Weekend Extravaganza

Part 1- Background

Andy was very tall, ran his own business and traveled quite a bit. He also had somewhat unusual sexual predilections. He was a dominant man in personality and felt that sometimes the best thing for a woman was a good old-fashioned spanking to show exactly who was the boss. After all, most women acted like spoiled little children anyway, might as well use the tried and true method of dealing with them. In this day and age however, the act of physically punishing a headstrong girl with a session over a man’s knee was frowned upon. Thus, although Andy felt the need on many occasions, to upend misbehaving girlfriends and put them over his knee for a good spanking he never actually carried out the deed. The internet opened up a whole new world for Andy, for online he was able to meet people with the same viewpoints as himself.

Linda was considered short in stature, only 5’2”, but her Irish heritage shined through with her fiery temper and independent nature. Although small in stature, she never shrunk from a good debate and was quite willing to hold her ground against any and all who chose to take her on. ‘I do what I want, when I want’. “After all I’m single and work for a living and pay my taxes and what I do in my spare time is nobody’s business but mine!”

Linda didn’t travel much out of her local area. Her work took her to various locations nearby but not much else. That was fine with her, she wasn’t much of a traveler anyway. That is except when she logged onto the internet, then Linda would travel the world. Online she would experience many new cultures, places and interests. Linda was, despite her outward projection a subbie at heart. The thought of being put over a man’s lap and having her panties pulled down and receiving a good spanking was not only what she was looking for but also what she needed.

They met online by chance, one or the other was searching for people of the same interests and sent a message and received a positive response. They corresponded, exchanging similar fantasies and stories, sending pics of themselves and others engaging in activities that they both enjoyed and found stimulating (spanking, enemas, rectal exams, rectal temp taking….) She sent him a few stories that she had written herself, describing what she was interested in and he had responded with enthusiasm. She sent a few pics that she liked and hoped he would too.

Eventually they did meet in person. After schedules and times were worked out he traveled to her area and they got together for the first time. It was not a momentous meeting. It was only a simple dinner out and conversation - no strings attached. They parted physically but did keep corresponding online, getting to know each other extremely well. What started out as sexual fantasies were now turning into conversations about everything under the sun.

Part 2 - Fun and Games

Their second meeting was a bit more adventurous. They rented a posh hotel room in San Francisco for the weekend. Each brought their favorite toys and a determination to finally act out their own fantasy. Actually Linda brought all the toys - Andy had been reluctant to put a suitcase containing sexual paraphernalia through an x-ray machine at the airport, possibly having to open it up and have it inspected in public. So he had sent a list and Linda had procured the items and brought them to the hotel along with some items of her own.

They arrived at the hotel separately. Linda being the first to arrive since she lived not far away. She had time to prepare herself and the ‘items’ that she wanted to use for their first sexual meeting. Andy’s fantasy would be fulfilled in time but hey ‘ladies first’.

When Andy finally checked in and arrived at the hotel room, he was a bit taken aback by the woman who answered his knock on the door. On closer inspection he realized this was the woman he had been corresponding with and had met briefly once before. She was dressed quite a bit differently this time however. Before him stood what appeared to be a young student of some kind, dressed in full catholic school regalia (plaid skirt, white blouse, white ankle socks and saddle shoes). “Are you my new tutor?” asked the student before him.

Despite suffering somewhat from a bit of jet lag, Andy was able to assess the situation and responded immediately with: “Yes, I’m your new tutor, my name is Mr. Foster. And you are Miss Roberts I presume”.

“Yeah”, Linda answered and swung the door open wide for him to enter.

“Excuse me young lady, I don’t think I heard you correctly,” Andy stated firmly - looking down on this’”student’.

“Yes Sir” Linda responded, rolling her eyes and backing up out of the doorway.

“That’s better” he said and entered the room, slamming the door behind him. He couldn’t help but notice Linda jump a little at the noise and grinned to himself. He tossed his suitcase on the bed and pulled the chair from the nearby desk and set it down in the middle of the room. While Linda watched in silence ‘Mr. Foster’ removed his jacket and tie, tossing them on the bed. As he began to roll up his shirt sleeves Linda knew that the games were about to begin and despite her wanting this she felt her stomach begin to churn and her mouth went dry.

She didn’t even try to resist as Mr. Foster grabbed her by the wrist and dragged her over to the chair. As he sat down he pulled her to him so that she was standing between his knees facing him, each of her wrists held tightly by one of his hands.

“Well, Young Lady, why is it that your mother felt you needed a special tutor this summer ?” Mr. Foster asked.

“Because…I..Uh…ummm….cuz…” Linda stammered. She gazed up at the ceiling trying to think of a good answer, but before one could come to her she felt two strong hands about her waist and she was lifted up and placed faced down over Mr. Foster’s lap. She found herself gazing at the intricate carpet of the hotel room, still searching for a good answer. A sharp smack on her upturned backside brought her back to reality however.

“I asked you a question Young Lady!”

“I wasn’t doing to good in school, that’s why” she blurted out and immediately felt several more sharp smacks. Although her bottom was covered with her skirt and panties the smacks had hurt and she began to wonder what a real bare bottom spanking was going to feel like. Her fear increased with each smack, so much so that she now firmly believed herself to be a young school student laying over her teachers lap, being asked questions that had to be answered and receiving a spanking whenever the answer wasn’t quite good enough.

“Mr. Foster” also noted the change in his ‘student’s’ demeanor. Earlier she had seemed somewhat bratty, even arrogant, but now draped over his lap, she was very quiet and seemed afraid to move. Her right hand was gripping his left ankle very tightly and she didn’t try to escape from her position. He had smacked her bottom with some force knowing the skirt and panties would absorb some of the sting. Andy longed to whip up Linda’s skirt and pull down her panties and view her white cheeks, but he knew that all this would come in time and at the moment what he needed to do was teach this young lady who was “boss”.

He pulled the back of her skirt up and gripped Linda about her waist, hugging her to him and proceeded to spank her with a new found energy. Each smack was received with an equally loud cry of pain. After 20 sharp smacks to Linda’s pantied bottom he stopped and rested his palm on her bottom. He waited to see what her reaction would be…..

When ‘Mr. Foster’ had flipped up the back of her skirt Linda had jerked up her head in embarrassment. ‘I’m laying over a man’s lap about to get a spanking!, I’m a grown woman, what if someone finds out about this?! I’ll never live this down……’ Her thoughts were interrupted as she felt the first smacks on her bottom. Without the skirt to get in the way what she now felt was almost unbearable and despite her wanting this she now felt herself crying out with each smack. She was almost on the verge of tears when the spanking stopped and she felt his hand come to rest on her sore bottom. She collapsed over his knee, all the energy gone now and simply hung from his knee feeling her bottom throb.

“And why weren’t you doing well in school?” Mr. Foster asked as he rested his hand on his students backside, applying just enough pressure so that she would be aware of her precarious position.

“Um.. I haven’t been feeling well lately and I…uh…guess I haven’t been able to pay attention in class as much as I should,” Linda answered after some thought. She could feel his hand pressing down on her backside and wondered if he had noticed her underpants. She had picked them out the day before. They were plain white cotton panties with little pink roses on them. She also wondered if she was about to feel his fingers slip under the waistband as he began to pull them down to expose her still throbbing backside.

“Not feeling well?” Andy thought to himself, this was his cue to begin the second act of this fantasy. He glanced over to the nightstand and saw the jar of Vaseline and rectal thermometer resting there. He reached over and grabbed first the Vaseline and then the thermometer……

Linda glanced up and saw Andy grasp first the Vaseline and then the brand new rectal thermometer she had placed on the nightstand earlier. She closed her eyes, just listening to the sounds of the jar of Vaseline being opened and the thermometer being unwrapped. When she opened her eyes again she saw the jar of Vaseline was placed on the floor right below her nose and the thermometer was sticking up from the center. As she gazed down and took in this new object she finally felt his fingers slip under the waistband of her underpants and begin to tug them down over her bottom.

Andy heard Linda gasp quietly as he pulled down her panties, she even lifted up a bit to make it easier. “This is going to be a great weekend,” he thought to himself as he took in the view. Her cheeks were only slightly pink from the spanking but he knew they would be bright red soon. He began to run his hand over her bottom and down her thighs, massaging each cheek, getting a good feel. Without saying a word he spread her cheeks wide and took a good look at her anus and surrounding area, this was the first time he had seen her somewhat naked. Her anus was clenched tight, he ran his finger along it but didn’t try to penetrate.

Linda felt herself blush as Andy held her cheeks apart. She had never felt so vulnerable before. She wondered what she looked like back there. She clenched her anus tightly, suddenly afraid he may try to insert something really large, images of bananas and cucumbers flashed through her mind. Thank God she bought the economy size jar of Vaseline she mused to herself and grinned. She felt her cheeks snap back into place as Andy released his grip on them.

Andy reached down and plucked the rectal thermometer from the jar of Vaseline. With his left hand he once again spread Linda’s cheeks apart. This was one of the moments he was looking forward to. He brought the tip of the thermometer close to her anus and slowly began to insert it, he didn’t even blink, but watched intently as it began to disappear into her rectum until only the last inch was left outside. He let go of the thermometer which now protruded from Linda’s rectum. As he held her cheeks apart he kept his eyes on that thermometer and was amazed to notice that it seemed to bob a little with each heartbeat. He felt his dick start to get hard and strain against his pants, it too seemed to jump with each of his own heartbeats.

Linda was surprised at how cold the thermometer felt, she liked it, ‘humm… next time maybe I should put it in the refrigerator before hand.’ Her heart began to beat a little harder as the thermometer went deeper into her rectum. She couldn’t think of anything appropriate to say at this moment so she just closed her eyes and took in these new sensations. “This is going to be a great weekend,” she thought.

Andy grasped the tip of the thermometer and started to draw it out, just before the bulb tip was about to reappear he inserted it back in. He did this several times, sometimes he would jiggle it around a little, twirling it. Although he had imagined doing this in his own fantasies he had never actually been able to do it for real and he was giving it his all. He tried to imagine how it would feel to have his own temperature taken this way. As he continued to play his dick got even harder. He had to stop and rest a minute, “I have all weekend” he thought, “relax…”

Linda couldn’t help but notice the thermometer sliding in and out of her rectum. She lay still taking in these new sensations. She felt her pussy start to get wet….wetter actually. Having her temperature taken as a little girl was never like this! She made a mental note to herself… “Find a larger thermometer!”. Just as she was about to drift completely into dreamland a loud voice brought her back.

Part 3 - Rectal Exam

“You do seem to have a bit of a temperature Miss Roberts,” Mr. Foster stated loudly as he examined the thermometer reading. “Have you ever been given an enema?”. Andy gazed down at Linda’s exposed backside, waiting for her response. He knew that no matter how much she may verbally protest being given an enema, it was all part of the fantasy, and soon he would have the pleasure of finally fulfilling his dream and hers.

The mention of the word “enema” sent a chill through Linda’s prone body. At last she was about to receive her first enema. She had read many stories and viewed many pics involving enemas and could only dream about actually receiving one, but now the moment was close at hand. She fell back into character and decided to put up a small pretense of hostility to the idea. “I don’t need an enema!, Please don’t give me one!, I’ll study real hard from now on!, I’ll behave!, I’ll do whatever you say!, Please Mr. Foster don’t give me an enema!!”. She was rewarded for her outburst with another volley of smacks to her now naked behind. “OWW!!” - HEY, THAT REALLY HURTS - DAMMIT!!”. She twisted her head and gave Andy a bad look, he responded with another slap, this time harder than all the rest. Linda now knew exactly who was in charge (for the moment).

Andy pulled Linda up from his lap and walked her to a corner in the room, pressing her face close to the wall, he gave her ass several more sharp slaps. He tucked the back of her skirt into its own waistband thus ensuring that her backside would remain in clear view. In addition he pulled her panties down farther so that they rested around the back of her knees. Satisfied with his handiwork he bent down and whispered in her ear: “You will stay still in this position until I say so, do you understand Miss Roberts?!”

“Yes Sir,” Linda answered meekly, grinning, but being sure he couldn’t see her doing so.

Andy grinned to himself as he walked into the bathroom. He was not surprised to find several items already placed in clear view ready to be utilized. He turned on the hot water tap and began to let it run. He poked his head out of the bathroom door and checked on his ‘student’. Linda was standing just as he had left her. He thought her backside looked a bit redder now and much more inviting. He selected the red rubber bag he was most familiar with, making sure the metal clamp was closed he started to fill it with hot water, when it was half way filled he opened a packet of soap and poured it in and continued to fill it with more water. He hung it on the towel bar and then turned to select a nozzle. He found a very nice one and attached it to the end of the hose. It was as he was about to leave the bathroom that he noticed the box of latex gloves on the counter. He grabbed two of them and walked back into the room.

Linda had heard the water running in the bathroom and was trying to imagine how her first enema from a man was going feel like. She had left several nozzles on display on the bathroom counter, she hoped he had selected the black one, it was her favorite, it was about 6 inches long with a bulbous tip. There was no way you could ignore it as it entered you. She also had left a box of latex gloves (size-large). She hoped he saw it and remembered her fantasy of being given a rectal exam. Before she could imagine anymore she felt her left arm being gripped and she was walked back to the chair still sitting in the middle of the room.

Andy walked her back to the chair and told her to stay there. He then went to the bed and opened up his suit case, pulling out a large T-shirt. He went back to the chair and sat down. He began to undress Linda, starting first with her saddle shoes and white ankle socks. He pulled her panties back up into place (he enjoyed the act of pulling them down). Next he undid Linda’s plaid skirt and let it fall to the floor around her ankles. He then unbuttoned her white blouse and pulled it off her tossing it on the floor next to her skirt. Last but not least he undid her bra and pulled it from her. Linda now stood in front of him, naked except for the white panties.

Linda felt like such a little girl being undressed by someone this way. She instinctively wrapped her arms around her chest trying to cover her breasts. She could actually feel her face blush bright red as she stood before him in nothing but her panties (at least he had pulled them back up). She felt a little less exposed when he put the T-shirt over her head and pulled it down over her. It reached almost to her knees and it reminded her of a nightgown or perhaps a hospital gown….. Andy pulled the latex gloves from his pants pocket and stated in as clear and strong a voice as he could muster: “I’m going to give you a quick rectal exam Miss Roberts, I want you to lie back over my lap like before.”

Andy hoped he sounded more forceful than he felt. His hands trembled with excitement has he pulled on the latex gloves. He glanced up to see a smirk on Linda’s face as she watched him struggle with the gloves. “Do you find something funny Miss Roberts!?” he barked at her as he propelled her back over his knees and whipped up the back of her T-shirt. “I doubt you will find this rectal exam quite as amusing!!” he snickered as he reached again for the waistband of her underpants.

Ounce again Linda found herself lying across Andy’s lap, her panties being pulled down. This time Andy was a bit more abrupt in her disrobing and she worried that he may rip her new underpants. She hadn’t meant to laugh, but she was having such a good time watching him struggle into the latex gloves, perhaps she should have gotten the extra large? As she watched Andy grabbed the jar of Vaseline and took it out of her view. From now on all she could do was lay still and see or rather feel what was going on behind her.

Before spreading Linda’s cheeks with his left hand he had greased his right index finger with a large dollop of Vaseline, which he now held poised above her little anus. He ran his finger up and down her crack, circling her pink rosebud a few times before poking it in a bit. Her anus felt very tight, and seemed to grip the tip of his finger. He wriggled it a little and felt her loosen up, after several seconds he began to push deeper into her. He pulled his finger completely out and re-lubricated it with more Vaseline before plunging it back in, this time going all the way in until his knuckles rested against her hole. As his finger traveled deeper into her rectum Linda began to squirm on his lap and he was forced to push down on her lower back to hold her down.

Linda gasped as she felt Andy’s finger begin to enter her rectum. The thermometer had felt small, slick and cold as it had slipped in but Andy’s finger seemed warm and very large. She began to struggle, trying to get away from his invading finger in her backside. She felt Andy push down on her lower back, holding her in position and she knew then that even if she wanted to stop now she would be given a rectal exam like it or not. It was this feeling of helplessness that caused her to cry out. Deep down she knew that no matter how much she protested, Andy would be able to do what he wanted. He was now the ‘boss’.

Andy slowly pulled his finger from Linda’s rectum and stripped off the latex glove. He rested his right hand on her bottom, but continued to hold her down. He had been a little concerned when she had cried out. He thought he may have hurt her, but soon came to realize that she had cried out not from pain but from being in such a helpless position. He knew that he was now in total control of her and even if she wanted to stop all activities that only he would have the final say. He was bigger and stronger than her and if he wanted to force himself on her he could. He could only imagine how she must feel at this moment.

“Well Miss Roberts, that wasn’t so bad now was it?”. Linda groaned out loud in response and both of them started laughing. Andy swatted her bare bottom a few times and then stood her up on her feet once more and then walked her into the bathroom and the waiting enema bag. Linda’s cheeks felt slippery as she walked and she could still remember the feeling of his finger deep in her rectum. She hadn’t noticed how long his fingers were until now. She would never be able to look at a mans hand from now on without mentally measuring the length of his fingers.

Part 4 - Watersports

Linda’s knees almost buckled when she saw the enema bag hanging from the towel bar. Andy had indeed selected her favorite nozzle, the slick black one with the bulbous tip and it hung from the hose of the bag almost begging to be inserted up her bottom. Once again Linda found herself laying across Andy’s lap. Linda wished her bathroom at home was as large as this one so she could keep a chair in it too. As before Linda felt the back of her T-shirt being pulled up out of the way and she trembled a little with excitement.

“You aren’t cold are you ? I can turn on the heater if you are,” Andy asked. Linda didn’t say anything, just wiggled her butt at him hoping he would get to work - the anticipation was killing her. “Oh well, I’m sure this enema will warm you up quite nicely.” He reached over and gripped the nozzle and brought it close to her upturned backside. He had lubricated it earlier and he almost lost his grip on it. He spread her cheeks with his other hand then pushed the tip of the nozzle up against her anus. He caught his breath as he took in sight of that nozzle snuggled up against her waiting backdoor. He began to gently push it in….

Her breath caught in her throat when she first felt the nozzle against her anus and then slowly demand entrance. The bulbous tip finally passed her tight anal ring with an almost audible pop and began to travel deeper into her rectum. This was the moment she had been waiting so long for and she wasn’t being disappointed. From somewhere far off she heard a metal clamp being unsnapped and immediately felt a warm rush of water enter her. As the flood traveled farther up her bowels she experienced her first orgasm. Her back arched and her legs stiffened, she let out a low moan of pleasure.

Andy immediately clamped the hose. “Cramps?”, “I’ll let you rest a minute, then we’ll continue, remember this is for your own good young lady.” When Linda seemed to calm down, he opened the clamp back up and began to massage her back with his left hand. With his right hand he began to explore her gaping pussy, she was practically dripping with juice. He had just slipped several fingers deep into her vagina when her head snapped up, her legs stiffened and his fingers became trapped by her pussy which seemed to clamp down around them with alarming power. His eyes opened wide at this new development, next time he gave her an enema he was going to bend her over the edge of the bed and make sure his dick was firmly planted in her pussy before he loosened the clamp. Just as the bag gurgled empty but before he lost all feeling in his trapped fingers Linda went limp.

Sweat was beading on her forehead and she was breathing hard. She had come twice during the enema. Next time Andy gave her an enema she would make sure he remembered to make use of the long vibrator she had left on the counter.