One Sexy Halloween Costume Pt. 01

A true story. Broken up into two parts. Each one explaining an orgasmic experience that started me down a new path.

A little introduction context-

I started cross-dressing at a young age, I don't know why but I loved trying on my mom's clothes whenever she left the house. I never thought it was that weird, but knew I should keep it a secret. Then I got to high school where I met Gabby, and consequently access to a more age appropriate wardrobe. Fast forward to the start of this story and I've been dating Gabby for almost 8 years now, even making it through a shaky college experience. She went out and partied with friends a lot and I usually made introverted excuses to stay back which resulted in drunk fights. At this point in my life I didn't masturbate much anymore, but when I did I fell into old habits. Usually it would happen when I got the chance to sneak on some of Gabby's bra and panties sets and would squeeze into one of her rompers or dresses when she left me home alone. I would prance around our apartment and pose in the mirror before aggressively grinding a pillow into oblivion. I could fit into her clothes pretty well as I was just a little taller than her at 5'8" but thin enough at 145lbs that most things somewhat worked. After college, she got a really nice paying job in Seattle, and I quit my waged job in our college town to go with her.

One Sexy Halloween Costume-

It was the start of October, and Gabby and I have been in Seattle for about 6 months at this point. As we do every year around this time, we started throwing around ideas of what we wanted to do for our couples Halloween costume. After landing on absolutely nothing, Gabby said she'd ask her new work friends for ideas and find out what they were doing when she went into work tomorrow.

The next day when she came home the topic came up again and she got a big smile on her face and said, "Oh yeah! I know what we are going to do for Halloween this year!"

She then gleefully explained how her coworker Amy had gone to a 'gender bender' Halloween party the year before and said it was a ton of fun. Amy had said the party was not happening this year, but Gabby and the rest of the girls decided on their own that they should try the 'gender bender' theme this year with all their significant others. I'm not going to lie, I was excited, but very hesitant considering the history of my closeted habit. After all I've been practicing being a girl for almost 10 years now, and I've never once shared my alternate state with anyone else. Maybe doing this would be a dead giveaway?

She sensed my hesitation and said, "Cmoooon, all the other girls said their boyfriends would be cool with it."

"Sure," I agreed. Trying to play it cool.

The next day I couldn't stop thinking about this golden opportunity. I realized that this was the first time I'd be able to buy women's clothes that actually fit me perfectly. This lead to me spending the entire day on Amazon looking at dresses, heels, bras, panties, wigs, etc. The whole time imagining myself in the various outfits I was adding to the cart and thinking about how sexy I was going to look. Holy fuck was it fun.

Before I realized it, Gabby had gotten home from work. I quickly logged out, shut the laptop, and ran up to greet her. While she was telling me about her day I asked if her and the girls had talked about the Halloween costumes anymore.

She replied, "no, why?"

I nervously responded, "I don't know, I'm just curious how serious we are supposed to take this?"

"Ohhh," she giggled "I saw costumes from the party last year, and they were pretty well done."

"Got it, hopefully I can pull off a skirt," I joked.

Gabby responded by spanking my ass and jokingly saying, "I can't wait to see your booty in a skirt."

I was giddy all night, I laid awake in bed thinking about what Gabby said. It seemed like she was really excited about this whole thing. I began to wonder if this was a bigger opportunity than I thought. What if she ended up loving what I looked like all dressed up? What if this was something we could bring into our love life? I fantasized about being my girlfriend's lesbian lover all night.

The next day I was tired from what little sleep I got. I decided during my fantasizing in the middle of the night that I was going to try and look as feminine as possible Halloween night. If Gabby has any attraction to girls in the slightest, I would get it out of her. After all, it seemed the idea of my booty in a skirt turned her on. With only 4 weeks to prepare for Halloween, I wanted to do as much as possible to rock that skirt, and so I once again researched the entire day. I watched makeup tutorials, practiced feminine mannerisms and posture, learned how to take women's body measurements for myself, and even looked up fit girl workout regimens and ordered some 15lbs ankle weights.

The next day I woke up after Gabby left for work. Went on a morning run to the gym and did a workout routine I saw on Instagram from this influencer known for her bubble butt. I won't lie, I got some weird looks from the small crowd at the gym as I did about 200 glute barbell raises, but I kind of liked it. I've never really pushed so hard during a workout before, I was dripping sweat and putting up as much weight as my glutes allowed. It was nice being noticed for lifting for once. After finishing up I ran back to our house, showered, hopped in my car and went to the grocery store to get some food to meal prep for the rest of the week. Actually, before Gabby got home I had plenty of time left and decided to do another workout with the ankle weights that really focused on my core and hips. From my research I found out that you can actually make your butt muscles not only rounder, but wider too. Plus with only 30 days to get my butt skirt ready, two-a-days were probably a must.

When I woke up the next day I was sorer than I'd ever been. My butt muscles felt like they were on fire the second I tried to roll out of bed. The pain had me instantly thinking 'not doing that today', but as I laid there I began fantasizing about Gabby slapping my ass again, but on Halloween and getting horny when she realized just how plump my booty had gotten. This got my ass running back to the gym and this soon became my daily routine while Gabby was at work.

Feminizing myself became my obsession. Gabby would ask why we were eating so much salad and tofu, but I just told her that I've been working out and trying to get lean for Halloween. I loved being open with her about it, and she was usually pretty playful about it.

The next week I decided I wanted to get into character more since Halloween was only three weeks away. I began putting on Gabby's thongs under my sweatpants before going to the gym. For my home workouts I had even more fun and would wear her yoga pants and sports bras too. This made me incredibly horny during my ankle weight routines which typically resulting in me pillow humping in the middle of my workout and cumming in Gabby's thong before finishing my remaining sets. I usually ran a load of laundry while she was working anyways, and it was totally worth it being able to see my booty popping in the mirror with each weighted ankle leg lift I did. After two weeks of this my legs were starting to look really amazing, and I dreamt of a future where Gabby and I wore leggings together to the gym.

When I wasn't working out, meal prepping, and doing house chores, I was reading cross dressing forums on the best way to be passable, and then surfing Amazon for the products to do it.

That week flew by, and with two weeks left I once again decided I had to do more. After reading so many cross dresser, transgender, and sissy suggestions on feminization I felt like I would never get to where I wanted to be to turn my lesbian fantasy into reality. I decided I should buy some heels to wear around the house and could start tanning a little bit since my thighs were so pale. But then again, I don't want to be a girl, I just want to embrace my fetish with Gabby. Maybe I'm going too far?

That night at dinner Gabby mentioned that she loved how lean I was getting, "You look really good honey, I can't believe how quickly you slimmed out."

I blushed and laughingly said, "Yeah well I want to fit into a size 3 for Halloween!"

She laughed with me and to my surprise started excitedly explaining how she has been talking about Halloween with the girls at work a lot recently. She said Amy's husband already has his dressed picked out and another girl can't decide if she wants her husband to be blonde or brunette.

"What color wig do you want to wear?" she asked.

"I don't know, I haven't really thought about it," I said knowing full and well that I'm leaning towards a blonde 18" wig with big beautiful curls.

"You should probably start looking at some things," she said before leaning over and playfully whispering in my ear, "Something that will make you look as sexy as me."

I smiled and said, "Not possible, but maybe I should go get a tan to help?"

"Haha oh my gosh yesss! I'd love to see that cute butt with a tan," she said, obviously having a lot of fun with this.

That night we got intimate for the first time in months. I knew I would be horny from all the cross dressing I had been doing, so I went down on her for a good 30 minutes to make sure she came before me. However, when it came to my turn I couldn't seem to get my blood going.

"Is something wrong?" she asked.

"I- I don't know," I stuttered nervously, "I think its just been so long I'm a little nervous."

"Don't worry about it babe, you satisfied me," she replied endearingly, "We will try again next week."

The next day I decided no more masturbating, my dick needs to be ready for when Gabby decides she wants it. I also was convinced that our dinner conversation about my costume commitment was what made Gabby horny last night, and that this plan had traction. So it was time to go all in. I broke out the wallet and ordered some things that were sitting in my amazon shopping cart: a sexy pair of black 5" strappy heels, a simple cotton thong to wear in the tanning bed, and a steel-boned waist trainer for working out. I also went out and bought a ten-day tanning pass and some supplements that would slightly boost my estrogen levels (temporarily) to help my body displace some fat to my hips and butt for the big Halloween day. I continued my gym routine daily with my new waist trainer, adding tanning in between my workouts, and practiced walking in heels for hours as I did the chores around the house.

At the end of the week I was feeling very confident and genuinely proud of myself. Something about strutting around the house in high heels was so empowering, feeling my sore ass flex with every step, watching my body start to get a nice tan, and seeing how feminine I looked every time I passed the mirror was extremely gratifying, but also made me extremely horny. This caused me to get hard a lot throughout the day, but I trained myself to just ignore my little prick whenever it tried to peak out of the top of my panties.

That night I finally had the perfect outfit picked out in my shopping cart after eliminating a lot of options. I also added along some 'passable cross dresser must-haves' that I read about. These included my wig, some acrylic coffin-shaped nails, nail glue, pink nail polish, fake eyelashes with glue, silicon breast forms with a prosthetic adhesive, clip on earrings, and a butt plug with lube. I was hesitant about the butt plug as I've never done anal play up until this point, but again, the online forums convinced me that it was a necessity for helping with feminizing the motion of my hips by making them swing side to side while I was practicing walking in my high heels.

Gabby had been working late a lot that last week and I could tell she was thinking about work a lot at home, so I gave her a lot of space in the evenings. She commented on my tan and mentioned she was going to wear a flannel and baggy jeans for her costume, but that's about all the Conversation we had about Halloween. My packages arrived midday on Wednesday, 2 days before Halloween on Friday. I planned on leaving the packages in the hallway so it wouldn't seem like I was being sneaky. Also my hiding hole that had the heels, thong, waist trainer, and supplements was pretty full.

I did open the one package with the butt plug so Gabby wouldn't find it, and took it upstairs to the shower to test it out.

As I stood in the bathroom I seductively pulled off my sweatpants and shirt while watching myself in the mirror. It was at this moment, standing in my high heels, thong, and waist trainer that I was truly taken away.

Minus my head, limp dick, and body hair, I was looking at the body of a sexy woman.

My entire body was now a dark bronze tan. My waist looked like it had lost nearly 3" on each side of my tummy. And then widened about 5" as it tapered into my new hips.

As much as I was astonished by my hour glass figure from the front. I felt truly confident in my plan when I went into my favorite pose - turning my body sideways, shifting my weight to my back foot while standing on my toes on my front foot and aiming my very own bubble butt at the mirror.

At that moment I felt prouder of my glute gains than any other muscle I've worked out in my life. The transformation of flat boy butt at the beginning of the month to the tan, round, plump cheeks positioned perfectly above my toned thighs and my white triangular thong tan line made me giddy.

After staring at myself for too long I stepped into the shower, to do what I came here to do. I read online to start slow and slip one finger into my butt hole at a time. I put a squirt of lube on my middle finger, and positioned one leg up on the side of the tub.

I reached around my backside with my lubed finger and slowly started rubbing my wet crack as the warm water ran between my cheeks. I felt my butt hole slowly begin to relax and I focused the motion of my finger more on the hole itself.

Lightly circling around it. I closed my eyes and visualized what it looked like as it slowly started to open up. I moved my slippery finger's position directly over my puckered hole's lips and slowly pushed it inside.

One centimeter at a time, I pushed until it was fully inside of me. I opened my eyes in surprise, and looked down to see I had gotten hard. I guess this startled me because my sphincter reacted by tightening around my engulfed finger - I noticed this made my cock twitch and I started to feel really horny.

I ignored my hard prick though, Halloween was to close. I took a deep breathe, closed my eyes, and again focused on the task at hand.

I began carefully sliding my finger out to the tip, and then gently pushing it back in again. As I repeated this motion I started to feel less friction as my hole slowly loosened once again.

After a few minutes I pulled my finger out and applied more lube while keeping my eyes closed this time. I hyper-focused on controlling my internal muscles as I reached back behind and lightly pressed two fingers against my hole and noticed that it was still open and allowing entry.

I pushed on the small opening with my middle and ring finger and felt it generously welcome the addition. I slowly started tested my depth again, and instinctively started to arch my back.

I put my other hand on the shower wall to balance and arched even more into this submissive position. I felt my body reacting to these new feelings, and my mind focusing more on these new sensations.

After a couple minutes of sensually fingering my booty-hole I was ready for more.

I slid my fingers out and reached over to grab the wet plug. I brought it to my opening and felt its warm presence from the shower water against my entrance which was once again loosened to welcome the larger object.

I very slowly pushed the plug inside of me, I felt it get wider and wider against my sphincter's perimeter until it hit a point of resistance.

This made me so fucking horny, and I eagerly began backing my ass into the plug while my hand met the pressure.

And... then... all... at... once... POP!

The plug plunged fully inside me as if my rectum had sucked it in.

My lubed hole immediately tightened up around it and my pelvic muscles started to flex as if embracing the new object. This caused my toes to curl and I felt my legs go weak.

My body began to shake as I felt wave after wave go through my entire being. I let out a soft moan naturally, and opened my eyes to see my dick spurting out stream after stream of cum onto the shower floor.

Woah... what... just... happened...

The rest of the night I was in a daze, my body exhausted from shaking. The insides of my pelvic area felt warm and fuzzy as I cleaned up and hid my toy before Gabby got home. When she did she was confused to see the 12 packages laying in the hallway, but I told her it was a surprise for Halloween and quickly shifted the conversation to her job. She went on about her day for what felt like the rest of the night. I felt bad because I was not attentive at all. I was just waiting for time to pass until we eventually went to bed, and I was alone with my thoughts. Staring at the ceiling.

What was that earlier? Why did it feel so fucking amazing? How did I cum from it? Why do I still feel horny? What is this empty feeling I have in my ass? Do I want the plug in me right now? Why am I already thinking about trying it again? What does it all mean?

I drifted off as I relived the new feelings and sensations in my head.