The Babysitter and the Widower

"Hi, kids! Hi, Mr. Anderson!" Lizzie was zooming up the street into our driveway on wheels. She had no idea how intense my roller skating fetish was.

"Hi, Lizzie!" Sarah and Marco ran to meet our babysitter as she braked to a stop.

"Look what I got, Sarah? New skates just like you!"

Lizzie was the curvier of the two Johnson girls, but her older sister, Jen, was taller and prettier. Lizzie had put on a few pounds since I saw her last, but she wore them well. It was all a matter of preference, and I liked the bounce of Lizzie's body.

Especially on roller skates.

"Are we going skating today?" Sarah was beyond excited, and so Marco started jumping up and down. He did everything possible to mimic Sarah; she was his hero.

"Maybe. Should we teach Marco how to skate?" Lizzie had her full attention on the kids, which gave me a quick moment to enjoy the scene. Her long, white t-shirt and spandex shorts were doing nothing to quell my mischievous thoughts.

"Dad, didn't you say it was going to rain today?" My trance was broken when I heard my name.

"Yep. My phone says it will be raining in an hour." The thought of Lizzie in a wet shirt got my cock stirring a bit more than it already was.

"We could always go to the roller rink, but I don't have a car today." Lizzie was home from college and didn't take a full-time job so she could babysit four days per week for me. Life was hard since my wife died six months ago, and the Johnson family was beyond compassionate and helpful since we found out she had cancer.

Becoming a single parent at 40 is not a task I would wish on anyone, especially with an 11-year-old daughter. I was not well-equipped to teach her what it was like to become a teenage girl. I was counting on Heather for that, but God had a different plan.

Sarah handled her mother's death much better than Marco did. Maybe it was because she was eight when Heather was diagnosed and Marco was only four. Maybe it was because even at 11, she handled everything with the grace and confidence of an adult. Maybe it was because of people like Lizzie and Jen taking her under their wing. It's hard to tell.

"I can drop you off at the roller rink if you need me to. I can work from home today and come pick you up when you want to leave. I don't have a lot to do today." I tried to make things easy for Lizzie and Jen when they watched my kids. It's the least I could do.

"That sounds great, Mr. Anderson! Thanks so much!" I felt good knowing they would get to do what they wanted, but I was unprepared for the question Lizzie was about to ask.

"Why don't you come skate with us?"

First, I hadn't been on roller skates since high school. The physical results of skating could be catastrophic. Single fathers and broken bones are not friends.

Second, I'm not sure I could handle watching Lizzie and others gliding around the rink without pitching a painful tent. I had never taken Sarah to the roller rink, and Heather never knew why I asked her to take our daughter the few times she asked to go. I was too embarrassed to share my fetish with Heather, and I was afraid she would have thought I was weird or perverted. I thought it was best left hidden from the outside world. Looking back, I wish I had taken the chance by revealing it to her.

I panicked. "I have a lot of work to do today, Lizzie. I'll just drop you and the kids off and come back home." I forgot that I just told her I didn't have much to do.

"You just said you didn't have much to do today, silly!" Shit. She remembered.

Panic response #2. "Ok, you win. I'll come with, but I can't stay long." What just came out of my mouth?

The kids cheered and I stood there with a dumb look on my face.

"Great! I just have to run home to get my shoes, and then I'll walk back here so we can go. The rink won't let me enter wearing skates." Lizzie's smile was one of her best features. Her blonde hair framed her face perfectly, and her smile could light up a room. Or a driveway.

"Why don't we all get in my car, and we can stop at your house so you can change footwear? Then, we can just go straight to the rink. Let me run upstairs and change clothes." The gym shorts I was wearing would not be able to contain the bulge that I knew would arrive very soon.

I walked into my bedroom and stared directly at a picture of Heather. What the hell am I doing? I just agreed to go to a roller rink with my 21-year-old babysitter and my kids, and I most certainly will be aroused more than any time since Heather died. She said she wanted me to do whatever I needed to keep me happy after she died, but she certainly didn't have this in mind.

"Calm down, Paul," I said aloud to myself. "You are just taking the kids to the roller rink."

I quickly changed into two pairs of boxer-briefs, thinking that would act as an additional layer of erection suppression. I threw on some cargo shorts and grabbed my Yankees hat. The Johnsons had taken the kids to a game a few weeks ago and Sarah bought me a hat with money she had saved up from working in the neighborhood yards. Naturally, I bawled when she gave it to me.

As I hurried downstairs, I thought one last time about where this little trip could lead to. I caught a glimpse of Lizzie out the window and decided to just go with it. After all, it wasn't every day that a 21-year-old blonde with a great body roller skated into my driveway.

Heather and I were married for 15 years. We met in college, and though she graduated a year before me, we continued our relationship without interruption. She was tall with beautiful brown hair and the most magnetic personality. What she saw in my frumpy ass was beyond me. Her parents loved me and her siblings treated me like part of the family immediately. It was too good to be true.

Then, the diagnosis. The cancer wasn't localized to her breast. It had spread to her lungs. At 37 years old, she had a death sentence, and we had no idea when her number would be called. Doctors said she had a 20% chance to make it five years; she lived for three. We had as much fun as we could in the first year, but the last two were pure hell.

Prior to her illness, our sex life was good. On several nights when my in-laws wanted to take the kids, we had long, passionate sessions of love. It wasn't sex anymore. It was an artistic appreciation of each other. It was beautiful.

We both had our flaws, like everyone else. She didn't like the little bit of belly fat that stayed with her after the kids were born. I didn't like the little bit of belly fat that I had carried since I was 14. We were in love, and we decided long ago to look past the imperfections.

About a year after she was diagnosed, she didn't have the power or stamina to have sex anymore. Given the situation, it certainly didn't make me look at her any differently, but she felt awful for me. She told me to go out and find a sex partner if I wanted to, but of course, I never did. I quit my job and got my real estate license so I could make my own schedule. I was fortunate to be able to be there for her final few years.

The Johnsons were also a tremendous help. We moved into the neighborhood about the same time as Larry and Kathy, and so we bonded immediately. They had two daughters, Jen and Lizzie, and always told us that if we had kids, their girls would love to be babysitters. They were right; both girls loved my kids from the minute they were born.

Kathy would cook for us at least once every week, and Larry would take me golfing or fishing every so often just to take my mind off the impending doom. The girls would take my kids on adventures that their mother used to love, and Heather adored seeing the pictures of their journeys, while dying inside that she couldn't be the one watching them hike or play mini golf. Kathy was a little aloof at times, but they were more than generous with their time and talent.

I snapped out of my reminiscent daze and went outside.

Fortunately, Lizzie had already taken her skates off and was standing barefoot ready to get in my car. She had small feet, and her toenails were painted green, my favorite color. She and the kids piled in, and we drove down the street to the Johnsons' home. Lizzie jumped out, opened the garage door, and grabbed a pair of flip-flops.

Mikey's Rollerama had been a staple of the social scene in our town for several generations. It was small, but grade school and high school kids would go there to learn how to skate or just hang out and listen to music. With Lizzie carrying her bright blue skates, we walked in to discover that the rink wasn't at all how I remember it. Granted, it was 9:30am on a Wednesday, but the place looked like a mortuary. There were maybe 20 people in the entire place, and all but two of them were old enough to be my parents.

The sign in the front window said they had open skating from 9:00am-1:00pm on Wednesdays, but I thought I would ask.

"Can we get out there?" The girl behind the desk looked to be about Lizzie's age, and this was likely her summer job.

"Absolutely! It's just four bucks per person. How old is the little guy?" She smiled and waved at Marco.

"He's seven. He doesn't know how to skate, so we are going to help him." I still couldn't believe I was here.

"Great! I'll let him in for free. Take these tickets and go over to the skate gate to get your skates!" She obviously liked her job.

Then, she leaned over to me and said, "Be careful out there. The old-timers don't always check their mirrors." I laughed out loud, and we headed for the gate.

As the kids were putting on their skates, I asked if the rink had anything to help Marco. They gave me a contraption that looked like a walker on wheels. It looked like something that everyone else in the building used in their daily lives.

Lizzie bent down to tie her skates, and when her hair flipped up, I noticed that she had a small tattoo of a rose on the back of her neck. I asked her about it, and she looked up at me with a bit of an uncomfortable gaze.

"Let's talk about that later, ok?" I had no idea what nerve I hit, but it was clear she was bothered, so I backed off.

I laced up my brown rentals that looked like clown shoes with wheels and stood up. Surprisingly, I wasn't shaky as we slowly made our way to the floor. Lizzie seemed to notice that I was relieved that I hadn't hit the ground yet.

"You are doing great, Mr. Anderson! It's just like riding a bike!" She touched my arm and smiles, which sent chills down my spine and a little blood to my cock.

"Lizzie, please call me Paul. We are both adults."

"If we are alone, I will, but in front of the kids, I prefer to show respect." She was always well-mannered and thoughtful. Wait, did she think we were going to be alone at some point?

As we stepped onto the floor, my legs wobbled a bit. Moving from thin carpet to hardwood was a big step for a guy who hadn't skated in two decades! Lizzie and Sarah made the transition with no problem, and they got Marco set up with his walker-trainer thing.

So far, so good. I was moving slowly but staying on my feet. Lizzie and Sarah were a bit in front of me, skating alongside Marco, who was having no trouble at all. He wanted to ditch the walker after a few laps, but the girls convinced him to keep it.

I had another chance to look at Lizzie from behind. Her shape was amazing. She was only about 5-3, but her toned legs looked sexy in skates. They led up to probably her best feature; her amazing ass. It was firm and voluptuous, and perfect for her frame. I don't know how often she went roller skating, but if her ass was any indication, she was on wheels often.

Just looking at her from behind stirred a little trouble in my nether region. It also didn't help my goal to not crash land. I nearly fell after turning too hard and made my way over to the wall for support. Lizzie didn't see me stumble, which I was happy about. It would be embarrassing to wipe out in front of her and my kids.

I smiled a little while thinking that this felt a little like high school. I was looking at the butt of an attractive blonde girl and trying not to fall. That's how I spent most of my junior year.

I was quickly reminded that this was very different, as Lizzie and the kids turned a corner and could see me ahead still gripping the short wall. I saw Lizzie motion for Sarah to stay with Marco, and then watched as she skated over to me.

"Are you ok? What happened?" Her face told me she was genuinely concerned.

"I'm fine. I just stumbled a bit, so I wanted to take a break. No broken bones yet!" I tossed a fake laugh her way to try to ease her mind, but it didn't work.

"I would feel terrible if you hurt yourself after I begged you to come." I couldn't help it; hearing her say "begged you to come" pushed some more blood down south.

"I'm good, Lizzie. Go and have fun with the kids. I'm going to sit for a minute." I don't think she could tell why I wanted to sit.

As she skated away, the nerves began to get to me. I just wanted to go home and get some work done. By the grace of God, there was nobody else even remotely attractive in the building, and the sight of 70-year-olds on skates didn't stimulate me in the least.

I sat on the carpeted bench just off the main floor for a few minutes as Donna Summer's "Hot Stuff" filled the rink with disco. I watched how great Lizzie was with the kids and wished Heather was here to see this. Although if Heather was alive, I wouldn't be in this building at all. Ever.

As the song ended, a voice came through the speakers announcing that it was time for the couples skate. The Rollerama had a live DJ on Wednesday mornings? Lizzie and the kids rolled off the floor and came to sit next to me. We watched as about five couples took the floor, each with the woman skating forward and the man backward.

The kids asked if I got hurt and I assured them that I didn't fall. I stood up to show them how well I could balance, and Lizzie jumped up next to me. She looked me right in the eyes.

"Mr. Anderson, I know we aren't a couple, but would you mind skating with me?"

I was amazed at the power of the human brain, because at least 30 questions went to my head at the same time. Why did she want to skate with me? What would the kids think? What would the old people think? What if I fell?

"I don't think we should, Lizzie. I don't want to leave the kids here alone." I tried to convince myself that was the reason.

"We can see them while we are out there. Besides, what is going to happen? Is some grandma going to try to hurt them?" She was so smart and quick.

Ignoring every red flag in my brain was difficult, but I finally agreed. She grabbed my arm and started to pull me toward the floor. I almost lost my balance and she shrieked and apologized. I laughed and told her that she has to be careful with an old man like me. We carefully wheeled our way onto the floor, and she turned backward. She put my hands on her hips as if we were at an eighth-grade dance. Her hip area was soft, and I couldn't stop thinking that my hands were just a short trip away from her incredible ass. My cock was near full throttle.

"I am supposed to skate backward, right?" I asked my 21-year-old babysitter.

"Do you know how to skate backward?" She smiled as she asked, which began to melt me.

Without answering, we rolled along. Lizzie was amazing on skates, and she skated backward with ease, all while towing along 200 pounds of nearly dead weight on wheels. Most of the floor was ours, as two couples had already bailed on the couples skate.

"Mr. Anderson, can I ask you a question?" Just as I was going to correct her, she added, "Paul. I'm sorry. I forgot."

"Sure, Lizzie. Is everything ok?" I was stunned by her question.

"You haven't had sex since Mrs. Anderson got sick, right?"

In the most cliché move of all-time, my balance failed me at that moment and I lost my footing. As I was accepting the inevitability of a hard landing, I forgot to let go of Lizzie, and she came crashing down with me. She fell across my midsection on her way to the ground, and I was pretty sure she brushed against my erect friend. Hearing her loud laughter was a reassuring sign that she wasn't hurt.

Before I could apologize, she said, "I knew you would react to that, but I didn't think you would tackle me!" I looked at her and laughed. Her sense of humor made her even more attractive, and I resisted the urge to kiss her right there, laying in a heap on the floor of a roller rink.

I had fantasized about this many times, albeit not with Lizzie. In my dream, I rented out a rink, and invited the hottest woman I could think of. We skated for a bit, then while I was trying to impress her, I fell hard. The woman got on the ground to check on me and I pulled her close for a kiss. We had wild sex on the floor, then got up and banged each other while skating around the rink. It played out many times in my head with actresses, singers, and even women I knew from the town... but never with Lizzie.

Yet, here I was; a 40-year-old widower at a roller rink with my 21-year-old babysitter right next to me, sprawled out with her tremendous ass commanding attention. If my kids weren't here, I might have made some kind of move. Thank God they were here.

"You want to make some kind of move on me right now, don't you?"

Holy Fuck. Was I thinking out loud?

"What? Lizzie..." My voice trailed off before I could answer. I didn't know how to answer her question anyway.

She jumped up onto her bright blue skates and held her hand out to help me up. I didn't need the assistance, but I took the free chance to touch her as I steadied myself. She looked up into my eyes, grabbed my engorged cock through my shorts for a split second, and whispered to me, "I know everything. Let's talk tonight."

I was frozen.

Marco came running out onto the rink in his bare feet, screaming, "Dad, are you ok?" Sarah skated after him, yelling that he had to put his skates back on to be out there. A security guard couldn't have done a better job.

This was a rare instance when I was glad I didn't have a Dirk Diggler 11-inch cock. It would have cut a hole in my shorts. We all skated (or ran) off the floor, and I announced it was time to go home. I made up a story about my ankle hurting, but the truth was I couldn't last another minute in this place.

We drove away from the Rollerama, my mind still racing to figure out what the hell had just happened. Lizzie carried on as if life didn't just get turned upside down for her. She joked around with the kids and asked me benign questions. The six-minute ride home seemed like 60, but we finally arrived at the Johnson house. I waited for Lizzie to get out of the car, but he looked at me quizzically.

"Aren't you going to work today, Mr. Anderson?" There it was again. That name. I know it's my name, but after what just happened, it sounded bizarre to hear it at that moment.

"Nah. I'm going to nurse this foot problem and just lay low today."

"You mean your ankle injury?" I had forgotten which body part I lied about.

"That's what I meant, Lizzie." The kids had no idea what was happening.

"Why don't I come over and help for the day? You don't want to be chasing these little monsters around on a bad ankle, do you?" Marco laughed at being called a monster. Lizzie turned around and flashed a smile at him. Her smile. Dear Lord.

Again, red flags be damned, I accepted her offer. I really wasn't planning on working because there was no chance I could focus. But now, I would be stuck to the couch to make sure I sold the injury to the kids.

"Do you want to put your skates in your house?"

"I'll bring them with. Maybe Sarah and I can skate around on the driveway. We can set you up in the garage with your leg up so you can hang out with us!"

While considering the level of torture this would be, my brain was trying to figure out what she meant when she said she knew everything.