Chapter 4

We drove into the center of town and parked on Main Street in front of the tailor’s shop.

“The tailor here is a friend of Ms. Connor,” Debbie said and opened her car door.

I was still wearing the baseball cap and boy shorts with no top. I hesitated a moment, since there were people walking up and down the sidewalk. I took a deep breath and got out of the car. It was a short walk from the car to the shop door and I made it without anyone noticing that I wasn’t really a shirtless boy.

Debbie held the door open for me and I darted in. There was a young woman behind the counter. She looked up from what she was working on when I stepped in.

“Young man, you can’t come in here with no shirt on. I don’t know...” She stopped talking when Debbie walked in, then continued. “Debbie ... Hi! ... Oh, is this ... Oh my God! She’s topless! Did you have her walking around like this?”

“Hi Ms. Jansen,” Debbie greeted the tailor, “this is Tissues and yes, she walked the entire mall dressed just like this.”

“Tissues! Hehehehe,” Ms. Jansen laughed, “Your coach told me all about that. At first glance she looks like a boy, but once you look you can see that she’s a topless little girl. Except for those gorgeous nipples, of course. Come in, come in, come in. I got the measurements you sent, but I need to take some additional ones.”

“Whatever you need Ms. Jansen,” Debbie answered.

“God, Debbie, where’s the bra I made you? Did you grow out of another one already?”

“No. Ms. Connor said I can’t wear it today. I’m being punished. And, God! I hope my tits don’t grow any bigger than this.”

“Oh, right. I heard a little about what went on last night. Seems it turned out good though. I think you should take your blouse off, though.”

Ms. Jansen came out from behind the counter. She was tall and thin and had wavy brown hair. She was dressed like a plain Jane in mom jeans and a flowered top. She locked the shop door and turned over a sign with a ‘be back at’ clock. At least we’d be alone in here, I thought.

Debbie pulled her blouse over her head and off. Her impressive titties bounced into view. Ms. Jansen pinched Debbie’s nipples roughly before turning her attention to me.

“Get naked,” Ms. Jansen said.

I didn’t have much on, so I was naked very quickly.

“There you go. Now you look like a cute little girl again!” She said.

I winced at being called a little girl again. But hearing Debbie refer to Ms. Jansen as ‘Ms.’ told me that she was in charge here, so I let it go.

Ms. Jansen grabbed my hand and pulled me behind the counter. “Up you go!” She said as she lifted me by my armpits onto a padded table. Standing on one end of the table, she had me lay on my back with my feet pointing at her. She grabbed my ankles and pulled me toward her until my butt was at the end of the table. Then she pulled my ankles up and apart, pushing my knees into my chest. In a matter of seconds, she had me completely exposed to her. My pussy and asshole were inches from her face.

“Wow!” She said staring at my clit. “You weren’t lying, her clit is fucking huge! It’s the biggest one I’ve ever seen, by far. She’s only fifteen? It’ll probably get even bigger.”

“No! Don’t say that,” I blurted out without thinking. “Please! It’s already so big.”

“I said that about my tits when I was your age. Now they’re twice as big as they were then,” Debbie said, holding her giant tits up with her hands.

“Help me here, Debbie,” Ms. Jansen said, “Hold her knees back and spread her as wide as you can.”

Debbie did as she was told. Looking down between my legs, I could see my engorged clit standing erect.

“I can see you’re a naughty horny little girl. You’re soaking wet!” She said.

Ms. Jansen went about examining my clit and cunny lips. Squeezing and pulling at them. She pulled the hood of my clit all the way back and turned my clit this way and that, looking it over carefully. She measured how long and thick it was with a measuring tape. Then she measured along my slit and even down to my asshole. She was writing all the measurements down. She kept shaking her head and I could tell that she was thinking hard about something as she looked over the measurements.

“You can pick up the clothes by Wednesday,” She told Debbie. “The rest will take some time. Things are going to have to be made special. I’ll talk to Ms. Connor.”

I could only imagine what the clothes would be like. I couldn’t imagine that she’d be making me clothes that were more revealing than what I tried on at the children’s store earlier. I dared not think about what she meant by ‘the rest’ of what she had to make special.

“I need to see her squirt – a really good one. What makes you cum hardest, sweetie?” She asked matter-of-factly.

“I ... I ... I don’t know. I had my first orgasm last night,” I replied. “But ... But Ms. Connor put beads in my butt...”

I didn’t get to say anything else, “OK. Debbie, come to the side here. Hold her knee back. Finger fuck her asshole. She’s plenty wet down there.”

Debbie dipped her middle finger in my soaking wet pussy and then wiggled the tip into my asshole.

“Oooooo ... mmmmm...” I moaned.

Ms. Jansen put my other knee behind her back, spreading me wide while keeping both of her hands free. She pulled my clit hood back with one hand and started squeezing and jerking my clit with the other.

Ms. Jansen and Debbie had me escalating toward and orgasm in no time.

“Fuck her harder!” Ms. Jansen ordered as she jerked my clit faster and faster. Debbie quickened her attack on my asshole, adding a second finger.

“Oh! Oh! OOOOOOOHHHHHHHH ... MMMMMM...”

“Spread her wider!” She ordered while pushing my knee back farther. Debbie did the same with my other leg and my pussy was pointing almost straight up.

“Oh! I ... It’s ... UUUUUHHHHHHHHH ... AHHHH! AHHHHH! AHHHHH!” I shouted as the first three squirts shot out of my pussy. Ms. Jansen and Debbie were making me cum harder than any orgasm I’d had so far.

“Don’t stop fucking her asshole!” Ms. Jansen shouted. I felt a third finger slip into my asshole, stretching me wider than ever. She and Debbie kept up their attacks on my clit and asshole, and I kept squirting. I just kept cumming and cumming. I lost count of the squirts and orgasms until finally the waves slowed down. Sensing that my body was slowing down, they slowed down and finally stopped their work.

“God! That was obscene,” Debbie said as the let my legs down.

“I’ve never seen anyone squirt so much!” Ms. Jansen said, “Look at this fucking mess she made!”

“Oh, she’ll clean up every drop,” Debbie said.

“Wait! I need to measure how far it shot. And besides, I think she owes us a big favor first. Don’t you agree?” Ms. Jansen asked.

“For sure,” Debbie said.

I was too out of breath to say anything. I just laid there with my eyes closed. What just happened was ten times more intense than anything that happened over the last two days. At least I had permission to cum this time.

Eventually, I felt someone climbing on the table as I started to recover my breath. I opened my eyes just in time to see a bald pussy coming down over my face. Looking up, I noticed two rather small tits, so this was obviously not Debbie.

“What are you waiting for? Lick my fucking pussy, you slutty little girl!” Ms. Jansen ordered.

I reached up and grabbed her thighs in order to pull my face up and into her pussy. I found her hole and licked around it, then stuck my tongue in. She started to moan and move her hips back and forth. As she humped my face, I felt her clit run back and forth over my tongue. After a minute or two she started humping faster and faster, then she clamped her pussy down so hard on my face. My head was forced back down onto the table and I couldn’t breathe. I heard her moan loudly and hoped that she’d finish cumming quickly before I passed out.

Finally satisfied, she relaxed, and I sucked in some air. Ms. Jansen stayed on top of me for a minute or two, her pussy hovering a couple of inches over my face. Once she recovered, she climbed down from the table.

When I looked up, the first thing I saw was Debbie’s huge titties swinging back and forth as she shimmied out of her tight jeans and panties.

“Get on the floor,” She ordered as she pulled her jeans and panties off and tossed them aside.

I quickly figured out what she had in mind. She had lay on my back with my legs spread. She got down and worked herself in between my legs until our pussies were a few inches away.

“I’m gonna fuck that huge clit of yours. Just like you did to your Mom,” she said as she scooted forward until our pussies touched.

I thought about last night when Mom and I were forced to do this, and I squirted right onto Mom’s pussy. After the massive orgasms I just had a few minutes ago, I wasn’t sure if I could get there again. But I wanted to. I wanted Debbie to fuck my huge clit until I squirted all over her pussy. Her tits. Everywhere.

SMACK!!

“Ouch!” I screamed as pain shot through my nipples and I pulled away from Debbie’s pussy. Ms. Jansen had slapped my nipples with a flogger. Looking at it, it looked much more severe than the ones that had been used on me last night. Instead of leather straps, this one had rubber tubes. I looked down and saw red stripes across my chest.

SMACK!!

“Fuck! That hurts!” Debbie shouted as the flogger landed on her massive left tittie, just below her long, thick nipple.

“Who the fuck told you to stop?” the tall, thin, still naked Ms. Jansen said.

SMACK!!

The flogger struck my pussy mound.

“Ahhhhh!!” I screamed. It hurt like hell, but my pussy quivered. Was this making me horny?

SMACK!!

Debbie’s pussy took a direct hit from Ms. Jansen’s flogger.

“FUCK! Fuck! Fuck! Ok ... Ok ... Ok...” Debbie reacted.

She started to scoot forward, and I matched her movement until our punished pussies touched again. She started humping quickly. I guessed that she didn’t want to get flogged again.

My clit throbbed as I started to hump her back. I could feel my clit move all over her soaking wet pussy.

SMACK!! SMACK!!

“Mmmmmmmm...” I moaned through the pain this time as two more swats fell across my nipples. “Punish them ... I need to be punished for having no titties ... Punish my horny nipples!” I screamed as I humped Debbie’s pussy faster and faster.

SMACK!! SMACK!! SMACK!! SMACK!!

“You Mother Fucker!!” Debbie shouted as two swats fell on each of her massive titties. They were too big for Ms. Jansen to hit them both at the same time. “Punish my huge fucking tits ... I need to be punished for having huge fucking cow tits!”

SMACK!! SMACK!! SMACK!! SMACK!!

Ms. Jansen continued her assault on my flat chest and nipples and Debbie’s huge titties. At the same time Debbie and I assaulted each other’s soaking wet pussies and begged to be punished. I could feel Debbie positioning her pussy hole nearer and nearer to my engorged clit.

All at once I felt my huge clit slip into her pussy hole to the hilt. Debbie gasped and froze for a moment.