Between a Cock and a Hard Place

Thanks for clicking on this story! This is a commission by anonymous. I hope you enjoy it. As always, if you have any questions or comments, please let me know. I love hearing feedback and ways I can improve.

******************

Part 1

James had been working as a waiter at Henderson's for about three years at this point. He started when he was still in college, but he kept working here after graduating. James was now 23 and was living on his own in a small apartment. He was single and was almost ready to give up on the prospects of a partner.

With his small stature and feminine physique, James attracted the attention of many men. He had the most perfect hourglass frame. From behind, he was often mistaken for a woman. His hips were wide and his ass was extremely plump. Occasionally, a guy would hit on him and ask for his number. In a few instances, a guy would get handsy and grab his ass. Almost every time, he would turn around they guy would immediately apologize and explain the misunderstanding. Sometimes, a guy would look him at his feminine facial features and continue to hit on him. Unfortunately, he wasn't gay and never really wanted to try it out. If he was, then he wouldn't be single anymore.

It wasn't that James was against penis or anything like that. He just wasn't attracted to men. His dream partner was a powerful futanari however. She would love him and treat him with respect. He always dreamed of being in a beautiful relationship with a much bigger woman than him. Which wasn't hard, seeing as he was only a mere 5'2. In his dreams, she would have control in the bedroom, but she was never too rough with him. Their sex would always be very passionate. This dreamed seemed unlikely however.

James lived in a city with some pretty harsh anti-futa legislation. The local government was always against futanari entering their society. Most of the lawmakers were old conservatives. They still had the belief that futanari were monsters who raped and pillaged at will. This was a common misconception however. Sure, futanari had more sex than any man could ever dream of. And obviously their semen was highly addictive and could take over anybody's mind. But, most futanari were just regular people trying to make ends meet. There are a few that are very dominant and use their massive cocks as tools for mind-control. But, there are also some crazy men out there too. So, it never made sense to James to cast out an entire population like that. It always seemed unjust and unfair to the hardworking futanari out there. For this reason, most futanari steered clear of the city, and unfortunately for James, never stepped foot in the restaurant. And with James' anxiety, he never really traveled alone. Unfortunately, he was almost always alone.

Henderson's was a nicer restaurant with some pricey food. It wasn't the fanciest place in the world, but it was a respectable establishment. It wasn't the type of restaurant that people would bring their kids to. Most people who would eat there were on a date or there for a business deal of some sort.

One night as they were winding down and almost ready to close, a woman walked in. She was an extremely tall, black woman with beautiful natural curly hair. Her hair was a nice caramel color that went well with her mocha skin. She was built like a weight lifter, but she had the facial features of a supermodel. Her suit appeared to be very expensive, and the cut accentuated her figure nicely. She was very curvy and had a beautiful shape. Normally, James would have been annoyed that someone walked in this late. However, she was so beautiful, James could only feel grateful that he would get to meet her. The hostess lead the woman to her table in James' section.

James walked over quickly, "Hello, my name is James, I'll be your server today. Can I get you something to drink to start with?" The entire time he was talking to her, James was completely enamored by her beauty.

"Hello Jamie!" The woman said while looking at the menu. "I'll start with a glass of your pinot noir. And I'll have the lobster. After you get my food, you will stay here while I eat. I need company and you will be mine."

James took her other to the kitchen and stood still for a second. "Did she just call me Jamie? Who the hell is this woman? She's demanding me around like a slave! I assume she meant that I will be her company, but the way she said it. It sounded so dominant and so different." James' mind was racing. She had completely occupied his entire thought process with only a few sentences. He could only think about her beauty and how she was acting.

James brought a bottle of wine and a glass back to the table. "Here you are ma'am." After pouring a glass, he handed the glass to the woman and picked up the bottle.

Before he could turn around and take the bottle back to the kitchen, her hand reached out and grabbed his ass. "Hey Jamie, leave the bottle here." She was so blunt and confident.

James turned around and placed the bottle on the table. He was blushing from how she was treating him. She was so dominant and almost seemed like she thought she owned the place. He wasn't used to getting hit on by women though. A tent was being pitched in his pants. It was embarrassing to face her with an erection forming while looking at her.

He could see her eyesight glance down at his growing bulge. "Ohh... your tiny, little prick is so adorable when stiff."

James' entire face went completely red and tears began to buildup. "I-ill, uh... I'll go and uh, check on your food, o-ok?" He was so flustered and confused about what was happening to him.

A smirk had formed on her face as he walked away. "You have the most perfect ass. With your cheeks and tiny penis, you would be a perfect bottom." James' walking hastened. "Hurry back Jamie! I'm not done with you yet!" She yelled to him.

In the back room there was some bottle of water for employees. James grabbed one and chugged it. He poured some on his hand and rubbed his face. He was burning up and was trying his hardest to cool off. "Why is she talking to me like this? It's humiliating to be talked to in that manner, especially in public. I've never met this woman before, and yet she's saying these things to me. Why?"

The order was eventually ready and James had to go back to this woman. He picked up the plate and made his way to her table. He had noticed that she had drank about two more glasses of wine.

He placed the plate in front of her and turned around. "I made myself perfectly clear earlier. You will stay here and keep me company while I eat, Jamie."

James reluctantly turned back to face her. He stood still with his hands behind his back and he was standing completely straight. "Yes ma'am." He managed to squeak out.

She pointed to the seat across from her with her fork. "Have a seat, we need to talk."

James looked around, hoping to see something that would make him have to leave. Unfortunately, the restaurant was completely empty. The chair rattled against the floor as he pulled it out. As he sat down, his face got red again. He fidgeted with his fingers and nails. He buried his head in his own lap and noticed that his erection was at full mast now. Something about how she was treating him was so odd. Humiliation was never one of James' kinks, but what she was doing to him was making him feel so horny.

"Look at me, Jamie." She demanded. For some reason, James did as he was told by this woman. "That's better. Now, I don't have much time tonight, so I'll make this quick." James looked down and saw that the lobster was almost gone. "I'm looking for someone to satisfy me, and I wasn't expecting to meet someone like you here. I'm just here for business for a few days, but I think you would be perfect for my needs. Now, I'll be back tomorrow and we'll talk more." She took a swig of her wine and swirled it around in her mouth. She spit it back into her glass and handed it to James. "Drink it."

James held the glass in his hands and was getting jittery. "I-I-I'm so-sorry. B-but I d-don't... uh, I can't uh..." He was stammering and stuttering so bad as she crossed her arms and raised her eyebrows. "I can't d-drink on the j-job, ma'am."

"I don't care. I told you to drink it, so do as I say. Drink it... NOW!" She put her hands on the table and scowled at him.

James jumped back in his seat and put the glass to his lips. He leaned back and downed the entire glass. It didn't taste really any different from regular wine. But it felt so incredibly wrong, yet so good.

She licked her lips like a predator. "Good girl. I'll see you tomorrow, my little Jamie."

She paid for her meal and handed the check to James. He took it back and put everything into the computer. He walked back and handed her the receipts. She took the pen and signed. She got up and walked out of Henderson's. James sat back down and looked at the receipt. On the tip line, all that she wrote was "NONE".

James slumped down in his chair as she left the building. He was in shock from the whole experience. He cleaned the table and helped close the restaurant for the night. After clocking out, he drove to his apartment. The whole time, all he could think about was that woman. She was so beautiful, she had such an alluring presence. Yet, she was so dominant and almost scary at times. He laid in his bed and his erection still was there. After a few minutes of jerking off to his usual futanari porn, he realized something. He didn't need the porn tonight. He turned it off and finished with just the thoughts of that woman. He came harder than he ever had, just from the thought of her. Then he remembered, she would be back tomorrow.

Part 2

James slept in and didn't have to be back into work until 3:00 pm. The whole time in his apartment, all he could think about was that woman. He never liked extremely dominant women. Obviously, if he was going to be with a futanari he would be the bottom. But he never really enjoyed being degraded and humiliated like that. For some reason, the way he was feeling towards her was unique. He had butterflies in his stomach as the time got closer to go back to work. All he could think about was her. Her beauty, her smell, her aura, the faint taste of her spit that he got. During his drive to Henderson's, he was just imagining her and how she would be today.

When he got to work they were swamped. The restaurant was absolutely packed. James was told to get to work immediately. The work never ended and it occupied his thoughts for the whole time. He didn't have time to think about anything else. The day was almost over and most of the other waiters had left and the restaurant was getting low on patrons.

Just then, in walked the same woman from last night. James had been so busy he had forgotten about her. Her hair was now braided into two long, thick braids that went to her shoulders. She was wearing a new, expensive suit.

James ran over to the hostess and got her attention. "Please, don't sit this woman in my section. I'm begging you."

"Why?" The hostess asked all confused at the situation.

James peeked around the wall to get a glimpse of the woman. "She was here yesterday and she was very weird to me and made me a bit uncomfortable"

The hostess begrudgingly agreed to help him out and walked over to her position. The woman and the hostess talked for a while. It appeared that the woman handed the hostess something and whispered something. The hostess lead the woman to James' section of the dining area. James was mortified by the sight.

The hostess walked over to him and reached into her pocket. "She demanded that you serve her. She handed me $200 and told me to make sure you two were given privacy." The hostess handed $100 to James. "I'm so sorry. I'll keep an eye out from the back if I can."

James walked over to the booth that she was sat in. It was in the far back corner on the dining area. He got over there and started shaking a little bit. It was so nerve-racking just looking at her. He reached for his notepad to take her order.

She raised her hand and stopped him from writing anything down. "I'm not ordering any food tonight, Jamie. Just grab me a bottle of rosier." She clapped her hands together. "Now, we've got matters to attend to tonight. So make it quick."

James rushed over to grab a bottle of the rosier she ordered. With the bottle in one hand and an empty glass in the other, he was ready to go back to her. After a deep breath and long exhale, he composed himself enough to talk to her again. When he got back to the table, he poured her a glass and left the bottle.

She pointed to a small portion of the booth next to her. "Sit down." She demanded.

There was barely enough room for him to fit. And she made no effort to move and give him more space. James complied with her orders and squeezed in next to her. He was touching her shoulder and was so close to her, he could smell her breath. Her body was so warm, almost inviting him to get closer. Her scent was so alluring, it was a magnificent odor that went straight to his brain. The mixture of her smell and the warmth sent signals down to his crotch. Again, he was fully erect around this woman. Her arm wrapped itself around his shoulders and felt like a warm blanket. She pulled him closer and his face was practically touching her enormous breast. His face got all warm and very red. James looked over to see the hostess, but she was on a phone call and had just walked away.

She took a drink of her wine and rubbed his shoulder a little. She put the drink down and reached for his dick. She squeezed and rubbed his package over his pants. "You have such an adorable little dick. You'll never be able to satisfy anyone with the oversized clit." His dick got harder from what she was saying mixed with how she was touching him. She leaned in close and whispered, "You like that, don't you? You like it when a woman overpowers you? You like that don't you, sissy?" She reached into his pants his stroked his penis with her index finger and thumb. "You love that my fingers are enough to get you off, don't you? Say it sissy. Say 'I'm a sissy and I love my mistress using my clit'."

James was getting incredibly hot and was breathing heavily. "I-I'm a sissy and, uh, I love it when my mis-mistress uses my dick." He whispered under his breath.

She sped up and could feel him getting close. She abruptly stopped jerking him off. Unfortunately, he wasn't able to hold back anymore. She had ruined his orgasm and he pathetic dribble of semen was smeared on his underwear. Tears were swelling in his eyes as he felt degraded and humiliated.

She dunked her fingers into her glass of wine and swirled it around a little. "I said you have a clit. That thing in you pants is clearly not a dick." She removed her finger from her wine and stuck it in James's mouth. "I'll show you a real dick."

She unzipped her pants and reached in. After fumbling around for a second, she revealed a girthy monster. It wasn't even hard, and it was at least ten inches. Easily five times bigger than his own. It was veiny and looked so menacing.

"Grab it." She ordered James to do.

James was still sucking on her finger like a newborn suckling at their mother's breast. He was in a trance by the sight of her cock. Never in his dreams did he think he would have ever met a real futa. It was amazing and felt like it wasn't real. He slowly reached his hand out towards her crotch. As he made contact with it, it twitched and pulsed. He wrapped his hand around the shaft and began to bask in the moment. The cock was so warm and thick. His hand couldn't even wrap around its entire girth. He squeezed it a little and it barely budged. It was firm and it wasn't even erect yet. It had the consistency of a flexing bicep. He was running his thumb along the large vein that stretched the length of her shaft.

She was getting a little excited by his touch and curiosity. "Give it a kiss, Jamie."

She pulled her finger out of his mouth with and audible "POP". His tongue was hanging out of his mouth and a sting of spittle landed on his chest. He mindlessly and slowly bent over to get close. The was heat coming off of her cock and was warming up his face. He planted a wet kiss right above where his hand was.

"Don't stop, sissy. Keep going."

James obliged and kept kissing more and more. He was traveling up towards her tip. His kisses were getting faster. When he reached the tip of her cock, he notices she was wet. Her dick-slit was leaking pre-cum and it was dripping down.

"Don't let any of it go to waste. Get a taste."

He put his lips right on her tip and his mouth was immediately covered in her jizz. James pulled back and looked up at the woman and licked his lips. The taste was intoxicating and it forced him to go in for another taste. He wrapped his lips around her and began to swirl his tongue around the head of her cock. It was heavenly, drinking her pre-cum and sucking on her cock.

Unexpectedly, she pulled his head off and made him sit up straight. "I knew you would be a cock-craving whore. But, I've got to get going now." She handed him a card and pushed him out of the booth. "I'll give you a week. If you don't call me in that time, deals off the table. Hope to hear from you soon, Jamie." She slapped another hundred dollar bill on the table for the wine.

She walked out the restaurant and never looked back at him. He was still in shock from the whole experience. He just came in his pants and sucked a cock at work. He looked at the card and it had a name on it. It read "Janelle Williams" and it said that she was some kind of a financial advisor. He looked at the number on the back and put the business card in his pocket. He clocked out for the night and went back to his apartment. Again, he jerked off to the thought of this woman. He was remembering her taste and smell. That alone was enough to make him cum. He went to sleep with her occupying his entire brain.

Part 3

The next morning after he had woke up and showered. James sat around and lazed about for the day. He was fortunate enough to have the next two days off from work. During the day he was playing video games, watching t.v., listening to music and not doing much of anything. The whole time he was thinking about making the call. He fidgeted with the card from time to time. He kept looking at her name and number.

The situations kept playing in his head. "What if I call and it was all a prank? What if this is all another one of her humiliation tactics? Is this the kind of woman I'm really looking for?" James' anxiety was going into overdrive and tearing him apart. His mind was firing too fast for him to handle.

The rest of the day was spent contemplating whether or not he should call. He was pacing back and forth in his apartment.

Eventually, he said to himself, "When is an opportunity like this ever going to happen again. If it doesn't work out, then I leave and forget it ever happened." He picked up the card and his phone and dialed the number.

The phone was ringing for a few moments when someone finally answered. "Hello, how can I help you?" A chipper young woman's voice said.

"Hel-hello, I was told to get into contact with a Janelle Williams." He wasn't sure what he was supposed to say exactly.

"Oh, you must be Jamie. I was told to set a time and date for a meeting between you two." It was very uncomfortable knowing that she knew his "nickname" was Jamie. "So, does tomorrow at 1:00 pm work for you?"

"Uh, sure. This might sound stupid, but where exactly do I have to go?" James asked.

The woman was clacking on her computer to update the schedule. "So, what I'll do is send you a quick text with the address. Does that work for you?"

"Yeah, that would be great. Thank you so much."

"No problem. Can't wait to see you tomorrow, cutie. I've heard so much about you already. Well, bye." And she hung up the phone.