Choices 30

Tina was a pretty girl in her mid-twenties. She always caught guy's attention and she knew it, she enjoyed it. What she didn't enjoy was being ignored. When Tina set her sights on a man, she was accustomed to getting him. This wasn't the case with Robert and it was frustrating her to no end.

Robert was a handsome thirty-something that worked in the same office as Tina. Even though he was fit and handsome, Tina would have never noticed him had he noticed her. It started one morning when they shared the elevator on the way in. Robert kept his nose buried in his paper, never acknowledging Tina. He was polite, letting her off the elevator first but she noticed he wasn't even looking at her ass when she glanced back.

Tina promised her fellow women coworkers that Robert would be hers one day. Over the next few weeks Tina tried harder and harder to get Robert's attention. She tried talking to him but he would only politely answer whatever question she asked. She tried dropping something and bending over in front of him in a short, tight skirt but he didn't seem to pay attention. She pulled out the low cleavage trick when she would corner him in the hall or his office but still no reaction. Tina was beyond frustrated. She was mad. She started to dislike Robert. Even though Robert hadn't wronged her in anyway she wanted to punish him and humiliate him for making her feel insignificant.

She talked to their coworkers. Robert had been known to date women. He wasn't gay, apparently. He lived alone. Besides that, the only other thing she knew about him was that he liked the State college football team. He had their logo on just about everything he owned. Which was funny because she was a big Tech fan, State's biggest rival. It wasn't much but it was enough, Tina thought.

Tina did a lot of research and found out Tech was much better than State this year. Soon, Tina was wearing Tech's logo on everything. As the game between the two teams neared she started teasing Robert about how bad his team was going to lose. At first Robert took it in stride but it soon started to get to him. The week before the game Tina was merciless. Finally, when Robert felt he had to defend his team, Tina struck.

As Tina was walking by Robert, who was eating in the lunch room, she commented, "Do you think State will even score against Tech this weekend? They are so pathetic."

Usually Robert would just laugh it off but enough was enough. "Oh I think they will score enough."

Tina stopped and place her hands on the table so she could look Robert directly in the eye. "Enough?" She asked loud enough to get everyone's attention.

Robert, who was painfully shy, was feeling uncomfortable with everyone listening. "Yes, I think they will score enough to win."

Tina had to fight hard to suppress the grin that was trying to cross her face. "Really? Would you care to bet on that... a friendly little wager?" She said innocently.

"Sure." Robert said, hoping this would end all the attention, "how much?"

"Oh, money is no fun, lets make it interesting." Tina said. Then she paused as if she was thinking about what they could bet on. "I know, whoever loses has to wear one thing the other person picks."

Robert didn't like the sound of that. "No. I don't think so," he said as he shook his head.

"I see," Tina said, "you think I'm going to have you running around the office in a small thong with the Tech logo on it in front of all the ladies or something like that?" Everyone laughed when they heard this. Robert turned red. "Don't worry, if you did that, it would be your own choice. Whatever the loser has to wear can be worn with regular office attire. Will that ease your mind?"

Robert had an image of a stupid Tech hat or Tech sweatshirt. He could do that. "Fine," he said and shook Tina's hand to finalize the bet.

That weekend Tech beat State 37-3. Robert dreaded going to work to listen to Tina brag, more so than the stupid thing he was going to be forced to wear. Tina on the other hand couldn't wait for Monday morning to get here.

Robert wasn't surprised when Tina showed up in his office first thing in the morning. She approached his desk with a certain swagger and a big grin. "Ok Tina, you won what do I have to wear?" He asked.

Tina laughed, "not much, just this." She then placed a small metal tube on Robert's desk. It was shiny, had a ring, a tube and a small padlock.

Robert had no idea what it was. "What the hell is that?" he said as he backed away from his desk.

"That is a chastity tube," Tina said with glee. "You put the ring behind your balls and your little dick in the tube."

Robert protested, "I'm not wearing that! Hell no! I never agreed to wear that."

Tina knew her next few words would be crucial. "You agreed to wear one thing I picked. I pick that. I win, you have to wear it or are you going to welsh on your bet, like I would expect a loser State fan to do? Besides, you can wear your clothes over it. That was agreed upon." Tina paused to let Robert think. "I'll tell you what, I won't even tell anyone you have it on. To be honest I want you to wear it because it turns me on. It will be our secret."

Robert thought about it for a few minutes. His head was swimming. He couldn't welsh on a bet but he didn't want to wear that. He didn't care that it turned Tina on but if she wouldn't tell anyone, it wouldn't be too bad. "Do you promise not to tell?"

"I promise," she said.

With much hesitation Robert picked up the tube and headed to the bathroom. The tube was small and bent downward. Had Robert not been so shocked he might have had a harder time putting it on but his dick was very flaccid and small right then. It was snug but he managed to close it up. He had planned not to wear the lock at all but the only way the the tube would stay on was with the lock in place to keep it from falling off. So he placed the lock on but didn't shut it. He pulled his pants up and was relieved that the device wasn't noticeable through his pants.

When he came back to his office, Tina was waiting. His face was red with embarrassment. "Ok, it's on," he told her. "It's totally ridiculous!" he said to let her know he wasn't happy. "but a bet is a bet"

"Let me see it," Tina demanded. "That's the only way I can know you are wearing it."

"Fine," Robert hissed. "A quick peek should be enough."

As Robert started to undo his zipper Tina walked closer. When he pulled down his underwear Tina saw what she had expected. The lock was open. Quickly, before Robert could move she reached forward and snapped the lock shut. Robert looked down in shock. At first he tried to play it cool. "Alright, very funny Tina. Give me the key," Robert demanded.

"I don't have it here," Tina replied. "You will have to come by my house tonight if you want to get out." Then she left him alone in his office with his thoughts.

For about a hour Robert studied the chastity device. He came to realize that any attempt to get it off could lead to some serious damage to his genitals. "No," he thought "it's best to let Tina have her fun and get the key at her place." He didn't want to make her made at the office. Who knows who she would tell she had locked his dick up.

The rest of the day Tina took advantage of Robert's situation. She would call him to her office to bring her coffee, or supplies. At lunch she had him carry her tray, fetch her napkins and pay for her meal. She always asked but she knew Robert was too scared to say no.

At the end of the day Tina gave Robert the address to her apartment. She made him wait a few hours before she allowed him to come over. When he arrived Tina answered the door wearing a skin tight, short, black skirt with a sheer, see through white blouse and black bra. She had a glass of wine in her hand and waved Robert in with the other.

Robert had always thought Tina was hot but a little to outgoing for him. Because of his shyness he wouldn't even let himself consider dating someone so aggressive. Still, as he looked at her now, he couldn't stop from thinking about seeing her completely naked. He had to remind himself why he was there. "Tina, I honored the bet, now give me the key."

Tina smiled. "See Robert, the problem we have is that we never determined how long the loser would have to wear the item."

"No fair!" Robert yelled.

"Oh, I would lower my voice if I was in your situation, Robert." Tina shot back.

Robert was mad but couldn't think of anyway to make Tina give him the key. He could overpower her and see if she had it on her but what if she didn't? She could call the cops. After all, he had put it on himself. He didn't even know if it was in the apartment. The thought of going to a locksmith was too humiliating. "Tina, how long are you going to make me wear this?"

Tina hid her smile when she heard Robert acknowledge she was in control. "That's up to you Robert. Do what I say and it will be off soon enough. If you won't do what I want you to do, you will wear it longer. Your choice. You always have a choice, Robert. Remember that. To start with, I haven't gotten to see my prize yet, so lets start with you removing your clothes."

Robert turned bright red. He started to protest but knew eventually he would have to anyway for her to unlock it. He slowly stood up and started stripping. He expected Tina to turn her head but instead she took a seat very close to him. She stared at him while she sipped her wine. When he was completely naked he tried to cover his dick with his hands. "Come now Robert, no need for that," Tina said. "I can't see your little dick with your cock cage on, move your hands."

Robert did as he was told. He couldn't believe he was standing completely naked in front of Tina. To his surprise his dick started to get hard but before it could grow much it filled the chastity tube. When it did, it pulled the ring behind his balls forward, trying to make room. It didn't hurt but it was very uncomfortable. He couldn't get hard despite his dick wanting desperately to. He was almost glad to be wearing the tube to keep Tina from seeing his excitement, but Tina did notice and she was elated.

By this time Tina was out of wine. She told Robert to go to the kitchen to fetch her some more. When Robert returned with the wine she apologized for the kitchen being such a mess. "Would you mind going in there and cleaning it up?" She asked. "Of course you don't have to, your choice."

Robert was pissed but didn't want to make Tina mad. He slowly turned and headed to the kitchen. Tina turned her chair around and sat sipping her wine as naked Robert cleaned her kitchen. By the time he finished Robert was a little more comfortable being naked. Tina was ready to see just how far she could push him. "Robert, I spilled some wine on the floor, would you be a dear and get it up?" Robert grabbed a towel and bent down to scrub the floor. "No, Robert you need to really scrub it. Get on all fours so you can put some weight behind it." Tina instructed. Robert did as he was told even though this exposed Robert's ass and balls to Tina, fully. Tina enjoyed watching Robert's ass shake as he scrubbed her floor.

She was wearing a pair of five inch heels with pointed toes. She took the top of her foot and placed it between Robert's legs. Then she started rubbing the top of her shoe on Robert's balls. Robert froze. It felt so good but it was so embarrassing. His dick strained to get hard but couldn't. He was getting more and more frustrated. "Don't stop scrubbing, Robert. We don't want a stain." Tina reminded him. Robert went back to work. While rubbing his balls, Tina couldn't help noticing Robert's tight brown asshole. She took her pointed shoe and stuck the tip up to Robert's asshole. He jumped at first but tried to keep cleaning as if a hot sexy woman wasn't poking him in the ass with her shoe. Robert's dick was now dripping but still restrained from getting hard by the metal tube.

Tina was getting wet too. She had never had so much control over a man. She wondered how far she could take it. After she had basically toe fucked Robert in the ass for a few minutes with her shoe, she raised her five inch heel to his asshole and pressed down. Robert jumped forward. "Aww Robert, I thought you might enjoy that. I can see by the puddle on floor, from your dick leaking, you liked having my toe in your ass. Oh well, your choice." Tina stressed the word choice. Robert was completely mortified to have Tina suggest he liked something in his ass. Even further embarrassed that his dick was responding with such excitement. Robert leaned back to where Tina had left her heal dangling. He was a bit confused. Did he do it because he wanted to let her have her fun so she would remove his cock cage or because he was so horny and desperate for relief?

Tina was over the moon. A man had basically offered up his asshole to her for her to penetrate. How delicious. She took some wine and rubbed it on her heel for lubrication. She knew she had him. She thought back to all the times he had ignored her at work. "Well he isn't ignoring me now," she thought as she pushed an inch or two of her heel up Robert's ass. Robert winced as the heel entered his ass. She didn't go too deep fearing that the heel may actually cut him. Still she slowly moved it in and out. Robert tried to adjust to this new feeling. He soon forgot about the sexy woman, heel fucking him in the ass and lost himself in the feeling of his ass being penetrated.

"What are you doing?" he heard Tina laugh, snapping him back to reality.

"Nothing." Robert said back not understanding why Tina was laughing so hard.

Tina noticed when she had stopped moving her heel in and out, Robert began to rock slightly on her heel. He was actually fucking it himself. He had even made it go deeper than Tina had. "You dirty little pervert. You are fucking my shoe. I bet no one in the office would have guessed you like it in the ass," Tina teased.

Robert was even more humiliated at the thought of Tina telling anyone. "No, I...I... was just trying to do what you wanted, so you would unlock my dick," he pleaded.

"Hmmm, it didn't seem like that," Tina teased. "Why don't you turn around and show me how bad you want me to give you your dick back."

When Robert turned around, Tina had her legs spread wide open with her skirt pulled up. Her wet pussy was on full display. He crawled up between her legs and eagerly went to work. Although Robert's tongue felt incredible Tina didn't let him know it. She humiliated him by asking him if he knew what he was doing or was this the first pussy he had ever seen? She would constantly tell him different ways to lick her. He felt totally demoralized being given instructions like he wasn't any good at giving a woman pleasure. After Tina came, many times, she instructed Robert to lay on his back on the floor. "I guess eating pussy just isn't your thing," she told him as she got up. "Since you aren't a good pussy licker, I'm going to have to make you my little ass licker," Tina said as she lowered her ass over Robert's face.

Robert had never licked an asshole before and didn't want to now. At first he just sat there with his mouth an inch away from Tina's asshole. His nose could easily smell her ass, even with the juices of her pussy all over his face. While waiting for Robert to start licking, Tina started playing with Robert's balls and cock cage. Robert wanted to get hard and cum more than he had ever wanted to in his life. "So you aren't going to be my ass licker?" Tina asked. "That's ok, your choice." She said as she stopped playing with Robert's locked-up dick.

Robert was desperate to cum. Slowly, Robert stuck out his tongue and touched it to Tina's dark, brown, tight hole. In heaven, Tina started playing with his balls again. When Robert stopped licking, Tina stopped playing. Soon Tina had Robert not only licking her asshole but burying his tongue in it. Tina was amazed at how easy it had been to turn a big strong man into her ass licking fool. She was glowing.

After a few minutes of having Robert lick her ass, she shifted her hips back so he could lick her pussy some more. This put her wet asshole directly over Robert's nose. As she started cuming she sat down on Robert's face, giving him no choice but to fully smell her ass. When she was done she knew she owned him, completely.

She stood-up and pointed to a chair. Robert did as instructed and took his seat. "Now, let's talk about getting that thing off your dick."

"Thank you," Robert said in relief.

"Tomorrow, I want you to come to the office early. Strip down to just this while you are in the elevator," Tina held up a pair of thong red panties with the Tech logo on the front. "I'll be waiting inside for you. The key to you're cock cage will be in the supply closet on the other side of the office. All you have to do is go get it. As you walk by me I will tell you on what shelf."

"What the fuck?!" Robert yelled.

Tina gave him a stern look. This time with a lower voice he asked, "I have to wear this all night? You aren't going to let me cum?"

Tina smiled as she realized Robert was concentrating on his dick and not the task she had just given him. "How can you cum when you can't even get hard, poor baby." Tina said mockingly. Robert then pleaded with her for release but to no avail. Finally, she shoved his clothes into his arms, including the Tech panties and told him she need to go to sleep.

"Tina, I can't wear this thong in the office." he pleaded.

"Don't worry, Robert. Just come a hour before everyone else gets there. I'll already have the key in place." Tina told him. "But, as with everything else, it's your choice." This seem to put Robert a little more at ease. He got dressed and left.

When he got home his head was spinning from everything that had happened. He had never let another person dominate him so thoroughly. He desperately wanted to stoke his dick until he came but the metal tube around his dick kept him from feeling anything. Tina was even controlling when he could play with his own dick. He went to bed very frustrated.

The next morning he woke up in pain. His dick was trying to get erect while he slept but was denied by the tube. He took a shower, put on the red thong, got dressed and headed into work. Robert wanted this bet over with.

The office building was dead. It would be at least a hour before people started arriving. He boarded an elevator and quickly stripped down to the red thong with the Tech logo. He prayed the elevator wouldn't stop on another floor to pick up someone else. When it reached his floor, the doors opened to find Tina was standing right there but to his horror so was every woman that worked on their floor. Tina quickly reached in and grabbed his pile of clothes off of the floor. Then she held the button for the elevator, so the doors wouldn't close.

Robert froze. He just stood in the elevator giving all the women a clear view of him naked, in his red thong. It wasn't until Tina whispered, "the key is on the third shelf on the right," did Robert snap out of his nightmare trance. He took off out of the elevator as fast as he could. The women were all lined up in his path so he had to run the gauntlet to reach the closet. As he passed, several swatted and pinched his bare ass. They all howled with laughter at the ridiculous sight of Robert in his thong. As he reached the closet he could hear the women chanting, "Ti-na... Ti-na... Ti-na..." As he closed the door he caught a glimpse of them giving her high fives.

True to her word, the key was right where Tina said it would be. He even notice a pile of clothes sitting on the floor. He was relieved about that too. As he unlocked his cock cage, he realized that even though he had never been more humiliated in his life, he had also never been hornier. When he took the tube off his dick it sprang to life. It was as hard as it had ever been. He couldn't help but start to stroke it. As he did he realized that even though Tina had made him her little ass licker, the only thing the office staff knew was that he had paid off a stupid bet. Not really a big deal now that it was over. Soon, Robert became aware that he was about to cum. His hand started stroking his cock faster. Just before he shot his load the closet door was flung open. He was looking directly at Tina and all the other women. There was nothing he could do, he had no choice. His cum was just starting to spurt from his dick. He couldn't stop stroking it. As he climaxed all he saw were camera flashes. All he heard was laughter, but most of all he heard Tina laughing the loudest.