Niece's Wedding Pt. 01

I take a deep breath and think I could yell out to get her attention. Nah! I type out. "I expect to see this posted when I wake up in the morning. I will be in touch about tomorrow night." I hit send, logout and go to bed.

I am sitting at my desk the next morning and I check RNAsh. Sure enough there is a 15 second clip of the dildo in her ass. "Buy the entire unedited 5+ minute video of me fucking my ass and fingering my pussy." Is captioned under it. No thanks I think with a laugh. I will have the real thing in a little more than 13 hours from now.

I reach out to the woman at work that does our business travel. I sell her a story of a friend that needs a room overnight. His dog got sprayed by a skunk, and the house stinks after the dog ran in the house. He is financially tight right now, and won't let me help out. Maybe if there was a room booked for a client that wasn't being used at the local Hilton. Maybe I could talk him into not letting it go to waste.

I hear her tone soften. "You know I was just thinking what a shame it is, that it's too late to cancel a room that was booked for a client that didn't show. I will send you the room number and access info for the app to access the room."

After I get the information I text Ashley.

ME - Hilton hotel 9pm

ASHLEY - What room?

ME - Text me when you get there for the room number and more instructions.

I hit send and put the phone in my pocket. During the day my Ring camera app goes off. I look and my lawn guys are there.

My Ring camera...hhmmm. I think of the box under the bed full of stuff that's gone unused now since Jen's death. A plan starts to form in my head. I am having trouble thinking about work, and I need to stop at the bank so I leave early.

I go to the bank and get $5,000 cash from my savings account. The teller that has known me for years looks at me funny in the bank. "A friend is in a bind." I say with a smile. She counts it out and hands it over.

I head home to get a few things out of the toy box as Jen used to call it. I pull out the long plastic box from under the bed. It's covered in dust. I open it carefully and put the dusty cover to the side. I see years of stuff we collected. Her favorite purple vibrator. I see it and I can see her in my head, propped up against the headboard fucking herself and teasing me. The bondage stuff. I can hear her complaining as I pull the straps too tight stretching her out.

I realize I am smiling and the memories and not getting emotional. Then I realize there is a big part of me looking forward to getting laid tonight. Maybe I am ready to move on. I pull some stuff out. The bed straps and restraints, fur lined handcuffs. The hitachi wand and power cord to charge it. Then I see a favorite of mine. The shocker. A small skinny wand that delivers a small shock. Fun to apply to a woman's nipples and clit. Oh the open mouth clamp I got as a joke when my wife accidentally scratched me with her teeth. Ashley is definitely getting that, and finally a real bondage blindfold/mask. The inside has a thick fake lambswool padding that keeps someone from peeking. You can't see a thing once it's on. On the way out of the house I get the battery powered Ring cam down from inside my door.

I stop at an adult store in the next town and get a large butt plug, and lube.

I have the room set. The straps are under the mattress, Ring camera facing the bed with the burner phone as a hotspot in the dresser drawer. On the bed is the bondage mask, butt plug, lube and handcuffs. With a note. "Strip, put everything on with your hands behind your back and lay across the bed. When I see with the camera, (and I draw an arrow pointing to the Ring cam) you are ready I will come join you. I then head down to the bar. I sit around the corner of the bar out of sight from the door, but in the right spot so I can watch it.

I play with a translator app I found. You can type in something and it will say it in any language, even English to English. I start typing in some saved phrases. Get on your knees. Open your mouth. Do you like that? Spread your legs. I am going to fuck your ass. I am laughing to myself. The longer I play with it the funnier it gets. I can't wait to hear Siri saying these phrases.

The bartender has just cleared the plate from my burger and brought me another beer when the burner phone dings. Let the games begin.

ASHLEY - I am here

ME - Room 765, leave everything including your purse and phone in the car. Carry only your car keys.

I see her walk in the lobby and look around for the elevators, and finally head for them. I count the floors in my head after I see the doors close. I then give her a 20 count. I use my phone and with the hotel app open the door. Just seconds later my Ring App dings. I open it and watch Ashley walk in. She walks in and stops to stare at the stuff on the bed. She picks up the note and then looks at the camera. That's right Ashley I am watching. I think to myself. I can see her take a deep breath. She kicks off her shoes, and proceeds to strip. She lays on the bed with her naked back to the camera, and her knees pulled up towards her chest. She has obviously had her ass fucked before. She probably thinks it's a bad angle, but it gives a great outline shot of her fingers lubing her ass. Followed by her trying to push the big plug in her ass. It takes her a good minute plus, of nudging in and out, a little deeper each time. I am disappointed the camera has no sound. That's ok I will hear her moans soon enough. She looks at the camera one last time, and puts on the mask. She has trouble cuffing her own hands behind her back, but gets it done. She lays down on the bed with her head turned away from the camera.

Let her lay there and think about what's about to happen. I take a few minutes to finish my beer and drop some cash on the bar, and head for the elevators. I click the door lock with the app, and walk in.

"Hello? Who is there?" Ashley asks nervously. "AO is that you?"

I open the translator app. "Were you expecting someone else?" Asks Siri. I almost laugh at it.

"N-no." Stutters Ashley.

All of a sudden I want her to say why she is here. I start recording a video and walk around the bed. I stand back at her feet. "Roll over on your back." Says Siri. I get a good look at her naked body. Yes she is overweight, but that gives her nice big tits with nice thick dark nipples that will be fun to chew on. Like the Christmas song says her belly will jiggle like a bowl full of jelly as I fuck her. "Spread your legs." Says Siri. Ashley doesn't move. I reach down and hold her ankle as I pull it out. She flinches at the touch, but then spreads her legs. There is her pussy. She is shaved nice and smooth, but she is dry as a bone. That's ok, that's why there is lube. It takes a moment to type in. "Tell me in detail why you are here, what you promised to do and why." Says Siri.

"I promised to have sex with you for $5,000." Says Ashley.

"The whole truth. The reason why." Says Siri.

Ashley sighs. "Fine you recognized me on my online porn site, and threatened to expose me to my friends and family if it didn't."

"Last chance Ashley. Tell the whole truth, including why, and tonight can be fun. Don't tell the whole truth and I can just use you for three hours straight." Says Siri.

"Fine. You think we are being unreasonable expecting our parents, as you said, to pay for our extravagant wedding. You promised me $5,000 to pay for some extras we want. If I fuck you, you won't expose me."

"Close enough. Did you like to dildo I bought you?" Asks Siri.

"God, it was big. At first I didn't think I could take it, but god it stretched me so good." Says Ashley.

"You have behaved so far tonight so I will give you a choice. I can fuck your ass first. It will probably be a bit harder, but quicker. Or I can fuck it last. If I fuck it last it will definitely be a longer fuck. Your choice?" Says Siri.

"Oh..um, I am scared. Are you really as big as the dildo?" Ashley asks.

"Yes. That's why you have the plug to stretch you out." Says Siri.

"Oh God! In my ass? Promise me you will go easy. PLEASE!" Begs Ashley.

"At first." Says Siri.

"Oh shit." Ashley mutters. "First I guess."

"Roll over." Says Siri, and I put the phone on the bed. I start taking off my clothes. Part of me wants to climb over her and put my dick in her hand so she can feel the size, but I decide just letting her ass feel it first is the way to go. I pick up the phone and focus on me pulling out the butt plug.

Ashley moans loudly with every pull. Her ass has a tight grip on it. I grab the back of her head and turn her face down on the bed. "Ssshhhh." I say. I take a moment and type out. "If anyone knocks because you are too loud, you will either end up fucking them to make them go away, or I will send the emails and you won't get paid. Do you understand?" Says Siri.

"Yes." Says Ashley.

I continue pulling and on the third pull her ass lets it go. Her ass is wide open. I squirt some more lube in her open ass and rub some on my dick so it's nice and slippery. I aim my dick down and push it in. Half the head fits in her open ass and it stops. I just push harder. "Shit, shit, shit, shit." Ashley gasps as I keep a steady pressure up as I push in. Her ass finally lets me in, and Ashley lets out a small scream into the bed. Slowly but surely I push in until I bottom out. "PLEASE!" She half cries out.

"Ssshhh. It's ok. I will stay right here for a moment while you stretch out." I say to here as I record her asshole stretched around my thick dick. I see her head turn. She is trying to place my voice, but I don't think she is getting it. I stay in her ass for a bit. It is so fucking tight. I have to fuck her. I pull back just and inch or two and push back slowly.

"Ooohhhh. Ooohhhh." She half cries half gasps as I just give her slow half strokes.

"Fuck." I groan as her ass grips me like a vice. Just to be safe I pull out and pour more lube in her. You can see the lube dripping in her open ass on the video. I push back in with a wet farting sound.

"Ooohhhhh. Oooohhh." She continues to gasp and cry out as I slowly fuck in and out of her ass. Little farts escaping now and again. After a few minutes of fucking she quiets down some. Still moaning and grunting, but no pleading or crying.

I can't believe how tight she is. Her ass is a fucking vice. I look down and there is a very pale ring around my dick, her ass she is squeezing me so hard. Fuck I want to cum. "Home stretch. Here comes the hard and fast." I say as I prop the camera against a pillow, aiming it as best I can. I grab her hips and fuck her harder and faster.

She yelps out and instantly starts begging and half crying. "Oh God. Oooohhhhh. PLEASE. GOD. OOOOHHHHH. PLEASE CUM. SHIT. SHIT. SHIT. PLEASE." She gasps into the bedspread. Her hands are straining and flexing in the handcuffs. "PLEASE. OH GOD. MY ASS. PLEASE I AM BEGGING!" She cries as I slam home one last time. I stay deep in her ass and I cum with a moan. I stay there for a moment catching my breath. "Please take it out. Please." I pull out and flop on the bed. She rolls over trying to use her handcuffed hands to hold her ass.

"Wow! I never imagined an ass would be so tight. Jesus, that was amazing." I say.

Ashley moans. "It wasn't amazing for me."

"Well it was for me." I say.

I can see Ashley's face turn towards me. She still can't place my voice. "Can I go to the ladies room?" She asks wiggling her handcuffed hands.

"Of course. Right after me." I get up and head to the bathroom. I piss and then use a warm cloth to wipe off the extra lube. I walk out and get the handcuff key off the nightstand and unlock one wrist. I leave them dangling off one wrist as a reminder. I get up and help her up.

"Can I take off the mask?" She asks.

"Once you are inside the bathroom, and then put it back on before coming out. If you didn't like the ass fucking I gave you, you really won't like the pounding I will give your ass if you try to take a peek before I tell you too." I warn her as I take her arm and walk her to the bathroom door.

"I understand." Is Ashley's only answer. A few minutes later she comes out. Feeling her way along the wall. I walk over to her and take her arm. She flinches at the unexpected contact.

I lead her to the bed. "Lay back against the pillows and get comfortable. I have a reward for you. You took the ass fucking like a champ, so you get a reward." I say. I reach into my duffle for the hitachi wand, and I pull the belt out of my pants. I pull her legs together and wedge the wand between them against her pussy.

"What is that?." Ashley asks as I tighten my belt around her thighs trapping the wand in place. I reach in and hit the medium button, turning it on. "Oh god a wand." She moans.

I smile. "So you have used one before?" I ask.

"Emily has used one with me before." Says Ashley with a sigh. I watch as her hips shiver a bit.

"I want you to feel good. After a few good orgasms I will stop it." I say as I sit back on the couch and watch.

Within a few minutes her first orgasm hits. "Ohhh. Ohhh. Oooohhhhhh." She gasps. I stand up and look and you can see the actual wetness on the toy and between her thighs. I sit back down quietly. Barely two minutes later. "OOOHHH. OOOOHHHH AAARRGGGHHHH!" She moans loudly.

"Sounds like that was a good one." I say.

Her whole body spasms. "Please too much. It almost hurts." She moans.

I take my time and talk slowly to drag it out. "Ok so you get to pick how much longer." I say and Ashley moans loudly.

"PLEASE!" She begs.

"Well if you wouldn't interrupt me. Now where was I? Oh yeah. Remember you are on medium now. So 3 more minutes on low, 2 on medium or 1 minute on..."

"SSSHHHIITTT!" Ashley moans loud enough to be heard in the hall. I put my hand over her mouth.

"Choose or stay like this for 5 more minutes." I growl in her ear.

I lift my hand from her mouth. "1 minute!" She gasps.

I reach between her thighs. "You are soaked!" I say as I feel for the top button and press it. You can hear the faster and stronger vibrations. Her whole body spasms and she groans so loud I slap my hand back down on her mouth. I am watching the seconds tick by on my watch. At 49 seconds she screams into my hand and I swear she convulses on the bed. I reach down and pull the toy out. It is dripping wet. I release the belt and she rolls over away from me shivering.

She lays there for a bit as her breathing slowly returns to normal. "Is there any water?" She asks softly.

I threw a bunch in my duffle bag before I left the house. I grab one, open the cap, and hand it to her. She drinks half of it in one go, and just holds it. "That was so sexy to watch." I tell her.

"What torturing me?" She asks.

"Torture is painful. That looked a lot like pleasure to me." I say.

"Until the end." She sighs. "Then it felt so good it hurt."

"See, it felt good." I say.

I let her relax for a moment when I start thinking about her blowing me. I stand up and toss a pillow from the couch on the floor by the bed. I reach over and playfully slap her ass. "Stand up." I say as she yelps. I reach into my duffle and pull out the mouth gag. I stand in front of her and stroke her hair back. "You have a very pretty face. I think you are going to look sexy with a dick in your mouth." I say.

"I haven't done that in a really long time, and you are so big." Ashley says, sounding a little nervous.

"Don't worry. It's like riding a bike." I say. "Let me see you open your mouth nice and wide. Let's see how wide you can open your mouth." She does, and to be honest. She can open her mouth wide, but I really enjoyed this thing the one time Jen let me use it. "One more time. Lets stretch your jaw a little. Let's give it a little warm up." Ashley opens her mouth, and I push the brace in her mouth, and squeeze the tabs. It ratchets open three clicks forcing her jaw open as the rubber coated metal hooks trap around her teeth so she can't spit it out. Her hands reach up to pull at it. I grab them and spin her around handcuffing her hands behind her back again.

"Ugh ugh. Glugh glahhh." Ashley tries to say.

"This will keep you from scraping me with your teeth. It's just a safety device." I say as I reach out and click her open one more click. She just moans. I pull her arm down. "Now get on your knees." She just moans in defeat and lets me guide her down. I take my dick and push it in her mouth. I don't have my head plus maybe an inch in her mouth, and she is gagging hard. She isn't using her tongue at all to be honest. I think it's the worst blow job I have ever had. I keep pushing my dick in and out just a little. It's still a bad blow job.

Screw it. I will fuck her doggie and cum in her mouth. I pull out of her mouth, walk behind her and push her forward, so her head & shoulders are on the ground. "Ok, not the best blow job." I say as I kneel behind her. "I will just fuck you, and pull out so I can come in your mouth."

"Uhn Aahhh. Ugghhh assss!" She says.

"You want me to fuck you nice and hard? Ok." I say as I rub the head of my dick up and down her very wet pussy lips.

"Ooooooo." She moans trying to say no to the hard fucking.

I laugh. "Don't worry, I won't be hard." I say as I push into her pussy. "Fuck." I groan. "At least it won't be hard at first."

I start a nice steady fucking. She feels so hot, wet and tight. She was nice and wet from the wand so it helped me push right in. She just continues to moan out "oooo. Oooo oooo." As I fuck into her. I am not killing her, but I am not going easy. After a little bit of fucking, and me thinking I am getting close a funny thing happens. Ashley orgasms. "Ooooo. Uuuuuuu. Ooooo." Her her pussy grips me tighter, as the lesbian comes from a guy fucking her. I am so close. I pull her up by her arms and put her back against the bed. I stand over her. She looks sexy. You can see the drool just dripping from her mouth. I hold my dick by her face and jerk off. At the last minute I flip the mask off her face. There is enough time for me to see her blink with the light, and then I see the recognition in her eyes as I cum on her nose. She shuts her eyes tight. Her eyes aren't my target. I put the tip of my dick in her mouth and finish cumming with two more spurts. She lets out a disgusted. "Uuwwwww." I don't think she likes cum.

I hold her head against the bed and look in her open mouth. It's a decent amount. I would have given her a lot more when I was her age. I wipe the cum off her nose and lip into her open mouth. I click the release tab, the gag collapses and her mouth closes. I pull out the gag and hold my hand over her mouth. "Swallow!" I say. For the first time Ashley can look me in the eye. She swallows and makes a face. "Get used to it. It's not the last cum you will be swallowing tonight." I say as I step back.

"Uncle, why?" Ashley pleads.

"I told you because you and your selfish fiancé have my best friend tied up in knots. You two are trying to have this extravagant dream wedding while your parents go into debt. It ends tonight." I say.

"But Uncle." She whines as she slowly gets up with her handcuffs on. "You could have talked to us." She says.

I lurch at her and push her face down on the bed. "I was there..Spank. When Jim tried to talk to you two...Spank. There is no talking to her... SPANK. She flips out and melts down...SPANK. She made her Mother cry..SPANK." I say spanking her harder and harder.

"I am Sorry!" Ashley cries out.

I sigh, as I grab the key for the cuffs, and I uncuff one wrist. I drop the key on the bed for her to get her second wrist. I sink back onto the couch. Ashley gets up and heads to the bathroom. She comes back with her panties on and is putting on her bra. "What the Fuck are you doing?" I ask.