Chapter 9: The Past Is In The Past

Author’s note: Those of you who, like me, have fallen in love with Jessica (and Katelyn and Alex) deserve a warning that this chapter contains some violent and painful backstory. Jessica’s life has not been easy, and not all the men she has come into contact with have been as caring as Alex is. Reader discretion is therefore advised.

December 27. The first ‘normal’ day after the holidays. I woke up, as usual, at around 7:00. For some reason, I can’t sleep in, no matter how hard I try. Jess was pressed up close against me, and a quick look over her shoulder confirmed that Kate had indeed joined us at some point during the night. Unlike yesterday morning, I wasn’t surprised or worried by that. Or at least, I wasn’t, until I realized that I hadn’t put on boxers last night before we fell asleep. I was nude, and in bed with my girlfriend’s sister. This wasn’t good, even if my girlfriend was lying in between us.

Before I could worry too much about that, Jess woke up. She flipped onto her back, and Kate rolled over to give her a hug. Jess then kissed me, and her hand roamed down my side. When she realized I was naked, her eyes went big. I nodded, to let her know that I had figured it out already.

“Coffee, Kate?”

“Coming right up.”

Kate swung her legs out of bed and headed for the bathroom. She hadn’t noticed. Note to self: no matter how good the sex is at bedtime, remember to pull shorts on before falling asleep!

Jess followed Kate to the bathroom, and I went last, pulling on my shorts. I left it at that - I figured if the girls were going to be dressed in t-shirts and panties, I was fine in boxers. Neither girl commented when I got to the diningroom, though both gave me appreciative looks. It made me feel kind of good, to get checked out by two hot girls at the same time. We sat and drank coffee, then had some cereal. Then it was time to cycle through the shower. I let the girls go first, and they went into the bathroom together. I guess they needed some sister time. When they were done, I went in and shaved and showered. When I came out, they were in the bedroom, chatting. I went to the livingroom and booted up my laptop to check email.

A few minutes later, both girls joined me so we could discuss the day. Kate said she was going over to her friend Tami’s place to work on a joint project that was due early in January, and that she wouldn’t be home till after supper. They wanted to get some good work done on it while school was out, and Tami was going to visit her grandparents over New Year’s. Katelyn had fallen behind in some classes in grades nine and ten, and the result was that it would take her five years to finish high school, rather than the usual four. Jess didn’t have to be at work until 4:00. I was hoping to return the rental car and then pick up my own car late in the afternoon.

I also had some bad news. One of the emails I had received was from the accounting firm that was winding up the company for us, telling me that they needed a meeting with me before the end of the year. So it looked like I had to make a quick trip to Ottawa. It was just as well, I thought, as I needed some clothes and I had some personal financial things to take care of as well, but it would mean being away from the girls for a couple of days. I said that if the car was done today, I’d plan to go there the next day, and come back on the 30th, or on the morning of the 31st at the latest. Jess gave me a funny look as I shared this news with them, but didn’t say anything. In fact, both girls took the idea of us being apart for a few days better than I had thought they might.

Kate left, then, with her antiquated laptop, and headed for Tami’s. I offered to give her a ride, but she said the walk would help get her ready to focus on their assignment when she got there. Jess made a fresh pot of coffee, and poured us each a cup, and we sat at the dining table together.

“I have a favour to ask you,” she said, once we were settled.

“Ask away.”

“Would you consider taking Kate to Ottawa with you when you go?”

Alarm bells started going off in my head.

“I don’t think that’s a good idea, Jess. Her flirting is getting to me as it is, and I just don’t think I could handle being alone with her for that length of time. I’m not sure I could control myself, if you weren’t around to keep an eye on us.”

Jess took a gulp of coffee. “You wouldn’t have to worry about controlling yourself.” There was an awkward pause. “You know Kate’s a virgin, right? Well, she doesn’t want to be a virgin anymore. And she asked me this morning if I thought you might be willing help her out with that.”

Complete silence fell over the apartment. I didn’t know what to say. Was this a trap? Did I just hear right? Did Jess just say that she wanted me to take her sister to Ottawa with me, and that they were both expecting me to have sex with her while we were gone? Surely not.

“Sweetheart,” I said finally, “did you just ask me to take your 17-year-old sister away for a few days? And did you just tell me that you wanted me to take her virginity while we were gone?”

“No,” Jess said quickly. “I asked you to take my sister away for a few days, and I told you that she wanted you to take her virginity. It was her idea, not mine. I just added the part about taking her to Ottawa, because I thought the trip might be fun for both of you if she went along. And in any case, you can’t pretend you’re not interested in her - you’ve admitted to me that she turns you on.”

I still wasn’t sure what was happening.

“Ok, so I can’t deny she’s hot, and I can’t deny I’ve ogled her from time to time, and I can’t deny that the physical stuff she’s done with me has gotten me worked up. And ok, so it was her idea. But you’re saying you’re alright with it? You don’t mind me going off and having sex with your little sister?”

“It’s ok, really - I don’t mind. I want her to have sex for the first time with a good lover, and you are the best lover I’ve ever met.”

My mind was whirling. What was happening here?

“You may hate me for asking this, but I have to. Can you honestly tell me that this is just about Kate’s wish to lose it? You’re not trying to sacrifice your sexy little sister to me because you’re afraid that if you mess up, I might get bored and wander off and leave you?”

Jessica’s eyes flashed with anger, and she leaned very close to me, pointing her finger at my face to punctuate her words. “You need to learn one thing about me, buster, that I thought you would know by now. I would never sacrifice my sister for anything. You are the best thing that has happened to me in a long time, and I would hate to lose you. But if keeping you somehow required me to sacrifice my sister, as you put it, I would kiss your ass goodbye in a heartbeat. This is about Katie, not about you and me.”

I leaned over and kissed her, gently, on the forehead. “I’m sorry,” I said. “I didn’t mean to hurt you. But I needed to know. We’ve all heard of cases where the girlfriend gets insecure, and decides she has to do something drastic to make sure that the boyfriend doesn’t seek greener pastures. Sometimes the boyfriend even asks for it. Little sister, daughter, best friend, whatever. ‘If you really loved me, you’d let me have her.’ And I would never ask you to do that.

“I believe you when you say that is not what you are thinking, but I have to admit that I am still confused. You really want me to take your little sister off for a few days away from you and have sex with her?”

“Let me tell you a story,” Jessica said, “about my sex life before you came along. You’ve never asked me about my experience, although you know I wasn’t a virgin when we met.”

“Neither was I,” I interrupted. “And I don’t need to know about your experience.”

“But I need to tell you about it,” she said firmly, “because it might help you understand why I am asking you to do this for Katelyn.”

She took a deep breath. “I had sex with three guys before you. Well, four, really - I’m not sure if the first one counts. My first boyfriend was a guy named Kyle. We went out every weekend - to the movies and the mall and stuff like that. Nothing fancy. Once in a while his parents would go out, and we would go to his place and goof around. We never actually went all the way, but he was the first guy I ever saw naked, and the first guy I ever let see me naked. We touched each other everywhere, and I sucked him off whenever we had the chance, and he used his fingers - but never his mouth - on me. We likely would have gone all the way, eventually, but his family moved away - his dad got transferred, and it all happened very quickly. I was heartbroken - I thought he was the only guy in the world.”

She paused for breath. “I’m sorry,” I said.

“Don’t be,” Jessica replied. “Neither one of us had any idea what love was. Still, until you came along, he was the nicest guy I ever fooled around with.”

She paused again. “I lost my virginity that summer. There was this guy, Todd. He was older. He was halfway through university. He had a car and everything. I was so flattered that he was paying attention to me, out of all the girls he could have had.” She sighed. “I was so naive. He asked me to go out with him, and I agreed. We went to a party, and then he suggested we go for a drive. He went up to this park down by the lake, and we pulled into a parking lot that was all surrounded with trees. We moved to the backseat and started to make out a bit, and I’m thinking ‘Wow, Jessie! You’re kissing a university student!’ Before long he had my shirt off and my bra undone, and soon after that he pulled my skirt up. I let him take my panties off, and he stuck his fingers up inside me, and told me how tight I was. I said I was a virgin. He said that he had hoped I would be. Then he asked if I wanted to have sex with him.

“It was stupid, I know, but I thought I was in love with him and I thought he was in love with me too. And I believed that if I didn’t give him what he wanted, he would have lots of chances to find someone who would. So I said yes. He got me to unzip his pants and pull them down, and then pull his jockeys down and take out his cock. He told me to suck it. I didn’t mind that - I’d done it before for Kyle, and if I am honest, I kind of liked doing it for him. So I got Todd nice and hard, and then he put me down on my back on the carseat, with my legs stuck up in the air, and he got on top, and he pushed it in. It hurt. I think it was the position I was in, partly, and partly how fast he shoved it in me. I just lay there, thinking it would feel better soon, and it actually did start to feel ok after a bit. I think I even came, just a little one, as he spurted inside me. My first thought when I felt him coming was ‘What if he makes me pregnant?’ I hadn’t thought of that before. My second thought was ‘This will feel even better next time.’

“But there wasn’t a next time. Not with Todd, anyway. He pulled out, and took my panties, and wiped his cock off with them, and then used them to clean me up a bit too. Then he pulled up his shorts and his pants, and told me to get dressed. We moved back to the front seat, and he drove me home, and when we got to my place he gave me a kiss and said ‘Thanks for helping me out.’ I had no idea what he meant. I guess I thought he meant by giving him sex. He said he would call, and I went inside and dreamt of getting married once school was done. He had kept my panties, and I imagined him with them under his pillow, so he could fall asleep while he was thinking of me.

“I called him a few times that week, but he never answered his cell phone. I was miserable. And then one day I ran into his little sister on the street. She was a year younger than me. I asked her if he was ok.

“And she laughed at me. Said he had wondered how long it would take for me to get the hint. He didn’t love me at all. He didn’t really even want to have sex with me, or at least not with me in particular. He was in some group at school, and they had a contest over the summer. The idea was to see how many girls each guy could sleep with in four months. It didn’t count unless you got to keep her panties, and could show the come on them.”

She paused again, and her voice broke a bit. “I counted double, because I was a virgin, and the come stains had some pinkness to them to prove it.”

Silence fell for a moment, and then I stood up and walked to her side of the table, and reached out to rub her shoulder. She stood and turned into my arms, and I held her for a moment. “You don’t need to tell me all this,” I said. “I don’t care who you’ve been with. I only care that you are with me now. I love you.”

“I know,” she said. “But I need to tell you. Come to the couch with me - hold me! - please? And just listen.”

How could I refuse? So we moved to the couch, and I sat down at one end, and Jessica snuggled up against me, leaning on my shoulder, with my arm around her. She took a deep breath, and continued.

“Number two was even worse, in some ways. It was just after Mom died. I had finished school, and we were almost out of money, and I needed to get a job so that I could support us. I was working part-time at the grocery store, but that wasn’t enough. So I decided to try waitressing. There was this place on the main drag that had a sign in the window, saying they wanted waitresses. So I dressed up in a skirt and heels and went in to drop off my resume.

“There was this guy behind the bar, and he asked what I wanted. I said I was applying for the job. He took my resume, and glanced at it, then looked me over. He said he could interview me right away if I wanted. I said sure, and he led me into this office space at the back of the place. He motioned me to sit in a chair by the desk, and he sat on the desk in front of me. He looked at me for a minute, with this funny look in his eyes, and then he said that he had to be honest with me, that they had already done some interviews and they had found this girl that they had pretty much decided to hire. But if I was willing to work hard at it, he might give me a chance to change his mind.