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CYOTF (New)

Hold Out

added 4 years ago BM S TG

"What's the endurence challenge?" Derrick asked sheepishly, still not fully committed to it.

"The rules are simple. You've got yourself a nice little pussy and as it so happens I'm in the mood for pussy. So I'm going to eat you out like an all you can eat buffet. You will have to keep from cumming. Every time you do, you'll become just a little bit more feminine. If you win, you'll be completely restored."

"But... if you win the first round, doesn't that mean I'll need to win twice?" Derrick asked. This was good, he was trying to establish all the rules before committing.

"No. For you it's instant death. Even if I've managed to turn you fully woman, winning once guarantees you'll go back to normal. However, once you've become woman enough, you won't want to," Lara smiled.

"H-how long do I need to hold out for?" he asked nervously.

"Well, I'm trying to be fair here. You have a brand new pussy that's sensitive and I'm very good at eating women out. So... let's say sixty seconds."

Derrick blinked, surprised at how manageable that seemed. "That's it? Shit that shouldn't be too hard," he chuckled.

"Careful," Lara grimaced, "normally your arrogance would have me extend the time, but it so happens I'm feeling generous. So, do you want to go?" she asked. Derrick glanced at me, then at her, then back to me as though looking for some suggestions from us.

"Okay, okay, when do we start?" he asked with a huff.

"Just as soon as you lay down and spread your legs. You can assume any position you want, just so long as I can get to your pussy," Lara explained, unfolding her arms as Derrick took up a standard laying position, spreading his legs open. "Jethro, take time will you?" she asked. I looked down at my watch and set it to the stop watch mode.

"Ready," I said. Derrick repeated my statement and Lara grinned. "Begin," I announced, pressing the start button.

1... 2...

"Oh, oh, ooooh, fuck!" Derrick shouted as I looked up to see him lurch and shake with an orgasm. "Holy fuck, what the hell?" he yelled at Lara who grinned like the cat that ate the canary. Two seconds, two seconds was all he could muster on the first round. "I really wasn't prepared for that," he mused as his body hair seemed to vanish leaving his entire physique silky smooth, save for his facial hair.

"I told you Derrick, I'm a Succubus. I'm very good at what I do. Feel free to change your position. I don't care how you hold out, you just need to," Lara explained.

Derrick sat up and huffed, seemingly considering what had happened. "Hey, my body hair's gone," he muttered.

"You can stop the game at any time, but all changes will be permanent. This first round's change was relatively minor."

"Let's keep going," Derrick declared. "I know what to expect now." With that I reset the stopwatch and announced we were ready. Derrick laid down again and Lara neared his hole. I gave the call to begin.

1...2...3...4...5...6-

"Ooooooh fffffuck!" Derrick howled again. "How... how long did that one last?" he cried.

"Barely six seconds," I answered. "You need to make it harder on her."

"I did, I clenched up so it wouldn't be as sensitive," Derrick replied, his beard retreating beneath his face to leave behind baby smooth skin.

"It doesn't work that way," Lara shook her head. "Come on Derrick, give me a challenge. Show me you want your manhood back."

Derrick agreed and we prepared for round three. Derrick was now sitting up, crossing his legs to limit access. Lara was determined though, I could see it in her eyes.

Round 3
1...2...3...4...5...6...7...8...9...10...

"Oh, oooh, oh, why are you so good at this?" Derrick cried. I watched as his feet seemed to be shrinking down, his size nine becoming a more dainty size five that actually seemed to fit his shortened stature better.

"That was a bit harder," Lara applauded. "Access was limited, but..." she let out her tongue, the monstrous pointed thing seeming to extend six inches before stopping, "My tonge can still reach."

"What the fuck?" Derrick hissed. "Hold on, so the rules state you have to eat my pussy right?"

"Just your pussy," Lara confirmed.

"Okay," he smiled, rolling onto his stomach, crossing his ankles and lifting up into a cobra stretch. I cocked an eyebrow rather impressed. Access to his pussy was certainly limited like this, but rules stated that it had to have some avenue of access. Something Lara reminded him of. He protested, but the threat of losing his masculinity permanently forced him to grudgingly comply opening his legs less than an inch.

Round 4:
10...11...12-
"Oh fuck!" Derrick called out, slamming his fist on the floor as a small volume of lubricant squirted from his pussy. His legs slimmed down to match his small feet. "Again," he demanded. I reset the watch.

Round 5:
10...11...12...13...14...
"Shit, of fuck, oh, oh, fuck why?" he hissed again, his waist seeming to sink and ass with it.

"You can always try a different position," Lara announced. At this point I thought she may just be feeling sorry for him, but not enough to stop. Round five and he hadn't even made it halfway. I shook my head. I had a feeling this would end badly.

"This is the best position I can think of," he replied, then resumed the stretch.

Round 6:
10...11...12...13...14...15...16...
He howled again as the floor beneath his pussy became moist and a puddle formed, spreading out from his hips. His ass began to expand, it's shape taking on a feminine bubble butt. I couldn't help but get hard looking at it. Lara scooted him away and handed him a towel to dry off while she cleaned the floor. I had to admit, she was a good sport.

Round 7:
15...16...17...18...19...2-
"Mmmmmh," Derrick squeeled as his voice suddenly went up a few octaves. His shapely ass began to tremble and quiver as yet another climax rocked him. As his voice changed so did his profile, ribs shrinking to match his hourglass waist. He decided to try a new position, this one on his back with one leg posted and the other overtop. Surely this would make it harder on Lara as she'd have to sit at an exceptionally awkward angle to get him.

Round 8:
1...2...3...4-
"Dammit that's not fair!" he screamed, Lara giggling.

"It most certainly is. Honestly, how did you not know I'd attack from below." I watched as Derricks thighs thickened.

"Oh, shit," he exclaimed, looking at his increasingly feminine lower half for the first time, voice now sounding prepubescent. To his credit, he decided to take the thighs as a hidden blessing. With no thigh gap he crossed his legs, only the tip of his slit being visible. Surely Lara would have a tough time reaching his most sensitive innards.

Round 9:
20...21...22...23...24...25...26...27...28...2-
"Okay, okay, fuck I give I can't hold it anym- ooohhh..." he hissed as a climax rocked its way through him. His eyes rolled in the back of his head. All I could imagine was that the feminization was starting to affect mannerisms and brain function. I mean, Lara did say at a certain point he would just give up, and here he was just about half way through when he gave in and allowed the climax. Sure enough I saw his nipples shrink just as two mounds began expanding under them. He made it to a small B cup before they stopped. He gave them a stare, poking at them with two masculine hands. The sensation sent a shiver through his body. He heaved a defeated sigh.

"You're not giving up are you?" Lara asked, sounding genuine. "You were almost half way. If you hadn't given up... well, who knows."

"Just... just give me a minute," he waived weakly.

Round 10:
25...26...27...28...29...30...31...32...33...
"Oh," Derrick squeeled, tensing up to stave off the climax.
34...
"Ah,"
35...
"No, no, no, oh fffffuuuhuhuck!" he cried, voice raising to an effeminite tone. His hands shrank, the large fingers narrowing and nails extending out to show the tell-tale signs of gentle breeding.

"36 seconds," Lara grinned. "You're getting there."

"But do we want to?" Derrick looked up, seeing a little black girl standing in the corner, invisible to Lara and myself, but being a manifestation of his conflicted mind.

"Who-"

"I'm you dummy!" she screamed. "Or at least, who you should be."

"I don't know what- oooh," he squeeled again, this time squirting a little. 39 Seconds was the final count to round 12. Derrick saw the girl grow a bit bigger, smiling as she did. His arms and shoulders thinned, looking much more feminine.

"Of course you do. I'm the female side of your brain. You know, the one that's going to win out. You should never have taken this challenge. Succubus or not, you're a rookie who hasn't even had your cherry popped. I'm sure Lara could stare at it and you'd cum. But don't worry, we'll be just fine. Just think! We'll never have to deal with Charity again, and we'll get to enjoy fucking again."

"No, that's not who I am. I'm a man," Derrick shot back.

"Hm... your current body says otherwise."

Round 13
40...41...42...
"Oh, yes, Lara, yes, fuck," Derrick screamed, his face and jawline reshaping to a narrow feminine one. Lara looked down, smiling to herself. It seemed she was having fun regardless of how this ended. I was rather concerned but it seemed that with Derrick's face, the last of his masculinity was gone.

"Derrick," Lara smiled lustily, "I'm so glad to see you're enjoying yourself. Did you want to stop the game?"

"No," Derrick replied in a voice he no longer recognized. "I can make it, I know I can."

"Math, really?" the girl in the corner scoffed, crossing her arms. "Girls don't need to think about math. Why crunch numbers when we can think about shoes, dresses, jewelry, and boys..." a glint appeared in her eyes as she turned her attention to myself sitting on the bed resetting the stop watch for the thirteenth time. "He's turned on, you know. He likes the feminine you, the REAL you. Just let me take over from here. You'll love it, I know you will," she offered.

He closed his eyes and signalled for us to begin again, likely thinking about math and tensing to reduce sensitivity and stifle oncoming climaxes.

Round 14:
40...41...42...43...
"11 x 12 = 132"
...44...
"120/6 = 20"
...45...
"6^2 = 36"
...46...
"13 + 56 = 69..."
...47...
"Sixty-nine... fuck I want to eat that Lara bitch out!"
...48...
"Oh, fuck, oh, Lara please, oh fuck, fuck, fuck!" Derrick screamed finally lurching back against a particularly strong climax. His- her hair began to grow out, flowing as though it had already been beneath the skin just waiting. Her tits were now a modest B cup and there was not a single masculine feature left. Derrick huffed, uncertain of what to do. The girl in the corner was huge, so big that she had to kneel and her head was still touching the ceiling.

"Let me take over," she smiled. "You've already lost. Let's just have fun."

"You're fucking with me," he hissed. "I could have had that one!"

"I'm just trying to have fun, Dernise, it's what everyone wants. What girls want. Jethro over there was a nice big cock. I bet it would fit in our virgin snatch nicely."

"No, I'm getting my manhood back, whether you like it or not."

Round 15:
Derrick tried to concentrate as best he could, using every trick he knew as a man to try and stifle the sensations his womanhood was feeling. Doing math, exercising breathing control, thinking of Kevin Spacey... it seemed to be working too.

...50...51...52...

"Oh, yeah, oh, Jethro fuck me harder," Derrick looked at the girl in the corner who bounced up and down on an invisible dick, looking like the mirror image of Derrick. He couldn't take it, climaxing at 55 seconds. I watched as his breasts ballooned to double Ds, ass push his back of the ground with newfound volume, and his lips and lashes all plumped and lengthened. Derrick was no longer man. Her eyelids fluttered as she now revelled in the climax.

"Just one more..." Derrick muttered. "Just one more round."

"Yes, Derrick, just one more round," Denise smiled, her phantom body now engulfing the whole room. "Just one more and we'll be the woman we're meant to be."

Round 16:

This was it, Derrick could feel it. Do or die, that was what it came down to. Denise was influencing his mind, a giant against what remained of his masculine mentality. But he would succeed. He knew Lara's techniques, knew what she would do, and knew how to block out the sensations. All he had to do was hold out.
...15...
"Alright, keep it up," he thought.
...30...
"Half way there..."
...45...46....47...
"Almost, just hold on," he saw Denise standing in the dark, opposite of him, crossed arms and a wicked smile. "That's right, you're almost there," she wispered.
...50...51...52...53...
"Well, this has been a lot of fun," Denise sighed, rubbing her hands over her breasts. "Though I was looking forward to seeing the final product."
...54...55...56...57...
"And still am," she grinned, lunging at Derrick. Her eyes flashed open and hands shot south to her clit, nails nearly scratching Lara as she gripped her button and played with it intensely.
...58...59...s-
"Oh, fuck yes, fuck, fuck, oh... oh... oh," Derrick screamed as she came, massaging her boob as her other hand tended to her pussy. Her breasts grew even bigger, reaching to doubl E cups as her ass became impossibly large. She collapsed into a puddle and heaved sighs of relief. After a few silent moments she sat up and looked at Lara, flashing a slutty smile. "Well, honey, it looks like we've both won." She slowly stood up and headed over to me, each step bringing with it more bounce in her ass and boobs. She reached up and pulled down my shorts, gripping my manhood and stroking it before kneeling overtop. "Hello baby, let's become acquainted. My name's Denise, and I'll fuck you anytime." Her voice was like honey, and her eyes held a lust comparable to Lara's. With introductions out of the way, she dropped, my dick penetrating her tight pussy and puncturing her hymen. "Ffffffuuuuuuckkkkk..." she moaned, eyes rolling in the back of her head. "Let's see if we can last longer than sixty seconds."


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