Bob Meets His Match

 

Bob is a tall, muscular twenty-six year old with a handsome face and a deep voice used to impress and demand respect. He has wavy blond hair combed straight back and a small, neat mustache and mini goatee. He was a football hero in high school. He was also a bully who would intimidate guys and have his way with girls. A mediocre student, he managed to obtain a bachelor's degree in business and finance at the state college with his football coach putting in a good word with his professors. He easily impressed women with his good looks and had an active sex life. He never dated a woman more than three or four times, having a love 'em and leave 'em attitude. Relationships with guys, except his best friend, Frank, were sports related and shallow.

 

These patterns continue today with Bob leaving a trail of disappointed and angry women in his wake. He is independent and emotionally self-sufficient and often seen as arrogant. He works as a stock trader and is a successful risk taker who is resented by his peers. His drinking buddy, Frank, is steady, sensible and well liked. Frank is attracted to the excitement of Bob's risk-taking behavior. He has been Bob's friend since high school and now tries to help him modify his more obnoxious behavior. Frank has a Sensitive/Secret position with the Defense Investigation Service (DIS) and Bob adds excitement to his otherwise quiet, conservative life.

Tonight, Bob and Frank attend a concert and end up sitting next to a beautiful blond. Bob falls for her immediately. They learn her name is Vanessa. Bob flirts with her, planning to intimidate the guy with her. She ignores him and strikes up a conversation with Frank. When Bob persists, she tells him she prefers Frank and gives Frank her phone number. Her date is actually a cousin from out of town.

Bob calls her the next day, as she knew he would, saying he is Frank and asks her for a date.

"Sorry, Frank. I only gave you my number as a put down to your obnoxious friend." Now Bob is in the unenviable position of having to admit he is, in fact, that obnoxious friend.

"You actually intended to get me to agree to a date by impersonating your friend Frank?"

"I would show up and turn on my charms."

"What charms? I didn't see any charms. Also, you must be stupid to think I wouldn't recognize your deep voice."

"I guess I got off on the wrong foot. I really want to make it up to you." This woman is obviously not going to be a pushover.

"You'd have to be on probation."

"Probation?"

"Until you develop a sense of humility."

 

"What do you mean?"

"You were rude to my date, not knowing he was my cousin."

"I'm kind of competitive, I guess."

"And used to having your own way."

"Yah. Well, I could be more flexible."

"How about having it my way?"

"Anything you say."

"I'll remember that."

"So, how about a date?"

"Report to my house at three PM sharp Saturday. Don't eat anything, don't wear underwear or socks, and don't be late."

Bob is intrigued and sexually aroused by these requirements. He agrees immediately. He tells Frank he has a hot date with Vanessa and Frank acts surprised, although he has been in communication with her in a conspiracy to teach Bob some humility. He likes Bob but is often embarrassed by his gross behavior, especially when they double date. In their conversation, Vanessa learns Bob's dating history, current habits, social hangouts, likes, dislikes, and place of employment.

Bob spends the week thinking of nothing but seeing Vanessa on Saturday. He now anxiously rings her bell at two forty-five. There is no response and after a few minutes, he phones her.

"I said three PM."

"You said don't be late. Not don't be early."

"You will learn to follow orders precisely in our relationship. I said three PM sharp. Do you understand?"

Bob's natural inclination is to argue and dominate with logic but he suppresses this. He does not want to mess up his chances with this beautiful woman. He also feels a strange excitement in being told to follow orders by a woman. This is certainly a unique experience.

"OK."

"Say yes ma'am."

"Ah...yes... ma'am." Yes mother.

"Now take your shirt off while you wait."

"What!?"

"You are being disciplined for not following orders and disturbing me prior to your appointment."

"But, I... You're really going to make me stand here exposed?"

"You will also learn obedience. Now take it off! And stay on the porch."

Bob looks at his watch and thinks, twelve minutes to go. I can do this. As he unbuttons his shirt, he feels a surge of stimulation in his cock. He is wearing low cut jeans and as he slowly pulls the shirt up and off, feels exposed and vulnerable in the breeze. He is proud of his physique, but displaying it by conspicuously standing on a neighborhood porch is not something he would voluntarily agree to do. But he is doing as he is told, being punished like a disobedient child. He experiences excitement not only from the exposure but also from his willingness to follow orders from a woman. Sexual stimulation is paired with the unique feeling of allowing someone else to be in control. The minutes tick by slowly as he stands helplessly, shifting from foot to foot, holding his shirt in his hand. After five minutes, the mailman arrives and stares at Bob as he leaves a parcel at the door.

Bob mumbles, "It's just a joke."

"Looks like the jokes on you."

At three o'clock sharp Bob rings the bell. Vanessa opens the door, pulls him in by his nipples and gives him a long, passionate kiss. "I think we're gonna get on well together, you handsome boy."

"Yes, ah, that is yes ma'am," Bob stammers. He's flooded with mixed feelings racing through both mind and cock. The only thing he is sure about is that this woman turns him on as no other has.

"Well, you might as well finish undressing."

He eagerly complies and his erection springs straight out. She grabs his cock and pulls him. "The playroom is downstairs." For a guy always in control and controlling others, he allows this fully clothed woman to pull him, naked and stumbling to keep up, behind her. He could only think of how fortunate he is to be near her, to have her attention and have a chance to please her.

The playroom consists of a bathroom, stationary bike, treadmill, wall hooks and hooks attached to ropes dangling from ceiling pulleys.

"Where's the bed?" Bob asks, innocently. Vanessa obviously earns her living as a dominatrix but Bob only sees her as a potential girlfriend.

"Upstairs where you may be rewarded after you finish your probation," Vanessa purrs, rubbing her hand up and down his cock with pre cum as lubrication.

Now Bob is in heaven, but just as he is about to ejaculate, she moves her hand up to pinch his nipples and gives him another passionate kiss. Bob moans in disbelief at the denied orgasm.

In a frustrated daze, he allows himself to be pulled to the back of the treadmill and onto the belt. Vanessa fastens a strap around his waist and hooks it to the front of the treadmill with a chain.

"I want to see that gorgeous chest glistening with sweat." She turns the machine on to a moderate three miles per hour to allow Bob to adjust.

At this point Bob realizes there are three-foot walls sloping up and out on each side of the belt. There is no room to step off to the side and rest. Since he is chained to the machine, he has to keep running with his partially erect cock bobbing wildly. The speed is now five mph.

"I didn't agree to be tortured," he shouts. There is no response and he looks back and around the room only to find he is alone. Vanessa has switched on an overhead heater, increased the treadmill speed and gone upstairs where she remotely controls a video camera. Bob feels anxious about how long he can continue. For the first time ever, he feels weak and insecure. He is sweating profusely from the heater as well as from feeling trapped and dependent on Vanessa to release him.

Just as his legs are about to give out, Vanessa appears. She slows the speed to one mph and watches him pathetically plod along, dripping sweat.

"That was cruel," he gasps.

Releasing him and caressing his sweaty torso, "You did good big boy." She scrapes and pinches his nipples and complements him on his torso. His cock immediately hardens. He raises his hands and she firmly lowers them. "You can take a shower now. Assuming you've worked up an appetite, I'm going to let you take us out to dinner." She smacks his butt in the direction of the bathroom.

She has laid out his shirt and jeans. After his shower, he finds his shirt won't stay closed as all the buttonholes have been elongated.

"My shirt won't stay closed!"

"I told you I love your gorgeous chest. I'm going to show it off."

The shirt is a tight fit to emphasize his muscles and now spreads open obscenely. He realizes this will be embarrassing and feels another jolt of stimulation at the thought of having to obey this woman at the cost of his self-respect. On the other hand, he is happy to finally do something to make this day's experience seem more like a real date.

She has picked an expensive, white tablecloth restaurant and Bob reddens, as the maître d' looks them over with a knowing smile. Vanessa looks sophisticated and refined while Bob looks and feels like her sexy boy toy. His embarrassment is the next step in her plan to instill a feeling of male inferiority. When the waiter appears, Vanessa does the ordering.

"I'll have a martini up with an olive and the boy will have a glass of milk as he is in training." Bob is too embarrassed to speak.

The waiter brings the drinks and asks Vanessa for her order. Then, still looking at her: "And for the young gentleman?"

"He'll have the split pea soup and the liver and noodles plate with turnips."

Bob is wide-eyed and speechless. She has managed to select every food he cannot stand. "But Vanessa..." he starts and then stops when the waiter turns to him with raised eyebrows. As he leaves to turn in their order he hears, "Just drink your milk Bobby." Two, twenty-somethings at the next table are obviously listening intently, glancing at them and giggling. Bob feels his face flush.

He forces himself to eat some of everything as he is starved. He had eaten nothing Saturday morning, as instructed and very little Friday night, thinking this was prerequisite to some exotic sexual experience. Now he thinks she must have some intuitive sadistic sense as he has no idea she had talked to Frank. He can only feel inferior and that she has the power to render him weak and helpless. Before he can sort out these feelings, Vanessa says, "You can have desert at my house and I'm talking about upstairs this time." Bob's ability to think rationally now quickly melts away. When he signs the credit card bill, she checks to see if he gave a good tip, "To that nice waiter."

When they enter Vanessa's house she says, "hands up" and rips Bob's shirt up and off. She kisses and fondles his chest and then squeezes his nipples hard between her knuckles. She has taken complete control.

"Ouch!"

"Off with the jeans."

He rapidly kicks off shoes and jeans as she keeps squeezing. His cock pops out at full mast. Vanessa sits in an oversized chair and spreads her legs.

"Come get your desert."

Bob is dumbfounded. And extremely frustrated.

"Let's go! You've got me all heated up. Come on all fours like the tiger you could be."

Here he is, upstairs but not in the bedroom, stark naked and ordered to crawl to a fully clothed woman to eat her juices. He has eaten pussy before but it was always to get a woman he'd seduced hot and into bed. Now he finds himself crawling to this obviously superior woman, giving her several orgasms on his hands and knees, and only touching her with his mouth and face. She becomes excited, grabs his head, and gyrates, covering his face with her juices and nearly smothering him. He feels helpless and even more sexually frustrated.

Finally satisfied, she pushes him away with her feet on either side of his face and asks, "Do you want to go home or sleep in the basement and have some fun tomorrow?"

"I want to sleep with you."

"I'm sure you'll earn that privilege in no time but you're on probation. Remember?"

Poor Bob ends up masturbating in the basement bathroom, unaware he is being videotaped through a one-way mirror. Vanessa makes a good living charging wealthy masochists for her services or blackmailing VIP types. Bob does not fit either of these categories. She has other plans for him. He inflates the air mattress provided and crawls into a sleeping bag. He fantasizes seeing her naked and that he will satisfy her and build an intimate sexual relationship. If only she wasn't so mean!