Katherine Ch. 02

Story Info
Katherine's first time anal with Denis.
2.6k words
4.22
46.3k
3
0

Part 2 of the 2 part series

Updated 09/22/2022
Created 08/23/2003
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Magicien
Magicien
51 Followers

After she undressed, Denis asked Katherine to kneel on the bed. Kat rested her slim stomach on two pillows – and her 38-D breasts hung down to receive his caresses, if that was what Denis desired.

He cuffed her wrists behind her back once Kat was in a comfortable position. The cuffs for her wrists were improvised. They were of bright orange plastic - made for some industrial use – possibly harnessing electrical cable. Surprisingly they were comfortable and they didn’t require a key to open.

“Now, to make sure you’re not going anyplace for the next hour or so,” he told Katherine in a cheerful tone of voice as he showed her the rest of the bondage gear.

He used the first two ropes for her arms. Each was securely tied at her shoulder and each went to a corner portion of the bed frame. The second set of ropes went around her knees. When they were tight Denis asked her to spread her legs “just a little bit more.” Then he pulled the ropes forward and tied them to the same two corners he had used to anchor her shoulder ropes. The last set of ropes were tied around her ankles, and the ends were tied to the bed frame on the opposite side of the bed. In that position Kat could feel the cool breeze on her naked backside. Her legs were wide apart and her shaved cunt was clearly visible.

For a while Denis was content to caress her breasts, feeling the smoothness of her skin, rolling her nipples between thumb and forefinger. Her nipples stiffened nicely. It was a shame – in that position he couldn’t kiss or lick her nipples – but he could squeeze them, first one and then the other, harder and harder. She closed her eyes as she got deeper and deeper into the sensations.

“Let’s see how you’re doing,” he told her. And if her dripping pussy was any indication, Katherine was doing perfectly well. His index finger, inserted up to the knuckle confirmed the truth of his statement. He slowly withdrew and then added a second finger to her wet kitty.

Katherine liked the feel of his fingers, wet with her cunt juice, as he first caressed the entrance to her vagina, and then slightly higher, just below her clitoris.

“Hmmm,” from Katherine.

“Slut,” from Denis.

He used his wet fingers to push back the hood of her clitoris, to touch her gently, to continue to increase her arousal. At one point he changed his position, lying next to her on the bed, so that he could squeeze her nipple as he teased her clit.

“Please, Denis, make me cum?”

“Not yet. First I want to see how anal you really are.”

Katherine had been on the verge of an orgasm for at least five minutes. It was as if Denis had some sixth sense that told him when to back off – when to slow down or to shift his attention to some other part of her anatomy – to keep her from that elusive orgasm.

“Please, Denis, this is torture …”

“Not yet. You told me you like it in the ass and I want to see how anal you really are.”

That had been their e-mail joke from the beginning of their relationship. Talking about her preference for anal stimulation, Katherine had told him it was her belief, ‘If one finger is good, two fingers are better …’

Denis got up from the bed and went to his briefcase.

“I only have a two more items, for the next part of our adventure.”

First Denis showed her a tube of KY jelly. Katherine had expected Denis to bring some sort of lube – and for moderate anal play KY would do the job – followed by a latex examining glove.

“I’ll start with my bare hand,” Denis told her. “I like the feel of your skin. But for deeper probing …” and Denis smiled his famous smile.

“Hmmmmm.” Katherine was starting to imagine the feel of at least two gloved fingers, slick with lube, deep in her rectum.

Denis knelt in back of Katherine on the bed. He began to caress the inside of her left thigh, just above the knee. Slowly he worked his way up her leg, teasing her, feeling the softness of her skin.

“You’re doing this on purpose. You’re very mean.”

“Of course,” from Denis.

G-d, his hand felt so nice. Kat was getting very aroused by the softness of his touch on the inside of her thigh.

“You’re driving me crazy,” from Katherine, followed by, “You’re a very mean bastard!”

Denis stopped for a moment to withdraw his hand from between Katherine’s legs. Quickly he smacked her twice, once on each shapely ass cheek.

Thwak! Thwak!

“Ahh!”

“Hold still. And be quite! Now I have to start all over again.”

And Denis did start all over again, just above her left knee, slowly tracing the path up her left thigh.

Katherine tried not to make a sound, but she was wiggly her sexy ass by the time Denis reached the top of her thigh. He didn’t spend a lot of time playing with her pussy – just enough to coat his fingers with her wet. Then he used his left hand to spread the cheeks of her ass, to expose the pucker of her asshole.

His first touch was very gentle, just his middle finger, pressing gently.

“Hmmm, that’s nice.”

“You like that, my finger back there?”

“G-d, you know I do.”

“And this?”

He went into her about an inch – very gradually – very slowly – giving her time to adjust to the gentle intrusion.

“Please …” from Katherine.

“Please what?”

“Please go deeper …”

Denis quickly withdrew his finger. He wiped off his finger tip, and quickly put on the latex glove, and then opened the cap of the KY tube.

“I will be a little cold at first, but my guess is that you already know that.”

Katherine was not an anal virgin, so the initial cold was not a shock.

Denis squeezed a dab against the pucker of Katherine’s asshole and then started again with his middle finger. He went in easily – first an inch – and then a second inch.

“Nice ass,” he told her.

Then Denis withdrew his finger a little, and began moving his hand in a slow circle, slowly stretching the tight ring of her sphincter. Gradually he worked his finger back into her asshole, gradually opening her as he went all the way in, up to his knuckle.

“You’re good,” Katherine told him, as she wiggled her ass some more..

“Thank you …” as Denis began to slowly finger fuck Katherine in the asshole.

“I really like this …Hmmmm …”

Denis moved forward on the bed and Katherine turned to him to kiss him on the lips. It was a pity - she wanted to caress his cheek as she kissed him, but her wrists were cuffed behind her back. Finally Katherine broke off the kiss.

“Ready for another finger?’

“Yes, sir. Please.”

Denis used more lube, this time from the tube onto his first two fingers. Katherine pushed back as he pressed and both fingers went in easily.

“Hmm.”

Denis let Katherine adjust, and then very slowly filled her rectum with both fingers.

“Ahhhhh.”

“Are two fingers better than one?”

“G-d, you know they are.”

“And this?” as Denis slowly began to finger fucked her tight asshole for the second time.

“Oh-My-G-d!”

“And this?”

Denis reached under Katherine’s belly with his left hand. Her cunt was dripping wet and her clit was very slippery. He continued to finger fuck her asshole as he pushed back the hood of her clit.

“You’re killing me.”

Then “OH-MY-G-D!” even louder than before.

The trembling started in her thighs. Katherine struggled to close her legs, but the ropes around her knees and ankles were too tight. It was much too intense.

“Please, Denis!” as Katherine exploded in the first orgasm. Being held in place made the orgasm more intense. She tried not to whimper, but that was impossible.

“Ahhhhhhhh … G-d …… Jesus.”

As the orgasm subsided, it all flashed back to her - being made to kneel - her head down - her sexy ass up in the air. It was so humiliating to have Denis lubricate her rectum with KY, to feel his fingers deep in her asshole, to feel his fingers moving in and out as he loaded her tight butt with lots of KY.

At first Kat was humiliated, being made to kneel in that position. But she couldn’t help liking the feeling of Denis’s finger deep in her rectum, moving in and out, stretching her, opening her. At the end, he teased her clit with his other hand, and the orgasm was simply incredible.

Now Kat was back in the present moment, kneeling at the edge of the bed again, tied, with her hands cuffed behind her back. And then her Denis’s touch, on the inside of her thigh, the way he began the last time. It was pure heaven, with just a little bit of torment thrown in for surprise effect.

"Please," she started to say.

"Don't say a word, not now, not until this is over."

"Please, Denis," she started to say again, but he slapped her on the ass before she could finish. She wanted to tell him she was too sensitive, that she needed a time out - but she knew he wouldn’t wait.

"Not another word, or I'll put a gag in your mouth." And then he slapped her on the ass again, even harder.

Kat often fantasized about anal sex when she was alone in bed at night. In her fantasy Denis would make her kneel on her bed when he fucked her in the ass. She would lie in bed and imagine Denis’s cock in her not so virgin asshole, being slapped on the ass over and over again as Denis fucked her. She would touch herself and dream, and finally have an orgasm as she imagined Denis shooting his hot cum deep into her rectum.

She wasn't sure how long he stood there, just behind her, looking at her, studying her, as she knelt at the edge of the bed.

Then Denis’s touch again, this time along the groove of her ass. He started at the bottom, just behind her pussy, and slowly traced a long line up to the base of her spine. How could he move his hand so slowly, yet still retain contact with her body? Then Denis made the slow trip south, along the same path. By the time his fingers reached the end of their journey, her pussy was wetter than before. She hoped he would enter her, play with her, tease her clitoris. No such luck.

There was a pause for a moment, then more silence, and then his touch again, just two fingers, spreading the cheeks of her ass for the second time. She knew immediately that she would blush, then instantly felt her face get red, as he spread the cheeks of her ass, exposing her anus, preparing her for his penis. Then the familiar cold as Denis squeezed more KY from the tube directly on the pucker of her asshole.

“Do I need to open you up some more?”

He had finger fucked her in the ass, two fingers worth, for at least five minutes, before her orgasm, so Kat was already pretty open. But her sphincter was tight, tight enough to squeeze him, to grip him, to give him pleasure when he finally put his cock up her ass. But for now he was only playing with her again, teasing her, arousing her, getting her ready.

Denis withdrew his finger, applied more lube, and he was back inside of her. There was more urgency now in his touch, more pressure with his finger tips, as he went into her again to the knuckle.

Then the familiar circling motion, opening her, preparing her. Kat tried to let herself relax, told herself it couldn't hurt, that Denis would never really hurt her. And then another voice told her that she really did want just a little bit of pain, that she really did want to be stretched, that she wanted to feel her Denis’s fullness when he fucked her in the ass for the first time.

"You can never use enough lube," Kat had read a Cosmopolitan magazines years ago, in an article about pleasing your man by giving him anal sex. Kat wasn’t sure men read Cosmopolitan; they never seemed to really know how to get a girl ready. But Denis did know how to get a girl ready to have her asshole reamed. She waited patiently as he took his finger out, held the cheeks of her butt open, and applied more ice cold lube directly to her asshole.

There was another moment of silence, and then Kat felt the head of his penis against the cheeks of her ass. He applied some more lube, Kat was glad of that. Then she felt his thumbs, opening her, exposing her. Then his penis, she was sure he was guiding it with one hand, as he pressed against her sphincter.

"Just relax and exhale, and push back. You’ve done this before." She had done this before and it worked like magic. He was inside of her, just barely. She gasped as she felt herself grip the crown of his penis.

Denis gave her a moment to catch her breath, and slowly, steadily, he began to fill her with his thick erect penis. By the time he hit bottom, there was a certain fullness she could not quite describe. And then the pain which really wasn’t pain, at least not to her.

Then he began the in and out. At first the strokes were slow, deep, and steady. G-d, she loved getting fucked in the ass.

For a while Denis was able to keep the strokes deep and slow, but as he began to build to his climax, he fucked her harder, more rapidly. He gripped the cuffs on her wrists with his left hand, holding her in place. At the same time he started slapping her bottom with his right hand, matching the tempo of his strokes, all the while driving his cock deeper and deeper into her ass.

The last minute was like a blur. Denis fucked her harder and harder, and Kat’s clit was rock hard and almost on fire, as his penis went deeper and deeper. She wanted to touch herself, to rub her clit, to help herself cum, but the cuffs on her wrists prevented her. Every nerve in her body was on edge. The lining of her rectum had never been so sensitive. Just before the explosion, Kat was sure she could feel the veins on his penis as Denis reamed her insides. Then she heard him whimper.

All Denis said was "Oh, my G-d."

There were the short, stabbing, very rapid strokes, followed by the gush of hot cum deep in her rectum, and the Kat felt her own explosion.

They both fell forward on the bed. Every nerve in Kat's body was on edge. She could feel his chest against her back, his belly against her ass, his legs against her legs. Finally he kissed her tenderly on the shoulder, covered her body with his own.

"I hope you enjoyed that," was all he said when it was over. There wasn't anything else that really needed to be said.

Magicien
Magicien
51 Followers
Please rate this story
The author would appreciate your feedback.
Share this Story

READ MORE OF THIS SERIES

Katherine Previous Part
Katherine Series Info

Similar Stories

Cheryl's Passion Ch. 01 Cheryl decides she needs a mistress.in BDSM
One Smoking Hot Ass Anal prostitute explores her limits with a mysterious client.in NonConsent/Reluctance
Evelyn in Captivity Ch. 01 Evelyn discovers her girlfriend's true nature.in NonConsent/Reluctance
The Naked Prison Ch. 01 All prisoners are to be naked on this special prison island.in NonConsent/Reluctance
Easy Cum, Easy Go Desperate Times Require Desperate Pleasures.in Anal
More Stories