Pussy Boi

Zack was slender, six-foot tall, good looking, with a nice smile. Very smart he loved gaming and computers. A Masters in Electronic Engineering got him a high paying job in NYC. He didn't blink at the monthly $4,000+ studio apartment rental on West 23rd street in Manhattan.

Zack's most notable personality trait was his intense shyness. He was incapable of talking with any female, no matter the situation. His college mates made fun of him. A few tried to help him out, but it was fruitless. At 25 he had never been on a date. A virgin. His only sexual experience was on a solo vacation to the Bahamas after graduation. He found a high-end web site to arrange an escort. Each night for a week they met for dinner at local restaurants. He had trouble even looking at her. But she got him a little comfortable. He managed to do some simple chatting. Desperate for intercourse the best he could manage was hand jobs. Even with the escort's experience she could not get him to slow down. Just a few light strokes and he exploded. Despite having already masturbated several times earlier in the day. She had a great week at a thousand a night for under five minutes of hand jobs.

Zack's way to avoid women was to bury himself in work, gaming, and masturbating. He averaged fifty orgasms a week. Dreamed of a magical girl next door finding him and getting married. But he knew that would never happen.

The next year he went on a two-week vacation. Same spot in the Bahamas. Figured he would find an escort there.

He arrived in the afternoon and got settled. Went for dinner at the resort's outdoor beach facing restaurant. He drank his bottle of beer and was watching an older woman several tables away. They were the only singles at the moment. She was a very attractive slender 50ish lady. So lost was he that he did not pick up that she had noticed his interest.

She waved over the waiter. He returned with a new drink and a bottle of beer. Zack did notice that and thought 'oh she must be expecting a man'. The waiter stepped directly over to his table.

"Sir the lady would like you to join her." Zack was close to a full-blown anxiety attack. Started to mumble no thank you.

"Sir, that would be quite rude. She already has your beer. Let me introduce you." He picked up Zack's beer and led him over.

"Ms. Jacqueline please meet Mr. Zachary." Zack sat with his eyes firmly on the bottles of beer in front of him.

"Zachary you are very shy, aren't you?" He whispered yes.

"Yes what?"

"Yes Ma'am." She had a slight frown.

"You need to learn some manners and social skills. Perhaps I can help you with that. Try again and think how you were introduced to me."

"Uh yes Ms. Jacqueline." She smiled.

"Again, without the uh. And do not mumble. Look at me and say it loud enough for the tables near us to hear it."

"Yes Ms. Jacqueline." He had sort of blurted it, so people did notice. It sounded odd in tone.

"Better. How long are you here?"

"Two weeks."

"Good I am here for 10 more days. Have you arranged for an escort?" She was smiling. Zack was blushing.

"Not yet. No Ms. Jacqueline."

"If you do, you will never find a girlfriend or boyfriend. Let alone a permanent partner."

"I'm not gay." He was flustered. Confused.

"You are a virgin correct? With no real sexual experience. How would you know?"

"I only like girls."

"Virgin, yes?" He was tearing up.

Softly "Yes Ms. Jacqueline."

"Speak louder and clearly. Try again. What are you?"

"Ms. Jacqueline I am a virgin." So off kilter Zack did not notice a female couple eavesdropping on their conversation.

"You have no real idea of what you are. Experience is necessary. Did you do anything for your escort last time?"

"Uh I paid her?"

"Language. Did you please her sexually? With your fingers? Cunnilingus?"

"No Ms. Jacqueline."

"Did you ask her for that?"

"No."

"Selfish and ignorant. A woman, no matter her looks or station, deserves your respect. You treated her like a whore. If you want women to have real sex, offer them more than money. Serious relationship? Relate to her. Connect emotionally. Learn to please her." He nodded. By now he was really looking at her as she spoke. She knew she had him.

"Maybe I can teach you to relate to women better. But you are limited. Your level of shyness may not be overcome. Adjust your expectations. And the type of relationships you seek. Fall in love? Marry and have kids? Not unless you want to settle for some very desperate unattractive girl."

"Sex. Learn how to touch her sexually. Learn cunnilingus. Each woman is different. Experience will teach you the basics. Maybe you will start to understand and adjust to her reactions and desires. Listen. Her body and voice will tell you. Maybe with that you can find something for your life. Like a friend fuck buddy." He immediately thought she was interested in that.

Jacqueline leaned in. "You are hard right now. Just speaking to me. It is ok. But you have no control." He was squirming and eyes looking down again.

"Can't you control that thing?"

"No Ms. Jacqueline."

"A solution is needed for that."

"Do not think I can. No matter how much I jerk off I still get hard around women."

"That can be solved easily. It will require your willingness and trust."

The waiter, James, took their diner order then refreshed their drinks. Jacqueline did the ordering. Zack said nothing.

Over the meal she quizzed him about his family, schooling, and job. Clearly he was a loner, separated from his family. Few friends and none in NYC. Only thing he learned is that she lived and worked in NYC on the East side. That pleased him. Maybe 20-25 minutes from his apartment. His mind started wandering. Maybe she wanted him as her boy toy? He was rock hard again.

She stared at him knowingly "Your dick is running your brain. Time for you to go to bed."

"Ok Ms. Jacqueline. Can we ". She cut him off.

"We will meet here for brunch tomorrow at 11 AM. Now off with you." He stood and started to turn.

"Zachary masturbate all you want tonight." He went crimson.

Zack slept just a few hours. Jerked off constantly. Shaved and tried to look nice and normal. Really couldn't pull it off. He was a good-looking loner nerd. And people could see it.

He arrived five minutes early to brunch. Jacqueline was waiting for him. He went to sit down.

"Stop. Be a gentleman. Say good morning properly." Pointed at her side. He stepped over.

"Good morning Jacqueline."

"Too familiar try again."

"Good morning Ms. Jacqueline."

"Better but not a formal enough attitude for a classy lady."

"Good morning Ms. Jacqueline." He bowed a little and offered his hand. She lightly placed her hand in his.

"Good morning young Zachary." Said smiling while her fingers lightly stroked his palm. She was dressed in a tight spaghetti top and no bra. He stared at her smallish breasts with nipples pointing out. He was hard. She watched his eyes then glanced down a second while smirking.

"Please take a seat and hide that thing." He sat. Crimson faced again.

"You need to relax and accept yourself. You cannot hide being a horny little toad."

She ordered for them. He got plain eggs, water, and juice. No coffee. She tried out some simple small talk with him. He failed miserably as expected. Just sat there squirming in a horny daze.

She got a call. Ended it with "Thank you James. See you in twenty."

She signed the check then strode off quickly saying "Come on young man."

He followed. Her loose flowing skirt caught his attention. Tried seeing the outline of her ass as the skirt flowed in the breeze. Anybody who looked would see his obvious hard-on. He looked like a puppy following his mama.

She opened her room door then turned.

"Wait out here. James will arrive shortly." She backed up closing the door in his face.

He was flustered and confused. Why not go in with her? Why was the waiter coming? Several people walked by. Embarrassed he just stared at her door.

He jumped as a large hand firmly grasped his shoulder moving him to the side.

"Mr. Zachary lets go in." James tapped twice then opened the door. Zack followed him in.

Jacqueline was sitting at the small table in front of large windows looking out on the beach. James took the other chair. Zack looked around for a place to sit.

"Just stand here at the table with us." Awkwardly he did.

"Thanks for helping James. Zachary you have one chance. Your first thought will be to say no. Then you will want to question what we do. Make up your mind. I am ready to spend my vacation teaching you. And James is already helping. Do not waste our time."

He gulped and nodded. "I really want to learn thank you." She frowned. "Ms. Jacqueline." James was smiling at him. He relaxed.

"Take all your clothes off." He started to say no.

"Do it now or leave." He was blinking and tearing up. He stripped and folded his clothes.

"Put them over on the bureau." They watched him as he did. She thought 'he has a very nice tight little ass'.

"Stand right here next to the table. Let's have a look at your genitals." He was blushing all over. His penis and balls were just above the table between the two of them. Petrified he stayed limp.

She cupped her hand underneath, lightly lifting them up. He jumped at the first touch. But almost immediately it started to grow.

"What do you think James?"

"Quite small Jacqueline. Is that full now Zachary?"

"Uh yes James."

She sharply said "Language. Do not be familiar or discriminate."

"Yes sir."

"Maybe eleven or twelve centimeters Jacqueline. No woman I know would find it suitable for intercourse. Certainly not satisfying." She laughed and let go of it. Cleaned her hand with a disinfectant wipe.

"James the women you know are used to your 22 centimeters." He grinned a big wide smile.

"You do too Jacqueline." Zack was flustered. They were lovers?

"Zachary please know we are both quite experienced. Very few if any women, or men receiving anal, could be satisfied by such a small penis. But there are many other ways to satisfy partners and lovers. Problem is you hide at home masturbating when you should be out eating pussy and sucking cocks." He flinched.

"I'm not gay."

"No arguments. You've been told. No way to know till you try it. I had flings with women at university. Fun. But learned I was not into women. Now let's look at your present. The first step to self-control."

James reached into the small bag he brought. Placed a box in front of Jacqueline. She opened it while explaining.

"Your first chastity cage. It will control that unruly penis. No more inappropriate erections. Since I'm taking you on, I will be your first keyholder. It will be locked up 24x7. Of course, it will be released for cleanings. Perhaps the occasional fun too."

"Uh Ms. Jacqueline really do not know " she cut him off.

"Yes or no?"

James added "You are very impolite. She is doing you a huge favor little man." He hesitated a few seconds. Felt like an hour.

"Yes Ms. Jacqueline."

"Little man the lady just bought you a wonderful gift and is committing to helping you find a woman. What do you say?"

"Thank you, Ms. Jacqueline." She nodded toward James. Zack froze.

"James is helping you here right now."

"Thank you, sir."

"Look at him and say it sincerely."

He looked straight at James "Thank you sir for helping me."

James grinned "Welcome little man." Said as he reached out and tapped Zack's penis lightly. Zack jumped. They both laughed.

"Goodness young man if you jump like that when anybody touches it you will never get sex."

She pulled out the pieces. Picked a ring like thing and grabbed his dick with the other hand. His penis shot to an erection. She smiled.

"James please get the ice bucket." She bent his erection down into the icy water. He yelped. Quickly she slipped the base ring on. Dipped the head again. Attached the tube over the shaft and head. Zack was too nervous to recognize she had experience doing this.

"All snug. Maybe a tad big. We'll get you into a smaller one in New York." Zack did consume that statement. She did want a relationship with him. Not the one he wanted however.

James pulled out a smaller box. It contained a small padlock. She locked the chastity cage.

"Zachary I will control your little worm. This key is mine. James gets the second one. Just for an emergency." She went over to the closet and locked her key in the lockbox. No way Zack could get at it.

"James dear thank you. Here hold onto these for me please." She handed Zack's clothes to James. Kissed him lightly on the cheek and he departed. When the door clicked shut Zack relaxed a little.

He jumped as she stepped back behind him and firmly cupped his ass cheeks.

"Stand still!" She kneaded them a little and spread them for a second.

Letting go she sat back down facing him. "Place you dick cage on the table." He did.

Looked him straight in the eyes. "Every gay man I know would love to fuck that ass. Well, and a few ladies with strapons." His eyes bulged.

"Here are the rules. Next nine days you are mine one hundred percent. You do as you are told. Nothing less nothing more. Got it?"

"Yes Ms. Jacqueline."

"Good. We are training you to respect, support, and serve a real woman. Maybe then you can find something long term. But I warn you. Most women who want to completely control a man will tire of you after months or years. Once they do you will be replaced. The more you meet her wants, needs, and desires, the longer the relationship will last. If she banishes you, it is your fault."

She reached out to run her fingernails on the underside of his balls. He jumped again.

"You need to learn to control that too. When a woman touches you stay still. If you are lucky maybe she will make you feel good."

"Do you want to have sex with me?" Said as she cupped and fondled his balls. He stared tongue tied trying not to squirm. His dick pressed hard against the plastic cage.

"Is that a no?"

"Ms. Jacqueline I want to make love to you."

"Such an inexact term. What acts?"

"Uh.."

"Language!" said as she slapped up into his balls. Just enough to get his attention to the possibility of something painful.

"I want to have oral sex and intercourse with you." She chuckled.

"Intercourse? With that little dicklet? I think not. What kind of oral sex?"

"Cunnilingus and fellatio." He was smart enough to start adjusting his language. Just needed to stop his 'uhs'.

"Fellatio? Are you kidding? That is what women do for a man they love or are sexually thrilled by. You could only get that from a prostitute. We will train you to orally pleasure a woman. But it is NOT just cunnilingus. It is the whole body if she desires." She stared at him awaiting an answer.

"Yes Ms. Jacqueline. Want to learn to give women oral."

"You mean to say worship her body orally." He nodded.

"What do you expect in return?" He was stumped.

"In return the woman will own your sex. And if she is interested, perhaps she will run your whole life too. Wouldn't that be nice?"

"Yes Ms. Jacqueline." He shifted a little nervously. She felt his weight move still holding his balls.

"Ask your question. Do not stand there like a nervous little schoolboy."

"Ms. Jacqueline what sex will I get?"

"Giving a woman pleasure with your tongue, mouth, and hands is sex for you. Yes?"

"Yes Ms. Jacqueline."

"Her orgasms and satisfaction are pleasure for you." Again he was apprehensive. She started to squeeze the trapped balls.

"Ms. Jacqueline will I get any sexual relief?"

"Of course silly. Just on my terms. If we ever find you a lady friend, she will decide."

"What will it be for us?" She frowned.

"Accept that I am doing this all for you. Whatever you get be grateful for it. But you must earn it. Learn how to please me. I love long massages and full body oral worship. We will start there. Pay attention. Learn what I like. A lady should not have to ask." He nodded and tried to smile.

"Let's start. Kneel facing me. Take my slippers off." She put the bottom of her right foot and inch from his face.

"Kiss it. Ouch. Dry lips are not sexy. Wet your lips and try again." He did.

"Better now the other." This time she waited to make him lift her left foot to his face and kiss it.

"That is always the first thing you do for me. It shows me you will worship even the lowest spot on my body. Now take each foot in turn and gently lick between each set of toes." He had a slight frown.

"Do not be silly I bathed before breakfast." He slowly complied. It wasn't so bad. She seemed pleased.

"Now suck each toe. Ten seconds each." He complied.

She reached into the bag James had left and pulled out a pack of condoms. Zack was confused. She handed him one.

"Put that on over the cage. Do not want any of your leaking excretion anywhere." As soon as he had it on, she reached down and put a thick nylon hood over his head. Only his nose mouth and lips were exposed.

"That will keep you from seeing things that will excite you too much." His mind raced. His dick strained against the tube. He heard a little noise. Next thing he felt were her hands guiding his head up and forward.

"Kiss it." Thrilled it was her nipple.

"Now lick it slowly around the areola. Good now take it all inside your lips and gently suck." His excitement grew.

"Now the other." He repeated the same things.

"Sit up. Give me your hands." She took them and placed them under and around her breasts.

"Gently squeeze and lift them a little. Make them higher and firm." Slowly he softly kneaded them. She let out a small sigh.

"Stop." He heard her stand then the sounds of her finishing undressing. She pulled him to the bed. He could smell a little scent. Was it perfume? Or was that her juices? Zack had no idea.

It was awkward as she pulled him on top of her then she twisted so she was face down with him sitting on the back of her thighs.

"First lesson is body massage. This is nonsexual. You will do this for thirty to forty-five minutes each time. Every woman I've ever known loves this kind of massage."

For at least twenty minutes she instructed him what to do. Started with her naked buttocks. He felt like he was on the edge of cumming, despite being locked up. She had him slowly work up her back ending with her shoulders and neck.

"Not bad for a beginner. Now do the whole thing again." He did.

"Mmmmm now just sit there awhile while I nap." He stayed in place, but it was a tiring position sitting up like that. And keeping his weight off her.

She awoke shortly and pushed him back off the bed.

"Kneel." She sat above him on the end of the bed. Spread her legs wide. Pulled his face into her crotch. Nose pressed to her vaginal lips.

"Keep your mouth closed. Just breath with your nose. This is the scent you want. It owns you. All you need is for her to be wet and happy." His penis was dripping fluid into the condom. He felt her pubic hair. When he watched porn all the girls' pussies were clean. No hair. He was apprehensive about pubic hair.

"Cunnilingus. Each woman will be different. Stay alert to her words and body reactions. I will give you instructions. But no woman should have to teach you." He blindly nodded. She was grinning.

"First lick the crease between the thighs and lips." She guided him to the left. Then the right. Turned him straight on.

"Slowly lick the opening from the bottom to the top. Not too hard. Slowly. Several times. That's it." Her juices were now flowing onto his tongue. His brain was scrambled with excitement.

"Reach up and spread the lips with your thumbs. Press your tongue straight into her. Slowly start to make a circle with it. Reverse go the other way. Put your lips inside her lips and very lightly suck. Keep your tongue circling. Taste the juice. Drink it." He swallowed.