Becoming My Neighbor's GF Ch. 01

This story is focused on a guy getting swept away in the world of crossdressing, only to find his neighbor has equal interest. Pretty tame stuff, compared to everything else I write. Enjoy!

*****

I had always considered myself somewhat feminine, but I never thought it would get this far.

I grew up in the suburbs, and my family was always a bit out of place to begin with. My parents were hippies, to put it bluntly. They were as progressive as one could get and when I got older they were open about it all. Yes, even the drug use. Getting high with your parents is a bit weird on the first go, but as time went on I had to say it was one of my favorite pastimes.

My own personality rarely reflected theirs. I was your typical guy growing up, running track and field in high school, then went to college to study business. It wasn't too far away, but it wasn't close enough to commute to school from home. The apple fell a little far from this tree.

I was back from my junior year and summer break had just begun. Truth be told, I had no idea what to do for the season. The past two breaks, I had jobs lined up thanks to some connections my parents had. But this time I was out on my own. Mom had a lot of trips for some volunteering efforts, and Dad was on business trips of his own.

Just myself and the house.

So I started to experiment. You see, the crowd I ran with in college was a bit different from my high school days. They were more nerdy and involved in the LGBT+ community. Two were gay, one was bi, and we were all pretty 100% convinced another was a lesbian, although she had yet to admit it.

It was a new world for me, despite the upbringing my parents gave me. There's definitely a different atmosphere at gay bars when compared to straight ones. People are more open about what they're into.

One of the things that intrigued me was wearing clothes not necessarily designed for my gender. Another person in our group had just come out at transgender, and the thought of looking like a woman had some appeal. I had to admit, I wasn't committed to my male wardrobe. I dressed that way because I thought I had to.

I don't know if BECOMING another gender was my goal. Rather, I just liked the look of women's clothing. The style, the designs, the cute outfits you could match with skirts, blouses, dresses... my mind was obsessed with this stuff.

So I took to the internet. One of the (many) advantages my generation has is all the resources available online, and I read up on how to work these styles into my life.

I started growing my hair out and taking care of it. Within a few months it was approaching my shoulders, and I had a fun time getting some use out of hair ties to make ponytails. Just like a girl!

Packages started showing up from popular women's clothing stores. I was too nervous to go out and shop, but I figured out how my size compared to women and ordered from there.

Mom was so supportive of me. From hippie parents, I guess that's to be expected. "Oh, if you ever need help on makeup, let me know!" She said, but I could already tell she had a dated sense of fashion compared to my generation's. Regardless, she was a godsend in learning the basics and understanding what certain types of clothing worked for my type.

As a month went by, I started to realize an issue that comes up for every woman that loves to shop; I was running out of money. My parents weren't too wealthy by any means, so most of my funding was from previous jobs I had worked outside of school. And without a job this season, I was coming up empty when those great sales happened.

Then my neighbor came into the picture.

I knew Ryan since I was a kid. He had lived here about as long as my parents, in a nice sized house with a sprawling yard and pool out back. He fit in well with the lower middle-class area, decorations to match every season, the whole nine yards.

The guy was good-looking, that's for sure. Short dark hair, blue eyes, a bit of stubble on his face and a light tuft of hair on his tanned chest. I don't know if he worked out, but he at least had a body that reflected a history of manual labor in the past. He was probably the first time I realized muscles were a turn on for me.

I had always wondered why he lived alone, until my mom dropped it on me when I was older: "He didn't always used to live alone. I never spoke with him directly about it, but he was married to a lovely lady ten years ago. When she didn't come home one day from work, I saw the article about a car crash in the paper the next day and... well... yeah. The poor man."

Despite all of this, Ryan seemed happy enough. We sat out on the porch with him every once and awhile, drinking to late in the evening. I found out the guy was only thirty-two years old, and I was surprised; that number was far higher than he looked.

He knocked at our door one day and mom greeted him. There was a project underway in his house, transforming the great room downstairs into two separate rooms. He needed more space for when his nieces and nephews visited, and wanted a separate office to get work done. But he was doing all of this by hand, not wanting to rely on shady contractors who may screw up his perfect home.

That's where I was offered the position. He'd pay me a good rate to show up for a few hours every day and work where needed. I didn't have any sort of experience in renovating a home, but he dismissed that; as long as I was willing to get my hands dirty, he could make use of me.

So we started in, getting most of our work done in the morning while it was still cool and we wouldn't sweat to death. Ryan was grateful for the help, and just as cheery as ever. I wasn't aware such a nice person could exist.

"You're worth every penny, Kyle." He'd comment. "I don't think people realize that a lot of muscle isn't really needed for this stuff. Just a willingness to learn and help out."

Good. I was trying to look like a girl and didn't want any more muscle, thank you very much.

As the weeks went on, my crossdressing at home progressed. I bought a few tank tops that could be worn in 'guy mode', although they would probably be a bit questionable.

For today, I put on a tight white tank top with straps going down the back and a floral design at the back. We weren't doing anything with paint or too messy today, so I felt it was a good time to try it out.

I was nervous at wearing women's clothing out of the house for the first time. Every crossdresser hates that first step. But I wasn't going anywhere too public, just down the street. And I had become comfortable enough with Ryan that this shouldn't be too awkward of an experience.

He greeted me with a smile like always and he tilted his head to the side as I walked in. Was this bad? Maybe I had made a mistake.

But then he smiled again and looked me over. "That's a cute top. You pull it off well."

And that was it. He walked to the kitchen to grab some water and got to work.

Huh. Honestly, I hadn't expected that reaction. I was expecting more confusion, more questions, some sort of attitude that said 'guess we can work with it.' But instead I received a nice comment; heck, it was a COMPLIMENT. And he even called it cute!

I got into the habit of wearing more of these as the summer went on. I added some short girl shorts to the mix, and soon my hair was growing down my back.

The compliments and nods of approval continued. Ryan loved my sense of fashion, letting me know which outfits he thought looked best, and how I looked better than most women he saw walking around this neighborhood. I don't think I'd ever blushed so hard and so frequently.

No comments about my gender, or anything else was ever brought up. He just accepted it. Why can't more people like that exist?

July started and the sun was really starting to bear down on us. Some outside work was needed at this point, and we were becoming pools of sweat after every session of working. Chugging bottles of water was helping, but not much.

"Hey, you want to take a dip in the pool later this week?" He asked one day.

I sighed with relief. "God, yes. I was wondering why you were holding out on me. I've been wanting to throw myself in there for weeks."

He laughed. "Well, I don't clean it much, but I'll do so for you. Just, eh, one condition."

"Oh, sure. What is it?"

"Uh..." He was hesitant for some reason. "You need to wear a bathing suit."

"Dude, I wasn't going to skinny dip."

A hesitant chuckle. "Um... I meant, I think it'd be cute for you to wear a women's bathing suit."

"Oh!" Ok, now I understood why this was strange. I paused for a moment to think about a response, and realized that I actually found the idea appealing. I'm dressing like a girl, so why not try to dip into the pool as one? "Sure! I don't really have a swimsuit in that, uh, gender. But I can order one right away. I've definitely had my eye on a few."

He was excited beyond words. "Great! I know you have an awesome sense of style. Excited to see what you whip up!"

Laughter was had and work continued. I couldn't have asked for a better friend to support me in this.

--

The suit came a few days later and I was relieved to find it fit.

When you're a man buying women's apparel, the sizing can be a nightmare. Well, it can be a nightmare for women too, I suppose. But trying to figure out what's going to fit a body type that an article of clothing isn't necessarily designed for takes obnoxious trial and error.

This one was a two piece. A bit bold, considering I obviously don't have the chest to support that style, but I found one that would work for even flat-chested ladies. It was a cute bright blue, and the bottoms had a strappy design on the sides. These weren't necessarily bikini-style bottoms, but more of a high boyshort design that almost came up to my naval. I understood that these weren't designed for certain packages to be stored, and I would need the extra room to store mine.

Despite how well it fit, there was still that glaring issue crossdressers face; the dick. I don't know why I overlooked that obvious flaw in this design. Even when I was soft, the bulge was still pretty apparent down below.

Oh well. It was just Ryan, right? I imagine he wouldn't find an issue with this, especially if he was the one requesting me to wear a women's suit. This shouldn't throw him off.

I shaved my whole body the day before. Chest, legs, armpits, even my arms. Being so smooth always felt wonderful, getting a little extra breeze when giving those parts some exposure.

I put on one of my more cute tops and shorts over the suit, then head out for the day. Ryan greeted me and we got to work as usual, finishing up a little earlier as we sweated harder than before. Ninety-four degrees wasn't usual for our part of the country.

"Alright, that's it for now." He wiped the sweat from his forehead, long since having taken off his shirt. As disgusting as sweat was, it was dazzling to watch the light reflect off of it as it ran down his firm body. "You bring a suit?"

"Yep!" I said with a smirk. "But I'm going behind the fence to reveal it. It's a bit much."

He laughed. "Too hot to handle?" But he followed me to the backyard and into the gated area surrounding the pool.

I reached down and peeled off my top first. Sweat ran down my body as well, and my lighter skin was a beacon in the sun today. My hair spilled down my shoulders as the top came off and my bikini shone in the light.

Then I peeled off my shorts, hesitating a bit at first. My butt looked great in these, as I had seen in the mirror. It hugged those curves perfectly, exposing a good amount of the bottom of the cheeks.

Revealed in swimsuit mode, I struck a pose for Ryan, hand on the hip and popping my leg to the side. I was LOVING how his eyes took in every inch of my body. My top fascinated him, and my butt drew some attention. But his eyes grew large as he saw the way my cock pressed against the front of the suit bottom. Admittedly it wasn't the most comfortable for me, but I could live with it for a few more hours.

"Wow. Yeah, you pick great outfits. As always." He smiled and scratched his head. "Uh, I need to head inside for a little bit and get some water first. There's towels in there if you need one. I'll be out in a bit."

There was some confusion on why he wasn't just diving in like he said he wanted a few days ago, but didn't think much of it in this heat. A pool was going to feel great.

I dove in and the relief of cool water rushing over smooth skin was magical. It flowed through my long hair, the water dripping off my skin as I emerged in the shallow end.

This was definitely an unusual experience, dressing feminine while swimming. My chest wasn't used to being wrapped up like this, and the weight of my hair was something to account for. But it was relaxing, and soothing. I looked cute and felt great doing it. It was a new feeling for me, a new type of high.

I decided to casually swim a few laps, going at a leisurely pace and taking moments to dip low in the deep end. Eventually I emerged and lounged at the side in the shallow end, resting my arms at the edge of the pool.

Being in tight women's clothing was having another effect on me, as I soon found out. My cock, struggling to exist in the tight confines of the bathing suit, was getting a bit more stiff. That's a little embarrassing. I reached down and rubbed the shaft through the fabric, my body shuddering as my fingers felt the bulge from tip to base.

Ok, probably shouldn't get all hot and bothered in this situation.

I was worried about the lack of my male companion. Honestly, I had assumed this whole deal was to get me in a swimsuit so he could admire me. I noticed the way he looked at me the more I wore my women's clothing around him. The way his eyes took in my figure, how he commented on every outfit I tried, how he worked closer to me whenever he had the chance. He had a thing for me, and I couldn't say I wasn't against having a thing for him. I had never considered myself gay before now, but there's a first time for everything, as they say.

I hopped onto the pool's edge and looked around. No one seemed to be in sight, so I lay on my back and let the sun wash over me. Normally I wouldn't need to check for something as innocent as sunbathing, but my cock was seriously throbbing at the moment, the head threatening to peek out of the top of the bottom of my suit. Despite the fence, I wasn't really into public displays like that.

After a few minutes, the concrete next to the pool threatened to burn my back to a crisp, so I got up and decided to hunt down a towel. Didn't he say there were some inside?

As I turned around to face the back of the house, I definitely caught sight of something I wasn't supposed to see.

In a window on the first floor off to the side, the curtains of his new office were pulled to the side just a bit. Inside, I could barely make out Ryan's form, sprawled out on a chair, with his hand working furiously at-

Oh GOD! He was jacking off to me!

Our eyes met and I have never seen such terror in a man. His hand moved from cock to curtains in a flash, and I assumed he was immediately taking every step to eliminate evidence of the action. Although I had already witnessed it for myself.

What the heck was I supposed to do? I figured I was arousing him in some way, but I didn't realize it was to that degree. It was making a bit more sense now why he felt the need to go inside instead of join me in the pool; I would have issues swimming with that big of an erection as well.

Unfortunately, he had taken my clothes inside, and that's where the towels were. And I wasn't about to walk home like this. I could stand wearing normal clothes, but a women's swimsuit was pushing my gender identity a bit far for the time being.

I gulped and slowly walked to the back sliding door. Was I angry? I guess so. Part of me was aroused, but I also felt a little used. Anger and horniness is a bizarre mixture of emotions, and I do not recommend it.

I walked inside and saw him standing there in the doorway of the office, just a few feet away. His clothes were all on, but his face was pale and his eyes were giving me the expression of a boy who had just been caught... well, you know. Masturbating.

"I... Kyle, listen... uh..." he couldn't even form a sentence. He knew he was guilty.

"Seriously, man?" I threw up my hands. "This is a little fucked up, you know that? I thought we were going to hang out together!"

"Christ... man... you just looked so fucking amazing in that suit... and..." he was sputtering, unaware he wasn't completing his thoughts.

"Well maybe this is what you want, huh?"

I reached down and slid down my swimsuit bottoms in a flash. My cock swung out, a semi-erection quickly beginning to form into a full erection as I took hold. I was proud of what I had down there, an average six inches and decent thickness to boot. I had shaved all the hair away, giving a nice clean look that shimmered with remaining pool water.

"Well? Huh? I assume this is what interests you."

I began to stroke myself for him, grasping the base of the cock and pumping gently. His eyes were mesmerized, watching my crotch with attention as I began to pleasure myself. There didn't seem to be any complaints about the water that was dripping to the tile and pooling up, and I doubt he would say a word.

Truth be told, this was hot as fuck. There definitely was something arousing about getting off with an audience, and having Ryan's eyes wash over me kept giving the energy I needed to continue. My manhood was standing as tall as it could and pulsing firmly in my grip, precum dripping from the tip and falling into the pool water below.

"Oh... oh fuck..." I muttered, fapping faster, cock throbbing as Ryan just gazed in wonder. Was there an erection in his shorts now? There better be.

Then he took it out. Guess he couldn't hold back. He was just as large as I'd dreamed, probably at least a good eight inches and very thick around, a nice tuft of hair at the base. Trimmed up just enough, like the rest of his body. Did this man have any flaws?

He started to rub himself with me, our gazes meeting each other on occasion, but most of the time just looking over the other's body. I took in every one of his muscles (not like I hadn't before), and they helped give me more momentum. His eyes just loved my outfit, the way it hugged my tight frame. And he sighed every time he watched my cock, watched the circumcised head throb, watch my fingers run over every ridge in the shaft.

As I soon learned, having an audience tended to make me finish quicker. As I stood there, spread my legs, and worked myself, I found my orgasm approaching with haste. I began to moan and reach with my other hand to rub my balls, cupping and giving them a nice squeeze.

I didn't really care where this went, and I doubt he did either. We both let out a simultaneous moan of ecstasy and exploded with cum, shooting lines right at each other. Surge after surge of thick white pleasure landed on the tile, shooting in an arc continuously. Our cocks throbbed as we held them at the base and our eyes rolled back as we stood there and enjoyed the bizarre moment.

Oh God, it was amazing. There was an air of disbelief and lust hanging around us, and we both had no clue what to do with it.

"That was... um..." Now I was the one who couldn't find words. Cum dripped from my cockhead and I tried to wipe it up, although I didn't have much of anything to do it with. Did I have some post-ejaculation guilt? Maybe.

I quickly pulled up my swimsuit and put my withering cock away. A towel flew at me, and I caught it, looking up to see Ryan with a smirk on his face.

"You might want to dry off."