His Teacher, The Transsexual

Greg was compelled to thrust his hips up at Ms. Sin's sucking mouth. She smiled around his cock, swirling her tongue over the shaft. Ms. Sin let all but the tip fall from her mouth, sticky with spit, she bobbed her head back and forth on it.

Greg couldn't last much longer. It just felt too good. He was inexperienced and when Ms. Sin started rolling his balls in her fingers, he knew he couldn't stop from cumming.

"Ms... MS. SIN! Gonna...!" He called out. To his surprise, Ms. Sin responded by making sure his cock was completely buried in her mouth, she caved her cheeks in, creating a cocoon of pleasure.

Cum pumped through his shaft and shot in gushes from the tip of his cock. Ms. Sin kept her mouth wrapped tightly around him, swallowing the load greedily. Greg struggled for breath, thanking Ms. Sin for what she was doing.

Ms. Sin swallowed the last drops and only then let his shriveling cock fall from her full lips. She flashed a smile at him. Greg, overcome by what they did, pulled her lips to his. Ms. Sin responded by sucking his tongue into her mouth. Greg could even taste his own cum but didn't mind. This was every wet dream come true for him.

Her lips smacked against his as their kiss finally broke. "Thank you.. thank you so much, Ms. Sin." He muttered more words of praise for her wonderful sucking. Ms. Sin unbuttoned her blouse meanwhile and Greg's eyes were treated to the feast of her breasts. She reached around her back and with a quick move pulled her bra off to, dropping that and her blouse on the floor.

The big globes slapped against one another and her nipples looked just too inviting. Greg immediately buried his face into the protruding flesh. His lips and tongue found her swollen nipples and to Ms. Sin's delight, he started to suck on them. She wrapped her hands around his head and cooed.

Greg finally looked up from her breasts and spoke, "I want to make you feel good too, Ms. Sin. Do you want me to... to...?"

He looked so sweet and innocent between Ms. Sin's breasts. Her hands petted his hair gently. She was so turned on that her erection was burning a hole through her skirt.

"You mean return the favor? You should know, Greg, if you we cross this line, there won't be going back. And if we start, we can't stop. I'm so horny."

"I know..." He looked down at the stiff tent in her skirt. His hands slid down her front and squeezed the thick mass in her pants, "What do you want me to do?"

Ms. Sin got up and grabbed her plush desk hair. She pulled it over to Greg's desk and sat down.

"I want you to get down on your knees."

Greg obediently dropped to his knees before Ms. Sin. He looked up at her for further direction. Ms. Sin was naked from the waist up. That wasn't enough. She fumbled with her skirt and dragged it down her thighs and finally off her high heels. She was naked now, sitting in her chair.

Greg's eyes bugged out when he saw her cock fully hard. It was nine or ten inches and looked practically as thick as a baseball bat. Her smooth, hairless balls looked like the eggs of an extinct dinosaur. Ms. Sin giggled at the expression on his face when he saw her cock. She loved that look.

"I'll take another kiss now if you don't mind. Right here." She pointed at her cock.

Greg inched forward on his knees until he was between Ms. Sin's legs. His lips gingerly touched her shaft. It was like electricity shooting through her cock.

"Do that again." Breathlessly, she told him.

Greg took that cue and kissed up and down her veiny shaft. His soft, young lips felt destined for her swollen, rigid cock.

Ms. Sin couldn't wait any longer to get her cock into her sweet mouth. She grabbed her cock and a handful of his hair. Ms. Sin aimed her cock at his mouth, "I'm going to feed you."

Greg opened his mouth wide. She used the opening to push her cock between. The head brushed through his lips, entering his mouth for the first time. She moaned and let it sit there for a minute, taking in all the pleasure.

Ms. Sin fed another inch into Greg's willing mouth. He didn't know what to do with his tongue and flicked it across her cock head. That encouraged her to go deeper. All at once, Greg could feel that giant stick hit the back of his little mouth, he momentarily panicked, trying to pull his mouth off her cock, but Ms. Sin wasn't having that. She held his head tightly.

"Don't work yourself up!"

Greg tried to calm himself down. That was hard when Ms. Sin kept fitting more of her cock meat into his mouth, until the head hit the opening of his throat.

"I want you to create a vacuum seal." She told him.

His lips and wet mouth wrapped tighter around her cock. Ms. Sin threw her head back, keeping her tight grip on his head steady. Her hips started to grind back and forth, jabbing her cock in and out of his mouth. Greg tried to repeat what Ms. Sin had done with his cock, and swirled his tongue around the shaft. Her cock was a lot bigger though. Each time it went deeper in his mouth and pressed into his tight throat.

"I knew I'd have you cock sucking in no time."

Greg suppressed choking on the big meat. He sucked and kept the vacuum seal around this big dragon. He remembered what Ms. Sin had done to him and reached up to rub her balls. His fingers tickled the big nuts.

"You're a fast learner! That feels so fucking good. I'm losing my will power. But I've GOT to have your ass."

Ms. Sin pulled Greg's sucking mouth off her swollen cock. The tip popped out of his mouth, a deep purple color and shiny from his saliva.

"The first cum has to be in your ass. Get your clothes off now."

Greg responded by pulling his shirt off and stripping the pants that had been at his ankles off himself. He threw them in the pile with Ms. Sin's clothing.

Ms. Sin admired the naked body of her young pupil. His pretty cock was hard again. She couldn't wait to get inside his tight little hole.

She pulled Greg into her arms and shoved her tongue into his mouth, tasting where her cock had just been. Ms. Sin's hands ran down Greg's slender back and stopped at his butt cheeks. She kneaded the soft skin which felt so good in her hands. Greg melted in her arms. Her fingers teased his crack.

Ms. Sin brought her hand between their lips and sucked on her finger. He pulled her next finger into his mouth and lewdly did the same. Ms. Sin slid those fingers between his crack and rubbed against his asshole for the first time. This hole was private no more. It was Ms. Sin's to plunder.

"Turn around." She whispered through their kisses.

Greg pulled away and turned his face away from her, turning his butt toward her. Ms. Sin spread his butt cheeks and smiled. She wrapped her arms around his waist and brought his butt down against the tip of her snake.

"Take it easy. Just ease down." Ms. Sin whispered in his ear.

Greg clenched his teeth together as Ms. Sin's cock head pressed through his sphincter. The tight virgin hole could have made Ms. Sin pass out, the intense pleasure was almost too much.

"Urgmumg..mm." Greg struggled to accept the thick cock flesh. Ms. Sin steadily used her arms as leverage to pull him lower and gently pressed upward with her hips, so that her cock dug deeper into his asshole.

"Oooh.. that's good, Greg. You've gotta give it to get it. Where has this Greg been hiding all year? Your grades would be a lot better if I had this ass all along." Ms. Sin moaned.

More and more inches disappeared inside Greg. Finally, Greg's butt cheeks sat flush with her thighs. Ms. Sin held him tight, starting to buck up against him, her body humped his. The tight walls of his ass constricted around her cock.

"Bounce up and down. I want you to ride my cock." Her lips kissed his ear and neck.

Greg lifted himself tentatively from her pole, the pain was intense, but so was the pleasure he felt. Being so filled by cock and being so close to Ms. Sin kept his cock rock hard too. He fell back down on her cock. Ms. Sin felt like her dick was in a vice. A pleasure vice.

"That's it, Greg. Keep that up for me."

Greg's ass gave great resistance with each intake of Ms. Sin's cock. She started snapping her hips up, thrusting her cock into his tiny hole.

"Your... cock... it's so big..."

Ms. Sin thrust every last inch into Greg, "Tell me you like it!" She told him.

"I... I like it. I like it! Your big fucking dick is amazing!" The words popped out his mouth.

"Tell me who owns your ass? Tell who owns it!" Ms. Sin thrust up inside him.

"You do... you do Ms. Sin! My ass is yours. Just please don't stop fucking it!"

"Oh Greg. Dear. I'm gonna have to cum soon. Oh baby, come here!" Ms. Sin lifted Greg's aching ass partially off her cock for a moment so that she could turn his body toward her. They embraced tightly, Ms. Sin's tits pressing against his chest.

Her cock slid all the way to the hilt in his ass again. They kissed each other hungrily. Ms. Sin thrust her cock wildly into his hole. Greg's entire body bounced up and down with each thrust like he was riding a pogo stick instead of Ms. Sin's massive piece of meat.

"Get ready for me to cum! This ass is begging for it!"

"Oh fuck, Ms. Sin, shoot inside me. Do it!"

Ms. Sin threw all her weight into each thrust and was met by Greg's eager humping of her cock.

"Here I COME!"

The second Ms. Sin's cock was buried all the way in Greg's ass, she unleashed her load. The sticky mess flooded Greg's ass. His little hole milked every drop. Their tongues mingled together as their juices did. Ms. Sin's was impossible to ignore as it pumped out of her cock.

"Tell me how you want every drop!"

"Oh I do, Ms. Sin. I want it!"

Ms. Sin didn't let up with her pace, thrusting in and out of him, her balls finally emptied inside him. Cum ran down her cock and off her legs. Both Ms. Sin and Greg struggled to catch their breath. Ms. Sin brought Greg to her tits. He kissed and sucked in her nipple.

A few minutes passed before anyone spoke again.

"Class dismissed." Ms. Sin smiled.

She helped Greg to his feet, admiring the handiwork she had done on his ass.

"So you're going to be the first one here on Monday, right?"

"Oh yes, Ms. Sin. I'll be here. I promise."

Ms. Sin cupped his face and pulled his lips to hers. "Don't make me come looking for you again. I'm not going to be so nice next time."

Greg pulled his clothes back on and waved goodbye. They both knew this was only the beginning.

Ms. Sin looked through her files, picking up her phone, she dialed a number.

"Hello. This is Ms. Sin. I'm Greg's health teacher. I'm calling because I think Greg would really benefit from one-on-one tutoring. Please call me back to set up a schedule..."

Ms. Sin's cock started to grow again, "The sooner the better."