tagToys & MasturbationA Cissy & His Dildo

A Cissy & His Dildo

bypegboy©

When I first moved in with Barbara, it was simply to split the living costs. She was a lesbian and wasn't interested in anything other than a casual friendship. But that didn't stop me from fantasizing about her. I did have one secret that I tried to keep from her. I love to wear women's clothing. I sometimes even fantasized about being a transvestite. But my female clothes wearing was done alone and no one knew of my passion. Until that one special day.

There were many times that I masturbated while wearing panties and a bra. Sometimes I would tempt fate and leave my door open. I did this when I knew that Barbara would be coming home from her job soon. I almost always got off with fingers in my ass, enjoying the sensation of tickling my prostate gland.

All that finger fucking of my ass made me want to buy a dildo so I could fuck myself good. One day I went online and bought a realistic looking dildo that was eight inches long. I was embarrassed to use my real name, so I had them ship it to "Cissy Patrick". It was my fantasy transvestite name.

The day it arrived I took off from work so that I could be there to receive it when it arrived. Unfortunately, Barbara came home for lunch and that's when the dildo arrived. Barbara answered and signed for the package. She looked at me with a mischievous grin and said, "I think I know what this is."

I was mortified. She opened the package and pulled out the dildo.

"Take your clothes off." She ordered.

"What!?" I stammered.

"You want to be fucked by this, right? Well, then take your clothes off."

My mind was racing but I did what she said. I took off my clothes and stood naked before. She went into her bathroom and came out with lube. She applied some to the dildo. She bent me over and teased my anus with the tip of her dildo. I moaned slightly.

"I not going to rush this," She said. And then she slowly inserted it in me. The tip came to my second sphincter muscle and it wouldn't let the dildo go any further.

"Relax," she said. "Open yourself up to it."

I took a deep breath and relaxed as best I could. It must have worked because she was able to slip the tip past and into me. As she continued to slowly push more of the dildo into me, I felt a rush of excitement I had never felt before. My whole ass seemed to come alive.

"You've got seven inches of this dildo in you. Does that feel great?"

I couldn't answer. The fullness sensation that I had was unbelievable. My whole body felt alive like I have had never felt it before. I could only grunt an answer to her.

"Uuhh."

"I'll take that as a yes." Barbara said. She then started to thrust the dildo in and out. At first very slowly and then a little faster, and then faster. I moved my butt to the rhythm of her thrusting. Not believing this was happening and yet. Oh, yes! And yet it was happening! As the thrusts became harder, my ass felt red hot and alive. A feeling of great intense pleasure started to well up from deep inside me. The intensity of it continued to increase. I realized that I would probably come without any direct stimulation of my cock. I could do this forever and ever and ever…..

"Oh, God! I love it!" I screamed, not caring if anyone could hear. And suddenly I was overcome by the most intense orgasm I had ever felt. Waves of cum shot out of my dick and onto the bed. I still couldn't stop moving my ass to her rhythm. I didn't want this wonderful orgasm to stop.

Finally the flow of cum became a trickle as my orgasm subsided. Barbara stopped thrusting but kept the dildo deep in my ass.

"You came quickly." she said. "I think you need to do this more often."

She laughed her sweet laugh and laid me down on the floor on my back with the dildo still deep within me. She looked at me and massaged my nipples for a few seconds.

"Thank you." I told her. "That was amazing."

"I really happy you liked it…Cissy."

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