Bloody Halloween First Time

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Luke (18) loses virginity to hot Annalise (24) on her period.
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RetroFan
RetroFan
671 Followers

INTRODUCTION & DISCLAIMER - In the Australian city of Melbourne in 1999, 18-year-old virgin nerd Luke has an unrequited crush on Annalise, a stunning 24-year-old blonde from Germany who rents a room from his parents while working on her PHD. Given Annalise is a reserved and somewhat humourless and stand-offish young woman, Luke doesn't seem to have much of a chance with the hottie 6 years older than him. Until the night of Halloween when an extraordinary series of events takes Luke to places he could only dream of with pretty Annalise ...

Please note that this story involves scenes with Annalise using the toilet and having her period, including graphic descriptions of period sex, so this story might not to be to everyone's taste. Otherwise, please enjoy 'Bloody Halloween First Time', an entry in this year's Halloween contest, and rate and comment. All characters involved in sex are aged 18 and older, and they and the events in this story are fictional with any similarity to real persons living or dead coincidental and unintentional.

*

"Happy Halloween, have fun kids," I said after handing out some chocolate frogs and chocolate-caramel koalas to a group of costumed kids who chaperoned by two parents were out trick or treating and they went on their way.

I closed the front door and went back to the living room where the six feet tall figure of Annalise sat on the couch. She looked at me with her big blue eyes, and swept the long blonde hair back from her pretty, doll-like face, crossing her legs as she did so. Under the short floral skirt she wore I caught the slightest glimpse of pure white cotton panty fabric, and looked away. Unfortunately my glance went to the C-cup breasts that filled the front of Annalise's white long-sleeved blouse, so I looked at the floor and her pretty bare feet instead. This didn't help at all, given I had a bit of a foot fetish.

"Third lot of trick or treaters tonight," Annalise observed, her strong German accent indicating her country of origin.

I nodded. "Yes that's right."

"I thought Halloween not so big in Australia, only in America and Canada," said Annalise, again crossing and uncrossing her long legs and unknowingly giving me a glimpse of her pants.

"It's getting bigger here," I said. "I mean when I was a kid, nothing much at all, but now we get trick or treaters every year." It was true, even on a cool and somewhat drizzly Sunday evening in Melbourne like this evening, it hadn't kept the trick or treaters inside. There were also houses in the neighboring streets of the eastern Melbourne suburb we called home that had put up decorations such as jack-o-lanterns, witches, black cats, monsters, aliens and ghosts. "Hope you're not too scared."

I laughed, but Annalise regarded me evenly with her blue eyes and did not laugh. "Why would I be scared, Luke? We have Halloween in Germany too, and there is no such thing as ghosts or supernatural. It is just silly superstitions. And trick or treating is dumb. When I was little girl, my parents tell me never to take candy from strangers, and when it is Halloween parents send their kids out to knock on doors and accept candy from people they do not know. Is very weird."

I should have known better by now than to try and make Annalise laugh. I had always thought that the notion of German people having no sense of humor was just an outdated ethnic stereotype, but it was certainly true of Annalise. It wasn't just me, Mum, Dad, my younger brother Dean had all tried various techniques to get Annalise to relax, laugh and have fun, but we were doing well to get a polite smile. Mum in particular had described her as 'hard work' and I had overheard Mum talking to her sister and mother, calling Annalise an 'ice queen', sentiments my aunt and grandmother agreed with having met our new house guest on a number of occasions.

"Watch that German girl Judith, her skirts are way too short for her own good and she might well try and steal Larry from under your nose," our aunt warned Mum one day. "I know a home-wrecker when I see one."

Despite not caring much for our house guest, I don't think that Mum worried about Annalise using her feminine wiles to steal Dad away from her. If anything Annalise was too cold to try and make a move on somebody else's husband, and Mum and Dad had been one of those couples who got together really young. No way would Dad stray, no matter how hot Annalise was.

Also not fans of Annalise were my aunt's two daughters who were around the same age as me. My cousins both had boyfriends, who were very impressed by Annalise when meeting her at a family picnic at St Kilda beach and spent the day fawning all over her. I don't think my cousins needed to be so jealous, Annalise was not impressed by their clumsy attempts to chat her up and was pretty dismissive of the two young men.

It wasn't just the lack of humor, Annalise also had some other characteristics that were often stereo-typed to German people. The most noticeable one was efficiency, and it didn't just extend to extreme punctuality. Annalise really didn't have time for small talk, with anyone she liked to get to the point and everyone else to get to the point, stand-offish would be the most accurate description of her overall personality. It wasn't that she was rude, it was just her way to be businesslike in all her interactions and it might have been part of her normal personality even if she was born and bred in Australia.

The same was also true of her interactions with her parents and younger brother. We had never met them, they were back in the city of Munich, Bavaria where Annalise had grown up, but their daughter/sister would call them and talk to them on her mobile phone. I had not one clue what she was talking about as I could not understand a word of German, but I did note that Annalise's conversations with her family were always brief and to the point -- no small talk and no laughter.

So who was Annalise and how did she come to move halfway around the world from Munich to Melbourne and living in our house? My Dad Larry worked in a senior position at the science department at a major Victorian university and post-graduate student Annalise had joined them on a major remote sensing project for three years working on her PHD.

Not having any friends or relatives in Melbourne, Dad and Mum had offered her our spare room to rent. They had sold the idea of Annalise coming to live with us to Dean and I as being the big sister we never had. However, Dean and I didn't need any convincing. One look at the stunning 23-year-old blonde and we were all in favor of Annalise coming to live with us, which she did in January 1999. It was the start of a big year for me, in which I turned 18 in February and would complete my VCE in Year 12 of high school.

Now it was October, and for some strange reason Dean's mates from school and the cricket and football teams all seemed to visit our house frequently, whereas before it was the kid whose family had a swimming pool that normally had lots of guests. I wonder what the reason for that could have been?

It wasn't just Dean's friends, it was my friends too. While younger brother Dean was the sporty type, I was definitely a nerd and into computers, video games, science fiction, superheroes, comics, fantasy, dungeons and dragons and the like. The other four guys in my group of friends -- Matt, Tony, Eddie and Chris -- had also been spending more and more time at my place this last year since Annalise arrived on the scene. This exasperated Jenny, the sole nerd girl in our group of friends, to no end.

"Here's an idea, whenever you're around Annalise don't ask her if 'she likes stuff', try and blink once in a while and don't walk around with your tongues hanging out like dogs," Jenny suggested to them one time.

Annalise definitely wasn't a fan of science fiction. In May, my friends were visiting and we were all talking about how excited we were about seeing the new Star Wars prequel, and how we were going to wear associated costumes to the premiere at the local cinema.

"But Star Wars is for children, you are not children, you are now all adults," Annalise pointed out to us as she went by, and some of my friends asked her if she liked Star Wars too, which as it turned out she did not. There was no mocking in her voice, no amusement, just stating the facts.

The reaction was completely different from my friends earlier this month -- Jenny the notable exception -- when they called by on Saturday morning to work on a group assignment for school. It also happened to be Annalise's 24th birthday, and having made some friends in Victoria's German community since coming to live in Melbourne, she was heading out for the day to celebrate Oktoberfest in the Dandenong Ranges. And of course, she was dressed in the traditional German clothes of a blue dirndl dress with a frilly white blouse and matching apron.

So was the sight of the birthday girl in her dirndl, blouse and apron distracting to myself and my friends? Well, we got very little done, giving poor Jenny a diarrhea problem, to phase it mildly. And when Dean and Annalise passed each other on her way out of the door to get her ride with her friends, what happened? My younger brother walked right into a wall that was dead in front of him, frightening the cat which ran away, growling and hissing, providing even more distraction.

I wished Annalise was wearing her dirndl, blouse and apron this evening for Halloween, but of course she was not. However I wasn't wearing a costume either, my tall skinny figure attired in jeans, a sweater and sneakers.

The cat, named Misty, was in the living room at this moment, a pure black cat which walked in front of Annalise. Again, I tried to make Annalise laugh. "A black cat walked in front of you on Halloween, Annalise, that's bad luck."

Annalise looked up from the textbook on remote sensing she had picked up. "Your cat walks in front of me all the time, it is not unlucky. Just dumb superstition."

Outside, I heard the rain getting heavier, wind blowing through the trees and across the road, the neighbors' dogs barked and howled. "Ooh, I don't like the sound of that," I said, trying to sound scared.

Annalise was her usual impassive self. "It is just dogs across road, they bark too much if you ask me."

I sat down on the couch. "You don't seem to be scared of anything, Annalise."

Again, a matter-of-fact response from the young German woman. "Only things that it is sensible to be afraid of in the right circumstances. People are scared of things that are silly."

I laughed. "That sounds like my friend Jenny's young niece. She's scared of the Melbourne Central Tower down in the city."

Annalise looked disbelieving, but at the same time not very interested. "Why would she be scared of a skyscraper?"

"Jenny said it's because it's big and black, and it has two antennae on its roof that look like horns," I said. "All kids are scared of something strange. When Dean and I were little kids, we were both scared of Halley's Comet when it flew by back in 1986, Mum and Dad said we were afraid it would crash into the Earth or something."

"I wasn't scared of Halley's Comet, and neither were any of my friends or relatives," said Annalise.

"No, but then you're older than me, you would have been 10 at the time," I said. "What about you though? There must have something illogical that you were scared of when you were a little girl?"

"No, there was not." Annalise was direct and to the point, and immediately went back to reading her textbook, putting an air of finality to my attempted conversation with her.

This particular evening I had no other sources of conversation. Mum and Dad had gone out to a dinner party to celebrate Dad's brother's birthday, and were staying overnight. It was kind of odd in Melbourne early this week. Tonight was Halloween, on Monday it was a normal day at work/school/university, and then on Tuesday it was Melbourne Cup day which meant a public holiday for the famous horse race. Then it was an ordinary week from Wednesday to Friday.

Dad had the day off work from his job at the university tomorrow and Mum had taken a day off from her job too as had my aunt and uncle, so they would spend the day tomorrow having fun and Mum and Dad would return home late tomorrow afternoon.

Dean had gone with Mum and Dad which might have seemed an odd decision for a 16-year-old with school tomorrow, but there was a simple reason for this -- video games. My aunt and uncle had a son and daughter the same age as us, and our cousins had some pretty cool games and were horror movie fans. So while the grown-ups were having their dinner party, my brother and cousins would spend the evening playing games and watching a scary movie.

Our cousins attended the same school as Dean and I -- it was a private school not far out of the city -- so Dean had taken his uniform and school supplies and tomorrow he and our cousins would catch the train to high school. It left me alone in the house with Annalise, which should have been a good thing, but it would have been easier to crack the exterior of the iceberg that sank the Titanic than penetrating the frosty exterior of ice-princess Annalise.

Again, I tried to find a suitable conversation for Annalise and I as she put aside her book. "Can you believe my uncle was born on Halloween?" I asked.

Annalise was matter-of-fact. "People are born every day of the year, it is nothing unusual."

"I wonder if Dean is having fun playing computer games with our cousins?" I mused.

Annalise shrugged her shoulders. "How should I know Luke? If you were so curious, call your aunt and uncle's house and speak to your brother yourself."

Changing her position on the couch, Annalise again crossed and uncrossed her legs, me mentally reprimanding myself for perving on her panties again when she again inadvertently showed me her underwear during this process.

I needed something to distract me from Annalise, both looking at her knickers and bothering her by trying to make small talk, and indicated a video I had rented from the local store. "You don't mind if I watch a movie?"

Annalise was glued to her science book. "Not at all," she said dismissively.

I turned on the television and inserted the tape into the VCR. The movie was appropriately a scary ghost movie from England set in the 1920s about a group of young men and women whose bus runs off the road and crashes on a wet and windy night on the border of Essex and Suffolk, this following a fun day trip in which the fine weather turned bad during the afternoon.

Trying to find a place to stay during the night and get help, they walk through the woods, pass an eerie church from which faint organ music seems to be audible to some but not all of the group and then to the large rectory house nearby. There are lights on in the house and the front door is open, but nobody appears to be around, so the group decide to spend the night there and go into the village for help in the morning. However, they quickly regret their decision, as the large red brick Victorian house is the infamous and much-feared Borley Rectory, and the young men and women experience no end of terrifying paranormal activity from the ghosts haunting the site during the stormy night.

An hour into the movie I was right into it. The film was eerie scary, better in many ways than shock horror, not to mention some of the young women looked pretty hot in their flapper dresses. That the wet Melbourne weather tonight matched the wet weather faced by the young people spending a terrifying night in Borley Rectory.

Annalise was indifferent to the movie, I just think she was grateful I wasn't trying to talk to her about dumb things that didn't interest her. She was like this with Dean as well when he tried to engage her conversation. We both had part-time jobs at a local supermarket, and one afternoon Annalise came in to buy some fruit. Dean, who was working in fresh produce, recommended some bananas to which she shrugged and said 'good to know.' I served her at the checkout and she spoke to me in monosyllables like I was a stranger, not like she lived at our house.

It was now completely dark in Melbourne, save for the moonlight intermittently seen between the clouds on a gloomy wet spring evening. Our sunsets had been later in recent weeks as we had put the clocks forward from daylight savings, and I was wondering if this meant the end of the visits from trick or treaters, when the doorbell rang.

Annalise immediately stood up, and I assumed that she was going to answer it. "The chocolate frogs and koalas are in a bowl near the front door," I said.

Annalise looked at me indignantly. "I am not going to answer front door, I am going to the toilet!" she said.

I blushed. "Oh, sorry Annalise," I said, stopping my video and making my own way to the front door, the doorbell ringing again. These trick or treaters were not patient. However as I got closer I heard teenage laughter and people running away, and nobody was in sight when I answered the door. Obviously whoever was responsible preferred the trick aspect rather than the treat.

Closing the door, I went back inside, and saw Annalise walking towards the bathroom that she, Dean and I shared, making haste for the toilet on her bare feet. I felt that warm feeling of anyone who had ever had a crush on another as I looked at the object of my affections, many sweet romantic songs from years gone by filling my head.

I had had a crush on Annalise ever since she arrived and despite or maybe because of her aloof and stand-offish nature I found her all the more desirable. To be honest, what other outcome did Mum and Dad expect to come from bringing a super-hot 24-year-old German girl into the house with their 18-year-old son? But I knew that my feelings for Annalise would remain unrequited. I had never been on a date much less had sex with any girl. How would I ever have sex with a stunner like Annalise?

About the only thing in my favor was that Annalise despite her good looks did not have a boyfriend at the moment, either in Australia or back at home in Germany. I had heard her talking to Mum and Dad about how she did have a serious boyfriend in her later years of high school and early years of university in Munich, but they had broken up long before she graduated.

But if Annalise was looking for a replacement boyfriend she wasn't letting on, and she would be looking for somebody older and way better than me. With my somewhat non-descript light brown hair, brown eyes and skinny frame devoid of any significant muscle tone, I was easily eclipsed by Annalise's stunning European beauty. I had about as much chance of going out with her as I had of visiting Saturn. Plus given she lived with us and worked with Dad, trying to get into Annalise's pants was probably a bad idea, a really bad idea.

I had only one outlet for my feelings with Annalise, and that was voyeurism, much to the dismay of my own conscience that would reprimand me for perving on Annalise and not respecting her privacy. Some of my voyeurism would come from sneaking glances up her skirts and dresses to see glimpses of her knickers, and perving on her in other clothes too. I especially enjoyed seeing Annalise in her nightwear -- an oversized tee-shirt over panties her long legs and feet bare -- and her stirrup pant leggings. The stretchy stirrups looked so good on Annalise's beautiful bare feet, plus when she bent over one could see her panty lines, the shape of her great bottom and between her legs the outline of Annalise's vagina. The truth was, Annalise made any clothes she wore sexy -- jeans and a jumper, shorts and a tee-shirt, a blouse, skirt and pantyhose -- and even if she wore an old sack it would look great on her.

RetroFan
RetroFan
671 Followers