Niece's Wedding

So I am a 50 year old widowed guy. I am not going to say I don't want to get remarried, or that she was my one true love. We did love each other, and I am just not ready. My wife passed away a few years back from cancer. Before she passed we had a very active and varied sex life. The old saying, "I will try anything once, twice if it doesn't hurt." Was us to a tee.

I will admit though the last few years have been lonely. My buddy Jim and I have been friends since we were kids. When his daughter Emily was born she started just calling me Uncle and it stuck. So now to his kids I am just Uncle. I will admit he has been great in keeping me from becoming a hermit after Jen died. "I don't care if you want to or not. Get your ass over here, or do X." He would bark at me. It was a bit of tough love that I needed.

Jen and I never could have kids. We both had, well I still have a good job. So we were, I am well off. Now add to that a very healthy life insurance policy. I don't think I will have money concerns ever again. I have always lived modestly and honestly there is no way I would spend my salary, never mind the life insurance and savings.

Jim works hard, makes a decent buck, but five kids, private schools his wife insisted on, etc was a burden. Savings or spare money is something Jim doesn't have much of.

His daughter Emily has always been very in your face. She never had any serious boyfriends I was aware of and then one day she is seriously dating a girl. More power to you. They are engaged to be married and I know the girls want a lavish wedding. They don't want to accept the reality of wants vs what Jim can afford. One day I friended Emily's fiancé Ashley on Facebook. She has a comment and link about sex workers are workers too, or something like that. I follow the link and fall into a rabbit hole. At the bottom of the hole I find Ashley's online porn site page. Holy Shit she does online porn, and doesn't hide her face.

Oh shit. Ok, um wait a minute. Create a new random email, sign up for the online porn site, and follow RNAsh. Her bio says she is a naughty nurse, bi, very sexual and kinky. She is engaged to marry the love of her life.....a girl. I spend the entire night looking and buying a few videos. Ashley fucking herself with a dildo in an exam room in work. Emily spanking her and leaving red hand prints. You never see Emily's face and she never speaks, but I recognize her freckled hand in the spanking video. I watch and look at all her stuff for the last two years.

I give thumbs up to a few kinkier ones. Emily fucking Ashly with a strapless strap on. Both Emily and Ashley are thick girls. Both have medium bellies that jiggle and their tits bounce. Both of them have nice thick dark nipples. In fact there is a short video of Ashley almost nursing on Emily's nipples she is sucking on them so hard. You can hear Emily moan a little.

Ashley even posts, buy X and help me pay for my wedding. She has an Amazon account linked for sex toys you can buy her and she will do a five minute video using it for you. I decide to send Ashley a quick Private Message. "Your toys are too small. They need to be more life-like." To be honest they are average in size, but I am not. I am very thick, not super long at about 7 inches, but I will stretch a woman.

About 15 minutes later I get an answer. "Every guy thinks he is huge."

I look on Amazon for a thick dildo. I reply "I will buy this so I can watch you fuck yourself with it and imagine it's me."

A few minutes later. "Prove it, and I will." RNAsh says.

What the fuck. I find an old cloth tape measure my wife used when sewing. I send back. "I need to watch your videos for inspiration. Five minutes." I jerk off watching Emily fuck her with the strapon. I am holding my iPad as I watch the video and decide I will cum on the screen and use it as the background for the picture. I need just a few minutes and I am coating Ashley's face on my iPad in cum. Thank god for windex. I put the measuring tape around my dick just under the head, lay my dick on the ipad, and snap a picture of my dick with the paused video. Ashley's look is wide eyed and mouth open as she is getting fucked. The screen is splattered in cum and my dick is to the side on the tape measure showing just under 6 inches with it just under the flared tip. So my head is a tick thicker.

A few minutes later. "Oh wow. Never actually seen one that big in real life." She says.

I tend to believe her but I play the part. "Before I order it I have one demand then." I say.

"You do!" She says.

"Yup. If you truly haven't had a dick this big. I want to see you naked on your bed when you open the box for the first time. I want an unedited video. Open the Amazon package, open dildo, and play with it. I love the look on a woman's face when I first push into her pussy. No cheating and practicing. In fact make it a ten minutes of you fucking yourself to orgasm, and I will double the tip after I receive it."

Less than two minutes later. "Deal. It's added to my list."

I refresh her Amazon and there it is. I buy it and send her the original tip for the video.

Before I can reply. "I can't wait for it to arrive." She texts and a moment later she is offline.

A few days later I am over Jim's when Emily & Ashley stop by. Fuck I can't look at them the same way anymore. The next day when I log on I have received a video on the online porn site, and a note. "Oh my god AO, (user name is AO8546 totally random) it was amazing. I hope you like the video. RNAsh"

I click play. First thing I notice is the address label showing clearly on the box. She opens the box and pulls out the dildo and is looking at it with a little awe. "Wow this looks big." She mutters as she cuts the hard plastic packaging. She has it out and is holding it in her hand. It's a realistic dildo with a flared head and veins. She turns it and looks at it. "No time like the present." Ashley says as she grabs a bottle of lube. She dribbles some on her pussy and uses her fingers to rub it in, and then slip her fingers around inside her pussy. She pulls out her fingers. And coats the dildo in lube. She looks up at the camera. "This bad boy would rip me in two without lube." I notice Ashley look past the camera and smile. Emily must be behind the camera watching.

Ashley lays back propped up against a bunch of pillows and spreads her legs. She positions the dildo between her pussy lips and looks up at the camera as she nudges it in. There is the look I have seen in the past. The wide eyed Holy Shit, look. "Fuck, this is thick." She moans as she holds it in place for a moment. She gives herself a moment to stretch and pushes it in deeper. She moans out. "Ffffuuucckkk!" In a mix of pleasure and pain if you will. Within a minute or two she has a slow in and out stroke going. I catch the audio go quiet for a second and again Ashley looks beyond the camera and smiles as she fucks herself faster. The audio picks back up to hear her moan. If it weren't for the audio program I run on my laptop for work training videos I create I probably wouldn't have noticed.

I go back and play with the levels, and I can just make out Emily's voice. "Faster, Bitch!" Hhhmm. Looks like they have a bit of a Dom/Sub relationship. To be honest with Emily's personality it's not surprising, but good to know. I notice Ashley has created a dark wet spot on the sheets, and is fucking herself with a pretty good pace. When her eyes go wide and she gasps as she holds the dildo deep in her pussy and orgasms. She shivers a tick, and lets go of the dildo. I watch as her pussy pushes it out, and her body slumps into the bed. Again I see the audio levels dip, and the camera zooms in a bit, and then a hand comes into the shot, picks up the dildo and pushes it back in Ashley's pussy. The audio picks back up to hear Ashley moan. "No, please."

I have to go back. Again I Jack up the levels. "That's not 10 minutes, Bitch." Says Emily. I let it roll and watch Emily fuck Ashley hard and fast with the dildo. Ashley's face is one I have seen before. This is So Big, but I don't want it to stop look. Her head rolls to the side. She is pulling on her nipples hard, and loudly grunting and Emily is fucking her when all of a sudden the video stops. Across the screen scrolls, "... that's 10 minutes!"

FUCK!

I go back to the video and start pulling clips with the audio jacked up with Emily's voice. I then go back and screenshot the address label on the box and enlarge it. It's blurry, but knowing their address it's easy to make out. I spend the next two hours reviewing everything again. Exam room video shows a certificate of some sort from a local school with Ashley's name. A picture she took in a work bathroom shows a paper towel dispenser with a local company logo with the city and state visible. Another picture of Ashley flashing outside of work shows a highway sign visible behind her through the woods separating the hospital from the highway. With the exit name visible. Another picture in front of a picture window shows the city in the distance. You can see two very distinctive buildings so you know which city, and that she is south of the city by about 10 miles. I then start looking at the pictures and videos with Emily in them and start looking for clues. Her hand, her rings, unique watch band and her freckles. I pull up her social media and pull a few photos showing her hands, rings and watch.

She wants to bust my chops? I will bust hers. I start to form a plan. Rather than use my phone email, I download the email app and log the app into the new AO email. I find Ashley's email on Facebook, and the next day when I know she is at work. I email her three screenshots, one after another. Her FB page with the sex workers link, the girls page with a link to RNAsh, and finally Ashley's smiling face on the online porn site. Under her smiling face I write. "Cutting it off exactly at 10 minutes wasn't very nice. It looked like you were close to another orgasm." And I wait.

About 20 minutes later I get an email. "Who is this?"

I reply with more screenshots with each clue circled. Her outside with the highway sign, the bathroom, exam room and a screenshot of a PIN drop on her workplace. "Tell anyone, including Emily that I found you or sent these, and I send your work, friends, family and the hundreds of followers you and Emily have on social media ALL the screenshots I have and your online porn site account info."

I get a quick reply. "No please don't. I can send you the complete video later. Please don't tell anyone."

"Oh it's going to cost you more than the entire video now. I will be in touch." I reply and log off. Now I need to let her sweat.

Email is a little slow. I need to get a prepaid phone. So I can text her. I head out at lunch to a local convenience store and buy a smartphone. For less than $100 I have the phone and prepaid service.

I go back and look at a group text Jim's wife sent out a month or so ago about a family cookout she included me in. I don't have three of the numbers in the chat so there are no names. I go through and read the chats and find Ashley's number when I see, "Emily & I will bring... From my burner I send her a text.

ME - Send me a picture in 30 minutes of you recreating the bathroom screenshot. Use your left hand to put two fingers nice and deep in your pussy.

Ashley - Who is this? How did you get this number?

ME - I know you and Emily, but I am going to get to know you a whole lot better I think. Oh yeah, 25 minutes left.

Ashley - Please don't do this.

I let it sit unanswered and after a few minutes I text.

ME - 19 minutes.

About 10 minutes later I get a picture of her in a bathroom stall on a toilet. Two fingers deep in her pussy and her engagement ring in sight.

ME - I said recreate it. I don't see the mirror or paper towel dispenser. You are in a stall. 8 minutes.

Four minutes later I get the correct picture.

ME - Next time follow my instructions.

I shut off the phone, and decide to let her worry. Later that night I log onto the online porn site and RNAsh has sent me a video. It's the full 13+ minute video. I can clearly hear Emily's voice. "You like that big dildo in your pussy you Slut?" Ashley just groans. "What, you want it harder?" Emily starts shoving it into Ashley hard. Ashley just moans and grunts as Emily fucks her. You can clearly hear Ashley's wet pussy making wet squishy sounds. The wet spot on the bed is now bigger. Ashley lets out a loud groan and rolls her hips to the side. She rolls away from Emily pulling herself off the dildo. She rocks back and forth on her side. Emily's hand pulls out of view and I can hear her say. "Imagine putting this thing in your ass." I hear Ashley just moan, and I see Emily's hand reach for the phone to stop the recording.

The entire 13 minute video was sexy as hell, but one thing keeps running through my head. Putting it in Ashley's ass. No woman has ever let me fuck her ass, in fact I stopped asking women before Jen and I married. I have never fucked a woman's ass. I back up the video a few seconds so I am staring at Ashley's ass. I am seeing myself spreading her ass cheeks and pushing my dick in her ass. I am hearing her groan like she did in the video. Before I realize it, my sweatpants are pushed down and I am jerking off.

I hate to admit it, but I am turned on and I cum quickly making a mess of myself. Ah well. I toss my clothes in the hamper and take a quick shower before bed.

The next day I keep replaying a dream I had over and over in my head. Ashley is naked on my bed holding her legs back spread wide, and I am about to push my dick in a woman's ass for the first time. I line up and start to actually push in and I watch Ashley's face. Her eyes can't get any bigger. Her mouth is wide open as she gasp. "Fuck so big!"

God damn that image stays in my head all day. Jim texts me later and tells me his wife is going out with the girls. If I bring two cigars and a bottle of scotch he will cook the steaks. Sounds like a plan.

I stop at a local liquor store that has a humidor. I grab two of my favorite cigars, a bottle of scotch and a 6 pack of beer to have with dinner. The steaks are done, and Jim has lit his fire pit. We sit around it each with a cigar and a healthy glass of scotch.

He is worried about Emily's wedding. Both parents are splitting the costs. He wiped out his savings paying his half, and now Emily is hounding him for $5,000 more for extravagant extras she has to have, and he doesn't have the money for it. He sees no way out except to take out a loan. "I can't let you do that." I say.

He looks at me almost a bit mad. "No way. You aren't paying for her wedding." Jim says.

"Nope, not paying for. An interest free loan with a flexible payment schedule for a friend." I say.

"No, Charlie! I wanted to do some work around here. I will take out a loan for the work, and a little extra." Says Jim. He then reaches out and holds my shoulder for a minute. "But thank you for the offer. I couldn't ask for a better friend."

I put my hand on his. "Says the man that has kept me from falling into a black hole."

He smiles and raises his glass. "To better days ahead." We sit there in silence drinking and smoking for a few minutes. That is until Emily comes charging through the back door.

"Jesus, there you are." Says Emily before the screen door can even close. "I need the suitcase. Where is it?"

I look over my shoulder. "Oh Hi Dad. Hi Uncle. So good to see you. Hey Dad, where is the suitcase? I would like to borrow it." I say laced with sarcasm.

"Yeah, yeah. Sure Uncle. What he said Dad." Say Emily with a sigh.

"I will tell you for a hug and a kiss." Says Jim.

"Really?" She sighs.

"Is it such a horrible thing for a Dad to ask his daughter for a hug and a kiss?" Says Jim still smiling.

"Fine." Says Emily. She gives him the quickest hug I have ever seen and a peck on the cheek. "Happy? I have to get to work." She says.

"Where are you going?" He asks. She sighs again, and explains her boss wants her to go with him to look at a restaurant he is thinking of buying in a resort area a few hours away. She will be gone the next two nights while they look at the area, the restaurant and its books. Jim just points back at the house. "Back corner of the basement." She storms back in the house without a word. "Man, she can be a lot of work sometimes." He mutters and he takes another drink. A few minutes later we hear a door close, a car start up and drive away. I can see the disappointment and pain in Jim's face. "Bye Emily." He says quietly as he takes another drink.

I get home slightly buzzed. Since Emily left I have been seeing Ashley's ass. I am mad at both of them for forcing Jim to take out a loan to pay for the extravagant bullshit. Nope sorry Jim I am helping out in my own purely selfish way. I clip just the video of Ashley on her side and Emily saying. "Imagine this in your ass." And I text it. Then I add.

ME - I don't want to imagine I want to fuck your ass.

ASHLEY - It's never going to be more than a dream. I don't have sex with guys.

ME - First off, never say no to me again. Second, your profile says you are bi. That means you fuck guys, and I know you have in the past. Third, since you like to sell yourself, I will pay you, $1,000.

I know that one hit her hard. I am turning her into a prostitute. I get no answer. Ok, let's turn up the heat. I start an email addressed to HR at her work, her parents and Emily's parents. With a screenshot of Ashley's online porn site front page. I screenshot it and send it to her.

ME - Reply in five minutes or I send it, and a 3 minute PowerPoint I have created to Everyone I can think of to expose you. Do you have any idea how many sexy screenshots are in a 3 minute PowerPoint?

ASHLEY - Why are you doing this?

ME - You two are being unreasonable brats to your parents about this wedding. If you can be unreasonable, so can I.

I get an evil thought. I know they really want that $5,000. More than that I want to save Jim from going into debt, and I realize something else I haven't felt in a while. I want to get laid. I mean I really do. I want to fuck Ashley.

ME - I know you want $5,000 for wedding bullshit. I will pay you $5,000 to fuck you for three hours. Tomorrow night 9-12a. Your mouth, pussy and ass are all open to me. Do it and I will give you the $5,000. You Must use the money for the wedding. If I hear your parents paid the extra $5,000 for the bullshit you want, I expose you. Now be a big girl, tell no one including Emily, fuck me, get paid and this is all over. You have one hour to decide. I will be on the online porn site.

I send it and power off the phone. I open the online porn site on my iPad and grab another drink. About 20 minutes later I get a message from RNAshley. "Fine, you win."

"Naked on your bed and send me a private video chat." I reply. A few minutes later I receive a private chat invite. I have my camera already covered again on my iPad. Ashley pops up on the screen naked. She looks upset, and like she has been crying. Tough! I start right up. "Do you have a butt plug?"

"Please don't do this. Please!" She whines.

Too bad. I am pissed she and Emily have Jim so twisted up. "Answer me!" I type out.

"Yes." She says sniffling.

"Go get it, and some lube." I type out.

She sniffles more and comes back with a smaller plug. "That's no good. Go get a dildo you can fuck and stretch your ass with." She comes back again with a decent sized dildo. "That will do. Fuck your ass with it, in whatever position you want. As long as I get a good view. In fact, record it and post it afterwards."

Ashley doesn't question it. She reaches forward I am assuming to hit the record button, lubes up the toy, lays back and pushes it in her ass with a grunt. It's not the best view with her thicker thighs and ass cheeks, but her pussy is obviously empty. She rolls over onto her hands and knees and continues fucking her ass. I have noticed the grunting has stopped and she is now moaning. She has one hand playing with her pussy with the other fucking her ass. She shifts on the bed and falls over. She takes the opportunity to lay on her side, bent at the waist, and pushes the dildo back in from the back while she reaches around from the front with her free hand and rubs her clit. I have been jerking off and cum into a paper towel to avoid a mess.