Until last night I had never had sex with a totally feminine male. Janie was my first. When I first saw her, she was wearing maids dress, black trimmed with white lace; white stockings attached to a white garter belt and a white maid's cap. Her black, patent leather slippers was beside the bed and her black panties was hanging from one ankle. Oh yes....she was in bed with Kay's husband, on her hands and knees and he was fucking her sweet ass. That was Saturday afternoon when Kay and I walked in on them. But that's another story for another time.
The next time I saw Janie, she was at my door, dressed in the same maid's outfit as I had asked her to wear. She was very nervous. She had seen the tattoo on Kay's left buttock and she had seen the red welts of a recent whipping my riding crop had left on her ass. She feared I would whip her, but that wasn't what I had planned for the evening. I introduced her to Billy-boy and Teri, then took her by the hand and led her into the bedroom. I sat on the edge of the bed and drew Janie down beside me, then I kissed her red lips. I kissed her as a man would kiss a woman....covering her mouth with mine, forcing my tongue between her lips.
Our tongues danced in the warmth of her mouth as I pressed her back on the bed, and lying half atop her, I ran my hand up under her skirt until I found her already hard cock beneath her lacy panties. I squeezed it gently, but firmly. She moaned into my mouth. I turned up her skirt and drew her panties down, then I ended our kiss, and kneeling on the bed beside her I took Janie's cock in my mouth. I allowed it to slide deep into my throat, but only for a moment before I drew my head back. Keeping only the knob between my lips, I clasped the cock with my teeth and swirled my tongue over the sensitive flesh of her glans. She moaned. She tried to lift her behind off the bed and force more of her cock into my mouth.
I held her down. She cried out: "I'm coming!" and came. Her cock jerked between my lips and her semen spurted into my mouth....warm and thick if filled my mouth and oozed down my throat. I Held his cock trapped in my mouth until I had drained, then swallowed every drop, then I lay beside Janie and drew her toward me. I held her tight and hissed her. She suck the flavor of her semen from my lips and tongue, the she slid downward, She turned up my skirt and pressed her mouth to my pussy. I pulled her around, got her to straddle my head and took her soft but still large cock into my mouth.
When her cock was hard again, I rolled Janie onto her back and mounted her. I lowered my wet pussy down onto the spike of her erection and let it slide slowly into me. God! it felt good, damn good. I sat on it for a moment or two, then I started to ride her....slowly at first, then faster and faster until I was about to come. I ground my pelvis against hers, pleasurably crushing my clit between us, grinding until I came and as I came the spasms of my inner muscles squeeze her cock and she came again.
After I had begun to breath normally, I got up, kissed Janie's lips and left her lying on the bed as I left the bedroom. I sent Billy-boy into the master bedroom to enjoy Janie and I took Teri into the guest room. Thus ended my evening with a cross dresser, a very enjoyable evening.
The next time I saw Janie, she was at my door, dressed in the same maid's outfit as I had asked her to wear. She was very nervous. She had seen the tattoo on Kay's left buttock and she had seen the red welts of a recent whipping my riding crop had left on her ass. She feared I would whip her, but that wasn't what I had planned for the evening. I introduced her to Billy-boy and Teri, then took her by the hand and led her into the bedroom. I sat on the edge of the bed and drew Janie down beside me, then I kissed her red lips. I kissed her as a man would kiss a woman....covering her mouth with mine, forcing my tongue between her lips.
Our tongues danced in the warmth of her mouth as I pressed her back on the bed, and lying half atop her, I ran my hand up under her skirt until I found her already hard cock beneath her lacy panties. I squeezed it gently, but firmly. She moaned into my mouth. I turned up her skirt and drew her panties down, then I ended our kiss, and kneeling on the bed beside her I took Janie's cock in my mouth. I allowed it to slide deep into my throat, but only for a moment before I drew my head back. Keeping only the knob between my lips, I clasped the cock with my teeth and swirled my tongue over the sensitive flesh of her glans. She moaned. She tried to lift her behind off the bed and force more of her cock into my mouth.
I held her down. She cried out: "I'm coming!" and came. Her cock jerked between my lips and her semen spurted into my mouth....warm and thick if filled my mouth and oozed down my throat. I Held his cock trapped in my mouth until I had drained, then swallowed every drop, then I lay beside Janie and drew her toward me. I held her tight and hissed her. She suck the flavor of her semen from my lips and tongue, the she slid downward, She turned up my skirt and pressed her mouth to my pussy. I pulled her around, got her to straddle my head and took her soft but still large cock into my mouth.
When her cock was hard again, I rolled Janie onto her back and mounted her. I lowered my wet pussy down onto the spike of her erection and let it slide slowly into me. God! it felt good, damn good. I sat on it for a moment or two, then I started to ride her....slowly at first, then faster and faster until I was about to come. I ground my pelvis against hers, pleasurably crushing my clit between us, grinding until I came and as I came the spasms of my inner muscles squeeze her cock and she came again.
After I had begun to breath normally, I got up, kissed Janie's lips and left her lying on the bed as I left the bedroom. I sent Billy-boy into the master bedroom to enjoy Janie and I took Teri into the guest room. Thus ended my evening with a cross dresser, a very enjoyable evening.
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