John was so eager to be taught. He hung on my every word, and when he brought to my attention, his interest in anal, I saw it as a chance to take John to a level of Sexuality he had never experienced before; Prostate milking.
Saturday night came, and it was always our date night. Where would we go? Sailing perhaps… a nice movie… a riverside evening picnic? No matter where John and I went on our date, I knew it would be a lot of fun, and I also knew it wouldn’t end until the next morning. He picked me up in his awesome sports car and showed me around. As we drove through all these quaint little towns, the wind blew my hair. I smiled at John, and he returned the same goofy grin.
He had no idea what I had in store for him.
Sailing it was. I loved sailing with John, we had a candlelit dinner and talked about stars and our mutual love of “negative space”. John was just one of those guys, you could be silly with. We drank and enjoyed each others company. We sat at the bow, and it didn’t feel like we were sailing, but flying. I looked over at John, and he was so sexy in the evening light. Dark hair, strong features. Sexy.
But I knew John, and this wasn’t our first date. John was quite submissive. Although I’m not a Domme, being with John made me feel powerful. I stole a kiss at that moment. One kiss turned into a very passionate make-out session. My lips made their way to his ear lobe, ” Have you been thinking about my ass all week John?” I smiled as his name and the thought of how excited he got parted through my lips. ” Tell me, John”
“Yes, Anna” He managed.
My hand slid down his chest and over the front of his pants to feel his erection. Mmmmm, now that was a big cock. “Mmmmmm, John, my you are excited” I squeezed as my mouth formed the word exxxccciiittteeeddd. He let out a hard breath.
” I want you to take your pants off, and stand in front of me, I want to see you” I smiled gently stroking the pads of my fingers over his cock.
John stood, almost a little embarrassed, and took down his pants. His cock sprung to attention, and my mouth watered. I started to stroke, wrapping my hand around his girth, and squeezing gently. He looked down at me, the ship sailing itself at a very slow pace. He looked beautiful in that light, this man who I was planning to devour.
” Sit, John” I patted the seat next to me. John sat slowly. I began to unbutton my blouse, as he began pulling his polo over his head. I got down on the ship’s deck, kneeling before him. Then I made a motion with my hand for him to “scoot” lower in the seat. He did. And when John was slouched down enough, I placed my hands between his knees and parted them wide.
I began kissing him, licking his thighs, as I could see the anxiousness spreading over his face.
I touched his cock, so gently. He was incredibly hard. I asked him if my hands felt good, and all he could manage was a nod. Pre-cum began to form at the tip of his member. I so badly wanted to lap it up, but I refrained. I needed John turned on, turned on to the point he would do anything, just to orgasm. Then I stroked and played, touched and kissed, never placing him in my mouth.
Finally ” Anna, please suck my dick- please- I can’t take all this teasing” I smiled, a very wicked almost sinister smile. I nestled in between Johns’s legs and commanded his full attention as I began to lick his throbbing dick head. He moaned enveloped in pleasure. I took my index finger and began to touch his taint, watching for his reaction. He didn’t resist. ” Just relax” I whispered. My finger wagged its way into his crack, and I played gently, never harsh. I found the entrance to Johns untouched ass, and I circled it.
Johns’s eyes grew wide.
I put him in my mouth and sucked his cock almost lovingly, adoring, and when his head fell back, I pressed my way into his Virgin asshole. He moaned, and groaned for me, intoxicated in a world of sheer pleasure. I stuck my finger in a bit deeper, finding his prostate, and I began milking John. His toes curled under me, and his hands held my head. He’d lean up to take a glimpse of his cock in my mouth, and the feeling of my finger milking him showed in his face. A thorough Prostate milking was exactly what John needed.
His cum began to drip and run into my mouth. He moaned and gently bucked his hips. I felt his cum gathering, forming a puddle in my mouth.
Prostate milking was exciting with John. His virgin asshole belonged to me. I milked him dry that night… but I plan to give him my ass on our next date.
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