Humiliate Me Pt. 02

Thanks to Oldbroad76 for editing.

PART 2

I was so damn confused! Arabella had been to our house twice since that night, and she acted like I had dreamt the entire thing.

The only bit of proof that it did happen was the note she left me. Without that, I would've thought I made it all up.

Every day I looked out my window, hoping and praying that I would see her. Whenever my parents and my sister were out, I waited for her to come over, but nothing.

Finally though, Saturday arrived.

I ran downstairs in jeans and a t-shirt where I saw my mum, dad, and sister in the kitchen.

"What are you doing, dork?" My sister laughed out at me.

"Erm, just going to my mate's." I quickly replied, having rehearsed it in my head a million times.

"Ha!" My sister, Jane laughed. "You don't have any friends."

"Jane, don't be so mean." My mum told her.

"Well, we're going out as well. Taking Jane to buy her first car, so we will see you tonight?" My dad asked.

"Erm, yeah, I'll see you tonight." I told them.

Could it really have been that easy? But somehow, it was.

They all left, and after I was sure they were gone, I headed over to Arabella's house.

My hands shook as I knocked on her door. It felt like an eternity until it finally opened, and there she was.

The beautiful Arabella stood smiling.

She wore a tight white t-shirt and jeans. Nothing overly sexy, but I knew what was underneath. I knew there were piercings on both of her big tits, and god, I hoped I'd get to see them again!

"Glad you didn't back out," she said in her soft, delicate voice. "Come in."

Her tone was still like that of my mum's best friend that I had known my whole life, not like the tone she took when I was naked. I wanted that other tone back.

I walked into her house, a house I had been in a million times, but this one felt different.

"So," Arabella said, closing the door, "I do believe you agreed to wear whatever I told you to when you clean my house?"

I turned around and looked at her, my cock already starting to grow.

"Y-yes." I stuttered out.

"Good," she said, "because I've picked a little outfit, and I don't want any whining or moaning, got it?"

There it was, the tone I wanted. I wanted her to call me names again and degrade me! Oh god, how did I not know that I wanted it!

"I understand." I whispered, wondering what she had in mind that I could moan about.

"Good, follow me." She said.

Arabella walked past without looking at me. Something about her total rejection of me just turned my cock on more!

I followed the beautiful, older woman up the stairs and into one of her bedrooms where I saw it. My mouth hung open, and my eyes opened wide when I saw the outfit she had in mind.

"There you go, put it on." She said, turning around and crossing her arms.

I looked at the bed where the outfit lay.

I grabbed it, feeling the black, lacy material in my fingers.

"But... but... it's a woman's outfit." I stuttered.

"Ah ah," Arabella sighed with disappointment, "I said no whining or moaning."

I looked at the skimpy maid's outfit in my hands. It looked like something a girl would buy from a sexy lingerie shop when they wanted to dress up for their man.

Never in a million years did I think I would be anywhere near something like this!

Did Arabella really want me to dress up in a woman's lingerie?!

"Hurry up, get dressed!" She barked out.

I looked at her again, still holding the outfit.

"Aww, what's the matter?" Arabella said with a mocking tone. "Too shy to get undressed."

I looked and her and gulped, realising my cock was definitely fully alert.

"Well, too bad," She said. "Get dressed now!"

I couldn't believe I was actually going to do it, but something deep inside of me just loved the humiliation.

I placed the outfit back down and then pulled my top off over my head, followed by my trousers going to the floor. Then I grabbed the outfit again.

"Erm, I don't think so." Arabella barked at me. "Those, too."

She pointed at my boxers, and I realised that she wanted me completely naked under this outfit.

I hated to admit it, but I was so fucking turned on!

Pulling my boxers down, my hard cock sprung free. When I heard Arabella giggle at my cock, I actually let out a moan.

"Hurry the fuck up, I don't have all day!" She then shouted.

In my panicked state I grabbed the outfit and started to put it on. What I didn't expect was that it had a woman's thong built into it.

I put my feet through the holes and pulled them up, feeling the soft, sensual material ride between my smooth ass cheeks. Then I put the top on, but something fell to the floor.

Dark, see through, thigh high stockings.

"Them too." She told me.

It was so fucking wrong! I was wearing a woman's outfit in front of my mum's best friend! But my cock was harder than ever before.

Picking up the stockings, I rolled them up my leg until my outfit was complete.

I turned and saw a full length mirror where I finally got a proper look at myself. This outfit was so small, so slutty! My hard cock was very, very obvious through it.

To be fair, my legs looked pretty good underneath the stockings.

And then a hand slapped and grabbed one of my bare ass cheeks.

"There we go," She said. "Follow me, and I'll show you what needs doing."

Her hand grabbing my ass made me gasp in pleasure, and my precum leaked inside of the outfit.

As we started to walk around the house, the thong between my ass cheeks felt strangely nice. I had never, ever done anything to my ass before, but feeling this material pressed against my smooth hole made my body tingle all over.

"Okay, you can start in here," Arabella said when we made it to the kitchen. "I expect it spotless, got it?"

"Y-yes." I replied.

"Good, get to work." She told me.

And then, she just left to go and sit in the living room.

I didn't really know what I was expecting when I came over. Honestly, I half hoped that I would get to lose my virginity and have sex with her.

But as it seemed, Arabella literally wanted me to clean her house while dressed like this.

So, I got to work.

I scrubbed every surface, polished every plate, and I vacuumed everywhere. As the minutes went by I got more and more used to being in this outfit. It was hard to describe, but there was a tingling feeling all over my body. When the thong rubbed against my asshole, I whimpered a little.

An hour later, I had finished the kitchen, the downstairs bathroom, and the hallway. I hadn't seen or heard from Arabella during this time. Until I went to do the living room.

I walked in and saw her sitting on the sofa, drinking a cup of tea and watching the TV. I paused for a moment as she looked at me.

"Did I tell you to stop?" She asked, looking at me like I was a piece of shit at the end of her shoe.

"N-no, sorry." I replied and started to dust all of the tables.

As I moved around, I had to bend over to properly clean the surfaces, and I felt Arabella's eyes on my exposed ass.

Just being in that room with her completely ignoring me had me even more turned on.

Then, after 10 minutes of dusting, I went to do the windows when I heard something.

"Mmm." It was Arabella's voice, more like a hum.

I turned around and saw her eyes at my ass, her jeans were open and a hand was down them.

Instantly my mouth filled with saliva, Arabella did nothing to hide it either.

"Don't stop, pervert." She barked at me.

With my cock pressed up against this flimsy, lace material, I turned around and started to do the windows.

Was I nervous that neighbours could see me dressed like this through the window? Sure, but I was too turned on to care.

"Oh yeah, make sure you get it nice and clean." Arabella whispered with a definite moan in her voice.

All I wanted to do was to turn around and see what she was doing, but I knew that wouldn't please her.

What I did find myself doing however, was putting on a show. I would reach high up, letting the skirt of this outfit expose my ass completely. Then I would bend over to do the corners.

"There's a good boy," Arabella moaned as I kept cleaning. "Now you know what it's like to be spied on when you're half naked."

In a weird twist of fate, I realised she was right. It had originally been me touching myself as I looked at her, but now it was her looking at me.

With the window finally done, I turned around and let out a loud gasp.

Arabella, the beautiful, perfect Arabella. She was on her sofa, but her jeans were gone. She still had on a black thong, and her hand was underneath it, rubbing her pussy.

God, I wished that thong wasn't there so I could see my first real life pussy.

"I didn't say you could look at me!" She shot back. "Keep cleaning!"

"Y-yes... miss." I replied, unsure what to say.

As I did the next window, Arabella's moans got a little louder and more consistent.

When I heard a slight wet sound coming from behind me, I could only imagine that she was fingering herself.

Next, I moved over to the TV, and I thanked god that I could see her reflection in it. Her thick legs were spread wide, and she was most definitely fingering herself.

"Oh god," she moaned, "that's it, you dirty little perv. Do you like your outfit?"

"Y-yes." I nervously replied as I sprayed window cleaner onto the TV.

"You like dressing like a girly little slut?" Arabella asked and burst into laughter.

My cheeks burnt red as I realised what I just admitted to.

"I asked you a question!" She then shouted, and I jolted up.

"Yes," I immediately replied, "I like it."

"You like, what?" Arabella asked in a "do not fuck with me" tone.

"I... I like dressing like a girly little slut for you." I told her.

"I feel so bad for your mum," Arabella then continued. "She thought you were going to grow up to be such a big, strong man. But you're not, are you? You're a weak, little sissy."

Ooooh fuck! My cock was leaking massive amounts of precum onto the outfit as it twitched constantly.

"Turn around!" She then barked out.

I immediately spun myself around and looked at her.

Her legs were spread, but she was no longer fingering herself. Unfortunately, her thong still covered her pussy.

"Come here." She ordered.

As I walked over I could see the mix of disgust and amusement in her eyes.

"Lie on the floor." She said.

I didn't want to question her, so I just laid down flat on my back, and then she stood up.

"I can't believe I'm actually doing this, considering what a pathetic worm you are," I heard her say, and then I heard the sound of something hitting the floor next to my head. "But seeing as you're all I have available right now, and you're already dressed like a slut."

My heart almost stopped when her feet landed on either side of my head. Looking up, Arabella was standing over me, and her bare, smooth, wet pussy was right there.

"Stick out your tongue," she ordered, and I immediately obeyed. "I know you won't be any good at this, so just keep your tongue out, and I'll do the rest."

Was this actually happening? Was I about to taste her pussy, the first ever in my life?!

As she lowered herself down, getting closer and closer to me, I knew it was true.

"Urgh," she sighed, "as if I'm going to let you taste me."

And then, finally, my tongue felt contact with her moist, delicate, delicious pussy lips.

If I thought that was it, then I was very wrong. Arabella pushed harder down, and her pussy pressed against my mouth, forcing my head to press against the carpeted floor.

All the way until her knees were resting on the floor besides my head.

I opened my eyes and could see her looking down at me. There was an evil smile coming from her soft lips.

Her hand reached down and gripped onto my hair.

"Keep that fucking tongue out." She ordered.

"Mmhmm." I moaned in response.

My senses were flooded with her delicious nectar. My tongue felt like it was inside of her warm, soaked pussy, and her lips engulfed mine. It was fucking amazing!

And then, she started to grind forward and backward. Slowly at first, her pussy pressed up and down against my lips. Sometimes she would go so far forward that my nose was practically inside of her.

As she got faster, she pushed down harder onto my face.

"That's it, you little bitch. Enjoy your first taste of pussy." She moaned and pulled my hair tighter.

It hurt, and I felt suffocated by her pussy, but I never wanted it to end.

After a few minutes, she was grinding up and down my face like I was a little fuck machine. My face was soaked in her juices, and she gripped my hair tighter and tighter.

"That's it, keep that tongue out for me," Arabella moaned. "You dirty little perv, keep that tongue deep in my cunt!"

"Mmmm!" I moaned but was quickly silenced when she pushed down harder.

"If I wanted to hear you, I wouldn't be suffocating you with my cunt!" She shouted back.

Although my eyes were open, I only got one second to glance at her as she rode my face.

After a couple of minutes, I started to struggle for air. She was really hammering my face against the floor, but I still loved every second of it. Her pussy tasted delicious, like I could live off of it.

"That's it," Arabella moaned. "You would never make me cum with that little cock, but at least I can make use of your tongue."

I stuck my tongue out as straight as possible, her swollen clit occasionally rubbing against it.

Arabella's moans turned animalistic, as she made sounds I never expected to hear from a woman. Her moans were so filled with lust.

"Yes! Fuck! That's it, you little bitch," She kept moaning. "You're gonna make me cum! Be fucking useful for once!"

I couldn't believe this was my mum's best friend! I never thought she would speak like this.

Every now and again I tried to gasp for air when her pussy left my mouth. Occasionally, all I would do was suck in her pussy juices.

My face started to turn red with the lack of oxygen, but Arabella didn't care.

"Fuck.... Make me fucking cum! Yes! Yes!" She moaned louder and louder.

Her grip on my hair tightened again, her legs started to twitch around my head, and then I heard the loudest moan out of her yet.

"FUUUUCCKK YEEESS YOU FUCKING BITTTCHH!!" She screamed out.

That was apparently all I needed.

To add more embarrassment, my cock erupted inside of this maid's outfit without even being touched by her or me.

"Mmmmmmm!!!" I moaned into her pussy as gallons of cum poured out of my dick.

"Are you fucking cumming?!" Arabella shouted as she kept using my face to fuck herself.

"Mmmmm!" I moaned back as my own body twitched.

"You fucking loser!" Arabella kept moaning. "This wasn't for you!"

Both of us got lost in our moans as our orgasms never seemed to end. The crotch of this maid's outfit felt drenched with my own cum, and Arabella's cumming pussy soaked my face.

When she pulled away I gasped for air, but all I could taste was her pussy.

"You actually just came inside of that, didn't you?" She said with disgust.

"I... I'm sorry." I panted back, still feeling a high from my orgasm.

"Well, you're going to have to finish cleaning with cum all over yourself." She spat out.

When I looked up, she was putting her jeans back on, but I was still panting for air.

"I'm sorry." I said again as I sat up.

"Oh, you will be," she said and sat down, giving me a dirty look. "Finish your work."

"Yes, miss." I replied.

After that I moved to cleaning upstairs. It was even more difficult since I had a gallon of cum inside of this outfit. Occasionally I would get cum onto something and then have to clean it again.

By the time I was finished, it was nearly 5pm, and I hadn't seen or heard from Arabella.

Finally finished, I went downstairs and into the living room.

"I'm all done." I told her.

"Hmm, I don't need to inspect it, do I?" She asked. "You know I won't be happy if I don't like what you've done."

"It... it should all be done." I told her, suddenly nervous about my work.

"Right then," she said, turning her attention back to the TV. "Get changed and go home."

I looked at her, hoping she would make me cum again, but she didn't even look at me.

I just hung my head in shame and went to put on my regular clothes. Before leaving though, she shouted from the living room.

"I expect that outfit washed and brought back here brand new!" She shouted.

"Okay." I replied, although I had no idea how to wash it without my family seeing it!

Two days later.

I knocked on Arabella's door filled with nerves. A plastic bag in one hand, I just hoped she was happy.

"Michael, I wasn't expecting you so soon?" She asked, smiling at me in a kind, loving way, not like she had used my face to fuck herself with a few days earlier.

"I erm," I whispered, embarrassed about what I was about to say, "I have the outfit all washed."

She looked at me with her beautiful eyes, and her kind smile slowly turned to an evil grin.

"Hmm," she said and grabbed the bag, "I will see about that, come in."

My heart fluttered as I stepped inside, wondering what I would get to do with her this time.

"Upstairs." She said.

She let me take the lead walking upstairs.

"Left, into here." She told me, and I walked into a spare bedroom.

Once in, I watched as she pulled out the outfit and inspected it for a few moments before throwing it onto the floor.

"Take off your clothes and lay down." She ordered with no emotion in her voice.

Thank you, god!

In a heartbeat I ripped my clothes off until I was completely naked. Then I laid back, my hard cock ready to go with whatever she wanted.

"So eager," Arabella laughed, "you really are pathetic aren't you?"

I didn't know what to say. Her hurtful words just made me want her more.

As she knelt onto the bed my body felt on fire as her long, sharp fingernails found their way to my calves. My entire body tensed up as she ran them up and down, gently digging into me.

"I must say," She whispered, "you did an excellent job the other day. My house is spotless."

"Thank you." I panted as her nails kept moving up and down.

With a little push she spread my legs a little wider, and then she moved closer between them.

"And you have been behaving well," she whispered again, her nails moving to my lower thighs. "I think you have earnt a little reward."

"A... reward?" I panted.

Her blood red nails moved to both of my inner thighs, edging closer and closer to my smooth cock and balls.

"Yes," Arabella whispered and smiled. "Even little perverts like you deserve a reward for good behaviour."

"Ooooh god!" I moaned, her touch, her voice - god, I fucking loved it!

Then her tone changed.

"You're not about to cum already, are you?" She moaned out and sighed, and then her nails left my thighs.

"No!" I shouted, not wanting her to stop. "I can hold it, I promise!"

She looked at me with disgust again. I could see her thinking about whether or not I deserved this reward.

"Hmm, if you say you can hold it," she said, her evil smile returning, "then I expect you to hold it."

"I will, I promise." I told her, although I honestly would've said anything.

Her nails returned to my thighs but even closer to my cock. This was it, I was about to have my second experience of someone else touching my dick!

With her right hand, Arabella pressed the back of her nails against my smooth balls and slowly dragged them all the way up along my shaft.

My cock twitched from the touch, and my precum stuck to her nails.

"You really do get hard for me, don't you?" She whispered, staring into my eyes.

"I've always gotten hard for you," I admitted. "I've fantasised about you for so long."

This brought a grin to her face, her lips parting slightly to show me those perfect teeth. Her eyes were slightly covered by her brunette hair.