The Bet

Bri squeezed her legs around my neck and enjoyed the ride. She mewed, moaned, groaned, and commended my efforts as her body rippled. And after another five minutes, she announced the arrival of her next big O.

It's probably some sort of macho thing, but hearing a noisy climax from her has always put a big smile on my face.

Satisfied, I withdrew my lips from her sweet folds and removed her legs from my shoulders. I stood and looked down at her as her chest rose and fell.

"Not sure I can get up," she said, opening her eyes.

"Well, you're gonna have to in a minute." I stepped out the shower and approached the sink.

I opened the cabinet and pulled out the tub of Vaseline I used in the shower on occasion. I grabbed the paper bag on the tray and pulled out a long transparent tube with a nozzle and a blue rubber bag that resembled a hot water bottle. I connected the contraption, lubricated its nozzle and filled the rubber bag with water at the sink.

"Is that..." said Bri, squinting her hazel eyes as I stepped into the shower. "Is that...an enema kit?"

"Uh-huh." I nodded.

She looked confused.

"Well, it's mainly used to help relieve constipation. But can also be used for...cleaning your back passage."

Bri stared. "Oh God." She closed her eyes. "And Mum warned me how weird men can be." Her head shook.

I chuckled. "It won't hurt. And it'll be a nice little warm up for later."

She sighed. "Fine...But I think I'm going to need another glass of wine first."

Once she gulped it down and placed her glass on the shower's ledge, Bri bent over at the waist, placing her hands on the ledge, too. I got on one knee and admired the view of her in this position.

I've said it a hundred times now, but man my girlfriend had a wonderful ass. Unable to control myself, I leaned in, planted my lips over her left cheek and then her right.

My left hand came up and took hold of a buttock. I pulled her cheeks apart and took a look at her backdoor. I'd seen it a few times during doggie style and cunnilingus, but had never gotten an ideal chance to examine this part of my girlfriend's body.

It was light brown--a nice contrast with her warm ivory complexion--and had the circumference of a nickel. At the center was the tiniest hole I'd laid eyes on. It looked as if it wouldn't accept anything bigger than a pinky.

Although from what I'd seen on the internet, I knew it could take a whole lot more.

I know the term "asshole" has never been a pleasant way to describe someone, but staring at hers I couldn't imagine why. I found it beautiful. A part of me wanted to lean forward and have a lick, but I found control.

I lifted the lubricated nozzle of the enema kit and pressed its tip against her rosebud. I was a little jealous of the small piece of plastic--getting the first crack at entering her in this way. But I felt Bri resisting as she tensed up and clenched.

"Relax, babe," I said, almost in a whisper. She let out a slow exhale. I gently pushed the nozzle forward and squeezed it through with a soft squelch. "See? All the way in."

"Really?" She looked over her shoulder. "That's not so bad."

"Told ya." I lifted the blue rubber bag, showing it to her, then raised my eyebrows and said, "Ready?"

She nodded. "As I'll ever be, I guess."

I raised the bag higher and gave it a firm squeeze. Water rushed out through its transparent tube, traveling downward, like an IV drip, and pumped into her rectum.

"Ooooh," Bri moaned. "That feels a little weird."

"In a bad way?"

"No. Mmmh. It's just a strange feeling of being filled up. And the water's cold--oooh...I can't believe I'm letting you do this to me."

I squeezed and squeezed the bag and was surprised to see how much water easily pumped inside her. I'd researched on my phone--during my cab ride to the pharmacy--on what to do and what to expect. And I'd seen women online taking torrents of water from hoses in their asses. But I still expected more resistance. How much room was back there, anyway?

Once the bag was empty, I gently unplugged the nozzle and stood. "You okay?"

"Yeah. Just feel kinda full."

"Technically, you are."

"What do I do now?"

"Well, I don't think you need to go all the way to the toilet to let it out. We're in the shower. You can just let it go down the drain right here."

"All right. Move aside before I squirt you."

I smiled. That wouldn't have bothered me as much as she probably believed. I stepped to the side nonetheless and watched with interest as Bri took hold of her buttocks.

She spread her cheeks, bent her knees and grunted. Water gushed from her anus in a long thick stream, punching through the water from the spraying showerhead and hitting the floor.

My cock flexed with fury. Even though I'd seen such images on the internet, watching in person made the experience so much hotter. There was also something about Bri sharing a personal moment like this with me that I couldn't help but love.

I felt closer to her than ever.

As the water flowing from her ass went down the drain, I noticed it wasn't as dirty as I'd anticipated. Apart from the--as should've been expected--little brown specks here and there, I'd describe the water as clean.

"How'd it feel?"

"Not bad, I'll admit. Actually, it felt kinda nice." She sniggered.

Happy to hear her words, I refilled the rubber bag from the showerhead. Our water had turned lukewarm. I got back behind my girlfriend.

"Think you can take it a couple more times?"

"I think so."

I spread her ass and reinserted the nozzle. I raised the bag and gave it a hard squeeze. As before, water ran down its tube and entered her bottom, causing Bri to moan.

After I squeezed out the last few ounces, I put down the kit, stood to the side and used both hands to pry open her cheeks. I told Bri to let it all out. She crouched lower and moaned as water flowed from her and splashed the floor. It looked even cleaner this time.

I refilled the bag two more times and we repeated the procedure. Water spurted out her ass as clear as it went in. It looked drinkable.

I wanted us to keep going. This was the most fun semi sexual experience I'd encountered in my twenty-six years of life. And Bri seemed to enjoy it, too. However, it was unnecessary and I had bigger plans lined up.

I placed the enema kit on the shower's ledge and turned off the water. We stepped out, grabbed a couple towels and dried off. I handed Bri the other glass of wine, took her by the hand and grabbed the paper bag on the tray.

"I'm afraid to ask what else you have in there."

"Nothing too scary. I promise."

We walked out of the bathroom, down the short hallway and stepped into our bedroom.

"Ready for the next part of the adventure?" I said.

"Mm-hmm." She nodded and took a sip of her drink. "It hasn't been too bad so far."

I took her glass, placed it on the dresser, then grabbed two pillows and stacked them in the middle of our queen size bed. I instructed Bri to lie on top of them at her waist. She removed her towel, dried her hair a little more and got into position.

I picked up my paper bag, pulled out the bottle of honey and then placed the bag by her side. I uncapped the honey and mounted the bed.

Bri looked over her shoulder and fixed her golden-greenish gaze on the bottle in my hand. "And what're you planning with that?"

"You'll see." I crawled behind her and placed her legs between my knees.

I lifted the honey bottle, squeezed it over her left buttock and then her right. I've always loved my buns covered in honey.

I dived in face first and slid my tongue up and around her right cheek, slowly licking the sweet condiment off. I crossed over to her other cheek and cleaned it spotless with my tongue, too.

Bri giggled. "Enjoy that?"

"Definitely." I reached for the honey. "But I think I'm ready for the main course."

I placed my left hand on her round little bubble butt and parted her cheeks with my thumb and index finger. I held the honey over her ass and squeezed out a dollop. It dripped between her cheeks and coated her light brown asshole.

It looked like the most mouthwatering pastry ever.

I tossed the bottle aside, placed both hands on her cheeks and pried them apart. I'd been dying to do this for almost as long as I'd known her. It was a literal wish come true. I moved my face in, pushing out my tongue and ran it all the way up her ass's split.

Bri giggled, again. "Oh God. I'm in a relationship with a pervert."

I smiled. "Like you didn't know that already."

My face dived back in and tongue slid up her ass two more slow times. Then I focused my attention on where the honey was concentrated. I lapped and lapped at her sphincter, enjoying the interesting blend between the sweet condiment and her asshole.

I polished it, and thought about adding more honey, but didn't like how it masked her natural taste. Instead, I continued licking her rosebud, slowing down the movement of my tongue. I circled her ring with its tip as my hands massaged her cheeks.

Bri moaned her feelings into the mattress.

Without the honey in the way, I was able to get a better feel of her sphincter. I couldn't help but enjoy the bumpy feeling of her ridges. It was a unique part of the skin. I also enjoyed the way her asshole tightened and loosened at my inquisitive tongue.

I stiffened it and pushed at her tiny opening. It resisted me, but I remained persistent with my prodding. Bri groaned as the tip of my tongue penetrated her half an inch deep.

I wiggled it inside her and stimulated the nerve endings inside her anus. Judging by her moan, my girlfriend liked the feeling.

I'd never eaten ass before, and a part of me believed it would probably leave a bit of a nasty taste in my mouth. But I found no such drama. I shouldn't have been surprised given how thoroughly we'd cleaned this area, but was surprised to find out I actually enjoyed her earthy flavor. Go figure.

I spread her cheeks farther apart and tried to drive my tongue deeper. I didn't make much headway, though. I only managed to squeeze it about an inch inside. The flexible structure of my tongue wasn't ideal.

I wiggled it inside her and extracted a throaty groan from Bri as her breathing deepened. I wondered if I could get her to cum this way, but there were other ways to try and make that happen. I wiggled my tongue for a few more seconds before I pulled out and stood on my knees.

Bri's back rose and fell as she recovered.

I reached for my paper bag and pulled out the tube of thick-water-based lube I bought from a sex shop. It got a high recommendation from the store's manager. I also pulled out the purple toy I bought from the same store and took it out its box.

"What's that?" she said over a shoulder.

"Just a butt plug." I held it up for her to see.

"That looks a little bigger than everything that's gone back there today."

I noticed the worry in her eyes.

"I know. But the lady at the store said it's a good size for beginners. They had bigger ones. Plus, I read on Reddit that it's a good idea to start off with toys and such before you take on the real thing."

She thought. "Okay...Where's the lube?"

"Right here." I showed it to her. "I'm gonna need you on your back. It'll make things much easier for you."

As she removed the pillows from underneath her frame, I uncapped the lube and squeezed it onto the butt plug. I used my fingers to coat the toy's entire bulge. I liked the thick durable feeling of the liquid.

With Bri on her back and her head by the headboard, I moved in closer and told her to lift her legs to her chest and bend her knees. I got on my stomach and used the excess lube from the plug to coat my middle and index finger.

I placed the tip of my index against her rosebud and moved it in circles. "Just gonna start with a finger first, all right?" I looked her in the eye.

"Okay." She gave me a small nod. She looked nervous.

I pushed my finger forward, which caused her to clench up as she closed her eyes. "Babe, relax. Just like with the nozzle in the shower. The pain is all in your head."

I watched her take in a few deep breaths, and as she let one out I pushed my finger forward. It was met with resistance from her tightness, but after a couple seconds her asshole yielded and accepted my digit.

"Mmmmh."

I pushed in until the first knuckle. "You okay?"

"Mm-hmm."

I pushed deeper until her sphincter was locked around my second knuckle, tightening and loosening. It almost felt like someone was sucking on my finger. I inched it farther and farther in until my finger pushed all the way through. Bri grunted.

"How's it feel?"

"Uh...less awkward than I thought it would be," she said, opening her eyes.

"You'll get used to the slight discomfort in a minute." I wiggled my finger, enjoying the strange feeling of her insides and then pulled out from her asshole. When her ring locked around my first knuckle, I pushed forward, again.

For the next two minutes, I inserted and extracted my index finger from her, wiggling it from time to time, relishing the warm sensation of her rectum. At first, Bri groaned and grunted softly as her asshole nibbled on my digit. Then she let out a hum with every deep breath as she accepted my presence.

"Ready for another finger?"

"Well, I've just gotten used to one"--she sighed--"so why not?"

I withdrew my finger until only the tip was left. I placed my middle finger at her rosebud and squeezed its tip alongside my index finger's. As gently as before, I drove both my digits through her sphincter.

Bri cooed as I maneuvered them.

"Mmmmh. Not so...hmm...bad." Her breathing was deep and relaxed.

After two more minutes, I withdrew my slippery fingers with a squelch. I grabbed the purple sex toy and placed its tip at her backdoor. "Remember to relax, hon, and stretch your legs a little wider."

Bri pulled her long legs farther apart and as she let out a deep breath, I pushed the plug forward. She closed her eyes with a raspy moan as the thick lubricated toy slowly pushed through her sphincter.

My eyes honed in on its entry. It stretched her hole into an O about two inches wide before it got swallowed whole. My cock flexed underneath my midsection. I pushed the plug in a little farther, flattening its round back end between her cheeks.

"Is it all in?" Bri opened her eyes.

"Uh-huh. And there's also something a little unique about this toy." I reached for the box it came in and pulled out a small remote control. I pressed its power button.

"Oooooh." Her back arched as her feet planted on the mattress. "It vibrates."

"Feel nice?"

"Well, it's not the same as a vibrator feels on my vagina. But I like it." She smiled.

"And the vibrations on this are adjustable." I pressed the little plus sign button on the side of the remote a few times, which caused a loud, muffled buzzing sound.

"Ooooooh." Her back arched. "Not so--mmm--high now."

I pressed the minus button three times. The buzzing died down.

"Mmh, much better," she sighed.

I lay on my stomach once more, moved my head over her vulva and ran my tongue up and down her wet slit, savoring her taste. I locked my lips on her swollen clit and sucked. Bri let out a hoarse cry.

I licked her clit, pushed my middle finger through her walls and curled it, stroking the roof of her pussy.

"Mmnghh, babe, hold on." She breathed hard. "I'm feeling...ahh, a little overstimulated right now. Let me take care of you for a second."

Once I removed my lips and finger from her, we switched positions. I sat in the middle of the bed and leaned back to rest against the wooden headboard. Bri was on her knees and forearms with her curvy derrière raised high in the air.

"Look how hard this thing is." She took hold of my erection and looked me in the eye with a smile. "It must be dying for some attention after everything you've done to me this afternoon."

She had no idea how right she was. My cock was furious with my patience.

Bri opened her mouth, stuck out her tongue and ran it up the front of my shaft, licking the tip and pulling away a thick string of pre-cum. Her smile showcased her teeth. I smiled back, moved her damp hair behind her shoulders and pushed my fingers through her golden locks.

Bri dropped her head, took in my glans, sucked hard and swished her tongue. I enjoyed her enthusiasm. She sucked my cock in deeper, taking in an eyebrow raising four inches of length.

She pulled up, slurping, and when only my cockhead remained between her lips she took in as much as she could manage. She repeated this two more times. Then her head bobbed at a fast pace as her hand stroked the last few inches of my shaft.

I closed my eyes and enjoyed her skills alongside the delightful sound of her slurps. It sounded as if she was in a rush to finish a bowl of soup. I loved it. And then, surprisingly, her bobbing gained speed.

I wondered what had come over her. She hadn't been this eager in weeks. Perhaps it had something to do with how I'd performed earlier with my tongue. Bri was one of the many women who like to reward a good licking. Maybe it had something to do with the humming toy inside her anus--which I liked to believe. Or maybe it was the wine, or a combination of it all. Either way, it was magical.

As her quick bobs continued, I thought about offloading inside her mouth. I'd been waiting for an orgasm for hours. But I knew she wouldn't be happy if I did it without notice. Although her mood left me unsure. It didn't matter, anyway. I wanted to save all I could for her backdoor.

Bri pulled me from her soft lips with a pop and made eye contact. "Wanna throat fuck me today?"

I gave her another smile. "What's gotten into you?"

"I dunno. I'm just horny right now."

While I climbed off the bed, Bri moved to the side of it and lay on her back, hanging her head over the edge. I stepped in front of her, taking hold of my cock.

I bent my knees and grabbed a tit. She opened her mouth. I guided my cock in and took hold of her other breast. We hadn't done this in a few months. It was our go-to position whenever Bri wanted to take me as deep as possible.

At a slow speed I thrust my hips and pushed my erection past her tongue, which brushed the top side of my shaft. This felt different--in an odd but good way.

I pushed deeper as I squeezed her perky apples for tits. They might not have been big, but felt great on a woman in her youth. I kneaded them and rolled her nipples between my fingers. The soulful moan I withdrew from her throat felt wondrous on my cock.

I retracted my hips and before my full length could escape her mouth, I slowly thrust forward again, pushing most of my erection past her lips. Seconds ticked by as I thrust.

I gained speed, pushing deeper and deeper.

My balls soon bounced off my girlfriend's face as I fucked her mouth and played with her tits. I wasn't always this vigorous with her, but knew it's what she wanted. Her hands were firm on my ass and jaws stayed wide open as she accepted my sharp thrusts.

The squelching sound of my plunges with her gags spurred me on. "Ahh. Yeah, babe. This is fuckin' great." I groaned.

On any other day, I would've kept going for a little while longer, but felt an imminent orgasm. Plus, her hot mouth had driven me to my breaking point. I couldn't wait any longer. I wanted her ass--now.

I thrust my hips a few more times, trying to lodge my cockhead inside her esophagus. Then I pulled out from her sweet lips.

"Had enough?" Bri looked up and into my eyes.

"Yep." I wiped my forehead. "I'm ready for the main event."

She rolled onto her stomach. "It was only a matter of time."

"You still scared?"

"Not as much as before, but I'm still gonna need one more glass of wine before we start, please."