Aaron to Ashley

To begin, I'm Aaron a 18 year old high school student, I have an older sister that goes to college in the next state. My dad is a doctor, he always either out of town or busy with a bunch of patients. My mom happens to be a fashion designer, she is also always traveling with her job.

Myself I'm very average teenager, nothing special to the ladies 5'6 130 lbs. Most of it is my ass and legs cause played soccer most my life. I never had a girlfriend let alone kissed one. I'm pretty shy so it's my fault, but it's hard when the opposite sex doesn't even look my direction.

I get made fun of cause of my brown wavy shoulder length hair, but I look goofy when I wear it short. Since my parents always are gone I hang out with my 2 close friends and acquaintance at my house. My best friend Ryan, Tiffany, and her obnoxious boyfriend James.

October 24th....

It's a Saturday a week before Halloween and we're all hanging out in my room. Naturally we all get on the subject of Halloween and we all haven't decided what we're going to be this year. I know a week before we're trying to figure out what we're going to dress up as.

Tiffany gets to thinking and says "I think James and I should be Hugh Hefner and a Playboy Bunny. What do you think about that babe?"

Looking over at James, he says "sure I don't care saves me the trouble of thinking of a costume."

Tiffany asks "what about you Aaron, any ideas? What about you Ryan?"

I look at her and say "I don't know, I'm all out of ideas."

Ryan doesn't say anything and shrugs his shoulders. Tiffany replies "You two are a lot of help."

Tiffany ponders which is never good and jokes aloud, "you two should have a boy and girl theme so James and I have couple to walk with!"

James immediately says, "yeah cause these fags are never separated from each other!"

Tiffany and James start to laugh and I get red in the face cause it's true and respond quickly "Stfu asshole."

Ryan just shakes his head and mumbles "whatever."

Tiffany not letting the idea die down comes up quickly with "Mr. and Mrs. Smith, that will be your guys costume idea. Who will be Mr. and who will be the Mrs.?"

Ryan having a more of a build than me says "Aaron, I wouldn't look good in women's clothes."

I give a dirty look at Ryan for assuming I'm even down with the costume idea and say "I didn't even agree with this, you can't sign me up for this!"

James lashes back "lets flip a coin, heads is yes, tails is no!" James is laughing hysterically cause he gets enjoyment out of trolling me. Flips the coin and lands on heads.

I say "no best of 3 not going to do it."

James says "okay" smirks and flips it again, *heads. I have an oh shit look on my face, plead "fuck that best of 5".

One more flip and heads it is. James replies "your fates sealed bro, or should I say Mrs. Smith?"

Tiffany exciting spouts "I'll do your makeup, this is going to be fun!" Ryan is just chill and so matter of fact about the situation. My heart is starting to pump cause I'm going to have to wear girl clothing.

October 25th....

A day has passed and I can't stop thinking about this and James constantly giving shit to me about it doesn't help. Tiffany always tells James to knock it off and she can't wait for Halloween night. I need to ease my nerves, so I think to myself. If I voluntarily dress myself it now it won't be so bad come Halloween night.

I go into my sister's old room and head towards her closet. My mom being a fashion designer my sister has a closet packed full of clothing. No ones home and I don't have to worry about anyone walk in so I feel normal. Lets see what's in drawer number one, panties. Hmm, I think to myself damn my sister has a lot of skeezy underwear. She has lacy boy shorts, thongs, and g-strings.

I'm kind of lost as to what I should grab. I like at school when girls wear thongs and can see them, so I guess I guess I'll grab a thong. I grab a black lacy thong with bow ties on it. The next drawer is the bra drawer, I found a matching bra. Not sure why I color coded, but I seen Tiffany do it so I think that makes sense.

Then the next drawer I find garter belts and nylons. I like seeing those on girls when I watch pornos or look at my mom's catalogs. I start undressing myself til I'm standing there bare naked to try on my sister's clothing. I think to myself what a pervert, but it's all for Halloween so I don't even think twice. I didn't realize how feminine his body was til I was about to try on girl clothes.

I started to slide the black thong up my leg the set the fabric snug against my crotch. I felt butterflies in my stomach for some weird reason. I thought to myself it's cause I'm trying on girl clothing. I feel myself to get a half chub, I don't think this is normal.

I take a breathe and put on a the matching bra. As soon as I hooked the bra which was rather big since my sister was a 34c, my boner was about to pop out the front of my panties. I'm only packing a 4" hardon. That's probably why I'm shy.

I had bigger problems, why am I getting an erection while wearing my sister's bra and panties? I tried making my boner go away, but It was stiff and not going away. I grabbed the nylons and slid them up my leg and my heart started beating. I'm so confused do girls get this feeling when they put on clothing.

I want to stop, but something is telling me to keep going. I hook the nylons to the garter belt and the best way to describe it the "female" in me started to take control. I grabbed a red strapless dress off the hanger and slid it on. I felt so feminine zipper the back up and looking in the mirror I looked girly since the dress hugged my "curves" just right.

I felt the need to stuff my bra so I went back over to the bra drawer and grabbed inserts that I had seen earlier. Why do I feel the need to have big rack? I keep questioning why I keep naturally doing these things. This is for fun and I'm looking for things to enhance my look. The last thing that was missing was heels and makeup.

I look in the corner and my sister has enough shoes to supply a shoe store. I picked black "5 stilettos, as soon as I put those on I felt on top of the world at 5'11. Then I went over to my sister's old make up stand. I was so lost, but I found red lipstick and some eyeliner and applied it. Can't say it looked good, but It didn't look bad.

I stood in front of my sister's full body mirror and was amazed to see I actually look like a girl. Why do I feel excited about this?! Am I gay? Something told me to shut up and to model myself. I walked up and down my hallway. Or should I say stumbled, walking in heels is no joke.

After about 25 minutes of doing my best runway impression I had enough in these clothes. Actually my boner was sore from tenting my dress so I needed to get out of these clothes and do the deed. As I got undressed I pulled off the cum drenched panties back in the drawer I felt a box in my sister's underwear drawer.

I moved the assorted panties and uncovered the box. On the top of the box it wrote "happy b-day slut! <3" I opened the box being curious and pulled out a 7" realistic dildo. I looked at this massive thing, well massive compared to my little excuse for a penis. This made me start thinking is this a sign telling something?

I felt the need to dress up again immediately, something was telling me I had to. This time I grabbed a different pair of bra and panties. I picked a matching pink bra and g-string. I grabbed a black halter top, grey mini skirt, and topped it off with sparkly silver stilettos.

I grabbed a bottle of lube that was in the box with the dildo and started applying it to the rubber dildo. I was breathing hard as I situated it on the bed. Like a porn star I grabbed my skirt and pulled it up, then pulled my pink g-string aside. I started lowering my bottom to the tip of the dildo and started to sit on it. As the head of the dildo started to penetrate my virgin bottom, I gasped and sat up.

The "female" in me told me to go back down and without think I lowered again and slowly edged the head into my ass. After about 3 minutes, 2 inches or so was going in and out. Occasionally I would sit up and hear a popping noise as it slipped out. I was so horny I felt the need to sit back down and re-penetrate the dildo in me.

Getting braver and braver I managed to stuff 5" in me, but that wasn't enough. The slut inside of me needed more, finally sitting on the dildo about 6.5" were submerged in my ass. I grabbed my rock hard boner and started tugging it. Less than 20 seconds later I shot the biggest load onto the floor.

Out of breathe and sweaty I sat there catching my breathe and taking in all that happened in the last hour. Immediately after my hole starting tightening up so I pulled the dildo out and the guilt set in. I felt so gay and disgusting. Looking in the mirror seeing myself head to toe in woman's clothing. Then looking at the dildo and feeling my hole start to get back to normal.

The clothes slowly came off and then I took a shower. I never felt this weird about myself and couldn't understand why I did it. I sat in the shower to wash off all that happened, but I kept questioning myself. Why? Why? Why?

October 26th....

The next day I hung out with Ryan, Tiffany, and James. I could only think about the day before. James smart ass started the conversation "you ready Mrs. Smith queer?! I couldn't even spit out a word and rolled my eyes. I felt like everyone in the room knew what I did the day before.

Then Tiffany cheerfully asked, well was more of telling me "Can we have a practice rehearsal day?!"

I quietly said "sure, If we can stop talking about it".

Tiffany excitedly replied "yes! don't worry I'll make you into a pretty lady! Promise".

All smiles, but Tiffany didn't know it was making it worse on my conscious. She is just so cheerful and nice it's hard to be mad at her.

James butted in "this is going to be fun seeing Aaron in girly clothes."

I glared and Tiffany said "shut up James, he said we're done talking about this." Two days from now would be a big life changer for sure.

October 28....

Tiffany showed up unexpectedly with two bags in hand. One with clothing and the other with makeup and products to make me look gorgeous. Feeling like a second home, Tiffany invites herself in and yells for me. I'm in my room and tell her to come upstairs says come up stairs.

Laying in my bed I look when she walks in to the room. I ask "where's James and Ryan?"

Tiffany responds "It's girls night silly" proceeds to wink and throw the bags on the floor and starts demanding things.

First she ask for me to get naked and I tell her "Look I don't know how I feel about this".

Tiffany with a pouty look replies "I went through all this trouble and you're going to quit on me now?!"

Now I'm acting like I don't want to continue, but her face finally makes me grunt "okay, only so you'll stop complaining".

Tiffany smiles and says "okay, here's a razor and some shaving creme. Get in the shower, remove all the hair from your chin down."

I argue with Tiffany responding "why? I'm not going to be naked for anyone why should I have to remove my body hair?"

Tiffany wittingly responds "You're a reflection of my work, I only do perfection."

She moves her hand in way that tells me to get into the shower. 10 minutes later I'm out and all my hair is removed from all of my body. I didn't need that much time since I didn't have much hair, most of it was masturbating so my friend wouldn't show up when the panties came on.

After I came back to the room Tiffany gave me body lotion to apply, I felt feminine putting it on my silky smooth legs. Then she started tossing matching cheetah print thong and bra. Then after a brown garter belt and stockings. I grabbed the panties, they were victoria secrets panties. Tiffany wasn't playing around and I knew it when I saw the quality of underwear.

Tiffany says "those are mine, I've noticed we had the same butt. Actually James noticed it when we were standing next to each other."

She giggled then I kind of blushed knowing James looked at my ass. I slowly put on the victoria secret thong. I had seen the same pair in my sister's drawer a few days ago and started to reminisce. The bra is a 34b, she was smaller than my sister, but I wasn't complaining.

This matching set would be something that if you saw a model wearing you would get hard instantly. I was wearing it which made me feel sexy. Unfortunately my lil buddy agreed and started to show. I was trying to hide and tried thinking about something else, but before I knew it my 4" erection was poking out.

Tiffany preoccupied with the dress and turned around and saw me struggling to hide my friend. She dropped the dress and said "Omg, I see why you didn't want to do this. You're getting excited from this!"

I was red in the face and defensively said "shut up, I don't feel comfortable and you bullied me into this!"

Tiffany feeling bad replied "calm down sweetie, you don't have to do this if you don't want to. You just look really cute and I thought I could make you in a pretty girl."

I'm slightly easing after hearing that responded "Don't tell James or Ryan about this, I will never hear the end of it."

Tiffany smiled and responded "okay Ashley, secrets safe with me." I was confused wondering why she said Ashley, but I accepted it and wanted to continue.

Being referred to as a girl made me feel great and uplifted. Tiffany called me Ashley and I complied with all of her requests after that. I put on the garter belt and stockings then finally putting on the blue sequenced dress that Tiffany brought. Finishing off the outfit with 6" blue stilettos.

Then Tiffany sat me down putting on all the make up and curling my hair. After about an hour and a half I was standing in front of the mirror. Tiffany was impressed with her work and sneaked a snapshot of me. Then secretly sent the pic to James and Ryan.

James response uncaring of what Tiffany would say replied "who's that hot chick? I'd give her a 9/10."

Ryan sent back "damn, she's got a nice body. Is that one of your friends?"

Tiffany showed me the text message and I got this self confidence after reading the responses. Tiffany replied back, yes "it's my friend Ashley. I hope you feel good about calling a dude hot and saying he has a nice body."

James responded quickly "fag, I was just kidding I knew it was Aaron all along. I bet he got excited being called a hot chick."

Ryan replied "oh, he looked convincing I wouldn't of known unless you told me." Tiffany again showed me the message and I rolled my eyes at James response and blushed at Ryan's.

The night felt like a fairy tale for me. Even though I had to change out of the women's clothing the new me would be there Halloween. Ashley would reveal her self to the world. Why was I thinking like this?

Despite being against the initial idea, I couldn't wait for it now. I denied it and played it cool when James poked fun about it. Ryan had got his costume together, it was a nice tuxedo suit and he had a gun holster to complete the Mr. Smith costume.

Tiffany had got me the Mrs. Smith black dress that was long on the right and had the open on the left side to show off some skin. I had put his costume in the closet and fantasized about it til the night came.

October 31st...

Tiffany had came over early to start working on my look for Halloween night. Same routine as before shower, shave, and let Tiffany makeover begin. Within a hour and a half I was head to toe Mrs. Smith. More importantly "Ashley" was coming together and taking over me.

My costume was complete with a black dress that fit my curves. 6" black heels and underneath was a garter belt that connecter to her leg holster and nylon leggings. Tiffany rewarded me with a black victoria secret lace thong and bra. Tiffany took the time to even put white tip press on nails to make me feel even more feminine.

I looked in the mirror and felt so sexy once I was all dolled up. Tiffany made my makeup look so lady like, not like the drag queens you see. She curled up my long wavy hair and I was one looked like one bad bitch when she was all done with the makeover. I hugged Tiffany and thanked her for the complete makeover.

Tiffany said "no problem, it's going to be hard keeping the boys off you tonight!" I grinned and looked in the mirror and it only boosted my confidence admiring the new me. Tiffany jumped in the shower and got into her playboy bunny costume. Together we could turn a whole crowds attention with how hot we both looked.

Ryan and James show up in their costumes and are waiting down stairs. I catch a peak of Ryan's costume and I can't lie he is looking studly, in his tuxedo. I see James next to him in his red robe and pipe in hand. James yells for us to come down stairs, "ladies were here, time to go!"

Tiffany and I both walk down stairs. Eyes are immediately glued to me, and I walk towards Ryan and Tiffany goes to James. I can feel James eyes burning me with his retinas as I'm approaching Ryan. Tiffany catches James and says "eyes on me champ, I'm your date remember?"

I smile overhearing that. James mutters "but, uh, she, he, Aaron,.."

Tiffany cuts him off with "shut up and kiss me dork."

I look at Ryan and he's speechless. Ryan finally says "I can't believe that's you Aaron."

I correct him on the spot, "Ashley" and smile and do a cute little pose with my hand on my hip.

Tiffany leads the way out and almost forgets to give me a purse so I can have something to hold my candy in. To be honest candy is the least important thing, it's just an accessory to make me feel more complete. It's almost a unspoken agreement Tiffany want's to make me feel womanly as possible.

We go trick or treating. Walking as a group we are turning heads left in right. Most of the attention is on me, some of the attention is on Tiffany. Dad's trick or treating with their kids get caught staring at me. Not by me, but by their jealous wives trick or treating with them.

At this time I'm full of confidence. Strutting my stuff while trick or treating. My date almost forgets that I'm Aaron and I notice Ryan keeps checking me out when I turn towards him he looks the other way. James is doing the same thing when Tiffany is not looking.

I don't mind them looking at me like a piece of meat, I know girls say guys a perverts. Why would we dress up like this if we didn't want them looking at us? Anyways, we all make are way around the neighborhood, hardly getting any candy. Mostly just to show off Tiffany's work of art or the new me "Ashley. We all head back to my place where things get interesting.

Tiffany and James only stay for a little bit when we get back. Tiffany goes into the bathroom with me and we have girl talk. Tiffany says "you want Ryan don't you? I noticed you were flirting with him while we were trick or treating."

My face lighting up red tells the whole story and I lie to her "No, he's my best friend."

Tiffany sees through my b.s.and says "okay, I believe ya girly, but I think James and I are going to head off. Going to let him going bunny hunting."

As she wiggles her ass. Then I figure out Tiffany is trying to give Ryan and alone time and I respond "okay, thanks I think Mr. and Mrs. Smith have long night ahead of us."

I smirk and we both hug. On the way out of the bathroom Tiffany hooks arms with James and says "have a good night, Mr. and Mrs. Smith."

It's about 1030 at this time and Ryan and I are sitting alone in the room. My confidence is going to make this night happen. I say "this is boring lets take some of my parents vodka and watch some movies."

Ryan agrees and we start pouring some mixed drinks. After about one lame movie and a few drinks the real fun starts happening. I'm laying on the bed and Ryan is sitting in the chair, he moves onto the bed and I look at him strange.