It was Christmas Eve the first time Cara and I had sex. A week earlier, she had walked in on me masturbating. Instead of turning around, she’d gotten curious and decided to lend a hand. After that night, we continued to tease and tempt one another. Fucking one another was inevitable.
There were a thousand reasons to worry about the future. I knew what was happening between us was more than just impulsive fun. Cara and I were drawn to one another. That came with challenges.
I was a junior attending college in another city, and she was still in high school and living at home. She was also my aunt’s stepdaughter. We’d practically grown up together. Nobody in our family would approve of us together. I couldn’t just call up and ask her on a date or drop by to hang out.
Instead of worrying, I was surprisingly relaxed. Before we fucked, I was worried that she was just curious or even bored and I was a distraction. I thought about her constantly and longed to be with her, but I didn’t know if she felt the same way.
My concern dissipated after we fucked. I was certain we were on the same page. I knew we would find a way to keep things going, even though it was going to be tricky.
I woke up Christmas morning knowing that we wouldn’t have a chance to fool around. The hustle of holiday preparation was over and now it was time to relax with our family. I didn’t feel the kind of anxiety I had all week about when we might be alone again. I knew it would happen at some point because we both wanted it.
We spent most of the day in the same room together with our parents and siblings and my grandmother. Cara did her best to keep her eyes off me, at least as far as I could tell. I had a harder time not staring at her. Even in a simple red sweater and corduroy skirt, she looked amazing.
Late in the day, after dinner, I went to the restroom and came out to find Cara waiting. Nobody else was around. She leaned in and kissed me on the lips.
“Hey, remember last night when we fucked?” she asked playfully.
I smiled and nodded.
“Of course.”
“Good,” she said. “That was really fun. Let’s do it again soon.”
She grabbed my hand.
“I thought you might like a gift,” she said.
She stuffed a pair of damp red panties into my palm.
“I took them off while I was waiting.”
I glanced down at her conservative, knee-length skirt.
Cara nodded.
“Think about that the rest of the day,” she said. “And when you jack off later. Think about me with no panties under my skirt. And how wet those were when I gave them to you.”
For the rest of the evening, Cara would cross her legs every time our eyes met. It was subtle, so nobody else could tell. It made my dick ache for her.
Later that night, lying in bed alone I wrapped her silky, damp panties around my cock and thought about how it felt to be inside her pussy. I pictured her riding me with her big tits bouncing in my face. I remembered the way she moaned my name when she climaxed. My balls clenched and I unloaded into her panties.
The next day, everyone left to go home. I wasn’t sure how I was going to contact Cara once we left. The best option would be to go by her house to hang out with her brother and hope we got a few minutes alone. Luckily, she had a better plan. While I was packing, she came to my room and slipped me a note on a piece of paper.
“I have an instant messenger account and webmail,” she said. “I don’t check it much, but I will now. We can make plans.”
I was surprised she even had an email account. I had one through my school, but not a lot of people were using email back in 1998. My parents didn’t have email yet and a lot of my friends from high school rarely checked their messages. I told her I would email as soon as I got home.
Our first few exchanges were chaste and overly formal. This was a decade before people were used to informally writing one another. We didn’t flirt or tease one another by email. It was small talk and comments about we both looked forward to seeing one another.
The chat sessions were a little more flirty. My personal computer was back at school, so I had to log on to the family computer several times a day and try to catch Cara online. There was a chance that someone could walk in on either of us at any time, so we couldn’t really engage in dirty talk. Neither of us wanted to quickly hide a chat window or stop masturbating when a parent or sibling walked in.
“I have a silly request,” she typed one night.
It had been almost a week since we fucked. I thought about it every night. She told me she’d done the same while touching herself.
“You can request anything,” I told her.
“It’s silly,” Cara wrote. “Considering we’ve already had sex. And we’ve done other things. But I want the next time to be special.”
“Special how?”
“I’ve never spent the night with man,” she wrote. “I’ve only been with one guy and it was always rushed. And it wasn’t meaningful. I want it to be romantic. Is that wrong? You can tell me I’m wrong.”
“You’re not wrong,” I told her. “I would love to spend the night with you.”
It wasn’t just the idea of having sex all night that appealed to me. I knew there was something going on between us that deserved to be nurtured. It was more than just the taboo that appealed to me.
“Can you get away all night?” she asked.
“Of course I can,” I said. “I can just say I’m going to visit some friends from school. Can you get away?”
“Yes,” she told me. “I was thinking about New Year’s Eve. I can tell my parents I’m staying with a girl from school. Is that weird? Would you rather be out celebrating with your friends?”
“There is nobody I would rather be with,” I wrote honestly.
My heart was starting to race. I was eager to see Cara again and find out where a night together might lead. My cock got hard just thinking about it.
“There is nobody at home right now except me,” she wrote. “Do you want to call me?”
I told her that I would. I grabbed the cordless phone and took it to my bedroom and locked the door. My father was at work and my sister was out with her friends, but my mother was home and doing chores around the house.
I called Cara’s house and she answered on the first ring.
“Where are you?” I asked.
“I’m in my bedroom with the door locked. What about you?”
“The same.”
“We have a New Year’s Eve concert at school,” Cara said. “It’s pretty much like any other concert. Only parents and family show up. Maybe a few friends.”