Owning My Friend's Mom - 4
When Greg felt the worst of her coughing was over, he began to praise her for a job well done. "Anne, that had to be the best blowjob I have ever had. You suck cock like a real pro. From this point on, that is what I expect of you whenever you are giving a blowjob." Stroking her hair, he continued. "As well, you will also learn to love the taste of cum. If the load is not deposited in your mouth, but rather somewhere on your body, then you will scoop that cum up and place it into your mouth. Protein shakes will become your favorite little whore snack. Is that clear?" Greg asked.
Mrs. C. still knelt at his feet, face red with exertion and shame. She simply nodded her head, too shocked to respond.
"Now Mrs. C., we are half-way through your punishment and you're doing great. Hopefully, after all of this is over, you'll realize the importance of doing whatever I say, when I say it."
Greg found the look of shock on her face was utterly priceless. It was quite obvious that she had thought her ordeal to this point was over. Reaching down, he grabbed a nipple and pinching hard, pulled her to her feet. Still holding her nipple, Greg pulled her toward the kitchen table. When she was standing before it, he positioned her so that she was facing the back door and then pushed her down over the table.
"Now, Mrs. C., I want you to grab the edge of the table in front of you with both hands. You will hold on to this table and not let go, no matter what happens. Should you let go, then your punishment will be doubled. I'm hoping by now, that you realize I am quite serious about your punishments." With those words Greg could see the knuckles on her hands whitening, as she instinctively tightened her grip on the table's edge.
"Spread your feet apart. Wider. Now keep your feet like that." Greg stepped back to admire the view for a few seconds. With her bent over the table and her feet spread apart, her nicely shaven pussy was clearly on display, as was her puckered little asshole. It was also quite obvious, to anyone who cared to look, that she was immensely turned on. Her pussy lips positively glistened with moisture and small rivulets of it trickled down her thighs. Grabbing the camera from his pocket, Greg snapped a few more pictures for his growing album.
Walking over to the back door, Greg bent and picked up one of Stacey's discarded flip flops. As he stood back up, Greg checked the lock on the back door and confirmed that it was not locked. Walking back over to stand in front of Mrs. C., he informed her that, "I am going to spank you now with Stacey's flip flop. This will be our little secret. Every time she puts this shoe on, she'll be oblivious to the fact that it was used to spank your pretty little ass." Walking behind her, Greg continued. "You will keep your head up through it all, and keep watching the back door. Just so you know, it is not locked, and anyone could come walking through it, at any moment to find you in this compromising position. Perhaps even Stacey will walk through that door, having forgotten something or other, and find you willingly humiliating yourself for me." Greg could tell the words were having an effect on her, since she began to visibly shake on the table. "Remember - don't let go of that table, under any circumstances," he cautioned.
With those final words, Greg reared his hand back and brought it down hard upon Mrs. C.'s left ass cheek. The responding CRACK echoed throughout the kitchen, as Mrs. C. shrieked in shock. Taking aim at the other cheek, Greg, again, smacked it as hard as he could. Another satisfying CRACK followed by an equally satisfying shriek followed. Greg then began a steady barrage on her ass, ensuring that he reddened every part of both of her cheeks and upper thighs. Her howls and sobs of pain, mixed with the CRACKs of each blow, were an intoxicating aphrodisiac, and, soon, had Greg hard as a rock and ready for round 2.
When she was a blubbering mess and her ass was a nice shade of dark red, Greg stopped his ministrations, and, again, stepped back to take a few photos. To her credit, Mrs. C. maintained her position and never let go of the table. Greg was actually beginning to feel strange feelings of pride for her. He was amazed at how easily she had been manipulated, and how well she was taking all of this.
"Now, Anne," Greg informed her, "we are almost done with your spanking. I want to make sure that this moment is forever etched in your mind, so that the mistakes made will never be repeated again."
At this, she began to panic and plead with him in an irrational voice. "Please, Greg, no more. I'll be a good little whore. I'll do anything you want, but please no more spanking. I beg of you." A note of hysteria was creeping into her voice, and, while her vehemence was moving, Greg knew there was one final thing he needed to do, to cement this moment in her brain forever.
"I'm sorry, Anne, but lessons need to be learned here. I promise it will be quick ,though," Greg says patting her affectionately on her back. Picking up the wooden spoon used earlier on her breasts, he then informed her, "I am going to apply one hit each with this wooden spoon to your pussy and asshole."
No sooner had the words escaped his mouth when Mrs., C. began to plead, "Oh please no, not that! Anything but that. It'll hurt too much."
Ignoring her, Greg continued, "If you maintain your position, then it will only be one each. However, if you move or let go of that table, I will be forced to tie you down to the table, and I will then administer 10 strokes to each," Greg finished menacingly.
With that Greg took up position, again, and, taking aim at her puckered asshole, brought the spoon down hard, right on her anal bud. An awful wail bubbled out of Mrs. C. as her back arched, shooting her crotch into the table, as if it could escape from the pain. Again, she never let go, and, after several moments, resumed her position on the table, quietly sobbing to herself.
"You're doing very well Mrs. C. Just one more and we're done with your spanking." This time Greg took aim at her soaking wet pussy, and, with an underhanded stroke, brought the head of the spoon up to hit her squarely on her shaven lips. If it was possible, her scream of pain was even worse than the one for her ass, moments before.
Walking around to stand in front of her, Greg held the spoon out to her and instructed her to kiss it, and to thank him for her punishment. Between sobs, she managed to mutter, "Thank.....you.....for...my......punishment."
"I think it appropriate, at this point, to formalize our relationship," Greg explained to Mrs. C. "From now on, you will refer to me as Sir, at all times. The only exception will be if your daughter is in the room. Then you may refer to me by my first name. Is this clear so far, Anne?" Greg asked.
"Yes.........Sir," she hesitatingly responded.
"Very well, now, you can see that you have given me another erection, and I think it only fair that you help me to relieve it," Greg began to explain as he walked behind her once more. Taking aim at her pussy, Greg shoved his cock into her wetness, and, in one hard stroke, buried it to its hilt. Her back arched, once again, but this time she pushed back against him ensuring that he was buried as deep as he could go. A soft moan escaped her lips, as Greg settled into a nice rhythm, thrusting into her cunt. With each jab, Mrs. C. pushed back against him, slapping his skin against her already reddened ass. Soon the tempo of her thrusts quickened, and Greg could tell she was nearing climax.
"Do not cum without permission whore," Greg cautioned.
No sooner had the words left his mouth, when she began to beg, "Please, Sir, let this whore cum for you. I need to cum so bad. I've been a good girl. I've taken all of your punishments. Please let me cum?" she pleaded.
"Very well. Since you asked so nicely, you may cum for me," Greg replied.
With that, Mrs. C. quickened her pace once more, and within a few seconds, exploded in an ear-shattering climax. 'Thank God, these houses were on large lots,' Greg thought, 'because, if the neighbors could hear, they would think bloody murder was happening here.' Her body convulsed and shuddered and writhed beneath him as wave after wave of pleasure rippled throughout her body. All of the pent up frustrations and emotions, she had kept bottled up over the years, suddenly came pouring out of her in one almighty orgasm, causing her to nearly pass out from the pleasure and relief. She realized then, on a very deep level, that, despite the obvious wrongness of the situation, it was something she needed, and had perhaps craved for years. She wasn't yet ready to put those thoughts into words, but just acknowledging them to herself was like a tremendous weight being lifted, from her shoulders.
Oblivious to all of her inner turmoil, it took all of Greg's self-control not to cum as well, while she thrashed beneath him in orgasm. Each ripple of pleasure for her translated into an amazing pressure on his cock, as her cunt gripped him with a fierceness he had never felt before. It was like someone was trying to milk the cum right out of his cock!
When at last her gyrations had ceased, Greg asked, "Whore, have you ever had a cock up your ass before?"
With shock, Mrs. C. tried to shake off the fog of her recent orgasm and answered hesitatingly, "only once Sir."
"And did you like it?"
"Not really Sir. It hurt a lot going in so we never tried it again."
"Well, that is unfortunate for you, because, like the women in your stories, I plan to use your asshole a lot. In fact I plan to make sure that it is filled all the time," he added, giving her ass a playful swat, as he continued to slowly fuck her pussy. "Now I'm going to leave this up to you to decide how this is going to play out. You can try to resist me, and I will be forced to tie you down over the table. I will then be none too gentle, as I force my cock up your ass, or you can willingly cooperate with me, and I will be as gentle as I can, while I break in your ass. Your choice."
Hesitating for only an instant, Mrs. C. Quickly replied, "No please, Sir. Don't tie me down; I'll do my best to take your cock in my ass. I promise." A secret thrill ran down Greg's spine to hear Mrs. C. using language like that.
"Alright then, because you asked nicely, I'll even use some lubricant to make this first time a little easier for you," Greg said as he reached for the bottle of vegetable oil on the counter.
"Thank you, Sir, I won't disappoint you, Sir," Mrs. C. quickly replied.
Pouring a little of the oil in her crack, just above her anus, Greg began to work the liquid into her asshole; first with one finger and then eventually two. As he slowly and gently began to thrust in and out of her ass with two fingers Greg could feel her sphincter begin to loosen up and relax, as she began to realize that it wasn't as painful as she thought it would be. When it was sufficiently loosened, Greg began to work a third finger into her ass. With very little effort she was able to accommodate this extra finger and even began to thrust back into his hand, thereby burying the fingers completely.
Murmuring in approval, "Mmmm......I have a feeling you're going to be a nice little ass-whore for me, with a little practice and training. Would you like that, Whore?" Greg asked as he began to try and work his fourth finger into her ass.
With a little grunt, she replied, "Yes, Sir, that feels good, Sir," her ass continuing to bounce against my hand.
Feeling she was ready, Greg slowly withdrew his fingers and placed the tip of his cock against her bud. Instinctively, Mrs. C began to tighten against him. Speaking reassuringly to her, Greg coaxed, "Now relax, Mrs. C. My cock is not much bigger than the four fingers I just had in your ass. I want you to relax your asshole and push back against me. I'll leave it up to you, to work my cock into your asshole." With that, he took his hand off of her back, where it had been resting, and, with his other hand holding his cock, pressed against her anus.
For a few moments, nothing was said, and then Greg suddenly felt pressure on his cock, as she began to push back against him. The inner war which had been waging within Mrs. C was now over, and a decision had been made. Mrs. C. was now going to willingly shove his cock up her ass! Greg couldn't believe how amazing this day was turning out to be. It was completely and utterly beyond anything he had thought possible.
Greg was shaken out of his reverie, when he heard Mrs. C. grunt as his cock head eased past her unbelievably tight sphincter muscle, and began to slip inside of her ass. 'It was the most amazing and tightest place he had ever placed his cock,' thought Greg. It took everything he had not to grab hold of her hips and begin thrusting as hard as he could into her. 'The victory would be that much sweeter, if she willingly violated her own asshole,' Greg thought.
Greg began to mutter encouragements to her, as she continued to struggle to take his cock up her ass. "That's a good little whore, Mrs. C. You can do it. You can take my entire cock up your ass. Make me proud, little whore, that's it." Her brow was furrowed in concentration, as tiny beads of sweat trickled down her temples. She was grunting with each push, but continued to slowly make headway. After several minutes had passed, she finally had his entire 8 inches buried up her ass. She paused for a few seconds, letting her body adjust to the intruder, before she began to pull back out several inches, and then thrust it back in again. Soon ,she had built up to a pretty good rhythm, and Greg found his body smacking against her reddened ass with each thrust.
As the pace quickened, so did her breathing. Greg quickly realized that she wanted to cum again, while being fucked up the ass. This completely floored him, since he had never expected her to enjoy this as much as he was. Grabbing her hip with one hand, and a handful of hair with the other, he yanked her head back, and growled, "Are you enjoying this, Whore? Huh? You like having a cock in your ass?" Greg punctuated each question with a hard thrust into her, bottoming out with each one. "Do you want to cum for me again, Whore? Do you?"
When she began to push back against him even harder, Greg was surprised to hear her grunt "Please Sir, let me cum again. This whore wants to cum while you fuck her in the ass."
Greg was shocked at her words, and for several moments was speechless. Finally he regained his senses and barked, "Go ahead, you dirty little Whore. Cum for me."
And just like that, the dam burst, and Mrs. C. Became like a wild animal beneath him. She was pushing off against the table, with each thrust, pounding his cock into her as hard as she could. Greg pulled hard on her hair, forcing her to arch her back and to keep her facing the back door of the kitchen. Greg was sure that some part of her was aware of the fact that, at any moment, someone could walk in and catch her in her most humiliating moment, but she was beyond caring at this point. Being forced to debase and humiliate herself, for her daughters male friend, while he rammed his cock up her ass, was just too much stimulation for her, and she soon found herself gripped in the throes of her second orgasm of the day. 'This one was even better than the first, if that was even possible,' she thought to herself.
Amazingly, Greg managed to hold off on his own orgasm, until he felt her begin to subside underneath him. Greg then quickly yanked his cock out and ran around to the other side of the table, grabbing her hair again and tilting her face up to his. With that, he shot his second load of the day. This time, Greg took aim at her beautifully flushed face, and covered every lovely inch of it, with white sticky strands of his cum. Greg couldn't believe he was able to cum so much, so soon after his first orgasm. When he had wiped the last dribble of cum off on her chin, Greg placed his cock at her lips and ordered her to clean it.
With only a moment of hesitation, she placed the cock, which had just been up her ass, in her mouth and began to suck it clean. When she was all done, Greg pulled out of her mouth and stood several paces away.
When she didn't move, Greg simply asked, "Well?"
It took her several moments to understand what he wanted, but when she did, Greg looked on with satisfaction, as she released the table, and, reaching up, began to wipe the cum from her face, and place the strands in her mouth. She continued this process, until she had cleaned all of the cum from her face, and licked her fingers clean.
When Greg was satisfied with the job done, he ordered, "That's good enough, Mrs. C. I want you to go upstairs now, and get a quick shower. Then I want you back down here again, dressed in only the blouse and skirt you had on this morning."
Rising unsteadily to her feet, Mrs. C. scooped up her discarded blouse and skirt, and quickly ran up the stairs. Thoughts of how drastically her life had changed, in only a few short minutes, were flashing through her mind, as she showered, and she began to wonder what else he had in store for her, today, and in the days to come. To her surprise and continued shame, those thoughts were beginning to turn her on - AGAIN.
Later that day, after Mrs. C. had cleaned up and gotten dressed again, Greg informed her that they were going out to lunch, to celebrate their new relationship. Greg could see she was nervous about this idea, since she feared discovery, but didn't want to argue with him, knowing that it would only result in further punishment for her. Her ass and breasts were still sore from their previous punishment, and she wasn't too keen on repeating it anytime soon.
Seeing her trepidation, Greg attempted to put her mind at ease. "Don't worry, Mrs. C. I thought a little trip to Blackfoot might be in order today." Blackfoot was a city roughly 30 minutes from where they lived, and was both large enough and far enough away that it was unlikely anyone thry knew would see them together. Greg could see her visibly relax at hearing that.
After arriving in Blackwood, Greg gave her directions to a restaurant he remembered eating in, several years ago, when he had come here shopping with his parents. It was almost 1:30pm, and most of the lunch rush had already departed, leaving the restaurant half-empty. As they settled into a booth and ordered their drinks, Greg looked around at his surroundings. They were in a booth in the back corner of the restaurant, and most of the tables around them were empty. The lighting was also dim enough that it afforded them some measure of privacy. After placing their orders for food, Greg leaned over the table and whispered, "You know, Mrs. C., when you stop wearing those frumpy clothes and get all dressed up, you really are quite a beautiful woman."
Blushing at the compliment, she dropped her gaze and whispered back, "Thank you Sir."
Greg took the opportunity, as they waited for their meals to arrive, to look around again at their surroundings, and that was when he noticed a man who looked to be in his late thirties, sitting alone at a table, several tables away from their booth. He would occasionally glance over, and Greg knew he was enjoying the sight of Mrs. Clark, sitting there in her too-tight blouse and tight short black skirt.
As Greg watched him continue to surreptitiously check out Mrs. C., an idea began to form in the back of his mind. Once their meals had been delivered, Greg leaned over the table and said, "You know what, Mrs. C.? I think I'd like it if you undid a button on your blouse. I'd like to see a little more of your breasts."
Mumbling a quiet "Yes Sir," she reached up with shaking hands and quickly undid the top of her blouse. Since there were only a few buttons on her blouse, this opened up the top of her cleavage to anyone who cared to look. When Greg didn't say anything further as they ate their meals, Mrs. C began to visibly relax, as she thought that, perhaps, that was all he wanted from her.