by: Anonymous | Story In Progress | Last updated May 2, 2024
Chapter Description: Stephen's girlfriend arrives and things get heated...
Stephen began to sprint the moment the door closed. His first stop was the shower. He was not going to have his first time with a girl be ruined by her complaining about his odor from football practice. Next he brushed his teeth for good measure. Stephen planned to shave as well but found he didn't need to. His face still looked and felt like he’d had a close shave even though it had been a few days since he’d last used a disposable razor,
“Weird, guess the universe is doing me a favor for today.”
He said as he chucked his football gear in the hamper. Stephen’s next agenda item was deciding what to wear. He decided to play it cool and put on a pair of black boxers, jeans, and a White V-Neck shirt. The final vanity ‘to-do’ item was making sure his drying hair didn’t look stupid. As he ran his fingers through the brown locks crowning his head he looked at his phone and saw a text from Katlynn letting him know she was on her way,
“Oh fuck the pizza,”
Stephen exclaimed, running for the kitchen. By the time the doorbell rang, he was just pulling the pizza out of the microwave. His panting breaths were audible as he opened the front door. Katlynn looked at him, raising an inquisitive eyebrow,
“You okay there, stud? You just work out or something?”
He kissed her,
“No, just finished getting the pizza ready, come on let’s eat.”
After thirty more minutes and a slightly awkward small talk exchange in anticipation of the evening's big event the couple stood in Stephen’s bedroom facing each other. Now that the moment was upon them the young man was starting to feel self conscious so he tried to get things moving,
“So, uh… how do you want to–”
He was interrupted as Katlynn put her finger on his lips. She gently guided him to the bed, motioning for him to sit as she started to strip in front of him. Stephen’s whole body felt hot as he watched her work shirt come off and then her pink polka dot bra she was wearing underneath. He’d bought it from Victoria’s Secret for her for her birthday with money he’d made working over the summer. The bra made her already decent rack look irresistible, but the plump pink nipples underneath were even better. Katlynn started swinging her hips back and forth as she pulled her jeans down next, revealing a tight pair of hot pink panties with white lacy trim. Those came down next and Stephen for the first time got a good look at her virgin sex. He felt his dick growing hard in his jeans as he took in her naked feminine form. He started moving to remove his own clothes but she interrupted him, grabbing his arm gently,
“No, let me.”
He surrendered to her intoxicating touch as Katlynn pulled his shirt off. She threw the shirt aside and traced her fingers over his pecs. Incredibly aroused, Stephen was already starting to get in the danger zone in regards to blowing his load early. He started to say as much but she put her hand on his lips to shush him again as she helped him to stand. The brunette beauty got on her knees and unbuttoned her boyfriend's pants, revealing the large erection currently tenting Stephen's boxers. The quarterback bit his lip in aroused anguish as her hands yanked his pants down around his ankles then suddenly pushed him back onto the bed on his back. Katlynn leaped on him and began passionately rubbing his cock through his boxers.
Stephen, gasped. What was she doing? This wasn't the plan they were supposed to be going to go all the way. Why was she masturbating his dick through his underwear when he was already so close to blowing his load? Stephen couldn’t let her continue, he had to tell her to stop or he’d cream himself and ruin their whole night, or at least the next embarrassing thirty minutes until his cock would be ready to go again. He went to say as much when something began to feel different with how Katlynn was teasing his cock through his boxers. It felt like she was holding a pad or something that was expanding as she rubbed his cock with it. He could even hear the rustling of plastic getting louder as she massaged him with the mysterious object. He could also feel the cool air of the bedroom on his upper thighs which didn’t make sense if he was wearing his boxers. Confused, Stephen looked down to see his girlfriend’s hand was now massaging his penis through what looked to be some sort of diaper for teens. The offending object had bright blue elastic sides and the padded body of it was decorated with blue and white stripes along with a graphic to mimic the front of boys underwear. Stephen stared at it in confusion and horror for a moment as the awkward encounter continued. He gasped as Katlynn suddenly rubbed his penis in just the wrong way and he crossed the point of no return.
“Oh, no no nuuuuuuuugggh,”
The boyfriend who had been so eager moments before moaned pathetically as his cock began to spurt and empty its load into the nighttime diaper that had appeared around his waist. To make matters even worse, Katlynn took her hand off at the point of climax, ruining Stephen's peak and making the prolonged climax painful and unsatisfying. As soon as Stephen began to come down from ejaculating, feelings of incredible embarrassment and frustration overtook his psyche. The diapered teen barely managed to hold his composure as he tried to not cry in front of his girlfriend and salvage the abhorrent situation,
“I'm so sorry, I didn't mean t-...... I mean I'll be ready again soon sor-....,”
Katlynn laid down next to him with a concerned expression on her face. She placed her hand on his chest.
“Are you okay, Stephen? Did you have an accident? Do you want me to get you a new goodnite?”
Stephen looked at her in shock, then looked down at the cum filled nighttime diaper he was wearing. He stood up in horror completely dumbfounded as his mind tried to make sense of what was she was saying,
“I don't… I mean I didn't… I mean.”
Katlynn started to tease his cock again through his new striped blue nighttime diaper as she attempted to console him. Stephen stared at her stupefied,
“Stephen, it's fine. I know you wear goodnites to bed. You've told me like a hundred times since we started dating. If you had an accident or something I can grab you a new one it's not a big deal. A lot of the kids at my work wear them too. I'll even put it on you if you want. You never know, it might be sexy.”
Stephen looked at her with his mouth open, completely speechless. She couldn't be serious. He tried to push back,
“Katlynn, what are you talking about?”
Continuing, the teen boy gestured to his current ‘underwear’,
I don't wear these diapers, or goodnites, or whatever they're called. We're supposed to be having sex and instead you're offering to put me in a diaper? And why were you rubbing me off? I thought you wanted to go all the way!”
Katlynn looked at him with a disappointed expression. She sighed and got up from the bed quickly. She began to put her clothes back on as she responded,
“I told you Stephen, we can't have sex till you turn eighteen. I know it's only a one year difference. but in our state it's technically illegal for an eighteen year old to have sex with a minor and I'm just not comfortable with that. Are you really going to spend our first night hooking up throwing a tantrum over your diapers? I mean you've been asking me to touch your dick all year and now that I'm here you're going to whine like a baby to me that you have to wear diapers to bed?”
Katlynn took a moment to composer herself but she was clearly very upset,
“Look, Stephen, I'll still drive you to school tomorrow but I think we might need to rethink our relationship. You're just not very mature and before you say anything, no, it's not because of the diapers.”
Katlynn finished getting dressed and walked out of the room as Stephen stared at her in horror. Getting a grip, he began to chase after her in his soiled goodnite,
“Wait, Katlynn, please don't leave. I'm sorry! Something crazy is going on. I don't wear diapers and I'm eighteen. please don't leave…”
Katlynn was already out the front door. Stephen moved to follow her but remembered what he was wearing and stopped. She called out to him as she got in her car,
“Learn to act like a big boy, Stephen. Then maybe one day a girl will want to have sex with you.“
Stephen's mouth hung open as she drove off. He sat frozen for half a minute with only his goodnite on staring down the porch till the empty space in the driveway stirred something in his mind.
“Wait, what the fuck? Where's my car?!”
The Curse of the Sundial (Commission)
by: Anonymous | Story In Progress | Last updated May 2, 2024
Stories of Age/Time Transformation