Classy Carissa...Or Is She? Ch. 4

It was a Saturday afternoon, warmer than usual for fall. Carissa looked at the clock, wondering when Jack would be home. He had gone to meet Trevor, a good friend and colleague, for lunch. Trevor was one of very few who knew the nature of Jack and Carissa's relationship.

When the phone rang, Carissa eagerly answered it, sensing that it would be Jack. She wasn't surprised to hear his voice…he told her that he'd be home in about an hour and that Trevor was coming with him. He also told her to change into a short skirt and to remember the rules…to wear nothing underneath it, or her shirt.

Puzzled and apprehensive Carissa walked upstairs to change. After freshening up, she slipped into the skirt and a pretty red t-shirt that buttoned up the front. She brushed her long chestnut colored hair and applied some liner and gloss to her full lips. She finished by spraying a bit of perfume on her neck and chest.

It seemed to be taking them an awfully long time to arrive. As she stood at the picture window waiting, she thought about Jack's request…surely it didn't mean….

Finally she saw Jack's truck driving up the street of their upscale neighborhood, Trevor following right behind in his car. She watched as they pulled onto the secluded driveway and as both men got out.

Trevor was in his late forties Carissa guessed…he was tall and broad, dark hair, silvering a bit at the temples. His most striking feature was his disarming blue eyes. She found him quite attractive.

Carissa opened the door as they stepped onto the covered porch. Before she had a chance to say a word, Jack said "Sorry it took so long, babe. We got to talking about you, and lost track of time."

"No big deal" she replied…wondering exactly what had been said about her. She turned to Trevor. "Great to see you again. How've you been?". She smiled warmly and gave him a light hug.

"You look awesome as always, Carissa. Things have been really good"….Trevor responded…and the chit chat continued as they sat down in the expansive, nicely decorated living room; Carissa and Jack sat on the large sofa and Trevor across from them in an overstuffed chair.

"Hey, Carissa...be a doll and bring out some beer, would you" asked Jack after a few minutes.

She smiled at Jack as she got up to do what he asked, and returned with 3 opened bottles and some glasses. She carefully set everything on the heavy wooden coffee table and sat back down next to Jack.

They continued to talk…about work, the weather, everything and nothing. Jack's hand went from resting on her thigh to slowly creeping upwards to the hem of her short skirt. She squirmed and shifted and eventually crossed her legs. Big mistake.

Jack immediately looked at her…unblinking and unkindly he said "Uncross your legs, now." She complied immediately. Once again his fingers found the hem of her skirt and he lightly brushed his fingers under it.

Carissa was mortified. Jack had never used her or displayed her in front of anyone. They had discussed it however, and he informed her that 'one day' he would desire to do just that. Had that day come?

Her head was down, sort of looking at the floor. She raised her eyes a bit to see if Trevor was looking at Jack's hands. Of course he was. Just then Jack pressed at her knee, nudging her legs apart. Reluctantly, she opened them a little. Another big mistake.

Again Jack looked at her. This time he spoke louder "Open your legs Carissa. Stop acting foolish". He turned towards her and pulled her skirt up barely exposing her, and slid his hand between her legs. Carissa was stiff and unwilling. This made Jack quite angry.

"You know that I expect for you to be available to me whenever and wherever I desire, Carissa. You'll be punished for your disobedience later. But right now I want you to go over and let Trevor look at you...show him anything he wants to see. Maybe once you know he's seen it all…and touched it all…you'll loosen up."

Carissa looked at Jack in agony. "You mean I have to show…show him everything???"

"Yes, Carissa. Go show him everything" he stated firmly. "Now". Jack knew that exposing herself this way would excite Carissa…she just didn't know it yet.

Slowly Carissa stood up and walked over to Trevor. She looked at Jack, hoping he'd change his mind or something…. although she knew better…

"Unbutton your shirt, Carissa" Jack demanded as if he were talking to a child. "Now open it so Trevor can see your tits". She did exactly as she was told.

"Go ahead, Trevor, she's all yours" said Jack.

"Very nice", admired Trevor as he reached up and lightly rolled Carissa's nipple between his fingers. He alternated between one breast and the other, pinching and tugging each nipple in turn.

"Now, the rest of it, Carissa" demanded Jack. "Pull your skirt way up and show Trevor your pussy."

Carissa inched the skirt up, exposing her nearly bare shaved crotch. She stood there waiting for further directions, risking that Jack would get mad at her again. And he did.

"What's the matter with you today? Spread your feet apart and open your pussy lips so that Trevor can see. You know better than this...now put your foot on the coffee table and show him your cunt, or I'll have to punish you right here and now."

Oh, that's the last thing Carissa wanted… 'please, not in front of Trevor', she thought. Immediately she placed her foot on the table and spread her pussy lips. Trevor leaned closer towards her and chuckled…adding to her embarrassment.

"She seems to be enjoying herself, Jack", he said as he slid his finger into her pussy, revealing that she was dripping wet. She blushed furiously.

Trevor continued to examine her…he tugged at the hood to expose her clit. He lightly flicked it a couple of times before sinking his finger deep into her aching pussy. Carissa moaned and tilted her hips in the direction of Trevor's hand. But he withdrew his finger… and she sighed in frustration.

"Now, I think you should turn around and let Trevor get a good look at your pretty ass", Jack stated simply. "Lean way over and stick your butt way out. "

Carissa quickly turned around and spread her feet and knees widely, she bent over, placing her elbows on the coffee table. She arched her back, and thrusted her ass up, exposing herself completely.

"Good girl." Jack said.

Trevor pulled at her cheeks, spreading them wide to expose her tight hole. Placing his thumbs close to her anus, he pulled her open. Jack walked over to stand behind Carissa. He watched as Trevor firmly massaged the outside of Carissa's tightly puckered hole, causing it to relax and open, making her moan. Once more he gripped the edges of her asshole with his thumbs and the tips of his forefingers, opening her even more. He lightly rubbed and pressed the pink puffy flesh with the pads of his finger…up and down and back and forth. She pushed her ass towards him…seeking penetration.

But he pushed only the tip of his finger in…he wiggled and twisted it, and pushed at the tight ring of her hole in every direction. Carissa desperately wanted full penetration, but knew she wasn't going to get just yet….

"You like that, don't you my little slut", asked Jack.

"Mmm…Yes", she said.

"Yes, what?" snapped Jack as Trevors finger continued to poke and tease Carissa's asshole. "Yes, Sir. I like it", she almost yelled.

"Then don't you think you should thank Trevor and tell him that you like it?"

"Thank you, Trevor. I like your finger in my ass." She replied.

"Yeah, she's pretty hot." Trevor sighed and smiled as he leaned back into his chair.

As Jack sat back down on the sofa he motioned for Carissa to sit next to him again. She stood up and walked to Jack and sat beside him.

"Lean back on the pillows… raise your hips and slide this one under your butt…pull your leg way back and put your foot on the back of the sofa …that's it …and keep your other foot on the floor." said Jack as he tapped her left leg and pushed on the inside of her right knee. "Now hold your pussy open. Wider. More." She used the tips of her first three fingers to pull her labia apart, which opened her cunt for view.

"That's it…just like that", he said, talking to her in a tone usually reserved for small children. She was very turned on and terribly wet. She was exposed from clit to tailbone and felt very vulnerable and a bit silly. She didn't understand why she liked this so much…

Carissa couldn't believe that she was lying here spread like this …but she did as she was told, although she didn't know what to expect next.

Jack and Trevor didn't pay her much attention. They talked about this and that, and Jack went to the kitchen to get more beer. When he returned he occasionally circled her clit with a wet finger, or briefly rubbed her asshole, still refraining from penetration.

She had lost track of time…it seemed as though she'd been laying like that forever when Jack announced that he was getting hungry, and suggested that they all go out for dinner.

Carissa released her pussy lips and began to sit up, when Jack stopped and looked at her. "What do you think you're doing?" he boomed.

"I thought…" she replied meekly when Jack interrupted her…

"Lay back down, exactly the way you were. I'll tell you when to get up, slut. I'll be right back." he announced as he stood up and went upstairs to the bedroom. He returned a moment later holding something in his hand. He sat back down between Carissa's legs. In his hand was a string of large beads.

Carissa's eyes widened as Jack explained that he thought the beads would make dinner a little more interesting. He gently rolled them around her wet slit, preparing them for insertion. Then he placed the first bead against her asshole firmly pushing and twisting it at the same time. With minimal effort the first bead slipped into her ass. He pushed it in deeper with his finger, sliding in all the way to his third knuckle. He fingered her deeply with the insertion of each additional bead …pushing and stretching the sides of her rectum every time.

Trevor watched silently as Carissa sighed and moaned, desperately wanting even more stimulation. But Jack wasn't ready for that just yet. 'Maybe later, when they get home' he thought, with a trace of a smile.

"Good Girl." Said Jack as he stood up. "Now, you can fix yourself so we can go. Don't take too long."

Carissa stood up, very aware of the fullness in her ass…and the plastic ring dangling between her ass cheeks. She smoothed her skirt, buttoned her shirt and fluffed her hair with her fingers. She dabbed some gloss onto her lips and they were on their way.

She scooted into the middle of the seat in Jack's big truck. "Keep your knees apart" ordered Jack. "Farther…more" he said in that condescending tone. Of course Carissa complied, pulling her legs apart as far as she could, her skirt hiking up in the process. The ride was sort of cozy…they talked and laughed…As they drove, Trevor stroked her pussy, always making sure to stop before she got too close to cumming. She was worried that all her wetness would start to leak onto her skirt.

Carissa sat between the two men in a big semi-circular booth. During dinner Jack and Trevor took turns sliding their hand beneath her skirt. Carissa couldn't eat…she had been on the verge of an orgasm for what seemed like hours.

Luckily they finished dinner quickly and Carissa hoped they'd be on their way back home in a very short time. As they were preparing to leave Carissa noticed Jack discussing something with their waiter. 'Now what!?' she wondered.

Jack leaned close to her and said, "It seems our waiter thinks you're pretty hot. I told him that there's something you'd love to show him. I want you to follow him to the office and show him what you have in your ass…and let him play with it if he wants to."

Carissa gasped in horror. "Oh Jack, I can't!! Please don't make me…" Jack interrupted her.

"Fine, Carissa. You've been very disagreeable today. Let's just go home and take care of this there." Jack said coldly. She knew she was in trouble, exactly how much trouble she did not know. "But first", Jack continued, "you will follow the waiter".

As Carissa slowly rose to her feet she looked at the waiter who stood patiently waiting for them. Jack pushed her towards him and they followed him down the hall. The young waiter opened the door and the three of them stepped inside. In the office there was a big oak desk, two wingback chairs, and the usual office accoutrements.

Immediately, Jack ordered Carissa to raise her skirt all the way up and to turn around. "Does she always do everything you tell her to do?" the curious waiter asked.

"She's my slut and loves to be looked at and played with", explained Jack. He then kneeled behind her, grasped her butt cheeks and pulled them apart, revealing the plastic ring and the string in her tight asshole.

"Whoa, dude…!" exclaimed the enthusiastic waiter "how cool is that!…"

Jack grinned at him and said "Yea, it is, isn't it…go ahead, give it a pull."

Carissa couldn't believe that they were staring at her ass and discussing it as if she wasn't even there.

"Are you sure?" the young man asked…"I mean… well… she won't mind or anything?"

"I'm positive' Jack replied. "Tell him Carissa…tell him that you like to have your ass played with."

"Yes, Sir" Carissa responded weakly, "I do… I really love to have my ass played with" she assured him.

With that the waiter gently tugged on the ring, causing a bead to barely peek out of her ass. "Wow" he whispered…

"Pull a little harder" Jack coached as he stretched her ass apart more.

The waiter slowly tugged at the string…causing the bead to slip out of Carissa's ass. She was terribly aroused, desperately needing relief. But knew right away that she wasn't getting any yet…

"Well, we really have to get going" said Jack as he slowly stood up. "Fix yourself, so we can leave. I don't want to keep Trevor waiting". The ring and bead swayed freely beneath Carissa's skirt, and the remaining beads rolled around inside her as she tried to compose herself for the walk to the truck. They walked to their table where Trevor was finishing his drink. He stood up and they all walked outside. Again Carissa sat in the middle and this time opened her knees shamefully wide without being told. But she was ignored. The men spoke to eachother without including her. She knew that Jack was still mad at her.

When they arrived back at the house, Jack immediately ordered Carissa to strip. She looked at Jack with pleading eyes, but his gaze was stern and unrelenting. Carissa peeled off her clothes.

"Now come here." He commanded.

Carissa looked at Trevor out of the corner of her eyes as she walked towards Jack. She stood before him…waiting.

"On my lap, ass in the air…knees apart" he demanded. Now she knew…

"Trevor", Jack said "do you mind giving me a hand? Pull her ass apart for me." She felt him pry her cheeks apart…and then she felt the first stinging ~smack~ on her ass. At the same moment she felt one of the beads being jerked from her clenched hole. She gasped in surprise and lust. The sensations overwhelmed her.

The next ~smack~ occurred at the same time another bead…and another, was pulled out. This continued until all the beads were roughly removed. Assuming that her punishment was finished Carissa relaxed on Jack's lap.

Just then Jack stuffed a wet finger into her now stretched anus…sliding it all the way in…simultaneously slapping her ass. Carissa, caught by surprise, grunted, and momentarily thrashed about. Trevor held her firmly, keeping her cheeks spread widely, allowing Jack to finger her ass deeply as he spanked her. After about a minute, he added another finger…stretching her sphincter even further as he twisted his hand and wriggled his fingers, while the stinging slaps to her ass continued.

After about a dozen or so slaps, Jack decided that she'd been spanked enough, and he wanted to watch her cum. The hand that was slapping her ass now found it's way to her throbbing clit. He circled it with his fingertips as he continued to pump her ass. Taking Jack's cue Trevor slid his finger into her slippery pussy.

Carissa whined and moaned…begging Jack to let her cum. 'Not just yet, my beautiful slut' thought Jack…he loved to watch her writhe in need and ecstasy as she sought relief.

Trevor slid another finger along side the first…her juices drenching his hand. Carissa thought she could not hold back her orgasm another second when Jack finally breathed in her ear…"Okay, Baby…you can cum now." He finally said.

The two held her tightly to maintain the deep penetration in both of her holes…stiring and probing her…Jack rolled her quivering clit between his slippery fingers.

Carissa bucked and thrashed wildly as her orgasm overtook her. Gradually her body began to relax…and her orgasm began to subside.

Exhausted, Carissa remained on Jack's lap. He stroked her hair…then kissed her. He carefully picked her up and carried her to the sofa, where he gently lay her down and covered his beautiful slut with a soft blanket.