting in the shower and then I'm going to order a pizza, so you better tell me which one to call, so you won't be embarrassed when you go to the door."

After my shower, I felt great. But poor Jill was sitting on the edge of her bed, feeling sorry for herself, she looked at me,

"You really are a sick bastard, doing it in my rear and don't think I didn't notice those pictures were up."

"What are you worried about?" " That you're husband and parents are going to see you getting your ass reamed? And yes, I enjoyed it, you've got a tight butt, and guess what, you survived, so stop complaining."

Jill looked at me, then just hung her head, looking at the floor.

I threw her panties and bra at her,

" Here put these on, the pizza guy will be here soon."

She didn't complain, I had her under my control, she was mine to play with, it's amazing how an ass fucking establishes who's in control. After putting her underwear on, she reached for her robe, and slipped into her heels. I couldn't put my finger on it, but something more was wrong with her then getting it in the ass.

Maybe she wanted me to go home, boy was she in for a surprise.

It was nearly ten o'clock when the pizza came. We were back in the den, when the doorbell rang, I almost went, but it was more fun to watch her humiliation.

"I can't believe you're making me go to the door, dressed like this, don't you care if I'm embarrassed?"

"Get moving Jill I'm hungry."

When she reached the door, I grabbed the back of her robe and pulled it half off, she tried to stay behind the door, but it only made things worse, her robe gaping open, exposing her garter belt and stockings, and then it happened,

The pizza boy said, "Hi Ms. Watson, is the coach here,"

Her worse fears came true, it was one of the boys her husband had coached high school baseball, years ago.

She mumbled, "No he's out," and slammed the door.

She threw the pizza down, and said "I'm ruined, and it's my own fault."

Tommy the pizza guy couldn't wait to tell his friends what had just happened, all the guys on the team had fantasized about her. This was one address and phone number he wasn't going to forget.

I pulled her down on my lap and cupping her tits, I said

"Nothing is going to happen, now let's eat and then I want to fuck your knockers."

"That's just great, as upset as I'm, you could be a little nicer."

It's funny for being so upset she ate two slices and had another martini. After a while we sat on the couch, I pulled her close and started kissing her neck while stroking her nylons, playing with her garter clasps, all the while getting my hand closer to her cunt.

"Stop teasing me, I want you to kiss me down there, you owe me."

I slipped her panties off and kissed her on her thigh just above her stocking tops, I was kissing her legs lightly, getting closer to her slit, she moved down some, spreading her legs getting closer to my mouth, at the same time I eased my tongue in her cunt, licking her clit and rubbing my face on her.

"Ohhh god ,don't stop, it feels so good, now make me cum."

I licked her swollen cunt lips as she held my head with her stocking covered legs, I was sucking and nibbling her clit, when she shuddered and had a wild orgasm, her whole-body trembling, I kept licking her juices, until she gasped,

" That was heaven, I haven't cum like that in years," She said, hugging me closely, then she softly said, "Now let's go in the bedroom and make me you're whore, and fuck my husband, it's his fault for leaving me alone."

When we got in the bedroom she walked over and picked up the picture of her husband and put it on the nightstand,

"I'll give him a front row seat; I hope he enjoys the show."

I mauled her tits and then pushed her on her back,

"Hold your tits together," I ordered, and she readily complied, I poured some lotion on her big tits and proceeded to fuck them; it was great to see my dick plowing between her boobs. She was moaning. "Do what you want I'm yours."

I lasted as long as I could, then I erupted all over her neck and face, for a senior citizen on Viagra I didn't do badly, for Jill it was another Friday night facial. She just lay there with her hands on her crotch almost passed out, with cum dripping down her delicate features.

hoover789
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