Incest/Taboo Tony's World

Hotel room booked in town. Can't take any chances of someone finding out. I'll collect you at the end of your block and we'll meet P there, she writes, confirming the plan.

My balls ache they're so empty today, I text Cindy about an hour later.

I'm not able to walk straight today after what you did to me last night with that weapon between your legs. You nearly split me in half, Cindy replies.

Everything that's happened with Cindy, her husband, and now what's going to happen with Pippa. It all makes me wonder what other things people are hiding.

I look around the restaurant and see couples of all ages, and I can't help but wonder what dirty little secrets they have. What goes on inside their four walls when they close the door behind them at night.

If the last three weeks has thought me anything, it's that things aren't always as they seem.

Look at Cindy and Paul. You're normal middle aged boring couple. On the outside you would just assume beautiful woman married not very attractive, slightly older man for his money, she plops out a couple of kids for him, and now they've grown to love each other. Maybe that's even partially true, but you would never guess what they get up to in the bedroom now.

Then there's Pippa, the mega babe. Definitely married for money, the dude is twice her age! She always seems to look down her nose at people, and she's not very likeable. But she's willing to spread her sexy legs and take my load in the hope of getting pregnant. Who'd have guessed. Definitely not me, but I'm sure as hell going to enjoy myself.

I see neighbors, parents of some of my friends, random strangers, all with their own stories and secrets. Everyone just got a lot more interesting to me. Then my mind wanders to my own parents, do they have some sort of kinky sex life they've managed to keep hidden? Maybe? Who knows? Fuck, I shouldn't be thinking about my parents like that.

After work I cycle home to see Mom and Dad, but also to grab some fresh clothes. I'm going to spend the night with Cindy again. It's ourr last night alone before Paul gets back tomorrow, so why not make the most of it. Mom has dinner on the table for me without even asking. When I finish I say I'm staying over at a friend's, and Mom is of course suspicious.

"You seem to be spending a lot of time with this friend of yours," she says as she stares me down looking for more details, the way mothers do.

"Yep, well if that's everything, I'll be on my way," I say, giving nothing away.

"You should ask your "friend" to stay over here sometime, we don't bite you know," she says.

"Sure thing Mom. OK, see you guys tomorrow. Thanks for dinner," I say as I walk out the front door and hop on my bike.

Cindy wasn't expecting to see me, but she is delighted I'm going to stay over with her again.

"It gets lonely in this big house when there's nobody around," she says. We're settled back on the sofa again snuggled up watching TV.

God I love this feeling being with her. Cindy has become more than just sex for me. I've never felt like this before about anyone. Don't get me wrong, we can't keep our hands off each other, we have a huge sexual attraction towards each other. But it feels more than that.

We spend all Friday evening watching TV and talking, then later on Cindy opens a bottle of wine. I'm not very experienced when it comes to wine, but it tastes nice, and we finish the bottle while watching a movie. When we eventually go upstairs, Cindy goes into her en suite to brush her teeth and do whatever else she does to get ready for bed. When she comes back out she has taken her make-up off, and has her hair held back in a cloth hairband. She's wearing a black nightdress that comes to her mid-thigh. She is breathtakingly beautiful.

I use the bathroom when she's done, then I climb into bed under the covers beside her. I only ever wear boxers to bed. When Cindy switches off the bedside light, I roll onto my side facing her and feel her shuffle backwards towards me. We meet in the middle, and her ass nestles perfectly into my lap as I wrap my arm across her gently pulling her in close.

"I love this," she whispers.

"Me too," I say back, feeling her soft hair brush off my mouth I'm so close to the back of her head. "I wish you were mine."

She says nothing for a while, but eventually says, "so do I."

My hand in resting on her toned stomach and her nightdress feels so soft. I'm fully erect in my boxers, and its wedged in between her legs and up against her ass. I got hard as soon as Cindy reversed herself into my crotch a few minutes ago, but both of us ignored it.

"We can do this more often," she says then. "Just the two of us. We'll find a way."

"I want that. I know I have to share you, but I want my share," I say.

"Make love to me Tony," Cindy says quietly.

I take my right hand off her stomach and use it to pull my boxers down, releasing my throbbing boner as it pokes into Cindy's ass. Then with the same hand I push her nightdress up her thighs, pulling it up over her ass as she stays lying on her side. I hook my thumb into the waistband of her panties and pull them down, leaving them around her knees.

I can feel her arching her back slightly which causes her ass to push into me a little, but this presents her hole in a more accessible position. I use my free right hand to guide my precum dripping cock to her slit, she's dripping too, and I slide it inside her slowly.

Her pussy feels perfect. Tight, but not too tight, and she adjusts to my large size so quickly. We fuck slowly like this for what feels like hours. We even talk as we screw.

"What fantasies do you have Tony," she asks during our slow sex.

"Oh you know, the usual stuff," I say, not really trying to think of anything.

"Come one baby, you have to have some," she says.

We're barely moving. My fat cock has her stretched, but I'm only pulling out an inch or two then grinding it back in gently. Over and over. It's actually fucking amazing.

"It's embarrassing Cindy, they're all just stupid shit. The usual stuff you see in porn," I say.

"Nah, not that crap. I'm talking about real fantasies. Stuff you would never do. People who are off limits, but who are fun to fantasize about," she says then, pressing me.

"Well, you actually," I say honestly, and she laughs. I feel her pussy tighten a little when I said that. She must still get turned on by the taboo of what we're doing.

"OK, yeah, that's what I'm talking about," she says. "Who else?"

"Pippa maybe. I mean, it's kind of hard not to fantasize a little about her, with what we're going to be doing. I know, it's not sex, but still," I say.

"Yeah, I get it. You should imagine I'm her," she says.

"Would you like that?" I ask.

"Yeah," she says, and she grinds her ass back a little harder. "Are you curious about what her pussy is going to feel like?"

"I've thought about it," I say.

"She's very good looking," Cindy says then.

"I know, she's gorgeous," I say, and I can't stop myself thrusting a little harder into Cindy as I imagine she's Pippa.

"Aaahh, that's it, give it to her," she says having felt me.

"You want me to put a baby in your belly Pippa," I say, playing along.

"Mmmm, yes, I need this cock to make a baby," she groans.

We continue on like this for another while, and I have to admit I like it. I had never been one for role playing before, but it's kinda hot.

"Call me mommy," she says then.

"You seem to like that," I say.

"Do what your mommy says, good boy," she says then.

"Yes mommy," I say, deciding to play along with this too.

"Do you like thinking about your mommy?" she breaths quietly.

Fuck, this is getting kinky now.

"Yes," I say without really hesitating. "I do."

"Mmmm, that's a good boy Tony," she says. "Your mom is a very sexy woman."

I hadn't expected our role play to veer in this direction. But it's really arousing me. I squeeze her hip a bit tighter with my right hand, and wrap my left arm that's underneath her body tighter around her chest pulling her in close. Then I pull most of my cock out of her hole, and ram it back in hard.

"Oh fuck Tony, don't go too hard on your mommy," she says, and I can't help but imagine it's my own mom saying it in the dark room.

I can't fuck her very fast in the sideways position we're in, but I give her long hard thrusts instead and she seems to be loving it.

"Sorry mom," I say. "I'll be careful."

"You're a naughty boy doing this to your own mother Tony," says Cindy.

"How can I resist a body like yours, I've wanted to do this for a long time," I say, really getting into it now.

I try not to think of my mother in this way, but you would need to be blind not to notice how she looks. She has a sexy hourglass figure, with a great ass and legs. She usually keeps them covered up, but you can tell she has a nice pair of tits too, a little more than a handful I would guess. Mom is very attractive, with shoulder length dark brown hair. She's a couple of years younger than Cindy at 49, and she keeps herself in great shape with her yoga classes and regular runs. A little secret of mine is I like seeing her in the hospital scrubs she wears for her job as a physiotherapist, they've always turned me on a bit.

But I don't normally think about my Mom in a sexual way. Until now that is. I'm realizing how much I like it, and this is a safe game to play. It helps that Cindy has a very similar bode shape to Mom.

"Oh my god, Tony, I'm cumming," Cindy says, clearly enjoying her role as my mother.

The quivering from her pussy as it clenches me tight is enough to finish me off, I had already been very close to my own climax for some time now. The smell of her pussy juice quickly fills the room and her hole feels like it's on fire. With one last hard thrust, I fill her cunt with my seed.

"That was nice baby," Cindy says when we both catch our breath after climaxing together. "That was a fun game, wasn't it?"

"Yeah, nice," I say, but I feel a little paranoid. "Just so you know, I don't want to fuck my mom."

"I know honey, it's called role play. Relax. I will never judge you," she says, reassuring me.

She just has a way of making me comfortable, no matter what the situation is. I'm still inside her, but we're both really comfortable so we just stay like this as we eventually fall into a nice peaceful sleep.

I wake up at 4.20am, and we must have separated from our spooning position at some stage because I'm on my back now and Cindy has rolled onto her front.

I need to use the toilet so I climb out of the bed and walk towards the en suite. I flick on the light and I see my reflection in the mirror. I'm naked, having discarded my boxers while we were having sex earlier. I'm in pretty good shape I think to myself. I usually keep my pubes shaved off, but I notice they've grown back a little. I make a mental note to shave them again before next weekend.

Just as I'm about to walk over to the toilet, Cindy walks into the bathroom.

"Hey, you needed the toilet too," she says as she skips past me holding her knees together. "Sorry, I can't hold it."

She sits down on the toilet, pulling the hem of her black nightdress up out of the way, and then she pulls her panties down around her ankles. They're black too I notice, I hadn't seen them in the dark earlier. Then I immediately hear her piss into the toilet with a strong force that surprises me. I haven't heard many women take a pee though, so this is probably normal.

When she's done, she reaches back and tears off a piece of paper to wipe herself. This is such an unexpectedly sexy sight. The whole moment is.

"Tony, can I ask you something?" she says while she reaches down and begins to pull her panties back up her smooth legs. She's staring at my soft cock hanging between my legs as she says this.

"Yeah of course," I say.

"Can I hold it? While you pee? I've never done that before," she says, surprising me.

"Sure, I guess," I say. A little weird, but whatever.

She stands up and doesn't flush, then steps to the side to let me stand in front of the toilet bowl. As soon as I'm at the toilet I really need to go. Cindy steps behind me, and then I feel her right hand take hold of my cock. She points it to the middle of the bowl, and then I release.

My stream hits the water with a splash, and I hear Cindy gasp. She keeps a good hold of my cock, but she starts to get a little braver as she moves her aim up onto the porcelain bowl, then back into the water again. I keep pissing as she does this, but her hand holding my cock is starting to have an effect. I start to harden a little while the piss keeps spraying out.

A few seconds later I can feel that I'm almost done, and then the flow slows and eventually stops.

"Shake off the last few drops," I say to her.

She does what I ask, and for some reason it's incredibly sexy. The gentle shake she gives my cock causes it to harden even more, and my shaft now really starts to swell in her delicate hand. She obviously notices this too, and she doesn't let go. Standing behind me, she transitions from aiming my cock while I took a piss, to now slowing jerking me off.

The lewdness of the situation is having a rapid effect on me. Here I am, 21 years old, with my friend's sexy 51 year old mother standing behind me jerking me off in the middle of the night, and I'm going to cum into her toilet.

Neither of us have said anything since she started the handjob, which has added to the experience, making it feel like we're doing something wrong. It feels unbelievable. When she reaches her left hand in between my legs from behind and grabs hold of my balls, I feel myself about to cum. I reach my left hand back and grab her ass cheek, squeezing it tight as my cum erupts from my cock, which looks massive in her small hand. The first shot hits the bottom of the open toilet seat cover, the second lands on the seat itself, and then the next few squirt straight into the toilet. I see the back of her hand is covered in a couple of cum ropes too.

When I'm finished shooting, Cindy releases my cock and brings the back of her hand to her mouth, then licks up the cum that landed there. She leaves the en suite without saying a word and gets back into bed. I follow her a few seconds later after deciding not to bother flushing.

Cindy and I spend a lot of time together over the next few days, knowing that from Wednesday the priority will be Pippa. My initial excitement has waned considerably. Cindy has been at pains to explain what we're doing is purely clinical. So reading between the lines, that means Pippa has no interest in me sexually. I'm not surprised, I doubt anyone is good enough for her.

We talked over how the sessions with Pippa will go, and we both agreed that it would be best if Cindy is in the room with us, mainly to help me perform. The plan is for me to insert my penis into Pippa just as I am about to ejaculate. She discussed this with Cindy apparently. Talk about demanding! I swear, if she wasn't so hot, I would tell her to go fuck herself, literally.

I can cum quick when I set my mind to it, years experience practicing knocking one out quick in my room could finally pay off. But I'm not sure I could bare the embarrassment of standing there jerking off in front of Pippa, even for me that's a bit too much. So I'll need some help to reach the finish line. And what better encouragement than having the sexiest milf in the state as my fluffer.

Brian is spending a lot of time over in the new girlfriend's place, so that makes sneaking over to Cindy's a lot easier. Paul gets back on Saturday, so it's back to the usual business each night. He has no idea Cindy and I have been seeing each other behind his back the whole time he was away on business, the dickhead.

I've grown so close to Cindy recently, seeing what her husband does when we're finished fucking really has an extra sting now. I want her all for myself. So when Cindy keeps our secret from her husband, it is a big deal.

My week at work passes without any drama. It's busy most days, which is good as it helps keep my mind off the weekend and what I've agreed to. Sometimes when I think about it, I start to freak out a little. Fathering a child, even in the circumstances, is a big deal. I'm only 21, I'm not even close to being ready to have a child. But then other times when I think about it, my horniness for Pippa comes to the fore and I get hard just thinking about getting to do this with her.

Flirting with some of the guests in the restaurant is a nice distraction this week also. I've definitely developed a bit of a taste for the more mature ladies, ever since I managed to nail Cindy Smith. I can't help but imagine what some of the other milfs would be like in the sack.

On Wednesday evening Cindy and I do a dry run of our plan for Saturday. We don't bother booking a hotel room, but Cindy picks me up at the end of my block at 8pm. She's parked up beside the sidewalk, and I casually sit in to the front passenger seat as I walk by her SUV. It's such a quiet street, there's very little risk of being seen. But even if someone did see me get into a car, there's nothing suspicious about that anyway.

We had another motive to do our little trial this evening, we wanted to spend a little time alone together. Cindy drives us to a secluded area in a nearby forest, a little parking lot for hikers but it's deserted at this time of the evening. We both hop into the back seat and when I hike up her skirt as she's on her hands and knees on the spacious back seat, I see she hasn't woren any panties. I fuck Cindy hard and fast, and before long the windows are fogged up and the car reeks of sex.

When we're done, Cindy drops me back where she picked me up. It feels dirty and cheap, and that's exactly what we wanted. It also feels like a real affair now, and I fucking love it. I get a big kick fucking Cindy behind her husband's back. He's an asshole, he deserves it, and I think Cindy is getting just as much of a buzz from sneaking around as I am.

Then before I know it, my alarm clock is going on Saturday morning. Cindy isn't collecting my until 8 this evening, so I need to get through a full shift at work first.

During my break I call down to the gym for a catch up with Brian. It feels like it's been ages since we talked. I do feel a pang of guilt when I think about him. I've spent more time in his house than he has over the last two weeks. And as for the unspeakable things I've done with his mother...

But as soon as we start chatting, I manage to forget about all that and Brian becomes my friend again. He tells me all about his new girlfriend.

"Yeah it's going well, but we'll see," he says. This is typical Brian, he tends to lose interest in his girlfriends pretty quick.

"Give it a chance man, I'm sure she's lovely. I can't wait to meet her," I say.

"I guess. We'll see, maybe after another couple of dates," he says.

I decide to have a quick workout in the gym before going back to work. I need to burn off some of this nervous energy I have inside me.

After cycling home when my shift finished at 3pm, Mom had dinner ready for me. I catch myself glancing at her ass when she's bending over the cooker, and I notice how nice it looks. But I make myself turn away, Cindy is a bad influence I think!

Her SUV is parked up waiting for me when I get to our meeting point. I made my usual excuse for Mom, she already suspects I have a secret girlfriend, and she's not trying to pry too much, so I may as well make the most of it.

The drive to the hotel takes about 20 minutes, and it's during that time when the seriousness of what's about to happen really sinks in. Am I making a terrible mistake? I know I'm helping someone and all that, but I'll have a son or daughter in the world, regardless of what anyone says. Am I ready for that? I know I won't be involved in the child's life, but will I be able to deal with that either?

There are so many unanswered questions and doubts. It's only when Cindy kills the engine and reaches her hand over to my knee that I snap out of my thoughts and realize we're in the hotel parking lot. We didn't speak a word the whole way here.

"Are you OK Tony?" Cindy asks, sounding concerned.

"Yeah, I guess. Just a lot to get my head around, that's all," I say.

Cindy phone rings and she answers.

"Yes dear, we just got here," she says, then pauses, I assume while the person on the other end speaks. "OK, we'll be right up. Room 324, got it."

Then she hangs up.

"That was Pippa. She's waiting for us. She sounds nervous too," Cindy says.

"Who's paying for the room?" I ask.

"I am. Pippa couldn't risk her husband seeing it on his credit card," she says.

"What's the deal with him?" I ask.

"Pippa doesn't have a great life, despite the wealth. Money isn't everything," Cindy says.

"She could leave," I say, not feeling overly sympathetic.

"And go where? She has no money of her own. She's trapped Tony. Having a baby of her own would mean more to her than you could imagine," she says, and I immediately feel bad. "Life isn't always black or white."

As we walk into the hotel lobby and towards the elevator, Cindy takes my hand in hers. It's a nice feeling, holding her hand. Cindy turns heads everywhere she goes, so it's a nice feeling when I see a couple of guys sneak a peak at her ass and then enviously look at the young guy she's with.

It's almost like I'm being pimped out. Maybe I am, in some sense. The thought is a fucking big turn on, even if it is just my imagination.

Pippa opens the door almost as soon as Cindy gives two soft knocks. She's wearing a flimsy light blue summer dress, with white dots all over. It comes down to a couple of inches above her knees, nicely showing off her lightly tanned legs. She's beautiful.

Any doubts I had on the way over disappear as my cock takes over and begins to stiffen already.

"Hi," Pippa says quietly as she steps to the side to allow us into the room. "Thanks for doing this," she says, getting to the point.

"Sure, don't mention it," I say, and I can't help but feel a bit intimidated in her presence. She's so far out of my league, out of almost everyone's league, it's crazy.

A few minutes of small talk later, mainly between Cindy and Pippa, Cindy decides to move things along.

"So, shall we get started then?" she says.

Pippa and I look at each other, nervousness now showing through her normally confident front only seriously hot people can exude.

"Em, I, yes, I guess so," she stutters.

"OK then. So, you get yourself ready on the bed Pip. Tony and I will give you some privacy. Come on Tony, we'll go into the bathroom," Cindy says, taking charge.

As we walk towards the hotel room bathroom, I glance over my shoulder and see Pippa reach both hands up under her dress and pull down her panties. They're white, high cut style that I would imagine she looks very well in.

Cindy closes the bathroom door behind us and I turn to look at her.

"Are you OK sweetie?" she says, "I know this is all a bit surreal."

"I'm nervous," I say honestly. " What if I can't do it."

"You'll be fine baby. I'm here to help you, remember," she says. "I've told Pippa how big you are, so she'll be ready for you. She's probably lubing herself up as we speak."

"I mean, what if I can't cum. I know I'm supposed to just put it in when I'm ready to, you know, ejaculate. But what if it doesn't happen straight away?" I say.

"You're over thinking it honey. If that happens and you need help, just pull it back out and I'll know what to do," says Cindy. "But so what if you need to use Pippa to finish yourself off. What does she expect. You're doing her a massive favor, remember."

"I like the room," I say, trying to find something different to talk about.

"I know it's so nice. Pity we can't stay behind to make use of it after Pippa leaves," Cindy says. "But you'll be back here tomorrow night again. We're going to try every night for a week and see if that's successful. Pippa is 40, so sometimes it can take a few attempts at that age. Then again she might get lucky and it works on the first try. The best thing is to do it as often as possible."

"OK, I'm ready I think," I say, and I start to unbuckle my belt.

Cindy steps in close to me and her warm body has the effect she intends. She slips her hand down into my boxers easily now that I've opened my pants, and her fingers wrap around my inflating shaft.

"Hmmm, there's my big boy," she whispers into my ear as she gently squeezes and gives me a few slow pumps.

I kick off my shoes, socks and pants, and Cindy helps me get my boxers off. Before I know it, I'm standing in front of the huge hotel bathroom mirror looking at this sexy mature woman hold me by my cock. I'm just wearing my t-shirt. In the reflection, my cock looks obscenely big in comparison to her hand.

I reach my hand around and cup her perfect ass cheek in my hand. She's wearing a pair of black yoga pants, so that's enough to give anyone a boner.

"That's it baby, you do what you need to do," she says, and then grinds her mound up against my thigh as she speeds up her strokes and I grope her ass some more.

I press my finger into her ass crack, pushing into where her little hole is.

"Oh you naughty boy," she says. I haven't had her ass yet, but she knows I want it.

She spreads her legs a little more for me and opens up her ass nicely, as I'm still feeling her tight little hole through her pants. I love the feel of the yoga pants material in my hands. I give her a few hard squeezes and slaps. I could play with her round ass all day.

After a while I feel her pull her mound off my leg as she gets down on her knees. Then she opens her mouth wide and engulfs my big tip, meeting it with her soft wet tongue. She immediately goes to work on me, and is slobbering on my meat as it's half way down her throat less than a minute later.

Cindy knows how to give head. Some girls in college would take my tip between their lips and just jerk me off with their hand. A fucking waste of everyone's time. But Cindy makes my legs tremble with her oral skills. She can deep throat me, which is an accomplishment in itself. But it's her overall work and timing, using both hands and mouth, ball play, everything combined, that makes her a special cocksucker.

She's pulling out all the stops right now, and before long I tell her she better slow down or my load will end up in her belly instead of where it's meant to go this evening.

"OK, I think we need to move this into the bedroom," she says, then opens the bathroom door while still on her knees.

"You ready Pippa?" she calls into the room.

"Eh, yes. Ready," I hear a quiet voice answer back.

"After you," Cindy says to me as she gets to her feet while holding my hand for balance.

Stepping into a room with a massive boner on show knowing one of the most beautiful women you've ever seen, who you have a major crush on, is going to be there is a lot harder to do in reality.

Ever since I agreed to this, I played all kinds of scenarios out in my mind. In most of them, I'm the pornstar stud, strutting into the room to Pippa. But now the moment of truth is here, it's a very different experience.

The first thing to hit me is an overwhelming feeling of inadequacy. What will Pippa think when she sees me like this?

Then, the worst thing possible happens. I start to lose my erection. I haven't even rounded the corner to where the bed is and I'm starting to droop. Fuck.

That's when I look up and see Pippa. I notice she has taken off her pumps and is sitting on the bed, leaning back on her elbows with her bare feet planted on the edge of the mattress.

She is a breathtaking sight, but it has the opposite effect on my cock than it should. Then when I catch Pippa looking down at my shrinking manhood and rolling her eyes, I wilt even more.

Cindy steps up beside me and sees the situation. She takes my cock in her hand and rubs her thumb over my piss hole, massaging my tip with the precum that she had flowing from me in the bathroom.

Leading me by the cock, Cindy guides me over to the end of the hotel bed, directly to where Pippa's feet are. Without wasting a second, she drops down to her knees again, between me and the bed, leaving me standing looking down on Pippa who has kept her legs spread with the front of her dress just about covering her pussy. Her perfectly smooth legs are fully exposed to me, and the rise and fall of her chest tells me she was ready for this.

Cindy takes my cock back into her mouth and quickly brings me back to full hardness. To make her position a little more comfortable, she pulls her knees up and slides her two feet forward between my legs, bringing herself to a sitting position on the floor, her back up against the bed.

"I still can't believe you're having an affair with him," Pippa says, obviously to her friend on the ground. "It's so strange seeing you like this."

Cindy has her mouth full and she doesn't bother answering. Instead she bottoms out on my pubic bone, her chin brushing off my balls. She holds me in her throat for longer than I was expecting, then draws her head back off my shaft completely and uses her hand to keep the pleasure going. She repeats this process again, and when she pulls her head back this time, I look at Pippa's face and see her eyes go wide when she sees my throbbing cock, which looks like it's about to burst.

Between the exquisite blowjob from Cindy, and looking over every inch of Pippa's body, I feel my climax beginning to approach. Cindy feels it too.

"Are you ready baby?" Cindy says, looking up at me.

"Yeah, I'm nearly there," I say, my heart pounding out of my chest.

When I say that, Pippa pulls her dress back with her fingers, exposing her most private area to me for the first time, indicating she's ready for me. My eyes lock on to her pussy, and I'm mesmerized by the sight. She is immaculately hairless, and I can honestly say it's the most perfect looking pussy I've ever seen. Which is exactly what I was expecting, I mean, everything else about her is perfect.

She looks ready, her slit is glistening with either lube or her own juices, probably lube. Cindy is still jerking me off, and when I feel my climax approach, I step forward towards the bed. Cindy lets go of my cock but stays sitting on the ground between my feet as I step over her with my legs apart.

In the spur of the moment, I place my left hand on the outside of Pippa's upper right thigh, then slide it up to her bent hip. Feeling her bare smooth skin is even better than I hoped. I then take my cock in my right hand and aim it at her entrance. I look up into her eyes and she's staring back at me. She nods once, telling me that she doesn't mind my hand on her hip, but mainly that she wants me to go ahead with this.

I push forward until I feel my tip against her outer folds. Even that minimal contact is enough to bring me right to the edge, and I find myself holding off my orgasm, I can't cum yet.

She feels wet, but I wonder if she'll be able to take my size. When I push my cockhead inside, I see how tight she really is.

She grimaces and stifles a whimper, then looks into my eyes and nods again. God she's beautiful. My fat cock widens even more when it hits me that I'm inside my fantasy woman. I push forward and manage to get two or three inches into her. She bites her bottom lip now, and her hands instinctively go to my waist.

That's when I know it's now or never to give Pippa the best chance of this working. Her well lubed but indescribably tight fuck hole is too much for me. I climb up onto the bed, first my left knee and then the right, my feet dangling off the end of the mattress where I left Cindy sitting on the floor. Now that I'm bearing down over Pippa, she looks a lot more vulnerable as I'm about to mount her. Placing my right hand on the bed close to her shoulder and dark brown hair, and keeping my left on her hip holding her in position, I drive my full length into her hard.

"FFFUUCK," she roars when I give her this first properly hard thrust. She's struggling to take my size, it's too much for her. She wasn't ready and didn't have time to adjust, but she wanted it this way according to Cindy. Enter her as I'm about to cum, that was the instruction. That might have worked with a needle dick, but not my girth.

Just as my balls hit against her ass and I bottom out, I feel the first rope of thick creamy cum shoot up my shaft and out of my cock deep into her cunt.

I can't hold back a deep groan as my climax ripples through my entire body. I pull my cock out about halfway, and then slam it back into this stunning woman again, shooting another splash, just as thick as the first.

I pull out again, and quickly thrust back in as hard as I can, burying her into the bed. She's doesn't seem in as much pain this time I notice, and I can hear a small grunt escape her mouth beside my ear. Rope after rope of my seed erupts from my cock as I try my best to make Pippa pregnant. I'm really fucking her now, rutting on top of her and shooting a massive load as I do. I feel her warm breath exhale in bursts against the side of my face as she grunts quietly as she takes every thrust.

I have an urge to kiss her, to push my tongue into her inviting mouth. But I stop myself, remembering the purpose of this copulation. I'm here solely to do a job, and kissing her would most certainly be an unwelcome advance.

Finally my orgasm subsides, and I can't help but let my weight down on top of her while I catch my breath. I notice she's breathing hard too, having taken a short but hard pounding. Her hands are still holding on to my waist.

After around a minute, I feel I should pull out and get off her. I really don't want to, I could fuck this amazing woman all night. But I force myself to dismount, and Cindy sees me making a move to do this.

"Keep your legs up when he takes it out, and push this pillow under your ass. Gravity helps," she says to Pippa. Some pregnancy advice I assume.

As I sit back onto my heels, my cock slides out and is immediately followed by a load of cum. Pippa tries to stop it flowing out with her hand.

I stand up and look down at Pippa for a second. She looks so hot, I can't believe I just had my cock in someone so perfect. I think to myself that I don't want to look like a weirdo staring at her, so I walk back to the bathroom to get my boxers and pants.

When I'm fully dressed I go back into the bedroom. Pippa is still lying on her back and is talking to Cindy, who is sitting in the armchair beside the bed. I try not to look at Pippa, focusing on Cindy instead. Cindy stands up and grabs her handbag, she's realized that I might be feeling a little awkward now.

"OK, that went well, didn't it," she says to Pippa, and then looks at me too.

"Yes," Pippa answers. Then as I turn to walk towards the door she says, "Thank you, Tony."

I don't think she's ever said my name before. I wasn't sure she even knew my name.

"You're welcome," I say, embarrassed. It feels like high school when the hottest girl in the school talks to you.

"See you tomorrow," she says then, as I open the door with Cindy walking behind me.

Cindy and I don't speak until we're in the elevator. We both know the magnitude of what's just happened.

"You did great," she says, and takes my hand in hers again. "I'm proud of you."

I smile to myself as we step out of the elevator and walk hand in hand through the lobby and outside to her car. Have I just impregnated Pippa? I don't know, but I sure enjoyed trying.​