Category: Mature Stories

Blackmailed

by ilovematurewomen©

Joey can't remember where this all started, his fascination with the school's guidance counselor, maybe when she would ignore him and instead entertain the jocks that went to her office for counseling or maybe this woman was just really desirable. Joey Jones was 18, a high school senior, and the captain of the chess team. There were other girls his age that he was interested in but there was something about the counselor that captivated him.

The guidance counselor was Mrs. Zilpha Rollins; she's the guidance counselor of Joey's high school for the past 10 years. Zilpha Rollins is a 43-year-old mother of three teenage girls. She's married to a state prosecutor of the local circuit court and a man almost 20 years her senior.

Aside from being on the chess team and being a true blue nerd Joey had other interests, most prominent among them is his fondness with computers such that he and some of his friends formed a group that helps with maintaining the computers of the high school. But Joey's favorite pastime was fantasizing about Mrs. Rollins. He would jerk off night and day imagining Mrs. Rollins in different sexual acts with him. One time the picture of Mrs. Rollins was published on the school paper, so Joey got a ton of that and used her pictures to masturbate on. Joey was bursting with sexual tension such that he could not take it anymore he had to fuck Mrs. Rollins soon or he will go crazy.

That opportunity came when Joey's club was asked to upgrade the existing computers of the Guidance office. So Saturday morning Joey's group were at school preparing for their work. When the computers were assigned to the members Joey volunteered to work on the computer of Mrs. Rollins. So the teacher in charge gave him the key to Mrs. Rollins' office and then he proceeded to her office. Upon entering the room Joey was met with a familiar scent, an erotic scent that always accompanied Mrs. Rollins the scent alone gave Joey a boner. He then inspected the computer of Mrs. Rollins and then turned it on. After booting up Joey went directly to the windows explorer to check the files of Mrs. Rollins. There was nothing out of the ordinary on her folders and files. But when Joey changed the explorer setting to enable the viewing of hidden files Joey was presented with several folders that were hidden.

So he opened each one of them some folders contained examinations others contained family pictures and a lot of DOS based games. By now Joey was beginning to get frustrated there was nothing exciting on Mrs. Rollins' computer. But when he opened the hidden folder named "XXX" he found out that it contained several jpeg files, named ZilphaAndJeric1, ZilphaAndJeric2, ZilphaAndJeric3 so he opened the pictures and to his surprise and utter delight the pictures where of Mrs. Rollins in various sexual acts with some guy. Joey's boner got harder upon viewing the pictures, although only in pictures, it was the first time that he saw Mrs. Rollins naked. He could not help but stroke on his member. But what intrigued him was that the guy with Mrs. Rollins was not her husband and the guy looked very familiar. Joey's heart skipped as he remembered who was the man with Mrs. Rollins it was Mr. Batte a former assistant principal of the high school, who left 2 years ago he was also an assistant coach on the soccer team. His eyes lighted up and an idea came up to him on how to get inside Mrs. Rollins' panties, the word was "BLACKMAIL" .

So he hurriedly copied the files from her computer and then shut it off. He was very excited about planning Mrs. Rollins' blackmail finally he'll get the chance to fuck this beautiful and sophisticated mature lady.

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It was Monday morning, Zilpha just got out of the shower and grabbed a towel and began drying herself off. She was thinking about Eric, and how she missed being fucked. Her affair with her colleague started on one of the school's affairs were the guy made advances on her, and being lonely herself she entertained those advances and that started their forbidden affair. Their affair was quite kinky such that Eric would take pictures of them in various sexual positions at first Zilpha was a bit apprehensive about the pictures but that didn't stop Eric from taking them, in time she grew accustomed to the fact that this experiment spiced up there relationship. Her affair with Eric ended two years ago when the he got transferred to another school. At first he would keep in touch with her but as time passed the letters and phone calls to the office became scarce and scarcer until the letters stopped coming completely. Zilpha just consoled herself that it was fun while it lasted.

Those thoughts aroused Zilpha such that she had to relieve herself. She could not rely on her husband for sex because he was just too old and uninterested with her; she had a suspicion that her husband was having an affair with another woman. And that too was part of the reason why she pushed through with her affair with Eric. So Zilpha, after drying off, locked the bathroom door and then sat on the toilet and then spread her long slender legs apart and then started to rub her pussy. While rubbing her pussy she imagined Eric ramming his cock in to her wet pussy. After a few minutes Zilpha came to an earth pounding orgasm.

"Haaaaaaaaaaahhhhhhhh" Zilpha suppressed a scream.

After her orgasm Zilpha lazily rubbed her pussy and rested on the toilet seat, her mind drifted to her previous encounters with her lover. Her daydream was cut short when she heard a knock on the door.

"Mom, hurry up, I have to use the bathroom. I'll be late for school!" her daughter yelled at her at the other side of the door.

Zilpha was startled from her self-induced slumber and hurriedly cleaned herself and then went out of the bathroom. She forgot that it was a Monday, the start of the school week.

When she arrived at school she went directly to her mailbox to check if she had any mail. There was one Manila envelope on her mailbox. But there was no return address on the envelope. So she just didn't mind the envelope and began a conversation with a fellow teacher. After engaging the Home Ec. teacher in some mindless conversation she went to her office and then opened the envelope. Zilpha was shocked when she saw the contents of the envelope. It was the print outs of the pictures of her and Eric making love in her house. She grew nervous as she tried to remember who sent her those printouts. As she inspected the package her cell phone received a text message that said

09173004418 – Mrs. Rollins I assume that you received the enveloped I sent you. If you want this pictures to remain our secret open your e-mail account and open the mail from zrlls@yahoo.com there will be instructions for you there.

Upon reading the text message Zilpha felt a chill run up to her spine. She was scared of what might happen if the pictures would be seen by her family, her friends, and the school board she would certainly lose her family, career, everything. She contemplated for a moment on what to do but after a few minutes of weighing the impact of those pictures on her she decided to follow the instructions from the text message. When she opened her account there were several unread messages for but she was only interested in the e-mail given by the text message. As she perused through the messages her heart raced in anticipation of what the message would be. When she had found the right e-mail she immediately clicked on it and as expected there were instructions listed for her to follow. First she was to log in to an IRC chat room and she would look for the nickname batboy from the names that were logged in.

Joey waited patiently for the for Mrs. Rollins' message, he had intentionally missed school so that he could wait for her reply. He was nervous yet very excited at the prospect of fulfilling his fantasies with Mrs. Rollins, he also was having second thoughts about pushing thru with his plan, he was concerned on how she will react to this – she might report to the police or she might tell his parents? But the thought of finally having his mature teacher for his own won out from all the other options. After an hour of waiting on a blank screen finally a message was printed on the screen

Teacher> Hello are you there?

Joey thought that her nickname was very appropriate for her, and her greeting was very pleasant to someone who wants blackmail you.

Bad boy>Yes!

Teacher> what do you want from me? She asked

Bad boy> we will get to that in a little while. Joey replied through the computer

Bad boy>it is important that you know were you stand on this deal. I have the e-mail addresses of all the important persons in your life and in one click of the mouse they will receive these very revealing pictures the next time they open their e-mail accounts. Do you understand?

Joey explained to her predicament to her. Then there was a pause for about 2 minutes, which irritated Joey.

Bad boy>you better not hang up on me now Mrs. Rollins!

Teacher>I'm still here and yes I understand you. But who are you? Is this you Eric?

Bad boy>you'll get to know me later.

Teacher>what do you want? How much will this cost me? Tell me!

She screamed through the Internet.

Bad boy>I don't want your money! I just want to have what old Mr. Batte has been getting.

Teacher>that's out of the question mister! I don't even know you and there is no way I am going to have sex with you.

Bad boy>Ok Mrs. Rollins say goodbye to your career, because right now I am going to send an e-mail to the head of the school board. Goodbye!

There was a pause for several seconds before Mrs. Rollins responded

Teacher>No please don't do that, Ok I'll agree to what you want!

Came her quick reply.

Teacher> so how will we do this?

Bad boy>Now that's a good girl? Ok I want you to stay after school and at around 6:00 pm I'll be right there at your office. Don't tell anybody about this or you'll kiss your lovely career goodbye.

Teacher>OK

Then she hung up.

That afternoon Joey went to school. While he was at his class he could not wait for 6:00 pm because everybody would be going home already. While Joey was delirious with excitement Zilpha could not concentrate on her job she was scared of what the man from the Internet will do to her. As the time drew near for their appointed meeting Zilpha was feeling anxious and she was thinking of backing out of there deal but she also thought of the repercussions of those photos on her family. So finally 6 pm came Zilpha readied herself. After about 5 minutes a knock came on the door. So she opened it and saw Joey.

"Oh Joey I don't have time to see you now, I am waiting for someone important." Joey knew that Mrs. Rollins would never suspect that it was him that got the pictures.

"In the contrary Ma'm I thinking that you will have all the time to see me!"

"What do..." Her voice trailed as it became clear who was the culprit behind this blackmail.

"It's you Joey?" her face turning a bit red in anger.

"Yes, its me" Joey confidently replied

"OK now this foolishness stops right here young man!" She replied in her most authoritative tone.

"SHUT UP! I am still in control here. Remember that I still had those photos!" Joey screamed at her as he entered the room and locked the door.

Zilpha, realizing that she does not stand a chance against what this young man has in his possession, pleaded to Joey.

"Why are doing this to me? What did I do to you to deserve this treatment?" she asked Joey

"I've been good to you, Joey"

"Good to me? Good to me when you ignored me on your classes and when my classmates make fun of me you were the first one to laugh at their Joey jokes. And all you have time for are the jocks of this school and a nerd like me could not even get inside your office."

"But Joey that's not true."

"Oh please stop it Mrs. Rollins, I'm not here to debate on this. You know why I'm here so quit stalling or I'll go home and one click of the mouse your career as you know it will be over." Joey told her with irritation in his voice.

"I should not have had that affair with Eric, it's just that he caught me when I was really very lonely." She tried desperately to appear very disappointed.

"Enough talk now!" Joey cut her short as he sat on her swivel chair.

"I think it's about time we get started." Joey commanded.

"You're really going thru with this, Joey?" she asked him but she really knows the answer.

"Yes, I do" he replied

"Well then, where should we start?" she asked him utter resignation.

"Stand in front of me." Joey instructed her

She turned around and just stood there in front of him.

"Please unbutton your blouse."

Zilpha hesitated for a moment then one by one she unbuttoned her white satin blouse. After having undone all the buttons Zilpha stood in front of Joey with her satin blouse draping over her bra covered breasts.

"Now remove your blouse and your bra."

"No Joey, I can't do this!" she protested.

"Your doing fine Mrs. Rollins, just do what I'll say and you will be fine." Joey reminded her.

So having no choice Zilpha slowly let her blouse fall to the ground and then gently unhooked her bra and let it drop to the floor. Now she was naked, from the waist up, in front of her student.

Seeing Mrs. Rollins' naked breasts gave Joey a major hard on such that he could not help but rub his rigid member through his pants. Zilpha just stared at his hand rubbing his throbbing member.

She imagined how it would feel touching a live cock again. Seeing her young student stroking his penis through his pants made her quite excited such that she was getting wet between her thighs.

"Now, play with your breasts."

Feeling aroused herself Zilpha did not hesitate to follow the young man's request. So she gently cupped her breasts with two hands and then kneaded them, squeezing them together and pinching her nipples all the while staring at Joey's hand on his crotch. Zilpha was beginning to enjoy this until

"Ok that's enough!"

Zilpha immediately stopped giving attention to her breasts. Joey could see that there was a hint of disappointment on her face when she stopped massaging her breasts.

"Come closer to me Mrs. Rollins!"

As she walked closer to Joey her eyes were still glued at his crotch area. Then Joey held her by the waist and pulled her to him such that she was leaning over Joey, then he gently cupped both of her breasts and then gently massaged her lovely orbs then he slowly licked one of Mrs. Rollins' erect pink nipples.

Zilpha tried to control herself; although she knows that she was being blackmailed in to doing this act she was enjoying what Joey was doing to her such that when she felt Joey's hot tongue on her nipple

"Mmmmmmmmmmmmmmhhhhhh..." Zilpha let out a faint moan expressing her satisfaction to her young student's actions.

Upon hearing his teacher's moan Joey knew that he has gotten his mature teacher aroused, so he unzipped his pants and pulled out his throbbing cock and then gently guided Mrs. Rollins' hand to his hard as a rock penis.

Once she touched Joey's manhood Zilpha instinctively enveloped it into her soft hands and then began a stroking motion, sending young Joey trembling in shear pleasure. Zilpha was surprised by the size of the boy's cock; Eric's cock was just half the size of this monster. The feeling of Joey's humongous member in her hand excited her even more so Zilpha kept on stroking her young students throbbing member while he sustained his onslaught on her bare breasts.

"Oh Mrs. Rollins that really feels goooooooood!" Joey expressed his satisfaction on the job being done to him by his mature teacher.

The two of them drifted into fits of pleasure until, a ring on the phone interrupted their sexual act. So Zilpha reluctantly let go of Joey's cock and then straightened up and then answered the phone.

"Good evening Mrs. Rollins, your husband has just arrived to pick you up ma'm!" came the voice of the on duty guard.

After putting the receiver down Zilpha immediately got her bra and put on her blouse.

"What's the matter, Mrs. Rollins?" Joey impatiently asked her.

"My husband's here to pick me up, hurry up now get dressed." She nervously told Joey.

" Okay, but Mrs. Rollins, remember I'm not finished with you yet!" Joey warned her as he got up and zipped up his pants.

"Ok Joey, but please leave right now before my husband catches you here! Please!!!" Zilpha pleaded to her student.

"But before I go can I have a goodbye kiss?" Joey mischievously asked her.

Without saying a word Zilpha kissed Joey on the lips but she was taken by surprise when Joey introduced his tongue to her mouth so Zilpha had no choice but to suck on young Joey's tongue. Then after a few seconds Zilpha pushed Joey back and then

"Now please leave right now Joey, before my husband gets here. Please!" Zilpha begged her young student.

So Joey sensing that Mrs. Rollins was on the verge of tears reluctantly let go of her and then went out the door.

*************************

Zilpha sat down on her chair shocked at what has transpired. She could not believe what has just happened to her, she felt ashamed of herself but at the same time she enjoyed it too. Her arousal was evidenced by a dripping pussy that needed to be taken cared of. Zilpha was confused, she could not comprehend why she enjoyed being touched by someone who was trying to blackmail her and she could not understand why upon touching young Joey's cock she felt an impulse to masturbate him in order to please him. These thoughts struggled through her mind as she stared on a blank wall waiting for her husband to come.

When Joey got out of the office he walked to the guardhouse where the phone call to Mrs. Rollins' office came from. There he saw Mr. Rollins getting out of his car, he saw a man about 60 years old with gray hair and a small frame, he thought to himself this man could not satisfy Zilpha and what would this old man do if he knew that 5 minutes ago he had been licking his wife's succulent breasts. So with that thought Joey suppressed a laugh and then headed home, he could not wait for tomorrow so that he could continue what he started with Mrs. Rollins.

When her husband arrived Zilpha she had already packed her things and she was ready to go.

While they were driving home, Zilpha was looking out the window, her mind wandered to the incident with Joey she kept rewinding the scenes that happened earlier. As the episode, which occurred earlier flashed into her mind she could feel her vagina getting wet, soaking her lace panties in the process. She imagined holding on to Joey's cock and then masturbating her young student until his white hot cum flowed out of his enormous cock. Zilpha's daydream was cut short when they pulled up on their drive way. After disembarking from the car Zilpha immediately proceeded to the bathroom, ignoring her daughter that met her by the door, she needed a cold shower. While she took a shower, she reasoned with herself, she could not let emotion dictate her actions she must be reasonable, she could not let Joey have her. It would not be right, although she was yearning for a man, she could let her student blackmail her in to fucking him. These thoughts played out in her mind as she lingered in the shower to cool down her aching pussy. When she finished her shower she made a decision, she would not accede to Joey's bid but give him an alternate proposition.

********************************** The next day, Joey woke very early; he was excited to go to school. So Joey got dressed and then went to school very early. At around 8:15 AM, when all the students where milling to their respective classrooms, Joey went to Mrs. Rollins' office. As he peeked into her room he greeted his teacher

Category: Mature Stories