Chapter 18: [EX] A Meetup With Carolyn

I’ve been neglecting Carolyn recently, and I don’t intend for things to stay that way. I’ve been beyond busy with getting back into the swing of schooling and trying to navigate the labyrinth that is Laura Sinclair, so my relationship with Carolyn has felt a bit neglected for a while. I think it’s about time that I correct that.

As much as I like Carolyn, we really haven’t spent that much time together in the grand scheme of things. It feels like we’ve been involved with one another for a long time, but looking at the calendar it’s actually been less than a month. So much has happened in so little time that those pleasant days spent helping Carolyn around the house, teasing each other, and occasionally taking breaks to fuck, seem like ages ago.

We can’t have sex in her home anymore; At least not with Darren roaming around. We’ve resorted to going to motels, but neither of us can do that as consistently as we’d like. On top of that, dates are hard to plan and execute due to the secret nature of our relationship. Laura and I also have a hidden relationship, but we’re at least able to really let loose in her apartment. Carolyn and I can’t even do that. It’s a frustrating state of affairs, to say the least. We can occasionally fit some time in to fuck, but I want more than that from our relationship.

Things can’t stay this way.

For now, because I have yet to come up with a good idea to rectify this situation, we are once again headed to our favorite motel. It’s not a permanent solution, but meeting up and having sex is better than nothing.

I called ahead, so getting the key to our room is a minute-long ordeal, and we’re on our way to the chosen room. She’s wearing a lacy black dress that hugs her figure wonderfully, highlighting her motherly curves. We reach the stairs, and I graciously gesture for her to go first. 

There’s no ulterior motives here, none at all.

The door to our room shuts with a click, and before I can turn the light on, her hands are all over me, drinking in every inch of my body. I follow suit, grabbing at her overwhelmingly lewd figure. God, how I’ve missed this. Laura’s beautiful and has a wonderful, lithe figure, but she lacks the obscene curviness that Carolyn has in spades.

It just barely struck me how truly lucky I am. Both of the women I’m involved with are exceedingly beautiful in their own right, and they’re fine with me having multiple partners? That’s gotta be like winning the lottery odds.

As we’ve felt each other’s bodies, we’ve slowly made our way over to the bed, which she delicately places herself on. I place myself on top of her, and our lips meet, beginning yet another long session of feeling each other up.

As much as Carolyn doesn’t like to be doted on in bed, she seems to enjoy these lovey-dovey moments before the action truly begins. The earnestness with which she’s returning my kiss makes how much she’s been missing my touch all the more obvious.

Slowly, and with great effort, we shed our clothing, taking short breaks from our coupling to remove bits and pieces of clothing before diving into each other once again.

Carolyn interrupts our tongue-fight and reorients us, so I’m sitting against the headboard of the bed, and she’s nestled comfortably between my legs. She lightly grabs my fully erect cock and introduces the head to her lips, giving it a gentle kiss, and leaving a trace amount of lipstick on it.

Her eyes lock onto mine and she gives me a little smirk, she knows that I want to throw her down and rail her, but she wants this to last. She continues teasing me, offering small amounts of pleasure, through light caresses and kisses delivered all over my body.

This is very standard for her. Once I penetrate her, she wants me to dominate her completely, but before that, she loves to exert the little bit of control I give her. She loves to make me squirm a little before I pound her into the bedsheets, and I don’t mind it at all.

Finally, however, it’s time to move on.

She delivers another light kiss to the tip of my cock, and uses a small amount of tongue to lightly lick the tip. Right as she’s about to pull away, my hands grab the back of her head. I’m done letting her have her way.

Her eyes lock onto mine, and I see the realization in her gaze. Her thoughts are plain as day.

He’s going to fuck the hell out of me.

I use her head like a cock-sleeve, pressing it all the way to my groin. The loud, wet, slapping sounds of her cock-pillow lips colliding with the base of my dick drive me to treat her even more roughly.

Despite how I’m treating her, she’s still using her tongue to masterfully bring me even more pleasure. I’ve gotten much better at sex since our first time, but I don’t know if I’ll ever be able to match this milfy succubus.

Saliva freely drips from my cock, leaving a large wet spot on the bed in between us. Strands of spit connect her lips to the base of my cock, giving her whole face a wet look. Her eyes are tearing up from how long she’s been down there, causing mascara to run down her cheeks.

I really don’t mind if she comes up for air. We have a system where she taps my leg if she can’t take it anymore, and she hasn’t tapped out. She never does. You’d think she’d be in pain, and struggling to breathe from how she’s being treated, but her eyes are rolled up from sheer pleasure. She loves this. She has the choice between air and my cock, and it isn’t even a competition.

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By the time she pulls my prick out of her mouth, gasping for air, the actual act feels like an afterthought.

I throw her backward onto the sheet and tackle her, penetrating her in a missionary position. The moment that I slam into her hips, she begins to frantically cum. Being treated roughly had her on the edge of her orgasm, so the moment I penetrated it sent her over. She begins to scream as I continue to thrust roughly inside of her.

Since the first time I had sex with Carolyn, I’ve gotten much better. More than that, however, I researched sex, and how to give women the best possible experience. After learning that what “good sex” is varies heavily from woman to woman, I experimented a lot to find what worked best for Carolyn.

I learned something then.

Carolyn’s multi-orgasmic, and not just a little. Once this woman is up there, as long as you keep thrusting, she’ll never come back down. Every successive orgasm feels just a little better than the last, and eventually, she loses control almost completely.

We’ve been in the same position for a few minutes now, and Carolyn can’t even bring herself to moan anymore. Every thrust causes a new wave of convulsions as her orgasms never cease.

Her eyes are rolled back and her tongue is lolled out as she tries to ride out the waves of pleasure that are dominating her entire body.

Everything has to come to an end eventually, however.

I have quite a bit of stamina anymore, but the sight of Carolyn lewdly losing control does me in. I thrust deeply into her and release, pouring my semen deep into her lovely snatch.

After the sex ends, the room is silent, with the exception of our heavy breathing, of course. The sex was amazing, as always, and we need a few minutes to rest before we can begin to function again.

Finally, Carolyn speaks. “I… wow.”

My heart rate has calmed down a bit, and my lungs are finally cooperating again, so I respond, “That was intense.”

We idly lay next to each other for several more minutes in the ensuing silence. Carolyn looks like she wants to say something, but keeps stopping herself.

Finally, she says, “I always thought I needed a man who would treat me right. Especially after my divorce.”

I let out a smile, “And I’m that man?”

“Let me finish. I spent a lot of time dating ‘gentlemen,’ but whenever I found one I was interested in, I’d always leave disappointed, and I never knew why. I think I’ve figured it out.”

“Go on.” I really don’t know where she’s going with this.

“You’re a kind man, Sam. I love that about you. But when we have sex… you’re different. You treat me like a cheap whore, in the best possible way.”

I’m not really sure how to respond to that. Luckily, it looks like I don’t need to. She rests her head on the crook of my shoulder, gives me a loving peck on the cheek, and falls asleep.

God, we really need to see each other more often.

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