Bobby Learns His Lesson

Story Info
Bobby gets caught chatting with a woman by his girlfriend.
6.6k words
4.24
35.5k
16
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

Allison put the card into the reader on the hotel door and entered the room with her friend Samantha in tow. "Bobby, you here?" she called out as she put down her shopping bags and looked around. She had been in the seminar all day and then went with Samantha to do a little shopping. It was nice that Bobby was able to accompany her to the seminar and spend time with her in the evenings when she was free.

"No sign of him," she said to Samantha, "he must be working out." Allison began to pull out the clothes she bought.

"That is a beautiful and quite erotic blouse" Samantha commented. "He is going to love it and that hot skirt" she continued, "It will surely turn his head. Hell, any man's head."

Allison removed the tags and looked at them again. "Mind if I use your computer to check my e-mail?" Samantha inquired. "My i-phone isn't working."

"Sure," Allison responded, still admiring her purchases, "it is on the desk." Samantha hit a key and the screen came to life with a chat session between Bobby and someone named Lisa of Paris.

"Euuuwww" Samantha said as she looked at the exchange and then called Allison over. Allison started reading the exchange.

Lisa of Paris: Oh yes...and you are rock hard...with pre-cum glistening on your penis ...want it soooo bad...

Bobby: my two fingers gently rub you

Bobby: you want me in you?

Bobby: i want you to cum first with my mouth

Lisa of Paris: my hips moving up and down and my hands come up to join your hands as they massage my breasts...

Bobby: yes Lisa yes

Bobby: my hands are full with your breasts and those nipples are pointing out between my fingers

Bobby: you feel me squeezing them and my tongue flicking your button

Bobby: faster and faster my tongue works you

Lisa of Paris: ohhhh yes...make me cum hard...oh yes...make me scream your name...oh Bobby...my pussy aches for release ... tongue my clit ... squeeze my breasts ... I am moaning ... please make me cum.. mmmmmmm ... Oh Bobby...your tongue feels so good...ooohhh don't stop...

Allison slammed the screen of the laptop down. "That bastard," she exclaimed!. "I, I will kill him." She was certainly embarrassed by the exchange, especially with Samantha discovering it. "Sorry Samantha," Allison said, her eyes clenched shut.

"No problem Allison, men will be men. I better get going" Samantha said as she grabbed her bags and headed out the door. "I will see you tomorrow morning."

Allison sat perplexed as to what to do. So do I leave now for the evening, wait until he comes home, or better yet teach him a good lesson? Hmmm, I will go with the latter, teach him a good lesson. She decided after a brief moment. Allison picked up her raincoat and headed out to do some more shopping. She would need a few items to teach Bobby a good lesson.

When she got back to the room Bobby was getting out of the shower. He came out of the bathroom with a towel around his waist. "How was the shopping spree there, sweetie?" Bobby asked as he put his hands on her waist and kissed her.

"Hmm, lots of fun." Allison said as she looked over his broad shoulders, formed pecs, and his washboard abs.

"Glad to hear it" he said. He walked into the bedroom to get dressed.

Allison cleaned up and put on her new outfit. When she walked out Bobby looked her over and whistled. "My, do you look hot in that." Bobby kissed her on the mouth and then placed soft kisses on the side of the neck. He didn't stop there and continued down her chest, trying to make his way down to her breasts.

"Woo there sailor. I did not hear liberty call being sounded. We need to keep our reservation."

The whole evening, Bobby demonstrated how horny he was and how he couldn't wait to get Allison back to the room and in bed. When they got back to the room Bobby slowly undressed Allison and laid her down on the bed. He then stripped himself and lay on top of her with his arms straight, straddling her head.

"Hmm," Allison commented as she reached up ran her hands up and down his toned arms and then following them to his shoulders and chest. She loved his strong pecks covered with soft hair. She always enjoyed running her fingers through it, feeling the firm muscle underneath. Bobby moved next to her on the bed and began to caress her breasts. His fingertips lightly traced the outline of each breast and nipple that now pointed up toward the ceiling.

After a few minutes he stopped caressing Allison's breasts and slowly dragged his fingertips down across her abdomen and then skirted her pubic area on the way down her thigh. He moved down on the bed and gently grasped her ankle and brought it up to his lips. Supporting her leg under the knee with his left hand and her foot with his right hand, Bobby started to kiss her ankle. His lips then traveled to her big toe that he took into his mouth. His warm, wet, and soft mouth covered her toe and she felt his tongue swirling over and around it.

Allison sighed enjoying the pleasure he was providing her. One by one Bobby took her other toes into his mouth making Allison melt into the bed. After removing his mouth from her toes he ran his tongue under the sole of her foot and then moved his way up her leg to her calf. He alternated between kisses and long strokes of his tongue that outlining her calf muscle. She moaned softly and believed his soft caress could not be matched by any other man. He always showed her how much he adored her body by paying attention to each part. Bobby progressed slowly and when he reached her knee he made eye contact with her. Despite the low light, she could see his devotion to her body and the desire to pleasure it in his eyes. He continued by kissing the sides and under portion of her knee and then began the long slow journey up her toned thigh.

Allison emitted another soft moan of approval as his technique aroused her further. Once again alternating between kisses, long flat strokes of his tongue as well as long thin strokes with its tip of his tongue Bobby began to drive Allison crazy with desire. Allison could already feel her vagina preparing for the upcoming festivities. It was already oozing with her juices which were slowly running down the inside of her thighs and onto the sheet. When he progressed halfway up the inside of her thigh, Allison could not conceal her delight any longer.

"Ohhh Bobby," she moaned. "you are driving me crazy. " Her moans continued with each louder than the proceeding. This encouraged Bobby to take his time in order to build up the desire so she would experience a toe curling orgasm.

Her breathing now labored, she moved her hands up to her breasts and began to massage them. As Bobby looked up at her, his penis grew harder. Nothing sexier than a woman massaging her breasts, he thought. As Bobby closed in on her vagina, his hard penis rubbed against her leg. Feeling how hard he was only added to Allison's excitement.

The chemistry between the two of them was always electric; each feeding off of the others actions. She couldn't wait until she felt his long hard shaft entering her. With his head only a short distance from her vagina, Bobby could smell her sweet juices, her female response to his male actions. He looked up at her vagina, the lips engorged with blood, the button of her clit peaking from its protective covering, he could now see her juices and knew that her vagina was already well lubricated. When his tongue began to trace the skin around her vagina, Allison massaged her breast with much more vigor. Bobby surprised Allison with one broad, flat stroke of his tongue over her vagina. Allison's arms then shot out to her side and she gripped a handful of the bed sheet with each hand and writhed to and fro on the bed. He repeated this action and then stroked her clit with his firm tongue sending pulses of pleasure through her body. Repeatedly stroking her clit with his tongue was driving Allison totally mad with desire.

"Oh God, Bobby, stick it in me." Allison requested.

Bobby obliged Allison's request and drove his tongue deep inside of her vagina, her thick sweet juices coating his tongue and lips. Bobby was himself excited and mad with desire. He withdrew his tongue and sucked Allison's clitoris into his mouth. He began flicking her button with the tip of his tongue and followed that with a swirling motion. Allison was writhing on the bed as her orgasm began to build. Bobby placed a hand under each cheek of her butt and picked her up so he could better apply his technique.

Allison moaned as she felt the orgasm build deep inside of her. "Yes Bobby, yes, drive me wild, make me cum with your tongue." Bobby sucked her clitoris hard and flicked it rapidly resulting in Allison bucking up and down as his hands held onto her butt.

"Shit," she said as she reached a heart pounding orgasm.

As her orgasm subsided, Bobby slowed and then stopped his attack on her clitoris. Bobby began to kiss his way up Allison's toned body. She could feel his hard penis travel up her thigh until it was perched in front of her vagina. Allison pulled Bobby's head and guided it so their lips met.

They kissed passionately as if it was the last kiss that either of them would ever experience. Allison tasted her sweet juices on his lips as she sucked his tongue into her mouth and caressed it with her own tongue as if it were his penis. Allison had to have him now. Reaching down she guided his throbbing member into her wet vagina. He filled all of her with one deep stroke and she began to experience that sensation that she had long waited for. Bobby slowly withdrew and lowered his hips, allowing his lover to feel his penis stimulate every nerve ending in her vagina.

Once again, he placed his hands under the cheeks of her fine butt and picked it up so the head of his penis pointed directly at her "G" spot for maximum stimulation. A jolt ran through Allison as his penis slid over the ridges of her "G" spot. She began to experience another body-shuddering orgasm. After a couple of independent convulsions, he knew her orgasm was over and he slowly lowered her butt to the bed. Allison, wanting Bobby to climax just as hard as she did, wrapped her legs around him. She could read his body and knew he was close to cumming himself.

"Fuck me hard," Allison whispered into his ear, her breath tickling the hairs inside his ear.

Excited from her vocal desires, Bobby drove his hard penis into Allison over and over until they were both on the verge of climaxing. "Fuck me Bobby, fuck me, make me cum."

"Look into my eyes Allison." Bobby requested in a slow soft voice.

Allison looked up into his eyes and they connected. Being able to see into each others' soul, it wasn't long before they both exploded in mind blowing orgasms.

Falling to the bed and supporting himself on his elbows, he gently kissed her soft lips. Bobby continued to place light soft kisses on her forehead, eyelids, cheeks, neck, and ears. Not a word needed to be spoken as he rolled to her side and pulled her into his arms. With her head resting on his chest, she listened to his heart winding down from the passionate lovemaking they just experienced. His fingertips stroked her back and shoulders and then ended up, as always, in her hair, his fingers working their way through her soft brown hair like a comb until they fell asleep in each others' arms.

The next day, they woke up as they had fallen asleep, in each others' arms. Allison knew it would be a day like no other in either of their lives. Bobby had some errands to run and Allison saw him off with a kiss. Allison went to her seminar and waited for the afternoon to arrive. It would be then that Bobby would learn his lesson.

It was 4 pm when Bobby entered the hotel room. "Allison, I am back."

"Be out in a minute," Allison replied. Allison came out of the bedroom wearing a black leather corset, short black leather skirt, black stockings secured with a garter belt, black stiletto boots, and a riding crop. Her long brown hair was up in a bun and she was wearing her black rimmed glasses. She certainly had that fantasy, super-hot librarian look. The corset did little to conceal her breasts and it fit snugly, leaving nothing to the imagination. She slapped the riding crop in her hand and commanded Bobby to come to her.

"I said, come over here," Allison reiterated.

Bobby laughed as he thought that this was just play.

"Take your clothes off."

Bobby was still laughing as he started to take his clothes off. After he dropped his shirt, he reached for Allison. She hit his hand with the riding crop, sending a sharp sting through his hand.

"Don't touch me unless I give you permission," Allison said. "Get the rest of your clothes off."

Bobby stripped down to his skivvies.

"Everything off."

Bobby took off his skivvies and threw them in the pile. Allison walked behind Bobby and told him to put his hands behind his back. Once he did, she removed a pair of handcuffs that she had tucked behind her and applied them to his wrists.

"Oooo," he said, "am I supposed to be scared?"

She then pulled out a blindfold and put it on him.

"My, my, have we been reading Cosmo again? How to spark your sex life?" Bobby laughed.

Allison then pulled out a pair of foam earplugs that he used on the pistol range. "I am going to put these earplugs in your ears and I want you to get on your knees and not move," Allison said, giving him a light whack on his butt with the riding crop. She rolled the earplugs between her thumb and forefinger and stuck them in his ears. She figured that any sound would be sufficiently muffled.

Bobby knelt there for about 5 minutes, blindfolded and with the earplugs in. The position was becoming uncomfortable and he wondered what was going on. After a few more minutes, he began to get a little concerned. This was not like her.

Shortly thereafter, Allison pulled the earplugs out.

"I see you were on Literotica yesterday afternoon, is that true?"

Bobby answered, "Yes, just looking at some stories."

"And the Lady of Paris?" Allison said as if she was interrogating a witness on the stand.

Bobby swallowed hard. "What Lady of Paris?" he said.

The whistling of the riding crop traveling through the quiet air was indistinguishable until it was too late, hitting Bobby squarely on his butt. "Ouch!" Bobby responded.

"Need I ask you again?"

"OK, I was chatting with her. It was all innocent stuff," Bobby said.

"Good, I am glad we are able to agree that you were online chatting with her."

Bobby was wondering where all this was going. Allison wasn't mad at him, she just wanted to have a little fun and teach him a lesson. She then removed Bobby's blindfold. His eyes began to adjust to the light. As his vision adjusted, he saw Allison in front of him and he began to make out other figures in the room. At first he thought he was seeing things. He then realized that he was correct, a woman came into focus behind Allison. Bobby suddenly realized that he was kneeling nude in front of a strange woman with his hands behind his back. Bobby was embarrassed and did not know what to do. With his penis shrinking, Bobby tried to get up. Allison pushed him back down and struck him with the riding crop on the front of his thigh, just inches from his shrinking penis. The strike convinced him not to try that again.

"Don't move. You see, Bobby," Allison stated as she slowly circled him, "I am not upset with you, just a little embarrassed. I am an attractive woman and our sex is fantastic. There is no reason for you to venture alone onto an online chat, especially using our logon. My friend Samantha asked if she could check her e-mail and I let her, thinking nothing of it until she discovered your chat session. She was offended and I was embarrassed, quite a bit. And now it is your turn to be embarrassed." And with that the riding crop struck Bobby's bare ass again.

"Shit!!," Bobby said as he looked at the women.

"Samantha is a member of my seminar group and she had nothing to do this evening so I invited her up for some refreshments. You don't mind, do you Bobby?"

Bobby was slow to respond and that prompted Allison to use her new found toy which she swung and hit Bobby's butt again. "Oooo! Of course I don't mind." Bobby said.

"Good, come on over here." She said to Bobby. Bobby got up and walked over to Allison. She took his shrunken penis into her hand and turned to Samantha. "It is usually bigger, I think he is a little embarrassed. Oh," Allison said as it pulsed and jerked in her hand. "it must be coming around."

"Oh yes, I can see it now." Samantha said. Samantha was a petite brunette with a slim body. Her olive skin and big brown eyes were features one could not forget. She was wearing a sundress that not only displayed the tops of her ample "C" cup breasts but showed off her nice firm legs as well.

"Watch, let's see what happens with this." Allison said as she leaned over and kissed the growing member. Bobby's penis responded immediately growing in her hand.

"Ahhh that seems to have helped it," Samantha said. "May I see what I can do?"

Sure Allison replied. She added another red welt to Bobby's butt. "Well, get going, Bobby," Allison ordered.

Bobby, wondering when all this would end, walked over to Samantha with his hands still cuffed behind his back.

"Oh, it seems to have shrunk a little again. I think he may still be embarrassed," As Bobby stood in front of Samantha, she reached up and took Bobby's penis into her hand. She gave it a few strokes and it once again started to grow again.

Allison swung of the riding crop once more adding another bright pink welt. "I can't believe you would get hard in another woman's hand. I apologize Samantha, how barbaric."

"It's okay with me Allison, no reason to apologize. I kind of like it, him in this position and us ladies in control."

"Yes, I guess you are right," Allison agreed.

Samantha kept Bobby's penis in her hand and began to rub the head with her thumb. Bobby's response was normal and immediate. Any sense of embarrassment was gone as he became excited by her touch and grew hard almost reaching maximum length and girth.

"Wow, he is as big as you said he was. I love the shape of the head, very big and the rim around the head very distinct." Samantha said while she outlined the head of Bobby's penis.

Bobby's penis began to jerk in her hand and Allison struck him again with the riding crop. Bobby winced and his penis immediately responded by softening,

There was a knock at the door and a voice said, "Room service."

"Open the door for room service, Bobby."

"I can't, I am not wearing anything."

SWACK!! (Another swift strike of the riding crop.)

"I didn't ask you if you were wearing anything, I told you to open the door." Bobby didn't move until Allison raised the riding crop again. As Bobby walked to the door in the buff Allison turned to Samantha and remarked "He needs to work on discipline."

Bobby turned his back to the door and pulled the handle down opening it just a crack. The room service guy looked through the crack at the empty room and didn't make a move until Allison called him in.

The guy opened the door the rest of the way and as he pushed the cart in, he spotted Bobby behind the door. Astonishment at Bobby with his now shrinking penis out there for all to see , the guy looked straight at the ladies while he pushed in a cart with strawberries, chocolate sauce, whipped cream and a bottle of champagne. He placed the items on the table in front of the women and opened the bottle of champagne before walking towards the door. Before walking out the door, the room service guy gave Bobby one last look and shook his head.

"Dig in," Allison said to Samantha as she poured them both a glass of champagne. They both started enjoying the strawberries. Allison then dripped some chocolate sauce off of a strawberry onto her boot. "Hmm, can't waste that. Bobby, lick that chocolate off of my boot." Allison said as she held up her boot and started tapping the riding crop on the leg of the table as a reminder. Getting the hint, Bobby walked over to her and with his hands still cuffed behind his back, started to lick off the chocolate.

12