Gender: Male Age: 48 Location: Upstate New York
|Introduction: Theresa looks to expand the circle of play . . .|
“Jillian, you are looking great!” Theresa complimented her friend as they sat down for lunch at the ‘La Casa Enchilada’, their favorite Mexican restaurant.
“Thanks Theresa” Jillian beamed, “of course you look terrific as usual” she laughed. They’d been having this weekly lunch date for the last several months and had become much closer than the casual acquaintance they previously shared due to the close friendship of their sons.
Jillian had been divorced for 3 years now and she was finally feeling almost normal as a woman once again. Getting out with Theresa each week had helped in that cause. Luckily the alimony she received from her attorney ex was enough so that she was still able to stay at home, having not worked at all after getting married. She was able to raise her son Mason in a comfortable, though never lavish, lifestyle and could still treat herself to the occasional shopping trip and lunch with her friend.
While Theresa stood at a spritely 5’4”, Jillian was long and leggy, at 5’10”. She usually wore light colored dresses which complimented her shapely tan legs and today her shoulder-length golden hair was just perfect. Theresa’s initial scan confirmed what she had thought many times before: ‘definitely fuckable’. She could well understand how Mason would get urges toward his mom, living in that house alone with her.
Family sex was not a subject that Theresa had been able to broach with Jillian yet but she would push general sex discussions so that Jillian would begin to feel comfortable disclosing such personal info. They had talked several times about Jillian ‘needing to get laid’ but not looking for a man in her life.
Theresa had even made a trip with her to the adult book and video store that she had become a somewhat-regular patron of to pick out a vibrator for Jillian’s home use. Jill was embarrassed by the whole subject at first but eventually admitted that she had had her first really good cum in years when she used her new toy.
How extensive Jillian’s sexual relationship was with Mason was an initial mystery to Theresa, as Jim wasn’t able to offer much detail; but it did not appear that they had actually ever had intercourse. Jillian would let Mason watch her as she got changed and showered while he jerked off. She had also done some masturbatory assistance for her boy, as Theresa had started with Jimmy years ago. But Theresa often found herself looking at Jillian the way that Missy had looked at her young friends Sara and Christina; she wanted her naked and she wanted to touch her and be touched by her. If their sons got involve too, that was fine.
“How ‘bout we have a margarita?” Theresa offered.
“What are we celebrating?” was Jillian’s response.
“We’re two hot chicks sitting in a Cantina, that’s worth celebrating, isn’t it?!” Theresa laughed.
*** *** ***
Their second margarita was halfway gone as their lunch plates were taken from the table. “Phew, it’s a bit warm in here, isn’t it?” Jillian commented. She fanned herself with her hand.
“I always get a bit horny when I drink, don’t you?” Theresa leaned forward to whisper across the table.
Jillian nodded her head after downing the remainder of her drink.
“I’ve got a secret, Jill . . . I’m not wearing any panties!” she continued in her loud whisper.
Jillian’s eyes opened wide. “What? In that flimsy dress? You little slut!” she giggled as she leaned over to the side to look at Theresa’s profile. She was wearing a yellow floral summer dress which ended above the knee. Theresa scandalously picked up the hem of her dress to flash her friend. “Oh, my” Jillian put her hand to her mouth and tried to keep a straight face as she gave Theresa a frowning look of disapproval. The two of them burst out laughing like a couple of school-girls and asked for the check.
*** *** ***
Jillian had driven that day and as Theresa sat down in the passenger seat she ‘accidently’ let her dress ride up so that most of her thighs were exposed. “When I get home I’m gonna have to use my toy.”
While Jillian had never had sexual thoughts about another woman, she could not help but begin to be aroused by the sight of her nubile friend rubbing her hands up her naked thighs in the seat next to her. Her mouth got dry as her pussy began to get wet.
It was quiet in the car, except for the sound of their breathing, for the remainder of the ride. Theresa pressed the hem of her dress against her mound with her right hand and Jillian kept stealing glances at her while trying to keep her eyes on the road.
As Jillian pulled into their driveway and put the gearshift into park Theresa reached out and gently held her wrist. “Come inside with me.” She did not bother putting any pretense into her request as her level of arousal was quite obvious. The flush of warmth that traveled through Jillian’s body was something that reminded her of the first time that she found Mason was watching her in the bathroom by opening the door a crack. It was a primal sexual response that she was glad her body was still capable of.
She nodded numbly as she unbuckled her seatbelt and followed Theresa into the house.
Theresa poured them each a glass of chilled white wine. “Go relax in the family room, Jillian, I’ll be right there.”
Jillian gulped her wine and topped off her glass after Theresa went up the stairs and went down to the large, open family room. She kicked off her sandals and settled into the L-corner of the sectional sofa.
*** *** ***
Theresa considered changing her clothes but decided to keep the dress on so that she and Jillian were on equal footing. She wanted her friend badly but did not want to make her uncomfortable or jeopardize their relationship. After getting what she came upstairs for she returned to find her hot MILF friend with her legs curled under her in the corner of the sofa, sipping on her wine with a look of excitement but also trepidation on her face.
“I brought you something” Theresa said quietly as she sat down near her and handed her one of the two vibrators she was holding.
“You have TWO of them?” Jillian asked in mild surprise.
“Actually, three” Theresa informed her, “one each for me, Susan and Missy.”
“Oh, my” was all that came to mind as Jillian downed the remainder of her wine. Her head was swirling with images of Terry’s two young daughters clutching vibrators to their crotches. “Have you . . . uh . . . done this, um . . . together?”
Theresa nodded as she stood up for a second to pull her dress up over her waist and sat back down. She kept her left leg on the floor but pulled her right up onto the couch to expose herself to Jillian. She licked her own torpedo-shaped tool once, twisted it to turn it on and then brought it down to her lips, which were engorged with blood and protruding urgently.
Jillian had never before had an up-close view of another woman’s privates, and certainly not in such a state of arousal. Getting changed before and after swim class didn’t quite count. She stared intently as Theresa brought her tool up and down her labia and gently probed her opening with the first 2 inches of its shaft. She moved it in and out several times and then pulled the vibrating tip up to her clitoris, where she applied light pressure and began to shudder. Jillian watched in amazement at the erotic sight of her friend releasing additional fluids to coat her vulva in a sheen of sex.
She found that her fingers were pressed against her own mound and the pressure on her clit was just a tease of what she really needed. She slowly stroked herself down her slit once and back up, this time fully contacting her most sensitive spot to send jolts of electricity through her body.
Theresa had switched the vibrator to her left hand so that she could reach out to Jillian. She looked her friend firmly in the eyes as she grabbed her breast and gently squeezed. There was a question of some sort on Jillian’s face, to which Theresa simply offered a nod in response. Jillian closed her eyes and groaned as Theresa found her nipple through her dress and pulled it with her thumb and forefinger.
Jillian turned so that Theresa could undo the button at the top of her dress. She could reach it herself but she found that she wanted her friend to do it. Standing, she faced Terry and pulled it off her shoulders so that it could puddle at her feet and she could step out of it. Her striptease evoked memories of doing this for Mason. It was wrong, very wrong for her to get naked for her son . . . but she loved it. This was wrong, very wrong, to be doing this with Theresa . . . but she wanted it and her body was telling her that she NEEDED it.
Her bra and panty set was pastel blue and lacy. The panties were high cut on the hips and also exposed a generous amount of her ass, though they were not a thong. Her hard nipples were clearly visible through the fine fabric of her bra and she smiled shyly down at Theresa as she saw the approval in her gaze.
Theresa stood and kissed her very lightly on the lips, then traced a finger down her neck and along her shoulder. As she slipped the bra strap down along Jillian’s arm she felt the goose bumps rise and heard her friend’s sharp intake of breath. Jillian accommodated the disrobing by pulling her arm up out of the strap and shrugging the right one down as well. Theresa pulled down the cups which held her friend’s 36-C’s and immediately planted her mouth upon her turgid nipple.
“Oh GOD, Terry” Jillian cried out as she pushed her chest into her face. She was still trying to take in this amazing sensation when she felt Terry’s hand slip into her panties, over her trimmed bush and down to her sopping wet snatch. The finger that went inside her there was so welcome, so trusted, and so needed. She grasped onto it with her cunt muscles like a baby to a pacifier as she continued to hug Theresa’s head to her tits.
The pressure of Theresa’s hand grinding on her clit with her finger buried deep in her twat caused her first orgasm. She shuddered and her cunt contracted against her friends finger 5, perhaps 6 times before relaxing. Fingers and hands began to fumble to get her own remaining clothes off and Theresa’s as well. She wanted to see her naked, to hold her body against hers.
Within seconds that feeling was a reality as they entwined their bodies and kissed passionately. Jillian’s hands began exploring every inch of Theresa. Her hips, her breasts, her shoulders, her back, her ass. It all felt so wonderful, so new. As Theresa lay back onto the sofa Jillian followed her down, placing her knee between Terry’s legs.
“You are so fucking sexy, Jillian” the words came so naturally as she pressed her cunt up against Jillian’s thigh and began rubbing it against her.
“Oh my god, you are so hot, Terry. I can feel the heat from your pussy. And holy shit, that cum felt so good . . . but I want more.”
They continued to fondle and kiss each other as Theresa rode Jillian’s gorgeous, tan thigh. Jillian grabbed the vibrator that was next to Terry’s head and moved it back to plunge it inside her. Terry took over so that Jillian could support herself with both arms as the plastic torpedo moved in and out of her drenched womanhood. Looking down to see her friend riding her leg, rotating her hips to put pressure on her clit as she slid up and down was so erotic; the sexiest thing she had ever seen in her life. She leaned back slightly for balance so she could squeeze her tits and pinch her nipples. “Ooooooh, Fuuuuuuuuck!”
“So you can talk dirty, huh? . . . do you wanna fuck, Jill? Do you NEED to be fucked?”
“God yes, I need to be fucked!”
“Who do you want to fuck you, Jill?”
“Mason” she practically whimpered, “Terry, god help me I want him to fuck me” she called, riding the vibrator in Terry’s hand while Terry humped her leg. “Or Phil, I’d fuck him too if I had the chance.”
The dirty talk complimented the physical stimulation to bring on her 2nd orgasm along with Theresa’s long-overdue first. They were both sweaty and shaking as they collapsed into a loving embrace.
They lay naked on the sofa together and Terry wasn’t yet satisfied. “Have you ever eaten out a woman, Jill?”
“No, I’ve never done anything like this with another woman, you have?”
“Um-hmm. Phil and I had a 3-way when he was in college with one of my friends. It was so friggin’ hot.” She paused then tentatively began “And . . . “
“And what?” Jillian urged.
“And . . . Susan . . . and, uh, Missy.”
“What! You’ve eaten your daughters’ pussies? Oh god, isn’t that illegal?”
“Well you’ve done things with Mason, right? And you want him to fuck you, right?”
“Yeah, I’ve fantasized about that, I guess, but all I’ve ever done is let him SEE me, you know.”
“And?” it was Terry’s turn to press.
“Well yeah I’ve helped him a few times to masturbate.”
“A few times?”
“OK, a bunch of times.”
“So you jerked off your son’s cock, right?”
“Yes, I’ve jerked off my son’s cock.” Jill admitted, eyes downcast.
“Well I’ve jerked off my son too” Terry went on quietly, “and I let him fuck me. I wanted him to fuck me and he has, many times.” The look of realization on Jill’s face was priceless as Terry continued. “I’ve eaten out my daughter’s and they’ve eaten me. And Mason . . .”
“What about Mason?”
“He’s fucked Susan, right here on this sofa.”
“God, are you sure? Did she tell you that?”
“I watched them, Jill. I fucked Jimmy right next to them as Mason put his dick inside my daughter. It was so fucking hot, Jill. I would have fucked Mason too but Sue picked him instead of Jimmy.”
“Oh my god! Has this happened more than once?”
“Just a few times with Mason here, but we do it almost every week.”
“And Phil? . . .” the question hung in the air. Jillian knew that Phil spent a lot of time on the road for his company.
“We, um, we had kept it from him at first, and I felt really bad about that, but for the last year or so he has joined in. He fucks me right in front of the kids and they love it. He fucked Susan too; you should have seen it, it was beautiful.”
“So why are you suddenly telling me all this?” Jillian absent-mindedly noticed that her hand had found its way to Terry’s snatch and was lightly rubbing it.
“Because I want you to join us, Jill. You’ve said yourself you need to feel sexy again, to have that part of your life back, or find it for the first time! You are young and fit and gorgeous, and the fact that you got divorced doesn’t mean you don’t deserve to feel the kind of things we just felt.” She paused while she found Jill’s pussy with her hand again and pressed her fingers against her lips. “Doesn’t this make you feel ALIVE? When’s the last time you felt like you did a few minutes ago.”
“I don’t think I EVER felt like I did a few minutes ago” Jill admitted.
“Come here” Theresa commanded softly as she put a hand to her head and pulled her in for a loving kiss, their hands still clutched at each other’s sex.
I hope you enjoyed this chapter . . .
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