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She looked at me and said, “one of my friends at college has used this several times with her boyfriend and she says it makes it much easier for the guy to get in you once you are relaxed”. She paused for a second and then reached back in the drawer and pulled out a small vibrator. She handed it to me and said, “Here try using this to get me loosened up and into it, I think your cock might be a little big for me at first”.I agreed and we got positioned on the bed so she could put her butt up in the air while she was laying on her stomach and she then took the pillows and put them under her to help support her in that position. I wanted to be as gentle as possible and figured that using the vibe in her pussy first would help her get excited and would also provide a little warmth and natural lubrication to it in the process.While I was doing that, I put some of the KY jelly on the fingers of my other hand and began to slowly message that on and around her cute little anal entry. At. Debbie looked up at me and said “my pussy is tired, how about I finally give you that ass you have always wanted”. Don’t worry it won’t hurt, I’ve already lubed up my asshole. Debbie laughed and we proceeded down the hall to what we now called our “den of pleasure”. I laid Debbie back on the bed and decided a little foreplay was in order. I kissed her passionately concentrating on her lips, neck and tiny breasts, I blew softly in her ear and asked her again if I could have her ass. Soon, my hand wandered down to her ass crack where lube had dripped into her ass giving me a convenient excuse to begin fingering her rosebud. Debbie moaned in pleasure as my finger entered her ass, first to the knuckle and then all the way in. As I gently manipulated her ass I added a second finger which brought out a low moan from her. Her sphincter throbbed as it opened and closed from my finger massaging her asshole. It was like it was calling out to me “fuck me, I’m ready” Then to my surprise Debbie.
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