A couple of winters ago my girlfriend and I got into making cute little bets, usually of a sexual nature but sometimes they were for pride or for control of each other. This was one of those times that she displayed her love of controlling a man.
Susie, my girlfriend in my mid-twenties, was my May December romance. We'd met through a working relationship with her company and over time got to know and respect or revere each other for our skill sets. She wasn't a particularly easy woman to get to know and most of the guys that tried got shut down pretty quick but she admitted she liked my confidence level and willingness to jump into the fray. At the time I was more interested in her cocky attitude and the fact that she was a hot little blonde with nice full 34d tits, a trim waist and 36 inch hips. She had a deep bronze tan that she wasn't afraid to show off when the time was right.
Both being baseball fans we were enjoying a very close final game in the world series when she pipes up and tells me she wants to put a bet on the winner of the last game. Never being one to turn down a bet, especially one of her "fun" bets, I simply asked her what the stakes were because I was definitely going to be all in.
"If I lose then I'll take you on any trip you want, including the Bahamas," she tells me, knowing that I've been dying to do some diving around the islands there. She'd made the stakes impossible to turn down. So I asked her what she wanted if she won. This was when I was going to get quite a surprise.
"If I win, then you have to be my slave for thirty days, any thirty days of my choosing, and do everything I say without fail. Oh, and most of the things you'll be doing," she hesitated, "you'll be naked."
Now, to be honest, I was a little put off by the stakes she was asking for but I had taken worse bets before and won. Plus, I really thought I had a guaranteed win here betting on my New York team. So I told her she was on, but asked why naked?
"Not too many women my age get to have a naked younger man around, especially one that's their slave. And with all the time you spend in the gym, it's fun to watch you strut around," she gleamed as she explained her reasons. She knew I was in on the bet and the flattery was just sealing the deal.
"Alright, I'm in, but if I win I pick the resort and the island we stay in when we get to the Bahamas," I told her.
When the last game of the series came a week later I had been anxious all week long listening to the sports channel and studying the statistics of the opposing team. I was still sure that I had the game pegged, even up to game day and had excitedly invited some friends over to watch the game and have a few beers. By the sixth inning of the game things were starting to look bad as neither team had scored a run in six innings. If the game ended in a tie then our bet would automatically default to the winner of the last game and would be screwed, or rather stripped of my free will and dignity no doubt, for whatever month she chose.
As the bottom of the ninth inning rolled around my girl Susie comes out and joins us anxiously watching her team as the first player takes the mound. She sat in a chair almost biting her nails as she watched the first pitch. The first two at bats were struck out with little effort. As she looked at me with a nervous look on her face, I was grinning from ear to ear beginning to sing in my favorite Bahamian accent. Getting so into my gloating I nearly missed the first pitch of the third at bat until I noticed a wide eyed look on her face. The third in the lineup knocked a third base run into deep center field.
"Looks like someone's cute little ass belongs to me," she exclaimed.
"Never gonna happen babe, I hope you've got your passport ready."
The forth in the lineup took the plate and we were both excitedly waiting for the pitch. When the pitcher wound up and the ball shot at home plate I nearly came out of my seat until the batter suddenly shot down the first base line running for his life. The ball was in the air as the camera followed it, the announcer repeating 'going, going, going, gone'. The game was over, score two to zero and I had lost my shirt, literally this time. Looking at Susie she was more excited than I'd ever seen her and had an evil grin on her face.
Nearly a month went by before I realized it and it was November. I was about to get out of bed one morning and I felt Susie's hand running up my back as she whispered 'wake up sleepy head'. Rolling over in bed that Sunday I looked into her wide eyes and she smiled at me.
"So, it would seem you owe me," she laughed.
"Huh, owe you what?" I asked her, half tired still.
"It's time you pay up on the world series, remember?"
Damn, I thought to myself, I had almost forgotten about it the past month had been so busy with work and all. I sorely hoped she wasn't serious about collecting as the weather was getting colder outside and the month was going to be quite busy for me...especially with the holidays coming up soon. I knew her better than that though. She enjoyed getting her own way.
"Alright," I told her, "but can I get a cup of coffee in me first before you start abusing me?"
"Certainly," she laughed. "But don't get dressed, for the entire month you're not allowed to wear clothing unless I say you can".
As she skipped out of the bedroom, leaving me laying there imagining the dirty fun we were going to have, watching her ass bounce in her lacey shorts made my dick spring to life. Feeling the semi-hard erection I had growing I crawled out of bed and strolled down to the kitchen to pour a cup of coffee and try to wake myself. Getting to the kitchen, Susie's maid Loretta was busy cleaning as I walked in. Loretta was a pretty little thing in her early thirties that came around three times a week. As I walked into the room it dawned on me that Loretta must have been warned about my new apparel restrictions. She looked up at me as I walked in, greeted me with her usual good morning sir.
"I'm sorry Loretta," I sighed, reaching for a mug. I wasn't really sorry, just a little embarrassed that I was standing there in the buff while the maid was cleaning the kitchen. It's not like I had anything to be ashamed of. I stood six foot three and weighed two twenty five. The four days a week playing racquetball and working in the weight room had kept me trim and given me a visible six packed abdomen.
"No, don't apologize," Loretta smiled, covering her mouth as she stared at my hardening eight inches that I could feel involuntarily twitching.
