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My Diapered Affair

By Diaperhump

This is not the story of the first time I got to enjoy diapers with someone else, though that one is fairly exciting and I might write that one down as well. This is the story of the second woman I diapered, how it almost didn't happen, and how hard it was for both parties to put an end to it.

First a little background about me, and the story. I am currently 32 at the time of this writing; I was 28 when it took place. I am a lifelong diaper lover, not an AB at all though I have found I have a bit of a strict daddy side. This fetish is 99 percent sexual for me, thus this story has a strong sexual content. There are no bottles, pacifiers, or baby talk in this story. No age play of any sort really, except when I made her call me daddy during sex.

I was working in a retail shop, what kind doesn't matter, when I met Katie (not her real name). She was 19, and looked very naïve and innocent. She had sexy long brown hair to the top of her waist. She had big beautiful brown eyes, a perfect smile, and the perfect ass for a diaper. That was actually the very first thing I thought of when I saw it. She had a few extra pounds to speak of, but was by no means fat. Her weight was in all the right spots. She had fairly large breasts, a small waist, and a perfect round voluptuous behind. I had really developed a taste for larger rear ends, I discovered they really filled out a diaper after the first woman I diaper (ok, definitely going to have to write that story too).

So we started to work together, and we hit it off fairly early on. She had a boyfriend which didn't bother me much (the first woman was married, yup good story), but you never know when it might bother the girl you're interested in. So I took my time, and played it cool, and over time it seemed like she did like me as well. So one day I asked for her instant messenger address so we could chat away from work, and of course that was my way of pressing the issue without a crowd of coworkers. Long story short, half way into our first online conversation I had convinced her to come over. Since this is a diaper story I won't go into the non diapered sex stories with too much detail. It was hot, we had a great time, said we would do it again, and we did, every chance we got.

A few weeks into the "relationship" we got to talking about our fantasies, I wasted no time in telling her mine. She was not repulsed at all, even curious. We almost did it right then and there because I told her I had some diapers right in my closet. Unfortunately she had to go, so we didn't get the chance that night. We had plenty of more chances to do try it, but I told her I was not going to push it. I wanted her to be comfortable with the idea completely before we tried it. So our regular, but still hot and steamy sex continued.

Meanwhile in my personal life.....I had been seeing a woman for almost two months shortly before I met Katie. However it had ended, quite abruptly about a week or so before I met Katie. One day everything was fine, the next she wouldn't return my calls. No harm, no foul, and I moved onto Katie. I even considered asking Katie if she would leave her boyfriend for me. However during a conversation Katie and I had she basically implied that we were just a fling, and she would not be leaving her boyfriend anytime soon. So when the other woman wandered back into my life as quickly as she wandered out of it I decided to give it another chance. Now I thought I would have to end things with Katie immediately. After some thought though I decided not too. After all, this girl could leave any second like the first time, and furthermore my girl told me she was not ready for a commitment. So to me that was permission to keep doing what I was doing.

Katie was aware of this woman coming back into my life, and she didn't seem to mind. She had her own boyfriend, so how could she be mad about me seeing someone. I did however make it clear to Katie though, that if I did make a commitment to the other woman she and I were done. I know it is judgmental of me, but I could never be a cheater. I didn't and still do not mind being the other man, but actually cheating was something I just couldn't handle.

So, as you probably already guessed, the commitment came. I ended things with Katie. We did however remain very good friends, even though shortly later I changed jobs. We remained in regular contact, talking almost daily. She had besides the sex become one of my best friends.

One night during a conversation I told her I had one very large regret. She didn't even ask, she simply said it, "You never diapered me". Smart girl I thought and the conversation went from there. She asked me questions about diapers that she had never bothered to ask when we were together. The whole thing got me very turned on, I couldn't help myself. I looked at the clock, my girlfriend would be at work for 4 more hours, and that only mattered if she decided to stop by. I had to have Katie, in a diaper, now.

Katie was there in fifteen minutes, which was amazing since it was a 25 minute drive. I don't think she wanted to be in a diaper that badly, she just wanted "us" again that badly. We came together, kissing, touching, and tearing the clothes off each other all at once. She smelled good, she felt good, it was right. I had already laid out an attends for her. It was one with a wait band, with six white tapes and attends written on tapes. I broke out kiss, and spread the diaper out. I laid her down on the diaper, getting it in the right position for the perfect diapering. Once I knew it was in place I got down on one knee, and began to lick her already wet pussy. I nibbled on her clit, which always drove her crazy. She was moaning, and almost whimpering, she kept saying how much she missed me, I stopped and told her I had missed her too.

She was more than worked up, and so I decided to finish the job of getting her diapered. After the last tape was fastened I began to rub her pussy through the diaper. I asked her if she liked the feeling, and she gave a very honest answer, "I didn't think it would be anything special, but it feels really really good". I smiled, and had her stand up. I rubbed her diaper all over as I kissed her; I turned her around and rubbed my now very hard cock up and down her diapered ass. Oh my god, that diapered ass. It was even better than I had fantasized, which believe me was pretty spectacular. I wanted to remember this forever, so I made her pose for me. She bent over, got on all fours; I even made her rub herself through the diaper. I still have those pics too.

Enough pictures though, I had to have this girl. She stood up again; I sat on the edge of the bed and made her got on her knees. She proceeded to take my hard cock in her warm wet mouth. Bouncing her head up and down, I was lifting my hips off the bed slightly matching her strokes. She stroked part of my shaft with one hand, I told her to rub her diapered pussy with the other so I could hear the diaper crinkle. After a few minutes of that I made her play with my balls, but I slid my leg out so she could hump my leg. She was like a dog in heat, humping that diapered pussy up and down my leg, moaning on my cock, sending waves of pleasure down my shaft.

She let my cock slip out of her mouth with a pop, wiping her lips she crawled up and straddled me. She began to hump against me as I sucked on her now rock hard nipples. My nipple play made her rock harder on me, and it was my turn to moan loudly. She could feel how slippery my cock was against the plastic with her spit and drool covering my shaft. She asked if I liked that feeling, I grunted my approval with a mouth full of tit. She of course didn't know of my screen name of Diaperhump (contrary to many beliefs it is not referring to a messy diaper). She got up went to my night stand and got the bottle of lube I kept in there. I covered my cock in it, and began to hump me again. Oh it felt incredible. I sat up, and kissed her and she humped her diapered pussy into me. I was matching her thrusts, harder and faster we went. I was about to explode, so I grabbed her and made her slow down. I broke out kiss and told her to get on all fours on the edge of the bed. She so, and as she waited for me to approach she wiggled her diapered ass for me. She asked me a question that nearly made me cum on the spot, "Do you like my diapered ass Daddy?" She and I had discussed me being called daddy during diapered sex. She was a little weirded out by it though, so I never thought she would do it, but there it was.

I rubbed my lubed cock up and down her plastic padded ass a few times as I undid one of the tapes on the side. I was able to pull the diaper to the side, and then I slid right into her diaper pussy. I held myself inside her, rubbing her diapered ass and relishing the feeling of her hot pussy that I had not had in what seemed like forever at that point. Slowly I began to fuck her. Long, deep strokes, holding her diapered hip with one hand, and reaching around, rubbing her clit through the diaper with the other. She was working her ass against me; I was mesmerized by her perfect diaper ass, as her diaper started to crinkle slightly. We were both close, and I told her I would not last much longer, "Fuck me hard in my diapered pussy Daddy". That was all the encouragement I needed. I took my hand off her clit, grabbed a fist full of hair and began to fuck her hard. Pulling her back onto my cock with her hair, slamming my cock into her, her diaper was now crinkling loud enough it seemed to echo in the room. Harder and harder with every thrust, I spanked her diapered ass, making a loud thud and crinkle when I did.

"Ooooh Daddy, please spank me, I have been a naughty girl".

"What have you been?", I asked, she knew the right answer, as it was something we had discussed.

"A dirty diaper slut Daddy". Yes she had I thought, and so I spanked her again and again. I yelled out I was going to cum. She told me to cum on her diapered ass, and that sent me over the edge. I pulled out and began shooting my cum all over the smooth crinkle white plastic. She immediately reached back and began to rub it around. I swear that gave me a second mini orgasm right there, and I came the most I ever had.

It was over, amazing, but over. We caught our breath, cuddled for a bit, and then it was time for her to go. I got her out of the diaper, cleaned her up some, she got dressed, and I walked her to the door. She asked if this was our official last time together. I had to be honest and say yes; after all I was going to have to deal with a lot of guilty feelings that I never had to face before. I didn't know how I would handle it. I asked her how she handled it. She told me that in her case she was not happy; she went looking for something else. In my case I was pretty happy with my new girlfriend, and it just happened, I didn't go looking for it really. So she didn't know what else to tell me, told me she would be in touch and was gone.

My girlfriend came over that night. I confessed my fetish to her, and she promised she would try it for me, sometime.

A week later I was talking to Katie online, and she asked how I was dealing with it. I told her how I reacted that night, telling my girlfriend about my fetish, and that she had said she would try it. Katie was happy for me, and I guess I was a little happy too. I didn't feel guilty anymore. So I told Katie there was no reason we couldn't still hang out and do things that friends do, and she agreed. However she still needed to be discreet since her boyfriend was always suspicious of her having guys for friends. I understood and told her my new girlfriend seemed to be the same way. I asked her if she wanted to go shopping with me that night, and she said sure. I told her I would meet her in an hour, that there was also a place I wanted to show her while we were out. She asked me where? I told her it was a nice quiet place, very secluded....."Bring a diaper Daddy"....

Katie and I had a lot more diaper adventures, if anyone cares to hear them I will write them down. Thanks for reading!

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