"Come on, please do it for me." My big sister whined at me again.
It was the middle of the day in the summer, I had just graduated and was waiting to go to college in the fall, I had a part time job at a motel but today was all mine. Joelle was pissed because her friend Kelley had fallen off her horse and now had a gash on her forehead and a swollen eye. She had planned on styling kelley's hair all afternoon for the portfolio she was putting together.
"Come on, please. I promised Ricky the full portfolio tomorrow. I don't have any other options. I don't know anybody else with short enough hair. You need a haircut anyway; after I'm done I'll make sure you look great." That was true. My boss at the Motel where I had a front desk job for the summer had told me to get a cleaner look and, at 18, the job I had was pretty sweet. I didn't want to get on the wrong side of him. I was tempted, but not enough to undergo the humiliation of my older sister making my hair all girlie.
"It's not as if you have anything planned for today, you're probably just going to sit here playing Xbox and eating chips, like you've done all fucking morning. What a waste of fucking time!" That was true too, and I was feeling dissatisfied with the day.
"Are you wearing mom's panties again? Do you want me to tell her?" Oh, No! That chilled me to the bone. How did she know? It had been a long time since she walked in on me jacking myself of in mom's panties and I had been much more careful since then. I glared at her. We both had secrets and that could be a destructive path to take.
She sighed. "Please, Jamie, do this for me. It'll be fun. Mike gave me some really good pot at the weekend. You can get stoned; I'll make you lunch and then play with your hair. We'll put some tunes on and have fun and when we're done I'll make sure you look sharp. Promise!"
That did it. Food, pot and an afternoon being friends with my big sister was too enticing. It didn't hurt that I found the idea of having a feminine hair style arousing.
"Ok, Joelle. You win. Where do we start?" I said with an overplayed sigh of resignation.
"Ohhhh thank you, thank you, thank you." She said gleefully. "You have a shower and I'll meet you on the deck with lunch and pot." And with that she happily disappeared to the kitchen.
I went to the shower shedding my t-shirt and shorts and mom's lacey white thong I stepped under the hot water. I was semi-aroused, I had been all morning since mom left and I slipped into her laundry basket and found the little thong that kept my dick deliciously constrained all morning. I soaped and shampooed myself, scrubbed and shaved using only Joelle's feminine soaps, none of my own, until I stepped daintily from the shower. My cock was rock hard and I felt a desperate need jack off but I refused, wanting to stay as horny as possible through the afternoon until I could find a time to slip away to mom's room to dress up and revel in my new feminine look as I came.
I dried off and rifled mom's lingerie drawer, finding red satin and lace french cut panties. I slipped the panties on, thrilling at how they caressed my aching cock. I pulled on basketball shorts and shirt to hide them and headed outside.
She was sitting excitedly with lunch and pot as promised and, as I devoured both, she chattered about hairstyles and fashion as if I were Kelley. She had only a little pot saying it made her distracted and horny and she wanted to be at her best.
In our parents bathroom she had everything set up. She sat me down, washed, conditioned and cut my hair. She dried it and curled it a little. She was wonderfully happy and chattered endlessly about relationships and friends and boys and even sex. She took off her baggy t-shirt when sge started running water and was wearing only a tight crop top and boy short panties. The sight and scent of her was arousing. I was in heaven, nicely stoned with her soft hands caressing my head and neck, favorite tunes and happy chatter in my ears it all felt wonderful.
She stood back and looked at me in triumph. Then she visibly slumped. "You look too boyish!"
I giggled. "What did you expect?"
"Girlish!" She replied. "But maybe some makeup will help for the photos."
Photos! I hadn't thought of that. "I don't want anyone seeing me like this." I complained.
"Well, Duh!" She said pointedly, "The only reason we're doing this is so I can show people my styling. Photos are not optional. Don't worry; some makeup will make you unrecognizable. Besides, you look pretty cute, certainly nothing to be ashamed of."
She pulled out some stuff from drawers and straddled my lap, sitting on my legs facing me. She concentrated hard as she worked on my face. Her movements on my lap sending spikes of pleasure to my already excited dick. Cheeks, eyelids, eyebrows, forehead, nose, neck and lips all got treatment before she rocked back to look at me with a satisfied grin.
"Voila!" She cried holding up a mirror. I looked completely different, very feminine, quite pretty, hot even! My hair was dark, almost black, and cut in a bob. My eyes looked bigger and my nose looked smaller. My face looked more round and my skin looked smooth. I was totally absorbed.
"You're amazing!" I said. "You totally transformed me!"
"Not totally!" She smirked, and her hips moved, nudging her pussy up against my hard cock. "Ha, I think you like it." She was rocking her pelvis playfully. Her pussy riding against my unyielding dick.
We both looked down, and to my horror the red lacey top of mom's panties showed, my hard on, straining below. She chuckled and reached down and pulled the shorts away as much as she could.
"Thought so!" She smirked, wrapping her fingers around my cock and stroking sensually. "Mom's panties!"
I gasped at the intense pleasure. "Not such a little brother anymore though!" She purred, watching my reaction, enjoying my desire and confusion.
She stroked me slowly, her movements obviously caressing her pussy too, her eyes growing wide as I began to loose control and triumphant as she released my cock just before I crashed over the brink.
She stood up saying. "Too early to celebrate, Jamie. We have work to do." Visibly relishing the squirming panting wreck before her, left desperate, she pulled me up and stripped off my shorts and shirt. "This won't do. We need girls clothes!"
She had me try on a variety of different outfits from her closet and from mom's before she settled on one for the photos. She also had me try a bunch of poses, snapping photos until she found the one she loved.
Finally, she said, "Ok. That's a really good one. Let's go back to the bathroom for round two! I'm so jittery, let's have some pot first."
"What happened to distracted and horny?" I asked joking, as we shared the pipe.
