Losing and Winning
Copyright© 2012 by Wayne Gibbous
Erotica Sex Story: Chapter 1 - I made a bet at work with a woman I knew and I won more than I ever dreamed possible.
I get along with most of the people I work with but I especially like kidding around with Debbie, one of the accountants in the office.
First, she's cute, about five-four, curly blond hair, blue-grey eyes, slender but curvy figure and just a perky, fun person. Second, she also turns me on in her sexy way being just flirty enough get my cock hard when we talk.
We're both single and there's just that bit of sexual undercurrent between us. She's a few years younger than me, I'm thirty-two, she's in her upper twenties. And she was also a big pro football fan like I was.
We both worked in Pittsburgh where I grew up. Debbie is from Cleveland and that's central to the story I wanted to tell you.
Now, that means almost nothing unless you're a football fan. The Pittsburgh Steelers and the Cleveland Browns are fierce rivals and their fans tend to be rabid supporters.
So, when the teams were scheduled to play one another, usually twice a year, Debbie and I would razz each other unmercifully. This came to a head right before their next match-up when Debbie said she was so sure the Browns would win she was willing to bet on it and challenged me to it.
"They don't have a chance and I'm willing to put money on it, big boy, so let's see just how tight a fan you are for your precious Steelers," she said one afternoon as we were leaving work.
"I'll take you on but it's got to be good, something really good," I popped right back. I had always had my fantasies about Debbie and one in particular fueled my next statement.
"The loser will clean the winner's apartment and do it naked, how's that?"
She laughed and said, "You're on. Hope you know how to dust and vacuum."
I really thought she'd turn my bet down, just laugh and tell me I was being stupid. But she didn't, she took it and I told her she was on.
Now all that had to happen was the game which was in three days.
I have to admit that I masturbated during the first quarter of the game, turned on when the Steelers were ahead by seven, just so excited that I would have Debbie dusting and vacuuming my place in the nude, her nice boobs out where I could see them while she paid off the bet. Oh, I was so excited.
Then, they lost. I sat there, not believing that in the last ten minutes, the Browns scored two touchdowns and trampled the Steelers. Shit.
My images of Debbie, naked, pushing my vacuum cleaner around vanished as I realized that it would be me, Ben, my cock hanging down, guiding her vacuum cleaner around while she giggled.
But the odd thing was, I was now hard as a rock. I was excited that I was soon going to be showing my equipment to this hottie I worked with.
The next day, I got to the office early but she wasn't there yet so I reluctantly went into my office to wait for her to show. Right before eight, I heard Debbie's voice out in the open office as she greeted some fellow workers and I braced myself for gloating.
"Hi, loser," she said as she put her hand up to her forehead making the capital L sign with her fingers. "How's Saturday?" she laughed.
"Yeah, you win, Saturday's fine," I groaned and she nodded and left as we both started our workdays.
Oddly, in a way, little was mentioned of the bet the rest of the week though it did enter my mind at times, usually giving me an erection as I thought about it.
So, it wasn't until we were almost ready to leave at the end of the day on Friday that she came over to my office and handed me a slip of paper with her address on it.
"So, when do you come to clean? I've cleared my whole day, anytime's good for me."
I told her about ten and that was pretty much the end of things.
Her address went into my GPS that evening and it told me that I was about twenty minutes away from her apartment so about quarter of ten the next morning, I got in my car and headed out.
I had showered and put on a teeshirt and a pair of shorts and sandals. That was all, no briefs, why bother.
I got up to the door of her apartment and pressed the bell as I stood there with my erect cock folded up against my abdomen.
"Well, the maid has arrived, come in," Debbie said grinning ear-to-ear. "I've been waiting for this," she added as I went inside.
"Here's the vacuum and some dusting cloths and a can of spray stuff. I'll just watch while you get ready."
She sat down smiling up at me as I pulled off my teeshirt and kicked off my sandals.
Then I opened my belt and undid the button at the waistband, then stopped and looked at her.
"Don't chicken out now, Ben, you lost, remember?" and I pulled my shorts down a few inches so the tip of my cock was out.
"Oh, I like this," she tittered, "Come on, get it over with."
I pulled them down another inch or two so about half of my cock showed.
"You're stalling, Ben, let's see it, all of it," and I slid them off down to my feet and kicked them away, standing there with my cock at a forty-five degree angle pointing right over her head.
"Hmm, okay, let's get busy. I love to watch a man do housework, especially like this," she said and I pulled out the electric cord on the vacuum and plugged it in and began vacuuming the carpet as she lifted her feet, grinning up at me. I moved it by her, leaning over, trying to get my cock as near to her face as I could, then on to the rest of the room.
I finished the carpet then turned off the vacuum and began dusting and polishing the furniture including the side table next to where she was sitting, bending over, putting my cock just inches from her.
"I like your work, Ben. Do you hire out on a permanent basis?"
"Oh, not usually, it would have to be for someone special."
"Just don't leave any marks on the furniture with that, okay? It looks like it could scratch glass, even," she laughed as I went around dusting the pictures on the wall.
"Well, maybe it isn't so big that it would cause a problem."
I had figured that my equipment might come in for a little ribbing and sure enough, there it was. While I'm not hugely-endowed, I have about six and a half inches and it serves me quite well. And whomever I'm with from what I've been told.
"Oh, I try not to cause problems with it. It really likes to give pleasure rather than problems."
She laughed again and I continued on dusting and polishing.
After a few minutes, she said, "I do provide coffee breaks for my workers, would you like to take a break?"
I said I would and she came back in a minute or two with a tray and we sat there having coffee, Debbie in a pullover and shorts, me, naked with my cock now hanging down some having become more used to being exposed.
Then, her doorbell rang.
"Would you get that? It's part of a maid's service, after all," she said grinning.
"You did lose the bet," she added and I got up and stood there as the bell sounded a second time.
"Do your job," she called out as I could envision every female I worked with standing in a group on the other side of the door.
So, I hung back and opened the door slightly, looking around to see a young woman standing there.
"Debbie invited me over, um..."
"Let her in, Ben, let her come in," Debbie shouted and I sucked in my breath and pulled the door open as her eyes widened and a smile broke out across her face.
"Um, thank you," she said and went by me while I closed the door, my face warm with embarrassment.
I slowly followed her back to the den and stayed by the door until Debbie said, "Come in, Ben, and meet my friend."
"Jennie, this is Ben, Ben, Jennie. He's here cleaning my apartment."
"Um yes, nice meeting you, Ben," she said extending her hand in welcome.
"Nice meeting you, Jennie."
"We were just having coffee. Would you like to join us? Then, Ben has to get back to work," she explained and soon the three of us were sipping coffee as Jennie asked, "Is this a special cleaning service you've hired?"
Debbie laughed and told her, "No, it seems that Ben lost a bet and he's here paying it off."
"Oh, perhaps I should bet with him as well," she laughed. "He could come over and clean for me."
"Ah, but you might also lose and have to clean for me?" I told her, after all, Jennie was a very attractive young woman and I'd love to have the situation reversed.
"Could happen, I guess," she said and then Debbie told me there was also a load of wash for me to do.
We finished our coffee and she showed me to the washer/dryer and the basket of laundry waiting next to it.
"There it is, Ben, all yours, mostly my underwear. I thought you might like to do that."
I laughed as I picked up a tiny thong and looped it over my cock.
"We should make you put it on, Ben, but you might stretch it," Debbie laughed as I took it off and dropped it into the washer. Next, I picked up a lacy bra and held it up to my chest.
"Well, there's one place I'm bigger than you," Deb said as I looked at the tag seeing it was C-cup.
"Yes, and I think you should show me. After all, you and Jennie are getting to see me and she wasn't even part of the bet."
"Does seem unfair, doesn't it?" Debbie said. "But, well, that happens, sometimes," she laughed as I kept lifting up her underwear and dropping it into the machine.
"Mmm, I like these," I said as I held up a pair of panties. It was the tiniest lace thong I'd ever seen and the tiny front panel was open in the middle. "Looks like this makes things convenient. Don't even have to take them off or slide them aside," I said grinning at her.
"Oh, I'll never tell. They are convenient, though," she told me as I went through the rest of her basket adding things to her wash.
There was certainly no dowdy, frumpy lingerie in Debbie's wash, I really wanted to inspect some of them closer but thought that might just be pushing things a little too much.
So, in went the detergent and I closed the top and dialed-in the settings for a gentle wash.
"Oh, a man who knows how to use a washing machine. How nice, Ben, you may attract someone even yet," she laughed.
"One of my many talents, I'm told."
"Oh, many admirers, is that it?"
"A few but honestly none that has ever worn anything quite like that little thong that's open in the front."
"It even seems large enough for you to fit through it," she said, nodding toward my crotch.
"It's something we could try, I suppose," I popped back with, hoping that she might agree.
"Well, it's in the wash, too late. Or, maybe..."
"I could get it out?" I began but she cut me off saying it was already wet.
"Maybe now you should strip and change the bedding," my boss for the day said and she led me into her bedroom where I began taking the sheets off, piling them on the floor, then pulling the pillowcases from the pillows and adding them to the pile.
Debbie went in the closet and came back with an armload of fresh linens and handed them to me so I began putting the bed linens on and sliding the pillowcases on. Soon, I had her bed nicely made as I stood there proud of my work as my cock hung slightly.
Jennie handed me the duster so I could do the furniture and pictures around the room, then I went into Debbie's bathroom and began straightening up her countertop and rinsing out her sink as they followed me from chore to chore.
"Ah, we use the same toothpaste, interesting," I commented as I cleaned and arranged her toiletry items.
"Does that thing ever rest?" Debbie asked me, nodding down to my middle.
I laughed and told them the truth, "I think being out like this, he thinks there might be something in the offing, something he should be on the lookout for."
"Every man's cock is an optimist," Jennie laughed as she picked up the feather duster from the counter and began sliding it back and forth along my cock's hard shaft.