Obsessed Ch. 03 - Progress... of Sorts

Note: All characters depicted are at least 18 years of age. Additionally, I do not condone spying on loved ones, especially for the purpose of sexual gratification. It is simply an element within the story as a part of character development. Thank you and enjoy!

October.

It's been a month since I began my perverted quest of spying on my mother every chance I get. As pitiful as that sounds, I have made some significant improvements to my mental health...in a way. Since I now have an active point of focus, I haven't drifted off in a surreal daydream in a while, which has greatly improved my academic performance, too. Ms. Lancaster hasn't found the need to keep me after school.

With that, however, I have fallen into a deeper, longing obsession with my mother. I have successfully peeked in on her multiple times:

- Her sleeping, with the sheet barely covering her. Looking so peaceful. It took a lot for me not to crawl into bed with her and pull her close.

- After the shower, with just an old t-shirt over her head (apparently, it's gentler for your hair than a towel? I don't know. It's just what she told me one day.) Seeing her walk about her room without a care in the world. Tits lightly bouncing with every step.

- Watching her getting dressed, which has become one of my favorite things to see. Almost every movement, so sensual and graceful. With every article she adds on, she checks herself in the mirror, adjusting it this way or that way, before moving on to the next piece of clothing.

- And finally, I even braved entering her room when she was in the shower once.

I was lucky. Her back was turned away from the mirror, because had she been facing the other way, she would have seen me crouched on the floor of her bedroom plain as day. This was the first and only time, so far. I'll need to be careful with the shower peep show.

But, oh...what a show that was! Her shower is encased in clear glass and is well vented, the steam hardly fogging up the glass. She was running her fingers, slick with conditioner, through her dark, wet hair. Droplets of water cascading down the channel of her lean back down to her gorgeous, round, behind. Oh, that ass! That incredible ass! Never fails to catch my eye as she walks away.

She started to turn, reaching into the stream to rinse her hands, and I was rewarded with a nice side view of those mouth-watering tits. I snapped a quick mental image before I scampered out of her room, avoiding being caught in the mirror. I hurried to my room, closed the door, dropped my shorts, and jerked my throbbing cock with the fresh image of my nude, wet mother in mind.

Two minutes in, and I was ready to cum. I quickly grabbed an old towel I had for the sole purpose of capturing my cum, and I let loose. I pretended I was cumming all over mom's tits. Several shots of cum exploding on her, hitting her neck, her chin, her nipple, and I just imagined it all dripping down her soft, tan skin. An extremely pleased, and happy look upon my mother's face.

Exhausted, I balled up the towel and tucked it back in the corner of my closet and threw my shorts back on, ready to enjoy a cozy evening cuddled up to my soon-to-be scantily clad mother.

We watched a few re-runs of a sitcom, followed by a late-night show before turning in. I jacked it once more to the feeling of her tits pressing against my arm, separated only by a thin tank top, before falling into a great night's sleep.

With the summer weather getting cooler in the last few weeks, she took every chance she could to jump in the pond. To avoid her getting suspicious, I did join her at least half the time. She never skinny dipped with me around, but I was still enamored by her in her swimsuits. With her being a fairly successful co-owner of a boutique, she is incredibly talented when designing and crafting clothes. Most of her wardrobe was made by her. So, when I say that her swimwear fit her like a glove, I am not exaggerating in the slightest! Everything is custom fitted to her.

And whether it's her preference, her slightly rebellious/carefree nature, or something else in her personality entirely, her swimwear never had any sort of cups, lining, gussets, or really anything to hide her nipples, or even her sexy cleft, from protruding through the material. Whatever the reason, I just try to not make it obvious that I'm staring at her pokies.

On the days I declined to join her, I waited a few minutes after I heard the back screen door close before running to the loft in the barn. Every time, without fail, I'd scope her out, through the binoculars I had stashed away, and watch as she stripped down to nothing. I just enjoyed jerking it to her swimming, tanning, and even rubbing one out herself on a couple of occasions. Those moments led to some very welcoming dreams of us masturbating together.

The first one I recall; --- we were together on the couch. Her legs spread, one hand pulling aside her black thong, while a finger circled her clit, and her other hand inserting a couple of fingers, all while gazing at me jerking my cock for her. She had one of her tits pulled out from her tank top, her button-like nipple hard, surrounded by a swollen areola. ---

The second dream; --- I was heading to bed and walked past mom's room. The door was cracked, her bedside lamp was on, and she was moaning softly. I crept up and peered in. She was nude, lying on her back, her head thrown back as she played with a vibrating wand.

I dropped my shorts and started masturbating with her. Then, suddenly she looked right at me through the doorway and...smiled! With a free hand, she gave me the "come hither" finger and I complied. Stepping out of my shorts pooled at my feet, I walked in just as nude as her, my hard-on leading the way.

She told me to stand at the foot of her bed and jerk it for her. She never let up on the wand, now doing figure eights around her clit. Again, I complied, and started stroking my cock. Our eyes locked on to one another.

"Mmmm...tell me when you're close," she said in a sultry, yet motherly, voice.

Not too long after, I felt my balls tighten.

"I'm almost there, mom!" I called out, gasping as my hand pounded away.

She scooted to the edge of the bed, a leg on either side of me. I felt the final surge before it released, and mom turned the wand from her clit and set it right under my balls, pushing up.

With her help I launched several ropes of cum at her, splashing her face, her chest, even her hair. Surprisingly, she seemed to be getting off on it, even sounding like it brought her to an orgasm. Shit! I never knew a woman could cum by getting showered in cum! ---

To no surprise, I jerk off a lot to that scene from my dream. I wonder if she has ever came that way? Hopefully one day, I may find out...firsthand.

The last dream that I can remember; --- we were skinny dipping in the pond, standing so close to one another that I could feel her breath. We were masturbating each other. My thumb playing with her clit while a finger glided in and out. My other hand massaging her tit and playing with her nipple. Her hands were both playing with my cock and balls, following my smooth and steady pace.

Our eyes locked, breathing in sync. And when we came, well.... ---

Well, and I doubt this ever actually happens... we came together. I woke up from that dream feeling incredible, euphoric even. Just the thought that my mother and I shared an intense, intimate moment like that, of climaxing together while gazing in each other's eyes, I doubt there's any other moment more beautiful than that.

Annnd...I think that's it. You're pretty much caught up with what I had been scheming about previously. At the moment, I'm getting ready to go to the Home Coming Dance the school put on at one of the hotels in town.

I wasn't originally planning on going, but a couple weeks ago my ex from freshman year, Sandra, came up and asked if I was going. When I told her no, she asked if I would reconsider if we went together...as friends.

This surprised me, considering she dumped me back then, but I wasn't dating anyone. And it certainly wouldn't hurt to try and obsess over some other woman in my life. So, I said yes.

...

The funky bass riff from "Dark Necessities" by the Red Hot Chili Peppers is bumping through my mom's speaker. We're in her craft room; mom at the sewing desk, adding the final touches to my vest while I stand in front of the full-length mirror admiring my mother's handywork.

The bold, navy slacks with an ivory button up shirt, pearled cuff links and studs to jazz it up. Light brown shoes with a matching belt and watch band. A burgundy silk tie, tied in a perfect Windsor, around my neck.

Clean shaved with pomade in my hair and a little bit of cologne spritzed on, oh yeah! I'm ready!

"Annnd that will...do it!" My mom exclaimed, jumping up from her desk chair.

I turn my head and watch her walking towards me. Tonight, as a single mother, home from work, showered, and without any other obligations, she's rocking a yellow pair of hip hugging, low-rise palazzo pants and a black, cropped tank top. Cozy clothes. I take a quick second to check her out, as I always do these days.

I take in her sexy, flat tummy left exposed from her crop top. Her cute little bellybutton with a small, silver studded piercing. Gazing up, I register that she's braless, her nipples, while still soft, protruding slightly through the material. I can't tell you all how much I really love that she's always braless at home when she doesn't have plans to go anywhere!

Her dark hair is up, tied in a messy top knot. A few curled strands framing her beautiful face. A proud smile on her lips. In her hand, my vest, a matching navy blue, with thin burgundy pinstripes running vertically.

She lifts it up and I slip my arms through. Before I even drop my arms, she snakes her way in front of me, fingers already slipping the buttons through the loops. She gives it a few tugs, making sure it stays where she wants it. She steps behind me and looks me over in the mirror, smoothing over my shoulders.

"Absolutely perfect!" She beams. "Oh my gosh, you are way too handsome to be my son, I can't even right now!" She let out a high-pitched squeal of pure excitement.

Admittedly, I blush a little. Hearing her gushing over how great I look isn't something I normally hear in the day to day.

"Ah! And the last piece to tie it all together!" She reaches for my navy suit jacket hanging on a heavy wooden hanger off the door. She opens it, and I slide my arms through the light, slick material. Being a little shorter than I am, I squat down a little as she tugs it up over my shoulders.

I stand up straight, still looking at my handsome self in the mirror, my mom's cute, smiling face peeking beside me while her hands reach around me to button up the top and middle buttons of the jacket.

"Ok, stand up straight, arms to the side..." she starts to smooth out the shoulders and sleeves, even bending down to smooth out the slacks. Not that I mind, I get to check out her cleavage, silently wishing that her tits might just pop out as she swipes down my pant legs with both arms.

She pops back up and looks back at the mirror.

"(Gasp), Oh my god! Baby! Look at you! Oh!" Her hands, clasped together, come up to her lips, eyes getting misty.

"Thank you, mom, for everything! You nailed it!" Before I finish my sentence, she clutches my arm and pulls me towards her in a tight, side hug, never minding that she just smoothed out the suit.

"If this suit doesn't get you at least a fifth date with this girl, then she clearly has no taste." She smiles widely, clutching my arm even tighter.

I start to chuckle, "Mom, c'mon! We're just going to the dance as friends."

"Don't 'mom' me!" she chides, playfully smacking my chest. "I'm a proud mama at the moment, and she better be speechless when she opens her door. Jaw to floor, the whole nine!"

Our eyes meet in the mirror, matching smiles for each other. I reach up with my free hand and squeeze her arm in love and appreciation.

...

Downstairs, I pull out the small bouquet and corsage from the fridge. Mom standing right behind the island.

"Ok, kiddo, first things first before you go." She slides over a box of condoms. "You better use 'em if you both get to that point in the night, and if it happens in my car, I want it thoroughly cleaned by Monday." Emphasizing 'thoroughly' with pinched fingers.

She then holds out her other hand, clutching what I'm assuming are her keys.

"If you drink even a drop of alcohol, you do not drive! You call, understood?" Her eyes serious and steeled.

"Got it, mom. Thanks." I reach out and she drops the keys in my hand, a smile returns to her lips.

"Knock 'em dead, sweety." She closes the gap between us and exchange pecks on the cheek. Then surprising me with a quick kiss on the lips.

"Have a good time, and again, if you need me, you call!"

"I will, mom. I promise." I smile back at her, trying my hardest to not make a big deal out of her kissing me.

It's not that it's never happened before, it's just really rare. The last time she kissed me on the lips was when I turned thirteen.

Internally shaking it off, I gather the flowers, tuck the three pack of condoms in my inside pocket, and head out to pick up Sandra. She has a lot of unexpected work to do if she is going to replace my vivid thoughts of my mother right now.

...

On the way to Sandra's, I reminisce about our four-month relationship those three long years ago. We were great friends, and always hanging out together. I don't know why I asked, but I did and surprisingly, she said yes.

Our first date was a semi-old-school date: a walk around downtown, stopping at a food truck along the way, chit-chatting about everything, and then finishing with a movie at the theater. To cap it off, when I dropped her off at home, I walked her to her door and we both expressed that we had a really fun time. I was about to kiss her, but hesitated. She didn't miss a beat and swooped right in, locking her soft lips on mine. We were no longer 'just friends' at this point. It was a long, hard kiss. Her hand cupping my face, pulling me into her.

After the initial shock, I leaned into it, pressing my body into hers, wrapping my arms around her. We made out right there on her front stoop for a few minutes before she finally broke away, sucking in her lips as if to savor the taste. Looking up at me, she smiled, "Goodnight, Grant." I replied with a smitten smile, "Goodnight, Sandra."

And with that, she closed the door, and I felt like I floated back to the bus stop on cloud nine. Our relationship only progressed from there. Less than a month in we were making out in her room with just our underwear on, dry humping each other. A week later, we snuck outside my house at night and skinny dipped in the pond. As we lay out on the bank to air dry, she gave me my first ever blowjob. To my surprise, when I came, she swallowed it all. Not one drop spilled.

I was in heaven at that point, and I thought that she would be 'the one.' We fooled around a lot more, but we never had sex. Three and a half months in, I started feeling like we were just in a rut. We hung out but didn't say much. We went out on dates, but at the end of the night, it never went past oral. I think she was getting the same vibe I was feeling, but we just never acknowledged it. Then, after four wild months together, she came up to me after school with a serious look on her face and said the dreaded words nobody ever wants to hear from their significant other, "We need to talk."

I was devastated. Crushed, and heartbroken. My first real relationship, and it just crashed and burned right before my eyes. My mom was my saving grace. She consoled me almost every night for a week, cuddling me, holding me close, stroking my hair as I sulked. That's when I started snapping out of my heartache enough to notice that I was resting my head in my mom's cleavage. Her soft, full breasts pressing into my cheek. At the realization, I noticed I wasn't sad anymore. I also noticed my pants getting much tighter in the crotch area. When my head hit my pillow later that night, it wasn't Sandra that I dreamt of...I dreamt of my mom.