tagTranssexuals & CrossdressersMy New Girl? Ch. 01

My New Girl? Ch. 01


This story is a departure from my usual subject matter, at least to a certain extent. I hope you enjoy it. This story is also a *romance* so if you are not interested in that aspect of a relationship please do not read it or comment as those comments will be cheerfully ignored since you have been warned.

The story is complete and will be posted in seven chapters every other day or so.


I'd noticed her as soon as she walked in the bar. I was out for the evening with a couple of buddies from work, shooting pool and having a few beers on a Friday evening. She sat down at the bar and ordered a mixed drink in a tall glass, a Tom Collins maybe? She appeared to be waiting for someone as she kept glancing at the door then at her watch. I assumed she was waiting for a man as she quickly shut down any man who tried to strike up a conversation with her.

"You gonna shoot pool or are you gonna stare at that girl all night?" Paul asked. This was the third time he'd had to remind me it was my turn to shoot.

"Yeah, yeah, yeah, keep your panties on!" I said as I leaned over the table and promptly missed the ball I'd been aiming at. Paul ran the table, taking the five dollars that we'd bet in the process.

"Well, you gonna go over there and talk to her?"

"Nah, she's shut down every guy who's gotten near her. I don't need the rejection," I said, dejectedly. At that moment she turned to scan the room and our eyes met. I know it sounds clichéd but it was like lightning had hit me. I knew then that I had to talk to this enchanting woman, even if she shot me down.

"Be right back," I said as I set my cue down so that Ron could try his hand.

"I thought you didn't need the rejection?" Paul asked with a smirk.

"Yeah, well, what can I say? Wish me luck," I tossed over my shoulder as I walked away from the table. As I got closer I noticed that she wasn't quite drop-dead gorgeous but she was extremely pretty, in an understated way. She'd stand about 5' 6" or so I guessed and maybe 120-125 pounds. Her hair was fairly long, down below her shoulders, and a dark chocolate brown. She had dark eyes, though I couldn't see the exact color from this distance. My hands were shaking so I decided to go past her, to the restroom, where I hoped to calm down a bit before I made a total fool of myself!

I pushed open the door, stepped up to the sink and splashed some water on my face. A few deep breaths and I was as calm as I was going to be. I dried my face and returned to the bar. My luck was holding, she hadn't left nor had the person she seemed to be waiting for arrived. I stepped up to the bar, ordered a beer, then plunged ahead.

"Hello. I hope you don't think I'm being too forward but I had to speak to you. My name is Steve, Steve Williams," I took a sip of my beer, hoping to cover the shaking of my hand. She turned, smiling at me. Her eyes were a dark chocolate brown, matching her hair. Her eyes twinkled as she looked at me, her smile growing wider.

"Well, hello to you, Steve. That's one heck of a pickup line you have there!"

"Um, I, um, well," I stammered, captivated by her eyes as they bore into mine.

"I'm Jamie, Jamie Miller, pleased to meet you," she said as she extended her hand, taking pity on me. I grasped it and the contact only confirmed the feeling of being struck by lightning I'd felt when our eyes had met earlier.

"L-likewise," I said. God I was behaving like a tongue-tied idiot! "Can I... um, buy you a drink?" Her drink was nearly empty so I felt safe offering her another.

"Thank you, Steve, but I'm going to be leaving soon. I was waiting for a friend but she just texted me that she's not going to make it." Jamie took the final sip of her drink and slid off the barstool. I knew I needed to say something or this lovely creature was going to get away.

"Um, can I... call you sometime? I know this sounds corny but I felt something when our eyes met earlier and I felt it again when we shook hands. I'd really like to ask you out, if you don't mind?" I was blowing it, I knew it, but I'd never felt like this about a woman I'd just met. She looked me up and down, trying to determine if I was just an idiot or maybe a stalker, when she reached over to a stack of napkins and, after pulling a pen from her purse, she wrote a number on it.

"Here's my cell. Why don't you call me sometime and if I'm free we can have a drink or something?" Jamie said with a smile. I grabbed the napkin and stuffed it in my pocket as she turned and walked away. I stayed at the bar for a while, sucking on my beer and staring at the number. I hoped it was her real number but what were the chances of that? I'd probably never see her again and when I called the number it would probably be a pizza parlor, but I had to try.

"So?" Paul asked when I got back to the table.

"She gave me her number. At least I hope it's her number. Of course with my luck lately it'll be a Chinese laundry!" I laughed, though I was secretly wishing for the number to be real.

"Well, if it's a dry cleaner's ask what they charge. The place near me charges out the ass!" Ron piped in as he clapped me on the shoulder. "It's your turn. Put your fin on the table, buddy, I'm feelin' lucky tonight!"

I didn't know if I was feeling lucky or not. I guess I'd know tomorrow.


I waited until after 1:00 PM before I called. I'd dialed the number, except for the last digit, a dozen times. Each time I ended the call before I punched in that last digit. I knew I was being a chicken but I didn't want to know that she'd blown me off. As long as I didn't complete the call I still had hope that the woman who intrigued me so much was going to be on the other end of the line. If I finished the call and it turned out to be someone else all my hopes would be dashed.

Like last night, I knew that if I wanted to ask Jamie out I had to make the call.



"Yes, this is Jamie."

"Hi, Jamie. This is Steve, from the bar last night?"

"Oh hi, Steve! I'm glad you called!" she said. Her voice sounded happy, as if she was smiling.

"I was wondering. Would you like to go out for dinner tonight?" I asked hopefully.

"I'm sorry, Steve, I can't—"

"Oh, that's okay. I understand..."

"No, you don't. I'm having dinner with my family tonight. It's my sister's birthday. I could meet you for a drink later, say around 10?" Jamie said hopefully.

"That would be great!" I replied, excited that she seemed to want to see me. "How about we meet at the same place as last night?"

"Sure, that sounds great. Hey, just in case the party goes long why don't you give me your number? I'd hate to think I was standing you up," she said with a hint of teasing in her words.

"Sure, got a pen?" I gave her my cell number, thanked her for agreeing to meet me, then I hung up. I quickly added her cell number to my phone then I spent the rest of the afternoon puttering around the house. I was too nervous to sit at home so I drove over to my parent's house. They loved it when I dropped in, since I didn't do it very often, but tonight I wanted company.

"Hi, Mom, Dad!" I called out as I opened the back door.

"Steve!" Mom said as she pulled me into a hug. "What brings you by?"

"Your cooking, Mary, what else?" Dad said as he too pulled me into a hug. He slapped me on the back, hugging me tightly.

"Now, Joe, stop that! Steve's welcome any time!" Mom said as she whapped my father on the arm.

"Actually I have a date later tonight for drinks but I'm too nervous to sit home. I hope you don't mind?" I said as I sat down on the couch, facing my father who took the chair opposite me. Mom settled down on the other end of the couch, a smug smile on her face.

"A date, huh? And you're nervous about it? What is this girl, a supermodel?" Mom said, teasingly.

"No, she's very pretty but she's not a supermodel. I don't know what it is. I can't explain it but I'm really attracted to her. I've never been attracted to a woman like this before. It's kinda scary, you know?" I said, focusing on my hands which were resting in my lap.

"Hmm, sounds intriguing," Dad said. "All I can say is be yourself and be polite. Get to know her for herself and you'll do fine."

"I'm glad you're thinking about dating..." Mom said as she trailed off, not wanting to bring up a touchy subject. It had been just over a year since I'd broken up with my long-time girlfriend. We'd met in my senior year at college and had been dating pretty seriously for over a year. We'd seemed to be doing well, or at least *I'd* thought so. I'd gone out and bought a ring and was planning to propose when she broke up with me. I took it pretty hard since I had no clue that she wasn't on the same page as me. It turned out that she'd found a guy at work she liked better than me. She let me down easy but it still shook my confidence and I hadn't dated very much in the last year.

"Well, don't get too excited, Mom. It's just drinks."

"Even so, I'm pleased to see you trying. Supper will be ready in ten minutes. Why don't you go wash up?"


After dinner Mom, Dad and I watched a new movie they'd bought and that kept me busy until close to 9:30. I kissed my mom goodnight then headed to the bar. For a Saturday night it was pretty busy but I was able to get a stool at the bar where I could see the door. I had just taken a sip of my beer when Jamie walked in. She glanced around the room and when she saw me she smiled widely as she hurried to my side.

"Hi Steve, I made it!"

"What can I get you?"

"Tom Collins, if you would, please." I signaled the bartender and placed her order. While we were waiting for the drink a stool opened up two seats away. Since the guy between me and the seat seemed to be alone I asked him if he wouldn't mind sliding over. He smiled as he noticed Jamie standing by my side. He slid over, tipping his

beer to me. Jamie quickly grabbed the chair just as the bartender returned with her drink.

"Umm, that's good," she said as she took a sip of the frothy drink.

"So how was your sister's party?" I asked, hoping it was a safe topic to begin with.

"Fine, my sister is a bit of a nag though. She keeps asking me when I'm going to settle down. Sheesh, she just got married last year and she's a year older than me! I love her to death but sometimes..."

"I wish I knew where you were coming from but I'm an only child. Do you have any other siblings?" From there we were off. I found out that she had an older brother, Josh, who was two years older than her sister, Emily. I found out she was 26, two years older than me, and a sales rep for a drug company. She loved her job but sometimes the travel was a hassle, especially during construction season. Her territory extended from Cape Cod all the way to Rhode Island. I told her I was an architect with a small firm that designed mostly commercial buildings, though with the economy we were branching out. I was currently working with a homeowner on a remodel of their home.

We talked for three hours, until last call, and from there we drove to Denny's for coffee. I'd never felt this comfortable with a woman before and didn't want the evening to end. However after our second cup Jamie let out a yawn that would have made a lion proud.

"God, I'm sorry!" she said, as a blush crept up her cheeks.

"No, I'm the one who should be sorry. I've kept you out way too late." I paid the check then walked her to her car.

"Well, goodnight, Jamie. I really enjoyed myself. I'd... I'd like to ask you out again," I said hopefully.

"I did too, Steve. I can't remember when I've had such a good time. I've told you things I've never told a guy before!" she said, blushing again. "I'd like you to ask me out again." She kissed me on the cheek and before I could respond she was in her car and driving away. I stood there, dumbfounded. My cheek tingled where she'd

kissed me and I felt more alive than I had in years.


I called Jamie the next morning to make a date for the following Friday. Between her work schedule and mine weekends were the only time our schedules allowed time for dating. Either she or I would call in the evening and we'd talk for a while but it was never enough. We couldn't wait until the weekend when we could actually see each

other. Our first real date was simple, dinner and a movie. I picked her up at her apartment, a small place across town from my own home.

"Steve! Come in!" she said as she answered the door. She wore a dark blue blouse and tan slacks. Her hair was done up, exposing her neck. She looked gorgeous. I pulled the flowers I'd brought from behind my back, handing them to her.

"Oh, they're beautiful!" she said as she took them into the kitchen. She pulled a vase from her cupboard, filled it with water, then she put the arrangement on her coffee table. She walked over to me and kissed me on the cheek. "Thank you, Steve. I can't remember the last time someone gave me flowers."

"I don't know who you've dated before but they had to be crazy not to bring you flowers!" I said honestly.

"Thank you, Steve," she said softly, glancing up at me through her lashes. I could see she was blushing again.

"Well, why don't we get going? We have reservations for 7:00." We had a quiet dinner, no dessert, and then we were on to the movie. It was a romantic comedy and in spite of being what one might consider a 'chick flick' it was actually pretty good. I'm kind of a sucker for romance and it was nice to see the couple get together at

the end. I didn't want the evening to end so I suggested going out for dessert. We ended up at a small café near Jamie's apartment where we shared a piece of pie and talked over too many cups of coffee. I dropped Jamie off at her apartment and this time I kissed her, lightly, on the lips. As I pulled away I noticed her eyes were still closed and she had a pleased look on her face.

"Goodnight, Jamie, I had a wonderful time," I said as I held her hands in mine.

"Me too, Steve. Goodnight." She opened her door, smiling at me as she closed it behind her. As I had the previous week I about floated to the car as thoughts of Jamie played out in my head.


We dated every Friday and Saturday for three months. During this time we progressed from chaste kisses at the door to some pretty heavy kissing in her living room after an evening out. The first time we really kissed it was unlike anything I'd ever experienced. Kissing Jamie was as close to having sex while staying completely dressed as possible; at least it was for me. I could tell she was affected as well because when we broke apart her chest would heave and her nipples would be poking against her bra. One time, after we'd been kissing for a while, I slid my hand up to cup her breast.

"Steve, we need to talk," Jamie gasped as she grabbed my hand, holding it against her stomach. I worried that I'd offended her and began to apologize.

"I'm so sorry, Jamie—" I began.

"No, Steve, you didn't do anything wrong. It's just that I think we need to talk before things progress any further." She leaned in, pecking me on the lips, her eyes asking me to understand.

"Okay, Jamie, I'm listening. Please, talk to me."

"I like you, Steve. I really like you. But I need you to understand that I'm kind of old fashioned. I'm saving myself for the man I'm going to marry and I hope you respect that."

"I do, Jamie. I understand completely. I have to say that you're a rare woman in this day and age. I admire you and your resolve."

"I also want you to know that because of my position on sex I am prepared to satisfy you in other ways..." She trailed off, her cheeks turning red, evidence of her embarrassment.

"What about you? Don't you need... relief?" I asked softly.

"Don't you worry about me. I'll be fine. After all, I've been dealing with this ever since I started dating."

"Still..." I said as I gazed into her eyes.

"Quiet now. I'll be fine. Me and my vibrator are old friends, really." She smiled shyly up at me then she leaned in, laying kisses along side of my neck.

"Alright, if you say so. But if you ever change your mind you let me know. I promise, we'll never go any farther than you want. I'm not some sex maniac who is going to jump your bones the first time I get you naked. I care for you, Jamie, a lot. We'll take things at your pace. I promise."

"I know, Steve, and I do trust you but I also don't want to be a tease. I don't know if I'd be able to maintain my resolve so I don't put myself in a position to be tempted. Thanks for being so understanding." She pulled me down into a fierce kiss. Her tongue slid between my lips and dueled with mine. When her hand released mine so that her arms could wrap themselves around my neck I slid my hand back up to her breast. As my fingers closed around her mound she moaned into my mouth while pressing herself even harder into my hand. God this woman was hot! I didn't know how she could be this hot and still be a virgin at 26 but it wasn't up to me to question her beliefs.

I slipped two, then three buttons on her blouse so that it opened enough so that my hand could hold her lace-clad flesh. Her orb filled my hand, round and heavy, the hot flesh encased within her bra frustrated me. Just as I was about to slip my hand around her back to undo the garment she pulled away.

"Front clasp," she hissed in my ear as she nipped my earlobe. I captured her mouth once more as my fingers found then released the clasp. The fabric parted, her globes now exposed. I gently tweaked first her right, then her left nipple, bringing both of them to instant hardness. She pulled away, her eyes wild with desire as she drew my head down to her chest.

"Suck them!" she growled as she forced her nipple into my mouth. I obeyed her request, sucking and licking her nipples. I switched back and forth until both nipples and most of her breasts were slick with my saliva. As I sucked I nipped the hard flesh causing small moans and groans to escape from her throat. I could hear her breathing accelerate as she fed more and more of her breasts into my mouth. Her body stiffened as her orgasm overtook her.

"Steve! Oh God, I'm cummmingg! Oh Steve! Don't stop, baby, don't stop! Bite me! Suck me, please!!!!!"

I nipped harder on her, pulling her nipples with my teeth, stretching them away from her full breasts. She shook and shuddered, her arms squeezing me fiercely to her chest. If I died now I'd have died a happy man being smothered by her flesh! At last she relaxed and I slowed my sucking, finally just licking the stiff nubbins with the tip of my tongue.

She opened her eyes lazily, seeming to have difficulty focusing at first. At last her breathing slowed enough to where she could talk.

"That's... never... happened... before..." she panted, the satisfied look on her face told me everything I needed to know.

"You've never...?" I asked incredulously.

"Not from just having my breasts sucked, no. I don't know what you did to me but I hope you keep doing it!" I grinned like a fool, so pleased was I that I'd been able to give this wonderful woman so much pleasure. "I knew you were a special man, Steve, and you've just proved it. No other man I've dated has *ever* affected me the way you do. It's almost as if you knew my body better than me. It's amazing."

"You're amazing, Jamie. You're a beautiful woman who is more responsive than anyone I've ever been with and I've only touched your breasts! I can't wait to see what will happen if we ever make love." Jamie blushed at my praise though she gazed at me with barely concealed desire.

"After what you just did I think you'd probably kill me, but what a way to go!" she exclaimed, giggling happily. I leaned back, resting against the couch as she snuggled into my arms. Her blouse and bra stayed open though in this position I couldn't really see very much of her. Jamie ran her hand over my chest, tweaking my nipples. I'd never had much sensation from my nipples but Jamie's touch was driving me wild. My cock, which had been starting to soften, began to harden again. I felt myself swelling, pressing into her bottom. I tried to shift my body so she wouldn't notice but that wasn't to be.

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