Fortune favors the bold

Writing on someone’s lower back wasn’t the easiest thing you’ve ever done. But honestly, you could read it without much problem, and you were satisfied with how it looked. What bothered you was if it worked at all.

Maybe Jennifer was going to see it and think you were some sick pervert. You didn’t want to ruin your friendship. The thought of your biggest crush hating you felt horrible. You wouldn’t be able to look into her eyes for the rest of your life.

Then there was Jake… Would he even mind? You and everyone else in the school knew he was a pervert but this was his mother.

“Elliot!?” you suddenly heard a female scream “What are you doing here!?”

Jennifer was awake and angry. The unexpected voice of the woman you just sneaked on left you unable to get anything else than an “Uhhhhh” out of yourself.

“Elliot, what did you do?” Jennifer repeated.

She was now looking at your hand. Her attention was directed at the uncovered sharpie in your hand.

Jennifer got up from her bed and started walking.

This was definitely your end. She was gonna slap you, tell you to get out of her house and never show up again. The only thing you could do now was take it like a man and apologize. You took a risk and it didn’t work. It was fine. You’d just never be able to forgive yourself.

You waited bravely with your eyes closed. Her hand was about to meet your face at a high speed. You’ve never been bitch slapped before but it couldn’t be that bad, right?

“...”

Huh?

You felt like you shit your pants 4 times by now. Why was it taking so long?

You slowly opened your eyes and what you saw took a weight off your mind.

There, in front of a standing mirror you saw the shocked expression of Jennifer. Her jaw dropped so low that you were worried about it getting dislocated.

She was staring right at the writing you put on her lower back. If she was mad about it you’d have known by now.

This was good. This was REALLY good.

You regained your posture and took a step forward.

“Jennifer, look at me.” you demanded.

The beautiful woman slowly moved her head until she met your eyes.

“Tell me what it means.” it seemed the answer wouldn’t come out of her by itself.

“You…” she stuttered, “You own my ass.”

It took her another few seconds to continue “Since when?”

“It doesn’t matter.” you needed to maintain control over the situation “Tell me, if I told you to show your bare ass, would you do it?”

She kept staring at you, visibly thinking.

“I guess I would have to… It’s yours.” she answered.

“Then take your pants off, get on the bed and stick your ass high in the air.” you commanded her.

She opened her eyes wide again, not expecting you to ever say that to her.

“Now!” there was no going back now. You wanted it and something told you that you would get it.

She jumped a little and took her pants off. Stepping out of them she proceeded to her bed. Jennifer didn’t break eye contact as she climbed up the double bed. Only when her boobs touched the mattress and her ass rose as high as it could, she looked away.

This feels so fucking good. You thought as you repositioned yourself in front of her huge ass.

Each of your two eyes landed on her buttcheeks. They looked amazing but it was getting a little dark in the room.

You moved closer. The perfectly proportioned piece of meat was now within your arm’s reach. And instinctively you smacked your hand on it hard. The clapping sound echoed through the room and into the hallway, followed only by the soft moan.

Wait. Did she just moan? You asked yourself.

You quickly tried to look at her face. And you saw that she was struggling. Was she trying to hide the fact that she liked it? It must have been pretty long since a man got intimate with her like this. You knew she used to date a few years ago, but at some point it seemed like she stopped for good.

That’s useful. You thought and slapped her cheek again.

This time she wasn’t as loud. But there was something. She was definitely horny. That didn’t just turn you on. It also put you more at ease with what you were doing. You didn’t want to **** her. You wanted to use her, but you also wanted her to enjoy it. And if you were right, she needed it as much as you.

You grabbed her butt with both of your hands and played with the flesh for a moment. The thong she wore looked comfortable for a woman, but it wasn’t sexy. So you put your fingers under the material and, with one swift motion, pulled it down to her knees.

That’s a cute butthole. You thought and chuckled.

You looked a little closer and noticed her pubic hair was trimmed to a landing strip. It looked nice but it would have to go away at some point.

Focusing back on her asshole, you pulled her buttcheeks apart. a drop of sweat ran over the little hole and continued to the south. Your hands moved toward it on their own and your thumbs spread the sensitive asshole gently. The touch caused Jennifer’s body to twitch.

Deciding the playtime was over, you unbuckled your pants and let them drop to the ground. You were so hard your dick stuck out of your underwear. After you pulled it down, you got as close to Jennifer’s ass as you could and placed your raging member between the two buns.

“Elliot! Is that your penis!?” came the shocked voice of the owner of the body ‘your ass’ was attached to.

“Yes it is, Jennifer. Now be a good girl and tell me where you keep lube.” your dick slowly slid up and down her ass.

“A… Are you gonna stick it in?” It sounded like she was scared, but fortunately for her that wasn’t your plan. You knew her asshole would need a bit of practice before you could fuck it.

“Not today, Jennifer.” she sighed relieved at that, and pointed her hand at the nightstand next to the bed. “It’s in the bottom drawer.”

You lightly slapped her butt with both of your hands and went for the lube as the hot MILF let out a short yelp.

Inside of the drawer you found the lube but something else caught your attention. There was a pink dildo, a silver butt plug and a small vibrator. It gave you a few ideas, but they would all have to wait for later.

You heard Jennifer’s quiet voice as you got up with the lube in your hand. “It’s so huge~” That was a big surprise. It didn’t sound like she wanted to say it out loud though.

You also never really thought of your dick as big. You knew it wasn’t small, but the few girlfriends that you had in the past never mentioned it.

You put lube on your hands, and started massaging her ass, her row and even put some on her butthole using your fingertip. Then you put some more on your hands and stroked your hard dick.

When everything was lubricated nicely, you returned your dick where it belonged, between her ass cheeks. Squeezing them together, you started moving in a slow and steady rhythm. As you sped up, you felt Jennifer move her body, matching your pace.

You weren’t sure how much she liked it rough, but as of now you were pretty successful. So you leaned forward and grabbed as much of her pretty blonde hair as you could with one hand. With no resistance she tilted her head back as you carefully pulled it.

That position wouldn’t work if she didn’t have such a huge bumper. You thought to yourself. Even with just one hand you were able to surround your dick with her flesh.

As you were getting close to cumming, you pulled on her hair harder and sped up the pace of rubbing your cock between the most beautiful pair of asscheeks you’ve ever seen. Both of you were panting, as if you were running a marathon. “Yes! Harder!” you heard Jennifer scream.

It looked like there was no trace of your handprint on her cheeks anymore, so you used your free hand to slap it as hard as you could. Jennifer moaned with pleasure, so you took the hint and slapped it again. With every slap you gave her, she moaned loudly and it pushed you to your limit.

With a grunt you released a long string of cum on the back of the sexy woman panting and moaning so hard, you wondered if she just had an orgasm.

As you finished cumming, you let go of her hair and heard her say “Jesus fucking Christ. I never came this hard.”

With pride flowing through your mind, you took a few steps back to admire your work. Jennifer had already lowered her ass to her feet, but she remained in the sexy position on all fours. Her back and ass were painted in your semen. Her sports bra was soaked in it and some landed on her hair.

You wanted to keep looking at her, but something in the corner of your eye caught your attention. The door to Jennifer’s room was ajar and the light of the hallway stood out in the dark room. As you looked towards the door, you saw something that might have been the biggest shock that day.

Through the gap you saw the figure of Jake, your best friend and the son of the bitch you just fucked like an animal. But that wasn’t all! Jake didn’t just stand there. He was holding his penis in one of his hands.

He was looking up and it seemed like he just came, because when he saw you looking at him, he instantly ran away.

Wow.

You knew Jake was a pervert, but you never expected him to be turned on by his own mother getting fucked.

You looked at Jennifer again, but were relieved to see that she fell over on her side facing away from the door.

Tired and still mesmerized by what just happened, you went over to her bed and laid next to her. With that, you felt yourself fall asleep quickly.