A Strange Halloween Night

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A kinky kindness turns into a cause to blackmail.
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michie
michie
506 Followers

This story is a complete fantasy that deal with blackmail, immoral behaviour and sex. If you are offended by any of those things it's likely better to not read it.

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My daughter was so excited for Halloween, it was the first year I think that she fully appreciated just what this day means. In previous years she wore whatever we put on her, went to a few houses and got some candy, candy she wasn't allowed to eat. That was then and this is now; what a difference a year can make. Now she gets to be anything that she wants. This is a desire that many of us can somewhat understand, but at the age of six you actually get to realize it. In that moment in time, for that night, you really become whoever or whatever you want. I love seeing the look of wonder and excitement in her eyes as I fit the different pieces of her costume and the enthusiasm she has for it all coming together.

She picked and I promised to make the costume. It sort of made me proud that she wanted to be Link instead of princess Zelda. Her dad made her a very cool sword out of some left over baseboard trim and metallic tape, the handle fastened together with blue electrical tape; she loved it. My job was to sew a green suit. My knowledge of video game characters being pretty much nonexistent I had to rely on the internet, and my son's reluctant tips, on how to get it just right. Also, being years since I sewed anything this had turned into a project of blood (needles and fingers), sweat, and gruelling hours. Of course, there was also a firm deadline of October 31st.

In the end it really paid off. She was utterly adorable as her blonde hair flopped out of her cap as she struggled to keep it under, I was willing to go far but not to the point of drastic hair cutting. She wasn't allowed to bring her sword to school, so their was a bit of pouting, but a few promises that she could use it in the night and off she went.

The entire thing reminded me of how much fun these things can be, fun that you lose sight of when it all becomes something else. In high school I would just pretend it wasn't happening because I really wasn't invited to any of the parties and later it just became a sense of anxiety. It was one of those days that reminded me of some of my awkwardness, and even later when I was invited to the parties they made me feel very uncomfortable and out of place. All these insecurities made me forget what it was all about. That day I decided that I would dress up to take my daughter out; maybe vicariously join her in the fantasy of the day.

I had to work with what I had, which wasn't really all that much. I had a few older black dresses that I didn't mind mutilating. I decided, given the resources, that being a witch would be the most accessible. I hadn't dressed up since I was little, I figured at the very least my daughter would prefer a costumed chaperone to a plain clothed reminder of the real world. I needed to make a loose fitting gown, but my ego wanted it to fit in the right places. I took my measurements, 32-28-40, I wanted a gown that showed my hips off. As I was letting out, and taking in, my mind drifted to dirty thoughts about some of the dads having wicked thoughts walking behind this witch.

My sewing skills must have been in hibernation, because once I got into it, the machine was pounding and the gown was looking spectacular. Something completely childish, and strange, always made me think about sex when watching the needle of the sewing machine go up and down. I laughed to myself about the juvenile nature as I worked through my well deserved day off my normal work. I even made a totally awesome witches' hat out of the cut fabric and the cardboard from some of my husband's shirts that I kept.

The costume was close to perfect, it hugged my waist just the way I wanted, was loose around my chest but gave the impression that it could fall open; it looked sexy. Despite that, I couldn't help but think that something was missing. I got out a pair of high heels. "Now we are talking!" I said to myself as I strutted in front of the mirror. My other inside voice wondered if wearing these "fuck me" shoes to trick or treat was the most mature thing to do. I finally won this internal argument by citing the spirit of the season, and the interest of being a bad girl, after all I was becoming a witch here not trying to be myself. In that, I made up my mind to go all the way, I was going to change my hair to black.

Dying my hair wasn't something that came naturally to me. I didn't really understand the first thing about it having never done it. Living vicariously can sometimes take of life of its own. I wanted to jump in now with both feet. I've had a love-hate relationship with my hair my whole life, but the relationship is a decidedly conservative one. Growing up I had long hair that was prone to frizz, the only thing that changed as I grew up was how I managed it. I never got into any crazy style and never thought about changing the colour. My natural colour really is quite nice too, being a deep brown that gets lighter at the ends. I didn't have any dissatisfaction with my hair, I just wanted to complete my seasonal look.

It was hard to convince myself that I had done it, looking into the mirror to see jet black hair looking back at me. It still sort of curled at the end and looked just like my long hair, but just now it was black, really black. Unsurprisingly, my son, the first one to see it, didn't care one bit. I don't think he even noticed. His mind was squarely on other things, being six years older than his sister his intentions for the night hopefully didn't culminate with a police report. He was just getting his stuff and then going to his friends house. I'd already made my peace to not get involved. I made one parting speech, and then tried to distance his nonsense from the rest of my night. My daughter smiling and running all the way from the bus to the place she left her sword was an easy, and almost complete, remedy to his obvious trouble inducing intentions.

"Mommy your hair!!" Lisa exclaimed as if the shock was almost too much to take in.

I smiled almost in embarrassment to the look of awe on her face. It's not like she was upset or anything, this just wasn't the mommy she knew. One thing is for certain, she was completely fascinated with this incarnation of her mommy. She stood under foot for the next half and hour asking every question she could think of. About the hair, about the dress, the sparkle I added, and in the end the fun we were going to have. It was relieving to know that she absolutely loved my embrace of the day. We spent the rest of the afternoon craving the pumpkin, talking about how much candy we would get, hair dye and dresses.

We had to wait for her friends to get there. I had offered to take a few of her friends out and they only added to the general excitement. Usually I don't put up with that much, but this day I was just going to let them squeal, yell and generally make noise in their anticipation. The other mothers were thanking me over the overwhelming noise of hyper children, when I noticed the sort of disapproving look I got from one of them.

"Hope your shoes stay on." She said to me as she was leaving.

"Excuse me?" I was taken back by the brashness of her comment.

Undeterred and unembarrassed, she gave me a serious look and said, "I think you know what I mean, I just hope you're wearing underwear"

I was so offended that I was at a complete loss for words. I couldn't just send her daughter back with her but the thought did cross my mind. How could she be so rude? I know I was having those thoughts when I was putting the whole thing together, but I didn't think it was really on display, I figured it was just my inner thoughts exaggerating the reality. My offence soon gave way to embarrassment and I went upstairs to re-evaluate my decisions as the kids spoke to each other in a language only their understood.

"Is it really that bad?" I said out loud looking at myself in the full length bedroom mirror.

I saw a witch looking back at me. Maybe the heels were a little much, but it was halloween, it's supposed to be a little sexy. I liked how I looked. I was even proud of it. Maybe she was just jealous. I started to get indignant in my mind, feeling that I still had to right to wear heels. I didn't matter to me that part of me was doing it to get looks from men, I figured that I was proud that I knew I would get them. Snide comments from other women were nothing new, just usually they weren't directly to my face. I can even admit that I have said a few of my own when I felt a jealous twinge about a woman's bust or something, but never to her face! Who did she think she was? With that little pep talk I decided not to change a thing; except I loosened the front a little just because I though it looked better.

My husband got home and expressed, likely, the right amount of shock over my hair, Lisa laughed along with his dumbfounded amusement. I took the girls out while it was still light, following not too far behind. I noticed some of the sly looks from some of the men out with their kids and got a mischievous feeling of self satisfaction from them. I instinctively angled my hips a little more suggestively with each bump to my ego.

The girls achieved their objective and came away candy rich, Lisa beaming with smiles from everyone loving her costume. I gave her the sword back that I was carrying, and the girls went inside to compare candy. Being a little kid tired, I offered to take over the candy handing out duty from my husband, and he went in to supervise the girls to make sure their candy was safe. It was a comfortable fall evening, I enjoyed sitting outside, every now and then giving some candy to the later coming kids.

After a while the kids started to thin out, and I started to take more notice of the houses around me. Across the street, there was the neighbour's son, Matthew, handing out candy from time to time and looking like he was in an awful mood. I knew that he went away for school last year, but I didn't know he was back, he must have been 19 or 20. He was tall, and sort of lanky, not really filled out yet and had a slouch in his walk, brown hair that was sort of purposely messy and some acne left from his teens. He looked rather sad so I went over to talk to him, just to ask what was wrong.

"What's wrong? It's one of the biggest party days of the year and I'm here giving out candy." Sounding familiar I had a bit of sympathy for his plight.

"You know my parents didn't even ask me if I had plans before they went out, just told me to hand out candy." He continued as if he couldn't wait to get this off his chest.

"I don't care anyways, they're just years I will never get back."

He went on and soon I felt like I invited myself to a pity party. He certainly was sulking and it was sort of starting to ruin my night. I really did feel bad for him, partly because I sympathized with a lot of what he was saying and partly because it reminded me of my nights handing out candy while my parents went out. It really sucks when you think that your parents are cooler than you at that age. At the same time his whining was pretty pathetic, I tried to let the first part of my empathy when the day and give him someone to talk to.

I tried to change the subject. That wasn't happening, he was dead set on being the most unfortunate boy in the world. I asked him about what he was doing for school and this was a big mistake. It turned out that he was sort of forced into taking a year off after some sort of mistake by his parents in the loan application. I was given all the details on that, and while he should have been more active in making sure everything was in order, I know I wasn't one to talk because I took care of none of that stuff at his age. He was working at a restaurant in the kitchen and hating every minute of it.

Matt obviously was having a pretty bad year, but the negativity was starting to overwhelm me. At the same time, I did notice the young man's eyes wandering when I thought I wasn't looking. The shy glances were amusing to me coming from a guy more than 15 years younger than me.

"You want to have a drink with me?" I asked him abruptly cutting off one of his many complaints that night.

"Drink what?" He responded throughly confused by the question.

"Oh, I'm sure your parent have something, you keep going on about everyone getting drunk tonight, so have a drink, maybe relax."

"Yeah, I guess they have something that can be mixed."

We walked into he kitchen and I sat on a stool beside the island in the middle. It soon became pretty obvious that Matt had no idea how to mix a drink. It was sort of funny in a cute way. All at once I had a very dirty idea and one that in time I would come to regret.

"Sit down Matthew."

"Err, why?"

"Just sit down honey, and take your pants down, ok?"

He was like a deer in headlights. I gave him a sultry look, but he was frozen in his place. I'm really not completely sure why I did. I wasn't attracted to him and I didn't go over there with anything like that on my mind. A lot of it was sympathy, I wanted him to have a good night, just something to remember. I didn't really think it over long enough to think of the implications and the fact that I was an older married woman. Part of the nastiness drew me to it. We weren't going to have sex or anything, I was just going to give him a blow-job. I'd been having sexual thoughts all day too, from my new look, to the comments and the looks that I'd been getting. I also figured it was no real harm.

He sat down on the chair, but made no motion to take his pants down. I helped him start the process as I crouched in front of him. His cock seemed to flop out of his underwear, fully ridged and hard. Whatever his apprehension was to make any move, his cock wasn't sharing the same reservation. I took it in my right hand, put it in my mouth and started to bob up and down on it. His whole body was tense, he was holding the chair with both hands with a grip that looked like it was going to leave an impression.

In less than 30 seconds.........."ahhhhh ahhhhh ahhhh...urrrrgh"

He gave me no warning so it hit the back of my throat with a bit of force, I took it out as Matt continued to cum. This was a really big load of cum and I used my hand to help relieve the whole thing. His entire body went limp in the chair, except for his cock, which was still semi ridged. His face had the look of complete satisfaction and I returned my attention to his twitching penis. I kissed the head, it was still leaking with cum, I used my tongue to spread it around the sensitive part. He recoiled from the sensitivity that some men get after a release, I didn't let him off that easy and did some more swirls with my tongue. I finished the blow-job with a nice kiss to the tip of his penis.

"What was that thing......that thing....the thing you did at the end?" He almost exhaled the words.

"That was just my little specialty, I know how sensitive it can be after so I give it a little tease." I was smiling looking up at him.

Most of the cum was on him, although some did hit me in the chin. I went to get the paper towel from the counter to wipe it up.

"Do any of the girls do that?"

"errr"

I noticed from the look on his face that I just probably gave him his first blow-job.

"Oh I'm sorry, I shouldn't have." All at once I felt like a dirty old woman stealing something that should have been special. Although my "victim" didn't seem all that upset about the matter.

"No, no! It was wonderful, please don't be sorry, it was amazing, I've never felt anything like it, I'm sorry I was so quick." His whole demeanour had changed and he couldn't get the satisfied look off his face.

"Was it........you know......your first?"

"Yeah, but it was the best thing ever, thanks Mrs......"

I cut him off, "just call me Michelle honey, my surname is a little formal after that." I said it laughing and feeling a bit of humour in what I did.

It really was a morally awful thing to do, but I didn't feel bad about it. I felt more like it was a harmless little blow-job, hardly long enough to qualify as one. I suppose it wasn't that bad I thought to myself. It was reckless and pretty thoughtless on my end but it did seem to make his night. He still hadn't pulled his pants up and his body seemed to be draped over the chair.

"Well, I better get out of here before your parents get back." I said in a winking tone.

It was in some ways the perfect crime. I hadn't even been over their 15 minutes in total, it happened so quick that nobody even realized that I wasn't in front of the house. I struggled with my balance a little bit on the walk home as my heels suddenly became hard to walk in as I amused myself with the depravity of my exploit. When I got the light in the front of our house I looked down and saw a long rope of cum that must have dripped from my chin onto my dress. I rubbed it into the black fabric, it felt cold and sticky. I was so light headed that I almost walked in with something that would have been hard to explain, luckily I caught it before anyone else.

The kids were all sleeping in front of the TV. Their slumber party was heavily leaning to the slumber side after all the excitement. I went upstairs to brush my teeth and get out of the stained gown. Looking in the mirror I was almost out of touch with the woman staring back. My look had changed, but there was more, something in my eyes that seemed foreign to me. If someone told me about someone doing what I just did, I would have been horrified and completely judgemental. Yet there I was and I wasn't shedding any tears, I felt almost high from the moral bankruptcy that I hit. I looked in the mirror and my disheveled black hair and naughty eyes and couldn't stop smiling about it.

I left the washroom feeling completely horny. I texted my husband two words, "Fuck me" he wasted no time getting to the bedroom. I didn't want to waste any time with anything else, I jumped on the bed on all fours, he got behind me, grabbed my hips and gave me what I asked for. After he came on my back, I collapsed on the mattress and him on top of me.

"Michelle, you need to change your hair more often." He said while trying to catch his breath.

It was just in time too, as our son was just making it back home, and without a police escort.

"Honey, can you go down and ask him what he did? I don't feel like moving."

Alone in the bed I felt so alive and dangerous. Whatever led me to this spot had just ignited a reckless and calming feeling. I felt very free in the moment. I justified my mood by thinking that it was ok and nobody got hurt. It wasn't like I was considering having an affair with the boy next door. I just made his night, he never even touched me, well not with his hands at least. The only thing I kissed of his was his penis. I told myself that this was a bit of mischief, not an argument of my heart. I felt no actual emotions for Matthew, I wasn't even attracted to him. Although I didn't allow myself to admit that he had a nice hard penis and more cum than I had seen in a long time. All these thoughts were dancing in my head as I drifted off to sleep.

When I got up it felt almost like nothing had happened and life would just go on. I left the house for when the mothers came to pick up their daughters. I wasn't in a confrontational mood and part of me was also embarrassed by the accuracy of her sentiment. In any event, I didn't give the entire night that much thought outside of that. It didn't change me as a person, it more felt like a brief step outside myself, in a way I got the real halloween experience. That year I was a nasty and naughty witch.

michie
michie
506 Followers
12