Cheryl's First Date

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, a twenty-three year-old t-girl, 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

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 Bonwit'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, 7-0.

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.