The Adventures of Tim and Laura: Surprise Mistress Questioning - Part 2

This will be a collection of erotic short stories about a couple named Tim and Laura and their adventures into exploring the world of BDSM and kinky play. There is no definitive timeline associated with them, as in some may be more vanilla and tame from when they were first getting into BDSM play while others may involve a deeper journey into BDSM with group sex and kinkier scenes. These stories will involve Mistress/slave role play, Master/slave role play, male and female chastity, and pegging from a couple that does BDSM casually and not hardcore or as a life style. Hopefully these stories will inspire those just getting into BDSM and testing the waters. I would also hope that these stories would give some newcomers or inexperienced readers that stumble across the Oxy blog and the Oxy-shop website some ideas as to what to do with those shiny new toys they just ordered.

Tim awoke to the now nearly constant aching of his balls as his morning wood strained in its cage.  This was the fourth morning of his new full time confinement within his chastity.  He knew he wasn’t going to be able to get back to sleep so he quietly rolled out of bed and went into the bathroom to relieve himself.  When he came back out, MIstress Laura had thrown the covers off herself and was laying in the middle of the bed with her legs spread.

“Why don’t you come over here and wake me up properly”, she said, beckoning him over to the bed.  Tim quickly complied and slid back onto the bed between her legs.  He made his way up to her already wet pussy and started to work his tongue slowly up her slit to her clitoris, swirling his tongue around it a couple of times before working down to her asshole and giving it the same treatment.  He repeated this a couple of times before clamping his mouth down over her pussy and gently sucking on it while alternating between flicking her clit with his tongue and slipping his tongue in and out of her pussy.  His cunnilingus skills quickly had Laura bucking her hips against his mouth as she moaned through her first orgasm of the day.

“Mmmmm, thank you slave, that was very satisfying,”  Laura said as she disengaged herself from Tim, who was still trying to lick and suck on her pussy in a futile attempt to get some sexual gratification for himself.  “Now, go shower and plug yourself.”

This had been the new morning routine for the last four days.  Tim would wake up, use the restroom, give Laura an oral orgasm, then shower and plug his ass.  Laura had surprised him with a new butt plug trainer set the first morning of his confinement.  She had informed him that he was to work up through the plugs from smallest to the largest.  Each day he would have to move up to the next larger size.  There were four total plugs in the set ranging from a diameter of 1 inch to 2 inches in ¼ inch increments.  Today he would be inserting the last and largest plug.  As he slowly worked it into his ass he wondered what her plan was after this.  A two inch diameter toy was really nothing new to them, Laura’s largest girlcock was a 9 inch long, two inch diameter realistic dildo that Tim had taken many times before.  As Tim was thinking all of this through, the plug eased past the largest point of its flare and his ass greedily sucked it in the rest of the way, quickly putting pressure against his prostate and making the tip of his cock bead with precum.  His legs shook slightly as he stood up and the plug shifted within him causing a wave of pleasure to pulse through him.  It was going to be hard to concentrate on anything else today with this plug in Tim thought.   

Since Tim worked from home, Laura was able to have him wear the plug as long as she wanted.  Typically she had him wear it for a couple hours after he started work and would then give him a break.  As Tim sat at his computer fidgeting slightly from the large plug in his ass pressing against all his pleasure points, he kept an eye on the time.  Having this large of a plug in was definitely different than any of the smaller ones.  Each little shift in position or movement reminded him that it was there and his cock was throbbing in its cage almost constantly with the occasional leak of precum beading up on the tip of his cock reminding him how full his balls were.  It was safe to say this was not going to be one of his most productive mornings.  It had been just over two hours since he had started working and he was anticipating Laura to text him at any time now to remove it.  Two hours later he finally got the text, “Slave, go remove your plug and prepare yourself for me.  I will be home in 1 hour and I expect you to be cleaned up and impaled upon your anal dialator when I arrive.”

Tim quickly jumped into action and practically ran to the master bedroom to remove the plug.  He was grateful to finally have it out, giving his bulging cock some relief, but missed it at the same time.  He quickly jumped in the shower and went to work preparing his ass for Laura, making sure that it was spotless inside and out.  After this was done he decided he had better grab a quick nibble of food and hydrate himself as part of his preparation for his Mistress.  She was so unpredictable lately that he had no idea what to expect from her anymore.  With 15 minutes left until Laura was to be home, Tim headed back to the master bedroom and pulled out his anal dialator toy, The Intimidator.  It was an 11 inch tall conical shaped toy that started with a 1.8 inch diameter knob at the top and then tapered from a 1 inch diameter to a 3.5 inch diameter at the bottom.  Tim plopped it in the middle of the floor of the master bath and then generously lubed it before slowly sinking down on it.  Even though he had just had the 2 inch plug in him, the slightly smaller knob of this toy still felt great as it popped inside him.  He paused for a second and then sank slowly down onto the toy.  As he slid further and further down the toy he could feel it slowly stretching him more and more until he was at his limit, a little over halfway at around the 2.25 inch diameter mark.  He then started to gently thrust against the toy slowly stretching himself further and further.  He had no idea how big this “horse cock dildo” Mistress Laura had talked about would be so he was preparing himself for anything.  Once he had worked himself down on it a few times, he bent forward, holding the Intimidator inside himself and scooted back to the wall, pressing the toys suction cup against the wall and positioning himself in the doggy style position.  He then pressed back against the toy, working it back to his maximum depth and then wiggled his ass against stretching himself out more and working it ever so slightly deeper into himself before backing off slightly and repeating the process again and again. 

“Oooh, that’s hot,” Laura said startling Tim.  He had been so lost in the pleasure and concentration of stretching himself that he hadn’t even heard her come in.  “Well, don’t stop on my account,” Laura said with a laugh as she stripped off her clothes while watching Tim stretch himself.  Tim watched as she pulled out a pair of black pleather, thigh high, high heeled boots they referred to as her Mistress boots and put them on along with a black g-string, and an electric blue pvc underbust corset. 

“Ah, that feels more like it,” she stated as she checked herself out in the mirror while watching Tim still working himself on his toy.  “Slave, put that toy away and meet me in the bedroom,” she stated before walking out.

Watching her tone ass saunter out of the room made Tims cock throb even more as he pulled off the toy.  He quickly cleaned himself and the toy up, and met MIstress Laura in the bedroom.  When he walked in, he saw that Laura had a towel laid on the bed along with three new dildos.

“Slave, I am going to introduce you to some new toys,” Laura said as she waved her hands over the three dildos.  “The first one is called the Inseminate Me.  It is 8.5 inches long and ,as you can see, it has four bulbs along its length, each larger than the last ranging from a 1.5 inch diameter to 2.2 inch diameter.  This one should open you up nicely and prepare you for the other two.  This one”, she said holding up the second toy, “is called the Realistic Dragon, it is 8 inches long, has a 1.5 inch diameter head and then flares rather quickly to just over a 2.5 inch diameter.  I think this ridge ought to feel rather interesting, don’t you?” she asked, indicating a thick ridge that ran along the underside of the dildo.                                      

“Mmmmm, yes ma’am, that should be interesting.,” Tim replied.

“And finally, the main event,” she said as she held up a replica horse cock dildo.  Tim was taken aback for a second.  He hadn’t really thought she meant a horse cock, just a big dildo, but it did look interesting.  “This one,” she continued, “is called the Stallion, for good reason.  It is 9.6 inches long with a 1.7 inch diameter head and a 2.5 inch diameter base.  I hope you're ready for this,” she said with a wink, laying it down on the bed.  “Now get up on the bed doggy style facing away from me slut!” she exclaimed, causing Tim to jump.

Tim quickly got into position on the bed and soon felt Mistress Laura squirting lube onto and into his ass, preparing him for the new toys.  Soon he felt the tip of the first toy nudging against his asshole.  His already pre-stretched ass quickly accepted the tip of the toy and he felt the first bulb pop in, quickly followed by the second, then the third, and finally the forth.  His stretched ass barely offering any resistance and accepting it’s full length.  “Wow,” Mistress Laura stated in slight shock as she slowly pumped the dildo in and out of Tim’s ass. “You must have done a good job stretching Slave, you easily took that one.  But the next won’t be as easy,” she said as she pulled the Inseminate Me out of Tim’s ass leaving it gaping slightly.

She quickly lubed up the Realistic Dragon and easily popped the head into her slave's ass.

“Mmmmmm,“ Tim moaned as his ass was being stretched and used by his Mistress.  His caged cock was rock hard in its cage and slowly dripping precum as it swung gently between his legs.  Mistress Laura could feel her pussy getting wetter and wetter as she watched the head of the dildo quickly disappear into her Slave as his ass slowly sucked more and more of the dildo into him.  The dildo had a slight bend to it with a ridge on the outside of the curvature.  She had rotated the dildo so that the head was curved down with the ridge pointing up.  She knew in this position the head of the dildo would rub against her Slaves prostate driving him wild and she could watch the ridge stretch her Slave’s ass.  Tim moaned louder as the head of the dildo passed back and forth against his prostate.  With each slow thrust of the dildo, he could feel the head rubbing against his prostate and the base stretching his ass more and more.  The combination of both of these sensations soon had him moaning and bucking his hips with each thrust, his cock constantly leaking precum now.

“Mmmmmm, my Slave likes this one, don’t you?,” Mistress Laura asked as she thrust the dildo in and held it in place causing Tim to buck his hips more and hump the air while grinding back against the dildo.

“Mmmmm,” he moaned, “yes Mistress it feels so good.”

“Well then this next one is going to feel even better,” she stated as she pulled the dildo from him.  “Slave, crawl further onto the bed,” she commanded. 

Tim did as he was told and shortly after felt Laura kneel up on the bed behind him.  He then felt the large, flared head of the horse cock press against his ass.  Laura had put the horse cock in her strapon harness and was intending to give him a proper fucking with her new girlcock.  After all the preparation and stretching, the head of the horse cock easily worked its way into him.  Tim gasped as it entered him and the flared head and thick shaft slowly started to sink into him.  The size of it put constant pressure on his prostate and nearly took his breath away.  Laura stopped with half the length into her slave and let him adjust to the size of her new member.  “How do you like it so far Slave?,” she asked

“Mmmmm, it’s big and feels so good,” Tim managed to get out.

“I am halfway in, do you want the other half?,” she asked

“Ooooh, Yes Mistress, please give me all of your horse cock,” Tim pleaded as he tried to rock back against her.

Laura smeared some more lube over her horse cock and slowly continued pressing it into Tim.  Her pussy kept getting wetter and wetter with each inch of dildo her Slave’s ass was swallowing.  It was making her so horny, she just wanted to plunge the horse cock all the way into him but resisted the urge.

Tim moaned as the horse cock continued to penetrate and stretch his ass.  The constant pressure on his prostate had his cock leaking precum again as waves of pleasure pulsed through him.  His cock felt as if it were trying to burst out of its cage.  Just when he didn’t think he could take any more, he felt Laura’s pelvis press against his ass cheeks.

“Wow!, I can’t believe you took that whole thing!,” Laura exclaimed as she bottomed out in Tims ass.  “That is so hot!”

All Tim could manage to respond with was a moan.  The thick shaft filled him up like he never had been before.  All the new sensations had his legs shaking and his hips slightly bucking against Laura.  Laura took all this as a clear sign to keep going and started to slowly thrust in and out of Tim.  She started out nice and easy, slowly picking up her pace every couple of thrusts until she was thrusting in and out of him at a steady rhythm.  Tim hadn’t stopped moaning and bucking his hips the whole time.

The steady pressure and movement along his prostate had Tim moaning non-stop as Laura picked up her pace.  Tim could feel wave after wave of pleasure emanating from his prostate to the base of his cock, and then out to the tip of his cock.  As Laura thrust in and out of him, his caged cock swung back and forth underneath him, adding to his pleasure.  Soon he felt an anal orgasm quickly building.  In his highly aroused state and after being locked up for the last four days allowed it to quickly build up and wash over him sooner than ever before.  His ass spasmed and convulsed around the giant cock in his ass as it continued to relentlessly pounded away at him.

Once Laura had settled into a steady rhythm she had clamped her legs together and could feel her pussy rubbing against itself with each thrust.  She started to fuck her slave with renewed vigor, determined to get herself off.  She was about halfway to her orgasm when she saw her Slave writhing beneath her.  “Guess we will see if you can have me than one anal orgasm,” she thought as she concentrated on working towards her own.

Tims moans continued as Mistress Laura kept pounding his ass with her huge horse cock.  Tim could feel another orgasm building as his cock strained in it’s cage like never before.  He could also hear Laura moaning as she worked closer and closer to her own orgasm.  Realizing that Laura was fucking his ass for her own pleasure now and not for his strangely aroused Tim even more and pushed him over the edge to a second anal orgasm, this time he could feel his cock pulsing and straining even harder in it’s cage.  Opening his eyes to look between his legs, he could see his cock oozing and streaming cum out of it as the orgasm wracked his body.  He could hear Laura moaning more and more and knew that she must be close.  Laura suddenly grabbed his hips and drove her horse cock deep into him spasming against him as her own orgasm overtook her.  As she rode her orgasm out fully thrust into him,  it was like one long, continuous orgasm gripped Tim and milked every last ounce of cum out of his balls until Laura pulled out of him with a pop.  Exhausted, they both collapsed onto the bed panting.             

After a few minutes Laura rolled off the bed, “Hmmmm, you took that Stallion easier than I thought you would.  Maybe I will need to find something even bigger for my Slave to work up to now.  Perhaps we ought to leave that cage on for a bit longer….,” she said with a wink.

“Oh boy,” Tim thought as he watched Laura getting ready to get in the shower, “guess I’m in for some more fun!”.