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I'm not very good with these so I will share a story that just about sums up what I am into.....
Diann led me over to the bed and we lay down next to each other kissing. Her tongue penetrating my mouth. She tilted my head back and her lipstick met with mine. It was a wonderful sensation. We both smelled of flowers and sensuality. I was so hard, my cock was sticking out of the tight panties I was wearing.
“You are my little sissy aren’t you sweet boy? Do you know what a sissy wants more than anything? Yes I think you do.” Diann said and reached over to the night stand and pulled out a 7inch black dildo. “Do you know what to do with this? “
I placed my lips on the black dildo and began to suck it. Diann took the back of my head and controlled the up and down motion, at first slowly, and then faster.
“Have you done this before?” She asked. “You are quite good at it.”
I kept sucking on the cock and worried I might cum too quickly. Diann slowly pulled the cock out of my mouth and placed it on a harness.
“My little sissy, I know what you want and need. And you know it too. I want you to strap this on my hips.”
I strapped on the dildo to Diann’s hips and watched how large it was as it swung from side to side. I could not believe it was going inside of my ass. However I was willing to do anything at that moment.
Diann then took my hand and walked me over to her desk. It was difficult to walk in high heels. She bent me over the desk and tied my wrists to the legs of the table and tied my ankles to the bottom of the other table legs. I then felt a cold liquid in the crack of my ass. She was putting lubricant there.
“You are very tight and are going to need this. In fact, it is going to be very uncomfortable for you for awhile. I am going to give you a butt plug to wear around the house and this will make anal sex less painful. But for now, you are going to have to take it like a man. Understand?”
“Yes Diann. Be gentle ok?”
“I will my lover.” Diann assured me.
As the strap on went into my sissy hole, I felt a wonderful sensation. It was huge but it touched my prostrate and made me so hard. I told Diann I was going to cum. She kept going deeper and deeper into my ass and shortly I had an orgasm all over the desk.
“I’m not done yet sissy boy.” Diann said.
Deeper and deeper, faster and faster, I began to here Diann have several orgasms as the large dildo massaged her clit and penetrated my ass. She moaned and screamed and when she had had enough, she slowly pulled the cock out of my tight butt.
“Very good for your first time. Next time, I will place a cock ring on you so you don’t cum so fast. Now I want you to take a shower, and when you are done, I want you to put on the clothes I lay out for you and come to bed. Ok sissy boy?”
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