Skinny Dippin' and a Lickin'

The day started out wonderfully. It was sunny but not too hot and with a very pleasant summer breeze that drifted the sweet scent of honeysuckle thru the house making everything seem relaxing, airy and full of life. "How could such a great day turn out so lousy?" Kassie thought a couple hours later as she stood naked and miserable with her nose pressed into the living room corner. Try as she might she never could manage to stay out of trouble for long and now here she was once again, about to get her soft bottom soundly spanked.

"All right Kassie, come here and present yourself for inspection, you know the routine." Jeffery, her husband, said with an exasperated sigh. He loved spanking her bottom but he greatly preferred doing it as foreplay rather than discipline. He hated hurting the woman he loved in any capacity but he knew it had to be done and done well. Kassie being 12 years his junior, still needed a firm hand to teach her to start taking responsibility for her actions and to think before she did things.

"Yes Sir." Kassie replied as she turned and walked toward Jeffery. Every step she took was a struggle. It felt as though her feet were suctioning to the floor. She stood before him, pleading with her eyes for him not to make her present herself to him, not to punish her for what she did. She didn't think it was such a big deal. After all, all she did was take a quick dip in the pool in the back yard. "Okay," she thought to herself, "so it was actually skinny dipping but they had a privacy fence! How was she too know that the neighbors were getting their roof refinished and that it was covered with men working!?"

When Jeff came home from work and seen her swimming nude while the workmen actually stopped working and were sitting along the roofline enjoying the view, he was livid! He yelled for her to get out of the pool, and spanked her soaking wet bottom all the way into the house and into the corner while the workers cheered. Once she was in the corner he still didn't stop, he just lectured and spanked her bottom hard for 5 more minutes making it so red it practically glowed. Before leaving her he ordered, "Move one inch, young lady, and your backside will be blistered every day for a week!" There wasn't any way she was going to move. Once during another punishment session, he had threatened that very same thing and she thought he wasn't serious so once she was tired of standing in the corner she sat down. She found out just how serious he was when she found herself with a very well punished bottom several times a day for a week just as he promised!

"You know the routine Kassie. No sweet innocent looks are getting you out of this so present yourself at once or I will double all the punishments that I have planned for you!" Jeff said.

Immediately she turned around so her back was facing him. She spread her legs wide and bent over at the waist; thrusting her already reddened bottom out. Reaching back she spread her bottom cheeks wide so he was presented with a perfect view of her pussy and anus. He didn't know what was redder, the blush he could see on her cheeks or the one his hand had caused on her smooth bottom. He knew she hated this, but he believed that a certain amount of humiliation always did her good. "After all, if she could present her body to the workmen while she was in the pool she most certainly could present it to her husband!" He thought.

"Mmmmmmmm...very nice view my dear! Now be sure to keep those cheeks spread wide." Jeffery said as he reached between her spread legs and ran his hands up her thighs. He quickly shoved two fingers deep inside her wet pussy, twisting them as they went inside. He fucked her pussy hard with his fingers making her squirm and moan aloud.

"Don't you dare cum young lady; you know you are not permitted to unless I give you permission!"

"Yes Sir, I understand. I will try not to." Kassie managed to say while trying desperately to hold back her orgasm. She never understood why she got so incredibly horny while being punished when everything usually hurt so badly.

Sliding his fingers from her soaking pussy, Jeffery spread some of her juice on her anus; Kassie tensed up, she hated anal play. Seeing her anus contract, Jeffery swatted her bottom hard, first on the left cheek, then on the right, leaving two perfect scarlet hand prints.

"Relax your asshole Kassie, or it will hurt more. I will be inspecting it, whether I have to force my way in or not!" Jeffery admonished her.

Instantly Kassie relaxed it as best she could. She knew that Jeff meant every word he said. He wasn't one to mince words, especially when it had to do with a discipline session.

Seeing that she had relaxed it somewhat, Jeffery roughly shoved his middle finger deep inside her back passage. Pulling it out slowly, and then ramming it in deeply, over and over again. Kassie cried out with each thrust but still managed to keep her bottom cheeks spread for him. It felt like he was rubbing her tiny bottom hole raw. After a few minutes Jeff felt her bottom relax a bit so he inserted a second finger and resumed his anal play. This made Kassie squirm a bit which earned her another hard swat on her bottom.

"I'm sorry for squirming Jeff, but please, please stop! It hurts so much!" Kassie pleaded to no avail.

"My fingers are nothing compared to my cock, which you will be receiving up this tight ass of yours shortly. Be thankful I am preparing you the way I am. It won't hurt so much now that I have you stretched out a bit." Jeff said, still fucking her ass eagerly with his thick fingers. After several more minutes of his ministrations Jeff finally pulled his fingers from her bottom, much to Kassie's relief.

"All right Kass, it's time for your next punishment. Go and get the hairbrush."

Walking a little stiff because of the pain in her anus, she went and retrieved the hairbrush from the implement case in the bedroom. She knew that soon her bottom would be on fire which excited her, but filled her with much dread at the same time. She walked back to Jeff, kneeled and held the hair brush out to him.

"Please Sir, spank me with this brush on my naughty bare bottom so I will learn to think before my actions." Kassie said, while a hot blush rose to her cheeks. She HATED asking for a spanking. She knew though, that if she didn't he would assume she forgot and she would get a reminder spanking on top of the impending hair brushing.

"Good girl Kassie. Get across my lap now; let's get that bottom nice and hot."

Kassie crawled over his lap and positioned herself with her ass high over his left knee and her nose practically touching the floor. She was so tiny and short that her toes were never able to quite touch the floor. Jeff quickly locked her legs under one of his to keep her from kicking. He rubbed her bottom for a few minutes. Her bottom was as soft and smooth as a newborn babe. He reached between and felt her wetness coat his fingers. Sliding one into her pussy Kassie squirmed and uttered a soft gasp. He quickly pulled his fingers from her and grabbed the hairbrush bringing it down sharply on her bottom.

SWAAAT! She bucked under the first blow but was unable to move much for he had her pinned firmly.

SWAAT! SWAT! WHACK! The blows were coming one every couple of seconds. Never in any certain order so she never had a clue where the next one was to land. He concentrated most of the blows on her tender sit spot and thighs. After just few minutes her tears where flowing freely. Her bottom was dark red and felt like it was scorched.

WHACK! WHACK! SWAAAT! "Are you EVER going to..." *SWWAT* "skinny dip..." *WHACK! * "...in the back yard again?" *WHAM!*

"No sir!" *WHACK* "I promise I won't!" Kassie said thru a sob.

"You'd better not or what you're getting tonight will seem like a smack on the hand!" Jeff said while continuing to swat her bottom. "One minute more and then your hair brushing will be over."

Whack! Whack! Swat! The blows continued for the minute but were dealt out slightly softer than when Jeff originally started. He wanted to punish her, not be overtly cruel. The minute seemed like an hour to Kassie but she took her spanking well, not once trying to cover her bottom.

Jeff finally stopped the spanking and started to softly rub her bottom, letting Kassie stay over his knees until her crying slowed. After a couple minutes, he heard her sobbing cease and told her to get up and stand in the corner. Hiccupping and feeling very punished she walked to the corner and stood facing the wall, wondering if her punishment was over or if she had much more to face. Her answer came a few minutes later when Jeff in a very stern voice, ordered her back over to him.

"All right Kassie, here is the deal." Jeff said. "You get to choose your own punishment right now. I'll give you two choices. One, you can submit to ten strokes of the cane and I'll fuck your ass gently, and slowly while you are lying across pillows on our bed. Or two, we can stick to my original plan of giving you four strokes of the cane but you will fuck me with your ass, right here while I sit on the couch. The catch is, you will have exactly one minute to impale yourself completely on my cock. Every ten seconds over that minute will be an extra stroke of the cane. So what will it be my dear? A guaranteed ten stokes only and being taken slowly and gently? Or are you willing to take your chances of receiving only four, by which you will have to take me up your very tight bottom quickly and painfully? Possibly earning yourself much more than ten strokes?"

Kassie stood stunned. Jeff never gave her an ultimatum like this! What a choice! Either way will be rough! She didn't think she could take ten with the cane, but what if she earned more by taking the other route? The cane was the most dreaded implement in their discipline arsenal. She absolutely loathed it, and whether it was one stroke or four, she couldn't sit for days after its use on her bottom. She had never earned more than six. Usually four was what was administered, with extras added on if she got out of position or interfered with the punishment. What a dilemma!

She thought for a minute and knew that he was getting unsettled by her taking so long so finally she made her decision.

"I-I'll take the four Sir, and take the chance of earning more." Kassie said softly.

He smiled at her decision and secretly hoped that she would make the time limit. He didn't want to give her ten. In fact he didn't want to give her over four, but he would if he she earned them. He knew the cane was horribly painful and made a decision that if she earned over six the others would be delivered light enough to only sting. Of course, she wouldn't know that right now.

"Good now you know the deal, you have one minute to impale your ass on my cock. Every ten seconds over that minute will result in an extra stroke of the cane. You are already getting four with it so if I were you I'd try very hard to hurry. Now go get the lube, the count down will start once you are lubed up. No dawdling on getting the lube either!"

Kassie hurried down the hallway to their bedroom where the lube was located. A deep sense of dreadful anticipation was sitting rock like in her gut. She could feel her juices dripping down her legs. She never understood how she could get so excited by being under his control and being in pain. She found the lube and hurried back to him, handing him the tube.

"Okay Kassie, you lube my cock and I'll lube your bottom hole. Once my finger stops spreading it the clock starts. Got it?"

"Yes Sir." Kassie replied

Jeffery opened the tube and gave her a pea sized amount on her finger.

"Sir? Is this all I am to get?" She said with a shocked look in her eyes.

"I said we would use lube. I didn't say we would use a lot of it. I want some friction on my cock when you fuck me, now lube me up."

The sense of dread doubled when she spread the lube and it was only enough to cover the head of his cock. He was a well built man with a very large cock. With only the head covered it left almost seven and a half inches un-lubed.

"Okay Kassie, turn around and spread 'em. Let me get you lubed up." Jeff said, his cock was now so hard it was hurting. He couldn't wait to get it buried up her bottom. He loved the tightness squeezing his cock that you get with anal sex. Kassie refuses to do it under normal circumstances so he takes advantage of it when its punishment time.

Kassie turned and bent over; reached back and spread her bottom cheeks wide to expose her anus to his ministrations. Jeff used more than a pea sized amount on her anus, unbeknownst to her. He didn't want to damage her in any way; he just wanted her to THINK that she was barely lubed. He made sure she was well lubed and pulled his finger away.

"The time starts now Kassie." Jeff said.

Kassie immediately reached between his legs and guided his hard cock to her back entrance. She felt the head touch her anus and started to slowly sink down, feeling it stretch her anus wider and wider. She let out a loud moan when the head finally popped inside her sore bottom. She started to lower herself upon him, taking him deeper, centimeter by centimeter. It hurt so bad that she didn't think she would make the time limit.

"Thirty seconds gone Love, better hurry it up. You still have over half my cock to take in."

With that she started to really push her way down, trying her best to ignore the pain radiating from her sore anus and bottom cheeks.

"Ten seconds left, your almost there." Jeff said with slightly clenched teeth. The feeling of stretching her wide and her anus contracting around his hard cock was almost his undoing.

She knew that it was now or never so she quickly sat herself roughly on his cock; taking the remaining four inches at once. She thru her head back and let out a loud groan of pain.

"Good Girl, Kassie! You took it all within the time limit! I'm proud of you." Kassie sighed in relief. "Now just rest a minute love, keeping me inside. Your bottom will become accustomed to having me in there and fucking me will be much less painful."

Kassie was grateful to him. She knew that if he really wanted to he could make her start immediately, causing her to have a much more painful time of it. She also knew that it pained him at times to severely punish her like she sometimes deserved, like this time but that didn't mean he wouldn't do it if it was merited. She felt the love for him grow in her heart when she felt his hands gently massaging her back as she waited for the pain in her anus to ease. She knew he loved her and couldn't wait for her punishment to be over so they could just hold one another and make love slowly.

Kassie started to slowly rock herself on his cock. The pain was easing a bit and she rocked faster and faster. She could feel every vein of his cock rubbing along the tight ring of her anus as it slid in and out of her. Her pussy was getting wetter and wetter. She could feel the wetness start to drip slowly to her thighs. The pain finally stopped and was replaced by pure, unimaginable pleasure Jeff reached around her, grabbing a breast in each hand, squeezing and gently tugging on her hardened nipples. He brought one hand down to start to rub and pinch on her engorged clit while still playing with her nipple with the other. After a bit, he stopped playing with her breasts and brought his other hand down to her pussy. While still tweaking and rubbing her clit with his right hand, he took his left and brought it to her pussy hole; shoving two fingers inside. He worked them in and out at a slow steady pace; doubly impaling her. She arched her back and moaned loudly, working herself up and down on him more quickly than ever before. Kissing her neck he said, "You feel so wonderful, so tight and hot! Oh Kassie, I love you. You have my permission to cum this time."

Hearing this she started rocketing herself up and down on his cock. His fingers on her clit and buried deep in her pussy had her panting and moaning, ready to cum.

"I love you too, Jeffery. I never thought anal sex could feel like this! Your cock feels amazing inside me!"

She could feel his cock getting bigger in her anus; stretching her wider and wider. The pleasure coming from her anus and pussy was almost more than she could take when she felt his hot cum flood the inside of her bottom.

"Ahhhhww, I'm cumming", Jeff managed to moan. His cock exploded inside her, filling her with his fluids. He started massaging her clit faster and faster, pressing down and swirling his fingertips around it. He fucked her pussy hard with his fingers until he felt her juices flow down onto his balls.

"Ahhh! I'm cumming, I'm cumming!" Kassie managed to say as her pussy started to spasm. Her anus clenched Jeff's cock tighter, causing him to moan aloud. She felt his cock shrink and slip out of her as she collapsed against his chest. His arms where still around her. His fingers were still resting on her mound, holding her to him. They stayed that way until their breathing returned to normal. Then they moved apart and sat on the couch with their arms entwined around one another.

Jeff cuddled with her until they both regained some of their senses. He had always loved anal sex, but her enjoying it as she had made it even more amazing. They rested for almost a half hour before Jeff leaned her back and reminded her that her punishment wasn't quite over. She still had a caning to contend with.

"Your rest is over, Love. Now get that nose pressed back into the corner. Spread those legs and thrust that bottom out so I can enjoy the view while I set things up for your caning."

With a huge sigh Kassie walked back to the corner and did as she was told. She made sure her bottom was thrust out well giving Jeff the best view possible. Her bottom hole was still sore but she knew that she would never think of anal sex the same way again. She had just never relaxed enough to enjoy it before.

Jeff sat and just gazed upon her, relishing the exquisite view. He wondered what he ever did to get so lucky. Having such a beautiful woman in his life, falling in love, and her actually loving him back, was the best gift he could ever have received. Having her trusting him enough to see to her well being, punishing her when she needed it, was an added bonus. After a few moments he got a chair from the dining room and moved it to the center of the living room floor. He made his way down to the bedroom and retrieved the cane. Taking a few practice strokes he listened to its angry hiss and pictured it leaving its mark upon her smooth bottom. He felt his cock stir and decided he'd better get a move on. The faster he got her caning finished, the faster he could bury himself in her hot pussy.

He stood behind the chair cane in hand and called her to him.

Kassie somewhat reluctantly and with a very cute pout on her face, turned and walked to him.

"Bend over the back of the chair and grab the front legs, Kassie. You know the routine." Jeff said ignoring the cute pout and sounding menacing. He couldn't let her out of the caning no matter how cute she is or how much he dreaded hurting her with the cane. He found punishing her very arousing. Even a caning, though he knew how painful it was for her, still had the effect of making his cock rock hard.

Kassie leaned over the chair reaching for its front legs. She was so short that even on tiptoe she could barely touch the legs. Jeff watching her struggle for a couple minutes tossed the cane down, lifted her by the waist and placed her hips along the back of the chair which allowed her to wrap her fingers tightly around the legs. This also meant that her toes couldn't reach the floor so she was suspended in the air and her bottom was perfectly positioned for the cane.