Taming the Boss Pt. 05

It had been five months since that fateful night, when John surrendered himself to his secretary, Amanda. Life had been extremely good for the lovers since then. Since Amanda moved in, his life was much more routined now. They worked out regularly, and Amanda was very strict when it came to nutrition. Thanks to Amanda, John was much less stressed at work too. She took care of it with regular blowjobs, handjobs, or footjobs. He was much more focused at his work, and the outcomes were clearly visible.

To top everything off, the sex was amazing. They had been trying out a lot of things. The morning cunnilingus has become a ritual. Amanda sometimes made him wear butt plugs during office. On other days, he had to wear her panties. Sometimes he had to do both. Within months, they had fucked in almost every corner of the mansion.

John was thinking about all he sat under the table, covered by Amanda's skirts, licking her pussy lovingly.

The next day was his birthday, and they earlier decided to have a quick dinner at the nearby restaurants. They got themselves a table beside the table with a nice view of the road passing by. The restaurant was pretty empty, except for two other couples seated at the other end. Having a quick glance around, Amanda asked John, "Do you think you can get me an orgasm before our food comes?" She grinned.

John did not need a second invitation. "Well, let's see about that." He smirked as he got under the table. Amanda lovingly guided his head under her skirts, towards her crotch. She was not wearing any panties, and John was soon kissing her inner thighs intently.

"That's a good boy!" Amanda exclaimed as she patted his head.

Encouraged, John started running his tongue up and down the slit of her pussy. The smell of her secretion filled his nostrils, as he pushed his tongue forward. A soft moan escaped her mouth, and she quickly looked around, making sure nobody was nearby.

"Oh yes, baby. Make me cum." She moaned as she pushed his head with both hands.

John lapped at her pussy lovingly, eager to make her cum. Just then, the waitress was back with their food. Not wanting to lose the challenge, John started rubbing her clit desperately with his tongue. Amanda could not suppress it any longer, and let out a rather loud moan as she reached her climax.

The waitress grinned at her knowingly. "Having fun down there?"

Amanda smiled. "Yes, he is such a good boy for me!"

"Lucky you!" She exclaimed as she finished serving the food. "Let me leave you two lovers alone. Enjoy the rest of the meal!"

John came out after a while. Her cum glistened on his face. Amanda smiled as she closed the gap and kissed him fully on the lips.

"Thank you, honey." She said after they broke the kiss. "Now let's enjoy the meal. We have a long night ahead" She added with a wink.

John was genuinely curious. "What do you have in mind?"

Amanda put her right foot on his lap and started rubbing his dick with it. "Eager, are we?" She teased.

"Well, you have been teasing about it for a week!"

"Don't worry, hon. I will not do anything you do not like." Amanda reassured him. "But you might lose your virginity today." She added with a slight squeeze on his dick.

John blushed at her suggestion. He was rather thrilled by the idea. But at the same time, he was a bit scared. "I don't know, Amy."

"Come on, baby. What are you concerned about?" Amanda asked.

"Well, I mean... Aren't guys supposed to do the penetrations? You know..." His voice trailed off as he felt her foot squeezing his dick more rigorously.

"Honey, I won't think of you as any less of a man."

"Really? Do you think this is very masculine?"

Amanda retrieved her foot, and got hold of his hands. "Well, these are just stupid gender roles anyway. It does not make you any less of a man, or a person whatsoever. You are still a very strong-willed person. This is quite apparent by the way you handle your business." She said as she stared deep into his eyes. "If you let me fuck you, I would rather think that you are secured enough to let me do it. Do you understand what I mean?"

John nodded silently.

"But if you are not comfortable with it, we can forget about it. I will never do anything you are not comfortable with. And I genuinely mean it."

John thought for a while, and then said. "Let's give it a try, Amy. But, please go slow, okay?"

"That's my boy!" Amanda exclaimed as she ruffled his hair.

Soon their meal was finished and Amanda excused herself to the restroom. Once inside, she put on the strap-on dildo she had been carrying inside her purse. When she returned, John had already paid the bills. So they quickly got to the parking and got inside the car. She quickly drove them home.

Once inside, Amanda stood in front of John.

"Get on your knees, baby. I have something to show you."

John obediently got down on his knees and looked up at her.

"Do you want to see it?"

"See what?" John asked, looking a bit confused.

"My dick." Amanda smirked as she pulled her skirts up.

John started at the pink dildo, but did not say anything.

"Well, what do you think?" Amanda asked.

"It's... big." John stuttered.

"Well, not as big as yours. It's only six and a half! Do you want to touch it?"

John nodded slowly.

"Go on, baby. The other end is inside my pussy. So you should be able to stimulate me too!" She winked.

John hesitantly grabbed the dildo.

"Rub it, baby. Rub it like when you masturbate." Amanda teased.

John started rubbing the dick up and down.

"How do you feel baby? Do you like it?"

"I am not sure. But well, it feels normal." John replied.

"Would you like to kiss it?" Amanda grinned. "Would you like to kiss my dick?"

John did not say anything, but instead leaned forward to plant a soft kiss on the dildo.

"Go on, baby. Make it wet. After all, it will go inside your ass. The wetter the better!" Amanda said as she grabbed his hair with her hands.

John hesitantly opened his mouth and took the dildo in.

Amanda started thrusting the dildo in and out of his mouth gently. "So this is how you feel when I give you a blowjob?" She grinned as she gradually increased the speed. She was getting excited herself, as she could feel the other side of the dildo rubbing on her clit.

After a while, John got used to the rhythm and started bobbing his head up and down on it.

Satisfied, Amanda pulled him off the dildo. She got on her knees and held his face with both hands. "I am proud of you, baby." She kissed him deeply on his lips. John put his hands on the back of her head and started kissing back. Their tongue played with each other as her hands fumbled around to take off his shirt.

Once she took her shirt off, they broke the kiss. "Off with the pants, mister!" She ordered as she started taking off her clothes as well. After they were both naked, she grabbed hold of his dick and led him to the bedroom.

"Go in front of the mirror, baby. On all fours, facing it!" She ordered pointing to the full length mirror.

John blushed, but got on all fours anyway. Amanda took the lube and started massaging his asshole with it. She first inserted her middle finger and fingered his asshole for a while. Then she put in another. "Are you ready, baby?"

"Yes, Amy." He replied.

"Beg for it baby. Beg for my dick."

"Please mistress! Please fuck me with your dick!". He begged eagerly.

"That's better!" Amanda grinned as she took out her fingers and stood behind him. She looked at their reflection on the mirror, and their eyes met. She firmly spanked his ass. "Whose ass is this?"

"Yours, mistress. I am all yours." John replied obediently.

Satisfied, Amanda applied some more lube on the dildo, and put it on the opening of his puckered hole. She held his hips by both hands, and slowly started applying pressure.

Once the tip was in, John moaned loudly. "Oh, Amy!"

"Oh yes, baby. I like the sound of it!" Amanda smirked as she continued pushing it deeper. "Scream my name, baby!"

"It feels so good." John moaned. "Please put it all in!"

With a final thrust, Amanda pushed the entire length of the dildo inside. She started spanking his ass, as she gradually built up the pace. "Look at the mirrors, baby. Look how I am fucking you."

John watched her boobs bounce as she continued thrusting the dildo in and out of his asshole. His dick was already hard as a rock, and looking at the sight, it started leaking pre cum.

After a while, Amanda took the dildo out and walked to the bed. She beckoned him with her middle finger as she laid down on the bed. John obediently crawled to her.

Amanda held the dildo with one hand, making it point upwards, and looked at John. "Ride my dick, baby!"

John got up and placed his ass over the dildo. Once the dildo was inside, he slowly sat on her crotch, taking the full length inside.

"Well, do you like it now?" Amanda asked him, as she rubbed his dick slowly.

"Yes, Amy! I love it! Please let me cum now."

Amanda took a quick look at the clock and kept rubbing his dick slowly. "Soon, baby." She winked. "For now, ride my dick!"

John started bouncing his ass up and down on the dildo, moaning loudly each time the dildo hit his prostate. Once the hour indicator reached 12, Amanda ordered. "Cum for me, John."

John immediately erupted all over her hands and boobs. This was more than he has ever managed to cum.

Amanda held her hands open in invitation, as she wished him. "Happy birthday, honey!"

John took the embrace and held her tightly. "Thank you, Amy. This was the best birthday ever!"

Amanda lovingly held him and patted his back while they slowly drifted off to sleep.