What It Feels Like for a Girl

A couple of years ago D told me about his shemale fantasies. I felt I understood why it was so intriguing - a hot woman with a big cock…the best of both worlds.

I knew how much I enjoyed having a dick in my mouth or in my ass. I wanted him to be able to experience it, too. First, I tried fingering him while he was jerking off. Next I bought a toy called the Rude Boy. D had never had a toy in his ass before. We inserted it and I gave him a hand job. Even though he seemed slightly uncomfortable at times, the experiment was exciting enough that he shot one of the most impressive loads I had ever seen. He tried it on his own several times, but was unimpressed.

We began discussing the possibility of a strap on. Before I bought one, I sent him photos of myself with my large realistic VixSkin dildo tucked into my panties. Seeing photos of myself with a cock turned us both on more than I imagined. The next time we saw each other I tried fucking his ass with a hand-held dildo. D laid on his back at the edge of the bed and I stood in front of him, holding the dildo at crotch level. It was a success. We both wanted to proceed to the next step.

I went to the store and checked out the harnesses and realistic dildos. I had images of D sucking cock in my head and I wanted it to look like the real thing. He knew I was running this special errand and demanded a photo preview. When I got home I took the first grainy images of myself wearing a strap on. I had purchased a harness with a removable bullet vibrator. It felt uncomfortable, so I took it out. After I took the photo I played with my new dick. I stroked it as I had seen D do to his own on so many occasions. I was shocked at how wet I had become. Even without the vibrator the motion of stroking rubbed the base against my clit. I ended up fingering myself while stroking my dick. I was picturing D on his knees sucking my cock. I wanted to rub it on his lips and face. I thought about watching as my dick slid slowly into his ass. I wanted to see him cum hard while I was fucking his ass.

When the day finally arrived to test my new equipment, I was excited. As always, D arrived at my house with his cock engorged and dripping in his jeans. I rubbed him through his pants and knew he was eager to be fucked. I went into the other room and got ready. I wore a leopard print nightie with black lace mesh and a built-in push up bra. With my cock sticking out from under the black lace trim I felt like a fantasy shemale. I entered the bedroom and sat on the edge of the bed. D knelt before me and began to lick my cock. I gripped his head in my hands. Soon he was taking the whole length of it into his mouth. I could see in his eyes how much he wanted it. Suddenly he pushed me down and straddled my face. He slid his dick into my mouth and bent forward to suck mine. His fingers slipped into my dripping, wet pussy. All I wanted to do was fuck him hard.

After I came, I had D lie on his back at the edge of the bed. I poured lube into my hand and began stroking my cock. I poured more lube and used it to massage his balls and cock, slowly working my fingers toward his waiting asshole. I worked the lube into his ass and then rubbed the tip of my cock against it. I slowly pushed my way inside him. I know that I couldn’t physically feel it, but I could mentally feel it. Seeing my cock sliding in and out while my balls slapped against my pussy was driving me crazy. My hips thrust while my hands worked his cock. Seeing the look on his face and knowing that he was experiencing his first proper ass fucking made me want to cum in his ass. I wanted to possess him and make him mine. As I sensed he was about to cum I did not stop thrusting. My body shook with an orgasm as I watched his cum shoot onto my hands, his stomach and his chest. When he was done I kept stroking. I stopped pushing, but did not withdraw. I wanted to enjoy the feel of my cock still deep in his ass as I rubbed his cum over his cock before licking it off.

And that’s how it all began…