Neighborly Blackmailing

Every person on this Earth enjoys sex. Sometimes you just don't have a sexual partner. A lot of us are happy with resorting to simple masturbation, but others need something a little more extreme. I was one that got bored just whacking it off when I didn't have a sexual partner in my life. I was always looking for something more. So a couple of months back I decided to purchase my first sex toy. It was a cyber skin mold of a porn star's vagina. It was pretty high priced, but I had faith it would be worth it. I bought it online and had it shipped to my house. At least I thought it was coming to my house.

I was supposed to receive my package in 7 to 10 business days. As a broke college kid, I couldn't afford the quick and speedy shipping method. After 2 weeks I still didn't have what I ordered. I called the company I bought it from and they assured me that it had been delivered already. I became fairly frustrated because I figured someone had stolen it. I just spent a good 200 bucks on something I won't ever get to enjoy. I was pretty pissed.

The next day I went out to breakfast with some friends. I just got home from college 2 weeks ago and had yet to get a summer job so I had a lot of free time. When I got home I noticed my neighbor Lisa was outside doing some yard work.

Lisa is a 42 year old mother of four. She had lived next door to me for the last 15 years. I used to hang out with her two oldest sons. They both moved away and her two younger sons are still in elementary school.

She noticed me getting out of my vehicle.

"Nathan! Can you come over here a minute please?" She yelled.

I really disliked when people used my full name, but I was eager to help.

"Of course, Lisa. How have you been?" I responded as I started my way over to her.

"Oh I've been okay. Things with the divorce are finally over so that's a relief."

"I'm sorry to hear about you and Paul. I wish things would have worked out for you two." I consoled.

"Well this is for the best you know so I'm just moving on with my life now, but enough about me. I need to talk to you about something."

"What is it Lisa?" I asked

She responded, "Well the other day there was a package on our porch that had your name on it."

My stomach sank.

"Oh yes, I have been expecting that." I responded nervously.

"Well, I kind of got curious and opened it."

My stomach turned and my heart dropped.

"I'm sorry that you found that."

"Don't apologize!" She exclaimed.

"I played around with it a little bit. I hope you don't mind. It's extremely realistic." She said. "How much did you pay for it?"

"Uhmm a little more than 200 dollars." I responded.

I'll admit that I always found Lisa attractive. She is an extremely attractive 42 year old woman. Long dark brown hair with an aging face, but has a fantastic body. She has a D cup chest with a flat stomach. Her waist is what always got me. It's tiny and tight for her age. She was always a fantasy for me and, although her talking about a sex toy with me was hot, I was embarrassed.

"Wow that is a lot of money to spend on a sex toy." She said.

"I know, but..." I started.

"For someone to spend that much on a sexual device... They must have an addiction." She interrupted.

"I wouldn't say that." I responded.

"200 Dollars?? You definitely have a problem. I think your parents should get you some help."

"No no no. No one else has to know about this right??" I begged.

"I don't know. I think your parents would like to know." She responded.

"Come on can't we make a deal or something? How about I finish this yard work for you and we can just keep it our secret?" I asked.

"I have an idea." She said.

"You're going to be my slave for the next week. I have a lot that needs done around this house and I could use you. You'll do exactly as I say. If you don't obey me I'm letting your parents know all about what I found on my porch."

"Well, I have no choice. Your wish is my command."

"Good you can start by finishing this yard work for me." She said with a grin.

So I went to work. While cutting the grass I just kept thinking of what in the world she will be having me doing this next week. I figured it wasn't that bad. I'll do some manual labor for her and then I can go on. I also wasn't too upset that I had to spend a lot of time with her. She was always nice to me and I didn't mind looking at her. I had no idea what she had planned.

I got the yard work done and she came out and told me I could go home.

"Good work. You can head home but come back here at 9am tomorrow. I've got a big day planned for you."

"Okay." I replied.

The next day came and I went over and knocked on the door. She answered wearing a tight pair of jeans and a black tank top that showed a lot of cleavage.

"Come in." She said as we walked through the house.

"So what are we doing today?" I asked.

"Oh you'll see. Come to the basement with me."

I followed her down to the basement. It was pretty clean, but empty. Cement flooring with steal posts holding the house up.

"Get used to it down here. It's where we will be all day today." She said.

"Okay." I replied.

"Alright, this is what is going to happen today. I'm going to go upstairs and grab two bags and bring them down. You have until I bring the second bag down to be completely naked."

"W-w-what?" I stuttered.

"You heard me and if you want your secret to be safe with me you better listen."

She walked upstairs. I couldn't believe what was going on. All I knew is that I had to get undressed and fast.

I got my shirt off and my pants half off as she came down with the first bag.

She looked at me and smiled as she went back upstairs.

I hurried and got the rest of my clothes off as she came back down with the other bag. I stood there completely naked in front of her. My hands covered my dick as I just stared at her.

"Good, you listened." She stated as she reached into one of the bags.

She grabbed a bunch of rope and walked over to me.

"Stand between those two poles." She commanded

I did as I was told. She grabbed a stool and stood on it in front of me.

"Give me your hand." She ordered.

I lifted my right hand up to her and she grabbed it. She reached it as high as it would go and tied my wrist to the metal pole tightly. She then did the same with the other hand. She got off the stole and looked at my completely exposed penis.

"Not bad. You might be more useful than I first thought."

I just stared at her.

"Now spread your legs so that they are touching the poles on each end."

I tried but they wouldn't reach.

"They won't go any farther." I said.

She then bent down and forced my leg to touch the pole and tied it there as hard as she could. She repeated the process with the other leg.

"Does that hurt?" She asked.

"Yeah."

"Good. Get used to pain."

She went back to one of the bags and grabbed a black whip out of it. She walked up to me and said,

"You're addicted to sex, Nate. After we are done with this week you aren't going to want anything to do with sex anymore. I'm going to cure you."

Then she pulled the whip back and smacked me on the stomach.

"Ahhh Fuck!" I shouted.

"That's nothing you little bitch." She said.

She started whipping me consistently. It hurt. My stomach was turning red along with my breasts. Then she moved behind me. She started smacking my ass as hard as she could.

"Ah ah fuck ah fuck." I let out a noise every time she hit me.

After about an hour of her whipping my entire body she stopped.

"Okay now for the real fun. I'm going to get on my knees and start playing with your dick. I'm going to do whatever I want with it, but you aren't allowed to cum. If you do there will be an extremely hard punishment that you do not want. Do you understand?"

"Yes I understand."

She then went down on me. She started stroking my dick pretty hard with her hand. It got hard fast.

"This thing is pretty big. I think I want it in my mouth. Is that okay with you?" She asked.

I didn't reply.

"Of course it is." She said.

She put it deep in her mouth and started sucking. It felt amazing and made my knees weak. She then started stroking the base of my cock and sucking on the tip. It was the best blowjob I had ever received. Then she stopped sucking and reminded me I can't cum.

"Don't cum. Remember what I said."

"I know." I responded.

Then she tortured me with her hand. She started furiously stroking my cock with her right hand. As fast as she could she was stroking.

"Don't cum Nate. Remember."

She continued to stroke it fast

"Don't you fucking cum. You'll regret it. You can hold it. Don't cum."

It was becoming impossible for me to continue to hold it in.

"Don't cum. Don't cum. God I bet you want to don't you? You just want to release it all over my face, but you can't."

She was torturing me and I knew I couldn't last much longer.

"Don't cum. Don't you..."

"Ah fuck!" I interrupted as I came all over her face.

"I told you not to Nate. You fucked up." She said as she walked upstairs.

She was gone for a while and I was just standing there thinking. I had no idea what my punishment was going to be. I kept thinking the worst but nothing prepared me for when she walked down the stairs.

She came down in front of me still wearing her black tank top but her jeans were off and in place of it was a massive strap on.

I gasped... I didn't know what to think. It was huge. It had to have been 10 inches long. It looked just like my dick, but bigger.

"Well, Nate I told you not to do it. Now we have to rearrange you."

She undid my hands and ankles.

"Okay get on your knees and face away from me."

I did as I was told afraid of further punishment. She tied my knees to the two metal poles I was between. She stretched my legs out pretty far but not as far as they were before. They were tied tight and I couldn't move them.

"Oh I'll be right back. I forgot something."

She ran upstairs and came back holding a black bra.

"Here put this on." She said as she handed it to me.

I obeyed and she got back behind me and clipped it together. Then she tied my hands above my head to the same posts as my knees. I was now on my knees tied to two metal poles, wearing a bra, with a strap on in my face.

"Well we have 3 hours until I have to go pick up my kids from school. For the next 3 hours you are going to be the female and I am going to be the male."

"What...?" I asked.

"You heard me. Who knows, maybe you'll enjoy it." She replied with a grin.

Then without hesitation she shoved the strap on right in my mouth and began to throat fuck me.

"Ah yeah suck that nicely bitch."

I had never been in a situation like this before. She was fucking my throat with no mercy. I was gagging and I couldn't breathe at all. I was gasping to catch my breath on every chance I got. She was relentless just going at it. My eyes watering and I couldn't breathe. I was miserable and she was having the time of her life.

After about an hour of relentless face fucking, she pulled out.

"That was fun wasn't it?"

"Oh yeah that was great." I said with sarcasm as I caught my breath.

I got a slap across the face.

"Don't be a smartass."

She went over to her bags and grabbed some more rope. She tied two long pieces of rope to the two metal poles in front of me. Then she said,

"You know I was going to use lube, but after that smartass comment I don't think I will."

"Lube for what!?" I exclaimed.

"For when I fuck you in the ass with my monster cock." She replied.

"Please Don't. I'll do anything else. Please." I begged.

She didn't respond. Instead she reached up and untied my arms. Then she bent me over and grabbed them. She pulled my arms as far forward as she could and tied them down to the two pieces of rope she had tied to the other poles.

I now lay bent over with the bra on my chest touching the ground and my ass up in the air as my knees were still tied to the original posts. I was in prime doggy style position and I knew it. I started to beg again as she walked behind me.

"Please don't fuck me Lisa. Please don't. I'll clean your entire house. I won't ever cum again. I don't care. Just please."

"You're so pathetic Nate. I'm going to love every moment of this. Your ass is mine."

She got on her knees behind me and set her strap on cock right on my ass.

"Look at this virgin asshole. I didn't expect you to be so tight. I might just split you open."

She spread my ass as far as she could and set the tip of her dick right on my hole. She started to press in on it and I felt it start to stretch.

"Oh my god. Please Lisa. I beg you please!" I exclaimed with panic.

She pushed harder and then she thrusted as hard as she could and about half of the strap on entered my asshole. It split my anus in half and I could feel it start to bleed.

"AHH!!! Fuck!!" I screamed.

The pain was unimaginable. My eyes started to water as I started to cry in embarrassment and humiliation.

"Aw look at that. You're bleeding. Maybe the blood will lube it up for you. Time for the other half." She said with no remorse.

She pushed hard and the entire cock was in my ass. It hurt so badly and I just had to accept it.

"Fuck you!" I yelled.

"Oh honey you can only dream of fucking me." She replied.

She then started to thrust in and out slowly.

"Ahhh." I let out

Then she started going faster.

"Ohh my god. Jesus Christ." I sighed.

And then out of nowhere she went full speed. She was pounding my ass as hard and as fast as she could. Her thighs slapping mine as she pounded me. My balls were swinging back and forth from the fucking.

"AH! Fuck! Fuck fuck fuck! Ah my god! Ah Ah Ah Ah Ah!" I was screaming and then she said,

"We still have an hour bitch! You better start enjoying this because I'm not stopping until you cum!"

I was confused as she continued to pound my ass. Was it even possible to have an anal orgasm? I didn't know. I never even thought of being fucked in the ass before. How was I supposed to enjoy it? All I knew is that if I wanted this to end I had to figure out how to.

Another 15 minutes passed as she continued to fuck my ass. She wasn't tiring one bit. I noticed the pain in my ass stopped and I could feel the strap on go in and out of my ass. With the humiliation gone at this point and the pain no longer there, I was able to focus on what was happening.

I had one of the most attractive women I know fucking me in the ass with a strap on. I couldn't see behind me but I could imagine her tits bouncing up and down as she pounded my ass. The thought kind of turned me on and then she spoke,

"Oh yeah. Its going in and out easier now, Nate. You know what that means?"

"Hmm! No." I responded with a moan.

"Your body is starting to lube it up for me. Your body is starting to enjoy this. You're enjoying being fucked in the ass!" She exclaimed.

I didn't know what the hell she was saying. I didn't know if she was right or just saying things to fuck with me, I was starting to enjoy this. My dick was getting hard as she pounded my ass.

"Ahh fuck! You're right."

"You love me pounding your ass don't you bitch?" she asked

"Yes! I fucking love it!" I yelled.

"You want me to fuck you harder Nate!!?"

"Yes! Fuck me harder Lisa!"

She started to fuck me harder as she started letting out little moans. I was loving this. I was enjoying being fucked in the ass. I started to feel an orgasm build but this was different. I didn't know what was happening, but it was feeling good and I wanted more.

"Ahh Ahh!! Fuck Lisa! I think I might cum!"

"Ah Oh yes baby! I want you to!"

"Ah fuck yes Faster!" I begged!

"Come on Nate! Cum for me!"

"Ah fuck! Ohhhh!! Fucking yes!! I'm gunna cum!!!" I screamed!

"Ah yeah Nate! Cum!" She demanded!

"Oh My God! Yes! I'm cumming!! Fuck! Ohhhh AHhhhh! Yes!" I shouted as I came.

"Hmmm yeah Nate. How was that?" She asked as she pulled out.

"That... That was fucking amazing Lisa." I responded.

I just had the best orgasm of my life. I don't care how I got it but that was the best feeling I have ever felt. I knew I loved it and I didn't care that I did.

Lisa got up and started to untie me. She freed all of my limbs and I stood up finally. She helped me remove the bra I had on and then I reached for my pants. I was weak and I was sore, but I felt great.

Then she took off the strap on, revealing her sexy black lace thong she had underneath. Then she grabbed the cock and put it in her mouth. She sucked on it a good 5 or 6 times.

"So you liked that?" Lisa asked.

"Yes. This was one of the best days of my life." I responded.

I got dressed and walked upstairs with her behind me.

"Well I have to go get the kids."

"Enjoy the rest of your night Lisa. See you tomorrow at 9?" I asked

"Tomorrow at 9. Don't be late." She replied with a grin.

I left feeling like a completely different person. I was beaten and battered but I was ready for whatever she could throw at me now. After all, I would have to be. We still had 5 more days of this.

The End.