My Happiest Halloween
An erotic Halloween story of a bored housewife and a teenager’s fantasy fulfillment
I didn’t have any happy Halloween memories growing up as a child. My stepfather was something of a control freak and he liked to keep the family terrified with stories of kidnappers, molesters, and other monsters. After listening to these stories all year round, the idea of going outside and actually knocking on strangers’ doors seemed like suicide.
I walked around the block with my mother and braved a dozen houses before asking to go back home. My mother, who saw Halloween as yet another chore, was happy to have it over with so soon. My half-brother liked Halloween more because it was an excuse to dress up like the monster he was.
For me, Halloween didn’t become special until Liz and Rob moved in next door. Rob was a marine and Liz was his stay-at-home hotwife. Looking back now, I realize their names must have been Robert and Elizabeth but to us, they were always Liz and Rob. My stepfather instantly hated Rob who he called “a dumb-ass jarhead” while my mom took up hating Liz because the twenty-something lady was “trailer park trash.” Have I mentioned that my parents were assholes?
I was seventeen when they moved in and that first Halloween; Liz dressed up as a genie to hand out candy. I was too old to go trick-or-treating but my half-brother visited her house on his trip. My mom ranted for an hour about Liz’s exposed belly button and how she was corrupting the minds of the young. I liked that idea. Anything my mom hated so much must have been naughty and fun.
A year on…
The next Halloween was much better. It had been a mixed year of blessings. My stepfather was rarely home because of his job, though we would find out later it was really because of the waitress at Applebee’s. My mother’s sister had moved back into town and to compete with her, my mom spent more time out of the house trying to play in my aunt’s social circles. Yes, my happiest year was when my parents were too busy to be with me.
Best of all, Liz’s husband was away in Saudi Arabia for six months and Liz always needed something done at her house. My mom wouldn’t let my stepfather over there so it was always me that went over and moved a table or mowed her lawn. I was a socially inept teenager so mowing a woman’s lawn was the closest I got to dating. Liz wore this white bikini in the summertime that contrasted with her kinky black hair and gave me masturbation fantasies for months. We never really talked much. I think she knew that I was always on the clock when I came over and that my mom was just waiting for a reason to ban me from coming over as well.
That Halloween my mother took my brother to my aunt’s house. My aunt was having a huge party and my mom wanted to make sure she helped out so she could hold it against my aunt. I wanted to go but since Liz was handing out treats this year, my mom wanted to make sure our house did too. My mom had a lot of grudges that year. I can’t remember what my stepfather’s excuse was for not being there that night but it didn’t really matter. He was gone so often that that point that I was forgetting to be afraid of the world.
The first time kids came to my door; I lingered on the steps to see what Liz had dressed as. She came to greet the kids and I couldn’t help but stare. Liz was wearing a wispy long black clock complete with a witch’s pointed hat. Even from across the yard I could see that her cleavage was threatening to spill out of the dress. When she bent over to drop candy in a bag, the dress seemed to shrink around her round ass. Damn, I wished I were a kid again.
Liz caught me staring and waved at me. After waving back I ran back inside. I was eighteen and under the impression that women could read the dirty thoughts in my head. My pants were uncomfortably tight and I debated masturbating right then. In the end, I decided to wait. I wanted to see more of Liz and get a better mental picture. I had my sex life all thought out back then.
A few minutes later, the phone rang.
“Hey you,” Liz said. “You didn’t dress up for Halloween.”
I didn’t have a witty response. I think I might have said something like forgetting to get one. Funny how I can think of a million flirty remarks to answer that question now.
“I was wondering if you could come over and help me out for a few minutes,” Liz said. “I promise it won’t take ten minutes.”
“Sure,” I said. Oh God, oh God, oh God. This was a wish come true. Now I could see her sexy costume close up and masturbate about it later with better details! When I was a teen, I tended to aim low with my wildest fantasies.
I was over at Liz’s in less than a minute. My mom would be pissed to know I was deserting my post but that just added to the excitement. Liz greeted me at the door and she was more stunning up close. She had silver spider barrettes in her long brown hair and a temporary spider tattoo over the top of one breast. Fake fingernails stretched from her fingertips like knives.
Liz had removed her cloak to show her very short dress. It was so tight that I could see the outline of her nipples, and this was when I was of the age that nipples were the most secret, intimate part of a woman. She also wore red lipstick that made her look sinister and so damn sexy at the same time. Liz was evil and forbidden. I felt corrupted already.
I was actually smart enough to say “trick or treat!” She laughed and gave me a Hershey’s kiss before letting me in. As soon as I stepped in I saw something that chilled my heart. Her house was filled with cardboard boxes and almost everything was packed away.
“Are you moving?” I asked. There was a lump in my throat and I realized that it wasn’t just an expression.
“November second,” Liz said. “Rob is being transferred to Washington. It’s where he grew up so we’re pretty happy about it.”
“That’s nice,” I said. That was all I could manage to say.
“It will be for you,” Liz said. “Do you have a girlfriend?”
I felt my face heat up as I blushed. “No,” I said. There was a bitterness in my voice that surprised me. It was a cruel question. I was the tallest, thinnest kid in school with the glasses to match. Making friends of my gender was hard enough much less a girlfriend.
“Good,” Liz said. She took me by the shoulders and pushed me down into the recliner. “I would feel really guilty if you were.”
“What are you talking about?” I asked.
That was when she knelt between my legs.
“Oh my God,” I said. Yeah, I was real smooth back then.
Liz laughed at my remark but it was a nice laugh. She unzipped my pants and I was quick to help her pull off my jeans. The sexy witch rubbed my erection through my underwear all the while looking at me. Despite the fact that she was touching me there, what really fascinated me was that only her dress was separating her breasts from my thighs.
“Don’t say anything, okay?” Liz said. She took off her hat and set it on the floor. She had red ribbons in her hair that looked like the Devil’s horns.
I nodded. Sure. Anything she wanted.
Liz unrolled my underwear and unveiled my erection. She lifted my cock and slowly stroked me. With her other hand, she gently scratched my balls with her fake nails. My cock never felt so large and hot before. I leaned forward and watched her, fascinated and bewitched.
She dipped her head and I moaned before her tongue touched me.
One long wonderful swipe of her tongue licked me from base to tip. Another swipe of her tongue went across my girth. Liz’s black lips then puckered and kissed my cock before opening to swallow me down. My hands gripped the arms of the chair as her mouth engulfed my entire cock.
I had no idea that a blowjob was so wet, hot, slippery, and fantastic. Her long brown hair was on my thighs and I loved the way they would pull against my skin as her head moved. Liz’s eyes looked up at me and I basked in the attention they gave me. Her red lipstick was coloring my cock, leaving the mark on her lips as she bobbed up and down.
Just when I thought it couldn’t get any better, Liz pried my hand from the death grip I had on the arm of the chair. Still sucking me, she reached into her dress and pulled out a single breast from her dress. I trembled as she guided my hand to her breast and I sighed when she pressed my fingers into her breast.
Liz didn’t need to guide my hand after that. I fondled her. The softness of her breast amazed me as well as how hard the nipple became. I had just enough knowledge of women to know that a hard nipple was a sign of arousal and I clung to that hard nipple as proof of what was happening.
My fingers squeezed and massaged her breast with a sort of reverence. I couldn’t believe I was actually touching a woman’s breast and my fingers wanted to touch every part of her so that I would never forget what it felt like.
I felt my orgasm approaching and I kept very quiet. Deep down I still didn’t believe this was happening and I kept waiting for Liz to stop. My climax was like being hit by lightning but I didn’t make a single sound. Liz’s eyes flickered up at me and I could see her smiling as I emptied myself into her.
It felt like I was ejaculating an ocean into her mouth but Liz swallowed all of me without a single hesitation. In fact, her fingers gently squeezed my cock until every ounce of me was gone.
When I was done, she gently pulled my hand off her breast. There were red marks on her white skin and I felt embarrassed. Liz didn’t mind. She pushed her breast back into her dress without comment. I pulled my jeans back on and handed her back her hat.
“Why?” I said. My voice was little more than a whisper at that point.
“Why not?” Liz said. The bewilderment on my face made her smile.
“Look, you have a fucked up family. Your dad is a gigolo, your mom doesn’t even have her own personality and your brother is a brat. You’re the only one of that family worth knowing. If you have to have a reason, just remember that you got a blowjob from your neighbor because she thought you were a nice guy. Deal?”
I nodded. There was that damn lump again.
“Good, now get home before your mom accuses me of cradle-robbing.”
Liz moved out two days later. My cock had traces of red lipstick for days and I was sad when they were all gone. I wrote a lot of bad poetry all about the virtues of older women and blowjobs. It was a week of heavenly optimism until Susan Vickers in English class made a joke about a pimple I was suffering. I had to admit, her insults didn’t hurt as much as they used to.
My parents got divorced a year later but only after dragging us through Hell first. The stepfather moved in with his waitress and I never saw him again. My mother married someone that was an exact copy of her last husband. As for my brother, he was still a brat.
I married a girl who looked a lot like Susan Vickers but with a better sense of humor. My wife was an outcast from her family like me, and it was something we bonded over. I turned Halloween into the biggest holiday of the year for us. We dressed up in all types of costumes from sexy to just plain weird. It was the one time of the year we celebrated how diverse my wife and I were from other people.
Late one sweaty Halloween, when her mermaid outfit was in shreds, she looked in my eyes and asked the big question.
“With your lousy parents, where did you learn how to make Halloween so much fun?”
“One spooky Halloween, I got corrupted by this witch…”
MY HAPPIEST HALLOWEEN is an erotic Halloween story presented by eroticprose.com. The home of sexy stories and erotica.