Disable your Ad Blocker! Thanks :)
Chapter 14
by The guy
Do you go?
Of course
Despite being ****, you went downtown with them, and had a surprising amount of fun, first you allow went to a park, taking in the pretty suroundings and smoking a joint by the river, then you all got dinner at a nice restaurant where Alex knew one of the staff who finessed a free bottle of wine which got everyone feeling toasty. By around 8 you hit the mall. This whole time you and Carly had been attached to your respective man's hips, they had been delightful, making you laugh, and being around Matt continued to make you feel happy but also confused. Now that you were at the mall though, it was time to split up, Matt and Alex headed off to check out a shoe store, leaving you with Carly who excitedly took you by the hand and started pulling you along.
"Where are we going?"
You asked.
"The spa! If you wanna be a crossdresser you've gotta try a little harder than that."
She gestured to your hairy legs, you blushed but realized, you looked a little silly, this might be commiting to crossdressing some but at least you would look good.
At the spa you were greeted by a few women with Adams apples, by the bulges and what you could gleam, about half of the people there were crossdressers, the other half were girls. A large Asian woman took care of you. Waxing your legs and shaving your chest, back ass, and jaw. She treated your skin with powder and lotion making it soft, and she painted your nails pink. Finally she picked off your calluses and at Carly's request, put you in makeup. Being manhandled and stripped of you masculine elements by this big sexy lady turned you on, especially when she cleaned out your ass, and when her face hovered just a bit over yours while she did makeup. From the little smiles she gave you and the bulge that developed in her pants, she was into it too. When she finished waxing your ass she gave it a little grope that you enjoyed so you didn't mention, at the end she even slipped you her number. Carly led you away from the spa, now looking like a real women,
"Just one more stop she said." You arrived at a victorias secret where you had probably the most fun. At this point you were already in it, Carly had eased your fear and going around looking at panties, tank tops and tight pants had the two of you giggling and pawing at each other.
In after picking out a few pairs of clothes Carly dragged you into a dressing room, you might've preferred separate ones but Carly was just SO excited to see you see on clothes and vice versa. She went first, with you sitting on the bench while she changed in front of you.
As she was stripping down naked you came to the realization that she had a penis too, through a bulge in her panties, when she took them off you saw she was wearing a purple cock cage. Noticing your shock she smiled. "Yeah I used to be a boy too, my name used to be Carl, but I started cross-dressing in middle school . I met Alex in high school and we were great friends, we kissed one night and I tried cross dressing in front of him for the first time, it was a pretty incredible night. Now I'm Carly."
"So you're trans?"
"I guess so."
She turned away from you, her big firm ass hanging out just a few feet from your face. You had to stare, Matt's cock might have been the center of your world the past day but you still loved a good ass.
Does anything happen between you two?
A Silly Little Wager
You become your best friend's for a week
Updated on Mar 16, 2020
by madmaniac
Created on May 13, 2013
by saphirblack
You can customize this story. Simply enter the following details about the main characters.
- All Comments
- Chapter Comments