My Evolving Transition – Ch. 01 - Sex Stories

My Evolving Transition – Ch. 01

... after work, Tiff came over to my loft. She was all smiles and quickly entered my open door. We went upstairs to my bedroom, and she showed me what she bought. I watched her struggle to unpack the plastic cover, my cock grew watching her. Once she unpacked the strap-on, I was mortified once I saw the size and thickness of the item.

She then left the item in my loft until Friday, which gave me time to inspect it. After she left, I tried in vain to insert it in my ass, but it was too big, so I tossed it back in its bag.

When Friday came, and after Tiffany arrived, I stood there watching her attach the harness and then tease me with it. I acted annoyed but deep down I was nervous. She made me suck her fake cock, which I reluctantly did while sitting on the edge of my bed.

“Now, come over here and lie down,”

she pointed. I then lay down on my back, while she climbed on top of me. Then we started kissing while wrestling each other’s clothes off.

After a few minutes of kissing, fondling, and teasing, she suddenly stopped and stood up. By now we were both naked. She then walks to the bathroom wearing her new toy.

“Now, turn over onto your stomach,”

she commanded, while in the bathroom. So, I rolled over onto my belly, I was grinning on the inside and soaking up her commands.

When she returned, I felt her caressing up and down my inner legs before spreading them apart slightly and repositioning my legs off the edge of the bed. She began kissing my ass before ...

... rubbing a cold liquid over my ass crack with her hands.

Tiffany then jammed the bottle into my asshole’s entrance and squirted the liquid inside. She gently rubbed it around my butt before slipping a finger or two inside, the sudden entry made me tense up. The lube felt good sliding in with her fingers. She slowly started finger fucking my ass with them, then a third finger, all in rhythm. My ass was starting to feel a bit numb, but her fingering felt so good. I let out the odd moan.

Watching someone on video performing and experiencing it, were two different things, from what I was experiencing now. I realized then, they were actors, and the feeling I felt was something unworldly. I was arching my back and pushing my ass into her fingers, wanting more. By now I had a big hard-on hanging off the edge of my bed, and pre-cum was beginning to flow out freely.

I was moaning more and more. It was then that Tiffany stopped and started rubbing lube onto her artificial cock.

When had finished, she slapped my ass cheek a few times. Then she shoved my head down into the mattress while jerking her fake cock.

“Stay the fuck down, I am going to fuck you like a dog,”

she said and started rubbing her fake cock up and down my ass crack. Almost teasing me with what was coming. Soon she was guiding her makeshift cock into my ass entrance. It slid in easily enough to a point until it went fully inside. It made me groan slightly in pain.

The excitement had transformed into ...