June had just brought in the mail and noticed a package addressed to her stepson, Jacob.

June knew that Jacob didn’t have a job or much money and wondered what frivolous item he had purchased.

She knew she shouldn’t pry but being his stepmother meant teaching him all kinds of life’s lessons.

June opened the package and wasn’t sure what she was seeing. At first glance, she thought it was a large flashlight, but upon closer examination, she knew it was something completely different.

Jacob had bought himself a Fleshlight for masturbating.

June was shocked at first but quickly got over it. She knew Jacob was older now and his interest in sex had clearly piqued.

Now that she was over the initial shock, she examined the toy even closer. It was made by a cheap knockoff brand. It was made of low-quality materials and June considered it a waste of money.

This was a life lesson that June felt was worth teaching.

“Jacob!” June called out, “Can you come here, please?”

“Coming,” Jacob called back.

A minute later, Jacob entered his stepmother’s room. His eyes immediately went to the Fleshlight lying on her bed.

“What is this?” June asked.

“I don't know,” Jacob responded, playing dumb.

“It was addressed to you. You must know what it is.” June countered, as she handed him the toy.

“Look,” June continued, “I'm not upset that you bought this. It's just that I think it was a waste of your money.”

“Why do you think that?” Jacob asked without admitting anything.

“Because it's a cheap piece of junk. And it's for sure not going to feel like the real thing. Just look at it, it doesn't even look like a real pussy.”

Jacob examined the toy. He looked at the shape and felt the material.

“It seems real enough to me,” Jacob commented.

“You think that seems real? Have you ever even seen or touched a real pussy?”

“I've seen a real pussy!” Jacob asserted.

“In person?” June raised her eyebrow.

“Well, no. But I've seen plenty of pictures.”

“Pictures? Those things are all airbrushed and don't even look like the real thing either.”

Jacob scoffed.

“How can I convince you that what I'm saying is true?” she asked rhetorically.

Jacob shrugged his shoulders.

June sat and thought of a possible solution.

“What if you saw an actual pussy to compare it to? Would that convince you?”

“I don't know. Maybe,” Jacob answered truthfully.

June steadied her nerves and began to unbuckle her shorts.

“If I do this, you have to promise me one thing,” June said.

“Okay. What is it?”

“You can't tell your father about this. This has to stay between us.”

“I promise,” Jacob agreed.

June pulled her shorts down her legs.

She then spread her legs wide and pulled her panties to the side. “There, you see. It looks nothing like the real thing.”

Jacob looked at his stepmother’s pussy and then at the toy. His eyes moved back to her pussy and remained there as he spoke.

“Okay. I see your point. It doesn't look exactly the same, but…” Jacob stopped mid-sentence.

“But, what?” June asked, still pulling her panties to the side.

“But just because it doesn't look exactly the same, doesn't mean it doesn't feel the same.”

“I can assure you it doesn't.”

“How would I know? Am I just supposed to take your word for it?”

June sat on his question for a moment. There was no way for him to truly believe her. Not unless she…

“Okay,” June finally responded.

“Okay, what?” Jacob asked, honestly not understanding what June was agreeing to.

“Okay, you can feel the difference. But again, not a word of this to your father.”

“What? Oh. Umm. Okay,” Jacob agreed, still not knowing June’s intentions.

“Push your finger into the toy. Move it around and get a good feel for it.”

Jacob did as he was told. He inserted his middle finger into the toy and moved in circles and then slid his finger in and out.

“It feels… interesting.”

“Now,” June took a deep breath, “push your finger inside me so you can feel the difference.”

Jacob removed his finger from the toy and looked at his stepmother. He watched her as she pulled her panties to the side again.

Jacob put down the toy and crawled onto his stepmother's bed. He reached out with his arm and slowly pressed his finger into his stepmom’s pussy.

“Oh,” June gasped at the sudden intrusion.

June immediately had second thoughts about allowing Jacob to insert his finger inside her.

But then Jacob began moving his finger as he did with the toy. First, he moved his finger in circles rubbing it along all of June’s inner walls.

“Mmm,” June let a small moan escape her lips as she began to feel pleasure from Jacob’s actions.

Jacob felt the softness of June’s flesh, but it didn't feel that much different from the toy.

Next, Jacob started sliding his finger in and out of June’s pussy.

June was getting extremely turned on now. She had to bite her lip just to keep from moaning even louder.

Jacob continued thrusting his finger back and forth. He began to pick up speed as he noticed his stepmother’s pussy begin to get warmer and wetter.

He was just beginning to get into it as was June when suddenly she stopped him.

“That's enough,” June insisted, slightly out of breath. “Did you notice the difference?”

“I noticed that you started getting wetter as I went on.”

June turned a slight shade of red at Jacob’s admission.

“See! It’s completely different.”

“I wouldn't say it was completely different. I just said I felt you getting wet. But that is why they recommend using lubrication with it.”

“Hmm,” June knew that he still wasn't convinced.

“Besides,” Jacob continued, “The toy isn’t meant for your finger. I bet it feels really good somewhere else.”

“I'm telling you, this thing is a cheap piece of junk. You'd probably get more enjoyment just using your hand.”

“I doubt it,” Jacob said. “Can I go now?”

Jacob had become turned on from his interactions with his stepmother and was hoping to go relieve himself in his room with his new toy.

“Wait. One more test, just to prove it to you. Take off your pants, and I will show you once and for all.”

“Take off my pants?” Jacob was caught off guard.

“That's right. You've already seen and touched me. Now don't be shy all of a sudden.”

“Okay.”

Jacob unfastened his pants and removed them along with his underwear before lying on his back on the bed.

June sat up over Jacob, holding the Fleshlight in her hand.

“Are you ready?” she asked.

Jacob nodded.

June brought the toy down to his cock and gently pushed. The opening of the toy gave a little resistance to Jacob’s cock before finally giving way.

The toy slid over the head of Jacob’s cock and continued down his shaft.

June pushed the toy all the way down until his cock was fully engulfed.

“How does that feel?” June asked.

“It feels good, but it's dry. The instructions said to use lubrication.”

“Oh, right. I don't have any lube though. Do you?” June asked.

“No, I don't.”

“Hmm. Okay. Let me try something else.”

June pulled the toy back up along Jacob’s cock until the head came free from the toy with a pop.

June set the toy down and leaned over Jacob’s cock. Her mouth got as close as possible to the tip of his cock without touching it.

She then gathered spit in her mouth and let it drool out of her mouth and down onto Jacob’s cock.

A long strand of spit landed on the head of Jacob’s cock and ran down one side of his shaft.

June looked at the spot running down the side of his cock and knew that his entire cock would need to be lubricated for the toy to work properly.

June quickly reached out and grasped his cock with her hand before all of the spit reached the base of his cock.

She worked her hand up and down his shaft and rotated her grip, working the spit all the way around his shaft.

“Mmm,” Jacob moaned as June’s hand rubbed up and down, and back and forth.

June felt the full girth and length of Jacob’s cock for the first time. She had already been quite impressed when she saw it, but to feel it in her hand was something else entirely.

As June’s hand ran up and down Jacob’s cock, she had almost forgotten why she had begun stroking his cock in the first place. She was now giving her stepson a full-on handjob.

“Oh, fuck!” Jacob moaned loudly, snapping June back to reality.

“Language!” June protested as she removed her hand from his cock. “That should be plenty of lubrication.”

She then picked up the toy again and pushed it down over Jacob’s cock. His cock slipped into the toy with much more ease.

She started slow and then began to pick up the pace. She stroked her stepson’s cock with the Fleshlight while also including a gentle rotation.

June watched Jacob’s cock as it exited and penetrated the toy over and over again. Her pussy began weeping as she imagined what it would feel like to have his cock thrust in and out of her own pussy.

She kept stroking his cock until Jacob said, “Oh, that feels so good! I don't think anything could feel better than that.”

June was happy that her efforts were giving Jacob pleasure but then suddenly remembered that she was trying to prove to him that the toy was inferior to the real thing.

June slowed her strokes and removed the toy completely. She took a moment to admire his hard, thick member as it stood straight up, effortlessly.

“I'm guessing you still don't believe me that the toy is far less pleasurable than the real thing,” June said, running out of ideas.

She had to prove to him the truth, one way or another.

“While spit is a good lubricant, I'm afraid it doesn't last as long as the real thing. Should we give it another go?”

Jacob had really been enjoying himself and didn't want to stop now. “Yes, please,” he nearly begged.

June set down the toy and leaned over his cock again. When she tried to gather more spit in her mouth she found her mouth to be dry. When she couldn't gather the necessary spit, she slowly extended her tongue and licked the head of Jacob’s cock.

June saw her efforts leaving his cock head glistening but she also tasted the bead of precum that had flowed out of his cock.

She wasn't turned off by the taste of his precum, it was just the opposite. June knew his cock would need more lubrication than just the head of his cock. She would need to lubricate the shaft too.

She moved her head down further to lick her stepson’s shaft. But as she did, the head of his cock entered her mouth.

She tried to lick his shaft without closing her mouth, but it was awkward, to say the least.

June slowly closed her lips around his cock and started moving her head down further. She pushed her mouth down as far as she could before sliding it back up to the tip. Then she pressed it down again. She repeated her motions over and over again, trying to coat Jacob’s cock in as much spit as possible.

At least that’s what she tried telling herself. Her head bobbed up and down on Jacob’s cock as she pressed her lips firmly against his flesh and her tongue swirled around his shaft.

More precum filled June’s senses, sparking her actions on further. Jacob was fully aware of his stepmom’s mouth on his cock, but he fought the urge to moan out in pleasure.

Jacob had learned not to make a sound lest he might make her stop. Jacob had lifted his head slightly and was watching June's mouth slide up and down his cock.

He knew that her mouth felt ten times better than the toy, but he wasn't ready to admit that to her just yet.

Almost as if sensing that she was being watched, June lifted her eyes to look at Jacob and found him peering back down at her.

June slowed her motions and backed her mouth up off of Jacob’s cock, “It should be well lubricated now,” June said as she wiped her mouth with the back of her hand.

June tried to play off her actions but they both knew what she had really been doing.

Without saying another word, June picked up the toy and began stroking Jacob’s cock again.

“Mmm,” Jacob finally let out the moan he had been fighting.

“It feels so good,” Jacob repeated.

“That's only because you don't know any better,” June remarked.

“Ohhh, please don't stop!”

But that is exactly what June did. She lifted the toy off his cock and considered her next move.

“Would you like to feel the difference with your cock now? Maybe that will convince you that I'm telling the truth.”

“Really? Are you sure?” Jacob said excitedly.

“Yes, but just this once. You can slide it in for just a minute, but nothing more. Just so you can see that I've been telling you the truth.”

June lay back onto the bed and pulled her panties off before spreading her legs and presenting herself to Jacob.

Jacob sat up quickly and adjusted his position until he was between June’s legs and his cock was aligned with her entrance.

“Are you ready?” Jacob asked.

June nodded her head, but was unsure if she was.

Jacob lurched forward and pressed his cock against his stepmom’s pussy. Without much resistance, June’s pussy opened, welcoming this new visitor inside.

“Ohhh,” June moaned.

June knew Jacob had an impressive cock. It was both thick and long, but feeling it now, entering her pussy, there was no doubt about it. Jacob’s cock was not only large, but it was much larger than his father’s.

Jacob continued deeper as he watched his stepmother’s expression. This was much more than just an education, she was truly enjoying this.

He pressed his cock as deep as it could go and held it in place as his stepmother instructed him. June said nothing. She simply lay there and felt her pussy mold around Jacob’s girth.

After a few minutes of sitting like that, Jacob slowly started to withdraw his cock. June moaned quietly as flesh ran along flesh.

Right before the head of Jacob’s cock fully emerged from June’s depths, she blurted out, “Wait!”

Jacob froze.

“Did you get a good enough feel to make an honest comparison?” June asked.

“Well, there is an obvious difference between the two. But I think I enjoyed the feeling of the toy sliding up and down my cock more.”

“Hmm,” June pondered. “That is just because of the motion of the toy rubbing against your cock. Not because it feels better than a pussy.”

“You're probably right, but…”

“Push it back in,” June cut him off, “Get a good feel for it. And add a little motion of sliding back and forth.”

“Okay,” Jacob smiled.

He slid his cock back into his stepmother’s pussy. He reached the full depths again and then reversed course. He backed it out without fully removing his cock and then pushed it in again.

He continued doing this, and with each thrust, he began to pick up the pace. Jacob was thrusting faster and harder.

His stepmother was moaning with each thrust as Jacob began grunting over her.

“Oh yes! That's it, get a good feel for it,” June encouraged her stepson to continue.

All thoughts of decency and morality were gone from June’s head now. She was getting fucked and she was loving every second of it. The last thing she wanted was for Jacob to stop now.

“It feels so good!” Jacob finally admitted out loud.

“It does, doesn't it?” June agreed.

Jacob was starting to feel that all too familiar feeling. He was feeling an impending orgasm approaching. He quickly weighed his options but decided that continuing and finishing inside his stepmother, would be a line she would not want to cross.

Jacob slowed his thrusts and then pulled his cock all the way out of June’s pussy.

Jacob was not the only one who felt close to cumming. June had been right on the cusp of one herself. She looked up at Jacob with a look of confusion.

“Why did you stop?” she asked. “Were you not enjoying yourself?”

Jacob didn't want to admit that he was about to cum; instead, he said, “I just figured that I had gotten enough of the real thing to make a judgment.”

June’s pussy was throbbing. She was so close and didn't want to stop now, so she came up with a plan.

“Before you make any hasty judgments I think you should know something. The toy will only give you one type of sensation, whereas the real thing can change your sensations based on the position you are in. I want you to try something and tell me how it feels next.”

June rolled over on the bed and lifted herself up on all fours, presenting her ass and pussy to Jacob.

“Try putting it in this way and see if that makes any difference,” June said as she looked over her shoulder at her stepson.

Before Jacob made a move forward, June suddenly sat up. She reached for her shirt and pulled it over her head before discarding it onto the floor. She then reached behind her back and unclasped her bra.

June tossed her bra to the floor and said, “I was getting a little overheated, but I'm much better now.”

As June lowered herself back down into the doggy style position, Jacob followed his stepmother’s lead and removed his shirt and added it to the collection on the floor.

He then scooted his body forward until his cock could reach its destination. He pressed his cock inside and grabbed hold of June’s asscheeks.

He started thrusting rapidly straight away. His cock slammed into June’s hot cunt as his hips bounced off of June’s ass.

“Yes! Yes! Yes!” June moaned with each thrust.

His cock was penetrating much deeper now, and June’s orgasm was making a quick return.

“Don’t stop!” June demanded. “I’m…I’m… Ohhhhhh!”

Jacob suddenly felt June’s pussy gush with more wetness as it tightly gripped his cock.

“Oh, fuck,” Jacob moaned loudly before remembering June didn't like it when he swore.

“You've got that right,” June huffed.

June needed a little break from getting rammed so hard after her orgasm. So she gave Jacob new instructions which allowed him to continue...