The Reluctant Babysitter

June 2, 2017

Growing up with two sisters and no male figure in my life was difficult enough, being the instant babysitter was even worse.  My mother came home Friday afternoon to tell me that I needed to watch the baby because she had to work all day Saturday.  When I tried unsuccessfully to pawn it off on my older sister, who already had plans for the weekend with her boyfriend, I was left with the only option left… do it and tried to get paid.  I negotiated some money out of it with mom and agreed to watch the little brat for the day.  It really wasn’t that big of a deal since she had been sick all week and the medication kept her asleep most of the time anyway.

The next morning, mom left for work and wasn’t expected back until late in the evening and my older sister was not going to be back until Sunday, so I had the place to myself… with the exception of the sleeping baby in the next room.  For the first hour, I simply did what I always do – nothing.  I watched a little TV while I ate breakfast.  I checked on the baby to make sure she was okay then headed back to my room.  It was weird how things got boring all of a sudden and I found myself wandering around the house, snooping on my mom and sister by rummaging through their stuff.

What I found was unbelievable.  It started when I went into my older sister’s room and after looking at her diary, I opened her nightstand to find two long dildos.  I knew she was having sex with her boyfriend, but I thought to myself – she was either not getting enough or “really not getting enough”.  I then went through her closet and found a few my favorite t-shirts she took from me and a secret box she had tucked away that had pictures of her in lingerie and a few of her in the buff.

I immediately put the box back and left the room.  I started to get paranoid that she or my mom would come home early and catch me.  So I went back to the living room and watched a little more TV.  After only a few minutes, I decided to continue my expedition by heading to my mom’s room.  Strangely enough, she too had secrets buried in her closet.  She never remarried and went on a number of first dates… maybe the reason why was that she never really needed to leave home.  She had all the cock she needed in her room.  After finding her skimpy and very revealing lingerie stashed in the back of her closet, I found a huge box of porn movies and sex toys and her favorite ones were in the night stand and apparently used often as they looked very worn.

I thought to myself, I wonder if mom and sis know what they each have in common.  Hell for all I knew, they may have actually picked things out for each other.  As I left the room and went to check on the baby, I kept thinking about how weird they were, but being 17 and still a virgin, I also wondered what I was doing wrong.  So, I decided to occupy my time the way they did.

I started by going to my sister’s closet and taking a pair of her tan pantyhose and best looking lingerie then found my favorite purple dress that she never wore, but I thought was fantastic.  I then headed back to my room where I jumped in the shower and shaved my legs.  After which, I slipped on the pantyhose and lingerie then after stuffing the bra cups I put on the dress I went to look at myself in the mirror but it was too small.  I moved it to the floor and got down on my knees and posing like a cute innocent little girl.  I then walked back to mom’s room and checked myself out in the full-length mirror.  If not for my hair and no makeup, I looked great.  I pulled out a pair of mom’s low heels and went to the bathroom to fix my hair.  I was letting it grow out a little bit, so with some careful styling and some hairspray, I was able to find a girlish look that fit.

I thought about working on makeup, but there was a knock at the door and when I walked to see who it was, a deliveryman was waiting for someone to sign for a package for my sister.  We never let anyone else sign for our deliveries because they tended to get stolen or misplaced by our neighbors.   So I took a chance and opened the door.  There stood a nice tall young man who was not really paying any attention to me, and was preparing the signature form so I could sign for the box.  When he handed it to me he just stood and stared.

I signed the form and as he handed me the box he asked, “Big plans for today?”

“Nope, just wanted to try and look pretty”  I said jokingly.

“Well you did a great job, you look great.” he said as he walked away.

“Thanks.” I replied.

“Have a great day.” he said as he got into his truck and drove away.

I watched him drive away and forgot I was standing on the porch in drag, so I rushed back in and shut the door quickly – hoping no one saw me.  I set the box down on the kitchen table and then went back to check on the baby.  It was almost lunchtime, so I made lunch and made sure the baby was able to eat so I could give her the medication she needed and put her back in bed for a nap.  Still dressed, she didn’t really recognize me and may have thought I looked like my sister.  After I got her settled down in bed, I went back to pampering myself.

I didn’t want to chance the makeup and ruin my look, since I already got approval from the deliveryman, but I did want more, so I went back to my room and started to jack off.  As I did, I was getting super hard, but still wanted more.  I kept thinking – what would the deliveryman do to me if we were alone together?  Just then, my hand sprang out from the tight pantyhose and I ran down the hall and pulled my sisters dildo from her nightstand.  Laid on her bed and started playing with it.  I remained hard as a rock as I stroked the long thin cock she treasured.  As I turned it, I was startled as it began to vibrate and shook right out of my hand.  I then took a firm grip and never let go.

I began to wet my hand and stroked the shaft up and down as if it were my own rock hard cock.  I then moved it down and slid it under the pantyhose and right next to my shaft and the vibration caused me to get harder and squirm and shudder. I then pulled it back out and tried something new.  I began to kiss the tip and then flicked the tip with my tongue. It was just a toy, but I was having so much fun, I just couldn’t stop.  I leaned over and reached for the lube my sister had in the nightstand and came across an inflated ball attachment.  As I brought the two together, I realized what the attachment was really for.

So I quickly inflated the beach ball and firmly secured the dildo to it.  I then got up and began to pull off the panties leaving me in the tan pantyhose, which were unsuccessfully holding my cock down.  I was getting a huge thrill from the tight hose wrapped around my clean-shaven legs; so rather than take them off, I tore an opening in the rear. I then squirted lube on my ass and ran my fingers up and down my crack slowly penetrating my virgin pussy.

I got up on my knees, holding the dress up around my chest.  I moved the bouncy ball sex toy behind me and slowly lined the long dildo up against my opening.  After a few failed attempts, I finally fit it in and the tip slid inside me nice and easy.  The feeling was so intense I fell backward sliding the rest of the cock inside me until it disappeared.  The initial pain caused me to cry out in ecstasy.

I leaned forward moving my legs so they could hold the ball in place as I began to slowly bounce up and down taking the cock completely over and over again.  I looked over to my left and could see how I was riding the shaft and began to really get into it, talking to no one, but wishing I wasn’t alone.

“Oh yeah… baby, fuck me.”



I continued to watch and listen as I rode the rod until my legs were tired and I was nice and wet…. Yes I said wet.  I had gotten so into it and enjoyed the ride so much I came all over myself catching most of it with the pantyhose.  I fell to my side and brought my knees up to my chest as the rubber shaft slid out of my pussy.  I started to drift off to sleep before hearing my sister crying in the other room.

I got up out of bed and cleaned up enough to cover up and checked on the baby.  After which I went to bathroom, got undressed and jumped in the shower.  After the shower, I wrapped myself in a towel and opened the door to find my mother standing in the hallway.  Standing there startled, I wasn’t sure if she noticed anything in her bedroom or worse my sister’s bedroom – since I hadn’t cleaned up in there yet.  While mom took care of the baby, I ran back into my sister’s room and grabbed all of the evidence and ran back to my room.

After I was done, I threw the comforter in the washer and went about the rest of the day – worried about being caught, but more excited about the new sensations I felt during one of the greatest days of my young life.



  • Ken September 15, 2017 at 4:04 pm

    Great story! I hope there’s more to it!

    • M. C. Questgend September 15, 2017 at 5:28 pm

      They are tied together… Part 2 is the Machine Shop and Part 3 is Not So… Home Alone.

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