It was my junior year of school. My high college sweetheart Mandy and I had parted methods and I was becoming much more comfortable with my kinks. Being in school I hadn’t really grown confident enough in them to ask girls to participate along with me but I knew what I liked for sure. After four years with Mandy I really embraced the school lifestyle, finding dates and hookups wherever I could.
Enter Katelyn into my life. I had actually known Katelyn in high college when I was dating Mandy. We were both on the track team together. I was a few years ahead of her and she never really registered on my radar, but according to her she had a gigantic crush on me in high college. While I doubt that’s why we ended up at the same college this culminated on my 21st birthday where she invited herself over to my house and she pursued a random hookup with me that resulted in us dating pretty seriously.
She was strong. She was confident. She was horny as fuck at all times. She was what every guy wants out of a school girlfriend – someone to push boundaries with. Some crazy to stick your dick in. That first night we were together she showed me her VCH piercing and introduced me to my first experience with squirting but that’s a story for another time. She was the sort of girl who would put in an all star performance, drain my nuts, cum twice, and then lay back with her vibrator because she wasn’t quite satisfied yet. In other words, way out of my league.
Katelyn was a tall 5’8″ and very fit. She was a non scholarship participant on our university’s swim team and had the body to match. She was fit in all the right places. She had shoulder length brown hair and an ass that she definitely got from her mother’s Jamaican side of the family. For a nympho she took her studies very seriously – often skipping out on social functions to study to my dismay. She would go on to receive a PhD in math some years later.
We had been dating for nearly a year when she came down with some bronchitis strain that really put a stop to our sexual exploration. It got bad – she was missing classes and frankly I was missing sex. It was mid November and finals were quickly arriving, so we needed to get her well so that her grades didn’t slip. Her parents booked her an appointment with a specialist back home and she asked me to give her a ride. She had her own car, but her coughing fits were so bad that her parents were worried that it would be dangerous for her to drive. That would be no problem of course. I could drive her back on Thursday night, stay with my parents through the weekend and we could make the trip back to school Sunday evening.
The drive was about 400 miles. With gas stops factored in we could make the trip in about 6 hours. Following my last class of the day at 4:00pm, I gassed up my car, and swung by her dorm to pick her up. I gave her a call to let her know I was parked outside and watched as she made her way down from the third floor – her dorm had an external staircase that led up the side of the entire building with a landing at each of the levels for entrance into the hallway. She was carrying her black swim duffel bag over one shoulder, with a 1 liter nalgene in her left hand. She was wearing grey bike shorts and a tight black shirt that didn’t quite cover her stomach.
She was walking down the stairs and as she reached the second floor landing she had a coughing fit. She doubled over. It lasted a solid 15 seconds, and as she coughed her shoulders slumped a bit causing her duffel to slip off. Her coughing ceased, and she remained motionless for a few seconds longer. Her head snapped up, and she looked down at me her face flushed. She motioned down to me holding up one finger and mouthed “just one second!” Fumbled in her duffel for her keycard then raced up the stairs.
I didn’t see her come back down the stairs, so it caught me off guard when she opened the passenger side door of my old civic. I feigned ignorance and asked “what was that about?” but I had already noticed she was now wearing my favorite jeans shorts – so short her front pockets hung out of the bottom. They showed just the right amount of butt cheek when she walked and tight enough to give her a perfect cameltoe. She had told me one drunken night that she could syntribate on her piercing just right while wearing them and would occasionally do that to orgasm in class. I thought about that a lot actually, so it was pretty surprising to me that her normally pronounced cameltoe was absent.
We were pretty open with each other sexually, yet while she knew about how much I loved her squirting, she wasn’t yet aware how much I would love to watch her wet herself and fantasized about it regularly.
She loaded her duffel in the back seat, and stated “oh, nothing I just forgot to take my cough suppressant.” She was obviously trying to play off her wardrobe change like nothing had happened, so I decided to play along on account of her being sick. She pulled a textbook out of her duffel, and hopped in the front. She was seemingly in pretty high spirits despite the cough.
“How are you feeling, anyway?”
“Not half bad” she replied with a chipper voice. “It’s just this fucking co~” she was cut off by another coughing fit. She recovered and said “really, it’s only this lingering cough.. but I feel fine otherwise! They just won’t let me back in class while I’ve still got it”
“Well we had better get on the road then” I said as I put the car in drive. “I’d like to get us in before midnight.”
“Do you mind if I study for a bit?” She asked. I shrugged – just glad she was going to get it out of the way early. It wasn’t going to be a terrible drive, but it would be long enough that I’d definitely want some company down the home stretch. “I was working though this proof addressing the minimum number of colors it takes to fill in a map with no two adjacent in a 2D plane…”
And with that, I pulled out onto the main road and put the setting sun at our backs.
Everything went fairly uneventfully for a while. She had this habit of taking a swig from her nalgene to punctuate a thought after reading back a statement to herself in her sing-song studying voice rhythmically under her breath. It was a little endearing. Such a hot little nerd, even when she was sick.
Her coughing had died down a bit – presumably due to the cough suppressant she took before leaving, but just before one of the last exits out of town she was hit with another fit. She covered her mouth and convulsed repeatedly.
Her coughing died down and she looked over at me red faced.
“Are you gonna be ok?” I asked.
“Yeah… but I’m really sorry, would you mind pulling off at this next exit?”
“Sure,” I said, as I put on my blinker. “Do you want me to just pull off on the side? Or…?”
I had assumed, hoped even, that she had coughed her way into wetting herself. I wasn’t going to bring it up of course. In a rare display of fragility, she took a sheepish tone.
“Actually, I think there’s a CVS off of this exit, I was wondering if you could stop there?”
“Sure thing! What do you need?”
“Well this is a little embarrassing, but ever since this cough started I’ve been using panty liners…” her cheeks were flush as she moved her hands out of her lap, “and I ran out this afternoon. I wondered I could just triple up on underwear, but we’re not even out of town yet and I’m… I’m… kinda a little soaked”.
Her shorts didn’t _look_ soaked, but with her flushed cheeks and pleading tone I wasn’t going to argue with her. I could feel the blood rushing to my cheeks. It’s like she had a radar for my arousal because despite her illness she changed her tone and asked me in a slightly more silky voice “Are you ok?” She raised an eyebrow and her eyes darted down to my lap and back up at my face. The redness in my cheeks must have betrayed my feigned apathy.
“Uh yeah – I’ll.. just discover that CVS.”
“Oh thanks so much… you’re the best boyfriend ever!” she bubbled, returning her attention to her textbook.
I continued driving, trying to glance over and see if there was actually any wetness in her lap – trying to not get caught while doing so.
We arrived at the CVS, a mile and a half off of the freeway. My brain was running haywire with the thought of what was happening between her legs, but I was doing my best to hide my excitement. While her nose was buried in her book, I shifted myself so that my penis would be restrained by the waistband of my grey basketball shorts and open front boxers.
“You… wouldn’t mind going in and buying them for me, would you? I don’t…” she looked down at her crotch and started again, “I’m worried someone will see.”
“Yeah, I can do that!” I exclaimed, my shaking voice betraying my confidence. It wasn’t that I was against buying her pads… it was just… let’s be honest, really hot.
“Thank youuu!” She called to me as I got out of the car. “They’re the Tenas and they’ll be in with the feminine products”
I stepped into the cool air of the CVS and made my way back to the “femine products” aisle. My mind was focused on my task as I walked towards the tena pads, but then I saw the “depends” and that put an idea in my mind that I just couldn’t shake.
I was a bit embarrassed as I checked out. I had never bought these before even though I had looked at pictures of girls wearing them hundreds of times on the internet. One time back when I was a freshman, my roommate had walked in on me with /r/girlsindiapers pulled up on my screen, and I had to play it off as a joke that my friends had sent me. “Can you believe some people are actually into this?” I had sheepishly asked him. Luckily I wasn’t in a compromising position yet so I was able to laugh it off. I don’t think he suspected…
That same feigned smoothness was on full display as I checked out. “Wow she sure is getting big…” I stammered as the clerk ignored me. I took my mile long receipt and headed out the door.
Back at the car, Katelyn was waiting for me. I was all in now… no turning back.
I silently thrust the bag in her direction as I entered the car and she pulled out princess pull-ups – L. “Is this some kinda joke?” She asked with a hint of anger in her voice.
I did my best to laugh it off. I probably could have come up with 100 other different excuses that I thought of after the fact… like they were out of the Tenas.. or in hindsight I probably could have just told her the truth: I thought it was hot but all I could come up with was a lame “hahah yeah, well I just figured since..” I finished my attempt at a joke by nodding towards her lap.
She coughed one of those internal suppressed coughs and then leveled her gaze at me for what seemed like an eternity.
Eventually I caved from her withering stare. “Ok ok… I hear you. I just wondered it would be funny. I’ve got the receipt, want me to go exchange them?” I stammered holding up my wad of CVS tape. I wasn’t really looking forward to that conversation with the clerk on why I was returning pull-ups and I was already figuring out ways I could just throw them away and eat the cost… or shit, in for a penny in for a pound, just go in and buy the Tenas and somehow “forget” these in the car to play with later. I had never bought diapers before after all…
“Nah. I suppose these will work as long as they’re not too small!” She said while wiggling out of her shorts and… 4? 5? Pairs of panties? At this point I can’t remember, but it was a few. She wadded them up and threw them on the floorboards before I could really inspect them for any wet spots. My heart racing I tore open the pack of pull-ups and handed her one. She looked it over, figured out which side was the back, raised her knees to her chest and put her legs through the holes.
It was a bit of a struggle for her to get it up over her hips without tearing the sides – particularly while sitting in a car. I often wonder if anyone walked by during the ordeal. She was a bit of an exhibitionist and wouldn’t have minded, but my heart was racing and I had tunnel vision watching her work them up over her hips and shaved pubic mound. Even if there were five people standing outside our window watching I wouldn’t have noticed.
She got them pulled all the way up and eventually wiggled back into her jeans shorts. The gusset of her faded denim shorts didn’t look particularly wet. Her multi-panty barrier must have done its job, or any errant wetness was contained within the darker spots along the seam where fading wasn’t as pronounced.
She raised her hips and bridged her shoulders against the back of her seat to flatten her stomach. She attempted to button her shorts. It took a bit of struggling on account of the pull-up, but she got them fastened. Her normally skin-tight tiny shorts were puffy in all the right places. The seam down the center was cutting into the padding giving the illusion of a cameltoe. As she settled in to her seat I caught a glimpse of the pink pull up elastic and padding peeking out where her shorts were too short to fully cover them.
“You know you’re gonna pay for this, right?” She asked me with the waistband of her pull-up poking out of the top of her shorts.
“I already am” I replied with the color rising in my cheeks as I started the car.
I tossed the remaining pull-ups on the back floorboards and made for the freeway. Katelyn went back to her math, reading to herself rhythmically under her breath and taking a swig of water after every corollary.
The drive went more or less uneventful from there. Out of respect for her illness I mostly just tried to forget the absolute fantasy that was playing out in my car. She finished up what she wanted to study in math after about 50 miles, and we were rocking out to Hot Hot Heat soon after. Occasionally she would let out a few coughs but her suppressant was more or less doing the trick preventing any massive convulsions.
Around mile 150, Hot Hot Heat turned into a Jimmy Eat World album and her energy changed. She wasn’t singing as much. Her knees were together and her toes were pointed.
Occasionally she’d bounce her knees a little bit. She was suppressing her coughing more, trying to minimize the impact on her full bladder. I realized what was up and it brought her situation to the forefront of my mind. I couldn’t shake it even though I was trying my hardest. I felt at least a little guilty for involving her in my fetish without her knowledge and was starting to doubt that it was a good idea at all.
“Hey babe?” She stammered out as she reached for the volume knob cutting off the chorus of Night Drive, “How much farther do you think it is until we stop for gas?”
“I’ve got about a quarter tank left. I figured we’d stop in our ordinary spot at the halfway mark.”
“Ok… it’s just, I think I’ve really gotta go…” a hint of desperation in her voice. A bit more than I would think was warranted considering the situation. Was she fucking with me?
I smiled back at her, “Kate, we’re making such good time. Do you really want me to stop, or can you try to hold it?” She bounced her knees a bit and slid her hands in an inverted prayer position up to her crotch.
“I guess I can try to hold it if you want, babe.” There was something in her voice. Something about the way she said it that made me suspect that she suspected that I was secretly enjoying this. I was. Every time she coughed I knew she was spurting a little here or there. I knew she was thinking about what she was wearing and getting comfortable with it, and I knew it was only a matter of time until we had this conversation. After all it seemed like every time we drove home together we had the same ” can you make it to the gas station?” conversation, and it was always around the same mile marker.
Maybe we had had one too many drives together where I had subconsciously slowed down a bit when she asked me that… but it was like she knew. Maybe now was the time to finally breach the topic. We continued down the road another 5 miles in relative silence – punctuated by her occasional squirm or knee bounce.
“Hey Kate, I’ve been meaning to bring up…you know what I would think is pretty h~” I started but at that second she began a violent coughing fit. One hand went to her mouth. Her left hand grasped my thigh for stability. She doubled over onto her knees, until her coughing died down.
I tried to keep my eyes on the road, but couldn’t resist glancing over.
With one hand still on my thigh, she sat back in her seat and slumped. I felt her grip on my thigh relax slightly. Her legs spread slightly and her right hand went from her mouth down the puffy space between her legs, her right palm resting on her pubic mound, fingers curling down between her legs. “I just can not hold it anymore” she admitted quietly enough that it was obviously not meant for me, but for herself. Her eyes closed.
Her right hand relaxed. She remained still for 20 seconds, her fingers feeling the warmth spreading between her legs. That’s when she came to and caught me staring. “Oh. My. Gawd. Eyes on the road please!” She yelled. She stared at me and I stared at her both of our mouths agape. I hit the rumble strip snapping me back to reality. She could see me breathing heavily, my cheeks flushed. I jerked the car left back into our lane.
She sighed. “Well I feel much better” she stated, relief heavy in her voice. Then in her regular more composed silky voice, “but it looks like you might be feeling a bit desperate yourself.” She moved her hand to my very obvious erection that had poked through my front boxer opening, now tenting against my basketball shorts.
I had the presence of mind to put on my cautions and began to pull onto the shoulder. She grasped my shaft through the fabric and began slowly stroking, moving the soft fabric up and down my dick. “If I didn’t know any better I would think you actually liked watching me lose control in my diaper, didn’t you, dirty boy?” She opened her knees a bit wider and crept the fingers of her right hand slowly up her inner thigh under the leg of her shorts. “You’re such a naughty boy! You set me up for that didn’t you?!” She feigned sultry anger as the car passed over the rumble strips and came to a stop. “Was that it? Do I have it right? You wanted to watch me lose all control in a diaper? You wanted to see me pee myself?” her grip tightened severely, almost painfully, as she pumped.
I looked over to see her rhythmically circling her fingers under the leg of her shorts and diaper. Her speed increased on my shaft. She loosened her grip slightly so the fabric would glide across my sensitive skin. She let out a performative high pitched moan with each stroke. She knew I was close and I was putty in her hand.
I barely had enough time to get the car off the road. As it came to a stop, it was all far too much for me. I could feel the pressure building between my legs desperate to get out. My glutes tensed and my hips bucked involuntarily into her hand. My kegels began twitching against my will. She teased me with a playful “Just let it all out for me baby. Cum for me.” I tried to hold back to save face, but my body betrayed me. I bit my lip obeyed. I came hard. Shockwaves of orgasm rushed over me. I shot rope after rope directly into the front of my grey basketball shorts. The stain was growing and there was absolutely nothing I could do to stop it.
She released her grip and cooed as she touched the wet spot that formed had where the head of my dick was straining against my shorts. I had pumped so much cum through my them that it wasn’t merely a wet spot but it had sticky white texture. She put her fingers to her lips tasting my cum and smiled devilishly.
“Awwe” she said in a fake pouty voice, “I guess you couldn’t hold it, could you?” She deliberately looked down at my lap and bit her lip. “Let’s get to the gas station – I think we both need a change.”