Lessons with Stepmom Ch 1: Awakening

I suppose what happened between my stepmom and I was inevitable, but looking back I wonder why it had taken so long. My parents had me very young, when my father was just starting school. They were a mismatched couple, my dad being an academic and my mom being a party girl. I never got to know her, from what I was told she got into nude modeling and was well known in the music video and adult magazine world and was in very high demand. When they split she had no interest in or means of supporting me so I stayed with my dad. Over the years, though he advanced and climbed the corporate ladder, his taste in women never improved. He had a parade of bedroom playthings that he would sneak into the house late or try to pass off as friends or coworkers, but it became obvious to me once I’d grown up that he was enjoying as much cheap pussy that all the money he earned could afford him.

By the time I was in college he finally settled down. He never got past chasing women many years younger than him, like he was stuck thinking he was still in his twenties, so my step mom was only three years older than me but, surprisingly, a pretty straight-laced girl. This was quite a departure from the barflies, strippers, and callgirls he had been taking to bed. I knew about her because she was a senior at my high school when I was a freshman. She wasn’t ragingly popular, but i remember her attracting more than her fair share of dates.

She was willowy thin in high school but later she had put on a pleasant amount of weight, so instead of looking like a starving Paris runway model she looked like a pin-up girl. She wore her brown hair in a modern, modest shoulder length style. She had big eyes and a slender nose that made her amusingly cute or sultry, depending on how she did her makeup. She dressed like a working woman now, but she still enjoyed pop music and would dance around the house when she was relaxing. We got along well, though being older and now my stepmother she tried to establish a parental order from the start.

One night while my father was away for a conference in Atlanta I had gone into his wardrobe to find a watch to use for the weekend. His wardrobe was actually as large as most people’s bedrooms, with a triple dressing mirror and several dressers and clothes racks. As I was ***********ing one i heard movement out in the hallway and footsteps coming into the master bedroom. I recognized the pace as my stepmother’s casual stride and heard her putting her purse and keys down on her mirrored vanity on the far side of the room. I hadn’t been expecting her back but apparently she had just gone out to eat and wanted to relax this evening. Not wanting her to find me rooting around in my father’s jewelry, I decided to hang back and wait until she left the room to sneak back out to mine. I stepped to the edge of the doorway so that I could watch for my chance.

I should have seen it coming, but she was in no rush to go about her plans for the night. She draped her thin jacket over her chair and put away her earrings and necklace. I was jolted by the sight when she pulled her blouse off and was down to a prim, lacy bra. My cock twitched involuntarily at the sight of warm female skin and I felt a bit of guilt for it. I quickly tamped that down. Why should I feel guilty? She wasn’t my blood, and I was old enough to date her if circumstances were different. Still, it added an edge to the feeling. I had peeped on girls before but this felt like a whole new level.

I figured that she was about to change or take a shower so I should just wait for my chance to make a break for it. She had unzipped and stepped out of her skirt so I thought that was the case. I made sure I was in deep shadow but still had a good view of the bedroom. She was unlikely to come into the wardrobe but if she did I could duck behind the heavy armoire. I felt my face flush with excitement as she took off her stockings and reached back to unhook her bra. Oh boy, was this a treat! I was going to have to play it cool because I’d never look at her the same from now on.

Her breasts were a delectable B-cup with very large areolas and berry sized nipples. I had thought she wore padded bras to make her boobs look bigger but it looked like she did that to keep from being embarrassed by high beams if her top was too thin. She pulled her panties down too and I was delighted to see an impeccably trimmed landing strip framing her tucked in labia. I got a view of her smooth, muscular ass as she walked back the vanity and undid her hair, letting it tumble down loose to cool off.

She sat on the edge of the bed with an undecided look on her face, wiggling her toes as she sighed heavily. I guess loafing for a while won on her priorities since she flopped down and stretched slowly. I got to see that she had a flawless, all over tan, thanks to my dad’s private garden off the master suite’s sliding glass door where she probably tanned nude on the lounge chairs. She didn’t have any blemishes or tattoos, just a toe ring on her dainty feet that I remember the popular girls getting as a symbol that they were with the in-crowd. She ran her fingers through her hair idly, twisting a lock in her fingers as she pondered something. She squirmed around until she had her head on the pillows, which then made her laying down with her legs toward me.

I almost gasped as she brought her knees up and let her legs fall to the side, so now I could see her pussy and pucker fully open. She rubbed her thighs to loosen up the muscles, her self-massage making her vaginal lips whisper open to show warm pink with the tiny bud of her clitoris starting to peek out. She made a little humming noise as she trailed a finger up and rubbed her slit slowly, sighing as she settled into a rhythm that soothed her horniness.

I forgot all about trying to leave for my room. I had only been planning on going out to a topless club that night, and there I was getting a show that was brightly lit and way hotter!

I stared and marveled at how beautiful and alluring she was on the bed, fully naked with her legs spread, one hand cupping a breast and the other starting to push two fingers inside her box. I squirmed a bit myself to get my cock away from the seam of my underwear. I reached down my pants and made room for it as I got harder from watching her enjoy her own body. Just the feel of gripping my shaft to take the pressure off the fabric of my pants made me start to throb.

The surprises were just getting started. She got up and went to the bed stand, opening a drawer and taking out a slim, silver vibrator. I gaped as she smoothly got on her back, holding the nine-inch sex toy like a lover was about to take her in the missionary position. She let her breath out loudly and ended with a moan as she got half of it into her moist channel. She rubbed her nipples with her eyes squeezed shut as she imagined a guy starting to work her over. She seemed to like it on the rough side since she pulled her nipples hard enough to distend the skin of her breasts and grabbed her ass hard enough to make white knuckles. She turned to the side and pursed her lips as she got a finger into her anus and she sawed the vibrator in and out of her cunt faster. She ran her tongue over her teeth as she enjoyed the sensations of getting both her holes stuffed at the same time. Maybe my old man hadn’t changed so much after all, since beneath her polite and proper exterior she was a pretty hot piece of ass.

She flopped on her stomach and got the metal toy back inside her, grunting rhythmically as she worked it in and out. That made me need to rub my cock through my pants to ease the frustration. After a while of this I realized that she was taking her time working herself up to good cum, so I gave in to a sudden temptation. I tiptoed across to the bathroom, grabbed what I wanted, and darted back to the wardrobe. My heart was racing not just with lust but also with an illicit rush over what I was doing.

With as much stealth as I could muster, I eased the door shut a bit so that I could hide behind it and still see through the crack at the bed where my stepmom was starting to fuck herself faster. My fingers trembled as I got the jar of her skin cream open and shoved my pants down. I sniffed it and let the sensation bring what I was watching in sharp relief as I could imagine how her skin smelled as she was masturbating. I vicariously joined her as I put a generous dollop of the slippery skin cream on the head of my cock and worked it up and down my shaft. My timing was uncanny as she started to plunge her vibrator deeper inside herself and moaned in time to the long, slow strokes. I slid my hand in time with her and found myself imagining being on my knees behind her, the two of us discovering how good we could make each other feel with a doggy-style screwing. She sped up and I grinned lecherously as I felt my own orgasm approaching. I hadn’t hooked up with a chick in almost a week so I knew I had a huge nut saved up. This wasn’t going to be the same as a girl making me bust but this was more intense than anything I’d felt before. I saw her back arch and she buried her face in a pillow to muffle the scream as she shoved the toy in as far as she could get it and twisted it around. I heard it buzzing at its fastest setting as she gulped another lungful of air before she screamed again, riding the mechanical stimulation that didn’t let up. I bit my own lip and stroked all the way down to the base of my cock as I fantasized about being balls deep inside her vagina as my cock spit streams of thick spunk across to splatter on the wall.

I suddenly remembered where I was and what I was doing so I shoved my lust aside and grabbed one of my dad’s shirts, trying to squeeze out the last of my cum that was still dribbling out of my softening dick. My heart was racing again in the urge for self-preservation as I wiped off my cock and the walls. I looked up just in time as I was sponging up the puddles of jism from the floor to see her getting up from the bed. I threw the shirt in the laundry and ducked to the back of the wardrobe, fighting to catch my stifled breath.

I caught a glimpse of her as she walked to the bathroom, a ridiculously satisfied look on her face as she fanned herself. Pressing my luck, I moved to watch her walk by. Her wonderful ass swayed deliciously and small trickle of pussy juice had run down the inside of her thigh. I wished that I could lick that clean and she seemed to have the same sort of thing in mind. She sniffed her toy before she started washing it off in the sink, humming a provocative pop tune as she dried it off and went to the shower. When she got it running warm and closed her eyes under the spray, I beat a hasty retreat to my bedroom, closing the door firmly and trying to calm down.

The next morning, I did my best to play it smooth as she joined me. I had needed to sneak her skin cream back into place as she went out for her morning stretch and swim routine, but she hadn’t seemed to notice anything suspicious.

“Good morning, Esther.” I didn’t want to call her my mom and she wouldn’t allow me to use her nickname from girlhood, so we had compromised.

“Hello, Alex.