It was a Halloween to remember. I was in my senior year of high school. As with any other holiday, my family was going all out. My dad went through the house trying to scare us with his gags in his zombie costume.
My sister Sarah at 16 wasn't into it as much as the rest of us but mostly did it for my parents' sake. Her 24D boobs were squeezed into her Tinker Bell costume, looking even more authentic with her naturally blonde hair.
My youngest sibling Ethan ran excitedly through the house as Sarah chased after him with his costume.
He ran right into me and I held him as he began yelling and fighting, the same thing every year. Sarah then attempted to dress him but he wasn't about to go easily.
"Ethan..." she said in her calm way.
"Yes Mommy?" he asked, still struggling against Sarah.
"Why don't you want to go Trick or Treating?"
"Because it's dark!" he exclaimed as if the answer was totally obvious, "something will get me!"
I threw up my hands in defeat and Sarah sighed, tapping her foot impatiently. Mom however, smoothed my brother's hair and said, "Is Captain America scared of anything?"
"No!" he shouted as if it was unthinkable.
"So if you have his uniform, you'll have his bravery. And you'll be unstoppable?"
Ethan stopped struggling to consider this. He then consented to dress up and Mom saluted him.
"Are you ready Captain?" she asked him, dressed in his Captain America outfit.
"Ready!" He exclaimed as he pretended to fly through the front door. Sarah looked at me and shook her head. She then kissed Dad goodbye as he stood by the door.
As she left, I dressed in my pirate costume and went to help Mom. I gave a loud smack to her plump ass in her blue miniskirt. She laughed as she looked me over, thankfully not seeing the boner in my baggy buccaneer pants.
"You look great Louis." Mom said with a smile.
"And you look beautiful Mom," I replied to which she smiled.
She kissed me warmly on the cheek before the doorbell rang again. As she opened it, two small twin boys, Simon and Steven, dressed as a cowboy and Indian, respectively, held up their bags.
"Trick or Treat!" they said in unison with almost toothless smiles.
"Well don't you two look handsome?" Mom asked, leaning to give them a mouthwatering view of her cleavage, "What bars do you two want?"
As I left, Mom called out for me to be safe. My friends were supposed to Trick-or-Treat with me but they had all been invited to Chester Harrigan's house for a party. All except me.
- -
Taking a bus uptown, I loved to Trick or Treat in the upper class part of the city. Sure enough, after only 6 houses, I had more than 7 and half bags of KING-SIZE candy bars and snack bags attached to my pants.
Screw those guys. I thought to myself.
I came to the last house I had and I rang the bell. After a few minutes, I heard shuffling inside and the lock clicked.
The door opened and there stood a silver haired woman stood there in a medieval princess costume which barely covered her her 36G boobs. She appeared to be in her fifties but had not a single major sign of aging to her name.
Her name was Lydia Henderson. My former babysitter when I was 4. It had been so long since I had seen her but she remembered me. "Louis Reynolds!" she exclaimed, wrapping me in a warm hug, "I can't believe how much you've grown!"
She smiled broadly as she released me. "I'm sorry," she said, "I don't have any candy. I just ran out just about an hour ago."
I started to leave but she stopped me. "Well actually there might be something," she said, "won't you come in?"
She had me come to the kitchen and sit at the table. She poured two tall glasses of milk and leaned over the place them in front of me. My cock hardened and I pushed it down, growing rapidly down my leg.
I looked up and met Lydia's eyes and she turned quickly though I could see her smile as she pulled a pan of fresh cookies from the oven. After she set them down, she went to get some plates.
"Thank you Ms. Henderson," I said as I helped myself.
"Lydia darling," she said with a warm smile, "I feel we know each other well enough to be on first-name basis."
"I remember you loved them when you were little," Lydia said, "always trying to sneak an extra before dinner."
I bit into one. It was delicious. Soft and hot with the right amount of chocolate chips. Just the way I remembered.
"They're still the best!" I exclaimed as I reached for another making her smile again.
"Same old Louis," she said, "if you hadn't came I probably would've ended up eating them all myself. But I'm trying to watch my figure."
So would any other man... I said to myself as we continued to talk. My eyes alternated repeatedly between her gorgeous eyes and even more gorgeous cleavage. She had a round ass which seemed to belong on a 20-year-old.
"I used to bake all the time you know," Lydia said, "my husband loved when I would bake for him wearing nothing but some 6 inch stilettos and an apron that said, "Heat up the Cook."
I nearly choked as my cock hardened to full power. She laughed again. "I know. TMI."
She saw my bulge. "Or did someone like hearing that?" I watched as she rubbed it gently. "I did some things I'm not proud of. I even considered doing porn after I and Henry divorced. But that was the '80's. No one would want to see me in porn now."
I remembered when I was little and I had found a box in her closet. She had done a photo shoot with many pictures nude. In one particular one, she had been in a leopard print skirt just covering her waist. Everytime I went over, I looked in that box.
"I don't know," I replied nonchalantly, "I'd love to see it."
She laughed and rubbed her ample bosom. "You really think someone would want to see these? My husband did for a while then he found someone else."
I was getting harder by the second, listening to her words. "It's not easy feeling discarded like a old shoe. But I always loved the feeling of a hard thick cock pounding my cunt and ass like raw meat."
"I can still remember you as a boy," she recalled, "running around the house naked with that abnormally large penis of yours flopping around while you always loved to wear my bra on your head always trying to catch me naked or undressing."
She reached over and undid my pants, my prick instantly shooting up leaking precum. "Look at that! Some things can never change..." she observed, "It definitely is still a beautiful cock..."
She began to stroke me slow with both hands and I moaned softly.
"Does that feel good Louis?" Lydia asked.
"Yes ma'am," I replied, my cock throbbing in her warm hands.
"Good. It's just my way of thanking such a sweet boy..."
I watched intently as she flipped her hair and untied her top from the back. My cock stiffened further as her heavenly boobs came into view. Round with pink areolas and puffy red nipples, they were gorgeous without an ounce of sag.
"I know I don't even have to ask if you like them," she said as she again started to jerk me off, "I just a love a good tit man." She then wrapped her ample bosom around my shaft and began to move them up and down.
"Holy shit!" I cried, barely containing my orgasm.
"Mmm..." she said, giving a lick to my head, "that feel good Louis?"
"Oh yeah..." I groaned, "it feels amazing..."
She began to fuck my cock faster with her tits, my head hitting against her chin. I pinched her tits, making her moan softly as she picked up speed, my cock drowned completely in her soft orbs.
"I know girls love to have this massive cock in them." Lydia said as she squeezed my prick tighter, "I've never seen one so large in my life." I was on the verge but her words were getting me even closer.