tagIncest/TabooJessica's Cougar Mom

Jessica's Cougar Mom


Standing there in her favorite black mini, low-cut silver top and stiletto heels, Jessica Holliday stared down to the end of the bar. She still could not believe what it was she was seeing. This was the reason Rob had stood her up? This was his "last minute emergency?"

They hadn't seen her yet, so she moved to a spot where she could easily see them, but they'd be hard-pressed to see her. Seething with rage, she was glad her Sensei in karate class had taught her techniques to channel her anger. She took cool cleansing breaths and let her rage melt away. In full fury, she could have broken some of Rob's bones, Jessica was that angry but it helped no one. She let herself breathe, calm down. Jessica had a temper, karate had helped her channel her aggressive tendencies. In a few months, she would achieve her Black Belt. She would have been ashamed if Sensei heard of her using her skills in a bar fight, it was beneath her.

Most people wouldn't have blamed her. How many people would have been able to remain calm at the sight of seeing their boyfriend with his hands all over their 37-year old mother? The two of them were making quite the little spectacle of themselves.

Okay, Jessica rationalized, I should be fair. He's not really my boyfriend; he's more of a fuckbuddy. Like Jimmy. Or Kaitlyn. Or Nickie. Or Nickie's brother, Tim. Jessica had also channeled some of her aggressive tendencies into matters sexual. She liked to fuck and she liked to fuck as often as humanly possible. Early on, the nineteen-year old realized that just one lover wasn't going to be enough. Neither was one sex, after dipping her toes in the pool of bi-sexuality, she went in for a long, luxurious swim.

Jessica went to the other bar on the other side of the club and ordered a Singapore Sling. Since childhood, she liked sweet things when she was upset. She'd just started drinking when her mother's boss, Alden Jackson, sat down beside her.

"Fancy meeting you here, Jessica," The handsome southerner smiled. "Your mother and I come here sometimes after work, for a drink."

Jessica nodded. She knew the handsome, dark-haired Georgia native and her Mom did a lot more than that, but she couldn't blame her mom for that either. He was nearly 6'6" tall, barrel-chested and had a voice that sounded like Bourbon going down smooth. There was an intensity to Alden that few men possessed, if Jessica was a few years older, she'd have gone after him herself.

Then, Jessica stopped herself. Why was she being such an idiot? She'd be 20 next week, she was an adult. If Angelica could go out with Rob, why the hell couldn't she make a play for Alden? Of course, that depended on if Alden was interested ... but the leggy, auburn-haired girl knew most men would be interested, providing they still had a pulse. She let her skirt ride up a few inches to show the tops of her stockings, she leaned forward a bit more to show some cleavage and her brown eyes met Alden's as she began to flirt with him.

"Is drinking all the two of you two do when you come here, Mr. Jackson?" Jessica's voice trilled. "Or may I call you Alden?"

"You may. What are you asking me, Jessica?"

"Wellll ... Mom's single, you're single. I know I don't come here for the music or the alcohol ... I come here because it's full of good-looking men and women. Just what things do you and my mother get up to?"

Alden smiled. "Wouldn't you like to know?"

Jessica placed his hand on her stocking-clad knee. "Yes, I would. Or perhaps you'd like to show me?"

Looking around to see that no one was watching, Alden smiled. Then, he moved his hand up her leg a bit. Jessica leaned forward and kissed him hard, letting her intentions be obvious.

"God, you're a hot little thing. You might just be as hot as your Mom!" Alden grinned.

"Buy me another drink and I'll let you take me somewhere and I'll show you that I'm even hotter!" Jessica giggled evilly. It was a bit of bravado on her part as she had no idea what kind of lover her mother was, but she was horny as hell. Alden would be her first older man, but if the rumors she'd heard around town were true, he would be an amazing fuck.

He was beyond amazing, not only was Alden steel-chested, his cock was like a piece of steel as well. Alden knew how to use it and the rest of his body, he had Jessica in many varying positions, but she came in all of them. He treated her kindly, but wasn't afraid to use her body sensually, to show her what she was capable of. From her training in Martial Arts, Jessica was very athletic, toned and flexible; she also had skilled hands and a wonderful mouth. They didn't stop fucking until well past 1 AM and wouldn't have even stopped then had Alden not had to fly to Texas on business the very the next morning.

Jessica arrived home by Cab around 1:30 and it was scarcely 10 minutes later when Angelica walked in the door. She staggered a bit, but didn't seem to be drunk ... aha, Rob got a little action tonight, Jessica giggled to herself. Well, to be fair, her raven-haired Mom was still a stunner and the silver mini-dress she wore clung to her like a second skin. She knew Rob had always thought Angelica was a MILF. She wasn't angry at him for taking the opportunity, it was just the sneaky he had gone about it that pissed Jessica off. Still, things had worked out for them both in the end.

"You're still up," Angelica nodded to Jessica, then sat down on the couch opposite her daughter.

"Yes, and you're just coming home," Jessica retorted. "So, how was your evening? What did you do?"

"Went to the bar, met Rob, went to a hotel and fucked him. What did you do?" Angelica smiled.

"Went to the same bar, saw you two together, had a drink, met up with Alden and fucked him," Jessica smiled back.

"HOW WAS HE?" Both of them said at the same time and then began howling with laughter.

Neither woman was ever dishonest with the other and both were highly sexual. It didn't bother either of them that they had fucked the other's partner, it was actually quite funny. Angelica had raised her daughter to be very open, because her own upbringing had been totally opposite to that.

"Alden's a wonderful lover Mom, very smooth, in control at all times, he was masterful and yet wonderfully attentive. It was some of the nicest sex I've ever had," Jessica recalled.

"He is good in bed, I will admit that," Angelica smiled. "But there's something to be said for youth. Rob was primal and savage, he gave me a good hard pounding. Sometimes, you just want to be fucked and he didn't seem to have a problem with that," Angelica laughed. "I should have asked you first though, sorry."

"Not a problem Mom, I don't own him. I'm just pissed because he cancelled our date with some bullshit excuse. I wouldn't have even found out the truth if I hadn't gone to the bar looking for some action. I was hoping to find either Nicole or Tim there, I could've gone either way."

Angelica smiled. "I admire you for taking advantage of all your options. I still haven't swung with another woman, I don't know if I'm ready for that," she told her daughter.

"You don't know what you're missing Mom, girls are great," Jessica sighed. "Hey Mom, I've got an idea ... why don't we switch things up a bit? You seem to be enjoying the younger dudes and I really got off on Alden, why don't we go out tomorrow and I'll point out some guys that will really get off on your MILF-ness and you can point out some mature studs that might dig a young hottie like me. What do you say?"

The perfectly-evil grin that crossed Angelica's face was the answer to that question.

It worked out exceptionally well. Angelica was so delighted with her daughter's idea. They went out the following afternoon and bought new outfits, somewhat similar, guaranteed to catch attention. Jessica was in a black leather mini that was so tight she could barely sit down in it, a low-cut top and some new stockings and kicky GoGo boots. Angelica managed to pour herself into a pair of black leather pants, black PVC boots with a stiletto tip and a white silk blouse that hugged her 36C tits rather nicely. Neither woman wore a bra, Jessica wore a thong for her own protection but Angelica was totally naked underneath. They walked into the bar arm-in-arm and there was a buzzing like a swarm of bees, the mother-daughter twosome attracted their fair share of attention and gossip.

Jessica's friends were delighted with Angelica, most of whom she had not previously met. Jessica left her mother to fend for herself, knowing she'd find her prey for the night and that whoever her mother chose, they'd better be on their best game tonight. Jessica and Angelica were both sexually insatiable, now it was Jess' turn to find a playmate.

She set her sights on Martin, a handsome stockbroker her mother knew "intimately". He was supposedly divorced, but Angelica clued Jessica into the fact that he and his ex couldn't keep away from each other. "You'll see why," was all that Angelica would say on the matter.

She sat down beside Martin and ordered a drink. He nodded in her direction and then the bartender's, paying for her drink.

"I've seen you in here before, you're always surrounded by a group of friends, including some very lovely women," Martin smiled.

"I come here a lot, but now you have me all to yourself," Jessica flirted back.

"Not quite." A melodious voice came from behind them and Jessica turned to see a stunning black woman coming to join them. She must've been nearly 5'10" and beautiful, regal in her demeanor. The woman smiled at both of them.

"My name is Diana ... I live with this beautiful stud here, but don't worry honey, we like to share and I can see you won't mind that at all, will you?" Diana purred as she sat down beside Martin.

"Not in the slightest," Jessica said, holding out her hand. "My name is Jessica, I believe you both know my mother, Angelica?"

There was a look that passed between the two that spoke volumes. Jessica now knew what her mother had been talking about and allowed herself to be taken home by the swinging divorcees. She had a blast and could see why Diana couldn't give up Martin – he was a bit on the arrogant side, yes, but he had a horse-cock that made you crave more. As for Diana, she was a wonderfully sensual and giving lover and whenever Martin was out of action or needed a break, Diana was all-too happy to fill in, kissing here, licking there and keeping Jessica in a state of fullest arousal.

Jessica also found that Diana's body was equally responsive to licks and caresses and she made sure that her partner was taken care of while Jessica tended to her. Martin was a stallion and both of them extracted a promise from Jessica that she'd return in the not-too distant future.

Jessica walked into their home and poured herself a glass of ice water, her mother followed not 10 minutes behind. She looked a bit disheveled, but not too bad.

"How were they?" Angelica giggled, knowing what had likely gone on between her sometimes-playmates and Jessica.

"My God Mom, do you have to ask?" Jessica sighed, sipping her water. "I made a good choice. Who did you go home with?"

"Tim and Nickie. Did you know that they ...?"

"Sleep with each other? Yes. They once told me that it's extra-hot with family. How was it, Mom? Did you have sex with Nickie? Did you?"

Angelica smiled. "I did, as a matter of fact, I had sex with her before I had sex with him. She was all over me most of the night darling, she was very flirty and attentive. She's got that gorgeous tanned, blonde body and those legs and tits ... I finally gave in to temptation and baby, were you ever right, a woman knows what to do. We must have been eating each other for 30 minutes when Tim finally joined in, he said he could never resist seeing his sister slut it up with another girl. It was so wild, they're both such magnificent physical specimens, you lucky, naughty little girl!" Angelica laughed.

"I'm sure they'll invite you back, those two sex fiends," Jessica laughed. "So, it didn't bother you sleeping with a brother-sister combo ... you know, the incest thing?"

"No. Some people might have been offended, but they're both adults and over 21, that's their choice. Who are they hurting?"

Jessica had always known her Mom was cool, but this devil-may-care attitude was a revelation. They cuddled together on the couch and shared a pot of tea before calling it a night, agreeing to go out again on Friday.

It became a regular, twice a week event ... they seemed to zero in on each other's tastes rather nicely. One night, Jessica went home with a female co-worker of her mother's that Angelica was sure had been flirting with her. Angelica was right, the woman was most definitely gay and Taryn's long, snaky tongue hit all the right spots. Her body was so leggy and model-perfect, you could come just looking at her. Angelica herself went home with Kaitlyn, the pretty strawberry-blonde's bubbly personality had been endearing herself to Angelica for a while now. Kaitlyn loved her sex sweet and playful, they had sex in the shower and then in Kaitlyn's room. Then Kaitlyn called her boyfriend and let him listen over the phone while they lez-fucked again.

After a number of weeks and wonderful sexual adventures, something fun happened that neither of them could have foreseen. The two women met up at the bar, Jessica in her tiny leopard miniskirt, Angelica in a tiger print, both in stilettos, both looking very "vampy".

"Mom, I've got somebody that's perfect for you."

"And I met a guy I think you'd like, was talking to him about 30 minutes ago. He's an author, his name is ..."

"Don't tell me ... it's Eldon and he's 28," Jessica said, staring at her Mom.

They both laughed, realizing they'd picked the same man. He was almost the same distance in age from both, 8 years older than Jess, 9 younger than Angelica. He had dark, wavy hair, a firm jaw and was beautifully groomed and dressed. Everything seemed perfect and no flaws were visible. The two women knew both of them had found several things about him that they liked, so what to do?

Jessica solved the problem. At first Angelica was leery, but so far, her daughter's hunches had been right. So it was that Eldon the author found himself being approached by the two very hot women he'd flirted with this evening. He thought he might be in trouble until Jessica said "So babe, how would you like to have the time of your life with two willing and very hot ladies?"

Eldon was taken aback, but he did manage to squawk out a passable "Yes", so they all hailed a cab and went back to Angelica's home. She and Jessica put on a little striptease show while he got comfortable, but Eldon wanted more. "Why don't you two kiss a little, you look like you're both into it?" He asked.

Angelica was about to say something, but Jessica pulled her mother close, their tits mashed together and they kissed, soft and sensual. From second one, it was electric and Angelica didn't fight the feelings ... what was it Jessica had said about it being extra-hot with family? It was true, her hands moved down Jess' body and fondled, stroked and caressed as they embraced, putting on a lesbian act for Eldon that truly was no act at all.

They separated and Angelica said "Baby girl, I ..." but Jessica shushed her. As a duo, they moved towards Eldon and undressed him. Then Jessica let her mother suck his cock while she got her pussy eaten. Her wet, trimmed auburn bush was devoured while her mother devoured cock. She'd never seen Angelica suck dick before, she thought her Mom might have a leg up on her in that department.

Once he was hard, Angelica insisted that Jessica ride his dick and she replaced Jess on his face, although facing her daughter as she rode. She wanted to continue their mutual exploration, so while Jessica fucked the dark-haired writer, she played with her daughter's tits and let their lips meet while they both were being tended to by Eldon. This was the hottest thing either of them had ever done, there weren't any regrets either ... both women were shaking and moaning as they fucked and got sucked and played.

"Oh God, Mom, you're so fucking gorgeous, his cock is so good, it's nice, it's all so damned nice," Jessica moaned.

"And I love these bouncy tits of yours baby and watching you move, it's fucking sexy," Angelica called out. "Let's switch now!"

They changed places and saw the goofy grin on Eldon's face. He'd only just now discovered that he was fucking a mother and daughter, they looked enough alike to be sisters. He just enjoyed his good fortunes and let his cock go deep inside Angelica's cunt, intent on giving her a good fuck. The walls of her pussy tightened around his shaft as he fucked her and Jessica's wet pussy was dripping on his lips as he ate her cunt.

"More Jess, more Eldon, I can fucking take it," Angelica screeched as she moved her hips back and forth. Jessica was moving in a similar manner as she rubbed her pussy all over the young author's face.

The three of them didn't last too much longer, Eldon cumming last. Mother and daughter shared his spunk, helped him clean up and sent him home an hour later, after some coffee to help him sober up. He was still a bit woozy, not from booze, but from the appetites of the two hellcats he had just fucked.

Angelica and her daughter were far from exhausted though ... they wanted some time alone to discover the new intimacies they had now shared. They had incestuous lesbian sex for hours after, finding that they were well-suited to each other. Jessica wondered what the two of them might do next? Then remembered Nickie and Tim had once told her that their parents were swingers. Might partying with an entire family be another route they could explore?

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