Will You Be My Valentines? - Cover

Will You Be My Valentines?

Copyright© 2018 by Mister NiceGuy

Chapter 1: Busy, Busy, Busy

Romantic Sex Story: Chapter 1: Busy, Busy, Busy - In this sequel to It Started With Christmas, 39 year old Alex continues to build his new relationship with 23 year old Jessica, who he met a couple of weeks before. But what about Katelyn, Jess's younger sister, who wants Alex to have sex with her? Can Alex change Katie's mind, or will the two of them hook up? And if they do, how will that change Alex's relationship with Jessica? (Tags will be added as the story progresses.)

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Cream Pie   Oral Sex  

Time is a funny thing. Some say that time flies. I’ve never been sure about that. I have a friend who once told me that the days and weeks drag by, but the months and years pass quickly. And, you know, I think that sums it up pretty well.

In any case, the second week of January both dragged along and flew past.

I’d headed back to Ottawa on January 6, the first Saturday of the new year, after spending two weeks - only two weeks? - in the city of Oshawa. I’d been stranded there, just two days before Christmas, by a car that needed a new clutch. And since the car I was driving was a specialty import, it took them a few days to get the part, and of course the repair shop was closed over Christmas. So there I was, stuck, far from home. No family. No friends. No Christmas.

And then I met her, behind the bar, in that hole in the wall place, just off Canada’s busiest highway.

Jessica.

23 years old. Long brown hair. Nice ass. And the biggest, roundest pair of brown eyes I’ve ever seen.

We talked. I’m amazed I could form coherent sentences, but we talked. And no, I wasn’t trying to chat my way into her panties. Hell, I’m nearly twice her age. I enjoyed checking her out, but that was as far as I thought it would go.

But we talked. I told her a bit about me. And she told me a bit about her. We learned that both of us had lost our parents. We learned that we both had a sister. Hers was 17, and under her care. Mine lived in Vancouver, and wasn’t speaking to me. I learned that her Christmas was going to be kind of bleak, because there was never quite enough money. And she learned that my Christmas was going to be bleak, because I had no one to spend it with.

I sat on that bar stool, downing one rum and Coke after another, until it was closing time. When she brought the bill, I paid it, and then, on impulse, slipped a couple of hundreds into the folder. I wasn’t trying to buy anything, and I didn’t think I’d ever see her again. I just wanted to thank her for making a really shitty night just a bit less shitty, and to make those big brown eyes a little bit happier. Then I called out my thanks, and stumbled out into the night, looking for a cab to take me to a hotel where I could crash for the next few days.

But she came out. She came out before I could leave, as soon as she opened that little black folder and found the money. She thought I’d left it by mistake, and wanted to give it back to me. I told her that I had left exactly what I meant to leave, and encouraged her to buy something for herself and her sister. And when she realized I was serious, those brown eyes brightened, just a bit, and she pulled me close for a hug and a kiss on the cheek.

And then she took a chance. Life is full of chances, I guess. Some we take, and some we let slip. She took this one, and asked me if I wanted to come home with her. She made it perfectly clear that she wasn’t inviting me home for sex. I was being offered the couch, not a spot in her bed, and not a spot between her legs.

It took me no time at all to take her up on her offer. I went back inside while she grabbed her stuff, and we walked the few short blocks to the little apartment she shared with her sister. She had some second thoughts along the way, and wondered if she was making a big mistake. But I promised her I wasn’t going to take advantage of her, and we went inside. She helped me set up the couch, and showed me where the bathroom was, and I went to bed.

It was probably the worst night’s sleep I’ve ever had in my life. The mattress on the couch was terrible - much too short, much too thin, and lumpy as hell. But the next morning, when I met Jessica’s little sister, Katelyn, and they offered me the chance to stay with them for Christmas, I jumped at it, even though I knew that it meant not having a decent bed to sleep in for the next few days. And as the days passed, and Christmas came and went, I fell for that woman harder than I have ever fallen for anyone in my life, and she fell for me, too.

And all that happened even before I told her that I was a multi-millionaire, so you can’t claim she was just being greedy. I’m not sure what exactly makes a gorgeous 23 year old fall in love with a guy that she thinks is an unemployed 39 year old, but it happened.

And the sex. Shit. The sex, when it happened, was out of this world. I’ve never had it as good as I had it with Jess. And she’d never had it as good as she had it with me. In her case, though, that wasn’t saying much, since her past experience with guys had been pretty bad. But that led to a problem. Because having heard about how good sex with me was for Jess, Kate wanted to try it too. And Jess thought that was a good idea.

And if I’d been in my twenties, I’d have done it in a heartbeat. Kate was hot, and what guy doesn’t want to have a chance to show a virgin how it’s done? But I wasn’t in my twenties. I was almost in my forties. And I just couldn’t do it. I was sure it would be fun at the time, but I was equally sure it wouldn’t be fun afterwards.

I had to go back to Ottawa for a couple of days between Christmas and New Year’s, and at Jessica’s suggestion, I took Katelyn with me. It was good. Mostly. She was still trying to convince me to make love to her. And she wouldn’t take no for an answer. I finally got her to drop it when I changed my no to not now, and promised her - against my better my judgement - that if she still wanted sex with me after she turned 18, and if her sister still agreed we could do it, I would make it happen.

Once we got that settled, we had fun. I introduced her to my goddaughter, Taylor, who was about her age, and she and Katie spent a day shopping together. Kate and I also spent a day exploring some fun foodie shops on the other side of the provincial border, and I introduced her to a bit of Quebecois cuisine, which she loved. And I got to know her as a person, not just as my new girlfriend’s little sister. All in all, it was a win.

Kate and I drove back to Oshawa, and the three of us spent New Year’s Eve together. And as soon as the business world started up again, we started looking for houses. I was ready to pull up stakes and move to Oshawa. There was nothing holding me back, and lots pulling me out. But I couldn’t move into their tiny, one bedroom apartment with them. We needed more space. And I had the cash, so we got an agent, and found a place that we thought would make a home. We made an offer, and it was accepted.

And then I left. The very next day, in fact. I left Oshawa on Saturday afternoon, after Jessica tried to fuck my cock raw. I’d hoped to take care of some things around my condo on Sunday, and meet with my financial advisor on Monday, and be back with the girls on Tuesday. But it didn’t work out that way. There was just too much to do.

I made the appointment with my advisor for Monday morning, and that went fine. We talked about how best to pay for the house, given the fact that I would be selling my condo, and that I had the money from the sale of the business and would have more soon from my parents’ estate. He recommended a short term loan, which he helped me do the paperwork for. So that was easy.

I also talked to my best friend, Kim, who I’ve known since we were two years old. She’s a real estate agent, and she agreed to handle the sale of my condo for me. We had lunch together on Monday. Kim was still a bit uneasy about the speed with which I’d made the decision to leave the city I’d made my home for the last two decades behind, but she accepted it. Kim is Taylor’s mom, so she’d met Katelyn - and she said she was looking forward to meeting Jessica as well. I promised her I’d make that happen soon.

On Monday afternoon, however, I got a couple of calls that changed my plans, at least a bit. One was from the lawyer who was dealing with my mom and dad’s estate. She needed to meet with me, she said, to work out some details. The other was from the accounting firm that had been hired to do the final work of wrapping the sale of the software company I had been a partner in, and figuring out who was owed what and when. I’d met with them for a full day the week before, as the CFO of the old company and the only partner who wasn’t going on to a job with the bigger corporation that had bought us out, but they had some more questions. Was I free Wednesday?

I didn’t want to say yes, but I did. I called Jess Monday night, and talked to both girls on speaker. I told them I wouldn’t be back the next day, as promised. They both tried to sound cheerful, but I know they were disappointed. So was I. I said I’d be back Thursday.

I met with the estate lawyer on Tuesday morning. There were only a few things that she needed to talk about. Most of the big issues had already been settled - the house emptied and sold, other assets liquidated. She went over, again, the smaller bequests that had been stipulated in my parents’ wills - the $25,000 for my niece Laura (who was my parents only grandchild), the few small charitable donations. She showed me the work she’d done on my parents final tax returns. The residue of the estate was to be split between my sister Jane and I, and she thought that she’d have a preliminary cheque for each of us within the next six to eight weeks.

I spent Tuesday afternoon at my condo, sorting and shredding some paperwork in my home office (so there would be less to pack and move).

Wednesday was a long day, but didn’t accomplish all it should have. There were still loose ends to be tied up. And while I wanted to go back to Oshawa, I also wanted to get as much done as possible so this would not be hanging over my head any longer.

So I called Jess again, early Thursday morning, as she got home from work, before either of us went to bed. I could hear frustration in her voice, but more than that I heard doubt. She was worried. She didn’t say it, but I knew what she was thinking. It had all happened too fast, and now that I’d had the chance to leave for a few days, I had moved on. It had all been a dream. I wasn’t coming back.

But nothing could have been further from the truth. Every day I was away from Jessica, and from Katelyn, strengthened my belief that they were who I needed to be with. But I didn’t know how to say that, so I said nothing, and trusted instead that the best way to help Jess feel better was to get back to her as soon as I could.

I met with the accountants again on Thursday, and by suppertime, they seemed to think that all was in order. I debated getting in the car and driving to Oshawa that evening, but I knew I was tired, and the prospect of killing myself by driving when I shouldn’t wasn’t appealing. Discretion, as they say, is sometimes the better part of valour.

So I texted Jessica, and said I’d arrive in the middle of the afternoon the next day. Jess texted back that she had to be at work at 4:00, and I said I’d be back well before that. I went to bed early, after starting a load of laundry. With Jess and Kate’s apartment building only having laundry in the basement, it was easier to go back with clean clothes.

Friday morning I threw my laundry into the dryer, shaved, showered, packed some clothes, and was on the road just before 9:00. I hadn’t taken time to eat breakfast, but a drive-thru solved that. It was a bitterly cold but clear day, and I made really good time, stopping only once to drain my bladder and get another cup of coffee to refill it with, so I pulled into the parking lot at Jessica’s place at a little after 1:00. Jess must have been watching for me, because as I unlocked the front door and headed up the stairs, she came out of the apartment. We met at the top of the stairs, and she threw her arms around me. It took me a second to realize that she was crying.

“Hey, hey,” I said, as soothingly as I could. “What’s wrong?”

She didn’t answer, at first. She held me for a minute or two more, then pulled back a bit, and led me into the apartment. She helped me take off my coat, then wrapped her arms around me again, nuzzling my neck with her lips.

“I thought you weren’t coming back,” she said. “I thought maybe I’d done something wrong, and messed it up. Or you’d realized, once you left, what a mistake getting involved with me was, and you were cutting your losses.”

I pulled back just enough so that I could take her head between my hands, and tilt her face up a bit. I leaned down and kissed her. God, I had missed those lips.

“I will always come back,” I said. “And getting involved with you was so not a mistake. It was the best thing that has every happened to me. Being away from you made me realize that even more than I did before.”

She kissed me, then pulled back.

“I’m sorry. I should have trusted you. And part of me did. Really. But part of me ... well, once you were gone, I started hearing all these little voices that said, ‘Duh. Like a guy like him would ever stick with a loser like you.’”

“For starters,” I replied, “you are not a loser. And for every little voice inside you that makes you doubt me, I have a voice that asks what a gorgeous woman like you could possibly see in an old nerd like me.”

She laughed, and wiped the tears from her eyes.

“I almost forgot. You’re likely starving. Katie made some soup last night. It’s on the stove, warming up.”

“I’m not starving, but I would never turn down your sister’s cooking.”

Jessica’s sister, Katelyn, is only 17. But she’s a phenomenal cook. She’s entirely self-taught, too, which makes me wonder what she’s going to be like once she’s had a chance to have some real culinary training.

“Well, if you’re not in danger of succumbing to low blood sugar, let’s wait a bit for lunch,” Jessica suggested. “That way I can show you what I see in you, even if you are an old nerd.”

She took me by the hand, and pulled me towards the bedroom.

“I was talking to Carrie the other day at work,” she said. “And I told her I was worried about losing you. She said that the best way to make sure you stuck around was to give you really good sex every single day. I’m still bleeding, so you’ll have to settle for a blowjob today, but I’ll be squeaky clean and fuckable again by tomorrow night.”

“Jess, you don’t have to -”

“Are you saying you don’t want a blowjob?”

I thought about it. But not very long. Then I shrugged.

“Who the hell am I to argue with Carrie?”

“Exactly,” she said, and she dropped to her knees, pulled down my zipper, and helped me step out of my pants and underwear. Then she pushed me down onto the bed, knelt between my legs, and took my cock into her mouth.

I’d had more sex during the two weeks I’d spent in Oshawa with Jessica than I’d had in the previous two years. Ok, maybe that’s an exaggeration, but not by much. I’d had the occasional girlfriend, but it was never very serious and it never lasted long. I had enough money to buy myself a couple of hours of female companionship once in a while, but I had also seen lots of guys spend tens of thousands of dollars annually in that way, and I didn’t think that was a good investment, so I tended to limit that to a couple of times a year. Most of my sexual activity involved my right hand, and while I masturbated regularly, it wasn’t a daily occurrence by any means.

So after getting laid regularly for several days, and especially after Jess had spent our last night and morning together trying to drain every single sperm cell from my body, I hadn’t felt the need to jack off while I was away. I’d had a lot on my mind, between winding up the corporation and finalizing the estate stuff, and unlike my previous trip to Ottawa, when I’d resorted to masturbating in the shower, I hadn’t had a sexy teenager with me who was intent on making me notice just how sexy she was. I’m not saying I didn’t think about sex during the 6 days I was gone - just that I didn’t feel an urgent need to get relief.

The source of this story is Storiesonline

To read the complete story you need to be logged in:
Log In or
Register for a Free account (Why register?)

Get No-Registration Temporary Access*

* Allows you 3 stories to read in 24 hours.

Close
 

WARNING! ADULT CONTENT...

Storiesonline is for adult entertainment only. By accessing this site you declare that you are of legal age and that you agree with our Terms of Service and Privacy Policy.