Gina Helps Joey Become Julia

Coming out to California to pursue my acting career was a risky move. But I thought it was totally worth it as there was nothing going on for me back home in Indiana.

I didn't think it would take long before I'd end up in the movie industry but I guess it takes longer than I thought.

So here I am waiting tables at bistro down by the beach. it's not a bad job. The tips are good and I get to eat good. And maybe I will get discovered.

I work with this older mature lady named Gina. She is a free spirited woman. a widow. She has a daughter in the military on deployment, so she's always alone.

She makes me laugh, and I make her laugh, and we have a good time working together. She keeps trying to set me up with guys for some reason.

I keep telling her I'm not gay. There was this one experience after high school. When I graduated, I was doing community theater and we didn't have very many guys in the troop.

They put on the play little women. And myself and another guy played women parts. I've always been thin, scrawny. And a little on the fem side.

After the end of the play, we were celebrating with champagne. And the other guy that was dressed as a girl like me. Was in the dressing room afterwards and we're changing out of our costumes.

We were both intoxicated, and before I knew it, he was on his knees, giving me head. But does that count as a gay experience?

He looked and was dressed like a girl. And I looked and was dressed like a girl, so I've never really counted as being gay.

Gina was always commenting on the rich guys that came in, and how they're only looking for some slut with big tits that they could abuse, and act out all of their porn fantasies with.

One day at work, she could sense that something was wrong with me. I told her I had gotten an eviction notice the place where I was staying had been sold, and the new owners were not gonna use it as a rental anymore.

It was hard to find affordable housing out here in Southern California. I told her I didn't know what I was going to do. I'd probably have to live in my car for a few weeks until I found something.

Gina told me to come stay with her. She said you've been to my house many times you know how big it is. you know I have an extra room and I'm always by myself. it would be nice to have some company.

I asked her if she was sure. And she said, totally. She said, besides it'll be fun hanging out. especially since we have so much fun here at work. So we can have more fun at home.

After our shift, she told me she would come over and help me pack. And the next day. She would help me move in to her guest room.

She helped me move in and for months we had a great time working and living together.

One night we were sitting there, watching TV drinking some wine and she was painting her toenails. She asked me if she could paint mine.

I said, no way, what if someone was to see my toenails painted how do I explain that? She said, no one's gonna see besides, it'll be fun.. I'm bored let me do it for you.

I agreed, and she painted my toenails, bright red.I had a good buzz on from the wine. And so did she.

She took my hand and was painting my fingernails the same color. I didn't realize it at first and then I pulled my hand away, but it was too late. She already had three fingers done.

Gina grabbed my hand and finished painting the other two fingers and said, give me your left hand so I can finish. I Protested again, but decided just to let her do it.

I said, What the heck, I can always take it off in the morning. And we both had off for two days, so I really had no plans. I wasn't going anywhere.

After she got them painted, she told me to blow on them to dry them. She had got up to go put her fingernail polish supplies away. When she came back, she had her make up bag.

I asked her, what is that for? she said it's for your makeover and started laughing. I said, no way Jose. The fingernail polish and toenail polish is one thing, but make up?

She said, it will be fun. And besides, I can make you look really pretty. You've dressed up like a girl before many times, you told me yourself.

I said, yes, but that was for the theater. I was just acting. Gina said you can pretend this is the theater and you can act around here. come on it will be fun.

My buzz was too strong to allow me to disagree. Gina proceed to apply some eyeliner, mascara. She applied eyeshadow some Lip liner, and lipstick.

Then she started plucking my eyebrows. I jumped back saying stop that, what's that for? Gina said I just need to shape them up a bit.

We had polished off a bottle of wine and decided to open up another. She was done with my make up and pulled me up and took me into the bathroom so I could see her work.

We were laughing and giggling, and when we got into the bathroom together, I was amazed. When I saw my reflection, I couldn't believe it.

We were still laughing and giggling. Then she said come on, and she pulled me into her bedroom. Gina said, I've got the perfect thing for you.

Gina went into her huge walk-in closet. She came out with a long brown wig on a wig head. She told me to sit down in front of her vanity, and she took the wig off and placed it on my head..

The wig fit snuggly, and she tucked it down, adjusting it to the right position. in the mirror now was this pretty girl staring back. I don't know if it was beer goggles from the wine, but I must've looked really good because Gina was amazed with her own work.

She stood me up, pulled me into her walk closet. I got to bed. I was starting to get a little excited and I was semi hard.

She pulled me into the closet, and was rummaging through her racks and racks of dresses. I didn't know she had such an extensive wardrobe since I've only really seen her in sweats in the living room or in a black skirt and white blouse at the restaurant.

She pulled out this silver spaghetti strap, silver sequin short, mini dress. She held it up to me and said this will look great.

I told her no way I'm not putting that on. It's not even much of it to cover up all of my private parts on my body.

Gina laughed and giggled and said come on. We're all girls here now, and she started undressing me when she pulled my pants and shirt off. I was standing there in my boxers.

Gina went over to her lingerie dresser, and she was searching. She pulled out a small nude color spandex thong.

In one quick swipe, Gina had pulled my boxers down. My cock sprang out immediately. It was semi hard when we started, but now it was fully hard and standing out erect.

Gina said, I knew this was turning you on that's what these are for, and she had me step out of my boxers and step into the spandex thong.

The thong was tight, but it stretched, and she helped pulled it up over my hips and around my waist. It felt weird snugging my balls, and pushing my hard on up.

The best feeling was the material stretching, pulling in between my ass cheeks. Gina slipped the dress over my head and pulled it down.

She turned me around and said beautiful perfect. Except for that bulge in the front we need to do something with that.

I said, what do you think you're gonna do with that? It's hard, it'll be a little bit before it goes down.

Gina said, you have to tuck it my dear. Confused. I didn't know what she meant. She lifted the dress up around my waist. She pulled the thong. Pulled it down, grabbed my hard shaft and bent it down, pulling it back under me to the side of my balls.

She held it there and pulled a thong back up. Now the sensation was totally different. My heart on was tucked back, and the tight spandex thong was holding it.

My blood was pumping, causing it to throb. Every time it would throb, it would pull the spandex thong across my asshole sitting shivers through me.

Gina lowered the dress and went over to her shoe rack and pulled out these silvery open toed scrappy, high heels. Placed them on my feet they were a little big she was definitely taller and bigger than I was.

After Gina got me in the heels. She stood up and stepped back.

She was saying, oh my gosh! you are way hotter than any of those sluts that come into our restaurant.

Gina, she pulled me out into the bedroom in front of the full length mirror. Standing there before me was this skinny hot brunette in this little sequin mini dress.

The dress was short it was only about 2 inches lower than my tucked penis. I could feel the air tickling my ass cheeks as the hem of the dress wiggled when I walked.

Gina pulled me back into the living room. we were drinking more wine. She was trying to give me lessons on how to sit on the couch in such a short dress.

She stood up. She started taking pictures of me. we were both super tipsy and I was posing with the wine glasses, drinking having fun.

Gina told me have you ever thought about being girl. She said, I don't think you're ever gonna be a manly man. you can have a lot more fun as a girl.

I laughed at her, and said, sure, yeah, right. She said, think about it. I could totally help you if you wanted.

I have a friend who helped her son go through hormone replacement therapy. Her son transitioned into a beautiful woman.

I told Gina, why would I want to be a woman I'm not gay. She said who said anything about being gay. Do you feel comfortable and have fun and enjoy whoever you're with. Then, what does it matter if it's a man or a woman, boy or a girl. Or vice versa.

We just continue drinking the second bottle and kick the heels off and I was so sleepy. There was no way I was making it back to my room. Tina grabbed a blanket and put it over me and I fell asleep on the couch.

I was dreaming. My hard on was still throbbing inside the spandex thong. I kept hearing people whispering in a conversation. I woke up, I saw Gina standing over at the kitchen counter, talking to one of her friends.

They both were smiling at me and said, good morning sleepyhead. I had forgotten I was dressed up still.

I was hung over and still groggy.

I needed something to drink. I took off the blanket and walked into the kitchen where the girls were.

I open the refrigerator door and was getting some juice out. Then introduced me to her friend, Margie. I said, hi Margie, and asked them if they wanted a glass of juice.

Margie was looking me up and down and was telling me how pretty I was. I was playing it off a little bit and said, what, this old thing.

Gina and Margie both told me you're a very beautiful woman. I would totally go after you if I was younger.

I laughed and told them, this was just drunken silliness fun Gina and I were having last night. Margie said silliness or not you look really amazing. You should dress like that more often.

I excused myself from the ladies and told them I needed to go take a shower and get out of this outfit.

I made my way back to my room. I looked in the mirror, and even though I didn't look as fresh as I did last night, they were right I was really attractive looking, but it's all smoke and mirrors, just the make up wig in the dress.

I took the wig off in the dress and laid them on the dresser, and was looking at myself in the thong. It was interesting not seeing my cock and balls in front of me.

I was looking at the spandex, the between my thighs, the smooth flatness of the front of my pelvis. I pretty much look like every girl I've seen in a bikini.

And with that thought, my throbbing hard on was pushing down on the spandex. I reached in an untapped and it, springing immediately straight out through the leg band.

I had to take care of it, so I started jacking myself off, looking at my reflection, standing there completely naked, except for the tan thong pantie.

It only took a few minutes and I was cumming. Since my cock was tucked back for so long and throbbing so much, it felt two sizes bigger than I've ever felt it before.

The feeling of the cum leaving my balls trying to push its way out the length of my cock. Was amazing. It had my legs shaking when the cum reached the tip of my cock and shot out.

I threw the thong up on the dresser with the dress in the wig and went and got in the shower and washed all the makeup off.

I was enjoying the warm spray and trying to wash my hangover away with the make up.

I heard Gina come into the bathroom and she knocked on the shower door. Gina handed me a bottle of near to remove the hair off my legs and body.

I asked her what do I need to do this for she said just do it for me. Trust me you'll like the way it feels.

I lathered up the cream all over my body and it was tingling. It felt weird at first then it started to burn. I started to wash it off, and I could see my hair disappearing off of my body running down the drain..

When I stepped out of the shower and started drying myself off, it was pretty amazing. My skin was more sensitive, it felt free.

I came out of the bathroom and Gina was sitting on my bed. She had a bunch of clothes laying there.

I said, what's this, what's up Gina said, I brought you some outfits. Do you want to try some more on?

I said maybe later tonight that was fun last night. She said pick an outfit get dressed. I want to take you out to brunch.

I told her, wait a minute there's no way I can go out in public trust as a girl. Dressing up here pretending is one thing. Going out in public there's no way.

Gina assured me that I looked really nice dressed as a girl and nobody would ever notice that I wasn't a girl. And she said if I do this for her this weekend, I didn't have to pay rent next month.

I agreed. Her eyes lit up. She was very excited. She said this will be perfect. We're gonna go to brunch with some of the girls you'll fit right in and don't worry no one will tease you or make fun of you.

Gina couldn't have been more happier she was saying she had her own Barbie doll. She couldn't wait to dress me up.

She told me how she used to have fun buying outfits for her daughter, but her daughter had changed and started to become more butch. And it was no surprise when she told her she had enlisted in the military.

Gina had her make up bag, and I let her do my make up. She fixed the wig, and then she was looking at some of the outfits.

She asked me, do you want to pick or do you want me to pick?

I told her go ahead, whatever you think would be appropriate for brunch.

She grabbed this red and black plaid wool wrap style short skirt and a white long sleeve T-shirt type bodysuit with snap crotch.

She had me put the thong back on. And then she handed me a padded bra. I tried putting it on. It was having a hard time trying to figure out how to hook it in the back.

She helped me get it hooked, and then grabbed a black pair of pantyhose and help me step into them. She pulled them up over my thong panties.

It felt amazing. I've had tights on before in theater, and I've always liked how they felt but since I had no hair on my legs, these were more electrifying.

She had me put on the bodysuit and it was skin tight. It hugged my body, and you could definitely see the bra through it.

The bra gave me some cleavage. It looked like I had some small B cup breasts. And the way the skin tight, long sleeve blouse with the scoop neck, hugged my body, it enhanced my figure. I looked like i was ready for ballet class. in a white bodysuit with black pantyhose under it.

Next she wrapped the skirt around my waist. She brought in these low, cut black boots with a 4" heel. She had a big black belt with a silver buckle she put around my waist.

She had me turn around and look in the mirror, and I looked hotter than I did last night. Don't give me wrong. I looked in the spaghetti strap short mini dress, but this was a more refined polished model look.

She went and grab some earrings. She had some old clip on from way back in the day and put them on my ears. She had me a little pocketbook.

She went and got herself dressed. I've never seen her look so nice as she did, when she came out of the bedroom.

She had on heels, white pantyhose, a gray short skirt, and she had on a similar top to mine. She looked really good.

She grabbed me and pulled me out. We got in her car. I was nervous, but I was just playing the part for her for the weekend.

And heck, who wouldn't want a free months rent. We were down by the beach not too far away from the bistro where we work. She pulled up to this fancy Mexican restaurant.

She pulled up to the valet. They opened the door for me to step out. Here was my debut. I was nervous, but I got out and stood there turned around and waited for Gina to come around the other side of the car. People were looking at us, two beautiful ladies.

The place was busy, and when we walked in, there was already a table for us with Gina's friends sitting there. Gina was whispering to me as we were walking. We need to give you a girls name for the weekend do you have anything in mind?

I told her I always like the name Julia. She said, perfect, Julia it is.

When we got to the table, she introduced me to everyone sitting there as her friend Julia.

One of the ladies was Margie and the others were really pretty. They must've been in the mid 30s they were definitely prettier than I was. They were gorgeous.

We were all drinking mimosas, and it was time for us to get up to go to the buffet to get our food.

I was nervous, but Gina, pat me on the leg and said you look fine.

I followed Gina, everyone else was behind us. we grabbed our plates and we're standing in line and the girl behind me started casual chitchat.

I was nervous because she was so pretty. She told me how much she liked my outfit and how good I looked. I responded by telling her the same. She asked me if I worked with Gina and I told her yes.

She told me that the bistro where we work is the place where all the hot guys come in with their trophies on their arm. Then she asked me how come I was still working there and that I wasn't hooked on some guys arm.

I told her I was too busy working on my career, how I was interested in acting and didn't have time to be in a relationship. which pretty much was true.

She said oh, do you wanna be an actress? Have you been on any auditions lately? I told her no, it's pretty hard out here. She said I have some friends that are always looking for actresses. I could introduce you to them if you want.

I got real excited and told her yes that would be great. But thought to myself, I want to be an actor, not an actress. Back at the table the three gorgeous ladies were looking at me. They kept whispering to each other and talking and smiling at me.

I was enjoying the mimosas and the food and having a good time and I'd completely forgot about being dressed as a girl. I guess I was really comfortable.

After brunch was over we said goodbye to the ladies and we're out front waiting for our car at the valet stand. There was a group of five guys in their golf gear and they were eyeballing us.

Gina kept teasing me, telling me that they had the hots for me. She said look at that guy in the black shorts. You're giving him a hard on right now. I got totally embarrassed. Because she said it so loud.

We got in the car and the guys are still looking at me as we drove by. She said, that was fun. Did you enjoy brunch? I told her I did and that her friends were really nice. She said, they really liked you and did you know the one you were talking to? That's Margie's son, well now her daughter.

I was shocked that girl was completely drop-dead gorgeous how could that have been a guy.

Gina told me how Margie's son struggled with his identity and how they finally came to terms with it, and Margie embraced him and helped him change into her.

And, she told me how successful she was. She had confidence as she transitioned, and how her and her friends own a company.