Snowboarding with Best Friend Pt. 01

*All the characters in this fictional story are all in their 30s*

*Main characters*

Eddy - Male (Discreet Occasional Crossdresser), 180cm (about 5.9 ft) tall, 80kgs, gym rat. In a relationship with girlfriend.

Toro - Male, straight, 173cm (about 5.7 ft), 85kgs, gym rat. Single for 8 years. Works night shifts.

*Story begins*

My name is Eddy. I live somewhere in Asia. It was getting close to the end of the year and my best friend, Toro, wanted to learn snowboarding. I have been snowboarding for years and he's always asked him to teach him. We planned out a snowboarding trip to Japan. I've been snowboarding in Karuizawa, a small town about 4 hours away from Tokyo in car, for a few years now and stayed at the same onsen (hot spring) hotel. We booked our tickets and began planning our trip.

I've been crossdressing on and off and the only people who knew are two older woman, who I've had sex with before, in my town and one girl back home in New Zealand. It took me a lot of courage to finally tell them about my little secret and they were surprisingly very chill about it. The last time I had sex with a guy was over a year ago. I'm a very picky person and I guess that's something I embrace. I've been thirsty for cocks for months. One idea suddenly came to my mind. Why don't I tell Toro? We're very close and would almost always do things together. But I've never imagined myself with him sexually. This is when it hit me, and I started to fantasize about our trip.

I started talking to one of the older girls, who I call big sis, about the idea of telling my best friend. We talked about the possibilities of how things would turn out and whether it would totally ruin our relationship or make us closer. I decided to take a leap of faith and tell him. For some strange reason I wanted him to know this side of me.

I called him up one day during the day and told him I'm coming over to plan our trip when he gets off work at 8:30am. He lives with his family but they're all at work during the day. I grabbed my other phone I use to take pictures of my sissy self and went over. The house was empty, and we went to his room. He has a computer desk, a couch and a bed in his spacious but simple room. We quickly decided on which car to rent and some other minor details. After we were done, I went to lay down on the couch while he surfed the internet while playing some music. My heart was beating, and I was extremely nervous about coming out to him.

"Hey, you'd be my best friend no matter what, right?" I broke the silence and said.

"Huh? What do you mean?" he questioned as he kept browsing the internet.

"I have something to tell you, but I want your guarantee that you wouldn't change how you see me and still be my best friend." I said slowly.

He turned around and said "Well sure. But you must tell me what it is first, right?"

"Well... I've always liked dressing up as a girl sometimes, in my room alone of course." I slowly said without looking at him directly.

I could see a frown on his face from the corner of my eye and thought to myself that this was a bad idea.

"Wow. Seriously?" he said.

I thought the worst thing that would happen was that we would never be best friends again and decided to go all out. I picked a photo of me dressed as a girl on my phone and showed it to him.

"Wow you look good, apart from all the muscles and the belly haha." he jokingly said.

"We're bulking ok! There's not much I can do right now unless we start cutting together!" I replied harshly, feeling embarrassed. "So, are you okay with me having a dark secret like this?" I asked.

"Hey whatever gets you off! I don't mind it at all. Heck we can even go on a ride on my Ninja and show off haha." he laughed and said.

I felt a sudden relief and was so happy that he acknowledged who I was. We continued to chat for a little while before I headed home for lunch. I felt like a little girl who told her crush about her feelings.

"Should I dress up while we're in Japan?" I asked myself on the way home. "Fuck, nobody knows who we are there, why the fuck not?"

The night before our trip I packed some makeup, a wig, some lingerie, a pair of heels and some girly clothes into my suitcase and placed my normal clothing on top. I looked at my lube and condoms for 5 minutes before finally tucking them in between my clothes and closed my suitcase. I was so excited I couldn't sleep from the thought of surprising my best friend dressed as a girl. I knew we were going into the hot spring together and no clothing or swimsuit was allowed in the pool. I can see his cock!

We arrived at the airport at 7:30pm the following day. We have a tight schedule ahead of us. I told the staff at the hotel that we were going to be late but would arrive before 12 to check in. We got to the car rental store and quickly drove off in our Toyota Sienta. We made stops and switched drivers halfway and finally arrived at 11:45 to check in. It was cold and there was snow on the ground. I went into the lobby to check in while Toro unloaded our luggage from the car. Our room was in another building on the ground floor. The staff showed us to our room and gave us a quick tour around the hotel.

There's a small passage underground which leads to the main building, where the hot springs are located. He showed us our tatami room. It was spacious and comes with our own shower. The staff told us the hot spring is available from 9am to 7am the following day with 2 hours of cleaning time in the morning. He then left and we settled everything down and decided to go to the 7-11 outside of the hotel to grab some food and drinks.

We came back and thought a dip in the hot spring would help us relax and sleep better as we're not used to sleeping on tatami. We changed into our yukata, Japanese robe, provided by the hotel and headed to the hot spring area. It was getting close to 1am so we were the only ones there. We both weren't shy about stripping naked in front of another guy. The hot spring area had a dressing room with a countertop and mirrors. The hot spring was to our right, divided by a glass door covered by steam. We put our clothes into the lockers on the left and headed in. The hot spring room wasn't big, but it was enough room for at least 10 people. 6 shower heads with mirrors, buckets and shower gel and shampoo on the left side of the concealed room and the pool was on the right.

I've seen Toro's body countless times over the years, but I have never seen him completely naked. I didn't want to be too obvious about my curiosity, so I didn't look below his head. We chatted and talked about how amazing this is as we quickly showered before jumping into the pool. My heart was beating so fast by the thought of seeing his cock and I rushed into the pool to calm myself first. He stood up and started to walk towards the pool as I looked at him. I finally saw his cock.

It was soft, uncut and soft. Covered with pubic hair. They softly bounced left to right as he walked. I think he saw me looking at his cock but didn't say anything as he was filled with joy when he stepped into the hot spring pool.

"Feels amazing right?" I asked with a smile.

"It sure is!" he replied as he sat down beside me and leaned his head back with his eyes closed.

I moved up a bit to take a glance at his cock. It was floating and his cock was semi covered by his seaweed like pubic hair. I locked my eyes onto it for a good 30 seconds before hearing

"Haha what are you doing?" he asked while laughing and moved up to look at mine.

"Nothing. First time seeing you naked haha." I replied. I was afraid to ruin the vibe.

"Stand up." he said, "let's compare haha." he laughed as he stood.

I took a big breath and stood up after him. I have a 18cm cock, when hard, and I regularly shave.

"Wow you're clean!" he said "I'm guessing you're about the same size as my older brother."

"Huh?" I asked with a frown on my face.

"We used to go skinny dipping together back in Australia," he explained while laughing.

We then sat back down and enjoyed ourselves. 10 minutes later we both got up and took another shower. I wanted to take the opportunity to spice things up.

"Hey, do you mind washing my back for me?" I asked. "My girl usually does it for me but you're the only one here haha." I added.

To my surprise he was totally chill with it. He stood up and came behind me. I could see him standing right behind me and my head was blocking the view of his crotch in the mirror. He started rubbing some shower gel on my back. I closed my eyes and enjoyed the feeling of his hands on my body. He was gentle. The feeling of another man caressing my body always turns me into Charlene, my crossdressing name.

I could feel pre cum started to ooze out of my cock as I enjoyed the backrub. I then returned the favor and gave him a backrub. We quickly showered and dried ourselves before heading back to our room.

"So hey, I brought some girly clothes with me. Do you mind taking some photos for me? I've always wanted to pose in yukata." I asked as we laid down the futons, Japanese mattress for when you sleep on tatami.

"Hmm. Sure, I can try." he replied.

"Don't worry. I'll just put on a thong. Nothing crazy." I said as I pulled out a leopard skin thong from my suitcase. I put it on under my yukata and got on the futon. I told him to cut out my head as he took some photos.

"Hey why don't you show your ass?" he jokingly asked halfway through. "You've got nice ass and maybe it'll look good!"

"Why not?" I replied and pulled up my yukata to show me ass. He told me to turn around and kneel. My entire ass was showing, and it felt embarrassing but hot at the same time. Knowing him fully accepting me and now telling me how to pose was overwhelming.

Suddenly I felt a soft slap on my left butt cheek. I let out a soft moan and turned around in surprise.

"I couldn't help myself haha. Sorry." he said while laughing and went back to taking photos.

"I kind of liked that. Do that to the other cheek!" I asked him. "But a bit harder?"

He stood up and gave my right cheek a harder slap. It turned me on so much. I was drooling in my thong. I was super wet. I don't get hard when I'm with a guy, but I get wet extremely easily and stay soft.

We finished our shooting session 5 minutes later and got into our futons. We chatted for a little bit and went to sleep soon.

We woke up at 6am to get ready for snowboarding the next day. It's like last night never happened and we carried on the day normally. I taught him how to snowboard and the entire day was him falling, getting back up to immediately fall again 5 seconds later. We had fun but were both exhausted by the time we left the ski field.

We had dinner and some sake before heading back to the hotel. We bought some liquor on the way back and decided to drink in our room later. We returned to our room at 8pm. Both exhausted, we decided to take a shower in our room and start drinking. I showered first and quickly, knowing Toro is always slow in the shower. I finished showering in less than a minute and spent the next 5 minutes cleaning my bowel with the showerhead. Not sure what I was expecting but I want to be ready for anything and everything.

I got out with a towel wrapped around my body and Toro got in right after. I started putting some makeup on as soon as he closed the shower door. I wanted to surprise him.

I put on my foundation and smokey eye shadows. Applied some powder before putting on mascara and lipsticks. I turned to my suitcase and pulled out my lingerie and my black nylon stocking. They were black with laces all around them and a see-through cup on the bra to show my dark pink nipples. I then put on my shoulder length blonde wig and put on my yukata before closing my suitcase. I slightly dimmed the lights and sat down at the kotatsu, Japanese heating table with blankets on the side to keep the heat in and prepared our drinks.

Toro came out 3 minutes later in his yukata with his chest showing. He was humming a song as he got out but stopped as soon as he saw what was in front of him. He was surprised.

There I was, sitting in my yukata dressed like a girl, waiting for him to join me.

"Waddya think?" I smiled and asked him in a girly voice.

He froze for a few seconds and replied "You look better than the photos. I'm surprised that you'd look so much like a girl."

"Aw thank you!" I replied with a big smile and added "Come! Let's drink!"

He sat down on the opposite side of the kotatsu and moved his legs into the blanket. Our legs touched and he said, with his eyes wide open "Stockings too?"

I giggled and continued to open our drinks and poured for the both of us. We started chatting and joking like normal. Every so often I would intentionally brush my feet around his legs, acting like it wasn't intentional of course. I started to feel hot from the heat and the drinks, so I pulled open my yukata just enough to let out some heat while slightly exposing my lingerie. Toro and I are both lightweight when it comes to alcohol, and we were tipsy. I took out my Bluetooth speaker and put on some soft music. I specifically searched for 'Erotic bed music'.

Under intoxication of alcohol, I started to let go of myself and let Charlene take over. I started to caress his legs with mine while looking at him. My eyes were filled with lust. I was seducing my best friend. I slowly made my way up his legs towards his crotch. He got spooked and pulled back a little bit.

"Hey don't overthink." I said softly, "Just enjoy the moment."

"I don't know about this." he said, "I'm sorry but I'm straight and you know that."

"Close your eyes then, I want you to enjoy the moment." I said, "Just let loose and let things happen, Toro."

He took a big sip of beer and closed his eyes. I knew I had him. I moved my feet up further and arrived at his cock. He was hard already. "Cheeky bugger." I thought to myself. I started caressing his hard cock with my nylon feet. Soft and gentle I moved up and down before "grabbing" his cock with both of my feet. His breathing became deeper, and he started to softly moan. His pre cum was so much that it made my stockings wet.

I knew it was time to take it to the next stage. I got up and sat next to him. He wiggled a bit to the side to let me fit into the blanket. I reached down to grab his hard cock as he kept his eyes closed. It was bigger than I thought and drenched in pre cum. I slowly stroked his cock in the blanket as he moaned.

I moved my mouth next to his ear and started blowing air into it softly. "You like this?" I whispered.

He nodded and didn't say anything. I told him to move back out of the kotatsu. He moved back and sat on his futon with his legs open and his hard cock protruded out of the yukata. I finally saw his cock hard. It looked like his head was going to pop out of his foreskin but needed a little help. I gently pulled the foreskin down and he moaned as I did. Soon his red cock head was out of its shell. Pre cum constantly flowing out of his head. I started fondling his cock head with my fingers while blowing air into his ear.

"Do you mind if I use my mouth?" I softly asked him for permission.

He took a big swallow and nodded, giving me green light. He then moved to lay down on his futon. I went down to kneel in front of him with my ass high in the air. I started sucking on his cock. It was so hot and wet. His pre cum was sweet. I licked his cock up and down to savor all his pre cum. I took a deep breath and took his meat completely into my mouth. He let out a big moan as I did. I started moving my head up and down while my hands caressed his body. Occasionally I would look up to see his reaction as I sucked him harder and harder.

"I haven't had my cock sucked in 9 years." he mumbled. I looked up and saw he was looking at me. We locked eyes with each other. This time his eyes were filled with lust, too. He was checking me out. I pulled down my yukata slightly to reveal my thong and my big ass. He was in awe.

"You can call me by my girl's name, Charlene." I said.

"Ok Charlene." he replied while still locked onto my ass. I got up and slowly walked to my suitcase. I took off my yukata as I bent down to open my suitcase, showing him my body as a girl. I took out the lube and condoms then walked back to his futon.

"When was the last time you fucked?" I asked him with a cheeky smile.

"Uh. A long time ago." he replied shyly. "I don't know if I can do this."

"Don't think about it." I replied and guided him to lay back down. "Just close your eyes and enjoy." I whispered into his ear.

I put the condom in my mouth and put it on his cock. I then applied a lot of lube on it. Finally, I got on top of him. I took a second to recollect myself. I'm about to fuck my best friend. This turned me on so much. I grabbed his cock and placed it at my pussy.

"You ready?" I asked while playing with his nipple.

He nodded. Eyes closed and arms laid down on the futon.

I slowly sat down. His cock was entering my pussy. We both moaned at the same time. I continued to swallow his cock with my boy-pussy until it was all the way in. I haven't had sex with a guy in a long time too, so I had to take a minute to ease the pain.

Slowly pain turned into pleasure as I moved my hips up and down. In no time I started bouncing on his cock. It was so hard and hot. I felt like he was going to melt my pussy with his cock. The sound of his hips hitting my ass was louder than the music and the entire room was filled with the noise.

I started to moan like a girl. My cock got hard, and I started to drench his belly with my pre cum. Suddenly he opened his eyes and grabbed my butt. We locked eyes as he thrusts his cock in and out of my boy-pussy with my hard cock bouncing around drooling pre cum all over his body.

No words were said but we understood each other. I continued to ride him for 5 minutes.

"You're gonna make me cum soon, you're so tight." he said.

"Cum for me. Go faster and harder." I looked at him and commanded.

He started fucking me harder and harder and I felt his cock tense up. "I'm cumming!" he yelled.

"Me too!" I moaned. I closed my eyes and leaned back. As I felt the pulse of his cock in my pussy, shooting his hot load into the condom inside me, I came on his belly. We stayed in this position for a second, savoring the feeling.

"That was amazing." I said and gave him a kiss on the cheek then ran off into the bathroom to clean myself.

*End of part 1*

*Please comment and tell me how you feel about the story. Your appreciation means a lot to me as a creator and helps me create more work like this. xoxo*