Housing Developments Ch. 02

I awoke the next morning disoriented. I panicked slightly when I didn't recognize where I was or by the fact I was wearing some women's nightie. It took a couple of seconds to remember and relax.

I was at a neighbour's, housesitting. Mr. and Mrs. Andrews were away on a Med cruise for a month. After dropping them off at the airport, I had the whole house to myself and started to discover... things. First was where Mrs. Andrews' clothes were. Then finding her sexy bikinis and nightie. Then figuring out that I enjoyed wearing her things as making myself cum.

I slipped my hand inside the panties I wore and had to peel off the sticking material so I could jerk off again. Afterwards, I stripped off Mrs. Andrews' nightwear and had a quick shower. No need to shave as I had never developed any beard let alone body hair. Even my pubic hair was less than sparse.

When I went to put back Mrs. Andrew's things in her walk-in closet, I decided rather than putting on my own underwear, I'd try Mrs. Andrews'. "Why not No one else is here."

I found which drawers she had her underthings and was in awe of my discovery. All sorts of different bras, panties and lingerie. I picked up a pretty purple bra with white trim. The cups seemed to be made from a light nylon material with hard wires underneath. It took me a few moments to figure out how it went on. The heavy metal stays dug into my chest.

With the matching tiny, French-cut panties sat high on my hips. My butt cheeks were totally exposed with a thin strip of material running between my ass-crack. The front was small but enough to hide me when I tucked myself inside.

I looked at myself in the mirror. While the outfit was a very sexy, I was very disappointed by the fact that my bra cups were empty and looked like deflated balloons. "Maybe I could find some socks or something to stuff in them?"

I rummaged around some more until I came across a couple of heavier material bras. I recognized them as sports bras similar to the ones my mother used to work-out in. They had stiff cups like Mom's except they were bigger. I took off the purple one and hooked the three hooks on the white sport one. The cups retained its shape. When I put the purple bra back on, it filled the soft cups and made it seem like I had tits! After putting a tee shirt on, you couldn't tell the difference.

I felt so good walking around the house with my sexy undies on. I purposely stuck out my chest to show off my big breasts. I swayed my shoulders back and forth as sexily as I could while prancing about. The cold marble main floor started to have an effect on my bare feet. So back to Mrs. Andrews' closet. I found some shoes, but as slight as I was, her shoes were too small. I'd barely squeezed my foot inside one and would never be able to walk. Then I remembered Mrs. Andrews and my secret. Mr. Andrews like to dress up too. I looked inside his walk-in.

Most of Mr. Andrew's closet was lined with men's fine shirts, trousers, suits and shoes, but the back wall was all female clothing. There were a couple of dresses but mostly just lingerie and corsets; none would fit since he was much bigger than I was. I peeked inside the drawers and found a number of sexy bras and panties. Most of the panties were ass-less. He also had a large selection of garter belts and stockings. Neatly lined up underneath were a number of shoes; all different styles and colours: red, black, white and pink. All had high thin heels of at least four and a half inches; the tallest had to be about six inches. None of them were platform.

I picked out a pair of pink mules to try on figuring it would be the easiest to wear. I sat down as I slipped my right foot in under the pink fur toe strap; then the left. The shoes were a bit loose still, my feet looked so sexy, but then I tried to stand. The five inch pencil heels made it impossible for me to balance. I teetered back and forth and had to sit down again.

Determined to figure this out, I stood up again using the furniture to help my balance. It took a number of attempts before I discovered how to stand and how to walk. With practice, I became more and more confident with my walking until I could take normal strides.

Over the next week and a half, I'd dress up in Mrs. Andrews' bras and panties and Mr. Andrews' shoes. I had to wear my boy stuff when I performed my lawn mowing job, but I'd rush back, clean up and dress up as soon as I was finished. Even then, sometimes I would wear some of Mrs. Andrews' panties under my shorts when doing the lawns.

Wednesday, Mom and Dad had to go out and so I'd have to fend dinner for myself. I ordered some pizza, but decided to make it more formal dining for myself. Of course that meant being dressed up more formally and so back to the closets.

I started with the sports bra so I would have breasts. Next was a black push-up, demi cup bra and tight cheekie panties. From my rummaging around, I found Mrs. Andrews garters and nylons. There was one that wrapped around my belly (which I later found out was called a waist cincher) and had three straps dangling from each side. When the front lacing was tied tightly, it sat on my hips and narrowed my waist. I slipped on some black translucent stockings with reinforced toes and heels and clipped them to my cincher.

I picked out one of Mrs. Andrews' elegant evening dresses. It was clingy and slightly sparkly with a low vee neckline that showed off my cleavage. The hem was about five inched above my knees and had a modest slight running up my left thigh. From Mr. Andrews' closet, I choose a pair of strappy side buckle shoes. They were black and had a five inch stiletto heel that clicked loudly when I walked on the marble flooring. With all the practice I've been doing, walking in heels became as natural as walking in bare feet.

I set up the table in the dining room. I bought a bottle of Chianti earlier so I set out a wine glass as well. I opened the bottle of red and poured myself a glass. The doorbell rang. It was only then that I thought. "How am I going to answer the door dressed up like this?"

"Ding-dong!" The door rang again. "Ding-dong!"

Fretting and panicking, I grabbed my wallet and pulled a fifty. I cracked the door and peered out showing only my head.

"Pizza Place Pizza!" The delivery person announced holding the hot pie out for me to take. On a closer look I realized it was a she. Cute, short red-orange hair with blue eyes and a slight freckled complexion. She stood about five feet tall and was about my age.

"Oh... Yes... Uuh..." I stammered as I took the pie from her. I went to hand her the bill but I let got too quickly and the wind blew it back inside. Acting on reflex, I let the door go to chase after it. The door swung open. I hid behind the door but not quickly enough. The girl had seen all of me. Credit to her, she said nothing although I could see her reaction in her eyes. I gave her the fifty for a 20 dollar pie. "Er... Thanks. Keep the change!"

I closed the door. My heart beat like a drum. My knees shook like a willow in the wind. Amazingly, with the excitement of being seen, I had an erection in my panties.

I managed to place the pizza on the dining table but had to sit and calm myself. I filled my glass and took a large gulp of wine. When finally calmed enough, I enjoyed my meal. I turned on some soft dinner jazz and sat at the table; my feet under my chair, my ankles crossed, my knees tightly together. My hand still shook as I placed a slice on my plate.

Being a proper lady, I used my knife and fork to cut off a bite. I opened my mouth and was about to put it in when I heard the front door unlock and open.

"Yeah... Too bad!" The voice said. "Thanks for the lift."

I was frozen in place.

There was a loud thud of luggage dropping to the floor and squeaky rubber shoes approaching my way. "What...? Who...? What!"

I looked towards the voice and recognized Alana immediately. My mouth was still agape with the bit of pizza at the end of my fork.

"James?" Alana asked. "James, is that you?"

"Er... yes." I answered sheepishly. "Hi Alana. Um... I thought you were supposed to be away?"

"There was an emergency and we had to... never mind me. What the fuck are you doing in a dress?" Alana demanded. "Is that my mother's?"

"Yes." Was all I could answer.

Amazingly, Alana wasn't really upset or mad or anything. She actually sat at the table and enjoyed the wine and pizza with me. We talked. I explained what happened and she seemed to be very sympathetic.

"James, I think you make a very nice looking girl." Alana smiled. "Hmmm, James isn't a good girl name though. You should think of a more proper girl's name."

"My mom calls me Jamie." I said proudly. "That could be a girl's name too, couldn't it?"

"Jamie it is then!" Alana said. "I think you need some make-up."

While I cleaned up the dishes and hunted for another bottle of wine, Alana went to her room to prep things for me. By the time I got there, Alana had changed clothes from the tee and short jean shorts and was wearing a very pretty pink crinoline dress with pink shoes and pink nylons. The top was a little less than modest square neck that showed slightly less cleavage than mine did but still revealed some of her firm, melon sized breasts.

"Sit!" Instructed Alana as she flipped her long blond hair behind her shoulder.

We both sipped the wine as she applied foundation and make-up to my face. She explained what she was doing so I could do it myself. When she was done, I looked completely different; very feminine but my short crop of hair really didn't belong. Alana went into her closet and returned holding a blond wig.

"I used to wear this before I could grow my hair out." Alana confided. "It's custom made but I think it will do."

She positioned it on my head and brushed it out. It was a bit loose but enough to stay in place. Alana clipped a black ribbon choker around my neck and then stood back. The transformation completed, her smile went from ear to ear. I looked at myself in the full length mirror and was amazed by the girl that looked back at me. Tears started to well up in my eyes.

"No! No! Don't cry!" Alana warned. "You'll ruin your make-up."

She handed me a tissue to blot the tears away.

"Oh thank you Alana! I look so..." I couldn't find the proper descriptive. I gave her a hug.

She hugged me back. The crinoline crunched into my groin. Still in an embrace, we looked into each other's eyes. Alana held the back of my head and pulled me towards her until our lips touched. Immediately I responded. Her tongue pierce through my lips and probed inside my mouth. My hands cupped her breasts; my fingers sought out her nipples. I gently pulled them out from her dress. I lowered my head and in rotation, suckled on my breasts.

Alana put her hand on the top of my head and pushed me to my knees. I lifted up her hem and with my head beneath, I fished my way through the pink crinoline until I found her panties. I took hold of the waistband and slowly pulled them down.

She didn't make it easy as she kept her knees tightly together, but I managed to pull them down to her ankles. I looked up to place my mouth against her bare pussy but something wasn't right. She parted her thighs and then from between popped a penis. It hit me square in the face.

I was about to protest, but Alana acted faster. She grabbed the back of my head with two hands and forced her cock into my mouth and down my throat.

I never had any other cock in my mouth other than my own. Even then maybe about four inches of it. Alana had to be about eight and she used all of it in my mouth. She thrusted her hips back and forth until she shot her load into my belly. When she finally released me, I found her sitting on her bed crying.

"Don't cry!" I said. "You'll ruin your make-up!'

That changed her sobs to chuckles. "Thanks! And I'm sorry I didn't tell you before we started."

"Tell me what? That you had a cock!?" I asked but not angrily. "Actually, I enjoyed it."

Alana was born Alan Andrews. She had always felt like she was born with the wrong parts. Mr. and Mrs. Andrews accepted her almost immediately after she told them of her true gender identity. Being young at the time, other than dressing as a girl, they could do little else but wait. When she became of age, her parents arranged for her to get breast implants. Alana wanted no questions that she was a girl or that she wasn't Mrs. Andrews' daughter so she got similar sized breasts to her mother's. But ultimately the thought of cutting off her male appendage seemed cruel, so she decided to keep it.

Alana was crying freely as she related her story to me. I sat beside her and tried to comfort her as best I could. I placed my arm around her shoulders and laid her head against me. That changed into a hug, then to an embrace and then into fully fledged making out.

"Jamie, have you ever been fucked before?" Alana asked. "I mean had a penis in your ass?"

I stood up and supported myself by placing my hands on the bed. "No. But I'd love you to be my first."

Alana stood up and smiled. From behind me, she pulled my dress over my bum and over my hips. As she pulled down my panties, she commented. "Very sexy. My mother has such wicked tastes for sexy things, doesn't she?"

I turned and watched Alana lifted her dress and showed me her hard cock. She placed it gently against my rear hole. A big gob of spit dripped from her mouth and hit her knob which she used to lubricate us. Slowly, she pressed it into me.

The feeling was not like my finger entering. It was so much more exciting; exhilarating; electrifying. It spread me open. I pushed back.

"Are you okay?" Alana asked me. "Does it hurt?"

"No! Please push it in!" I pled. "Push it in! I want it inside me!"

She held my hips firmly and pushed forward while I pushed back towards her. Slowly at first until it popped all the way in. "Oh god! Fuck that feels incredible!"

Alana pulled out a couple of inches and pushed it back in to test to see if I was still okay. I groaned in ecstasy so she fucked me a little harder. "Shit! Your ass hole is so tight!"

"Oh my gawd! I have never felt anything like this before. My whole body is feeling it!" I cried out. "Please fuck me! Fuck me harder!"

Alana pumped harder and harder. Her grunts her louder and louder. "Oh fuck! Oh fuck! Jamie, I'm going to cum. I'm going to shoot my load inside your ass!"

"Yes! Yes! Fuck me! Come inside me!" I begged. "I want you to cum inside me!"

"Uuh! Uuh! Uuuuhhh...!" Grunted Alana as she emptied whatever cum she had left in her balls.

I collapsed my face onto the bed. I whimpered as Alana slowly withdrew herself from me. I could feel my hole still gaped open a bit and her cum oozed out. Alana dropped to her knees and lapped up any leakage. Then her long tongue entered and dug out any remaining sperm. My knees trembled as she made me orgasm numerous times.

Exhausted, we laid side by side in her bed and fell asleep.