Will You Merry Me?

Who was your first love? Why did you let them slip away? Would you rekindle that relationship if you could and make up for lost time?

This story follows Davey and Jenn as their paths cross every 20 years on Christmas Eve. It's about chance meetings, immediate attraction, stepping outside your comfort zone, and romance. Oh, and sex, lots of very vivid and erotic sex.

TAGS: Anal Sex, Anal Play, Blowjob, Hairy Pussy, shaved pussy, Mature, Swallowing, Nipples, Romantic, Creamier, Ass play, Light Bondage, Big tits, Cunnilingus, Love, Romantic

WILL YOU MERRY ME?

1983

It was my first day on the job as one of Santa's elves at the Irondequoit Mall in Rochester. The Christmas rush was on, and the hot spot for this time of year was Santa's village in front of the JC Penny's. It was a vast display of North Pole workshops punctuated by an impressive Santa's Castle. Santa's throne was outside the castle, perched on a mountain of gifts. This was the epicenter of experiencing the magic of Christmas if you were a kid or, like me, a college student looking to earn extra money.

Santa's Castle housed the team break room so the elves and Santa could take a break without walking through the mall and getting accosted by kids. I entered through the back door to be greeted by Kevin, the North Pole photographer and boss of the operation.

"Welcome to the North Pole, elf Davey."

Fuck me. It sucked that I needed a job over the holidays, and it sucked even worse the only job I could get was as an elf. I'm six foot one, for Christ's sake.

Kevin gave me the rundown and handed me my elf costume. My co-worker Jenn would be in soon, and she could give me the particulars like how to deal with crying kids, angry moms, and vomit. Yeah, some of these kids get so freaked out they puke. Wow, this just kept getting better and better.

Our breakroom was broken into two areas. A room with a couch, some chairs, and little else lit by the frosted windows that let in mall light. A second room was a dressing room where we could change into our costumes.

I emerged from the changing room in my elf costume. Yes, it was humiliating at twenty years old to be dressed as an elf, especially in red tights that did nothing to hide my genitals.

"You look good, kid," said the guy playing Santa. "A little tall for elf work. Hunch over. Keep that tunic low, or people will see your hard-on".

"I don't think I'll get any hard-ons working as an elf."

"You will when you see Jenny Jugs," he said with a lascivious smile.

"Jenny Jugs?"

"Santa's other helper. She should be here any minute."

Great, I thought to myself. I got a horny Santa who's hot for one of the elves. Looking out a scratch in the frosted window, I saw a line of kids waiting for Santa to emerge from his castle. It was about to be game on.

The door opened, and a woman entered wearing a heavy winter parka. She had her back to me as she took it off to reveal her elf costume. Similar to mine with a red tunic, she had a fantastic ass wrapped in green Capezio tights. The tight fabric wrapped itself around each ass cheek and left little to the imagination. If she was wearing underwear, it had to be made out of dental floss. She turned to face me, and I could see that amazing ass was just the appetizer. She had huge breasts. Absolutely huge. While her elf tunic did its best to hide her amazing tits, there was plenty to see. I did what any guy would do, and I stared.

"Davey?" I heard my name and looked up at the big tit girl who was smiling at me.

Davey? Are you going to elf with me this year? I can't believe it!" With that, the attractive elf ran up to me and wrapped me in a tight embrace. I felt her breasts pushing against me. Santa took down his spectacles to watch.

"Jenn?" I said as I broke the embrace to get a look at her.

It was Jennifer Ostern, my high school classmate.

"I haven't seen you since Suzi Lyman's grad party," she said with delight. "That was almost three years ago!"

Santa looked at the two of us.

"You two know each other?"

"Since 5th grade," Jenn said with a smile. "We graduated from Hamilton in '82. Oh, man, this is great. Davey is such fun."

I had not said much of anything as I was still in awe of Jenn's huge breasts. This was not how I remembered her. Not at all. She wasn't flat-chested in high school, but her boobs were nothing much to speak of. But now, this was unbelievable.

"It's the boobs, right?" she said with a smile.

"Excuse me? What?" I stumbled for words after getting busted for gawking.

"The boobs. I know the look. I get it a lot--the summer after we graduated, I had a boobspurt, and they just got big. It might be because I quit running. My dad says it's because I like beer. So, yeah. I probably look different to you."

"You look great, and I can't believe it's been almost three years."

In my mind, I was saying, I can't believe how big your tits are.

"Hey, I'm sorry to break up the reunion," Mall Santa interrupted, "and I would love to hear more about your visit from the titty fairy, but we've got cranky kids out there, and it's time to do our thing."

"Right, Santa!" Jenn said with a smile, then hugged me again and bent over to put on her elf shoes. With her perfect ass just inches from my face, Santa nudged me and pointed to my tunic, where my hard-on was pressing against my tights.

"Why don't you take a minute to settle down before joining us outside?" he urged as he patted Jenn on the ass and ushered her outside to the cheering of all the kids.

I rearranged myself and followed the two to Santa's throne. Jenn was on one side, I was on the other, and from my vantage point, I could see the round of her breasts clad in a tight turtleneck behind her tunic.

While I wished I had more time to stare at Jenn's tits, the job of wrangling kids and keeping them happy and in line took up most of my afternoon. The kids were great, but from my position in line, I could hear the moms gossiping about the elf with the big boobs and was that appropriate for Santa's village.

A dad escorting his two young kids elbowed me and leaned back conspiratorially.

"How did you land this job, kid? Lots of milk for your cookies. Am I right?"

I smiled but was put off by the commentary. Then again, I also had been fixated on Jenn's breasts, and I wondered if I was any better than that horny dad.

Santa's village closed at seven, and we retreated to the castle to change into civilian clothing. Our Mall Santa, who was a damned good Santa with a real pot belly and natural beard, headed out in his outfit, having another event to attend as Jolly Saint Nick.

Jenn used the changing room first as we talked through the door.

"How was the first day?" she asked.

"Not as bad as I would have thought. I thought the kids would be monsters, but they were good. The parents are too much."

"Tell me about it," she replied. "I got groped at least three times by some of the Dads."

"That's not cool," I said in her defense.

"Comes with the territory. But I appreciate your support. Hey, you want to get something to eat?"

I realized how hungry I was, and we headed to the TGI Fridays at the end of the mall and enjoyed a plate of nachos and potato skins while we caught up on the past three years.

Jenn got into several colleges but was currently attending our local community college.

"I don't know what I want to do yet, and spending almost six thousand dollars a year to attend a university seems crazy. I'm saving money, though. I also work as a cashier at the Price Chopper Grocery on Genesee Street."

She had been dating Jimmy Malone, who graduated a year ahead of us. He was already selling real estate and had an apartment.

I told her about the end of my recent relationship at college. Claudia was a handful, extremely high maintenance, and I don't think she was ever that into me.

Jenn wanted to get out of Rochester as soon as possible. She was saving money to get a good car and then roll out. She dreamed of heading West, North, or even South. I had to agree; there wasn't much here for either of us.

I walked Jen to her car and made sure she got in safely. She hugged me warmly and told me how excited she was that we would work together for the next few weeks. I drove home to my parents' house and fell asleep fast. Those kids sure did wear me out.

The next few days were busy at the mall. The place was packed, and the lines at Santa's Village were long. While I loved entertaining the kids as a six-foot elf, it was the break time in Santa's Castle when I got to sit and talk to Jenn, which I looked forward to.

Mall Santa told us about his time in California: warm beaches, Hollywood, and Disneyland. Considering the almost sub-zero temperatures outside, that sounded amazing. He was a bit of a kook, was always in costume, and we suspected he might be stoned half the time. But he was great with the kids. Kind, compassionate, and always knew the right thing to say. No child ever cried in his lap.

Jimmy Malone came by to pick Jenn up one evening and got a look at me in my costume. He was the kind of guy who needed to make a jackass comment about anything, and he unloaded on me.

Jenn told him to knock it off. She had changed into her civilian clothes, and I could only marvel at her shape as she walked off with Jimmy. The guy was an asshole in high school and now worse. Why do nice girls always fall for assholes?

"So, you've fallen for Jenny Jugs," Mall Santa said as he watched her ass twitch as she walked away.

"What? No. She has a boyfriend and..."

"Kid, I call it like I see it, and you've fallen for Jenn Jugs."

"You shouldn't call her that,"

"Again, I call it as I see it, and those are some major league gazongas."

"We could use a Mrs. Claus around here to keep you under control," I replied.

"I just call it as I-"

"-see it. Yes, I know."

"Hey, you got a car? Can you ride ol' Santa to the Tap Room on Liden Street?"

"In your outfit?"

"No one ever charges a Santa for drinks at Christmas time."

I drove Mall Santa to the bar and watched him wander in. Whoever that old-timer was, he had the Santa game down cold, and I doubt he paid for a meal or drink all December.

At home that night, I pulled out my senior yearbook and flipped through the pages. I stopped on Jenn's old photo. It was a classic female senior photo with a black top off the shoulders and a pearl necklace. Her cleavage showed, but there wasn't that much to offer. That difference between three years ago and now was astounding.

As I drifted to sleep that night, I saw Jenn standing in my bedroom. She wore all-black tights and a skin-tight top that seemed to be painted on.

"I don't want to wake your parents," she said as she slipped into my bed. This was the bed of my childhood, only a twin, so when she crept under the sheets, she was practically on top of me. As her breasts pressed on my chest, my cock began to swell. There was no way she could not help but feel it against her body.

I could feel her hand make its way down my chest and then over my boxers as she gently massaged my hard-on.

"I've seen you looking at my tits at work."

Despite my attempts not to get caught looking, I knew it had been evident, but they were so big, and she was always on my mind.

"You want to see them?"

I nodded yes, unable to believe what was happening. Jenn moved to straddle my waist as I lay on the bed. My cock was now pressing hard against her ass. She had to be feeling that. She smiled and pulled her black top over her head, revealing her massive breasts with large cherry-red nipples with a pronounced dimple on the tip. Grasping her left breast with two hands, she leaned forward, bringing it to my face. Just before she placed it in my mouth, she drew back, teasing me with the nipple. Moving forward, she gently traced the tip of her nipple around my lips before slowly inserting it into my mouth to meet my waiting tongue.

Her nipple was large and fleshy. I could feel the bumps around her areola as my tongue circled and searched her flesh. She shifted her ass, and that was it. I was going to cum. Nothing could stop it now. The orgasmic sensation began in my legs, and my cock released streams of thick hot semen.

It was then I awoke, dazed and confused. I looked for Jenn, only then realizing I was alone in my childhood bed. I reached down to feel my withering cock finding it slathered in my cum. It had been my first wet dream since I was a kid. I lay back in bed, tired and frustrated from my dream encounter.

The next day, I was walking into the mall when I saw Jenn getting dropped off. She waved and ran over to me.

"Hey, my car is in the shop. Can you give me a ride home tonight?"

"Sure, glad to," I responded as we entered the mall. It was another day of kids, costumes, and time spent with Jenn. I could take or leave the kids and the costumes, but spending time with Jenn was special.

Jenn took off her parka to reveal her robust full figure clad in festive Christmas colors.

"Wow, you look great," I began, but as I did, the images of our dream sexual interlude flooded my brain. I blushed and turned away from her to hide my unexpected embarrassment.

"What's up? You okay?"

"It's just so warm in here. When I come in from the cold and hit the heat..."

I continued to divert my eyes out of fear of looking at her and getting redder in the face or, worse yet, sporting an erection.

Jenn playfully grabbed my arm and held it as we walked toward Santa's Village. Her friendly embrace flooded me with warmth and pride. People would think we were a couple, and for those few moments, I imagined us off on a beach together. Then Mall Santa ruined the moment.

"Hey, no fraternizing allowed at the North Pole." He said with a chuckle, knowing he had ruined my fantasy.

"Right you are, Santa," Jenn said as she released my arm and gave him a military salute. We entered Santa's Castle, and Jenn entered the changing room to get her elf outfit on.

"You hitting that, kid?" Mall Santa asked.

"No, I've told you before, we're friends."

"Kid, I've been around a very long time, and I know lovestruck when I see it, and I'm looking at it right now."

Jenn exited the changing room with red tights and a tight turtle neck. Her firm nipples tented over her breasts as she brushed off the frumpy tunic she would then place over her top and hide her natural talents.

"Skip the tunic today and give the dads something to enjoy while in line," Santa said.

"Really, Santa?" Jenn said, rolling her eyes. This was years before HR departments even knew how to spell the word harassment. Jenn smiled and let it go, as she always had.

Santa gave me a nudge and made the big titty gesture outside of her view.

I entered the changing room and took my elf outfit from my bag. Jenn's bag of civilian clothes was on a hook, and the zipper was slightly open. As I changed, my mind wandered, and finally, I could resist no longer. I opened her bag to find her civilian clothes neatly folded for after work. I was tempted to smell her clothing but decided against it. I changed and joined her and Mall Santa for another day of pre-Christmas fun.

It was time for our lunch break, which Jenn and I usually took at the food court. But today, her boyfriend was coming by, so she ran into the changing room and emerged in her civilian clothes. I went to the Sbarro pizza, dressed as an elf, got my slices with the employee discount, and returned to Santa's Castle. Mall Santa was sleeping on the old couch as I ate my slices to his snoring. Through the open door of the changing room, I could see Jenn's elf outfit hanging on the hook. With Santa in Slumberland, I crept into the room, took Jenn's tights off the hook, and put the moist crotch to my face.

Wearing the elf outfit was hot work, and we both sweat a few pounds off that season. I knew her fragrance would linger on the leggings and was not disappointed.

I inhaled her savory scent, which went right to my brain like a drug, causing my hormones to rush frantically. I inhaled again. Her fragrance smelled like warm figs with a touch of sweetness. The smell of her laundry detergent was unable to overpower her natural essence. I desperately inhaled several times, huffing her sweat perfume. I carefully put her tights back and nervously ate my slices.

Jenn returned to work, put on her outfit, and joined me at Santa's side. She was quiet most of the afternoon, lost in thought.

She revealed her boyfriend had broken off their relationship on the drive home. She didn't see it coming, but he was involved with a co-worker and wanted a clean break before Christmas.

"It's sad not to have a boyfriend during the holidays," she said with a lilt in her voice.

"Tell you what, you can have me as your work boyfriend," I said. "We spend all day together; people call us Mr. and Mrs. Elf, so there you have it."

"My elf boyfriend! What's our backstory?" she asked.

"Our backstory?"

"Any good story has a great backstory. How did we become us?"

"Okay, we both attended North Pole High School, and you were in charge of bows on the gift wrap committee."

"I think I should have worked with the reindeer."

"Okay, you are Donner's wrangler."

"His name is Donder. Are you sure you are an actual elf?"

"I am. I'm in charge of stocking stuffers. It's a thankless job because everyone forgets about my toys when the big toys roll out. But I get unlimited Toblerone bars, so play your cards right, and I can hook you up."

"Sorry, I don't want any. Chocolate is terrible for the reindeer, so no thanks to your triangle chocolate. That Donder gets into everything."

"You are not making this backstory stuff easy," I said. "We first dated 200 years ago. We've been thinking of getting married.

"We're going to get married! I love that. Are we going to have kids? Little elves?"

"Sure, at least fifteen. Maybe twenty."

"Wow, that feels like we spend a lot of time dipping your candy cane in my hot chocolate," she said slyly.

"It's the North Pole. Other than making toys, those elves are all getting it on."

"Okay, well, let me add that the gals in gift wrap are so jealous of me because they all wanted to date you, but I got you first."

"Yeah, that gift wrap team can be pretty catty. Every guy elf in stocking stuffers has a crush on you. I'm pretty sure the entire place does."

"Aww, that's sweet. But 300 years ago, I met you, and that's all I need."

I was lost in the narrative the two of us were spinning, a fantasy life spent together. Sure, it was a fantasy that we were elves who worked for Santa, but it felt so good.

"I like this story. It makes me feel loved," she said. "How did you propose? Was it romantic?"

"At the gingerbread ball. I got down on my knees in front of the entire toy team."

I got on one knee to recreate the proposal.

"Will you merry me?" I asked.

"Wow, you asked me to marry you. Like Merry Christmas?"

"I did. It's how elves propose."

I got serious for a moment.

"Will you merry me?" I repeated.

There was a pause, and Jenn joined me in my fantasy moment.

"Of course I will. I mean, dating for 100 years seems like enough?"

Jenn's smile seemed to wipe away all the sadness. She leaned in and kissed me on the cheek. We held close for a moment, very close. It felt like she was waiting for me to kiss her. Perhaps she was thinking about kissing me? It was uncertain and awkward, and I let the moment pass, not wanting to appear to be capitalizing on her breakup.

"We're getting merried. Thank you for that."

Jenn exited the car, and I waited until she was safely inside the front door.

Deep down, it wished it were true. I could easily see spending my life together with Jenn. I saw houses, families, and holidays and even getting old. All happily merried to Jenn.