Jesse and I had known each other since diaper days. Her mom, who I called Aunt Pat, was my day care provider when my Mom went back to work. Aunt Pat was also my god mother and spent more time mothering me than my mom. Jesse and I played together every day. When it was time for us to begin school, I walked her to and from school every day.
That was until Jesse began developing into the beautiful woman she would become. I stopped by to pick her up halfway through our freshman year and Aunt Pat told me some boy had given her a ride to school. Her mom was pissed that she didn't tell me. There were days when one of us were sick, but this was the first time I walked to school by myself because Jesse wanted to go with someone else. She was so sweet and loving when she saw me come in and apologized for forgetting to tell me. Then she walked away with some football jock.
Her mom saw me walking home by myself, well actually my mother insisted I check in with Aunt Pat on my way home.
"Jack," she said, "you need to start distancing yourself from Jesse. She's beautiful on the outside but ugly on the inside. I hate to talk about my daughter this way but she's fucking evil."
And that's when I started distancing myself from Jesse. We lived in a small town, attended many of the same classes, and parties but I knew she had no compassion for my feelings or probably anyone's feelings. She went through boyfriends like I went through underwear. I don't know if she was having sex with any of them, but she had the reputation of being a dick tease, which I would learn firsthand.
We happened to both end up at a backyard bonfire in our senior year, I had brought an outdoor chair as the host recommended. Jesse ended up sitting on my lap. Jesse was one of the most beautiful girls in my school and she was sitting in my lap, wiggling her ass on my hardening cock. She had to feel my erection building. That was bad enough, but she kept rubbing those wonderful tits in my face. She kept bringing her face to mine to say something privately. Her lips were so close to mine I tried to kiss her.
Our lips actually touched before Jesse shouted out loudly, "Eww Jack, that would be like kissing my brother."
I stood up quickly, dropping Jesse onto the ground and left with my chair.
Aunt Pat was knocking on my door the next morning, I invited her in as my mom was at work.
"Jack, did you try and kiss Jesse last night," she asked. I wondered what was worse, the embarrassment of Jesse's exclamation last night or being grilled by her mother. I nodded yes.
"And did you standup knocking her to the ground?" Fuck I thought and nodded yes.
"Jack, she got exactly what she deserved, and I told her the same thing. There's an evil streak in that girl that came with puberty. Please Jack, I love you like my own son, stay away from her."
She gave me a big momma bear hug which made me feel so much better.
After graduation, Jesse and I went off to different colleges. We would occasionally run into each other while home for holidays. I was studying accounting and spent my summers interning at different firms. A local firm made me a generous offer before I started my senior year. I had developed a knack for writing small pieces of software to automate routine accounting tasks. I would not be a millionaire, but my future looked bright. I needed to wear shades as the old song went.
Jesse returned to our hometown, and she got a job as a nurse at the local hospital. We would cross paths occasionally, do the polite chit chat shit and then go our separate ways. I joined a darts league in my area and played three or four nights a week at local pubs. Jesse and I would frequently cross paths during the matches.
Supposedly, she was fucking her way through all the doctors at the hospital, married or not. I followed my Aunt's advice and kept my distance. Jesse always engaged me, and I kept my answers short.
My own love life was doing okay. Most accounting offices were usually evenly split between male and female. My job frequently required me to visit my firm's clients so there were always new pretty faces. I'm not saying I dated a lot, but I considered my dates high quality, something headed long term and not a one night stand.
Alice was probably the longest term woman I dated. There were more feminine type soaps and shampoos in my bathroom than mine. She was my plus one at Jesse's wedding. Alice was in awe of Jesse's beauty.
"Fuck," she said, "is she my competition or am I safe now that she's off the market."
"Everything you just said is wrong Allice, Jesse is an evil witch who had ripped more men's hearts out that I can count. Usually involving public humiliation. Ask her mother. And Jesse will never take herself off the market."
"You told me her mother was your day care provider; did you guys ever mix it up?"
I gave her the bonfire story.
Jesse and her husband came over to chat. As they were leaving, Jesse said she wanted a dance later. I told her Allice had filled my dance card that night.
Alice and I got along really well, at least that's what I thought until I came home one night a few months after the wedding and most of her stuff was in cardboard boxes shoved into her car.
"Are you breaking up with me Alice?"
"Yes, I am Jack. But I'm sure you won't mourn our ending. You might not love Jesse, but you've seen and experienced the pain falling in love with her can cause. And you're never going to let it happen to you again. So, you'll never really love me as much as I love you. You'll say the right things and do the right things, but you'll never let me in. And that's what true love is Jack, opening up yourself to someone, even though it might end in catastrophic damage, because you love someone that much to take that risk. You don't love me that much and I don't think you ever will."
She got up and left, part of me wanted to chase after her, part of me knew she was right. We were still friendly; I had to visit her office a couple times a month until I found out that she left for another company.
It was about a year after Jesse's marriage that I found her and her luggage sitting on my front steps.
"It's been a while Jesse, what's up," I asked.
"My husband threw me out and I have no place to go, can I stay here for a while? I heard you and Alice split up."
"Were you cheating on your husband Jesse?"
"That's not important right now Jack, can I stay?"
"What about your mother Jesse?"
Jesse stared at the ground, her lip quivering. Normally so confident, maybe the real Jesse was breaking through, unlikely I thought.
"She said no Jack, my mother said no."
"Two things Jesse, I want a firm end date, and no men in my house. You're a guest, not a roommate."
"How long will you let me stay Jack, I need at least two weeks to find a new place."
"Two weeks it is Jesse, let me help you with your bags."
Jesse didn't tell me that she cheated on the husband doctor with another doctor who was married causing an uproar in the hospital. Jesse was suspended without pay for two weeks for violating hospital policy.
She needed a computer to use so I set her up with a separate ID, it was a pretty high end computer with three large screens and other stuff I used to write my programs. I also installed a key tracker and other spyware on her ID. Jesse was usually out most nights, frequently not coming home until after I went to work the following day. Within the first week, I had access to all her financial accounts, emails, documents and pictures. I spent a couple of nights jacking off to photos and videos of Jesse performing various sex acts with different men and women and sometimes with both. In the end, she was a beautiful woman. All that shit I downloaded to my space on the dark web.
Financially, Jesse was a mess. Her credit cards were all past due, and her credit score was in freefall. I didn't know how she was going get an apartment with her that credit score. I went through her emails. There were several where she ridiculed me to her friends, calling me her puppy dog who would do anything for her. I don't think so bitch.
Her emails also revealed her upcoming divorce was in trouble. Jesse was asking for the world, and her husband was waving the prenup in the air. He was having difficulty supporting his claim that she was unfaithful. I found a video of her and the doctor she had the affair with, and I sent it to doctor husband and the cheaters wife, using Jesse's old email account.
Jesse was crying on my couch when I came home the next day, which was two days after she was supposed to move out.
"What's up Jesse?"
"My divorce is tanking, somebody sent my husband a video of me and my lover together, now he can exercise the prenup. I stand to gain nothing when the divorce is finalized."
"I'm sorry to hear that Jesse, but how does that effect you moving out which was supposed to happen last weekend?"
"I just don't have the money now Jack, I just went back to work today, and it will be at least a month before I have enough money for rent and a security deposit. Please Jack, for old time's sake, you have to give me more time or maybe you can lend me the money to move out."
"The only reason I let you stay here was for old time's sake. You've used that up and I'm not going to lend you any money."
"Just a month Jack, please."
"No Jesse, go see one of your lovers, not your puppy dog." Jesse missed the puppy dog comment.
"I've tried my lovers Jack, none of them want anything to do with me. I've fucked too many of them over or they're aware of how many men I've fucked over. I spent the day on the phone, it was the most humiliating day of my life. They were mean to me Jack, downright mean."
"I'll give you to Friday Jesse. That will be three weeks, if you're not out, you'll find your stuff on the curb." I got up and headed to the pub for a dart match.
I checked Jesse's emails the next day. People were being mean to her, most just told her to fuck off. Some reminded her of the humiliation she inflicted on them. My favorite was the one telling her friend that I wasn't caving to her like I always did. and she was afraid I would follow through with my threat.
Jesse was crying on the couch when I came home on Thursday, obviously not ready to move out.
"Please Jack, I need more time."
"Not happening Jesse. Come on, I'll help you pack."
She dropped to her knees, "Please Jack, I'll do anything."
"Seeing you on your knees gives me an idea." I started pulling down my zipper.
"You have to be kidding Jack; you're like my brother."
"Yes, you've told me that before in front of all our friends. Oh, I want you to strip first, it's been a long time since we shared a bath."
"I can't do that."
"What, the strip part or the sucking my dick part because I've heard you're pretty good at both."
She was still on her knees when I started pulling her luggage out of the hall closet.
"Fine Jack, you win. If I suck you off, how long do I get to stay?"
"Sunday at noon Jesse."
"That's like two days, my blowjobs are worth more than that."
"You are not in a position to negotiate Jesse. And just to set expectations here, every two days will require escalating sex acts to extend an additional two days."
