Mike's first transgendered experiences part 10.

Please go read 1 -- 9 before reading this one.

Cheryl enters my life.

I had been about a month since I had last seen Enna. She hadn't returned my calls or texts, so obviously we were over and I needed to move on. I was still working at the Big Box store and was at work one day when I was approached by this older lady who came up to the counter I was working at. She said, "Excuse me, can you help me find the TV section."

I tried to just point her in the right direction, but she seemed so lost and out of sorts that I decided I'd walk her over there. Along the way, she told me her husband used to handle these things, but since he was gone, she had to do it herself. I showed her several TV options helping her select the TV that would best suit her. During our conversation, she introduced herself as Cheryl. She was probably in her mid to late 50's, short brown hair, which was styled. She was about 5'5" inches tall medium build with a bit of extra weight, but she did have a nice set of tits, which were still plump and full. After I helped Cheryl get the TV in her cart, she asked me for my name and thanked me for helping her and went on her way.

A few days later I was stocking some shelves, when the manager came across the portable radio and said, "Mike there's a customer requesting your assistance in Electronics."

I walked over to the area to see Cheryl standing by the counter. I remembered her and said hello when I arrived. Cheryl said, "Mike, I know this seems weird, but I couldn't get the TV hooked up, so I was wondering if you could help me set it up?"

There were no rules saying I couldn't help her out at her house, but it seemed like an odd request. But being the compassionate individual I am, I decided I would help her. Cheryl wrote down her address and I told her I'd come by tomorrow at 4:30 after work, to help her out. The next day after work I drove to her house. When I arrived, she let me in and I worked for a while getting her new TV set up. It was just about dinner time when I finished and since she had already started cooking Cheryl insisted, I stayed for dinner. I tried to decline her offer, so I could just go home, but she wouldn't take no for an answer. I stayed with her for dinner and we had a great conversation. Through our time together that night, I learned her husband of over 20 years had passed away a few years back from cancer. Cheryl told me they traveled a lot, never had children, most of her family was gone and since he had a great job she never had to work. Cheryl had come to rely on him for everything. Seems he paid all the bills, handled all the major issues and purchases and even thought the house was paid for and she was well off financially, she had no idea how to maintain a house or handle things like buying a TV. Cheryl was pretty alone in the world and was still trying to figure out how to do things he handled. I felt bad for her, but seems their marriage was blissful and full of excitement.

I sat with her after dinner and had a drink while we talked more. I hadn't even considered her sexually; I was just appreciative of her kindness and was truly enjoyed meeting her. Before I left, I gave her my number and told her if she needed anything, or someone to talk to she could call me. Over the next couple weeks Cheryl and I did talk more; and the more we talked the more I enjoyed her friendship. One night after a very long day with customers and my ignorant supervisor I was just about to leave when Cheryl called me. I was telling her about my bad day and saying that was just planning on heading home, decompressing, getting drunk and going to sleep when she said; "Why don't you come over and have a drink with me? We'll put on some music and you can just relax and tell me all about it."

I figured, "What the hell" and agreed to head over. When arrived at Cheryl's she was wearing black high heels, a black miniskirt, with black nylons and a silky off red colored shirt, with a few buttons open exposing a bit of her chest area. She invited me and gave me a long warm hug as I entered. I sat down on her couch while she poured me a drink. She sat down next to me, leaning in my direction. We chatted about my day and when I finished my drink, she refreshed it rather quickly. After my tension was gone and I vented a bit, my mood changed and I was having a much better night. It wasn't long until the alcohol kicked in, along with my hormones and suddenly I was very interested in seducing her. But it seems, she was more interested in seducing me. Before I could even begin to make a move, Cheryl leaned in and placed a soft kiss on my lips. I was quite taken-a-back by this but surely had no issue with it. We both stared into each other's eyes for a moment and both leaned in for a deep French kiss. My hand cupped her face as her hands rested on my legs. I reached my hand downwards and I felt the soft silkiness of her pantyhose as I rubbed my hand up and down her leg.

I felt tingling in my stomach I hadn't felt in a long time; at least tingling for a woman. My dick started to get hard and I wanted her. Cheryl and I spent a long time on the couch making out. I cupped her breasts over her shirt, felt her hand rubbing up and down my thigh. Our breaths thickened as I felt her start to unbutton my jeans. Her trembling hands working on getting my zipper down as I was trying to pull her skirt further up. Cheryl pulled from our kiss and unbuttoned her shirt sliding it off. Her tits were big and plump and being held up by her bra. She reached behind her and unclasped her bra, pulling her arms through it, letting it fall to the floor. Her tits dropped as my hand reached for them. We went back to kissing as I touched and caressed her breasts, her hand reaching down into my pants grabbing my cock and slowly stroking it. I was so tuned on. It had been a long time since I had been with a woman, but I was enjoying every minute of it.

Cheryl slid off of the couch and down onto her knees. She pulled at the side of my jeans sliding them down. She lightly kissed along my knees and inner thighs as she reached for my underwear. She slid those off and edged in closer. Her head dipped sone and she put my hard cock in her mouth, I leaned back further and felt excited as her warm mouth slid up and down my shaft. I watched the back of her head bobbing up and down as she was sucking me off. Cheryl spent the better part of five minutes sucking me off, until she pulled away. She got back onto her feet and kicked her heels off. Her saggy tits hung as she unzipped her skirt, letting it fall to the floor. She had no panties on, just the pantyhose. I could see her pussy, lightly covered in hair, as she stood in front of me. Cheryl slid out of her pantyhose standing in there in all her glory. She edged further towards me as my hand slid between her legs. She was soaking wet and wide open. Her husband must have been hung, because her pussy was wide and loose. I caressed my hand back and forth along her wet lips as my mouth sucked one of her nipples. Cheryl pulled me off of the couch as she leaned down to the floor. She laid on her back and pulled me on top of her. I was so horny and so ready to fuck her.

Once I was on top my dick slid easily into her. She was wet, warm and sticky as I penetrated her. I pumped back and forth at a slow deep pace, hearing her moan. Our eye contact was immense as I slowly made love to her. Cheryl wrapped her legs around me and our kissing increased while I slid in and out of her pussy. It was a great feeling to be back inside a woman and as much as I was enjoying the moment, I was used to a hard cock deep inside my ass. After a while of being on top of her, I rolled over pulling Cheryl on top of me, without breaking from being inside her. She adjusted herself once she was on top of me and rode me for a long time. I could feel her wetness spewing from inside of her all over my crotch. I cupped and sucked on her tits, bringing her to her first orgasm. She leaned down kissing me deeply as she continued sliding me in and out of her.

Just after her second orgasm, she pulled herself off of my cock and slid herself backwards. Cheryl kissed her way down my body, until she reached my dick. She put my hard cock back in her mouth and sucked me off for a while longer. I wanted to be back in her, more importantly I wanted to fuck her in the ass, because that's what I had been used with the transgender girls. I leaned forward and up pulling Cheryl from my dick. I placed her on her knees and climbed in behind her. I slid my cock back into her pussy and was pumping back and forth listening to her moan. I was so curious on whether or not she preformed anal, that I took the pad of my thumb and started rubbing around her asshole. Cheryl reacted acceptingly as I continued to rub her ass while slamming my cock in and out of her. I mustered up the courage and placed my middle finger in my mouth getting it all wet with saliva and sild my finger deep in her ass. Cheryl's head leaned back in pleasure as she moaned deeper. I continued fucking her with my cock and my finger as she orgasmed again.

As I was getting closer to orgasm, Cheryl pulled away from me, letting my cock pop out and said, "Sit back on the couch, I'll be right back."

Surprised, yet curious on what she was doing, I climbed back onto the couch and watched her walk towards her bedroom. I was catching my breath just looking down as my body and stiff dick when she returned to the room. Cheryl was holding a bottle of lube in her hand. She got down onto her knees and poured a bit out onto her hand. She used her hand to start stroking my cock. The cold lube, coupled with her warm hand and tight grip was erotic. I started lightly thrusting my hips up and down as she continued stroking me off. Cheryl's head dipped back down and she placed my cock back into her mouth. Her hands rubbed up and down my inner thighs getting closer and closer to my ass cheeks each time. Cheryl pulled my hips further towards her, edging my bottom further off of the couch. She spread my legs further and was just rubbing all over the under part of my legs. I knew what she was about to do and got even overly excited. Within a few strokes, I felt her soft trembling hands slide up in-between my ass cheeks. Her fingers twirled around my asshole as her head continued bobbing up and down on my cock. She pulled her hands away for a second as she lubed her fingers up, returning them to my ass. I felt the coolness of the lube hit my asshole and I was begging her (in my mind) to ram her fingers deep inside me.

With a few deep penetrating rubs, I felt her slide a finger inside me. I groaned in pleasure as it dived in and out of me. Cheryl was fingering me, as she was giving me head and I was loving it. I closed my eyes and just sat back enjoying being pleasured. Cheryl fingered me for a while until I was loose and open and then slid a second finger inside me. I moaned out in pleasure as she continued ramming her fingers deep in my ass, while her mouth continued sucking my hard cock. Her focus was more on fingering me than sucking me, but I didn't mind. I could see her arm swinging back and forth and felt the pressure of her fingers bringing me closer to orgasm. Cheryl pulled my cock from her mouth, looked up at me and asked, "Do you like it?"

"Yes." I replied. "Just like my boyfriend used to do it," Slipped from my mouth.

Cheryl's eyes affixed to me, like a billion questions were running through her mind, but instead of asking, she just kept ramming her fingers in and out of my ass while her mouth retuned to my cock.

The feeling was intense, erotic and satisfying and as I was getting close to orgasm, I wanted to cum in her. "Cheryl," I moaned out. "I want to cum in you."

Cheryl withdrew her fingers from my ass and pulled her mouth from my cock. She climbed on top of me on the couch sliding my hard cock deep inside her soaking wet, warm pussy. Cheryl started riding me again slowly at first, with long deep rises, but driving down harder and faster as she brought herself to another orgasm. Her sloppy wet pussy continued bouncing up and down on me until I was ready to explode. "I'm going to cum Cheryl," escaped from my mouth.

I moaned in pleasure as I shot my load deep inside her pussy. It had been forever since I came in a girl and the pleasure was more than I could take. Our mouths met as I expelled every drop. My ass wide open, wet and tingling from being finger fucked. Her pussy pulsating as she was coming down from her climax.

After we caught our breaths, Sheryl asked me, "Did you say, like your boyfriend used to?"

"Yes." I replied. "I recently got out of a gay relationship." I didn't want to try to explain transgender to her, so I just said boyfriend.

"Are you Gay?" She asked.

"No, I am Bi-sexual." I replied.

Cheryl said, "Have you dated many men?"

"No, just a couple." I told her.

Cheryl and I talked for a while about my experiences and hers. It seems her and her husband had many adventures during their lives together. Sheryl admitted she had been with a woman and had two men at once, but always stayed loyal to her husband.

I asked Cheryl, "How did you know I'd like anal?"

Cheryl replied, "I didn't know, but I was hoping. I always loved fingering and fucking my husband and he enjoyed it, so I was hoping you would too."

I asked her, "Fucking him?"

"Yes." She replied. "We had a very kinky sex life, I fucked him with my strap on a lot and he fucked me in the ass a lot."

Cheryl followed; "I actually like it in the ass more than the pussy, so anytime you want anal is fine with me."

I about got rock hard again. In my mind I thought; Did I just find the woman of my dreams?

Cheryl and I spent a while lying around naked, smoking some cigarettes and having a couple more drinks. I left there that night feeling very glad I had met her and even though she was way older than I was. I was thinking maybe this could be more than just a fling.

To be Continued...