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.
