A Lucky Fuck

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The twisted fantasy of a horny MILF!
2.2k words
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I love sex and since I have all the money in the world so I can spend all my time doing it! Sex is included in all aspects of my life. I never wear clothes except for when I'm out or in a teasing mood. When I was a teenager I would start rubbing my pussy whenever I was bored. I always have my pussy and ass stuffed, when I'm shopping, when I exercise and even at Church.

One day I was shopping for some new toys when out of the corner of my eye I saw a very hot guy. He was looking through some porn. I decided to have some fun with him! I walked in front of him and dropped a HUGE dildo on the floor. I had my back to him as I picked it up. I didn't bend my knees so I gave him a good look at my stuffed ass and pussy. When I turned and looked at him he was blushing and covering the growing bulge in his pants. I held up the dildo and said, " I prefer the real thing!" I rung up my purchase and as I did so I slipped the guy my address.

I arrived home in a state of huge arousal. I pulled out my boob and pressed it against a scanner to open my front door. I was already half naked as I walked through the door. My pussy needed some attention and I was feeling especially naughty. I was in the mood that night for some Italian so I called up Bottecelli's and ordered some Italian sausage. The delivery boy arrived and I greeted him at the door in a full body stocking. His jaw dropped when he saw my huge tits squashed together in my transparent outfit.

I had a very special tip for him!

The next morning I awoke with the delivery boy's cum still on my face. I licked my lips remembering my dinner the night before. I got out of bed and headed o the bathroom to clean myself of. I fulfilled my morning ritual of soaping myself up and giving my ass a good clean because you never know when you will be getting surprise butt sex!

It was inevitable I was horny again and I needed an orgasm BAD! I was pacing my dungeon wondering what to do when my doorbell rang. Who could it be? It was the guy from the porn shop! I couldn't believe my luck! This was going to be awesome!

I told him to stick his dick through the mail slot so I could size him up. I was waiting to see his member pop through when he said, "it doesn't fit!" I couldn't believe my ears. I flung open the door and saw he wasn't kidding! Oh my god it was a 12in MONSTER! Never before had I seen a dick like that attached to a man!

It was time to get a little kinky. I made him strip on my terrace in front of the whole street. I smiled and slammed the door leaving him outside... naked. I was going to make him work for this. "Before I let you in I think we should get to know each other, what is your name?" "Alex" "Are you going to do everything I tell you to do, Alex?" "Yes, anything!" "I must warn you Alex... I get freaky" "That's great I love freaky, please let me in!" "No. Climb over my wall and meet my in my backyard... bye"

With that I went to the window to watch the show. He ran across my front lawn with his huge dick bobbing about wildly. He was shaven and his balls were proportional to his dick i.e. they were HUGE! The only way over was by climbing my neighbor's tree and jumping over the wall. I watched his cute bum work as he shimmied up the tree. He made it over with little difficulty and stood in my garden.

"I will be out in a minute!" I cried. I was putting on my work clothes. I was wearing an erotic leather outfit. Each piece of my clothing was fastened to my body with a lock. I strutted outside with my toy box and stood on a pedestal above him. "This is how it's going to work Alex. You are gong to complete a series of challenges and your reward for completing each one will be a key to a piece of my clothing. The grand-prize is I. If you complete all my challenges successfully then I am yours to do with as you please."

"It is unfair that I must put your huge dick in me if you can't do the same so to complete your first challenge you must take a dildo of the same length in your ass!" I searched through my box but none of my toys were big enough. He breathed a sigh of relief but then I remembered the HUGE dildo I bought yesterday! I ran inside and got it.

I threw him the dildo and a few bottles of KY and sat down to enjoy the show. For 15 minutes he struggled with no success. I decided to step in and give him a helping hand. "You aren't using enough lube". With that I grabbed a bottle of lube shoved the nozzle up his asshole and squeezed the entire contents into his ass. He moaned as he was filled with the slippery goo. "Now push the damn thing in!" I yelled. He gingerly rubbed his opening with the tip and gently pushed. "Harder!" He hesitated so I grabbed the toy and shoved with all my strength. I gave it my all but I only succeeded in getting it halfway. "Now you do the rest!" I sat back down and waited. With much moaning he got it all in. "Good... now keep it in while you unlock a piece of clothing of your choice but if it falls out as you walk towards me you fail."

Alex scrunched up his face and stood up. He took very small steps towards me. He chose to undo my top first. Now the only thing holding my big tits in was a very tight black bra. With a sigh of relief Alex let the dildo slide out of his ass. It fell to the floor. I laughed when I saw it was covered in shit. "Alex", I said whilst shaking my head, "Haven't you ever heard of an enema?" "No, what is that?" "Let me show you. Come upstairs you dirty little boy".

I lead him upstairs by his dick. I was more then well aware that he was watching my tight bum bounce up and down as I walked. We entered the bathroom and I bent him over my knee as I sat down on the toilet. I slowly stroked his ass. I probed his asshole with the nozzle of the enema and he winced. "Poor baby, did mommy's dildo hurt your cute little bum? Its ok mommy will sooth the pain with a sexy enema". I carefully pushed in the nozzle in and let the cooling water do its work.

"Tell mommy when to stop" I let the bag run empty. "Do you want more? ... Ok" I emptied a second bag. He asked me to stop halfway through the third bag but I coaxed him to finish the bag. "Good boy" I gave him a little spank. "Now your second challenge is to hold it in for 10 minutes. I am going to lie on the floor and you are going to stand over my face with your legs apart. If anything lands on my face you fail!" "Yes mommy"

While I was down there I admired his god-like penis. I decided to make conversation. "So Alex is your girlfriend as hot as me?" "I don't have a girlfriend and even if I did she couldn't possibly be hotter then you Miss... umm?" "That's so sweet. You can call me Davis... Miss Davis" "Ok Miss Davis" "Why don't you have a girlfriend if you have a cock like that?" "I don't know?" "Well those girls don't know what they are missing!" "Thanks Miss Davis" "Oh would you look at that, times up. Well done!"

He freed my boobs while he emptied his bowels and I let him play with them while he finished up. I wiped his ass and made him climb into the shower. While he rinsed himself of I set up his next challenge. I left a note on his towel "Hey Stud put these on and meet me downstairs" Next to the note I put a cock and ball ring and a butt plug.

"This is how it's going to work. We are going to play a video game, its called Pong. To make it more difficult for you the devices you are wearing will vibrate on full intensity. Let the game begin!" Alex was struggling to focus and I guess I wasn't helping because every time he was winning I would reach out and play with his dick. It came down to a tiebreaker. I didn't want him to lose because I secretly wanted to fuck that gorgeous cock, so I narrowly let him win. I presented my skirt as a prize.

"Alex the next challenge is simple. I will suck your dick for 5 minutes and if you cum you fail" I got on my knees and got to it. Wow this guy has such amazing focus! No matter what I did he didn't budge. I turned on the cock and ball ring. I fingered his ass and even put all 12in down my throat! But he stood solid as a rock and hard as one to if you know what I mean!

I took my time removing my thong. The time had finally come for us to cum!

"Alex before we do this I must ask you for one more thing... can I be your girlfriend? Will you fuck me whenever I need it?" "Of course Miss Davis!" "Okay then Alex before you do this, or should I say me, I have to show you something"

I led him downstairs to a locked door. "To open this door I have to put this dildo in my pussy and this one in my ass and say the password. For you to open the door you need to put in the butt plug and insert your dick in this slot and say the password." "What is the password Miss Davis?" "The password is 'I am so horny please let me in'. The plug and slot both have sensors to identify you by size and depth. Lets try it out" Alex placed his cock in the hole while I fitted the plug in his backside. "Please insert the dildo into Miss Davis to verify yourself," said a computerized voice. I did so. "Hello Miss Davis, who is your guest?" "He is my new boyfriend. His name is Alex." "Hello Alex, it is nice to meet you. Welcome to Miss Davis' Sex Dungeon."

The door opened and I showed Alex the main bedroom. The walls were covered in a large array of toys and other gadgets. "I'll explain how to use all of those later come on let me show you the living room!" There was a large TV on the wall. "This TV plays all the porn channels in the world but you need to insert this special plug into yourself to change channels. I put it in my pussy but I guess you could put it in that cute ass of yours." The shower was huge. It had a bed in the middle for you know what and the toilet had a built in enema machine. The dungeon was filled with all sorts of straps and scaffolding which allowed a person to have sex in any position they wished.

"So Alex what do you want to do first?" "This is all very amazing but if you don't mind right now I just want to fuck you... HARD!" "Race you to the bed Alex!" We made out for a few moments but our lust could wait no longer! In his rush to fuck me, his dick missed my pussy and plunged deep into my ass. I screamed but the pain quickly changed to pleasure. It truly was the biggest thing I had ever had in me! His strokes became more frantic; he pulled out and sprayed me!

He sprayed all over my ass, on my back and on my neck. It went in my hair. He flipped me over and continued to cover me in cum. He coated my face and near drowned me when I attempted to swallow some. He plastered my tits and my stomach. You could have wallpapered the room with all that cum! I looked at my invisible watch and he smiled at me as he continued to coat me in his cum. It just didn't end. We got into a 69 and he ate my cunt while STILL spraying my face! He teased my clit and stuffed his tongue deep in me. Soon I was coming as much as he was! I sprayed his face whilst he sprayed mine.

We turned around and started making out still gushing our sex juices all over each other. The juices mixed and covered us thoroughly. When we had enough energy we got up and walked to the shower. We let the water wash over us as we lay in the bed in each other's arms.

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AnonymousAnonymousover 13 years ago
Your delicious ass would love it

Hey, found your story, lucky Alex, I think with a piss enema you both could have had much more fun lol, like we did! Talk soon Jack!

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