Peg

He confessed that when he began to tire that first night after delivering the first four or so loads into Peg's bottomless stomach, that he consented to let her work his prostate when she said that would go a long way toward earning that magical facial. He didn't describe what she actually did, but Tate gathered that she was deepthroating him while her magic fingers diddled his gland. "She made me cum for what felt like two minutes straight and never spilled a drop."

"So I nut, she swallows the whole thing and she keeps me hard but I'm so tired. Then she just picked up my legs, put them over my shoulders, folding me in half. She sat on my legs in that position. She's tiny but it doesn't take much weight once I was in that position. Uncomfortable as fuck, but I could do fuck all to get her off me.

"Then she stuck her fingers of one hand in my ass and started jerking me off with the other. Those nails, inside me? And they're natural, not acrylics so they're strong and she can use them like daggers if she wants. Just... Whoa." Lee paused. "I've never felt anything like that. Her fingers and those long nails. It was amazing. And she's, like, humming or whistling some tune, smiling. She's enjoying this.

"I wanted to explode but she'd just ... I dunno, sense that I was getting close to cumming and then back off and say 'Not yet!' and laugh. Or else just keep humming and squeeze my nuts hard. I knew what she was doing and I couldn't do anything to stop it. It was really uncomfortable being in that position, but she was just keeping me on edge, so there was so much pleasure at the same time. She held just enough pressure to keep me in that position with no restraints. She said she wanted to see my face as I realized that she'd won and would collect her prize.

"Before I knew what was happening, there was so much pressure building up. And the things she was saying to me, just in that quiet whisper, was so filthy and hot. I wanted to cum so badly but she wouldn't let me.

"She just slowly jerked me off for ... it felt like hours. And when I thought I couldn't take it any more finally just lightly scraped a nail against the head of my cock and *boom* I exploded. She aimed my cock and made sure I covered my face and then she squeezed my nuts so my mouth was open and made me swallow the rest. She just giggled that cute little laugh the whole time. She looked so happy. Then she made me clean off the fingers she had up my ass with my mouth. She was still crushing my 'nads so I wouldn't bite her fingers. Those nails, man. I wasn't gonna mess while they were on my balls." Lee looked like he was recalling something that happened to someone else.

"Every guy she does this "wanna be my boyfriend?" bit with, she teases them, humiliates them, milks them dry, makes them cum on their own faces and throws them away. With her skills, she could get money or whatever from guys. Anything she wanted, really. Fuck, she'd make a mint on a sugardaddy site. She doesn't though. She says it's more fun this way. That taking confident men, teasing them to the point where they would agree to do the most degrading shit, sexually crushing them and then leaving them begging for her to treat them even worse gives her an orgasm that cocks can't. She says she's never had to get a facial under that condition even once. No one has been her 'boyfriend' so far."

Other tidbits Tate learned were that "Peg" wasn't even her name. It was Elena. Telescope gave her the name after she got him into prostate stimulation. He liked it so much, she would tie him down and use a strap on and then bugger him for hours. She called him "The Fountain" from how much he sprayed. Then she started making him eat his own cum, the same way she did to Lee. She said he was a bit rude when they first met, so she insisted that she was extra cruel with him; she didn't say what that meant and Lee said he didn't want to ask. Whatever it was, it was permanent. She broke him so badly and now he can't cum any other way. Now he has to beg her to come over and give him relief. He just didn't trust anyone else to do it the way Peg did.

And, apparently, Telescope was actually a little smaller than Lee but was a grower.

"She said I was good in bed and we can still be fuckbuddies, but if I wanted something regular with her, she'll make me eat my own cum at the end of each session with her. She'd make me eat two loads if she spent a full night."

"So, she's stayed the night at least once a week for, what? A month? And each time since...?" Tate asked.

"Yeah. The last few weeks were..." Lee paused with that far-off look again.

"She's currently seeing a fund manager she says is at least two inches longer than me and maybe two bigger around. She says he makes her squirt, cums buckets and has both incredible stamina and control." Tate nearly swooned at the idea of skinny Peg spraying girl cum. Lee didn't notice and continued on.

"She said she'd held off doing the 'boyfriend' bit with him so far but would do it this weekend on him. She already knows he's the one to actually win her prize but isn't sure if he even wants it. If he goes for it, she'll cut me off and block me then and there." Lee seemed genuinely bummed a bit. Tate knew better than to actually feel sorry for him, but he could sympathize with the feeling. "Dude, I can't explain how fucking amazing she was in bed. The fact that she was kinda plain looking under all that just made it so much hotter. The other day, after fucking me senseless and as she jerked me off to facial myself, she said that if I really wanted, she may be able to talk the new guy into letting her give me his chocolate cream pies."

Tate's eyebrows raised.

"Eat his cum from her ass." Tate cringed. "But then she'd have to piss on my face to remind me who to thank. You gotta understand, she had me so close on edge I'd say almost anything to get relief. She's like a little ninja giving the hottest torture ever and I needed to cum sooo badly." Tate didn't ask further. Her humiliation and degradation of Lee was extensive but his short term need for her brand of pleasure was so extreme, he refused to see it. Everything she was proposing was just ... awful. But there he was, explaining it like it was a treat. A perverted Stockholm Syndrome.

Tate answered a knock at the door at 12:30 a.m. that Saturday morning. There was Peg, cheeks flushed a little, wearing five-inch stiletto heels with black hose, what looked like white flakes all over her face, a short black over coat that hung open and exposed her front and nothing else. The small nipples on her flat chest had small barbell piercings through them and looked like delicious dark berries. Her pussy was hairless but looked to have been recently and thoroughly used; and there was her heavenly musk. She smiled at Tate as she walked past, a little wobbly. She lifted the back of her coat and flashing her small, porcelain white ass and smirking as he gawked at her. Buried in the center of it was a flash. It took a second, but Tate realized it was a metallic butt plug.

She went right into Lee's room. Hushed voices spoke in the room and she strutted out a few minutes later, her smile was the satisfied one of a woman used to getting her way. Seeing herself out, she stuck out her tongue at Tate, showing the stud piercing there and raised the buttplug to gently wipe it across Tate's lips and blowing him a kiss as she closed the door. Tate didn't move for a good thirty seconds, before wiping his mouth. Tasting whatever she put there didn't seem like a good idea.

Lee emerged a minute later, his face flushed a crimson red and wet, with his toothbrush in hand. "She didn't even make it to midnight before she begged him for a facial. She'll be by Tuesday night after their next date.". Tate didn't say a word, but he was rock hard and when he went back to his room, he came quickly.

Finally, the universe felt a little more friendly. Maybe she should have licked his lips?