How I became a GURL -- Part III -- Fulfilling the

Now that I was fully versed in being a gurl, I needed to know if I could turn a man on in person, not just looking through a glory hole. I wanted to have a man treat me totally like a woman, take me to a hotel and make love to me, completely as a woman.

But where to find the guy?

The answer was a chat line. I got an account as a girl -- I signed on as Jennifer, explained what I was and what I was looking for. As you can tell my voice is very fem (listen to my voice into or watch my vid it you don't believe me, giggle) and it was pretty easy to turn guys on and grab their attention.

Of course I got all kinds of messages, most of them pretty lewd and straight forward -- the kind of stuff a guy says when he is jacking off to your voice while watching porn. I already knew I could inspire lust like that. I wanted something more.

Finally there was a nice guy who just flirted with me, treated me like a woman and tried hard to get a DATE. This was SO exciting. This was something I had been wanting, needing, longing for since I was 15, although I hadn't known it. A man wanted me as a GIRL! Like he would want any girl!

It was clear he wanted to meet me to sl**p with me, but somehow that seemed secondary to our conversations. So I agreed to meet him at a local Dennys on a weekend night. He told me he'd be in a booth reading a certain book and I could come in and meet him and we'd go from there.

It was several days until our date, and I was in a constant state of excitement and anticipation. I couldn't wait!

Finally the night arrived. It was cool and a little rainy. My wardrobe wasn't very big yet, and a bit conservative, but I put on my cutest outfit. White stockings, white pumps, a pink teddy with garters, pink frilly panties -- very virginal stuff -- and wore a tight gray sweater and a long purple pencil skirt that went below my knees -- certainly not the kind of slutty stuff I like to wear now. My wig was blonde/brown in a very cute page boy style. With my nails painted and makeup on, I looked at myself in the mirror. What I saw staring back with me was a cute, virginal young girl, very sweet looking but also somehow very sexual. In some ways I couldnt' belive how good I looked, and in others I felt like I was seeing myself in the mirror for the very first time.

I drove to the Dennys, but once I parked I was seized with uncertainity. Not doubt as to what I wanted and who I was, but the idea of just walking in the restaraunt as a woman. Suddenly I doubted how passable I was, how I'd feel if people stared and whispered. Today I could care less and get off to the stares and whispers, but that night I was nervous.

After setting in the car for 20 minutes I finally took a deep breath, got out of the car and began walking up the sidewalk. Halfway to the door a handsome man came walking toward me, and as he neared he asked "Jennifer?" I was thrilled and relieved; I wouldn't have to go inside, but here was my date!

I apologized for being late and explained why I was. He told me it was OK, that he was so glad I showed up. I told him I wasn't sure if I looked like he expected. He said I was more beautiful than he had anticipated and that I looked like a sexy 1960s starlet.

My heart fluttered. It was my first real compliment as a woman -- at least the first one I had gotten without having a cock inside me.

We drove across the highway and got a room at a Motel 6. We went inside, turned off most of the lights and then he took me in his arms and kissed me deeply. I swooned. It was heaven, the first time I had actually kissed a man on the lips. I almost went limp.

After we necked for awhile I had him lay down on the bed, while I stripped off my sweater and skirt. Once he saw me standing there in my pink teddy, graters and white stockings and pretty pink panties, he moaned -- I mean he moaned! Deep, lustful and awed. I can still hear it all these years later. It was a moan that told me how fantastic I looked, how much he wanted me, how much of a woman I was!

Boy did I reward him for that moan. I dove on his cock and sucked him like I'd never sucked anyone! His cock was very thick, probalby about 4 round and 6 long. I had never taken one so thick, but from the way I was bobbing up and down on his meat you'd have thought I had one that size in my mouth nightly! He was moaning with pleasure, and very, very hard! I couldn't stand it anymore and begged him to fuck me!

Naturally I didn't have to beg long. He stood up, I laid down on my tummy and put my ass up in the air. I felt his hands grasp my panties and pull them down. GOD! That felt SO INCREDIBLE!!!!
With my panties down I felt him lube my cunny and then the pressure of his cock at my opening. No one that big had ever been inside me before, but in the days of waiting I had been using a flashlight as a dildo, and that was about the size of his dick, so I opened right up and in he went!!!!!

I was in total heaven as he thrust in and out of my ass. Here I was with a handsome gentlemen fucking me, all dolled up in my pink lingere, laying face down on a hotel bed with my ass up in the air! It was so feminie! I was so feminie!!!

Finally, but too soon, I could tell he was about to cum. There was no rubber, so I told him to cum all over my ass. He pulled out and seconds later I felt a huge load of hot cum splash all over my ass cheeks and thighs! I came into the sheets as he coverd me with his hot juice!

He collapsed on the bed, breathing heavy like men do after they cum, drew me into his arms and kissed me deeply. I loved it, I knew now that I had finally become for real what I had always been inside -- a woman, and in a since I had just lost my virginity as a woman!

After awhile he got up to shower, and then realization of what had just happened hit me! I got up, dressed quickly and left without even saying goodbye. It was a little rude, but I knew he was happy. I wished I'd stayed though b/c there might have been more dates later! But for now, I drove home happy and hard -- a girl for real and a new life ahead of me as a woman!
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Categories: First TimeShemales
Posted by jenn1
3 years ago    Views: 843
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3 months ago
Awesome story Jenn so beautifully written too
First time is so amazing & s unforgettable
Thanks for sharing
3 months ago
Good girl, no man can resist a sissy dolled pink teddy, graters and white stockings and pretty pink panties.. soooo exciting!!
6 months ago
You are such a lucky gurl to find out who you are sexually so young.
1 year ago
great series, too bad you didn't keep in touch. first loves are so special
1 year ago
Fantastic Jenn1you did it and now you need todo it againandagain have great stories to rtell of all your adventures
1 year ago
wow amazing sexy story
2 years ago
What a lucky guy,I would have had to chase you through the parking lot and made several more dates
2 years ago
Here is how to become a shemale.....

and loving it
2 years ago
love your stories they are very good, hot, and they also made me very horny :)
3 years ago
Jen, that was HOT!!
3 years ago
Ooooo baby that was so sexxxy
3 years ago
wonderful sexy story! thank you!
3 years ago
more keep it comming
3 years ago
This is the best i've read in sometime you are greast aloso jacked off to your story thanks
3 years ago
very well written stories! Keep them cummming...