Sins from my Stepmother, Book 1 (Ch 1-3)
From a young age, Teddy Carlson has been aware of his stepmom’s beauty. Workmen would wolf whistle her on the street. His girlfriends would seethe with jealousy at her curves. Even Teddy couldn’t help but steal a look when given the chance.
One summer, while staying at his sprawling family home in Greenwich, Teddy and his stepmother, Jill, did a bad, bad thing…
My name is Teddy Carlson. I’m twenty-two years old and I fucked my stepmother. Not just once in some momentary lapse of judgement. But again and again…and again.
Before you judge me, there’s a few things you need to understand. First, Dad and I never exactly got on like a house on fire. He was the CIO of a large hedge fund which meant that he wasn’t around much. He travelled to Europe regularly and commuted during the week to Manhattan for meetings.
When he was home, he was either at the office working late or in his study with the door firmly shut. I tended not to see him except at breakfast or dinner, and then, the conversation was largely unbearable. Dad would inevitably turn to sport, our single subject of common interest. “Hey, Teddy, you know the last time the Yankees played the Cubs at Wrigley on an 101 degree day, Bernie Williams hit two homers?” I’d nod along, feigning interest, as he reeled off a series of even more mind-numbing stats. Finally, Mom would interject by trying to steer the conversation to art – her single subject of common interest with Dad.
That was my best guess at how he’d landed her. Mom had been an aspiring art collector and Dad had introduced her to a lot of the prominent art dealers and artists on the East coast. Dad also came from good stock. His mother was a direct descendant of Teddy Roosevelt and his grandfather on his father’s side had been a Big Oil man.
So Dad was a tedious, well-connected workaholic. But the other thing you need to understand is that Mom was a living wet dream. A former Guess model and Miller Lite girl, she was tall, curvy and gorgeous. At thirty-eight, she had somehow managed to remain ageless and maintained her killer body. She’s five-foot-nine with never-ending legs, generous breasts and full hips that scoop dramatically into her slim waist. People who say Barbie’s proportions are unrealistic obviously never met my stepmother. Her face is pretty too, with long eyelashes, sculpted cheekbones and big, blue eyes that tease and smile at the same time. Her long brown hair rests on her shoulders in thick, tousled layers like in one of those Pantene Pro-V commercials.
One memory seared in to my brain from my early teenage years is of Mom parading around the house one evening in nothing but her heels and underwear. I was sitting on the couch in the living room watching TV when a flurry of long limbs and blow-dried hair burst in front of the screen.
“Teddy-bear. Do you know where Silvia left the dry cleaning? I’m running late for dinner with the Blackwells and I can’t find my red cocktail dress.”
Mom stood before me in matching off-white, La Perla bra and panties and Manolo Blahnik stilettos. Some subtle gold hoop earrings hung from her ears and a tiny bit of mascara on her eye lashes highlighted her sparkling, blue eyes. Aside from the missing dress, she was otherwise ready to go.
“I think she left them hanging on the chair next to the other sofa,” I said, trying my best not to gape at Mom’s perfect body.
Mom trotted across the room, her heels tocking on the hard wood floor. I watched her slim, sexy back as she lifted the dry cleaning onto the sofa and then bent over to sort through the garments. My eyes followed her long mane of brown hair down to her heart-shaped ass. Her panties stretched tightly across each cheek as she bent further down.
“Found it!” She cried, springing back upright, causing her 35Cs to bounce up and down from the sudden motion. They were thrusting proudly off her ribcage and bulging out over the fabric of the balconette bra like a pair of over-inflated water balloons. Her smooth skin pushed out just a touch beyond the top edges of the silk. And then she was gone as quickly as she had arrived, her long legs striding back down the hallway.
So Mom was incredibly, painfully hot. And I wasn’t the only person to think so. From as early as I can remember, Mom commanded the attention of men. I’d watch with amusement as their jaws dropped and they went goggle-eyed at the sight of her swaying hips and never-ending legs. When I was younger, she would pick me up from the front gate of school in her Range Rover in full hair and make-up, fresh from a photo shoot. As she stepped out of the car to greet me, the Dads on pick-up duty couldn’t help but stare at Mom’s full breasts and perfect ass. The school teachers and other Moms would look on with furrowed brows and clenched teeth with a mixture of awe and disapproval.
It was around about that time I realized Mom wasn’t your average Connecticut Mom. And that was saying something because there was no shortage of hot Moms in Greenwich. We lived in a neighborhood of Tudor-style houses and sprawling mansions owned by hedge fund managers, property developers and Connecticut bluebloods. Many touted their own trophy wife.
But Mom was different. Aside from being beautiful, she had a rebel flair and an innate sensuality about her. She was famous around town for having kicked one guy in the groin after he cut her off in traffic and stole her car park outside Whole Foods. Another time, we were paying for gas at the service station when the man serving us couldn’t stop gawking at her cleavage. “Careful Ed,” she said reading his name tag with a bemused smirk on her face, “you’ll sprain your eyes”. He turned bright red and undercharged us by accident.
But I know what you’re thinking. ‘That’s it? You slept with your stepmom because she’s hot and you didn’t get on with your Dad?’
Well, kind of. But if she was your stepmom, you would have tried to bang her too.
And if you think that’s bad, I haven’t even told you the worst part yet. Trust me, I don’t try and fool myself. I’m under no illusions. What happened that summer’s afternoon will stay with me for the rest of my days.
But, there is one other thing I haven’t mentioned. The spectacular, earth-shattering sex. Mom fucked me back every bit as hard as I fucked her and, boy, did we have a good time.
I can’t pinpoint an exact moment when the attraction between me and Mom became mutual. As I think back on it, it was more of a series of episodes, each one building on the last.
It was 1997 and Connecticut was experiencing its hottest June in fifty years. I was back home for summer after having just completed my second year at college. I’d spent the year playing wing for my college water polo team, the UCLA Bruins, and I was determined to spend next season playing center forward. For those of you who don’t know water polo, it’s basically the equivalent of QB1 in football. Coach’s intense training program meant that I’d already beefed up a lot since leaving school, but I’d been told I needed to get bigger still. So I signed up to an even more stringent diet and strength program for the summer. I worked out twice a day, mixing it up between weights and cardio. Fortunately, there was a premium gym in our neighborhood and plenty of space in our sunny back yard for drills. I could use our pool for laps too. It’s 25 yards and boasts some of the best views in Connecticut.
Not surprisingly, Mom got right behind my decision to beef up and eat more healthily. She had always lived a healthy lifestyle herself. She went to the gym or did pilates each day to maintain her figure. She put me on a detox program and made sure our double-door fridge was always stocked full of healthy sources of protein. She even whipped me up a green smoothie each morning and brought it into my room if I slept-in late.
So Mom became my number one cheerleader and nutritionist. And I certainly wasn’t complaining. Often, I’d be doing drills on the neatly trimmed stretch of lawn next to the pool while Mom egged me on from her sun lounger. Sometimes she’d just look up at me and smile, lift an eyebrow over her sunglasses and then tilt her head back down to her book. During my breaks, I’d steal a look at her firm breasts bulging out of her French bikini or her tanned legs stretching out across her lounge chair.
None of this was particularly unusual. Mom and I had always had a pretty good relationship. There was never any wicked stepmom dynamic like you see in the movies. Sure – Mom was fifteen years younger than Dad and a trophy wife of sorts – but she genuinely cared for me. She’d never had any kids of her own as Dad didn’t want any more.
But it felt like her affections started to take on a new character after we started going to the gym together. We had a family membership at Elixr, a three story-fitness center downtown. Mom and I started sharing rides given we were both going most days of the week. We had each set a goal to reach by the end of summer. Mine was to put on an extra ten pounds of muscle while Mom decided she was going to regain her old measurements from her modelling days; a ridiculous 35-24-34. If you’re not sure what that looks like, picture Denise Richard-like curves.
We’d usually start together on the treadmills where I’d do a full thirty minutes before moving to the free weights, while Mom kept on with her cardio. I’d watch with a mix of amusement and pity as the other guys in the gym lined up to use the equipment closest to Mom’s treadmill. They would stare mesmerized as Mom’s jugs bounced up and down beneath her exercise top. I couldn’t blame them really; I made sure I got a good eyeful too. It also made me feel a little less weird about wanting to screw my own stepmother.
I can remember being the envy of the entire weights section one morning when Mom came over to me and asked if I could show her how to do crunches on the Swiss medicine ball. Most of the visitors didn’t realize we knew each other. Every eye in the room was transfixed by Mom’s body. Her chest was heaving, as the strapping, preppy-looking college kid held her thighs firmly in place for a few reps. I almost felt proud as we left the gym together.
After that, the touching and the feeling became more frequent. It started with technique, but quickly turned into pressing and squeezing. I’d be driving us home from the gym and Mom would reach across from the passenger seat and try to wrap her thumb and forefinger around my bicep. “Gee, honey. Looks like all those bicep curls have been paying off,” she would say, giving it a few squeezes. “You must be swotting away the girls.”
I shrugged. I was. My birth mother had been a stunner like Mom and thankfully I’d inherited my looks from her, not Dad. I was six-foot-one, broad shouldered and confident. I’d lost my virginity when I was sixteen to Missy Mansell, a popular varsity cheerleader, two years my senior. She’d told me my dick was a lot bigger than some of the seniors she’d slept with.
I enjoyed the extra attention from Mom and became increasingly more brazen with my compliments too. One morning, she turned up for our gym session in a pair of new shiny, high-rise leggings and a tight gray t-shirt cropped just above her belly button. Her tits stretched her crop top far out in front of her body and I watched them bounce against each other heavily as she came down the stairs. They were easily the size of cantaloupes.
“Whoa, Mom. Looking good,” I blurted out before I had a chance to stop myself.
“Thanks honey. They’re sexy aren’t they,” she said running a hand down the contour of one of her slim legs.
“They sure are,” I said nodding. “The guys down at Elixr are going to choke on their protein shakes.”
“Hmmm. I’m not so sure that’s a good thing Teddy.” A sly smile crept across her sexy lips as I led her out the front door.
Then there were the times I felt like I’d caught her checking me out. I came down to the kitchen one morning in nothing but my boxer shorts. Mom glanced up from her coffee and I could have sworn she took a double-take. By that stage, I’d filled out to a well-defined 180 pounds. I made myself a coffee at the counter and turned for the milk to catch Mom gazing right at my ass. Mom dropped her eyes back to her copy of Vogue, apparently absorbed in an article about at-home hair dye.
But it was on the Fourth of July that things really started to get blatant. It might sound tame, but the memory of that night alone still makes my cock stir. I’d been out all day at a friend’s barbeque and was fairly boozed when I got home at around midnight. As I stepped out of the taxi at the front of our house, I heard a lively buzz of talking and laughing coming from inside. Mom and Dad had been hosting a dinner party and it sounded like it was still going strong.
There was no way I was going to get stuck making small talk with a bunch of Dad’s drunk friends. So I headed down the side of the house to sneak in from the back.
I was crossing the back patio when I spotted a solitary, feminine silhouette smoking by the outdoor table. I walked up in the direction of the pool and quickly realized it was Mom.
“Whoa, Mom!? Busted!” I said, surprising her from behind with a squeeze on her shoulders
“Teddy!?” she said, jumping. “When did you get back?”
“I think the real question is: What are you doing smoking?”
“Not a word. It’s a one-off.” Dad bought Mom a holiday house in Lake Como years ago on the condition she quit. I hadn’t seen a cigarette touch her lips since I was a teenager. If he caught her smoking, there was a good chance WWIII could break out.
“But you told Dad you’d never smoke again,” I said, stirring.
“Do you always do as your father says?” she asked, squinting her eyes and blowing a stream of smoke at me. She looked even sexier than usual in a ridiculously low-cut, black cocktail dress that barely covered her full breasts.
“You got one for me?”
“But UCLA’s star center forward doesn’t smoke.”
“He does tonight,” I said helping myself to the pack of Davidoffs on the table.
“Fine. We can be naughty together then,” she said leaning over with her Zippo to give me a light. I took a long drag, stealing a glance at Mom’s lap as I pulled back. Her dress was riding up her thigh, showing off her tanned legs.
“So how longs this been going on?” I asked.
“Only when your father’s being an ass.”
“A pack a day then?” Mom smiled, but didn’t laugh.
There was a long pause.
“How was your party?” she asked.
“Good. You should see the Buckley’s new pad in Riverside. Its made for a party.”
“Meet any girls?” she asked before wrapping her lips around the straw of her cocktail.
“Let me guess. They were all getting around in their itsy bitsy bikinis taunting you boys.”
“Yeah, that’s about right,” I said smiling, stealing her glass and taking a sip of whatever she was drinking.
“What about me? Think I need to go in for a lift yet?” she asked, cupping her hands under her tits and hoisting them up and down a couple of times.
“C’mon, Mom. You’ve got great tits,” I said. “And you know it.”
“I know,” she said with a wicked grin, looking down at her cleavage. “I do, don’t I?”
“Most girls my age would kill for a pair like yours.”
“You’ve become quite the silver-tongued devil, haven’t you, Teddy?”
There was a roar of laughter from inside and Mom glanced at her Montblanc. “Shit,” she said, stubbing out her cigarette and standing up. “I better get back. You coming to say hi?”
“Uh-uh…You can have all of that fun to yourself,” I said.
“Remember, Teddy,” she said sternly. “This is our little secret.”
She leaned down and gave me a kiss on the cheek. Then her lips moved to my ear, lingering for a long second. “Don’t stay up too late, you big tiger,” she whispered.
I watched her make her way back up the garden path in her high heels, her hips swaying more than usual. I tilted my head to get a better view when, suddenly, she stopped and bent down to adjust her stockings. Mom spotted me through her legs, gawking at her upside down. She pulled back up and gave me a long, probing look. And then a smirk crept across her elegant face before she turned and kept on back to the party.
When I eventually did make it to bed that night, I almost ripped the head off. I lay in bed, madly jacking my cock with both hands, mentally pounding Mom doggy-style. Her ass quivered and her big tits swung back and forth with every lunge. I still remember blowing a giant load all over the carpet. So much for having trouble getting it up drunk.
I collapsed on my pillow, drifting off to sleep. There was no doubting it anymore: I had a seven-inch johnson with my 38-year-old stepmother’s name on it.
Thanks for reading. These are the first three chapters of book one of a four book series. If you’d like to receive notifications of new chapter releases, subscribe to my profile page.
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