Bobbie's Dilemma Bobbie shivered as she pulled up the white stockings and attached them to the tabs of her garter belt. She knew that she only put on this lingerie when she was to receive a sound spanking from her fiance Gary. She had meet Gary almost two years earlier when she attend a class that he taught at the local Collage. Bobbie had just left a relationship with another of the "Bad Boys" types that she found so exciting. Bobbie never missed Gary's Computer Class because she found him to be very attractive. Gary was a successful 36 year old business man who taught classes at the Collage because he liked meeting students and wanted to help them be successful. Gary was not like the guys she usually fell for but with his broad shoulders and brown eyes and hair, Gary was certainly tall dark and handsome. As she opened the drawer and put on the lacy white panties that they had bought at Victoria's Secret to go with her punishment outfit, Bobbie remembered the first time Gary had ask her to see him in his office at school. He told her that the Dean had asked him to tell her that she was flunking all of her other classes and was on the verge of being kicked out of school. He said he was very concerned because she was doing well in his class and offered to help her with her other classes so that she could get off of probation. It was only after she had gotten her grades up and finished his class that he finally was comfortable about asking her out. Gary had always found her to be attractive with her auburn hair and green eyes. He especially liked her outgoing personality that sometimes boarded on sassiness. This was different than his strong silent nature and she helped him loosen up and have some fun. As she fastened her bra and looked in the mirror she realized how much better she felt about herself since being with him. When she was running around with her "Bad Boys" Bobbie was drinking a lot and out till all hours almost every night. She also did not have a lot of self confidence, and let these guys treat her very badly. Now she had finished school and was doing very well at work. She had stopped drinking and was in the best shape of her life. Gary especially liked her bottom, although at times like these she wished he did not like it so much. As Bobbie took out the short print dress that Gary insisted that she wear when she was to be punished, she remembered the first time Gary had spanked her. They had been going out for about a year and she was about to finish her last year at collage when she met Tom at a local bar. Tom was a lead singer in a metal band named the Mutant Strain who was the "Bad Boy" of all "Bad Boys". Bobbie wanted to have one last fling before finishing school and so she started to party with Tom behind Gary's back. One night when driving home from a Mutant Strain show she was pulled over by the Police and charged with drunken driving. Tom was with her and put a vile of cocaine in her glove box as they were being pulled over and told the cops that it was her's. Not knowing who else to call, Bobbie had Gary come down and get her out of the mess she was in. A few days later Bobbie pleaded guilty to driving under the influence and with Gary's help, had all other charges against her dropped. On the way back to her apartment, Bobbie and Gary had a long talk about their relationship. Gary told her that he loved her but could not put up with her running around and drinking and driving. He told Bobbie that when she acted like she had that he felt like taking her over his knee and spanking some sense into her. Gary then said that until she could prove to him that she would change that they were through. Two hours later Gary was very surprized when Bobbie came to his door and asked to come in. She told him that she was very sorry about what had happened and that she would do any thing to make it up to him. Next she told him that she deserved a spanking and asked him to give her one. Gary told her that if he did spank her, he would be very severe with her. She still shuddered when she thought about that first spanking and how surprized she was when he pulled her skirt up and then later pulled her panties down. He had spanked her very soundly, but she smiled as she remembered that it was as he was finishing up the her first spanking since she was 8 that he ask her to marry her. As Bobbie picked up her rosewood hair brush she remembered when Gary had taken her to Crabtree and Evelyn and bought it as a special engagement gift from him. In the three months since Gary had spanked her about once a week using the brush four times when she was especially bad. Tonight, Bobbie knew that she deserved the brush. She had made a scene today at lunch when the waiter who was serving her seemed to be paying more attention to her blonde girl friend, Gail , than he was to her. After screaming at the waiter and her friend she broke two of the wine glasses on the table and stormed out of the restaurant. Although she knew that the owner Joe, who was a good friend of Gary's, would never tell him about the scene she felt very bad about it. She had called Joe and her friend Gail latter that afternoon and apologized to them both. But this did not seem to be enough and she knew that she could never really forgive herself if she was not properly punished for the way she had acted. So she came home and put on her spanking clothes and apprehensively waited for Gary. Gary was surprized as he walked into his house and found a straight backed chair with a hairbrush on it in the center of his living room and the woman who he was going to marry in two months standing with her nose in the corner. Although he had spanked her frequently in the past months this was the first time that Bobbie had ever prepared herself without being told. After laying in his coat on the back of the sofa Gary positioned the chair so that it was centered in the two decorative mirrors that he had put in the room. As he glanced over he noticed Bobbie fidgeting like a little girl in the corner in her cute yellow and red floral print dress. He loved the way that she looked with her red high-healed pumps and the white stockings that covered her long legs. As he sat down he called out in his most commanding voice, "young lady come here". Bobbie looked around and bitting her lower lip slowly walked over to Gary. As she came into range Gary took both of her hands and pulled her in front of him and looked in her eyes and said "tell me about it". Bobbie then proceeded to tell him about her misadventures at Joe's. Gary sighed and said "What have I told you about your childish temper tantrums young lady". This made Bobbie angry as she pouted "It was not childish". "Well what do you call it when a grown woman, makes a scene because some waiter comes on to her best friend and not her". Bobbie bit her lower lip and said "I don't know" as she looked down at her feet. "Well I know Young Lady" Gary said as he started to pull her over both of his knees. "I call her a sassy little brat who needs to be taught a good lesson". Bobbie was soon stretched out with her hands and feet on the floor and her bottom sticking up over his lap. The hem of her dress had ridden up to the top of her stockings and he took the time to admire the view before he proceeded to lift the skirt of her dress to the middle of her back. As the seat of her white satin panties were exposed she new that he would leave them on as he warmed her up with his hand. He had told her that he loved seeing her bottom bouncing in these before he bared her for more severe punishment. Gary ran his right hand up both of her legs and started to rub her bottom through her pants and continued to lecture her about her conduct. Bobbie felt her stomach tighten as he placed his left hand on the small of her back and lifted his right hand from her behind. He brought it down with a loud "SMACK" on the fullest part of her right cheek. He spaced the initial spanks out to about one every three seconds, concentrating on the full upper flanks of both rounded globes. Although not as hard as she new she would get later, by the time the first five minutes were up Bobbie was really starting to feel the 100 or so smacks she had already received. At this point Gary waited until she stopped wiggling and the adjusted her stockings and garter belt so that they perfectly framed her pert panty clad bottom. He then lifted his right knee slightly, so as to get a better angle at her butt and wrapped his left arm around her waste. Bobbie gasped as she new that she was really in for it now. Gary now increased both the power and tempo of his spanks so that the spanks landed all over her bottom about one every two seconds. For the next couple of minutes, Gary kept up the pace of about 30 spanks a minute. By now Bobbie was kicking her legs frantically and gasping "OH" as every spank landed. For the next two minutes Gary concentrated the slaps on the crease between her thighs and the upswell of her buttocks where the lace edges of her panties ended. By the end of this series Bobbie was starting to plead with him saying, "Please, I'll be good, I'll be good" When this started Gary new that she was ready for the serious part of her lesson. As he stopped and lifted her to her feet Gary looked deeply into Bobbie's eye's. Although not yet crying, tears were starting to well up in her eyes and her lower lip was trembling as he stroked her hair. After a few minutes he gave her a hug and a kiss and ask her if she was ready for the rest of her spanking. Bobbie took a deep breath and finally said "yes". Gary now pulled her down over the inside of his left leg because he knew from experience that he would have to clamp his right leg over the back of her legs as the heat from the brush started to build up. As he told her to Lift Up" so that he could pull her panties down, Bobbie grabbed his left leg with both of her arms so that she could have something to hold on to. As he pealed down the panties that he had bought her for just such an occasion, he noticed that her bottom was a bright pink with scarlet blotches around the tan lines where her bottom ended and her long legs began. He smiled as he noticed how her damp panties stuck between her legs as they were turned inside out at the top of her stockings. He rubbed his hand over her bottom feeling the heat that had built up in them. As he picked up the brush he knew that the would get much warmer before the night was through. Bobbie's hair brush was an oval shaped rosewood beauty that was about 10 inches long with stiff bore bristles. As he rubbed the back of the brush on her rounded backside he positioned Bobbie so that her bottom stuck up over his knee and placed his right leg over the back of both of her legs so as to keep her in place. From the first smack of the brush Bobbie stated to wiggle her bottom and continue her pleading with each spank. Gary slowed the pace down as he paddled her. Every 5 or 10 seconds a loud "SPLAT" would punctuate Bobbie's pleas of "No, Please stop, Please, I'll be good, Please Gary Please, I won't do it again". As the brush reignited the fires in her twin checks, Bobbie reached her right hand back not so much to cover up as to have something to hold on to. Gary paused and being sure not to twist her arm clasp her hand in his and placed it in the small of her back. During this part of the spanking Gary used a patten of spanks descending from the top of each cheek down to the top of each thigh in about five overlapping slaps. After using this pattern about 5 times on each globe, Gary noticed that Bobbie had finally started to cry outloud and was rhythmically squeezing her right hand in time with the spanks. This was his queue that it was time to start ending her punishment. Pausing for a few seconds as he rubbed the back of the brush along the base of her bottom he told her that it was almost over and that she would have to count the last twenty out loud. He started on the outer base of her right buttocks and proceeded to use short wrist snapping smacks in five series of fours across the base of both checks as she kept count with heartfelt sobs of "One, Two, Three, ..... As he finished, he surveyed his handy work and felt a deep love for the woman sobbing over his knee. Her bottom was a deep red as it clenched and shook. Gary picked up a bottle of baby oil that Bobbie had set next to the chair and began to rub the oil into Bobbie's hot cheeks. Bobbie began to moan as Gary's fingers part her checks and linger over her tight little butt hole. Finally Gary slips his hand between her thighs where he is not surprized to find the soaking wet pussy of the woman he loves. As he picks her up and carries her to the bedroom, Bobbie thinks that although there would probably be many more sessions just like this they both knew that they were a perfect match.