Don't Do The Crime If... Ch. 04

This is a continuation of my story of how my neighbor blackmailed me into doing things that I never thought I would do... and I am loving it. You should probably read the first three chapters so you can see how I got into this mess.

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"I'm going to give you a choice Slut. You can go downstairs and just keep walking out the back door and I will send your sexy pictures out to everyone you know before you get to your own back door, or, you can go to the kitchen and find the three cucumbers I bought and bring me back the biggest, fattest one. Now go and either bring me back that big fucking cucumber or keep walking and hope the internet goes down for the next few years."

I quickly walked out of the bedroom and down the stairs. I had no intention of leaving and quickly searched the counter for the cucumbers. I found them wrapped in a plastic grocery bag and laid them out on the counter. All three were huge. I picked the biggest one and ran back up the stairs wondering what she was going to do with this giant vegetable. I knew it was going into me but I wasn't sure how or where.

When I walked back into the bedroom, Gwen was waiting. She was holding a washcloth and a tube of something. I handed her the cucumber and she used the washcloth to clean the cucumber.

"Get back up on the bed and sit back against the headboard and spread your legs Slut."

"Yes Mistress."

I did as she instructed. I sat back against the headboard with a pillow behind me and I spread my legs as wide as they would go. Gwen took the tube and spread a thick layer of clear gel on the cucumber. I realized it was lube and I was hoping that she wasn't going to try to fit that giant cucumber in my almost virgin ass.

"Play with your pussy slut. You are going to have to be nice and wet to take this monster in that slutty cunt of yours."

"Yes Mistress but I don't think that will fit, it's too big." I pleaded while pushing two, then three, then four fingers into my tight pussy. I was trying to stretch myself as much as I could before she fucked me with that big green cock.

"Shut up slut, you can take it and you will. What you won't do is cum until I tell you that you can cum. Do you understand?"

"Yes Mistress."

"Say it! Tell me what you are going to do and what you aren't going to do."

"Mistress, I am going to take that big cucumber in my pussy..."

"Sluts have cunts, not pussies. Now start over."

"Mistress, I am going to take that big cucumber in my cunt and I won't cum until my Mistress gives me permission."

"That's better, now let me see your fingers."

I pulled out my fingers. They were covered with my juices.

"You really are a slut. Look at how wet your cunt is just anticipating fucking a cucumber."

I hung my head in shame until I felt a cool slippery cucumber hit my hand.

"Now take this and fuck yourself while I make a nice video for Scott and me."

She handed me the cucumber and as I held it in my hand, I realized that I couldn't even fit my fingers all the way around it.

"You have five minutes. You will fuck yourself with this cucumber for five minutes. You will not cum before then and once the five minutes are up, you can beg me to allow you to cum at which time I will decide whether to let you cum or not. It will be up to you to convince me that you deserve to cum so don't disappoint me."

"Yes Mistress."

Mistress Gwen handed me the big cucumber and I leaned back against the headboard and spread my legs as much as I could. I started out rubbing it along my slit, getting some of the lube onto my pussy. I looked up and saw that Mistress Gwen had her phone out and was videoing me. I was embarrassed and scared as the cool vegetable that looked far too big to fit in my pussy slid between my slick pussy lips. Although I was scared, I was also getting really turned on and I could feel my pussy getting really wet again. I don't know if it was the impossible size of the cucumber or the humiliation of Gwen filming me that started to get me really going but I was now determined to put on a good show.

I positioned the smaller end of the cucumber against my opening and twirled it lightly. It was so big that even the slightest push caused my pussy to be stretched and the cucumber to rub against my clit. I kept pushing and slowly twirling my big green vege until I felt my pussy begin to open and take in the monster. With less than an inch starting to slide into my stretched pussy, I could already feel it starting to burn. As I pushed further, I felt a release and my pussy suddenly opened and allowed the thick vegetable to fully penetrate me.

I continued the slow pressure and soon had worked several inches inside of me. My pussy lips were burning at being stretched but I could also feel them adjusting to the thickness. After two minutes I had at least 3 inches of cucumber inside of me and I was slowly pushing in another inch. I stopped to let myself adjust and as my muscles became accustomed to the giant intruder, I could feel the pain starting to melt away and the slow burn of pleasure rising in me.

By the time three minutes had passed I had 6 or 7 inches inside of me and I started a slow fucking motion, sliding in and then out and then in just a little further until I had about 8 inches inside me and I was really fucking myself. It was huge and filled me like nothing ever had before. My pussy lips were wrapped so tight around it that I had trouble pulling it out. I could see my inner lips clinging tightly around the girth of the cucumber as I pushed in and pulled out.

By the 4th minute, I was like a fucking machine, hammering that giant vegetable in and out of my stretched cunt and I could feel my orgasm approaching. I had never felt such incredible pain and pleasure.

At five minutes I was begging my Mistress to let me cum. "Please Mistress, may your Slut cum? Pleeeeaaassseee. I neeeeeed to cum soooo bad. Pleeeeaaassseee Mistress."

I was having trouble breathing as I slammed that fucking cucumber into my cunt. I wanted to cum so badly. I was now twisting it as I pushed the big vegee inside me sending an even more urgent message to my brain for relief.

I wanted to open my eyes and see how long I had been going. I didn't think I could keep it up much longer but I didn't want to stop either. I really, really needed to cum.

Finally, Mistress Gwen stopped filming and looked at me.

"Do you really want to cum my little Slut?"

"Yes Mistress, please let your slut cum. I will do anything, just let me cum."

"Leave that in your pussy and turn over and get on all fours."

"Yes Mistress."

I shoved the cucumber as far inside me as it would go and then rolled over and got on all fours. I reached underneath to grab the cucumber and continue fucking myself when Mistress Gwen swatted my hand away. I was afraid she was going to make me stop but instead she grabbed the end of the green monster sticking out of my cunt and twisted it.

"I am going to count to five and when I get to five you can cum. Do you understand?"

"Yes Mistress, thank you Mistress."

"Aaauuuuggghhh!" I gasped as she twisted the cucumber and pushed it deeper into my aching cunt. At this angle more of the thick shaft slid inside of me. She then started fucking me with it, fast and then slow and then fast again. She started counting slowly.

By the time she got to three, I didn't think that I could hold off any longer. The pounding my pussy was taking was going to set me off. When she hit four, I was in pain, holding back my orgasm as she continued her relentless pounding.

When she finally said "Five," and pushed the cucumber into my wonton cunt as far as it would go, I started cumming. Fireworks went off all over my body. I started to shake uncontrollably and I had the most extreme orgasm of my life. It was like I had never had one before or at least the ones I had, had only been minor tremors compared to this major earth shattering quake.

I thought I was going to black out when Gwen pulled the cucumber out and I collapsed onto the bed. I had never felt such a feeling of emptiness. I could feel cool air inside my pussy, something I had never experienced before. I must have been gaping open, a massive hole left by the giant cucumber. I just lay there exhausted.

I lost track of Gwen. I'm not sure how long I laid there before I realized that she was shaking my shoulder. I must have dozed off.

"Get up Slut, we're not done."

"Yes Mistress."

"Get down on the floor, on your knees."

I slid down onto the floor while Mistress Gwen climbed onto the bed. She positioned herself on all fours, with her ass facing the side of the bed.

"Now, fuck my asshole with your tongue Slut and you better do a good job."

I licked her tight asshole earlier but I didn't stick my tongue inside. I positioned myself with my face peering directly at her ass. Her scent was more pungent now but just as intoxicating. I gently licked around her pink little star before pushing the tip of my tongue slowly into the tight circle. It was closed tightly but the more I licked and stabbed at it, the more it seemed to loosen up. I could now stick the tip of my tongue into the tight passage.

Gwen moaned slightly as I pushed more of my tongue into her ass. She reached back and pulled her cheeks apart which opened her up more to me. I pushed further into her, making my tongue as stiff as possible. Soon I was tongue fucking her delicious asshole.

"Now my pussy Slut. Make me cum!"

"Yes Mistress."

I literally dove into her dripping pussy, licking and poking my tongue into her open slit. I was lapping up as much of her juices as I could while also trying to tongue fuck her luscious hole. I felt Gwen arch her back and then she reached back and grabbed my ponytail, pulling my face further into her pussy. My nose was buried in her slit and my tongue was swirling and flicking her clit as fast as I could. When I sucked on her swollen clit, she started to cum. She was pulling me so hard into her that I could barely breathe as she coated my entire face with her juices.

Finally, she released me and I gasped for air. Gwen was shaking. I could see her leg muscles twitching as she lay on the bed, her orgasm working its way through her body. For at least two minutes she lay still on the bed and I just knelt there on the floor. Finally she looked up at me and I though I almost detected a smile.

"Go home slut, but I want you back here same time tomorrow. I want you to wear black stockings and a garter tomorrow. If you don't own some, go buy some. And don't be late."

I got up and started to walk out, already thinking about going to the mall to buy stockings and a garter belt when Gwen added, "Oh, and by the way, my husband has his poker buddies over on Friday night and you are going to be the entertainment. They are going to want to fuck every one of your slutty little holes so tomorrow you better be prepared to have that virgin ass of yours fucked." Then she turned her head and lay on the bed as I Ieft the room both scared and excited about tomorrow.