The thoughts of a lady in transition as she explores her feelings for a teenage boy.
Cheryl's First Date
by deargirl
Jimmy is a teenager who lives on the same floor as I do in my apartment building. I rented my apartment as a girl, and everyone in the building only has seen me as a girl, including Jimmy. I think he likes seeing me, maybe a little more than most! He is about nineteen, and his apartment is at the opposite end of the hall from the elevator, right next to mine. He is tall, almost six feet, with wavy black hair and very good-looking. He plays football for the local college, so he is quite muscular, too. All in all, he is a very handsome boy.
Every time I go out, I have this feeling that someone is watching me walk down the hall to the elevator. All girls understand what I mean. I just know that a man’s eyes are on the back of my skirt, watching me walk. And almost every time I go out, as I wait for the elevator, Jimmy comes out of his apartment and joins me. Oh, he is very polite. He smiles and always says, "Good Morning, Miss Silkwood," or "Isn't it a nice day today, Miss Silkwood?" When the elevator comes, he lets me go in first, but then moves around to stand a little behind me. I can feel his eyes on my bottom all the way down to the ground floor. The feeling is exactly the same as the one I have when I walk down my hall to the elevator. It is really very flattering.
Today, we were in the elevator together, and he was standing behind me and a little to my right, in a corner. Suddenly, he asked me, "Miss Silkwood, do you like football?"
I turned slightly, smiled sweetly, and said, "Of course, Jimmy."
"I play quarterback for my team, Miss Silkwood, and I was wondering if you might like to come watch me play sometime," he said shyly. Just then, the elevator stopped at the third floor, and all sorts of people pushed their way in. There must have been twenty. I was sort of shoved backwards, right against Jimmy. For a second or two, I was pushed tightly against him. His face went into my perfumed hair, and I felt how very hard his masculinity was against the back of my dress. His hard bulge pressing against my soft bottom was unbelievably exciting.
The kids readjusted themselves, and the crush let up. I modestly moved away. I knew I was blushing. I turned to him and breathed, "I would love to, Jimmy. When is your next game?"
"Really? Friday night, Miss Silkwood," he said breathlessly.
"I'll be there, Jimmy," I whispered, "Oh, and by the way, Jimmy, my name is Cheryl."
"OK! Thanks, er....Cheryl," he said as we stepped out into the lobby.
He looked at me with such puppy-dog eyes that I almost giggled. I didn't though; he seemed so excited, and I was also more than a little turned on. I smiled at him very sweetly and cooed, "I'm looking forward to it. I've never known a quarterback before! I hope I will see you after the game to congratulate you."
"I will have them save a seat for you, Cheryl, right behind our bench on the fifty-yard line, and I will definitely see you after the game.” He went out the front door, and I just stood there a moment, not quite believing what had just happened. Was I, twenty-three years old, really going to a dinky junior college football game on her very first date? I had spent years on the hormones until my breasts swelled to a 34B and my penis shrank to less than 2”, avoiding men until I was secure enough as a woman. I was a girl in every way but one, and now, on my very first date as a woman, I was going out with a teenager? I must have been crazy to accept his offer.
I did not see Jimmy all week, and I completely forgot about his game until I checked my mailbox on Friday morning. Inside, was a ticket with a row and seat number, very official, with a little note taped to it. It said, "For you, Cheryl. I hope you enjoy the game. -Jimmy". Well now there was no question. I absolutely had to go.
That afternoon, when I got home, I took a long bubble bath with lavender aromatic candles burning. When I got out I patted dry, then spritzed my perfume behind my ears, at the pulse points in my wrists and temples, between my breasts, at my femininity, and behind my knees. Then, in my bedroom, I slipped on a pair of pink satin panties, trimmed in nylon lace. Then I cuddled my breasts into the matching nylon lace bra. I slid a beautiful hand-embroidered pink silk full slip over my head, and it slithered down my body. The bodice is the same thin, delicate nylon lace as my bra, and there is even more lace at the hem. Then I sat at my vanity and pulled on my thigh-high nylons. They are very sheer, nude, with lace tops and teeny little bows embroidered over my heels. I slipped my feet into my black patent pumps. They have 2" heels and a pretty strap that goes over my ankle. I buckled them, then started to brush my hair. When it was soft and shining, I fastened a few locks in a tiny black velvet bow just above my left ear.
I carefully put on my makeup, making my eyes delicate and big, and using a pale pink blusher on my cheeks. I then applied a tiny bit of perfume to my lips to set my lipstick, following it with a hot pink lip-gloss. I put on my crystal drop earrings and crystal heart pendant. I surveyed myself in the mirror, and I looked like a very sweet young lady, which is just the look I wanted.
From my closet I took the new blouse I bought at Macy's last week. It is pink silk chiffon with a sweetheart neckline and tiny puff sleeves. It is so pretty! I slipped it on, then pulled up my skirt, a black rayon sheath. It is just snug enough to flatter my derriere, but not so tight as to make me look slutty. Once again, I surveyed my look, and I thought I even looked fresher and daintier than before. I put my things into a little black patent clutch purse and got my fur out of the closet. I wore my white rabbit jacket. The fur is very silky, the satin lining is very feminine, and it cinches tight at my waist, emphasizing the drape of my skirt over my hips. One last look in the mirror to satisfy myself, and I picked up my purse and left.
At the game, I asked a handsome young usher if he could help me find my seat. He was very eager and led me right to it. "Here it is, Miss," he said. "right in the middle of the row." He smiled at me, with that look men reserve for sexy ladies, and I smiled back, shyly, as I worked my way into the row and sat down. I was in the front row, right at the fifty-yard line! All the rest of the row was filled with girls, so I assumed this was where the players' girlfriends sat. I was older than all of them, and they were dressed in ratty jeans and sweatshirts. None spoke to me. I guess I looked a little too classy and feminine for them. I primly crossed my legs and composed myself for the game.
Then Jimmy's team came out onto the field. He came to the bench right in front of me and put down some things. Then he looked up to where I was. He came right over. "Wow, Cheryl! You look beautiful tonight! I am so glad you came."
"Thank you, Jimmy," I simpered, smiling at him. He was in those tight football pants, and I thought he looked very good too.
"Cheryl, I'm going to score a touchdown just for you," he boasted, then turned abruptly and ran back to his team. I was so flattered! His team got the ball first, but the boy who caught it was tackled almost immediately. Then Jimmy got the ball and threw a long pass. It was caught, and the boy got to the ten-yard line before he was tackled. Once again, Jimmy got the ball, but this time, he lunged forward. He didn't throw it. He raced right into the line, and through it! He was in the end zone for a touchdown! I was standing, screaming like a high-school girl. He pointed right at me, then made a low courtly, sweeping bow. I was positively thrilled! Unbelievably, for the whole rest of the game, no one else scored on either side, and Jimmy's team won, 6-0.
He came over to me right after and asked if he could walk me home. "I have to shower and change. Will you wait a few minutes?" he asked. I, of course, agreed, and I went to the snack bar and had a hot cocoa while I waited for him. He came out in about fifteen minutes, and he looked so handsome! I took his arm and we left the park. I clung to his arm and my heels clicked prettily on the pavement as we walked. I chattered about his amazing touchdown and how very handsome he looked in his uniform, and he kept saying how glad he was I came. When we got to my door, still clinging to his arm, I murmured, "Thank you so much, Jimmy, for inviting me." And I got on tiptoe and gave him a soft kiss on the cheek. He looked down at me, and my heart leaped. In his eyes, I could see that he was going to kiss me. He leaned down and took me in his arms. I slid my arms up around his neck and fluttered my lashes shut. His mouth touched my lips and my desire flared. He kissed me so very tenderly, almost worshipfully, that I could not help responding emotionally. When he felt my response, he licked my lipstick. I parted my lips for him and his tongue slid into my mouth. My heart was beating wildly as our tongues danced. His tongue wrapped around mine, deeply touching my feminine soul. He held me very tight, and I could feel his maleness hard against my skirt. It was a very deep, long, lingering kiss that made my pulses pound. Finally, almost reluctantly, he broke the kiss. I pushed away slightly, breathless, touching his shoulders and tenderly stroking his muscular upper arms. Desire for him was coursing all through me, and I heard myself whisper, “Would you like to come in for a little while and have a drink with me, Jimmy dear? It’s still early.”
He looked deep into my eyes and I could see how much he wanted me. He touched my cheek softly, with just his fingertips, and murmured, “Yes, very much, Cheryl.” My heart leaped in my breast as I handed him my key. He unlocked my door and ushered me into my apartment.
Still trembling from his very passionate kiss, I turned and locked my door behind us, then walked into my living room. I have decorated my apartment in very feminine style, with a mirrored wall, soft, thick carpeting, and delicate furniture upholstered in rose satin. He was just standing there, devouring me with his eyes. I sat daintily on my pretty loveseat and patted the cushion next to me. “Sit here by me, Jimmy,” I invited.
Now that he was in my apartment, I knew from the way he was looking at me that our date was about to get considerably more intimate. If he were to find out the secret in my panties and reject me, I did not know if I could bear it. His male presence was so strong that I felt overwhelmed with desire for him. I could feel my heart pounding in my breast as he came and sat next to me. My emotions were on overload as I admired his boyishly handsome face and looked deep into his dark eyes. I glanced down and saw the swelling bulge in his slacks and realized with delight that I was the cause of his erection. He was reacting to me as any man might react to an attractive woman, and that realization was extremely exciting to me. A warmth began in my bosom, spreading slowly throughout my body until I knew I must be positively glowing. I could feel myself trembling in my panties. I wanted him so!
He put his arm around me and looked deep into my eyes. “You are so beautiful, Cheryl, so very beautiful,” he whispered. I placed my hand gently on his pants as his lips met mine. As he kissed me, I stroked him, feeling him pulse under my soft hand. His kiss was very intimate, and he fondled my breast through my blouse as his tongue thrust deep into my throat.
I wanted our kiss to last through all eternity. I wanted his hard maleness deep inside my quivering body. I wanted him to possess me, to own my virginity, to make me his girl forever and ever, but I was so timid. I wanted to please him so very much, but I was so afraid that when he lifted my skirt and lowered my panties I would lose him forever. Despite my deep, feminine emotional reaction to him, my fears were very real to me, and a tiny corner of my mind tried to find a solution to my problem while he kissed me. Suddenly in a flash of inspiration, I knew what to do. When he broke the kiss, I breathlessly murmured, “Jimmy, darling, I really would like to show you something. May I?” He smiled at me indulgently, and I disengaged myself from his embrace and went into my bedroom. “Wait right there, sweetheart,” I cooed.
I went to my lingerie drawer and took out my very sexiest slip. It is midnight black nylon satin, with a nylon lace bodice and a lacy hem. Like all my lingerie it is, of course, scented with my perfume. I brought it back out to the living room. “Jimmy, do you like this?” I asked, holding it up in front of him. “It is so very soft and silky,” I purred. I rubbed it against his cheek, then his lips, allowing him to sniff the scent. I could tell in his eyes that I was driving him crazy. I sat next to him again, looking at him adoringly. I undid his fly, and his maleness stood up like a rod, stiff and straight. “Ohhh, darling, you are so hard!” I sighed. I began stroking his penis with my silky slip, letting him feel the delicate luxury of a lady’s lingerie on his erection. I could feel him begin to pulse heavily under my gentle caresses, and I leaned next to him, giving him breathy butterfly kisses on his ear, his cheek, then his mouth. When my moist, trembling lips touched his, his whole body stiffened, and I could feel his hot semen shoot into my slip.
I was so totally involved in his pleasure that suddenly, I had the orgasm that had been building in me since his first kiss. My whole body quivered, then I spontaneously poured out my love into my panties. We clung to each other in a desperate kiss until we were both spent, then he held me for a long time, until my trembling quieted and I relaxed against him. I knew that I would give myself to him next time, without hesitation, regardless of what might happen.
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What happened to me when I went to the movies.
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. I began to look at the screen, and the leading man was, at that moment, passionately kissing the heroine. That definitely made me feel even more alone.
Ten or fifteen more people had come up into the balcony since I arrived, some men and some women, so I began to look around to see if there might be any other interesting men, but none were seated near me.
Suddenly, I was amazed to see my young man come back in again. 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 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. I realized that this was what I really wanted. 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 to the core of my being.
I reacted to his kiss with a woman's emotions. I felt so 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 was 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, which of course, he was. 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 into the bathroom.
As I sat to tinkle, I began to think. I knew if I went back to him, and I wanted to with all my heart, I would get so lost in his kisses, so utterly captivated, that I would lose all control. He would find out about me, and everything about this wonderful day would be spoiled. The more I thought about it, the more sure I became. I renewed my perfume, blotted myself dry, smoothed down my skirt, put 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 had I gone back to his arms and his kisses as I longed to do.
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