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Teresa lorded over Jeremy, the springs on her mediocre dorm bed giving her a bit of a bounce as she stood over her best friend. He was a little bit worse for the wear, decked from head to toe in a French maid's outfit that seemed more fitting for a Japanese maid cafe more than bedroom fare. At least it accentuated his close-cropped brown hair and figure, even if he was sorely wishing the latter wasn't true. To pass the time, the young maid tossed and turned lightly on the bedspread, his arms already tied with a few belts through the headboard above him by his good friend.

"Last time I bet about what grade you get in Intro to Psych," Jeremy shouted upwards as his arms squirmed in the makeshift bonds.

With a sly look on her face, Teresa simply cooed back, "Believe me, Jer, you might just be thinking otherwise soon!"

The two had been best friends ever since childhood, growing up together in the same neighborhood. Going to university together was just another added bonus. In fact, the only reason they made these silly bets mostly hedged upon the fact that they were both uncomfortable with the entire concept of "friends with benefits," but this was a fine way of skirting the issue. Through the past few years both Teresa and Jeremy were able to explore themselves fully and intimately, feeling complete comfort in exploring each other's particular sexual inclinations. This, in particular, was quite the wild afternoon.

Teresa quickly dropped to her knees, having them fall next to her lovely maid's sides as they straddled his silky black garments over his stomach. She squirmed a little bit, just to tease a reaction out of her dear friend. He squirmed breathlessly with an adorable blush, his typically cute feminine reaction to her advances. Smiling in approval, she knew the time was right.

"How are your breasts this evening, my dear servant?" Teresa quickly groped where Jeremy's breasts would be if he were as feminine as he usually acted, squeezing his chest and nipples and swirling her hands around with a hearty laugh. Her own pair was quite bountiful, as rich as two perky oranges, as she leaned her chest in closer. Her straight, flaming-red hair brushed across her breasts, partially draping the captivating view, as she let her thin frame taunt her captive friend however she desired.

Jeremy, still completely flustered and huffing at what was to come, couldn't respond. His mind was already slipping off into a blissful place, and she had barely begun! If he got off already that would be a waste of this week's bet, and that was the last thing he wanted. Still though, Teresa knew how to shop around, and slipped a little bauble out of her back pocket of her jeans as she lightly sat on her friend's pelvis, purposefully putting pressure onto the base of his enlarging cock with her backside.

She eyed the little ring with interest, wondering if the text on the packaging could possibly live up to its promises. Then again, it did cost enough in order to justify its potential worth, and her friend Steve would never steer her wrong in matters like these.

Teresa sat up a bit and slipped her hands beneath Jeremy's puffy skirt, making sure to tease the outside of his legs and his ass as she slipped his silk panties a little bit down his shaved legs. She always liked that about him, how he really did like being femmy beyond belief. Dangling the ring off of her index finger, she pressed the sex toy against Jeremy's enlarged head, slipping it past his ridge with a bit of force as he arched slightly upwards at the powerful sensation, quickly relaxing as Teresa coaxed the object to the very base of his shaft.

The shapely female simply grinned from ear-to-ear, looking directly at Jeremy as she tapped his cockhead for attention before swirling his enlarged manhood with the tip of her index finger. Without any further ado, Teresa slipped a hand underneath Jeremy's length so she could massage his balls within her palm while her other hand began stroking.

Jeremy's gaze was fixated only on the ceiling as his dear friend started working, eye rolling back into his head as he felt himself reach his usual seven inches of engorgement. Amidst all of the stroking and molding, Teresa finally felt the benefits of the cockring activate, giggling in pleasure as Jeremy's balls became malleable, almost as if they were made out of a constantly-expanding clay as she started crafting them to her own specifications.

Teresa slipped both of her palms down to the rapidly growing testicles, feeling them pulsate with a wealth of his seed, knowing that the second effect had kicked in. Not only would he fill with an abundance of seed, he would keep doing so until he expelled three times the maximum his body could possibly withstand. She blushed wildly, knowing that this was one of the few fetishes of hers that she kept secret, even from the maid below. She hated keeping these little tidbits here and there, and she knew that she could trust him, but sometimes she dreamt of nothing more than being completely covered in his cream, within and outside, smearing it all around his sexy, femboyish self.

The minutes passed as her hands continued sculpting a masterpiece, already making his spheres already reach melon-levels and continues onward, knowing by their purple hue that her friend must be in searing, pleasurable pain from their fullness. Teresa paused for a moment, his sack looking as if they contained two hefty watermelons, as she laid her chest down upon them. Her breasts added additional pressure, and she knew from his wildly throbbing cock that his body couldn't take the build-up any longer.

Whimpering emanated from Jeremy's mouth, nicely high-pitched to the point where they melted quickly into squeals. The time was right. Today, though, his balls looked so adorable in their shaven state, and the wealth of cum within them made them spectacularly soft. Taxing her brain, Teresa believed Jer could hold out for another minute or two longer...

Teresa slid up a bit more as her breasts and stomach rubbed against his immense balls, slowly kneading them around through her own bodily thrusts as she wrapped her lips slowly around his thick, throbbing head. Two full lips wrapped around Jeremy's crown and slowly worked down his shaft, adding saliva as lubrication to her beloved's length. He may not be able to even release a drop of pre, but he may as well have the additional pleasurable sensations he would normally have. He deserved that much, at least to her.

Some minutes had passed before she knew that Jeremy was well beyond any sort of release he had in him, herself soaking through her panties with her own honey as she anticipated the best part. Her lips left his delicious cock, a few strands of saliva still trailing between his head and her mouth, as she raised his manhood upwards. Grabbing the cockring, Teresa removed it in one expedient motion.

Cum immediately burst forth from Jeremy's tip, shooting upwards into the air as if he was a human volcano, spraying his seed all around the room nearly a foot and a half in the air out of sheer force. As his juices poured around the room like a heavy rainstorm, the flow soaked his bed, the two pseudo-lovers, and made an absolute mess of his desk and the finished homework that laid upon it. The lamp on the nightstand fell over after a huge slosh and spurt, and the room darkened even more once a particularly large eruption thickly soaked the window.

Jeremy's musky odor lingered in the air as Teresa stradled on top of his cock for the last few minor pulsations, enjoying the sensation of milking him between her cheeks. Squishing her way up to his chest and laying on his soaked silk clothing, Teresa gave her exhausted friend a kiss on the lips. They usually shied away from such obvious means of affection, but this was a reaction better than she ever could have expected and she cared for him enough to thank him in the sweetest way she could.

Breathlessly and wordlessly, she laid on his chest for a long while, breathing in time with him and stroking along his drenched arms. As she rested her cheek next to his, she thought about what they would bet on next week. No matter what, there were two things clear in her mind: she was going to let him keep the ring, since the smile on his face was more than reason enough to know that he would want it for his own.

...and that, no matter what, she was going to lose next week's bet. Her maid, without a doubt in her mind, truly deserved it.