My First Encounter

Story Info
The reactions he gets when he becomes a she.
1.7k words
4.22
104.5k
3
6
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I constantly thought about how feminine and desirable men might make me feel if they looked at me as a girl. I decided that the only way I would ever find out was to stop dressing privately at home and go out into the real world as a woman. I had lots of dresses and lingerie, but I just had to get some new clothes for this excursion.

I went shopping, and I bought the prettiest blouse, a lovely skirt, a darling slip, sheer nylons, a pair of sling-back sandals with 2" heels, a necklace, earrings, an ankle bracelet, and a pretty little purse.

The blouse was a pink silk poet's blouse with a ruffled plunging neckline and satin cuffs. The skirt was a baby blue linen sheath. The slip had a frothy lace bodice and hem, with satin ribbon bows worked into the lace. The necklace and earrings were crystal drops, and the ankle bracelet was very thin, fine gold, with a tiny crystal heart charm. I was bound and determined to have a real experience, no matter what. My feelings were so very strong!

I took a long bubble bath, brushed my blonde ringlets until they shone, and made up very carefully. Then I got all dressed. When I was done, a little of the lace from my slip showed at my neckline. I thought I looked very pretty. I put on my new spring coat to hide my figure a bit. It had a satin lining and felt so feminine. Then I picked up my new purse and went out.

I walked to the train, to go into into the City. At the station, I could feel men looking at me, but none said anything to me at all. My coat did not let them really see me. All they saw were my legs and heels, the bulges in my coat that were my breasts, and my face and hair. On the train, I still got the feeling that men were eyeing me, but no man sat in the seat next to me. It was so wonderful just to be out as a woman. That feeling, all by itself, is so marvelous.

I got off the train and strolled out onto the street. The feeling that men were looking at me was even stronger here. Of course, there were lots more men. I decided to go to a movie, so I went up to a nearby theatre. There was an older woman in the kiosk, and she looked at me and smiled warmly. "Don't you look pretty today, dear!" she said. I was so complimented! This was a woman. Telling me I looked pretty! I was on cloud nine. She gave me my ticket and I went in. It was warm in the lobby, so I opened my coat. The ticket taker inside was an older man, maybe in his sixties or seventies. He looked me up and down with great admiration. He made a point to touch my hand as he took my ticket. He was so obvious! I was positively thrilled.

Inside, in the dark, I removed my coat altogether and hung it over my arm. I slowly began to climb the carpeted steps to the balcony. There were only two or three people sitting up there in the late morning, and I wanted to savor the feminine feelings I was having because of the two people I saw coming in. About halfway up, in an aisle seat to my right was a very handsome young man. He glanced up at me, and I could see that admiring look in his eyes, even though he was no more than eighteen at best. I lowered my lashes and kept climbing, but more slowly. I could actually feel his eyes on my skirt as I went up the steps past him. I just KNEW he was twisted around in his seat watching my bottom sway as I climbed.

I sat in a row about five above him, on the other side of the aisle. By then, he was watching the movie again. I placed my coat and purse on the seat behind me, crossed my legs, and let one high heel dangle out into the aisle. I made sure my skirt slid up my thigh, so that a tiny bit of the hem of my slip would show. Sure enough, in a minute or two, he swiveled around in his seat. I could tell he was surprised to see me sitting so close to him, because he turned back very quickly, like he was caught looking. My heart was pounding. My feelings were so indescribably feminine! I had never felt so much like a girl before in my whole life. He looked back again, and I demurely lowered my lashes. Through my eyelashes, I could see he looked at me longer before turning back around. The next time he turned around to look at me, I smiled softly at him. He abruptly got up from his seat and went out. I was crushed! I thought I was going to have a genuine encounter, and I felt sort of spurned. But that is an emotion too, and I love strong emotional feelings.

Ten or fifteen more people had come up into the balcony since I arrived, some men and some women, but none were seated near me, so I began to look around to see what I could see.

I was amazed to see my young man come back in again after about five minutes. Instead of leaving as I thought, he had just gone out for a while, perhaps for a drink or to go to the men's room. My heart fluttered again, wildly. He came back up the steps, but he did not stop at his row. Instead, he came all the way up to mine and stopped! He bent over me. I knew he could smell my perfume and see my bra down the neckline of my blouse from that angle. He whispered, "Pardon me, Miss," and started to pass into my row. I put my legs out into the aisle, and he slipped past me and sat in the seat one away from me, leaving an open seat between us. There was no one else in the whole row. I looked at him, and he looked at me. "Hello," I whispered, and slid into the seat next to him.

I couldn't believe what seemed to be happening. It was just as I had always dreamed it would be. He smiled and put his arm around my shoulder. When his hand touched my silk blouse, it was like an electric shock. No man had ever touched me as a woman before. It was incredibly exciting! I couldn't help snuggling up next to him. I looked at him and could see what he wanted in his eyes. Oh, I wanted it too, so very much! He leaned over, and I caressed his cheek, fluttering my lashes shut. He had a sexy little stubble, and my heart began to pound. Then, he kissed me.

My arm slid up around his neck, and I responded. This was what I had wanted since I was a little girl! A man treating me as the object of his desire. His kiss was intense and very passionate. He moaned deep in his chest and kissed me like I was the answer to every dream he ever had. His hand moved to my skirt, and I got scared. He was sure to find out if he touched my panties! I took his hand in mine and moved it to my breast. He stayed there, fondling my bra through my blouse as he kissed me. It was a long, lingering kiss, filled with his desire, and it thrilled me.

I reacted to his kiss just as I had always imagined, with a woman's emotions. I felt extremely feminine, and it seemed like I excited him, and that was so satisfying to me. What also thrilled me was the way we appeared to any people who might have looked over at us kissing. I realized anyone who saw us would never doubt that the girl he was kissing so passionately as a beautiful, desirable woman. The thought that everyone was just automatically treating me as a total female was what really fulfilled me and made me tremble with excitement as I kissed him back.

He kissed me for a very long time, then almost reluctantly moved slightly away. He was breathing very heavily, his body trembling like mine, his hand still on my blouse, so I knew I had affected him a lot. He hugged me tight, and I laid my head on his shoulder giving him tiny, soft butterfly kisses on his neck. I had never, ever felt so completely, absolutely feminine before in my life! That kiss was the most exciting experience I had ever had.

I knew if I stayed with him much longer, he would insist on getting far more intimate. After all, the first place he had tried to put his hand was on my skirt. This would probably have been my downfall, and I was pretty sure I was feeling much too feminine to control him, or myself for that matter. I whispered, "I have to go to the ladies' room, darling," making it sound like he was the cause. He took his arms from around me and smiled. I smiled back, very sweetly, picked up my coat and purse, and went up the balcony steps to the girls' bathroom. I could feel his eyes on my bottom all the way up, so I exaggerated my walk slightly to please him.

I had never been in a ladies' room before, and this one was really something. It was two rooms, really. A room lined with mirrors, vanities, and cushy little seats, and further in, an actual bathroom. I could see that my lipstick was really smudged, so I sat down at a vanity and began to fix my makeup. A lady came in, and in the mirror, I saw her smile when she saw me repairing my lipstick. I think she was one of the people in the balcony, watching him kiss me. That made me feel very, very good. A final check in the mirror showed that my makeup looked pretty again, so I slipped on my coat and reluctantly left the theatre, letting my good sense rule my emotions. All the way home on the train, I wondered what would have happened if I had gone back to him as I dearly wanted to. And I still do.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
6 Comments
AnonymousAnonymousover 20 years ago
What a kiss!

Great story. Extreemly erotic and very arousing. I hope to read of further adventures of this young temptress.

AnonymousAnonymousover 20 years ago
Thank you for introducing me to this lifestyle!

Your stories have allowed me to glimpse into the thoughts of a transgendered woman. I guess that is the proper term. I found the stories entertaining and moving and I find you attractive. Does MtF mean you have had the operation or that you live as a woman? I look forward to more stories.

AnonymousAnonymousover 20 years ago
lips ahoy

i am transfixed by your beautiful mouth, in particular, your full, sensuous lower lip. i have always found a full lower lip to indicate sensuality. i can think ofno woman with a better lip. i would love to nibble in it, lick it, suck it. perpaps you like it bitten some, a gentle twinge of pain could be very provocative. in all, i would love to reveal what must be a very beautiful body, to lick and suck and taste, to take you in my mouth, to insert my tongue, full length into your man pussy...to taste your cum. you make a tremendous woman, far more enjoyable than the many i have been with, i'm sure. good luck, darling!

AnonymousAnonymousover 20 years ago
Wonderful start

Your story really got my attention. I was only sorry that it was so short. Please continue when you can.

AnonymousAnonymousover 20 years ago
Sexy but composed

I certainly would like to have the honor to meet you. You seemed to be worth the time to take it slow and find out

how to be friends. Should friendship lead further, it would be on our terms.

Show More
Share this Story

Similar Stories

Morning Delight What happens to her when he comes in?in Transgender & Crossdressers
Cheryl's First Date Ch. 01 How she feels on her first date as a girl.in Transgender & Crossdressers
With Her Blessing A wife's understanding saves her marriage.in Transgender & Crossdressers
Back to School TG gets new gob, meets someone new and someone from the past.in Transgender & Crossdressers
Staying Together Compromises lead an unhappy couple to true happiness.in Transgender & Crossdressers
More Stories