Gurlyboi

By Cumm Slutt

Published on Sep 11, 2017

Transgender

DISCLAIMER: All characters are fictional, no relation to anyone living or dead, all are 18 or older. If you do not like sexually oriented material, LEAVE NOW.

Harry, 19, was on his knees with a 40-somethinng guy's cock in his mouth locked in the man's office, slurping on it hungrily, cuddling his bloated balls and a finger squarely up his clutchinng asshole, the guy's hands guiding his head up and down his thick cock, feeling his fingers tighten as he got closer to cumming.

"Oh fuckk... oh fuck bite my fucking cockhead.... hard... it will make me.. ouu yesss yes yes yesss. Gonna cum.. gonna.. oh fuckkkk!" and shuddered, hot spurts of cum hitting the back of Harry's throat, swallowing just as fast as he could, ignoring the gag reflex (he learned how to do that long ago).

Harry said softly, "Seventy-five... did you like it?' and held out his hand.

"Oohh fuckkkk yess... here's a hundred... see you next time.... Tuesday, early again, before anybody's here, ok? Wanna wear something gurly?'

"Ouuuu yesss.. darling!" Harry groaned, just the mention of it getting him going. He waited for the guy to let him out, giddy with delight to have earned the hundred. In the first 3 days of the month he'd made enough for all his bills for the entire month, sucking and getting fucked - 3 guys on the 1st, 2 on the second, and now this guy on the 3rd - $500 total. He had one more appointment this afternoon, he'd eat breakfast at the gurlyboi diner, then get ready...

"Hi Harry!" Josephine tittered as Harry walked in, from behind the counter. "What can I get for ya today?"

"Mmmmmm... 2 eggs over easy, turkey bacon, hash browns with ketchup..." Harry smiled, sitting at the counter. He and Jo had been friends for quite a while. They'd had a little affair, like most guys would do, but were now just friends. Just then someone he didn't know came in and sat down right next to him, surprising him.

"Hi! I'm Jenni, good to meet you!" and held out his hand.

"Hi, I'm Harry, good to meet you too!" and shook his hand.

"You don't look hairy to me.... you have nice, smooth skin, at least what I can see..." and they both laughed and laughed. "I'm 20, legal at least in this state, and you, honey?"

"I'm 19, let me buy you breakfast, doll..."

"I thought you'd never ask...!" Jenni giggled and accepted, the two eating voraciously.

"You live nearby?" Harry asked, making conversation.

"Well, in the alley out back, for now..." he bowed his head. "But, I've got a guy lined up for 2 days from now... maybe... $20 at least!" he said proudly.

"Honey, we gotta talk... " Harry said, paying the bill and leaving Josephine a tip. "Come to my place..."

"To... or in?" Jenni grinned as they left, walking a few blocks.

"Yummmm.... both, darling!" Harry moaned with delight... he knew this was fate in the making!

Harry unlocked the door and locked it behind him. His apartment was clean, two bedroom, one bath, not luxurious but spacious.

"First, let's get this out of the way..." Jenni moaned and they instinctively locked lips, passionately making out!

"Ouuuu baby, now this is in the way..." Harry moaned, feeling their hard cocks in their panties. Harry sunk to his knees and pulled out Jenni's throbbing hardon and sweetly started to suck him, then Jenni laid down and they 69'd, sucking each other into glorious orgasms! They both swallowed each other's loads, kissing and rubbing and enjoying their post orgasms. Then Harry deliberately started fingering Jenni's asshole and slid down to lick it out....

"Ouuuu baby that feels so good! Please, don't stop!" getting on all fours. By then, Harry was hard again and slowly eased his cock inside Jenni's ass, fucking him, seeing if he was a virgin. But, his asshole yielded easily, but firmly, giving him a great amount of hot, burning pleasure, and he fucked him until he came inside him, then tongued his own cum out of Jenni's ass.

"No need to return the favor, you passed all the tests!" Harry groaned, making out with Jenni.

"Tests? What do you mean?" Jenni looked at him quizzically.

"I wanted to see how you behaved and reacted to my loving, babe.... and you did wonderful! Would you like a job? Like, partnering with me? Starting this afternoon? I've got a date at 3pm....." Harry said softly. "And it is for my regular fee, $75.... not no 20 bucks!" Harry giggled. "You're worth at least that! I'll call him and see if he wants double the pleasure for $150....."

"Bruce? Harry. Got a friend... ouuu yess I can have him cum along with me, both being gurly.... $150 ok? Great! See you then, before your wife gets home, darling... be ready!" and Harry hung up.

"There! Date is set. And he always pays for the cab, too. Let's get ready, hunny..." Harry filled Jenni in on Bruce's wants and desires, and that his Dominatrix wife would be home at precisely 5:30 pm from work and would catch them in the act......

......................................................................................

Bruce hung up and he absolutely quivered at the thought of two... yes, two, gurlybois cumming to play with him! He stripped and showered, dried off and began putting on his makeup, then pulling stockings up his shaved legs, fastening a bra and garterbelt, attaching garters to his hose, and slipping on his high heels just as the doorbell rang!

"Hi Brucie! This is my new friend, Jenni... " and Jenni made out with him, both tasting each other's lipsticks.

"Tea, ladies?" Brucie offered, and they all primly sat down at the dining room table, sipping tea as Brucie felt up both of them, getting them turned on, making out with each of them, and both returning the pleasures being afforded.

"Ouuuu Brucie... let's get comfortable, honey..." Harry cooed, leading him and Jenni to Brucie's bedroom, all of them making out passionately along the way. "Now, baby... lay down and prepare for thrills you've never even imagined!" Harry cooed, one sitting on each side of him, slowly removing his panties which were soaked in precum. "Jenni, would you do Brucie the honors of licking out his cummy, wet panties for him while I start to suck his hard fucking cock? I will certainly save some for you...." and bent down and took his pulsing cock in his wet, lipstick'd mouth as Jenni put his panties over his head and started licking his precum from them, and alternately making out with him as Harry sucked his cock for him, totally thrilling him!

"NNnooooo.... Brucie, you can't cum yet, darling..." Harry moaned, taking his mouth off his cock, admiring his lipstick stains. But we can rub cocks together, hon..." and got on top of him, slowly kerking them both sensuously. "Jenni... why don't you give Brucie a footrub with your hard, thick penis and cum all over his toes, then lick his toes off. We can cum all we want, just that he can't...." Harry cooed.

"OUuuuu darling Brucie... I just love your feet and toes! Can you feel my throbbing hardon on them, baby?" Jenni groaned, getting into it.

"Nooo... you can't cum, baby..." Harry moaned, feeling him tense up and wrapping his fingers hard around his cock to stop him. "There, better?"

Jenni exploded all over his feet and wriggly toes, shot after hot shot of creamy cum, then bent down and started sensuously licking his own cum of them, savoring in it. Harry leaned back and kissed Jenni hotly, exchanging mouthfuls of hot cum, hen turned back to Brucie and made out with him, giving him a big wad of hot cum to enjoy.

"Oouuuuu fuck, gurls.... you both are so fucking HOT!" Brucie groaned. "Fuck me in my mouth and ass, darlings!"

"Ouuuu that would be wonderful! But.... we gotta cage you so you own't cum, honey..." Harry giggled, getting up and getting some ice cubes out of the mini-fridge. "Get your cock and balls to cool down, baby!" and held them on his groin, feeling him shrink almost immediately, the cold making his arteries contract, draining the blood from his hardon. "There! That's better!" and affixed the cage on his cock and balls, then had him flip over on all fours.

"May I start to fuck your mouth for you, Brucie?" Jenni asked sweetly, guiding his hard-again cock to his lips, of which Brucie started to immediately suck his cock for him.

Meanwhile, Harry spread his asscheeks wide and lubed up his canal thoroughly, slowly pushing his cock up his lubed ass, and began fucking him over and over. "Do you like that, Brucie? Huh? Is this making you feel like the dominated whore slut that you are? HUH????" Harry taunted him.

Suddenly the door opened and in came Sue, his Dom wife. She assessed the scene, moved Harry out of the way once removing her dress to show her Dominatrix outfit, and pushed the handle of her whip up Brucie's asshole, fucking him with it...

"OHHH DARLING! You're home and caught me being a whore slut to these gurlyboi's....making me suck their cock and get fucked by them... hit me, beat me, make me feel cheap!" Brucie blubbered, shaking and moaning.

Sue replaced thw whip handle with a huge big black strapon vibrating dildo and plowed his stretched asshole with it. On the inside of the dildo was a 'clittifier'..... a hard nub that would stimulate her dripping clitoris, plus transmit the vibrations to her, making her orgasm violently. The more she fucked his ass, the better it was!

"Uncage him... both of you sluts get down on his cock and make him cum!" she ordered, whippinng his back with every thrust of her vibrating dildo.

Harry and Jenni complied, releasing his cock, sucking it, makng him hard and throbbing, laying against him, rubbing all three of their cocks together in a frenzy, all three of them orgasming from the masturbational frotting, all shooting load after load of cum on each other while Sue orgasmed repeatedly, sliding thevibrating dildo out of his asshole. Harry got behind Brucie, licking his asshole out while Jenni licked up all the cums, sharing it with Brucie and with Sue, heavily making out with both, then all of them collapsing, groaning and grinning!

Finally Bruce stood up, went over to his wallet, pulled out 2 hundred dollar bills plus a fifty... "Here, oh fuck this was so fucking worth it, wasn't it, Sue?"

"Ohhhhhh fuckkkk yesss.... I orgasmed sooo fucking much...!" she groaned, smiling....

Harry called a cab and they left and went back to his apartment, changed, then went and bought Jenni (James) a whole new outfit - shirt, slacks, sportcoat, socks, shoes.... the works! His first new outfit since he could remember! They went out to dinner, splurging on steak, lobster, shrimp and scallops, went back to the apartment and collapsed; gorged!

...............................................................................

The next morning they got up, James more than happy to have slept in an actual bed with clean sheets, then to eat breakfast with his now-good friend Harry and take a shower together, playing extensively, then getting dressed and going out for lunch at a nice place was a totally different situation than he was in yesterday! They did more shopping, James purchasing more clothes (albeit less expensive than the day before, but with his own money this time from his earnings from last night) and so grateful to be able to! As soon as they got back to the apartment he gave Harry an extra special blowjob just to thank him again! Harry got a call, somebody who talked to Bruce, and wanted 'the twosome' to service him the next day and harry set it up.... it was apparent that they made a good pair!

..............................................................................

Next: Chapter 12


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