Mies First Transgendered

Mike's first transgendered experiences part 12.

Please go read 1 -- 11 before reading this one.

An all-anal night.

Several weeks had gone by for Cheryl and I and as usual we spent time together when we could. I always enjoyed her company and our sex time although I started to see her health deteriorating. She would shake a lot more and her memory didn't seem as sharp as it once was. Turns out she had the onset of Parkinson's disease and the medications she was taking were not helping here anymore. The disease eats away people quickly and usually causes other underlying issues. I wanted her to get better and I wanted to see her become healthier again, but unfortunately that was not going to happen. As I knew we were drawing to a close in our relationship, I tried to make things pleasant for her, surprise her with little gifts like trinkets and flowers, but nothing was going to stop the inevitable, which was our splitting up.

I was at work one afternoon when Cheryl called my phone. She asked me to come spend the night Saturday night until Sunday and I agreed. As we talked more during the week, I wanted her to have fun and be reminiscent of her husband and the sex they use to have so I asked her if we could have an all-anal night. I heard her laugh on the phone and say, "Yes, we surely can." I insisted to her that no other parts of genitalia could be touched until we both orgasmed from anal, then it was all free paly. Even though I could not see her face, I knew she was smiling ear to ear.

Saturday night arrived and I went over after work. We had dinner and watched a movie cuddled in her bed. As the night got late, we decided to get ready for bed. I hadn't pushed for sex during the movie, she seemed to be a bit on edge and a bit shaky, so I was concerned for her health and wellbeing than getting laid. All I wanted was her to be comfortable and feel safe. Cheryl went into the bathroom first to get ready and when she came out, I went in as she changed in the bedroom. When we laid down in bed and cuddled in closer, she slid up deeper into me and started kissing me. As our passions ignited our hands softly and slowly caressed each other's bodies. Her hands skipping past my dick and sliding down in between my ass cheeks with her fingers tantalizing my asshole. She rubbed slowly and gently getting me even more turned on as my hands still caressed her face and arms. As I started sliding my hands down to pass by her pussy, I felt she was wearing the strap-on. She must have slipped it on under her nightgown while I was in the bathroom getting changed. I smiled through our kiss, passing by her pussy and went right for her asshole. My hands rubbed along -- the best I could -- around the strap of the strap-on teasing her ass.

As my fingers played with her asshole, her fingers played with mine. Cheryl leaned back and away from me grabbing the lube that was resting on the upper portion of the bed. She squirted her fingers and then some on my fingers as we went back to rubbing each other's asses getting ourselves even more turned on. Finally, I couldn't take it anymore and I wanted her toy in me. I rolled Cheryl on her back and lifted her nightgown up past the strap-on. I grab the lube and started stoking the toy. I slid myself on top of her, adjusting to the right angle, slowing letting myself down not her fake cock. I felt it slide into me as I groaned in pleasure. I rode her toy slowly and softly leaning down to her continuing our kissing as the dildo slid in and out of my ass. My dick rock hard in anticipation of being fucked, but also cumming all over her. Cheryl lifted herself and pulled her nightgown over her head, letting her big plump tits free. I couldn't help myself and cupped and caressed them as I bounced up and down on her fake dick. I rode her for a while just bounding up and down, letting my cock flap freely. I didn't touch myself and she didn't touch me, we were both just enjoying the position, maintaining our agreement, knowing eventually I would cum from being fucked. As would she.

I must have been on top of her for 5, maybe 8 minutes, when she moaned out, "I need your dick in my ass."

I climbed off of her, sliding her fake dick from inside me as she started to get up. Cheryl got on her knees and pulled the sides of the straps holding her dick on, letting the strap-on fall to rest behind her bended knees. I slid in behind her squirted some lube on my cock, stroked myself for a few seconds, lined up my angle and slid my had cock deep inside her ass. She moaned in pleasure as I slid all the way in. I pumped back and forth holding her hips and pulling then backwards as my hips thrust forwards slamming my cock deep inside her ass. Cheryl moaned in pleasure, sometimes squealing aloud as I continued fucking her hard. "Don't stop mike, don't stop," sprang from her mouth as I pumped, bringing her closer and closer to orgasm.

"Put it in my pussy!" She cried out, as I slammed her ass harder and harder. I pulled from her ass, as she slightly lifted her hips. I slid deeply inside her wide open, soaking wet pussy pumping about 10 times, until she had her first orgasm.

I mouthed out, "So much for all anal!"

Cheryl chuckled and said, "I needed you in my pussy."

After I stopped pumping, just letting her catch her breath and come down from her orgasm, Cheryl whispered out, "Well I came, now it's your turn."

I pulled my hard cock from inside her pussy as she swung around towards me. On your knees she demanded and pointed at my side of the bed. I wasn't going to argue and assumed the position. Cheryl fumbled a bit getting the strap-om back on and tightened, but after she did, she slid right up behind me and pushed my hips down into the right position.

She mouthed out the words, "I'm not stopping until you cum."

"Okay," I replied, knowing I wanted her to fuck my ass hard, until I came.

I felt the cool sensation of lube hit my asshole and I was so excited to be awaiting her to fuck me from behind. Cheryl slid the dildo back inside me and began pumping me, slowly at first, but the bringing herself to a nice modest pace. Her hands resting on my lower back as I felt her weight and thrusts driving her fake dick deeper and deeper into me. My moans increasing, my love for cock developing further. My cock rock hard, ready to explode. Cheryl pushed my upper torso down so my face was on her pillow. "Cum for me baby, cum for me," sprang from her mouth as I knelt getting my ass pounded by her toy. I whimpered in pleasure as she continued pleasuring me. In my mind I already knew at this point that I was going to be dating men, or women with strap-on's. There was no other sensation like this. The absolute loss of control while someone else rammed their hard cock deep inside me, making me want to squirt cum and be a little sissy girl. Yes Cheryl keep fucking my tight ass.. Just keep fucking me.

I felt pleasure deep inside me I had never felt with Sara or Enna. Maybe because it was a woman with a toy. Maybe because she could so this all night, without having to worry about cumming., All I knew is I wanted this always. My cock was so hard and throbbing and at the point of explosion, but still holding back from releasing as to enjoy every bit of being fucked. Finally, I started screaming in pleasure. I wanted to stroke myself so bad, but I made the rules, so I couldn't touch myself. I just wanted; hell, I needed her fake cock to make me cum while being fucked. Within seconds I felt pre-cum slip for the tip of my cock and I knew within seconds I was going to burst. The feeling of her pumping me, the sound of anal sex, her heavy breathing and my pre-cum sent me into overload.

"OMG Cheryl. Yes! Fuck me baby. I'm going to cum."

With a few more pumps, I exploded all over her sheets. Every thrust of her fake dick deep in my ass, made me cum even more. My legs shook, my body quivered as I am positioned face down, ass up, being rammed by a dildo, cumming without even touching myself.

"Holy Fuck!" I screamed as she continued ramming my as hard and deep.

When she finally finished and withdrew the toy from me, she rolled me onto my chest. She ripped the strap-on off and climbed right on top of my face, placing her wet pussy right on my lips. I ate her pussy until she came all over my face. I felt her legs quiver and heard her screaming at the top of her lungs. There was no doubt we both had been overpleased tonight.

We fell asleep naked in each other's arms. Her room dark, warm and dry. Not surprisingly every time one of us got up to use the bathroom, or rolled over to a more comfortable position, we would end up fooling around more. During the course of that night through Sunday I fingered her pussy and ass, as she stroked my cock, fingering my ass. I fucked her hard, as she rode me and from behind. I fucked her in the ass again. And yes, she fucked me more with the strap-on again to the point of being sore and achy. I wanted more; I just couldn't take anymore. Before dawn had broken, I think she came 15 times and I came 4.

It was- unfortunately -- the last time I saw her. But It was the best night of female sex -- with toys -- I had ever had and I truly wished she was younger or not sick, so we could have stayed together. But I wanted more out of a relationship and still wasn't sure if I going to want children or get married, or just date guys. All would be answered in the following years.

To be Continued...