Babysitter's Secret...

NOTE: I published this story under another Literotica ID: MonkeyWrench00. I'm sharing it here too. (I use this ID for a more feminine persona when I chat. If you see me in the CD chat room here, hmu!)

This piece was inspired by a chat I had with Cutesissytoy! Thanks for the imagination fuel!

This, is a tale as old as time: Single suburban middle-aged man meets hot young girl. Hot young girl babysits for aforementioned man. Middle-aged man fucks young girl, finds out she's a crossdresser, keeps fucking her.

But when it all started, I wasn't aware that any of this was going to go in that direction.

I met Cathy (we'll call her "Cat") shortly after I moved into my new neighborhood. I was recently divorced, but fortunately I was in good enough shape financially, that I could afford a nice new house, in a nice, secluded neighborhood. I had a nice, large lot that kept me at a pleasant distance from my neighbors, there were lots of trees, etc. What more can you ask for?

I was out grocery shopping one day with my kids in tow, and they were brimming with energy. I'd been burning the candles at both ends recently. My wife had taken off with some prick asshole, and the judge awarded me custody. I must've looked beleaguered because the cutest, sweetest girl came up to me and introduced herself while I was rapidly putting back copious amounts of junk food and candy that my kids had taken off the shelves.

"Hi Mr. Carpenter! Looks like you've got your hands full. Need any help with your kids?" I looked at her quizzically, and she continued, "I'm Cat! I live down the street. My parents are the Findley's." Ah. The Findley's. They had a pretty sweet Tudor. "I go to a local college, so I'm staying with them right now."

"Well Cat, we're just wrapping up here, but if you ever want to do some babysitting, let me know."

She beamed at me, "I'd *love* to." We exchanged contact information, and off I went with my little monsters.

Now, the full impact of this exchange took a little while to settle in. Cat, to put it lightly, was fucking hot. And the fact that she was in college, sent my head spinning. She was legal. Now normally, I don't pursue younger women (especially not that young) and I barely fantasize about them anymore. What's the point? From the perspective of a young woman, I could see myself as a gross older man. Nothing is more pathetic than an older guy who thinks he's going to score with a younger chick. That's Penthouse Forum shit. Doesn't really play in the real world. Besides, younger chicks don't get your jokes or cultural references.

Now - let me clarify - I'm not a "gross" older man. I'm in my early 40's. I exercise. I'm in good shape. I'm still rocking a 34 inch waist, I've got broad shoulders, a square jawline, and all my hair. (Alright, it's thinning just a little. I also have a 10" dick, and no problems getting it up. Women my age dig me, and if I had the time and energy, I'd be knee deep in pussy.

But that was the thing. As a single father, my number one mission is my kids. They were having a rough time adjusting to the divorce, so I didn't see the need to complicate anything by bringing strange women around. I've got needs, sure, but I sublimated them for the good of the kids. Maybe I was in denial and avoiding dating, but I'd rather spend an evening watching Spongebob than trying to get into someone's pants.

So, cue "Cat". The older man-younger woman/babysitter trope was already a staple in my fantasy arsenal. In the 5 minutes I had alone each day, in the shower, I exercised my thoughts about Cat. She was 19 as we know. About a head shorter than I was. She was lean, and had a cute, soft - somewhat boyish face. That was no problem for me, I liked "handsome" women and tomboys. She was also a snappy, if not provocative dresser. When I'd seen her in the grocery market, she was wearing a short white pleated skirt, black thigh highs, chucks, and a cute top. She had on bubble-gum pink lipstick, and her hair was done in braids. Instant hardon. After our introduction, I would spend my morning shower-time jerking my cock to one fantasy after another about her.

But there was something off about her. I could swear I saw an Adam's Apple, but I wasn't too sure. And in subsequent chance meetings, I noticed that her hands were a bit larger than they should've been for her frame. I reasoned that she was probably still growing, but sexuality being what it is these days, who knows.

The question started to eat away at me. I was trans and CD friendly. I'd had some strange experiences as a younger man, and I was always looking to replicate them. It was the primary reason why my wife had left me. I confessed to her about my experimentation, and she turned immediately cold. She was convinced I'd "never be completely hers" and eventually seek out gay relationships. I tried to convince her that it was just a period of my life that had no bearing on our marriage. We'd had a good sexual life together. I never disappointed her. So, what was the big deal? But, she left. Doesn't pay to be honest, I guess.

I was starting to become obsessed with Cat. I was thinking about her constantly. I knew a real relationship with her was never going to be possible, but I wanted to push the envelope and see where things could go. I also wanted to figure out what was between her legs.

Around this time, I decided I needed a sexual outlet and started to date. I hired Cat as a baby-sitter on these occasions. I decided that I wasn't going to try and fuck Cat. That'd be just too weird. She was old enough to be my daughter for chrissakes.

So, Cat would come around and sit for my kids. She always had a smile for me. When she'd look at me in the eyes, it never failed to produce a blush. I also had her run errands for me. At $20 an hour, she was eager to help.

On one particular occasion, I couldn't take it anymore. I was going to make a move on Cat, or at least determine "what she was". I'd had her watch the kids while I ran out and got some groceries. When I returned, I gently encouraged the kids to go into the basement playroom and plug into their respective screens. Hell could erupt through the street, aliens could invade, Godzilla could start trashing our 'burb, but the kids would be in Fortnite-land, and ne'er would they budge.

Once the kids were secured downstairs, I paid Cat and made my first move. "Hey, uh. If you're not in a rush, could I ask you a favor? It's nothing important, but I could use your help with something. If you have to run though, it's totally cool."

Her face lit up again and she gave me a somewhat naughty smile - at least I think she did. "Of course Mr. Carpenter!" She moved a little closer to me, and I caught a hint of a citrusy perfume. I could feel my cock twitch in my pants. "What do you need?"

Like I said, I'm a big guy, so I really had to think this one out. "Well. I have a leaky faucet upstairs that I need to replace, and I need help turning the valve off." I motioned to my shoulders, "With my size, it's difficult for me to maneuver under that sink. Could you just pop under there and turn it off? I'll give you an extra $20 in danger pay." I laughed.

She cocked her head and narrowed her eyes slightly. The corners of her lips twitched upwards in a smile. "No problem Mr. C. You don't even have to pay me!"

"Alright. C'mon." I wanted to get behind her to look up her skirt - it was a cute pink miniskirt - and look at her supple, toned legs, but I got in front of her. I could swear I heard her softly whisper, "mm hmm." as I walked ahead of her.

The bathroom was connected to my bedroom. I noticed her scanning the environs as we walked through.

We got to the task at hand. She knelt on a bathmat and started moving things around. I'd purposely hadn't offered a flashlight, so I could get some extra time checking her out. She was wearing a white thong, and I caught a glimpse of it as her skirt rode up on her ass. Still though, I couldn't tell if there was anything else down there.

"Hang on, Mr. Carpenter..." I had also purposely never offered to let her use my first name. It was a huge turn-on for her to call me "MR. Carpenter". Jesus, I'm such a pig!

"Found it." Her body leaned further under the sink. "Whoops!" she exclaimed, and without thinking, I put a hand on her lower back.

"You ok?" I asked. This was a tense moment. This was either the moment, where she would make hasty excuses, back out and ghost me on future babysitting requests, or this would be the ultimate fantasy moment that millions of American men dream of, but only few achieve.

"Yup! Got it!" Her tone sent waves of relief through me. Her voice was light and cheerful, and my hand remained on the small of her back. Still, you never know, so I gently removed it. I didn't want to be an asshole. If anything was going to happen, she could meet me halfway. That's one thing incels and whiners don't get. Less is more. I put it out there. If she was amenable, she'd let me know about it.

And she did.

I heard the valve turn, and then she slowly extracted herself from under the sink. As she was getting up, she bumped her ass into my crotch. "Whoops." She said. She turned and leaned back on the counter. "You know Mr. Carpenter..." One of her feet was touching mine. She made no effort to move it. "You know...I could use that extra $20 bucks...but..." She let her voice trail off, and she let her eyes wander down to my crotch, which at this point displayed a significant bulge. "I could also use something else...Would you like to do a favor for me?"

My throat was dry.

"What..." I managed to croak out.

She stood an inch from me and placed her hands on my belt, then sank to her knees. "I think it would be a mutually beneficial favor actually..." She started to undo my belt and glanced towards the doorway. She sauntered away towards it, and my heart beat faster as this freckle-faced blonde, with a cute, upturned nose swayed her ass back and forth. She locked the door and returned to my belt.

She sank to her knees and opened my fly. She parted the opening in my boxers, which exposed only a part of my shaft. She gave it a little kiss, all the while maintaining eye contact. She tugged down my pants and boxers and let out an audible gasp as my cock sprang upwards. Her eyes glittered. "Ohhh daddy...". I'd never liked how these kids use "daddy" in sexual situations, but right now, it was just fucking hot. "You're SO BIG daddy." She started kissing my cock lightly, up and down the shaft. The kissing turned to licking. She stuck her nose under my balls and inhaled. "Mmmm.... I love a man's musk...." she moaned. My cock twitched.

Her soft hands stroked my cock. Gentle strokes that twisted around its circumference. She spit on it, and kept stroking... It was going to be extremely difficult to not shoot my load. She then swirled her tongue around my cockhead. Oh my god, I thought I was going to explode. Here was the real test though. How much could she get into her mouth?

She started to open her mouth wide, and slowly started to swallow my dick. She coughed and gagged once, and then pulled off. I make it a habit, never to pressure anyone about sex at this point. If a woman can't take it, I generally call it quits. Hurting someone isn't sexy to me. Once she composed herself, she laughed and looked at me, eyes red with tears. "Hang on!" she breathed heavily, "I can do this!" She smiled, cleared her throat, and went back to it. Slowly and diligently, she relaxed her jaw and worked my cock towards the back of her mouth.

Soon, I felt it hit her throat, she gagged a little, but she wasn't quitting. She worked it deeper into her throat. I was incredibly impressed. Then, she started humming! The vibration was superbly arousing...holy shit. I started to work my cock back and forth, hearing her "gluck gluck" as I fucked her throat. My balls started to pull up, and I could feel myself getting close. Before we got any further, I had to know.

I pulled my cock out slowly, despite the protests in her eyes.

She coughed and sputtered as I slid my slimy monster cock out of her mouth. She was gasping, her mouth ajar and her chin covered in saliva.

I grabbed her ponytail and pulled her up and around. I brought her up against me, so her back was resting around my chest. I slowly moved my hands into the waistband of her skirt...

"Mr. C, NO!!!!" I froze. I let go of her ponytail and took a step back. She turned to me. There was the hint of tears glistening in the corners of her eyes. She cleared her throat again. "There's something you should know..."

I held a hand up and smiled and nodded. "It's ok. I know." She cocked her head, and I took a step forward. "It's ok." I turned her around again - she hesitated slightly - and I moved my hand inside her waistband again. My fingers sought out what I had been imaging was there, a cock and balls that paled in comparison to mine. I squeezed gently, then put my fingers on top of her cockhead - still concealed by the thong. I started rubbing her cockhead, like I would with a real clit. Small, repeated circular motions. She leaned back against me and started to moan.

"Good girl." I said. "Good girl." She gave me a quick glance with that last emphasis and smiled. Maybe I was projecting, but there seemed to be relief in her eyes. She closed her eyes, and sank back against me, grinding her soft ass into my crotch.

By now, I was more than worked up. I had to come. My cock pressed hard against her and throbbed.

"Do you think you can take this cock in your pussy?" I whispered hoarsely.

"Yessssss, daddy, yessssss...." She hissed.

"It's big, girl. Think about it."

"I can do it daddy...I've put big toys in my pussy before..."

"This ain't no toy sweetie."

"I know..." She turned, grabbed my cock, and started twisting it. "I want it..."

"Tell me. Tell me how you want it...tell me how bad you want it..."

"I want it so bad daddy.... I want to feel it in my pussy...I want you to slam into my tummy...I want to feel your big meat throbbing inside me...I want you inside me so bad, daddy..."

That was it. I spun her around and she supported herself on the sink. Mechanically, my hands went to the drawer where the lube was. I pulled her thong to the side, and I spurted a liberal amount of lube into my right hand. I poked a finger into her tight hole, then another, massaging around the lube. She was hot in there. Now she was hot and wet.

My cock was iron-hard. I teased her hole, slowly edging my cockhead against her ring. I started to insert myself and it was hard going. She was tight...so tight...She wouldn't be after this...

She was moaning and started inhaling and exhaling sharply.

"You ok?"

She nodded her head and gave me a thumbs up. She couldn't talk. I kept pushing slowly.

"Unh unh unh uhn...."

Inch by inch, I worked my way in. Finally, I was balls deep. "Congratulations. You're now a bottom."

"Yay..." she gasped.

"Do you want me to fuck you, or do you want to quit?"

"Fuck me..."

"C'mon."

"Please daddy...fuck me...fuck me hard...rail the shit out of me....!"

I slapped her ass hard and she quivered and slowly started to move my cock. Gradually, I increased the tempo. I was watching her face in the mirror. Her hair was plastered to her forehead with sweat. Her eyes were practically rolling up into her skull. Her mouth was agape, and she was drooling. Good cunt.

I gripped her hips tighter as I kept fucking. I could hear both of our sets of balls slap back and forth...Suddenly, I didn't hear hers anymore.

"Daddyyyy....my g-spot...I'm.... I'm...unnnnh....CUMMING...!"

I heard her grunt in a syncopated rhythm to the fucking she was receiving, then she cried out, as I heard spurt after spurt jet out of her cock and splatter against the cabinet.

That was the final straw. "Here I come!" I managed to croak out. I pulled her sweat-slick ass against me and ground in as deep as I could go. My orgasm boiled out of my balls, and I let out a yell after my thick cum started to explode into her anal cavity. Creamy, clotted, globular projectile after projectile slammed into her guts.

"It's so hot daddy..." she cried.

My legs trembled until well after I was drained and empty. I slumped over her for a minute or two. When I pulled out, she cried a little as my cockhead finally exited. She slumped down to the floor, and I bet she was marveling at the cold air filling the space where my hot cock had been.

She crawled towards me and took my cock in her hands. I was a little sensitive so, I jumped.

"Let me clean you off..." she whispered...

I put my now deflating cock into her mouth, and I don't know what kind of magic she was using, but I was getting hard again. She increased her suction and used her fat wet tongue like she was slurping on a straw. God knows how I had any juice left in me, but I came again.

I stumbled back.

"Holy fuck, that was good."

"Tell me how good I was daddy."

"You were so good sweetheart...You suck cock like a pro, you fuck like a pornstar...you have a beautiful body... you have a beautiful face...I just want to fuck all your holes until I die..."

That seemed to make her happy. She started laughing sweetly.

I picked her up, cupping her ass in my hands, and she wrapped her legs around my torso. I kissed her, moving my tongue inside her mouth, letting hers slide all over mine. I can't remember the last time I made out with someone that young.

Our lips parted with a smack of broken suction.

"I can't wait to fuck you again sweetie..."

"Same, daddy. Same."