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Awkward Conversations With Jeanine

Awkward Conversations With Jeanine

by silverisgold
19 min read
4.67 (23900 views)
adultfiction
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Author's note: I've not been writing much lately, so this was a quick stroke story to "unclog the pipes," proverbially. It's not intended to be realistic or a great story, but I needed to put something out.

I hated being at Aunt Jeanine's. My parents would make me go there every stupid summer when they went on their big long camping trips for two weeks. I don't know why they always went to stupid Minnesota when there were so many closer places they could go that were way nicer, but it was every single year for some reason, like they couldn't get enough of that spot and the surrounding area. Not only that, but I was 18 now, for god's sake, and I was a decent guy, a good student, I lettered in both basketball and track, and I really didn't do a lot of dumb things. I could be trusted alone for several years, but when I made this point to my mom and dad, they were having none of it and insisted that I was going to Jeanine's yet again.

Aunt Jeanine was fine, nice enough, I did really like her, but she wasn't used to entertaining young people. She wasn't particularly homey or much of a cook. Her home betrayed exactly what she was, a long-single woman who obviously was enjoying her "cougar phase" of life. She had a deluxe bar which I wasn't allowed to touch, a hot tub that I really wasn't interested in, and her wifi package didn't even lend itself to gaming. She was just this long-widowed gal who played the field and didn't seem to understand me very well. My only release at her place was her workout room, which was quite frankly spectacular, and me being an athlete, I tried to use it as much as possible.

On the other hand, she had been one of my most secret masturbation fantasies for years, which ramped up my discomfort. She was 7 years older than my mom at 55, but due to decent living and a bit of judicious aftermarket alterations, she could have passed for her mid 30's easily. She had red hair down past her shoulders in a nice do that framed her face well, big sparkling hazel eyes that went from blue to green, a very pretty face complete with high cheekbones and plump lips, and to top it off one of the most rocking bodies I've ever seen on a woman in my life. I'd stolen looks and furtive sniffs of her undies over my the years, but when I found out that her 40G cup breasts were the result of a reduction rather than an enhancement, I almost felt sick. What, I wondered, had they been like before? Add to that a narrower waist, wide hips, and an ass that seemed like she was built for doggystyle and serious pounding, and I often found myself so focused on her eyelashes I could practically count the crumbs of mascara on them in an attempt not to stare.

Not that I wanted to acknowledge that particular bit of deviant thinking too much. Mom, Jeanine, and their mother all had TITS, and the last thing I wanted to ruminate on was their build, as it seemed way too Oedipal for me to admit with any comfort. But while I typically pursued the hard-bodied track girls, the truth is that women like Jeanine got my blood boiling and my dick hard quickly. Ironically, it was one of those athletic girls that set me on my way towards my eventual odd destiny.

One of the good things about Jeanine is that she didn't mind if I took off here and there, and was cool with not ratting me out to my parents provided I didn't come home slobbering drunk or something similarly stupid. I was waiting for my girlfriend Cat to come pick me up so we could go to a party at Billy Bower's house, standing outside, when she sent me a text.

Cat: Tommy, I cant come get you. I don't think we should go to the parti

'Great, she's tipsy already,' I thought, as Cat's grammar was always perfect until she got a few drinks in her.

Me: Why not?

Cat: Im sorry but I want to see other people. I'm sorry to tell you like this but I can't talk abotu it right now. I'll talk to you later.

Me: What?! Is this some kind of sick joke?

Cat: No, I'm sorry. I'll talk to you later

Me: Cat, call me please

Me: After 7 months together shouldn't we at least talk?

Me: CAT

The bubble delayed for a second and then turned green. Dammit. She turned her phone off.

What the actual fuck just happened? I looked up, stunned. My phone chimed again, and I looked down. It was a message from my friend Elaina.

Elaina: Hey, are you and Cat okay?

Me: I don't think so. She just sent me some weird text messages about wanting to break up.

Two seconds later, she called. "Hey Tommy," she said with a rueful tone.

"What's going on?" I said with a slight edge I tried to muffle.

"I...I don't know how to tell you this, but I think Cat...look, she went into a room with Daryl Crabbe about an hour ago, and then I saw her dash out desperately and hit her phone on the back porch. I didn't know what to make of it, and at first I didn't want to assume they were even doing anything bad, but she definitely came out looking pretty...uh, well, like she just got fucked. I'm...Tommy, I'm...I'm sorry to be the one to tell you."

I felt like someone just hit me in the spine with a bat. I had no breath, no words. I was just...numb.

"Tommy...Tommy I'm sorry..." she said.

I breathed deeply, counting to myself. I couldn't let myself break down. Not now. "Yeah, Elaina. Thank you. You're a good friend, and I appreciate you telling me. It couldn't have been easy. I'm...I'm going to go. Run off some frustration. I'll call you tomorrow, okay?"

I hung up, turned my phone off before she or anyone else could check in on me, and promptly screamed into the arm of my jacket as hard as I could.

I stared up at the sky, unsure what to do. Seven months! Seven months of my senior year I wasted on that girl! I could have been swimming in the cheer and dance squad girls, but instead I was with that dumb girl who insisted she wanted to go to college with me and play house living together and I had put up with her annoying vegetarian rants and lack of giving head for...seven months I wasted!

I was pissed, and walked back into the house, past Jeanine sitting on the sofa.

"You okay Tommy?" she asked as I stormed inside.

"Yeah, great," I muttered as I blew past her, whipping my leather jacket off and throwing it on the bed. I looked down at my button up, and realizing Cat had given me that, I pulled it off quickly as well. I paused, trying to collect myself, closing my eyes and breathing deeply.

"You look ready to snap a neck," she said from behind me, and I turned around to face her. Jeanine was leaning against the doorframe to my room, a highball glass in hand. Judging from her coloring and speech, I gauged her to be about two or three cocktails into the evening. She paused, glancing down at my torso. "Damn, Tommy, when did you become such a young stud? I bet you have to beat them off with a stick."

I mildly smirked for half a second at the comment, but then replied "Well, the only one I've been letting in to my radius the last few months just broke up with me. I heard she's been cheating on me."

Aunt Jeanine covered her mouth with her free hand, then quickly set her drink down and came over to me, wrapping me up in a sweet, but a bit close hug. As per usual, her enormous tits crushed against me, which was damn distracting, as was her perfume. Her hips moved a bit towards mine, and I tried to pull away a bit lest she figure out that her proximity was causing certain results, but that made he pull me in even tighter. I was slightly mortified, but she made like she noticed nothing through my casual slacks. If anything, she lingered more, then pulled back and gave me a warm look, reaching up and brushing my hair over a bit.

"Okay, come with me," she declared, taking me by the hand into the living room. She sat me down at the bar, going behind it, pulling out a glass, scooping in some ice from her counter ice maker, and then pouring some whiskey and a mixer into the glass. As she stirred, she tilted her head, looked at me, then put another splash of whiskey in, and then pulled out two shot glasses she filled with tequila. She lifted one and indicated a toast. We clinked glasses and then downed our shots. I could tell, despite the slight kick, that this was expensive liquor.

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"I don't want to get drunk" I joked.

"I'm not trying to contribute to the delinquency of a minor. I just figure a couple stiff drinks will help you let go of some tension."

"I don't know if that's going to do it."

"It's just the start. Trust me," she said with a wry smirk. I shrugged, and took a healthy swig of the cocktail. It wasn't bad. "Come on," she said, grabbing our shot glasses and the tequila bottle as she led me to the back yard.

Her back porch had a very nice hot tub in the back, but I had barely used it ever. "Come on, get those clothes off."

"No, Jeanine, I hate hot tubs..." I began.

"Nonsense, you've barely ever tried it." She went over to the bench that doubled as a storage space for all of her chemicals, and pulled out a scoop of some crystalline substance. "These are lavender salts. It'll relax you and put you in a great mood," she said as she dumped them in.

"Aromatherapy? That's your solution for my heartbreak?"

She interrupted me by coming up to me, placing her hand on my cheek sweetly. "Tommy. My wonderful, good-hearted, sweet, gorgeous nephew any woman should count herself lucky to even spend a few minutes with. Trust me. Let your Aunt Jeanine help you lick your wounds tonight. It'll be way better than what you would have done alone."

I didn't say anything, but instead acquiesced with a nod. She brightened up immediately, going back to set the dials, and fuss with the tub.

"I'll go grab my..." I began, just as Jeanine whipped off her top and reached around to unhook her bra.

"Nah, fuck it, let's just free ball it," she replied with a grin, dropping her bra as I looked away and held up my hands.

"Whoa, whoa, whoa..." I began.

"Tommy." I kept my gaze averted. "Tommy..." she called, with a bit of pleading to her voice. I reluctantly looked at her.

"Tommy, relax. Are you going to assault me just because you see me naked?"

"No, but I mean..."

"Then relax. You're an adult now, so I'm going to start treating you like one. I've had all kinds of friends in this tub, and we barely ever wear clothes in here. Truthfully, I'm a tiny bit of a nudist and I love being naked here. It's so freeing, you won't believe it. Now stop being a big baby and get in the fucking tub," she smirked. I stood there for a second, but eventually I couldn't think of a good argument, so I gave up and stripped down, getting in the tub right behind her. I felt a little flushed and embarrassed, so I tried to look up at the night sky so I could avoid her gaze, or worse, the sight of those massive breasts, floating up with the whirring jets.

"You feeling a bit uncomfortable seeing your old aunt in the buff?"

"Um, no, I mean...maybe a bit. I don't know. It's odd, that's all."

"Fair enough. But you're an adult now. I just realized tonight, maybe a bit slow on the uptake, that you're all grown up, so I should really treat you like it from now on. I know I'm not always the best at dealing with kids, but..."

"You asked me if I wanted to build a fort when I was 16, Jeanine..."

"Fair enough. But again, you're grown. And to be frank, I'm way better at adults than I am kids."

"Okay."

"Besides, isn't this better than sitting in your room being angry over McKenzie fucking you over?"

"Catherine," I corrected her.

"I don't care, and I'm trying to tell you that you shouldn't either," she smirked, giving me a salute with her cocktail as she took another sip. I joined her, and we sat in silence for a couple long, but comfortable moments. After a few, she asked sweetly "How do you feel?"

"Still tense, but a bit more relaxed."

"Fair enough," she mused. She waded over, pouring two more shots and handing me one. I tried to avert my eyes a bit at her topless state as I reached out.

"Hey, Tommy. Knock it off."

"I'm sorry, I just didn't want to...to..."

"See my tits? Big deal. They're just tits. Besides, I know you like tits, so what are you acting so prudish for?"

I looked at her. "What do you mean?"

"You used to rifle through my laundry to look at my underwear when you were younger, and stare at them when you thought I wasn't looking," she grinned, as I silently attempted to protest. "Didn't think I knew that, did you? It's fine, I really don't care if you look. I'm not modest at all." she added, giving them a little shake for added effect.

Feeling myself flushed, I instead stood and came towards her, grabbing my shot glass and clinking it with hers. We drank, then she gave me a glance up and down. "Very nice, by the way." I glanced down and realized with slight horror that my dick was semi-erect, and quickly went to cover it. She quickly grabbed my biceps, holding my hands back slightly. "Relax. Dicks have no conscience. I'm perfectly aware that your cock doesn't care that it's your aunt's tits out, it just sees tits and a woman and it just goes, hey, time to screw." I went to protest, but she continued. "Just relax. We're grown adults, it's fine, it's not like we're going to lose control and just tear into each other."

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"Okay," I gave in, throwing up my hands.

"Good," she says, settling back into the water. I started to sit down across from her again, and she interrupted, "Hey, why don't you come over here and sit by me and I'll give you a little shoulder rub. It'll make all your problems melt away, I promise."

I shrugged and sat next to her. She started in, and within about 30 seconds, I realized how goddamn good she was at this.

"I'm sorry kid...no. No. I'm sorry, Tom. You're a fine, amazing, handsome, considerate, brilliant, caring, hardworking younger man, and you deserve better than what you just got."

"Thanks Jeanine," I said, suppressing a shudder. The truth was, something about hearing the new inflection in her voice, her calling me Tom and addressing me like a man, turned me on deeply. I knew I'd likely end up beating off tonight thinking of her, but I was trying like hell to push that down right now, lest I do or say something stupid. I figured I'd let her finish he shoulder rub, then beg off and escape to bed, as this was really starting to get me going.

"I mean it," she punctuated by hitting a spot on my neck that seemed to dissolve major tension. I grunted involuntarily. "Your ex is an idiot. If you weren't family, I'd drag you out of this tub and jump you tonight just to show you how amazing and desirable you are."

"Uh, thanks," I giggled a bit. The comment made me slightly uncomfortable, but on the other hand, maybe it was the alcohol and back rub talking, but the idea of having Aunt Jeanine's tits in my face as she rode me wasn't the worst image at the moment. I stopped thinking and just felt. We sat in silence for a long while, her deft, strong fingers working over my muscles, making her way from my neck, down my back, and back up and out again. I began to feel like Cat was miles and weeks ago, and I locked in on the moment we had.

"It's just not fair. You deserve lots of love, pampering, affection, and great sex, and yet you're here alone with your old aunt while your ex plays around and your parents are running a train up north..."

"WHAT?!" I blurted out, turning around and looking at Jeanine, who put her hands over her mouth immediately, her eyes beyond wide with shock.

"I...I...forget I said anything..." she stammered.

"I don't think I'm going to be able to do that...um...can you explain, please?"

"I...I'm sorry, I can't tell you..."

"Jeanine..." I began, trailing off, before I took a very deep breath. "Just tell me. You just said several times that I'm not a kid anymore. So what did you mean by that commnt? Whatever it was, I was probably going to find out anyway. Just..."

"Okay, okay," she acquiesced, waving me off. "Your..." she paused for a few moments, looking down as she gauged her thoughts. "Your mom and dad are swingers. They're up at a campout right now they do every year, that's a big swinger event, and after that they usually go and hang out with a few other couples and get real freaky for a few days or so."

I was stunned into silence for a few moments. Finally, Jeanine broke it by shaking her head, turning around and pouring one more shot for us. "You look like you could use it," she muttered. I nodded my thanks, and we clinked glasses again before downing it. "I'm sorry, I can't believe I let that slip out."

"It's okay. It actually makes a lot of sense," I said, slowly nodding to myself.

"It does?"

"Yeah, it explains so many things...how long have you known?"

"About...23 years."

"Damn!"

"Yeah, they've been horny fuckers for a long time," she smiled, reaching out and rubbing the small bit of gooseflesh on my arms. "Get back in the water," she urged, and we sat down side by side again, only this time she put her arm around me and leaned against me softly. It was nice, sitting here with her like this. Her skin felt great, and I was starting to really relax. We sat like that in silence for some minutes, barely caring. Finally, when the jet timer went off, she spoke.

"I'm sorry again."

"It's okay," I smiled.

"When did mom tell you about...it?"

"What do you mean?" I quickly snapped my head over, looking at her, realization dawning...

"You slept with my dad?!"

"Oh, relax. It was only a few times, years ago, and your mom was right there watching."

I shook my head, not sure if I wanted to think about that. "I'm starting to prune," I muttered, and rose up, with Jeanine right behind me. She quickly grabbed a towel and pulled it around me, rubbing it on me affectionately. Her leg touched against mine, and it felt electric, her skin so very soft and warm, and I had to resist the sudden urge to crush her against me. I snuck a glimpse at the water trailing down her glorious breasts, noticing for the first time that her areole were decently large, almost as big as my palms, though didn't look out of place on her massive mammaries. I shook my head again, looking up to see her smirking slightly, knowing full well I was busted.

"Sorry, I'm just a bit weirded out by that fact. I thought my mom would have put her foot down on doing anything sexual with family."

"Oh, she did eventually. Said it was too weird. But at first, she was fine with it since..."

"What?"

"Your...your parents both have a slight taboo sex kink. Your dad used to ask me to pretend to be his daughter. Then your older sister was born, and he cut that out right quick," she added, drawing ever so slightly closer. "I think that made him feel a tick ashamed. I just found it a bit hotter, then again, I'm slightly more wild than your dad." She was drying the same part of my back and arms slowly, most pretense seeming to melt away at this point. We were close enough I could almost feel the steam emanating off of her body.

"How so?" I asked.

"How am I more wild than your dad?" she drawled. "I...well, I don't know if I should tell you this, but I have this little fetish. I like to pick up younger guys, and have them role play as my son. We'll set up a little scenario, like I walk in on them watching porn in my living room, and I'll chastise them, but then we'll end up watching it together, and then pretty soon we'll be fucking, and while they're pumping away inside me, I'll ask them to call me Mom, and I'll cradle them in my arms with my legs around them as they squirt all their warm cum deep inside me. My head swam with warmth, buzzed, and I let my gaze yet again go down to Jeanine's perfect tits, feeling myself harden, as my cock dragged upward against her trimmed bush and soft yet flat skin of her belly. "Oooh," she cooed as she felt it brush against her. "Someone's very happy." she asked, reaching a finger down and very softly tracing it along my extended length. I slightly shuddered.

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