The waiter stopped by the table, checking to make sure everything was okay, and asked if the couple would care to order another round of drinks. Jake looked across the table at his sexy date, and ordered two more beers. They had to wait at the bar for a while before getting a table and had already put away a few drinks on empty stomachs, so both were feeling loose and relaxed.
It had been quite a surprise to Jake when Lisa, one of his ex-girlfriends, had called him up and offered to take him out to dinner. Although they had a rough break-up several years ago, she remembered that his birthday was this week and suggested that they go out to a nice restaurant. There was also the hint that she missed his company and wanted to get back together with him, at least on a short term and casual basis.
One of the things that Jake had always liked about Lisa was that she always wore sexy clothes when she went out. Tonight was no exception as she wore tight black leather pants with spike heeled pumps, and a white top with a plunging neckline that laced up between her ample breasts, clearly exposing her cleavage. Her blonde hair cascaded over her shoulders in spiral curls. Lisa had a few extra pounds on her, but few men would hold it against her as she was nicely proportioned. Jake noticed a few men in the restaurant taking longing glances at his date, and he was delighted with their envy.
While Jake had offered to drive that night, Lisa had told him to meet her at the restaurant. Later, as he walked her out to her car, he made his move and it was accepted. Pausing beside her car and kissing passionately for a while, Jake slid his hand down to feel the warm leather of Lisa’s pants stretched tightly over her perfectly curved ass.
“Listen, Jake,” she said softly. “I don’t want to take things too fast. I mean, I sort of forgot how hot you were and lost control, but really we’ve got to take it easy.”
Jake said he was willing to take it easy and was prepared to say good night, when to his surprise, Lisa asked him to come over to her apartment for a little while. Although she made it clear that he wouldn’t be spending the night there, he readily accepted the invitation.
Lisa’s apartment was only a short distance away. It was in one of the newer, endlessly sprawling complexes that seemed to be popping up all over on this side of town. Overpriced rent with stunning curb appeal, yet the interior proved to be your average boxy apartment that you’d find in any complex. Her apartment had two bedrooms, and she mentioned a roommate that was out for the evening.
At the time they had been a couple, Lisa had lived in a different place, but to his surprise, Jake recognized a lot of the same furniture and decorations from her previous apartment. He settled in on the familiar sofa and Lisa brought them both some fresh drinks from the kitchen.
They talked and laughed about times in their past, the band he had played with when they had been together, and eventually began kissing again. Much to his surprise, Lisa quickly removed his shirt.
Assuming that Lisa had changed her mind about taking things slowly, he tried to get her out of her shirt as well. To his surprise she backed away, but then dropped to her knees in front of him and began to slowly unbuckle his belt and undo his jeans.
Jake’s cock had already been getting hard, and he was relieved when she pulled the rigid length from his tight bikini briefs. Stroking his cock with one hand, she removed his pants with the other. Just as she was moving in for what Jake assumed would be a fantastic blow job, he heard a familiar voice from across the room.
“I knew he’d be easy to reel in. The male sluts always are.” Standing in the hallway that led back to the bedrooms, was Raven.
Jake had been punished by the mysterious Mistress Raven and his former conquest Tammy several months ago. It was a painful lesson that he didn’t forget. Raven had called him every few weeks, insisting that he come over to her house, presumably to be punished by her and another ex-girlfriend. Jake had refused every time. Now it seemed that with the help of Lisa, she had trapped him once again.
Jake would have run for the door but he was completely naked. He pleaded with Lisa, but her attitude had completely changed.
“You bastard,” she said, gathering his clothes and getting up from the floor, “You didn’t really think I could forgive you. Did you?”
Lisa had planned to go out of town years ago, but those plans had been canceled for some reason and she showed up unexpectedly at a club where Jake was playing. Catching him in the band’s dressing room while getting a blow job from one of his groupies, their relationship had ended on the spot. Jake could only assume she was out for some sort of revenge, with the help of the sadistic Raven.
Strolling into the living room coolly as if it were her apartment, Raven wore form fitting black leather pants and heels similar to Lisa’s. A black silk top was visible beneath her open black leather biker jacket.
Jake tried to get up, but Raven ordered him to stay seated. She was brandishing her riding crop in one hand and Jake knew that it was best to obey her. At least they were here at Lisa’s apartment, and not down in Raven’s playroom with her whips and other surprises.
Raven pulled a set of handcuffs from a pocket of her jacket and quickly cuffed Jake’s hands behind his back. The two women then placed his clothes in a plastic garbage bag and Lisa brought a short pink satin robe from her bedroom. They did all this in a matter of seconds and it was obvious to Jake that this had been carefully planned in advance.
Jake was ordered to stand up and the pink robe was draped over his shoulders and roughly tied around his waist. His cock, still hard, bulged clearly beneath the thin shiny fabric.
“We’re going for a ride,” is all that Raven said as she and Lisa each grabbed one of Jake’s shoulders and pushed him towards the door.
The hallways and stairs of the apartment buildings were open to the weather, and the concrete was cold under Jake’s bare feet as the two women led him down the steps and out to the parking lot.
The trio passed a group of young guys who were on their way up the stairs, and had obviously been out for a few beers. Jake hoped they might try to rescue him from his plight, but all they did was laugh and whistle at the two hot babes in leather hauling off their helpless man who was wrapped in a woman’s bathrobe.
Crossing the parking lot, Jake begged Lisa to let him go. He explained that what had happened between them had been years ago and was not worth any trouble now. The two women said nothing and all he heard was the sound of their high heels clicking on the cold pavement as they forced him across the parking lot.
Jake was roughly pushed into the tiny back seat of Raven’s car. The bag containing his clothes was tossed in on the other side, and they strapped on his seat belt to make any escape attempt impossible. Once the two ladies were up front, Raven backed out of the parking space, and quickly drove to a familiar part of town. The radio was off and the two women said nothing. For Jake it was an uncomfortable silence, not knowing what his fate would be. When they were a few blocks from Raven’s townhouse, she spoke at last.
“You probably figured that we were taking you to my house. We’ll be there for a while. Lisa wants to punish you, but don’t worry, we’ll let you go before morning.” Although she spoke in a calm voice, Jake was far from being at ease.
Lisa started to chew him out for making a copy of their sex video, when he had supposedly given her the original tape. She went on to say that it disgusted her to kiss him and fondle him, but it was the only sure way to lure him into their trap. There might have been more to say, but she shut up as soon as they pulled into Raven’s garage and the door automatically closed behind them.
In short order, Jake was pulled from the back seat and led down to the finished basement of Raven’s townhouse condo. He was stripped of the satin robe and commanded to kneel before the two women, who sat on tall stools at the bar, his hands still cuffed behind his back.
“Before Lisa starts punishing you,” Raven began. “I’ll give you a few minutes to beg for mercy. Maybe if you licked our shoes she will take it easy on you.”
Two pairs of shiny black stiletto heeled pumps were just inches from Jake’s face and he immediately started licking the smooth patent leather. He tried to devote equal attention to all four shoes, and paused periodically to look up at Lisa and plead for her mercy.
“You just go ahead and beg, you worthless little cheating slut. Raven told me all about your collection of homemade porn. I should have guessed that such a sleazy bastard like you would never give me our tape without making a secret copy for him self.”
“Please, Lisa,” Jake pleaded. “That was a long time ago, and Raven probably gave you the tape back. That was the only other copy I had. You can take my keys and go search my apartment right now if you want. You won’t find another copy.”
“A search won’t be necessary because I believe you,” said Lisa. “However, you still need to be punished. I’m very glad that Raven gave me this opportunity.”
Both ladies got off their stools and Raven ordered Jake to stand facing one side of the pool table. Although he got up and started to walk towards the table on his own, Lisa couldn’t resist grabbing him by his cuffed wrists and forcing him up against the rail.
Raven appeared to his right side with her black leather bag. She pulled out several paddles and laid them on the table.
“I suggest you start with a good spanking, just to get his attention,” Raven said in her usual condescending tone, and forced Jake to bend over the pool table, pressing his nose into the green felt.
He wasn’t sure which paddle Lisa had selected, but she wasted no time in swatting his bare ass with it, and it hurt like hell. She was muttering a bunch of obscenities and insults at him, but Jake couldn’t hear most of them with the loud cracking of the paddle on his buttocks. In no time the pain was too much to bear and he started sobbing out loud.
The spanking stopped, Raven grabbed a handful of his hair and lifted his head off the table.
“Does that hurt really bad?” she asked, mocking him.
Jake tried to respond but the words were lost in his sobs. Raven scoffed at him and reaching into a pocket of her leather jacket, she pulled out his bikini underwear. This was promptly stuffed in Jake’s mouth before Raven forced his head down on the table again.
“Try this paddle,” he heard Raven suggest to Lisa. After a few moments, the spanking began again. This paddle made a louder smack on his bottom, yet Jake didn’t think it hurt as much. He wasn’t sure if Raven had given Lisa a less severe paddle or that his ass was simply going numb with pain.
It was still a painful spanking and Jake fought back his tears and moans, his musky underwear in his mouth quickly soaking up with his saliva. At the point when Jake was sure he would pass out, Raven said,
“Let’s take a little break. I think he’s a little too beat up to run away right now,” and started removing his handcuffs. To his relief, she also ordered him to remove the gag from his mouth and simply throw it on the carpeted floor.
“Go behind the bar and fix us two rum and cokes, slave,” Raven ordered.
Rubbing his sore wrists and flexing his stiff arms, Jake quickly hurried behind the small bar. He didn’t dare ask where anything was, but having cleaned the basement playroom a few times in the past, he quickly found the right glasses. There was also a small bin of ice cubes in the freezer compartment of the mini fridge under the counter.
Setting the mixed drinks on the bar in front of the ladies, who had already sat down, he stood obediently awaiting his next orders. Tears were drying on his cheeks, and his cock was slowly starting to get hard.
Raven had removed her leather jacket, revealing a shimmering black silk tank top. The lace-up cleavage on Lisa’s blouse had come loose with all the activity and her ample breasts looked like they would spill out at any minute. Her hair was slightly ruffled and she glowed with a thin sheen of sweat.
Raven must have spotted him eyeing them, his cock now fully erect, and ordered him to get down on all fours in front of them, to act as their foot stool while they enjoyed their drinks. Jake got down on the floor as ordered, and the ladies swiveled around on their stools, placing their spike heeled feet on his back and tender buttocks.
Jake was oblivious to their conversation as they sipped their drinks and prodded him with the pointed toes and sharp heels of their shoes. While he was relieved to get any kind of break from his punishment, there was still the fear of what else they had planned.
It didn’t seem long before Jake heard their empty glasses being set on the bar. Raven ordered Jake to stand facing the side of the side of the pool table as before. She pulled two wide leather straps from her bag and fastened one on each of his wrists. Then each wrist cuff was fastened with a short chain to one of the metal rings he knew were hidden just below the rail.
Standing there helpless, Jake assumed that the spanking would continue. The collection of paddles was still laying on the pool table. To his horror, Raven pulled the multi-tailed whip from her leather bag.
In no mood to hear any pleading from Jake, she picked his soggy briefs up off the floor and stuffed them into his mouth. He could hear her mumbling some instructions to Lisa, who seemed more than eager to try the whip on her ex-boyfriend.
Although it hurt like hell, Jake couldn’t help notice that Lisa was clumsy with the whip. Clearly lacking Raven’s skill, a few blows glanced almost harmlessly off his shoulders. After a while though, she seemed to get the hang of it and whipped him repeatedly on the shoulder blades.
Jake’s screams were muted by the gag as he pulled at his chained wrists, trying to break free. Lisa was cursing at him and whipping him with a steady rhythm. The pain was unbearable, when all of a sudden Raven ordered Lisa to stop.
It was a shock to Jake that Raven had used the same commanding tone with Lisa as she would a lowly slave.
Lisa refused and the whip landed several more times on Jake’s back. They argued briefly and Jake though he heard momentary sounds of a struggle, but then heard only their high heels clicking loudly up the basement stairs.
Although Jake wondered what the sudden argument had been about, he was glad that his punishment had stopped. Raven had whipped him before and it had been bad, but the whipping from Lisa had left his back raw and painful like nothing he had experienced before.
A few minutes later, he heard one pair of high heels slowly coming down the basement stairs. Daring to look over his shoulder he saw Raven carrying what looked like some first aid supplies.
“You deserve to be punished,” she said, placing the supplies on the pool table. “But there’s no reason for you to be skinned alive by an amateur.”
Although Raven was clearly disgusted, he thought there was a hint of compassion in her voice. She removed his gag and explained that Lisa had whipped him too hard and had cut his back in several places.
“It’s nothing that won’t heal up soon since I stopped her in time, but there may be a few small scars. I assume you’ll wear them like badges of honor.”
Jake didn’t know what to say, and winced as Raven cleaned his wounds and then applied bandages. At last, she released his bonds.
“Put this on,” she ordered, handing him Lisa’s satin robe. “I’ll take you back to your car. Don’t give me any trouble or I’ll cuff you and stuff you in the trunk.”
Jake obediently walked up the stairs in front of Raven. The living room was dark and Jake could see Lisa sitting on the couch in the shadows. It looked like she was somehow restrained in her seat but a brief glance was all he got. There was no time for either of them to speak before Raven quickly steered him towards the garage.
She let him sit in the passenger seat, and he noticed that his bag of clothes was still in the back. Although Raven had paused before going up the stairs to put on her leather jacket, he assumed that his bikini briefs had been left on the basement floor. She could keep them, he thought.
The night was cool as Raven drove quickly through town. The heat was off and Raven was comfortable in her leather, but Jake was freezing in the thin bathrobe. He thought about reaching for the heater controls, but then decided against it. It was a silent and uncomfortable trip, but at least it was a short one.
Raven pulled up behind Jake’s car in the complex parking lot.
“The next time I call you and tell you to come over to my house, I suggest that you do so,” Raven said. “Lisa and I were very aggravated that we had to go through the extra trouble of trapping you. If you had come over weeks ago when I called you, she may not have gotten out of control. Something for you to think about. Now get out,” she ordered and handed him the garbage bag filled with his clothes.
He started to ask if he could put his clothes on in her car, but Raven leaned over and opened his door.
“Give me that robe,” she commanded as he stepped out, his bare feet on the cold pavement. Jake tossed the robe on to the passenger seat and had barely closed the door before Raven took off with a squeal of tires.
Naked, Jake crouched next to his car and fumbled through the bag for his car keys. Thankfully there was no one in the parking lot at this late hour.
When he finally got back to his apartment, he used several mirrors in his bathroom to check the wounds on his back. They were not as bad as he feared, and healed up to nearly invisible scars over the next few weeks. Thankfully, so far there had been no phone calls from Raven.