Building Up Billybybbw4youngercocks1©
This is a story about my first encounter with an older woman - and I never looked back since, thanks to my father's then-girlfriend. She is now my stepmother.
My father and I were on our own for four years after my mother's death. Things were rough in the beginning, but not as difficult as they had been the last several years of Mom's life.
She wasn't always a woman who swung between bright and dark days before she died. When my parents met back in high school, Mom was a striking, tall blonde with perfect skin, a killer figure with 36C tits, and a dazzling smile.
She'd been a teenage model and a vivacious cheerleader who had more than her share of jocks and other popular guys she could have easily dated seven nights a week.
No one could figure out why she chose Dad, at least back then. When I asked her on one of her "bright" days why, Mom told me the more popular and good-looking guys were only out for sex while Dad truly loved and cared about her...plus he'd been an excellent math tutor. Ha.
He was a skinny kid when they met, with dark brown hair and eyes and no taller than five foot ten. In a photo of him and Mom at their prom, she towered over Dad by at least two or three inches. He was fairly good-looking in a quirky way, and while his appearance didn't break mirrors or scare old people, he wasn't "GQ handsome" either.
Their relationship was a true life tale of opposites attract: my stunning and gregarious mother who dressed perfectly and still turned heads and my low-key father with slightly above average looks and long hair who preferred to dress "grunge."
Dad asked Mom to marry him after they were together for six years and he'd finished college. He still had his long hair, but somehow Mom urged him to clean up his appearance. He finally got a haircut just before their wedding.
The first few years of their marriage was idyllic, and both were thrilled when Mom became pregnant.
When she miscarried, things gradually took a turn for the worst.
Mom wouldn't let Dad touch her for a long time, and she would spend several days at a stretch in bed. The cheerful beauty became a cross between a withdrawn shell of her former self and a screaming harridan who threw things at Dad if he was in the same room.
Dad still loved her and wanted to find help for whatever was wrong. When he did, Mom didn't resume being the woman she was before her miscarriage, but was functioning to the point she and Dad were sleeping together and the house was once again peaceful.
Then she became pregnant a second time...with me.
I remember Dad saying he'd walked on eggshells for months until I was born. He knew pregnant women could be moody and he was prepared to deal with that, but when she started spending days in bed after I was born, he worried that Mom was "sick" again.
He had Mom committed to the city psych ward after he'd caught her standing over my crib, about to put a pillow over my face. They called it postpartum depression - but Dad suspected deep down that she was disappointed I hadn't been born a girl.
The doctors eventually diagnosed Mom as bipolar and gave her medication. She functioned well when she took it, but like many people who take pills, she always had periods when she "felt better enough that she no longer needed them."
As I grew up, like Dad, I walked a tightrope around my mother. When she was on her meds, she was almost like the girl he'd fallen in love with back in high school. Her appearance and the house were immaculate, she cooked huge meals, laughed at the most silliest things, and I was "her sweet Billy, just as kind and handsome as his dad."
Off her medication - which became more frequent as I grew into a teenager - she stood in bed, wouldn't bathe or even comb her hair. The house was a disaster unless Dad and I cleaned it, and we were responsible for our own meals. Mom would yell at Dad for the most minor infractions, if she bothered talking to him at all.
And she'd unleash most of her abuse on me.
"Why couldn't you have been a girl, Billy? I should've killed you when I had the chance, but your father got in the way and locked me up!"
"He loves you, Mom," I'd tell her. "He did what he did to save you because you were sick."
"No he doesn't! You're just like him, someone who will just go out and rope some girl into marrying you, get her pregnant, and then lock her away in some hospital like your dad did to me! It's both your faults I'm the way I am! If he didn't lock me up so he could see other women, and if you'd been a girl, I wouldn't need to poison myself with those pills!"
I'd come to terms with her disappointment in me being a boy after a lot of time in therapy myself, but why Mom was convinced that Dad was having affairs was incomprehensible. She was the only woman he loved and stood with her in spite of the rampages that resulted from her illness.
It had broken his heart when he signed commitment papers after she attempted suicide with her medication when I was fifteen.
Mom was home within a week and things seemed fine for about six months before she went off her pills again. Most men would've thrown up their hands and left her, but I admired Dad for sticking with her in the long run, even if my relationship with her was shaky at best.
The bottom fell out of my already chaotic world when I was sixteen and came home from school.
Mom's "dark days" had become more frequent, but I never expected she'd successfully commit suicide. I called for help and tried to revive her, but it was too late.
Dad was also heartbroken. No matter how much Mom had put us through over the last several years, we still loved her.
It took him a long time to get over her death, and when he did, he started going on the prowl for women, sometimes bringing home two or three a night after work.
He was still in his forties and as his longtime friend from high school Sally would say, he'd "grown into his looks." He was no longer a skinny kid, but a well-muscled man of 215 pounds, and got plenty of attention from women.
I despised all of them except Sally, but she and Dad were just friends.
His former scrawny appearance got passed on to me. Sally always reminded me about how much I looked like Dad at the same age, but unlike my father, there was no beautiful model and cheerleader picking me out among the jocks and other better-looking guys at school.
Embarrassed about my mother's suicide and Dad's subsequent promiscuity with women, I pretty much kept to myself during high school right up until graduation, not talking unless someone spoke to me first.
I'd dated (and had sex with)- albeit rarely - a few girls, but with scars left behind from years of Mom's emotional battering, I was gun shy about getting serious with any female.
After the long trip through what seemed to be a dark tunnel, a ray of bright light appeared at the end of it when I turned twenty.
Her name was Kathy.
She was the antithesis of my mother; while Mom had been a tall, gorgeous blonde with a knockout figure, Kathy stood five foot three and weighed around 145 pounds.
I found her very pretty for her age - only two years younger than Dad - with long dark hair and blue eyes that lit up when she smiled, which was often.
Her tits weren't anything to complain about either; in fact, they were bigger than Mom's. If I could guess Kathy's bra size, it had to be at least a 40D (Another trait I inherited from Dad: I'm a breast man).
I liked Kathy right away, which was unusual. I don't know what drew me to her; perhaps it was her sense of humor, welcoming smile, her outgoing, accepting demeanor, her gorgeous rack, or that she was just plain devoted to Dad.
It didn't take long for her to become a permanent fixture in our household as his girlfriend, and I couldn't have been happier that he finally settled down.
The effects of Mom tearing me down so much remained despite therapy, so when Kathy started building me up, I didn't know how to react.
When she kissed my cheek one time and told me I was becoming "one fine-looking man" just like Dad, my face actually turned red.
I don't know if it was from the compliment...or her tits pressed up against me when she kissed my cheek.
"Don't be so shy and modest, Billy," she'd say. "You can do anything you set your mind to and get any girl you want."
It was the result of such encouragement from Kathy that I finally went to college. I was a couple of years older than most of my classmates, but being told by a woman I could do something gave me the push I'd needed for a long time.
Dad spent a lot of time away from home with his job as a producer in television news (when he wasn't man whoring around before Kathy entered the picture), so when I'd come home from classes, Kathy was the person I saw more often.
I always knew when Dad came home either from a long night at the station or one of his trips. The familiar sounds of bed springs, along with moans and cries drifting from their bedroom, found their way to my ears more times than I could count - even with my door closed.
To say I woke up many nights to the noise and got a hard-on would be an understatement. It's a wonder I don't have a hairy palm from all the jerking off I did when I heard Kathy talk dirty and imagined those amazing tits bouncing while she and Dad fucked.
Kathy had been living with us for about six months when she and I had sex the first time. Neither of us planned it that way; it just happened.
Dad was called out to assist in production on a major breaking news story and gone well into the next day, so it was just Kathy and I at home for the entire stretch.
She just returned from an appointment and came up behind me with a warm smile and tugged on my hair, which was pulled back into a ponytail at the base of my neck.
It was all I could do not to turn red yet again. "Hey, Kathy."
"Your dad still out?"
"Yeah, he called about fifteen minutes ago. They're still doing a live feed about that bad pile-up on the Interstate. Death toll is up to twenty-three. Guess he's working through the night."
She looked disappointed. "Oh."
"Looks like you're stuck with boring old me."
"You are not boring, Billy. How was class?"
"Nothing earth-shattering, but I got through it."
"Good. You're going to go places."
"Well, I wouldn't get excited just yet."
She placed a hand on my shoulder. "Why not? You're smart, kind, hard working, and not exactly hard on the eyes."
I felt myself turn crimson. "You're piling it on deep, Kathy."
"No, just speaking the truth. Look at you, Billy. I don't think I've seen a man your age blush as much as you do."
Her comment made my face feel warmer, especially since she said "man" instead of "boy."
"What do you expect from me being around such a gorgeous woman?" I managed to reply.
God, Billy, what the hell did you just say? I thought. Shut up, shut up, shut up! You have no idea how to approach women...
Kathy gave me a sexy stare. "Now I know you are your father's son."
"Really? Is that bad or good?"
"It's an excellent thing. You need to stop being so tough on yourself."
"Sorry, it's just that -"
"I know what your mother did and said to you, Billy. Dad told me everything, but you need to understand that she was ill and probably didn't know what she was saying. Not all women are like her."
"Yeah, well, I'm not much of a chick magnet anyway."
Kathy took my hand and led me to the couch before she loosened my ponytail. "That's up for debate."
Before I could react, her lips found mine, and her tongue slid into my mouth as we locked into an intense kiss. When Kathy began rubbing my crotch, it was almost as if my hands had minds of their own, grasping her tits and massaging them over her top while our tongues explored each other's mouths.
I finally broke the kiss. "Are you sure we should do this?"
"Your dad's gone for the night, I'm horny, and you need some...let's say 'reassurance'."
A groan escaped my lips when she unbuttoned my shirt and tossed it aside. She made no hesitation in pulling down the zipper of my pants. I lifted myself up a little so she could pull them down and off, and felt a little embarrassed that I was now naked in front of her.
Kathy bent down and gave me another quick kiss before removing her own clothes.
"Stop blushing," she moaned against my lips. "You have a beautiful body."
My mouth fell open when she kneeled between my legs and slid her mouth down my hard shaft in one swift gulp. I felt the tip of my cock hit the back of her throat. Kathy wrapped one of her small hands around the base of my erection and stroked it upward as she brought her mouth down to meet it.
I couldn't remember the last time someone had given me a blow job that was so damned HOT!
In spite of how wrong it felt that Dad's girlfriend was going down on me, I loved what she was doing with her beautiful mouth.
I opened my eyes and looked down at her bobbing head. Kathy definitely knew what she was doing when it came to sucking dick, and didn't even gag on my cock while she deep throated it. No wonder Dad groaned so much when they were in bed!
I couldn't stand it any longer. Within minutes, I busted my nut.
I expected Kathy to pull her mouth off of me, spit in disgust, and bitch at me about coming in her mouth, but to my surprise, she swallowed every bit of my load without a single complaint.
What was even more amazing was the fact I was still hard after I'd come.
She rose from her knees and kissed me. I could still taste the residue of my seed on her tongue as she tangled one hand in my hair while the other stroked my cock.
"I think someone's ready to fuck," she growled.
I don't know where it came from, but a bolster of confidence suddenly overcame me when Kathy lay back on the couch and spread her legs. I began teasing her a little, running the tip of my cock up and down her pussy for a few minutes before I pushed it inside her.
"Oh my God, Billy," she said with a gasp. "You feel so damn good!"
I started with a steady rhythm and gradually increased my speed. Kathy's moans grew louder as I took her right there on the couch, assured that Dad wouldn't walk in the door as she and I went at it.
Even if he had, I was at the point where I didn't give a shit. There was no turning back now.
Kathy's eyes were full of lust as we continued to fuck. "You like this? Does it feel as good to you as it does me, Billy?"
"Hell yeah, baby," I hissed. "You are one hot, dirty little MILF, aren't you?"
She began thrusting her hips in time with mine and roughly grabbed my hair. "Fuck me. Harder."
Wow, what a woman! I thought.
I pounded her pussy as hard as I could, my eyes fixated on those wonderful tits. The sight of them bouncing in time with our thrusts drove me crazy and I knew it wouldn't be long before I lost my load again.
Feeling my cock twitch in Kathy's pussy, I knew I was about to come. I lost control of my body and what seemed to be an endless amount of pent-up sperm went inside her. It was almost as if I couldn't stop coming.
She pulled my head down for one last kiss when we finished. We lay together for several minutes until we caught our breaths before I finally pulled out.
"What do you think of not being good with women now?" she asked.
I grinned at her. "That may be up for debate."
Kathy laughed and hugged me. "Now THAT'S the Billy I wanted to see for a long time!"
Dad came home around sunrise the next morning. I knew that for a fact, because I was awakened by the noises coming from his and Kathy's room.
I not only had jerk off material from hearing her and Dad fuck the shit out of each other, but also the memory of Kathy and I doing the same thing downstairs the night before.
It wasn't the only time she and I had sex. Nights when Dad was away, we'd sleep together in their bed. Nights he did come home, Kathy would wait until Dad was asleep and then sneak into my room for some additional action.
"I have to keep both of my men happy," she muttered in my ear during one of our stolen nights.
Eventually, Kathy got pregnant. She and Dad were married a month later, and she gave birth to a little girl early the following year.
To this day, whether Hunter is my half-sister or my daughter remains a mystery, since she looks like both Dad and me.
I became a much happier, more confident man both emotionally and sexually, thanks to Kathy. I doubt without her support, I'd ever met Lelani, my current girlfriend - who, by the way, is thirty-seven to my twenty-four.
Did I mention Kathy also ruined me for dating women my age? Not that I am going to complain anytime soon...it's a good kind of ruin!