Alana's Journey

Author's Note: After all the nice comments from the 5 chapters of The Poker Game, I wanted to write something for all the people who have wanted a character to have more involved in their transition. Once again this takes place in Fantasyland.

This story will focus on the journey from Alan to Alana with her as the main character. It can probably be read as a standalone, but you'll probably enjoy it more if you read The Poker Game chapters. I did my best to make sure the timelines from the first stories blended with this one.

I try to be a stickler for spelling, grammar, and continuity. I hate using the same adjective twice in a short span. Actually if anyone can help me with a synonym for moaning, I'd appreciate it. There's way too much moaning going on and everything in the thesaurus suggests a word that means a complaint instead of pleasure.

Anyway I hope you enjoy this one!

Alana's Journey -- The Poker Game Saga

It all started when I came home from school and there was a laundry basket in my room. Who knew at the time that the freshly washed clothes would change my life forever!

My mom was nice enough to do my laundry, but she never folded it. I changed out of my school clothes into a t-shirt and shorts. Then I dumped the basket on my bed and started folding. I folded some t-shirts and then onto boxers. My boxers were all black cotton. I was halfway through the pile and I saw a hint of pink, a color I would learn to love!

I reached to see what the pink thing was doing in my laundry, because I didn't own anything in that color. My hand touched the softest material I had ever felt and I picked the item up. It was a pair of my sister's black panties with a pink bow in the center of the waistband. I would later find out they were called boyshorts and I had occasionally seen my sister wear ones like that.

My sister Victoria was a year older, but we had a very similar body type. She always liked to show off her body, forcing my mom to yell at her to put on some clothes when she would walk around the house in a t-shirt with no bra and panties. Victoria was a very pretty girl with very pretty friends. I always wished I would end up dating one of them, but anytime I mentioned it, Vicky would call me a name and tell me there was no shot.

So I was running my fingers over my sister's panties. They really felt amazing. As I was stroking them in between my thumb and index finger I was hit with a dilemma about what to do. If I gave them back I knew she was gonna accuse me of stealing them. That would lead to more names, she would probably tell her friends I had some sort of panty fetish and then I would really have no chance with them. I decided to fold the panties and put them at the bottom of my drawer underneath my boxers. Vicky had so much clothing she would never realize.

My family was, for lack of a better term, rich. Actually my Mom's parents were. I never got the full story, but it had something to do with oil and gold. Anyway we were well off, but my parents didn't let it go to our heads. My sister and I had to earn every cent they gave us with good schoolwork and chores. I spent my money on video games and hanging out with friends and Vicky spent her money on clothing and shoes.

A few weeks had gone by and I had forgotten about the panties in my underwear drawer. I was getting dressed for school and I grabbed my last pair of boxers. Staring at me in the face was the pair of black boyshorts with the pink bow. I ran my fingers over them and for the first time chills ran up my spine. I was running late so I got dressed quickly and went to school.

All day I couldn't get the panties out of my head. I thought about my sister walking around the house wearing them and I thought about her hot friends and what kinds of panties they wore. This led to some unfortunate erections that I had to hide.

The second I got home I ran to my room to open my drawer. I grabbed the panties and went into the bathroom that was attached to my bedroom. I quickly stripped naked and pulled the panties up my legs. The material felt amazing as it touched my body. I never had a lot of body hair and I bet that was why they felt so good. I was hard already from fantasizing all day, but if it's possible I got even harder, and there was no way my dick was fitting inside the boyshorts. That didn't matter much, because of what I had planned.

I stared at myself in the mirror and felt ashamed. I was wearing my sister's underwear and about to jerkoff. Then I stroked the material and ran my thumb over the pink bow. My dick throbbed. I thought screw her. With all the teasing she put me through, I could at least enjoy myself at her expense. She would probably go crazy if she knew what I was doing.

I reached down and stroked my dick. A small drop of precum dripped out and I was off to the races. I looked at myself in the mirror and focused on the panties as I masturbated. I was tugging with my left hand and I moved my right and up and began to rub my nipple. I had never done that before, but in my current situation it seemed right. My nipple was hard and I felt a jolt go through my body the second I touched it. I immediately blew a load into my sink, luckily keeping my panties clean. They were mine now!

My underwear drawer was refilled with newly cleaned boxers and the panties went back to their usual spot. I was still a little embarrassed about what I did with them, so I tried to forget. Then a few weeks later I was low on underwear again and there were the panties. My mom and sister were going shopping after school for a prom dress so I would have the whole house to myself.

All day I was thinking about what I would do when I got home and if I wanted to explore a little more. I got home to my empty house and put on my panties. My hand subconsciously went right to my nipple and I had an idea. What would it feel like if they were covered?

I went into my sister's room and opened her dresser. The first drawer had panties, probably about 30 pairs. No wonder she didn't miss the ones I was wearing. Next I opened her bra drawer and there were just as many in there. I didn't think Vicky had huge boobs, but on that day I learned she had a C cup. Not wanting her to think one was missing, I found a black bra at the bottom with a pink bow in between the cups. A perfect match!

I looked at my watch and saw I had plenty of time before they got back. I was ready to go have my fun, and I don't know what made me do it, but I opened her bottom drawer. My eyes were hit with a color splash of lace. The drawer had stockings, garters, and nighties. As I liked to do I stroked the material and felt everything. Then I felt something hard. I had no choice but to continue looking.

I grabbed the object and picked it up. It was a replica of a penis, a big one! My sister had a dildo in her drawer! I stroked the shaft and immediately knew it was larger than I was packing. My mind went to what my sister was probably doing with it and I quickly put it away. I checked the three drawers to make sure they were the way she left them and I went back to my bathroom with my new bra.

I stood in front of my mirror in my panties with my hard nipples. I felt a twinge of being ashamed again, but my excitement took over. I covered my chest with the cups, put my arms through the straps, and after a couple tries I was able to clasp the hooks behind my back. I would later learn the trick of hooking it and then spinning it around.

I checked myself out and I didn't think I looked ridiculous. I mean I looked like a dude in bra and panties, but from the neck down if I had some boobies I wouldn't be half bad. I checked my watch again and made myself cum before everyone got back. My bra joined my panties in the bottom of my drawer.

I continued to play with myself anytime I had the house to myself. It became much easier when Vicky went off to college that fall. Not only that, but all the clothes she left behind were available to me.

One day I was going through her drawers and I touched the dildo again. I started to wonder about it and if there was anything I could do with it. I did my best to ignore the places it may have been as I started to stroke it. Then I brought it to my lips and I kissed the head. It was just a piece of rubber, but it was the hottest thing I had ever done. That was good enough for that day and I put it away before going back to the bathroom to jerkoff.

I added playing with the dildo to my masturbation activities. I would put it on the bathroom counter, bend down and suck it while I jerked off. I had never considered that I might like to suck on a real penis though. I was just enjoying myself and I would worry about the future later.

My routine was interrupted when winter break hit and my sister was home from college for a month. I would have to be extra careful. There was no way I was going to risk playing with the dildo. Getting caught with that would be way too embarrassing to recover from, plus I'm sure she would be embarrassed too if my mom found out that she had it. Sure she teased me and I had been invading her privacy for months, but I really loved my sister and I was sure she loved me.

One morning I was woken up by the sunlight entering my room. I was really horny and I had to do something about it. I checked my phone and there was a text:

-Hi Honey, Aunt May was in a car accident and was sent to the hospital. Vicky and I are headed over there. She sounds okay, just a little scared. We'll probably be there all day. Love, Mom.

I hope Aunt May is okay, I thought, but then I selfishly thought about myself.

"Yes, I have the house to myself!" I said out loud to no one.

I texted my Mom to check in and she confirmed that it was probably just a concussion and whiplash. They would be spending the day at the hospital until they gave the okay to bring Aunt May home. She said she would text me when she was on the way home. Wow, the house to myself and a warning when to stop messing around! Other than my Aunt getting a little banged up, this was turning into a great day.

I went right into Vicky's room and started to search. With all the time in the world I was really gonna have some fun! I was tired of just having a touch of pink on my black lingerie and wanted to go for the whole thing. I picked out a pink thong and matching pink bra. I never wore a thong before and it was the perfect time to try one. I had become and expert at putting on a bra by now and the feeling of the string going in between my cheeks made me question why I didn't try a thong sooner.

Since I was in exploring mode I opened the closet. Vicky had tons of dresses and skirts to go with her casual clothes. I didn't think I was ready for those and there was a good chance I would have an accident on one of them that would be hard to clean. I was about to give up when I looked on the top shelf. I saw a bit of hair and then I remembered that Vicky had worn a blonde wig one Halloween when she had cut her hair too short. It looked just like her normal hair now. I put on the wig and grabbed the dildo.

I was so worked up I decided not to go to my room. I was gonna do it right here. I had plenty of time to clean up if I needed to. I stood the dildo up on her makeup table.

I said, "Alexa, play, Cyndi Lauper- Girl's Just Want to Have Fun!"

The song started to play through Vicky's Amazon device and I bent down to start sucking the dildo. I didn't want to cum right away so I worked on the fake penis before I started to rub my real one. My concentration was broken when I felt a huge slap on my ass.

"Yeah! Work that cock! God I missed this ass so much!" A male voice said.

I froze and wondered what was going on. Who was in the room with me and who just spanked me?

"Damn Vicky you are so hot. You could've waited for me though. I would've texted you, but my phone blew up. I'm happy you told me where the secret key way," he said.

Holy shit! It was Vicky's boyfriend Doug. He thinks I'm her. I'm so fucked.

"Vick?" Doug said, "You can stop playing with that. The real thing is here."

I had no choice. I let the dildo slide out of my mouth and I turned around in shame. Doug did a double take as he looked me up and down. My lack of tits and erect penis sticking out of my waistband was a dead giveaway.

"Alan? Is that you? Holy Fuck! What the hell are you doing?" He asked.

"I don't know," I said.

"It looks like you put on your sister's underwear and are sucking on her toy," he said.

"Um," I said, speechless.

"Do you do this all the time?" He asked.

"I don't know," I said.

"I had no idea. I thought you liked girls. Vicky is always telling me that you want to go out with one of her friends," he said.

"I do," I said.

"Dressed like that?" He asked.

"I don't know," I said.

"Did you like sucking on that fake dick?" He asked.

"I don't know," I said.

"Seems like there is a lot you don't know. Maybe I can help you," he said.

Doug unbuckled his belt and dropped his pants and boxers. His hard dick popped out. I stared at it.

"Does this help?" he asked.

My jaw dropped as I checked out his dick. It looked familiar. How could it? I've never seen another man's dick before, let alone his. I inadvertently licked my lips.

"Look familiar?" He asked.

"Yeah," I said, "How?"

"It's the same one you were just sucking on," he said.

"What?" I asked.

"I had a replica made of my dick for your sister as a graduation present. She was supposed to take it to college to use when she missed me. I guess she forgot to take it," he said.

"You mean this is the same as yours?" I asked.

"You know what replica means, right? It's the exact size and shape," he said.

"But how?" I asked.

"They make a do-it-yourself kit," he said.

"Oh," I asked.

"As you can see I'm all boned up. Any interest in trying the real thing?" He asked.

There it was. A man was asking me to suck his dick. Not only a man, my sister's boyfriend.

"I don't know," I said.

"I think you do. I saw you lick your lips, Alana," he said, giving me a girl's name for the first time.

"But Vicky," I said.

"She doesn't need to know. Just like I don't have to tell her you dress up in her underwear and play with her toys," he said.

He had me. It wasn't quite blackmail, but I didn't think I had a choice.

"This stays between us?" I asked.

"Scout's honor," he said.

"And you'll be gentle, let me do it at my own pace? I've never done that before," I asked.

"You looked like a pro when I walked in on you!" He said.

"Doug!" I said.

"I'm sorry, as long as you put my dick in your mouth and suck it, you can do it however you want. In fact I'll sit on the bed and put my hands behind my head," he said.

"Okay," I said timidly.

"Nice!" He said.

He sat his bare ass on my sister's bed and looked at me. I walked over and dropped to my knees. Was I was really going to do this? I stared at his red swollen head and saw a glistening spot of precum. I licked it off. I had tried mine many times and it tasted about the same.

"Mmmm, thatta girl!" He said.

His encouragement was nice and I decided to just go for it. I opened my mouth and took his head inside. The second I closed my lips I knew this was totally different. While the dildo was rubbery and cold, his dick was hard as a rock and warm. I hadn't even started yet and this was already better.

I moved my mouth deeper as I gave my first blowjob. He had a big dick, but I knew it well from the dildo. Without all my practice there was no way I could've done this. I was sucking and tonguing his dick as he moaned. That was another difference between pleasuring a real man and an inanimate object.

My first attempt at oral sex only lasted about five minutes. Being a total rookie from both sides, I had never been blown either, so I didn't consider how it would end. I was focusing on making him feel good and another difference popped up. His dick started to get bigger in my mouth. I should've known what was about to happen as this had happened to me multiple times while I was jerking off. Instead of stopping or looking up for guidance, I just sucked harder and faster.

"Ohhhh so good! I'm gonna cum!" He yelled out.

Oh shit! He's gonna cum in my mouth! I tried to loosen my jaw and pull back when I felt a warm splash coat my tongue. It tasted nice and I reflexively swallowed it. The next spurt hit and I was felt guilty. My sister's boyfriend was cumming in my mouth. I was supposed to be getting blowjobs not giving them! I tried to pull my head off him completely. I had to get out of there. Doug had other ideas. As I reached the tip I felt a hand on the back of my head, pushing me forward.

"Not so fast," he said, "Finish what you started Alana! Don't you want your treat?"

"Mmmmm," I groaned.

Of course I couldn't answer with his huge dick in my mouth and it probably sounded like I was agreeing. He took my mumble as a yes and held me in place until I swallowed every drop. When he finally slipped out of my mouth I was mortified.

"That was amazing Alana!" He said. "Are you sure that was your first time?"

"I...I..." I stuttered, "I've gotta go!"

I ran out of the room and into my bedroom, slamming the door. I went into my bathroom and gargled with Listerine. I couldn't believe I just did that! I looked at my reflection. I was wearing a blonde wig, and my sister's pink bra and panties. There was a huge wet spot in the middle of my crotch. I reached down and felt the sticky substance. Holy crap, I came from giving a blowjob and didn't even notice!

I was startled from a knock on my door.

"Alana, are you okay?" Doug yelled.

"Please just leave!" I said.

"Okay. I just wanted to say thanks." he said.

"Please just go!" I said.

"Okay," he said.

I waited to hear the back door close and then the sound of Doug's pickup truck's engine starting. I stripped out of my lingerie and got the black bra and boyshorts from my drawer. I put them all in a garbage bag.

Next I got dressed in my normal clothes. I put the wig back in my sister's room, since that would be the thing she would notice was missing. I did a quick sweep for evidence and made sure everything was exactly as she left it. I couldn't tell if the room smelt of sex, so I picked up one of her perfume bottles and sprayed the room. I drove to the back of our local supermarket and threw the bag in the dumpster. I was done with this part of my life...or so I thought.

Two years had gone by since my morning with Doug. I hadn't thought about it or my lingerie fetish at all. Then I met Kelly. Kelly was a hot girl, hotter than I ever thought I would get. My friends joked that she was only with me because I had money. My response was along the lines of, who gives a shit!

I had a great time with Kelly. It was even better because my roommate was expelled for cheating and I had the dorm room all to myself. She gave me my first blowjob and it felt amazing. I went down on her and she finally let me fuck her. I lied and was embarrassed to tell her it was my first time. After that things got a little kinky. She wanted me to handcuff her one time and another she wanted me to spank her. She thanked me for helping her fulfill her fantasies and begged me to tell her mine. I told her I didn't have any and that being with her was good enough.

"Come on Alan, tell me what you want," Kelly said, "I'll probably do it."

"There's nothing I want, I'm happy with everything the way it is," I said.

"There has to be something? Sex in public? A threesome? What guy hasn't fantasized about two girls at once?" She asked.

"Not me, I just want you," I said.

"Bullshit!" She said. "Tell me something."

She finally got me to cave and I couldn't believe the words came out of my mouth. Doug was the only one who knew my secret and she was about to.