tagTransgender & CrossdressersTwinsies Pt. 01: First Night Out

Twinsies Pt. 01: First Night Out

bySkylar_Macy©

Hi there. My name is Clara. This is the story of how my twin sister, June, and I became a lot closer.

She was always teasing me about the fact that she had been born about an hour earlier, saying that she was older so she was in charge. We were identical twins even though we were different genders. Despite being born Clark, a boy, I looked a lot more feminine than she looked masculine. This got me a bunch of teasing in school.

She and my single mother consoled me whenever I had left the school for being teased about looking like my girly sister. She always looked like the picture of femininity while I looked a lot like her but felt I was supposed to wear guy stuff since I had the tools of one.

As we went along in our school years her and I started to drift apart for quite a while. She was always hanging out with her friends while I spent time at home with Mom and the TV. When her and I did get to spend time together we had a blast.

One day in our senior year of High school she had a couple of her friends over at our house and Mom wasn't home. She let me have the TV while they stayed in her room. Suddenly she came out to me with a really embarrassed but excited look. "Hey, Clark? Can I ask you a huge favor?"

I looked at her with a suspicious look, "what's up?"

She sat next to me and placed her hand on my knee, "Would you be willing to let us give you a makeover?" she finally said.

I looked at her with a mix of surprise and anger, "How dumb do you think I am? You just want to try making me look like a clown and putting it online." I crossed my arms and turned my head away.

"No, no. Sarah actually wants to try and Amber wants to see if it is possible to make us look like the same person. We both know we look similar already. You just don't have that girly touch yet. Name your price and you can have it. Please, Clark?"

I looked back at her and saw she was looking at me with those sad and longing puppy eyes. She knew they were my weakness with my dear sister. I sighed heavily, "Ugh. Anything I want?"

"Anything." She confirmed.

"Hmm, ok. Here is my price, three things: first I want the box set of the cell 25 books"

"Done! Next ya nerd?"

"From now on every Sunday instead of church like those weirdos our Sundays are for you and I time. No friends or others."

"Awww. That's adorable."

"Oh shush. I miss actual time with you. This is the longest we have talked in the last month. Third I want a BJ from Sarah."

"Deal! Now come on." she hugged me then grabbed my hand and pulled me to her room where the two girls were sitting on their phones waiting.

They looked up, "wow, you actually convinced him. What did it cost ya?"

"Something geeky, something sweet and sappy, then something we can discuss later.". She turned to me, "Now, you go to the bathroom and use my spare razor and the blue bottle to take off ALL of that man fuzz."

I rolled my eyes. She knew I didn't grow much body hair except on my legs and even that wasn't much. I walked into the bathroom across from our rooms and stepped into the shower. The water was soothing as I grabbed the blue bottle. I squeezed out some of the pink foam inside and began to spread it over my legs. Once they were covered I grabbed the purple razor on the shelf and began to shave the thin hair on my face, crotch, legs, armpits, and my butt for good measure. I felt so exposed and so weird but it didn't feel bad, just different.

I stepped out of the shower and toweled off with the teal blue towel that was on the rack. I then wrapped it around my crotch and walked out. My sister was just outside the door and handed me a set of underwear. They were women's panties, the kind they call tangas, I think. I took them, "Why?"

"If you are gonna get done up like me you gotta dress like me and I don't think you wanna show yo bidness in front of the girls do you?"

I sighed and turned to put them on. They cupped my toned butt cheeks without riding up my crack. It was almost comfortable while making my ass look fantastic. She suddenly grabbed me by the shoulders and pushed me back into her room in front of the other two who looked at me in the panties. I was scared they were gonna laugh but they just complimented me on how my hips and butt looked.

June came in behind me then went over to her dresser. She pulled out a hot pink shirt and bra. I stood there and let her put the bra around my chest then accepted the shirt. "Don't put it on yet.". She got back into her drawer and pulled out a couple of kind of large breast inserts.

"Why do you have fake boobs?" I asked confused. My sister had a rather decent bust.

"Guys always like them bigger." Amber said in answer to my question.

I stood there as she put the inserts into the bra. They were cold but they definitely gave the appearance of me having actual boobs. I then put on the pink shirt. It was really thick and tight spandex so it sort of formed my figure to be a bit more hourglass shaped. June then threw me a pair of thin pink short shorts and had me put then on before sitting me down in a chair in front of her makeup stand. I looked into it and saw myself in the pink shirt and bra with boobs and thought I saw my sister without her makeup and skin products.

The girls stood up from my sister's bed. They came up behind me and looked at me through the mirror. I gulped deeply as they smiled at me. June turned the chair around and grabbed a bottle. She called it primer and put it onto my entire face. It felt kind of good to feel her soft hands begin to rub my face. She ordered me to close my eyes which I easily obliged. I heard one of the girls I assume was my sister, whisper something to another. The recipient giggled, "that's not a biggie. Happy to if this is what we get to do for it."

June kept applying the creamy substance until I could feel it coating my entire face. One of the girls grabbed my hand and suddenly my nails had something cold being put on them. June capped the bottle and grabbed something else which she smeared on my face in a few lines like a glue stick. She then took a brush and gently fluttered it over my face, everywhere that she smeared the stick thing. Next she capped whatever that had been as the one on my nails was still doing her thing. A new set of hands touched my face up on my eyes. Next came what I am guessing was eyeliner because it felt like they were trying to poke my eye out.

Next one of them used a nice fluffy brush and put something on my cheeks gently and it felt pretty nice. To be honest the whole experience had felt lovely, being pampered and all. They finally stopped messing with my face as the one was finishing up on my nails. Just made me keep my eyes closed for just a little longer as she put an odd net over my shorter hair. Then a large clump of hair I guessed was a wig was set into place on my head. She let me open my eyes but when I looked over at the mirror it had been flipped, "Not until you are finished dressing and then you can see the whole image."

I shrugged and stood there as she walked over to the closet and pulled out a few articles of clothing. She set out an entire outfit for me and began to help me dress in anything I didn't know. I slipped on a pink plaid button up paired with a pair of skinny jeans with designs on the butt. Then a denim jacket over that and a small purse to match. To finish the whole ensemble they gave me a set of denim blue heels to put on.

I stood wearing all of it with three girls looking at me in awe. June walked me over to the full length mirror and had me wait there. On a count of three she flipped the reflective plate and I was stunned. I genuinely thought it was a normal piece of glass and my sister was on the other side. My eyes were now covered with a lovely pink glittery eyeshadow and a sexy black eyeliner complete with near perfect matched wings. My cheeks had a cute rosy pink blush to them along with a silvery glitter that highlighted my cheek bones. My lips were painted a bright pink to match my now colored nails. I looked just like her, so much that most wouldn't be able to tell us apart at all. My dick actually began to harden a little with how good it felt to look that good.

My sister stood next to me and hugged me with one of her feet popped into the air, "See? I told you we would look even more alike. You like it?" She asked.

"Surprisingly yeah. It almost looks natural." I said examining my face in the mirror.

"Good. Okie just one more thing." She turned me to her and held up a little spray bottle. She told me to keep my eyes closed again until she said and then sprayed me in the face about three times. My face was covered in a liquid that seemed to be drying quickly. She told me it was to set the makeup and help it stay longer.

"How long are you planning to have this last?" I asked worriedly.

"For our whole night out. Amber is gonna drive us to downtown and we are all gonna enjoy a girls night." she said happily.

"Whoa. I never agreed to go out in public like this." I said hesitantly.

"Don't worry you look just like me. Everyone will think we are all girls." She said sweetly with the eyes, "Please, Clark?"

"Uuuugh fine. You know I hate it when you use the eyes."

She squealed excitedly and got dressed up in a leather jacket and leggings while all three started doing themselves up. Amber went with a dark purple look and Sarah a light blue based look. June of course did hers to match mine in all the pinks and we were off. Amber and Sarah were up front with June and I in the back of Amber's smokey grey Camaro as we drove the couple miles away from home to get to downtown. Amber pulled into a tall parking garage then parked up on the top level. Before we got out June turned to me and said, "You are probably gonna want to change your voice a little. It has gotten to be kinda low for a girl."

"Would something like this work?". I said trying my best to make my voice like June's. All three girls looked at me with surprised looks, "What? She's my sister. We have close voices, I just had to make mine a little higher."

After they checked my laugh and walk, which both came naturally to me even in a set of high heels, we all went over to the elevator and went down to ground level. Sarah and June were the first to get off with me and Amber in the rear. Once we hit ground level the doors opened to reveal a couple of older guys who looked at the four of us and were almost completely dumbfounded. June and Sarah stepped out followed by Amber and I. I looked in a window on the wall as we were walking out and noticed one of the guys checking out my butt as we walked away. I could feel my face turn bright red at this.

I did my best to put it out of my mind as the four of us walked around downtown but I was oddly flattered. Once Amber started to complain about her feet from her heels we went into a restaurant. It was an old bar and grill called Wally's Well. I had been here before and enjoyed the food they served. This time was different though. By this time all of the party types and drunks were in full swing and they were quite prevalent here. A whole crowd of guys were hooting and hollering at each other over in one of the corners. They seemed to be in a contest of longevity.

Sarah laughed as Amber whispered something in her ear. I looked over curiously at them but they just waved it off. We all sat down and ordered a few baskets of fries and drinks and sat there while they all gossiped about odd stuff. A server brought the items and a second one placed a couple bright pink and blue drinks in front of both June and I, "From that gentleman over there." She said and pointed to a rather handsome fella at a table with a couple of guys.

June waved but I just lowered my head in embarrassment. June didn't hesitate and sipped at hers. I was a little reserved but decided to try it after a little encouragement from Sarah and Amber. It obviously had a little alcohol in it but it wasn't strong. It honestly tasted like a sour bomb pop and I liked it. I drank it down decently quick over the next half hour. I could slightly tell it was affecting me when my sight focus had deteriorated a little and things were a little blurry at a distance. Once my first was empty a second almost immediately was placed in its place. Before I could drink any of it though the need to pee hit me like a brick wall.

I stood and excused myself real quick. June said something but I couldn't hear with the hollering and I couldn't hold it so I bolted. I opened the door and went to one of the stalls. I pulled my dick out and stood there feeling the lovely release of my bladder before it killed me. As soon as I finished I came out of the stalls and went to wash my hands. I looked into the mirror and checked the makeup on my face to be sure that it wasn't ruined at all.

Nothing was out of place so I felt confident that I was still ok. That's when another stall clicked, "Well. Isn't a lady supposed to be in the other restroom?" said a masculine voice. I turned and looked into the eyes of the guy who had bought the drinks for us. He looked at me closely, "Unless you aren't exactly a lady." He smiled.

I got scared. He came close and placed his hands on the sink behind me, pretty much trapping me in place. His brown eyes looked intently into mine. I could smell his musk and it was oddly nice. His stubble made him look rather quite handsome in a rugged way. My heart began to beat very rapidly as this encounter continued. Finally, I panicked and pushed past his arm then ran out of the bathroom and straight to the booth. I sat down next to June and sat in silence.

"You ok? What happened?" June asked me.

"The guy who bought us the drinks just tried to trap me in the bathroom." I said, "Can we go home now?"

She set her hand on my back and looked at Amber who nodded and got up with Sarah. They left while we sat there together. June put her phone on the table and hugged me, "Did he try anything? Did he hurt you?"

"No. He just tried to keep me from moving away. I think I was almost starting to get turned on at the same time that I was panicking. I just want to go home and be done with this."

"Ok. Amber just left to go get the car. It'll be ok." She said soothingly. Suddenly she got a text and we stood and left the bar. Amber was waiting just outside and we left downtown headed for home.

We pulled up to the house and Amber parked outside on the street. We walked in and went upstairs into June's room. We all sat on June's bed as they tried to console me. I wasn't as shaken anymore. More just really confused. I had actually felt kind of turned on by a guy.

"Are you ok, Clark?" Amber asked.

"I think so. I am just really confused now. I was getting turned on by a guy. I felt so trapped and helpless when he put his arms on either side of me."

June hugged me, "Well. We do have a couple things to help you feel better if you would like. Firstly, do you like being dressed up like this?"

"Kind of. It feels almost natural to be dressed this way."

"Good. I am glad you like it. Anytime you want to you can come over and I will help you get dressed up like this. I can even teach you so you don't have to ask when you want to. Next. Well, we have a couple surprises for you. I still have one thing that I owe you. Sarah?"

Sarah smiled and stood up in front of me before kneeling down in front of my knees. She pulled them apart and moved forward towards my crotch. Her manicured hands reached up and grabbed the waistband of my leggings. She pulled them down in the front and I lifted my butt to let her take them off. After tossing them aside she leaned in and gently licked the head of my cock.

I wasn't wide, only about as wide as maybe two fingers but I was a bit long. From the base I measure about 9". Sarah smiled and took the head of my dick into her mouth and began to suck hard. June stood and walked off to the bathroom, disappearing for quite a while. I was barely paying attention at the moment though as I was preoccupied with the absolute ecstasy that was Sarah wrapping her lips and tongue around my dick. She expertly sucked on my head then began to move down my shaft with her blue painted lips. As I was getting my cock sucked by one gorgeous girl another grabbed my cheek and pulled my head back. Amber pulled me back until my head was on the bed and she began to kiss me deeply. They stopped very briefly to both undress me the rest of the way then undress their own sexy figures, Sarah in front of me and Amber behind.

June sat down on the bed next to me while I laid there between these two beautiful girls. Amber pulled away and Sarah increased her efforts on my dick. I felt like I was getting close when I felt something touch my bright pink lips. With my dick being sucked so powerfully I wasn't thinking straight and I opened my mouth freely. That's when I officially got my first taste of a real penis. I felt the head slide past my lips and rest on my tongue. It didn't go any farther than that though. Once I tasted the fleshy texture of it my first reaction was a feeling of acceptance. I was surprised to think that I kind of liked it until I realized what it was. Then shock took over and I pushed it out of my mouth. I looked up to see Amber above me with a decently sized dick hanging over my face.

"What the hell?" I exclaimed.

Amber looked down at me and cupped my cheek, "You ok? I hope I didn't hurt you. You seemed to be enjoying it for your first time."

"Why do you have a dick and why were you putting it in my mouth?" I said trying to be angry. Sarah released my engorged phallus from her mouth and waited.

June leaned close, "It's ok, Clark. You were liking it based on what I saw. What's the matter?". She rubbed my exposed body.

"I was liking what Sarah was doing. I am a guy and I am not gay."

June pushed me back down with her hand on my chest, "You we're getting into sucking her girl dick and you can't hide it. Tonight you are one of us girls and can let yourself enjoy it like you were." I tried to argue again but she shushed me. "Clark. Just try it open mindedly. If you genuinely don't like it then we will stop. You are getting sexually doted on by three very attractive chicks. Does it really matter how it is done?" She had a point.

I conceded and laid my head back down, "Ugh. Why can't I say no to you?" She leaned down and kissed my cheek.

Amber and Sarah moved on the bed in an odd position under me where they had their legs in an X-shape on the other side of the bed with Amber's girl dick in front of my face and mine in Sarah's. June opened her night stand and pulled out a bottle of some kind as she stood on her knees behind me. She popped it open and with a wet squelching noise she began to rub a gooey, slick lubricant onto my butt. Sarah pushed my knees apart a bit more which brought my cock down into her mouth again. She began to move her head up and down as she sucked on me hard. June slathered the lube onto my tight ass very liberally before sticking a couple fingers through my muscle to loosen me a bit. I gasped as the feeling hurt a little bit but as she began pressing down it felt really good. I instinctively and unconsciously clenched my anus at the feeling of being penetrated for the first time though.

Amber looked into my eyes and cupped my cheeks as my loving sister leaned over my back. June started to kiss and suck on my neck which involuntarily sent a loving moan of pleasure through my lips. She leaned back up and grabbed my ass to give my naturally plump bum a nice hard squeeze. I moaned again and she went back to trying to loosen my sphincter with her fingers. She removed her fingers which was when I felt her tongue replace them as she began to lick my asshole. It actually felt pretty good and I was almost liking her tongue in me.

Amber held my cheeks caringly and started to move my head slowly, inching my face closer to her girl dick that was protruding from her lap. The idea was still odd but with the cock belonging to such a hot naked girl I was intrigued. I kept my eyes locked with hers as I let her move me. I lost her gaze as I looked down at her cock. I let my lips come in contact with it before she pushed a little harder and her cock parted my lips and pushed through them. This lovely girl dick spread my soft painted lips as it entered my mouth deeper and deeper until it hit the back of my throat. She stopped pushing my head and loosened her grip but began to rub her hands through the hair of the wig. I just sat there holding a dick in my mouth.

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bySkylar_Macy© 3 comments/ 9359 views/ 19 favorites

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