Horny Widower Finds Holiday Cheer

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Christmas was coming up in just over a week, but a subdued Benny struggled to find much in the holiday season to celebrate.

Desperate for some holiday cheer to come his way, Benny put on his favorite red jeff cap, which matched his red sweatpants, and broke out his ugly green Christman sweater again, so that he could at least look like he was feeling the holiday spirit.

As Benny grabbed his car keys and walked out to his car, he thought about his current situation. He chafed at Antonio's suggestion that his fooling around with neighborhood wives jeopardized potential future business.

But, like any aging parent, Benny wanted to be a help to his son, not a burden. As much as he disagreed with Antonio that his actions imperiled their business, he felt he had to respect Antonio's feelings.

Still, Benny was depressed.

It did not help that Jody had ghosted him since the Elena incident, telling Benny after it happened how "mortified" she was by the whole thing. Much like Antonio feared, it seemed unlikely he would hear back from Jody anytime soon.

The afternoon rush hour was in full swing. The store was crowded when Benny walked in.

Noticing the lengthy line in front of the cashier, Benny spotted Mary's husband, not a hair out of place, in a gray business suit, white shirt and red tie, talking to two utility workers who stood behind him in line.

Benny felt an immediate adrenalin rush upon seeing him.

"There's that guy that Antonio said I should apologize to!" Benny thought to himself. "Well, fuck him."

Benny began walking toward the milk aisle but stopped himself.

"Oh, fuck it." He reconsidered. "I should just get this over with. That way I can tell Antonio I did it and make him happy."

Benny turned around and walked directly up to the much taller man, trying to figure out what he should say to him. When he reached him, he interrupted his conversation with the utility workers.

"Excuse me, buddy." The older man started, holding out his hand for a handshake.

Mary's husband looked down at Benny quizzically, at first, returning Benny's offer of a handshake, while warily listening to what he had to say.

"My name is Benny Baninno, and I want to say I'm sorry for hitting on your wife at Kelly's Bar a couple weekends back. Maybe I got a little carried away. My son told me he saw me grab your wife's ass right in front of you and that I'm lucky you didn't punch me in the mouth!"

The two utility workers standing behind Mary's husband burst out laughing and her husband yanked his hand away. His suddenly bright red face looked like it was ready to blow a gasket.

The man trained his eyes on Benny. His angry response pulled no punches.

"No offense pal, but you must have had a few too many that night!" He said loudly, for everyone around him to hear. "Maybe you were imagining things! I only remember you because you're wearing the same goofy red jeff cap and sweatpants that you wore that night! I doubt my wife remembers you at all!"

Benny was taken aback by his nastiness and incensed by the unfounded accusation about having too much to drink.

A red-faced Benny stewed momentarily but thought about what Antonio said. Rather than respond, Benny simply turned and walked away, feeling the eyes of everyone in the store upon him.

He heard the guy trash him to the utility workers as he walked to the door.

"Hehe. I have no idea where that shit came from! What a crazy old nutjob!"

Benny left the store and got into his car. He wished he had pushed back on the guy and told him he got his wife's phone number that night.

As he drove, a humbled Benny faced another truth about that night. When Mary danced with him, it seemed like she was trying to impress her friends, more than anything else. Even when he got her number at the end of the night, she barely made eye contact with him.

Mary probably only danced with him to be polite to an old man.

Driving to the next store to get the milk, Benny decided not to tell Antonio what happened. It would only feed his fear that Benny's actions were a risk to his growing neighborhood-based business.

When he got home with the milk, he said nothing about what happened. He quietly ate dinner and spent little time with his family in the living room before retiring upstairs to his bedroom by 9pm.

Sitting in his easy chair, next to his bed, Benny could not get his altercation with Mary's husband out of his head. Clearly, the guy resented him for hitting on his wife. But instead of simply acknowledging it, and accepting, or not accepting, his apology, he treated Benny like he was an old drunk, and pretended the whole thing never happened!

Benny sat back and stewed some more over the insulting things this jerk said to him, getting angrier by the minute. Finally, he pulled Mary's number up on his phone.

"Fuck it. What have I got to lose?"

Throwing caution to the wind, he typed out a text to her:

"Hey! It's Benny. Do you remember me?" the text read.

Almost immediately, he received a response.

"How could I ever forget you, Benny! It's nice to hear from you!" Mary wrote.

Benny's heartbeat quickened.

"I'm glad you remember me!" He texted back.

Realizing her husband was full of shit, Benny was back in business.

"Can you meet me for a cup of coffee tomorrow morning around 10am?" He followed. "We can meet at the Big Coffee Co. on Florence Ave."

Within a minute, he received a text back from Mary.

"Absolutely! It's a date!"

His self-confidence restored; Benny decided to get some sleep. Tomorrow promised to be an interesting day.

It was a mildly cold Wednesday morning. Antonio was in the kitchen pouring himself a cup of coffee before leaving to meet his small crew at a nearby apartment complex where they would be painting two units.

He turned when he heard his father's footsteps coming down the stairs and was surprised to see his dad with a clean shave, already fully dressed in his gray sweats, wearing a Santa Clause hat.

"Good morning, Antonio!" Benny said with a big smile and an extra pep in his step.

Antonio, still not over his displeasure with his father and worried that he might have to lay off his painting crew after the holidays, immediately got down to business.

"So, Dad. Have you heard anything more from Stan and Jody about giving them an estimate?" he asked, anxiously.

"Not yet." Benny replied, defensively, noting the frustration and worry in his son's tone. "I'm sure I'll hear soon!"

"Ok. I hope so. I need to let my crew know whether I can afford to keep them into the new year. That job would make a big difference." Antonio said as he finished his coffee.

Benny decided it would be best if he did not tell Antonio where he was going. Antonio left a few minutes later.

Benny left the house a half hour later, arriving at Big Coffee Co., five minutes early. Before getting in line, he texted Mary, telling her he was already there, and asking her what she wanted him to order for her.

She texted her order back to him, along with an apology in advance for being a few minutes late. Benny got in line, keeping an eye on the seating situation to see where he could find a table that might offer them a modicum of privacy.

After getting their drinks and securing a table for two in the corner, he looked around and saw Mary, wearing a long black parka, walking into the café. He held his hand up and waved at her.

The smiling and clean-shaven Benny stood up as she approached.

They exchanged a friendly hug before Mary took off her coat and placed it on an empty chair.

She was dressed casually, but Christmassy, wearing a red and white cashmere sweater, black yoga pants and tennis shoes.

"I'm so glad you could make it, Mary! You look absolutely stunning, today!" Benny said as he sized her up. "I love those earrings! What are they? Christmas Trees?"

"Ahh! You are so sweet and thank you for noticing my earrings! Yes, they are!" Mary said to him, smiling, as she gave him a closer look at them.

"Well," the talkative Mary continued, "I got so much of my last-minute shopping done yesterday! You're lucky you texted me when you did last night. So, other than going out to dinner with my husband, Steve, when he gets home from work tonight, I looked at what I had to do today and realized I had done most of it already!"

Benny waited until Mary sat down before sitting down himself. He made a mental note that her husband's name was Steve and that she was free the rest of the day.

Mary sat down. Her coffee drink sat before her, piping hot.

"That's great!" He said to her. "I like to prepare for everything I do, as early as possible."

"Oh. I'm jealous. I can never catch up on the things I have to do." Mary confided.

"I finish my Christmas shopping by August." Benny bragged. "I've always been that way."

Benny sat back and looked at Mary, sitting across the table from him, in all her beauty. After everything that happened, he considered himself lucky to be in this position. Now, he wanted to see how far he could take things.

He decided he would try the same approach with Mary that he used with Jody, since it worked like a charm with her.

He took a deep breath.

"You have such a beautiful smile, Mary." He said to her, his voice slightly unsteady. "I'm sorry. You remind me of my wife, Rita. I lost her three years ago. She was my world and since she's been gone..."

"Oh Benny. That's so sweet." Mary responded, seemingly surprised by Benny's sudden display of vulnerability. "I-I don't know what to say."

"Look. I'm glad you joined me." Benny continued after taking a deep breath. "I really didn't ask you here to lay that on you. You remind me of her though. She loved life and enjoyed meeting new people. That woman drew me out of my shell!"

Mary smiled warmly. She reached across the table and put her hand on Benny's hand.

"That's ok. That's really touching, Benny."

"Thanks for saying that, Mary. The holidays are still really tough."

"Well, that's why I'm glad I'm here with you!" Mary said. "I must admit, my friend, Susan, told me about you and Rita and how difficult the holiday season still is for you. I believe we met for a reason! There is nothing that brings me greater joy this time of year than spreading holiday cheer, especially to those that could use some!"

"That's a great sentiment, Mary. That's the way I've always been!" Benny chirped, elated that his neighbor, Susan, had vouched for him to Mary. "It's great to meet a kindred spirit!"

Mary and Benny talked, non-stop, for almost an hour, chatting as if they were old friends.

He learned that she was 51 years of age, and her husband, Steve, 55, was her second. They had two children, ages 21 and 18. While Steve was the father of their younger child, the older one was from her first marriage. She and Steve had been married fifteen years, and she said nothing to Benny that indicated any problems between them.

They spent a lot of time talking about their children. Benny told stories about his army service so many years ago, that took him overseas, which, he noticed, seemed to impress Mary a great deal.

Benny also learned she was in the homecoming court, along with his neighbor, Susan, back in high school. She told him she spent most of her adult life working as an administrative professional for a pharmaceutical company, and that in her early twenties she was a part-time lingerie model, which gave Benny an instant woody.

They both shed tears together as Benny recounted stories about his late wife, Rita, from how they met, and built their lives together to her losing the fight against a debilitating disease. Mary had to use napkins to dab her tears.

Finally, after more storytelling by both, there was a lull in the conversation.

"So, Mary." Benny said in a slower cadence. "I know we've been here a while. I wanted you to know that I find you to be an incredibly unique, beautiful, woman."

"Oh, you are such a sweet man, Benny." A gushing Mary responded. "This has been a great morning. I've really enjoyed talking to you!"

"Look, Mary, one more thing." Benny continued, ready to lay it on the line. "I'm not trying to put you in a difficult spot, but I would give anything to make love to you, just once."

As the words left his mouth, he noticed Mary blush, and nervously avert her eyes downward.

"Ah. I don't think." Mary began, uncomfortably, causing Benny to try to rescue his teetering plan.

"I don't want to come on too strong." Benny quickly followed; his eyes fixated on Mary. "Obviously, this is up to you. But just seeing you, and talking to you, is bringing all these memories back."

Mary looked back up at Benny and smiled sympathetically but was clearly uncomfortable and at a loss for words.

"Maybe I didn't say that right." Benny followed, now desperately trying to find the right combination of words that might get Mary to yes. "There's only one Rita in my life and there only ever will be one Rita. You just have this spirit about you Mary, and a love of life that brings all those feelings back to me."

Benny finally stopped talking, but his eyes remained focused on Mary. Mary's eyes were averted downward again, seemingly afraid to look at Benny as she tried to formulate her response.

After a moment, Mary looked back up to Benny, who awaited her reply with trepidation. She spoke slowly.

"Oh, Benny. I-I really don't want to make a habit of cheating on my husband, but if you invite me back to your place right now, I'll say yes, as a special exception."

Even the ever-optimistic Benny could not believe it. His face lit up. He leaned forward, reached out and took hold of Mary's hand.

"That's great, Mary! Except, my son and daughter-in-law and my grandson live with me. Can we go to your place? You said your husband isn't home."

Benny looked directly at Mary, still holding her hand. She again averted her eyes downward to her empty cup of latte and seemed to be reconsidering the whole thing. Benny squeezed her hand tighter.

He watched her take a deep breath, before finally breaking the silence in a soft voice.

"Okay Benny."

The energetic Benny stood up.

"Okay then Mary. Let's go before you change your mind!"

Mary slowly stood up and started to put on her coat.

Benny quickly moved around the table to help her with it.

"Thank you, Benny!" Mary responded, smiling at Benny, moved by his gentlemanly act, as a coatless Benny took her by the hand. They turned and exited the coffee shop together.

As Mary led the two of them toward her car, Benny spoke up.

"How about I just follow you to your house. I know if you are over on Garfield, that's not very far."

Mary used her key fob to unlock her car door.

"Just follow me." Mary responded, conspiratorially. "When we pull up to my house, park across the street. We shouldn't walk into the house together. Wait until I let myself in."

"You got it." Benny said, electrified, that Mary was openly plotting with him to cheat on her husband.

"Benny, one more thing I need to know. Are you sure you're up for this?" Mary asked, in a tone suggesting she was looking for assurance that Benny would not keel over in her house.

So desperate at this point to get in this woman's yoga pants, Benny was ready to suffer any indignity, including Mary's insinuation he might no longer be man enough to fuck her properly.

"I think I'll surprise you." He said, simply.

Breaking away from Mary, Benny walked over to his car and got in.

Setting her remarks aside, Benny was congratulating himself on how much more quickly things transpired with Mary than they did with Jody, as he drove closely behind her on the way to her house.

When they turned onto Garfield Street, Mary parked her car in front of the fourth twin from the corner. Benny parked across the street and waited for Mary to get out of her car.

Mary got out of her car, walked up to her front door, and let herself in.

Turning around from the doorway to look at the street, she slyly motioned with her left hand to Benny.

Benny left his Santa hat behind as he got out of his car and walked up to Mary's house. She held the door open for him as he walked into her living room and then closed it behind him.

"This is a really nice house, Mary!" The chatty Benny said to her as he looked around her living room, noticing a fully decorated Christmas tree between the brown leather couch and the distinctive brick fireplace. "Let me guess. You were the interior designer here, weren't you? Or did you pay a professional thousands of dollars!?"

"Oh Benny. You're too kind!" A blushing Mary responded, as she took off her coat and draped it over a chair.

"I did it myself, with my husband's input. Well, he gave an eensee weensee bit, anyway." she added, chuckling.

"These are great hardwood floors, too." Benny continued, as he moved a step closer to Mary, who was looking around her living room, admiring it herself.

"I'm just sorry I didn't have time to straighten up a bit before you got here." Mary said before turning to look at Benny, who now stood inches away from her.

Benny was ready to make his move. Mary's voice dropped to a near breathless whisper.

"Can I offer you a drink?" she asked, nervously.

From up close, Benny noticed she was shaking, but he was ready to press on.

"I'm just drinking in your beauty right now and that is all I need, Mary." He said, his eyes glued to hers.

"Oh. You are a sweet-talking man." An apprehensive Mary responded, her voice cracking.

Benny put his arms around her waist and pulled her in for a kiss.

Mary responded to the only slightly taller Benny's kiss by wrapping her arms around his skinny shoulders. Now holding each other tightly, their kiss grew more intense.

Benny could tell that Mary was warming up to him. Grinding up against her, his emerging erection was becoming quite apparent. Mary's eyes were closed, as their kiss lingered. Benny prepared to ratchet up the action.

He reached up and glided his hand under the waistband of Mary's yoga pants. Getting no resistance, he immediately slid his index and middle fingers over her labia. An already moist Mary was welcoming, opening her legs slightly, enabling him to find her clit more easily, and tease it with his middle finger.

Confirmation that her arousal was growing came when Benny felt Mary slide her own hand inside his sweatpants, taking hold his hardening cock and beginning to stroke him.

Standing in the living room, at the foot of the stairs to the second floor, Benny and Mary were embracing, kissing, and fondling each other's private parts.

Benny upped the ante again, when without warning, he dipped his fingers deep inside Mary, practically lifting her off the floor.

An overwhelmed Mary removed her tongue from Benny's mouth, and her hand from his sweatpants, as she held onto him tightly, her eyes closed, and her mouth agape.

Benny digitally probed her, finding, and focusing upon her G spot, sending shockwaves throughout Mary's body.

"Aaaahhhh, aaaaahhhh!" She squealed loudly in unbridled delight. "Aaaaahhhhhhhh!"

Mary, offering no protest, was getting off on his Benny's finger fucking.

"Aaaahhhh! Aaaaahhhhh!"

After getting Mary off so quickly, Benny pulled his moistened fingers from between her legs and fed them to her. With one arm still wrapped around her, a randy and wobbly Mary eagerly slurped her wetness from Benny's fingers.

"Let's go up to your bedroom." He whispered in her ear.

Saying nothing but offering him a furtive smile, Mary took Benny's hand and led him up the stairway.

Checking out her ass as he followed her up the steps, Benny was ecstatic at how quickly things had progressed. His mind raced with what he should do when they got to her bedroom, but first and foremost, he wanted to make sure, at this advanced stage, he did not do anything to blow it.