The Sleepover (Patreon)

“Hmmm, I’m not sure it’s a good idea love.” His mother remarked.

“Mum please, we’re old enough now it’s fine nothing will happen.” Jessie replied.

“I just don’t think it’s appropriate for a boy to be sleeping over a girl’s house, what does her mother think about it?”

“She said its fine.” Jessie said beginning to get quite frustrated.

“We’ll let me talk to her first.” She responded, not entirely convinced by her son’s truthfulness and decided to leave the conversation.

Jessie shook his head and returned to his room, sitting back down at his desk in a huff. His friend Misty had invited him over for a sleepover, her mother was quite progressive and didn’t have anything against the idea of a boy and a girl being close friends and sharing those types of experiences together. Jessie’s mother however needed a bit more convincing, she had been his age once upon a time and knew exactly what teenagers his age got up to when they were no longer under the watchful eyes of their parents.

She trusted her son, but a parent’s trust could only go so far, she was afraid he would make a mistake and the last thing she needed was her son who was soon to graduate from high school getting someone else’s kid pregnant.

She toyed with the phone in her hand for a moment before dialling the number her son had given her.

“Hello, sorry is this Misty’s mother?”

Jessie tried listening in on the conversation but his mother caught him lingering in his bedroom doorway and quickly shut herself out of earshot in her own room.

“She’s on the phone with your mum now, can you hear what they’re saying.” Jessie said sitting on his own phone with Misty.

“Not really, just relax my mum will convince her that its fine, I can’t wait to see you!”

“Yeah me either.” Jessie said blushing.

If only his mother knew his real intentions and feelings towards Misty, than there was no chance he would be allowed to see her, it would appear that her suspicions were warranted after all. Jessie had had feelings for his best friend for some time now, they had been friendly for years but they had grown much closer in this past year since coincidently sharing most of their classes together they ended up spending a lot of their free time helping each other with their studies too.

Jessie quickly said his goodbyes before hanging up the phone as he heard his mother’s footsteps approaching his room.

“I spoke to Misty’s mother.” She paused looking at her son for a moment.

“Annnnnnd?” Jessie asked nervously.

“And we discussed it; as long as she’s at the house supervising then I guess I don’t have a problem with it.” She sighed somewhat dejectedly.

“Yes!” Jessie cried, running over and giving his mother a hug. “Thank you so much.”

“Just don’t make me regret it.” She said embracing her son.

“I won’t mum, I promise.” Jessie replied, ignoring any feelings of guilt from his deceptiveness.

He would be careful, they both would, he wasn’t entirely sure Misty even felt the same way about him but this would be the perfect opportunity to get even closer to her.

The sleepover was that night; reluctantly his mother was insistent that she would drop him off ignoring his requests to take the bus. It was around now that he wished he had spent the time getting his own license, but his mother was insistent that he would need a job to support owning a car and he couldn’t be bothered getting one until after he had finished school. He had grown used to taking public transport everywhere; it was pretty reliable and ran quite often in his area so he didn’t mind. It made him feel quite kiddish however, being dropped off by his mother.

“Did you pack your pyjamas, toothbrush, and clean underwear?”

“Yes mum, yes mum, yes mum.” Jessie sighed as his mother listed stuff off like he was a forgetful child.

“Don’t just yes mum me, this is your first sleepover l I just want to make sure I don’t get a phone call an hour from now for me to drop off something you forgot to bring with you.”

“I have everything I promise.” Jessie replied, growing more impatient with the juvenile conversation they were sharing.

The drive wasn’t much longer but thankfully it was spent in relative silence, his mother held her tongue back and decided not to give him a lashing about things he might be thinking of doing and instead opted to give him the benefit of the doubt this time.

“Alright this is it.” She said pulling up the drive way.

“Thanks mum, love you bye!” Jessie said quickly before running out the car.

He quickly knocked on the door before realising his mother had followed behind him.

“Mum, you can leave now I’m fine.”

The door opened and instead of Misty her mother was their waiting.

“Jessie hello, good to see you and this must be your mother lovely to meet you in person, come in the two of you.”

Jessie cringed as he realised his mother was invited in but thankfully Misty was waiting in the hallway and ushered him into her room.

“You can sleep in here with me tonight, mum said she’s fine with it there’s an inflatable mattress you can use.”

“Sounds good to me.” Jessie replied, sounding rather coy.

They hung out for a bit just chatting and eventually his mother came into the room.

“Alright I’m off now.” She looked at her son expectantly.

“Ok thanks, I’ll see you tomorrow.” He told her casually before turning his back to her.

Much to Jessie’s dismay she strode over and gave him a hug.

“Give mummy a kiss goodbye.” She said being overly affectionate.

“Mum stop.” Jessie grumbled as she smothered him and planted kisses on his forehead.

“I’m not leaving till you give mummy a kiss.”

“Ok fine!” He almost shouted eventually turning around to kiss her quickly on the cheek much to her satisfaction.

Throughout the entire interaction Misty was giggling away, and Jessie’s face was blushing crimson from all the embarrassment he found himself unable to escape from.

After his mother said her final goodbyes Jessie and Misty were finally left alone to enjoy the night. It was going rather swimmingly, they were playing games and watched a movie, talked about school and their future plans. Jessie was really swept up by Misty and found himself enjoying her company even more in this significantly more intimate setting.

Finally after a late dinner of takeaway pizza they were about ready to go to bed when Jessie’s mother called him over after catching him returning from grabbing a drink of water from the kitchen.

“Hey Jessie, just a quick word if you don’t mind?”

“Ummmm sure, that’s fine.” He replied, feeling a bit put off.

He awkwardly followed her back into her room, his nervousness growing after she quietly shut the door behind them.

“Now your mother said that you haven’t ever been to a slumber party before, is that true?”

“Ahhh yeah I guess.” He replied with a shrug.

“That’s ok sweetie, I know it can be a bit of a daunting experience being away from home for the first time, that’s why I think it would be best that you wear one of these.”

Jessie watched sceptically as suddenly she produced a crinkly pink diaper from a package.

“That’s for babies?” Jessie said looking quite rattled.

“No they’re pull ups, I know being away from home can be known to cause accidents so it’s better to be prepared until I know you won’t have an accident and ruin my sheets, besides there would be nothing more embarrassing then waking up to a wet bed.”

“I’m way too old for those, I don’t wet the bed.” Jessie cried, muffling his voice in an attempt to make sure Misty wouldn’t hear him.

“Nevertheless, while you’re under my roof you will be living under my rules, unless you don’t want to come over here anymore.” She replied with her arms crossed. “Now can you put these on yourself or do you want me to help you.”

“But those are for girls!” Jessie cried again, spying the pink padding and seeing the princess motif on the front for the first time.

“Alright, that’s enough from you mister, if you’re going to act like a naughty toddler then that is exactly how I’m going to treat you.”

Jessie fell back on her bed in shock as his trousers were wiped out from beneath him, his underwear quickly followed leaving his lower half naked and exposed.

He offered a feigned attempt at resisting as Misty’s mother expertly thread the crinkly pull up over his legs till it sat snugly around his waistline.

“There, it fits perfectly.” She decreed triumphantly.

Jessie was humiliated; she forced him to stand while she made sure the leak guards were in place ensuring it affording him the best protection.

“Ok you can go back now.” She said with a satisfactory smile.

“But what about my pants?” Jessie asked in disbelief.

“I think it’s better you can see your padding, you wouldn’t want any leaks and this way it will be easier to tell and Misty will be able to keep an eye on you.”

Jessie hesitated and had to brush away a tear before she took his hand and pulled him back into Misty’s room where she said goodnight to the two of them.

“Ready for bed?” Misty asked.

She was either completely oblivious or just acting like there was nothing out of the ordinary perhaps for his benefit as she said nothing about the pink pull up he was wearing.

Jessie nodded timidly and he clambered into his sleeping bag before Misty turned off the light. He quickly realised that there was going to be no chance for things to go any further between the two of them. As he finally closed his eyes he never worked out that he had forgotten to use the bathroom before going to bed. But more unfortunately his body was clearly well aware and in the silence of the room it was only broken for a moment by a quiet hissing sound as he filled his pull up completely unaware of his humiliating act.