A 'normal' date

Reality seeps away again, my vision blurs at the edges and slowly blacks out before slowly returning.

I find myself in a classy looking apartment, tastefully decorated sitting on a couch next to a stunningly beautiful blonde with shoulder length wavy hair, it looks like something that you’d wear to the beach and doesn’t really suit the elegant black pencil dress she’s wearing, but when someone is that beautiful, anything looks good on them.

“Uh hi, Earth to James? Are you receiving?”

Shit, I didn’t know her name, is it even possible to ruin a date in a simulation? I just threw out the first thing I could think of and hoped the Sim would play along.

“Yeah, sorry Daisy, just got woozy there for a second, I’m alright now”

Daisy furrows her brow, saying “Uh alright, you’re OK now though?”

“Yeah no really, I don’t know what that was.” It’s time to test things out then I suppose.

I think hard, ‘you really like me and hope I make a move’ and direct the thought at her. Daisy’s expression subtlety changes, she’s looking at me a bit more wistfully now I think. I lean in to kiss her, she mirrors me and leans forward as well to meet me half way. We spend a few minutes making out before I place my hand on her thigh, beneath her dress and start moving it up her leg. Daisy pulls away suddenly, “Hey, wow, slow it down Mr.” Shit, that was unexpected, but after a seconds thought I think to myself this Sim really is quite clever, if everything went my way I’d never get a chance to use the control so it puts some roadblocks in the way so I can have some fun creatively problem solving my way through. After a moment I think I’ve got something that can work.

‘Daisy, you’ve got some intimacy issues so you avoid having regular sex with guys until at least the 5th date. However, you think anal is less intimate so you always offer up your asshole to guys on the first date.’

Daisy speaks up again, “Listen James, before we go any further I need to say something. I’m not really comfortable having normal sex on the first date, I just think it’s something special that should be done later on.” I play along and look downcast, she grabs my hand and gets a playful look in her eyes, “But that doesn’t mean we can’t do anything. If you want, you can fuck my ass instead.”

Giddy with how well the Sim is working I eagerly nod, saying, “Anal on the first date. Wow. That’s kinda intense. Girls don’t generally do that.”

Daisy steps back off the couch, unzips her pencil dress and slowly slides it down her lithe body, “Yeah well, I’m not like most girls.”

“How does that work out for you though? I mean, how do guys react when you tell them?”

“Some guys call it quits then and there, most guys get really excited – God, what the deal with guys and anal anyway? Most of the time they act like a kid in a candy store when I tell them; I’ve just never thought of it as a big deal… Practically no guys make it to a 5th date though.” A melancholic expression briefly crosses Daisy’s face and she says more quietly, “I kinda like it this way though, it means I never get too close to anyone.”

“Do you ever get worried about what people say if guys started telling others what you’re like?”

Daisy slinks over to me, stopping between my legs and begins working my stiff cock out of my trousers. “No, fuck what those people think. If they want to have a go at me for what I’m like let them, besides, it helps me ID the ones to keep out of my life. ”

Daisy finally manages to fish out my thick 7 inch cock from my pants and eyes it for a second before turning around, bending over slightly and presenting her ass to me. She stands like that for a few seconds before turning her head back around to look at me and saying, “Well what are you waiting for? Do you need an official invitation or something?”

Gulping I reply with a smile, “I mean, that’d be nice”

Rolling her eyes Daisy reaches back around with her hands grabbing her cheeks and spreading them giving me a perfect view of her asshole and pussy, she’s literally dripping wet, thick strands of it hang down from her pussy making it look incredibly appetizing. Another time I think to myself. “I, Daisy of the House Cromwell hereby give you permission to enter my asshole” she says with an exaggerated posh accent facing away from me.

“What, just like this? Don’t you want to grab some lube or maybe get me wet with your mouth? Won’t it be uncomfortable if I go in raw?”

“Aren’t you just a nervous nelly, no it’s fine honestly, I’ve had lots of practice so I’ll be OK as long as you take your time.”

Despite what she’s just said I still rub the head of my cock around her asshole a bit, trying to smear my precum around it.

Daisy must have felt the liquid warmth being rubbed on her ass because she turned back to me and asked, “What are you doing? I told you I’d be fine”

“I know, but I still wanted to do that for my benefit okay?”

Daisy gives me a warm smile and turns her face away. While I’m still rubbing the head of my cock on her asshole, she suddenly lowers herself down and I feel the head of my cock slip inside her eager asshole. It feels like heaven, having her muscles wrap around my cock and slide their way down. Daisy didn’t stop here, she kept lowering herself further and further down onto my dick, it took less than 10 seconds before she had worked her way down to the base. Christ if this was her version of slow what did she think fast meant?

“Holy shit your ass feels amazing, I love the way it feels on me.”

“L word already? Easy on there James, don’t make this out to be more than it is” She starts bouncing up and down on my lap. Daisy’s good at this, she expertly bounces up to the perfect height every time, high enough to keep the head of my cock still buried in her ass without it slipping out before bouncing down and having her asshole swallow my cock down to the base. It’s amazing that even without lube her asshole just glides up and down my dick, hugging it tight the whole while. I feel a wet warmth on my balls and it takes me a moment to realize it’s her pussy juice dripping down onto me. I reach around her hips so I can rub her pussy and give her some relief. But I only manage to touch her there for a second before she grabs my wrist and pulls my hand away, it comes away drenched. She says without turning around, “James. No. Even if it’s not sex, I still can’t have you touch me there, not so soon” She sounds strange. I nod even though she can’t see me and turn my attention back to her asshole.

I start meeting her bounces half way and keep at this for a few minutes before trying to change positions. “Daisy can you turn around, I want you to ride me cowgirl”

“I prefer it this way”

I think ‘Daisy, you want to turn around and face me’

“Please Daisy?”

“Alright”

She finally pulls herself all the way off my cock for the first time and faces me, she climbs up onto the couch, puts her feet to either side of me and starts lowering herself down. My eyes are glued to her face, Christ she’s fucking beautiful. She grabs my cock in her hands and positions me at the entrance to her asshole. “Hey eyes down here champ, the views better”

“Barely” I say but still can’t help but look down. Her pussy is still soaking wet and drooling lubricant, it’s trailing to her ass then down my cock. It’s hardly necessary with how easy it is to enter her ass but it makes her asshole feel so much slicker now. She slams herself all the way down in one go suddenly, leans forward to hug my neck, resting her head against my neck and starts bouncing up and down again. “Jesus Christ, I can’t believe you’re letting me fuck your asshole like this on our first date, this is insane. I’ve got a huge fetish for anal so you’re perfect for me.”

I can’t see her face but she sounds strange again, “Well you’re in luck, I’m an anal only girl for the 2nd, 3rd, and 4th date too, a real all you can ass fuck buffet for 4 nights, so get as much use out of me as you can while you can.” She says while rhythmically bouncing up and down without pause.

“What about the 5th?”

“Well, I tell guys I want to do vaginal on the 5th date. I mean, I don’t really, but I just say that to see how they react. Most guys don’t come back for a 5th time… Listen, James, if you really like anal, come back to see me a few more times, I’m into it too and I’m up for whatever you’ve got in mind as long as it involves my ass, you can do whatever you want to it, I don’t have many limits these days. Just don’t come back a fifth time OK?”

“You really don’t want to see me a 5th time? Just 4 dates and goodbye?”

“Isn’t that what you want? An easy girl that’ll let you pump her ass full of cum without complaint, a girl you can dump with no strings attached? I mean I’m literally giving you permission to pump and dump me, a chance to use my asshole like a cheap whore and leave, most guys would kill for that.”

“Well I’m not like most guys I echo back at her.”

“We’ll see.” She lowers her voice and whispers into my ear, “James I need to you really start fucking my ass, show me how much you like it, don’t be afraid to be rough.”

She raises herself so just the tip of my dick still inside and holds herself there. With the couch underneath me to bounce off of, I start to really piston into her asshole, feverishly fast, balls deep every time. 15 minutes of this rabid assfucking continues before I feel and see Daisy spasm and twitch on me, she was cumming from anal and I was in love. The muscle contractions of her ass from the orgasm set me off too and I blew my load inside her soon afterwards. We sat there for long minutes, I grew soft inside her before she abruptly got off me. Daisy grabbed some nearby wet wipes and wiped away the cum leaking from her asshole. Despite the pounding it took, it didn’t look any worse for wear. Surprising me, Daisy reached back with her hands and pulled her cheeks open again, showing me her asshole, it pulled open too, gaping slightly and looking slightly red and puffy. “How’s the view? Enjoy the aftermath?”

“It looks amazing, I can’t believe after everything it took that it still looks as good as it does.”

“Yeah like I said, I’ve had a lot of experience.” Daisy started walking off toward the bathroom. Saying over her shoulder, “I had fun James, but I’ve sorta got some stuff to take care of, do you think you could leave and lock up while I shower?”

I was definitely coming back for more dates.