Warning: This story contains descriptions of sexual acts between consenting adults. If you might be offended by this, or if you are not yet 18 years of age, or if it is illegal to read materials of this kind where you live, then please stop now.
My Halloween Date
by Daddy Bear
Every year, our homeowner's association has a Halloween party at the clubhouse. It's usually a lot of fun and people put a lot of work into their costumes. This year, my neighbor, Jimmy really outdid himself.
He got a short blue skirt and tight, pale yellow top from his wife, and dressed up just like her. In fact, I'd seen her not so long ago in that same outfit. To top it off, he put on some red lipstick, shaved his legs (not that his legs were all that hairy to begin with), and was wearing some blue heels.
As for myself, I was decked out in an old baseball uniform, my cap arranged jauntily on my head. As soon as I walked in, I headed over to greet that sexy girl, Jimi.
She was talking to one of the neighbors, facing away from the door, so she didn't see me come in. I walked up behind him, put my hand on his ass, gave it a squeeze, and said, "Well, hello there, sexy." He gave a little jump, and turned around with a nasty look on her face, but when he saw it was me, he got back into character, slapped my hand away, and replied, "Oh you brute!"
I'd always suspected that Jimi was kind of faggy, and this just cemented that opinion. I decided that I was going to have a little fun with him (her?). Jimi was definitely all girl tonight.
"What are you drinking, sweetie?" I asked. "A Fuzzy Navel," she said. How girly is that, I thought to myself, and when to get some bourbon and another Fuzzy Navel for her. I slipped the bartender a couple bucks to put a little extra peach schapps in Jimi's drink.
When I got back, I handed Jimi the drink and asked, "Hey, where's the wife?"
"Oh, she's being a party pooper," he said.
"Mine, too," I replied, "She said that she wanted to be around when the kids came trick or treating. You can be my date instead." At that, she blushed a little. She's getting into this, I thought to myself.
We talked with some more of the neighbors, none of whom could believe how sexy Jimi looked, and I joked that Jimi was my date for this evening. Every time I said that her face got a little redder as she denied it.
Then, the band started playing a song that Jimi particular liked, and I asked her to dance with me. Again, she was kind of hesitant, but in the end, the booze won out, and she said OK. We got out there and started shaking our booties.
The next song was a slow one, and looking into her eyes, I took her and pulled her close to me. She resisted a little at first, but then gave in and we pressed up against each other. There was no denying the attraction now. I could feel her little dick was stiff as it pressed up against my bigger and even harder cock. Maneuvering ourselves to an out-of-the-way corner of the dance floor, I groped her ass and we ground against one another.
When the song ended, we held onto each other for a little longer, then looked at each other, and went, "What just happened?" I said, "Let's go outside and get a little fresh air." I took her and led her out.
Once outside, we found a secluded spot where no one could see us. I pulled her close again, but this time, leaned in for a kiss. Holding her tight, I could feel her little thing get stiff again, and mine got hard again, too. I held her tight and pushed my tongue into her mouth, and she moaned.
I hiked up her skirt a little and slid my hands up under it. She was wearing a thong, so her ass cheeks were bare. She moaned again as I groped her ass and pressed herself harder against me. I don't know long we were out there, making out like a couple of teenagers, but after a while, I could feel her tense up and then jerk a little. Holding me tight, she whispered, "Oh, Dan, you just made me cum in my panties."
That made me smile. I whispered back, "Oh, Jimi, you're such a sexy girl."
At that, she dropped to her knees. She undid my baseball pants, reached in and found my hard cock in my jock strap. Looking straight into my eyes, she fished out my hard cock and licked the head, making me tremble a little. Seeing that that had the desired effect, she took the head into her mouth, and slid down the shaft.
"Ohhhhhh, Godddddddd," I moaned. She was making love to my cock with her mouth, and it was apparent to me that she'd done this before. She was amazing. I knew I wasn't going to last long, and I didn't really want to be caught out with my pants literally down around my ankles, so I just went with it.
Pretty soon, I warned her, "I'm going to cum." She kept right on sucking, if anything a little harder, and soon, my balls tensed up and I began squirting my cum into her mouth. She stayed down on it, swallowing every drop, all the while looking straight into my eyes.
When she did come up for air, and I had pulled up my pants and she had smoothed down her skirt, she gave me a kiss, and I could taste my cum on her lips. We hugged each other tight, and she whispered in my ear again, "Oh, Dan. That was so sexy. I need to go get cleaned up, but I want to do this again sometime."
"God, yes, Jimi. Me too," I managed to reply. Then it hit me that I better get myself back together and the lipstick wiped off my lips and neck before I headed home. I gave her another quick peck, and then she was gone.
When I got home, I headed straight upstairs to take a shower. My wife called out from the kitchen, "How was the party, dear?"
"It was fun," I replied, "You should have come with me." But, obviously, I was glad she stayed home.
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