Chapter 2 Zack’s Vacation Studies
Zack was a mess three days later. Thrilled with his opportunity to worship Jacqueline and learn from her. Spending many hours each day massaging and giving her cunnilingus. Having one or two meals with her each day. He was in love. But his penis and balls were killing him. Constantly trying to erect. Balls aching badly for release. He was used to cumming seven to ten times a day. It had been more than three days since his last release.
Jacqueline works as a Licensed Therapist in NYC. And she is a Doctor of Psychology. Her plan to ensnare him was simple. Be his hot, older, first, dominant lover. Train and use him for her pleasure. Deny him relief until he cheated on his chastity. She knew he was smart enough to figure something out. When he did break chastity, and was caught, her control would be complete.
Zack had hardly seen anything new of the Bahamas. That changed mid-morning. He was awoken from his disturbed sleep by James. Surprised it was almost ten. They got into a Jeep and picked up Jacqueline. A short drive brought them to a secluded cove on the water with just a narrow beach.
James handed Zack two beach recliners to carry. He took out a large basket and cooler. They setup where nobody could see them except from out on the water.
“Strip. Nobody will see us here.” Zack took off his shorts and shirt. Naked except for his cage. He looked around still worried about being seen.
“Young man we will not be seen here. But never do this anywhere else in the Bahamas. We do not have nude beaches or clothing optional clubs. Lay on your back behind Ms. Jacqueline’s chair.” James pointed and showed him. Zack ended up on his back with his head underneath the spot where she would sit. Facing away from the water.
James reached down and gently pulled Zack’s head between two of the canvas strips of the recliner’s slatted bottom. James pushed a small firm pillow under Zack’s shoulders and neck. Zack was now trapped looking up at the chair’s back. He knew what was coming but still felt nervous. And excited.
Jacqueline stepped over his head and the chair raising her skirt. He briefly saw her hairy pussy and her ass.
As she sat she said “Zachary this will be so much fun.” She settled and he was taking part of her weight right on his mouth. As trained he wet his lips and opened his mouth some, so her outer lips were just inside his lips. He remained passive. Licking kissing or sucking waited for her to instruct.
“Jacqueline here’s your juice and wine. Brought some Scones and Crumpets.”
“Pussy Boi gentle suck.” He started a slow steady suction. Pulling her lips in a little further then releasing them to retreat. Making sure they did not touch his teeth or tongue.
Jacqueline and James chatted away like old friends. Enjoying their drinks and breakfast snacks. Zack was totally ignored. He could not see Jacqueline smile and wink at James who nodded grinning. Zack tried to follow their conversation, but it was not easy. She squeezed his ears constantly with her thighs.
“Keep sucking like that with a light tongue now. Make her wet.” Zack concentrated softly pushing the tip of his tongue slowly up and down between her lips.
It had started as a very warm morning with a light breeze. But now just after eleven it was getting hot with no breeze. Zack was sweating profusely. From the excitement, exertion, and the heat from her body.
Jacqueline was drinking wine quite freely. Getting a little tipsy. Ecstatic she got to do this with James. They had been lovers on two of her previous visits. And had shared a threesome with a gorgeous girlfriend of his. But exposing herself to James, using a submissive pussy slave, especially outdoors, was thrilling.
“Orgasms now.” He sucked firmly and quickly while using the bottom of his tongue right on her clit. Orgasms flowed quickly. She swam in them. Took momentary looks at James through glazed half-closed eyes. James watched passively. But she did see his huge bulge.
Zack had practiced this in her room about ten times already. While she sat in a chair, or on the end of the bed, or laying back on the bed like a pillow queen. Her stream of orgasms had been around three to five minutes each time. But this morning it went on. He struggled, swallowing her juices, and with her sweat covering his face and ears. The more orgasms she had the more she put her weight on him. Breathing through his nose became very difficult. She seemed to not notice.
“Do not stop!” She leaned forward putting most of her weight on him. Pulled her skirt up so she could grab fists full of his hair. She rode his face and cut off his air. She was grunting now, truly out of control for the first time.
Finally she clenched his head as hard as her legs could. Letting out a long guttural moan. She looked straight at James who was now masturbating. Her last orgasm lasted almost thirty seconds. She finally sat back just as James spurted his cum onto the ground.
Zack gasped. He was dizzy from the lack of air. He pulled in some of her sweat coughing. He started to calm down then realized his dick hurt. It have been trying to get erect. His balls wanted to explode.
“James that was so lovely. Thank you for such a nice outdoor brunch. Let’s stay awhile before we go back.”
“Jacqueline I so enjoy our time together. Someday we need to do this in another country where we can play openly.”
“That is a good idea. We can set up something for next year. Maybe Mexico at one of the adults only resorts.” James was nodding and grinning at that. Zack was thinking, if they would do this here, how wild might they be in a place like that?
“Zachary its been five minutes.” He resumed the gentle suck. She had been teaching him about after orgasm oral. Gentle suck and swallowing the juices still left. He expected it to be maybe ten minutes, like the previous days.
Jacqueline and James resumed their chatting. Now more focused on their travels and experiences. Including a few stories about visiting adult beaches and sex clubs. Zack knew about those. But would never have visited any. Too scared. Now he was worried she would take him to one. He was stunned to be like this during sex, with James right there. But a beach with others walking by and watching would petrify him.
He drifted some. Zoned out just trying to relax and not overheat. Gently sucking away.
“Here Jacqueline give the boy some water.” She shifted lifting her weight off him pulling up her skirt again. Smiled down at him as she slowly poured the water right onto her bush. It ran down her pussy into his mouth. He drank it all. She loved the sight of this nice looking young man literally drinking her juices with water. He might turn out to be a great sex toy for some lucky woman.
“Do you need more Pussy Boi?” He blinked yes. James handed her another bottle. This time she spread it around some so her thighs got a nice shower. Zack followed the stream of water.
“Your reward for being a good little pussy licker is more practice. This time when we finish I want twenty minutes of constant orgasms.”
The scene was exactly repeated. At the end Zack was close to passing out again. Jacqueline collapsed exhausted.
James put things in the jeep and helped her to the front seat. Zack had trouble even standing. James guided him to the jeep too.
They dropped him at his room. He got the instruction to stay in. James would order him room service.
While Jacqueline shared a late dinner with a very nice older British couple, Zack’s package was delivered. The previous evening he had gone online and purchased a small ladies vibrator. He was desperate to ejaculate. Since he couldn’t jerk it he figured he could vibrate it to orgasm. Holding the vibrator to the cage. He had seen it once in a porno. Guy in the cage tied down. Woman held the vibrator on the cage until he came.
Midnight came and Zack already had ejaculated four times. The dick hurt like hell but he could still finish. Balls still ached. He waited a few minutes and then started again. After ten minutes he was getting close to coming. So engrossed he did not hear the card click the door open. Jacqueline led James in and they stood at the end of the bed. Zack looked like a deer in the headlights. Started crying. She just glared at him.
“Clean yourself up! Quickly!” He scrambled to the bathroom getting rid of the soiled towel then using a clean one to wash the cage and dick slit. He came back out and saw she was red faced. She pointed to a spot in the middle of the room. Signaled him to kneel. She slapped his face as hard as she could. He just looked down.
They sat down. He stayed kneeling and sobbing.
“What do you think James?”
“Lifetime wanker. And hand jobs from whores. He’ll never stop.”
“Too bad. He is a good oral sex machine. But no woman wants an addicted weenie pulling machine. Zachary do you have anything to say?”
He just stayed there crying. Both were smiling at each other. Jacqueline had set him up perfectly.
“Zachary you are going to live a long lonely miserable life. Every night and weekend spent masturbating to some porn. Even the desperate mentally ill women will not want to marry you. The prostitutes will just take your money and laugh their asses off. One hundred dollars for a two-minute hand job.” He wanted to lay down and curl up.
“Last chance.” He shook himself and looked up meekly.
“No more fun. No more nice lady helping you out. No more experienced gentleman trying to help you learn. We’ve wasted too much time already. Last chance is blind immediate obedience no matter what. Well?” Zack tried to straighten up.
“Yes Ms. Jacqueline.”
“What else!”
“Will follow your instructions blindly and immediately.”
“They are orders. Anything. What I say. When I say. You do.”
“Yes Ms. Jacqueline.”
“Be quiet tired of hearing your lies. Like the Ad says ‘Just do it!'” She glared at him and he shrank. She left quickly like she was very mad. Grinning once she got past him. James knew what to do.
James sent Zack into the bathroom to pee and bath. When Zack returned there were BDSM restraints at each corner of the bed. Some others were on the bed. Zack started to speak.
“Shut up pussy boi. Do not want to hear another word from you. Understood?” Zack nodded. James pushed him to stand facing the bed. Quickly his ankles were secured to the feet of the bed. A ball gag was strapped onto his mouth. Zack was shaking with fear.
“Bend over. Do not move. Do not make a sound.” James loudly pulled his leather belt off.
Whack. Zack’s ass felt like fire. He tried to stay quiet, but a grunt escaped.
“Noise. It doesn’t count.” James proceeded to whip his ass slowly, steadily, and hard. After several minutes Zack had gone limp.
“Until you leave for the airport you stay in here bound on the bed. Cage locked. Twice a day I will come let you out to use the bathroom. And have a quick meal. Day you leave will give you the cage keys. If I give Jacqueline a good report, she will agree to meet you once for an appointment at her office.” James left. Damn he would not see Jacqueline till after he returned to NYC.
Zack did not know what to think. But he had plenty of time to.
Jacqueline relished the last several full days of her stay. She arranged with the resort for James to have time off. They spent most of each day together. Traveling, enjoying the beach and ocean, and making love. She reveled in the thought of Zachary tied to his bed. No erections or orgasms, while they did.