Becoming Mindy

Hi. This is my story from an unsure, shy, awkward boy that was pretty feminine to a proud, confident and comfortable transgendered girl. If you're not into reading about transgendered people and their stories, as well as their sex lives, then please move on. I know I made some foolish decisions, but I am a completely healthy person today and those decisions, albeit foolish, helped make me into who I am today. I hope you enjoy my recounting of my journey.

----

Where to start?

I guess I should start with that I've loved to wear panties. In high school, I would sneak into my mom's room and put on her panties.

While I was straight, at least so I thought, my fascination with panties never stopped.

In college, after my parents died in a car accident. I had my first gay experiences, including my first crossdressing experience for Halloween my freshman year. After my parents passed away and since I was an only child, I basically came out and began to openly experiment with my sexuality with both men and women.

However, my true passion was dressing as a woman and having sex.

I was somewhat of a natural at school and graduated with an MBA by the time I was 23. I had attended school at Stanford, which had opened me up to the San Francisco gay scene, and took a job in Los Angeles after I graduated.

My parents had left me, as an only child, a rather large trust fund. While I couldn't really touch the principal, the interest left me with another seven figures to play with and after college, made finding a job much easier since money wasn't an object.

However, I hated my job, even though I had been there less than a year, and would spend weekends having mindless sex, sometimes with guys and other times with girls. Standing at 5'7" with a narrow, almost feminine frame, both guys and girls were attracted to me. While I was 23, I looked younger.

In fact, this all started during one of those weekends when I invited a guy I had met back to my place. Of course, the clothes came off and it wasn't long before he was fucking my ass from behind.

Since I had kept my body shaved, starting in college and continuing after, he started calling me a sissy fag as he fucked me. He told me I would be a better girl than a guy. I had one of the best orgasms of my life as pounded me and called me those names. As he fucked me, all I could think about was how much fun I had dressing a woman in college.

Once he left, the thought of dressing as a girl in panties consumed me and I found myself wearing women's panties all the time. I also found crossdressing porn in the Internet.

I was hooked and a month later, I had purchased makeup, wigs, heels, dresses, skirts, blouses, lingerie, fake nails and stockings. Of course, money was not an object.

I started dressing regularly as a girl when I was at home and I had a couple more sexual encounters with guys. I was becoming obsessed with cock. In fact, I was paying more attention to the guys in porn scenes than the girls.

I wanted to get fucked again as a gurl.

I posted an ad on Craigslist saying I was a new CD and wanted to find a guy that would treat me like a lady and fuck me like a slut.

I got numerous responses, but the guy that caught my attention was a middle-aged married man who said he hardly had sex anymore with his wife and being with a CD was a fantasy of his.

We agreed he'd come over to my place the next day, which was a Saturday.

Since he was to be over around 2 in the afternoon, I started getting ready around 9 in the morning. I started with an enema and then a bubble bath. While in the bath, I made sure to shave every inch of my body and put in my medium butt plug.

Once out of the bath, I covered myself liberally with lotion and then I slid on a pair of panties, yoga pants and tank top.

My makeup was next. I took some extra time and decided to go super slutty around my eyes. I had to admit, I looked good in the mirror when I was done. Combined with my youthful male looks, I looked 18-19 in makeup.

I topped off the look with some French-tip fake nails.

I then took everything off and started to dress for him. I put on a bra that held my breastforms, my gaff to hide everything, a pair of thigh highs and a short dress that definitely showed off the top of my thigh high stockings.

I had timed things perfectly, because I got a text from him just as I finished putting on the dress telling me he was on his way.

I put on my blonde wig, removed the butt plug, and slid on a pair of platform pumps.

I was nervous beyond belief and decided a couple of shots of whiskey were in order to calm myself. Just as I finished the second shot and used some Listerine to freshen my breath, I heard a knock on the door.

"You look gorgeous," he said in a voice that sounded as nervous as I felt.

"You're too kind," I gushed back in my best feminine voice.

I asked if he wanted a beer or something and wanted a beer. I told him to have a seat on the couch and watch the game, which I had on the television.

I got the beer and joined him the couch, making sure to sit close to him.

We made some nervous small talk as we watched the football game on the television. I realized he was too nervous to make a move, so I took it upon myself.

As he was saying something about his wife, I moved my right hand to his lap and gave his cock a squeeze through his jeans with my manicured hands. He stopped mid-sentence and let out a gasp and I as I turned to face him, he moved into kiss me.

I've never been one, up to that point that was into kissing the guys I was with, but this was different. It took about five-seconds for our tongues to connect and the passion was immediate.

We rearranged slightly on the couch so his arm was around me and was pulling close to him as our mouths never parted, but I was now stroking him through his jeans with my left hand. His hands, however, were all over me.

I had never been so turned on in my entire life.

He pulled me onto his lap as our kiss continued and I began to work to get his shirt off. Once I did, I began to kiss his chest and work my way down.

I slid off his lap onto the floor on my knees and started to get his jeans off. However, I realized I had never tried to unbuckle a belt or unbutton a pair of jeans with fake nails, I couldn't manage it very well. He noticed my predicament and undid it all himself so that I could get his jeans and boxers off.

Once I did, I saw his cock, which wasn't huge but about 6", and very hard. I felt a gush of pride that I was able to make him this hard. Of course, I knew what was next and started to suck his cock.

I still hadn't perfected the art of deep throating, so I alternated between sucking the tip of his cock and stroking it with my hand. Based on him moaning, he had no complaints and I really enjoyed the power my gurly look had on him.

Before he got too close to cumming, I pulled back and looked at him as I grabbed a condom and lube out of the table drawer next to the couch.

"Put this on," I said to him in my best seductive and feminine voice. "I need this cock in me."

As he put on his condom, I stood and removed my dress and gaff. I was standing before him in just my bra, which contained my breastforms, thigh high stockings and heels. The obvious hard cock that was sticking out from my shaved body betrayed my wig, makeup and everything else that made me look like a gurl.

However, he put me at ease very quickly.

"You are so fucking hot," he said as he stood and started to apply the lube to his condom-covered cock.

His words lit a fire in me as I stepped into him, wrapped my arms around his neck and kissed him with a passion I've never had before.

"You want to fuck me," I asked him when our kiss broke.

"Yes," was his simple reply.

I got down on my hands and knees while motioning for him to get behind me.

"Then fuck my ass like you've always wanted to fuck your wife but she wouldn't let you."

He didn't need any further encouragement. It was a good thing that I had used the butt plug to relax my ass, because he pushed into me without a care for me and had his entire length in my ass in one thrust.

"Oh my god," I exhaled. "Your cock feels so fucking good. Now, fuck me."

He did. He pounded my ass for thirty minutes. We started in doggy on the floor, moved to reverse cowgirl on the couch before we ended up in a missionary position, kissing again, on the floor.

I came without touching once in doggy and came again while I played with my cock, which wasn't softening at all, while in reverse cowgirl.

While we were in missionary on the floor, I had an orgasm without cumming from my cock. It was the most amazing feeling I'd ever had. Pure euphoria.

He told me he was about to cum and I told him I wanted him to cum in my mouth.

He quickly got up and removed the condom as I got onto my knees in front of him. I started to suck the tip of his cock as he stroked himself.

I felt him tense up and shoot his first load in my mouth as well as the second. It was obvious he hadn't cum in awhile because there was a lot of cum in the first two shots.

Realizing I was about to choke on the cum in my mouth, I pulled back to swallow, but as I did, his third and fourth shots landed squarely on my face. After a quick swallow, I started to move my mouth back to his cock to swallow some more, but his fifth shot was before I got all the way back, leaving me with a cum mustache.

He filled my mouth with his smaller final shots as I sucked the last of the cum out of his cock.

He fell back onto the couch and after I cleaned the cum off my face with my panties, I joined him the couch. We positioned into a spoon position and watched the football game with me in his arms.

He slowly traced the side my body with his right hand from my hip to my shoulders. I melted back into him and could feel his cock hadn't gone completely soft. His cock was between my ass cheeks and pressed forward and back with my hips and could feel him thrust forward when I pushed back into him.

A few minutes later he was hard again.

"I haven't been able to recover so quickly in years," he whispered in my ear.

I turned my head back toward his and smiled. He moved to kiss me and I met his tongue immediately with mine. As our tongues began their familiar dance, I reached down for his cock and positioned it the opening of my ass.

Taking the hint, he thrust forward and easily entered my already opened and lubed asshole.

It was the first time a cock had entered me bareback.

"You really are a slut, aren't you," he whispered into my ear. "You want it bare, don't you?"

I turned my head and nodded yes as I looked into his eyes as he began to thrust into me continuously.

I kept looking into his eyes as he fucked me in a modified spoon position.

"You're loving this," he said as he pointed to my cock, which was hard again.

"Fuck yes," was my gasped reply. "I love having you fuck my sissy ass."

He reached down and touched my cock, which exploded and shot my cum halfway across the living room floor. As I shot, it triggered a body-wide explosion of fireworks in me that must've lasted a minute.

I don't know if I blacked out for a little bit or what, but when I was able to gather my senses, he moved me onto my stomach and entered me as laid himself on top of me.

He adjusted himself to where his arm was wrapped around me under my throat and his mouth next to my ear.

Every time he thrust into me, my body would be forced into the couch, which caused my throat to press against his arm. This resulted in a mini-firework display throughout my body every time he thrust. Unbelievably, I felt my cock get hard again.

"Your ass feels fucking amazing," he whispered in my ear. "I could get used to having this ass at my disposal. Would you like that? You could be my personal piece of ass on the side."

I was hardly able to talk with the euphoria I was feeling and his arm against my throat, but I was able to manage a coherent sentence, albeit in a muffled and distracted voice.

"You can have, oh god that feels good, you can have my ass any time, fuck, fuck, fuck, my ass any time you want."

"Tell me how much you love my cock in your ass," he whispered as he spanked my right ass cheek.

"Fuck, fuck, yes, spank my ass as you fuck me. Your cock feels amazing. I love your cock in my ass. Fuck me. Fuck me hard. Spank me too."

He lifted his arm and as he lifted me he put into a little bit of a wrestling choke hold as he fucked me and began to spank my ass with his right hand. He was now using me as his own fuck toy and taking some sexual aggression out on me.

I loved it. Every minute of it and I felt my cock explode again under me leaving a cum spot on the couch as he continued to push me into it.

With the choke hold, spanking, fucking and my explosion I was now in a constant state of orgasmic euphoria.

He was relentless as I think he was trying to pound me through the couch. However, I felt him begin to swell and he was ready to cum.

"You want to me to cum in your slutty sissy ass," he asked me. "A good slut whore wants cum in their ass. Are you going to be a good slut whore for me?"

"Yes, please cum in my ass," I was barely able to say. "Fill my slutty ass with your cum."

I felt him tense up and shoot his cum in my ass. I had never felt that before, but it triggered another orgasm sensation in me.

Once he was done coming, he collapsed on top me, but kept his cock in me, which I could still feel twitching from his orgasm.

While I couldn't move under him, I don't think I would've been able to anyway since I was wiped out from the experience.

After a few minutes, we had both caught our breath enough to where we were able to adjust back into a spoon position. He wrapped his arms completely around me and I melted back into him.

I had never understood the cuddle craving that many women have after sex until that moment. It was perfect and when I turned my head back to see him and smile, he met me with a sweet kiss and that turned into a slow tongue dance. With the brutal fucking that had just taken place, it was the perfect show of tenderness.

We remained snuggled together for another ten minutes before he told me he had to leave because wife would be expecting home in another 30 minutes or so.

I told him I understood as I stood to slide my dress back on. He got dressed as well and I walked him to my door. I put my arms around his neck and he put his hands on my hips.

"Can I text you and see you again," he asked so innocently that it was like it wasn't the same guy that I had just fucked me in such a forceful fashion just 20 minutes ago.

"So long as you fuck me like you just did," I replied smiling and looking in his eyes.

"That's why I would want to see you again," he said and matched my smile. "And next time I'll bring you a gift or two."

"Ahhh, that'd be sweet," I said feeling excited to be so wanted. "You don't have to do that, but I won't turn down presents."

He bent in and kissed me and I returned the kiss as our tongues began what was becoming a very familiar dance. We kissed for a minute or so.

"I've got to stop or I'll need to bend you over and fuck you again and I need to be home soon."

"You can bend me over right now if you want," I said. "I'm ready anytime you want me."

"You're evil," he said with a big smile. "As tempting as that sound, I need to be going. I'll text you soon."

We kissed again and he left. I was really hoping he wanted to bend me over one more time and was disappointed he didn't. I felt like I could get fucked all night long and it was only 4:30.

I had an idea. I grabbed my phone and sent a text to one of the guys I had been with recently as a guy.

"Remember how you said you find cross dressers hot," was my text.

I went to touch up my makeup and get prepped again.

"Yes. I do," was his reply.

"Surprise," I replied to the text and included a selfie of me all dressed up.

"Holy fuck, is that you?"

"Yes, but I go by Mindy now when I am dressed up. Want to cum over?"

"Fuck yes. I'll be there in 30 minutes."

Once he got there, we fucked two times that night and once again on Sunday morning.

----

This was all three years ago. I have a lot more to share.