Down the pink rabbit hole

Not really seeing much of a choice you stammer....”okay. I’ll do it.”

Lily once again pretends that she can’t hear you, “I’m sorry what was that? What are you going to do?”

“I said I’ll do it. I will wear women’s clothes. But this is just so I can make enough money for school and to pay Ms. DeMorgan back.”

Lily smiles and puts her arm around you, “good boy, or should I say good girl. Now go pack your stuff up and go home. Since we are off the next couple of days this will be a great opportunity to introduce you to the world of womanhood. Wear this same outfit tomorrow and meet me at the La Senza in the mall.”

With your head spinning you silently nod while Lily hands you her makeup kit and says, “you’ve watched me do your makeup long enough. Make sure to put some on before you come. I also want you to use a little mascara. If you struggle you can watch a tutorial on YouTube or maybe your sister can help you.” With that she walks out shouting “see you tomorrow.”

Ever since you were little you never had any issues falling asleep. You always showed up to big tests well rested and were never tired before giving a presentation in class. Last night you didn’t sleep at all. Tossing and turning about what your future was going to look like. At 7:30 AM you heard a notification on your phone. Looking at it Lily texted you “make sure you shave all hair below you waist and any chest hair that you have in addition to your armpits and face. First rule of being a girl is no excess hair.”

After showering and shaving it was time to put on Lily’s clothes. Even though this would now be your third time wearing women’s clothes this time it felt different. This time you had clean dry clothes of your own to put on. This time you were actively choosing to wear women’s clothes.

After getting dressed you felt different. While your legs were never hairy they were never this smooth. And the way the panties cradled your smooth cock and balls was making you horny. You felt your cock partially swell but just not get all the way hard. And once again you felt that tingling sensation in your nipples. You pulled your leggings down, your panties to the side and started to stroke your cock.

No matter what you did you just couldn’t seem to cum. That is until you absentmindedly touched your nipple. WOW! That felt great. After playing with your nipples your cock finally started to get hard and you had one of the best orgasms of your life, even if your actual cum was a little more watery and noticeably less.

Cleaning yourself off you redressed and put on your makeup, remembering to put on mascara for the first time. Afterwards, you made your way to the mall where Lily was waiting for you with another soy latte. “Okay let’s go get you some panties and lingerie!”