MIkes First Transgendered Pt. 11
My turn to be fucked.
I had seen Cheryl several times since out first night together. At least once if not twice a week I would go to her place after work or on an off day and she would make dinner and we would have a few drinks. Most every time, we'd end up having sex and on occasion I would fuck her in the ass; and she on occasion, would finger me while giving me head bringing me to orgasm. But surprisingly to me she hadn't mentioned or asked me if I wanted to be fucked with her strap on. Tonight, was going to be different.
I arrived at Cheryl's for dinner. She was wearing a beautiful long flowing dress with her black pantyhose and high heels on. I could smell her cooking when I walked in the door. We sat at her dining room table enjoying our meal and conversing, but all I could think about was eating her pussy and having her ram a dildo in and out of me. After we cleaned up, we headed into the front room. Cheryl poured me a drink and we sat on the couch. After getting quite buzzed and horny I slid off of the couch and down in front of her. I guided her legs open and started kissing up her pantyhose. Cheryl moaned in pleasure as I lifted her dress further and further up, as my lips made their way further up her inner thighs. Cheryl lifted her hips, pulling her dress up past her hips as I reached for her panty hose sliding them down and off of her. Her dripping wet pussy stared at me as licked my lips. I kissed my way back up her thighs, finally putting my mouth and tongue on her clit.
Cheryl's head leaned back and she moaned in pleasure as her hands rested on the back of my head. I swirled my tongue around her clit, licking up and down her wide open, wet pussy lips swirling my tongue inside of her opening. I sucked and licked her pussy to her first orgasm, feeling her juices all over my face. I pulled her from the couch and walked with her hand in hand to her bedroom. As we got to the edge of the bed, we kissed deeply as I unzipped her dress, letting it fall to the floor. I unhooked her bra, leaning my head down to her plump big saggy tits. I swirled my tongue around both nipples as my hands held and caressed her tits. I felt Cheryl's hand working on the button and zipper of my pants, getting them open sliding her hand inside my pants grabbing my hard cock. I pulled my shirt over my head as she got down on her knees helping me out of my pants and underwear. Cheryl, put her wet warm mouth around my cock and started bobbing back and forth sucking my dick. I moaned in pleasure as I watched her head sliding back and forth across my shaft.
I pulled Cheryl up from her knees as I climbed onto her bed, my back flat on her mattress. I guided her on top of me in a 69 position. Cheryl's legs covered my head and face, as she backed in to the right position. She let her hips fall, putting her dripping wet pussy right on top of my mouth. Her head leaning down as her mouth wrapped back around my cock. I licked up and down her wet pussy bringing her closer and closer to orgasm, while she continued sucking my cock. I used her pussy juice and my saliva and wettened my fingers sliding them up and down in-between her ass cheeks, working them around her asshole. I got her lubed up enough, that I slid a finger deep inside her ass. Cheryl moaned in pleasure as I continued eating her out while fingering her in the ass. Her mouth and hand working my stiff cock.
After a few minutes Cheryl came all over my face screaming aloud as her hips thrust back and forth; her body quivering from orgasm number two. Cheryl was so overwhelmed by her orgasm, that she couldn't focus on sucking my cock any more. I didn't stop I just kept trying to ram my tongue inside her pussy while my finger kept ramming in and out of her ass. When she finally came down from her orgasm, Cheryl pulled my knees upwards, letting me feet rest flat on the bed. I felt her fingers start rubbing around my ass cheeks, eventually sliding deep enough that they were rubbing and caressing my asshole. I moaned in pleasure, because I wanted her to finger me. Somehow, she got her finger wet enough and slid it deep inside me as her head bobbed up and down on my shaft. We both lay here in this hot 69 giving each other oral sex, while fingering each other in the ass. And I couldn't get enough! Loud moaning sounds emanated from my mouth, as she whimpered in pleasure. When I slid a second finger into her ass, she almost instatntly returned the favor sliding a second finger deep inside me.
"OMG," I moaned out as she kept fingering me harder and deeper, as I did to her.
"Fuck me in the ass Cheryl", sprang from my mouth as she pushed her fingers harder and deeper inside me. I had stopped eating her pussy, cause the pleasure of her mouth wrapped around my cock and her fingers deep in my ass, left me unable to continue eating her.
"Please fuck me in the ass!" I moaned out.
"With a strap on?" She asked.
"Yes," I replied.
Cheryl pulled herself off of me as my fingers slid out of her and her fingers slid out from inside of me. She walked over to her dresser digging through a drawer. I watched as she pulled out a long silver panty style strap on. She untangled the straps, slowly sliding it on and pulling the straps tight. I was in awe watching her put it on, seeing that it was more designed as a long sleek dildo than a real cock, but I didn't care. I just needed to get fucked. Cheryl pulled some lube from a different drawer and walked back over to the bed. She stood just adjacent to my face letting me see the long silver dido attached to her. I pulled her in closer and began sucking the silver toy strapped to her. Cheryl watched as I pleasured the toy, as if it was a real cock.
Cheryl arousingly said, "You must have made your boyfriend a happy man."
I pulled the dildo from my mouth, smiled and said, "Yes I did."
I guided Cheryl down onto the bed, flat on her back, taking the lube from her hand. I squirted a generous amount on my hand and lubed up the silver dildo. I reached behind me sliding my wet fingers up and down along my asshole, sliding a finger inside myself. I climbed on top of her and positioned myself. I reached behind me and placed the strap on right at my asshole and slowly sild the long silver dildo deep into my ass. I moaned out in pleasure as It slid all the way in. It surely didn't feel like a real cock, but surely was filling and satisfactory for this situation.
I bounced up and down on the strap on, as my cock flapped up and down in rhythm. I looked down and was watching the smile across Cheryl's face, as her tits swayed back and forth with my motion. Occasionally Cheryl would reach out grab and stroke my cock as I rode her strap on. I was in heaven and was truly enjoying this dildo in my ass.
"Oh My God Cheryl," I moaned out. "It's been so long, since a dicks' been in my ass."
Cheryl knew I was enjoying every moment of bouncing up and down on this dildo, while my cock flapped up and down, rock hard. I wanted to cum, but I wanted to ride this dildo for a long time.
After bouncing up and down for several minutes enjoying her dildo up my ass, Cheryl asked me, "Do you want it from behind?"
"Yes." I replied."
I slid off of the strap on and climbed off of Cheryl as she started to get up. I got on my knees as she slid in behind me. She pulled my hips closer to her, adjusting my height. I felt her slide that strap on back inside my ass as she thrust back and forth. I moaned out in pleasure. Her hands rested on the side of my hips as she continued slamming it in and out of me. "Yah that's it baby, fuck me." I moaned out.
I needed that cock in me and I needed to be fucking pounded like a sissy slut taking a big hard cock. Cheryl's hips were thrusting back and forth at a good pace, as she fucked me like I should be fucked. I could hear her moans and her breath thickening as she pounded my ass with her strap on. "I want to make you cum," She belted out as she picked up her pace. My cock was rock hard, my mouth wide open, face down on her pillow squealing, my body in absolute pleasure as she pounded my ass. No matter how much I wanted to deny it, or chalk up my experiences with Sara and Enna as experimentation, there was no doubt that I loved cock and loved being fucked in the ass.
Cheryl's hands grabbed my hips firmly and she started pulling me towards her as she rammed her dildo deep in and out of my ass. I whimpered and squealed in helplessness, as she pounded my ass with her fake cock. "OMG Cheryl," I cried out. "I wanna cum so hard."
Cheryl leaned down on top of me placing her chest on my back. She reached around me and used her right hand to stroke my cock as she continued fucking me. She was going to bring me to orgasm rather quickly. It wasn't more than a minute later that I was crying out, "Fuck Cheryl, I'm going to cum."
Cheryl picked up her pace, pushing every inch of that dildo deep inside me while her hand was jacking me off. I started cumming all over her bed. My cock squirting like it never had before, shooting every bit of my cum all over the place. Pulse after pulse, with every thrust of that dildo pushing inside me made me squirt more. "Oh, fuck Cheryl!" I screamed out. "Don't stop, please don't stop," as she kept banging my ass.
Cheryl didn't stop. She lifted her body from mine, placing her hands back on my hips, slamming her dildo back and forth inside me. I reached new heights of pleasure after cumming I had never reached before. Cheryl kept fucking me for at least two more minutes, while I begged her for more cock. When she finally withdrew that strap on from deep inside me. I fell chest first onto the bed in complete exhaustion. My legs shook and my ass was open like never before. Cheryl laid down next to me and was gently stroking my face and neck. She was winded and shaking herself. We laid around for a while talking and enjoying our naked time together. Before the night was over, I fucked her in the ass until I orgasmed and even rammed that dildo in and out of my ass as she watched me fuck myself. I couldn't get enough of having her toy ramming in and out of me that night.
I wanted to spend the night, but had to work early in the morning. When I left her house and drove home my thoughts revolved around making this more permanent with her. But would I be satisfied long enough or permanently with a strap on or toys? Or would I need a real cock, like I was getting before her? There was no doubt I needed cock more than pussy, but I surely loved her pussy too.
So many questions, with no answers in sight.
I had a few more weeks with Cheryl, until I realized her illness (which I'll explain in the next chapter) and her age started to concern me more. But I did ride and take that dildo several more times before I said goodbye to her.
To Be Continued...
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