This happened to me about 2 years ago when I was 22, the summer before my last year at college (yes, I was on the 5 year program). I'd decided to spend the summer in town rather than go back home so I could hang out at the beach on the days off and party on the weekends. Though I'd moved out of the Fraternity a couple of years ago, the rent in the summer was so cheap I decided to move back in for the 3 months provided I'd get my own room – which I did.
I took a job at the local Walgreen's to help pay the bills - this is where I first met Josie. She was a pharmacology student at a nearby college while I was studying Poli Sci at the university. We hit it off pretty well, one party led to another, led to us in bed, led to us dating.
That summer was pretty much a blur, and though she was only 21, Josie was quite a bit more experienced than me in bed. I though we were trying a lot of new things, every possible position, keeping the lights on, making love in the shower. Only later did I learn that Josie was starting to get bored. See I guess my lack of experience made her hesitant to talk to me about some of the things she really wanted to try. It was 3 weeks before the next year was to start and she later admitted that she'd decided it was time for a change. There would be plenty of guys back to school come the start of the year, so she decided now was as good a time as any to figure out if she was going to stay with me or leave me and find someone more exciting.
That Friday, as usual, we went out with a group from work after it closed. We went clubbing, drinking, and ended up back at her place where I'd often spent the night. It was about midnight but since both of us had the weekend off, she grabbed a couple more beers before we headed off to bed. We normally end up having sex before going to sleep, but that night I just kept getting more and more tired. By the time I fell in bed I couldn't have had sex with her if I'd wanted to (she later admitted that she'd put a mixture of a diuretic and sleeping pill in my beer).
In the morning I woke up to her saying, "Oh my god, what happened." I sat up thinking something was wrong, and then realized her hand was on my crotch and I was completely wet. "You wet the bed! You wet the bed like a little baby," she said. I just stammered, not sure what to say.
"Well at least you're still hard," she said, "move over here and at least get out of the wet spot." Next thing I knew she was on top of me and just really attacking me. I mean our love making can sometimes be intense, but this was a whole new level. She came at least 3 times, getting me even wetter with her cum, the last time my orgasm setting her off again. We collapsed together and when we regained our composure a little, she just said, "don't worry about it, accidents happen to all of us." I started to say something but she just said "sshhhhhh" and kissed me.
Throughout the day I was so aroused from our lovemaking that morning I just couldn't get over it. 2 or 3 times throughout the day she'd say things like "how's my baby doing," or "aren't wet again are you." It was always said with a big smile so I just took it all as a joke.
That night (Saturday) we went out clubbing, dancing, had a great time. She was grinding against me the whole time like she'd never done and was just more wild than ever. I was walking around with a hard on virtually the whole night – thank goodness the it's really dark in that club. When we got back home she went in the kitchen and came out with 2 beers. This time though, she said, "Race ya." We'd done this several times and I usually won, but she was a good challenge. No different that night as I beat her again.
She just smiled and said, why doesn't the victor come get his spoils, as she stripped on the way to the bedroom. Well I was right behind her and we fell into making love quickly, both very turned on from the day. However, after 5 or 10 minutes I started to get tired. She just stood up, looking at me, "Really? I remember what happened last night and I will NOT have you getting my bed wet again just because you party too late."
I looked at her confused, thinking that was all behind us. "I won't wet the bed again," I said.
"I know you won't," she yelled over her shoulder as she left the room. She came back in, "and I'm going to make sure of that. Tonight you're wearing a diaper," she said as she brought in a pack of adult diapers.
"What, no" I tried to protest but it was getting harder to push her away (later she admitted that she'd also spiked my beer that night as well).
"Look, I don't know what happened last night, but I don't want a wet bed again tomorrow morning. Here's the deal, you wear diapers tonight, if you're dry in the morning then no harm, and in fact to make it up to you, I'll do anything sexually you want, anything."
So I figure, what's the big deal, I'd always wanted to see her with another girl and here was my chance, so I gave in, half asleep as she pulled the diaper around me, then pulling me next to her I drifted off.
The next morning I woke up with her hand on my penis, rock hard, only then did I remember I had the diaper on. I heard her whisper, "someone was very bad and wet himself again last night."
I suddenly realized she was right, my head was spinning and I didn't know what to think, but she kept stroking me. "You were very bad, you know that," she said.
"Yes, very bad" I said, playing along as she rubbed me harder and harder. I'd never seen her look like this before - so turned on. "Tell me how bad you are," she whispered.
"I'm so bad," I croaked.
"Does the bad boy want to cum?"
"Oh yes" I said as I was already so close. She squeezed my balls and rubbed me through the diaper, looking her in the eyes. I saw them glaze as suddenly I came, so hard. I saw here tremble, almost as if she'd cum at the same time.
She sat on my face and was wetter than I'd ever seen her in my life. My tongue just touched her and she started to moan, cumming harder than I'd ever seen her, flooding my face with sweet juices. After about 10 minutes I realized I really had to get up and pee. I asked her if we could stop for a minute so I could, but she said no use the diaper.
At this point I figured what the hell. As she ground her pussy against my mouth I started to pee. I felt her hand on the diaper, heard her mutter, "Oh god" and she came. I'd never known anyone to cum like this, clamping my head so I could barely breathe, her whole body shaking, literally squirting cum all over my face.
She rolled off me and just looked at me, smiling. She told me how that was more intense than anything she'd ever experienced. How she'd never done anything like that and couldn't believe how much it turned her on. She asked, almost casually if id mind wearing diapers for her again some time, not all the time, but maybe to mix things up.
At this point I'd had more intense sex in the last 48 hours than I could ever remember. "Sure" I said, if you'd like that. She just cuddled next to me and said she had a confession to make. She told me that she'd put the drugs in my beers the last 2 nights as this had been something she'd always wanted to try but knew I wouldn't just agree to it.
I was a little pissed at first, but then just laughed... what the hell, no one got hurt and she sure did loosen me up.
That was 2 years ago. We've now tried a lot of things neither of us ever thought we'd do and our sex life is anything but boring. Still this is one game she really enjoys and brings up from time to time – like when we were driving to some friends 5 hours away. She said she'd take the first leg driving, and again slipped me something in my coffee. I fell asleep virtually as soon as we left the driveway, waking up a couple hours later. She looked at me and grinned, "Oh, it looks like someone's been a bad boy again," realizing the front of my jeans were soaked - but that's another story.