Bobby Learns His Lesson

Samantha, whose excitement had been building since she entered the room, squirmed a little in her seat at the sight of Bobby licking chocolate off Allison's boot. Although the whole scenario was getting her pretty excited, she remembered that the plan was to make Bobby as embarrassed and sexually frustrated as possible.

She knew it was her turn and dripped some whipped cream on the instep of her foot. The white of the cream was in stark contrast to her olive skin. It began to run down her instep and between her toes.

"Bobby," she called, "it seems I have dripped whipped cream on my foot. Can you get it so it isn't wasted?" Samantha took off her sandal and raised her foot to help Bobby out.

Totally red with embarrassment, Bobby made his way on his knees over to Samantha.

"Make sure you get it all Bobby," Allison said as she watched with total enjoyment.

Bobby licked the cream from her instep and followed its trail to her toes.

"Some got in between those toes there Bobby," Samantha pointed out. Bobby, on his knees, looked up at her as he took her toes in her mouth. As Bobby's tongue swirled around the digits and sucked, Samantha closed her eyes in pure joy. Samantha did a great job of hiding her excitement and when Bobby was done getting every bit of the cream, she traced a line with her big toe down his chest, over his abdomen and then to his crotch, where she ran it up and down his penis. This is making me too hot, Samantha said to herself as her heart pounded and her juices began to flow.

"Ok, Bobby, enough; come here" Allison said. Bobby got off of his knees and walked over to Allison. His semi-erect penis bobbing with each step. Allison had regained her composure as she was getting excited as well. She dipped a strawberry in chocolate and then used it as an instrument to cover Bobby's penis with chocolate. When she was done, she took a big bite out of the strawberry, drank some champagne and then leaned forward and began to lick the chocolate off of his penis.

Bobby thought he was going to come right then and there. He glanced over at Samantha who was watching closely and sucking the chocolate off the end of a strawberry. Allison's technique made his penis hard as a rock and throb. She took the hard penis into her mouth. The movement of her cheeks indicated her tongue was swirling around the member. Bobby's knees buckled but he caught himself.

The combination of her mouth and tongue must make a man crazy with desire, Samantha thought.

Allison recognized that Bobby was getting too turned on and stopped, leaving his penis bobbing and his senses frustrated. She looked over at Samantha and gave her a head nod as a prompt that it was her turn again.

Samantha, whose dress was hiked up fairly high on her thigh, dropped more whipped cream, this time landing on the top of her thigh. From its point of impact, it left a trail of white sweet foam as it slowly ran down the inside of her lower thigh.

"Well, what are you waiting for, Bobby?" Allison asked said. Bobby knew the drill now and went over to Samantha and knelt before her. She spread her legs, putting one on the coffee table, while the other was over the arm of the chair, giving Bobby a look up her thighs, just short of her crotch.

That was not what we discussed, Allison said to herself, referring to the conversation she had with Samantha earlier.

Bobby leaned forward and caught the cream with his tongue before it made its way to the seat cushion. His broad tongue made its way up the inside of Samantha's thigh. When she raised her leg, Bobby got a view of a red thong. Bobby thought he would have a little fun and started to lick further up her thigh. The scent of Samantha's womanhood was drawing him closer to her moist vagina and her heavy breathing served as encouragement to his thoughts of putting his mouth over her.

Once again the sound of the riding crop hitting bare skin brought everyone back to reality, especially Bobby. "No, no, no," Allison said. "There was no cream up there Bobby."

"Oh" said Samantha. "Shouldn't that be my duty to punish him as he was licking where there was no cream?"

"Why, I guess so" Allison agreed. She leaned forward to give her the riding crop but Samantha refused. "I would rather use my hand."

"Come over here Bobby and turn around and bend over." Bobby obliged and Samantha looked at his firm cheeks that were decorated with red lines and welts from the riding crop. The view of his butt and his hands cuffed behind his back were quite stimulating for her. She drew back her hand and looked at Allison who gave her the OK with a nod of her head. Smack went the first blow. There was a brief pause as Samantha smiled and examined her hand-print on Bobby's right cheek. She then landed the second and a third blow. Although not as painful as the riding crop, it did sting making Bobby wince. Samantha then inspected her work and ran her fingertips over Bobby's butt which resulted in an increased blood flow to his penis.

The girls looked at Bobby's buttocks and laughed at the red marks. Feeling no pain from the bottle of champagne, they sat and took turns teasing Bobby as the afternoon wore on.

"Ooops" Allison said after spilling champagne down her chin and onto her breasts. "Bobby, I need some help here," she said as she undid the front of the corset. She opened it and pulled it apart providing Bobby with the access he needed to clean her up. Bobby anxiously began licking up the champagne that was running down the top and sides of her right breast. He took her now exposed nipple into his mouth and sucked all the champagne off and then some. He then licked the champagne running down the side of her breast and made sure he got that area right under the breast. Allison grabbed his head and brought it to her left breast that had some champagne on it as well. She directed Bobby's head right to the nipple and held his head there as he licked and sucked all the champagne away. Allison's moans of pleasure were truly erotic and she ran her fingers through Bobby's hair as his tongue flicked against her erect nipple.

Samantha looked on with great interest. Her breathing labored, her hands discreetly massaging her right breast dreaming of Bobby's mouth and tongue on it.

"Oh, God," Allison said as she threw her head back and Bobby gently nibbled on her nipple. Bobby's penis was hard as a rock now and throbbing uncontrollably. He wanted so much to stroke it but with his hands behind his back there was no way for him to relieve himself. He held out hope that he would get relief from Allison or Samantha. That wouldn't be the case, at least not immediately.

Samantha, mesmerized and excited by the action in front of her, was glued to the action. Bobby was an attractive guy and to watch him restrained and pleasing a woman, while handcuffed, was pretty hot. While Allison sat with her head back and eyes closed enjoying Bobby's attention, Samantha's hand slid down and under her dress. She removed her panties and began to rub her clit while closely watching the action. She inserted one and then two fingers into her aching womanhood as she watched Bobby pleasing her friend. Samantha wanted some more action and she didn't want to wait.

"Oh, Bobby," Samantha said. I have seemed to have dropped my chocolate covered strawberry and can't find it. Please help me."

Bobby left Allison's breasts and walked over to Samantha. This time there was no bounce in his penis as it was engorged with blood and stiff as a board. Bobby knelt down and saw that there was chocolate sauce on her thigh, but no strawberry. Bobby lapped that up and noticed that the chocolate sauce ran under Samantha's dress. Samantha looked down at him and picked up her dress only to reveal the chocolate sauce led to the strawberry between her thighs, right before her shaved vagina. Bobby wondered where the thong went as he started to lick up the chocolate with long, broad strokes.

Bobby followed the trail of chocolate to the strawberry, which he consumed in a couple of chews and one gulp. Before him was Samantha's vagina. He could see juices flowing from her engorged lips. He looked over at Allison who was very excited at that point, sitting back in her chair and squeezing her right breast with her left hand while her right was busy massaging her own clit.

Bobby followed the trail of chocolate sauce to the center of Samantha's womanhood. As he got closer there was a scent of both chocolate and her juices. When he reached her pussy he flattened his tongue. Starting at the base of her vagina, his tongue traveled slowly upwards parting her lips.

"Oh shit!" Samantha cried. She grabbed the back of Bobby's head and drove it into her aching pussy, leaning back in the chair in pure ecstasy.

Bobby's face quickly became covered with the liquid mixture and slid to and fro as he licked up her special sauce. He flicked his tongue over Samantha's clit a few times and she immediately reached an orgasm, an orgasm that had been building since he lapped up the whipped cream on her foot. Samantha bucked and writhed in the chair holding Bobby's head against her pussy that was contracting with a desire for something to fill it.

Feeling her orgasm subsiding, Bobby withdrew his face from between her legs. A shiny brown mixture of her juices and chocolate covered his chin, nose and most of his cheeks. Samantha leaned forward and licked some of the mixture from his cheeks and chin.

Before things got too out of hand , Allison cleared her throat and said, "Oh, look at the time. You are going to miss your dinner date, Samantha." A reluctant Samantha looked at Allison and took the hint. She wiped off her mouth and kissed Bobby on the forehead. Before she departed she put her thong around Bobby's neck. It would be one less piece of clothing to remove when she got back to her room in order to please herself with the vibrator.

The hotel door closed. "Alone at last," Allison said. Her heart still raced from watching Bobby please her friend Samantha. She looked at Bobby, his penis red and pulsating and his face still showing the remnants of the Samantha's chocolate-juice mixture. Allison picked up a napkin and was going to wipe it off, but stopped. She then bent over and kissed Bobby on the lips in order to sample some of the mixture.

"Hmm," she said, "that is tasty. You are a lucky man Bobby." Bobby looked at her. His penis ached and was in need of some relief. "Get on your feet, this party isn't over." Allison said. Bobby stood up and Allison took hold of his hard penis and led him over to her chair. She sat down, put some whipped cream on his penis, and began licking it like an ice cream cone. Bobby's penis became even harder receiving the attention that it longed for. Bobby could feel that all too familiar tingling in his balls meaning that his orgasm was building. As Allison sensed this she pulled his penis from her mouth.

"Allison, I'm sorry that I went on chat without you. I will never do it again. I can't take any more of this my cock is going to explode. Please don't leave me this way."

"Can't take any more of this? Is that what I just heard? Ok well then let's get on with something else." She went to her bag and pulled out a black dog collar and a short leash.

"I promise that this won't make your little penis any harder." Allison said. She pulled off Samantha's thong replacing it with the collar and leash. Allison then led him to the corner of the bed. "Thank the lord that we stayed in a decent hotel with a head and foot board." Allison said. She tied the leash to the foot board giving him enough room to move around and access to the end of the bed. She then blindfolded Bobby again.

Bobby thought to himself, I wonder who will be there when this comes off. Allison reached in the bag and pulled out two remaining items; a tube of lube and a strap on dildo. I always wanted to see how it felt to be a man, she thought. And Bobby will feel what it is to be on the other end of a penis. Once strapped on she walked over to Bobby with her new manhood bobbing. She positioned Bobby at the end of the bed and bent him over so his head was resting on the mattress. Allison squeezed out some lube in her hand and applied it to his still hard cock, balls and then around his butt.

After coating everything with the slick liquid and briefly massaging it, she inserted a well lubed finger into his butt. Bobby let out a long and guttural, "Ohhhhhh Allison, what are you doing?"

"Feel good, Bobby?" Allison asked as she inserted a second finger and massaged his prostate.

"Oh god yes Allison, oh that feels so good."

"Hmm baby, here I have more for you." Allison withdrew her finger and eased the dildo into position. "Here we go baby." Bobby was still stretched out from her finger and the dildo slipped in easily.

"Oh, what the hell..., Allison?"

"Yes, it is me Bobby, no one else." She removed the blindfold so he could see the two of them in the mirror.

"What the hell are you doing?" Bobby inquired.

Allison pushed the dildo in further and that shut Bobby up and he moaned in discomfort.

"How does that feel Bobby? How does it feel to be on the receiving end? I am enjoying it," Allison commented. "Being in control, dictating the terms, yes I love it."

They both watched in the mirror as Allison put her hands on his hips, withdrew the dildo, and then slowly eased it back in. Allison could see that Bobby was beginning to enjoy it. Allison reached around and grabbed a nipple between her thumb and forefinger. Slow rolled between her fingers and gave it a hard squeeze.

"Ohhh, shit," moaned Bobby. As Allison built up a rhythm, Bobby's breathing began to become labored. Both of their hearts raced with excitement as the dildo traveled in and out.

Allison suddenly stopped and withdrew the dildo. She unhooked Bobby from the bedpost, turned him around, and then pushed him back on the bed. She threw an ankle over each of her shoulders and re-inserted the shiny dildo fucking Bobby hard. She was possessed now with the power that the 8 inch pleasure tool gave her. With Bobby's ankles over her shoulders, she drove the dildo into him. Allison grabbed a hold of his penis which was still hard as a rock. She was going to give his relief, but on her own terms. When she started to stroke his penis Bobby began to moan. Bobby's angle on the bed was perfect for the dildo to stimulate his prostate. With her stroking his penis and the stimulation, the feeling was beyond anything he ever experienced or imagined.

"Oh Allison, I am going to cum."

Allison stopped stroking his penis and said, "Open your mouth."

"What?" Bobby replied.

"You want to cum, open up your mouth."

"But Allison ..."

"Look, you want me to fuck your ass all night? If you want to cum, then open your mouth."

Bobby had to cum. His cock had been hard for hours. With his ass up in the air and his ankles over her shoulders, his penis was pointing directly at his face. Bobby reluctantly opened his mouth and Allison continued to stroke his penis.

"Ohh Allison, Ohh baby."

"Keep that mouth open Bobby." Allison stroked him faster and all that cum that had been building up over the hours spewed over his chest, face and some into his mouth. Allison continued to pump his penis making his body convulse wildly. Finally Allison stopped and removed her hand. She looked down at Bobby whose face was speckled with his own cum.

"How does that taste Bobby?" Allison said as she scooped some up on her two fingers and put it into his mouth. "Close and suck Bobby." Bobby did as he was told.

Allison unsnapped the dildos straps leaving the dildo in his ass and dropped his ankles. She stepped back and washed her hands in the nearby sink. She dried her hands and donned a black dress that was hanging in the closet. From the jacket of the pocket she withdrew a handcuff key and threw it on Bobby's chest.

"Don't ever let me catch you chatting again or cheating on me Bobby. The embarrassment you will experience today is nothing compared to what you will experience." With that said, Allison departed the room.