A College Whore Pt. 03

(Thanks everyone for reading! I already have Part 4 almost done :-) )

Sean was pacing back and forth in his room, still in the cum-soaked panties. 'Is this guy blackmailing me? That asshole!' Sean thought.

Furious, Sean texted back: "DELETE THAT NOW."

*bzzz*

James texted back. "Nobody will see them, besides us. As long as you keep making me happy like you did tonight. I'm still thinking about your tongue... it's going to be hard to sleep tonight, dreaming of you ;)

Surprisingly, that was enough to make Sean feel a little better. Seeing how satisfied he made James once again filled him with pride. Sure there was still a sense of humiliation that Sean felt, but weirdly, he liked the way the humiliation felt. 'Gosh... why does he make me MELT?!' Sean thought.

Eventually, Sean decided to lay in bed, like he was instructed, and stay there. He put on some TV, and after a few hours, he drifted asleep.

The next morning, Sean had woken up pretty early. He had overheard some talking going on upstairs and figured Derrick and/or Andrew were back. Sean immediately remembered the panties and looked down. The inside was now sticky from the dried-up cum, sticking to his crotch in some parts. Sean put some basketball shorts over the panties and continuously checked the mirror to make sure nobody could see them. He knew James had instructed him to wear them at all times- until he gets more pairs, and he was worried that if he bent over then they'd be visible. After putting a shirt on, Sean walked over to the bathroom to shower, freshen up, then made his way to the living room where he said hi to Derrick and Andrew.

The three talked for a bit, as they ate breakfast together. Sean was incredibly self conscious of the panties he was wearing. Eventually James woke up and joined them, and like before it was as if nothing happened between him and Sean yesterday. All 4 roommates were talking about boyish things: girls they hooked up with before, sports, and movies.

"I hooked up with this girl named Candy, a few nights ago- she was freaky as fuck!" James said.

"Wait was that the girl who you said left her panties here?" Derrick asked.

"Naww that was some other girl- I fucked Candy right after her. I dicked her throat down so hard."

"TMI bro..." Andrew said.

Derrick and James laughed. Sean pretended to laugh too, but he was confused-- was *he* 'Candy' in this story? He tried to sneak a glance over at James without making it obvious, but he couldn't get any clues from James' face.

Eventually, Sean walked over from the kitchen to the sofa, and put the TV on.

*Bzzz*

Sean took a look at his phone, and it was another text from James, who was now standing against the fridge- texting away. It was a repeat of the pic of him with cum on his face. Underneath it was a message: "YOU'RE Candy. btw. I hope you like that name... it'll be our little code name for you ;)"

Feeling horny, Sean played into the 'game', and texted back: "I love my new name, sir! I can't wait to have more fun with you soon." Sean's cock started to get hard again in his shorts. Horny, he wanted to feel James against him again. Still though, for some reason he felt calling James 'sir' was more dignifying than calling him his 'daddy.'

"Attagirl. BTW, there's some errands I need you to run today, ok? These will help make our sessions more fun. Last night, I ordered some packages online for us to use. I paid extra for overnight shipping, and had them mailed to a PO Box in your name. I want you to go over, bring them back home, take them to your room. Understood?" James' text asked.

"Yes sir, *tongue emoji*" Sean sent back. After that, James texted Sean the address to the PO Box, with instructions to pick up the package before the PO Box station closes at 5pm.

Sean spent the rest of the morning playing some video games with Derrick, while Andrew went to the gym with one of their frat friends. Meanwhile, James was watching a movie on his laptop. In the mid-afternoon, Sean left the apartment, shoes on and all, and headed over the PO Box station with his backpack.

The lady at the PO Box took his name, and then led him to his box, where there were quire a few packages- most of which couldn't fit in Sean's backpack. Sean brought them all home by taking an Uber, and when he arrived, Derrick immediately inquired about them: "Damn bro, you've been splurging! What'd you buy?"

"Uh....." Sean had no idea what was in these packages, but he knew they would somehow be sexual in nature. They were all relatively light so he assumed they were clothes of some kind.

"I uh.. got some books for school!" Sean said, as he continued to make his way downstairs.

Quickly, Sean locked the door and began to open each package. As soon as he opened them, Sean became a little scared.

Inside the packages was a French maid costume. A black, quarter-sleeved French maid dress with white ruffles, and a white headpiece. In another package was a purple bra that matched his panties as well as black stockings. The 3rd package contained lipstick, lipgloss, a general makeup kit, and finally, the last package contained 2 inch, high heeled shoes.

*knock* *knock* Sean quickly scurried to the door, and checked who it was. Luckily it was just James.

Sean opened the door, and James walked right in, closing it behind him, before kissing Sean. Sean immediately felt himself melt, as James' tongue entered his mouth.

After they broke off the kiss, James spoke up. "I got you a new outfit, *Candy*. I was hoping you'd have it on already, but I'm actually glad, I caught you before trying it on. Because I forgot to give you, *THIS*" James said, showing a shopping back, with women's shaving razors in it.

"Go in the bathroom, shave your legs, arms, and face, and don't come back until you're all smooth. I'll stay here in your room to make sure nobody sees all this." James said.

"James I don't know if I could commit to this. The Halloween Harley Quinn thing was just a one-time joke.. This is taking this a little too f-" Sean started.

James immediately cut Sean off (like he usually does), by pulling out his phone, with the camera roll opened. There was a whole album of photos and videos of Sean in compromising positions. "You came from a small town, conservative family right? It'd be a shame if someone shared these with your folks-- who are easy to find on Facebook... along with all the girls you managed to snag... Were those all lesbians? Or bisexuals? I was always wondering how you pulled so many 10's, but I guess some chicks love that feminine shit." James said, half threateningly, half mockingly.

"Another thing." James said, now with his hand on Sean's right cheek. "It's sir, or daddy. And you already agreed to be my property remember? So this isn't even blackmail, this is your master telling you what you need to do."

On the verge of tears from James' facebook threat, and cruel dig at his sex life, Sean meekly replied with a 'yes sir.' And grabbed the bag from Sean, and proceeded to walk to the basement shower, where he got in, washed himself, and proceeded to shave. It didn't take too long, given that Sean didn't have much body hair to begin with, and already had a clean shaven, smooth face.

Sean got out, and saw that his shorts and shirt were missing, with just his panties on the floor. James must've quickly snagged them. Putting the panties on, James dried himself with the towel, and ran over to his room, where he quickly closed the door behind him.

As he got in, James had him stand in the center of the room as he inspected Sean's body. "Nice, you look completely smooth." He said. James did a quick pull of Sean's panties from the front and noticed that Sean had not shaved his pubes. "I guess I forgot to tell you to do those. You don't have to completely shave them, but tomorrow make sure you trim them in a girly way."

"Yes sir." Sean said.

"Before you start changing, we need to do something about this." James said, pointing to Sean's hard-on in his panties. "Take your panties off. Lie in your bed."

Sean immediately went to the bed, and took the panties off. Soon after, he saw James pull his pants down, and take his own boxers off, throwing them to Sean. "With your left hand, hold these against your face, and breathe it in. With your right hand, beat off until it's all out of your system, then wipe the cum back into your panties."

"Yes sir." Sean responded, taking the boxers. Holding them to his face, he could feel the musky, sweaty aroma against his face.

"I went on a run while you were picking up packages." James said, proudly. James then came to Sean's side, and pushed the boxers closer to Sean's face, so that they were practically against his mouth.

While it smelled musky, Sean found the dominance erotic, and maintained his horniness. Sean then began masturbating. And after some time he ejaculated, and then wiped it against the insides of his panties, then putting them on. Putting the panties back on as they briefly brushed against his smooth legs felt admittedly nice. With his erection subsided, the panties fit noticeably better at the front.

With his panties back on, Sean looked over and saw James had recorded him. Tempted to scream, James opened his mouth, but stayed silent, knowing he had no strength to debate this with James.

"Should I put the maid costume on now... sir?" Sean asked?

"You may, Candy. But it's a uniform for you, not a costume." Start with the bra and stockings, then you can put on the uniform.

Sean obliged, grabbing the purple bra and putting it on. He figured James had guesstimated the sizes, and sure enough the bra felt about a few sizes too small, as it was rather right. Sean struggled putting it on, but he vaguely remembered wearing one when he dressed up as Harley Quinn that now, oddly-defining day. After getting it on, Sean began to feel a sense of pride. He looked at the mirror, and with his flaccid cock, and hairless body, he did look rather feminine. Next he rolled up the black stockings, which actually felt great against his smooth legs. "You have such nice legs, goddamn." James said.

"Thank you sir!" Sean said, half-faking the gratitude. Nonetheless, he was still embarrassed to be changing in front of James like this, into such an utterly feminine outfit, and thus didn't want to directly face him as he did- not caring if he was being recorded or not at this point.

Next, Sean put on the actual uniform itself. Like the bra, it was definitely tight, but manageable to put on. The quarter sleeves were absurdly short yet poofy. The end of the skirt was rather short, and if he bent over, his panties would be easily viewable to anyone behind him. The top of the dress was corseted, and as soon as Sean noticed, James came behind him and said " Let me help you with that, Candy!" Before tightening it as much as he could.

Sean gasped for air, as soon as James aggressively pulled the strings tight. With the corset now tied in a bow at the back, Sean's figure in the dress looked rather curvy. The bra was slightly padded, giving off the impression of small, yet perky tits. Sean wanted to walk over to the mirror to get a close look at himself before James handed him the shows. The shoes were a glossy black, and luckily for Sean, had a small heel to them, so they weren't too uncomfortable.

"You don't have to go all out on your makeup today, since you probably don't know how to do most of it. Just add some lipstick and some mascara if you can- but I want you practicing frequently, when you're alone down here." James ordered.

"Yes sir." Sean replied. Sean grabbed the makeup kit and walked over to his mirror, where he applied the red lipstick. Back when Sean had 'crossdressed' way back when for Halloween, he learned how to apply black lipstick and white face paint for his Harley Quinn cosplay. He also wore a corset back then but he didn't remember it being as tight as how James made his maid uniform. "Sir, I'm sorry, but I don't know how to add mascara," Sean said.

"That's okay- but make sure to practice, I'll test you later this week." James replied.

With the lipstick on, Sean fully examined himself in the mirror. While his hair was medium length for a man, he was able to move the front of it to the side to make it look sorta like a pixie cut. It was certainly passable. It was an interesting feeling, seeing himself all dressed up and in makeup. Like he did back in 12th grade, he really did look like a girl here. Especially as James, now stood behind him- much taller and bigger than him.

"You look gorgeous, Candy. Stand against that wall and blow some kisses, I'm going to take pictures." James told him.

Sean didn't want any more pictures taken of him, especially not all dolled up like this. And with him blowing kisses, and the pics of him with cum on his face like before... "Do I have to?" Sean asked, meekly.

James responded in a stern manner. "Candy. Don't make me repeat myself. I DON'T like repeating myself. What's a few more pics? Unless you want everyone from your hometown and classes to see what we've collected so far?"

"Ok... *sir.*" Sean said, pissed off. He liked the authority James had in their newly established hookups. But he could do without the blackmail.

Sean posed as seductively as he could. He bent over, gave some kissy faces... Stuck his tongue out. And after a few clicks, James seemed pleased with what he gathered.

"Great job, Candy. Now come give your master a blowjob as a thank you for all your new outfits. "

"Yes sir." Sean replied.

Once again, Sean blew his flatmate, wrapping his red lips against James' shaft. When James finally came he groaned a big sigh of relief, as Sean swallowed- looking up at his 'master.'

"Keep your outfit on for the rest of the day/night. We'll have more fun tomorrow." James said, walking out- not even thanking Candy/Sean for the blowjob.

"Yes sir." Sean said.

To Be Continued...