Made to Maid Ch. 02: Transition

I stood there staring towards my girlfriend Cheri as she walked away. She had found my panties balled up inside the corner of a fitted sheet while we were changing the bed linens. After insisting I wasn't having an affair or that another woman was in our bed and acknowledging the panties were not hers, Cheri was left with the one only possible answer; they were mine. And I confessed they indeed were my panties. And in fact I was now wearing panties under my sweats.

After displaying my wardrobe for her, Cheri said... no, ordered me to "Get dressed!" and "Don't forget your boobs!"

The panties were the ones caught in the sheets; pink bikinis with an embroidered red rose in the front just above where my crotch was. As I stepped into them, I didn't realize how hard I was as I couldn't tuck myself under. I carefully positioned and secured my custom, self-adhering double-D breast forms to my smooth, genetically hairless chest and supported them with the ultra-red demi-cup bra Cheri picked out for me to wear. It was a cheap and slutty bra I picked up at some adult sex shop a couple of years ago.

The top was just a tight fitting, cotton, cropped tee with a low scoop front. Pulled over my big breasts, the thin cotton was near transparent and my bra was clearly visible. The huge pointy nipples really poke through.

The skirt was a short tartan that barely covered my bum. Sitting or bending would make it impossible to be any sort of a lady.

I pulled up the pink knee socks and strapped on my black, four and a half inch stiletto Mary Janes.

As the saying goes: "In for a penny; in for a pound!" If I'm going to be a slutty school girl...

I quickly applied some light make-up, mascara and lipstick and then brushed out my hair before pinning in a cute, Hello Kitty barrette.

Concentrating on making myself pretty for Cheri (and me!), my erection had ebbed enough for me to tuck it under and hide any protruding lump. I checked myself in the mirror and smiled. And then it hit me. "What the fuck are you doing?"

I guess in my sub-conscience, I always dreamed of being caught and sissified. But like a dog that finally catches a car...

I took my first, precarious step towards Cheri, then a next and a next. My heels clacked on the floor like thunder during a raging storm. My knees quivered; my legs were barely able to support me. As I appear around the corner to see Cheri sitting on the chesterfield, I froze in fear.

"Come on, darling! Don't be shy!" Cheri beckoned with a wave. As I approached, she smiled. "Oh! Don't we look the slutty sissy!"

I stood there in the middle of the living room shivering like I was standing outside in 20 below zero weather. It was worse when I turned and noticed the front picture window drapes were open and anyone walking by could see in!

"What's wrong, sweety? Afraid someone outside might see you? Don't worry. No one will suspect you are a man anymore. Especially dress like..." Cheri mocked. "No one will mistake you for a BMOC. Maybe more of a BSOC; Biggest Slut on Campus!"

Of course Cheri's comments didn't make me feel any more secure. I still stood there and quaked. Her comments continued.

"Let me see how the panties fit on you." I pulled up my skirt and at her gesture, showed bot the front and back. Cheri grinned. "Nice. Very nice. A lot of girls would be so jealous of how nice and round and girly your bum looks."

"My! My! And what big breasts you have. Are you cold? You must be cold. Your nips are hard and poking straight out!" Cheri sneered. "Lift your shirt. I want to see them!"

Letting go of my skirt, I raised my shaking hands and pinched the bottom of the shirt with my trembling fingers and thumbs. Slowly, I pulled the hem up over my boobs. "Wow! They look so real!"

Even with the bra on, my weighty boobs pulled forward and I supported them by cupping them from underneath.

"I guess I'll have to teach you a few things. When women want to show off their tits, the bend forward a bit and thrust their boobs forward while they push their hips back." I did as she suggested. "Mmm... Much better!"

Cheri rose up from her seat and moved towards me. Looking up at her face was straining my neck so I could either look forward or down. She stood in front of me. She undid the belt holding her robe closed and let the robe drop. She was wearing her satin, French knickers beneath. But something dangled from out of a leg hole. "Pull them down!"

I grabbed the shorts and pulled them down. She was wearing her strap-on; eight thick inches of meat!

We bought it as a lark but soon incorporated it into our regular bedroom activities especially when I wanted sex but she couldn't. So not our first time using it, but our first time using it with me as a girl. I felt a painful strain grow inside my panties.

A hand grabbed a hank of my hair and held my head while her right hand grabbed the base of the strap-on and point it upward. She pushed my head down far enough so she could gently slap my face with her cock. "Do you want to suck it?"

I nodded yes. Difficult to do with someone holding my hair.

I opened my mouth and sealed the fat knobby part with my lips which I found difficult to do bending over with crooked knees and wearing high heels. Cheri steadied the back of my head with both hands and started to pitch her hips forward shoving more and more of her cock down my throat. Unknowingly to Cheri, I've practiced and succeeded in my ability to not gag as she hit the back of my gullet. With as much as she could shove in, my nose smashed against her harness. The tip blocked my airway preventing me from breathing. I started to panic and tried to pull away but Cheri held me there. Only when I started to choke did she free me from her grip.

I was still bent over gasping for air when I noticed Cheri was behind me. She kicked my feet apart and flipped up my skirt. Rather than pull my favourite panties down or aside, Cheri grabbed it through the leg holes and ripped the ass open. Her long razor nails grazed my asshole.

"Uh, Cheri?" I knew what was probably coming but was concerned with the unshaded picture window. Something firm slapped against my cheeks and then ran up and down my crack. My saliva from sucking provided the slippery lubricant that allowed Cheri to start her penetration. The head of her cock pressed against my hole. "Uuuhhh..."

Cheri back off a bit then pushed forward. My hole started to stretch. Sher repeated it until I felt her knob open me enough to pop in. I moaned. "Oh gawd!"

Cheri continued to pump, pushing more and more of it into me. I was having a bit of trouble keeping my balance but Cheri held my hips which helped keep me steady. She pulled out enough to only leave the knob in me before sliding it all back in. I know it was only eight inches long but it felt like a ten foot pole inside of me.

The thrusts became a little shorter but firmer and faster until finally Cheri was smashing her hips into my ass. It was hitting me in that right spot and I knew I was going to C...U...M...!

"Uuuhhh! Uuuhhh! UUUHHH!" I spurted huge wads of cum inside my panties. Bent over the way I was, I could see a big wet spot grow making the material almost translucent.

Cheri had unsnapped her harness leaving her cock still inside of my ass. She dropped the harness and moved to the sofa. She held her legs up in a vee and with a crooked finger instructed me to come and eat her pussy.

I was about to kneel in front but Cheri forbade it and made me eat her while still standing and bent over obviously still on display in the front window. As I ravished Cheri's sopping slit, the cock in my ass slipped out and fell on the floor. Cheri wrapped her legs around my head, crushing my face in her cunt until she came. Holding the back of my head and humping her hips, she fucked my face as she orgasmed hard.

I felt her body collapse and let her powerful grip on me release. I looked at Cheri a heaving, splayed heap on the couch. My face soaked by her girl cum felt cool as it dried and tightened my skin. My ass ached. Not a painful ache but a wanting, throbbing ache; wanting to be fucked again ache.

Wanting to talk with her, I stood waiting for Cheri to recover enough; still on display in front of the window. Her eyes finally fluttered open. She looked up at me and grinned.

"THAT was awesome!" Cheri told me. She patted the seat beside her for me to sit down. "My pussy is still tingling!"

I wasn't sure how to broach the subject and decided maybe a direct approach would be best. "Uh... Cheri? Are we okay? I mean, you don't seem to be upset or anything like that."

Cheri smiled at me. "Well, you see. When I was at university, my (air quotes) girlfriend and I... Well let's just say we enjoyed each other. I learned that I was bi and liked having sex with both male and female partners."

I was taken aback. That was the first time she had ever mentioned something like that. She had never expressed any interest or even hinted anything close to being bi.

"It was something I hid since we started dating. I thought you might think it weird. So when I found out about your secret, it was like a dam bursting and it all came flooding back." Cheri continued. "You're the best of both worlds."

"You mean... We're okay?" I asked tentatively.

"Yes. We're okay. By the way." Cheri looked at me. "Do you have a girl name?"

"Yes." I shook my head positively. "Molly."