Billy can’t remember where this all started, his desire to be 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. Billy James was 18, a high school senior, and was active in school sports. There were other girls his age that he was interested in but there was something about the counselor that excited him.

The guidance counselor was Mrs. Wendy K; she’s the guidance counselor of Billy’s school for the past 10 years. Wendy K is a 53-year-old mother of two grown boys, that are on their own now and out of the home. She’s married to a Oil Engineer that is often away. Billy’s playing sports is ok but he prefers to be home on his computer playing games and surfing the internet for Foxy Mature women. That he and some of his friends formed a group that helps with repair of the computers. But Billy’s favorite pastime was fantasizing about Mrs. K. He would jerk off night and day imagining Mrs. K in different sexual acts with him. One time the picture of Mrs. K was published on the school paper, so Billy got a few of those and used them cum masturbate on. Billy was bursting with sexual tension such that he could not take it anymore he had to fuck Mrs. K soon or he will go crazy.

That opportunity came when Billy was asked if he could upgrade the existing computers of the Guidance office for Mrs. K. So Saturday morning Billy were at school preparing for their work. When the computers were assigned to the members Billy went to work on the computer of Mrs. K. So the teacher in charge gave him the key to Mrs. K’s office and then he proceeded to her office. Upon entering the room Billy was met with a familiar scent, an erotic scent that always accompanied Mrs. K the scent alone gave Billy a boner. He then inspected the computer of Mrs. K and then turned it on. After booting up Billy went directly to the windows explorer to check her files. There was nothing out of the ordinary on her folders and files. But when Billy changed the explorer setting to enable the viewing of hidden files Billy 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 Billy was beginning to get frustrated there was nothing exciting on Mrs. Ks’ computer. But when he opened the hidden folder named “XXX” he found out that it contained several jpeg files, named Private 1, Private 2, Private 3 so he opened the pictures and to his surprise and utter delight the pictures where of Mrs. K in various sexual acts with some guy. Billy’s boner got harder upon viewing the pictures, although only in pictures, it was the first time that he saw Mrs. K naked. He could not help but stroke on his member. But what intrigued him was that the guy with Mrs. K was not her husband and the guy looked very familiar. Billy’s heart skipped as he remembered who was the man with Mrs. K it was Mr. Rob Perry 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. K’s 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. K’s blackmail finally he’ll get the chance to fuck this beautiful and sophisticated mature lady.

It was Monday morning, Wendy just got out of the shower and grabbed a towel and began drying herself off. She was thinking about Mr. Perry, 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 Mr.Rob Perry would take pictures of them in various sexual positions at first Wendy was a bit apprehensive about the pictures but that didn’t stop Rob from taking them, in time she grew accustomed to the fact that this experiment spiced up there relationship. Her affair with Rob 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. Wendy just consoled herself that it was fun while it lasted.

Those thoughts aroused Wendy 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 Rob. So Wendy, 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 Rob ramming his cock in to her wet pussy. After a few minutes Wendy came to an earth pounding orgasm.

“Haaaaaaaaaaahhhhhhhh” Wendy suppressed a scream.

After her orgasm she 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. It was her husband saying he was off to work and would be out of town for over two weeks.

Wendy 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 Eh. teacher in some mindless conversation she went to her office and then opened the envelope. Wendy was shocked when she saw the contents of the envelope. It was the print outs of the pictures of her and Rob 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. K, 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 bilj@yahoo.com there will be instructions for you there. Upon reading the text message Wendy 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 MIRC chat room and she would look for the nickname big-guy from the names that were logged in.

Billy waited patiently for the for Mrs. K’s 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. K, he also was having second thoughts about pushing through 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?

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

big-guy> Yes!

Teacher> what do you want from me? She asked

big-guy> we will get to that in a little while. Joey replied through the computer

big-guy> 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?

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

big-guy> you better not hang up on me now Mrs. K!

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

big-guy> 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.

big-guy> I don’t want your money! I just want to have what old Mr. Perry 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.

big-guy> Ok Mrs. K 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. K 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?

big-guy> 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 Billy 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 he was delirious with excitement. Wendy 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, she 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 Wendy readied herself. After about 5 minutes a knock came on the door. So she opened it and saw Billy.

“Oh Billy I don’t have time to see you now, I am waiting for someone important.” Billy knew that Mrs. K would never think that it was him that got the pictures.

“On 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 Billy?” her face turning a bit red in anger.

“Yes, its me” Billy 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!” He screamed at her as he entered the room and locked the door.

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

“Why are doing this to me? What did I do to you to deserve this treatment?” she asked Billy

“I’ve been good to you, Billy”

“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 Billy 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 Billy that’s not true.”

“Oh please stop it Mrs. K, I’m not here to debate 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.” He told her with irritation in his voice.

“I should not have had that affair with Rob, it’s just that he caught me when I was really very lonely.” She tried desperately to appear very disappointed.

“Enough talk now!” Billy cut her short as he sat on her swivel chair.

“I think it’s about time we get started.” He commanded.

“You’re really going through with this, Billy?” she asked him but she really knows the answer.

“Yes” he replied

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

“Stand in front of me.”Billy instructed her

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

“Please unbutton your blouse.”

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

“Now remove your blouse and your bra.”

“No Billy, I can’t do this!” she protested.

“Your doing fine Mrs. K, just do what I’ll say and you will be fine.” Billy reminded her.

So having no choice Wendy 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.K’s naked breasts gave Billy a major hard on such that he could not help but rub his rigid member through his pants. Wendy 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 she 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 Billy’s hand on his crotch. Wendy was beginning to enjoy this until

“Ok that’s enough!”

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

“Come closer to me Mrs. K!”

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

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

“Mmmhh...” Wendy let out a faint moan expressing her satisfaction to her young student’s actions.

Upon hearing his teacher’s moan Billy 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. K’s hand to his rock hard cock.

Once she touched Billy’s manhood Wendy instinctively enveloped it into her soft hands and then began a stroking motion, sending young Billy trembling in shear pleasure. She was surprised by the size of the boy’s cock; Rob’s cock was just half the size of this young mans cock. The feeling of Billy’s humorous member in her hand excited her even more so Wendy kept on stroking her young students throbbing member while he sustained his playing with her bare breasts.

“Oh Mrs. K that really feels goooooooood!” He 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 Wendy reluctantly let go of Billy’s cock and then straightened up and then answered the phone.

“Good evening Mrs. K, your husband has just arrived to pick you up ma’m!” came the voice of the on duty guard. OMG Wendy thought he said he was going out of town this morning.

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

“What’s the matter, Mrs. K” Billy impatiently asked her.

“My husband’s here to pick me up, hurry up now get dressed.” She nervously told Billy.

“Okay, but Mrs. K, remember I’m not finished with you yet!” Billy warned her as he got up and zipped up his pants.

“Ok Billy, but please leave right now before my husband catches you here! Please!!!” She pleaded to her student.

“But before I go give me a goodbye kiss?” Billy mischievously asked her.

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

“Now please leave right now Billy, before my husband gets here. Please!” Wendy begged her young student.

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

Wendy 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. Wendy 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 Billy’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 Billy got out of the office he walked to the guardhouse where the phone call to Mrs. K office came from. There he saw Mr. K 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 Wendy 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 Billy suppressed a laugh and then headed home, he could not wait for tomorrow so that he could continue what he started with Mrs. K.

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

While they were driving home, Wendy was looking out the window, her mind wandered to the incident with Billy 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 Billy’s cock and then masturbating her young student until his white hot cum flowed out of his enormous cock. Wendy’s daydream was cut short when they pulled up on their drive way. After disembarking from the car Wendy immediately proceeded to the bathroom, ignoring her husband that was her by the front 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 Billy 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 Billy’s bid but give him an alternate proposition.

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

“Good morning, Mrs. K Did you sleep well last night?” He asked Wendy in effort to mock her.

Wendy was startled to see Billy this early, but she kept her composure and answered her young student’s query.

“Oh its you Billy, I did not sleep as well as I would like to.” She answered him without hesitation.

Then Billy entered the room and locked the door behind him.

“Well, Mrs. K are you ready to continue where we left off yesterday?”

He asked his teacher while he got her hand and guided it to his throbbing cock and rubbed his cock with it through his pants.

“Billy, I have something to tell you.” Wendy interrupted as she removed her hand from his crotch.

“What?” Billy irritatedly asked her.

“Billy I can’t let you have intercourse with me, because that would not be right. I’m old enough to be your mother.” Wendy explained to Billy with determination written all over her face.

“Ok, if that’s your decision, fine. Just be ready for the consequences of that decision.” Billy calmly told her while heading for the door.

But before he could turn the knob open, Wendy grabbed his arm and

“Wait, I’m not finished yet. I said we can’t have sex but I can do a lot of other things to pleasure you, like shall we say masturbate you? But that’s as far as I can go Billy. Please understand?” Wendy presented her proposition to her blackmailing student.

“What if I say no, Mrs. K?”

“Well as I told you that is as far as I can go, Billy.” Wendy held her breathe as she waited for his answer.

Billy thought for a moment, He could say no to her proposal and she would be true to her word that masturbating him was as far as she could go, then he would email those pictures and that would start a scandal of sorts. Then Mrs. K would suffer the consequences but he still would not have had her. But if he agrees to her proposal, at least he would be rewarded by a hand job from his mature teacher.

“Ok, Mrs. K I’ll agree to what you’ve said, but that would not just be a one time affair.” Billy countered an offer.

“Ok, Billy, then that’s settled. You’ll not expose those pictures if I masturbate you.” Wendy clarified with him.

“Now can we start?” Joey impatiently asked her.

“We can’t do it here Billy. Someone might barge into this office any time.”

“Skip school tomorrow morning and go to my house so that we’ll have some privacy.” Wendy explained to Billy while she hands him a piece of paper containing her address. “But ... but...” Billy was trying to protest but Wendy placed her finger on Billy’s lips and then gently kissed him on the lips to stop his protestations.

“Now, Billy be a good boy and return to your class. And I’ll see you tomorrow.” Wendy told her young blackmailer after she broke their kiss.

“Well ... Ok Mrs. K.” Billy finally ended his protest, he was mesmerized by Wendy’s kiss.

After Billy went out, Wendy sat down and heaved a sigh of relief. After contemplating on what happened Wendy smiled to herself, she was getting out of this trouble anyway.

The very next day Billy, woke up at around 6:00 in the morning and by 7:30 he was standing across Wendy’s house. He could still see her husband’s car on the driveway, so he concluded that he might still be in the house. So Billy patiently waited until 8:00 then he saw Mrs. K’s husband went out the house and then boarded the car. Now he was sure that Mrs. K was alone in their house. Billy waited for another 10 minutes before he approached Mrs. K’s house, he wanted to make sure that the car was not about to return.

Wendy made breakfast early and then took a bath. She told her husband that she would not be going with them this morning because had to finish a report that was due this morning. When her husband finished breakfast she hurriedly cleaned the kitchen and changed to her office uniform, which was a white satin blouse and an aqua green skirt, which was just cut above the knee. By 8:00 she was already pretending to work on some papers on her desk. By 8:10 her doorbell rang, Wendy immediately got up and opened the door it was Billy.

“Good Morning Mrs. K” Billy greeted her.

“Good Morning, Billy comes in.” Wendy replied as she guided him in, trying to project a smile.

“Sit down, make yourself comfortable.” Wendy told Billy acting very hospitable.

When he was seated, Wendy sat beside him and then gently placed her hand on his thigh, in an effort to calm his nerves thus giving him an instant boner.

“So Billy, are you ready?” Wendy asked him, she was eager to get this thing over with.

“I’m ready Mrs. K, I’ve been ready for you the past 2 years.”

“Billy, I think if we are going to do this you should call me Wendy, at least while were doing this.”

“Ok Mrs ... err ... Wendy” Billy stammered his excitement growing with each passing second.

“Ok, Billy just sit here while I get something from my room.”

She got up and went upstairs to her room. When she returned she brought with her a towel and a bottle of hand lotion and then she sat beside him on the couch.

“Billy you can take it out now” Mrs. K ordered him.

“Take out what?” Billy was confused by her demand.

“I mean take off your pants.” Wendy told him as she faked a smile.

Billy anxiously followed her command he was really very excited such that when he pushed his jeans down, his cock sprang up, jutting from his nest of dark pubic hair. All ten inches of its glory.

Wendy was surprised at how it looked, it was enormous and its purple head looked like it will be bursting any time now. But Wendy gathered her composure and acted as if seeing such a humorous cock was just an ordinary thing for her. Then Wendy got hold of the bottle of lotion applied some on her palm and then she enveloped Billy’s cock with it. Billy jerked as Wendy’s hand made contact with his cock. He could not believe it, his fantasies are becoming a reality the woman of his dreams was giving him a hand job. As Wendy continued to stroke young Billy’s cock she too felt a tingling sensation forming between her thighs, the same sensation that she felt when she held Billy’s cock in her office. She was getting turned on again with what she’s doing to her student. Such that She shifted her position, she was know kneeling on the carpet between Billy’s spread legs, but still stroking his manhood.

“Oh Wendyyyyy ... that feels really goooooooooooood!” Joey expressed his satisfaction as Wendy milked his penis.

Encouraged by Billy’s reaction Wendy cupped his balls squeezing them gently while her other hand continued stroking his cock. Billy felt that he was nearing an orgasm, so he stopped Wendy from stroking his cock and then “Mrs ... Err Wendy, can you take off your blouse?” Billy asked her, he would not cum yet without feeling her body.

Without hesitation Wendy stood up and then unbuttoned her blouse and then took it off. She is now just in her bra. Then Billy pulled her in to him, such that she was leaning over him on the couch and her bra covered tits were just a breath away from Billy’s lips. Then he reached behind her and unhooked her bra and as her bra fell harmlessly on the couch Wendy felt Billy’s breathe brushing on her pink nipples causing it to stand erect. By now Wendys pussy was drenched with her love nectar, her breathing grew heavy in anticipation of what Billy might do next. Then without saying a word Billy licked one of her nipple and then gently sucked on it. Bringing about a soft moan of satisfaction from his mature teacher.

“Ummmmhhhhhh...”

Wendy felt guilty when Billy reached out and licked her breasts Wendy knew she should stop him, but she couldn’t. She was being carried away by the moment. Such that without Billy asking her she wrapped her soft hands around his massive cock and then started to jerk it off again.

“Oooooooooohhhhhhhhhh, Wendy” Billy moaned as he continued to suck on her creamy white breasts.

After a few minutes of Billy’s pleasurable playing with her bosom Wendy was on the verge of an orgasm such that

“Hhhhhhuuuuummmmmmhhhhhh...” Wendy moaned as she bit her lip to stifle her cries, her body hardened and her grip on Billy’s cock tightened as she came.

Billy was not aware that Mrs. K had an orgasm because he too was on the verge of cumming. The pressure of Wendy’s intense stroking was just too much for Billy to take such that

“Wendyyyy ... I’m cummmmmmming...” Billy screamed as he squirted his sperm all over her hand some of it hitting her skirt and her exposed belly.

As Billy violently came in her hand Wendy continued to milk his cock until it went limp on her hand. She then sat down beside him; she too was exhausted from her orgasm. After regaining her bearings she immediately got the towel beside her and then wiped her hand with and then she reached for Billy’s cock with it and then cleaned it from his sticky cum.

“Was it good Billy?” Wendy broke the silence as she continued to clean his cock.

“It was the best, Mrs ... err ... Wendy”

“Ok, now hurry up and zip up your pants coz I’m running late for a meeting at the office.” Wendy ordered her young student as she gave his limp cock one final rub before placing it inside his underwear.

“When can we do this again Mrs. K?” Billy impatiently asked his teacher as he felt his cock beginning to get hard, caused by Wendy’s rubbing.

“Just let me know, so that we can make arrangements like this, coz we have to be discrete about this Billy we don’t want anybody knowing about what we have been doing or else we can’t be doing it anymore.” Wendy explained to young Billy.