As luck would have it, my boss informed me I had to attend an all day conference in a city about 2 hours from us, on a Friday. Being that it was an all day affair, he told me that the company would pay for a hotel if I wanted to stay over for the night after the meetings.
I mentioned this to Maggie, who said they were going to be on October break for a long weekend (she works in a school). She wanted to know if I could work it out so that she could attend the trip with me. I knew my boss wouldn’t mind (it wouldn’t cost them any extra), so I told her if she could get her mom to come stay with the kids for one night, it would work out.
Luck was in our favor, as her mom agreed to spend a day with the grandkids. I booked a hotel in the area, and looked around at the hotel website to see what we could plan for the evening. The hotel had a nice restaurant overlooking the water, so I knew dinner wasn’t a problem. When I looked for a “nighttime entertainment” spot, I found that the hotel had a bar/nightclub that seemed to cater to the late 20’s and 30’s crowd that we would fit into. After looking at the calendar, I found that the Friday night we were going to be there was going to be a costume themed party. (This was the closest Friday to Halloween). I wasn’t sure if my wife would go for that, but I got a phone call, and figured I would run it by her that evening.
That night I mentioned it to her. She surprised me by saying, “That sounds like fun”
“What kind of costume should we wear?” I asked, knowing that we would have to come up with something a little more original than we normally wear.
“I’ll take care of that”, she said, “You just worry about booking the hotel and your workday”.
As always, time flew by, and the week of my day trip was coming up. Maggie informed me that she had everything taken care of, including my costume. I asked her what she came up with.
“Oh, I made a trip to the goodwill store, and we’re all set”, she said, matter-of –factly.
“Can I have a hint?” I asked.
“No”, she said. “After dinner, we’ll come back to the room; you will put on your costume, and go down to the party and wait for me.”
The meeting day came, and after saying goodbye to the kids, we left early in the morning for the drive. Maggie slept during the trip there. She kept the car to spend the day shopping, and she was going to check into the hotel in the early afternoon.
After lunch, I got a text message telling me what room we were in. The afternoon dragged on, and eventually it was over.
At dinner, Maggie was quite flirty with me (after a few glasses of wine), and we were both charged up for the evening ahead. When we got back to the room, she got out a bag with clothes for me. I was going as a hobo/clown, and she put makeup on my face and got me dressed. She made no attempt at putting on her own costume, and told me that I was to go down to the party and wait for her.
“How will I know when you get there?” I asked.
“Oh, you will definitely know”, was all she said.
With a kiss, she sent me out the door. I showed my room key at the bar to gain entrance, and made my way to the bar to get a beer. From my bar stool, I noticed quite a variety of costumes, ranging from silly to scary to sexy. There was a mixture of couples, single guys, and party girls out to have a good time.
I was on my third beer, and beginning to get worried that Maggie wasn’t showing when I noticed that a woman in a “prostitute” costume near me had a familiar voice.
I looked over and saw her costume. I hadn’t recognized her earlier, because she was dressed completely out of her character. She had on a wig, which changed her hair color from brown to red. Her “prostitute” costume was complete with a leather mini skirt, which barely covered her ass, fishnet stockings, with garters showing just below the hem of her skirt, and a low cut satin top, that revealed almost all of her luscious breasts.
She inched her way over to me while she was sipping on her drink, which I gathered was just purchased for her by the person she was talking to; a “bandit” dressed in tight jeans, cowboy boots, a black cowboy hat, a denim shirt, and a bandana that covered the bottom half of his face.
They moved up next to me at the bar. I had a close look at both of them as they were talking. As Maggie was talking to him, she played with her red hair, twirling it in a flirty way. The bandit whispered something to her, and as he did, he slipped a dollar bill into her garter, and walked away to a table. She turned to me, while waiting for a drink order, and asked me, “so…. Do you like the costume?”
My first instinct was jealousy, but then I realized that with her wig, and my costume, that it was going to be fun to play a little game. I also realized how turned on I was by this game.
“I like it, I give you an A for creativity”, I replied.
“Just watch a little while longer if you want to enjoy a show. I am sure enjoying my new attention”, my wife answered.
At this time the bartender brought a drink order to her. She borrowed a tray, and went over to the table where the bandit was now seated.
There were 3 other guys at the table: a pirate, a police officer, and a doctor. (All in costume of course) She gave them each their drinks, and they all tipped her by putting dollar bills in her garters. They asked Maggie to join them and she slid in the booth between the guys. A few minutes later, a waitress, dressed as a nurse, came by selling shots, which were contained in a test tube. I watched as guys purchased quite a few of them. I couldn’t tell what was being said, but I heard my wife lean in a little to hear what was being said to her. I saw her laugh, and I noticed the doctor pulled out a $20 bill and place it in my wife’s garter. Maggie then stood up, took one of the shots, and placed it between her bulging cleavage. She then got up on the doctor’s lap, facing him, and slid her body up his, so that he could drink the shot directly from her cleavage. I noticed that some of the drink spilled on her, but she made no attempt to wipe it off. As she was sitting on his lap, I noticed the doctor had his hands on her ass. I couldn’t tell, but it looked like the far hand was under her costume! Could she really be letting him cop a feel of her butt? Or even her little pink hole!?!?
For the next 15 minutes, Maggie went from lap to lap with each guy getting a little bit bolder. Her hands would drop down in front of her from time to time and I couldn’t see what was going on but it sure looked like she was feeling their packages as they were taking the shots.
After this was repeated with the other guys, Maggie excused herself to go to the restroom- she stopped by me on the way back, laughing, and said, “you might want to come over and join us- but don’t forget to give me a tip”.
She grabbed me by the hand and took me over to the table, placing another shot between her boobs, and bent me backwards over the table, sliding the booze down my throat. I wanted to blend in, so I tipped her too. Instead of the garter, though, I grabbed her crotch area and slid the $20 into the front of her panty area. The back of my hand brushed up against her panty and she gasped, the stimulation was too much for her! I noticed she was quite wet too.
Over the next hour, Maggie took turns dancing with all of us on the dance floor. I noticed she got quite a few looks with her outfit. While there were many other seductive costumes, she was the only one to successfully get dollar bills stuffed in hers.
I took my turn dancing with her, and Maggie rubbed against me while we slow danced. She told me she was quite turned on. She told me that each of the guys had gotten a finger in her whilst groping her butt on the dance floor. She said she even had one in her butt. Maggie said she couldn’t take it anymore, she was so wet as worked up she wanted to fuck right here in the dancefloor! She didn’t even care with who!
I had always had secret fantasies about watching her get fucked but never thought it would go anywhere. I never even brought it up with her for fear she would think I was crazy and now here we are and she is begging for some sex!. I knew I didn’t need to worry about anyone recognizing either one of us, and quite frankly, with the costumes that the guys were wearing we wouldn’t recognize them either. When our dance was over, Maggie excused herself to the restroom again, and on her way back to our group, a man in a tuxedo stopped her. I then watched them talk for a minute, and he sat down in a corner chair, as Maggie gave him a lap dance. I was amazed at her talents as she ground her ass into his crotch.
Maggie slid her way up to her “customer” and I watched him press his face into her chest. She held her spot for about a minute, and then slid back down, adjusting her top as she did. He slipped something in her garter, and she walked back over to us.
She was standing by me, and I could tell her face was flushed, even under the exorbitant amount of makeup she was wearing.
“I was rubbing my pussy against his crotch, and he pulled his dick out. I was grinding on it then pulled my panties to the side and started riding his shaft. He exploded on my pussy and in my costume. I couldn’t help it, I came too”, she reported to me. I looked down and could see her pussy was wet, with some leaking down her leg.
I wasn’t jealous at all, and also noticed the $100 bill in her garter.
The police officer noticed the $100 bill, and asked her how she got it.
Maggie told him that a “customer” had paid her for a lap dance.
“For a hundred bucks each, can we get lap dances too?” I asked, daring her to tease a little more.
This peaked the other guys’ interest, except the pirate, who had drunk so much he had passed out.
“I’m in for a hundred, you know, for a private lap dance”, he said. The cowboy bandit and the police officer were in agreement.