AMA - The Divorcee: Day 02

You're naked in front of her now, in front of 'Cassandra', as she'd liked to be referred to during this roleplay. As she shifts her body on the bed so that she's on all fours with your dick right in front of her face, you look at her once more. As much as you'd like to pretend that this 'Cassandra' is someone entirely different, all you can see is Cassie; and when she looks at you, with your dick in her hand, the longing look you've seen her have is replaced by a look of hunger. A look of hunger that would be impossible to get in a night, no matter how wonderful the date was. She can't hide that she looks at you with the eyes of a woman who is finally achieving something she's dreamed about for years; not someone who only just met you.

She takes your dick into her mouth, slowly and gently wrapping it with her lips, while her tongue plays with the tip. The pleasure makes you moan, and look away from her for a moment, or the image of Cassie giving you a blowjob might push you over the edge quicker than you'd like. As you look away, and see inside your bedroom, something you would consider weird happens -- you don't feel weird about this at all.

You look down on Cassie still pleasuring your manhood, and you look at your surroundings again, thinking the sight of Cassie giving you head inside your own bedroom would bring back flashes of the past... but it doesn't. Like an idiot, you start laughing to yourself; which causes Cassie to stop what she's doing.

"What's so funny, Jay?" Cassie asks, having paused her blowjob, but still stroking your dick with a steady pace.

"I'm just laughing at how stupid I was being." you tell her, and she raises an eyebrow in curiosity.

"What do you mean?" she asks. You grab her by her chin and direct her body to go upright like you are so you can be face to face. You give her a strong passionate kiss, hugging her back tightly, and then surprise her by pushing her onto the bed.

"I mean, I was stupid for being scared of what could happen; when there was nothing to be afraid of." you tell Cassie, but she still doesn't really understand what you mean.

You position yourself in between her legs and lift them up so you can take off her panties. As Cassie lays naked beneath you, you take in her natural beauty. Her erect nipples that you're tempted to devour, her toned torso you run a hand across as you feel her sweat on your palm, and her cute shaved innie pussy that's glistening with her juices.

"Cassie--" you moan, as the anticipation of penetrating her is building, resulting in your dick becoming fully erect.

"It's Cassandra" she tries to correct you. You go on top of her and kiss her once again. You quickly move down to her neck, planting kisses and licks as you move your fingers to her entrance to feel how wet she is already. You go back upright, and tease the entrance of her pussy with your dick.

"No, Cassie. I don't need to pretend. I want this. I want you." as you move your hips slowly to penetrate her. The heat of her pussy enveloping the head of your cock.

"Oh! Mr. Craig! I want this too! I've wanted it for so long!" she shouts, as she wraps her legs around your waist and sits up with her hands on the bed propping her up. Cassie doesn't wait for you to set the pace, and starts gyrating her hips and grinding on your lap.

The sensations it sends your dick is intense as her movement and pace are constantly working the glans of your dick. If she goes any further, you feel it'll take you over the edge as well. Before you reach the point of no return, Cassie stops gyrating and just plain vibrates, as her body shakes with her first intense orgasm.

"FUUUUUUCK!" she shouts as her arms lose strength and could no longer prop her up. You catch her in your arms, so she doesn't fall on the bed.

The momentary pause in her movements gives you the opportunity to explore her body with yours. She places her arms around your neck to support her, giving you the opportunity to cup her breasts in your hands and start sucking and flicking her nipple with your tongue, alternating between each nipple.

As Cassie regains her energy back, she starts moving her body up and down on your shaft. Stimulating your dick once again. You return to kissing her, and her hands grab your face as she hungrily makes out with you. Her lower body movements have been slowed down by having to multitask, so you grab her waist and start moving your own hips to fuck her at your pace.

"Oh God, Mr. Craig! This feels incredible!" she starts shouting. "I never want to let you go. I have goosebumps in every inch of my body." she adds, before her moans become louder and louder with every pump of your dick inside her. "Don't stop, Mr. Craig! I'm about to cum!" she shouts, but she catches her breath momentarily and tells you in a softer voice "But don't stop until you cum inside me", right before she groans a loud guttural groan to signify her climax.

Not wanting to disappoint her, you increase the pace of your pumps as you grip her waist even tighter for support. She rests her head on your shoulder now, her arms still around your neck, and bites your shoulder before she climaxes once more. The pain from her bite sends mixed signals in your brain as the pleasure you're experiencing with your dick is getting close to the edge, while there's a stinging pain from your shoulder.

In an effort to mask the pain, you pump into her even faster, shaking your entire bed as you do. Once Cassie rides the final wave of her orgasm and releases her bite from your shoulder, you feel your climax coming ever closer.

"Cassie --" you try to warn her. "Don't stop Mr. Craig, I'm on the pill." she replies understanding what you wanted to say. Without any more reason to hold back, you release your seed inside your daughter's best friend with a loud groan of pleasure as you do. "I feel it inside me, my body feels so warm" she tells you in between deep breaths, her exhaustion obvious.

"I love you, Mr. Craig" she says as she stares into your eyes with a deeply satisfied and euphoric smile.

"I love --"

~ DING DONG ~

~ DING DONG ~

~ DING DONG ~

~ DING DONG ~

Stupid-fucking-piece-of-shit-doorbell

CHAPTER 32.1

Who's at the door?

A 'new' neighbor

"JUST A MINUTE!"

You shout, as the doorbell keeps ringing. You're going to kill Stella if it's her, since you gave her a spare key for this exact reason. Okay, not this exact reason, but for there to be no need for her to use the doorbell, at least.

You look back at Cassie who is just laughing at this whole scenario.

"If that's Stella, I'm going to kill her," you jokingly tell Cassie, before giving her a quick kiss and standing up from the bed. You head to the bathroom in your room to grab a bathrobe to cover yourself up. Once you've gotten the bathrobe, you see Cassie laying on your bed naked and still breathing heavily; but more noticeably, she's just staring at the ceiling with a wide grin on her face.

You can't wait to tell Stella she has the worst timing, so you rush outside to get that over with. It doesn't escape your notice that the door to your bedroom is apparently slightly ajar and you may have failed to close it properly earlier.

"Be right back," you tell Cassie as you make your way out of your bedroom. As you get out of your room and rush to the main door, you slip on something wet on the floor by your bedroom's doorway and you almost fall to the floor. Luckily, you keep your balance by holding onto the wall before you completely faceplant.

The doorbell keeps being rung as if Stella just wants to annoy you and Cassie now. When you open the door, you're surprised to see it's not Stella at all.

"Hi, I'm really sorry to bother you..." and you phase out the rest of what she's saying as an incalculable amount of rage and annoyance swells up inside you as this random person had the audacity to ruin such a wonderful moment for you.

Once you snap back into reality, you realize this person hasn't stopped talking, "... I have a ball gag you could borrow if you really don't want to stop--" you cut her off and ask, "I'm sorry, who are you?"

"Like I said a few seconds ago, I'm your next door neighbor, from 303? Name's Vivian." she tells you. "Paul and Eric live in 303." you reply, not sure why she would lie about that. "From what I was told before I moved in last month, they were moving to the suburbs." she tells you.

The information shocks you a bit as you didn't even realize that somebody else moved into the apartment next to yours for an entire month already. "I'm sorry, I haven't been updated for a while, but why are you here?" you ask her.

"Oh wow, you really didn't hear a word I said did you?" she says, a bit offended. "Anyway, I know I didn't ring your doorbell at a particularly good time, and you're probably annoyed with me, but your bedroom noises kind of penetrate the walls to my bedroom." she informs you.

"Oh... shit. I'm sorry. I never knew that was a problem." you tell her honestly. You really didn't know since Paul or Eric never complained to you and Diane before; but you're not surprised as to why that is.

"Hey, like I said earlier, I normally wouldn't give a shit and let you guys do you, but it's kind of the second night in a row where someone's screaming their lungs out, and it's Monday tomorrow, so I have to get up early for work. I hope you understand." she informs you.

"Fuck. Yeah, of course. I'm sorry again." you tell her. You outstretch your hand to offer her a handshake, and so you can introduce yourself as well, but she curls her lip in disgust, and you realize it's probably because she knows where your hands have been just a few minutes ago. You wipe your hand on your bathrobe but don't offer her another handshake.

"I'm Jay by the way. I'm sorry again for this. Weird way to introduce myself to my new neighbor." You tell her.

"Don't worry about it. Honestly, I thought nobody lived in your apartment before tonight." she admits. You rub the back of your neck out of embarrassment, not really sure how to react to that. You have been a recluse these past few months, but discussing the reason behind that would be awkward at this time.

"Anyway, like I said, I really need to go to bed. Sorry again for cutting your night short." Vivian tells you before walking back to her apartment. "Good night!" you yell out just before she enters her apartment, and she waves a hand at you in response.

Wait... did she just say she has a ball gag you could borrow!?

CHAPTER 33.1

What happens next?

Pillow Talk

You close the door to your apartment after having talked to your new neighbor, Vivian, and you make your way back to Cassie in your bedroom. You see she's sitting up on the bed, her back resting on the headboard with the covers covering from her breasts down like in those Hollywood movies.

As you enter the bedroom, Cassie whistles and teases, "Looking good, Mr. Hefner", referring to you only wearing a bathrobe.

"Aren't you a bit young to know about Hugh Hefner?" you jokingly ask her.

"Old enough to be one of his girlfriends." she jokes back.

"See, now I know you don't know who you're talking about. You need to be blonde to be one of his girlfriends." you tell her.

"He also needs to be alive to have a girlfriend." she replies with a chuckle.

You lay down next to her on the bed under the covers, and she immediately cuddles you. You wrap your arm around her while she rests her head on your chest and places one of her legs on top of you.

"Why would you think I don't know who Hugh Hefner is?" she asks you.

"I don't know. Didn't he, like, die before you even reached high school?" you jokingly answer.

"It's called the internet, Mr. Craig." she answers you with fake annoyance, as if the answer was obvious, but she still has that happy grin on her face.

"You look for perverted old men on the internet?" you try to tease her.

"Seeing as I just had sex with one, that shouldn't surprise you." she teases back, and she laughs as she knows she hit a nerve with you.

"I'm not that old!" you react, acting like you were offended. You both end up laughing at how it's your age that you were sensitive about and not being considered perverted.

The two of you take a moment to bask in the new level of comfort you've found with each other. It was only last night that you didn't even want to be in the same room as her for fear of doing something inappropriate; and now, you're cuddling next to her naked body and joking about Playboy and perverted old men.

"Was that ever a dream for you Mr. Craig?" she asks, genuinely curious.

"What? Being a rich old guy? Can't say it was a dream or even a goal of mine. I'm happy that I can make a good living doing what I love, and that's enough for me." You answer her. She actually moans a little hearing your answer. Maybe it's 'Magic Touch', but you'd like to think she just appreciates your answer.

"What about the multiple girlfriends part? Was that ever a fantasy of yours?" she asks you again. The loadedness of the question is not lost on you, and you take a moment to think about how you should phrase your answer.

"In all honesty, I never had to think about it. I got Diane pregnant when she and I were 17, and my dream's shifted into just being a good dad to Stella after that." You answer her.

"You've been a great dad to Stella!" She reacts enthusiastically. "This'll sound icky since I'm naked in bed next to you, but you were a great 'dad' to me too." she admits, blushing a bit from embarrassment.

"But Stella and I are both adults now and need less parental guidance than we used to. So now that you've made being a great dad a reality, and have more available time to fantasize, is having multiple girlfriends something you'd ever want for yourself?" she continues, not letting you dodge the question. You're curious as to why she cares about it so much, but decide it's best to just answer her question instead of acting defensively.

"After tonight, I really don't need to fantasize about it either. I know I'll be happy with you, and all I need to think about now is making you happy." you answer her honestly, omitting the fact that if you had enough points before, you would have bought the trait 'Normalized Polyamory' to not have to choose between her and Tanya.

Having given more thought about it though, you realize that that was selfish of you. Cassie was sure about her feelings for you and Tanya wasn't. Choosing Cassie only means that Tanya has a clearer answer for what she needs to feel about you once you tell her about being in a relationship with Cassie. That wouldn't be too bad, right?

Cassie gives you a quick peck on the cheek after your answer. "I know you're being honest when you say you want to make me happy Mr. Craig, and I'm sure you'll be amazing at that... but what about Ms. Tanya?" she asks. "Didn't you say you were still thinking about your feelings for her?" she adds.

"I was unsure of my feelings for her earlier, but what I am sure of, is that I wouldn't want to lose you just to explore what I feel for Tanya further." You answer her honestly.

"What if you don't have to lose me?" she asks you.

CHAPTER 34.1

What happens next?

Pillow Talk, Pt. 2

"What do you mean?" you ask her to clarify, genuinely confused at what she's asking you. "What if you could explore those feelings you may have for Ms. Tanya, and not have to lose me?" she clarifies.

This relationship isn't even a day old, and she's already asking you if you want to date other women. You're not sure how to interpret that.

You take a moment once more to think how to properly answer her. You don't want it to sound like you'd think that would be great since you can have your cake and eat it too, but there's a reason why the idiom is you can't have both. 'At least, not without the help of magic', you think to yourself.

"Stella and I talked about it earlier," Cassie admits before you can answer her. "She and I agree that forcing yourself into a monogamous relationship may not be the best thing for you right now." She adds, and you can't help but cover your face with your free hand as you let out a chuckle.

"That's what Tanya said too." you tell her. "Why is it so important that I don't jump back into a loving monogamous relationship yet? Especially, when that loving monogamous relationship would be with you?" you ask her, genuinely curious about her reasons, since you honestly thought about pursuing multiple relationships yourself.

"What's important is you find loving relationships. That doesn't just have to mean me. It includes Stella, and maybe Ms. Tanya if you want to explore that. It's loving relationships you need, not necessarily monogamy." Cassie responds, to which you immediately respond, "I'm not sharing you.", which elicits a laugh out of her, as you've become possessive of her already.

"No one can compare to you." she tells you, then gives you a sweet peck on the cheek. "So you don't have to worry about that, but that's not what I'm saying. For me personally, I don't want to be the one to make you choose between me and somebody else that you may have feelings for. Especially after you told us that you're not sure what you feel about Ms. Tanya. Why shouldn't you be able to explore that?" she asks, and the only answer you can think of is that you'll hurt someone's feelings if they become jealous. Weirdly enough, that's why you want to buy 'Normalized Polyamory' in the first place.

"Wouldn't it hurt you to see me with someone else?" you ask her, since that's the main reason that's holding you back from exploring that option anyway. "I've seen you with someone else my entire life Mr. Craig. I was never jealous of Mrs. Cr-- Ms. Diane. All I ever wanted was to be with you. I didn't care if I had to share you with her." she admits.

"I never wanted you all for myself. I just wanted you." She adds, with a bittersweet tone; as if she's happy that she's with you now, but it had to cost you months of pain beforehand.

"More than that, I don't want to force you to give up on someone who you can bring genuine happiness to, and be given that in return." she continues. You find it unbelievable how open she is about you meeting, and even dating, other women. It sounds too good to be true.

A lot of things in your life lately sound too good to be true, but that's with the help of the Affection Multiplier. So it's even more unbelievable that every girl you've been with, plus your own daughter, thinks it's best for you to explore your feelings more fully; and that's without the help of magic.

"I can always just stay friends with Tanya." You tell Cassie, not wanting to make it sound like she's not enough to make you happy.

"Of course, but what if she doesn't want to just be friends? What if you don't want to just be friends with her down the road too? Will you force yourself to choose between her and me? Like I've already said, I don't want to be the one to have to force you to go through that." Cassie tells you.

It's at this point you realize that she just genuinely wants you to be happy and not have to go through a similar kind of pain like you've gone through these past few months, or cause others that kind of pain too. "Who am I to argue with the universe?" you jokingly ask her, which now makes her confused.

"Apparently, everyone agrees that I shouldn't limit myself and explore my options. You, Tanya, Stella, the app..." you tell her, which she immediately picks up on, "The app? What do you mean?" she asks.