A Philophobic Affair Ch. 01

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A sexy new mom, a hot old friend, and lots of drama.
8k words
4.29
37.3k
46

Part 1 of the 3 part series

Updated 06/08/2023
Created 03/09/2017
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(Hello again readers... This may be my last incest story, normally it isn't my cup of tea. The idea came from a friend, JT, and originally I crinkled my nose at it, but once I began writing it, I got into the story. Thank you to RP for editing the story, and thank you for reading... Enjoy!)

*

How does a person turn the ripe age of twenty-five and still not know jack shit about who they should be with or how the hell to have any sort of healthy relationship? I suppose there are a lot of people out there who have the same troubles I do. But they can at least fake it. I don't know how the fuck to do that, though I wish I did.

Ten years of dating. Ten long years of dating. And seven awful relationships were all I had to show for it. The only person who has been a constant in my life was Abby. And I haven't actually seen her in nearly six years.

I met Abby when I was about fourteen. That was when I had taken up babysitting to escape my dad. I was tired of coming home right after school to find him scream at whichever wife he had at the time. So I'd try to have something lined up to do for most evenings. And then Abby came along.

Her workaholic parents both did their jobs until about ten at night, and then volunteered a lot on weekends to keep themselves even busier. She was too young to be left at home alone so I jumped on it And she turned out to be the most fun, and the easiest kid to take care of.

We became friends after a few years. When I left my hometown at the age of 19 to live with friends across the country, we kept in touch. Some people may think it weird for a 19 year old to keep in touch with a 13 year old, but she was the only close friendship I had. Well, in all honesty hers was the only relationship in general that I maintained over the years. Even the friends I've lived with haven't really spoken to me since I moved into an apartment on my own when I was 21. In all honesty, I haven't initiated any conversation with them either.

I feel like a fumbling idiot, and my most recent ex knew that. I guess in all fairness she has been the only one to end our relationship somewhat politely. She was the one who suggested I start taking some sort of action to figure out what I wanted in my life. Actually that was pretty good advice. I just needed to take action. But I needed to figure out exactly what I needed to do.

I haven't been back home since I was 19. I figured that would be a good place to start over for me - to try and figure out what I needed to do to find my direction. To be honest, the only thing I was actually looking forward to was getting to see Abby after so long.

The city bus rounded the corner, and my stop was coming up just ahead. It felt strange having to take the bus again to get home. I was used to having my own car. But since I wanted to get out of my situation as fast as I could I decided to sell my car and take a flight back home. I also sold most of my stuff. It's a good thing to do if you want a new start I suppose.

When I got off the bus the entire street looked different. Almost all of the houses had new siding. The yards had changed, and some new residences had been built in what had been a field behind my street. It all looked so different that I didn't feel any sort of nostalgia as I walked towards my dad's massive house. As I slowly drew nearer to the house I was beginning to regret my decision to come back.

"Too late now," I muttered to myself as a reminder.

Once I got to the front deck I notice that it had been rebuilt and stained. Judging from the lack of mistakes and flaws, this wasn't my father's work. That meant he had to trust other people with his home. That seemed very unnatural for him the way I remembered things. Old age must have been catching up to him.

I didn't have keys to get in. But my dad had said his wife would be home. So I knocked softly on the door. For a moment there was no answer. But I could hear frantic sounding steps coming up some stairs.

"Just a minute!" an anxious, and panicked sounding voice sounded from within the house. I relaxed a little, knowing that she must have been busy trying to keep things clean. My dad was a neat freak, and terribly overbearing, even though most of the messes created in the house were from him never cleaning up after himself.

When the door finally whipped open, I found myself mesmerized as I saw a blond muscular woman staring up at me. She was wearing a business blazer, which exaggerated her massive cleavage, and skirt which tightly fit her very petite waist. The breasts were probably fake, but I didn't care. My cock didn't either.

Despite looking flustered, and with her laugh lines showing, she looked stunning. The perfect trophy wife for my father.

"You must be David," she stated, beaming a brilliantly white smile. "I was just cleaning your room. I wasn't sure when you'd be home, so I came from work." She was speaking quickly, which made it more difficult to pay attention as her cleavage was a lot more attention-grabbing than her voice or the words she was offering. It was taking all the concentration, and focus I had to keep looking in her eyes rather than at her chest.

"Here, let me take your luggage. You must be tired." She took my bags from me and rushed back into the house. I tried to pull myself together and follow her back into the house, then downstairs to my room. I was glad to be following her so I wouldn't have to try and hide the raging hardon bulging my pants.

I found myself unable to pay attention to the details and changes of the house or room while she was there. It was almost as if she were blinding me.

"Um," she hesitated. "I wasn't sure how you would like your things so I - I just...um..." She was looking around nervously. It took me a moment to realize that she was expecting me to be like my dad.

"I know my own sons can't stand it when people touch their things or move them s-so-"

"It's perfect!" I said reassuringly. "Thank you so much." I smiled, and tried to hide the fact that I was really just wanting to check her out. As she began to look at me, I subtly moved my hands to my crotch area; trying to hide my cock, and holding back from proclaiming that I'd like to see what she looked like underneath the sexy secretary suit.

She seemed to be a little surprised at my kindness, and I was entranced by her eyes as she looked me up and down, almost scanning me.

"It's no problem," she replied. "Hey, listen. Your dad will be home late tonight, but I should be back in time to cook up something around five o'clock. I really need to head back to work now, though. You're dad has some appointments he needs some help with. Feel free to eat whatever you want, and do what you need to do. Just make yourself at home. Um...I'm Gina," she said as an afterthought. She held out a manicured hand. As I felt how soft her hand was as I took it, all I could imagine was it wrapped gently around my cock, tugging me into her mouth.

"It's nice to meet you, Gina" I managed to choke out. She smiled at me and briefly held my cheek, unexpectedly, in a gesture of care.

"Okay, I'll see you later!" She quickly rushed off before I felt, and heard a popping sound at my middle. Once I heard the front door close I looked down, and it didn't take much brain power to realize that I had broken the waistband of my underwear. My erection was ready to spring free as soon as I undid my zipper. I'd have to be careful before taking my pants off...and I really needed to. My cock was throbbing, and I desperately needed to get off. I could feel it pulsing against my hand while I tried to get it out.

"Fuuuuck!" I moaned.

As soon as my pants were off of my legs, I chucked them to the side of my bed, and spread my legs a little. The air gently flowing around my legs made me feel more free, and refreshed.

It only took a moment to get my cock out, but the frustration made it feel like it was taking forever! Once I was laying down on my old bed. I felt like a hormone filled teenager again as I lubricated my hand with the lotion that was always by my bed. I forgot I had even left it there. I was using a six year old lotion to lube myself. But at the moment I didn't care. I didn't bother teasing myself, or try to hold back to make it last longer. I wanted to cum, and I wanted to cum now!

I used one hand to cup and play with my balls while frantically stroking my cock up and down in the perfect rhythm that I had created for myself.

"Fucking hell!" I growled into the air.

I had trouble keeping quiet. But then remembered somewhere in the back of my mind that I was alone here. So I kept moaning and growling as I fucking well pleased.

As my lust took over, the image of her came into my head. I began to imagine her lying with her legs spread wide on my father's bed, moaning softly and touching her little clit. Fuck! The way her pussy lips would be spread would look so inviting... I wanted to watch her touch herself in reality...

Would I get caught? I thought to myself.

I imagined her moving her head to see me standing there, with my hand frantically jerking and pumping my cock. Rather than getting surprised or angry, I imagined her smile, and then force her fingers inside of herself, finger fucking her pussy with a rhythm to match the speed I pumped my cock.

"Holy, fuck!" I hissed into the air.

My mind then wandered to Gina riding me with her sexy little business suit on, her tits bouncing up and down inside that shirt. I would rip her shirt open and start sucking those massive tits while she rode me like there was no fucking tomorrow.

"Oh fuck! Oh fu-u-!"

I cut off in a loud growl as my cock exploded harder than it had in some time. I felt dizzy and lightheaded for a moment as I tried to get my breath back and gather myself. It wasn't until I got my breath back that I realized I had cum on my chin. I had never had that hard of an orgasm on my own before.

The tired and tingly feeling washed through me and was so strong that I couldn't even get up to grab the kleenex box that was on a ledge above my head. I ended up poking the edge of the box until it fell onto the bed beside me. Once I was done cleaning myself I let my eyes close and fell right to sleep.

****

I woke up hearing someone knocking on the front door. The first thing I felt was something poking into my forearm. When I opened my eyes I saw my arm resting on top of the kleenex box, my pants on the floor, and used tissues lying around my middle.

"Shit!" I muttered before carefully picking them up, and putting them in the small trash bin close to my bed. I carefully managed to put my clothes back on before rushing up the stairs. That's when I began to notice the changes.

The floors were a dark hardwood, and the kitchen upstairs had been completely redone with marble counter tops and sleek black cupboards with stainless steel appliances. The entryway was actually a hall now, rather than having no separation from the living room. The walls were repainted to an off white color, and the furniture was now all black and red leather. It looked quite different in comparison to what it used to. But after all that had been six years ago.

I heard footsteps going down the porch as the visitor thought no one was here. Swiftly I made my way to the door and swung it open to see a tall woman with golden brown hair and light olive skin making her way down the yard with her back turned to me.

"Sorry! I was downstairs. Can I hel-" I was unable to utter another word as she turned and I saw her bright green eyes. It was Abby!

"Ab?" I asked after a moment, shocked.

"Hey!" She rushed to me, quickly wrapping her arms around me, her body melting into mine. It felt so inviting. And she smelled as nice as she always had. She had to be using the same fruity spray.

I held her tightly to me, trying to remember the image of her as I a little girl. As we parted, I could barely see it now that I was standing in front of this drop-dead gorgeous woman with amazing eyes.

"Fuck!" was all I could say. I immediately covered my mouth, not believing I just swore in front of her. She laughed it off and rubbed my shoulder.

"Don't worry. I'm not at all innocent or impressionable," she giggled.

"Christ!" I managed to get out. "Sorry, it's just that...my fucking God you look...I mean...you're a woman now. Where'd my little Abby go?" She chuckled.

"She's still here," she replied. "She's just a little different. What about you, old man? Is that a grey hair?" She reaching high to play with my grey-free dark hair. As she was reaching I was avoiding looking at her cleavage.

"You still can't reach," I chuckled putting her hand back down.

"Still a giant." She smiled. To make it easier not to look at her, I moved quickly and put her onto my back. She used to love getting piggy backs. But now she was squirming, and it wasn't helping a thing as I was slowly getting hard again.

"You can't just surprise me like that!" she chuckled nervously clinging onto me. I laughed.

"Oh, come on. You used to love this." She groaned uncomfortably into my shoulder. And although I should have been getting my thoughts together, all I could feel was her warm breath against my neck.

"Ok fine," she said. "I'll ride you to the coffee shop where I left my car. But no more after that!" she insisted. I chuckled, holding onto her while letting some fresh air into my lungs. The more I breathed and walked, the more I could clear my head.

"So what have you been up to, tallness?" she asked. "Last time I talked to you, you were happily living with your girlfriend." She sounded like she was trying to get her mind off of the helplessness.

"More like numbly living with her,"I admitted. She leaned her chin gently on my shoulder.

"Wanna talk about it?" she asked. I thought about it for just a brief moment.

"Coffee first, drama after. I need to wake up a little first," I chuckled.

"Were you sleeping?" she asked. I readjusted her to a slightly more comfortable position on my back before nodding.

"I'm sorry. I could have left you alone for a few more hours if you needed."

"Nah, it's fine," I replied. "I was just taking a power nap," I said. You know, right after fantasizing, and jerking off to the image my stepmom riding the fuck out of me, I thought.

"You could have told me to fuck off and go home," she laughed. I shook my head.

"Uh-uh. Not to you," I said softly before getting an idea in my head. Once we crossed the street, we were only about another block away from a small coffee shop and convenience store.

"Ready?" I asked.

"For what?" she asked confused. I bend down and broke into an intense sprint, with her squealing and holding onto me for dear life while her tits rubbed and bounced against my back.

Dear God, keep it together dude, I thought to myself.

I've had plenty of hot girls who were just friends, so I knew how to reign in these urges. But I seemed to be doing an awful job of it right now! Maybe it was the shock of my new mom being a damn sex symbol. Then seeing Abby's equally hot body right after...

"David!!! Stoo-o-op!" she squealed and her legs locked around my waist. I don't know if she could feel my cock rubbing against her leg, but the excitement made me go even faster until we were in front of the little shop. She jumped off of me and landed clumsily. Her legs sprawled, and her hands and elbows slammed on the pavement to protect her head from slamming on ground. I turned quickly to see if she was okay... But I couldn't help laugh at the angry and shocked expression on her face.

"You mother fucker!" She shouted. I laughed harder and thought 'if only you knew'.

"Here," I held out a hand for her and she took it, letting me help her up.

"Douche nozzle!" she hissed. I laughed more at her creative profanity, trying to mutter out an apology. Unfortunately as soon as I could open my mouth, all I could do was laugh more. When I moved to approach her, she jumped back looking ready to run if the need should arise.

"Okay, okay. I won't do it," I said. She was still glaring at me.

"Come on, pinky swear?" I asked. She shook her head.

"Make it a king swear and I'll believe you." I rolled my eyes with a smile on my face. A king swear was like a pinky swear according to her. But instead of using pinky fingers, you use pointer fingers. And if you break the promise you get to break the other person's finger.

"Fine." I held out my finger, waiting for her to do the same. She hesitantly did, wrapping her index finger around mine. Once a moment passed, I continued to look at her while she loosened her grip. And I suddenly felt my chest tighten. It was almost like I had tears in my eyes. I didn't realize how much I had missed her until now. I jumped to pull her into my arms, and at first she protested.

"You promised!" She cut off when she felt me hugging her and nothing else. "Wha-?"

"I missed you, Abby," I admitted. "A lot." She calmed down and hugged me back.

"Where were you all those years?" she asked.

"You and I talked almost every month for hours," I chuckled, not understanding her question. "You know where I was."

"Of course I know where you were. But...where were you?" she emphasised. She was asking where my mind was; how I really was. What place I had managed to retreat to within myself.

"I don't know," I answered honestly. She took another breath and held me even tighter for a long moment. I relished in the warmth. It had been a long time since...well, as far as I can recall this actually may be the only time I've been held like this.

"Come on." She slowly pulled back. "Let's get you something to eat, and go for a drive." She smiled. I smiled back.

"That used to be my line."

****

"Okay, this is weird." I said as she drove me through quiet part of our town.

"What?" she asked. I waved my arms towards her, shaking my hands like I was in an outrage.

"You driving! It doesn't feel natural!" I shook my head.

"That's because you've been away for too long," she chuckled. I sighed.

"I have," I agreed. She continued down a dirt road that used to be the end of the town. But now there were houses there.

"Christ, this place has changed!" I muttered. She laughed.

"Maybe you just haven't changed enough to not be so shocked by everything," she commented. I looked to her and couldn't help but noticed how her natural, nice sized tits moved as the car kept going. Wanting to slap myself for lusting after her, I shook my head.

"I should have at least visited a few times," I commented while staring out of the window.

"Yeah," Abbey responded tersely. "And you should have brought your girlfriends along. It's supposed to be a girl who is a 'friend' that judges them first, because we're the one's who see through the bullshit that blinds guys for a short period of time." I laughed.

"Yeah," I replied. "I don't think there was any bull shit to see through. Except in me." She gave me a look before nearing the old baseball diamond that now had grass and weeds growing on it. It looked like it hadn't been used or maintained for some time. She pulled over and popped the trunk.

"Come on." She grabbed her french vanilla coffee and opened the door, walking to the back of her car. I took mine and joined her to see that she had lined the trunk with old couch cushions so that you could sit comfortably in it. I was impressed as I sat down beside her.

"What gave you the idea to do this?" I asked. She took a long sip of her drink.

"Well...imagine yourself as a fifteen year old girl," she replied. "You own a car because you're smart with money from an early age, your parents are gone for the weekend, and the senior star basketball player thinks you're hot - and older than fifteen." She looked at me. I groaned, rolling my eyes.