Fisting Jennifer

Jennifer and I had been chatting online for a long time. We had gotten to know each other quite well. Jennifer was gorgeous, in her late forties with boobs to die for and lovely luscious clean shaven pussy. Jennifer was kinky, she loved having her nipples treated harshly, and she had some other kinks that she wanted to try out. Work took me to Jennifer's home state of South Australia so I sent her a message to see if she wanted to catch up. She was willing and able. I was staying at the Stamford Hotel at Glenelg and I had a magnificent view across the ocean from my room.

When you chat with someone online, you always hope the chemistry is there when you meet them. I was at the bar and saw Jennifer alight from a taxi. She looked divine, as I caught her eye and gave a polite wave from the bar. We greeted each other with a kiss, inhaling the fragrance of a perfume I couldn't quite identify. Jennifer caught me glimpsing at her breasts, breasts that I had seen exposed many times in photos. It was better to see them in real life, and better to know that perhaps that evening I would be getting my hands on them and having my way with them.

We had a nice meal, and both of us commented it was so much better to meet face to face, rather than chat online. I added that online should only ever be the entrée; and Jennifer quipped that she hoped she was the main course. I assured her she was the signature dish in my menu plans. We flirted with each other shamelessly. There was chemistry between us, we both oozed sexual tension.

When my gaze involuntarily slipped again to Jennifer's boobs, she offered," I hope you are going to do more than look at them, they are yours to use this evening."

I responded, "I'm glad to hear it Jennifer, we should finish up here quickly, I urgently want to get my hands on your gorgeous form."

Jennifer laughed and feigned coyness.

We quickly finished our meal, and I took Jennifer's hand and led her to the lift and then up to my room. I had prepared for the encounter and was very happy that it had played out well so far. We were both attracted to each other and wanted a kinky time.

"Ready for tender torment," I said as I took Jennifer in my arms and kissed her sweetly. Her body responded and the room was electric with lust.

"I want you to take me hard," whispered Jennifer in between kisses and I promised I would, warning Jennifer playfully to be careful of what she wish for.

My hands worked their way over Jennifer's back and the side of her tits. I gave her neck a love bite as my fingers worked their way to her nipple and I gave it a hard tweak through the fabric. We were both breathing heavily, overtaken with pent-up lust. I threw Jennifer playfully on the bed and straddled her.

Squeezing and groping her tits through the fabric, before I unbuttoned the blouse to reveal an exquisitely sexy bra. I fondled Jennifer's tits through the bra, staring in to her eyes as I did, before taking one and then the other breast out of their lacy confines.

"I've waited a long time to get my hands on these," I offered.

I continued to fondle and squeeze them, paying particular attention to her succulent nipples. I knew she liked rough nipple play. She knew I liked to give it. I went about teasing and tormenting her nipples with unbridled lust. Seeing how far I could twist them, pulling her tits up by the nipples as far as they would go and then shaking her tits vigorously as my fingers clamped harshly on her nipples. Jennifer revelled in the rough treatment.

"I think I have nicely warmed up your tits Jennifer, but let me assure you, your pussy and bum will not be neglected."

Jennifer purred her approval in response and I directed her to strip down to just her knickers, enjoying the sight of her tits swinging free as she did and then the lovely sight of her just in her knickers. I reached into my luggage and pulled out a red marker pen. I had Jennifer cup her breasts and push them upwards as I wrote "Use My Tits" across them, commenting how her body was going to be a canvas for a kinky masterpiece as I did so.

I asked Jennifer to put her hands on her head and close her eyes, and to spread her legs slightly as she stood there. I spanked her covered bumcheeks with my hand, before adjusting her panties to partly expose the flesh beneath.

"Keep your hands on your head Jennifer. Keep them there while I redden your bum."

A half dozen solid slaps with my hand were then followed up with a pause as I picked up my nice little soft flogger. Some light flogging follows until Jennifer's lovely bum glows a nice red. I have to encourage her to stand still and keep her hands on her head, but for the most part she does so and does so well. I have Jennifer spread her legs slightly further, and then I tease the inside of her thighs, tracing my fingers gently upwards and then running them along the edge of her now very wet knickers. I could smell Jennifer's beautiful arousal, her hot wet cunt. I teased her inner thighs for what no doubt seemed like an eternity, slowly increasing the teasing stimulation of her pussy, pushing my fingers against it through the fabric. Jennifer's moans increased in frequency and intensity.

"Please," Jennifer was heard to beg breathlessly.

I asked her to spread her legs slightly more and I promised I would up the ante a bit. I reached around from behind her until my forearm rested across Jennifer's stomach. With my other hand, I then spanked her thighs lightly and then more firmly on her pantie covered vulva. I held her steady and insisted she keep her hands on her head as I continued the light spanking.

"Do you want to cum Jennifer?" It was a silly question and Jennifer moaned the obvious yes.

I released Jennifer from my grip and stopped the spanking of her soft thighs and wet cunt. She took of her knickers, finally exposing her hot wet pussy. I took of my own pants and shirt, exposing my hard cock that had been oozing pre-cum for a long time, the purple head glistened. I told Jennifer to kneel on all fours on the bed and she did so without hesitation. I put a nice collar around her neck and then a pair of heavy duty clamps from the hardware store on each nipple. Jennifer whimpered in pain and pleasure, begging me to make her cum. I went round behind Jennifer and teased her slit and clit with the engorged head of my cock, before relenting and burying it into her sodden snatch. I spanked Jennifer's bum and fucked her hard. It was a short fuck. With her nipples clamped wickedly, her bum being spanked and my cock pistoning into her vagina, Jennifer came screaming, her hands clawing at the bed sheets as she did. My cock soon exploded deep into her convulsing pussy, pulse after pulse of sperm shooting from my cock and mingling with Jennifer's abundant pussy juice.

We broke off our fuck as Jennifer collapsed forward and my cock slipped out of Jennifer's muscular sticky sheath. Sperm bubbled out of her now vacant hole and ran on to the bed. We hugged as we both recovered from our first climax. There would be more. I got up and poured both of us a drink. Jennifer took the heavy duty plastic clamps off her nipples; the teeth of the clamps had left their mark on her soft flesh. I picked up the marker pen again and wrote more on Jennifer. On her stomach I wrote "Fist my pussy", and an arrow obviously pointed down. On one inner thigh I wrote "Cum in here" and the other "Spunk my hole".

I had plenty more in store for Jennifer. We playfully kissed for a while, before my fingers found their way to Jennifer's nipples again. I traced the writing on her tits with my finger tip. Jennifer had grasped my cock which was hard again, and worked my balls over with her fingers. Pulling, tugging and twisting at them nicely. Squeezing my cock as she did so; getting it wonderfully hard again. I finally pushed Jennifer's face down to my cock, and she gobbled it greedily, as her hands continued to work my balls with erotic vigour. Jennifer's mouth danced over my cock, and she paid special attention to the head that was again oozing pre-cum. My toes curled uncontrollably. It took an effort on my part, but I removed Jennifer's bobbing mouth from my cock and I whispered that I had a nice little surprise for her.

The hotel room had a nice big bathroom. I directed Jennifer to go in there. In it I had placed two ice buckets, each with a bottle of champagne. I directed Jennifer to put her hands on the uncluttered vanity area and she looked directly into the all-encompassing mirror. The light was brighter than it was in the bedroom itself and the redness around her nipples and the teeth marks from the clamp were more vivid.

"I am going to play with your pussy for a while Jennifer. I want you to keep looking into the mirror. Your job is to guess the object that I am fucking you with. I have selected a number of fun items."

Jennifer queried what I was writing on her bumcheeks, and smiled when I said, "Insert objects here", and I joked that I had to follow the instructions. Before I commenced the insertions, I put a clamp on each nipple and hung a good sized pyramid shaped weight from them. This had the desired effect of pulling Jennifer's nipples down and would swing furiously when I fucked her cunt.

"I will fuck you with the object until you guess what it is, or until you cum. Every time you answer incorrectly I will repeatedly whack your backside with this paddle," I said, lifting up the paddle so that Jennifer could see it reflected in the mirror.

"Please fuck me," replied Jennifer obscenely.

I put some lubricant on the first item and slipped it into Jennifer's pussy. She yelped that it was cold and her first response that it was metal. I jabbed the first item into her pussy rapidly and deeply. Watching Jennifer's face in the mirror and seeing her weighted tits swing. Since it was the first item, I gave Jennifer some hints.

"I am twirling it Jennifer," and she replied instantly "a baton!"

The next item was more organic, and Jennifer guessed it correctly as a banana made its way into her cunt and I fucked her with it momentarily before withdrawing and replacing it with the next item. This time Jennifer guessed that it was a dildo and I spanked her ass cheeks to let her know that her guess this time was incorrect. I fucked her deeply with the object and she moaned with pleasure before finally guessing correctly that it was a salami. I continued to fuck her with it deeply, withdrawing the large thing almost all the way out of her hole, before plunging it deeply in. She clearly enjoyed the girth, and her tits swung wildly. I finally withdrew it and again Jennifer quivered as another cold metallic item plunged into her now gaping gash.

"It's not uniform in shape," Jennifer offered as I fucked her with this object, telling her to be specific with her guess.

"It's fuckin' cold," she added.

I turned the object around and put in base first. Her cunt stretched wickedly around the solid invader.

"It's a coke bottle," she said and I whacked her asscheeks in response to the incorrect answer.

Her ass cheeks were now bright red and her cunt was distended around the object that I was driving into it. I loved the way her cuntlips clung tightly to it each time it was withdrawn. Just as I thought she wouldn't guess it correctly, Jennifer blurted out at the correct answer - deodorant bottle.

The next item was another salami, shorter, but wider than the first one. Her now well worked over hole took it relatively easily and Jennifer guessed correctly. I pushed it deeply into her and her push out the invader herself. Her now vacant pussy gaped noticeably. Next was not just one, but three items all the same.

"Vegetables of some sort, let me guess properly," said Jennifer before adding with some trepidation, "carrots".

Her guess was correct. The next item took some getting in and it wasn't one that I could effectively fuck her with.

"This one is tricky Jennifer, I'll allow you some leeway on this guess as long as you are close enough," I said.

With the object deep insider her I ticked her clit and Jennifer groaned.

"It's not coming out until you guess correctly," I said, continuing to torment her clit.

"Fuck leave it in there, I am going to cum, pleeasssssseeeee keep touch my clit," begged Jennifer.

I watched in the mirror as Jennifer's eyes rolled back in orgasm. My fingers dived around her clit. With a lemon embedded in her cunt, Jennifer flailed uncontrollably in orgasm, her knees buckled as I continued to squirm my fingers around her clit.

I took my fingers from her clit as her orgasm started to subside and Jennifer leaned forward panting.

As she regained her breath I commented that she still hadn't guessed correctly.

She added, "Something big and round, a mandarin perhaps?"

"Close enough, it is a lemon, you can push it out now," I responded.

Jennifer strained until the lemon evacuated from her cunt. I had her take the clamps off her nipples and we both went back to the bedroom where Jennifer asked what I had in store next.

"Lie back on the bed and spread," I said.

I put some soft cuffs on each wrist and the short length of rope that run from them I tied them to the bedposts.

I found the bottle of lubricant and spread it over my whole hand and then her cunt.

"You are still gaping nicely," I commented.

"I started with three fingers that slid easily into her cunt and quickly had a fourth in there,"

"What do you want me to do Jennifer?"

"Fist my cunt. I want you to fist my cunt and keep fisting me," Jennifer replied without pause.

I continued to churn four fingers into her, only stopping occasionally to stretch her out a bit more my applying pressure to her opening with two fingers from each hand.

I kept this up for quite a while, and Jennifer started to writhe against her restraints, another orgasm was beckoning and I continued to jab my four fingers into her and pressured her clit with my thumb.

"Fuckkkkkk..." she screamed and gasping Jennifer climaxed again.

For about five minutes I left my fingers in her pussy but ceased the clitoral stimulation. As she lay there, I slowly started to rock my fingers that were still wedged in her cunt.

"It is now time for my whole fist Jennifer."

I again jabbed my fingers into Jennifer's cunt. I positioned my thumb along my four fingers which were now bunched tightly together. The tip of my thumb was now joining the other four fingers and I was slowly able to inch more and more of my thumb in with each thrust, but I was not yet passed the knuckle. I added a bit more lube to the situation and more of thumb was now able to push in. I was not rushing, just letting Jennifer's cunt become more and more accustomed to the stretching. Finally Jennifer's cunt gave in and my fist lodged itself wholly inside her. Jennifer cried out at the instant her cunt enveloped my whole fist.

For the best part of an hour I fisted her. She was in ecstasy the whole time. Her cunt was now thoroughly stretched. My fist was able to slide in easily now and I enjoyed how her distended hole clung to my wrist. When I had finally had enough I withdrew my fist from her cunt which now hung open slackly. I released Jennifer's wrists from the restraints I had her sit on the bed and gobble my cock for a short period time, it was oozing pre-cum and had been for virtually the whole time I fisted her.

After only a short period of time gobbling my knob, I told Jennifer that I would take her gaping cunt from behind. I had her kneel on the bed and my cock obviously went straight in. I love the look of a stretched out cunt swallowing my cock and at just the right angle, my cockhead rubbed blissfully against the underside of her pussy wall. I came inside her, groaning as I did, in part filling the warm cavern with even warmer cum. When I pulled out of her gape, a river of cum dribbled out and down Jennifer's thighs.

We were both spent. Jennifer had had her cunt thoroughly stretched out and fisted to oblivion. She had cum numerous times and my cock was well and truly relieved. When we left, I noticed that Jennifer's gait was not quite the same as when she arrived, slower and somewhat more careful. A sure sign that things had gone well...