Training Rebecca Ch. 03

Story Info
Blackmail forces her to act the slut.
5.7k words
4.6
223.3k
34

Part 3 of the 11 part series

Updated 10/19/2022
Created 06/23/2005
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Part III (Saturday)

Rebecca Dunbar awoke early on Saturday morning. She did this without the alarm being set; it was just her routine and she didn't change it just because it was the weekend. She donned exercise attire and went downstairs. Upon entering the home gym, she saw a box sitting on the table. She went in search of Maria and found her in the laundry room.

"What's with the box in the gym?" she asked.

"It arrived yesterday with instructions to put it there. The deliveryman said you'd be expecting it."

She returned to the exercise room and opened the box. Inside was a note explaining that she was to wear the enclosed item while exercising, a minimum of half an hour a day. She pulled out the wrapped item and opened it. She turned it around and around. It was a strap with a leather phallus attached. She thought at first he was going to make her wear a dildo, but a card on the plastic wrap showed a picture of a girl with the strap around her head and the wide end where the phallus attached was at her mouth. This was too much. He had disrupted her life when he was with her, and the butt plug made her conscious of him even when he wasn't.

She made a decision, put it back in the box and started her routine. Maria knocked and entered a few minutes later with the phone and handed it to Rebecca who was pedaling the stationary bike.

"You have chosen to ignore me," the voice said when she picked up the phone.

"No, sir," she hastily replied. "I was just about to start my exercises," she lied, "and had just opened the box. Was it from you?"

The line went dead. Damn him, she thought as she handed the phone back to Maria and thanking her for bringing it. After her housekeeper had left, she went back to the box and retrieved the fake cock. The package called it a pecker gag. The leather made her mouth bulge as she inserted it. She pushed slowly until it hit the back of her mouth and she gagged. She looked and realized she still had a little farther to go past that point. She put it in again until it reached the gagging point. Then with a will she relaxed her mouth and throat muscles and pushed just a little. No gagging. Just a little more. She pushed the last little way and gagged again. The offending article was rejected as she hacked and coughed. She wanted to cry but refused to let herself. She sat down so she could concentrate. In again, she tilted her head up for easier entry, muscles forced to relax, and the last little push was made without gagging. She swallowed around it and found it quite uncomfortable. She thought about not buckling it, but he seemed to anticipate her every move, so she buckled it behind her head. It wasn't long enough to block her breathing but breathing through her mouth was out of the question.

Rebecca slowly and carefully moved back to the exercise bike and mounted. The rest of her exercising was done at a measured pace. She couldn't get to the point where she was breathing hard and she didn't want to start gagging around the "Pecker gag" since it was buckled on. By the end, her throat muscles seemed to be relaxed around it and she unbuckled it and took it off. Her mouth was very dry and she took a drink from her water bottle before stowing her new "toy" in the back of the cabinet.

She went up to the master bath where she looked at the clock and took out the butt plug. It felt heavy and she could feel something metal inside the rubber. After a few moments, it gave off a beep. She sat on the toilet and took a shower. It felt funny soaping her hairless pussy, but it was also erotic she agreed reluctantly. She finished and dried before her 30 minutes was up and reinserted the plug, which soon beeped. The entire focus of everything he made her do was aimed at stirring her sexuality. And despite her best efforts to the contrary, her body was betraying her.

She dressed in sloppy clothes for ramming around the house, and spent a while piddling about the home office. The boys came in to say they were going out to an amusement part with Maria. Rebecca usually took them out someplace on Saturday, but she didn't want to go in a skirt without panties, and she didn't know when Kyle would call again. After they left she changed into a bikini that set off her curves and went out back to lay in the sun by the pool.

The phone rang about 2:00 and she went inside to get it.

"Good afternoon," said a familiar voice.

"Good afternoon, Sir."

"Are you spending a pleasant day at home?"

"Yes, thank you Sir." The small talk was getting on her nerves. She been expecting his call all day and wanted to at least know what he had planned for her.

"Come to my house tonight at 8:00."

"Yes, Sir."

"And Rebecca?"

"Yes, Sir?"

"Bring a mouthful of cum."

The line went dead before she could respond. Why was he doing this to her? She saw red for a minute, the phone still at her ear. Her fingers clutched at the receiver, wanting to scream at the top of her voice. He was arrogant, barbaric, with no thought for her wellbeing. He disregarded every convention of civilized society. Then, without making a conscious decision, her brain started working to figure out how she could accomplish this task. It is 2:00 now. She would have to find someplace with men in it early. It would be light at 7:30, so it would be hard to find a place outside. The next few hours should have been peaceful ones at home, but he had disrupted her life again as she considered the problems she would face this evening and their potential solutions.

At 6:00 she dressed in her shortest and tightest skirt, which covered the obligatory garters and stockings. She chose a push-up bra and tight, low-cut sweater to accentuate her curves. Her hair, she let down and left a bit wild. Then she finished off by adding bright red lipstick and her highest heels. Who is this woman, she asked herself when she looked in the mirror?

At 6:30 she left the house. Maria's raised eyebrows were her unspoken comment. Rebecca drove to a middle-class bar and grille and parked. The bar wasn't very crowded and she ordered a drink and looked around. There were only a couple of possibilities she thought as she eyed a balding middle age man alone at a table and a man about mid-twenties in a suit at the end of the bar. She had to play this out; it couldn't happen too soon. She looked at her watch, 6:50. She took a sip. Other people came in. A group of guys celebrating after a game of some sort sat in the corner, and a couple took a table. She was jarred with the realization that she hadn't been sitting properly. She looked around as though he could be there spying on her and slid off the stool. Try as she might, she couldn't get on the stool with the back of her skirt up, not without lifting the whole damn thing to her waist anyway. So she just stood and sipped.

7:00, time seemed to stand still. When no one else came in, she decided to strike up a conversation with the hunk in the suit and see if something could develop. As she made her move an attractive redhead entered the bar and joined him. Strike one at 7:10.

When no one else had entered 5 minutes later, she went over and asked if she could sit at the table with the middle age man. He indicated a vacant chair and she sat down. He wasn't particularly attractive, with a middle that kept him at arms length from the table. Now what, she wondered? They introduced themselves. Would he like to buy her another drink? He would, and went to the bar as she downed the rest of hers. By the time he returned with the drinks it was after 7:25 and she knew she had to make her move. She took a good swallow of the fresh one to steady her nerves and reached out and put a hand on his arm.

"Maybe we could go somewhere," she started.

"Where?"

"Someplace where we could be alone," she tried to speak seductively but it didn't come off.

"Are you a hooker or something?" he asked.

She blushed at the insinuation and took a drink to calm her nerves. "No, just looking for a good time."

"I've never seen you in here before," he wasn't too sure. She was definitely a cut or two above anyone who would look at him. "Are you a cop?"

She shook her head. "I've never been in here before. But I want to make you feel special tonight," she said feeling desperate now. It was almost 7:35.

"If you're sure."

She took his arm and led him out of the bar. "Where is your car?" she asked.

He pointed to a Pontiac a couple of cars down. She groaned at the proximity to the door and steered him away to her Mercedes at the edge of the parking lot. She hit the button and the doors unlocked. She opened the back door and motioned for him to get in.

"Right here?" he asked.

"I don't have a lot of time right now, sweetheart. Maybe later we can meet and do it right." She couldn't lose him now. She pulled her sweater and bra down to reveal her breasts. He reached out and stroked the left one. She slid across the rear seat and he followed, closing the door. She unfastened his pants and pulled his cock out and he reached over so he could run a hand over her breasts. She pushed him back and sucked him in; working the way Kyle had taught her. His moans gained force every time she swirled her tongue around the head. She started bobbing her head quickly now, and she reached under to massage his balls. He leaned forward so he could play with her nipples and the combination sent him over the edge. She sucked 'til her mouth was full, then raised her head and continued to bring him off with her hand.

Now what? She opened the door and got out, but he didn't move. She tried to talk but jism ran down her chin and she scooped it up with a finger and sucked it in. She reached in and grabbed his arm to pull him out but he pulled her back in on top of him and as her stomach hit his knee, the precious cum she had been saving was spit out all over him.

Damn, Damn. Damn. She looked at the mess that had spewn all over his pants and wondered if she could suck it all up. But it was already soaking into the material. "Out," she yelled figuring he could not cum again no matter what she did. "Just get out." It was 7:47. He scrambled out pulling his soiled pants up and looking bewildered. She hit the lock button as she ran back into the bar leaving him there. She look around and with little choice picked out one of the jocks. She leaned over and whispered in his ear that he looked like a real stud and she wanted to give him the best blowjob of his life.

"What?" She repeated what she had said elaborating on what she would do for him. The others looked on quizzically.

"You've got to be kidding?"

"You heard me right, Stud," she whispered. "Shall we?" she said grabbing his hand.

"Hey guys, this broad wants blow-jobs. Shall we oblige her?" At first they wouldn't believe it, then the whole group became animated, talking and laughing about the needs of a slut as she reddened even more and pulled her hand away.

Eight minutes to go. There was no time for this. She went to the end of the bar as asked for a plastic cup. The bartender handed it to her and she grabbed his hand and dragged him into the back room. The jocks watching the proceedings hooted and hollered behind her. She didn't even take down his pants, but knelt, unzipped the bewildered 30 something, fished him out, and grasped the base firmly. She sucked on the head while milking him with her free hand. Now her mouth followed the hand up and down his cock. The jocks out in the bar had taken up a chant and were clapping in unison shouting, "Go, Go, Go, Go, Go." She closed out the sound and concentrated on making him cum. His hand went to her hair and held it firmly. She felt a certain amount of power in feeling him get harder and harder—then he was spewing into her mouth. When it was full, she spit it into the cup and then went back for the rest. A glob had fallen meanwhile on the curve of her right breast. She rose, spitting the rest into the cup, and turned to go.

"Lady...," he said, his cock still twitching from the hole in his pants.

But she was gone. The jocks were still chanting and had moved over toward the bar. They saw the cup, the cum on her chin, and the glob above her sweater, and broke into cheers. God, what ass holes, she thought as she ran through them and out the door. As she scrambled toward her car in high heels, she scooped up the glob with a finger and flicked it into the cup. Her cheering section followed her outside and she could still hear them yelling and laughing as she spun the tires leaving the parking lot.

The car clock said 7:57. She raced the 7 or so miles to his house holding the precious cup in her free hand and praying that all the cops in the area were on doughnut break. The car squealed to a halt in his drive and she ran the last leg of the race to the door emptying the contents of the cup into her mouth and throwing it aside. Thirty seconds later she was ringing the doorbell and breathing heavily through her nose. Her watch, she had forgotten to take it off. It read 8:04 as she dropped it on the table. She glanced down at her nudity and prayed that no one was looking this direction. The minutes ticked by. Her breathing had slowed but the mouthful was becoming uncomfortable. She heard an elderly couple walking down the sidewalk and she turned toward the door, feeling very conspicuous. She didn't know if they looked toward the house or not. At 8:08 the door was opened. She recognized the secretary from Kyle's office, attired as she was except for an apron.

"You're late," was her only comment, as Rebecca brushed past to take up Position #1. Rebecca waited several minutes there before hearing muted footsteps behind her.

His voice sounded displeased. "You will be punished."

She could only nod.

"Did you come prepared as I asked?"

She nodded affirmatively again.

"Let me see." She tilted her head back and opened so he could see the thick, milky liquid she had worked so hard to obtain.

"Close your mouth, but don't swallow," he said holding a stick with leather at the end. "I will give you your choice of punishments. Both will involve your breasts. I can tie you up and you will receive 10 on the underside of each tit. Or you can hold them up for me and I will hit each 4 times. Of course if you let one fall, it will receive 2 extra penalty shots. If you lose the cum with either choice, there will be 4 penalty shots each. Which will you chose?"

This is a choice, she said to herself?

"wogggggannnn."

"O sorry, I forgot. Would you like choice 1?"

She shook her head no.

"Choice 2?"

She hesitated. The better of two evils is still an evil. But she finally nodded yes.

"Good. Stand up, grab both nipples and lift them as high as they will go. This will hurt, but you will want to remember the part about maintaining a full mouth."

He flicked the rod, testing it. Then he snapped it with his wrist and the leather cracked on her right breast just below her fingers, making it jiggle. Her eyes opened wide and a gurgling sound escaped from her mouth. A red welt appeared to mark the spot. She steeled herself for the next one and it stung equally as much in the same place on her left breast. She closed her eyes and a growling sound came from her throat. She tightened the grip on her nipples. There was no way she was going to let this go into overtime.

He changed ends and ran the handle through her bare slit. The end was slick with her moisture as he held it up for inspection and nodded.

"One," he announced.

The second one left a mark an inch to the right of the first on the right breast and a similar one soon appeared on the left. She had no idea the underside was so sensitive and wanted desperately to let go and massage the hurt away. Tears filled her eyes, but she refused to give him the satisfaction of crying. She couldn't even close her mouth to grit her teeth.

"Two."

Her mouth was salivating and the excess moisture gave her more than a mouthful. The excess was trickling down her throat and she had to swallow it little by little.

Crack. The leather hit an inch to the left of the original mark on her right breast. A tear trickled down her cheek unbidden as the injured breast stopped wiggling. He reached toward her and began massaging her clit. Shit, she thought when the realization hit her. If he brings me off now there is no way I can hold this damn cum in my mouth. She resolved not to respond. But the events of the past hour had made her too horny and there were too many distractions to her resolve. She was soon moving against his hand.

Crack. The leather tip came from below and popped against her left breast.

"Three." His fingers continued manipulating her clit even as he hit her. Her fingers were cramping from holding her breasts up by the nipples. But she just had to get through two more strokes.

"Are you ready?"

She nodded tightening her grip on the already painful nipples. The fourth one snapped an inch below the first one on the lower curve of the right breast. He could see the momentary pain in her eyes before her resolution took over. It didn't seem quite as bad now that she was close to orgasm. The fingers continued to rub her soaked pussy. Her body was betraying her again.

"You would like to cum?" it was hardly a question.

She shook her head no, then yes. She didn't know what she wanted. The taste of cum was strong in her mouth and she thought of the bartender.

"You seem uncertain. Do you want to cum?"

Yes, she shook her head, yes. He could tell she was on the verge of an orgasm and stopped rubbing momentarily.

"Very well. You have done well. You may cum on the last stroke. Hold them higher." Rebecca pulled her nipples up. "Higher still." They were taunt now, with the nipples pointing straight up, gripped by fingers holding as tightly as possible. Everything there was sore. The nipples hurt from her abuse during the last 15 minutes and the rest ached from the welts he raised. She set her feet firmly, preparing for the end.

"I will count down from 30," he said. "You will cum exactly at the end. And just to show that I can be lenient, I'll hit you the last time on the count of 2. Don't cum early—or late," he added.

She nodded. How on earth did I get myself into this?

"30." His fingers started rubbing circles around her clit again. Time seemed to stand still as she listened to his voice and lived in the moment of eroticism that swept over her.

"20." She was breathing hard through her nose. She swallowed again as a bit of slime slid unbidden down her throat.

"15." Her concentration was complete. Nothing but his voice and the hand at her pussy mattered.

"10." Her moans became louder and more frequent. This was it.

"8." He increased the pace. She had to wait.

"7." She knew she would never forget the taste of his cum.

"6." She pushed her cunt against him as hard as she could.

"5." So close, breathe out.

"4." So close, breathe in.

"3." She squealed through her nose. She held her breath.

"2." Crack.

"1." The pain had turned to pleasure.

"Cum Rebecca. Cum for me my slut." She struggled wanting to swallow as her insides contracted and wave after delicious, painful wave of orgasm washed over her. She didn't think to release her nipples and didn't realize how much they ached. Her knees shook and she straightened her legs to keep from falling down. He kept working her clit all through the orgasm. She started breathing in painful gasps through her nose. As she came down, she was sure this couldn't be happening to her.

Her mind cleared, and she lowered her nipples and let them go. A sharp pain told her the blood was flowing back into them. Her hands and fingers opened painfully.

"Open your mouth."

He checked. "Swallow."

"You are a bastard," she said when she could speak. "Sir."

He raised an eyebrow and pointed to the couch for her to sit. She did so thankfully since everything still quivered and her legs were like jelly.

12