Kitten Ch. 06: First Anal Experience

Kitten and I had been letting our relationship develop naturally. She had become my collared sub, she loved being submissive.

There were certain requirements attached to her submission. She was to have a daily, over my knees, bare assed, bare handed spanking. She was to be totally nude during the spanking.

She received five whacks, and was required to say, "Thank you Sir, four more please, Thank you Sir, three more please," with every swat.

If I was busy during the day, she would remind me in the evening that she hadn't had her daily "maintenance" spanking.

I would put down what I was doing, have her lie her beautiful nude body across my lap, and spank her beautiful bare ass.

I believe what she liked most besides the swat on her ass, was the fact that between swats, I would finger her always wet pussy and bring her to the edge of orgasm, then pull out and swat her again.

I discovered early in the relationship that she had a very large, soft G spot just inside her pussy, and she LOVED to have it massaged. It made her squirt if I didn't stop. So between swats, I would massage that G spot, stopping just as she was on the edge of an orgasm.

At the end of a spanking, I would ask her why I spanked her, and she would say, "Because Sir loves Girl." She was required to call herself "Girl" instead of referring to herself as "me".

At the end of her daily spanking, I would have her stand beside the bed with my shoulder on her left hip. I would wrap my left arm around the front of her bare hips, supporting her. I would then slide two fingers into her pussy from behind and roughly massage her G spot!

She would immediately begin to howl like a wolf and squirt.

When I did this, her squirting took on a whole new dimension. It wasn't like squirting, but more like pouring water out of a pitcher, and it continued as long as I would roughly massage her G spot.

She squealed and howled and said, "I'm, I'm, I'm," as she was cumming the whole time.

I tried once to see if I could massage her until she could no longer squirt. After 10 minutes, I gave up. My arm was tired and she was still flowing like a faucet.

After the squirting, she was allowed a few minutes to compose herself. She usually turned and fell across the bed.

Then she was required to go into the bathroom and get a towel and mop up the huge puddle her squirting had left on the floor. It was usually 2 feet wide and 4 to 5 feet long, and often ran out into the hallway.

Even she was amazed. After the first time, she looked and laughingly said, "That's all from me?" I just laughed in disbelief as she mopped up the puddle.

Kitten was always required to wear short dresses or skirts, and to sit on her bare ass wherever we went in public with her knees shoulder width apart.

She loved knowing that if someone were lucky enough to look in her direction, they would probably see her always wet pussy.

My one caveat was that if there were children about, she would conceal herself with a napkin, if we were in a restaurant. Children were never to be involved, and she had readily agreed to this at the beginning of our relationship.

When we were in bed before or after fucking, (we never made love, it was always a fuck, even though we loved each other) or sometimes during a long fuck, we would talk about the things that turned her on, and the things she thought she wanted to do sexually.

Fortunately, I'm not a jealous man and enjoyed when she talked about having a DP or a Gang Bang, or that she would like to have a woman in our bed and let me watch her with a woman, or her watch me fuck another woman.

I asked how many men she wanted at the Gang Bang and she said she didn't know.

I suggested eight, to which she said "Whoa! more like two or three plus you to start, Sir."

I told her that she would have to start anal training (stretching) as she had never had anything bigger than one of my fingers in her ass.

I also told her that I wanted her to start strengthening her Kegel muscles. She didn't know what that was, so we looked it up.

She loved the idea of being able to milk a man's cock with her pussy. So I bought her a porcelain egg which I inserted into her pussy daily so she could exercise her Kegels during the day.

She eventually got very good at it, much to my pleasure!

I also bought her a series of ever larger jelly butt plugs to wear part of the day until she was sore. She would text me if we weren't together and ask permission to remove it...which I always granted.

Over a few months of this training, she learned to love having her butt plug in her ass.

I tried to fuck her ass one night. Using lots of lube, and going VERY slowly, she winced at first, then once I was in her, deep in her ass, she really got into it! She had a huge orgasm and, of course squirted.

Afterwards, when we were lying nude together, spooning, and I was giving her aftercare, she started crying.

I asked what was the matter and she told me that while I was fucking her ass, it felt very good, and her orgasm was stronger, and different from anything she had ever experienced, but that she was really sore and didn't know if she wanted to do it again.

She said sadly that she was sorry. I comforted her and told her all would be well.

I knew what the problem was, so a week later when her ass was back to normal, I invited a young friend of mine to the house for dinner.

She was to wear her white strapless, bandeau top dress and no underwear. She immediately squealed because she knew what that dress meant.

She was only allowed to wear that dress when she was going to get fucked by someone she didn't know.

Our guest arrived and when she greeted him at the door, and saw that he was only a few years older than she, and very good looking she got all girly and was excited.

She looked at me with that, "Is he really going to fuck me tonight?" look.

I had seen him in action at a play party. His cock was very long, about ten inches, but not so big around.

She liked him a lot. I told her that later in the evening, he was going to fuck her ass.

DEER IN THE HEADLIGHTS!!

She started to cry and asked me please not to require her to do this!

I said dinner was ready, and she was to serve us as soon as the table was set. She composed herself, and set the table and served dinner.

She was terrified, remembering how badly she had hurt after I had fucked her ass, even though she loved the feeling once I was in and she had had huge orgasms.

She had told me that the feeling was incredible, and stimulated her differently and a lot stronger than when her pussy was fucked. She just said the pain afterward was excruciating and she wasn't sure she could do it again. She said she hoped I wasn't too disappointed in her.

I had started inserting the jelly butt plugs into her ass regularly, having her wear them until she was comfortable, then I would go up a size. This went on for two months.

She had graduated to a very large Jelly. I told her how proud of her I was, and as a gift, I bought her a stainless, jeweled plug, and then a stainless plug with a tail...

She liked the jeweled plug, but she LOVED! the tail and would wear it around the house, and once when we went out to dinner under a long dress.

I was regularly fingering her ass with one or two fingers when I was fucking her, and she got very wet and loved the feeling of having my cock in her pussy, and fingers in her ass.

Knowing how afraid of it she was, I never tried to fuck her ass with my cock. Then I figured it was time, so I invited the young friend of mine to dinner.

She nervously served our dinner, ate hers in the kitchen as I had her do whenever I had company.

I could see her anxiety throughout the evening. She lit up whenever the young man addressed or thanked her, then the look of anxiety would return to her face.

About 30 minutes into the meal, I asked her for a "Wet check".

This was something I required of her whenever I asked. She was to turn and face me, averting her eyes, stand with her feet apart, her hands to her sides, and say, "Ready Sir".

I would then reach up her dress or down her jeans and run my middle finger across her clit and into her vagina, briefly massaging her G spot as I did. She loved this procedure and was always wet.

This evening I slid my hand up her inner thigh to about 4 inches from her vagina, and felt her wetness running down her leg.

I looked at her and said, "Nervous?" She shook her head meekly and smiled and said, "Yes sir".

She always jumped and squeaked a little when I first touched her clit. This was something I had done once in a while in restaurants after I was seated and before she was allowed to sit, or in stores when not too many people were watching.

She loved when I "Wet checked" her, especially if there were some men, preferably construction types, nearby and might see what she was required to do.

After dinner, Kitten removed the dishes to the kitchen and put them into the dishwasher. My guest and I adjourned to the living room with a drink.

After she was finished cleaning the kitchen, it seemed to take much longer than usual, I asked her to come into the living room and present herself to our guest.

This meant standing in front of him, with feet apart, arms at her sides, palms facing forward, and eyes averted. She did so.

I could see she was visibly shaking and breathing heavily. I asked if she was ok, to which she replied, "Girl is a bit nervous, Sir."

I said, "You are shaking".

I asked if it was because she thought our guest was attractive, or because he was going to fuck her in the ass in a few minutes.

She turned and ran into the kitchen and threw up in the trash can.

I followed her into the kitchen and got a wet towel and applied it to her forehead, swept her hair behind her ears, and said, "You can do this, and I have told him to go very slowly and to use a lot of lube.

He has done this many times, and I will be there to ensure you are ok".

She calmed down and turned and hugged me. I took her in my arms, hugged her tightly, told her I loved her and wouldn't require her to do anything that I thought would harm her.

She looked up into my eyes, her eyes were teary and said, "I love you Sir, I am yours to do with as you see fit, and I'm ready to do this".

We returned to the living room after she regained her composure.

She returned to her "Present" position in front of our guest and apologized for her behavior.

He looked up at her, smiled and swept her hair behind her ears, took her face in his hands and kissed her forehead.

I could see her visibly relax.

I knew she was ready.

I told him to perform a "wet check" on her.

As he gently slid his hand up her thigh, I could hear her inhale deeply. He said her juices were running down her leg.

I told him to ensure what he felt had run down from her pussy, so he ran his hand up to her pussy and apparently slid two fingers into her. She braced and said, "I'm, I'm, I'm, I'm...breathing was shallow and her eyes had rolled up and she was looking at the ceiling.

I said, "What?" She said in a broken voice, "May... Girl... cum, Sir?"

I said, "Girl may not cum yet, NO!"

She was shaking and her knees were collapsing, and she fell to her knees in front of our guest!

I told her to compose herself!

Of course when she collapsed, the young man had pulled his fingers out of her and reached to catch her by the shoulders.

I had him sit back in his chair, told Kitten to stand and present herself to him as she knew she was supposed to. She whined a bit, stood and presented herself.

I told her to remove her dress so our guest could see her body and decide whether or not he wanted to fuck her.

She reached down to the hem of her dress, rose up and pulled the dress over her head, folded it and placed it on the chair behind her, and again presented herself to our guest.

Every time I saw her remove her dress and watched her body move, it took my breath away. Her breasts were firm and round with eraser size pink nipples hard and standing at attention in the center of her perfect pink areola. Her waist was slim but obviously muscular. She worked out vigorously 5 days a week. Her hips were perfectly formed with beautiful round buttocks standing proud and firm above Her muscular thighs. She was a sight to behold.

Our guest was also breathless, as he had never seen her nude.

He looked at me as if to say, "Are you shitting me?" His eyes were wide with wonder and he had a big smile on his face.

I said, "touch her." He stood and gently ran his fingertips across her brow, down both sides of her face, down her neck to her shoulders.

I had previously told him not to touch her nipples or vagina when he was doing this.

He gently touched her from her face to her feet, running his fingertips around her breasts, to her tummy, to her thighs and lower legs. He started back up her inner thighs almost to her vagina then went around her hips to her ass and lower back.

He went up her back to her shoulders and down to her breasts and gently brushed her nipples. Kitten was shaking again!

She looked at me sideways, and I asked if she had something to say. She said, "Yes Sir." I said, "Say it." Kitten looked our guest in the eyes and said to me, "Please, Sir, Please let him fuck me now!"

I actually felt sympathy for her. She was an incredible tease, and I had watched her tease men almost to the point where they had to walk away just to keep from ripping her clothes off and fucking her right where they were. She delighted in it!

I thought she may have had enough. Her self control impressed me. I told her to go into the bedroom and wait in the "Present" position, and we would see her in a while.

She ran to the bedroom!

My guest looked at me and smiled and said, "now? Please?" I said, "Yes, but take it slow on my signal."

We went into the bedroom and she was standing with eyes averted, feet apart, arms at her sides with hands facing forward...shaking, and I could see a string of her lubrication hanging a couple inches below her pussy.

She was ready for anything!

I said to my guest, "She's yours, Enjoy." He immediately took off his clothes.

When she saw his fully erect ten inches, she gasped! Upon further inspection, she realized he was not nearly as big around as I am, even though he was a fair amount longer, and she laughed a nervous laugh.

He looked at me and I said, "Dude, she's not laughing at you, she likes what she sees." How anybody could think ten inches was laughable was beyond me.

I could see relief on his young face and I laughed to myself.

He then turned to her, told her to get on the bed and present her pussy to him. She backed to the edge of the bed, lay back, opened her legs wide.

He cast a glance my way, and I laughed at his obvious astonishment that he was about to devour this beautiful, willing creature!

He kneeled in front of her and he proceeded to eat her pussy like it was his last meal. He licked her clit, slid his tongue down and parted her inner lips, and pushed it into her juicy pussy.

She gasped!

He licked her pussy and sucked her clit into his lips and I assume he was licking on her clit and sucking at the same time.

She said, "Sir, May Girl cum...Please?" I said, "Kitten, cum as much as you like."

Her squeal turned into a moan and she grabbed a handful of his hair and she screamed, "I'M, I'M, I'M CUMMING, AAAaaaaaaahh!"

Then she squirted...she sprayed like I had never seen her spray before.

He was surprised as she sprayed in his mouth, on his chin, and past both sides of his face! He backed off, looked at her pussy, looked at her face, and turned and looked at me.

I nearly fell down laughing! Her juices were dripping off his nose, his chin and his ears. His eyebrows and his hair in front were wet.

He looked at me and said, "SHE'S A SQUIRTER!" I laughed and said, "Oh yeah, I forgot to tell you that."

I said to him, "Are you ready to quit?" He laughed, flipped me the bird, and dove back in.

They played for nearly half an hour that way, he eating and fingering her pussy and her asshole, much to her delight! She squealing and moaning, and writhing at his touch! She was having back to back orgasms, and spraying all over his face!

Then I told them it was time to get down to business.

I had her slide up on the bed, turn around, hang her head over the edge of the bed because I was going to fuck her throat.

She did, and I handed him a dozen condoms and said use these, fuck her pussy, then we are going to fuck her ass.

He put on a condom, started fucking her pussy. I was fucking her throat, and when I would get it in deep, she would gag. She loved to gag for some reason.

He looked at me and commented on how her pussy tightened whenever she gagged!

I asked if he had ever experienced that, and he said, "Not to this degree, she's squeezing my cock very tightly. I've never felt anything quite like this before, It feels really good."

I said she had been exercising her Kegel muscles, and has gotten quite good at it.

We fucked her in both ends for a while, she was gagging and cumming, and was in heaven. I told her it was time to roll over and ask him to fuck her ass.

We pulled out and she got on all fours and, looking at me, said to him, "I'm ready, would you please fuck my ass?"

He pulled off the condom he had been using and replaced it with a fresh one...as I had required.

I walked around behind her, and squeezed some Anallube into her ass, then put some on my finger and inserted it into her ass and spread it quite liberally around her opening.

She was squirming the whole time I was lubing her, and said she wanted very much for this to happen.

I watched as he presented his Cock Head to her anus. I could tell she was anticipating pain.

I reached under her and started massaging her clit. She calmed down and pressed back to accept his very long cock. I heard her grunt just briefly when his Cock Head parted her anus and slid in.

She was still anticipating pain when he very slowly pushed his cock about six inches into her.

She asked him to be still for just a minute. I could see her ass relaxing, and she was moving against my finger massaging her clit. Then she said, "Ok."

He pulled back about four inches, then pushed it back in. Several times he did this giving her only about six inches.

I backed off, and upon insertion, she arched her back, squealed, said' "I'm, I'm, I'm," and I nodded yes to him, and he pulled out about four inches, and slid all ten inches into her..

She grunted and squealed, and practically screamed, "OH, GOD! FUCK ME! PLEASE GIVE ME ALL THAT BEAUTIFUL HARD COCK! OH,GOD! HURT ME WITH THAT THING, PLEEEAASE FUCK ME HARD!"

He and I looked at each other, and I nodded, and he began to slam his cock into her. I could see his balls slapping against her pussy! I watched in wonder every time he slammed into her, her tight buns would jiggle a little.. What a beautiful sight!

Kitten was squealing, screaming, moaning and laughing all at the same time, and saying, "OH, GOD! PLEASE DON'T STOP!"

He slam fucked her for about five more minutes. She screamed! Then he groaned and said, "OH FUCk! I'm cumming!" and I could tell he was past the point of no return!

He slammed into her faster and deeper, raised his head and growled, saying "AAAAAAHH!" Or something like that. Then he collapsed on her, pushing her to the bed!

They lay like that for a few minutes, both breathing like they had just been chased through the woods by a bear.

He pulled out and rolled off Kitten. I was checking with her how she was feeling and she just looked up at me and said, "Thank you, Sir!"