Last summer was the best experience I had ever had, but it had to end some time. Mom and Jenny surprisingly didn’t catch on to anything that had happened, at least nothing that they mentioned to me. I had decided to go to a college that was close to home, but I wanted to live in the dorms as it was more convenient for me. It was definitely hard being fully on my own, but I was able to get through it.
During my first semester, I met my girlfriend Anna in a class that we shared. We bonded over our love for technology (both of us are Computer Science majors), and we began to date after a couple of months. I lost my virginity to her, and we have had sex a bunch of times since then. We love each other very much.
A couple months prior to the summer, I confessed my secret of crossdressing to her. She was really supportive, and she was actually excited more than anything. She’s bisexual, so maybe that had something to do with it? Either way, I’m really lucky to be with her.
As summer drew closer, Anna talked more and more about how she wanted to see me dressed as a woman. We decided that, once my mom and sister leave for their trip, we would start the process. She wanted to see the transformation happen before her eyes, so I wasn’t to do anything before she got there. While Anna was from out of town, she used the excuse of taking a short summer class to stay on campus, so she was going to be here for most of the summer.
This year, Mom and Jenny decided to go on a longer trip than normal. Jenny had just graduated, so she wanted to have one last hoorah before starting her new job. Mom had some extra vacation time built up, and she figured that this was the best time to use it. They decided on a whole month-long trip! That meant that I had twice as long to enjoy myself and have fun with Anna.
Day 1
Like last time, I helped take the suitcases to the taxi that was in front of our house. Mom and Jenny had a lot more packed this time, so it felt like there were bricks in their luggage. Mom gave me a longer hug than normal, saying she was really going to miss not seeing me for a while. She was a little worried that I would be bored out of my mind and couldn’t handle being alone for that long. I reassured her that I’ve done it before, and that Anna was around to keep me company. “She’ll be doing much more than that,” I thought. We gave our final goodbyes as they got into the cab, and it drove off.
Once the cab turned the corner, that’s when I texted Anna that it was time. “I’ll be there in about 30 minutes,” she texted back. The anticipation was killing me, I didn’t think I could wait that long. But soon, her car pulled up into the driveway. As she got out, I couldn’t help but stare at her. She was so gorgeous with her beautiful legs, sexy clothes, and perfect makeup. I still couldn’t believe I was dating her.
“Are you going to keep looking me over, or are we going to get to work?” she said, snapping me out of my trance. “Sorry, you just look so pretty,” I said. “Aww,” she blushed, giving me a peck on my lips. “Now, come on, I want to see you look pretty, too.” We walked back into the house and closed the door behind us.
We figured that the best way to start off was for me to take a shower. I stripped down and headed for the bathroom. “I’ll pick your clothes out while you’re in there. I guess your sister’s clothes are going to have to do for now until we get your own clothes,” Anna remarked. “My own clothes?” I questioned, but that was soon out of my mind as I got into the shower.
I took the bottle of Nair again and made sure that every inch of my body was covered with the cream. After a little while, I turned on the shower so everything would wash off of me. I touched my skin and it was back to being smooth. I was already getting hard from the erotic sensations, I’ve missed this so much. I cleaned the rest of myself with the feminine soap and shampoo and stepped out of the shower. I looked around the bathroom to see if there was anything that might make Anna happier, and I found a bottle of lotion. I used some of it on my skin and it made me even softer than before! I put on the dressing gown and left the bathroom.
On Jenny’s bed, Anna had just finished laying out the clothes for me to wear. There was a pair of pink panties with a matching bra (different than the set from last time), along with the breast forms. She had also put out a pair of short shorts with a light pink crop top.
Anna turned around and saw me for the first time with hairless skin. She smiled and said, “you look so sexy, especially with that dressing gown.” As I took off the gown, she could see that even the hair around my genitals was gone. “Mmm, I think I like you much better this way. But if we’re going to go all out, we have to something about your penis.” It was rock hard at that point, and tucking would be too difficult with it this way. Anna apparently knew what to do now.
She got on her knees and started playing with my penis. First, she stroked at a slow pace, but increased her speed gradually. Since I was already turned on, it didn’t take long for me to be at peak hardness. I was about ready to cum when she stopped. She waited almost a whole minute before taking my member in her mouth. She bobbed her head back and forth, with me loving the way her lips felt grazing my penis. She used her tongue to continuously heighten the sensations I was feeling, and soon I just couldn’t take it anymore. I cummed in her mouth like there was no tomorrow. She began to suck in order to get every drop of cum that was coming out of me, and my penis kept shrinking until it was just a little nub. That was the first blowjob I’d ever had, and it was amazing. Anna swallowed my cum and smiled. “Now you’ve got your own little clitty.”
Anna helped me tuck my now soft penis and had me slip on the panties. She picked up the breast forms, salthered some glue on them, and stuck them to my chest. She then took the bra and put it on me, easily hooking it behind me. I finished everything off by putting on the shorts and top. Seeing myself in the mirror, I smiled, knowing that this was just the beginning.
Once Anna had fully looked me over, she said, “Damn, you’ve got one hot body. Especially that cute little butt.” She then slapped me on my ass, and I think I blushed a little.
Before we started on hair and makeup, she got her suitcase out and opened it up. She then took out her own set of makeup, saying that it was probably better not to use my sister’s. She also took out a hair dryer, a curling iron, and some scissors.
Anna took the scissors and cut just a little bit off the bottom part of my hair. She used the hair dryer on my hair while she brushed it out a little. Once my hair was dry, she took the curling iron and used it to add a little style to my hair.
She announced that my hair was finished and we started on makeup. She gave me the foundation, mascara, eye shadow, and lipgloss, wanting to see me do it myself. Just like last summer, I took the foundation and applied it evenly to my face. I looked to the eye shadow, and the one Anna had for me was blue and glittery. I closed my eyes one at a time and applied the shadow to my eyelids. I then took the mascara and carefully used it on my eyelashes. Finally, I twisted off the wand of the lipgloss and covered my lips with the red color. I looked at myself, and I was breathtaking.
I then turned around for Anna to see my work, and she was shocked. “Baby, you look so sexy. I’m surprised you did that good of a job. I don’t think I can call you Leo anymore, you need a feminine name.” I thought about it for a little bit and said, “what about Lauren?” “Oh my god, that’s perfect!”
At this point, it was about 4:00 in the afternoon. “What should we do next?” I asked. “Let’s do a slumber party!” she practically blurted out, which is probably what she had planned from the start. So, with that, we moved to the living room.
First, we painted each other’s nails. She started off with painting my toenails in a bright pink color. She took some nail extensions out of her bag and glued them onto my fingertips. She filed them down into an oval shape before painting them with the same pink as my toes. Once my nails had dried, I did the same thing to Anna’s nails. Everything had become harder to do with my longer nails, but I honestly couldn’t complain. Soon enough, we had matching nails.
We felt a little hungry and decided to order a pizza. While we waited, we played truth or dare. I started off and said truth.
“How sexy do you feel right now?” Anna asked.
“Very sexy, a lot more than the last time I dressed up actually.”
Anna also chose truth. “I guess I’ve never asked you this, but when did you find out you were bisexual?”
“I was a little tipsy at a party in high school, and I made out with one of my friends. We then went into one of the bedrooms and did it, and it was the best sex I had ever had.”
“That sounds so hot.”
I then chose dare. “I want you to answer the door to the pizza guy once he gets here.”
“What? I don’t think I can do that.”
“Come on, you look completely like a girl, no one will think you are a boy. All you have to work on is your voice.”
I agreed, and she coached me on how to make me sound more feminine. I eventually got the hang of it. Once she proclaimed that I was ready, the doorbell rang. I hastily got up and answered the door. There was a teenage boy standing there with the pizza in his hands. He kind of stared at me a little before getting out, “Uh, cheese pizza, $7.50.” I hand him the cash and said, “here you go, and keep the change” in my new girly voice. I took the pizza, thanked him, and closed the door.
“Oh my god, Lauren, he was practically drooling over you!”
“If only he knew what I had tucked between my legs,” I said, and we both giggled.
As we ate our pizza, we talked about what the rest of the night looked like. Anna had the idea of watching a movie, but she wasn’t sure which one. I agreed with that idea. I took our plates and cleaned them in the sink.
Anna had gone to her suitcase and grabbed two matching pink babydolls, figuring that we should get comfortable. We both changed into them and snuggled on the couch. We found a chick flick and began to play the movie.
We only got about halfway through the movie before we were making out. The feeling of our lips touching, both of us with lipgloss on, was newly found sensation, and I was loving every minute of it. Once the movie ended, Anna suggested that we move to the bedroom.
I was about to take everything off before Anna stopped me. “I want us to have sex like women, no dick is needed.” I shrugged and we went back to making out, practically jumping onto my bed. I began to rub my pretty nails all over her body. I pinched her nipples, and she let out a moan. I then peaked my head under her babydoll to work on her nipples more. But now, I decided to use my mouth. I started to suck on her nipple and she moaned even louder this time. I swirled my tongue around and kept sucking, her moans being almost melodic. Then she let out a huge scream, and she cummed in her panties.
Knowing her, I knew she wasn’t done yet, so I moved my head down towards her vagina. I pulled down her panties, seeing how wet they had become. Keeping my hands up near her breasts, I began to eat her out. I played with her nipples while my mouth explored her opening. She was moaning even more than earlier. “Oooh, Lauren, I think I’m about to cum again!” Just as she said that, I could feel her spasming as her legs tightened around my body. One last twist of her nipples made cum fly out of her. After multiple spasms, my face was covered. I licked every last drop out of her vagina and went back up to kiss her so she could get a taste of her own juices. We then collapsed on the bed.
“That was amazing. I’m going have to return the favor to you sometime,” Anna exclaimed, still catching her breath.
This was going to be one hell of a month.
Day 4
“Hey Lauren, I think we need to go out and get you your own clothes.”
I wasn’t surprised that she brought this up again. I definitely didn’t want to keep wearing Jenny and Anna’s clothes, but I just didn’t think I could go out like this. I mentioned my concerns to Anna.
“I know this might be going a little fast, but I think you’re ready. You look nothing like a boy, and you’ve mastered your feminine voice. Worst case scenario, you will be seen a woman who’s just a little shy.”
She was right about that, and after a little more begging, I gave in. Soon, we left for the mall, and once we got there, I just felt butterflies in my stomach. This is such a big step, but I felt confident enough to step out of the car and walk inside with Anna. The mall was busy enough that day, so luckily nobody was paying attention to us. First, we went in Victoria’s Secret.
“You should pick out at least 5 matching sets, but there is probably more to get,” Anna told me.
“How much is all of this going to cost?”
“Don’t worry about it. My parents gave me a credit card to buy whatever I want.” I forgot her parents are rich, they own some big company on the east coast.
Since we knew my size, I didn’t have to try anything on (definitely glad about that). Once we were done in there, we had such a variety of items. There was panties (bikini, boyshorts, and thongs), bras (regular and sports), sheer pantyhose, and nightwear (babydolls and a nightgown), all in a range of reds, blues, and pinks.
We then moved on to one of the clothing stores. Anna didn’t say what I should get here, but she definitely veered me towards the more girly items. We soon had skirts, short shorts, frilly tops, and even a couple of dresses. This time, though, she wanted me to try on everything. We both went into one of the dressing rooms and I modeled everything for her. I actually was having fun, all of the nerves were gone at this point.
I got my original clothes back on and Anna said she was a little turned on from seeing me try on the clothes. We opted for a quickie as I pulled down her panties and fucked her with my pretty nails. We had both become extermely turned on from doing it in public, and she cummed twice, while I cummed once. We made sure our hair and makeup was still okay, stepped out of the dressing room, and paid for the clothes.
The shoe store was next, where I tried on too many shoes to count, all in varying heel sizes. We decided that I only needed a pair of sandals, some pumps, and a couple of high-heeled open-toed shoes.
The last store we went into was the beauty store. Anna said that I should choose my own makeup, she didn’t want to make an decisions for me here. I looked around a little and found two shades of lipgloss (red and pink), an eyeshadow palette, and some nice black mascara. Then I went to find some nail polish, which is my favorite thing to wear. I found a bright red, a baby blue, a light pink, a white, and base/top coats. I said that I was finished and we payed.
Before we left the mall, Anna mentioned she wanted to do some shopping on her own, but she wouldn’t be long. I said that was fine, and I would grab us some lunch. I bought a couple of light sandwiches from the food court and found a booth to sit at. After about 10 minutes, Anna came back from her shopping and we started eating.
“How did you feel about today?” she asked.
“It was good. I felt uncomfortable at first because I thought people would catch on to me being a guy. But after a while, I realized that nobody seemed to notice, or they just didn’t even care if they did notice.”
“I told you that you look like a woman, so I’m not surprised there weren’t any issues. But I think what also helped was the way you are moving now.”
“What do you mean?”
“Well, I think this might just be your heels, but you have started to sway your hips while you’re walking. And you have become more delicate when picking up things, probably because of your new nails.”
I guess I never realized it, but she was right. All of the things I was wearing forced me to change my movements, and I’ve been doing it enough for it to become second nature.
We finished up our meals and left the mall. I didn’t ask Anna what she had bought on her own, but she mentioned that it was a little surprise for me later in the week. I obviously didn’t know what that was, but I would soon find out that it was more than I would have ever expected.
To be continued…
