Two Mature Dommes

As Grace and Emily finished their shower together, they stepped out and began to dry each other taking the time to enjoy the curves of each other’s mature body. The longtime lovers were getting ready to go out and celebrate Emily’s birthday as she was turning fifty. Grace who was now fifty-two had promised her that they would go on the prowl for a new ‘victim’ for lack of a better term. Both of the ladies thoroughly enjoyed breaking young men and teaching them the proper way to treat all females.

Helping each other dress in nice lingerie including garters and stockings the excitement of both of them continued to grow. It was Grace who suggested that they both forgo panties and Emily laughingly agreed, saying she might be tempted to flash a few young men! Finishing up by putting on short dresses with plunging necklines and spike heels the ladies headed out for what they hoped was a birthday celebration to remember!

Grace drove them to a different club than where they usually went telling Emily that she had heard lots of young women came here which of course meant young men would be there as well, in hopes of scoring with a girl. Grace parked toward the back of the lot in a less noticeable area, explaining to Emily that she was just planning ahead! Grinning with delight, Emily kissed Grace fully on the lips and then they strode into the club to see what they would find.

Happily upon entering they discovered the club was nearly two thirds full, elevating their hopes for finding their prey! Spotting a table in the middle of the club, they seated themselves and started taking in the people around them while waiting for the waitress to come by. As they were enjoying the first glass of wine, a couple of young ladies came into the club which was filling up quickly. Looking for an open table and not finding one they saw Emily and Grace sitting there with two open chairs and asked if they could join them. Grace quickly agreed thinking that the two gorgeous women certainly couldn’t hurt their chances of attracting some horny, young males.

Almost like clockwork, a few boys came by trying to score with the younger ladies, but were quickly rebuffed, much to their chagrin. They chatted like old friends even though Grace and Emily were old enough to be their mothers. After a half hour of turning down potential suitors one rather shy young man came over and made an awkward attempt at interacting with the young ladies. Both of the mature ladies recognized quickly that this boy was very unsure of himself and was likely quite inexperienced with women. What could be a better find for two women looking for a new “play toy”?

After getting him to tell them his name was Tim, Grace said that she thought Tim was a man’s name and he looked more like a ‘Timmy” and as such that was going to be his name tonight! Then Grace questioned the young man about whether he had ever made love to an older woman, one with lots of experience in teaching men about pleasing a woman properly. Hanging his head somewhat he answered in the negative, further humiliated by the giggles of both the young women at the table. Emily inquired if either of them were interested in going home with the youngster, which again brought forth a lot of giggling and a resounding denial of any interest. Grace noticed how red his face seemed to be getting, adding to her pleasure.

Grace then grabbed his forearm, squeezing tightly, and led the boy onto the dance floor. Seizing on the moment with a slow dance song playing, Grace pulled Timmy close and whispered in his ear, asking if he thought he could please her if he went home with her! Totally taken aback by her question, he tried to stammer out an answer, but before he could finish Grace slid her hand down and grabbed ahold of his crotch, squeezing hard, and discovering a hard cock. While still squeezing hard, Grace looked right into his eyes and asked if he wanted to come home with her, guaranteeing him that his balls would be drained by morning!

Seeing a slight nod of his head, Grace pulled him back to the table, announcing loud enough for others around to hear, that Timmy was going home with her, and Emily since he was her birthday present! And she hoped that he had what it took to survive the night! The laughter from the young ladies again added to his feeling of humiliation. And with that Grace and Emily each grabbed one of his hands and led him into the parking lot.

Grace then informed him that they were going to take him home and teach him how to properly pleasure a woman. Emily told Timmy how happy she was that he was her present and that she was looking forward to draining his balls! Standing next to their car, both ladies took whatever liberties with Timmy they wanted and spent some time squeezing his genitals and pinching his nipples through his shirt. They both assured him that they would bring him back tomorrow after he proved that he had learned his lesson! Emily then ordered him to slide into the back seat of the SUV and she slid in next to him.

On the drive back to their house, Emily managed to get Timmy’s fly open and was able to get to his cock and stroke it to get him fully erect. By the time they pulled into the garage, Emily had his pants part way down his thighs and was working his balls over as well as his cock. Timmy felt like he was in heaven with all the attention she was paying to his genitals. Grace went around and opened his door and pulled him out with Emily right behind him. His jeans slid the rest of the way down his legs acting like a binding around his ankles as the two women stood him up. Reaching around him from behind, Grace unbuttoned his shirt and Emily quickly removed it for her leaving Timmy bare chested and a little surprised how quickly things were moving along. With Grace still holding him, Emily removed his shoes, jeans, and underwear leaving him totally naked. Grace pinched his nipples and Emily fondled his balls, the combined actions bringing Timmy to a full erection.

Emily gathered his clothes and threw them into the back seat of the SUV and Grace locked the vehicle even though it was in the garage, explaining to him that he would need no clothes until they decided to take him back to his own car. Feeling his unease at this comment, they again each grabbed him by a wrist and led him into the house.

Leading him into the living room, Grace stood behind him holding his elbows back so that his chest was thrust out toward Emily. “Now Timmy, Emily is celebrating her 50th birthday today and you are the lucky boy that has been chosen to give her multiple orgasms! But because we can tell you have little to no experience with women, especially mature cougars like us, we know we will have to train you in proper servicing of pussy. Now relax, we won’t hurt you, much!!”

“Do you like my cleavage, Timmy?” asked Emily. “I saw you staring while we drove home. I bet you want to suck my lovely breasts don’t you?”

“Yes, I, I, I do Emily,” stammered her present.

Grace quickly reached between Timmy’s legs and grabbed his balls. Without hesitation she squeezed hard and twisted them, bringing forth a screech of pain from the shocked Timmy. “Now you must learn your manners first, Timmy. Whenever you speak either of us you will call us Mistress Emily and Mistress Grace! Do you understand?” inquired Grace as she gave another hard squeeze.

“Owwwwwww,” was Timmy’s response followed by “Yes Mistress Grace!!” Still being held by his balls although not being squeezed, he felt his legs tremble as he feared she would inflict more pain.

Releasing his balls, Mistress Grace ordered Timmy to drop to his knees, which he immediately did, fearing yet another painful response from Mistress Grace if he hesitated. “My, my,” exclaimed Grace, “I think little Timmy is already learning that he needs to do exactly as he is told!”

Standing next to each other looking down at Timmy on his knees, Emily and Grace embraced and Emily told Timmy to watch closely. As he knelt there, the two best friends enjoyed a nice long tongue swapping kiss, causing Timmy’s mouth to drop open. Glancing down at his rock hard cock Emily announced, “I think it is time the little boy gets a reward!”

Quickly agreeing, Emily, then Grace, dropped their dresses right before him, leaving Timmy staring at them in bras, garters, stockings and their spike heels. Timmy stared in disbelief as he was now looking directly at two naked pussies. “Oh there is more Timmy,” purred Emily. Both of the ladies then turned showing their lovely asses, bending forward and spreading their cheeks leaving him to gaze at their puckered rosebuds. “If you are lucky, you will be getting more intimate with our special spots later,” cackled Grace, raising some fear in Timmy’s mind as he had never ever touched a woman’s rosebud.

“Let’s get him in the bedroom, so we can see if he has any idea how to eat pussy,” laughed Emily.

Grace demanded, “Crawl behind us, Timmy. We will let you ogle our beautiful ass cheeks!”

When they entered the bedroom, Timmy noticed the large king size bed and the wooden frame that supported it. He nervously noticed that there were leather cuffs and straps attached to various points on the frame. But before he could really process for what all those might be used, Emily lay back on the bed with her pussy right at the edge of the bed, then spread her legs wide. Grace directed Timmy between her lover’s silk covered thighs.

“Alright Timmy get your tongue to work on that gorgeous pussy. Lick my lover and make her orgasm all over your face,” ordered Grace. Sensing his hesitation, Grace grabbed the back of his head and pushed him forward until his face was in her pussy. “Come on, lick!!! Long strokes with your tongue! Suck her clit gently! Come on get with it!” Grace continued to demand of Timmy.

With a tone of disgust, Emily asked, “Have you never eaten pussy before boy? Are you a pussy eating virgin??”

“No Mistress Emily, I have licked pussy before, but only a few times” whined Timmy.

Grabbing him by the back of his neck, Grace pulled him away from Emily’s womanhood telling him to watch how it is done. And with that, Grace got down and started to show Timmy how to eat a pussy properly! Timmy watched with his mouth agape, having never seen a woman eat another’s pussy! He was enthralled and put his face closer to see all the action.

“Oh baby, you are the best, Grace. Please keep eating me, as I don’t know if little Timmy will be able to master the art of pussy worship,” snickered Emily. As Grace continued to lick her friend, Emily noticed that Timmy now had a fully erect cock, and it looked rather wonderful. But Grace continued her oral skills and before long a huge orgasm snuck up on Emily and she exploded, drenching her lover’s face with her juices. Timmy looked shocked at what had happened!

“Now that is how you please a woman, Timmy. Let’s see if you learned anything? Get your face back in her pussy and eat her until she has another orgasm” demanded Grace. When she saw Timmy hesitate, Grace forcefully shove his face back where it belonged and Emily closed her thighs around his head and squeezed a little, demanding that he start licking or else!

While Timmy went to work trying to mimic what Mistress Grace had done, Grace pulled his wrists behind his back, telling him that didn’t need his hands for this task! And before he knew what happened she had handcuffed his wrists, leaving Timmy nervous as to what she was planning. Emily then grabbed him by his ears, pulling him tighter into her sacred pussy as she started to climb toward an orgasm. While Timmy was focused on making her cum, Grace slipped cuffs on his ankles and locked a leather collar around his neck.

“Stop worrying, nothing bad will happen to you tonight!” laughed Grace. But the fear of what was happening took Timmy off his focus on Emily’s orgasm and Emily roughly pushed him away as her climax eluded her.

“You little bastard” screamed Emily, scaring the daylights out little Timmy. “Do you know what happens to little boys like you who don’t get me off with their tongue?”

“No Mistress Emily, but please let me try some more. I will do better!” cried the scared looking Timmy.

“Oh you will do better all right when I have punished you for your failure boy,” retorted Emily as she slid herself to the edge of the bed and sat up. Then without warning she yanked Timmy across her lap and informed him that was going to get a good hard paddling for his poor performance! So saying, she locked one leg around his legs as she was sure he probably did not have much experience being spanked either, and she didn’t want him squirming away while she blistered his little bottom!

Grace walked around so little Timmy could see the paddle she had gotten for Emily to use. She described how it was made from hard oak and was well varnished. Grace also told him that she was sure he would be bawling like a little boy long before Emily finished with him. Timmy was really starting to worry now about what was to happen, but before he could form a protest or even speak up, Mistress Emily landed the first smack across his bottom, bringing out a squeal of pain from his mouth.

“Now you are going to get 24 more whacks just like that one, boy!” exclaimed Emily. Grace saw the look of terror on Timmy’s face and then stated, “Your bottom is going to be so sore little Timmy, you can’t imagine how hard Mistress Emily is going to paddle you. And you know what? I bet both Mistress Emily and I will have wet pussies when she finishes.” Timmy heard the laughter of both Mistresses and knew he was in for some serious discipline.

As Emily rained down the strokes of her paddle, Grace enjoyed watching Timmy’s face and seeing the expressions of pain he was feeling. By the tenth stroke the tears were flowing, at the fifteenth smack the bawling started, the twentieth stroke resulted in Timmy begging for his Mistress to stop. By the time Emily delivered that final whack of that hard wooden paddle, little Timmy was a sobbing little boy much to the pleasure of his two mature Dommes.

Pushing him off of her lap, Emily again laid back and spread her legs and demanded that Timmy get his face back in her pussy and eat her to another orgasm. Fearing more pain, Timmy quickly knelt and again starting licking as his Mistress had demanded. With his hands still cuffed behind his back, he tried to focus on pleasing her in spite of how sore his ass was felling and after several minutes he heard her moan.

“That’s it boy, don’t you dare stop!” warned Grace. “If you do a good enough job maybe Mistress Emily will let you fuck her! She always gets so hot after beating a boy like you. I can feel your cock is all hard, maybe just maybe you will be given such an honor as to slide it into her hot tight pussy!”

Hearing Grace’s words, Timmy sped up his licking, taking long strokes and being sure to lick her clit on each stroke. After several more minutes and feeling his tongue tiring, Mistress Emily clamped her thighs around his head tightly and exploded in a wonderfully satisfying orgasm that lasted for a full minute and left her gasping.

“Well, well little Timmy, it seems that you performed much better after your little ass paddling! But as Mistress Grace warned, now I am horny for a hard cock! Do you want to put yours in me and try to please me again?” inquired Mistress Emily.

“Oh yes, please Mistress Emily, please let me put my cock in your pussy! Please!! I promise not to disappoint you!” begged Timmy.

Unbeknown to Timmy, Grace had slipped on one of her strap-on dildos and walked up behind Timmy holding two rings as well. “Maybe she would prefer my cock instead little Timmy. I think it is bigger than yours!” laughed Grace. “Face me boy so I can put these rings in place before you are allowed the privilege of fucking a real woman!”

And showing no mercy, Grace forced his balls through one ring so that it sat tight above them causing him some discomfort. Then grabbing the smaller ring, Grace quickly slid it up the length of his cock until it was nestled against his belly. “There, now we don’t have to worry about you staying hard or having a premature ejaculation and ruining Mistress Emily’s pleasure!”

“Now get up here on the bed with me boy, and give me a good fucking!” demanded Emily. “And if I don’t enjoy myself, well let’s just say that spanking you got before will seem like nothing as I will give you ten times the pain!”

As demanded, Timmy got into position fearful of not pleasing Mistress Emily. He hesitantly started to push his erect cock into her, feeling how hot and wet she was. “Come on boy, get with it! I want to feel some good thrusting! I have had much bigger and better cocks in me before, so disappoint me!” barked Emily.

After watching Timmy for a few minutes as planned, Grace exclaimed, “For heaven’s sake Timmy thrust harder and faster! Or do I need to show you how it is done?” Letting Timmy continue on for a few more minutes and in spite of how much Emily was enjoying his youthful cock, Emily told him to stop! Crestfallen Timmy started to withdraw, only to hear Mistress Grace bark at him, “No keep your cock in her wet pussy, all the way in! Now I will show you what we mean when we say to give a woman a proper fucking!”

Confused, Timmy did as he was told and then felt Mistress Grace get behind him on the bed. Then he felt her smearing something cold on his asshole and probe it with her finger. With so little sexual experience, Timmy was totally shocked when he felt her strap-on push against his hole! “Now this is how you should be fucking Mistress Emily!” he heard Mistress Grace casually state. As he realized what was about to happen, he remembered how large her dildo was and started to panic. Unbeknownst to him, Grace had swapped the large dildo for a much smaller one since she was sure he was an anal virgin.

“Hold on little Timmy, here it comes!” cackled Mistress Grace as she rather forcefully shoved the 6 inch long, 3/4 inch thick dildo deep into him, then holding it fully inside him to allow him to adjust to its size, even though it was the smallest one she owned. Grabbing his cuffed wrists, she demanded, “Now hold still while I fuck you, boy!”

Even though it filled him, Timmy realized that the dildo didn’t really hurt even though he still thought it the big one he saw Mistress Grace wearing earlier. As she slid the well-greased strap-on in and out, she explained to him that she wanted him to match her thrusts with thrusts into Mistress Emily, which he readily agreed to.

After a few minutes of slow and easy, Grace started to pick up the pace, going faster, harder and deeper, causing Timmy to do the same. “Now here is the deal little Timmy. I am going to continue to fuck you harder and faster and you will do the same to Mistress Emily. And I will continue until you make her have a good hard orgasm! And don’t worry about me because I can keep this up for a long time no matter how sore you become.”

As Timmy tried his best to please Mistress Emily, he felt the increased pounding of his soon to be sore asshole by Mistress Grace. It seemed she was really intent of making him get Mistress Emily off! As he continued to thrust in and out of her warm wet pussy, he nearly started to ignore the constant plundering of his poor hole that is until Mistress Grace started smacking his ass cheeks extremely hard with the same paddle Mistress Emily had used on him.

Feeling the intense pain from the paddling, he heard Mistress Grace’s stern warning, “Now fuck her faster boy! I want to see her have a nice hard orgasm from your little cock. And if you don’t deliver, I will be using a wide leather strap across your ass next, and I guarantee it will be very painful!”

Mistress Grace’s words caused Timmy to really increase his efforts and to concentrate on Mistress Emily’s pleasure instead of his own. After what seemed like forever to him, he heard Mistress Emily start to moan loudly and then Mistress Grace encouraging both of them to keep going while she continued to blister Timmy’s bottom. When it struck, her orgasm seemed to overtake her entire body in Timmy’s eyes, as Mistress Grace continued to thrust hard into him. Finally Mistress Grace ordered him to stop and hold himself deep in her divine pussy while Mistress Emily rode out her orgasm.