Edited by Talynnda
Prologue: After graduating from UCLA in 1976, Jeff settled in the L.A. area and eventually became an talent agent. He represented several highly paid actors and actresses and became a respected member of the film industry.
Jeff and Rebecca corresponded regularly. Not knowing if Rebecca's husband might read her letters, Jeff kept the contents bland and platonic, never mentioning their tryst. In spite of the distance between them, Rebecca received a birthday card from Jeff every year, and she responded in kind. Rebecca and her family remained in New Jersey, and the three thousand miles between them prevented Jeff and Rebecca from even an occasional fling.
Jeff sent congratulations to 51 year-old Rebecca on the birth of her grandchild, and sent a sympathy card and flowers when Rebecca became a widow at 55.
Soon after Rebecca's sixtieth birthday, Jeff decided to take a brief vacation and returned to New Jersey to see Rebecca. Rebecca had informed Jeff that she had moved into a nice apartment in a senior community. From his parent's home, a few miles away, Jeff phoned Rebecca and asked if he could take her out to dinner. Rebecca gladly accepted.
Jeff knocked on Rebecca's door, taking a deep breath to try to calm himself. After all these years, seeing the woman who'd been his sexual mentor might be strange. The door swung open and there stood Rebecca, lovely and radiant.
Rebecca smiled and said, "Hi Jeff, please come in. I'm almost ready."
"Hi Rebecca," Jeff said as he stepped inside. "I've missed you."
Rebecca swung the door shut and held her open arms toward Jeff. "I've missed you too."
Jeff hugged her tightly and asked softly, "Okay if I kiss you?"
"I'd like that," Rebecca said.
Jeff pressed his lips to hers briefly, then stepped back and gazed at her.
"You still look gorgeous," Jeff said honestly.
Except for a few wrinkles and some slight puffiness under her eyes, Rebecca's face was as lovely as ever. Her beautiful brown eyes still seemed to gleam seductively. Her smile was still mischievous. Rebecca's hair was now an attractive blend of gray and white, and was worn in a short but feminine style. Her figure was still terrific as well. In eighteen years, she didn't appear to have gained more than five pounds. She wore a conservative black dress tastefully trimmed with silver, with a hemline above her knees (she still had shapely legs), and a neckline which revealed a bit of her still ample cleavage.
"You mean not too bad for an old Jewish widow?" Rebecca smiled.
"I mean still sexy, period."
"Thanks, Jeff. You've turned out to be a handsome man, and I'm not just returning a compliment."
"Thanks, that means something coming from you," Jeff said with a smile.
"Let me grab my purse and we can leave," Rebecca said.
Jeff took Rebecca to her favorite restaurant. Over dinner they rekindled their relationship. The initial nervousness they both felt quickly faded. When they each pulled out small pairs of eye glasses in order to read their menus, they laughed. Rebecca confessed to being near-sighted, while Jeff was far-sighted. Knowing that Jeff used to find her Southern accent a turn-on, Rebecca laid it on a tiny bit thicker than she normally did. Rebecca was relieved that though Jeff was now a wealthy and influential member of the film industry, he was still very down-to-earth. Jeff was glad that Rebecca was still honest and open. After Jeff complimented Rebecca's hair style, she casually informed Jeff that she didn't dye it because she was allergic to hair dye.
At one point, their legs touched under the table and rather than moving her leg away, Rebecca rubbed her leg subtly against Jeff's. He felt an involuntary stiffening in his pants. Their eyes met, gleaming into one another's. Gazing into Rebecca's beautiful brown eyes once again, Jeff felt the same desire he had many years earlier. Rebecca could feel the passion in Jeff's eyes like liquid blue fire. She wondered if this young hunk could actually want an old grandma like her, or was she just seeing what she wanted to see?
On the ride back to her apartment, Rebecca tried to make small talk while she mentally undressed Jeff. He had been the best lover she'd ever known, and she could recall every detail about his muscular body and his memorable erection. Trying not to stare, Rebecca thought that Jeff was more handsome than ever. He still possessed a full head of medium brown hair, worn fairly short. She longed to have his full, sensuous lips kiss her all over like they had years before. Rebecca noticed Jeff trying to catch glimpses of her legs as he drove. She moved so that her hemline rode up a little higher. Trying to ease the sexual tension with more small talk, Rebecca asked Jeff about meeting Hollywood stars, and about living in Southern California.
Even before they parked the car, Rebecca said, "Now, you are going to come in for at least one drink."
"I'd like that," Jeff smiled, "Thank you."
When they were back in Rebecca's apartment, Jeff sat on the couch, hoping Rebecca would sit next to him. Rebecca poured two glasses of wine, handed one to Jeff, and sat next to him. She had put on her eye-glasses to pour the wine, and in the comfort of her own apartment, she just left them on.
Tired of small talk, Rebecca asked, "The difference in our age and religion never mattered to you in the least, did it?"
"Not in the least. If anything, it made it even more exciting," Jeff said, looking her in the eyes. "Did it matter to you?"
Rebecca shrugged and said, "I was raised to believe that Jews should only marry Jews, and there should be no sex outside marriage. It also seemed wrong to want to have sex with a young man who was twenty-something years younger than me. I broke three taboos at once. I felt guilt, but never regretted the best sex in my life."
Jeff took a swallow of wine to wet his rapidly drying mouth, then set the glass on the end-table.
"Rebecca, I'm less shy than I was eighteen years ago, so I'm going to ask you something and I hope you won't be upset with me. I've been feeling that old desire ever since I set eyes on you again, and I was wondering if you were having similar feelings?"
Rebecca's pulse quickened. She replied, "Yes, Jeff, but I didn't think you'd want an old lady like me after screwing all those young, Hollywood actresses. So, you really still find me attractive?"
"I'll be glad to prove it to you again," Jeff smiled.
Rebecca chuckled, remembering things that were said the first time she'd seduced Jeff.
"You're sho'nuff still a naughty boy," Rebecca grinned.
"You never complained about that," Jeff smiled and moved closer to Rebecca.
"I still ain't complaining," she purred.
Jeff slid his hand along Rebecca's cheek and into the hair along the side of her head. She smiled seductively. Jeff slipped his other hand around her shoulder, pulled her even closer, and pressed his lips to hers. When she felt his tongue brush her lips, she opened her mouth and their tongues intertwined. Rebecca hadn't made love in several years, and one kiss from her young lover made passion flood through her mind and body. She wrapped her arms around Jeff and squeezed her breasts tightly against his powerful chest. After a moment, Rebecca's hand slid up Jeff's thigh until she found the large bulge in his pants. Jeff moaned quietly as she rubbed his growing erection through his pants. When Jeff began to fondle her breasts, it was Rebecca's turn to moan with pleasure. She hadn't felt such a fire in her furnace since the last time she'd had sex with Jeff, eighteen years before. Rebecca knew what she wanted next, and knew that Jeff would want it too.
Rebecca deftly unbuckled Jeff's belt, unhooked his trousers, and slid down his zipper. As her fingertips found the waistband of his underwear, she discovered the tip of his erection already seeking escape. She hooked her fingertips into his waistband and slid it down until his hard-on was freed. Then, she wrapped her fingers around the long, stiff shaft and squeezed gently. Feeling Jeff's cock throb in her hand excited Rebecca even more. Jeff raised his hips from the couch to allow Rebecca to slide his pants and underwear down. Rebecca resumed her grasp on Jeff's erection, and kissed him passionately once again.
Pausing for breath, Rebecca said with a smile, "I remembered you had a big dick, but I think it's even bigger now."
"That's because you make me so hard, honey."
"I'm glad you still think I'm sexy."
"Are you gonna leave your glasses on?" Jeff asked.
"If it's okay with you," Rebecca said, "I wanna see your sexy body and big cock crystal clear, not just a blur."
Jeff smiled and said, "Sure, it's kinda sexy." Then, Jeff reached behind Rebecca and unzipped her dress.
Rebecca grinned and said, "Maybe we should go into the bedroom before we get too carried away."
"Whatever you want," Jeff smiled, and stood. He stepped out of his loafers and out of the pants and underwear which were around his ankles. Rebecca took Jeff by the hand and led the half-naked younger man to her bedroom. She snapped on one small, dim lamp for the romantic mood.
After Rebecca and Jeff entered her bedroom, Jeff wrapped his arms around Rebecca and pressed his lips to hers. Jeff enjoyed the feel of the fabric of her dress as it rubbed against his hard-on. Rebecca put her hands on Jeff's firm buttocks and pulled her pelvis against his. Jeff then hooked his fingertips into the shoulders of Rebecca's unzipped dress, slid them down, and helped the dress fall to the floor. Rebecca unbuttoned Jeff's shirt and pushed the fabric off of his powerful shoulders. She ran her hands over his muscular chest. The lean boy she remembered now possessed large, sculpted muscles which she wanted to savor.
Next, Jeff hooked his fingers into the shoulder straps of Rebecca's slip, and slid them off her shoulders. Her slip joined the growing pile of clothes on the floor. Remembering Jeff's preferences, Rebecca had worn a black bra, black panties, a black garter belt, and black stockings. She was still a vision of sexuality.
Rebecca looked down at Jeff's cock. It was sticking straight out like a flagpole. She grasped it with her right hand and squeezed gently. She felt it throb in her hand. Jeff moaned quietly.
"Sit on the bed," Rebecca instructed, as she fondled the erection.
Jeff smiled and sat on the edge of the bed.
Rebecca knelt before him, without ever releasing her grasp on his boner. Jeff leaned back on his elbows and smiled at Rebecca. She returned his smile as she stroked and fondled his hard-on. Then, she used the long, painted fingernails of her left hand to gently scratch the underside of Jeff's scrotum.
"God, that feels so good," Jeff moaned.
Rebecca ran her nails up over Jeff's balls, through his pubic hair, and then back over his balls. At the same time, her right hand lovingly caressed his erection. Rebecca then leaned forward, pressed Jeff's rod into her cleavage, and moved slowly up and down. Jeff watched, smiling as the older woman teased his stiff member. When Rebecca felt sticky wetness on her breast she was delighted.
"You still get wet right away and I still like that," Rebecca chuckled.
When Rebecca slowly licked the pre-cum from the tip of his dick, Jeff moaned and propped himself up on his hands. When she began to lick his cock's head, and up and down the shaft, Jeff inhaled sharply and sat upright. He looked down at the head of gray hair bobbing in his lap, and ran his fingers through Rebecca's soft hair. The fact that the woman licking his dick had gray hair and glasses wasn't a turn-off to Jeff. He'd prefer a sexy older woman to a repulsive younger woman any time.
Rebecca held Jeff's stiff cock between her fingertips and gazed at it. In the soft light it glistened with her saliva. It was even longer than Rebecca remembered, proportionally thick, and curved ever so slightly upward. The perfectly shaped, circumcised head was now swollen and pinkish due to Rebecca's fondling.
Rebecca smiled at Jeff and said, "Watch it disappear." She slid her mouth over Jeff's hard-on, and didn't stop moving slowly down until her lips stopped at the base of his cock. Then, she slowly raised her head until the entire ivory shaft reappeared. Rebecca grinned at Jeff, and he returned her smile.
"Wanna see it again?"
"Yeah, angel," Jeff said.
Once again, Jeff watched the entire length of his dick slid into Rebecca's warm, wet mouth. Jeff moaned and ran his fingers through her white hair. As Rebecca's mouth continued to move up and down on Jeff's rod, Jeff felt himself starting to lose control. Not wanting to cum just yet, Jeff decided on a change in the action.
"Hey, honey, let me finish undressing you," Jeff suggested.
"Sure, baby," Rebecca said and stood up. Jeff rose from the bed and moved behind Rebecca. He unfastened her bra, and, from behind, slid his hands inside the bra. He cupped her ample tits and ran his fingertips over her nipples. Jeff was pleasantly surprised that Rebecca's boobs had sagged only a little, and were still sexy to behold. Next, he moved in front of Rebecca, hooked his fingers into her black panties, and slid them down. Jeff recalled that eighteen years earlier, Rebecca possessed a neatly trimmed triangle of dark pubic hair. Now, her muff was just as dense, but there were a few gray pubes mixed in. Jeff found it to be as sexy as ever. When Rebecca's panties fell around her ankles, she stepped out of them. They wrapped their arms around each other and pressed their mouths together once again. Rebecca enjoyed the feel of Jeff's hard-on pressing against her stomach. Jeff slid his hand down between Rebecca's legs, through her soft, curly pubes, and over her slit. She was already wet.
"Hey, sweetie, would you do something for me?" Jeff asked.
"Anything you want, baby," she said.
"It's my turn to do you. I want you to kneel over my face," Jeff grinned.
"Are you sure? I still get pretty wet," Rebecca asked.
"I'd still consider it a compliment."
"If that's what you want, baby, I know I'd love it," Rebecca smiled.
Jeff laid on his back on the bed. Then, Rebecca climbed up next to Jeff, grasped the headboard for balance, swung her knee over his head, then lowered her pussy to his eager tongue. Rebecca sighed as Jeff ran his tongue the length of her moist slit.
"I'm glad my baby still loves to give a good licking." Rebecca grinned and ran her fingers through her young lover's hair. Jeff moved his flattened tongue forcefully against Rebecca's clit.
After a minute, Jeff said, "Remember what I'd always say to you when we'd make love?"
Rebecca looked down and smiled, "You mean if there was anything I wanted you to do differently, I should spell it out for you?"
"Yeah, I'm glad you remember. Well, that still applies right now." Then, Jeff swirled his tongue around Rebecca's clit.
Rebecca moaned and panted, "You still eat my pussy better than anybody." She ran her fingers through Jeff's hair, and moved her wet muff back and forth against his mouth. Jeff had made her hotter than she'd been in many years.
A couple of years before her husband died, Rebecca had come to the conclusion that her sex life with virile men would be almost non-existent from that point on. She would be left to masturbate when the horniness became unbearable. Now, her young, gentile lover had his head between her legs, and he was sporting a wonderful hard-on. He made her feel desirable again. She reached back, wrapped her fingers around Jeff's stiff cock, and fondled it lovingly. Jeff's moan was muffled by her muff.
A few minutes later, Rebecca was grinding her pussy against Jeff's mouth, as she gripped the headboard. Waves of pleasure swept through her body and mind.
Through partly-clenched teeth, Rebecca moaned, "Ohh yeah baby... Lick my pussy, you naughty boy...Lick it, Jeff... Make Momma cum... Ohh Jeff... Ahhh... Ahhh... Aaahhhhhh..."
Rebecca shuddered as the orgasm swept over her like a tidal wave. Jeff continued to lick even as he sensed the increase and change in Rebecca's wetness. Making his mentor cum was all that Jeff was focused on at that moment.
Rebecca moved her wet box away from Jeff's talented tongue, and panted, "I get so sensitive... let the old lady catch her breath." She rested her weight lightly on Jeff's powerful pecs and straightened her glasses. Jeff smiled up at Rebecca as he felt her wetness on his chest. Rebecca returned his smile. Much of Jeff's face glistened with her juices. Rebecca pulled some tissues from a box on her nightstand, and gently wiped Jeff's face.
"Thank you, my naughty boy," Rebecca whispered.
"My pleasure," Jeff grinned.
"Now, let the old lady suck some more young cock," Rebecca said with a smile.
Then, Rebecca repositioned herself across Jeff's thighs, facing him. She curled her fingers around his cock and stroked it lovingly. Next, she bent forward and ran her tongue all around the head of his dick. Jeff shuddered as the sensation flowed through him. While she pleasured him, Jeff ran his fingers through Rebecca's soft, white hair. In a couple of minutes, Rebecca had gotten Jeff's cock good and hard again. Without releasing her grip on his hard-on, Rebecca got to her knees. Then, she swung one knee over Jeff's hips, held his rod straight up, and lowered her pussy onto the stiff dick. She moaned as she felt him fill her.
Rebecca slowly raised her pelvis until she felt that Jeff's hard-on was barely inside her, and then she slowly lowered herself. Again, she slowly raised and lowered her hips. Rebecca wanted to savor the feeling of having a stiff cock inside her pussy. It had been a long time. Gradually, Rebecca began to pump more rapidly. She looked down at Jeff, who was breathing hard and in pure bliss. Jeff reached up, fondled her bouncing tits, and did his best to lick her nipples.
After a few minutes, Rebecca panted, "Jeff, will you fuck me doggie-style?"
"I like a lover who knows what she wants," Jeff grinned. "Sure honey, I'd love to."
Rebecca dismounted Jeff, and got on all fours on the bed next to him. Jeff kissed Rebecca briefly, then positioned himself behind her. Holding his hard-on between his fingers, Jeff rubbed the sensitive head against Rebecca's moist slit. Rebecca moaned as she felt the long, stiff cock push slowly into her. She felt it throb inside of her just as it started to slide back out. Jeff pulled out almost all the way, then eased his rod back in again. He pushed his pelvis tight against Rebecca's shapely ass, then moved his hips in a small circle. Rebecca could feel the stiff dick move inside of her.
"I love the way you fuck me, baby," Rebecca said over her shoulder.
"Oh... you're still so tight, honey," Jeff moaned.
Jeff began to thrust more rapidly. His pelvis slapped against Rebecca's ass. For nearly twenty years, Rebecca had fantasized about having sex with Jeff again. Now, her young stud was fucking her into ecstasy once again. It was at that moment that Rebecca wanted to see Jeff's face and body while he fucked her. As good as the doggie-style felt, Rebecca didn't want to be looking at a headboard when she came again.
Over her shoulder, Rebecca said, "Hey baby, let's change positions again."
"Just tell me what you want," Jeff panted.
"I'll show you..." Rebecca said as she reluctantly pulled away from Jeff's erection. She turned, laid on her back, and spread her legs on either side of Jeff.
"Fuck me this way. I wanna watch you fuck me, and when you're ready to cum, I'll finish you off the way I used to."
Jeff aligned his ivory shaft with Rebecca's hairy snatch and guided it inside. Rebecca gasped as Jeff's long dick re-entered her. She was panting through her mouth as Jeff pumped her. Jeff kissed Rebecca on the lips, then down her neck, and then arched his body so that he could lick her nipples. At the same time, he continued to slide his hard-on in and out of her wet pussy. Rebecca was glad that Jeff had remembered how much she'd enjoyed this maneuver in the past. The simultaneous sensations made Rebecca's mind dizzy with lust. She ran her fingers through his hair as he licked her nipples and fucked her pussy. Rebecca looked at Jeff's torso. His chiseled muscles glistened with perspiration. She ran her hands over his firm abs, and then further down until the fingertips of her right hand found her clit. The index finger and middle finger of her left hand scissored around the slippery erection which was pumping in and out of her.