The Bet Pt. 01

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A sissy make a bet with high stakes.
1.7k words
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I have always had feminine features; 5 foot 4, short length brunette hair, pale skin, pouty lips, big blue eye, long eye lashes, hairless body, small frame, wide hips, bubble butt, and a tiny shrimp of a ick. I always get mistake for a girl, and being 21 with a soft voice didn't help at all.

I worked at a small ice cream shop. One day at work my co-worker, John was teasing me about looking girly. John was around 40 years of age, 6 foot 6, broad shouldered, a muscular dad-bod, with a long black beard.

"If you were a girl I would make you scream, Daddy all night long." John said.

"You need to hush." I snapped back.

"What? You don't think I can?" He laughed.

I replied, "You can't even get a girl to go out with you."

John laughing, "Ok, I bet you that I can get you to call me Daddy before the end of the week."

"What! Me? Whatever! You wish! What are the stakes?" I said laughing.

John smiled saying, "If I make you call me Daddy, you have to dress as a girl for Halloween next week, and go out to the parties dressed up that night."

"Ok, today being Monday, if you can't make me call you Daddy by Friday night, you have to pay me $50, Bet?" I said holding my hand out.

"Bet!" He said, grabbing my hand shacking it.

The rest of the day he followed me around slapping my ass. It got where I was expecting for him to slap my ass. I was wearing tight stonewashed jeans, every time he slapped me it would sting. He would slap only the right ass cheek. It started to hurt.

"You have to stop!" I shouted at him when slapped me again as I walked by to put up something in the freezer.

Looking at me and smiling saying, "You have to say, please Daddy stop spanking me."

I looked at him and gave him my angry look, and walked off. At closing time after we cleaned up the store, I was standing at the time clock. He walked up and placed his hand softly on the small of my back, slowly moving it down to my right ass cheek. I rolled my eyes expecting to get slapped again, but he started rubbing it softly in a small circle. I started relaxing because it felt so good.

Smack! As he slapped my ass harder than before.

"Mmm..." I exclaimed.

I can't believe I let out a small noise, I hope he didn't think nothing of it, I thought to myself.

He grabbed my hips and pulled me back against him. I felt his warm bulge against the top of my ass. He started to grind on me.

Leaning in and breathing into my ear, "Just call me Daddy, and we can stop this, or do you like feeling my Cock?"

I push him off walking away, feeling my face turn hot. Not knowing why, was I mad, embarrassed, or something else. It surely can't because of the attention. I went to the parking lot, got in my car and drove home.

Tuesday morning, after getting to work. For the first hour, John just followed me around and stood inches from my ass. Every time I bent over to pick something, my ass bumped his groin. He would grab my hips and hold me there firmly and start grinding against me.

One time he surprised me, and I let out a soft moan, "Mmm!"

John said, "I know baby girl, you like Daddy doing this. You have been such a good girl letting Daddy do this."

Smack! He slapped my ass.

Breathing deeply I moaned, "oh..."

"Oh what? Baby girl," John whispers in my ear.

He turned me around and pushed me against the wall. It surprised me so much I started blushing.

He looked into my eyes saying, "Daddy wants to make you such good girl, but I can't until you call me Daddy."

He smiled and walked away. This kept happening for the rest of the day, he would follow me around and not touch me for an hour or so. Then he suddenly would, getting more passionate every time. I loved the attention and started wanting to be touched. I started noticing he was walking around with a big bulge in his pants.

When the day was over, standing at the time clock he walked up and grabbed my hips and grinded hard into me, and kissed my neck. I almost melted feeling his lip against my neck.

He whispered in my ear, "wear thongs tomorrow with those tight ass black jeans that you wear."

Then he walked off.

I just stood there breathless for like 20 minutes. I went to the store and bought a couple pairs of thongs. I then went home and layed down trying not to think of John.

Wednesday morning came early, I had a sleepless night thinking of being human handled by John. I got up, took a shower put on a pink pair of thongs and the black jeans. I rushed to work wanting to see John, as soon as I got there he was all hands, slapping my ass, and feeling my ass up and grinding against me every time we were cleaning the back.

Now since it was Wednesday, that means it is inventory day and we have to count every after we lock the store up. It was my week to count the freezer, but forgot my jacket for all the excitement of getting ready for work.

"John, can I borrow your jacket?" I asked John.

"Only if you call me Daddy." He exclaimed.

I rolled my eyes and went into the freezer with a jacket to count. After about 10 minutes he walks in and hugs me from behind. He felt so warm, I also was missing him touching me. I started grinding my ass against his bulge. He reached under my shirt with his left hand and started playing with my nipples that were hard from the freezer.

"What no bra? You naughty girl. You need to start wearing bras Here let me warm you up." he moaned.

Taking his right hand, he grabbed my hand and placed it on his waist line of his pants. My fingers slid down his pants and touched the biggest hot feeling I have ever felt. It felt so surreal, I was breathless. This was the first time touching an other man's cock. It was like it was living and had a mind of its own. I wrap my tiny hand around his huge cock to start stroking it, but he started thrusting and fucking my tiny fist, as he pinched my nipples with one hand and with the other hand he had undone my black jean and was rubbing my clitty throught my pink thongs..

"Ohh.. yes." I moaned.

"That's it baby girl, moan for Daddy." he purred.

"Yes Da...." I moaned, stopping before I said the whole word.

"Go ahead call me Daddy " he said.

I shock my ahead no, biting my lip. He grabbed my pants and pulled them down, leaving me standing there with only my pink thongs and shirt on, in the freezer. I felt the cold air on my ass. He bent me over his knee and started spanking me. It felt so amazing to be spanked in the cold air.

I started moaning, "harder."

Then he stood up and threw me his jacket and walked out, leaving me not knowing what just happened. He didn't cum or let me cum. I pulled my pants up, I put on his jacket and finished counting inventory. While counting I could smell him on the jacket I was wearing. It turned me on, so much when I left I went to the store and bought a couple of girl clothes; bras, low cut jeans, and girly shoes. I went home that night dreaming of him all night.

Thursday sunrise, I jumped out of bed, I got dressed in tight low cut white jeans with a blue thong on. Getting to work, I walked in the store. He didn't look at me or speak to me. I tried getting his attention,. I bent over in front of him, stood in front of him, flirted with him. He just ignored me the whole day. I went home upset. I started to cry into my pillow.

"Why am I crying over this dude, I'm not gay. I don't know what is wrong with me." I said to myself.

Friday morning I went into work dressed very feminine, hair pulled up in a ponytail tail, tight low cut pink jeans, purple pair of thongs and bra. He just walked by me without saying anything or looking at me. At the end of the he walked by me going the time clock.

"Daddy." I whispered.

He stopped and said, "did you say something?"

"Daddy!" I said crying

He turned around, grabbed my face and kissed me. I melted in his arms.

"That is my baby girl." He moaned.

He pushed me to dropped to my knees and unbuckled his jeans and pulled his massive cock out. It was massive and thick, 8 inches at least. I can't believe what I'm doing. On my knees staring at this hung cock. I wanted to please him so much, so that I could get more attention but did I really wanted to taste a beautiful Cock.

He placed the head of the cock against my lips, I opened my lips a little bit. He slowly thrusted in my mouth, it tasted and smelled musky, with a slight salty taste.

I started sucking the head as he started petting my hair. It made me feel so safe and wanted.

He start face fucking me saying, "Daddy love getting head."

I moaned and kept bobbing my head trying to swallow as much as I could.

"Make an ahegao face." he said moaning.

I pulled his cock out of my mouth, as stuck my tongue out, with my mouth open wide. He started jacking off his cock in my face.

"I going to cum, baby," he moaned

His cock erupted, shouting cum in my face, in my mouth, eyes, and hair. I grabbed his cock shoving the head back into my mouth letting it finish spewing cum deep in the back of my throat, I gagged on the amount of cum but I loved the taste of everything drop.

"Now it is time to talk about the bet." he said.

To be continued.

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ThegentlesoldierThegentlesoldier12 months ago

I’d love to read about Halloween

AnonymousAnonymousabout 1 year ago

We need the second part with the halloween bet

AnonymousAnonymousover 1 year ago

Hot story, want more

CDsRsoHOTCDsRsoHOTover 1 year ago

Hot! Would love to pull up on the back of your purple thong while kissing you deeply in that walk in freezer!

AnonymousAnonymousover 1 year ago

Fuuuuck this was hot, my only regret is how short it is. More please!

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