tagTranssexuals & CrossdressersChanging Room Prank Ch. 05

Changing Room Prank Ch. 05


I know it may have been some time since the last chapter, so if you've forgotten some of the story or if you're just jumping into the series, I'll give you a quick summary. In chapter 1, Alice began her journey as a cross dresser after what was initially a simple prank turned a platonic sleepover into 3 way for her and her friends. During the date however she met a classmate who was clueless to her true identity. In this chapter they go on their first date. In the other chapters Alice reconnects with her friends and struggles with her sexuality and new persona. She is constantly developing herself so if you read these for the plot, you might want to read the preceding chapters to fully understand the writing. As for the few but inspiring dedicated fans, the pleas to write more do not go unheard; I read all of your fantastic comments!


The week came and went and Kenny was still texting Alice with much enthusiasm. He no longer needed Ethan's help, though, and we weren't talking as much now. I wanted to know if he was excited or scared, or if he was going to try and make a move on Alice, but he wouldn't divulge too much information any more. Before, he would rush to me with every new text and consult me. I would practically write the entire conversation as I was texting for Alice too. I found the coincidence funny but there was no one I could tell. Now, though, Kenny would barely tell me if he even texted Alice that day. I knew he did, obviously, but I wanted to know what he was thinking and what he was planning. Unfortunately, I had to wait for Friday, when he planned our date.

While Kenny and I were growing apart, Greg was mirroring his behavior and started to border on ignoring me. I couldn't blame him, though: the last real conversation we had ended when I stormed off his porch after he kissed me as Ethan, not Alice. I was almost outraged that he had tried this, but after only a little bit of reflection, I realized how much I was overreacting. I had never told Greg that I wanted to be his friend as Ethan and much more as Alice. He was confused when I pushed him off, and when he called me Alice casually he thought he was just flirting, but he didn't realize the significance it had.

To me, it seemed like the entire persona of Alice was nothing to Greg, and he was just another horny teen looking for the next place to stick it in, but I knew he was so much more than what I gave him credit for. He cooked meals for me, he took me on dates, he held doors for me, and when we had sex, we made love. Greg was a lover and took nothing more than he gave. I was lucky to have him. I was really lucky to get any guy. I don't think anyone else in my class would be OK with Alice. I forgot how much I should be thankful for Mark as well.

Maybe Mark didn't just ask for a blowjob whenever he felt horny: maybe he knew that it made me feel like a woman. This was a stretch, but it was still a possibility. I remember the first time he saw me dressed on my own. He called me Alice, and he said she was beautiful, and when I told him I wanted to be a girl, he assumed his position as a man. He told me I had to please my man. Was this him being horny, him wanting to help me realize who I was, or a little of both. I hoped it was the latter, or was all that just a lie so he could fuck me? I hadn't considered it before. I quickly shook out those thoughts. Mark wouldn't have created that elaborate plan just for an orgasm: I convinced myself then that Mark cared about me, but I was going to have to see in the days to come how he really felt about me.


The date night approached, and I started to stress about what I was going to wear. It was early in the week, but I was already worried about my very limited wardrobe. I couldn't make any excuses to get out of the house during the week and getting Alice's clothes in through the front door was always a very tense time, so I decided to order them online. I began browsing for casual dresses then got carried away and started gazing upon gowns and party dresses. I remembered what I was doing then got back to it. I ordered a modest floral dress and large purple belt to match the flowers on my dress.

I decided that I should order some shoes to go with my outfit, and then I went down a slippery slope of online shopping. I ordered a pair of light purple pumps, and then I got really adventurous. I added stockings and a garter belt to my personal collection as well as a black g-string and a petite black satin nightie. I knew that I wasn't going to let Kenny get anywhere near the stage where I invited him in to see my underwear, but I was fantasizing, and I didn't want to stop. Then, I took another big step and decided to order a bright pink vibrator. I felt so naughty doing it, but I couldn't stop anticipating its arrival even though I had just ordered it.

With my outfit sorted, I was finally able to relax and take care of the erect dick in my pants. I hadn't cum since I was at Greg's, so I was expecting to get off quite quickly. I got started with my usual routine by loading up a video on the internet and then pulling my pants down, but for some reason, I couldn't climax. I sat there masturbating, but it just felt like something was missing. Dismayed and shocked, I gave up after a few near-climax moments, feeling they were enough for tonight.


Friday came around and I was taking books out of my locker when Kenny walked joyfully down to me and stopped, leaning against my locker with a smile.

"You did it! The date is tonight, and I can't thank you enough for your help. "

"Thanks, but I just helped you get what was in your heart onto the screen, you did it too."

Kenny blushed, "That's it, thank you so much again, any more great advice for tonight? Do you know what Alice might be expecting?"

Of course I did, I knew exactly what Alice wanted. It was almost too easy. I told Kenny what cologne to wear, and what kind of shirt he should wear for tonight. I wanted go on and describe to him everything I wanted to see in a man, but if I had gone any further, I would have sounded like a stalker. As far as Kenny knew, I had never even met this girl, and I was already prepared to tell him all about the way she cut her sandwiches! He thanked me for the cologne suggestion, but questioned my decision to go with a collared shirt. I told him it would be an evening date, and she would expect it, but he just told me he would consider it. "Fine, I guess we'll just have to see what Alice thinks," I thought. It was too easy to be right. The bell rang and we both went to our classes, and I never got the time to meet up with Kenny again, but a few hours longer to wait wouldn't be a tragedy.

I went home and started my transformation into Alice. First, I got in the shower and began slathering my legs, arms, and anywhere that needed it with shaving cream. Luckily, as far as hair went, my face wasn't an issue. I had barely managed to grow some lip fuzz over the course of a month a couple months back, so facial hair would not be a problem in my transformation.

As I finished the last stroke on my leg, I smiled and reached down to feel the smoothness of my legs. It was nothing new, but it felt so feminine and was a symbolic process for me. It was also, as usual, an arousing experience. The stroking of my soft legs got me in the mood, but again, for some reason, I couldn't climax. The shower had a track record of housing some of my most explosive orgasms ever, but this time it failed me. It still felt like there was something else I needed and this missing piece wouldn't let me cum until I found it. I rinsed off.

I took out my newly acquired makeup kit, and with the help of some online tutorials, I began applying it. I was proud of myself after I had finished. I had been getting better after practice, but this look was almost professional: it was like it was something I'd been doing all my life. I slipped on my underwear and bra, and tucked loose ends into their place. I was walking out of the bedroom when I heard the doorbell ring.

I looked outside and saw a mailman's truck. Startled, I rushed to put on my guy clothes to answer the door, but I suddenly remembered my make-up. Even if I had wanted to take it off, I wouldn't have enough time; these mailmen didn't wait very long. I threw off Ethan's shorts I was putting on and grabbed the red blouse I had grown so attached to. I heard more knocking this time, and louder, as I was doing the buttons on my blouse. I was only a little more than halfway buttoned up when he knocked and yelled, "Anybody home? I'm about to take off now." I raced down the stairs still only wearing nothing but my panties from my waist down.

I flung open the door and exclaimed "I'm here, wait!"

The mailman almost dropped his jaw. "Um, p- package for Alice Johnson." He was stumbling over his words at seeing me. There I was in panties and a bra, with a blouse that was buttoned barely enough to cover my stomach. It must have been straight out of a porno!

"I'll sign." I took the clipboard from his hand and gave him my signature. I handed him back the clipboard but he didn't move. "Excuse me?" No response. I assumed that all the blood in his brain had gone south. "Can I have your package now?"

"What?" He looked shocked, and I had expected that. I chose my words carefully, just enough to be flirtatious but also casual.

"The box under your arm. I think that's for me?"

"Of course, sorry." He was brought back to reality and handed me the package. I thanked him, then closed the door. I could tell the makeup had done its trick.

I went upstairs and emptied the contents of the package on my bed. I took the dress belt out first and laid everything out on the bed. Then, I pulled out my light purple shoes with a modest but tricky heel. Next I took out the unmentionables and set them on the bed too. Then, beneath all the clothes, I suddenly remembered the toy I purchased all those nights ago, the pink vibrator. It was bigger than expected; I estimated it to be about 9 inches. I grasped it and held it for a while, before hiding it in a box under my bed. I put on the garter belt, then the stockings, rolling them up my legs. It gave them a lovely curve and elegance. Then I slipped into the floral dress and fixed on my belt. I sat down on the bed to adjust my shoes, and then took a step in front of the mirror. Staring back at me was a girl ready for an evening out with a handsome companion. I hoped Kenny was putting in half as much effort, but that was unlikely.

When the time came for the date, I went downstairs for a quick drink to calm down, but unfortunately I was interrupted by the doorbell yet again. Kenny was there waiting for me. I opened the door and greeted him with a hug.

"Hi, how have you been?" I asked gleefully while releasing my arms from around his shoulders.

"Fine, and you? You look great, by the way. I feel a bit underdressed now,"

"Thank you, I've been looking forward to this date all week."

"You don't think I look underdressed?" Kenny asked nervously.

"Maybe just a little, but it's fine. I love your cologne, though, you smell great." Hopefully now Kenny would take my advice more carefully.

We continued the meaningless small talk to his car and talked about our weeks during the drive. When we got out of the car, the first thing that I noticed was the smell. Even though I couldn't see it, the smell of salt sea told me we were at the marina.

He went around the car and opened the door for me. He held out his hand and helped me out of his car. I abruptly got up and nearly fell over, as it was one of the first times I had ever worn high heels, but Kenny caught me. Although when he did, he may have been trying to sneak a feel of breasts, which was worrying for me, seeing how I had stuffed my bra with tissues. I got my balance back and we began to walk down the boardwalk together. It was still light out and quite warm, but there was a gentle breeze that would occasionally blow my dress up a little, causing me to force it back down and blush in the process. Kenny just laughed along with it and took my hand.

We continued down the boardwalk until we got to the restaurant where Kenny had reserved a spot. When we walked in, I saw him slip the waiter a bribe and whisper something into his ear. I couldn't tell what he said, but I'm assuming it's what helped us get the most desired table in house, right by the window, with a perfect view of the sea. We ordered our food and chatted nonstop until it came. We talked about anything that came into our minds. Whilst I was rambling on about something that probably had no point or interest at all, Kenny sat and admired everything I did. What I had to say wasn't important, but Kenny would have watched me go on and on forever. Alice may have only known Kenny for a week, over text, but I felt we could tell each other anything, and I almost did. During another one of my stories, I casually mentioned urinals in the bathroom and, as if that wasn't enough, the ending would be a dead giveaway as to my gender.

"Why were there urinals in the girls' bathroom?" he asked. He sat up and looked at me with a quizzical look.

"Oh, we were in the boys' bathroom," I lied.

"What were you doing in there?"

"That's where Mar-," I elongated the 'r', stalling to think of a girl's name in place of Mark's. "-rrla, Marla, decided it would be best." I cringed internally at that, and I immediately cursed myself. Couldn't I think of anything better?

"OK, then," Kenny was still unsure about the semantics of this story, but that wasn't important to him. I finished my story rather hastily, and left many unanswered questions, but I quickly changed the topic.

The sun was going down, and the light was escaping us. Kenny signaled for the waiter to come and the attendant lit the candle for us.

"Oh, romantic," I giggled.

"I just want everything to be perfect for you," Kenny and I locked eyes across the table. He put his hand on mine. My heart was racing. I responded by slowly and softly brushing my foot against his calf. "Wanna get out of here?" I nodded at him and this prompted Kenny to ask for the check and quickly pay. We walked out of the restaurant, hand in hand, and strolled down the boardwalk once again. We walked by the water and past the closing vendors. There were still street performers out, though, only now their music was soft and serene. The temperature had dropped a little while we ate, and I never noticed how little women had to keep themselves warm with. I shivered at the sense of a cool sea breeze passing by my bare skin on my arms and legs.

"You're cold, aren't you?" Kenny asked.

"It's just the wind," I replied.

"Here, you've got nothing to cover yourself with," He took off his coat and placed it over my shoulders. Everything felt so right at the moment, the sun was setting over the waves, there was the pleasant drone of a violin in the background, and Kenny had just shown me how selfless he could be, as he had been doing during the whole evening. I leaned up on my toes and placed my lips gently on his. I came back down on my heels and Kenny smiled at me. He was nothing but content. The coat fell on my shoulders and he put his hands around my back. We stood there in close conditions with our foreheads gently touching each others. I grabbed his shirt just below the pockets and pulled Kenny's body closer to mine. We kissed again, and Kenny pulled me in as well. The moment was straight out of movie or from a dream of mine.

Our kiss progressed and opened my mouth just a little to let his tongue only just enter. We Frenched under the setting sun and I threw my arms around his neck. I was elated, and couldn't describe the feeling I had. I loved the way he always opened doors for me, and I loved the way held my hand when we walked, and I loved this kiss, but could what I felt for Kenny be love? I had known him for a couple of years, but that was as Ethan. I had known him as Alice for only a week or two, and already I felt loved by this man like no one else has. I know it was terrible of me to do so, since I had had such a great time with Greg last week, but it felt so right. I didn't want to complicate things now, so I pushed all that aside and fell back into the experience. We were like that until the sun was finally out of sight.

When it did start to get too dark, we walked back to Kenny's car. We sped off down the road, but he missed the turn back to my house.

"Where are we going?" I asked. I could tell where this was headed.

"I know a place around here with a great overlooking view of the city. It's also very secluded." I was almost sure I knew what he was talking about. "It's called Dawson's Ridge," he said, confirming what I was speculating. It was a quintessential hookup place for kids in the area. Many of my friends have bragged about getting laid up there and how easy girls get with a great view and a little alcohol. "Ever heard of it?"

"Yeah," I replied almost unenthusiastically. I turned to look out the window. Here I was, driving in a decent car, to a romantic setting with a very handsome man. It was the perfect high school love story, but I wasn't the perfect high school girl. Maybe in Kenny's eyes I was, but there was the one little issue under my dress that he still didn't know about. I was going to have to do something before it got too serious.

When we arrived, the view was no less than everyone had made it out to be. I could see for miles, and the town looked so pretty on a clear spring night. "Alice, I just want to tell you that this was the greatest day of my life because of you, and I really loved spending time with you."

"Thanks, I feel the same way. This has been an amazing date so far and I can't thank you enough."

"My pleasure," he said. "You know, you look beautiful under the moonlight." We locked eyes yet again and we both moved are heads closer together until we were back to where we had stopped on the boardwalk. "This is fine, just a little kissing," I thought, but how far would it go? He put his hand on my thigh but I brought it back to my waist instead. I didn't want to discourage Kenny because I did want this, but I had to, or else he would get a possibly nasty surprise. To compensate, I put my hand on his thigh and slowly moved up until I felt his throbbing cock in his pants. They were tight pants, but Kenny was definitely excited. I massaged his crotch over the pants. I knew it what it might lead to, but I kept doing it anyway. I wanted to show him that I wanted to do this too, and I wanted so much to please him, but I just couldn't go that far. He put his hand back on my thigh, and then I broke the kiss and brought my hand back to my lap.

"I'm sorry, I can't do this."

"It's fine, we can take it slower if you want," he desperately answered.

"No, it's not that. I really like you and I want to do this, but I just can't, I'm so sorry."

"That's fine, I guess." Kenny slumped back into his seat. I awkwardly glanced around the car. "You're right, though, maybe not on our first date. I mean, we've only known each other for a couple weeks." I smiled weakly back at him. At least he was trying to be understanding about it.

He drove me home with little conversation between us. I didn't want such a perfect night to end this way. When we arrived at my house, he again opened the door for me and walked me up my walkway. I stopped before the door and took his hands in mine.

I looked up at him and spoke, "I really did enjoy tonight, it was the most fun I've had in a very long time. I've never been with a guy who makes me feel this way. I'm sorry tonight didn't end the way you maybe had planned, but I still want to go on another date with you."

Report Story

byLittleblackdress54© 7 comments/ 38652 views/ 38 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: