A Web of Sex, Lies and Sex

Hi. My name is Ryan, and this is the story of how I became overinvolved in a complex relationship with my Mom's sister Jen.

A little bit about me and my family. I am an only child, actually the product my Mom's previous marriage. She originally married young - age 20. I was born by the time she was 22. She never told me directly, but I've gathered from things she said over the years that I was an "accident". She and my bio Dad - Jim - got separated then divorced shortly after I was born. I guess he felt like this wasn't what he signed up for, and the strain of having a newborn ended their union.

I hardly know anything about Jim. He was only involved with me very sporadically early on, and the last time I ever saw him was when I was 4. Mostly, I remember him and my Mom screaming at each other over the phone, or worse when he'd show up randomly to pick me up. I guess he was trying to be a Dad (kind of), but was too much of a fuck up to pull it off. Mom never talked about him after he disappeared. I think she had nothing good to say at all, but she didn't want to damage my self esteem by trashing him, something I was always grateful for.

She started dating and managed to snag a man within a year. I grew up with my stepdad, David, and we got along fairly well. He's a good guy, and I was happy that my Mom was happy.

Fast forwarding a few years, and I'd met my Aunt Jen, my Mom's little sister. I didn't know my Mom's side of the family well, and hadn't seen her since I was little. She was a good amount younger than Mom. She appeared in our lives when I was around 15 years old. I think she was around 29 or so when she moved close to us.

Over the next couple years Jen and me actually became pretty close. She looked and acted much younger than her age, and would just hang out with me from time to time, almost like we were the same age. She introduced me to punk rock, metal and Wu Tang Clan. She'd also take me shopping at the mall so I didn't have to endure the embarrassment of going with Mom. Mom was always pushing me to get these horrible clothes, and made a big fuss about the prices there. I could just hear the laughter if the in crowd at my school saw her fussing at me in public.

Jen had a surprisingly good sense of fashion, and would guide my clueless self to nice clothing. She would even buy them for me sometimes, despite the fact that I knew she had almost no money.

So, Jen and I became close. By the time I graduated high school we had started hanging out pretty regularly, going to see movies together and stuff like that.

When it came to my Aunt Jen, though there was another layer to her situation. As time went on she became more and more erratic with her behavior. Honestly, she was starting to show obvious signs of mental illness. I have no idea what she might have had, but it involved serious mood swings, social self destruction and bouts of serious paranoia. I heard Mom and David talking about her, and it seemed there was always a problem. They tried to get her professional help, but Jen completely rejected the possibility. She was one of those people who thinks doctors are con artists and she could fix her problems with all this new age crap she was into. Mystic crystals, burning incense, "astral projection", all that hippy stuff.

Jen remained interesting to me despite all these things. She was the most lively person I'd ever met, and I was kind of fascinated by her. Even to the point of daydreaming about what it must be like to be like her. Even though she was 33 by then, she definitely didn't act like it. She always wore these outfits, not quite the "Hot Topic" look but reminiscent of it. For example, she'd wear what you'd call "fuck me boots", stockings, short skirts and these shirts with a very low plunging neckline. She always wore these tight faux leather jackets that ended just slightly lower than her waist, no matter the weather. It definitely got my attention, I'd never seen a female dress like the dedicated party girl that she was.

Things really changed when I was 19. Embarrassing though it was, I still lived with Mom and David. They would "tease" me all the time about it, but I could tell they weren't really joking and kind of wanted me to leave already. I had a job, but it didn't pay very much. I had no idea what I wanted to study in college, so I hadn't gone yet. I also wanted to avoid the crappy community college that would have been my only choice by then.

Back to Jen - after showing occasional bizarre behavior for a couple of years, she finally cracked and had what I'd call a nervous breakdown. This was triggered by the stress of losing her job. Her former job had been as one of those promotional beer girls that go to bars (often dress skimpily) and try to promote Coors or whatever with giveaways and stuff. It fit her for a while because her strong personality was actually an asset there. Despite all that, her boss fired her as a result of all the problems she'd been having. Showing up late, getting into arguments with the other beer girls, acting as if she was drunk, actually being drunk or high - the works.

Mom and David tried to support her and tell her to get help, but she was pretty unapproachable. She often wouldn't even answer her phone for weeks at a time. A couple times she randomly showed up at our house and would talk nonstop about things that were one step above pure gibberish. Even though it was super weird, I have to say that it was nice to see her glowing and so happy when she was like that. She got herself in some trouble with her landlord by not paying rent at her place, and my parents had to bail her out a couple times as this dragged on. They were pretty kind to her as it became obvious she had some significant problems.

That summer of my 19th year Mom and David unexpectedly planned a vacation to Thailand. David had tons of frequent flyer miles that were going to expire if they weren't used. I agreed to watch the house and take care of our dog, but I had to work late evenings some times. My parents arranged for Jen to be there too and water the plants, walk the dog and all that housesitting stuff. It was plain from our conversations that they thought I'd be a good influence on her, and that they wanted to give her something to do to earn some money to support herself.

For the first couple of days I didn't see Jen at all. They were my days off and I didn't mind, but I had to work evenings the next day. I don't know if she actually knew my schedule or if it was just random, but my Aunt Jen actually showed up that morning. She didn't call or anything, and I was busy sleeping in, so she ended up marching straight into my room and woke me up. I was sleeping in just my usual boxers and had to pull up the blankets to cover up my bare chest.

She seemed to almost sparkle as she woke me. She was clearly in the grip of one of her hyper phases. She said "hey, Rynie. Today is great, I just know it, wake up sleepy head!" She was talking in almost a baby voice - Rynie was a pet nickname she coined a couple years back to tease me about being young when we'd go to the mall. The way she said it this time, though, it was almost a pet name.

So, to describe how she looked, it looked like she'd gotten pretty dolled up for some reason. I'd seen her dressed like that for work before, but this was our house at 9:00 am. Her hair looked good for a change, not showing the self neglect she had in the past few months. She had straightened it, and it had blonde highlights and a hint of brown hair beginning to grow out at the roots.

She was wearing a short plaid skirt that was pretty close to a classic sexy schoolgirl outfit. Her blouse was a white button up shirt that was wrinkled kind of fashionably. It had short sleeves that showed off her arms and the first two or three buttons undone. Under that she had on a white tanktop that covered her cleavage but was so tight that it displayed her figure very well. She was one of those shorter and super slender girls who still have a great chest. I'd guess she was around a C cup, but they looked really big on her slight figure. She had on her black "fuck me" boots with black laces all the way up the side. She didn't wear stockings this time, leaving a good amount of bare leg showing with her plaid schoolgirl skirt. She was light skinned and emphasized it by wearing black liquid "catgirl" eyeliner over her intense brown eyes.

My aunt or not, she honestly looked hot as hell.

As for me, I only had on baggy boxers under my sheets. As awkward as it is to talk about myself, here goes. I am half Jewish on my Mom's side and had inherited the golden brown skin color some of us have. I had short, wiry brown hair and stood 5'11" tall. I honestly knew I had a good chest from starting to work out. It was probably my best feature and I could fill out a t-shirt quite nicely. In short, I was young and looking pretty good.

I said something like "urgh, it's early..." as I tried to wipe the sleep from my eyes. With her standing there in my room, I couldn't really get out of bed as I was 90% naked. She took this as laziness and hopped on my bed, at the foot of the bed. She was bouncy and energetic, kneeling on my mattress down by my legs. She smiled, her brown eyes lighting up as she said "it's... time... to... get... up!" The pauses were her wrestling with my sheets to pull them down. She won the sheet wrestling contest leaving my chest and boxers were in plain view.

"Don't you want to wake up now? It's late already and I'm going to put some coffee on. Come on, Rynie, come hang out with me!" I was basically powerless before this onslaught and groaned once again about it being early. She scooted up the bed until she kneeled next to my chest. Giggling, she started to run her fingers down my bare chest playfully. "Ooh, what do we have here? Someone looks like they've been working out." I squirmed around and tried to escape but she just continued to run her hands down my chest and back as I turned away.

She smelled really good, like a darker vanilla smell. Kneeling next to me and with her hands running all over my bare skin, I started to get my morning hard on. Shit! I reached down and tried to restrain it by tucking it into the waistband of my boxers. This left the head peeking out though, so I was forced to lay on my stomach to avoid major embarrassment in front of my Aunt.

She started to settle down a little bit, and while kneeling over me her touches on my exposed back turned into gentle light touches. Basically a caress.

"Aw, babe, sorry you're so tired. Come down with me to the kitchen as soon as you're up, ok?"

As I mumbled my response she leaned over me and gave me a little kiss on my neck. It was a couple notches more than a peck. I couldn't help but notice her perky breasts pressing into my back while she did this. A shiver went down my spine, and I was pretty mortified at what I was feeling. She rolled over my body to get off the bed, then, laughing again, gave a smack each to my boxer covered ass cheeks. "Nice boxers, Ryan." She looked back and gave me a playful but intense kind of look as we locked eyes for a second, then she finally left my room.

She didn't see me hard, right? I mean, that boxer comment didn't mean anything, right? Shit. Naw, she didn't see. I'm sure.

Right.

I felt like a mac truck had just hit me after her very high energy performance, so I did get up, threw on yesterday's jeans and joined her downstairs. My focus was acting super casual to drive home the point that nothing was weird and it was no big D.

She didn't physically assault me again, she was more in one of those sparkly upbeat moods that actually made me happy because she was happy. Even though I knew it was part of her problems with mood swings, you couldn't help but mirror her buoyancy when she was like that. True to her word, she put on coffee and made some eggs and bacon for both of us. It was good, and I started to settle down some. She sat down to join me.

She'd taken off her boots, I noticed and started complaining that she wasn't used to them yet. She sighed dramatically and put her bare feet and legs in my lap under the square table. I decided my best option was to play along with her fun side, and said "aw, I'm so sorry to hear that." I began massaging her bare feet and legs to show my sympathy. She really liked that and put on a show sighing and saying "Mmmm. That's so nice."

To fast forward through the rest of our day, we spent it together. She was friendly almost to the point of clinginess, but I still really liked her company as we took care of the dog, the plants and other house stuff. After that, I rested in front of the TV and Jen (of course) joined me on the couch. I had my feet up relaxing and then she unexpectedly started to snuggle her way under my left arm. This wasn't that strange for her to do, considering how she was. The problem was that I couldn't stop noticing her breast squeezed against my side. At some point she'd unbuttoned a couple more buttons of her white blouse. I tried really hard not to stare, but as I looked down at her, her tight, thin white tanktop looked like the fabric had relaxed quite a bit. I found myself sneaking peeks against my will at the cleavage this exposed. Then she snuggled closer and crossed her arms as if she was cold. The gap got bigger and I found myself staring at one perfect pink nipple. She had a bra on, but the cup apparently rode low on her breasts.

Shit! Powerless once again, I felt myself growing hard through my jeans. What the fuck was wrong with me? My body was acting like I was going to take advantage of my aunt who probably had special needs. NOT something I was ok with. My dick was honestly throbbing, trying to escape the restraining denim. Without getting up (which would have been a bad idea), I pulled a blanket off the back of the couch and put it over both of us.

"Mmm, that's so nice. Perfect." The problem was solved for now, or so I thought. Under the blanket, she was lightly resting her hand on my thigh. I froze, unable to do anything as she was leaning into me. She remained intent on the show, but her hands began lightly stroking my upper thigh and leg. It was almost absentminded, kind of like automatically petting a cat in your lap. This didn't help the fact that my cock was practically screaming - I'd gotten hard enough that I really needed to readjust it in my pants.

Her stroking knuckles brushed against my cock.

Shit!!

Once again unable to do anything, I could feel my cheeks turn red and hot with embarrassment. And some other feelings I really needed to not be there at that moment. She hadn't felt it, I told myself. No way. She sat up for a second to stretch in a feline like movement. This put her weight on my thigh for a moment. And then the back of her hand once again made contact with the iron rod pulsing between my legs. Her touch seemed firmer and lingered longer than the first time she'd brushed against it, then her hand let up on me.

It had happened again! I started to feel even more flushed and even felt the beginnings of perspiration on my forehead. To make the disaster complete as I looked over to see her reaction I found myself taking in her tits again. Her stretched out tank top was loose on the top, but still tight on the bottom. So, when she straightened up the milky white, pale skin of her tits peeked out. I found myself taking in the soft pink halo of her areola, as the material pulled down to just above her nipples. "Where the hell is this girl's bra?" I thought feverishly.

I started freaking out. I pretended to check the wall clock and be shocked at the time. "Oh, shit! Sorry, but I've got to go to work now, I'm late!" In truth, I didn't really have to leave for at least an hour, but it gave me an excuse to make a full retreat upstairs. All I could do was pray that she didn't see the obvious flagpole tenting my jeans before I turned my back on her and bolted.

In the bathroom, I splashed cold water on my face and hands and soaped them up. I finally got to adjust my aching cock to point upwards towards my belly. When I took it out, it looked... angry. More red than usual, and the head was kind of a light shade of purple. It was actually hot in my hand, and I couldn't stop myself from rubbing it rapidly for a minute. It felt so wrong I tried to stop myself, but Jen moving around downstairs decided the issue for me. I didn't want her to hear the sounds of my fevered jerking off session, so I put away my hard dick, threw on my work shirt and slacks and ran out of the house.

Oh my God. I'm like, some kind of molester.

Work was completely boring and mundane. I showed up more than an hour early. Nothing was going on. That unfortunately left me plenty of time to obsess about that sweet pink nipple I'd seen. It was like it was burnt into my brain permanently. I even got hard at work a couple of times, but was able to keep it under wraps by hiding it with binders and stuff I carried.

By the time we were done, it was 11:30. I was the last person to leave there in hope that my Aunt would be already asleep and in bed. I needed to get off sooo badly, but I knew I was too paranoid to do anything while Jen was still up. The thought of her catching me beating off to her body was unbearable.

The house was dark as I pulled up, which gave me hope of getting some relief. As I walked in, I saw the blue flicker of the TV from the living room. Sighing, I went to check it out instead of running upstairs to my room. Maybe she had fallen asleep watching TV.

Nope.

I thought I'd be fine anyway, as I was really tired from working late. Being fatigued had settled me down quite a bit.

Jen was sprawled out on the couch, and immediately flashed me a brilliant smile as I walked in the room. At least she didn't look mad or anything. "Hey, babe. Welcome home." I said hi back, and took in the scene. She had unbuttoned her white blouse all the way, leaving the tank top to loosely cover her. And then I noticed her legs. She was laying in a very relaxed and unladylike position. Her short, plaid schoolgirl skirt had ridden up high, and I found myself looking at the white spot between her legs. Surprisingly, she was wearing simple cotton panties instead of something racy that you might expect from my crazy Aunt.

I laughed. I don't know, the situation just suddenly seemed like a farce, and it seemed so typical of the trainwreck that was Jen that it was almost cute. Then I placed the smell in the room. Pot.

OK...

Sighing in tiredness, I walked over to the couch. where Jen moved her legs and patted the cushion next to her for me to sit. I saw the remains of a blunt smoking out of an old blue coffee can on the floor.

"Oh, my God, I'm so sorry. You're so tired from work, and I haven't even offered you anything yet!" She reached behind her and gave me a freshly rolled blunt and then got up. I heard some tinkling sounds from the kitchen and then she returned with three beers. I had dealt with so much that day I kind of gave it all a mental shrug and lit up the joint. I had only smoked pot two times before, at a friend's house. It just seemed like the thing to do. As I exhaled my toke, Jen handed me a freshly opened beer, and I took two big swallows. Apparently, I was going to solve my problems by getting fully crunk with my aunt. You know, the one who made the problems.

So, the next part of the night is pretty blurry. I remember laughing a ton with Jen, us giving each other foot rubs, making fun of the TV shows. My memory did record that somehow we started a game where she sat on my lap and tried to push me over by wiggling. It's exactly like it sounds. In reality it involved Jen rubbing her ass all over my stiffening crotch with that sexy schoolgirl skirt flaring out. So, basically her panties were going to town in my lap.