A Bet is a Bet, Part 1

Story by icetigress on SoFurry

, , , , , , , , , , , , , , ,

#1 of Experimentation

Dal's weekends are usually boring, but a little one-on-one with his roommate turned things around in ways he never expected.


Saturday evenings at Dal's apartment were anything but exciting, and this Saturday was certainly proving to be no different. Normally it was: get up, shower, have breakfast, run a handful of errands, back home, eat dinner, and game for the rest of the night. If his roommate, Gypsy, was home, he'd often challenge her to PvP. She always accepted, and always lost, but she was gracious about it. "They're fun but I'm not that great at them," she'd always admit with a laugh. She was pretty chill, for a mare. And one helluva cook, when she decided to put some effort into it!

Dal was fidgeting away at his computer, indulging in some Mass Effect for the evening, and occasionally yelling into his headset.

"Oh come ON, what the hell was that?" he shouted at no one in particular. His continued grumblings caused Gypsy to poke her head into the living room.

"Yo," she yelled, getting his attention. "I get you love 'pwning n00bs' or whatever, Dal, but can you keep it to dull neigh or something? I can hear you over my headphones while I'm reading." She raspberried at him as he playfully flipped her off with a grin.

"First off, Gyps," he started. "You don't 'pwn n00bs' in Mass Effect. You kill things. Of course you'd know that if you'd ever played it before. And second..." He pondered for a moment before looking at her and smirking. "Don't stick it out unless you plan on using it."

"Pretty sure I'm not your type," she teased, recalling having walked in on him once or twice with another stallion. "Tell you what, though. I'm gonna sit out HERE and read now. And I'm gonna throw popcorn at you every time you yell at your computer."

"Hey wait," he started, but Gypsy had already disappeared back into her room to grab her things, and shortly after, had plunked herself on the couch. She had her headphones on, book in hand, and a bowl of freshly-popped popcorn on her lap. "Gonna share?" She quirked a brow and eyed him over the top of her book. She threw a piece at him, which booped him square in the nose before falling to his lap.

"There you go, enjoy!" she said with a smart-assed grin. She went back to her book and happily munched away on her snack.

"Fine then," he took his headset off, got up, and strode over to wear she was laying. She looked up at him, a bit of surprise in her emerald eyes as he helped himself to a large handful of her popcorn and stuffed it his mouth. "Thanks!" He thanked her through a full mouth, and went back to his computer.

This exchange went on for a couple of hours, neither of them tiring of the other's antics. Gypsy got to the point where she had put down her book and nearly started a food fight right in the living room. This continued until there was pretty much no eatable popcorn left.

"Welp," she stated. "So much for that. I'm still hungry though. You want anything from the kitchen." The mention of food got Dal's attention.

"You cooking?" he asked hopefully, turning away from his monitor. Gypsy just laughed at him as she moved toward the kitchen. He always enjoyed her cooking, and she knew it.

"Maybe," she answered. "What's in it for me?" Dal didn't even have to think that one over.

"I'll let you beat me at Halo tonight," he said, hoping the offer was enough. The vanner tilted her head to consider his offer, her long black and white mane spilling over her shoulder.

"Don't outright let me win," she started. "But don't crank the difficulty on me again. That's the only reason I get my ass handed to me when we play!" The stallion's ears perked.

"Deal!" he exclaimed. "Now get cooking, I'm starving."

"Could've fooled me," she muttered teasingly as she disappeared into the kitchen.

"Hey, I heard that!" Dal yelled, trying not laugh. He heard her laugh to herself amid the clanking and clattering of dishes.

Gypsy spent the next 30 minutes in the kitchen, and while Dal couldn't put a finger a on what she was making, oh man, did it ever smell GOOD. His mouth started watering, so he wandered to the kitchen to see if she was nearly finished.

She must have gotten changed without him noticing, because she wasn't wearing her PJ pants anymore. Now she was rocking her favorite denim shorts, and, though Dal was more a fan of the gents than the ladies, he couldn't deny that the mare in front of him had a great ass. 'Too bad she wasn't a guy,' he thought to himself, staring off into space.

"Dude, what the hell?" she exclaimed with a smirk, snapping Dal out of his ass-induced trance. "Take a picture, it lasts longer!" She chucked a piece of carrot at him, which he somehow caught without thinking. He inspected it momentarily, and then popped it in his mouth.

"Sorry, Gyps," he said, swallowing the carrot bit. "The smell of that stew got me all zombified here." He started shuffling forward like a zombie. "Steewwwww...." She laughed at him when his hoof caught a kitchen chair and he stumbled.

"Stick with brains," she quipped. "You'd be better off for it. And so would I." She stirred at the stew on the stove, throwing in the last handful of veggies with a few spices. She tested some of the beef off the ladle, and by the look on her face, you'd swear she'd been turned on. "Mmmm, damn I'm good! This should be ready in about five to ten minutes. Let's get that X-box set up!"

Dal ducked into her bedroom to grab the controllers while Gypsy dug around under the TV stand to get the actual console set up. She was still digging and fidgeting with the cables when Dal emerged from his room and was greeted with the sight of Gypsy knelt on the floor, rump raised in the air while she set up the X-box. He stopped and stared, his pants suddenly a wee bit tighter.

'Stop it, you,' he mentally chastised himself. 'Not a dude, man, what the hell?' During his mental self-scolding, Gypsy had turned and noticed him staring once again. She watched in amusement for a moment, and got a wicked idea in her head before whistling and bringing him back to his senses.

"Hey, pony-boy," she quipped, sitting up. "Earth to Dal!" He shook his head and blushed.

"S-sorry," he stuttered. He set the controllers on the couch and cleared his throat. "Food, yes??" She laughed at him and got up to move to the kitchen.

Dinner was ready, and quickly served. Dal was practically salivating as she prepared his bowl of stew. They sat and ate dinner, chattering back and forth about the prior week's events.

Gypsy cleaned up their dishes, and set them to soak in the sink.

"Alright, pony-butt," she turned to him, with a devilish grin. "Care to place a small wager on our match tonight, best two out of three?" Dal stood silent, staring at her for a moment, opening and closing his mouth and trying to say something.

"Uhh...sure?" he replied. "What did you have in mind...?" He hesitated. He knew that look, and knew it meant she was up to no good, but he played along anyway.

"Well," she started thoughtfully, moving toward the living room, motioning for him to follow. "I figured... since you've been gawking at my ass all night, we can make this interesting." Dal blushed hard. "If you win, you can have this ass that can't seem to stop staring at. But if I win...I get yours." Dal's eyes went wide at her challenge, his pants tightening even more this time. He thought about it momentarily, and decided to accept, knowing there was no way she was gonna beat him. She was admittedly horrible at the game.

"Deal," he said, sticking out his hand. She shook his hand in agreement, smirking confidently.

"It's a bet then," she said in a low voice. They made it to the living room, plunked on the couch, and got settled in. "Let the games begin."

The first round of one-on-one firefight went by rather quickly, as Dal quickly asserted his dominance. He laughed out loud as Gypsy grumbled and gave him side-eye.

"Aww don't be sore, little mare," he teased. "You didn't think you'd actually win did you?"

"There's still two rounds left, smartass," she glared. "Now it's ON." Dal chuckled at her sudden burst of confidence, thinking 'Ooh, I'm so scared.

Round two took a bit longer. Gypsy fought tooth and nail, but eventually ended up winning the round. Dal's jaw dropped. Never once has she played that hard against him. Had she been practicing...? Was this a set-up...?

"How in the hell...?" Dal exclaimed, as the smug mare beside him stretched her arms over her head in victory. "That was just a fluke!" She laughed at his surprise, and poked him in the side.

"Sudden death now, hoss," she grinned. "It's anyone's game." Dal buckled down. He was determined to NOT lose this round....right? Right...? The thought of losing excited him, and he didn't know why. He shook his head and focused.

"You're not winning this one," he poked. "This is my favorite level."

Round three. They both went shot for shot, kill for kill. They were both tied for kills in the last 30 seconds of the game, and Dal was concentrating on losing. Wait no. Winning. Winning, right...? Yes, winning. Must win. He's totally got this...

Until Gypsy whoops in triumph beside him as she lands the final killshot on Dal. She jumps up and does a little victory dance, wiggling her rump at him.

"Winnah, winnah, chicken dinnah," she laughed, still dancing around. Dal just stared wide-eyed at the screen, looking disappointed that he lost. In his head though? He was kind of thrilled. He had never been topped by a woman before. And definitely never been pegged. Does it feel like a real cock? The thoughts running through his mind had his blood rushing down from one head to the other.

"Lucky shot," he grumbled. He leaned back on the couch, his pants doing nothing to hide the very obvious tent that had formed. Gypsy eyed his pants, and then smiled brightly at him, moving forward. She reached down for his hand. This was actually gonna happen. He put his hand in hers and she helped him to his feet.

"Lucky, my ass," she raspberried at him, leading him to her room. "Or rather....lucky, YOUR ass, I suppose." He diligently followed, his mind swimming with ideas. Was it a dildo? A buttplug? Or...dare he wonder...did she have a strap-on...?

She stopped him at the foot her bed, and had him wait while she went to her closet turning on her bedside lamp along the way. She rifled through her things for a few moments, trying to find that strap-on she bought a few months ago. She had never used it, and this was the perfect opportunity to break it in. She chuckled to herself as she found it.

"So uh..." Dal gulped nervously. "How do we um...how...how do we do this...? I've never done this with a woman." He glanced toward her closet, and caught a glimpse of Gypsy slipping out of her shorts, and stepping into a black-strapped...strap...that she tightened around her hips and thighs.

"If you don't know how to have sex, pony," she started. "Then I have no idea what goes in your room with your dates." Dal blushed furiously and felt he could very well be glowing as this point. Shit, he thought he was being quiet. Guess not. "Now drop 'em like a good hoss." More blushing. Fuck. This was happening. "A bet is bet. You're not a welcher. And I already know what your dick looks like, so no being shy." Dal couldn't believe what he was hearing. This was a whole other side to his roommate that he didn't know existed. Trembling with...excitement?...yes, excitement, Dal slipped his pants and underwear off, his cock springing up, stiff as can be.

"Alright, alright," he responded, standing gloriously nude in the soft light. "Let's get this over with." Gypsy smirked, and stepped away from her closet, sporting a black and pink horse-cock strap-on. He gulped hard. He thought back to some of the dates he brought home; none of them were THAT big. "That's uh...fuck, that's REALLY big, Gyps."

"I have faith you can handle it," she said, gripping his chin and kissing cheek. "Besides, don't act like you aren't excited." She gently ran a finger along the underside of his stiff cock, a bit of pre lightly glistening on the tip. Dal couldn't help himself, that light touch felt wonderful; he let out a soft moan and then gasped as she gripped the base of him.

"F-fuck, Gyps..." he moaned, his hips instinctively thrusting forward as she gripped him tightly. "Nnnghh, shit...." She had taken his head in her mouth, and sucked him a little before standing in front of him. "Holy...shit..." He was practically panting, and Gypsy had a look of pure enjoyment and triumph on her face.

"Get your knees, Dal," she told him firmly. She felt a heady rush of power as the big stallion knelt in front of her. "I promise to use lube, but I'd like you to start this off. Now...suck my cock." Dal looked up at her with a look of nervousness and excitement in his eyes. She could tell he'd never done this with a woman.

"Okay," Dal said meekly. He leaned forward and slipped his muzzle around the fake horse cock in front of him, surprised at how realistic it felt in his mouth. He took it as deep as he could to the back of his throat, taking almost half, and Gypsy held him there for just moment, drinking in the delicious sight before her. She let him go, and he slipped his mouth off the strap-on, leaving it spit-soaked.

"Oh, that's perfect," she cooed. She urged him to sit on the edge of the queen-sized bed while she wandered to her bedside stand to grab her lube. She walked back and stood in front of him again, taking note that his cock was now throbbing, with more pre leaking from his head. "Now...do you wanna be on your back? Or on your knees?" She slathered lube along the fake cock so it practically shone in the lamplight.

"Uhh..." Dal hesitated for a moment. "Both...? Start on my knees, finish on my back...?" Wait, did those words just come out of his mouth...? She grinned at his response.

"Excellent," she smiled. "Now, on your knees. I promise I'll go slow." The big stallion turned slowly and knelt on the edge of the bed, lifting his thick tail and presenting his tail-hole. Gypsy stared appreciatively for a moment before wetting her thumb and rubbing against that dark donut. Dal moaned, his cock twitching from the touch. "You like that?"

"Mmmff," he groaned. "Yes. Yes." He was panting now, and never dreamed in a million years that he'd be presenting his tail-hole to a mare.

"Good," she said quietly, moving closer behind him, rubbing the flared tip of the horse-cock strap-on against his puckered donut and pushed a little, eliciting a gasp from the stallion. She reached over beside her on the bed, and grabbed the lube, applying a generous amount the head of the strap-on, AND to Dal's tail-hole. He squeaked a little from the cold lube, but soon relaxed.

Gypsy pushed forward again, this time slowly popping the flared head into Dal's exposed donut. He moaned loudly, panting a little, trying to adjust to the size that was invading him. Gypsy paused a moment to allow him to relax, and slowly started pushing forward a bit more, sinking more and more of her fake cock into her roommate's ass.

"Holy...fuuuuck..." Dal moaned as Gypsy pushed deeper. "That's....fucking huge...". It was; this was definitely the biggest cock he'd ever taken. And he was absolutely loving it. He'd dated and fucked and been fucked by plenty of decently-hung stallions, but none that were THIS size. "Mmm...m-more..."

"You want more?" the mare repeated back. "You got it." She pushed even further, deeper into his ass until she was almost buried to the hilt. She heard the stallion grunt and knew she was at his limit. She held herself there for a few moments allowing him to adjust to the size that just stretched his ass.

"Fuck, that feels amazing," he groaned, instinctively pushing back. "Don't stop. Keep going." There was almost a plea to his tone. He wanted to cum. Badly. And he would. When she allowed it.

"I'm glad you're enjoying yourself," she was practically moaning herself, watching his ass swallow her fake cock like a champ. "I know I am." She started moving in slow, rhythmic thrusts, pulling out almost all the way before sinking back inside of him, over and over.

"Harder," Dal pleaded. He wanted to see if she could measure up to his past partners.

Gypsy grinned, and started thrusting harder and faster, the intensity causing Dal's leaky cock to slap against his belly, and his heavy balls to slap against his cock. The sound caused the mare to buck against him, pulling him back into her thrusts. His deep, loud groans only served to egg her on.

"Such an eager pony," she teased, slowing up her thrusts, and holding the length inside him. "But you need to get on your back now. I can't have you leaking pre all over my bed, and I just washed this blanket." She smirked and drew back, slowly pulling out the flared head of her strap-on, causing Dal to grunt.

"Just...gimme a sec," he panted, trying to catch his breath as he rolled on to his side. "Fucking hell, Gyps. Why do I feel like you've done that before?" The mare smiled at the almost-praise.

"Not to a stallion," she replied. "Other mares, though...?" She smirked and winked at him as she grabbed the lube to prepare her fake cock once again, watching Dal slowly rub his own cock. "Now get on your back. You can finish doing that in a moment." The panting stallion smirked back at her, shifting himself on to his back, his legs hanging off the edge of the bed.

Gypsy stepped forward, and leaned down to hook her hands under Dal's knees, lifting both of his legs over her shoulders, and angling the flared horsecock at his ass once more, rubbing against to lube it up.

"Much better," she cooed, starting to press the head inside his ass once more. "And you can go ahead and stroke yourself if you want. In fact, I'd prefer it if you did." Dal grunted as the head popped inside his ass once more, and immediately took his leaking cock in his hands.

"You're such a pervert," he quipped, moaning as she pushed deeper and deeper.

"Says the stallion getting his ass plowed by a mare," she shot back, chuckling. She didn't wait this time, swiftly pushing the remaining few inches into his ass in one thrust, causing his cock to pulse a bit as he was stroking himself and a guttural groan to escape his throat.

She gripped his thighs, holding him tight against her pelvis, quietly watching him through her half-lidded eyes as he used both hands to slowly stroke his marble-colored length, his head slightly flaring and leaking pre onto his soft belly.

After holding still for just a moment, she let loose like a mad-woman. She started pulling back to the head and thrusting it all back in, over and over, until she was practically jackhammering the stallion's ass, causing him to moan and grunt out loud.

"Fuck...fuck...yes..." he was panting hard as the lovely vanner plowed in and out of his ass, making him take more than anyone else had before. "Don't...stop...so...close..."

"That's right, pony," she herself was panting at this point with how hard she was thrusting into him. "Cum for the mare. Cum for me." She demand was almost feral, and Dal could swear he heard something between a growl and a purr in her voice, almost like she was part cat. 'Gods, I'm wet,' she thought to herself. 'Definitely gonna need a few minutes with the showerhead after this...'

"Fuck...I'm gonna...I'm gonna..." Dal groaned stroked himself furiously as his roommate fucked his ass, and was unable to hold back. His head rolled back as he grunted and panted, his pumping fists coaxing out rope after thick rope of white, virile semen onto his belly and chest, the spurts sometimes landing as far as his neck.

Gypsy pushed the fake, flared horsecock deep, giving shallow thrusts as the stallion came hard all over himself. Only when his cock stopped gushing did she slowly pull out of his ass, popping out the head, and moving collapse beside him on the bed after slowly letting down the stallion's legs. They both panted hard, trying to catch their respective breaths. She leaned over and pecked a quick smooch on his cheek.

"Well...that was..." she started, looking for the right words. "Intense. Who knew anyone could cum that hard?"

"It really was," he agreed, slightly sitting up to inspect his mess. "And I certainly no idea I could cum like that." He held up his hand, regarding the sticky mess he'd left behind. "I'm surprised I didn't get any on your bed." He grunted as he sat up, his dripping cock hanging slightly limp between his legs. "Though I can't say the same for your carpet. Sorry about that."

"Aw, for real?" she gave a hefty sigh and set carefully, her core absolutely screaming at her. She knew she was gonna pay for that workout the next morning. "Well, you're cleaning it then. Not MY fault you're a messy pony."

Dal just side-eyed her at her comment, smirking at her comment. "Actually..." The stallion carefully stood up and stretched, slowly gathering his pants and making his way out of Gypsy's room. "Totally is, and I'm not complaining. But I'm grabbing a shower. It's all yours when I'm finished."

Gypsy watched the strong stallion saunter out of her room. She stood up, and regarded the slight wet mess on her floor at the foot of her bed.

'Well, that mess isn't totally his,' she thought to herself, grinning a bit. 'I think I'm gonna have to challenge him again next weekend. And who knows....maybe I'll lose this time...' She unstrapped the fake horse cock from her waist, giving it a quick wipedown with a nearby towel and her toy cleaner before storing it back in her closet. She heard the shower start running, and decided to take a moment to herself.

"Well, now that he can't hear," she said aloud to herself. "Time to quickly take care of myself." She grabbed her trusty wireless vibrating egg, laid herself out on her bed, and closed her eyes, imagining what the next weekend might have in store.