Tamra's Evening

Tamra was excited. It was Friday evening; she sat in the passenger seat of the car, her eyes were taped shut, and most of her face was obscured by the largest sunglasses she had ever seen. It must be getting dark now, but she could not tell. She had walked in from work at about 4 p.m., and her boyfriend, Jo, was sitting waiting for her. He ordered her to sit down, and she had complied, not sure what was going on.

It still was not clear, but he had read out a list of things she had done wrong over the last few weeks, everything from forgetting to put the trash out, to burning the potatoes on Sunday; there were at least 40 things read out. She had been told it was unacceptable and that she needed to be punished. Excitement had blossomed between Tamra's legs at that statement, but then she was ordered to do something that did not sound like punishment at all. She had to go and change into a dress suitable for a grand hotel, and pack a bag for the weekend--clothes she would look smart in, but that would enable easy access and mobility.

She had put on a beautiful red dress that flowed around her body and normally only came out for entertaining, then packed another smart dress and two skirts, underwear, and 3 tops, all her classiest ones. She picked up a pair of dress shoes with a slight heel and put on a red pair that matched her dress, with a three-quarter heel. Last of all she grabbed wash and makeup bags. She arrived back downstairs with everything in her small Gucci suitcase.

Sitting by the door was a large case, much bigger than her boyfriend would require for the weekend. God only knew what he had in there. Jo walked in front of her holding a butt plug; it was not the largest they owned, but it was one of the bigger ones. He held it in front of her and pulled from a table beside him a pepper spray. He smiled and sprayed the plug heavily; the bounce-off stung her eyes.

"Turn around, bend over, and pull your dress up," came the instruction.

Tamra complied, and as she raised her dress a hard slap that made her cry out landed on her arse. "How dare you put knickers on! Remove them now," came the annoyed statement from Jo.

"Sorry, Sir," she replied, in something little better than a whimper.

Tamra pulled her panties down slowly. They stung the area that had been slapped, but they dropped to the floor, and she stepped out of them. Quickly she bent back over again and raised her dress, not wanting yet another slap. With force that made her gasp, a finger with lube on was pushed into her little brown star. In a slightly rough manner, it was spread around, then the finger removed. Moments later, the plug was pushed against her ring. Even though it wasn't really touching anything other than lube, she could feel the heat. The force with which it was then pushed up made her cry out a second time. There was no delicate work it in; it was forced hard.

"Wait, stop, no," she yelped. The burning was almost unbearable, but the stretching that was being forced was the issue.

Two hard slaps landed, one on each cheek. Tamra sobbed. "Do as you are told. Naughty little girls take their punishment without comment." The words almost spat into her ear. The next push forced it in, her sphincter closing around the spine, the burning in her arse the most unpleasant punishment she could recall. She sobbed, tears rolling down her face.

As she fought the pain, she whispered, "Thank you, Sir."

Jo tuned her around and sat her down on the chair by the door. He delicately dried the tears from her eyes, and from her face. Then he said in a kind voice, "Close your eyes, and keep them closed." Before she closed her eyes, she saw in his hand some sunglasses. They were huge, with big round eyes that would cover half her face.

Tamra closed her eyes and moments later she felt tape being pushed onto her eyelids and then onto the top of her cheeks, firmly holding her eyes closed. After a moment the sunglasses were placed on her face, creating a black view for her.

She had been guided to the car, and strapped in. She heard the bags being placed in the back, then they drove off. She had no idea where they were going, and the lack of sight was making her focus on the burning in her arse; the plug was painful and uncomfortable.

The car stopped, and Jo got out, from how long they had driven, and the sounds that burst into the car when the door opened, Tamra guessed they were in New York. She heard Jo saying something to somebody, but she could not make it out. Several moments past, the sounds of the city coming into the car. Suddenly her door was opened, and she felt a hand on her. Then Jo said, "Come on, dear," and helped her out of the car.

Jo guided her up some steps and through some big double doors. She was trying to work out where she was exactly, but everything went quiet as they got into the building. Walking with the burning butt plug was really uncomfortable, and she was just moving where Jo directed; she had no idea where she was. They came to a stop and a voice said, "Good Evening, Sir, how may I help you?"

From beside her Jo said, "I have a reservation for the weekend, name of Smith."

There was a pause then the voice said, "Arr, Mr. and Mrs. Jo Smith, you are booked in until Sunday with late check-out of 4pm."

"That's us," Jo said.

"Excellent, can I just take a credit card swipe please?" the voice said.

There was some movement and Tamra heard a pin being entered, just as a presence appeared beside her, she could tell somebody was there but nothing more, then a voice beside her said, "Which room?"

The first voice said, "1207." There was a pause then and before he continued, "Here is your key, Mr. Smith, the junior suite with a balcony overlooking the park. Please enjoy, and if you need anything, please give us a call."

"Thank you," said Jo, then she felt her arm taken again, and she was moving at the mercy of Jo.

Tamra felt them enter an elevator, and heard the bong of the bell as a floor was pressed. As the car swiftly moved up, Jo spoke, "My good man, when we get to the room, would you like a cash tip, or would you prefer to bend my wife over the bed and spank her bottom as hard as you can, then have her give you a blow job?"

There was some very uncomfortable huffing and then a reply, "That is not appropriate, sir. I could get fired."

"I am not going to tell anybody, and Tamra here will do exactly as she is told, won't you, Tamra?" Jo said.

Tamra was not happy at all with this. A BJ for a complete stranger was a serious escalation of her punishments. However, she said, "Yes Sir, I will do whatever you order."

There were more uncomfortable noises, then he said, "Can I just get the blow job?"

"You have to spank her too," Jo said. There was silence for a moment then the bell went as they arrived at the 12th floor. Before the voice said any more, they exited the elevator, and were walking along the corridor. They came to a stop, and the sound of an electronic lock filled the air. The door was pushed open, the smell of the room rushing out to greet them. The bellboy entered first with their bags, then Tamra felt her way in, with Jo behind her guiding, but also closing the door.

Jo pushed her gently and she felt her legs touch the bed, she knew what was expected, and bent over the bed and pulled her skirt up revealing her naked arse with the large plug in, and much as she tried to hide her sweet little bald pussy, she knew that was visible, too.

She held position, not having a clue who was looking at her. She heard some hushed chat, but could not make it out, then she heard a bag being unzipped, and movement around.

"Now, Tamra," Jo said, "my new friend Darryl here is going to administer your first spanking, and after he is finished, you will thank him like the naughty slut you are."

"Yes, Sir," Tamra replied. As she felt fingers on the butt plug, it was pulled from her arse. The burning remained; the pepper spray now being inside, it was not comfortable at all. She was sure it was Darryl that removed the plug; it was clumsy and hesitant. Then the bellboy said, "I have never done this before. I hope it is OK."

There was a pause then a swish filled the air and Tamra's cheeks exploded in pain, as a short tawse crashed into her arse. She squealed in pain, feeling the welt already appearing.

"Again, harder," Jo said in encouragement.

The Tawse swished again louder, and just above the first site it bit into her flesh. She yelped; the pain was overwhelming, her legs momentarily giving way, before she caught herself and straightened them.

"Sorry," said the Darryl, but before he could say anything else, Jo said, "Don't be sorry, you are doing what she wants. More and harder."

There was a moment of quiet and Tamra knew she needed to speak, she didn't want to, but if she didn't the punishment later would be even worse, so she said, "I want this, Darryl. The more pain, the better. You need to make me cry; my bottom must be so red I can't sit."

There was still no movement, and she felt she needed to add something. "If you don't believe me, feel my pussy. It is so wet, now," she didn't want him to feel her pussy, but if she did not help Jo achieve his aim, she would disappoint him, and that was not something she wanted.

Fingers pushed into her pussy; it was wet, as it had been since the moment Jo had said the word, "punished," a few hours ago. They did not stay long, but it appeared to convince him, because another swish happened, hitting the tops of her legs. She was still crying out, as another landed almost on top of the first. She was now leaning heavily on the bed, needing it to cope with the pain.

Again, the swish came, and then again. The burning inside her arse was now the lesser pain; her cheeks felt like she had sat on hot coals. As three more strokes landed, and she sobbed, she felt breath on her neck, and in her ear Jo whispered, "Is it humiliating to have a bellboy spank you? Is your arse on fire? That is a tiny amount of pain compared to what you will experience this weekend."

"Yes, Sir," she whispered, between sobs. More swishes, and they started to cross the ones that were already there. It was beyond discomfort now, and she was close to collapsing onto the bed. More than 20 strokes had landed. Then they stopped.

"Remove all of your clothes," came the instruction. Tamra slipped her shoulders out of her dress and let it fall to the ground, then removed her bra, spinning it around and unclipping it. She finally stepped out of her shoes, and stood beside the clothes, naked.

She felt Jo beside her, and he said, "Turn around and sit on the bed slowly."

Tamra complied, and as she sat, Jo right beside her, she felt the most unpleasant feeling. She was sitting on something very rough; it seemed to bite into every welt. She dare not move more than she had to, to steady herself into a stable position. Sitting on the bed, whatever she was on moved, and she guessed she was possibly sitting on course sandpaper. It was so unpleasant, and new, she had never had that before.

The new punishment made her horny, she wanted to be played with, to cum. Something new always excited her more than anything else: new pain, new humiliation. That made her cum so quickly. However, that was not to be yet. "Tamra, Darryl is about to present you with his cock. Make sure he is appreciated for punishing you so well."

"Yes, Sir," she replied, as she reached out and found Darryl in front of her. At arm height she found his rock-hard cock sticking out of his trousers. It was not that long--six inches as a guess--but it had a reasonable girth. She slowly ran her hands up and down the length, as he moved closer. She bent her head and moved it to the cock. Without sight it was not perfect, but she took him into her mouth. Eager to please, she slipped her lips down his shaft, and touched the base into her hand, her hand and mouth working together, her tongue playing with the head as she started to suck and then move up and down on the cock. Tamra let her tongue play with the head of her cock, flicking it, making it flinch and bounce in her mouth, tossing the base hard. She could tell that the bellboy was not that old and not going to last long.

Jo could clearly see what she was feeling that the lad was not going to hold back for long, and said, "When he cums, you drink it all down, not a drop spilled."

Darryl moaned, "Oh god," the thought of her swallowing his cum making him rush headlong towards his climax. Tamra took his cock deep and to the side as the jet of cum sprayed, hitting the back of her cheek and slipping down her throat. She controlled the flow, swallowing several times to stop cum from leaking from her mouth. Darryl pulled away, clearly done.

"Now move back and lay on that bed. Just wait for me to see Darryl out, then I might let you cum." Jo's instruction was firm.

Tamra complied; it was nice to remove the welts from the sandpaper, but she guessed that was the start of a weekend that would be filled with pain and humiliation that she had never considered before. The door opened, then moments later closed, she heard Jo coming back, and he removed the glasses, then the tape. Carefully and slowly, she opened her eyes for the first time in almost 2 hours.

In a blurry mess, light flooded into her eyes, see could make out the shape of Jo, but everything else was lost in a blur. She blinked and rubbed her eyes, and slowly the room came into focus. It was massive, with big windows looking out onto a private snow-covered balcony, beyond which there was open space, which she guessed was the park that was mentioned at reception.

She blinked a few more times and tried to focus back in the room. Jo had moved away from her and was taking things out of the bag. There was a load of things she had not seen before, mixed in with lots of stuff they had used to cause her the pain she loved before.

As she wondered at this massive room, and how Jo had paid for it, he reapproached, carrying the largest butt plug they owned, and the lube. That plug was a little too big, it always hurt, and it was very early in the weekend for it to come out; he must have some big plans. For a moment her mind raced with all the things he might have planned for her between now and Sunday afternoon, which caused massive flutters between her legs.

Without a word, Jo pushed open her legs and started to apply lube to her arse. As he did this with one hand, he started to play with her clit with the other. Her clit really didn't need that much encouragement; between being spanked and the ideas running through her head, she was already close, and she moaned loudly as his fingers danced on her body.

As she was starting to lose herself in the build of the orgasm, she felt his hand move away from her arse, and then the plug push against it. It was already ready after the one that was removed not five minutes ago, and the large plug started to slip in with ease. She was trying not to move her body, but the orgasm was rapidly overcoming her body. The plug going in reignited the burning from the pepper spray that had subsided.

"Oh god, I'm going to cum," Tamra moaned. As the pressure behind the plug increased, forcing it in, it was matched by force on her clit.

"Good girl, you get that nasty orgasm out," Jo said in a calm voice. Just as the plug made it fully in, she felt her arse relax around it. As her orgasm flooded out, she pushed into his hand. She moaned and shook, the pleasure of her release washing away pain and burning for a moment.

As the spasms started to die away, Jo moved to right beside her and whispered into her ear, "I have so much planned for you this weekend; the pain will be like nothing you have every experienced. And I have some things planned that will be far more humiliating than blowing a bell boy." There was a pause, then he continued, "If you make it through the weekend without using your safe word, I will be impressed. I know that those words are making you horny, that the idea of all that pain is overwhelming your thoughts. But that orgasm is your last until tomorrow night, you must not cum again until I instruct you that you can tomorrow."

"Yes, sir, I understand," Tamra said, not really caring. If what he said was true how was he going to punish her more if she did climax?

Like he had read her mind, he continued, "And I know in that clever mind of yours you have just thought about ignoring me. So, I have this, which will only be used if you cum before you are allowed too," he pulled out a very large dildo, that she did not recognise. It was a good 10 inches. "I have been stirring a pot of chopped and crushed chilli peppers with this for a week. If you cum, it goes up your cunt for 30 minutes. If you cum again, it goes up your arse for 30 minutes. You get the idea. I promise this will not be nice pain; it will be the worst thing you have ever experienced." Jo's voice was calm and clear.

"Yes, Sir," was all she said.

"Now, spread your legs as wide as you can," he said, picking up the tawse again.

Moments later, it fell hard on her pussy, stinging her lips and crushing her clit. Then again, the same. She grunted in pain, and practice and will stopped her from moving. By the fifth slap, she was yelping through gritted teeth, but didn't move. At ten, her vulva was burning and she was sure it was a deep scarlet. She had tears running down the sides of her face onto the bed as she coped with this torture.

Jo's fingers slipped into her pussy; it made the raw skin sting, but she was used to that. Jo tutted, and withdrew his fingers roughly. There was a second then the tawse slapped down again on her raw vulva, harder than before. Tamra shrieked; she did not recall ever being hit that hard.

"QUIET!" Jo said, loudly and firmly. "If you do that again a gag goes on."

Tamra was not sure she could take another hit like that without some noise, but within a moment she discovered that she could take it with a much quieter, but more forlorn, yelp of, "Owwwww!"

The punishment was rough and just kept coming. The burning of her vulva was starting to get overwhelming and, against her best efforts she started to move when struck, trying to protect her pussy from the next hit. She looked down; her lips were an angry red, felt like they were on fire, and definitely beyond anything she had experienced before.

She was not sure how many slaps she had taken when Jo forced his fingers into her pussy for a second time. She flinched. She could not stop herself; the pain of just being touched now too much to take.

"Arh, that is better," Jo smirked to himself.

"I have never hurt that much. Thank you, master." Tamra spoke softly and slowly, controlling the feelings that were flooding through and over her body.

Jo walked away for a moment then came back with her round brush. It was about 4 inches long, with hard plastic teeth all around the body to comb her hair. With no pause, he pulled her lips apart and pushed the brush in. Every tooth seemed to catch her sore lips as it forced up, and as soon as they were past that initial pain, they dug into the walls of her sensitive pussy. Jo forced it in until all the brushing part was inside her and her lips semi-closed around the handle.

"Like that?" Jo asked.

"Yes, sir," she replied, but the pain was preventing any real thought; she was just agreeing.

"Good," Jo said. "How about a little electrical play?"

"Yes, sir." Again, Tamra just agreed.

As Jo walked back to the case, he said, "On your hands and knees."

Tamra complied, being careful as she moved. Her pussy hurt with any movement, but a fast movement almost made her collapse on the bed. She would be feeling her pussy pain into the middle of next week, and he had barely started.

When he returned, crocodile clips with wires leading from them were placed on her nipples. She winced as he let them go, crushing her nipples, with the teeth biting into her.