Category: Halloween

By Sexy HypnoGirl

I walked up the driveway of Tom and Cindy’s house and rang the bell. There were several cars parked outside, and it looked like their Halloween party was in full swing. However, the house seemed quieter than I thought it should be. Normally, these gatherings got pretty loud. I remember that the neighbors called the cops on us last year. Cindy answered the door dressed as a genie or a belly dancer or something.
“Great,” I thought to myself. “Why didn’t Tom tell me this was a costume party?”
Cindy smiled and gave me a quick hug, and as she pressed against me I thought again about what a lucky guy Tom was.
“Everyone’s in the living room.” Cindy told me with a quick smile “Come on, you have to see this!”
I followed her to the living room, where a small crowd was gathered around a loveseat. Seated on the loveseat were a very attractive blonde dressed as a southern belle, and a guy in a pirate outfit. I noticed the blonde first. She really was a knockout. She was wearing a green dress, a sexified version of a pre-Civil War southern belle’s ball gown, with a dark green ribbon in her hair. She was seated facing the pirate, lightly clasping both of his hands in her own. Cindy turned to me with a smile and shushed me before I could greet any of the party-goers I knew.
“Look into my eyes.” The blonde was saying. “Look deep into my eyes. Deeper. Deeper.” Continue reading “Halloween Vampire”

by FantasyWife

When I was 19, I feminized a man for the first time on Halloween. I had a date with my boyfriend for the big Halloween Parade in NYC. We decided to dress as the opposite sex together. He was ready to dress in drag and I was going as a man. I was wearing his trousers and a blazer that I had stolen from my senior prom date. I slicked my long hair back into a manly ponytail and finished off with a thin mustache in black eyeliner. I have to admit, I looked damn sexy. But my boyfriend looked even better! I really enjoyed transforming him from a jockey guy into a sweet blonde bimbo. Continue reading “A NYC Halloween”

By British Paige

A few years ago, I got invited to a Halloween party by a woman named Maxine who worked in the same building as I. I didn’t know her very well, but being new to NYC all the way from England, I decided I should go meet some people and be social. I dressed up as a Fairy, picked up a bottle of wine, and went over to her place. I walked in the door and noticed there was quite a bit of a crowd there, most also in costumes. Some people were dancing, some were drinking and talking, some were outside, some were playing cards and board games and etc. Maxine spotted me, walked up to me and hugged me saying she was happy I came. I gave her the bottle of wine, and she grabbed my hand, and said she would introduce me to some people. Annoyed that she couldn’t seem to find her husband at the moment, she proceeded to acquaint me with some of their friends. She asked if I wanted a drink, and I said yes. I could tell she already had a few. On our way to the kitchen/bar, she got distracted by someone else calling her name from across the room, and said she’d be right back. Not a moment later, this man in a Joker costume standing nearby asked what I wanted to drink. I said I didn’t care, but something fruity. So he poured me a glass of vodka with cranberry juice. We got to talking, he said he was new to the city as well, and had come to this party with a friend, as he pointed to a man in an Ape costume playing poker. The guy waved over at us.
Continue reading “New girl in town”

By JockStud009

It looked like it was going to be another boring Halloween party. I decided to go as a football jock since I already had the body for it. I play football for college and played in high school, so the uniform wasn’t a problem. I grabbed a clean jockstrap and stuffed my massive nine inch dick into it and got into the uniform, except for the padding. There was no need for it at the party. I walked over to the mirror and looked at myself in my uniform and even I was impressed by the massive bulge between my legs. “It won’t be too difficult to get laid tonight or get some fags to suck my cock,” I thought to myself as I rubbed my semi-hard sausage through my tight white pants.

I arrived at the party and it was the usual group of people. Zombies and witches were everywhere. I went over to get some punch, which had already been spiked. It didn’t take long for a sexy “witch” to come up to me and start hitting on me. “Nice uniform,” she smiled. As I turned to put down my glass of punch she smacked me on the ass. “This is going to be a great party” I thought to myself. Continue reading “The Witch and The Princess”

By PrincessMindFokker

When his wife first brought up the subject, Mike thought she was kidding. He thought that she was teasing him and that she’d never want to go through with it.

But she wasn’t teasing, she was very serious.

The plan was that they’d go to the Halloween party in elaborate costumes, so that no one would recognize them, and she would sleep with another man. He was to watch, silently complicit in her sexual betrayal. The thought of this should leave him cold, he told himself, yet he found himself so aroused at the thought that it drove him mad.

For months this plan had consumed their sex life. She’d bring it up constantly, whispering in his ear teasing taunts about her Halloween lover. At first she’d even bring it up as they made love. He wasn’t sure if the timing was deliberate, but he noticed that she always mentioned her cheating on him right as he came. Deliberate or not, he found the connection between the pain of her betrayal and the pleasure of orgasm becoming linked in his brain. Continue reading “Halloween Lover”

Halloween is one of our favorite holidays at NiteFlirt!!

How could it not be? A day where  everyone is encouraged to dress in their sexiest costume is exactly the kind of celebrating we can get into.  And no one does sexy like the Flirts on NiteFlirt.

To get everyone in the Halloween spirit, we’ll be sharing some of our Flirt’s favorite Halloween stories through Halloween! Want to hear more? Then give us a call!