Jessie’s Sister, Jill

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“I told Jill she could kiss you…” My fiancee, Jessie, had just told me she wanted me to kiss her little sister.

“Isn’t that a bit contrived? Should I kiss her during a game of spin-the-bottle?” She didn’t like that, she was being serious.

“I see it as you take her for ice cream when the Sun’s going down, and sit with her on a bench and as it’s just getting tough to see you give her a nice kiss, no tongue…maybe a touch of tongue.” Jessie was always particular about the way things should be done, but this was surreal.

“She didn’t think you were patronizing? I know she must of been absolutely embarrassed when you suggested it.” She frowned and pinched my arm. I kind of hoped she’d drop it and go in her house and go to bed.

“Well, that’s the problem, isn’t it? She’s the shyest girl of all time and she’s twenty and has never had a boy kiss her for real. All I’ve told her is that it’s alright if she kisses you.”

“How would this be a ‘real’ kiss, you’ve planned it all out for her?” The real issue was eternally unspoken. She wanted me to kiss her sister because she thought Jill would get too sick or even die before she got the chance to find the right guy to kiss.

Most of Jill’s shyness stemmed from her disease, cystic fibrosis, but it was more of Jessie’s fear that half of her sister’s life was over at twenty, and that she had a better chance of dying in her twenties than not. I understood what she wanted, but didn’t think her first-kiss plan was best.

“You love her right? She’s had the biggest crush on you since she was twelve. It wouldn’t be some erotic thing, it’d just be a nice kiss from the only boy she trusts and most likely fantasizes about.”

“Jess, I’m too old for her–she should be kissing another twenty-year-old who has absolutely no experience with females. It’s better when it’s awkward.” Jessie stuck her tongue in my ear and rubbed my inner thigh with her hand. I eventually agreed to consider her proposition, mainly because she pushed her gorgeous cleavage into my chest in such a mind-numbingly erotic way.


I’d forgotten the kiss proposal, and Jessie hadn’t mentioned it for weeks when I was alone with her sister, Jill, in their living room one evening in early June. Jessie was supposed to be home from work around eight and I’d driven Jill home from her cashier’s job around six, so I didn’t bother going back to my house.

We watched consecutive episodes of her favorite show, a kid’s horror series, and she asked me if I wanted ice cream. It was the first nice night after a week of rain so I thought of going out for a bit.

“Wanna go get ice cream at the stand out in Drake instead?” It was about twenty-five minutes drive, but it was very good, her sister’s favorite anyway. She paused the DVD, thought about it for a second then hopped up off the couch.

“Ok, let me change.” She returned in a light sweater and shorts. She looked so different than her sister, she was barely five foot, had straight dark hair, her breasts were the butt of many training-bra jokes, ‘though her ass was shapely similar to Jessie’s, and she was as cute as she was shy.

She had her girlfriends, but I was pretty sure that I was the only guy close to her age that she’d ever had a serious conversation with. I had a brotherly fondness for her for as long as I’d known her. I’d started dating her sister in high school and as I got closer to Jess I’d gotten closer to Jill.

The fact that Jill’s illness could accelerate and she could be dead in a matter of weeks to months from some basic infection broke my heart. She was the sweetest girl I’d ever met and her shyness just made me feel more sorry for her. I initially experienced all of it through Jessie, but as time passed Jill became more and more comfortable with me and it just magnified those earlier feelings of pity.

I knew how to help her put her special vest on that shook the mucus from the walls of her lungs, and had spent hours pounding her fragile body in the old way–when she’d trusted me enough to let me see her sick. It had initially been sympathy for my girlfriend who experienced her sister’s illness in such a heavy way, but as I got to know Jill my feelings became more centered on her.

“Can I drive, Danny?” She’d finally gotten her learner’s permit that winter and had taken drivers-ed but hesitated to go for the driving test. I gave her my keys. Her smile was adorable. We were off, she drove with a foot on each pedal, left on brake, right on gas.

“It seems like you’re getting better at this, when you gonna go get your license?”

“Not too soon, eventually I guess… If I get my license you won’t have any reason to come over when Jessie’s at work.” She blushed. God, everything she felt you could read by the different shades of pink on her cheeks.

“That’s not true. Besides, if you had your license you could drive to my house anytime you wanted to hang out, or take me to a drive-in movie. You couldn’t do that now, could Kartal Escort you?” Flirting with her was fun but usually short lived, she’d just get too embarrassed and it felt like you were torturing her. The pink on her cheek turned pinker, not quite red yet.

“There aren’t any drive-ins around here, Danny.” She giggled, so amazingly girlish.

“Then where do you go with all your boyfriends on Thursday nights?” She had various doctors’ appointments, usually on Thursday’s because that was the night her mother didn’t work. Jessie and I had a running joke for years about who she was dating that Thursday.

We’d talk about her going to some pancreatic specialist as if he were some hot new guy in school–how he’d stack up against the kidney specialist, where he’d take her, a whole assortment of personality traits and illicit plots that we’d tease her with.

“I don’t have any boyfriends, Danny.” She was flush now, I figured I shouldn’t make her too nervous, she might crash the car or something.

“Well, when you do I hope you torture them as much as your sister tortures me.” We were quiet for the last few minutes of the drive, finally arriving at the soft-serve stand in the middle of nowhere.

“Jilly, you want a Slushie too?” She shook her head. She got apple flavored ice cream, I think I got banana, but I was more interested in the cherry Slushie. We sat down at the picnic table, only then did I remember my future wife’s little ploy to get Jill her first kiss. I shivered. I thought about it for a minute, but it didn’t seem like it’d go over well, she might enjoy it but then we’d both be too embarrassed.

I watched her eat her ice cream, it wasn’t sensual, just reminded me of how a kid eats an ice cream cone. Her hair was in a pony tail, she wore beige shorts with a little stain from her ice cream and white socks and tennis shoes. She was cute enough to kiss, smiled enough at me, maybe I could kiss her…

“Want some of my Slushie?” She’d finished her cone and looked at me while she sucked on my ice drink. A minute later the coughing ensued, but only for a couple minutes, short coughs, no wheezing, too much cold. I put my arm around her.

“You’re cold, wanna go home?” Hugging her and picking her up and carrying her around and wrapping her in blankets were all things I’d done before under the guise of fun, but this was the first time I’d done so while feeling attracted to her.

“In a little while. Jessie isn’t home yet, the sun isn’t down all the way.” She took the melting ice cream cone I’d neglected and licked it. It left a trail just to the right of her mouth.

“You ice cream thief…” She looked at me funny, her eyes were big and round, I impulsively licked the little bit of ice cream from her cheek. Her eyes got wider, surprised, then her face flushed, but it was mostly desire this time. I kissed her full on the mouth, she kissed me back, it only lasted a second or two, but it was a genuine kiss. I guess Jessie was right. To my surprise Jill reached her left hand behind my neck and kissed me back. This time the kiss lasted and we touched tongues for a very heady instant. She pulled back, a little put off by her own forwardness.

“That was nice, Jilly, let’s go.” I grabbed her hand and lead her to the car before she could process much of what happened. I drove home, she didn’t say anything on the way home, just smiled and nodded when I tried to act casual about a strange happening at an ice cream stand. As far as I could tell she liked it. I guess I’d have to let Jessie find out for sure.


I didn’t have to wait long for the report on Jill’s impression of our kiss. The next night Jessie came over and was giddier than usual.

“Danny, she told me all about it. It was so cute, she was worried about how I’d feel about it and said she wouldn’t talk about it if I didn’t want to. Of course I dragged every last detail out of her. She said it was great and said it was like electric and how she grabbed you and kissed you back.” Jessie jumped me on the couch, she kissed me and straddled my thighs.

“You’re such a good boy, you don’t even know how much I love you for being so sweet to my sister.” We made out for a few minutes.

“I think I have an idea.”

“Oh, you’ve no idea.” She ravished me. I felt like I a 19th century virgin on her wedding night.


The summer went by fast, it was the day before Labour Day and I was at Jessie’s. Jill had been in the hospital for a week in July with a bad lung infection. Things never really got awkward with the whole kiss thing, and I spent time with her alone but there was no more kissing.

The desire was there for me at times and it was evident on her face plenty, but it never came down to a kiss. However, she was openly infatuated… She’d want to do things for me, like wash clothes I left at her house, she made me pies on my birthday and for my Fourth of July BBQ, mostly little things. She wasn’t really nervous around me at all Yakacık Escort anymore.

I was with Jessie on her bed, when she made her second, and more astounding proposal.

“She ‘loves you’ loves you. Would you sleep with her?” I wasn’t sure what she meant. Was she jealous of her little sister’s crush on me?

“We’re getting married in December, why would I wanna ruin that?”

“You know, every time she gets sick, I get unbearably nervous and think she might go away. I just want her to experience as much as possible, you know?” Evidently she wasn’t jealous, she was asking me to think about having sex with her little sister. I didn’t say anything immediately so she continued:

“Aren’t you attracted to her? You’re gonna say, ‘she’s like a sister’ but I’m just talking about if you’re attracted to her at all.”

“You’re not serious, you’re talking about me having sex with Jilly just so she can have sex…I don’t think you understand how silly this is, she could live ’til she’s fifty. There’s no reason to think she’s gonna die next week or next year…really, we could die in a car accident and she can get married and have kids.”

She had that look on her face, that heartbroken ‘I love my dying sister’ insane look, the place where rational discourse would always lose out to emotion.

“Danny, you know her, she isn’t going to let some guy fall in love with her if she’s sure she’s gonna die before she’s thirty. She loves you by accident. You were here when she first thought about boys as boyfriends and husbands, and became her friend when she started feeling things for boys…realistically you’re the only meaningful male she’s ever had in her life. Plus, you love her like I do.” Now she was getting super psychological.

“Jessie, she’s an adult, she isn’t going to have sex with her sister’s future husband–especially if she knows her sister’s arranging it. This isn’t as harmless as a kiss.” …And it’s actually insulting that you think of her as a helpless little girl who needs her big sister to pimp her boyfriend out as to let her experience life. Of course I kept that last bit to myself. No need to wake up sans testes.

“Well, let her make the decision. If you think I’ve created her desire for you, you won’t think it’s morally wrong to let her decide. You’re attracted to her, I’m not going to hold that against you no matter what–in fact you’ll be a saint in my eyes if it’s a good experience for her.” I mulled it over, this was the sort of thing she’d hold against me even after we we’re married. She’ll still prod me to sleep with her sister just because she’d still be on the verge of never experiencing someone ‘penetrating’ her?

“There doesn’t have to be a lot of thought put behind it, Dan. I’ve talked to her enough about you that I know where she stands. We both know it would only be between the three of us, sharing something for a brief time. It’s as simple as you taking her to the fair tomorrow then taking her home with you. I have to work all day then all night, just take her home with you and be gentle with her then I’ll pick her up in the morning.

She loves the fireworks, if it’s warm enough she’d absolutely love laying outside on a blanket and watching the fireworks and have you hold her. Jesus, Danny, it doesn’t even have to be sex. Just hold her and kiss her and make her feel good, you make her feel good about herself like me and Mom could never…”

“Jessie, I get it, I love you, even if I think you’re a little off on this one. Tell her I wanna go to the carnival and that I’ll pick her up if she wants to go. If we go back to my house I can pretty much guarantee it’s not going to be anything more mundane than watching the fireworks or TV.” Finally, she was placated and let the night get on.


I picked Jilly up for the carnival around seven. She wore a flimsy white skirt, yellow tank top and the same white tennis shoes, no socks this time. Her dark hair was straight and down her back, a little braid down the right side of her face. She wore more make-up than usual, not too much, but her lips were shiny. It was clear to me that I’d developed a little crush on her over the past few months.

“You go to a BBQ today, Jill?”

“Yeah, at our Aunt Jodie’s house. Did you?”

“Yeah, went to my grandma’s.” We didn’t say much on the ride into town to the park where the yearly carnival was held. We parked and walked around and looked at everything for a while.

“You wanna play a game or go on a ride?” She just nodded. We played the typical darts and balls and goldfish type games. We ate hot dogs and popcorn. It was all very fair-ground type stuff.

“Sit with me on the ferris wheel?” She shook her head.

“You don’t wanna sit with me?” Her face flushed.

“I don’t like it when it stops at the top.”

“I won’t let you fall out. Please go with me.” I insisted and she relented, we waited in line for a bit. Finally got a spot on the ferris wheel. She sat against Kadıköy Escort me in the seat, I put my arm over her shoulders. She smelled nice. As we got higher she tensed more, but eventually lay her head on my shoulder.

“You look very pretty on a ferris wheel.” She looked up at me ready for a kiss, but that wasn’t quite my intention.

“Thanks, Danny.” I guess the ferris wheel’s purpose had been to initiate a comfort with close contact, because when we got off she walked right up against me and it was easy to put my arm around her waist. They started closing down the rides, as the fireworks display wasn’t an hour away.

“You wanna stay here and watch the fireworks or go home or go somewhere else?”

“Your house has the best view, can I come over?” Oh boy, it couldn’t have been closer to Jessie’s plan had Jessie been on a live-feed in our ears. My house did have a great unimpeded view, very little light pollution and no one else around at all.

I bought a house just outside town the year I started working full-time after college. I loved how country it felt out there, yet it wasn’t far from town. Jessie had helped me pick out the house but she’d resisted every suggestion of moving in. She felt like she’d be abandoning her sister and all. Co-dependent or not, I knew I was going to marry Jessie and had already accepted all her baggage years before.

“Yeah, no problem, I just cut the grass so we can sit out on the lawn if you want.” She smiled and we left for my car. This was easy, I wasn’t going to get in trouble with myself, we were gonna watch the fireworks then I’d take her home or at the most we’d just fall asleep in my bed or on the couch after.

A half hour later we were sitting on my back lawn on a blanket with sodas and crackers, her legs were covered because the temperature was dropping. The first rocket exploded and she announced that she liked watching them laying down. For the most part I watched her watching the fireworks as I lay next to her. I never really cared that much about colors in the sky.

But she seemed to think it was fantastic, and commented on all the different shapes and such. It lasted for a half-hour or more. We lay on the blanket as the smoke wafted about the sky.

“You’re shivering, let’s go inside. I’ll make you tea or hot chocolate if you want.” She opted for hot chocolate wrapped in my blanket on the couch. She looked pretty worn out from the day, I told her she could go sleep in my bed.

“Aren’t you tired, Danny?”

“Yeah. If you want I’ll drive you home, but I thought you’d be cool with just staying over. I’ll sleep right here.”

“You don’t have to sleep on the coach, let’s just go to bed.” Ok, we’ll just go to bed. We went to the bedroom, I brushed my teeth, she did something in the bathroom. I stripped to my shorts and t-shirt, she got in beside me and removed her skirt under the sheets as nonchalantly as she could manage. She giggled nervously as I brushed up against her trying to turn the light off. Finally, it was dark, but then I could hear her breathing next to me and it just hit me, this wave of desire ran down my body.

“Danny, I’m freezing, is your AC on?” The way she said it was as perfect as any of the experienced invitations I’d heard from her sister or any other woman. But hers was virginal and had that note of innocence to it–that maybe she didn’t know how much her saying she was cold in my bed might turn me on.

“No, it’s off. I could get you another blanket or one of my sweatshirts if you want?” The test.

“No, that’s ok…” A second invitation. God, she was aware of her power as a female and she was the one casting the line. I moved to her, put my arm over her side, held her middle as she spooned to me. She accepted, holding my right arm with hers. I put my left arm around her shoulders and held her against my chest. Her breathing became heavier. I kissed her cheek and we lay still for some time.

“Danny?” I was half-asleep, feeling out her flat tummy over her tank top, stroking her naked shoulder.

“I thought you were asleep?” She moved, at first I thought she was trying to get away from me, but really she was just turning to face me. She moved back toward me, put her arms around me pushed her A-cup boobs into me, head against my chest.

“I sleep better on my right side.” It was dark but I could see enough to know she was wide awake. I put my right hand on her lower back.

“I sleep better with a proper goodnight kiss.” She kissed my chest. I moved her chin up toward me and planted my mouth on hers. She sucked on my lip and then on my intruding tongue. I let my hand wander toward her panties, played with the edge in my fingers, pulling up a bit.

I ran the pointer of my other hand over her pantie covered slit, she shivered and kissed me harder. She rubbed my stomach under my shirt as I explored her more, slipping my hand under her panties from the back, cupping a cheek, rubbing her thighs, tippling her pussy. She was a carnival of small noises and didn’t shy away when I finally put my hand down the front of her underwear and cupped her furry mound. I probably would of been bummed if she shaved, it wasn’t coarse hair either, it was downy and didn’t seem that thick.

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