Author's note:
Whilst this works as a stand alone story, reading the earlier chapters will give you better context. In case you can't be bothered with all the previous 45k words, here is a synopsis for you:
Rune, the runt of the family, and only son, grew up with four over achieving sisters and, shunned by his parents and siblings, lived the life of a loner, dressed in his sister's feminine 'hand me downs'. He was befriended by Becca, a hot soccer player, at College. She discovered he had a pair of his sister's underwear and encouraged him to live the life he wants to live, dressed as a woman, something Becca, and his landlords, finds a huge turn on. Along the way Rune's had an interludes with Becca, nights out with her team and a dirty weekend away with his landlords and lost his anal cherry to one of Becca's team mates.
And remember, this is not real life. It is just a story folks. Any resemblance to anyone, anything and anyplace is purely coincidental.
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The message had been simple.
Becca: My place NOW.
I was ahead of where I needed to be with my next assignment so I welcomed the interruption. Maybe she wanted to go get some dinner somewhere. It had been raining all day so I made a mad dash to my car and headed over, cursing the fact that the shitty air conditioning was struggling to clear the condensation on the inside of the windscreen on the short 10 minute trip over there. You could add a car aircon service to the list of jobs I never got around to over summer and now regretted.
She answered the door and pulled me excitedly through the doorway.
"You've got to help me. I need to come up with some inspiration for an outfit."
"Okay," I replied. "When for and where?" I was a little puzzled. She'd never asked me for clothing advice before and she seemed really frantic.
"Tonight, silly! In forty five minutes. Drayk asked me out to dinner." She jittered. "I'm just not sure what to wear."
"Drayk?" I asked.
"Drayk. Him. The guy. That guy!"
'So. He has a name.' I thought. "When did you find out his name?"
"Last night. Simone and I went out for pizza over at Luccio's over on Dudley yesterday. He was there. We had pizza with him and his buddy Cal and then went out for beers."
I had been so tired from my night with Becca and Simone that I'd crashed early. I shook my head at the thought of her having that much energy to go out, especially after her big soccer game the previous day.
"I was so excited by seeing him that gave him a hand job at the booth and then he fucked me in the back seat of his truck."
"Simone too?" I inquired.
"Drayk is not her type. Neither is Cal. They just ate pizza and watched me from the booth get slammed up against his rear window in the parking lot."
She led me through to her bedroom and pointed at the small walk in dressing room. I went in and had a look. I'd never seen this before. There seemed to be three sections; the athletic and sports section, the everyday section, which had some pretty nice stuff in it, and the glam section.
She had a couple of pretty nice LBDs hanging up there, but also a stunning red dress with a high neckline, tight bodice with mid thigh length and a lengthy split on one side. Pulled it out and put it on her messed up bed. I found some black 'high on the calf' boots with a two and half inch heel and a black double breasted long coat.
"Oh, great thinking," she said as she inspected my choices. "Unless you were slutting me up, I'll need some panties and bra too."
I went back to the dresser and looked in some drawers. Regulation bras and underwear in one and some racier stuff in another. I pulled out a few and looked at them, and grew harder in my tucked position in my thong.
It took me a minute but I found a high waisted thong that would rise above the slit in her dress and a matching bra. They were both delicate and shear.
She then told me to sit on the bed and she stripped and went out to the bathroom. The shower started. I got up and looked around the room. It was pretty messy, with a few piles of clothes and some dirty dishes here and there. I snuck a peek in her bedside drawer and immediately saw a pink Hitachi vibrator, a tube of strawberry lube and several condoms. Ohh, and some chewing gum.
I went back to the bed and waited. The shower finished and the hair dryer started. Then some sounds of drawers and the like opening and closing. Then nothing but random sounds.
She eventually came back into the room and resumed her excited chatter. Her makeup was flawless, her hair straightened and her eyes sparkled. Her naked nubile body screamed 'sex'.
She pulled on the thong and stood up, giving me a show. It hardly hid anything but it looked amazing on her. Same with the bra.
"I think you are enjoying this and I bet you are hard down there," she said, "I'd love to take care of you, but I need to save myself for Drayk." She went over to a pile of clothes and found me a cotton pair of hipster briefs. Throwing them to me she said "Jerk off into those if you want. They need a wash anyway."
She went to her wardrobe and returned with a pair of black lace top thigh high stockings and carefully put them on and then stood, giving me another look at her when she had finished. I gulped at the sight before me.
"Go on, you know you want to!"
I stood by the bed and wrestled with my jeans and thong, freeing my dick and seeing it harden immediately. I pulsed it once and a healthy drop of precum appeared.
I watched her complete the outfit, mesmerized and all the time stroking myself and thinking of my dick sliding into her warm pussy and hearing her moan.
She looked at me and smiled. "Close your eyes and finish the job."
I closed them and really went for it. My pre cum flowed my dick felt amazing and I pictured her again, standing there in that flimsy thong. I could feel my orgasm build and I reveled in the thought of what was about to happen.
I felt her next to me before I heard her. "Oh god, you look so sexy with that face of yours all screwed in ecstasy."
I was so close.
Her hand replaced the one sliding on my erection and I opened my eyes just in time to see that she had aimed me right at the crotch of the underwear she had thrown to me.
She turned and went to wash her hand.
A car horn beeped outside and her phone, which was on the foot of her bed, chimed.
'That will be him!"
