My Secretary Jennifer (Chapter 3)

by NiteWriter                                                                                                                                    (1997)

Well the tone was pretty much set after two days of fucking Jennifer. I was enjoying myself more than you could imagine and I know she was too. I was positive I could do just about anything to my cute redheaded secretary.

The next day, Tuesday, before I went to the office I picked up a few things at the store. Once we reached lunchtime I told Jennifer to come into my office while the other girls were out to eat. She had on the sexiest short skirt with black mesh stockings. She sure looked hot today.

"Pull your skirt up," I ordered.

When she did I pulled her panties and stockings down to her ankles. "Squat down," I commanded.

Jennifer obeyed wondering what I had in store for her this time. I had a banana, which I peeled in front of her. I reached between her legs and positioned it on her slit. Then I began inserting the long piece of fruit into her cunt. I pushed very slowly so it wouldn't break and I would get the maximum penetration into her hole. Jenn closed her eyes while I filled her lovely twat with the banana. A few seconds later only a little was left sticking from her hole. So using my thumb, I gently pushed the rest in.

"You can stand up now," I replied when I finished. "You'll work the rest of the afternoon with it inside you. See me at the end of the day."

With that Jennifer pulled her panties and stockings back on, fixed her skirt and returned to her desk. On a number of occasions throughout the day I could see how uncomfortable she had become, but not once did she go to the ladies room.

At the end of the day Jennifer hurried into my office after every one had gone. "I'm so horny you just got to fuck me," she begged.

"Take your clothes off," I ordered eager to comply with her request.

Jennifer stripped immediately. When she slipped her panties down those gorgeous legs I noticed how stained they were from the banana. There was a slimy mess stuck in the crotch of her delicate underwear. I grabbed them showing her the glob of slime in her panties. "You've been a naughty girl Jennifer. You made a mess in you panties."

I leaned to her, kissed her, and then whispered, "open your mouth." She obeyed, but reluctantly. I took her dirty panties and wiped the stained mess onto her tongue. "Eat it." I ordered. " Jennifer timidly closed her mouth and then swallowed it down.

"Now lay down on the desk," I requested next.

Jennifer laid back on my desk spreading her legs open for me. I pushed a finger into her cunt and I could feel the gooey banana. I knew it would be pretty well mashed up after being inside her all day. My cock was rock hard anticipating fucking her stuffed cunthole, so I grabbed it and shoved it into her. What a messy fuck it was. As I penetrated her hole, a thick slime oozed from her as I pushed in deeper and deeper. Then I started fucking her hard. Her cunt was slippery yet sticky and the banana was seeping out all over her crotch.

After five minutes of fucking her sloppy hole, Jennifer went into an orgasm. Seeing her cum made me lose control too, so I quickly pulled out, crawled up on the desk and knelt over her face shoving my cock into her mouth. Like a hungry whore she sucked off the banana coating from my hard shaft while I came in her mouth.

Once she finished eating my cum I climbed off the desk. Then holding her cunt open with one hand and probing with the fingers of my other, I started scooping out the remains of the banana. She was so excited from having it jammed up her twat most of the day that she went into another orgasm almost immediately. As her body convulsed, out oozed more of the messy fruit. It was a warm, slimy and gooey mess mixed with Jennifer's cunt juices. With a big glob of it on my fingers, I reached to her mouth smearing it across her lips, feeding it to her. What a horny bitch she was becoming. She lapped from my hand and swallowed it right down.

I returned to her cunt shoving two fingers all the way in. Then I worked in a third and fourth finger and began jamming her hot sloppy hole over and over while she was still cumming. She screamed out in pleasure as most of my hand easily slid in and out of her gooey messy hole.

"Ohhhhhh! God...Yessss..."

"It feels so good..."

She clutched my hand between her legs as another climax built within her body. Jennifer had another orgasm. As she held my wrist I backed out slightly and then began pushing into her again. Only this time I inserted my whole hand. Slowly I pushed as she felt me penetrating her body and she was letting me do it. She was going to let me fistfuck her tiny little twat.

"You're a nasty little whore Jenn," I remarked as I shoved deeper.

"That's it, take it up your tiny cunt."

I pushed hard and her soft pussy spread open gobbling my hand as it disappeared inside her hole. "Ooouuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuu..." Jenn let out a long moan as my fist passed through her tight little opening.

I had fisted her. Beautiful Jennifer, in the midst of a tremendous orgasm, had my entire fist inside her body.

"You're a nasty slut Jenn," I groaned pushing in deeper.

"That's it,... take it way up into your fuckin' little cunt."

I jammed deeper feeling the depths of her hole. I was making her squirm, as I felt around inside her lovely body while continuing to speak nasty to my darling Jennifer.

"I'm gonna make you cum again, you fistfuckin' whore."

I started fucking her hole, enjoying the feel of her wet slimy cunt. She was so hot too. The inside of her body felt like it was on fire. She squirmed and moaned continuously as I fist fucked her cunt over and over and over.

"Ohhhhhhhhhhhh!... Ouuuuuuuu!... Ouuuuuuuu!...

Ouuuuuuuu!... Ouuuuuuuuuuu!..."

My fingers probed and explored deep inside Jennifer, feeling the soft warm flesh of her inner body. After five minutes of ravishing her tiny fuckhole I sunk my fist as deep as I could up into her body. Then I leaned down to lick her throbbing clit to get a taste of her. I sucked on her hard clit and she went into a violent orgasm, her whole body shaking and shuddering endlessly.

Once her orgasm subsided I gently eased my hand from her throbbing hole. Jennifer was pretty exhausted; after all she had been carrying around a banana inside her cunt all afternoon and now had been fist fucked for the first time. I lost track of how times she came.

Once she dressed, she kissed me deeply while we embraced each other. She literally smothered me with her love. Jennifer was one horny hot bitch. What an obedient slave she had become. I was totally convinced I could get her to do anything. I'd actually turned her into my personal whore.

On Wednesday the other two girls were off for the day. I planned on having another fun filled day with Jennifer since we'd be in the office alone. Before heading to work I stopped off again at the supermarket and picked up two of the largest cucumbers I could find. They were at least ten inches long and a good three inches thick, maybe more. I thought what lovely dildos they would make for Jennifer's tight little cunt.

Jennifer was already in the office when I arrived. I went right into my office and prepared for another stimulating day with her. I laid the cucumbers out on the desk then called Jennifer into the office.

"Well Jenn," is my hot little slut ready for some more fun today." She smiled when I said that and anxiously started removing her clothes. Once she stood there naked she noticed the cucumbers on the desk.

"Are those for me," she asked?

"Yes, just for you my dear," I replied.

I grabbed one of the cucumbers from the table and ran it up between Jennifer's legs. "Ten inches," I commented as I wiped it across her slit. "And look how big."

She knew what I was about to do and she was eager for it. She bent over and leaned on my desk offering her body for what I had in mind.

"Spread your legs apart more," I ordered.

When she moved them apart I placed the cucumber at the entrance to her precious hole and began sliding it around her slit picking up some of her juices on it. Then I began pushing. She closed her eyes as the hard cylindrical object began entering her body. It forced her pussy lips apart wider and wider making room for the thickness to pass through. I pushed more making Jennifer's cunt expand wider than ever before as the cucumber slowly fucked into her cunt hole. Once the thickness stretched her hole enough, I pushed about three inches in. "Ooooooooouuuuu!" She moaned out loud as I twisted and wiggled it. Then I pushed it more penetrating her hole deeper.

Jennifer grunted softly from the discomfort of having such a big object open her tender vagina. Five inches were in and I kept going.

"Easy," she whispered. "Please go easy."

I pushed on it slowly until at eight inches I encountered a little resistance. The cucumber was about as far in as it would comfortably go.

"Only two more inches, baby." I remarked. "I want you to take it all."

I pushed harder and I could see the discomfort growing on her face. But that didn't stop me. Jennifer wasn't stopping me from forcing it inside her hole either. So again I pushed and the cucumber began to disappear between her legs, up into her body. Only a tiny piece of green was visible within the soft folds of her pussy. Then with two fingers I pushed one last time and forced the remaining end up into her cunt and watched her sweet young fuckhole close up around it.

"Ohhhhhhh!... Ohhhhhhh!... Fuck.... It's so big." She cried out.

"My God Jenn, you took it all," I groaned in disbelief that she let me do it.

She moaned and moaned while placing her fingers on her cunt to feel that the entire thing was inside her.

"You're so nasty letting me do that to you Jenn," I commented.

"Stand up," I ordered.

Jennifer obeyed, but I could see how uncomfortable she was trying to straighten up with the hard cuke inside of her body.

"Slut," I called to her.

"Yes," she answered.

"Keep it inside of you until I say you can take it out. Is that understood?" I instructed.

"Yes..., Yes..., I understand." She answered in a trembling voice that appeared obvious she was becoming more uncomfortable.

"You like having things stuffed in your cunt, don't you? I inquired.

"Yes, oh yes," she answered.

"Maybe you'd like something in your ass too?" I asked. "Let's see if you like both holes filled at once. Now kneel down so I can fuck you in the ass."

She was so obedient. Immediately, Jennifer inched her way down onto her knees holding the cuke inside her with one hand. I then knelt down behind her and fingered her anus. It was incredibly tight. She was so tensed up trying to hold in the cucumber. It was going to be tough getting my cock in her asshole while her cunt was so stuffed. So I reached down to her cunt and told her, "relax... let it come out. Let me get my cock in your ass first, then we'll stuff your cunt again."

With that the cucumber started to appear and I pulled it from her hole. It was wet and shiny coated with all her cunt juices. I handed it to her and returned to her ass. I placed my hard cock at her anal entrance and shoved in penetrating her asshole. She gave a quick little grunt from my abrupt insertion. Once inside her ass I pushed and buried my cock all the way up inside her rectum.

"Okay, slut. Now shove the cuke back in and fuck yourself with it."

Jennifer reached underneath herself putting the cuke at her own cunt and pushed. As she shoved it deeper I could feel the hard cuke penetrating her body as it pushed on my cock on the other side of the membrane separating her cunt and rectum.

"Okay, now fuck yourself with it. Fuck yourself like a horny little slut, Jenn."

And she did. She completely let herself go. She fucked the cuke in and out as I started fucking her asshole at the same time. She began crying out in pleasure as her self-cunt fucking became faster and faster.

"Oh, God... Fuck me.. Fuck me....." she screamed.

I didn't know what she liked more, shoving the hard cucumber up her cunt or my hard cock in her ass. In any case she was masturbating herself vigorously sliding the ten-inch cucumber in and out of her little cunt. If she kept this up she certainly would be on the verge of cumming soon. I was getting close myself.

"Harder... Fuck me harder...," she cried out.

Well, I didn't want to cum just yet. I was having too much fun. I pulled from Jennifer's ass and grabbed the other ten-inch cucumber. I placed it on her asshole and started twisting it, slowly working it around her just fucked bunghole. The cucumber was gigantic too. I squeezed it between her asscheeks at the entrance to her tiny little puckered hole. She knew what I was going to do. I almost couldn't believe that I was going to shove this huge vegetable inside her ass. And Jennifer made no effort to stop me either.

I pushed and twisted it. Her asshole began opening up ever so slightly for the giant veggie. She let out a little whimper. "Oooouuuuuu..."

I pushed harder and harder knowing the pain must be growing. "Ooooouuuuuuuuu... Ouuuuuuuuu," again she whimpered. Finally I pushed a little harder stretching her asshole open enough to penetrate her ass with the big cuke. She let out a long loud grunt while sucking in a lot of air trying to cope with the pain of her asshole being pried open so wide and the cunt fucking she was giving herself with the other cucumber.

"Uhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh!
"Uhhhhhh.. Huuuuhhhh.. Uhhhhhhh.. Huuuuhhhhhh.. Uhhhhhhhh.. Huuuuuuhhh"

Slowly I pushed the cucumber through her asshole into her gorgeous rectum, three inches, four, five, six. Another long moan and grunt began as I continued stuffing her ass. "Uhhhhhhhh.. Huuuuhhhhh.. Ohhhhh God..."

Seven inches, eight,.... "Uhhhhhhhhhhhhhhh... Huuuuuuuuuuuuuhhhhhhhh... Uhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh!"

Nine inches, ten, "Uhhhhhhhhhhhhhhhhhhhh!!!! My God!!!" Jennifer screamed.

Only a little tip remained visible protruding from her asshole. She was nearly delirious. Her reactions were partially from the pain inside her ass and the nearness of her orgasm from stuffing herself up the cunt. I was consumed in my lust from what I was doing and seeing.

"How's that my sweet darling slut? Like big things in your ass?" I remarked.

She didn't answer and I didn't expect her too. Her moaning had become not of discomfort, but now of pure pleasure from having both of her holes stuffed with such large objects.

She was now jamming nearly the full length of that cuke in and out of her hot cunt, while I held the other deep in her ass. She started begging for her precious ass to be fucked with it and hard. "Ohhh!!! Ohhh!!! Fuck!!! Fuck me!!!" It was more than I could handle seeing this gorgeous young woman giving herself such a nasty fucking. I began pulling the cucumber out of her ass and ramming her asshole with it. She screeched in pleasure each time I jammed it deep up her ass. "Ouuhhhhhhhhh!... Ouhhhhhhhhhhhhhh!... OUHHHHHHHHHHHHH!"

"You love having your tight ass fucked, don't you, you little whore?"
I swore at her.

"OUHHHHHHHHHHHHHHHH!!! OUHHHHHHHHHHHHHHHHHHH!!!" She kept screaming.

"C'mon Jenn, CUM. I want you to CUM."

I rammed it up her ass again.

"Ouhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh!" Her responses were that of a woman consumed with the need to orgasm.

"I'm gonna make you cum, you horny bitch." I yelled. "I'll make your asshole cum like a fucking slut."

Again I pulled it out of her bunghole and shoved it back in deep.

"Ouhhhhhhhhhhhh!!!! Ouhhhhhhhhhhhh!!!! Ouhhhhhhhh!!!"

Her moans and screams were out of control. There was no stopping her. She was going to cum real soon.

After about ten minutes of furiously fucking Jennifer's anal hole with the cucumber, I pulled it out and quickly shoved my cock in. The quick change in her ass set her over the edge. Her asshole gripped my cock as her whole body convulsed in a tremendous orgasm. She screamed for more as I buttfucked Jenn hard. "Fuck me... Fuck me up my ass... Oh, God Fuck my asshole."

She was nearly in tears as her tight ass made me ready to burst. I was ready to explode and I wanted to feed it to her again. Of course, I knew she would eagerly eat it up.

In my frenzy, I called to Jennifer, "I'm going to cum."

I quickly pulled out and she knew what to do. With the cucumber still in her twat she spun around as I said, "take me." She took my engorged cock in her mouth again without question. Even though she was hot and horny and having an orgasm, I know she knew what she was doing. She liked doing nasty things like sucking my cock after I assfucked her. And it really aroused both of us.

She sucked me in her mouth. Then I held her beautiful head in my hands and fucked my hard cock right down her throat burying her face in my crotch. I looked down and saw her lips plastered against my groin while she shoved the cuke all the way into her cunt again. She began moaning with my cock down her throat. She was cumming again. Another orgasm was rocking through her body. Beautiful Jennifer had masturbated herself to another orgasm while I held my cock in her throat waiting to cum.

Suddenly, she let go of the cucumber and it slowly slid out to the floor. She grabbed my buttocks and tried forcing more cock down her throat. My shaft started throbbing flooding her gullet with sperm. She pulled off as I kept shooting thick gobs all over her beautiful face and she coughed up some sperm from her throat. What a sight. I could see all the white creamy cum in her mouth. She was panting heavily trying to catch her breath, but begged for more. "Cum, more cum... Mmmmmmmmm"...

Gorgeous Jennifer with my cum running down her face was sucking up my cream like it was candy. "Eat it up Jenn, swallow it," I coaxed her on. But she hardly needed encouragement to eat from my ejaculating cock. She had no plans of wasting it anyway. I had turned my secretary Jennifer into a cum hungry whore.

Then another blast of jizz from my cock went right into her open mouth. She swallowed it and began smearing my hard shaft around her face as more cum dribbled from me. Jenn then licked me clean sucking my cock in and out of her sweet mouth making sure she got every drop.

We finally recovered after lying on the floor for about ten minutes. "You're such a nasty little cunt," I whispered to her. She smiled at me in a way I knew she enjoyed every second we were together.

Jennifer got dressed and gave me a kiss goodbye. Already I'm thinking of what I'll do to her tomorrow.

It's been almost a month now since that first Saturday when I caught Jennifer masturbating. It's hard to believe what we've done since that day. Jennifer has actually become my personal whore. She's does anything I tell her to. I have yet to reach her total fulfillment sexually.

One day when the other girls were out to lunch, Jennifer wanted to give me a blowjob. She said she needed to taste my cum again. She was particularly horny that day. So instead of making it easy for her and just letting her suck me off, with her still fully dressed in her nice skirt and jacket top, I stripped down, sat on the sofa and first let her suck me hard. Then I made her lick my balls and suck them into her mouth. Afterwards, I told her if she wanted my cum she had to lick my ass and slide her tongue in my crack. I told her I expected her to lick and suck on my asshole. She did it and did it happily. First she licked my entire asscrack giving me a thorough cleaning. Then she buried her face between my asscheeks and her tongue worked asshole like I'll never forget. Somehow she managed to get her lips on my anus and sucked it. What a feeling. I called her an asslicking whore when she did that. That turned her on more and she forced her tongue through my pucker. I could feel it sliding in and out of my ass as she tongue fucked my anal hole. That made me cum, so she quickly had to stop to eat my sperm. She never passes up getting a mouthful of my hot jizz. She was such a fucking whore that day.

Well that's my secretary Jennifer. I often wonder how long this will last. I wonder what she does at home with her husband? How could she have any energy left for him after our daily escapades?
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NiteWriter
 

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