The Bet
It was Saturday night and the Red River Rivalry football game was on. I was a Texas boy so my team in burnt orange was facing off against Oklahoma University. I had met my girlfriend a month before so we were still getting to know each other. We were both adamant fans. She liked OU and I liked UT. Well, before the game got started I told her I would like to place a bet on behalf of UT. She was down for it and asked what the bet was. I suggested the loser had to wear whatever the winner wanted for a night. She quickly agreed but said nothing too skimpy. I proposed that if she lost then she would have to dress like a baby for me, diaper and all. She laughed, agreed, and retorted by saying I would have to wear a pink maids dress. Wow, this was the best of both worlds for me. If I won she would be diapered for me and if I lost then I had to wear a pink maids dress. We both agreed and as the game proceeded I got nervous. UT was losing bad and I was stuck in a corner. I decided to shoot for the moon on this one so I confidently told her I wanted to double the bet even though my team was losing. The loser would have to wear the pink maids dress and diapers. With more of a scoff than a laugh she agreed. As the 4th quarter clock ran out I knew I was in for an experience. UT lost the game and now I had to get my dress and diapers ready. Luckily, I had both on hand unbeknownst to her. I figured this would be a great way to let her know about my habits without is sounding weird. We made a date for the next night. I was to meet her at the mall at 5:30pm and she would take me to Victoria’s Secret to select a bra and panties for me and a nightie for her. As I met her at the gate to the mall I saw a smirk on her face. With a quick embrace and a kiss she grabbed my hand and practically dragged me to Victoria’s Secret. We were only there for a few minutes but it felt like hours. She selected a matching pink set with sparkling silver stars for me and a turquoise nightie for her. We had dinner and then went to a movie. I squirmed the whole time because I knew what was coming. When the movie was over she told me she would meet me at my place in a few minutes. My heart was racing about as fast as my truck in traffic and when I got home I quickly unpacked my items. First the diaper, followed by the panties, bra, and petticoat. Finally I slid on the dress and let it fall into place. I smoothed the folds and tied the white sash while I waited for her contemplating my fate. Shortly there was a quick knock at my door and I dutifully answered it like the maid I was dressed as. When she caught sight of me she burst into fits of laughter and I turned many shades of red. She had me curtsey for her while she made some phone calls telling her friends. When her laughter had subsided we decided to watch a movie. After that was over she was feeling really hot. I took her to my room and seductively undressed for her. I left the diaper on so she couldn’t see exactly how turned on I was. What ensued next was by far the most mind blowing sensual moment I have had. She pounced on me like a cougar and I devoured her with my tongue. Back and forth my slippery devil slid in her mouth bringing her to new heights. I moved lower and caressed her perfect breasts. She started to get even more turned on. With a quick jerk I had her lying naked in front of me while my *gift* tented the front of my diaper. She grabbed my manhood as I slowly flicked my tongue inside her most precious area. When she started to squirm I took one finger and slowly slid it in and out of her. She arched her back and told me, “You are driving me crazy, Harder” With that I added a second finger while my erection pushed on the folds of my diaper. With a scream she came and a redoubled my efforts. I slowed my rhythm with two fingers and she pushed into me. Her vagina was heating my fingers and I added to the steam with extra friction. As I pulsed back and forth she arched her back once more and came a final time. With her last effort she collapsed on the bed and kissed me full on the lips. Because tonight was about her I did not push my needs, I simply wished to please her. Many diaper lovers are all about themselves and are only concerned with getting off. I loved this girl too much to press my concerns. With a final kiss I placed my hand on her bare breast and drifted off to a blissful sleep.
I can hardly say I learned my lesson by losing the bet. But this was definitely a learning lesson for both of us. She learned that I would do anything for her, and my secret desires were expressed and fantasies made real. Perhaps I should place more bets like this in the future…
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