GF Teases Me Through Diet Challenge

Oily fingers swirled around my asshole as my cock strained against its plastic prison. Making matters worse, Amber's tongue was dancing between my balls and taint. My brain was melting down and my cock felt like it was going to explode in both a good and a bad way. I'm a low key, boring guy, so how'd I get myself into this position? I had a few too many beers, not that I was drunk, but rather I did not lose a prescribed amount of weight and beer was a contributing factor. Let's back up a few weeks to help you understand.

My girlfriend Amber is five foot six, slim waist with D cup breasts and long legs. She's fairly athletic, so her stomach is perfectly flat and her ass, a thing of wonder. This month her waist length hair is a honey brown and she has huge blue eyes. I love this woman with every fiber of my being. Our sex life can get a little spicy and for the most part she is willing to try new things, although she has not let me in her ass as of yet. We both obsess over oral (she can cum three plus times a session with my tongue on her clit). We also have a budding toy collection and are not afraid to incorporate them into our sex life.

So, here's what got me into the aforementioned situation, I was struggling to lose weight and walked around probably 15 pounds above ideal. The real challenge was I lacked the discipline or maybe motivation to do something about it. This is where my clever GF jumped in and suggested I'd be much more motivated if I had a carrot to chase. Not sure I needed that from her, but I was getting kinda desperate, so I listened to her proposal.

"What do you care about? cash and sex, that's what drives you and I can't influence your cash, but I can control sex, so I'm proposing a weekly weigh in, if you drop three pounds per week, I'm your oral slave for the weekend. Want me to drop to my knees, just say the word. Want a blowjob alarm clock? Just tell me the time you want to wake up with my mouth wrapped around your cock. Feel like cumming all over my tits or even face, I'm happy to take your load." extolled Amber with a wild eyed grin.

I stared blankly for a moment pondering the opportunity I was just presented already pondering watching my favorite show while my naked GF licked up and down my cock. Then it occurred to me, she was a devious woman and there may be a downside as well. "What if one week I do not lose the three pounds?" I queeried, a little afraid of the answer.

"You'd be a dumbass to mess up that offer and I'd probably lock you in a chastity cage for the weekend and tease the hell out of you. In fact, you'd be my oral bitch, on your knees whenever I felt like it and you would not get to cum." shared Amber with a daring look in her eyes.

She was probably right about the dumb ass part and that sounded like the perfect motivation to make this happen. I immediately took the deal without really thinking through the details and timing.

It was Sunday night and we established my base weight. My next weigh-in would be Friday morning. I was pretty confident and was very careful with my meals, even upping my exercise routine. Friday morning my GF met me in the bathroom with a bottle of baby oil and a small clear cock cage, both sitting conspicuously on the counter.

"Are you ready to get the blow job of our life or lose access to your cock for three days?" asked Amber with a devilish grin on her normally angelic face. It was starting to feel like she was enjoying this more than I was.

I stepped on the scale and didn't breath until it read 211. That was four pounds less than my start weight. A sly smile rolled across my face and I made eye contact with Amber, she winked, pulled off her robe and dropped to her knees.

Amber had my cock and her tits covered in baby oil before I even said a word. She moaned her way through the most erotic BJ of my life, begging me to cum on her tits between deep throats and rubbing my balls and taint the entire time.

"Cum in my mouth baby, I know you love that, just grab my hair and cum in my mouth" begged Amber.

I did exactly that and dumped a huge load down her throat while holding her pony tails. She gagged a bit, but for the most part kept her tongue in action as I spurted into her mouth. She was right, this was easily the best BJ of my life. Amer got up, licked her lips and walked off.

I later found her in the kitchen wearing one of my shirts that completely exposed her ass as she made breakfast.

"I knew that would work, you keep up the diet and exercise and I'm our personal cum dump, In fact, if you lose the full 15 pounds by the end of the five weeks, you can use my ass." dared Amber as she bent her ass around for me to get a good view of her perfect globes.

Anal was was not in our repertoire and she knew I was interested, so this was a hard motivator, but I also knew it wouldn't be that easy.

"And If I do not hit my goal?" I tentatively asked.

"Oh, then I fuck you in the ass, maybe even have Bob, my bi friend from work come over and fuck that tight little ass of yours." Shared Amber, looking me dead in the eye.

I froze, would she really do that? That 'I dare you' look on her face said yes she would. Was she really that serious about my losing weight? Would I put my own ass at risk? Fuck... I wanted to fuck her butt badly, there is something about the taboo nature of it and the sounds a woman makes when here ass is violated. Hell, I was getting hard again just picturing it.

I could not even think straight and I'm sure she knew it. This first week was pretty easy, so I had some confidence I could make it happen and get to sink my cock into Amber's little bottom, so in my semi clouded judgment I agreed to her terms, blocking out the image of her bi coworker using my own ass for his twisted pleasure.

I spent the weekend with her mouth virtually attached to my cock, it was spectacular. I woke up to a blowjob, went to bed to a blowjob, came on her face, tits and hands and selfishly enjoyed every minute. Naturally my mouth was attached to her clit a fair amount of the weekend as well, but for sure I was on the better end of the orgasm train.

The next week was fairly similar as I just barely made the three pound drop. This time I tied her hands behind her back and fucked her face as well as had her lay on the bed with her head hanging off the edge so I could do more of the same. She kept up the dirty talking as I used her mouth. "That's it baby, fuck my face, make me take your cum down my throat, I'm your blowjob bitch this weekend."

I was in heaven and Amber was wildly enthusiastic, even buying me slimmer waisted pants as the effects of the weight loss started to show. Then it happened.

I had several off site meetings the third week and had taken clients drinking. I knew I was at risk, but had kept a steady exercise regimen and hoped it balanced out.

The Friday of the third week, Amber lined up the bottle of oil and the yet unused chastity cage on the counter as I stepped onto the scale. I had indeed lost weight, but only one pound. She looked me in the eye, picked up the cage and dropped to her knees, I grimaced knew it would not be as pleasurable as last weekend.

I wasn't sure if I was turned on or mortified by her ease at lubing up and shoving my cock into the plastic cage, but within moments I heard the distinct click of a lock closing and looked down to see my dick pressing against the clear interior of the cage.

Amber stood up, still keeping a hand on the cage. She then rubbed my balls a bit and dragged a nail across my taint making things worse for me. She pulled me into the bedroom by the now very full tube, spun around and sat down on the bed.

"You had a good thing, who would screw that up? Now get on your knees and make me cum." Demanded Amber.

I did as told and within second's she was grinding her clit into my mouth as her body shook uncontrollably. My face was covered with her cum and my dick ached.

"I could get used to this, good thing you are working from home today, I'll need a few more of those to make up for the last few week" Explained Amber with a wink.

I looked down at the overstuffed cage as Amber's perfect ass wiggled out of the bedroom.

I wore sweats that day just trying to keep the pressure off my tortured cock. It was of little use as even walking around caused the lock to clack against the cage and send an arousing vibration to my confined dick. The result was to make me harder and of course reminding me I could not touch myself. It had only been a half a day and I was losing my mind.

At one point Amber came to my desk, bent over in front of me and fondled my cage. Boobs in my face, she Slipped her fingers down to my balls and whispered in my ear how hot this was making her. I was still oily from the cage install and she worked my thighs, balls and taint with ease as my head tilted back and I started begging to cum.

She growled an evil sounding moan into my ear and told me to get on my knees.

I sighed and slid out of my office chair as she slid in, pulled her leg's up and presented her now shaved pussy. " I wanted to make sure I was extra eatable, so I shaved it, do you think it's pretty?" asked Amber.

I answered with my tongue and soon felt the cage bite into my cock as it pulsed helplessly in a plastic prison. Amber came within minutes, holding my head to her clit and moaning loud enough to startle the dog.

She got up and thanked me before sauntering away. I got nothing done for the rest of the day.

Naturally she asked that I wake her up the next morning in the same fashion that she had done for me. Saturday at 7:00 am I obediently licked her to consciousness as her thighs clamped down around my head. Morning wood and a hot GF had my caged cock throbbing against the bed the entire time.

I had now learned to pee with the cage on and was finally getting used to it when Amber demanded I drop my pants so she could inspect me. This was pure torture. Now on her knees in front of me, she rubbed baby oil into my nuts and taint while simulating a blowjob on the cage. I could sort of feel her hot mouth and definitely felt the vibrations of her moans. My cock pulsed, but with no contact on the sensitive head, there was no chance I could cum.

"I don't want you to get too comfortable, baby, remember, you did this to yourself, you could be spending the day with my lips wrapped around your cock instead of this torturous cage, but you chose beer instead" poked Amber. I groaned.

And with that Amber licked my nuts and around the cage. My cock was now smashed and distorting itself trying to escape the clear tube. I moaned in frustration as she again dragged a nail across my taint.

"I guess this means you probably want a cock up your ass, so maybe we should start preparing you for that." shared Amber as her oily finger went into my ass.

I was too dumbfounded to move away and the sensation was pretty hot. "You like that, don't you? How about two oily fingers? Does that feel good, maybe I need to rub more oil on your poor nuts too, yeh does that feel good baby, Oh look at your cock, all smooshed in that cage with nowhere to go." Chided my now wild eyed girlfriend.

Amber's narrative stopped as she again put the cage into her mouth and pretended to suck me off. Naturally I could feel nothing and just groaned in frustration.

"Poor baby, I bet you wish you could cum, well, tell you what, If you let me put a plug into that tight little ass, I'll take the cage off and let you orgasm once. Would you like that?" Asked Amber.

I was in no position to say no and just nodded.

"OK baby, strip and get on the bed, let's get that little ass prepared for Bob."

I froze. Was she kidding? Was this just dirty talk? My hard-on subsided a bit as I walked to the bedroom and sat at the end of the bed.

"Lay back with your feet on the bed and your knees bent, I promise this won't hurt too much."

I did as told and felt more oil on my ass and then the pressure of what I assumed was a plug. It hurt a bit, but she went very slow and once the large end got past my muscle I just felt full.

"I want to get you used to cumming with something in your ass." Explained Amber as she unlocked my cage and slowly eased the tube off my rapidly growing cock. Next came the ring and a huge sigh of relief from me.

More oil was doled out and Amber began an erotic hand job. "How does it feel to have your ass full baby, it is turning you on? Your cock seems to like it."

I moaned as she then deep throated me, reveling in the sensation my cock had missed for the last few days.

"I think you're kind of into this, maybe we should get a strap on, wouldn't that be fun, I could actually fuck your ass, don't worry baby, I'll hold your cock while I violate your ass, so you'll get to cum too." Amber was clearly on fire, I had never heard her talk so dirty in the past.

With that image in my mind or maybe in spite of it, I shot a giant load all over Amber's tits and face. She never stopped stroking me as I twitched and moaned through a giant, much needed orgasm.

She smirked and licked her lips as she reached into her end table and pulled out a different cage. "This one is metal and has openings so I can lick you, but you still can't quite get hard, can you? Ohh, poor baby." Mocked Amber.

After rubbing on more oil, Amber clicked an ominous looking steel ring behind my balls. The constriction and feel of her lubed hands on my balls brought my cock back to life and it throbbed to nearly full length. There seemed to be no chance she could get me into the new cage and I hoped she could see the futility.

She placed the steel barred tube over the end of my cock and kept a steady pressure. The sensitive head slid begrudgingly into the cage and Amber smirked up at me. The lube was doing exactly what lube does and my head soon bumped against the end of the cage. Most of my dick was still visible and it seemed like an impossibility the cage would ever connect with the ring, but Amber kept the pressure up and against all odds, the tube end was soon contacting the ring and access to my cock became a fading memory. The snick of a closing lock sealed the deal.

My cock now pulsed helplessly in its shiney new prison. The meshy steel seemed to have even more finality to it than the clear plastic. Making things worse, Amber stroked the cage and sent faint sensations through my tortured cock.

"That was hot honey, thank you for playing along, let's pull that plug out now."

I moaned again as it slid out of my distended ass. Amber seemed to be enjoying this far more than I would have ever expected.

The rest of the weekend played out similarly and she let me out Sunday afternoon, but only if I would take a 6" vibe in my ass while she blew me. My brain was mush at this point and she had the vibe on high as I shot cum down her throat.

Sunday night she unlocked the cage and told me I had two weeks left to lose some weight before she let Bob use my ass. It did not feel like she was kidding and my already sensitive asshole twitched a bit.

The following week was filled with a sparse diet and a dangerous amount of exercise. I went into Friday on wobbly legs and the hope I had genuinely lost weight. I had just stepped out of the shower when Amber walked into the bathroom. The steel cage and lube were already staged on the counter. She smiled and motioned to the scale.

I stepped on and the numbers spun. They stopped at a perfect 200 lbs. I had hit my target a week early and I couldn't tell if Amber was delighted or disappointed, but I pointed to the floor and she knew what I was after. I reveled in the combination of an oily hand job and a deep throated blowjob that this woman had perfected. Leaning against the bathroom counter all I could think about was how close I had come to failure and how much less fun that would be.

"Cum in my mouth baby, you earned it, fill me up and make me swallow like a good girl does" moaned Amber before putting my cock back in her mouth and doing a tongue swirl that was making my knees weak. Her moans sent a subtle vibration into my dick that I'm sure were touching my soul while oily fingers massaged my balls.

Fuck, I loved this woman.

I was getting close and she could tell. The moans became more intense and her bobbing up and down on my cock grew faster. I was right on the edge when she pulled up and looked up at me "You know we are still doing this for one more week, right?" Winked Amber before diving back down on my cock.

I came, thrusting into her mouth as she held her fist wrapped around the base of my cock and milked me through an intense orgasm. After I calmed down a bit and Amber cleaned up I asked "So, wait, I hit my target, why are we waiting an extra week, are you bowing out of giving up your anal cherry?"

Amber leaned into me kissing my neck and grinding into my dick "We agreed to a five week program, that means you have another week, although you don't really have to lose any weight, you certainly can not gain even a pound or it will be your ass that gets violated." Moaned Amber.

This chick was diabolical and seemed to absolutely love pushing my buttons. I trundled off to work that day with a shit eating grin on my face and images of Amber's ass wrapped around my hard cock. Later in the day I was out grabbing lunch and passed an adult toy store that we had frequented in the past. Wonder what I could grab that would tweak Amber's mind a bit, maybe a chastity belt for her? Hmmm.

I wondered the aisles for a bit until I came up on a display of remote control vibrators. We had dinner plans tonight and this would definitely add a fun twist to the evening. Maybe even knock her down a few pegs. I grabbed a jeweled butt plug, some lube and an app driven vibe that nestled against her clit and wrapped into her pussy I assumed intended for her G spot. My face was consumed by an evil grin.

That evening I shared with Amber that we had reservations at a relatively swanky restaurant. What I did not share was that I had phoned ahead asking for a secluded table. I also explained instead of a blowjob before we left I had a special toy she would be wearing.

Amber gave me a side eye as she wrapped up her makeup. She looked gorgeous, her already tall frame perched on 4" heels and well muscled legs exposed by a relatively short dress. Classy, yet a bit of naughty. Very Amber. I handed her the toy and the illustrated instruction sheet it came with, having already charged it and installed the app on my phone. "Oh, we're upping the kinky game, are we?" asked Amber with a raised eyebrow.

"Hey, you upped your teasing game last week, now it's my turn. Put the toy in and let's go get dinner." I commanded.

"Ummm, yes sir, I'll put your new toy in my pussy so I'm nice and wet when we get home."

Little did she know, the toy was remote controlled. Knowing we'd both be drinking we grabbed an Uber and about mid way on the drive to the restaurant, Amber leaned in and whispered a breathy whine about the pressure on her clit and how it was really distracting. I took that as my cue and clicked the app open, setting the vibe to about quarter power with a slight oscillation.

Amber's eyes shot wide open and her hand went over her mouth. "Are you fucking kidding me? How am I supposed to get through dinner? Oh god, uhhhhh." moaned Amber trying not to be obvious as the Uber driver checked his rear view mirror.

"Remember when you took such great delight in tapping my cage or massaging my nuts, making me crazy? This is my version of that game and just so you understand what the evening will look like, I have the vibe on low." I stated, watching Amber's eyes dart about as she contemplated her fate.

Just to show her the potential, I zinged the vibe up to 75% and then back down and Amber gave out a yelp that again had our driver's eyes in the rearview. Amber whispered into my ear "You're fucking demonic, what do I have to do to keep you from turning that on while we are in public?"