FWB

When I met Adam a few months ago, I knew instantly that we would connect. He's a rare breed. Tall, dark and handsome but also incredibly compassionate, patient and open-minded. We met for the first time at a house party of a mutual friend. Adam and I had many shared interests, including biking and gaming. We've become close friends in the months since that party.

Our closeness has had limitations, though. I've never shared with Adam one of my biggest secrets - that I'm an avid crossdresser who yearns deeply to be taken by a man. To be honest, it's not something I've felt comfortable sharing with anyone. That all changed recently in the most incredible of ways. Before I get to that, though, I have to share some background on who I am and how I arrived at this point.

Since graduating college over three years ago, I've found that I'm my truest self when I'm dressed as a beautiful, seductive woman. However, it's been a part of my life that I've felt compelled to keep to myself, like so many others. I've had relationships with women for most of those years, but I've never shared this side of myself with anyone and those relationships have never lasted very long. During the days, my work colleagues and friends know me as Sam Walsh. Deep down, though, I know my true identity is as Samantha.

In that time, I've slowly transformed my body, my wardrobe and my appearance to more closely resemble who I am deep down. I've been fortunate enough to work from home, so I've had the freedom to explore and work on these desires frequently. In fact, I usually work in women's clothing, often with my hair and makeup done as if I were going out on the town.

While I initially wore wigs, I ultimately decided to grow my hair out. It took over 2 years to reach the length it is now, but I'm proud to say my mid-back length, curly, light brown hair is all mine. I've also become quite the expert at applying makeup as well. I've never been particularly hairy, but what body hair I did have I had permanently removed with laser hair removal. I go back periodically to get touch-up work done, but my body is smooth and hairless all over.

I've also spent several years wearing corsets to reshape my waist to be more feminine. Years of biking has given me a thick, firm ass to die for. On top of it all, I've worked incredibly hard on my diet and exercise to maintain a fit, soft, and feminine look to my body. I'm only 5'6" with narrow shoulders, so making my body look feminine hasn't been incredibly difficult. I honestly don't know how passable my face is, since I've not once shown Samantha to another person, but I believe I could pass.

As you can see, a significant portion of who I am has been kept in hiding for quite a while. In fact, most of my decisions revolve around what would be best for Samantha. From diet and exercise to how I spend my money, Samantha is always at the forefront.

I had spent so much energy hiding my true self, that it only took one fateful night for it all to erupt out of me.

*** Hanging out ***

On a Saturday night in July, I made my way over to Adam's house to hang out for the evening. This had become a regular event for us. Adam's gorgeous girlfriend, Alicia, was a waitress at a top-tier restaurant in the city and worked every Saturday. That regular window gave Adam and I plenty of time to hang out, play games and drink.

On this evening, though, we decided to try out a bunch of new mixed drink recipes. Adam had made a run to the local package store and bought a few hundred dollars of all sorts of liquors. For two straight hours we goofed off in the kitchen, mixing up any drink recipe we could find. The liquor flowed like a river and before long, we were both feeling it.

While I was failing miserably at Super Smash Bros, Adam got up from the couch and disappeared into the bedroom. When he emerged, he had a slutty school girl outfit in his hands. He held it up for me to see.

"Look at this, man. Alicia bought this the other day. She's so fucking hot when she wears it," he said to me as he dangled the cloth around clumsily.

What came out of my mouth next can only be explained by my highly inebriated state.

"I bet I'd look hot in that outfit, too," I replied.

Adam laughed at the suggestion, before adding, "I'll bet you 10 bucks you won't put it on and wear it the rest of the night."

"Make it twenty and you've got a deal," I shot back without even thinking.

My brain didn't have enough time to process what I had just said before Adam tossed the outfit onto my lap. I could hear the voice of Samantha screaming to be let loose inside my mind. Without thinking, I stood up, stumbled into the bathroom and began undressing.

I pulled the red g-string panties up my legs. The front barely hid my junk while the back was little more than dental floss. My bubble butt would be on full display. Amazingly, the white, frilly top fit almost perfectly, fully exposing my smooth waist. The red, white and black plaid skirt also fit nicely and was just long enough to hide my front and back, but that was it. The long, white stockings felt luxurious on my smooth skin and rounded out a sexy, seductive outfit.

I had my long hair pulled through the back of my baseball cap as usual, but I decided to let it loose, tossing my baseball cap on the counter. The only thing that was missing was my makeup, but it was clear that the outfit did all the talking anyways. I looked at my curves in the mirror and felt slutty and sexy. I could feel myself getting aroused when the voice from the living room shocked me back to reality.

"Hey, what's taking so long in there! This game isn't going to play itself."

I felt Samantha take over as I flung the bathroom door open. I strutted into the living room, swaying my hips from side to side for full effect, though I nearly fell over from being so drunk.

"Well, am I hot or what" I snarled at Adam, who had a shocked look on his face.

"Well, shit," was all that he could muster.

In that moment I felt overwhelmed with sexual confidence. While Adam sat on the couch, I turned my back to him and began to slowly sway my hips back and forth. I moved my body with as much sexual energy as I could. I occasionally lifted the back of the skirt up, showing off my firm, thick ass. After dancing for a few moments, I turned to face Adam.

His eyes were large and wide and he was now hugging a pillow close to his crotch! Adam had a boner and was trying desperately to hide it! His face turned beet red as he realized I knew. I smiled, bit my lower lip and winked at him before sitting down at the other end of the couch.

After a minute of awkward silence, he finally blurted out, "Holy shit, Sam."

"Call me Samantha," I shot back in a non-serious tone.

Adam didn't know how to respond. After a few minutes of silence, the awkwardness in the air became too much.

"Do you want me to change back?" I asked him.

"Uh, I guess not. A bet is a bet, right?" he responded.

With that, I decided to take charge. I grabbed a controller and tossed it in his lap as I started another session of Super Smash Bros. Not knowing what else to do, he followed my lead. Before long, we both got into the game and burned away an hour before we finally called it quits.

At that point, it was getting to be late and there was no way in hell I wanted Alicia to catch me wearing her outfit. I looked over at Adam and asked, "So, can I get changed now? And can I get that 20 bucks?"

"Yeah, man. Just grab it out of my wallet on the counter. I'm never betting against you again," he shot back in a dejected tone.

I got up off the couch, stopping in front of Adam one last time to lift the skirt and jiggle my ass in front of him. I stepped into the bathroom and transformed myself back into Sam, baseball cap and all.

As I stepped out of the bathroom, I flung the school girl outfit onto Adam's lap and said, "I'm gonna head home. I'll see you later."

"Alright, later dude," Adam replied as I made my way to the front door.

After a short walk to my apartment a couple blocks away, I collapsed into my bed and quickly passed out.

*** The next morning ***

I woke up to a horrible hangover and a strong sense of regret. Unfortunately, my memory of what happened the night before was fully in tact. Samantha had gotten out of her cage and put on the performance of a lifetime. In front of my best friend.

As I got up from bed, I noticed the notification light on my phone was flashing. I quickly grabbed it and saw that I had a text from Adam. The few words it had made my heart sink and only deepened my regret.

"Hey dude, we should get together today and talk."

What was he going to say? Was he going to end our friendship over what happened? Was he angry with me? My mind raced endlessly. I responded, hoping we could get together quickly.

"Anytime. Just say where when."

After just a minute, he responded:

"Starbucks. 15 mins ok?"

I wanted to get this over with and the Starbucks was just 5 minutes away. I quickly responded.

"Yup. cya there"

After a super fast shower and tossing on some shorts and a t-shirt, I bolted to the Starbucks. A double-espresso actually sounded perfect right about now. I ended up getting there before Adam, so I went ahead and ordered and found a seat outside. Adam got there shortly thereafter and had a seat next to me. He immediately started the conversation.

"So, about last night..." he started, before I immediately jumped in.

"Adam, I'm so sorry. The alcohol just got to me and ..." I blurted out before he subsequently interrupted me.

"Dude, it's ok. I'm not mad. You just ... you surprised me. You looked like you had done that before. You know, acting like a woman. Dressing like that. I'm not judging. Not at all. I just want you to know that if that's something you do, it's cool. You can tell me. That's all I wanted to say," Adam said sincerely.

That was a huge relief, but I wasn't entirely sure how much I wanted to say. Samantha was such a key part of me, but I wasn't sure if Adam was ready for the entire truth. Not yet, at least.

"I mean, it is something I have done before. Every now and then," I responded with a half-truth.

"Ok, cool. I mean, it makes sense. If you had told me you had never cross dressed before I would have been stunned. You looked like a natural last night," he responded and laughed.

"Thanks I guess? Don't worry, I won't freak you the fuck out again. You looked stunned when I came out of that bathroom," I replied, hoping to find out a little more about what he was thinking.

"Yeah, well, you did stun me. When you started dancing, I ... uh ... reacted a little unexpectedly," he said while blushing.

I laughed, punched him in the arm and said, "I noticed!"

"Oh god, this is not the conversation I wanted to have, you asshole," he said back jokingly, before saying in a more serious tone, "In all seriousness, I just want you to know that you can be yourself around me. Whatever that means. I don't want you to feel like you have to hide anything about yourself. I hope you know that."

Those words meant so much to me and I knew he meant them. I couldn't help but think there was something more behind the words, but I decided not to read anything into it.

"Thanks Adam. That actually does mean a lot. When I'm ready to share more about myself, you'll be the first to know," I said softly and sincerely.

"Good. Now, can we agree that neither of us will say a word about this to Alicia?"

"Oh god, absolutely," I responded.

We hung out and talked for another few minutes before we parted and went about our days.

*** The next weekend ***

Adam's words only deepened my longing to let Samantha run free more often. I spent the entire work week at home living solely as Samantha. My spirit felt free and I felt less apprehensive about this side of myself. The week flew by and by the time Friday came around, my mind turned strongly to the next day.

I always looked forward to hanging out with Adam, but this weekend felt different. On some level, Adam had met the real me and was completely supportive of her. He even reacted very positively to her, even if it caused him some embarrassment. That alone made our relationship feel different going into our next meet up.

On Saturday morning, though, I got a text from him that surprised me.

"Got a surprise for you. See u tonite"

I was intrigued. I didn't respond, instead letting the anticipation eat away at me as 5 PM drew closer and closer. By the time it finally arrived, I nearly sprinted to Adam's place.

As he opened the door to let me in, I couldn't get all the way into his apartment before I said to him, "Ok, you gotta show me what this surprise is."

"Damn. Nice to see you too. Thanks, I had a great week. Alicia is good. I'm good," he replied sarcastically.

"Sorry man. Your text just got me a little anxious," I responded apologetically.

"I'm just fucking with you. Come on in and I'll get it," he said.

I walked over to the couch and collapsed into my normal spot while Adam walked into his bedroom. He quickly reemerged with a box in his hand and tossed it in my lap.

"Here. This is for you," he said to me.

"What's the occasion?" I asked him.

"Just open the damn box, Sam," he shot back playfully.

I opened the box. My eyes grew wide as I saw the school girl outfit I had worn just the week before.

"I don't get it," I said to him, genuinely confused.

"I wanted to show you I was serious about supporting you. You really seemed happy and ... I don't know... liberated when you were in that outfit. It was like you were a different person. Happy. Energetic. So, I got you your own that you can take with you," he said to me in a thoughtful voice.

I nearly burst into tears, but I composed myself enough to think about what to say. My mind was flooded with emotions and a million different thoughts. Adam had met Samantha and wasn't freaked out by her. He saw her as a happier more liberated version of me and he wanted that for me. I'm sure it must have been hours that I sat there staring at the outfit in silence before I finally formulated a response. Even still, the words that came out of my mouth caught me off guard.

"Can I wear it now?" I asked him.

I immediately caught myself and course corrected by saying, "Sorry, that was dumb. I don't want to make you uncomfortable aga,"

"Yes. Absolutely," Adam cut me off. He added, "Like I said, I want you to feel completely free to be yourself around me. If that means wearing a slutty school girl outfit, then do it."

I could tell he was sincere beneath the light laughter. Still, the part of me that had grown used to keeping Samantha hidden away was screaming in my head "do not do it, he'll freak out." Yet, I believed Adam and I decided to ignore that voice.

I gave him a big, thankful smile as I got up and made my way to the bathroom. Just like the weekend before, I got undressed and put the school girl outfit on. I tossed my baseball cap on top of the pile of clothes on the floor and let my curly, brown hair flow free. I desperately wanted to put makeup on, but didn't bring it with me. I certainly wasn't expecting this turn of events.

This time, a far more sober version of Samantha made her way out of the bathroom and back into the living room. What I heard next nearly floored me.

"Hi Samantha. You look great," Adam said as I walked slowly into the room.

My heart jumped at being called Samantha. There wasn't a tinge of sarcasm or negativity in his voice. It was sincere and real and it made me feel beautiful. I still wasn't sure of how to navigate all of this, so I decided to be playful.

"You just want to see my ass again," I said jokingly.

Adam laughed then smiled and winked at me. In response, I turned my backside to him and quickly flashed him. Without looking back at him, I collapsed on the couch in my usual spot, my heart pounding in my chest. I avoided looking at Adam, in part because his actions had unexpectedly turned me on. My cock was beginning to grow and harden and I needed to calm down before I pitched a tent with my short skirt.

I was eventually able to calm myself and we amazingly settled into our normal routine, despite my considerably different attire. In fact, Adam seemed completely unfazed with all of this. He consistently referred to me as Samantha and I never once corrected him. We drank. We talked. We played games.

A few times through the evening, though, I was sure I saw Adam staring at me out of the corner of my eye. I didn't know for sure, but each time I got up to get something or go to another room, I felt like his eyes were on me. I dismissed the thoughts as wishful thinking.

The evening eventually came to a close and Sam reappeared, box in hand, to make the walk back home. I wasn't sure what the future held, but Adam had given me a precious gift that evening. One that would ultimately change our relationship forever.

*** The following week ***

The next day started off like any other. I did some chores, ran some quick errands and ultimately spent most of the afternoon at home watching Netflix and playing games.

Around mid-day, I heard my phone vibrate on the counter. I reached over to grab it and saw that Adam had texted me. His message intrigued me.

"How's my Samantha doing today?"

My Samantha? I often hate text messages because the tone is never truly clear, but I got the feeling this was not sarcastic. I hesitated to respond for a few minutes, which apparently prompted him to follow-up his original text with another.

"You looked beautiful last night."

Oh my god. My heart immediately started racing. What was going on? Adam was now referring to me as Samantha and telling me I was beautiful! Without thinking, I shot off the first response that popped in my head.

"Didn't even have my makeup on, silly boy."

Samantha was now driving this conversation. She was in full control and I was thrilled about it.

"Well make sure u bring it next time," Adam responded pretty quickly.

"Ok. Gonna bring my own outfit too if thats ok," I responded.

"Sure, but may have another surprise for my girl," he shot back.

At this point, my heart was racing and my cock was as stiff as a steel rod. I was so turned on and excited. Saturday couldn't get here soon enough! Before I could respond, Adam sent another message.

"Send pics of u in ur fav outfits. Would love to see them."

Holy cow! My mind instantly scanned my closet and all the things I could model for him. I could model my skimpy, pink teddy or my two piece black and white bikini. Maybe my skin-tight sexy red dress or my slutty cheerleader outfit with the black thong.

I finally settled on the skimpy pink teddy. I ran to my closet, pulled the teddy out and rushed to throw it on. I bolted to the mirror to make sure my makeup and hair looked good. I applied lotion to my arms and legs, giving them a nice glisten that I hoped would come through in the picture.

I set the phone up on my dresser and aimed it toward my bed. I sat on top and tried various poses as the timed camera app took picture after picture. After a few minutes, I grabbed the phone and sorted through the photos.

I found the perfect one. It was a shot with my legs pressed together as I laid face down facing away from the camera. It showed off my perfect, thick ass beautifully as I looked back at the camera over my shoulder. I deleted the other pictures and quickly sent this one to Adam with no hesitation.

After just a minute, I got a message back that put me on cloud nine.

"Absolutely stunning, Samantha. God damn!"

I absolutely glowed. I was also ridiculously turned on at this point. I grabbed one of my favorite dildos out of the closet and quickly applied some lubricant. I wasted no time, collapsing back onto my bed to begin pleasuring myself. I climaxed quickly just thinking about the entire exchange that had taken place. I moaned Adam's name the entire time.