My phone rang. It was Monday afternoon of spring break and normally I would have at least checked to see who it was, but I was working. It wasn’t how I would have liked to spend my time off from school, but there I was. I had been scheduled nearly every day that week thanks to the influx of tourists in town to spend their own spring break in Miami.
When my phone started ringing for a second time right after I let the first call go to voicemail, I figured I should at least see who it was in case it was important. Excusing myself from the cash register, I walked into the back room and saw that it was my sister.
“Hey, what’s up?” I answered.
She sighed, “It’s Nick’s father. He tripped down the stairs at work this morning and broke his foot.”
“Oh geez,” I added.
“Yeah, I just talked to him and he’s fine, but Nick was insisting he come home from Singapore to help him. I managed to convince him to stay, but now I’m flying to Oregon tonight. Mike wants to make sure he has someone around if he needs help.”
“Oh, okay, well I get off at 4 if you need a ride to the airport or something.”
“Thanks, I was hoping maybe you could bother watching Skyler?” My cock twitched when she said it. “I know it’s a huge imposition, but I don’t want her to miss her dance practice on Thursday, otherwise I’d take her with me.”
“Yeah, it’s no big deal,” I replied, making sure I didn’t sound too excited.
“Thank you so much, we’ll pay you, of course,” Sarah assured. “I hope it doesn’t cause you too much trouble at work.”
“Don’t worry about it,” I replied. “I’ll be home in a bit.”
I was pretty excited I had an excuse to take off work now. And it turns out, my boss was pissed when I told her I couldn’t work this week because I had to take care of my cousin. She kept complaining about how she couldn’t afford to have me take off with so many tourists in town and stressed the fact that I was inconsiderate, lazy, and horrible at my job—all things she neglected to mention when I offered to work extra hours this week. After listening to a slew of insults and making a few attempts to explain that I had no control over a family emergency, I left. I still had a couple hours left of my shift, but I was sick of her shit.
Sarah was surprised to see me home so soon, but laughed when I told her what had happened.
“Did you tell her you quit, at least?” She asked as she packed her suitcase.
“No, she wouldn’t shut up long enough, so I just walked out.” I sat on the other side of her bed as she continued to gather things she’d need for her trip.
“Amazing,” Sarah approved. “Don’t tell your parents, though.” Her words followed a look of caution.
“Yeah, I wasn’t planning on it,” I replied.
“Your mother would probably have a panic attack and drive down here,” She added. “Although, they were glad to hear that you have a girlfriend.”
“You talked to them?”
“Yeah, your dad called yesterday,” she paused before adding a t-shirt to her suitcase. “Sorry, was I not supposed to say anything?”
“It’s fine,” I shrugged. I didn’t really care.
“Oh, by the way, if you want to have Dagny over while I’m gone, that’s totally cool,” Sarah added. “I want you to at least have a bit of a spring break since you’re stuck here watching my kid.”
“My spring break just got ten times better now that I don’t have to work,” I replied. I could have added that I was pretty ecstatic about watching Skyler because I knew I’d get to see her naked a lot. But I felt it was better to keep that to myself for obvious reasons.
After dropping Sarah off at the airport that evening, Skyler and I were left to our own devices. At the time, I was still really conflicted. I felt guilty for taking advantage of her the other night but at the same time, I couldn’t wait to do it again. Besides, it’s not like she was bothered by it.
If Skyler had ever been scared or told me she didn’t want to kiss me or something, I probably would have stopped. But she was just a curious kid.
“Can we go there?” She asked pointing out the car window.
“No, that’s a casino!” The traffic was backed up, so I was taking a detour back to Coral Gables.
“I’m hungry!” She whined as we continued driving down the road.
“We just ate!”
“But we didn’t have dessert!” The voice from the back seat inserted.
“Fine, we can stop for ice cream,” I gave in. But Sarah had given me one of her credit cards that I could use while she was away. I stopped at our usual spot and we each ordered cones. As I ate mine, I couldn’t resist watching Skyler lick her ice cream and imagine she was licking my cock instead. My guilt was magnified, but so was my desire…
When me made it back to the house, it was getting late so I told Skyler it was time to get ready for bed. That night, she got changed by herself. As for myself, I breathed a sigh of relief. I had successfully resisted the temptation to—I didn’t know what exactly. But I knew I wanted to watch her get changed, hug her, kiss her, throw her little body onto her bed and rub my cock all over her…
Once she was dressed in a pull-up and ready for bed, she came to find me. I was sitting at the desk in my room, surfing the web on my computer. She walked in and placed her head on my shoulder, peeking over at my screen.
“Hey!” said before turning to face her.
“Cant we play a board game before I have go go to bed?” Skyler asked quietly.
“Sure,” I replied, beginning to admire the image of the girl before me. I swallowed hard seeing her kn her pull-up. It fit her snugly and the pink hearts and flowers on it only added to her cuteness. Her ribcage was clearly visible while her nipples barely protruded from her chest. Despite her lack of tits, I still wanted to stick my cock right in the center and then rub myself all over her. I wanted to feel her skin—perfect the way only a child’s could be, rubbing against my cock.
“Or, we could…” that’s when I grabbed each of her hands and spread them apart as I pulled the half-naked child into me. Our arms were spread out to either side as we kissed each other. She laughed.
I felt the vibration from her quiet giggles as I made out with her. That nigh, she tasted sweeter than ever before. My cock responded excitedly. Following its lead, I let go of her hands and began to run my fingers up her arms. I was soon rubbing her shoulders and ran my hands underneath, feeling her hairless underarms. Without the slightest hint of hair or stubble, they were completely flawless. From there, I continued to touch down her sides, all the way to her pull-up. I pulled against it lightly, but didn’t take it off. Not yet, anyways.
“You’re so beautiful,” I said when I pulled away. I looked her up and down—admiring her innocent body.
“Thank you,” she replied politely to the complement. The 5 year old didn’t know of anything else to say in such a scenario.
“You know, Dagny and I do a lot more that kiss,” I said. At that point, I was transfixed on her childlike beauty. My senses were overwhelmed and there was no more denying myself.
“Like what?” She asked.
I paused for a moment, “Well, we like to get in bed and make each other feel good.” I knew I shouldn’t go any further. It would have been far too easy to put an end to this little game we’d started and never look back. But the temptation was too great. There was be no one around to stop me and up to that point, Skyler had even wanted me to kiss her.
“Like how?” She followed up.
“If you want, I could show you…”
“Okay!” She seemed excited, if a bit nervous.
“I want to get comfortable first,” I said before stripping off my t-shirt. I paused, but then started to unzip my jeans, too. Still sitting in my padded office chair, I peeled them off and dropped them onto the floor along with my shirt. Now I was only wearing my boxer briefs and Skyler, only her pull-up.
The girl said nothing as I pulled her onto my lap. I felt her pull-up depress against my thigh as I supported her weight.
She wrapped her arm around my neck, “so now what?” I didn’t know how to answer, but leaned toward her and our foreheads touched. Taking a deep breath, I did the one thing I knew I shouldn’t. I reached one hand down to my boxer briefs and pulled them down just enough to unleash my cock.
It brushed gently against her pull-up. Skyler didn’t notice at first, amused by pushing her forehead to mine and giving me a naughty stare that I found quite erotic. As soon as my cock touched the skin above her pull-up, though, she looked down and realized what was happening.
“Eheek, your wiener touched me!” She squirmed in my arms and pushed away from me. Her tone remained playful, however. Her effort only caused my cock to rub against her even more.
“Dagny touches it all the time,” I replied, as she resorted scooting out on my leg towards my knee. “She even kisses and licks it sometimes.”
“What the?” Skyler made a face and wrinkled her nose, “But that’s where you pee from!” She looked at it with curiosity.
“Yeah, I guess it’s a little weird,” I chuckled at her expression. “But it feels really good. If you want, I mean—I could show you.” She had one hand in her mouth, holding it sideways while the other grasped her wrist. I could tell she was nervous as she looked at my cock, just inches away from her thigh.
“I guess so,” she shrugged. With her reluctant approval, I stood up from the chair and moved towards my bed with the girl in my arms. My boxer briefs fell the rest if the way off, causing my cock to rub up against her pull-up and stomach again. She didn’t say anything this time, though.
Pulling back the covers, I laid her in the center of my bed. I began making out with her like usual, but this time I felt my cock rubbing against her pull up and thighs as I leaned over her. Then I started kissing down her chest, paying attention to her nipples and I made sure not to forget about the birth mark at the bottom of her ribcage.
I looked up at her as I continued downward. She was watching closely while I kissed her stomach and belly button. Eventually, I had made it to her pull-up. The elastic fabric conformed onto her hips and fit her snugly. I never had a diaper fetish before Skyler. But then again, I’d never liked little girls either. I kissed her pull-up just once before placing a finger in either side of her waistband.
On one swift motion, I slipped her pull-up down, exposing her pussy to my gaze.
“Woah,” she giggled as I pulled her pull-up all the way off her feet and tossed it aside. Alas, we were both naked together on my bed. Her hairless pussy mound was so inviting and clearly begging for a kiss, too.
“Ready?” I looked up and asked. She nodded slowly and I could tell she was a bit unsure. Regardless, I moved into position and began by planting a few kisses running down her mound before reaching her lips.
“That tickles,” she laughed when I began to lick her. “Oh, it feels so weird!” As I went on, she began to laugh and squirm. I could feel her legs begin to move on either side of my face. Holding her hips with both hands, I made out with her cunt, diving my tongue in as far as I could. This went on for a while with more soft murmurs and an occasional squeal from Skyler.
“Stop, I think I have tuh ah,” the girl started to squirm frantically, letting out several more cries as she did. I continued licking her through her orgasm. Only when it was clear it had all come to an end, did I come up for air.
“How was that?” I asked, seeing her panting to catch her breath.
“It felt good,” she lazily turned her head to one side, looking towards my closet door. I leaned in fo kiss her cheek and rubbed her chest for a moment. After putting it off, my cock was more than ready for release.
“Ew, it’s leaking me!” Skyler noticed the precum that was steadily flowing from my cock. It was indeed leaking onto her leg. Resting my cock close to her and feeling it brush against her was electrifying and it was time I had an orgasm for myself.
“Guy’s start shooting stuff out of their cock when they feel good?” I explained.
“What’s a cock?” Before I could answer her question, she looked down and figured it out for herself.
“Want to help me?” I asked. “All you have to do is stroke it.”
“Hey, that’s what you did the other day in my room,” she realized, referring to the night when I rubbed her hand over the bulge in my pants.
“But now you’ll get to watch and see the jizz come out,” I replied.
“Is that jizz?” She asked, referring to the drop of pre-cum on her leg.
“No, that’s just the stuff that comes out before that,” With that, I guided her hand to my cock and with my other hand, placed my shaft in her hand.
“Your thingy is really long,” Skyler noted as I led her wrist in a motion to start jerking me off.
“My girlfriend thinks so, too,” I replied. With my guidance, Skyler continued her movements.
“This feels really naughty,” she noted. I tickled her stomach lightly in response. Feeling the girl’s soft hand running over my cock quickly had me close to my climax.
Too impatient to wait for her hand to do the job, though. I grabbed a hold of my cock and with several final motions, my cum squirted out onto the 5 year old’s body. She made a note of surprise when she felt the first strand land on her stomach. Then she squealed and squirmed when she saw the large quantities of semen that came shooting towards her chest.
I held Skyler in place while my cum shot onto her. Once it had finished, copious amounts had splattered across her stomach and up to her chest. Some had dripped down her side and I aimed my final few squirts in between then girl’s legs, painting her pussy with my translucent cum.
“You squirteded a lot!” Skyler said when she looked down at her body to survey the damage. The tip of my cock was resting on her cunt as it deflated.
“Here, I’ll help clean you up,” I kissed her forehead before getting up to grab an old t-shirt from my dresser. I wiped the cum off of the little girl’s body before picking her pull-up off the floor of my room and helping her back into it.
Once she was dressed again, I could see that our fun and definitely worn her out. Her eyes looked as if they might close at any moment, as if she was trying not to fall asleep.
“You can sleep in here with me tonight,” I offered, lifting the covers over her.
“I’m not tired,” Skyler answered, but I knew she was. I continued tucking her in and while I normally would have stayed up for a while longer, I climbed into bed after her and settled in. Still completely naked, I settled in and cuddled the child. Even though I was no longer horny, feeling my cock rest against her pull-up was everything.
Skyler was soon fast asleep. As for myself, well, I stayed up for quite a while and eventually stared at the ceiling. As I laid there, sharing my bed with the little girl, I had a deep sense if satisfaction accompanied by the familiar feelings of guilt I’d experienced the first few times I’d taken advantage of Skyler. All the while, I was excited for all what could possibly happen now that we had a whole week to ourselves. There was no going back now.