Something Old, Something Newbydenny9©
Author's Note : This is a continuation of 'Denny, His Mom and Her Best Friend'. The reader might be wise to read that story prior to reading this one.
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A new meaning for the word 'cougar' has been coined by a local newspaper columnist. She says that 'cougars are older women who hunt younger men'. Barbara Hoey was a cougar. After seeing her former student getting a blow job from her best friend who also happened to be his mother, she knew that she was going to seduce him. Ordinarily she would only secretly lust after the young studs in her classes but because she feared losing her job as a teacher she never acted on her feelings. That was about to change.
Her friend Janet Mitchell's son, Dennis, was going to be a safe seduction. He was no longer officially her student although he had been just the previous year. Thus even if she was found out there could be no official sanctions taken against her. The boy was no longer a minor. His mother might be upset with her if she found out but she couldn't very well make noise about it since she couldn't risk exposing her own incestuous affair.
That evening while having a soothing bubble bath, Barbara started planning her seduction. She was not too concerned about being successful as she had known the boy his whole life.
She was so close to his mother that she had been pleased as punch when Janet had asked her to be Dennis' godmother. She had baby-sat the youngster until he reached twelve. In fact she had only stopped baby-sitting him when she became aware that he was infatuated with her. His puppy-dog eyes had started to follow her every movement and she became increasingly uncomfortable as he reached puberty. She even thought she had detected erections the last couple of times she had helped out her friend.
Janet and she would lounge around on weekends and she would catch the boy ogling her more and more as he passed through his awkward teenage years. Although she recognized that he was growing up she had never thought any lascivious thoughts due to the fact that he was still just a little boy and more importantly he was her best friend's son. However, when he was placed in her senior Math class last year, she had started to realize that he was developing into a young man.
Still she was careful not to do anything foolish. She had too much to lose. Besides that there were lots of handsome young studs around town since this was after all a college town.
She recognized that she had a lot in common with these young men. The most important wish for a young man is to get laid as often as possible. Barbara was likewise inclined. She wasn't interested in getting married which was a relief to them. They certainly weren't ready for kids. Neither was she unless they were in the eighteen to twenty-five age group.
Perusing these thoughts, Barbara' hands had started to fondle her breasts and to play with her clitoris. The picture in her mind of Janet sucking Dennis' rock- hard cock made her increase the tempo of her stroking as she caressed her own sex organs.
She wasn't sure that it was just the thought of Dennis' prick that had her so aroused. She recognized that she had always found her best friend extremely beautiful and desirable but she had always been afraid to act. Perhaps, she mused, she could seduce Dennis AND his mother. Wouldn't that be a turn-on?
Soon she was shoving her fingers in and out of her vagina and she could feel herself on the verge of cumming. Finally her body stiffened and she came noisily. She knew it wouldn't be long before she would have Dennis getting her off instead of relying on her own fingers.
After the relaxing bath she remembered that she and Janet had been invited to a college friend's wedding in Hamilton which was a 5 hour drive away. They had discussed going but felt that the drive would be too onerous and they would be too tired to enjoy the reception. Perhaps she could suggest that Janet ask Dennis to drive since Janet's husband had said he didn't want to go.
Furthermore she could suggest that they stay overnight. This way they could really enjoy the festivities. Of course, Barbara was planning on enjoying Dennis even more. She decided that she would broach the topic to Janet the next day at school.
When she made her suggestion to Janet during their lunch period a day later, Janet was almost too eager. Barbara then quickly realized that Janet had already started to envisage herself getting the opportunity to spend the night with her son away from her husband. After Janet agreed to look after the hotel reservations, Barbara realized that the only way she could seduce Dennis was to keep Janet occupied. That could be arranged she realized.
Janet enthusiastically reported Dennis' acquiescence to be their limo driver to the wedding which was only a week away. Janet then in her enthusiasm made the mistake of inviting Barbara over for a barbecue the next day. Barbara knew this was her golden opportunity.
The middle aged Math teacher arrived at the Mitchell home dressed rather provocatively for a school teacher. Her ample bosom was barely being held in by the low cut tank top that she had worn deliberately. Her flat bare midriff accentuated the curves leading to the short-shorts that she wore. High-heeled sandals emphasized her long tanned legs.
Neither Dennis nor his father could keep their eyes off her and both had difficulty keeping their hardened dicks from tenting out of their shorts. Dennis was disappointed that he had a date and would have to leave. He even considered canceling but as his date was the daughter of his father's best client, he felt obligated to go. After all he owed his father. He still felt guilt because he was fucking his mother right under his father's nose. It seemed the least he could do.
He knew that he would be thinking of Miss Hoey when he got his date alone and it would be Miss Hoey that he would be visualizing when the inevitable happened before he took her home.
The barbecue was full of banter and sexual innuendo, the dirty laughter increasing with each glass of wine. Every time Janet left them alone, Barbara would flaunt her ample breasts in Ben Mitchell's face and giggle when she saw how flushed he became.
"Why don't you come to the wedding, Ben? You and Dennis could share the driving. We could have a great time. " The emphasis on 'we' was not lost on the middle aged man and his cock hardened even more as he wondered if he would actually have a chance to fuck this sex goddess. He had dreamed of her many times and had even visualized her when making love to his wife.
After further discussion and teasing, he was ready to jump her right there but was restrained by the return of his wife.
"Ben has decided to come to the wedding after all, Janet. Isn't that wonderful!" she cooed without even waiting for his decision.
Janet, in turn, was totally flustered and babbled on about why he hadn't wanted to go. She saw the chance of being alone with their son rapidly disappearing. She was caught in a quandry. She couldn't very well try to talk him out of going since she had originally pretended to try to talk him into accompanying her.
When he said that he had changed his mind and was looking forward to going she feigned joy but was heartbroken inside.
Barbara however was ecstatic. She knew that her best friend's husband was hoping to have the opportunity to get into her pants but she was experienced enough to keep him at bay. She was going to seduce the younger Mitchell not the older.
While all this was going on, Dennis was drilling his manhood into Carol Babcock, who like him was a freshman at the local college. She wasn't bad looking and he actually was pleased that his father had arranged this date. They had gone to a movie and after exchanging a few kisses they had started to explore each other's bodies.
They were parked in the same rest area on the highway that Mrs. Green had taken Dennis to a few weeks earlier. While he had been licking Carol's pussy he had reminisced about Mrs. Green's initiating him into such sex acts.
Dennis had used Mrs. Green to learn about sex and for his own pleasure but since he had started to fuck his own mother, he hardly saw her anymore. Besides that she had seemed a little disinterested and less needy than she had been. (author's note – the reader may want to read a previous story that I posted entitled 'Mrs. Green and Her Son Bobby')
He had only agreed to date others his own age to throw suspicion away from the illicit affair that he was having with his mother. His sex drive seemed insatiable and although he was fucking or sucking his mother almost every day, whenever he went out on a date, his goal was always the same – to prove his manhood by scoring with as many females as possible. He knew that getting laid was really all that he was interested in.
The girl had made him wear a condom and he hated them. He never had to wear one with Mrs. Green or with his mother and he would bet that Miss Hoey wouldn't make him wear one either. He knew that they were too experienced to get pregnant. The young girls were always hesitant to let him in without 'a raincoat' on and indeed he too was concerned that he might get one of them pregnant. His mother had drilled that into him. Indeed he remembered how she had caught him with that girl Laura which had led to the two of them becoming incestuous lovers.
After cumming and getting his date off, he dropped her in her driveway and promised that they would do the date bit again. When he arrived home, Dennis hoped that Miss Hoey would still be at his house but the house was dark and there was no sign of anyone. Just thinking about her in that sexy outfit that she had been wearing made his young cock lurch. Automatically wanting release his thoughts now went to his mother.
He started up the stairs thinking that maybe his father had drunk himself into another stupour and he and his mother could break their promise not to do it when dad was in the house. Just as he was about to peek into the master bedroom he heard his father's voice bellowing, "Take it Baby! Your cunt is so fucking tight! I can't hold out much longer…Fuckkkk…. I'm going to cummmm!!!!!!!"
"Nooooo…. Ben! Wait!!! Wait for me! I want to cum too! Don't cum yet you bastard!"
But it was too late, Dennis could hear the final animal grunt and could just make out their shapes as his father exploded into his mother's cunt.
Then all he heard was his mother's voice berating his father. "You fucking, inconsiderate bastard! Why couldn't you hold off a little longer? I'm so fucking close to cumming!" He was shocked even more when he heard his mother ordering his father, "Get down there and finish me off with your tongue!"
Dennis scrutinized the dark to see if his father would do what he had been commanded to do but it was impossible to see much. A minute or so later he could hear his mother's familiar manta, "Oh god! I'mmm…cummminggg!!"
He couldn't tell if his father had gone down on his mother or not. Perhaps he had used his fingers to bring her to orgasm. Maybe she had masturbated herself! There was no way of knowing. The room became silent until he heard one of them start to arise out of the bed. Dennis retreated as quickly and as quietly as possible to his own room.
He kind of expected his mother to show up in his room once his father had fallen asleep but their agreed upon rule must have kept her from visiting her son. He fell asleep with no clothes on atop the covers hoping that she might still visit him. After all he was used to her waking him up with her mouth wrapped around his young cock. Alas that did not happen this time.
Dennis was surprised when his father reported that they would be sharing the drive to the wedding and that they were going to go and stay over the night before as well so that they could all really have a good time. For a brief second, he was disappointed but when his father reminded him that Miss Hoey was going as well, he remembered that he had hoped to get an opportunity to fulfill his fantasy of fucking his former teacher. Now he would have two nights to try instead of just one.
Finally the day of the drive to the wedding had arrived and Miss Hoey did not disappoint the men. She showed up in a light summer sundress that was barely held up by its spaghetti straps. The light material bounced teasingly just below her buttocks. She was obviously wearing no stockings and the men tried to visualize what kind of panties she was wearing. They almost fought over who would drive first and who would get to sit in the rear seat with her.
Barbara solved the problem by encouraging the father to take the wheel first as she would feel more comfortable knowing that the more experienced driver was behind the wheel. Normally this would have upset Dennis but he realized quickly that it meant he would be sharing the back seat with this incredibly sexy older woman. His mother was forgotten.
Within blocks the heat from her thigh touching his was having a profound effect on Dennis. He couldn't take his eyes off her legs. The dress was running well up her muscular thigh and when she turned to look out the window he thought he could see her white nylon panties.
The monotony of the drive and having taught all day was making both of the women sleepy and they put their heads back and started to nod off. Dennis took this opportunity to look down Miss Hoey's cleavage. "God!" he thought. "Her tits are so big and beautiful! I want to touch them and suck on them!"
Just then the car hit a pothole and Miss Hoey's head rolled onto his shoulder where it stayed. Carefully, Dennis removed his arm from under her and placed it around her other shoulder almost like they were cuddling. Fortunately traffic was very heavy and his father was giving total attention to the road. Dennis' fingers came in contact with the side of her right breast and he held it there afraid to move.
Getting bolder he started to let the sides of his fingers caress the breast gently through the thin material. There was no reaction from Miss Hoey. She seemed to be sound asleep now. The hem of her dress was right at her crotch now and it was just barely concealing her pussy. Dare he go further?
Just then the car lurched to the right and Miss Hoey's head fell into his lap. Still she slept! He on the other hand was wide awake! Actually his cock was trying to force its way out of the tight confines of his jeans. Her cheek rubbed against its length and he had to stifle a groan.
Then his eyes looked down to see that her behind was now totally exposed as her dress had ridden up her ass when she had fallen over. She was wearing a sheer pair of thong panties that barely covered the crack of her ass. He was in heaven and hell at the same time. If he touched her and she awakened, all hell would break loose but here was this goddess that he had adored for years and lusted after for 10 long months in her classroom, just begging to be touched.
His uncontrollable hormones won out and he placed his right hand on her ass tentatively. When she did not wake up he boldly started a circular motion with his fingers gradually getting closer and closer to the thong. He detected a muffled murmur from her throat and looked down to see her face still buried in his crotch. Oh what he wouldn't give to open up his jeans and stick his rock-hard cock into her beautiful mouth.
It was dark enough in the car now that Dennis felt reassured that his parents would not be able to see what he was doing so he decided to risk everything. He pushed aside the thong and started to caress Miss Hoey's clit and proceded to spread her outer lips. Breathlessly he waited for a reaction. She still appeared to be asleep but he could hear gentle whimpers coming from her throat.
He was getting bolder and he inserted first one and then two fingers into her pussy. She was sopping wet! Then he realized that he was finger-fucking the woman of his dreams. Her cheeks seemed to be moving over his cock now and he feared that she was about to awaken. He stopped his tactile probing and held his breath.
Before he knew what was going on, he felt Miss Hoey's fingers pulling down his fly! Could this really be happening?
Miss Hoey had never really been asleep and had hoped that the young stud would take the bait. When he had gotten up his nerve to stick his fingers into her cunt she knew that she could safely pretend to awaken. His thick cock lying against her cheek had actually been uncomfortable and she was now relishing the fact that the façade was over. She knew that Dennis could not resist now.
Licking the head of the boy's penis within inches of his parents was as brass as anything she had ever done in her life. If Janet should look back through the darkness would she be able to make out what was going on? Would she dare expose them if she did? Although Janet didn't know that Barbara had observed her sucking off her son, Barbara was pretty sure that Janet might be afraid that Dennis would expose their incestuous affair if she angered him. What else would explain her giving in to him in the gym store room?
While she licked up and down Dennis'shaft, the boy showed his willingness to please her in return by continuing to thrust his fingers in and out of her moist pussy. After several minutes of mutual pleasure, they both could feel that they were on the verge of orgasms. Unbelievably Dennis showed incredible restraint for a young man and he willingly concentrated on attempting to bring her to the precipice of sexual fulfillment.
Her body stiffened and she fought to keep herself from crying out as she peaked. She swallowed Dennis' cock which helped stifle her scream. She let loose a wave of fluid that flooded the boy's fingers. He smiled in the darkness pleased that he had been able to make this mature woman cum just with his fingers. He couldn't wait to do the same with his tongue and with his young cock.
When she got herself under control, the teacher raised her head from the boy's lap slightly so that she could fondle his balls and stroke his shaft as he pushed it in and out of her hot mouth. She knew that he was on the verge of cumming when he ran his fingers through her hair and forced more and more of his rod into her mouth. If she hadn't been such an experienced cocksucker she might have gagged when it reached all the way into her throat but she had been face-fucked by larger cocks than this and knew how to adjust her breathing accordingly.
Dennis was feeling the need to explode in her mouth but while the pleasure that her tongue was giving him felt so good he was trying to delay as long as possible. He was also fighting to keep himself from crying out her name at the top of his lungs and telling her what he wanted her to do with his cock and his cum. Indeed telling the female to suck his cock and to eat all his cum were almost second nature to him now. He wanted to tell this woman what a cocksucking cunt she was but knew he would literally have to bite his tongue.
Finally he could control himself no longer and he drove his rod straight up into the waiting mouth while at the same time forcing her head down into his lap to meet his throbbing cock head. Jet after jet of cum flew from his piss-hole and splashed against the back of Barbara's throat. She sounded like she was gagging but he could not let her head free until she had received every ounce of his jism.
After quite a few convulsions he could tell that she had drained him of almost all that he had and only dribs and drabs were being ejaculated now. He was amazed that he had ejaculated loads of white hot cum into the mouth of his former teacher and she had swallowed it all. God he wished he could announce to the world "Miss Hoey sucked me off in the back seat of my parent's car and she swallows!"