The Executive Lifestyle Experience Ch. 03

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

Sara quickly lowered her gaze.

"I told you before, you must never look a Master in the eye."

"Yes, Master Scott."

McCafferty circled his kneeling young associate slowly, watching her carefully as he toyed idly with the whip. God, she was beautiful, he thought. So talented, so pretty. Another man's wife... demure and innocent. But he would soon change that. He could sense the sexual hunger just beneath the surface... the hidden slut that longed to be free... The naked lust, overmastered by the prim demands of polite society.

"I am going to ask you some questions, Sara," McCafferty announced, now circling behind her. "You will answer truthfully, honestly and openly. If you fail to do so, I will know, and there will be punishment. Do you understand?"

Sara gulped, dreading what might happen next.

"Y... Yes, Master Scott. I understand."

"Good..." He brushed the crop softly down her upper arm, teasing her. "How long have you had fantasies of being dominated by a man?"

Sara blushed. She took a deep breath. She didn't want to divulge her most private thoughts, but this man could somehow almost read her mind. If she tried to be evasive, she was sure he would know. Embarrassed though she was, she decided the truth was by far the safest option.

"Ever since I can remember. I... I don't know exactly."

McCafferty circled slowly around where Sara knelt, idly flicking the crop.

"Tell me... Tell me what you remember."

Sara was mortified, but she knew she had no choice. She spoke softly, nervously.

"When we were kids, we used to play games... innocent really. I remember once, my brother and his friends captured me... They tied my hands behind my back with rope and wouldn't let me go. They kept me as their captive for most of the afternoon. They were just playing, teasing me... But I got the strangest rush from the feeling of helplessness. It did something to me. Looking back now, I know I was getting sexually aroused, but I didn't recognize that at the time. I just knew I really liked the feeling."

"Interesting," McCafferty observed, tracing the whip across Sara's upper back. "Go on... what else?"

Sara hesitated, collecting her thoughts.

"When I was in my senior year of High School, three of my girlfriends came over to my house for a slumber party. We were camping in a tent in the back yard. Sometime during the night, we started playing strip poker. When I lost, I ended up outside, naked, with my hands tied behind my back, being led around the block, on a leash, by my fully dressed friends. I was scared out of my mind, and humiliated to be in such a predicament, but at the same time, it aroused me terribly."

Sara blushed, looking at the floor.

"Well, well," McCafferty said, now tracing the crop softly down Sara's upper arm. "That does indeed sound interesting. I think you need to elaborate."

Sara whimpered softly. Oh, god, he was going to make her tell the whole story. She would surely die of embarrassment!

"I'm waiting. Do you need a few strokes of the crop to loosen your tongue?

Sara flushed.

"No, Master Scott."

"Then I suggest you tell me, in exacting detail, what happened that night.

Sara took a deep breath, steeling herself.

"We were in the tent, having fun, joking around and playing cards. It was after midnight, when someone suggested that we play strip poker. I was kind of scared to do it, but the other girls were for it, so I reluctantly agreed. Before we started, my friend Wendy insisted that we all pledge to each other that we wouldn't chicken out when we got down to our underwear. If we were going to do this, she said, we had to be willing to risk everything. I was really worried, because I didn't think I could strip all the way. But the other girl's made the pledge, and insisted that I do so as well."

Scott smirked knowingly.

"Such naughty teenaged girls... Go on... tell me what happened."

"Then Wendy really blew me away. She said that to make the game really interesting, whoever lost would have to run naked out to the front yard, and loop around the house, before they could come back and claim their clothes. I said 'no way', but the other girls looked like they were considering. Lisa pointed out that it was nearly two in the morning, and any normal person would be in bed. It was very unlikely anyone would be seen. I knew she was right, but it still seemed crazy-reckless. There was a street-light out front, I argued. Running naked around the front of the house would be like running naked in broad daylight. If anyone was awake, they would be able to see from anywhere on the street."

Sara whimpered slightly as McCafferty traced the outline of her breast with the crop.

"Go on, slave," he insisted, as he continued to play with her breast. "Continue your story."

Sara blushed at the liberties he was taking with the crop, but she took a deep breath and continued.

"The four of us discussed it, and eventually agreed to do it. Someone said that it had to be a little bit scary, or it wouldn't be as much fun. They tried to assure me that nothing bad was going to happen. Streaking through the neighborhood sounded pretty risky to me, but I was out-voted, and reluctantly agreed to the terms."

"So you decided to play," McCafferty noted as he continued to slowly circle. Every now and then, he would trace the crop down some part of Sara's body, caressing her with the supple leather, teasing her with the implied threat of what it could do. "Were you scared?"

Sara blushed.

"Yes, Master Scott... It was ok at first, because I was lucky enough not to lose too much. It was kind of exciting, actually, but more than a bit scary... I dreaded having to take off something intimate, and the thought of losing the game made me feel faint."

"Definitely a high-stakes game as far as you were concerned," McCafferty observed. Tell me what happened... In as much detail as you can remember."

"Yes, Master Scott." Sara took a deep breath. "The first few rounds were easy enough, with the different girls losing socks and shoes... nothing very serious. Then, things began to get more intense. I was soon down to my bra and panties. I was really getting scared, because if I lost again, I would have to give up a piece of my underwear. But I was also very aroused. My panties were soaked..."

"Yes," McCafferty observed. "Fear does that to many woman... Go on."

"Then my luck changed. I didn't lose again, while the others lost several rounds. After a while, Wendy and Julie had both lost their shirt, pants and bras, and were naked from the waist up. I still had on my bra and panties... Then Julie lost the game. She had to stand up and remove her panties, leaving her completely naked. I was so glad it wasn't me. Those of us who had not lost, quickly got dressed, but we wouldn't let Julie have her clothes back until she had run around the house."

"That must have been fun," McCafferty observed. "So... did Julie do it?"

"She looked really scared. She begged to be let off, but the others refused. A bet was a bet, they said... I didn't say anything. I was feeling sorry for Julie, and didn't like the idea of streaking out front, anyway, so I would have called it off. But Wendy and Lisa insisted she do it. Finally, at the other girl's insistence, Julie left the tent, stark naked, and ran around the house. We all went with her, giggling at the sight of Julie running around the yard completely naked. When we looped around the front of the house, the streetlight out front lit up everything, but Julie kept running and it was all over in just a few seconds."

Sara paused, squirming slightly in her bondage. She was turned on, aroused by her predicament and the story she was relating.

"We got back to the tent, breathless and giggling, and Julie quickly got dressed. Everyone agreed it had been a rush, even Julie. After we calmed down, we decided to play again, and ended up playing several games. Somehow, I always avoided losing, although I would get terrified every time I got close. Once, I lost my bra, which embarrassed me to no end, but I was never the girl who lost everything. In the end, each of the girls except me had taken a turn running around the house, some of them twice."

"But that changed, didn't it," McCafferty observed when Sara paused to take a breath. "You ended up losing."

Sara nodded.

"Then, the unthinkable happened. I lost it all, and I was supposed to get naked and do my lap. I panicked, and I refused. The other girls cried foul; after all, each of them had made the run when they had lost. But I just couldn't do it. I couldn't. So I refused."

"You bad little girl," McCafferty scolded playfully. "Welshing on your bet... how shameful."

"The other girls thought the same thing," Sara admitted, ruefully. "They forced me to do it. They pushed me down and held me while one of them stripped off my panties. Then they tied my hands behind my back and pushed me out of the tent."

Sara blushed at the memory, her breathing deep and ragged.

"I was naked and outside. With my hands tied behind my back, I couldn't even try to cover myself; I was completely exposed. The other girls didn't even come outside with me. They just zipped up the tent and began playing another round of cards. They told me the only way I could get my clothes back was to make the run."

"Such a predicament," McCafferty sounded amused. "What did you do?"

"I tried to hide. I was mortified to be outside naked, but there was no way I was about to run out under that streetlight. So I did the only thing I could think of. I crept over to the edge of the woods and tried to hide behind a bush."

"So how long were you out there," McCafferty asked, now drawing the crop along the exposed skin of Sara's upper back.

"I don't really know. It was probably five minutes or so, but it seemed like forever. After a while, I heard someone unzip the tent, and then the three of them came out. At first, they didn't seem to know where I was, but then someone, Lisa I think, spotted me. The girls came over to where I was hiding. They told me I could be out there all night, if I wanted, but I wasn't getting back in the tent or getting my clothes until I had run around the house."

"So they forced you to do it," McCafferty observed.

"Yes," Sara admitted. "I begged and pleaded, but they would not relent. Finally, Wendy announced that since I wasn't going to do it voluntarily, they would make me do it. She had Julie take off the leather belt she was wearing, then passed the end through the buckle, so that it formed a choke collar and leash. While the other two girls held me by my upper arms, Wendy slipped the makeshift collar over my head and pulled it snug around my neck. Then they led me, pulling at the leash around my neck, out front. The three of them decided that, since I wouldn't do it voluntarily, I had to be punished. Instead of just making me run around the house, they led me around the entire block, walking slowly, taking the side-walk."

"Oh, my," McCafferty observed. "I'll bet that was embarrassing."

Sara gasped, blushing at the memory.

"Oh my god, yes! It was like a quarter of a mile walk, along residential streets. Even though it was in the dead of night, about 2:30 or 3, I was terrified. I was stark naked, with my hands tied behind my back, being led like a slave, by a leash around my neck. Worse, there were streetlights every so often. Every time we passed under one, I felt so wildly exposed I almost fainted."

"But you survived, didn't you," McCafferty challenged. "Not only that, but it turned you on, didn't it?"

Sara blushed even more.

"Yes," she admitted. "It turned me on. I don't know why, but knowing that anyone might drive by, or could look out and see me, made me very hot. I felt so helpless, knowing that my friends had complete control."

"So what happened then," McCafferty asked. "When you got back to the tent?"

Sara looked startled, her face now very red.

"N... N... Nothing, really. We stopped playing cards and eventually went to sleep."

McCafferty looked at her carefully, scrutinizing her. Several seconds passed as he studied her. Then he made a decision.

"I told you, Slave... If you lied to me, there would be punishment!"

He grasped Sara's cuffed wrists in one hand, lifting them up and forcing her to bend over. He flipped her skirt up, exposing her pretty little ass, then raised the crop in his other hand.

<Whack!>

<Whack!>

<Whack!>

<Whack!>

McCafferty hit each cheek of her ass, twice, in rapid succession. These blows were harder, leaving a stinging red imprint on each cheek. Sara cried out with the pain, struggling briefly to get away as McCafferty held her tightly.

"Ahhhhhh.... Ahhhh! Oww! Oh, please, don't hurt me!"

"Punishment is supposed to hurt, Slave," McCafferty said as he released Sara's wrists and allowed her to kneel back up, the skirt of her dress once more draping over her red ass. "If you don't want to be hurt, I suggest you stop lying to me!"

He worked the catch at the back of Sara's neck, releasing the halter straps at the top of her dress. When he pushed them off her shoulders, the material fell to Sara's waist, leaving her breasts exposed. Her hard little nipples stood erect and exposed on the soft smooth flesh of her perfect breasts. With her hands bound behind her, there was nothing she could do to cover her nakedness.

"Oh my god," Sara whimpered. "No... Please."

"Stand up, Slave," McCafferty growled, gripping Sara's upper arm and helping her to her feet. "It's time to see what you're hiding under that sexy little dress."

As Sara stood, the dress, now a bunch of clingy material around her hips, started to slide. McCafferty gave it a little push, and it slid off her hips to puddle on the floor. Sara was now completely naked.

"Very nice," McCafferty commented. "You are a very beautiful, sexy woman, Sara. Now step out of the dress."

At McCafferty's urging, Sara stepped out of the little puddle of material. He reached down and picked it up, then reached over and retrieved Sara's panties.

"Stay here," he commanded, taking the dress and her panties into the next room. When he returned a moment later, he did not have them.

"I've locked your clothes in the safe," McCafferty told her. "If you are good, you can have them back when it's time for you to leave. Until then, you are my captive, and will do as I say."

"Oh, god," Sara gasped, now acutely aware of her nakedness. "Yes, Master Scott."

"On your knees," McCafferty ordered.

He held her arm to steady her, as Sara sank back to her knees on the floor.

"Now, tell me, Slave," McCafferty said in a low, menacing voice, "what happened when your friends took you back inside the tent. Do not lie to me again, and make sure you tell me every detail. Do you understand?"

Sara was breathing raggedly, her face flaming red.

"Yes, Master Scott," she gasped. "Oh my god, this is so embarrassing."

"Not half as embarrassing as what will happen if you don't tell me exactly what went on," McCafferty said pointedly. "Now, tell me what happened."

Sara swallowed nervously.

"When we got back to the tent, my friends realized how aroused I had become. My pussy was so wet I had pussy-juice running down my thighs. They made me spread my legs so they could see how wet I was, saying that I must secretly like being naked. They took turns fingering my p-pussy, teasing me, and laughing as they took me to the brink of cumming."

Sara paused, blushing. She took a deep breath to muster her courage, then continued.

"When I asked to be released, they refused. They wanted to keep me naked. Someone said they liked having me as their slave, and suggested that it would be fun to make me do stuff. They soon decided that the three of them would continue playing strip poker, and whoever lost would have to make out with me. Whoever won got to direct what we did to each other, for a period of 5 minutes."

"I think Julie lost first, and she was naked. The other girls insisted that she make out with me, so she came over and we began to kiss. I had never kissed a girl before, but it was kind of nice, much better than I expected. I was embarrassed, since we were both naked, but I had my hands tied behind my back, and had to do whatever they decided. I kissed her back, and she was petting me... feeling my breasts and putting her finger in my pussy. I was so turned on, at that point, that I soon didn't care how embarrassing it was... I just wanted to cum! Julie kept fingering me as she kissed me, and soon I was kind of humping her hand, which made the other girls giggle."

"Did you cum?"

Sara blushed even more.

"Yes, Master Scott, I did. As she kissed me, Julie rubbed my pussy until I had a massive orgasm. I had been very aroused at being naked and tied up, and it was a huge release."

"Then what happened?"

"The other girls told Julie to lay back and make me lick her pussy. I protested, saying the five minutes were up, but they told me it didn't matter. I had to do whatever they said, and they wanted to see me eat Julie's pussy. I didn't want to do it, because I had never done anything like that, and the thought sort of revolted me. But I didn't have much of a choice. Julie grabbed my head and pulled me to her crotch. With my hands tied behind me, there was nothing I could do to stop it. I begged to be let off, but Julie just rubbed my face in her crotch and told me to do it. I didn't like the smell, and I kept my lips shut as she rubbed her pussy all over my face."

"They let you get away with that?," McCafferty asked. "I would have forced you to lick her."

"Oh god...," Sara whimpered. "They did force me, Master Scott. After a few minutes, somebody slapped my butt and told me to get my tongue into her. I finally gave in and did it. It wasn't as bad as I expected, and I sort of got off on being forced to do something sexual that I didn't really want to do. Then Julie started moaning, humping against my face, and I kind of liked being able to do that for her. She finally came, squeezing my head between her thighs and thrashing and moaning. It was quite a turn-on, actually."

"Afterwards, the others gave Julie her clothes back, and they started to play again. I had to stay naked, my hands still bound behind me, while I waited to find out who lost next. It was Wendy. When she was naked, the others insisted she make out with me. Wendy refused to kiss me on the lips, saying I 'smelled like pussy'. But she sucked my breasts and played with my pussy, then she lay back and insisted that I go down on her. I gave up resisting and did what she wanted, licking her until she had cum. It went on like that for the rest of the night. The others played strip poker until one had lost, then I had to lick her pussy until she had cum. By the time we finally got to sleep, I think I had eaten each of the girls at least twice."

"Did you enjoy it?"

"I don't know, Master Scott," Sara replied thoughtfully. "I don't think 'enjoy' is exactly the right term. I'm not a lesbian. I didn't really like the idea of giving oral sex to another girl, but it was a real turn on to be forced to do it. The feeling of helplessness, of being a slave, was very arousing for me."

"Did you cum with any of the other girls?"

Sara blushed all the more.

"Yes, Master Scott, I came several times. Not every time, but I was very turned on, and I came several times as the other girls were fingering my pussy."

"Did any of the other girls eat your pussy?"

"No, Master Scott, they didn't."

"Have you ever had your pussy eaten?"

"No, Master Scott, I haven't. My husband never really tried to do that."

"His loss, but back to your girlfriends," McCafferty mused. "Did you ever repeat your little campout?"

"No, Master Scott, not really. I think we all enjoyed it, but we also felt guilty, like we shouldn't have let things go as far as they did. The next day, everyone was a little embarrassed, but we also knew we shared a secret, and that made us even closer as friends. No one ever talked about what had happened, and we never repeated it... There were some other incidents, but nothing that really stands out... My girlfriends knew I got turned on by being exposed, and they sometimes tried to push me into situations that would humiliate me. Once, at a pool party, Julie and Wendy yanked off my bikini top and threw it to a group of guys. I dove into the pool and had to remain there until I could persuade them to give me my top back."