I’ve been dressing in women’s clothes for what seems like my whole life. It started, like most CDs, with my mother’s bras and panties. I loved the feeling of satin and lace. I would find ways to try on my mom’s dresses or sneak into my female cousin’s closets and try on their dresses and heels when I slept over. I loved feeling like a girl. 

One night, when I thought my mom was going to be out late, I decided to play dress up. I went full out with makeup, her nicest dress, heels, and even her fox fur jacket. I thought I was Little Miss Cutie. 

Unfortunately for me, my mom came home early because her date was a jerk. She caught me all dolled up. She went ballistic and started screaming and yelling at me. I was so embarrassed. 

The next morning, my mom and I sat down and talked about how boys go through fazes of experimentation and sometimes we try things for the experience and so on. I knew where this conversation was going. So, I assured my mom that it was a one off and that I was just experimenting but I “thought it was weird” wearing girl clothes. 

My mom seemed to be satisfied with the answer and that was the last we spoke of it. But, it was not the end of my dressing. In fact, I somehow felt like it motivated me to keep dressing, because my mom “knew” but I would need to keep it my little secret.

I was sixteen years old when I became best friends with Mandy. She was the sweetest, kindest, most fun girl I’ve ever met. Our birthdays were one day apart in the summer, so even though we were both sixteen, we were both sophomores. 

We talked about everything, music, life, family, you name it. We told each other everything. We even were teammates on the High School Swim Team. We became inseparable.

One day, I mustered up the courage to confide in her that I liked to wear women’s clothing.

She squealed with excitement. “Why didn’t you tell me this sooner??? I can’t wait to give you a makeover!” she said. I was so surprised. 

I sheepishly asked, “You are ok with this?” 

“Ok…this is wonderful!” she said. “I can totally practice being your fashion designer and image consultant! We are going to be the hottest chicks in the school!” she said with delight. 

 “We are not just besties, now we are best girlfriends! Oh my gawd, I can’t wait to make you into a hottie!”  

I was floored, but excited. I had someone who was in my corner but would keep my secret. Mandy and I really were best girlfriends. 

Each time we hung out, Mandy was trying new looks on me or having my try on skirts or dresses she brought. I loved it.

One night, she was very adamant that she was going to make me look as cute as possible. She even had me shave my legs. She started handing me matching dresses and heels, having me try on all these looks. Mandy even got me a real hair wig. 

“Girl, what has gotten into you?” I asked. 

Mandy replied, “Can’t a girl help her best girlfriend look like a hottie?” 

I responded, “ Generally, not without a reason.” 

She was grinning like a Cheshire Cat. “Well, you’re right, there is a reason…We’re going on a double date!” she said. “With a boy from eWest High and his cousin, please don’t be mad, but he’s so cute and so is his cousin.” 

I started to panic. “I can’t go on a date with a boy, Mandy, he’s going to know I’m a guy.” 

Mandy giggled. “Not after I’m done with you!”. She assured me that this was going to work.

My head was spinning. Mandy went above and beyond and I have to say we were both looking like hotties. We figured out how to tuck my penis, and she made me wear a padded bra. Mandy said, “I told them your name is Makayla and that your Mom is very religious, so you’ve not been with any boys.” 

“Makayla, really?” I said somewhat incredulously. 

Mandy responded, “Yes, Makayla…I’m digging that. I doubt they would believe you were a girl if I told them your real name, Caleb!” 

“Mandy, I can’t do this, I’m so scared. What if someone recognizes me? What if my mom sees me? What if he figures out I’m a guy?” I said as I was hyperventilating. 

“You need to stop.” Mandy said. “We are going to be fine. I promise you this is going to work,” she assured me. 

“Look, they are both Seniors, both football players, super hot, super dumb. They are not going to know and we are going to have fun. Now relax, and get your hottie on, bitch!”

I trusted Mandy so much that I decided to just relax and let my inner girl shine. 

We met the guys at the mall on the other side of town and Mandy was not kidding, they were both such hot guys.

“Hey guys, this is my bestie Makayla. Makayla, this is Tony and Gage” she said. I took a deep breath and said, “Hi guys, Mandy and I are really excited to hang out.” Yep, I was doing this.

The guys were super nice and attentive. I paired with Gage and found myself relaxing and letting Makayla come out. We held hands as we walked the mall and chatted. He told me he was worried that I was going to be ugly or Mandy’s nerdy friend and that it was going to be a lousy time. Then it came. Gage looked at me and said as he blushed, “I actually think you’re hotter than Mandy. A lot hotter.”

I brushed my hair behind my ear and giggled, and said, “I thought the same thing about you too. I’m so glad I said yes.” He moved in and was about to kiss me when Mandy yelled, “Come on, lovebirds, we are going to be late for the movie.”

Mandy and I ducked into the ladies room before the movie started and Mandy grilled me. “Well…Makayla…I told you they were hot and you didn’t need to worry.” 

I responded, “Well…Mandy…you were right, he’s already into me.” 

Then Mandy said, “ You better freshen up your lipstick, I don’t know how much of the movie we will be watching.” She was right.

I don’t think any of us watched one minute of the movie. Gage’s big, strong arms felt so good around me as well as he was such a good kisser. I was so turned on, but it felt really weird being tucked. His hands moved to my freshly shaved legs, and my hand moved between his thighs. The deeper we kissed, the more excited he got. Luckily for me his hands moved to my ass as I started to rub his crotch. 

I was all in on this. He squeezed my ass and started to suck in my neck. My nipples were rock hard and poked through my bra. I slid my hand down his pants and felt his excitement. I gently massaged his cock as he whispered in my ear how turned on he was. 

I felt a little precum leak out onto my hand and I pulled my hand out and licked it off. His eyes got huge. 

I whispered in his ear, “Do you want me to swallow the rest?” “Fuck yeah!” He whispered back.

I was so ready to go down on him when the stupid movie ended. Mandy came over and said, “Makayla and I will meet you boys in the lobby, we need to freshen up.” 

Back in the bathroom, Mandy and I compared notes. “Oh my god, Mandy, my head is spinning, I was ready to blow him. What are we going to do now? “ I asked. 

Mandy said, “ What do you think we are going to do? Think like a girl, we leave them wanting more.” 

Not the answer I was hoping for, but I let her take the lead. We exchanged information, kissed a little more, then kissed the guys goodbye.

The whole drive back to Mandy’s house, we giggled and called each other sluts as we recanted each other’s make out session. “You licked his precum off your hand in front of him, Makayla, I’m shocked at you!” Mandy cackled. 

When we got back to Mandy’s house, we went straight up to her room and we both got undressed. When I finally untucked, my cock sprang right out because I was still so turned on and excited. 

“Shit girl, I didn’t realize you had that between your legs.” Mandy said. 

I laughed and said, “This girl has a lot to offer.” 

Then Mandy shocked me and told me to lay down on the bed.

She slinked up next to me and started to stroke me. Fuck! I was rock hard as she leaned over and we started to make out. Her lips were so soft. 

“Am I a better kisser than Gage?” Mandy purred. 

“I don’t know, am I better than Tony?” I responded. 

I could not help but rub her nipples and then suck on her breasts. I slid my hand down and took off her panties. She was as wet as I was hard. Then Mandy climbed on top of me and slid her warm, wet pussy onto my rock hard cock.

There we were, two besties, made up like sluts, consummating our friendship. It felt so good, so natural, so right. It didn’t take long for both of us to cum. We fell asleep, with me still inside her. 

We were awakened by the sounds of her parents drunkenly coming into the house. They went into their room and I think passed out.

I turned to Mandy and asked, “So what now?” 

She kissed me on my lips and said,“I guess we are besties for life, and I guess you are bisexual.” 

We both laughed and kissed. She really is my best friend.

The next day, Gage called me, and we talked for about an hour and agreed to go out again. 

I immediately called Mandy, freaking out, “Mandy, I just told Gage I would go out with him. What am I going to do?” 

Mandy laughed, “I guess I’m going to dress you up for your man, slut!”

The plan we made was that the boys would pick us up at Mandy’s house, but we would go our separate ways. We went out shopping and picked out outfits for our dates. Mandy did her usual magic and turned me into a total hottie. I felt like such a sexy baby. 

The guys picked us up and we went to their respective cars. 

Mandy winked and said, “Make sure you two behave yourselves.” 

I responded, "Yes, mom.”

Gage and I went to get something to eat. It was crazy that I saw people I went to school with, but no one recognized me. I giggled when one of the guys in my math class blew me a kiss when his girl looked the other way. Gage did not take kindly to it, but I told him I knew him and he was approving of my choice of guy. I don’t think he bought it.

After we ate, Gage suggested we go back to his house because his parents weren’t home. I started to panic, what should I do, what if he discovers I’m a guy, what if he hates me. 

As those thoughts were flooding my brain, he leaned in and kissed me.

I breathed out and said, “Let’s go!”.

I was all in. His house was really nice. As I hung up my jacket, I noticed his Mom had a fox fur coat. I don’t know what possessed me, but I put it on and slinked over to him. “Does this fur make me look sexy?” I asked seductively.

“Why don’t we go upstairs and I’ll let you know,” he responded. I don’t know what has gotten into me, but I knew Makayla was about to be unleashed.

Within moments, we were locked in a deep kiss and we started to undress each other. He was completely naked. I knew I needed to keep my bra and panties on. The fur felt even softer on my body and helped to hide my tuck job.

Suddenly, I got a text from Mandy. It said, “In case you’re not sure…”. Then it was a 15 second video of Mandy going down on Tony. I had to laugh. 

I looked over at Gage and his rock hard cock. I slinked over and began to kiss his tip. I think his cock was twice the size of mine. I started to lick his shaft and massage his balls with the sleeve of the fox fur. He was writhing in pleasure. I could barely fit his cock in my mouth, but a girl has to persevere. 

I got him to sit on the edge of the bed so I could get on my knees so I could deepthroat him. I used the fur to massage his legs as I gagged on his cock. It was glorious.

“Oh my god Makayla. That feels so fucking good!” I was very proud of myself for getting a guy this hot on my first real blowjob. 

His cock was so yummy, and I felt like a total slut just going up and down with my mouth. It was amazing.

"I’m going to cum," Gage moaned. “Makayla, I want to cum inside you, I want to fuck you!”

Oh no! I had to think fast.  “Gage, I’m not ready for that yet. I’m not on the pill; I don’t want to get pregnant," I said. “But, so you can leave all that goodness in my mouth so I can swallow that tasty treat,” I purred. 

Holy sh*t, what did I just say!?! Well, the next thing I knew, he grabbed the back of my head and I gagged on his rock hard cock. I was dizzy with pleasure. The fur, his cock—it was all so fantastic.

It didn’t last all that long before he had a cum explosion all down my throat. I came in my panties, which I hoped I wouldn’t have to explain. Thankfully, he laid back on the bed and I slipped into the bathroom to clean up.

He met me at the door with a deep kiss. “That was incredible, Makayla.”

"Yes, it was," I said with a delighted grin.

We got dressed and Gage drove me back to Mandy’s house and we kissed good night.

Mandy met me on the porch and asked, “Did my video help?”.

“For the first part, but I needed to wing it when I deep-throated him," I purred.

“Holy sh*t you slut, he blew his load on you?” Mandy was legitimately shocked. 

“Well, not on me, all down my throat. My mouth is still full if you want to taste,” I slyly suggested.

“My god, girl, you’ve gone from a chicken to a full fledged whore…I’m so impressed,” Mandy said. “I got Tony to shoot his load tonight, but he came on me, not in me. Ha ha” 

“Any leftovers?” I purred. 

Mandy smiled and said, “My parents aren’t home, let’s go find out…Makayla.”

As we lay there after another hot fuck, I whispered to Mandy, “Girl, as good as Gage felt, it’s even not close to being with you.” 

Mandy looked in my eyes and said, “That’s because we love each other Sis.”

"Yes, we do, Sis, yes, we do,” I responded.

It’s crazy, I gave my first blowjob, swallowed my first huge load, and lost my virginity within a week or so. I’m not sure what my next step will be, but the possibilities are endless and thrilling for me…and Makayla.