The Seduction of Glenda

by Phil E. Hebe

Caution: This Erotica Sex Story contains strong sexual content, including Consensual, Drunk/Drugged, BiSexual, BDSM, Spanking, Light Bond, Gang Bang, Safe Sex, Oral Sex, Anal Sex, Sex Toys, Slow, .

Desc: Erotica Sex Story: A just graduated teenager learns about love and sex and submission to an older man.

There was an article on page eight of the Tribune. Thirty per cent of new graduates could not find jobs. Glenda felt very lucky to be employed in one of Chicago's biggest accounting firms. It was only a clerk's position, but it was better than nothing. She was sure her 5.0 GPA helped a lot, the interviewer seem impressed with that, and that she took accounting classes in high school.

The train was slowing for Union Station. Glenda folded up the newspaper and crammed it between the seat and the side of the car like she always did. When the train stopped at the platform she stood up with her purse and lunch bag in hand, got in line with the rest of the people in the aisle to disembark. It was a pleasant autumn day, only a bit on the chilly side, so she didn't mind the seven minute walk to the company's offices. If it warmed up like the forecast promised she decided she would eat lunch in the plaza in front of the building. Maybe she could talk Sally into joining her.

She sat in her cubicle, at her desk, in front of her computer, and signed in. Glenda flipped the pages of her desk calendar to Monday, October 1. It was an anniversary of sorts, she had been with the company for three months. Her boss passed by her cubicle and she said, "Good morning." he mumbled something, and she knew that was the most she could expect. He was not the friendliest of bosses. She put the first set of accounting sheets in front of her and started entering the data from them into the computer. It was a boring job, but there was a pay check once every two weeks and for that she was thankful. At ten-thirty she went to the break room and sat with a bunch of girls about the same age and pay scale as her. Like most companies, there was a hierarchy to be observed. At twelve noon Sally and Glenda went down to the plaza, ate lunch, talked small talk about this and that, including their dread of the coming Chicago winter. Glenda threw half her cupcake to the pigeons. It wasn't that good anyway. Then it was back to the salt mines, as they called it.

It was late afternoon when one of the executives visited her. She saw Mr. Monroe every now and then in the aisles. She knew he had something to do with customer relations. She guessed him to be in his late twenties or early thirties. A polished kind of handsome, dressed in a conservative dark suit with a white shirt and tie like all the executives.

"I understand that your birthday is this week, If you are not doing anything Saturday I would like to take you out for supper to celebrate."

She was flabbergasted. She almost said, "Me?" as if he might be talking to someone else in her cubicle, instead answered, "That would be nice."

"I'll pick you up at eight."

"Let me give you my address."

"I got it from personnel. 1009 Rugers Ave, Glenview. Right?"


"Good, don't forget, Saturday at eight."

She was still trying to catch her breath as he left. Okay, she thought, he got the info from personnel, maybe it is some kind of company perk to take employees out on their birthday.

Her graduation dress was the nicest outfit she had, so she wore it Saturday night. He took her to The Top of the Rock Restaurant. one of the classiest in Chicago. Everything she ate was excellent from the soup to the dessert. Afterward, at the front door of her mother's house he gave her a kiss on the cheek. "Here," he said, "happy birthday." and handed her a little, gift wrapped box. As soon as she was inside she tore off the wrapping. The box was marked, Tiffany & Co., one of the best jewelers in Chicago. Inside the box was a pair of gold earrings. She knew Tiffany's was not cheap, so who paid, the company or Mr. Monroe?

Back at work she could swear he was avoiding her. She hoped he would come visit her cubicle, or for even a chance meeting. It was disappointing that he didn't, but she knew she was probably hoping for too much. Why would a man of his caliber want with her anyway.

They had what she thought was a chance meeting the next week in the elevator. Before she could say anything he said, "I have been going out of my way to avoid you. I swear this place is one big rumor mill and I didn't want to give them any fodder for their dirty little minds. It is bad enough everyone would say I am robbing the cradle. I ambushed you in the elevator to ask if you would like to go to the theater this Saturday, there is a revival of the play Phantom of the Opera at the Boswell Center, and I was lucky to get two tickets."

"I would love to."

The elevator stopped at his floor and he just had enough time to say, "See you at seven," before the doors started closing. Immediately her mind went into a whirl. He wants to date me again! Why me? Why would the cool cat want to date the meek mouse? I need a new dress by Saturday. Can I afford it? To hell with can, I will somehow.

She got her frock thanks to a loan from her mother. He picked her up promptly at seven in his red Corvette. "You look lovely tonight, and I am glad to see you found a use for my gift."

Glenda touched the earring. "I have been meaning to thank you ever so much. It was the nicest birthday gift I received."

"My pleasure, I assure you."

They stopped for a drink after the play. The waitress knew Mr. Monroe and never asked Glenda for ID. He ordered scotch on the rocks and white wine for Glenda. After the second glass she was kind of giddy. He took her home and kissed her sweetly on the lips. "Do you want to go dancing next week?" he asked

"I'm not much of a dancer?"

"That's okay, fake it."

Another new outfit. Luckily, she just received her paycheck to pay for it.

They drove out to the Aragon Ballroom. She was afraid to go out for the first dance, wondering why she ever agreed to go dancing when she was so inept at it. On the dance floor he told her twice to just relax and let him lead. Things got much better, after the second glass of wine, plus his dancing made up for her inexperience. The kiss at the end of the night lingered on. She felt herself pushing her body against his. She knew she couldn't be more happy.

"I would like to show you my apartment next week." That broke the spell. She knew that, or something like, was going to rear up.

"I'll be frank with you. You're the first man I ever dated, the first one I ever kissed. I know what you expect, but I don't think I can give it to you."

"I tell you what, I will take it real slow. The instant you are out of your comfort zone say stop and I will. Deal?"

"I don't know."

"Okay, just try it once, if you don't like it, say so, and we won't go there. I won't bite, I promise."

"Let me think about it."

For the next two days that was all she could think about. He is thirty, twelve years my senior. With his looks he probably bedded dozens of girls. Why me, I'm no prize. I wonder what it is like to have a man touch my body, as good as it looks in the movies? Why not go ahead, what have I got to lose, only my virginity? What if I don't like it? He promised to stop, will he really? What if he doesn't, would he rape me? How am I going to find out whether I like it or not if I don't try? I'm a fraidy cat that's why. I have been a fraidy cat all my life, it's time to stop.

He called on Wednesday. "Have you thought about coming to my apartment?"

Only non stop. "I'll go."

"You sound nervous. I promise, I'll be gentle. I won't rush you. I'll stop when you say stop. You will like it, you'll see. I'll come by at eight."

His apartment was on the twenty-eighth floor of a downtown high rise. It was a one bedroom. The living/dining/kitchen was all one room. The outside wall was glass from floor to ceiling, from wall to wall. His furnishing were ultra modern, all black and white, chrome and brass. The only color was a green potted ivy hanging from a chain in front of the window. In one corner was a telescope on a tripod. The lights were set on low. There was soft music playing in the background. A bottle of wine and two glasses were on the cocktail table in front of the couch. She almost laughed, it looked right out of a movie of a bachelor pad.

They sat, they talked, they drank wine. They kissed, sweet chaste kisses. They got up and went to the window. He pointed out the John Hancock building, the Trump Tower, The Willis Tower. She loved the vast expanse of Lake Michigan with a ship way in the distance. His arm was around her waist and he was behind her. He nuzzled her neck. He kissed her ear, and then blew gently into it. His other hand went around her waist then slid slowly up until it cupped her breast through her blouse and bra. He heart started beating hard. Okay, this is it. This is the beginning of the seduction of Glenda, she thought. He led her back to the couch. "Before we sit down, do me the favor of taking off your blouse and bra." she turned beet red. "In the bathroom if you wish." That was better, at least she didn't have to feel like a stripper. She was a nervous wreck. She wanted to do it, for him, he was so kind to her. She wanted to do it, for herself, she told herself it was time to grow up. She was trembling and the bra did not want to come lose. Glenda was on the verge of tears. Do it, damn it, kept running through her head.

When she came back out she said, "I'm sorry."

"For what?"

"For having such small breasts."

"There is nothing for you to be sorry for. They are delightful. Look how nicely they stand out with the dark nipple right at the apex. Come here and sit next to me."

He didn't attack them like she thought he would. He kissed her lips, her nose, her eyes and to her ear. His hand warmed her exposed stomach. She felt herself relaxing. He left a trail of kisses from her ear down her neck, across her chest to her breast. He sucked on the nipple and gently bit down. She ran her fingers through his hair and held his head against her breast. It felt nice what he was doing. She felt arousal building in her sex. He alternated between breasts and occasional French kissed her on the mouth. They stayed that way for an hour, maybe two, she didn't keep track of the time only the thought that she didn't want him to stop.

When he did stop she thought, Is that all? She expected more. Before she could ask he said, "I promised to take it slow. We went far enough for tonight." She went toward the bathroom where she left her clothes. "Do me a favor, don't wear a bra when you are with me. You have no need for one, your breasts don't sag. Although it isn't absolutely necessary, I would also prefer button down the front blouses, and you might consider showing off more cleavage. You should be proud of your breasts, they are perfect." When she came back she stuffed her bra in her purse.

When he walked her to her door and kissed her good night he gently squeeze her breast. Next Saturday again?" he asked.

"Same time?"


Glenda could not remember ever being so happy. On her way home from work she stopped at J. C. Penney's and bought a button down the front blouse that had a scoop neckline.

Her mother asked, "What's got into you?"


"You are so damned cheerful. I bet it's that man your seeing, that Mr. Monroe."

"Yes, Mom, it is Mr. Monroe." Glenda knew his first name was Adam, but he never suggested that she use it. That was okay, with the age difference she felt like she should call him Mr. Monroe.

"He is a very nice man. Don't lose him," her mother said. Glenda noticed how Mr. Monroe turned on the charm when he talk to her mother. She could see how her mother would be pleased with him.

He complimented her on her blouse then promptly unbuttoned the two top buttons exposing even more of her chest. They stopped at a little bistro on the way to his apartment. I bet he wants to liquor me up for the big one. she thought. She noticed some of the men were trying to look down her blouse. She almost started giggling. She could not believe they wanted to see her small breasts.

When they were in the apartment she said, "I noticed your telescope. Are you interested in astronomy?"

He laughed, "No, it's to spy on my neighbors. They in turn spy on me. It is a favorite high rise past time."

"You are kidding, right?"

"No, I'm serious." He swept the area with the telescope, stopped, made some adjustments, and said, "Look."

She peered through the eyepiece. She saw a man and woman watching TV. The man had his hand up under the woman's blouse. "They are good for a little show every night," he added. She watched, feeling like a Peeping Tom, and at the same time wanting to see more.

"Now I want you to go into my bedroom and take all your clothes off, and lay down on the bed. I will be with you shortly." What he asked was a lot more than she had expected, but she was determined to do it. Glenda was positive she loved him and would do as he asked. She went in with both anticipation and anxiety. She noted the heavy drapes on the window were closed. At least no one could watch her from afar as she stripped. She was happy to give Mr. Monroe her maidenhead, but worried about the pain. She laid stiffly on the bed, her legs closed and her arms at her sides. Relaxing was impossible. Her first inclination was to hide her sex beneath her hands, but then realized just how stupid that would be. She wondered if he was going to come in naked. He didn't, he was still dressed.

He put his hand on her stomach. "Relax. You are stiff as a board. You can't hope to enjoy sex if you are going to be like this." She tried to loosen up, but he had to tell her twice more to relax. It was his roaming hand that finally did it. They went all over her body, they squeezed her breasts, and massaged her feet, but avoided her crotch. Adam started kissing her, he sucked on her nipples, her fingers and toes. Glenda was aroused and spread her legs hoping he get the message. She almost pleaded with him to play in her sex, but the words won't come. When he did play in her sex he avoided her clit. She tried moving herself to have his fingers, at least, brush against it. Finally he plucked at it. He pinched it between thumb and forefinger. He twisted it and pulled on it. The climax came on in a rush. She arched her body between head and heels. It went into spasms and bucked. Her breathing stopped. She saw a blaze of colored lights in her mind's vision. Her body broke out in a sweat. She thought, It is a hundred times, no a thousand times better than masturbating. She laid on the bed totally limp, totally drained, completely happy.

He stood next to the bed. Adam took out his penis. Her first though was, So that is what a real one looks like. "Take it in your mouth as if it were French kissing you. Tonight was all its doing, thank it for your pleasure filled evening," he told her. Glenda sat up and took hold of his cock. It was hot to the touch. She slid it over her lips into her mouth. She licked it with her tongue. It tasted salty and spicy. She let it slide back out, stared at it, memorized the shape of the head and the dark purple veins running down the shaft. "Thank you for such a wonderful time tonight," and she meant it with all her heart.

After she recuperated and was dressed again he brought out a Playboy magazine. "I want you to get your pubic hair waxed." He opened the magazine to a pictorial of six girls, four were facing head on toward the camera. Adam pointed to one of them that had a dark stripe down her pubic mound. "That is what is called a runway." He pointed to another girl. "That is what I want you to look like by next Saturday," he said, pointing at the girl's bald pubic mound and the dark opening to her sex.

The procedure was painful. She reminded herself that it was for him. She hoped the redness would go away by evening. Glenda looked at herself in the mirror. It looked strange to her not to have any hair down there. She tried to remember when was the last time her crotch looked like that, probably when she was eleven. She hoped Mr. Monroe liked it.

Everything went just like the previous week right down to the muted lighting and soft music. "Go into the bedroom, undress and come back out. When she returned, naked, the lights were on full. She looked at the glass wall and remembered the telescopes, but there was no place to hid. "Come here, I want to see you in the light." She stood in front of him. He ran his hand over her pubic mound. "Very nice, just the way I like it. Now turn around and let me see your backside." She turned, looked at the windows, and wondered if there was anyone looking at her through their telescope. He ran his hand over her buttock. "Nicely curved," he said

"Too big," she retorted.

"All the more to be spanked."


"What do you expect me to do if you misbehave?"

"Oh," was all she said. I hope he is joking, she thought.

They went into the bedroom. "He took out his cock. "Tell my penis what you want tonight." She fell to her knees in front of him and said, "I want you inside me."

"Are you sure? I have been taking it easy and not rushing you."

"Yes, I'm sure." She kissed his cock. He undressed and she admired his build. He too had a completely hairless body including his genitals. He told her if she wanted to have intercourse she would have to earn it. He taught her how to treat his genitals, to suck cock and lick his scrotum. He treated her just as good as last time. He slammed his cock into her just as she began her climax. It was a wild ride for both of them. If there was pain, she didn't sense it, the climax overrode all other feelings. The only thing that she was sorry about was all the blood she spilled on his thousand count, Egyptian cotton sheets.

"Kiss my penis and tell it how much you enjoyed it in your body. I think it is time you started calling it, My Master." She told him in glowing terms how much she enjoyed losing her virginity to it and at the end said, "My Master."

He gave her a morning after pill, something she did not even consider. She scolded herself for being so dumb to let him come inside her. They taught her better than that in sex education class, but it felt so good.

Glenda went into the john and washed herself while humming a happy tune. When she came out she went to her pile of clothes and picked up her panties. "Give them to me," he said. When she handed the panties to him he said, "From now on when you are with me you do not wear panties, or panty hose or anything else that would block free and ready access to your sex or anus. You might want to consider a garter belt and thigh high nylons."


"Of course, it is a erogenous zone. I have full intention of playing with it." She was shocked at the idea.

They settled in a routine. Every Saturday night they did something. He took her to concerts, symphonies, stage plays, and sometime to a fancy cocktail lounge. She went to her doctor and got on the pill. They had sex every Saturday except when it was that time of month. The first time she stayed over night she was sure her mother would give her holy hell. All her mother asked was, "Did you enjoy yourself?" She knew her mother married young, fifteen, to a much older man. Glenda wondered if it was in her genes to like an older man. She knew her mother liked Mr. Monroe a lot, which helped.

Adam took her to a party. There were nine other couples there. They all knew Adam, wondered where he's been hiding the past six months. There was only one person there that Glenda knew, Anna, the Personnel Director of the accounting firm they both worked at. Glenda was introduced to Bill, Anna's husband. Glenda guessed the woman to be about thirty, good looking, with a great figure that Glenda envied. Bill was on the husky side. A good looking man. Anna and Bill made a good looking couple together.

"So, is your new girlfriend going to be cooperative?" Bill asked. Adam did not give him a straight answer, but Glenda had the idea he was talking about sex and wondered what "going to be" meant.

At about midnight two of the women were naked. They took men upstairs for about fifteen or twenty minutes at a time. Glenda guessed they were whores, that they were rented out for the night. One of the women asked Adam if he were interested in going upstairs; he just shook his head no. When Glenda asked Adam about them he said it was just part of the night's entertainment.

They went back to their routine dating every Saturday. One night after they had been to a cocktail lounge and Glenda had too much to drink she accidentally knocked over a full glass of wine on his coffee table. He got out some rags and wiped up the mess she made. "I guess this means I will have to punish you," Adam said.

"Are you going to spank me?" She was just drunk enough to wonder what it would be like to be spanked by him.

"I have to, you were a bad girl." He went into his bedroom and came back seconds later. "Hold out your arm." When she did her wrapped a leather cuff around her wrist. "Now, the other arm." A second cuff was put on. the two cuffs were held together with about twelve inches of chain with a snap hook in the middle. In her drunken state she found the whole thing amusing. "Now stay right there," he said. Adam took down the hanging potted plant and put it on a side table. "Come here," he told her. She obeyed and wondered what the hell he was up to. Her mind was spinning and she couldn't put two and two together. He took hold of the chain and lifted it up along with her arms and snapped the hook to the chain that the potted plant hung from. It dawned on her then that she was standing buck naked in front of a floor to ceiling window, with her arms chained to the ceiling and his intention was to spank her. She started giggling at the absurdity of the situation. "You're going to spank me for your telescope friends can watch?"

"Exactly. Now turn your back to the window so my friends can watch the spanking." He started. Her first thought was, Damn he slap hard. Her second thought was, Oh, this is going to hurt. When he finished he had her stand there so his telescope buddies could view her reddened ass.

After he released her from her bonds they went to bed. After the sex, while they were laying snuggled together he asked, "So, how did you like your spanking?"

"It hurt, but you doing it made it okay. No, more than that, you doing it made in erotic. I hurt and was aroused at the same time."

"Maybe you should spill your wine more often."

"Maybe I will."

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