Derek couldn’t believe he was doing this. He couldn’t believe that he’d agreed to do this. Sure he owed Scott. He’d saved his life a couple times and kept him from becoming an omega by letting him back into the pack but this? Derek wasn’t sure there were reasons to let Scott do this to him.
This, of course, was his current costume for the job he’d been given. Derek was wearing thigh high white stockings, a lace short slip, a pleated short skirt and a plain white shirt. Most people knew the costume for what it was, a catholic school girl costume. Only Derek wasn’t wearing it entirely traditionally. Because instead of any kind of underwear he was wearing a tight cock ring and a lazy prostate massager in his ass, and Derek could feel it intensely.
He had earned his place in the pack by agreeing to whore himself out to who ever paid Scott enough for it. And lately the pack had used Derek to pay off debts and bribe people to do things for them. That’s what tonight was about. Tonight he was the property of Adrian Harris who had some odd tastes.
Derek had had to be edged around the clock every day for the last week. Before being put into this costume and sent out into the night. His large cock leading the way as it raised his skirt up. Not something he needed since the skirt only just covered his ass, leaving the rise of its bulk exposed.
But that wasn’t the worst of it.
No… the worst was that people kept stopping him and wanting to take pictures. A few cheeky guys had lifted up his skirt as the photos were taken so his swollen cock was clearly visible. His face was red and he wanted to get this over so he could get back home and feel like he wasn’t a piece of meat on display. The cat calls were starting to get to him. Men, women, didn’t matter, they were all yelling things and making offers to teach him what that ass or his lips were for.
And this was how he turned up on Harris’ door step, his cock hard and leaking, his skirt raised in the front, and his face red as Harris looked him up and down.
“You know… when McCall said he could provide… entertainment… If I’d let him out of detention early… I had thought he was joking. But then he showed me that lovely photo of you blowing him. I was convinced enough to place an order…” He lifted up the skirt, showing off Derek’s smooth groin and his swollen cock. “They did keep you on edge all week, didn’t they boy?”
“yes sir.” Derek blushed.
“Good. I like my boys on edge and needy.” He weighed Derek’s cock in his hand. “Leave the skirt in the hall, if it’s not there when you’re done, than you’ll just have to go home without it.”
“yes sir…” Derek blushed harder as he took the skirt off and dropped it in the hall, his stockings framing his smooth hard groin.
“Excellent. Let’s start with a little oral first… I think you’ll look good with my cock in your throat… after that I want to see how many times I can fuck the cum out of these big balls of yours.” Harris’ hand squeezed Derek’s balls making him wince. “And if you’re good enough… I might start letting McCall or his friends send you to detention in their place… I could always use a good cock sucker under my desk to help me pass the time…” Harris smirked as he tugged Derek’s balls leading him into his apartment.
Derek knelt between Harris’ thighs while nursing on his hard prick for hours. He’d lost count of the number of times the teacher had creamed his throat while sitting on the sofa lazily watching tv. Eventually he did get around to fucking Derek’s tight ass. Thank god for werewolf healing, but it also felt like a curse when every time you had sex was like losing your virginity all over again. And by the third time Harris had started to notice that Derek wasn’t getting any looser.
“Fuck… no wonder he uses you… you don’t seem to loosen up…”
“G… good gen-genetics…” Derek panted, his cock still rock hard and drooling cum as he flexed his ass around Harris’ cock. He wasn’t massive or anything, but when you’re virgin tight every time, even average felt absolutely massive and like it would tear you in half. The sounds he made, the sobs, all of it fed Harris’ ego.
Hours of fucking and Derek was starting to think the good teacher was as pent up has he’d been this week. Slowly, little by little his clothes came off, and Derek was completely naked in front of a large picture window facing the street as Harris fucked him slowly. By the time he was done with him, Derek could barely stand and started to reach for his clothing, hoping the skirt was there.
“Changed my mind.” Harris came up behind him and slotted his cock between Derek’s glorious buns. “Leave the clothes, you can wear a different costume home.” Derek was confused but Harris kissed him, walking him to the door before shoving him out the door with something in his hands. He looked down to see a pair of grey knit socks and a note that said, on your feet. Derek hung his head and put the socks on, happy he wasn’t totally naked but wishing he’d been allowed at least some kind of covering for his still rock hard cock.
He slowly worked his prostate massager back into his ass and hoped that the streets were a little less crowded on his way home.