The Transformation of Sally

by Phil E. Hebe

Copyright© 2016 by Phil E. Hebe

Sex Story: She was tired of being a mousy girl, and wanted to live an exciting life, so she went after a bad boy. It turned out to be a lot more than she expected.

Caution: This Sex Story contains strong sexual content, including Ma/Fa   Slavery   Heterosexual   Fiction   Incest   Brother   BDSM   DomSub   MaleDom   Light Bond   Spanking   Gang Bang   Oral Sex   Safe Sex   .

She saw him in the dance club many times before. He was easy on the eyes, good looking with a nice build, but not extreme with either. He had the reputation of being a bad boy, and that was what she was looking for. It took all her gumption to flirted with him. He ignored her. That was disappointing. She tried again the next weekend. She flirted and he gave her a quick smile, nothing more. Sally blamed it on the fact that she was too plain looking. She didn’t know whether to give up or try one more time. Third time was supposed to be luck, right? Sally went all out with new clothes. She wore a button down the front blouse that she only buttoned up to her breast bone, and a low cut bra that pushed them up and out. She wore a pleated mini-skirt, thigh high stockings and a four strap garter belt. She was nervous and promised herself if he did not respond she would give up and return to her introverted ways, maybe give up on the dance club since not many guys wanted to dance with her, and those that did were usually three sheets to the wind. As soon as she caught his attention at the dance club she winked, and smiled her best come-hither smile.

He came over to her and her heart started beating faster. “You don’t want the likes of me,” he said.

“Why not?” Sally asked.

“I am very demanding of my women. I expect them to do what I want them to do. You don’t look to be the type.”

“That is exactly what I want.”

He looked at her like she was crazy. “Why would you want that?”

“I have been meek all my life. I want to start living it up.”

“Don’t say I didn’t warn you. Are you free next Saturday night?”

“I am free whenever you want me.”

“One more question. Do you have any STD issues?”


“Good, neither do I.”

They exchanged names, phone numbers, and addresses.” He told her he would pick her up at eight sharp. “I want you to wear what you are wearing now, but no bra.”

“Yes, Sir.” She was so excited she could not stop smiling.

They danced several dances together. He said, “Just so you understand, when I said I am very demanding I meant sexually. You sure you are still interested dating me?”

“I’m not a virgin if that is what you are thinking.”

He took her to a supper club that had bare breasted waitresses, several of whom came over to say hi to Tommy. They looked at Sally like she was a cockroach that should be squashed, or at least an unwelcome amateur.

At two AM he took her back to her apartment. She was tipsy and giggly. In the hallway out side her door he unbuttoned her blouse, pulled the ends out of her skirt, and pushed it off of her breasts. He stared at her nicely shaped breasts with their bright pink nipples. Judged them not too big or too small. Tommy took out his cock. “Get on your knees and kiss the glans if you want another date.” She thought that was the stupidest thing she could do in the hallway, what if someone saw her, but her knees were already bending. Even at half hard she saw he was well hung. She took it into her mouth until the red rim passed her lips. She washed the tip with her tongue. He straightened her up by her shoulders. “I will pick you up at seven-thirty. You are to wear a mini-skirt similar to the one you are wearing. No panties or anything else that would cover your pussy. I like the nylons and garter that you are wearing. I want you shaved down there, clean smelling, and good tasting.”

She French kissed him good night. On the other side of the door she leaned against the jamb, wondered what she got herself into, and if she were up to it.

He picked her up at exactly seven-thirty PM. The first thing he said was, “Show me you followed my instructions.” She raised her skirt to show him her crotch was bare. “Very good,” he said. They drove to the downtown area and saw an off Broadway play with cocktails afterward. At her door he pushed her back against the wall, and knelt in front of her. Tommy raised her skirt to her waist and said, “Hold this.” He started by licking her mons, and worked his way to her slit. The tongue wormed its way inside and squirmed around. She could not believe how far his tongue got in her pussy. She thought of the singer with the long tongue, but for the life of her she could not remember his name. At the moment she could not think of anything except how good the tongue licking felt. He stood up and Sally wanted to scream, “No, don’t stop.”

“Next Saturday I am going to fuck you. You are to answer the door naked. I will be here at nine o’clock. He saw the look of bewilderment on her face. “Is that a problem?”

“No. Naked. Nine.”

That night, in bed, she masturbated thinking of both him eating her that night and his promise to fuck her the next Saturday. It was no better at work, her mind constantly went back to last Saturday and next Saturday. Her boss told her if she was ill she should go home. She could not very well tell him her illness was thoughts of sex.

After dinner on Saturday she started preparing for his visit. Never before had she been so meticulous. She started with a douche followed by a hot bath, shampooed her hair, and very carefully shaved her underarms and crotch. The last thing she wanted was a bloody nick. Deodorant was used on her underarms and a vaginal spray on the inner part of her sex. She combed and blow dried her hair; trimmed and polished both her finger and toe nails. Applied her makeup. Misted herself with her favorite cologne and finished with skin softener on her hands. Sally very carefully looked at herself in a full length mirror. She thought she did the best she could and hoped he wasn’t too disappointed. She knew she was not the ideal woman men wanted with big breasts, narrow waist, and flared hips.

Ice was in the bucket along with a mini bar she set up on an end table. Lastly she found some love song cd’s, put them in the changer, and lowered the lights. It was eight-forty- five. The next fifteen minutes felt like eternity. Every second she looked forward to his visit. Every other second she told herself she was stark raving mad for agreeing to be fucked without, at the very least, a bouquet of flowers. The doorbell rang and she jumped like she just saw a spider. Sally looked through the peephole to make sure it was him. When she opened the door she made sure she was standing behind it to block any view of herself. She told herself she was acting stupid. He was going to see her whether she wanted him to or not. Holding her breath Sally turned toward him after she closed the door.

He held her at arms length, and slowly looked at her from head to toe. She felt herself shaking. “You are beautiful.” She felt like crying from joy. All her doubts were in vain. They went into the living room. She mixed his favorite drink and offered hors d’oeuvres. They talked about things that happened the past week while they snacked. He kissed her, a sweet, soft kiss. So he wasn’t going to fuck her like a whore and leave, fear number two expelled. Tommy took his time, kissed her face, her eyes and blew gently in her ear. He worked his way down to her breasts and tongued her nipples, and then sucked on them. His hand went to her crotch. It petted the outer lips before his fingers pushed inside her. He stopped and completely undressed. She saw a completely hairless body, even the genitals. He pulled her body until her butt was right at the edge of the couch, and widened her legs. When he knelt on the floor between her legs she thought, here it comes, just what I wanted. His tongue went into her pussy and her face got a dreamy smile. As far as she was concerned he could do that all night.

“Okay, time for your spanking.”

Sally could not believe what he was saying. “What? Why?”

“You never, ever question me. Your only option is to do what I say or break off our relationship. Now you force me to spank you extra hard. Get up!”

“Yes, Sir.”

He arraigned her like he wanted over his lap and then spanked her hard enough to make her cry. They sat back next to each other. He apologized for having to spank her so hard, but also made sure she knew it was her fault. Tommy licked away her tears. They went to her bedroom. He again made soft gentle love to her. He showed her the French tickler and how to roll it on. It was her first orgasm that was not self induced.

They laid side by side after she cleaned him up. “I just want you to know the spanking wasn’t for your pleasure, because I am sure you didn’t enjoy it, but for mine. You will be spanked every time we make love.”

“I understand.” Although she wasn’t sure she did.

“Are you on any birth control?”


“We need to remedy that. I’ll make an appointment for you and call with the details.”

The next morning he dressed but refused to let her. They ate breakfast. “At the front door as he was getting ready to leave, she said, “I had a wonderful time, even in spite of the spanking.”

“I am glad. I know I am not the easiest man to get along with.” They kissed and he left. She closed the door and started giggling with joy.

He called and said her doctor’s appointment was for 1:30 on Tuesday, could she possibly get off work. She assured him it would be no problem since she had both unused sick days and vacation time. He picked her up at 1:15 and they drove directly to the doctor’s office. She had to fill out the usual paperwork, and was given a gown. She met Doctor Gwyn. He wanted to know what kind of birth control she was taking and she admitted none. He raised an eyebrow as if to say you are going out with Tommy and your not on birth control? Shame. She got on the table and put her feet in the stirrups. While he was examining they talked about birth control methods. He strongly suggested an IUD, and she agreed. The doctor asked Tommy, “Have you decided? Tattoo or branding.”

Tommy answered, “It’s way too early to think about that.”

Doctor Gwyn inserted the IUD, and cautioned that there might be cramps and bleeding for the next couple of days. “Anything more than that come back and see me.”

Tommy said to the doctor, “Check her anus while we are here.” Sally was not happy with the doctor pushing a tube in her butt, but knew protesting would not get her anywhere. The doctor said, “She has a healthy anus. Anal penetration should be no problem.” That was not what Sally wanted to hear. Tommy paid the bill and drove Sally home. On the way she asked “What was that about tattoo or branding?”

“Don’t you worry your pretty head about that.”

Sally lived for Saturdays. Every Saturday evening she saw Tommy. They went to whatever was the attraction in town, a stage play, or concert what ever the music, a new movie playing at the Ritz or Rialto, sometimes only the dance club where they met. Some Saturdays they didn’t go out, but indulged the evening in sex. Their sex play had progressed into light bondage. He liked to tie her up spread eagle on her bed. He bought a fifteen inch slapping whip that he used instead of his hand for her spankings. Sometimes he hung her by the wrists from a hook he had installed in the ceiling and spanked her that way. He used the whip lightly on her breasts and the outer lips of her sex. When he was horny was the only time he was strict, otherwise he was very loving. She could put up with his sexual demands because she was deeply in love with him. No matter how he hurt her, or what he demanded during sex play she vowed to take it.

Tommy invited Sally to his house on a Friday evening which was most unusual. When she arrived he told her to undress completely which was always expected of her when they were at her apartment so she always greeted him naked, and if they were going out that night he picked the clothes she was to wear. It got to the point that he also bought all her clothes.

What now?” She asked once her clothes were off. He showed a chip from The Bellagio Casino. “This is you,” he said. That made no sense, but they were interrupted by the door bell ringing. Tommy said, “Stay right here and show no modesty in front of my friends.” He went to answer it.

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