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Introduction:

Aunt Leah got me into dressing like a girl and I liked it. Then we started going out on dates and my life would never go back to the way it was.

This story has been edited from the first drafts. I unintentionally blended events across chapters one and two so I merged them into a single story.

My Aunt Leah by Jodi S.

Aunt Leah’s Porsche was in the driveway when I got home Saturday afternoon from work at the Discount Store. I parked behind my mom’s car and found her and Leah drinking tea in the dining room.

“Hello Ladies!”, My mom presented her cheek for a kiss. “Sorry I’m so messy, but Mr. Miller had me cut up all the boxes for the recycle bin.”

“Ahem. Forgetting something?” I kissed Leah also.

“My apologies, Princess.” Princess Leah was my pet name for my moms best friend. She’s not really my aunt but that’s what I have been calling her since I was a baby. My mom and Leah get

together at least a couple times of week and meet at the gym regularly. Originally from Berlin, Leah was a model before she met her husband, a fashion and celebrity photographer. They had twin

girls together before he decided to come out of the closet, so they divorced, but remained friends until his death a few years later from an unexpected illness. Between her money from modeling and

the inheritance from her former husband, Leah was very well off.

My mom, my older sister Dina, and myself live in Hollywood Hills. Not that one, the one in Florida. No movie stars and no hills either, while Leah has a large waterfront home in Fort Lauderdale a few

miles north and east of us.

Leaving on my boxer briefs, I put the rest of my dirty clothes right into the washer and peeked out to see if the coast was clear before scampering to my bathroom. In the shower I could feel my long

blonde hair between my shoulder blades as I rinsed out the shampoo. Looking down as I lathered up my skinny body, I was totally disappointed. Completely hairless except for a tiny patch of peach

fuzz on my groin, I looked more like a girl than a boy. I tried to work out and bulk up but all it got me was more toned, except for my gluteus maximus, which turned it into a bubble butt. Today at work, I

was organized the shelves when I heard a voice behind me, “Miss, excuse me miss. Do you have duct tape?”

I turned around and the lady just looked at me. I guess with my long hairless legs sticking out of my khaki shorts and a slightly too tight polo shirt, she still thought I was a girl. I sighed and showed her

where the tape was. I get it all the time. With feminine features, no facial hair, full pink lips and bright green eyes, at least half the people I meet aren’t sure what I am. My hair doesn’t help. Long

straight and blonde, I leave it loose and really don’t want to cut it. Even in blue jeans and a plaid lumberjack shirt, people aren’t sure if I’m a femboy or a lesbian.

While I was washing my torso, I began to think about aunt Leah. When I bent over to kiss her cheek, I got a good look down her shirt at her abundant cleavage as well as a whiff of her perfume. ‘It’s

so wrong’, as I felt the inevitable begin to happen. ‘Well, she’s not really my aunt, and she’s so hot.’

Needless to say, I lost the moral battle with myself as my load splattered on the tile.

****

Reading on the couch later that night, my older sister, Dina, sat down next to me. “What’s wrong?”

I closed the book and looked at her. “I’m not happy at work. I’ve been there over a year, I do more work that anyone else, but since I’m part time, I get paid less than all the other full timers. I

keep getting more responsibility so I asked for a raise and he offered me fifty cents more per hour.”

“It was worth it when it was all I could find, but I think I’m going to look for something else. Maybe something with tips so I can make more money.”

She nodded. “I see. Well, just don’t burn your bridge with him, he should give you an excellent reference for you new employer.”

She kissed me on the forehead and went to leave but stopped. “I heard Aunt Leah talking to mom. She wants to clean and paint her garage but doesn’t know who to call. It’s a pretty big job. Maybe

you should talk to her."

Dina called Leah herself and promised me for Saturday.

Aunt Leah had backed both cars out of the garage, so I pulled in behind them. She was moving boxes around when I walked up.

“Jodi!”, she exclaimed as she hugged me.

I hugged her back and could clearly feel her nipples against my chest. I had worn shorts and a tee shirt in case we started today and Leah was in shorts and a tank top with a bra, but it must not have

been very substantial.

She took me by the hand and led me into the garage.

“I want to take all this stuff down from the shelves. Clean the shelves and paint the wall behind them and then I’ll go through all this stuff and put back what I want to keep and get rid of he rest. Once

that’s done, I want to paint the rest of the walls and the ceiling. It’s a big job, but I think you can do it. I can pay fifteen dollars per hour. What do you think?”

I didn’t have to think long. “Piece of cake, Aunt Leah. I don’t know how long it will take but I’m sure I can get it done.”

We stated right away by taking everything down from the shelves and placing the boxes and other stuff on the floor of the garage in a long line so that Leah could pick through it.

The cleaning supplies I was moving almost hit the ground when I looked around. Leah had bent over and I could see her thong panties creeping up from the back of her shorts. Holy crap, I’m pretty

sure my mom doesn’t have any thong panties.

I must admit, Aunt Leah had a rocking body. Nice ass, as I could see very well, bigger boobs than my moms. All in all, a curvy figure that she keeps up with in the gym.

When I put the bucket down I got a nice view down her shirt at her perfect cleavage. I better stop looking or something embarrassing would be coming up.

“Aunt Leah?”

“Yes, Dear?”

These shelves are very dusty, we are going to need particle masks before we can start cleaning them. I have allergies and I don’t want you inhaling God knows what that’s up here.”

“Yeah, you’re right. The closest hardware store is around thirty minutes away. Could we make our own?”

We used old tee shirts from the rag bag to make bandanas and I used the shop vac to get most of the dust off the shelves before cleaning them with spray cleaner and rags. It was afternoon before

the shelves were clear and clean, but they were much nice looking now.

“Let’s break for lunch. How about leftover chicken and cole slaw?”

“That’s great, Aunt Leah, but I’m so dirty I don’t think I can come in the house.”

She looked at me, “Yeah, you’ve been working so hard. Go upstairs and use the girl’s shower and then get some shorts and a shirt from Ali’s room.”

Upstairs, I knew right where Ali’s room and shower were. I had played with them many times when I was a kid. They were older and very pretty and I worshipped them.

After my shower, I wrapped a towel around my waist and went to hunt for clean clothes.

I checked the dresser and the top drawers had panties, bras and stockings. The second row was full of tops and the bottom had plenty of shorts, but nothing was designed for a boy. The closet

Things I could find were a pair of stretchy athletic shorts and a tee shirt. But the tee shirt was a baby tee with little tiny sleeves. I finally found a tank top that didn’t look totally girly and hung down far

enough to cover my crotch, since she didn’t have any undies that I could wear. I checked myself in the mirror.

Shit, I looked like a damn girl. I know Leah wouldn’t care, but still.

Downstairs, Leah had put a platter of cold roast chicken, cole slaw and potato salad on the table by the pool.

She didn’t make a comment about my shirt and shorts, so I sat down and took a sip of iced tea. Leah never drank soda, only homemade iced tea or seltzer water.

After lunch, we relaxed on chaise lounges by the pool in the shade.

“Jodi, we can’t do much else until the wall gets painted. I’m not in the mood to go shopping today. Can we go pick up all the supplies tomorrow? If you don’t want to work on Sunday, I understand.”

“We can go tomorrow. We are going to need paint, rollers, roller pans, drop cloths and probably some other stuff. I can start a list and we can go first thing in the morning.”

Leah said, “Are you in a hurry to get anywhere? I was going to take a swim and would love if you could stay a while and join me.”

“Sure Aunt Leah.”

“Just Leah, please.”

“Sure Leah, I would love to take a dip. It’s still pretty hot out.”

With no plans for the rest of the day, I had time for a swim before going home.

Leah went to her room to change and I waited until she was gone before taking off Ali’s shirt and getting into the pool. Luckily the shorts stayed opaque when wet even though they were pretty tight and clingy.

My eyes were closed as I was leaning back, sitting on the steps when a shadow passed over. Leah had changed and was back. She was wearing a black one-pieces swim suit with a light robe over

it and holding towels for us. She turned to set the towels on a chair and take off her robe. The swimsuit was entirely backless except for where it did a pretty meager job of covering her bottom. At

least half was hanging out. I could see the crease at the bottom where it met her legs. I could feel and uncomfortable stirring in my shorts. I turned away to pretend I hadn’t seen her and she came

down steps and began to swim across the pool using a breast stroke to keep her head above water. She took one lap and joined me on the steps.

“Sorry you didn’t get a full day in, Jodi. Your mom said you may quit your job?”

“Yeah, Stu is a decent boss, just cheap. I’ve been there a year and I had to ask for a raise. He’s got me stocking shelve as well as the running the cash register, I know for a fact that the cashiers are

all making more than I am.”

“Don’t burn your bridges, he could offer you a good reference if you find something better.”

Leah pushed off and turned over on her back and floated, barely. Her face, boobs and toes were the only parts out of the water and her nipples and aureoles were clearly outlined on the thin wet

fabric.

After a minute or two she stood up and asked, “Can you float? Or are you too skinny? Oh dear, I didn’t mean it like that. It’s just that it takes a certain amount of body fat to float and luckily my butt

keeps me up.”

I shook my head, “You’re right, I sink like a rock. I’ve tried and tried and even in salt water I still sink.”

“Come here Jodi, let me help you.”

I paddled over, tried to float and quickly went under. Before I could stand I felt Leah’s hand under me lifting me to the surface. I went up and with her help could float, kind of.

“Put your arms over your head to counter-balance your legs.”

I did and she used less pressure and I began to sink, so she lifted me up again.

“Yeah, if you fall overboard I hope you have a life jacket.”

She didn’t stop holding me so I leaned back with my eyes closed and let her keep me from sinking.

“Jodi, I’m sorry that I said you were skinny. I think you are in perfect shape, you have a really nice body.”

“Easy for you to say, Leah. You used to be a model and I don’t think anyone would mistake you for a man.”

“What do you mean?”

“Especially from behind, I get mistaken for a girl more than I would like.”

“Oh, that’s because of your beautiful, long, blonde hair. And don’t get any ideas about cutting it, I love it. Don’t worry about a thing. You’re young. Enjoy it while you can. I was a scrawny teenager

when I was your age and look what happened there.”

Her voice was mesmerizing and I was so relaxed it came out without really thinking. “I’m sure you were as beautiful then as you are now.”

When I realized what I said, I froze and pretended like nothing had happened.

She let me go, so I let my feet fall to the bottom. She was looking straight into my eyes. “That was really sweet, Jodi. You are really a nice guy.”

When we got out of the pool, I quickly wrapped the towel around my waist. I may be skinny but what I had in my shorts wasn’t. Leah returned with my clothes, shook out most of the dust and set

them on the chair.

“You’re welcome to take Ali’s things, but they’re wet. You’re just going to have to wear your old stuff home. Maybe you could bring a couple changes and a swimsuit if you are going to be working here

for a while.”

In the laundry room I went to change into my work shorts when I looked down. The stretchy fabric showed the outline of my dick clearly as well as my balls. Since I’m circumcised the outline of my

dick head was clearly visible. Oh no. I was lying on my back in the pool and Leah’s face was right there. I tossed the wet stuff into the washer and put on my dusty shorts but my shirt was sweaty

and grimy.

Leah walked me out to my car in the swimsuit and robe and sent me home with a kiss on the cheek.

The garage project took longer than expected. After the ceiling and walls were freshly painted the concrete floor looked a little dingy. I put down a special epoxy paint and it came out great. I quit my

job at the discount store and started working at Leah’s house over the summer. Leah wanted to remodel both girls rooms. They rooms were dated and needed a freshening up and Leah wanted to

surprise them. We started by creating a design plan. Then, a complete paint job and new lighting. A company was hired to rip up the carpet and put down hardwood flooring. They had agreed to

move all the furniture out into the hall and haul off the old carpet. With the limited space, we could only do one bedroom at a time. With all the upgrades, the old furniture didn’t look good any more and

Leah ordered Ali a new bedroom suite.

Once the room was completed and the furniture installed, it looked so perfect that Leah took pictures of it before it was lived in.

“Jodi, what do you think?”

“It’s amazing. It looks like something out of a magazine.”

“You know what, Jodi. You have done so much around here and I really impressed on how much you know about all this stuff”

“You created the design. I just helped with the easy stuff and what I didn’t know, I looked up on YouTube.”

“You’re too modest. I’m going to start getting busier. The magazine wants me to start a column on South Florida. Not a serious piece, just trending restaurants, who’s who around town and charity

events. I’m going to be going out more and spending more time in my office.”

Masters degree in journalism qualified her to work as a free-lance editor for an international fashion magazine. Leah worked from her home office laying out and editing articles.

“OK.” I didn’t see where this was leading.

“I won’t have time to do all the things I’m used to. Keeping up with cleaning crew, landscapers, scheduling routine maintenance and the like. I would like you to offer you a permanent position as

household manager. You would oversee maintaining the house.

It would be a great relief if you would think about it.”

“There’s nothing to think about, Leah. Congratulations on your promotion.”

She wrapped me up in a hug and planted a big kiss, this time on my lips.

“I knew I could count on you. You are going to be turning eighteen soon. I have been paying you cash, but I think a salary would be more appropriate. You can open a bank account and I can use

direct deposit and we can get you debit and credit cards. Plus, I need to deduct it and can’t do that if I keep paying you cash.”

I didn’t even ask what my salary would be. Truth be told, I was smitten with Leah and would have worked for free just to be around her and be her friend.

Now that Ali’s bedroom was complete, it was time to move all her clothes back into her new dresser. I just pulled out the top drawer of the old dresser and carried it into her room. The top drawers

contained Ali’s underwear, so I went back to get myself a drawer full of shirts, so that I didn’t have to go into Ali’s things. When I came back in, Leah was holding up a green satin teddy trimmed in

lace. In the drawer was the matching panties and lacy shorts.

“Look, Jodi. This color perfectly matches your eyes.”

She pulled me in front of the mirror and held the lingerie to my chest from behind. I had to admit, it was a close match. Not too many blondes have green eyes, but I did.

Leah whispered in my ear. “I’d love to see you in it.”

My eyes were wide as I looked at hers in the reflection of the mirror. My mouth was suddenly dry and I didn’t know what to say. I didn’t want to let her down, but this was a pretty big thing to ask. I

wasn’t gay. Heck, I never had a girlfriend or a boyfriend.

“Come on. I would love it. I’ll give you an extra days pay if you say yes.”

I made up my mind. “No Leah.” She winced. “I don’t mean no I wont do it. I mean I’ll do it, but you don’t have to pay me.”

She smiled and flashed her white teeth, truly happy.

I took the negligee and went to change in the bathroom.

“Aren’t you forgetting something?”

Leah was holding up the matching panties and shorts. I took them with me into the bathroom. I looked at myself in the mirror and sighed. I wasn’t really sure what was going on. Leah gave me lots

of hugs and kisses and we had become pretty close but this was something I never imagined. I know I look like a fem, but I don’t dress like one. Until now.

I undressed and slipped the panties on. I had to carefully put my junk in to avoid my balls spilling out and the only was I could get my dick in was to turn it sideways. I slipped on the shorts and it

helped hide it, barely. The teddy went on pretty easily, just slipped over my arms and tied it in the front. I arranged my hair to the front around my face and down my chest. Damn, I looked prettier

than most of the girls at school. I had a semi, but I didn’t think I was going to get hard. I turned the lights down and in the dim light, I looked downright sexy. Heck, I would do myself if I had the chance,

but there was something missing. I opened the top drawer and there was tubes and vials of Ali’s makeup. I chose a pale pink lip gloss, I wasn’t ready for real lipstick.

Leah had turned down the lights in the bedroom also. I took a breath and could feel myself shaking with fear. What if she laughed at me. Fuck it. I stood up straight and walked into the bedroom.

Leah was sitting on the chair in front of the vanity and gasped when she saw me.

“Oh my! You are absolutely stunning. Are you okay? Is everything all right?”

She was so sweet that I lost most of my nervousness and turned and walked away before turning around and standing in front of her.

“Jodi, you look absolutely beautiful. I have wanted to ask you to do this for so long, but I was afraid that you would turn me down.”

“I can’t say no to you Leah. I’m glad you like it.”

“Have you, um, ever done anything like this before?”

Laughing, I told her the truth. “No, I was too chicken.”

It was Leahs turn to laugh. “You don’t have to worry. I love it. If you like it, you can do it all you want in the privacy of our home.” She paused. “When is your birthday?”

“Next month.”

She held my face in her hands. “Jodi, I need to you promise me something.”

“Anything for you, Leah.”

“Promise me that you won’t let me do something I would regret.”

Her lips came to mine and she held them there. I tried to slip my tongue between them and finally she pushed me away, breathing heavily. “Let’s get these clothes put away and I would consider it a

favor if you wore that for a little while longer.”

Kristen’s room took even longer for some reason. There were delays on shipments and we managed to get it done before the twins came home for Thanksgiving. I hadn’t seen them for a couple

months and neither knew about their bedrooms. My eighteen birthday fell on a Thursday, so my parents decided to have a backyard barbecue for me on Saturday afternoon. We had a small group of

my friends and relatives over and my cousin was acting as DJ when Leah, Alexa and Kristen came out the back door. Alexa and Kristen ran over and practically knocked me down.

My friends from school were notably impressed watching me get hugged by two cute college babes.

“Jodi, thank you so much.” said Alexa.

“Our rooms look fantastic, we just love them!”

I held out my cheek for a kiss from Leah and everyone went back to mingling.

As the party was winding down, Leah found me in the kitchen getting more ice.

“Are you busy tomorrow? The girls are going to South Beach with some friends and I thought that maybe you and I could go out to lunch.”

“Sure. What time?”

“Whenever.”

“Ten too early?”

“Ten is fine.”

When I got there at ten, the twins hadn’t even gotten out of bed yet. They had gone out the previous night and were sleeping in. Leah took me to her side of the house. Her suite on the first floor had a

master bedroom, master bath, her home office and a small living room with a television and shelves full of books. She took me to her living room and we sat on the couch.

“I was hoping you could see the girls, but they got in late.”

“Me too. It’s all right.”

“It’s a little early for lunch, so would you like to just hang out and relax a while? I was thinking of driving to Boca later.”

We usually went to Las Olas, it was practically around the corner. “Not Las Olas?”

“No, I want to do something special.”

We were chatting when I heard a voice call out. “Mom? Are you here?”

“In here, Kristen.”

“Jodi!”, she exclaimed when she saw me. “Oh My god! I was just thinking about you when I woke up in my new room. What are you doing here?”

“Kristen! That’s not polite!”

“It’s OK. I’m just visiting. We may go out to lunch later.”

“Oh cool. Mom can I borrow the SUV? Six of us want to go and it’s the only vehicle that can fit us all.”

“Sure dear. Just be careful.” No sense preaching. The twins were responsible and Leah realized that sometimes you just have to trust them.

They came down a later wearing shorts and tank tops over their bikinis and carrying beach bags to say good bye.

“Bye Jodi,” one kiss on the left cheek, “Bye Jodi” and a kiss on the right. “Bye mom!”

*****

Leah stood up and took me by the hand into her bedroom. I was confused and was more confused when I saw the clothes on her bed. I looked at her. She gave me her puppy dog eyes. “Please? For me?”

On the bed was a pair of cream colored pleated shorts and belt, panties and matching bra, a white camisole, a sheer white long sleeve blouse. On the floor by the bed was a pair of wedge sandals

that matched the belt.

“Please Jodi?”

“Shoo. You’re not watching me change.” She scampered out of the room.

Sighing, I had a feeling this was what she had in mind. Every time I got done working, she insisted I shower and when I came out there was always an outfit waiting for me on the bed upstairs. But it

was always lingerie for wearing around the house when we were alone. These were going out clothes. I suppose I knew because I made sure to shave my legs and underarms before I came over. I

slipped on the panties and to my surprise they had a pouch in front that kept me out of danger from falling out. Around the house it wasn’t an issue but if we were going out it could be a real problem.

The bra went on next, then the cami, and the shorts. My normal shorts came nearly to my knees, these shorts barely covered my ass. I put on the belt and slipped on and tied the sandals around my

ankles. The sheer blouse covered my torso but had no buttons. Just a tie at the bottom. I fluffed my hair out of the collar and stood in the mirror. I liked the sandals. The lift made my butt tighten up

and stick out. The back seam was buried in my crack, just like a hot girl. The only problem was my package. Without some way to tuck it down and under it was pretty noticeable.

I modeled the outfit for Leah. She adjusted my collar and smoothed down my blouse.

I looked down and said, “Leah, I can’t go out like this. These shorts are too snug. My package is sticking out.”

Leah looked down, “Oh dear. I didn’t think it would be a problem. I’ll have to let you borrow a pair of Kristen’s gymnastic briefs. They should tame your trouser tiger.”

I offered to go get them, partially to test out my new sandals and partially to let Leah look at my ass as I walked away. I was feeling sexy so I gave it an extra wiggle for her.

Changing my panties upstairs, I was sorry not to get to wear the sexy pair but the microfiber gym briefs did a good job of concealing my bulge.

Downstairs I held out the first pair I had tried on. “Leah, what are these? They hold me in better than regular panties.”

“I ordered them online. They are made especially for men.”

“I really like them. I’m going to have to get some.”

“No honey. You’re going to have to let me get you some. We’ve never been out like this before. Do you think you can do it?”

“I don’t know. What do you think?”

She got very close and kissed me on the lips. “I think you are so damn sexy.” Leah went into her walk in closet got undressed without bothering to close the door. Slipping into a tight, white mini tank

dress and matching wrap, she eased into some white pumps. With a little bright red lipstick and a quick brush on of some makeup she was ready to go.

From her jewelry box, she took out a thin gold chain and matching bracelet. “These are perfect for you.” and put them on me before holding out her hand and leading me to the garage. “Shit, I almost

forgot. You need a purse.”

I had forgotten also. I never needed one before. Into the small white purse went my wallet, phone, hairbrush and lip gloss.

The Porsche Cayman was a hard top so I didn’t have to worry about our hair blowing around on I-95 north.

“Have you ever been to Mizner Park? No? It’s a pretty cool open air dining and shopping district with all kinds of shops and restaurants. We can walk around and if you see something you like, we

can go in for lunch.”

In line for the parking garage, a space opened up on the street and Leah wheeled into it. Reaching for my door, Leah stopped me. “You need to learn to disembark like a lady. I’ll open your door then

you turn both knees to the right and ease both legs out at the same time. Not one at a time like a boy.”

After I stepped out, Leah shut the door, took me by the hand and we strolled down the walkway. Boutiques, bistros and bars lined each side of the street. We looked in the window of a salon. I could

see myself in the mirror. With my long blonde hair, long smooth legs, green eyes, pink lips and feminine features, no one would mistake me for a boy.

“There’s one more thing,” Leah said as she led me into the salon.

“Do you have an opening? I know it’s last minute and we don’t have a reservation, but it’s my daughters birthday and I would like to treat her to a makeover.”

“Mom?” I looked at Leah with wide eyes.

A beautiful asian lady came over and said, “I have a few minutes before my next appointment. I can do it. I don’t think she needs much of anything. I can have her ready in less than twenty minutes.

Please come sit.”

Leah had been taking me to the salon the past few months, but only for facials, mani-pedis and a little facial hair grooming, but never makeup.

May-Lin was right. In fifteen minutes a complete stranger was looking back at me from the mirror. She brushed my hair and handed me a hand mirror to look closer. I looked at Leah, who beamed

back at me. Oh well, In for a penny, in for a pound.

The first two men we saw outside the salon were two handsome preppy college aged guys and their jaws dropped. Leah laughed and blew them a kiss. She was so happy and it was contagious.

We walked all the way to the outdoor amphitheater then crossed the street and came back down the other side.

We were getting a little hungry, so we stopped to look into a sushi restaurant. “You want sushi, birthday girl?”

“Yummy”

From the table in the window we got to see all the people walking by and plenty of them got a good look at us too. And we got plenty of looks.

Over tea, I reached for Leah’s hand across the table. “Thank you Leah. This was very sweet.”

“I’m the lucky one, Jodi. I haven’t had this much fun in way too long.” The table was small so Leah had no trouble leaning forward, so I leaned forward also and out lips met in the middle.

On the way back to the car, Leah stopped to look in a shop window and dragged me inside. To the salesclerk, “There is an emerald necklace in the window, could I see it please?”

The clerk brought a velvet platter with the necklace, matching bracelet and earrings. Three emeralds were on the necklace and the bracelet and the earrings were matching emerald studs. Leah took

off my gold chain and replaced it with the emerald necklace and added the bracelet. She turned me to the mirror on the counter and whispered in my ear, “Do you like them?”

“Of course, but I know what you are thinking and I refuse.” The clerk was hovering close so I leaned over and whispered into Leah’s ear, “And besides, the prices in this place are ridiculous.”

She smiled at me. “You let me worry about that,” and waved the clerk down the counter and talked to her in quiet tones. In less than five minutes, she was done and I wore the jewelry out of the store.

“You are right. Even at half price, they made a healthy profit. But, I had to get them. They are perfect on you.”

Leah pulled down to a bench and we sat there people watching. “Do you see a single woman as pretty as you?”

Just then two women, obviously trophies, came out of the store beside us laughing without a care in the world.

“Besides those two?”

“Oh, poop. This place is full of their type. All flash and no cash, looking for a sugar daddy.” She bit her bottom lip, hard. “Oh god Jodi. That came out all wrong. I’m so sorry.”

A quick peck on the cheek perked her right up. In her ear I whispered, “That’s not how I feel. I would be with you if we both were poor as church mice.”

Holding hands all the way home, I couldn’t help myself from looking at Leah’s profile as she drove. She was so beautiful, she could have any guy with a snap of her perfect finger. I didn’t know where

this was going, but I hope it wasn’t leading to my heart being broken.

We pulled into the empty garage. Once inside, Leah texted Alexa and they were still down in South Beach and weren’t sure if they would be home for supper. Leah led me to the kitchen and took out

a bottle of champagne. “I know I shouldn’t but I think we could have one glass to celebrate. If you want me to, I’ll put it back.”

I though about it. “My eighteenth birthday and coming out party? I think one glass will be fine. I won’t drive home for a while.”

Leah lit some candles on the same table where we had our first lunch together. I had opened champagne and did a credible job of it. With the sun still in the west the shadows were falling across the

pool area as the music came from hidden speakers. We chinked out glasses together and made a silent toast as we gazed into each others eyes. The champagne was tart and tasted a little like

apple cider. I liked it. Too bad I’d have to wait three more years to enjoy it again.

Looking at Leah, I could tell something was off. She wasn’t looking at me, she looked almost afraid. She was nervous! Scooting my chair next to hers, I waited until she turned her head towards

mine and I raised my lips to hers. I set down my glass and held her face with both hands as I kissed her. For the first time, her lips parted and I felt her tongue slithering back and forth inside her

mouth. Her hands circled my chest and we explored each others mouths. I had dreamed of this moment for so long and it was perfect. I slid my hand behind her head and pulled her to me tighter

and plunged my tongue deep into her mouth and she sucked on it eagerly. My other hand, she slid it down to cup her full breast and I could feel an erect nipple under my palm. I put one of her hands

inside my blouse and she did the same for me.

We kissed for an eternity before she slid her tongue into my ear and whispered, “I want you!” before taking me by the hand and leading me to her bedroom. When the door was closed we stood

together kissing and I took my hand and slid down the zipper of her dress. She stepped out of it and stood before me in just her high heels, stockings, panties and bra while she undressed me. When

I was down to my bra and panties I stretched out on her bed and took off my sandals. Leah eased off her shoes and snuggled beside me in bed. We had gotten lipstick all over each other so she

offered me some tissues and we cleaned each other up before kissing again.

This time, lying in bed together in just our bra and panties, my cock was beginning to hurt in the gymnastic briefs. I pulled them down and let my cock and balls pop out to keep them from killing me.

Leah immediatley started stroking me so I took at as permission to undo the front clasp of her bra. Her tits burst out and her nipples came to full erection.

Wasting no time, I began to suck one and then the other. Leah’s eyes were closed and she began to moan. I wriggled out of my briefs to let her get better access to my throbbing cock and swollen

balls. She cupped my balls then moved her head down my stomach and I couldn’t see what she was doing but I felt her hot, wet lips wrap around my cock. It felt so good that I gasped and heard

myself start to moan. Leah moved between my legs and now I could see her pretty face with my big, hard dick plunging in and out of her mouth. When she looked up at me, I knew I was in trouble.

“Leah, stop. I’m going to cum.”

I didn’t know she could smile with my dick in her mouth but she did it. I tried to pull out, but she grabbed my ass with both hands and forced my dick all the way in her mouth. She couldn’t take the

entire thing but it didn’t stop me. My cock started throbbing and shot jet after jet of hot cum right in her mouth. She choked a little and some dribbled from her lips and down my shaft but finally it was

over. She slid my dick out of her mouth with and audible smack and licked the dribbles from her lips.

Cuddling beside me, I said, “I’m so sorry. I couldn’t stop.”

“Don’t be sorry, I loved it. Although your load was way more than I expected. Been saving that up for me?”

As we snuggled, I felt myself getting hard almost immediatley.

“Take off my panties and get on top of me.”

By that time, I was fully hard again. As we kissed, Leah reached down and guided me into the hot, wet folds of her pussy. I took a few easy thrusts in and out before I was able to get it all the way in.

Afraid I was going to come again, I stopped. “I’m sorry, Leah. It feels so good and I don’t want to cum so fast again.”

She pulled my chin up and kissed me. “First time?”

I nodded.

“Then don’t worry about it. Enjoy yourself but don’t cum inside me. Pull it out and shoot it on my tummy.”

Now that the pressure was off, I was able to enjoy myself and I may have lasted two or three minutes. At the last second, I pulled out and the first spurt hit Leah right on the cheek, the second on her

tits and the rest landed on her belly. I was horrified but she was laughing.

Reaching into her nightstand, Leah said, “Just hold me.” and started rubbing a vibrator on her pussy. In less that two minutes she was arching her back and groaning. Finally she screamed, “Oh

God, Yes! Oh Jodi, I’m cumming.” Convulsions wracked her body and it took minutes before it was over.

She rolled over and looked at me. “That was fantastic. Thank you, Jodi. You are an amazing lover.”

After showering I put on the pair of new man-panties Leah had given me and put on a pair of tight athletic shorts and a cropped tee that left six inches of belly showing.

Without makeup I looked more like my normal self, but I took off my new necklace and bracelet and put them in Leah’s jewelry box.

We were watching TV in her den when the twins came in to tell us they were home. They knew I was there because my car was in the driveway.

They joined us on the couch, one on each side and told us about their day at South Beach.

“It’s changed so much in the past few years. Now people are flying in from all over to party. It’s packed everywhere. We left early and stopped in Hollywood for a late lunch.”

Kristen spoke up, “How about pizza and a movie later?”

Without waiting for and answer, she picked up her phone and dialed, “Hello Aunt Shelly? This is Kristen. We are going to watch a movie and order a pizza, can Jodi stay over tonight? Okay, thanks. Good bye.”

“Well that’s settled. Finally, a man around the house.”

We didn’t start the movie until nine and I must have dozed off before the end, because when I woke up I was on the living room couch with a pillow under my head and covered with a blanket. I put the pillow and blanket on the couch in Leah’s den and crept into her bedroom.

I leaned over and whispered, “Can I get in bed with you?”

She smiled and pulled back the covers inviting me in.

It was almost dawn when I woke again. I eased out of bed without waking Leah and went into the den. I didn’t hear anything but rather sensed it. I opened up one eye and didn’t see anyone but I could

see a shadow on the floor from the doorway. Someone was watching me. Then the shadow was gone. Later, I heard voices and found Alexa and Kristen in the kitchen making a pot of coffee.

“Hey sleepyhead. Sorry to leave you on the sofa but you were sound asleep.” Said Alexa.

“That’s okay. The couch was pretty comfy.”

Kristen gave me a sideways glance and I realized it was her that looked in on me sleeping in her mother’s den. “Where’s mom?”

“Right here.” Leah came walking over tying her robe. Not the robe she wore when she and I were alone. This one covered her tits and ass.

Everyone was hungry so I offered to make egg sandwiches. I was about to get the frilly apron Leah had given me when I remembered the girls were there.

Eating breakfast on the terrace, Alexa asked, “Kristen, have you seen my yellow sundress with the Hawaiian print? It’s not in my closet.”

“No. I didn’t take it.”

Leah and I looked down absorbed in eating our breakfast. We both knew where the sundress was, hanging in Leah’s closet. I wore it two weekends ago.

My mom had invited a houseful for Thanksgiving dinner, including Leah and the twins. Up until now I hadn’t really thought about the implications of what we were doing. Being with Leah and not being

able to kiss her or hold her hand was very confusing and difficult. The person I was most worried about was my mom, then the twins, then my sister. I wasn’t worried about my dad, he would

probably want to give me a high five. Leah and my mom were best friends. If I wrecked their relationship, it would be devastating to me. The twins would feel betrayed and I have no idea what Dina

would think. She would probably be very angry with Leah.

After Thanksgiving was over and everyone was back at school, Leah and I were able to resume our relationship.

I had an appointment to get an estimate to pressure clean the roof and when it was done I went back inside. Leah was on the living room couch in matching black, lacy panties and bra and sheer

black stockings. I stripped off my shirt and kicked off my shorts and shoes. As I walked across the room I could feel my cock springing to life in my white, lacy man-panties with the penis pouch. As I

stood before her Leah said, “Oh you poor thing. It looks so uncomfortable. Here let me help you.”

She pulled down my panties and my cock sprang free, pointed right at her face. She leaned forward and licked the pre-cum from the tip before slurping my cock into her mouth. She held my hips as

I fed her my cock. I pushed her hands away and made her suck my dick with just her mouth, them took her head and began fucking her face. I was still learning to pace myself and since I had a full

load, I pulled out at the last minute and shot a huge hot load all over her face. Some she was able to catch in her mouth and some dripped down onto her tits. I was so horny, I just pushed her back

on the couch and jerked her panties down and buried my face in her crotch. So much for romance. She was already wet from sucking my dick and after some sucking and tounging her pussy was

swollen as well. I haven’t gotten Leah to orgasm from intercourse yet, probably because I cum too quickly, but if I try hard enough, I can get her off with my mouth every time. This time was no

exception. I peeled back the hood to expose her clit and starting sucking on it. It was like a little dick and I gave it a blow job while three fingers slid in and out of her hot wet cunt. Finally, I sucked her

clit and some of her large labia into her mouth while furiously lashing it with my tongue and she began to yell. “Oh God! Oh Fuck! Don’t stop, Oh God don’t stop. I’m going to cuuummmmm….” She

humped my face then froze and collapsed in a heap on the couch. One thing she really loved, was to get fucked right after cumming. I got a sofa cushion to protect my knees and knelt between her

legs. My cock was like a rock and I rubbed the head up and down her wet, swollen pussy lips. Soon she was writhing and trying to push herself on my dick. She began to beg. “Oh please, Jodi.

Please make love to me. I need you so bad.”

I teased her. “I can’t hear you. What did you say?”

“You heard me you bastard. I need you to fuck me. Please fuck me right now. If you don’t fuck me half to death with your huge hard cock I’m going to die. Fuck me! Fuck me! Fuck me!”

I pushed my dick a little way in but the head did not pop in. She grabbed my hips and tried to drive me into her but I pulled back. I teased her a little then shoved it halfway in. She started whimpering.

“Oh please fuck me. Please Jodi, stop teasing me and fuck me.”

I used my hips to drive myself all the way in. I held it there and she was frozen with her eyes closed. I put her legs over my shoulder and began to pump my eight inch cock in and out of her pussy.

With the cushion, I was at the perfect height to fuck her without much effort and I got a perfect look at my lover. I could see why she was so successful as model. Everything that one expects in a

beautiful woman she had and more. Big beautiful eyes, big full lips, full breast with large nipples, tight tummy and best of all huge sexy labia and clitoris. One reason I was having trouble lasting was

that her swollen labia would wrap around my cock and with my girth, the friction of them sliding up and down my shaft made for an incredible sensation. I looked down at my dick working in and out.

Once Leah gets excited enough, her clit comes out and doesn’t go back for a while. It was eagerly peeking out but I know that after she came, it was probably too sensitive to play with but I decided to

try. I wiped some of her juice on my thumb and gently placed it on her clit. She shrieked. “Oh God! Oh Fuck. Oh Jodi, I’m going to cum again.”

It was a race against time. I needed to get her off soon or I was going to blow my load deep into her pussy. I grabbed my balls hard enough to hurt and that gave me the two minutes it took before she

started to cum. As soon as I felt her pussy start to clamp around my cock, I couldn’t hold it any longer.

“I’m cumming. God Damn it Leah, I’m going to shoot my hot sperm in your pussy. Take this load right in your pussy, Damn it!”

I collapsed on top of her breathing like I had run a race. When I looked up she was smiling at me.

I was sheepish. “I’m sorry, Leah. I don’t know what came over me.”

“Are you kidding me? I begged you to fuck me to death and you nearly did. I’m glad I didn’t die because I want you to fuck me like that any time you want.”

I took her by the hand and led her to bed. We were lying there for a few minutes when I heard her say, “We are so fucked.”

I had to agree. “What can we do?”

“I don’t know. Let’s give it some time. Maybe we can figure something out. I really care about you and I know you care about me too, but I don’t know what our families are going to think. I don’t care

about anyone else.”

“I feel the same way. I know that I have zero experience with relationships, but the thought of not being able to hold your hand drives me crazy.”

Leah suggested we go out and get something to eat.

“I don’t know. Are you sure? I don’t feel like getting dressed up and all that stuff.”

“How about casual? Maybe Mariners?”

Mariners was a waterfront raw bar practically around the corner. It catered to boaters and was a local legend.

“Fine. How should I dress? Girl, boy or anbi?” Girl meant a dress and makeup, boy meant cargo shorts and a polo, and andi (androgenous) meant that most people couldn’t figure out what to call

me.”

“How about boy?”

In a pair of shorts, sandals, a tank top over black lacy bra, Leah looked very sexy. She was showing a little bra and side boob through the arm holes of her top and her full breasts were sure to attract

envious glances. From my dresser in her closet I got a pair of boat shorts, boat shoes, no socks, crew shirt and a woven belt. With an anchor chain necklace and an oversized dive watch, I could

probably pass for a boy. Except for my long blonde hair, my full pink lips and big green eyes. I was used to it.

The hostess gave us a waterfront table overlooking the water on the outside deck just like we wanted. Leah had been here many times and she wasn’t someone you would forget. On the way to our

table I could see the eyes of every guy and half the women watch Leah and trying to figure out who I was. Her daughter? Her pansy son? Her lover? Nah. I was used to that too.

Leah ordered the grilled seafood platter and a large glass of white wine. I chose the crab cakes and a perrier. Crab cakes aren’t health food, but they are homemade and taste delicious.

My perrier came with a plastic cup, so I looked at Leah and tipped it towards her wine. She poured me a couple inches. It was dark and no one could see.

We had to walk through the entire restaurant to leave and when we got up from the table, her hand fell into mine. I could see the puzzlement on some of the faces as we walked out hand in hand.

I waited for Leah to open the car door for me, instead she pushed me against that car and kissed me. In the dark parking lot and I kissed her back. It wasn’t sexual, it was longing.

She broke away and whispered in my ear. “I can’t lose you. I love you.”

“I love you too.”

We made love once more before falling asleep in her bed.

The twins came home for Christmas holidays and that’s when things became really difficult. I was so used to being with Leah, it was almost impossible for me to stop touching her, stop hugging her

and stop kissing her.

My mom and sister had been invited to a New Year’s Eve party within walking distance in our neighborhood and I told them that I was going to spend it at Leahs. The twins had some friends over and

there was probably twenty-five people total. Several guest had offered to bring their personal specialty, so Leah provided an open bar and a DJ. Two friends had been invited to spend the night.

Alexa’s room had two full beds while Kristen’s had one queen, so the twins slept in Kristen’s bed and gave Alexa’s room to their guests. I was asleep on the living room couch when I was awakened

by someone sitting beside me. I rolled over and saw it was Kristen. She didn’t say anything instead, she began stroking my head. I didn’t say anything or stop her. Soon, tears were flowing out of my

eyes and soon too, from hers. She left as silently as she came and returned to bed.

January greeted us with the first real cold snap of the year. We made plans to get me some decent cold weather clothes and go out to a fancy restaurant for dinner and dancing. Leah tried to buy me

a Burberry Herne double breasted trench coat for twenty-five hundred dollars but I refused. Instead I found one from Brooks Brothers that was almost identicle for a little over three hundred.

We decided to go to Kristoff’s on the Water. It was super classy with a world reknowned chef and a beautiful dance club overlooking the intracoastal waterway. Instead of driving, Leah used her

airport limo service to provide us with a town car and driver to and from the restaurant.

I was no so used to shopping for ladies clothes that I no longer got nervous. I went in dressed as a girl and no one ever questioned it. At Sak’s we found the perfect outfit. Mini dress, pumps and

head band in ultramarine blue. Leah was with me in the dressing room helping me take off my new dress and when I got it on the hanger I turned around and Leah kissed me and pushed me against

that wall. I was in panties and a bra and soon she was stroking my rapidly growing cock. When it was sufficiently hard, she dropped to her knees and started sucking it. She had a new trick to hold

and tug on my balls while she sucked me and put it to good use. I was just getting into the rythym and I assumed she was giving me a quicky blow job, but instead, she hiked up her skirt, puller her

panties down and bent over holding with her hands on the wall of the dressing room. She was so wet that I was able to shove half my length in her in one thrust. She grunted and whispered, “More.” I

started banging her and my hips slapping into her ass started to make an embarrasing amount of noise and when she started moaning, I knew we were in danger of getting caught. I manged to

wrestle my panties down and off and I reached around and stuffed them in her mouth to keep her quiet. I reached into my purse and pulled out my hairbrush. I wet it in my mouth and pressed it

against my milf lover’s asshole. She was saying something but it was muffled by the panties in her mouth. My spit wasn’t slippery enough, so I wiped some of the slickness from my shaft and coated

the hairbrush handle and pressed it in inch by inch until it was buried all the way in her ass. When I thrust my cock into her, my abdomon caused the hairbrush to plunge deeper into her ass. She

started fucking me back and I knew she was close. I was lucky her mouth was full, because she started screaming and I had to hold my hand over her mouth. I let myself go and dumped a huge load

into her waiting cunt.

As we got dressed, I whispered in her ear, “You are going to be leaking everywhere, I couldn’t hold back. Put your panties over your pussy and put mine over them. I’ll just have to do without.”

She whispered back, “But you are going to get the inside of your dress all wet and messy. Give me the stuff and wait here.”

She got a five pack of microfiber bikini panties and had the clerk add them to the other items and brought them to me. I was pulling them up when she stopped me.

“You’re still too messy.” and proceeded to lick me clean.

It was delightfully chilly when the town car dropped us off at the front of Kristoff’s precisely at nine pm. When the valet removed our coats, I could see eyes widen. Leah looked incredible in a caviar

and white matching skirt and jacket with a sheer white blouse underneath and I was feeling super sexy in my blue dress and matching pumps. Leah had requested a booth that over looked the rest of

the dining room from above. We had pre-ordered the ten course tasting menu with wine pairing.

Two hours later, we were sipping coffee and I could hear the music faintly thudding through the walls. Stopping by the ladies room first, the music was deafening when we entered the dance club. A

DJ was onstage spinning EDM when we walked in. From the bar I retrieved a paper napkin and stuffed little balls in my ears to avoid getting a headache. We danced a while but between the music

and the guys trying to join us, we weren’t having much fun. It wasn’t even midnight when the car picked us up.

“Do you want to stay out a little longer?” Leah asked.

“Okay.”

When the car pulled up in front of the club, there were at least one hundred people waiting in line to get it. The driver opened the door for us and we scooted out. The doorman next to the bouncer

waved at Leah and waved us right in. I flashed the indentification card Kristen had loaned me and we breezed right in. We were all the way to the dance floor before I realized that it was a gay club.

We kept our purses with us while we danced a couple of dances and after we went to a quieter part of the club to hydrate with some sparkling water. The decibel level was low enough that we could

talk without too much shouting when two stunning ladies came up and introduced themselves. Sasha, the black haired one was around six feet tall with a shimmering blue sequin dress and Cara,

the red head was perhaps five-seven and decked out in a black skirt and white blouse.

“I’ve never seen you two here before, I’m sure I would have remembered.” purred Sasha.

“First time for both of us.” replied Leah.

“Welcome. This is our home away from home.”

I spoke up. “Thank you. I’m Jodi and this is.”

“Leah” Sasha interrupted. “How nice to see you.”

The confusion was evident on Leah’s face.

Sasha chuckled. “I don’t know if I should be flattered or insulted. Leah, after all these years?”

Leah gasped, “Simon?”

“In the flesh. Or should I say ‘in a dress’?”

“Jodi, this is the manage of my gym. Simon by day and Sasha by night.”

Other than a slightly deep voice and a small adams apple, I would have not known.

“A pleasure to meet you Sasha.”

Sasha continued, “When I first saw you Leah, I was hoping Shelley was with you. That would have been the highlight of my month.”

He meant my mom. “Sasha, maybe it would be better if you didn’t tell my mom that you saw us here.”

It was now Sasha’s turn to be confused. She looked at Leah, then me, then Leah again.

She was so funny that I had to laugh. “Shelly is my mom. She doesn’t actually know that Leah and I are dating.”

She clamped her hand over her mouth and her eyes were as wide as saucers. “Oh. My. God.” She made the zipping motion over her lips. “No one will hear it from me. Besides, no one would believe it anyway.”

I was still laughing. Leah was usually so composed and care-free. Looked at Sasha. “You don’t even know the half of it.”

Sasha told us, “Don’t move. This deserves a celebration. I’ll be right back.”

I turned to Cara. “I’m sorry if we have been rude. I didn’t mean to shut you out of the conversation. I guess you can see that this was totally unexpected.”

“No, it’s fine. It was unexpected for me also. So you two are gay?”

I looked at her and slowly shook my head from side to side.

“Now, I’m really confused.”

We were at a stand up table so I took her hand and guided it under my dress and onto my man panties with the dick pouch. When she felt me her eyes widened. She guided my hand under her skirt and I felt, well, not much. I cupped her and realized that I was holding a vagina. Oh my God! Four women and two dicks between us.

Cara winked at Leah, “Well hello sister.”

Sasha arrived with a bottle of domestic sparkling wine and poured us all a glass.

“Cheers!”

We topped off our glasses and made our way to the dance floor. I danced with Cara while Leah and Sasha danced. Cara pulled her lips to my ear. “This is so fucking hot. I feel like a freak here

because everyone is gay or bi or even a few straights looking for a walk on the wild side. But to finally find someone like me is awesome. You have to give me your number so we can keep in touch.”

I leaned closer. “Ok, after the dance. Do you work at the gym too?”

“No, I’m a lawyer.”

She didn’t look a day over twenty-two. Seven years of college meant that she was at least twenty-five.

“How old are you?”

“Twenty seven. You?”

“Eighteen.”

“Holy Fuck!”

“No shit!”

We went back to the table and we swapped numbers with our phones.

“Let me get this straight. You are dating your mom’s friend?”

“Best friend. I call her Aunt Leah at home.”

“Fuck. And your mom doesn’t know?”

“Hell no. And she doesn’t know about all this either.”

“When Sasha saw you two she said, that’s Leah and who is that beautiful creature she has with her. You are one of the prettiest girls I have ever seen.”

“Thanks. I just got lucky.”

It was getting late when Leah and Sasha got back so I suggested that it was time to go home. Back in the car Leah started rubbing me under my dress and I got hard in an instant. I whispered

something in her ear that made her laugh. I handed her my phone, pulled up my dress and pulled down my panties. After giving myself a couple strokes to make sure I was really hard, Leah took my

picture from the neck down. It was perfect so I texted it to Cara.

After we showered and were lying in bed, Leah said, “So, pretty amazing. You and Cara each have a femboy. Oh, by the way, did you tell Sasha about me?”

“No, she has no clue.”

“Well, after that pic she does.”

I thought about what I was going to say.

The sticky part was that now Leah and I were girlfriend and boyfriend although she made me dress like a girl and everyone thought that we were a lesbian couple, my mom and dad had no idea that I

was even in a relationship. I gave up even pretending to resist and let her dress me up and do my makeup and it got to the point where I didn’t want to be a boy any longer. When guests came over, I

dressed in girl clothes. Lipstick was now a must have first thing in the morning and thigh high stockings and high heels were my new normal.

My blonde hair was nearly down to my waist and dressed up with lipstick, no one could tell that I had a package. Leah made sure to be attentive to me and she kissed me all the time no matter where

we were. We went to the Florida Derby at Gulfstream Park and while standing in line to bet, she kissed me and felt up my tits right in front of everyone. The elderly gent processed our tickets and said,

“Have a good time, lovebirds.”

There was never any doubt. I was totally in love with her. Smart, rich, confident and she would toss me on the bed and I let her do anything she wanted. Every time. Staking everything on one person

or one circumstance was risky, but I was too in love with her to consider anything else. She had my heart and showed me how to be what I was. A sissy panty boy.

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