Skinny Dipping Ch. 02

"Best, be careful, Beverly; he has a hairline trigger," Cybil said, snickering.

"What am I spanking him for?" Beverly asked.

"He can't seem to avoid touching himself. Even though I ordered him not to masturbate until I saw him," Cybil said.

"A good spanking will make him compliant," Beverly said as she squeezed his wood between her legs painfully.

"I hope, so I hate chastity devices," Cybil said. Jeffrey was about to ejaculate from the pressure, but Beverly squeezed the intersection between his cock and his balls painfully just before he could. The deft pressure closed off the semen in his balls, and he immediately stopped.

"Did anyone say you could cum, Slaveboy?" Beverly asked.

"No, Miss," Jeffrey said.

"You are lucky Beverly stopped you; I would have made you clean the couch with your tongue," Cybil said.

"I like to spank the balls occasionally. Jeffrey spread your legs wider," Beverly said.

Jeffrey spread his legs farther as Beverly slapped his ass. Jeffrey felt humiliated yet turned on by his predicament as moisture from his constant excited state seeped from his urethra. Cybil moved to the couch to get a better view of Jeffrey's ass and privates. Cybil changing her position to get a better look at his privates caused Jeffrey even more shame. Angela had switched her SLR to video and was now recording the action as her vibrating egg edged her closer to release.

"Look at his tight little rosebud," Cybil said.

Jeffrey remembering Cybil's finger had just violated him there, felt deliciously exposed as more humiliation washed through his senses.

"Count the strokes Jeffrey," Beverly said.

"One," Jeffrey said.

Smack!

"Swat his nuts, Cybil. Let him know his place," Beverly said.

Cybil struck his balls. The sight caused Angela to go over the edge as she screamed quietly as her body quivered. She accidentally turned off the video recorder and took a burst of rapid photos as her finger inadvertently held the shutter button.

"Two," Jeffrey grimaced.

"No, that does not count," Beverly said. Says who? Jeffrey thought as he still felt pain.

Angela recovered from her orgasm and resumed video recording, and this time she did not keep her hand near the buttons. Angela lazily teased her sex as she breathlessly continued to watch.

Beverly spanked his bottom again. "Two," Jeffrey repeated.

Another smack on his ass. "Three," Jeffrey cried out.

Thirty blows later, she let him up. Jeffrey sat on the floor and took a sip. The beverage was delicious, but he could not recognize the flavor. The unwitting boy took another drink. Cybil and Beverly waited as he drank the liquid.

"I would rather stay, but I have to go. Nice spanking you, Jeffrey," Beverly said.

"Goodbye, Miss," Jeffrey said.

"See you later, Beverley," Cybil said.

Beverly left after kissing Cybil on the cheek. Cybil was glad to see her go; she wanted Jeffrey to herself.

"Finish your drink and go get the box from the spare room. First door to the right down the hall," Cybil said.

Jeffery downed the remainder of his drink and stood up. He walked down the hall and into the guest room, and as the lad reached for the cardboard box as he felt faint. The nineteen-year-old suddenly passed out, landing on the bed next to the mystery package. He woke up two hours later, restrained to the bedposts. Each of his limbs was stretched to a corner post, leaving him spread helplessly upon the bed. This room was on the opposite side of Angela's house, so she could not spy on this action.

"Good, you are awake. Beverly had to go, so now you are mine alone," Cybil said.

Cybil stood over him, tapping a riding crop against her leg. She wore an underbust corset and thigh high stockings, but nothing else other than a leather choker with a gold cast druid rune adorning it. The underbust corset displayed her large breasts to full effect, and her sex was clean-shaven. Jeffrey had never seen a beautiful woman nude before, and Cybil was exceptionally gorgeous. Her gym, hardened body was terrific. Her breasts stood straight out without a hint of sag, even though they were quite large. Several black candles were burning around the room.

"Why am I tied up, Mistress?" Jeffrey asked, fear invading his voice.

"I like it this way. Do you like being helpless for me, Slaveboy?" Cybil asked.

"Yes, but why do you have the whip, Mistress?" Jeffrey answered.

"I did say your training would begin, right," Cybil said, tapping the equestrian training implement against her palm menacingly.

"Yes, Mistress," Jeffrey said.

"Good, do you notice anything different about yourself?" Cybil asked.

Jeffrey looked at his hard-on, and it was longer than it had ever been. His dick was now two thirds longer. His cock was now porn star material.

"Do you like it, Slaveboy?" Cybil asked.

"How did it happen?" Jeffrey said.

Cybil struck his chest with the crop.

"You forgot to say, Mistress," Cybil said.

"Sorry, Mistress," Jeffrey said. She hit his right nipple, causing him pain.

She smacked the other nipple and then his balls with the crop. He cried out in pain.

"The Elixir you drank has two remarkable effects. One is your penis increase; the other is you will never grow body hair again," Cybil said.

She struck his sack again, and a whimper escaped his mouth once more.

"Silence, Slave, if you can't take this quietly, I will have to continue until you do," Cybil said.

Cybil swatted both nipples and his sack again, and this time he remained silent. Oddly, Jeffrey felt intense excitement from the pain. Cybil could tell what was up, and she thrashed his nuts again. He did not even whimper, but he regretted it immediately as she stopped torturing him. Jeffrey needed her to hit him again.

"Do not worry; I will have plenty of occasions to administer the pain you crave. I like to cause pain," Cybil said as her lip curled. Cybil knew his wishes before he realized them himself.

She slapped the crop on both nipples and his balls again. Toying with him, she waited until he relaxed before hitting his scrotum once more. The suddenness of it caused him to cry out. She quickly hit him with the equestrian whip, and he managed to remain silent.

"Good job, Slaveboy. Now we will play a game. But first, I will have to open my Amazon shipment," Cybil asked.

Cybil opened the mystery box, and out from within came a variety of sex toys. She unpackaged them one by one and held them up for Jeffrey to see. There were a variety of whips and paddles, plus several anal toys. One of which was a menacing-looking deep purple anal plug devise. She also had purchased other intrusive and pain threatening devices, most of which were far out of the naïve lad's comfort zone. She did not tell him that most of the items were Beverly's order because she wanted the Slaveboy on edge.

"Do you see these fun items, Slaveboy?" Cybil asked.

"Yes, Mistress," Jeffrey said.

She placed the items one by one on the guest dresser top. She left several things in their package. Finally, she held the purple anal plug up for Jeffrey to see.

"Do you know where I want to shove that device?" Cybil asked, smiling lusciously. Cybil had purchased the items through amazon and was thankful for how discreetly they were delivered. Redding was a small and talkative town.

"Yes, Mistress," Jeffrey said.

"Do you want me to shove this thing into your ass, Slaveboy?" Cybil asked.

"No, Mistress," Jeffrey said, fear breaking through his voice.

"Good, that will make this game more fun. I am going to sit on your face, and you will lick my pussy. If you can give me an orgasm in under three minutes, I will ride your cock until you come. If you fail, I get to shove that monster in your virgin ass," Cybil said.

She climbed on the bed and straddled his face. Jeffrey had never licked a woman's sex before. Although she was insanely excited, Cybil knew he had no chance of bringing her off in time. Jeffrey licked her urgently for three minutes. He licked her labia and tongued deep into her hole, but the inexperienced and foolish lad did not lick her clitoris at all.

"Time is up, Slaveboy," Cybil said.

She climbed down from the bed and grasped the purple anal intrusion device. She waved it slowly in front of Jeffrey's face.

"This monster will stretch you, good Slaveboy," Cybil said threateningly.

"Please don't, Mistress," Jeffrey said.

"How do you know you don't like it until you try it?" Cybil asked, leering at him knowingly.

"I don't think I will, Mistress," Jeffrey said.

"You like pain, don't you, Slaveboy?" Cybil asked.

"Yes, Mistress," Jeffrey said.

"I will lube it up good and go slow. If you are a good boy and do not cry out, I will give you another chance to earn your first time," I said.

Cybil untied one leg and retied it to the head bedpost, and then she did the same to the other leg. Now his legs fastened in an "u," his private region exposed, Jeffrey's anus was subject to Cybil's terror-inspiring plan. She lubed the anal plug and slowly rubbed it against his tightly clenched opening. She used her finger to open it up a bit as his sphincter clamped down on her finger.

"Relax, I know you will enjoy this," Cybil said, chuckling.

She wiggled her finger around in his opening and added another.

"Are you sure, Mistress?" Jeffrey asked.

"Yes, most Slaves enjoy prostate stimulation," Cybil said.

Cybil began slowly spinning the tip into his orifice. Turning it, she forced it slowly up his rectum. Jeffrey found the pain intoxicating but did try to hide his reaction from Cybil.

"I have never done this before; it is fascinating," Cybil thought. Jeffrey sucked air into his lungs as his tight hole slowly opened. Fascination evident on her face, Cybil enjoyed his discomfort; she inserted the anal toy agonizingly slow. Jeffrey could feel the device inching in as it approached the most extensive section. His sphincter strained open by her forceful intrusion, as an intoxicating pain enveloped his senses. Jeffrey endured the pain increase until it finally went past the most bulbous part, and his opening relaxed around the narrow shaft. His penis was dripping fluid in his unabashed excitement. The pain slowly lessened as his rectum contracted.

"That wasn't so bad, now was it?" Cybil said.

"It hurt a lot," Jeffrey said.

"But now it feels good, doesn't it?" Cybil asked.

"It doesn't hurt anymore, "Jeffrey said.

"It will on the way out," Cybil said as she had experimented with one on herself earlier.

"You like the pain. Tell the truth that is true, right?" Cybil said.

"Yes, Mistress," Jeffrey said.

Cybil showed Jeffrey the next toy, a huge strap-on dildo, still in its packaging. She wagged the veined 12-inch penis replica in front of his nose; even through the packaging, it inspired fear in him.

"Now the next inning of our game. I will let you lick me again, and if you can make me cum within four minutes, I will ride your cock. If you fail, I will screw your ass. That violation will hurt even more than the last toy. Now, do you want me to coach you as you lick?" Cybil asked.

"Yes, Mistress," Jeffrey said.

"It will cost you," Cybil said.

"What will it cost, Mistress," Jeffrey said.

"I will tell you later, but the penalty will be severe if you fail," Cybil said.

"If I fail?" Jeffrey repeated, his voice less than confident.

Cybil climbed back onto his face, and she reached behind her to caress Jeffreys balls. Jeffrey began to lick again.

"Now, for the coaching method, it is like the game hot and cold. If I like what you are doing, I will caress your boys. If I do not like it, I will smack them," Cybil said.

Cybil let Jeffrey lick her labia for a minute and then smacked his sack.

"One minute is gone, Jeffrey," Cybil said.

He began to tongue her hole, stabbing in and out of it. Soon she smacked his balls again. Jeffrey licked up from the cervical opening and accidentally licked the hood of her clitoris. She caressed his boys. He licked her pearl harder, and she began to buck on his face, but a full three minutes had already passed.

"You only have one minute left," Cybil said.

He licked furiously, and she climaxed just under four minutes. She untied his legs and climbed on his erection. He could feel the circulation slowly returning to his legs. She lowered herself down upon him, enjoying how he stretched her wet sex. She had never had a cock this big in her before, and Jeffrey gasped as the velvet envelope engulfed his sensitive shaft. Her moist sheath felt better than anything he had experienced around his swollen shaft. He let out an unrestrained moan.

"If you cum without permission, I will make you lick your cum out of me," Cybil said.

She began moving her sex up and down on his cock, knowing full well he had no chance of controlling himself. Up and down, she rode as his body stiffened. The butt-plug was now pressed against his prostate at the bottom of each cycle.

"I can't hold out," Jeffrey admitted.

"You best, or I will punish you," Cybil said.

Jeffrey tried desperately not to climax, but he had never felt anything so stimulating before. The sensations on his penis were fantastic, and the prostrate stimulus added another level of exquisite pleasure. He plummeted beyond control, and his penis ejaculated. Jet after jet saturated her inner folds.

"I warned you not to cum, didn't I?" Cybil said.

"Yes, Mistress. I am sorry," Jeffrey said.

"Now for the best part," Cybil said as she cupped her hand over her dripping sex and moved back over his face.

"As you penance, clean it out, good slave or I might still violate that tight ass of yours with Beverly's toy," Cybil said.

Jeffrey reluctantly did as she wanted and licked the repulsive liquid out of her semen moistened folds. He was surprised that it tasted less disgusting than he had imagined. She moaned as he licked her out. The mischief of it soon had Jeffrey fully erect once more. He licked her clit again, wanting to please her. Cybil, thrilled by the sense of power and the sensations, climaxed again. She shuddered, her nervous system overloaded with delight, and when she was back in control, she noticed his erect penis.

"Good, you are ready again," Cybil said.

She moved back onto his shaft and lowered her pussy onto him. He had to pee but welcomed the sensations anyway. She rode him violently, wanting to climax before him. Cybil looked out the bedroom window to see Angela, now dressed in a pale blue shift, taking pictures of them through the window from the yard. The thin sack-like covering looked more like a beach coverup than a dress, and it barely covered Angela's bottom. Cybil was too busy to worry about that now; she would have to deal with it later. Angela's parents were away, and Cybil already had a plan.

"I won't be giving you permission to cum; I like you licking it out too much," Cybil said.

She shuddered just as he ejaculated once more. She quickly moved her semen soiled sex back onto his waiting mouth. Jeffrey did not hesitate to lick this time, as he wanted to please Cybil desperately. He licked this smaller load up quickly and licked her pearl again. She climaxed. Cybil could hear Angela's camera shutter clicking away.

"What time does your mother get home?" Cybil asked.

"Four o'clock, Mistress," Jeffrey said.

"We better take a shower then; it is three," Cybil said. She untied him and led him into the bathroom.

Once in the shower, she kissed him for the first time. She forced her tongue into his mouth, and he willingly accepted it. She made out with him as they washed one another. She was in control. She stopped kissing him long enough to remove the plug from his anus. The removal of the device hurt as Cybil had foretold. She washed it off and set it on the edge of the tub.

"We will play with this later. I have two weeks off. My friends and I could only afford the houseboat for next week, so I expect you to come here every day for training. Tonight, you will tell your mother you have a date; then you will take me to dinner. Pick me up at six-thirty," Cybil said.

Jeffrey went home, confused by the events of the day. He entered his mother's piteously clean house and contemplated the recent acts in which he had engaged. The youth had no idea why he reacted as he did, but he was thrilled to be a virgin no longer. He waited for his mother's return and thought about what details he should tell her. Jeffrey kept few secrets from his mother, as she and he were close, especially after his father's passing.

When she arrived, he spoke to his mother and asked permission to go out that evening, even though it was only a courtesy. Jeffrey was a nineteen-year-old man and could do as he pleased. Constance Nixon never would tell him, no, but she was still an influence. He always did as she wished out of deep respect. Jeffrey told his mother about Cybil and how he had met her while at the river days earlier. He informed her that he thought she was in her early twenties but was unsure exactly how old she was.

"Is she a local girl?" Constance asked. Jeffrey's mother had grown up in Redding and moved to the bay area while married to his father. After divorce, she moved back to get childcare help from her mother; she knew most of the city's longtime citizens.

"I think so her mother lives here in town as well," Jeffrey said.

"You said that her last name was Clark?" Constance asked.

"Yes, her mother's name is Beverly," Jeffrey said.

"I knew a Janet Clark; her parents owned a house on Tehama," Constance said.

"Cybil lives on Tehama," Jeffrey said.

"Probably, the same family," Constance said.

"I will most likely be late getting in, don't worry about me. I will call the second anything goes wrong if it does," Jeffrey informed his mother.

Later that Monday evening, Jeffrey changed into his only dress shirt and slacks, kissed his mother, and left his home. Jeffrey drove back to Cybil's house. Cybil was waiting for him in a green evening gown, and the dress complimented her green eyes perfectly. The thin straps and cut of the dress were such that Jeffrey could tell she was braless. The dress was Cybil's favorite because the silky material caressed her breasts as she moved.

"We are going to my stepmother's good friend Sharon's club," Cybil said.

She led Jeffrey to her car in the garage. Her vehicle was a low-slung Japanese two-door front-engine convertible, and the convertible top was open.

"Jeffrey, take off all your clothes, and I will lock them in the trunk," Cybil said.

You want me to ride naked in the car, Mistress," Jeffrey asked.

"Would you like a spanking first?" Cybil asked.

"No, Mistress," Jeffrey said.

It was only six-thirty in the evening, and it would be light for at least an hour, but Jeffrey did as Cybil wished. She opened the trunk waiting for Jeffrey to disrobe and place his clothing into the boot. Jeffrey reluctantly took off his shirt and folded it neatly. Cybil pinched his nipple harshly, "Hurry up; I don't have all night," Cybil said.

Jeffrey bent to remove his only dress leather shoes. Cybil took one of them from him. He released his belt and stepped out of his slacks next, as Cybil caressed his back teasingly. He slipped off his socks. Cybil spanked Jeffrey's backside with his shoe through his boxers," I said, hurry up."

Jeffrey was excited again as his boxers tented to reveal. Cybil set the shoe down and pulled his boxers off herself. She put them in the hamper next to the washer and dryer in the garage.

"You won't be needing these," Cybil said.

"My private parts will show through those thin slacks, Mistress," Jeffrey complained.

"I know, are you arguing with me?" Cybil asked, spanking his flanks suddenly with his shoe.

"No, Mistress," Jeffrey said.

She pushed him over into the trunk and swatted his bare bottom ten times with Jeffrey's shoe.