A New Friend

It had only been about a month since I'd moved to a new city; I was living with one of my friends I'd grown up with. He'd moved a few years before me and offered me a spot on his couch until I could get on my feet and find my own place. Aside from him and our other roommate, I didn't know too many people; I'd met a girl after my first few days in town and we'd been dating ever since.

My roommate invited me to a party his friends were throwing so I figured I'd bring the girl I'd been dating along with me to break the ice since I wouldn't know anyone else. The party was in a nice gated community in a large apartment building; the apartment itself had two floors of it's own over looking the downtown skyline. I introduced the girl I'd been dating to my roommate and his friend who was hosting the party; she wandered away and they began to compliment and congratulate me telling me just how attractive she was.

"Thanks. She's alright, I guess. I like her a lot." I told them.

The host of the party was named James and he was a pretty cool guy; we clicked almost instantly and had a lot of the same interests and hobbies. It felt like I'd known him my entire life much like my roommate; he introduced me to a few of his friends from school who had all moved here together. His best friend was named Darien and was a very openly flamboyant gay man; I'd never had a problem with gay men, in fact they were quite fond of me.

I was somewhat of a late bloomer but once I bloomed I began to really take care of myself. I started working out and packed on quite a bit of muscle mass, began styling my hair, dressing stylishly, and tanning regularly. Before I was a pale, extremely skinny and anti-social person; you would have never caught me at a party a few years before this. With my newfound look I began to garner the attention of just about anyone I'd pass by; this was not something I was accustomed to as I generally hated people.

Before I knew it I was constantly surrounded by the girls in my very small city.. But much to my surprise I was drawing the attention of men far more than women. I very much embraced this as I began to branch out and attend more parties; I accepted the attention of anyone who would give me any. I loved to strip my shirt off and dance around, grinding on any girl who'd dance with me. I considered myself to be quite "pretty" for a guy and I suppose this intimidated a lot of people as I began to hear the "gay" rumors.

"Oh, he must be gay. Look at the way he dresses."

And so on.

Then I moved to a much bigger city.. With a much larger gay population and I began to notice just how many men would check me out; it got to the point of where I would feel harassed just about everywhere I went and honestly made me uncomfortable. I understood how women must feel on a day to day basis.

Anyways, back to the party.

Darien was the life of the party and with good reason; he was calm, cool, and charismatic. Everyone seemed to love him. The girl I brought connected with him just as quickly as I'd connected with James and before I knew it they were exchanging phone numbers, social medias, and plans to hang out after this. While he was extremely flamboyant if he didn't want you to know that he was gay, you would never have known.

One late night probably a week or two after the party, I was hanging out on my couch in my apartment watching a movie by myself. It must have been around 4 AM when I got a message on Facebook from Darien. We'd become friendly since the party and he was getting along with my girl pretty well so he was around fairly often. He'd never messaged me before and it was late so it was a little strange but I figured I'd chat him up.

"Hey sexy" He opened the conversation.

"What's up bbygirl?" I jokingly responded. As I'd said earlier, I'd become accustomed to receiving attention from any and everyone so I was always a little playful.

"Just chillin in bed watching Netflix." He responded.

"Nice. I'm just hanging out watching movies in my bed too.. AKA the couch." I joked.

"Oooh. Naked?" He asked.

"Not exactly.. I don't know if my roommate would be okay with that." I told him.

"What? That's stupid. You don't have a separate room?" He asked.

"Nope. I'm on the couch until the lease is up." I explained.

"Damn. No naked time for you."

"Yeah, I gotta go elsewhere for that." I replied with a crying emoji.

"Well, there's always room for naked time in my room.." He boldly responded.

"I'll keep that in mind if I ever switch teams." I told him. I was a bit uncomfortable at this point but I wanted to keep it light; besides he was a friend.

"You could play for both teams.." He continued.

"Hell, it IS 2019 right?!" I continued to joke with him; although I don't think he was joking anymore.

"Exactly!" He excitedly responded.

I sent a silly tongue out emoji to verify I was only joking around but he continued..

"Even if you wanna just be naked and need somewhere to be, my room is available with or without me." He said.

At this point I figured well, maybe I misjudged the situation and he was really just trying to be a good friend and offer me a place to have some time to myself. But then he kept going..

"So you can be in peace or have me help you be in peace.. Hehe." He said with a winky emoji.

I was at a loss for words; it was clear to me what his intentions were from the start of the conversation now. Ah well, it happens.

"Whatta sweetheart." I responded short in hopes to end the conversation.

"I try.." He said. "Just know I like to "give a hand" to my friends." He added.

I decided it was time to stop joking or flirting or whatever you want to call it; I suppose I was essentially leading him on. I didn't respond to that last one.

"Sorry if you think I'm a weirdo." He texted me about an hour later.

I'd already fallen asleep and woke up to be reminded of our conversation from the night before and it felt a bit tense and awkward.

"Haha, it's all good." I assured him.

While Darien was a good looking guy and fun to be around; I'd never been attracted to another man in my entire life. But that's not to say I haven't been just a bit "curious" so to speak.

I'd seen transgender porn online and while it made me feel sick at first; I grew to enjoy it. There were women with big breasts and firm asses.. And dicks to go along with them. Something about it clicked for me; I was so attracted to the femininity behind it; the submissiveness. From there my curiosity began to peak as I dug deeper and deeper into the fetish and this is where I began to stumble upon cross dressers, fem boys, sissies, and so on.

Trans was one thing.. But the rest? That was an entirely different thing. I found myself increasingly turned on by the thought of having a man dressed as a woman completely submit and succumb to my every need.. My deepest desires. Perhaps they could fulfill me in ways a woman couldn't. How could I know? I couldn't.. But I sure could fantasize about it.

Now, on the opposite side of the spectrum I'd tried watching gay porn; no men dressed as women, no transwomen, just straight on man on man sex and I couldn't handle it. It did nothing for me and kind of made me feel sick once again; my cock couldn't keep hard. I believe it was just the masculinity involved; the testosterone, the sweat, the body hair.. It was not for me. I preferred femininity; smooth and slender bodies.

A few more weeks went by and I hadn't heard from Darien; I believe he was embarrassed after what I assume was his late night horny rambling with his cock in hand the last time we spoke. But then out of the blue, he texted me.

"Hey, we're having a little get together at my place tonight. James and some other people from the party you came to. We'd love to have you over."

I'd never been to his place before so I grabbed the address, hopped in the shower, and headed over there. I arrived around 9 PM so it was still a little early.

"I'm here." I texted him.

I parked on the street and headed into the lobby of his building. He came down to greet me and we went up to his apartment; to my surprise I was the first one there.

"Where's everybody at?" I asked.

"They should be here within the next hour." He told me.

Oh boy. This was bound to be uncomfortable for the both of us.

"You got here quicker than I expected." He said. "I still need to get ready and take a shower and everything. Make yourself at home, I'm sure James will be here soon."

He went to his room to hop in the shower as I breathed a sigh of relief; crisis averted.. Or so I thought.

About 20 minutes later I heard the shower turn off and Darien hopped out of the shower.

"Is James here yet?" He shouted down the long hallway.

"Not yet." I yelled back.

"Has anyone showed up?" He asked.

"Nope.. Just me." I responded.

Then there was silence; until I could hear the wet thumping of his feet as he walked down the hall. He came around the corner and our eyes met; he was standing there in front of me with only a towel wrapped around his waist. His long brown hair was soaking wet and hanging down to his shoulders as the water dripped and dripped down his extremely effeminate body. My eyes innocently wandered down from his eyes following a streak of water from his hair as it crossed over his chest and down his abs to the tight V cut above his towel line.. And that's where I stopped.

I saw the bulge of his cock through the towel and my eyes quickly averted; I coughed and turned my head towards the television. I think he was aware that he had caught my attention as he laughed aloud and approached me.

"What?" He asked.

"What?" I said, a bit flustered as he continued to approach me.

He sat down beside me and laid back against the back of the couch; I scooted forward so that I was sitting on the edge of the couch leaning forward as if I was intently watching the TV. Really I was just trying to ease the tension. Darien raised one leg and extended it out; his foot in front of my face. My eyes began to wander again as they trailed up his smooth and moist legs. I realized what I was doing once again and shook my head and turned back toward the TV.

Darien crossed his legs over the other and then pulled forward so that he was sitting on the edge of the couch with me; he inched over closer to me until his thigh was placed against my own. I began to move down the couch a bit hoping he wouldn't catch on but as I moved further away he grabbed my inner thigh and rested his hand.

"I'm sorry about the other night.." He began. "All those weird messages I was sending."

"Oh, don't sweat it man. You were just joking." I said.

"Well.." He said. "I'm only apologizing because I wasn't."

The sexually neglected younger self inside of me was intrigued; I began to feel all tingly. I was flattered but still incredibly uncomfortable. He started to massage my thigh a bit and I could feel something happening under my jeans; all the blood was rushing to my cock and I jumped up out of nowhere.

"I., uhh.. I need to use the bathroom. Where's James? Is anyone else coming over?" I awkwardly scrambled to find my words.

Darien kicked back once more on the couch with a smirk on his face.

"Yeah, they're coming. Don't worry." He laughed. "You can use the bathroom in my room, last door on the left down the hall."

I quickly rushed down the hall and into the bathroom where I slammed the door behind me. I took a deep breath and looked myself in the mirror; my cheeks were a rosy blush red. I took another deep breath before taking a piss.

I flipped the switch to the lights and exited the bathroom; Darien's room was pitch black and had no windows. For a split second I saw a dark silhouetted figure standing in front of me; long hair and a curvy slender body. I would have sworn it was a woman. I was shocked. Before I knew it I was being gently pushed backwards against the wall; a small soft hand reached under my shirt and ran it's way down my muscular body and abs.

I exhaled deeply and froze; I threw my hands back and in the air against the wall. The hand had made it to the top of my pants and was now reaching into them; the skin on my stomach above my cock began to twitch. I was completely caught off guard; I couldn't speak or move. I was stuck.

The soft hand gripped my cock tight; it was already half way hard and I could feel it continue to grow in the palm of the person standing before me. My eyes closed and locked tightly shut; the person before me I thought to myself.. There was no one else here and I knew it. It was Darien.. But I couldn't deny just how good his touch felt.

He used his other hand and grabbed one of my wrists and shoved it down around his waste as he moved in closer to my face; I turned my head quickly as I could to avoid kissing him. He placed my hand around his waist and dropped the towel that was covering his lower body; he moved my hand until it was on his ass cheek. He pushed his hand hard against mine making me get a nice firm grip on his ass; it was smooth and soft just like his legs and hands. It wasn't too muscular; it was actually quite fat.. In fact it was larger than the girls ass I was seeing.

I gripped and squeezed his ass as my other hand moved down to do the same to his hips; I pulled and spread his ass apart as he moved closer towards my neck. I could feel his breath on my neck and I felt a little bump on my leg; his cock was hard as a rock and it had just touched my leg as he was about to kiss my neck.

"STOP." I yelled as I came to my senses. I released my grip on his ass and hips and he took a step back. "I have to go." I said, as I quickly ran from his room and out of the apartment.

I couldn't believe what had just happened.. I was all for flirting and having fun but what had I just done? My cock was hard the entire car ride home and I could feel the moist tip of pre-cum leaking out and through my boxers. I couldn't get the image of his silhouette out of my head; I couldn't stop thinking about his soft tough and his feminine body standing before me, dripping wet.

But still, I felt sick to my stomach. When I got home my mind continued to wander and I started to think about how hot he'd look if I dressed him up like all the videos I'd seen on the internet; how good he'd look with some skin tight stocking and a garter belt wrapped around his thick thighs. How his ass would look outlined and secured tightly within a nice thong. I stroked myself to orgasm thinking about all of this.. and I still felt sick. Was I gay? Does this make me gay? I still love women and I love pussy.. And I'm not attracted to men. But he got me hard and I busted a nut thinking about fucking him in the ass. That's pretty gay. I was at war with myself.

I had already cum.. But I still felt curiosity,

"What the fuck was that!" I texted Darien.

Hours went by before he responded; I'm not sure if he had actually invited anyone over for a get together or if it was just a plan to get me alone.

"What happened?" He responded, finally. It was already around 2 AM.

"Why'd you do that?" I asked.

"I don't know.." He said. "It seemed like you kinda liked it..."

I didn't know how to respond; I did kinda like it but I didn't want him to get the wrong idea. I started to type and then I'd delete everything I'd just wrote over and over again before giving up. I suppose he'd watched my confusion play out from his phone because he finally asked.

"Have you ever done anything with a guy before?"

"No." I responded sternly.

"So that was your first time?" He asked.

"We didn't technically do anything.." I replied.

"I know.. But I touched your cock." He said. "And you were grabbing my ass."

"Please stop." I said again, sternly.

"I'm sorry.. I really thought you were interested." He apologized.

I could feel the sincerity and I understood his confusion; I did let things go further than I should have.

"It's my fault." I told him. "I should have been more up front. I guess I was leading you on a little bit. I liked the attention."

"Well you know.." He started again. "I wouldn't tell anyone."

My heart began to race.

"It would just be between you and me." He continued.

My cock twitched between my legs.

"I don't know." I told him. "I like your body.. It's just that.." I was terrified to finish the sentence.

"Is just what?" He asked.

"This is going to sound stupid.. But I'm not attracted to men." I started to explain. "You're very feminine and you have an extremely feminine body but.. When I felt your dick press against my leg I freaked out."

"Oh.." He replied.

"But God.. I have to be honest. Your ass is amazing." I told him.

"You think so?" He asked.

"Yes. Honestly, it's bigger than most of the girls I've been with." I told him. "I'm an ass man."

"Hmm.." He started; we were essentially playing one big cat and mouse game with the other. "What if.."

I could feel myself aching with anticipation as he continued to finish typing his sentence; my self control was fading and my hormones were taking over. I could feel the testosterone coursing through my veins straight to my cock.

"What if the next time you came over, I leave the door unlocked and you can find your way into my room.." He laid out the scenario. "I'll leave the lights off like they were tonight, so it'll be pitch black."

My cock was rock hard as he proceed to tell me his idea.

"I'll be on my bed waiting for you.. On my hands and knees." He said; my mouth was all but watering at the thought of his ass. "Face down, ass up, with my back arched. I won't say a word and you can "stumble" around and do whatever you want until you accidentally "slip" inside of me."

"I don't know.." I was still hesitant. "I'm nervous. I've never done anything like that."

"Would it help if I put on some women's lingerie?" He asked.

Ding. Ding. Ding. We have a winner.

"Seriously?" I asked.

"Yeah, I'm serious." He assured me.

"That is exactly what I want." I told him.

"You like that?" He asked.

"I've always wanted to try that.." I responded.

"You know I used to do drag, right?" He asked.

I had no idea.

"I'm really good at doing my make-up like a girl and I have a ton of wigs and outfits." He told me. "Here, I'll send you some pics."

He sent me several pictures of him completely dressed as a woman; from face to body.. and especially ass. He had everything I was looking for and to top it all off, he looked 100% like a legitimate woman. I was in shock and awe.

"Okay, let's do it." I was sold.

We arranged to meet up the next night as his apartment; very late at night. I could barely sleep that night knowing what I had just agreed to. I was so anxious, nervous, and excited.

The next night I arrived at his house and much like the night before I texted him to tell him I was here.

"Okay, come on in. I told the security guard in the lobby I was expecting someone so just tell him and he'll let you in."

My heart was beating out of my chest; I was somewhat embarrassed to speak to the guard in the lobby. It was passed 2 in the morning; surely he knew why I was here. But I didn't care; all I could think about was the ass that was upstairs waiting for me. I made my way inside and the guard prepared the elevator for me; it was the longest ride up of my life and my cock was pressing hard as a rock through my shorts.

I stepped out and up to Darien's door; I received one more text just before entering.

"Tonight, I'm not your friend Darien. Tonight, I'm Amber and I'm going to do everything and anything you want me to do to please you."

Fuck. I felt a bit of pre-cum drip out of my cock as I read that. Just as he'd promised the door was unlocked; the apartment was completely pitch black aside from some candles he'd lit in the living room. I quietly closed the door behind me and then I heard some loud clicking and thuds against the hard wood floors coming down the hallway. I was a bit panicked as this wasn't apart of the scenario he'd laid out for me last night; I was frozen in the middle of the living room again waiting to see who was going to turn that corner.