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.
