Will You Merry Me?

Freddy, the waiter, brought out my first cocktail, which was superb. I read the menu even though I knew what to order when a hand took my drink from me.

"I'm not done with it, Freddy."

"And I'm not Freddy."

I looked up to see Jenn sitting next to me in the cozy booth. She was dressed in a stunning silver dress which hugged her body. She was sixty or soon to be sixty and looked twenty years younger--a timeless beauty.

"This is a surprise," I said with a smile.

"My cousin has several kids, and they have kids, and Christmas Eve at her house is a shit show. I made an excuse and left."

"What was the excuse?"

"I had a date. A reoccurring date. A Christmas date every twenty years."

She had a bag from CVS in her hand, which she placed in her coat pocket.

"Last minute gift shopping at CVS?" I kidded. "I hope you got that clock radio I was dreaming about."

"Cholesterol and blood pressure meds," she replied. "The perks of getting older."

Freddy came by, and Jenn ordered a twenty-five-year-old Glenlivet.

"I am impressed; you know your scotch."

"No, I Googled it when I walked in the door. But don't let Freddy know. I want him to think I'm either a wealthy heiress or a high-priced hooker. Please tip him like you can afford to hang out with either of those girls."

"Well, if this is a date, I will."

"Yes, it's a date,"

Our meal was superb, the drinks were strong, and Jenn and I covered the last twenty years of our lives. She never left Rochester, but her life got better. She was a cancer survivor and began running for the first time since high school. She had her mind set to run a marathon.

I told her of my career in engineering and how I began working for Amazon fifteen years ago. The money was good, but the job was dull.

"How do we keep ending up together on Christmas Eve?" she asked. "I think we could sell our story to Hallmark for a movie."

"We might want to leave out the divorces and dead husbands part," I said.

"And the clinical depression and sense of hopelessness and bad, bad decisions," she added. "We might have to keep out all the wild sex, too."

"OK, maybe this isn't for Hallmark after all." I said, "But damn, that sex was good."

"If I can be honest, it was great," Jenn said as she savored the Glenlivet.

A few more drinks and our filters were lowered. Anyone within eavesdropping distance would have heard some very spicey conversation.

We left the restaurant and looked across the street at the closed Irondequoit Mall. We were looking into the past. It was a time machine where we materialized every twenty years, and here we were again.

I pulled up my Uber app.

"Where to?" I asked.

"Well, we've fucked in the mall, we fucked at that hotel over there. How about we fuck in your childhood bed?"

I always loved how direct she could be and prayed there was an Uber driver out there at this hour on Christmas Eve. The app spun, and then.

"Got one!" I said with excitement. "Chris, and he's in a red Camry. Three minutes out."

Jenn snuggled in close to me for warmth. Despite wearing our winter coats, she felt wonderful to hold, and I turned to face her. Our faces moved in for a gentle kiss that lingered.

"I hate to break up this moment, but I'm looking for Davey."

We broke our kiss to see a red Camry with an older driver. We each did a double take as the driver looked like Sant Claus with a flowing white beard.

"Wow, that was quick, and I wasn't expecting..."

"You weren't expecting Santa? Yeah, I get that a lot this time of year."

Jenn and I climbed in the back as Uber Santa drove us toward my home. The backseat of the Camry was cramped, and she leaned into me. Placing her hand on my inner thigh, she gently rubbed my leg, knowing full well my cock would expand from her touch.

"He looks just like our stoner Mall Santa," she whispered.

Jenn was right; the Uber guy looked like our Mall Santa from 1983. But that guy was at least in his sixties back then. He would be over 100 now, so he had to be a different guy.

"Shame about that mall," Uber Santa commented as we passed its empty remains.

"I used to work there," he said nostalgically.

"So did we," Jenn replied. "We were Santa's elves."

"Were you our Santa?" I asked.

"Come on. That would make me about 100 years old,"

"We never said when we were elves."

"The mall has been closed for three years. They stopped doing Santa's Village about ten years ago. I assume you worked as elves in your teens, so I'm thinking it was in the mid-1980s. About that time, I worked at Radio Shack, next to the Spencer Gifts."

This Uber driver missed his calling as a detective.

Uber Santa then talked about the good old days of Radio Shack, but I was lost in the warmth of Jenn's touch and the thought of feeling her body against mine.

We arrived at my house. Jenn stepped out the passenger side, and I left the driver's. Uber Santa rolled down his window.

"Thanks for the ride, Uber Santa."

"Hey, Davey, she's still a knockout. Even with the silver hair and without the big tits."

And with that, Uber Santa drove off, leaving me bewildered.

I saw Jenn in the streetlight's glow, shivering from the cold.

"Hurry up, I gotta pee bad," she said as she danced, trying not to wet herself.

Taking her hand, we went inside to find that the gas had been shut off and the heater was not working.

Fortunately, there was firewood, and it was only a moment before I had a roaring fire while she used the bathroom. When she returned, the fireplace put out more than enough heat to warm the living room.

I made a bed on the floor from several comforters and pillows. The warmth of the fireplace and the yellow glow made this the perfect spot for what might happen.

As we shed our coats, I couldn't help but notice Jenn's chest was smaller than the last time I saw her twenty years ago.

She sat in front of the fire.

"You're looking at my breasts."

"No, no, I wasn't."

"You are. It's okay, you've seen them before. You know what they were like when we were twenty and then forty, this time it's different. I had a cancer scare a few years ago. I had a double lumpectomy. They removed several masses from my breasts."

"I'm so sorry to hear that. God, life has not treated you fairly."

"It's okay, I'm okay--one hundred percent in the clear. So, believe it or not, Jenny Jugs got a breast enhancement."

"You know about Jenny Jugs?"

"Yeah, Mall Santa was anything but subtle, and it was the 80s. He tried to brush up against my boobs nearly every day."

Jenn reached back and undid the top of her silver dress, letting it fall away, revealing her naked torso. Her breasts were smaller than twenty years ago when they had been reduced and much smaller than forty years ago when they would have made a porn actress jealous, but they were perfect in every way. A subtle scar was evident below each breast, but nothing more.

I then saw the elf necklace reflecting the firelight.

"They look great," I said, unsure what to say in such a situation. "How did they..."

"Trust me, you don't want to hear the details, but while other women's boobs get bigger as they age, I seem to be going backward."

"Can I..."

"Touch them? I wish you would."

She approached me, put her arms around my neck, and pulled me in for a passionate kiss.

I tenderly kissed down her neck as she pushed my head toward her nipples. I felt the texture of her skin on my tongue. Her nipples were hyper-sensitive to my exploration. I brought my hand up, gently massaging her soft breasts, and then kissed them with passion.

She slipped out of her dress, leaving only her thong between us. I lifted my shirt over my head as she undid my belt and gently slid her hand inside, grasping my cock gently. Her hands were warm, and my girth grew at her touch.

Dropping to her knees, she pulled my pants and underwear down and began to stroke my growing cock. I was stiff in seconds. She gently placed her mouth over the tip and let her tongue circle my glans. The warmth of her moist mouth felt wonderful, and I wanted to ram my cock deep inside, but she beat me to it, gently sliding down and engulfing my manhood until her lips were around my hilt.

Her slow-burn blow job went on for several minutes. It was tender and torturous, and I wanted it to stop, or I would finish too fast.

She withdrew my cock from her mouth and looked up as she masturbated me.

I wasn't sure what she needed, so I decided to ask.

"Do you want me to treat you like a..."

"Whore? No. That was a challenging time for me. I felt ugly and wanted to be treated ugly. Please treat me like you care, even if that's false."

"I do care. I've always cared."

"Then show me."

I laid her on her back, the fire illuminating her body, then knelt between her legs and began to kiss her belly. She was softer than twenty years ago, with a slight muffin top that her clothing hid. For a woman of sixty, she was amazing. She put her hand on my head, pushing me downward toward her waiting pussy.

I kissed and licked myself downward, coming to a well-trimmed silver bush. She opened her legs, and the bush slowly parted, revealing her wet labia, waiting for me to taste. I remember how large her clit was and made sure to suckle it gently before taking my tongue and doing a slow drag down her pink opening and then back up. She shuddered from my deliberate attack and pressed my head inward.

Opening her legs wider, I licked her pink wetness up and down, always returning to her clit. She pulled her legs back and held her knees so her ass tipped up toward me. She wanted me to taste her ass, and I was only too eager. Pointing my tongue, I gently circled her dark flesh entry, feeling the folds of her puckernut on my tongue, and then pushed my way inside and shattered that last taboo.

"Oh God," she cried with pleasure as the nerve endings around her were startled into firing.

Empowered by her reaction, I pushed inward and began licking and tonguing her ass. She was clean and tasted of rich, dark avocado honey--tangy with a burnt flavor of a distant sweetness. I remained eating her ass until she pulled at me to come up to her face.

She began exploring my mouth with hers, licking her dark flavors off my face. The taste of her earthen insides flooded her with adrenalin, and she aggressively reached down to grasp my cock. She guided me toward her pink slit and, with two hands, one on each of my ass cheeks, pushed me inside her. The wetness of her pussy and my moistened cock created a fapping sound as I sank deep inside her until my balls rested on her ass. I then withdrew slightly and pushed in again.

Her pussy made wet sounds, and I could hear air escaping as I increased my cadence and began to ride her.

"Wait, wait, wait," she said, pushing me off. "I gotta pee so bad."

I rolled off her as she hopped up and quickly walked to the bathroom. I laid on my back, my head on the couch pillow, the blankets beneath me, looking at her fantastic ass. It was bigger than before, with little hints of cellulite, but she remained so inviting.

I could hear her pee, flush, wash, and she returned. The firelight lit her long legs, and I could see her whole body as she stood over me. Her pubic hair was thin and delicate,

a mixture of gray matching her head. Her face was natural. No Botox, no lifts, just an unassuming woman who, despite years of depression, remained as beautiful as she was when I first met her.

I lay on the ground, stroking my cock while looking at her. She walked toward me, stood over me, then kneeled so her pussy was on my chest, inches from my face. She ran her finger through her moist slit and then placed it in my mouth. I sucked her finger savoring her pussy's flavor, which now had a hint of salt from her urine. I pulled her forward so her essence could flood my olfactory senses. She shuffled forward until my face was between her legs and lowered her pussy to my mouth. My tongue, mouth, and nose went to work as she slid forward and back on my face, riding me gently. I could feel the bump of her cleft and her swollen clit.

She rode my face for several minutes, and I felt her heat rising. I don't think she expected an orgasm to arrive this quickly, but I could sense it was on its way.

"I think I'm going to cum," she moaned and tried to pull off my face so she could delay the action. I held her firm. I wanted her to cum this way. I wanted to feel her body on my face as she went through the pleasure contractions.

She began to get wetter, and the flavor of her pussy's emissions changed. I was now tasting sweetness. I assumed this was an indicator of her body's chemical reaction to my tongue's work, and I was right. She slid forward and stopped with my tongue pressing on her ass entry. Her body went rigid, and she shook as she let out a long gasp. Her puckered hole pulsated with pleasure. She pushed herself against my face and then rode it until she was spent.

Jenn rolled off me and lay silent before the fire. I slid behind her and held her as she peered into the flames.

"That was my third orgasm with a man...ever."

"Are you sure?"

"Very, it was beautiful. It was..."

"Long overdue."

She smiled and held my arm, stroking it. I wondered what she was thinking about.

"I want another," she whispered.

"Don't you want to rest?" I asked.

"Do you need a rest? Because I don't," she replied.

"Well, no, but I didn't finish yet, so..."

"Let's see what we can do about that," she replied.

Jenn turned over and got on all fours, facing the fire. She bent down so her ass was up, face down, leaving me staring at her waiting ass. She widened her stance and pussy, giving me a full view of her two entry points.

She reached between her legs and began to swirl her fingers around her vagina. I crawled toward her, examining her tight puckernut in the firelight. She was perfectly groomed, hairless, around her knotted hole. I ran my finger gently up her pussy, stopping on the button of her ass, and pressed lightly.

"I want you to explore me, try something new. There's so much I've never done."

Jenn moaned with pleasure. I wasn't sure if it was spontaneous or just a courtesy moan telling me she liked what I was doing and to keep at it.

I pushed my finger against her sphincter, gently ringing her back door.

True confession. I had never had anal sex, and from the looks of it, that was what Jenn was offering. I poked my finger deeper into her dark hole and felt my balls swell in anticipation.

"I've never done anal," I confessed.

"Then that makes two of us," she replied.

"Should we?" I asked. "What if it hurts?"

"How did we make it to sixty and never had anal sex?" she asked.

"Our history of bad choices; I guess that's another."

Sitting up, she said, "Open my handbag."

I crawled over to her handbag. Jenn let the fire warm her. I handed her the handbag, and she pulled out the CVS bag.

"You need cholesterol meds right now?"

"Not exactly."

She pulled out a small bottle of lube and threw it to me. It was pina colada flavored.

"Pina Colada flavored lube?"

"They had a lot of flavors, but I wasn't in the browsing mood. Be thankful I got it at all, or you would not be fucking my ass tonight."

"So, this is happening?" I said.

"We are on our third date. I think anal on the third date is acceptable. Lay down. I want to be able to see your face.

I lay on my back as she straddled me. Grasping my cock, she slid it into her pussy which coated my penis with her thick effluence. I was happy to be inside her and would have been glad to finish with her riding me with her snatch, but she pulled me out, bent forward, moved up, and blindly guided my cock to her waiting asshole.

She widened her stance yet again, allowing her anus to open slightly; I spread her ass cheeks apart and slathered the lube on my hand, then gently stroked her from behind, wiping the lube from her perineum to her darkest hole. She reacted with a groan of pleasure.

The lube was slightly cold, but her body's warmth heated it. Jenn bent forward, and I moved my fingers to her rear, poking in a forefinger and sliding it in deep. Another groan of pleasure and I pulled it out with a wet pop. I immediately reentered with two fingers, doubling her pleasure and pain. I knew she needed to be loosed before penetration. I spread my fingers against the smooth walls of her rectum, and she groaned in appreciation.

"I'm ready for you," she moaned.

With that, I withdrew my fingers, and she grasped my cock, pressing it against her anus. The tight hole opened slightly, having been teased by my fingers, and she guided the mushroomed tip of my cock through the small opening, which expanded to take me. There was a bit of resistance from her first sphincter, but I pushed through.

She put her hand on my chest to slow me, and I could see she was wincing in pain.

"I can stop."

"No, just go slow."

Her outer sphincter relaxed, and I slid in slightly, coming to another barricade. This was her inner sphincter, the last guardian of the darkness.

Since she was sitting on my cock, I couldn't push, so she did. With a determined look, she pushed herself against my cock, and the second sphincter relented, and I slid effortlessly through into the tightness of her chamber.

"Ohh, it's in. Oh God, that's...that's so..."

Jenn could not finish her thought as she fought through the mixture of pain and pleasure mixture.

She winced as I slid deep. The smoothness of her dark passage was unlike a vagina. It was softer, tighter, and I slid to a halt when my cock was fully engulfed. She was not moving or pulling.

Jenn slightly groaned, but I could hear the pleasure in its tone. She took over and began to slide back and forth, working my cock up into her ass. The smell of pina colada lube and Jenn's earthy essence filled my senses as she used my cock to churn the millions of nerve endings in her ass, causing them to fire almost all at once, bringing intense pleasure.

She arched back and leaned back on me with her hands, expanding the gap of her pussy as she forced herself deep into my cock. I was almost there. I could feel my ejaculation swelling.

Sliding my fingers in her empty vagina, I could actually feel my cock through her distended vaginal walls. The sensation of my cock in her ass and my fingers massaging her sugar walls caused her pussy to water profusely. So much for post-menopausal dryness.

Her sphincter began to pulsate and tighten around my shaft as she continued to arch back. With two fingers on each hand, she massaged her nipples, then moved her fingers to her clit.

She let out a huge breath and winced as her orgasm rose in waves like water filling a bucket that would soon overflow. That was all I needed, and I began to cum violently. It had been a while since I had sex or masturbated, and my load was hot, thick, and under extreme pressure.

I could feel my semen filling her rectum, looking for any place it could go. Despite the airtight seal she created around my cock, rivulets of semen and moisture escaped her ass and into my pubic hair at the base of my cock.

She relaxed and placed her hands on my chest to support herself as she tried to get her breathing control. The heat from the fireplace had created a sheen of sweat on us both. Drops of sweat trickled from her armpits, and a bead of sweat collected on her nipple and then fell.

She was only seconds behind me with her orgasm. Her fingers were moving at a furious pace as she worked her clit. The combo of her fingers and my cock made her orgasm the strongest I'd ever felt. Every muscle in her body clenched, and her rectum pulsated as she shook. My ejaculation was done, and the aggressive squeeze her sphincter was putting on my cock was turning painful, and then it was over.