Fisting Cheryl

First impressions whether they be online or in person are not always accurate. I had posted online a thoroughly debauched tale of fisting and stretching – one of many. It is always good to get feedback and I often get asked if the stories are real or 100% fiction. The answer is a mix of the two. One of the stories elicited a response along those lines from a reasonably new user from the particular site I posted too. It is easy to become dubious of new posters that have profiles with very limited information on it. Are they actually the gender or age they say they are? Do they really live in Sydney, or are they in Nigeria and just want to give me a hand collecting some lottery “winnings”?

I did respond to this particular user, but only in very general terms and politely suggested it would be nice to know more about them as the profile was pretty “data poor”. She responded quite promptly and politely, explaining that she was only new and was just getting the lay of the land. She did close off with saying that she knew what she wanted and really hoped my story was a lot more than just fiction. We corresponded for a little while and I learnt that she did live in Sydney - a north shore girl – St Leonards to be exact. Her name was Cheryl and she was a 36 year old brunette.

I must admit although I became convinced that she who she said she was, I became less convinced that she was interested in the kinks that I was, let alone in participating in anything of that ilk. She shared some photos of herself with me (and vice versa) and she looked both good and real. This made a change from the person that had an hour earlier said she was local and wanted to meet ASAP if I emailed her some “details”. When I had asked that particular person for a photo, I was provided with a grainy photo of a woman from the 80s and I could see a Russian street sign in the background. By contrast, the photo Cheryl showed me was recent and clearly from Sydney. She was attractive and carrying “a little extra padding” as she said she did, and this did not bother me at all – to the contrary in fact. I won’t say Cheryl she was plain looking, or anything like that, but it is perhaps fair to say that she would not stand out in a crowd.

One Friday night I was online fairly late and Cheryl bobbed up on Instant Messenger. She said she’d been out with a few drinks with the girls and was really horny and had been unable to find a man to fill her needs. I said if I lived closer (I am on the Gold Coast) I would be around there in a flash. She responded with:

“Hopefully to fist my hole, like I read in your posts. I NEED MY HOLE FISTED AND OPENED NOW.”

This was much different from her usual correspondence and the capitals were her emphasis. Clearly she was a “hole girl” like I desired after all.

She quickly followed with message “God I wish you here using my hole” and then added: “I am lying naked on my bed with a huge dildo in my cunt and a smaller one in my bumhole. It’s not enough though. I need someone like you here with me.”

My cock instantly sprung to a attention and throbbed as I thought about Cheryl. A natural response of course! Filthy chat for an hour ensued and I agreed that I would travel to Sydney to meet in person the next week. I travel frequently to Sydney for work, so it was no drama at all. The next day, Cheryl was back online again and told me she had a horrible hangover, but that everything she had told me was true and she did want to meet. Over the next few days she showed me various pictures of her cunt and asshole either filled with a toy or object or gaping open. She had quite the holes.

I flew to Sydney the following Friday afternoon, did some special shopping, and settled into an upmarket hotel at Darling Harbour. I was to meet Cheryl at 6:30 for drinks and dinner in one of the Darling Harbour restaurants and she arrived on time and well dressed. She was obviously nervous but as we got chatting over a lovely Hunter Valley Verdelho, she was pleased that I came and pleased that looked like my photo. Cheryl had had problems with fakes as well.

As we moved quickly on to our second bottle of wine and started on our delicious mains – I had wok tossed prawns and Cheryl had lamb shanks, we started to talk about sex. It was then that Cheryl informed me that her vagina had been occupied for the whole day and still was now. Her mischievous smile met mine and I asked what was in there.

“I have a big dildo as the occupant,” she replied and gave a mock apology for taking it upon herself to stretch her hole a little for my arrival.

“All great performers warm-up,” I commented.

She then went to talk about how my stories had really turned her on and while she had met a few men who liked to do what she liked to have done – most she said never lived up to their words. I guess it was a comment as much as a challenge. We talked about why she liked fisting and why I liked to fist. She said she saw some old European fisting pictures in an ex-boyfriends porn stash when she was in her very early twenties. At the time she said she was appalled her ex-boyfriend had a porn stash and that it contained such “gross” things, and she broke up with him over it. She laughed at her own naivety then. She explained that as the years progressed as did her sexual horizons and she explored more things. Online one evening playing and looking at porn she said she came across some fisting videos which made her think about her poor old ex-boyfriend whom she now thought she treated rather unfairly, but also they made her very wet and from that point she had tried fisting herself and in her own words had become rather proficient at it.

“Simply, I like a fist in my fanny,” she concluded before adding, “Or any other things that can be made to fit.”

She did expand on the fact that her fisting partners as opposed to her vanilla partners in the past spent a lot longer focussing on her than just her own needs. She asked me to elaborate on why I liked fisting.

“Simply, I like to put a fist in a fanny,” I said and she laughed.

I did though discuss the visual side of things, the wonderful way the right woman submitted to it, and the ability if you do it well to bring a woman to earth shattering orgasms.

Cheryl also admitted to something else. She just wanted to check with me that it was okay that she was a bit of “squirter”. I was more than fine with this, quietly ecstatic to be perfectly honest.

However, we didn’t prolong the conversations for too long as it was clear there were things that we both wanted to do. My hotel was in walking distance, but Cheryl apologised mischievously that she would be walking a bit slower than usual.

It was only a short walk so it didn’t matter too much. When we arrived in the hotel room it was clear that we both wanted to get started. Cheryl quickly took her blouse of smiling and stepped out of her business slacks. She apologised for wearing granny undies but said they were necessary to assist in keeping the occupant in place.

“Would you like me to unveil?” she asked and I nodded without hesitation.

She got herself up on the bed still wearing her bra and panties. She slowly slid her panties off and spread her legs wide to reveal the end of a black dildo sticking out of a strained and glistening cunt.

Without speaking I shuffled over and slowly, ever so slowly, withdrew the lodger from its lodgings. Her cunt barely closed at all as the dildo was withdrawn. It was a big dildo but not gigantic but the fact that it had been worn all day was miraculous.

“Please take some photos on my phone as we go for my collection – no face shots,” she said before adding, “Do you like my big cunt?”

“I do indeed and I can see that my usual preliminary stretching activities are not needed,” I replied as I took a nice “before” picture with her phone.

Nonetheless, I still took my time and I fucked her slowly with the dildo that until now had been her occupant for the entire day.

“Mmmm yes, but I need much, much more,” muttered Cheryl languidly.

“Patience, my dear Cheryl,” I said quietly before withdrawing the dildo completely and leaving it by the side of the bed.

I kissed Cheryl passionately before unbuttoning her bra. I sucked and licked her nipples, but unlike my usual sessions, I would leave her tits largely alone as she wished. It was a shame as they were a beautiful pair.

I knew from her photos that her cunt was large and I had bought an array of things to use on it. I left my average sized dildos and vibes in the suitcase and went straight to the bigger of my inflatable models. I lubed it up and inserted it. As it nestled in nicely, I pumped it up slowly, a single pump at a time and a brief interlude between pumps until it could not be comfortably pumped any further. I then deflated it and administered it a number of more times. I took some nice photos of her bulging cunt.

Next I got out the dinner candles I had bought – red in colour. Although I do enjoy wax play – I would not be lighting them this time – I had an embarrassing little episode once with a fire alarm that wasn’t disconnected as thought. I would however be inserting the candles deeply into Cheryl’s cunt and I went about doing it. I worked three in easily and I fucked her slowly with them. I managed to get eight in – the last two down the centre which displaced the others outwards and further stretched her big hole.

I left them there as I took off my trousers and underwear, moved up her body and straddled her face – feeding her my rock hard cock. She adjusted herself to get comfortable and inhaled my cock as she stared into my eyes. She paid particular attention to my bulbous cockhead and I came grunting and spurting a load of cum – a gooey geyser across her facial features. She smiled sweetly and happily, and licked her lips.

After I came down from my climax, it was time to really get busy with Cheryl’s hole – I withdrew the candles slowly – one by one. I got out my cuffs and restrained her wrists to the bed head and I also put some cuffs around her ankles and ran some rope from the ankle cuffs to some fixed points in the room. For the next hour I teased her hole, her clit and indeed her whole vulva and inner thighs. I pushed her over the edge numerous times. I mostly used my hands and my fingers and a small but intense little vibrator that I used on her clit. I pushed my fingers into her but never deeply. Her hole was still very open and with the teasing I was able to get four fingers and my thumb in but at this stage did not try and work in past the knuckles. I knew this is what Cheryl wanted, but I wanted her to be patient for the time being.

After her fourth climax I decided it was time to give her a fisting of a life time. Even though her hole was distended, I continued to take it nice and slow with a copious amount of lube. One last twist of my wrist and my whole hand lodged itself in Cheryl’s birth canal and Cheryl moaned deeply “fuck yes” and then groaned gutturally as her sodden cunt became completely occupied. The squelching noises emanating from her snatch were mind blowing. Now that my fist was in there completely I could really get to work.

“Look me in the eye and tell me what you want me to do Cheryl,” I asked.

“Fist my big fucking cunt hole. Stretch out my fucking big cunt hole with your man fist and make me soak the bed.”

The depth of her need was obvious and I started to drive my fist deeply and rhythmically into her completely compliant cunt. Her pussy lips stretched around the base of my wrist when I withdrew and nearly inverted when my fist descended back into the wet depths of her cavernous cunt. Over and over I repeated this until on the brink of an orgasm I ripped my fist out and spanked her pussy. She flailed, she screamed, she came, and she squirted. She squirted all over me, all over the bed and on to the carpet.

I stopped spanking her pussy and took some pictures of the aftermath as she slumped back against her restraints and caught her breath. I took a close up picture of her sodden, red and open hole.

I then repeated the dose, but this time really twisting my fist inside Cheryl who writhed again against her restraints. Even though she was so very wet, I made sure there was lots of lube so could I really pump deep and strongly into her. Again she climaxed and this time I put my mouth on her huge cunt as she came and she squirted all over my face, I was momentarily blinded by delicious cunt juice. That was a first.

“Fuck that was good.” said Cheryl as she lay there panting and then followed by saying that her hole needed a short rest and she wanted to suck my cock for a little while. I took off her restraints and I had her kneel on the floor with her hands behind her back as I fed her my rampant cock which she inhaled again with vigour, staring into my eyes as she did so. Languidly, I fucked her willing face before exploding deep down her throat. She continued to suck my softening cock that would no doubt be hard again very soon.

She finally stopped sucking my cock and asked, “Is another fisting out of the question?”

“A fisting and more Cheryl. I have a few things to try on you that I haven’t tried before. I went shopping especially...”

“Oohhh,” she cooed.

This time I laid on the bed and had her put her feet either side of me. I raised my arm up and with my other hand I guided her down on to my four fingers. Instinctively she rocked up and down on my fingers and commented that she had never been fisted this way before. I am always happy to deliver a new experience. It didn’t take long before I was able to slip in all my digits in again passed the knuckles. I had her lean forward and balance on the wall behind the bed, and suggested to her that this was going to be very vigorous.

I thrust up hard into her cunt as she drove down. Once we synchronised our rhythm it was heaven. Her cunt grunted and I could feel the wetness emanating from her overused hole running down my thrusting arm. It was a short but frenzied ride for her to orgasm. As she peaked she nearly fell and again she squirted all over me but less voluminous than before. I had kept my fist inside her this time as she came and I felt her cunt quiver uncontrollably and it continued to quiver until I withdrew my wrist slowly. I looked up at a hole that simply hung open slackly. I asked her to hold still while I took some photos of the gaping maw that her cunt had become.

I had her kneel on the bed and spread her asscheeks and I put a blindfold on her. Cheryl’s puckered little bumhole looked so out of proportion compared to the gaping fault line below it. I lubed up her bumhole and spent a little bit of time loosening up her sphincter just a little bit. When I could fuck her bum easily with two fingers I went back and focussed on her cunt. I wanted to put some massive objects in it. The first was a big bunch of celery – it was the biggest I could find in the grocery store. It took some time, but it finally went in. It looked like the thing was actually growing out of her cunt. I took some photos of it wedged in there, but could not really fuck her with it. When her cunt ejected it, her hole virtually didn’t close. Since the bed was completely wet already, I went to the fridge, got out the bottle of bubbly and two glasses, shook it a little, popped the cork and jammed the neck of the full bottle into Cheryl’s cunt. Champagne went gushing everywhere and Cheryl yelped and thrashed around at the coldness filling her cunt. When I had I collected two glasses worth of gushings, I then followed up with more depravity. I filled her cunt up with strawberries until it was overflowing with sweet fruit and I had her push them out collecting some in our champagne. I proclaimed that we had made a “Champagne Cunt Cocktail” and I had her sip from one of the glasses while I sipped from the other.

I had one more thing that I wanted to try and stick in her cunt. It was going to take some effort, but if ever there was the right time and right hole it was now. I had inserted salamis in pussies before, but I wanted to try something along those lines but much larger. When I had gone shopping I purchased the largest sausage of luncheon meat I could find. It was much fatter than any salami but much springier. It was sheathed in the slippery plastic that is typical of the product.

I told Cheryl, “I am going to put the largest item you have probably ever had in your cunt and probably ever will. I want you to spread your ass checks wide for me.”

I used plenty of lube and I was able to compress the roll of manufactured meat down enough to get it into the entrance of her hole. It was clearly a strain but she were willing and what a sight it was as I slowly slid the massive meat into her cunt before bottoming out with still a good portion of the deli item sticking obscenely out of a hole that was now finally stretched to its limits. I took photo after photo of the meaty log in her cunt. I didn’t leave it in you too long as I could see she really was straining. When I took it out her cunt it did not close. My work on her cunt was completed. I had one more activity to do though to finish off. I opened up her bumhole a bit more, slowly slid my cock in there, and fucked her asshole. When I came I withdrew and we hugged for a little while before showering together. We were both totally spent and the dawn was appearing. We left the hotel together as there was no point trying to sl**p in that ruined bed. We bade farewell in the lobby of the hotel and vowed to meet again.

95% (31/2)
Categories: BDSMFetishMature
Posted by Ravisher71
2 years ago    Views: 1,252
Comments (8)
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13 days ago
very hot story!
2 years ago
very hot
2 years ago
hot wow
2 years ago
Great story!
Every fist loving man should meet A Cheryl at least once in their lives.....Lucky you!
2 years ago
2 years ago
Very Hott! We might hafta try some of this next time we fist:)
2 years ago
Well written and amazingly hot.
2 years ago