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My education continues Part 4

"A truth based dstory of my education in anal ways"

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One must read at least part 3 to understand this….but then it will become apparent what is up quickly

“What? I understood turnabout is fair play, but what exactly do you mean? John and Brad aren’t here and I am not sure I want them to fuck me,” I said.

Madeline rolled over, her glistening breasts and my favorite hard nipples facing me causing a stirring in my groin.

“Who said anything about them. It is my desire to have your ass myself,” she said.

“How is that possible?” I asked naively.

“Let me show you.” She smiled as she got out of bed, went into the bathroom and closed the door. I was wondering what that all meant and, being ignorant at this point of adult toys, I really was flummoxed as to what she meant.

“Okay, you ready?” Madeline said.

“I guess so,” I replied apprehensively.

She slowly opened the door and came out, smiling. My eyes must have bugged out of my head; I know my jaw dropped in wonderment. She was dressed in a red and blue tinged corset, her breasts exposed but support by the bustier style, a garter belt and sheer black stockings on her legs, and an obscene 9” by 5” strapon dildo sticking out hard from between her legs. In her had was a smaller and thinner dildo and some lubrication.

“What do you think, sexy?”

I immediately was erect just from the sheer sexuality of the display, long hair over one eye and splayed about her shoulders, nipples erect and a big sexy smile on her face. She moved forward and kneeled on the bed.

“Lie down on your back and spread your legs,” she said seductively.

I was eager to comply, erect and heart beating fast with anticipation. She was going to plug my ass with those toys? Really? You are kidding. Not since the brief affair with a friend in my exploratory days had anything been in my ass bigger than a finger. I had quite forgotten it as a subject for eroticism.

She put the items on the bed as she got between my legs and leaned forward, rubbing her warm oiled hand up my stomach to my chest and resting the hard warm lubed dildo alongside my own hard cock, giving me odd sensations of warmth and hardness. She then moved up and straddled me and placed the dildo on my chin.

“First, I want you to lick and suck the strawberry crème off my cock before I continue with your education into ass sex.”

Reluctantly, as I have never sucked anything besides Madeline’s pussy and ass at this point, I opened my mouth and let the enormous cock head into my mouth. Clearly, she had warmed the rubber cock in hot water before adding the strawberry lube to it. I moved my hands to her nipples and breasts as I took more of the fake cock into my mouth and got into moving back and forth on the veined item. I was getting more and more excited and hard as a nail, and she seduced me into this kinky sex. She took my hands from her breasts and moved them so that I was stretched and she was confining me, holding my wrists down. She began to move her hips back and forth, her cock fucking my mouth gently as I began to get into the scene. Moving my tongue around the fake cock head made me wonder what a real one would be like.

This went on for a few minutes until she withdrew the cock from my mouth and moved down til she was supine over me and her mouth was over my erection. She took me in her mouth, and then I felt something nudging my asshole gently, wetly. She moved a finger inside me as she took all of my cock in her mouth and ran her tongue around my hard cockhead.

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She sank her finger all the way in and twisted it a bit, expanding my hole. It didn’t really hurt, it just felt like a pressure. The more she manipulated my hole the more relaxed it became. She kept sucking me as she continued sinking a second and then a third finger inside me til I felt a bit stuffed and she was plunging her hand in and out gently.

The feelings were incredible. Only once I had something penetrate my ass and I had been years. The tingling it created throughout my body amazed me. I was hard as I had ever been and her mouth was egging me on while she fucked my ass with three fingers slowly at first, and then a bit faster, in preparation for what was to come. Suddenly, she sat up, ending all the fabulous things she was doing to me, leaving me wanting more.

“Okay, it is time. I want you to roll over and get into the doggie position,” she said.

I complied and was naked on the bed with my legs spread and ass hanging out. She took the skinnier dildo, lubed it up a bit and began to circle my hole and then moved it forward. There was a little tinge of pain as it first went in but it was accepted readily and caused a throb in my cock. She began slowly and then, once again started to thrust it in and out faster. Her other hand began to milk my hard cock, causing the foreskin back and forth over the sensitive head, exciting me to no end. After a few minutes and me starting to groan and moan in pleasure, she pulled it out.

“Okay, my love, now for the main event,” she said.

I leaned forward with my head and shoulders on the bed and my warmed and lubed as hanging up in the air. Madeline moved forward on the bed and lodged the big cock head on my slightly opened hole and began to push. The opening grew and as she got inside, the pain hit as she came up against the last ring causing me to flinch and ow in pain. She hit it a couple of times, and I almost told her to take it, before my muscle stretched and accepted the hard dildo. It sank into me filling me as I had never been filled before. She lightly pulled it back and forth, beginning a pleasure I had never felt – stuffed in the ass and hardness bobbing. I was amazed and hot as a result. Amazed that this was so pleasurable – why did everyone think this was so wrong? It felt incredible!

Madeline began to fuck me harder, and I got back up on my hands and she bent over me fucking and rubbing her hard nipples on my back, kissing and gently biting my neck and shoulder. She began to stroke and bottomed in my, her minuscule pubic hair rubbing my ass as she plundered me. I was groaning and moaning, as she thrust the dildo faster and faster in my ass. I began masturbating to the thrusts and shortly felt a huge buildup happening starting at the base of my balls. She was going crazy, really thrusting now and suddenly withdrew fully as I suddenly groaned loudly and sprayed cum everywhere in a massive orgasm. Wow.

My ass was feeling cool air inside, and I was still dripping cum as I collapsed on the bed, coating myself in my orgasmic cum, satiated and exhausted from all the effort.

“My love, that was incredible!” I said. “Now I see what you felt and why you were so excited to bring me here this weekend and explore this new aspect of sex.”

She lay on my back and kissed me.

“I thought you might like it. Get ready though, I feel there will be much more exploring to come,” she said.

I smiled and said,” I am open for any suggestion at this point!”

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Written by juanmoretime1
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