Chapter 8

I was in a car with Samantha’s mother. If I recalled correctly, her name was Jennifer, but I always just called her Samantha’s mom. After just being caught sleeping with her daughter, it felt extremely awkward in the car. Although it had been a few years, Jennifer wasn’t like the kind, gentle woman that I remembered. Rather, she had a sort of angry frown on her face, and she actually managed to intimidate me a little.

That only increased the silence in the car and made things feel even more awkward. Actually, now that I thought about it, this was probably for the best. After all, I didn’t want to be lectured about sex or anything from her. I just hope she didn’t try to tell my mother what happened. She would definitely ground me. Then there were my sisters. They would tease me relentlessly. My oldest sister, who ended up driving me to her house, would feel betrayed.

It really was a conundrum. In fact, I was already starting to sweat. It took a moment to realize that Samantha’s mother had the heat on in the car up to the full blast. I unzipped my coat and pulled it off. For some reason, my movements caught Jennifer’s eye, and she glanced at me several times out of the corner of her eye. As a matter of fact, she had been glancing at me a lot. It was almost like she wanted to say something. That made the hot environment even more unbearable, so I decided to speak first.

“Um… about your daughter…”

“She’s a slut.” Jennifer immediately snorted. “I don’t mean to insult your choices, but I think you can do better?”

“Huh?”

Although I knew I should have expected something like this, it wasn’t as easy as it looked. My brain was hardwired to see the world a certain way. Men were men, and women were women. It was like with every conversation I had to remind myself that things were reversed here. Although Jennifer looked angry, I could stop imagining the fretting mother. In my mind, I had pushed Samantha down quite aggressively, and so to continually have people put the blame all on her left me flummoxed.

“I mean, look at you! You’re a very attractive man. Plus, you’re smart and popular. I mean no offense toward my daughter, but we’re not even sure if she’ll make it into college. I just don’t want a sexy thing like you being dragged down by my good for nothing daughter.”

However, it seemed like Jennifer didn’t understand why I said ‘huh’. As she eyed me up and down, she thought I was questioning the statement entirely. Yet, despite all my best efforts, her words continued to shock and surprise me.

“Am I really that hot?” I said, feeling just a tad bitter.

If I was really hot, then I wouldn’t have been girlfriendless for years. Even if the values had changed that much, I found it hard to believe women found me attractive. I would have definitely had more success as a man before the switch.

“Hey, if you were 18, I’d…” Jennifer suddenly coughed. “Ah… never mind that. I’m just saying, you should find a girl who has the ability to take care of you. You want a girl who can take care of the babies you make, right? If you got my daughter pregnant, she totally wouldn’t have a clue what to do.”

“Hey, I supposed you’d know better?”

I meant it to just slightly tease her, but once again, I was off my mark. She stiffened suddenly and then gave me a side look.

“I know how to please a man, at least.” Her hand suddenly came out and touched my leg for a moment.

My entire body stiffened. I wasn’t dumb. Being surprised or caught off guard at the moment was one thing, but I was able to figure out the situation quickly enough. Wasn’t this one of those sex fantasies in reverse? The man drives the hot babysitter or her son’s girlfriend home, and then he shows her how a real man acts?

Her hand pulled away from my knee. It was only a few seconds. It could even be a playful pat, but her fingers did linger. The reason I even doubted it was because it seemed so foreign to me. Samantha’s mother was pretty good looking herself. She had bigger breasts than her daughter and a nice round butt. Damn, was I even thinking about this? Didn’t I want to test this world and see where I could go?

However, this was Samantha’s mom we’re talking about here! She was a married woman! Then again, wasn’t that perfect? She’d never talk to anyone about it. She’d have more of a reason to keep it secret than anyone. In a snap second, I made a decision. As her hand started pulling away, I reached out and grabbed it.

“Huh?” She made a surprised noise.

“Is that so? Tell me more.” I responded, putting her hand back on my leg.

She didn’t glance back over at me. Actually, the complete opposite. She stared forward so hard that you would swear all of her focus was on the road. Yet, her hand didn’t move away from my leg. Half of me was screaming that this was wrong and I was an idiot. That other half of me was extremely turned on. Ever so slowly, my pants started to fill out as one side started to present itself more and more.

“You know…” She suddenly spoke, partially like she was talking to herself, “My husband and I haven’t had sex in ages.”

“R-really?” I didn’t know what else to respond with, but clearly, I knew where her mind was.

“He never wants to experiment. The other day, I wanted him to go down on me and he told me to take care of it myself. I never even got to experience anal.”

“A-anal?” Her mind had already jumped to full sex, she was moving fast even for me.

As she spoke, her hand had started to gently stroke up and down my thigh. My dick was now hard, and if she just glanced over, she’d see how aroused I was. I was just a little tempted, but with the smallest provocation, things had already gotten to this extent. Now I was a bit scared. Once again, she mistook what I said.

“Anal is when you stick it in the butthole, darling.” She responded.

Of course, I knew that! Did she think I was an innocent virgin? Well, admittedly, yesterday, I hadn’t even had sex yet, but I at least knew stuff and watched porn. I actually rather favored anal. Then a thought came to me. This was another world where everything was backward.

“Wait! Your butt or his?” I let out a cry.

She burst out laughing. “You’re really cute when you’re flustered.”

She had slowed her driving down, and suddenly her hand went up my thigh and touched my dick.

“Oh my… someone is hard, isn’t he? Is this talk turning you on?” Her fingers wrapped around my dick through the pants without hesitation.

“Ah!” I let out a noise at the sudden feel.

“Hehe… no need to be embarrassed. I’m really wet too.”

She actually grabbed my hand and then put it up her skirt. My hand touched the underwear underneath and I realized it really was wet under there. My hand pulled away.

“It won’t bite…” She laughed. “Isn’t it way wetter than my daughters? It’s tighter too.”

I wanted to call bullshit instantly! I guessed tightness would be equivalent to bigness for guys, but that wasn’t something she could control. She had pushed a baby out that thing! There was no way she was tighter. She seemed to see the disbelief in my eyes, and somehow that excited her more. Her fingers were now excitedly stroking the head of my cock as she drove with one hand.

“I know what you thinking…” She laughed. “I pushed a baby out there, how can I be tighter?”

“…” Well, she wasn’t wrong.

“It’s simple. It’s a little thing called kegels.”

“Kegels?” I had only vaguely heard the name before, but I couldn’t recall.

“Believe it or not, the pussy is a muscle, and that muscle can be trained. Young girls like Samantha are too naïve and embarrassed. They depend on their virgin status to be tight enough to please a guy, but all that does it makes it hard to stick it in. Mature women like me practice. We not only can go a lot longer, but we can squeeze on command. I don’t mean to brag, but I could grab your cock tighter than a virgin loli!”

It turned out that Jennifer was far more perverted than I had ever anticipated. I could only give a noncommittal noise because I had no clue what to say to anything, she was telling me. It was almost an overload finding out just how lewd this woman was. I felt like I was floating in a dream and was just waiting to wake up.

Yet, even after a moment, I was still in the car with her, and her hand was still stroking the head of my cock. Wet fluid from pre-ejaculate had created a spot on the end of my pants, but she didn’t mind as she continued to rub it. It was at that moment I realize that she had missed the turn to my house and was driving somewhere else.

“Wh-where are we going?” I asked nervously.

“Ah, just thought we could go somewhere private.” She responded.

“Um… actually, I kind of need to get home.” I knew I was suddenly chickening out, but it turned out that this was too big of a step for me.

I was only a virgin 24 hours ago. Upgrading to a horny MILF was too big of a step for me. I needed to start a bit smaller here.

“How about we just park somewhere secluded, and then I finish you off?” She asked, glancing at me and biting her lip.

“S-Samantha…” she blinked as I said that word. “That’s right, we can’t, because of Samantha.” Even I barely knew what I meant.

Somehow, the half of me that was too frightened was starting to win out now. It got too real too quickly. Samantha was just as innocent as me, so teasing her was fun. Jennifer was completely different, and even if it lost me my man card, I suddenly wanted to put a stop to it.

“When I’m done, you won’t even be thinking of Samantha…” She purred, turning into an alley, pulling up and stopping.

Glancing around, I realized we were hidden between two buildings and there was no light. It was actually a perfect place to park without being seen. Had she been heading for this place from the get-go, or was it pure luck that she happened to turn here?

“S-Samantha’s mom…”

“Just call me Jennifer.” She said, moving forward across the seat and then smiling seductively. “Or, you can call me mommy if you like.”

“Y-you’re husband…” I barely managed to get out before she put a finger over my lips.

“This will just be our little secret, okay? I’ll make you feel really good, I promise.” She leaned close to my ear. “Don’t worry, I know you want this as bad as I do.”

Although somewhere in the back of my mind, I knew this scene would be horrifying by this world’s standard, I was still a man at heart. She was a sexy woman who was coming on to me hard, and those words were like dangling a steak in front of a starving person. It wasn’t scary, but rather incredibly hot! My lips found hers, and I suddenly found myself kissing this beautiful older woman.

It had only been fifteen minutes since the start of this car ride, yet things had already progressed to this point. While our tongues danced excitedly in each other’s mouths, her hands worked with precision to fish out my penis. Once she had it completely out and stroked it a few times with her hands, she broke her kiss from me.

“It’s okay to cum in my mouth if you want.” She chuckled. “Stupid little girls like my daughter will spit, but I always swallow.”

As if to punctuate that fact, she opened her mouth and swallowed my dick. My eyes bulged as she didn’t hesitate to deep throat the whole thing. She definitely couldn’t have done that much without practice. However, it kind of made sense for this world.

Men in the old world would try to last the longest they could. Some would take penis pills, practice with toys, or read manuals with hopes they could satisfy a woman. Therefore, women in this world were probably just as insecure. She had clearly practiced deepthroating and supposedly Kegels as well, all for a guy who didn’t appreciate her. So, who cared if I had my fun with her? Why should her tight pussy and amazing mouth go to waste?

I leaned back and decided to enjoy the ride. It had already gotten to this point. Wasn’t it every man’s dream to have a daughter and mother combo? Maybe I’d even get them both at the same time? I’d really need to play my cards right with Samantha though.

“Ahhhh….” I moaned as she sucked deeply on my cock.

She hadn’t come up for air once, sucking hard on the glands with my cock head pushed against the back of her throat. It felt absolutely amazing. My hands grabbed the back of her head and I ran my fingers through her soft hair.

This world was actually really amazing, right? I was letting myself get worked up over the fact everything was reversed, but why should I? Isn’t it great that women are aggressive with sex? It’s like I have a superpower! I can fuck any woman I want! Rather than wondering what I should do, I should just take advantage of this world while it’s still this way. Who knows, tomorrow, this woman could be back to her regular, kitchen mom self who wouldn’t do this kind of affair in a million years. Samantha could go back to ignoring me. I could end up back in the virgin zone. In that case, I should just enjoy it all as much as I can!

With conviction growing in my eyes, I began to thrust my cock into Jennifer’s throat. Her suction was too good though, and even though I had already cum with Samantha, I found myself cumming again. True to her word, she sucked it all down. When she was done, she pulled away, licking her lips like she just had a treat.

“Mm… you taste like cherries.” She said.

Another bullshit line, but I kept myself from laughing in her face. Instead, I made a light chuckle that I hoped she interpreted as nervous.

“Was it good?” She asked.

I nodded, trying not to say anything so that I appeared shy and bashful.

“I’m glad.” She smiled and then sighed. “I want to fuck you so bad, but my husband is going to start wondering where I am if we take any longer.”

“R-right…”

“I’ll take you home, okay?”

“Wh-what about you?” I asked, looking down at her skirt, which was up a bit.

She laughed, pulling it down. “You’re really cute. Don’t worry about me. I’m a big girl, but I like how you think. A lot of guys don’t care about the girl once they’re done.”

Even with reversed values, it seemed like there were some biological things that couldn’t be reversed. A guy blew his load and then it went soft and he lost a lot of his sex drive. Poor women in this world. At least in my world, men were the chasers of sex, so they had an incentive to last longer and satisfy the women. In this world, they were selfish lovers. It probably was rare for women to climax during sex. That meant, between worlds, on top of everything else, women in this world were hornier and more sex-deprived.

True to her word, Jennifer drove me home without incident. She had been a bit forceful for a bit, but she hadn’t lied at all. I did really enjoy it, and she hadn’t even pushed me. I had put my dick away and we had moved in silence. She would occasionally glance at me and smile. It was clear that she was into me. It was weird coming from an adult woman who was twice my age, yet also kind of hot.

Just as she pulled up into the driveway, she grabbed my knee. “You should stop by more often.”

“Ah… yes.” I said, not sure how else to respond.

Then, glancing around and seeing no one peaking out my windows and her headlight on blinding anyone if they did look, I leaned over and kissed her cheek real quick. She blushed in a satisfying way, but just as I went to leave, her hand suddenly reached out and grabbed my dick.

“You fucking tease!” She responded, her eyes shooting me a horny glare.

She let go a second later and wasn’t even looking at me by the time I recovered. Her eyes remained ahead as if it hadn’t even happened. I slowly got out and then closed the door. Without another word or looking at me, she reversed out of the driveway and then drove off.

My first day in a new world and I had already experienced so many things. I returned back to the house, a dazed expression still on my face. I couldn’t imagine what tomorrow would bring.