With a little help

In a couple of days time I found myself preparing for the day, my mind consumed with thoughts of training that evening. Would Tom come through with his sister's things? How would I look in them? How would the guys react?

In my excitement I chose to wear the thong under my normal clothes which only heightened my impatience as the day dragged on. The thin piece of fabric nestled up between my cheeks and stimulating my asshole was a constant reminder of what was to come and made it impossible to concentrate on my classes.

Finally the time came for training yet still I had to wait, watching from the sideline as the guys ran drills. My mind wandered as I watched, and I began to imagine myself as a sexy girl, rubbing down the guys mid game or running out to an injured player, the envy of opposition teams who all wanted to fuck me. By the time the session ended I was so lost in thought that it was Tom slapping me on the shoulder that woke me from my daydream.

"Think I might have pulled something out there..." he said with a wink. "Mind helping me out?"

Snapping out of my reverie I quickly followed him inside then we made our way to the massage benches. While the area wasn't exactly a separate room, it was tucked around a corner where nobody really went unless they were looking for me. So far it had been private enough.

As we entered, Tom fished a couple of items out of his sports bag and placed them on the massage table - a platinum blonde wig and black padded bra as promised. As I turned my gaze from the items to Tom I found him grinning at me as he scanned my face.

"I thought you would like them... go on, try them on." he said eagerly.

I quickly complied, pulling off my tee and going for the bra first. I slipped each arm into it then found myself embarrassingly unable to fasten it. Tom helpfully took control, turning me and rather expertly sealing the clasp, his fingers brushing against my bare back and sending a shiver down my spine. The smooth material pressed tight against my chest only heightened my excitement and once it was secure and I reached for the wig I found my hands shaking with anticipation.

I pulled the wig onto my head, careful to tuck my shaggy hair up inside before pulling it down tight. I cleared the fake hair from my face with a flick of my head, then turned to Tom.

"Here..." Tom said, reaching over and rearranging me slightly, tugging at loose strands and setting them right before taking a step back to admire his work. The wig was just over shoulder length, the smooth, straight, soft fake hair tickling my shoulders and neck pleasantly. He stared at me in silence for several moments as I smiled nervously back, eventually having to ask him, "So?".

"Oh, shit... yeah you look... amazing." Tom gushed, his eyes wandering over my face and chest. As he ogled me hungrily I realised I was still clothed from the waist down. I quickly kicked off my shoes as daintily as I could before peeling off my socks and track pants, revealing the black underwear beneath - the simple thong similar enough to the bra to almost appear a matching pair. Flashing what I hoped was a seductive smile at Tom, I turned side on, raising a hip and showing him my exposed cheek in the process. His audible gasp was evidence enough of his approval, the sound causing my cock to twitch and my hole to quiver.

Suddenly Tom's hand was on my ass and he was pulling me close, wrapping my smaller frame in his muscular arms and holding me tight as he groped my exposed cheeks. I snuggled in close, his sweaty aroma intoxicating as I felt myself melt into him. I felt so soft and cute and... feminine in his arms, and as I felt his cock hardening through his shorts it was only natural for me to reach out and caress him.

"Thank you Tom..." I whispered breathlessly before sinking down to my knees, pulling his shorts and underwear down as I went. Soon I was in the familiar position of sucking Tom's cock again but this time it was different. As I gazed up at him from under the wig, hoping I looked as cute as I felt I could see a new kind of lust in his eyes. It was as if he was watching me with new-found desire which only served to spur me on and in no time I was bobbing my head back and forth wildly as I did my best to pleasure him.

Just as I felt Tom's cock twitch between my lips and his heavy breathing started to become full blown grunts of pleasure, I heard the sound of footsteps approaching. Tom seemed oblivious and with him so close to climax I didn't want to stop but I sensed someone coming and when I spotted a shadow cross the floor I yelped and pulled back from Tom.

It was in that moment that Tom erupted, my hand still stroking him rapidly as he shot jets of thick, warm cum all over my nose, lips and chin. Despite his loud groans of pleasure I distictly heard a shocked gasp from behind him and I knew we had been caught. My heart pumped fast as my fingers continued to stroke Tom's member, the last pulses of his orgasm petering out, and finally I leant to the side to peer past him, spotting the onlooker.