Being thirty and already developing a beer gut, I began working out at the local gym. And since I worked nights, the equipment was readily available, which was cool. No crowds.
After a month or so, I got to know some of the regulars, mostly retired guys, some into their eighties, God bless them! Mostly it was just to say hi, but a few became as regular as clockwork, so I sort of bonded with a guy named Abe.
He was hunched over from Arthritis and age, but still happy-go-lucky at 75. He reminded me of an old gent I knew growing up, always with a smile and a joke.
Then one day, Abe didn’t show. The second day I became concerned and asked his friend Benny. Abe had suffered a stroke. He’d let me know the visiting hours at the hospital.
Benny’s eyes were red the third day when I approached and I feared the worst. Sure enough, Abie had passed away. I asked about the wake but Benny explained that the Jewish faith requires immediate burial and then they sit Shiva, a time when family and friends come to the house to give condolences. I arranged to accompany Benny.
The huge house was packed, people sat in groups, some solemnly, and others like one of the many Irish Wakes I had experienced. Benny led the way to meet the widow, who Abe referred to as “My Ruthy,” and I was shocked when I met her. Sitting erect in her chair, she was a striking woman, Red hair, green eyes, chiseled cheek and chin, her makeup exact, not a tear stain to be found. I thought he must be mistake: This woman was 20 years younger than Abe.
She stood as Benny and I came near. Her voice was strong and clear. “Oh, Ben, how good of you to come! It’s been so long!” They spoke of Benny’s deceased wife, about old times, then Ben said, “Esther, this it Jake, from the gym.”
She beamed as she took my hand. “So, you’re the young man Abie spoke of! He kept promising to bring you home to meet me. He so enjoyed your chats, said it made him feel young again!”
“Thank you, Ma’am, he was quite a guy. I’m very sorry for your loss.”
“Please, call me Ruth, and yes, thank you. Well, my husband would say he hated these things. He didn’t mourn someone who died, he celebrated their life!”
I smiled, “Sounds like something he’d say.”
People poured in and we drifted away, getting a sandwich and drink before saying goodbye. Esther said, “Thank you so much for coming. I wish we had more time to talk. But, obligations.” She looked around the crowded house.
“Maybe another time,” I replied, not knowing what to say. She smiled and I saw a tear begin to well up, and she squeezed my hand.
“You remind me of him, in his younger days.” with that, she pulled me down and kissed me on the cheek, and whispered, “Maybe another time.”
Weeks went by, and I thought often of Abe and Esther. I concluded from talking to Benny that although younger, Esther was still 66 years old and that Abe had convinced her to get cosmetic work done whenever she felt old. Face lift, tummy tuck, eye lift, new breasts (which Benny went on in detail to describe how Abe loved them.) Whatever her age, I felt strangely drawn to her, and found myself somewhat aroused at her memory.
Did I mention I’m a bartender? In a Steak House, and I don’t mean Outback. It’s fairly high-end, mostly adults, many of the more mature variety. No children’s menu, so very few whining rug rats, which reflects the austere atmosphere.
Dressed in white shirt and red tie, I pour Cosmos and Dirty Martinis for all the upper crust, and they complain and I smile as I simply pour it into a different glass, and, Viola! a perfect drink! it’s like a game.
Dinner clears out early, and usually by midnight, I’m closing. One Sunday, late, I had just bid farewell to my last customer, when the door opened, and a man in a black suit stuck his head in. “Sorry, Sir, closing up,” I called.
He smiled and stepped in, and behind him was Esther, dressed in a black pants-suit that reeked of money, with three inch heels making her about five foot six, gold everywhere, fingers, neck, ears, wrists, and that bright red hair and green eyes. She moved to the bar as her driver stayed at the door, and she took my hand.
“I know this is sudden, but they had a memorial for Abe at the Country Club tonight and provided me with a limo for the night. It ended early and I thought, ‘Who do I know who is still awake at this hour?’ And I remembered Abe promised to take me here some day. I hope you don’t mind?”
I realized my jaw hurt from smiling. “No, not at all! I was getting ready to close…”
“Even better! George here is at my disposal for the entire weekend, right George?” He smiled and nodded. “Finish up, and we’ll take a ride, if you don’t have plans…”
“None that I can think of.”
In fifteen minutes, I climbed into the back, where Ruth sat with two drinks, the dim lights giving her a sexy glow. “I hope you like Scotch. Abie had a thing for Single Malts.”
“That’s always been my favorite, too. Boy, you pour a healthy drink!” Clinking my glass to hers, our eyes measuring each other as we sipped. Hmm, which brand is this?”
“Macallan’s. Abe called it, Mother’s Milk!”
Through the glass, George asked, “Where to, Ma’am?”
“Surprise us, George. Someplace not too bumpy, we don’t want to spill!”
He closed the partition and we were alone. “So,” she asked, “was that too forward of me to just show up like that?”
“Not at all! I’m happy you did. How are you making out? I was going to ask Benny for your number to see if you needed anything.”
“Ha, Benny? He’s an old perv! For thirty years he’s been flirting, even with Abe right there! Abe took it as a compliment if men came on to me.”
“He realized how lucky he was to have you. That’s good, right? I bet it happened a lot, too!”
“Why do you say that?” she asked coldly.
“Oh, I didn’t mean anything, just that you’re very attractive and he must have seen a lot of guys taking a second look,” I blurted, hurriedly.
The stare turned into a smile and she said, “Thanks, Jake, but you don’t have to say that. I’m way past my prime.”
“So what, so am I? Sexual prime for a male is 18, and a woman is like 35! It doesn’t mean we close up shop.”
She got a big grin then and said, “Why did you bring up sex, Jake?”
I felt myself blushing and the words wouldn’t come out right. She was playing with me and enjoying it. “I just meant… not that part, but life in general… I didn’t mean…”
“Hush! I’m just teasing you. Abe used to love when we would go out, and men would hit on me! He enjoyed watching them try their lines on me, and I would flirt back as he listened in. In his last few years, he wasn’t able to… perform, if I can be blunt. So, we played, sometimes.”
I smiled and thought about it. “It must have been tough on the guy to think he was getting to first base with you, only to find you were married.”
She was settled back in the leather, looking so natural, a woman who liked to be in charge. The plunge in her top came pretty far, and I found my eyes drifting.
“No, Jake, I’m not just a flirt. Abe said it many times. If I only flirted and never followed through, I would only frustrate myself, and he was right.” She sipped the Scotch and purred as she went on. “If we both agreed the guy seemed safe and acceptable, we would invite him to our room, if you catch my drift.”
Wow, I thought, Abe really loved her to do that. Or else, he got off watching, which was cool, too.
“As a matter of fact, Abe planned on inviting you over for dinner, so we could meet. Does that shock you?”
It was sinking in, now. I swallowed hard and re-poured for both, as I gathered my thoughts. “So, Abe would watch you with the other man?”
“Sometimes, but some men can’t perform with an audience. Occasionally, Abe would wait outside, to be sure of my safety. If he did watch, afterward, he loved to tell me how beautiful I looked. He was such a sweet giving man.”
We rode in silence, and she said, “Jake, most of those men were in their fifties, much closer to my age. If you’re not interested, there’s no hard feelings.”
“I’m interested, a lot!”
She reached behind my head and pulled me to her, and our lips tingled from the Scotch. She whispered, “Are you circumcised?”
A strange question, but I nodded. She said, “I have this thing… I love to taste a man.” with that, I felt her hand slide up my leg, getting right to it, feeling my growing cock in the slacks. “If I’m too forward, let me know, okay?”
I nodded, as I slid back on the wide leather seat and she knelt between my legs, expertly opening my belt and loosening the slacks, and I let my hands feel those tits that had Benny all worked up. They were definitely not the boobs of a 66 year old!.
The zipper on her top gave way and she shrugged it off her shoulders as I arched my hips for her to drag my slacks down.
The street lights through the windows made her seem to dance with their movement. Her eyes flickered with fire as she yanked down my briefs, and my 7 inches sprang free. “Ooh, nice,” she whispered as she held it, pushed away a pubic hair, then bent to lick it.
Her tongue was rough like a cat’s, and my cock jumped as she licked again, then she smiled at me as she plunged down, swirling her tongue in her warm saliva.
I got her black bra open and felt for her nipples. The breasts were too firm, but better than sagging, and the nipples still had their sensitivity. She squealed when I tweaked them, sucking faster because of it.
Her hand kept stroking as she said, “How’s that, baby?” and I could only grunt in reply. She crawled up and kissed my lips saying, “I want your come, baby, I need your come.”
She slid back and sucked again, jerking while she did. Older guys must have needed the extra work to get off, but I was fully loaded, and she had me ready to shoot in minutes. I told her so.
When I could hold back no longer, I groaned, “Coming!” and the first spasm let loose a thick stream of come, shooting deep into her throat. The second held for an instant then I shot again, another thick glob. She stayed on me, swallowing for all she was worth. Finally drained, she slid up, wiping her chin.
She brushed her hair back with her hand. “I must look a mess!” I thought she looked totally sexy, with no top, those brand new tits sitting high, that sexy hair disheveled, and I told her so. She smiled weakly, and grabbed her drink. “I’m sorry, I only like oral with circumcised, for some reason.”
I said, “Thank you, Mom and Dad for doing that!” and laughed. “You’re awesome.”
She smiled again. “That was Abe’s favorite, but he hadn’t shot that much in years! Thank you.”
I slid closer and felt her tits as she watched, amused. “Very sensitive, huh?” I asked. She nodded as I could see her enjoying it.
I let one hand slide down to loosen her slacks, and she stopped my hand. “That’s not necessary, honey, you did your part.”
I looked at her. “Oh, Okay, I thought… never mind.”
As I removed my hand, she grabbed it. “I came when you did, baby, you don’t have to do anymore.”
“I don’t have to do anything. I wanted to.”
“Jake, I don’t want to disappoint you.”
“Believe me, you can’t.”
We kissed again, and to prove my point, I took her hand and put it on my rising cock. She was pleasantly surprised as I bent her back and gently sucked her nipples as she moaned and stroked me back to full size.
We rolled around and her slacks and panties fell away, and I allowed her to mount me, the easiest way with my six foot frame. I didn’t want to crush her.
She climbed on and I slid in easily. She was right, she was well-stimulated. She bit at my lips as I forced my full length into her. She squirmed on my pole, sloshing it around her juices and she sucked on my tongue. What a wild one!
I let her do the work, it was her choice to make, and she began slowly, then she was rocking back and forth. She leaned way back and I slid my fingers to her crack and teased her some more and she squealed again. I was hoping the driver wouldn’t be alarmed as she grunted and groaned and began up and down, pounding her neatly-trimmed pussy onto my throbbing cock.
She peaked, then shuddered and collapsed on me, having orgasmed loudly. “OH Baby, I came! I came!” she panted, but I was close to the end now, too, so I took over, holding her hips and ramming into her, and she responded, wanting me to reach my orgasm, too.
In a dozen hard thrusts, I was there, too, and shot into her, holding her hips down on me as I came again. We panted as our lips found each other, gasping, kissing, purring, groaning.
The kisses softened as did my cock, now totally spent. She slid off and slowly dressed, and I did the same.
“Thank you, Jake, Abe would have enjoyed this.”
“Did you?” I asked.
She turned, stared straight in my face. “It was my best night with a man in forty years, no lie. Thank you, I will always remember it.”
“So, is this goodbye, then?”
“Dear Jake, what are you, twenty five?”
“Thirty, but what does it matter?”
“You mean you want to see me again?” she asked.
“If you’ll have me.”
She beamed, kissed me briefly and lowered the partition. “George, I think you’re done for the night. I feel like having breakfast. You, Jake?”
I grabbed at her half-exposed boob. “Maybe lunch, too!”