Halloween Shenanigans

This is a Halloween story about my sister-in-law Dorothy.

Most of us have been in this position. Something forbidden looks attractive. Imagining that with every person there is a sex driven beast that just needs the right encouragement to come out from the shadows. You know, the whole all women are just two drinks away from lesbian sex thing.

Then there's Dorothy.

If I'm being honest, Dorothy is not all that attractive. She's what you would call "plain". She's on the tall side and was a high school basketball player years ago. She used to have great legs and a nice ass but in her fifties even that has faded. Her tits are really small and not the least bit perky. She and her husband Frank (my wife's older brother) are kind of righteous prudes. And, truth be told, she's kind of a bitch. Even with all of this, I have always wondered if there was a hidden slut buried deep in that cold personality of hers.

My wife's bothers and us usually end up going to social events with small or large groups together. They all seem to live where they grew up, never moving on with life. On this occasion, it was a big Halloween party thrown at "some guy" from high school's house. It was a big house that he inherited from his parents - 6 bedrooms, pool, giant yard... you get the picture. I should also mention that Frank and Dorothy don't do anything spontaneously. We had to get together and plan our costumes just in case, god forbid, we might overlap. It ends up the I am going to do the full Scotsman in a kilt outfit, my wife is going as a cat, Frank was in a full body head to toe skeleton costume, and Dorothy is going to be one of those Octoberfest girls (quite possibly the Octoberfest girl with the least amount of cleavage on record).

Knowing this in advance, I decided I'd have some fun and bought the same costume as Frank. My plan was to slip away, change costumes, and see what I could get away with.

Party night comes around and we all meet up, dressed as planned. Dorothy is in the traditional German dress with the shoulderless shirt and a half bra that had to be stuffed a little to "help the girls out a bit".

It was a big party and kind of crowded which was definitely to my advantage. I went a got everybody drinks making sure Dorothy got a strong one. She's not much of a drinker so it shouldn't take long for her to start feeling it. My wife wanders off to some people she hadn't seen since we moved away. Frank starts looking for people with whom he could relive his glory days as the high school band drum major. Well glory days for him anyway. The rest of us were tired of hearing him talk about it.

Dorothy was hanging in the kitchen being kind of a wall flower and nursing her drink so I slipped away and switched costumes.

I came back to the party and saw that Frank was now outside. My wife was still off with her friends, and Dorothy was still of the kitchen (and a little red in the face) with her empty cup. I got her another drink and circled around behind her. Putting my hands on her midsection I rubbed up and down a little and brushed my cock against her ass. She gave me one of those coquettish looks and brushed it off with a playful "stop". I let her get back to her drink and her wallflowering.

A short while later I came up from behind again and slyly put my hand up her skirt.

Yep. Granny panties.

She pushed back against my hand and said "what's gotten into you" but nonetheless smiled and blushed a little. So far so good. I left her with her drink and her thoughts.

I found her shortly thereafter waiting for the bathroom. Since coming in from behind seemed to be working, I came up from behind and rubbed my hands from her belly to her tits while nuzzling her neck. She pushed her ass back and wiggled a little into me while frantically making sure no one saw but made no attempt to push me away.

While she was in the bathroom I scouted the second floor and found a dimly lit guest bedroom. When she came out, I took her by the arm and pulled her into the bedroom, closing the door. She made like she was resisting but didn't put up much of a fight.

I pulled up my mask just a little bit but not enough that she could see who I was and started kissing her neck. She was moaning and clearly liked it. I reached behind and unsnapped her half bra and pulled it off, letting the stuffing fall to the floor. She jumped a little at that and said "Oh my god you are a pervert" but once again did not put up much of a fight.

I moved down and started kissing and sucking her nipples. Like I said, her tits were small. Looking at them now, I saw that she essentially has huge pointy nipples and not much more.

As I was moving from side to side on her tits (with her loving every minute of it), I started stroking her pussy over her panties. She didn't resist at all and actually parted her legs some to give me some room to move my hand a bit. It seemed like she was going into some kind of a trance from it all. She was doing nothing in return or to protest. It was like she just closed her eyes and let it all happen.

Not wanting to break the trance, I quickly moved down and pulled her panties straight off. She made a loud gasp and said in a shocked but hushed voice "you're crazy" but again, didn't put up any kind of fight.

I pushed her back on the bed, spread her legs, and dove in on her pussy. As I expected she had a full giant bush. It was obvious she tended her bikini line but there was no hint of ever trimming at all. I spread her labia and could tell that she was really wet. I started gently with my tongue, just kind of tickling her inner labia, avoiding her little clit for the moment. Head back, eyes closed she was obviously enjoying herself. Now she started talking.

"Oh my god what are you doing? You haven't done that since we were first married."

"That feels amazing, oooohhhhhh!"

I guess Frank was pretty vanilla.

She started getting really wet and abandoned talking in favor of making quiet moans. Clearly she didn't want anyone to hear. I focused on her clit at this point and she started bucking her hips a little. Taking the cue, I slipped one finger in her pussy and then another and started on her g-spot. She was clearly lost at this point having turned into a ragged breathing mess. After a couple minutes she started with the "Oh my god oh my god don't stop oh god." She had a body wracking orgasm clearly unlike anything before.

I should mention at this point that both of my brother in-laws have always complained about their whistle dicks. They're small and they know it.

I don't have that issue.

Someone once commented on a picture of my cock that it could feed a family of four.

I thought about putting my now hard cock in her mouth but thought if she had a minute to collect her senses and saw my much larger than her husbands cock she might freak out. I also thought to myself that I had better go big or go home. So I did the next logical thing and pulled my cock out and started working it into her pussy.

At this point she just made a kind of a startled gurgling sound. Clearly she now realized that I was not her husband but was in such a state of orgasmic bliss she didn't know what to do. Apparently she decided to just go with it because she just laid back and closed her eyes. Her pussy was tight. I mean really tight. Clearly Frank was indeed the owner of a whistle dick. I worked it slowly and after about a minute she relaxed and accommodated all 8" of my rather fat cock. I started picking up the pace and she started with the "oh gods" again. She had her eyes closed and was clearly in a mix of stunned disbelief and sexual fervor. I kept going, increasing the pace. The "oh gods" kept coming. To my surprise she actually started pinching and pulling on her nipples. After about 3 or 4 minutes (this was intense), I picked up the pace and came like a freight train thrusting hard and fast. That brought her over the edge to a place I don't think she had ever been. Her body was actually convulsing and the only intelligible thing I could make out was "holy shit" and "Jesus".

Before she could recover I quickly pulled out leaving her pussy gushing my cum, tucked in and closed the flap on the front of the costume (which wasn't easy), picked up her bra and panties, and ran out of the room.

I quickly went to where my main costume was stashed, cleaned up a bit, and changed back to my real costume. The skeleton and her underwear were hidden so I could get them later. I went back to the party and about 10 minutes later saw Dorothy coming down the stairs looking totally self conscious as she now no longer had a bra or underwear. She probably still had a little cum leaking out of her pussy too.

Her husband came over to ask where she'd been and whether she was having good time at the party. She mumbled something like "yes it's a nice party" but was clearly having some sort of turmoil in her head. I imagine it was something like "Oh my god I just had sex with someone who was not my husband but holy shit those was the most intense orgasms I have ever had."

Later on I went over to talk casually with her for a bit but she all of a sudden excused herself and hurried to the bathroom. I guess the cum kept randomly leaking out because she repeated that mad dash at least two more times. It was also fun watching her make sure her skirt stayed down and she was continually checking to make sure her braless tits weren't showing through the white top.

As the party wound down, I went and got the other costume, her underwear, and the camera.

Did I mention that I had a spy cam set up in the room?

The next day my wife went out for a bit so I hooked up the memory card to have a look. It was perfect. Clear sound and picture. You could see that my cock was clearly not her husbands and that she wasn't fighting any of it. In fact this would be the perfect blackmail footage. Maybe I'll get her to suck my dick yet...