The unlucky Babysitter

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
Post Reply
NudeBaG
Posts: 1946
Joined: Tue Oct 06, 2020 2:59 pm
Has thanked: 2017 times
Been thanked: 4041 times
Contact:

Re: The unlucky Babysitter

Post by NudeBaG »

Jeepman89 wrote: Fri Apr 03, 2026 12:45 pm I just hope Daniel doesn't interfere with the girls' fun with exhibitionist Ricky!
Or…
If he does,
The girls might get 2 naked boys to play with.
I know they said they’d already seen Daniel.
But they didn’t see him hard.
Or touch him.
I’m just hoping for a lot of touching😁
NudeBaG
Posts: 1946
Joined: Tue Oct 06, 2020 2:59 pm
Has thanked: 2017 times
Been thanked: 4041 times
Contact:

Re: The unlucky Babysitter

Post by NudeBaG »

The girls are 9, 10 and 11?
Ricky might be about to give a pre-sex ed lesson on boys
User avatar
Jeepman89
Posts: 1725
Joined: Sat Oct 12, 2019 12:10 am
Has thanked: 4993 times
Been thanked: 1807 times
Contact:

Re: The unlucky Babysitter

Post by Jeepman89 »

This should be good!
NudeBaG
Posts: 1946
Joined: Tue Oct 06, 2020 2:59 pm
Has thanked: 2017 times
Been thanked: 4041 times
Contact:

Re: The unlucky Babysitter

Post by NudeBaG »

At the pace you’re going, hoping for another amazing chapter yet today🙏🏻😁
TheMilkman
Posts: 60
Joined: Thu Feb 22, 2024 7:17 pm
Been thanked: 196 times
Contact:

Re: The unlucky Babysitter

Post by TheMilkman »

I was so close. The window was just in reach. I had to get there quickly even if I'm sure I wouldn't see anything. And as my head popped up I saw it. Three starving girls with their hands on underwear. I think he saw me. Thank God he's trying to fight them off. It would be majorly inappropriate if something were to happen. And then I saw him smile. Ricky just relaxed his body as the underwear dropped. It looked so wrong. All he had to do was pull them up but instead he walked out of them. What is happening? Why is he doing this? Doesn't he know it's inappropriate. And then all the girls blocked my view. I squinted trying to see what was going on. Handshakes maybe? Was he just now introducing himself to them? Oh boy is that lame this late in the game. And then I saw it. Well not entirely. The girls were blocking my view. It was like the hands of a clock going over then below. I was so startled I almost slipped.

Oh wow. Look at that. I Marnie am witnessing religion for the first time. So this is what a helicopter looks like. I think I like the imitation of one better. My eyes just spun watching it go around and around. My sisters were also in awe watching the single blade of a fan spin until it didn't. Slapping against the inner thighs it stopped. I couldn't stop myself at giggling at how goofy, and ridiculous, and memorizing, and big, and.... I lost my train of thought. Something had just ran through my brain. What was it used for?

"I call this one the grazing giraffe." Ricky just went on as his dangle slowly rose like a giraffe. My cheeks were burning and I was loosing my train of thought. Suddenly our eyes met as Ricky smiled. "I call this next one pinball." The thought of what he was gonna do next was almost too much. I was anticipating his next move with wild vigor until I wasn't. "I'm just gonna need two big paddles." I watched as his eyes zeroed in on target. I was sick of waiting and just wanted him to get to business until I decided to follow his eyes. I looked down as I saw two big puffs in my shirt. Yeah he's looking at my shirt 😏. MY SHIRT 😳. As I pulled my head up my sisters were laughing so hard. Ricky just bit his lip as he waited for me to respond.

"Wait...I don't know...." I couldn't find the words as my siblings were trying to push me forward. I froze as my eyes locked on it. With a nervous laugh I spoke. "Hahaha, wow Ricky you don't mince words." He just shook his head as he nipped the bottom of my shirt. I grabbed my chest pushing it closer to me as I spoke. "I don't know about that one mister, I'm a little...I'm a little.." I couldn't come up with the words while I was looking at something that wasn't little. Ricky just grabbed my hands pulling them apart as he spoke. "Your a little worried you might run out of quarters?" Ricky just shook my body letting my chest bounce. My blushed face unsure of how to proceed but Ricky knew.

Unaware to the gathering upstairs someone had just entered the home...
NudeBaG
Posts: 1946
Joined: Tue Oct 06, 2020 2:59 pm
Has thanked: 2017 times
Been thanked: 4041 times
Contact:

Re: The unlucky Babysitter

Post by NudeBaG »

Keep going!
Not sure I like the idea of him getting physical with the girls, but THEM getting physical with him, I like!
Freesub
Posts: 959
Joined: Sun Mar 10, 2024 2:10 am
Has thanked: 167 times
Been thanked: 1041 times
Contact:

Re: The unlucky Babysitter

Post by Freesub »

NudeBaG wrote: Sat Apr 04, 2026 10:01 pm Keep going!
Not sure I like the idea of him getting physical with the girls, but THEM getting physical with him, I like!
Hey, so far he's only asking to see, which is absolutely fair
NudeBaG
Posts: 1946
Joined: Tue Oct 06, 2020 2:59 pm
Has thanked: 2017 times
Been thanked: 4041 times
Contact:

Re: The unlucky Babysitter

Post by NudeBaG »

The girls are learning a lot, it seems.
How much more familiar will they get with ‘Mr Winky’?
Can’t wait to find out😁

I like the idea of the girls becoming more and more brazen.

Hoping they overcome that timidness and take full advantage of finally getting alone time with a willing naked boy

No nudity for them though, stick to the cfnm angle🙏🏻
NudeBaG
Posts: 1946
Joined: Tue Oct 06, 2020 2:59 pm
Has thanked: 2017 times
Been thanked: 4041 times
Contact:

Re: The unlucky Babysitter

Post by NudeBaG »

TheMilkman wrote: Sat Apr 04, 2026 9:51 pm
"I call this one the grazing giraffe." Ricky just went on as his dangle slowly rose like a giraffe. My cheeks were burning and I was loosing my train of thought.
Does this mean Ricky got an erection in front of all of them?
Just like that?🤯
TheMilkman
Posts: 60
Joined: Thu Feb 22, 2024 7:17 pm
Been thanked: 196 times
Contact:

Re: The unlucky Babysitter

Post by TheMilkman »

Marnie was hesitant but I could feel her mind starting to change. I knew what she wanted. Her nervous energy was about to explode and so was mine. My fingers were close to lifting her shirt finally giving me a nice glimpse at these warlocks. And then the door burst open.

"What's going on in here!?!" Ms. Smith shouted as she turned me around. Her eyes just dropped as she gasped. "You naughty boy!" Before I could explain she grabbed it pulling hard as she dragged me out of the room. My face was shifting between two constants. 😳...😰. The door closed behind me as I was pulled down the stairs. It was all too much as I felt things slamming up and down. As he hit the living room she let go turning around. "What do you think you're doing with my girls?" I didn't know what to say. My eyes just dropped. Right in front of me were two large ones keeping a couple buttons on her shirt far apart. "What were you about to do in there?" My eyes just dropped. Between us was a good sized measuring stick and above that two ripe watermelons.

I just shook my head. Without warning she grabbed my ear. I had to think of something fast. "I'm sorry Ms. Smith!" I screamed in pain until she let go. "Now tell me what was about to happen." What do I do? Her face was a bit haunting. I just gulped down all the saliva I could before speaking. "We were just gonna play a game." She didn't seem amused as she quickly asked what the game was we were gonna play. With another gulp I spoke again. "Just a little game of pinball." Her eyes narrowed on the divider between us. "Pinball huh?" Without warning she just grabbed it again from underneath. "With this thing? Were you gonna play pinball with this?" My face imploded as she wiggled it up and down. I couldn't respond. And then she just smiled. "And what were you gonna use as paddles?" She had a little bit of a chuckle added to the end of her words. I couldn't run away because she was holding me. Ms. Smith leaned forward more as she gently spoke.

"Tell me Ricky." Her grip loosened as her finger slid up the shaft. "What were you gonna use as paddles?" I felt like I was holding my breath. They were right in front of me. Her shirt looked like it was about to burst open. "B-b-b-b-b." I stuttered with the words as her hand shifted cupping underneath. "Boobs." I just let it out as she let it drop pulling her hand away. With one eye closed she looked me up and down. "Oh you little devil you," she said, stroking my chin. "I should make you walk home boner and all." I just hung my head in shame. "But I won't." My eyes popped. Her voice was becoming alluring. She just whispered into my ear. "I mean, you were so close." What is she talking about! Close to what? "To seeing them." I felt all the hairs on my body stand up. I just let her talk. "I think I should punish you, after I finish changing. She just bit the tip of her finger as she dragged me back upstairs.

I didn't know what was going on. I slowly saw the girls bedroom open as they peaked out. "You three are in so much trouble, I'm gonna punish you after him." And like that we were in her bedroom. I didn't know where to look. "I'm sorry I'm sorry I'm sorry." Ms. Smith just smiled as she crossed the room. "You better be mister, you're supposed to be watching my girls, now you're gonna watch me." Something just kicked in me as I raised my hands covering my eyes but one finger was loose as I witnessed her pants hit the floor. Soft pink panties were my view. And then my hands dropped. This was so wrong. I saw some of the biggest butt cheeks imaginable. "Ricky you're so naughty." Her words were laced with tiny giggles and finally I took the hint.

"Oh Ms. Smith I promise you're the only girl for me." I sure was lucky as I got another gentle chin stroke. "Oh Ricky you're so cute." That's when she did something unbelievable. She picked up my hands bringing them to the buttons on her shirt. This must be illegal. I shouldn't be doing this but my hands just started without me. And then I saw it. The biggest purple bra ever. My head was starting to spin. "Do you feel like a big man?" Oh baby I felt like the biggest man. This all seemed unreal. I guess it was time to dig it. As I reached for it she grabbed my hands. "Ah ah ah mister, don't you want to play like adults?" 😳. I am the luckiest kid alive. Thank the Lord for this blessed day. I just nodded. "Real adults like to roleplay." And like that she moved to the closet. She just started laughing as she wrote something down on paper. Then an outfit was tossed to me.

"Put this on and memorize your lines." It was a cowboy outfit. Is this really what adults do? Ms. Smith moved to the door as she pointed to the closet. Without hesitation I jumped inside pulling together my new attire. This was gonna be crazy. Finally I was gonna get some. Huh? No pants. I guess she was really hungry for me. I pulled on the cowboy hat, shirt, holster, and boots before I read my lines. This is what adults talk about? Ok I guess. "Ok are you ready?" Ms. Smith just gave me a good ah huh. Without much more warning I jumped out from behind the door as I shot finger guns and thrusted my hips forward.

"Check me out, I'm the biggest rooteist tootienst gun in the west." I pumped forward with three big bangs from my mouth. "I'm cowboy Ricky and I'm ready to ride..." My words dribbled off as laughter took over the scene. I turned with shock because not only was Ms. Smith there but so were her three girls. And in the center of it all a camcorder recording the whole thing. "Where you riding to big boy?" Marnie asked as she zoomed in the camera. I just tried to cover myself as best I could. "What's wrong, sheriff Ricky? Got a snake in your boot?" Ms. Smith asked through a loud laugh. I whole body was red with embarrassment. "Your not gonna do anything with that video are you?" I asked shaking my head and holding my crotch. All the girls snickered eyeing each other.

"I think it will make a wonderful Christmas video for the whole church to see." 😳. They were bluffing. No way would they do that. "What do you say girls?" Again the laughter wouldn't stop. "I think he'll be the rooteist tootienst cowboy in the whole Sunday sermon," Marnie added after her mother. I just took another look at myself as the girls apologized for their naughty behavior. "Wait I apologize too," I said bouncing between my feet. Ms. Smith just shook her head. "Not good enough mister, in fact your punishment isn't over." Crap now what. "I think this cowboy needs to learn a lesson, this dirty cowboy likes to spank his horse and thats not right." What exactly was she getting at? She just took the camera from her daughter pointing it right at me. "And what do we do to people who spank animals?" I just stood frozen trying to process what was about to happen until it did.

"Spank them back!" All the girls shouted in together. My eyes dropped as I turned my butt cheeks a bit to see the target of so many eyes. And then it hit me with a gasp as Ms. Smith closed one eye focusing the lens on me. As I shifted the girl darted at me. I juked left then right and jumped into the bed. Hands reached for me as I scrambled for the door. Ms. Smith zoomed in following my rear as I leaped into the hall. I slid on the rug as I ran to the stairs. The front doors gotta be locked I'll try the sliding glass door. I saw it just behind the couch. I just have to dive over it and I was home free. And I one big jump I dove right over the couch or that's what I would have liked to have happened. As I slid over the arm of the couch something snagged and before I realized it my gun holster was stuck to the arm.

"Yippe ki yay mister babysitter." I heard the girls come down the stairs as I struggled to brake free. "Quick Mom get a shot of his big old booty." I was trapped. I tried to pull back or forward but it was no use. "Hey wait, I didn't do anything wrong we were just playing around!" I shouted trying to wiggle free. "Oh yeah keep wiggling it for the camera," Ms. Smith said zooming in. That's when I heard a new noise. Some kinda pat or slap. I turned my head to try and see what it was. I watched what looked like flour being patted in each girls hands. "Ok your hands are ready, we don't want them to stick to this fat butt." I couldn't let them just humiliate me. "Hey! My butts not-." My lips curled as a hand smacked cheeks.

"Quiet you! That was fun!" Marnie moved over letting her sisters get close. "Ready girls?" Ms. Smith got a good view as the girls pulled their hands back ready to go to town as Ricky held his breath.
Post Reply

Who is online

Users browsing this forum: No registered users and 11 guests