Start simple with the briefs

As I got myself ready for school I looked over my new garments which were spread out across the bed. The thought of wearing each of them gave me a thrill, but as I held a pair of the briefs in my hands, fingertips softly rubbing the smooth, black fabric I realised that these would be the most sensible to start. There was football training later that afternoon and even in my shorts, nobody would have a clue that I was wearing these underneath.

I slipped them on, the silky smoothness against my cock and balls in contrast to the slight discomfort their tightness caused. Once I slid into my pants I was pleased how good they still felt as I moved around... today was going to be great!

The day was mostly uneventful although I did catch myself swaying my hips about a little more than usual from time to time, relishing the sensation of the feminine garment against my skin. However, it was not until football training that my new underwear made their true debut.

It was after training, I was rubbing down Tom, one of the guys who sometimes liked to use me, his naked back shining with oil as I diligently worked his muscles. My cock was semi hard, crushed into the front of my knickers which felt great and I began to lose myself in my work until I felt a hard smack on my ass. I yelped and looked back over my shoulder to see big Bill leering at me.

"Hey slut." he said, not unkindly - the guys who fucked me liked to call me dirty names when we were alone. "Got something for big Bill today?"

I felt his hands tugging at my shorts, pulling them down but suddenly he stopped and let out a low whistle. "Oh my... aren't you looking sexy today..." he said, pulling at my shorts again, taking them down my legs and guiding me to step out of them.

"What is it?" asked Tom, rising from the bench and moving around behind me. "Holy shit bitch, look at that ass! You're hotter than my fucking girl man, and she won't even suck my dick."

One of them tugged off my shirt, pulling it off me and tossing it aside before both stepped back to admire me. I was blushing profusely, embarrassed at being inspected so thoroughly and yet I felt a thrill at being looked upon with such lust.

"Damn girl..." exclaimed Bill, "turn around for us... show us what you've got." I complied, turning slowly as I looked at the floor, then once I had completed the circle I placed both hands on the bench and bent slightly at the waist, pushing out my ass in what I hoped was a sexy pose.

"Oh yeah..." continued Bill, "so fucking hot. I'm gonna fuck you so fucking hard."

I gasped as he began pulling the knickers down my legs, mumbling, "Come on guys... it's nothing you haven't seen before."

Bill was pawing at my ass now, his big fingers probing between my cheeks, then spreading hs saliva over my hole.

"No man... uh... babe..." Tom said, his breath slightly laboured as he watched on, "this is different... you look fucking smoking. You know, a few more little things and you would look hotter than most of the girls in school."

I began to ask him what he meant, but in that moment Bill pushed his cock inside me, driving it to the hilt. We both moaned in pleasure, then Bill took up his rhythm, slow at first, getting us both ready for what was to come.

Tom continued, "My girl has a few wigs. They're nothing special, just some cheap things she's worn to parties and stuff. I bet I could sneak one away... that ass and a sexy hairstyle. Damn, ain't no guy in the team wouldn't want to fuck you."

Bill grunted as he picked up the pace. "Yeah, that sounds fucking hot..." he huffed.

Again, Tom spoke, "She also has these bras that are a bit like, padded. They push up her tits and make them look bigger. I could probably swipe one of them too... You would look hot as hell."

By now Bill was slamming me with his cock, his hips slapping loudly against my ass as he railed me. I was unable to answer Tom, but in my mind I was screaming yes, please, thank you. I couldn't believe the effect a simple pair of underwear could have on the guys, and couldn't wait to see what the rest might do to them. The fact that Tom was so eager to help me was also mind blowing, I had never felt so accepted as my new self. As Bill fucked me harder than he ever had before and my thoughts wandered to all the slutty things I could wear I was suddenly cumming, my balls clenching tight and my cock dribbling out several wet squirts of seed.

Bill didn't take much longer, finishing off with three or four ruthless thrusts before exploding deep inside me. Once I finally caught my breath I thanked Tom.

"Anything for this hot piece of ass..." he replied as he moved in behind me, taking Bill's place. As Tom took his turn I began to imagine how I would look, fully dressed up as a girl and the thought excited me. By the time Tom and I came in unison, both of us couldn't wait to see the the next phase of my transformation.