My Wonderful Obsession 20 free porn video

My Wonderful Obsession Part 20: A New Job I'd been thinking about money, or more specifically, the lack of it, since Julia's pool party the weekend before, when I concluded that I needed to look for a different part-time job. The letter from Dr. Cooper only made me think a lot harder about it. I was still earning about four hundred dollars a month from my catering job with the Taylors, but even with the additional hundred or so that Mom paid me it wasn't quite enough to cover my clothing, entertainment and savings budget. Paying for hormone treatments was going to cause real hardship! And what if I wanted to get my driver's license and buy my own car? Not much chance of that happening. An idea had occurred to me while we were eating out the night before. Our server, a young girl about my age, wasn't exactly the best waitress I'd ever encountered. Not only did she take forever to come and get our order, she brought Mark the wrong salad and actually argued with him about what he ordered, even when I told her I'd heard exactly what he said. The incident wasn't a big deal, but it caused us both to feel annoyed when we should have been enjoying our time together. When it came time to leave, I reached into my purse for tip money as I often did, but Mark wouldn't let me leave any. "She doesn't deserve a tip," he said flatly. That incident reminded me of another, which couldn't have been more different. Earlier in the year, after singing the Pocahontas song at my voice recital, I'd gone out to a restaurant with my drama friends and had the world's best waitress, namely the 'southern belle' Chelsea, to look after us. She was so good at her job, and made everyone feel so entertained and special (me in particular), that she got a huge tip even though her guests were all poverty-stricken high school students. I recalled what Chelsea had told Ben, when he said she could be a detective: "Yes, honey bun, but ah can make a lot more in tips workin' here!" 'Could I do that?' I asked myself. I knew I loved to serve people, and I was good at it - my three years working for the Taylors had proven that. But serving at catering functions was a lot different from waiting tables in a restaurant setting. I'd heard horror stories about waitresses being abused by nasty patrons, both male and female - and I knew that the job was a lot more busy and stressful even without the abuse. I wondered, frankly, if I might be a little too nice for that kind of career. So I decided to ask someone whose opinion I could trust. And no, this time it wasn't Kath. My first call was to Mark at work. I'd never phoned him there before! "Hello, thank you for calling Medi-Tronic Systems. How may I direct your call?" answered the receptionist, whom I thought had a very pleasant, musical voice. "I'd like to leave a message for Mark McCowan if I could, thanks." "You can speak to him now if you like," she said in a friendly way. "Oh, are you sure? I don't want to disturb him if he's busy ..." "That shouldn't be a problem, miss - I'll get him for you. Can you hold?" "Yes." I immediately heard music, so I assumed I'd be waiting a while. I was wrong. "Hi, this is Mark. Can I help you?" I'd been on hold for maybe five seconds. "Yes sir," I said in my sexiest voice. "I desperately need a man to take me to dinner tonight. Can you help me with that?" I heard laughing at the other end. "Sandra, you NEVER call me at work! What's up?" It sounded like he thought I was joking. "Mark, we really DO need to go out tonight. Do you remember the name of the restaurant where Chelsea works?" "Yeah, I think it's called Milestones Grill. How come you wanna go there?" I tried to explain what I had in mind, comparing Chelsea to what we experienced the previous evening. Mark agreed with me wholeheartedly. "I don't even remember what the food was like," he said. "Chelsea was such a great server, the place seemed like a five-star restaurant." "Totally!" I replied enthusiastically, glad that we were on the same page. "But what if she's not working tonight?" "That's why I want to call ahead - if she's there I'll make us a reservation at one of her tables." "So, let me see if I can figure this out - you're asking me out on a date? Or is this just a business meeting with Chelsea?" I hoped Mark was just having some fun with me. "Mostly a date of course, you silly man. But just an itsy-bitsy bit of business too - do you mind, darling, sweetie pie, honey bunch?" "Oh, I suppose I can handle it. As long as it's not another GUY you're doing business with ..." "Never in a million years!" I laughed. And that was a promise. ***** We arrived at Milestones at six-thirty. I recalled that the restaurant was very popular and was surprised that it was no problem booking a table, considering that it was prime dining time. Mark said he thought the reason might be it was early in the week. The hostess, a very attractive girl of about eighteen or nineteen, showed us to our table and placed menus in front of each of us. "Chelsea will be your server this evening," she said in a high, musical voice that made me wish mine was a lot more feminine than it was. "Notice anything about the staff in this place?" Mark asked, as he scanned the room. "They're all girls - and they're all wearing black?" I guessed. "Yeah - but they're all model material too," he pointed out. "And here I thought you only had eyes for ME!" I pouted. He shook his head and put on a guilty expression. "Busted again," he deadpanned. A moment later my favorite waitress appeared at our table. "SANDY!" she exclaimed, as I rose to give her a big hug and a cheek kiss. "Y'all haven't been here in AGES!" "Better late than never," I apologized. "Do you remember Mark?" My boyfriend rose and held out his hand, but Chelsea ignored it, hugging and cheek-kissing him as well. "Ah never forget a handsome man," she said with a flirty expression and a gleam in her eyes. I think Mark was a bit taken aback, but he recovered fast and beamed a smile back at her. 'Typical male,' I thought - 'such a sucker for a flirt!' "Nice to see you again, Chelsea," he said. "Y'all are looking better than ever, hon," she complimented me as I sat down again. "Ah just love your taste in clothes!" Hearing that, I was glad I'd decided to wear something pretty - one of the cute sundresses I'd picked up at Macy's, a spaghetti-strapped pink and white number with a very short flouncy skirt. "It's probably just my tan, Chelsea," I replied. "And how about you? Like, you look gorgeous, and I love that outfit!" "Just mah uniform, hon - nothin' special ..." It sure looked special on her, I thought. It was all black, with separate skirt and top. The top was very flattering, loose fitting and off one shoulder with a wide band of fabric over the other, and the skirt was form fitting and quite short, revealing a pair of perfectly formed thighs. Her long blonde hair was arranged on one side, cascading over her bare shoulder, and her eye makeup was quite dramatic. I glanced back at her legs and noticed she was wearing nude pantyhose, and on her feet were a pair of cute black patent leather shoes with about three inches of heel. Naturally, I wondered how it would feel to be dressed so sexy like Chelsea! "So what can ah get you two beautiful people to drink?" she inquired with a raised eyebrow. Mark and I looked at each other. "Well what we'd REALLY like is a bottle of your best champagne," he replied with a wink and a big grin, "but then you'd have to check our ID, so how about a couple of virgin strawberry daiquiris instead?" "YOU know how to show a girl a good time, dontcha honey?" Chelsea laughed. "Sit tight - ah'll be right back!" "Don't you just LOVE her?" I asked Mark in a low voice when Chelsea was out of earshot. "She makes you feel so good ... and welcome - you know, like you're family." 'She also gives such nice compliments,' I thought. "And we waited, what - two seconds to get served?" he added. "A little different from the place we went last night." I nodded. "That's why I wanted to come here, Mark. Like, I'm thinking of looking for a restaurant job instead of doing catering - with tips I could probably earn a lot more." Mark looked at me with a smile and nodded in approval. "I'll bet you could. Maybe you should get a job HERE." "Oh, I dunno - this place might be hard to get into ..." "Well, it's sure busy - more customers mean more tips, you know." Just then Chelsea appeared carrying a tray with two very spectacular looking red drinks in tall dessert glasses. "Here we are ... ladies first," she said, placing one in front of me with a flourish. "And one for the handsome gentleman!" She waited for a moment till we each took a sip. "So what d'y'all think?" "Best virgin strawberry daiquiri I've had all day," Mark replied with a straight face. "I love it!" was all I could add. I noticed that Chelsea was staring at my left hand as I took another sip. "Ooh - y'all have a ring! Let me see it!" I held my hand out for inspection and she immediately grabbed it for a closer look. "VERY pretty ... is it an engagement ring or just a promise ring?" "A promise ring," I replied, recalling why I'd decided to wear it on my left hand - so I could pretend it meant something even more special! Chelsea gave Mark a stern look and said, almost as a warning, "I hope these sparklers are real diamonds, bub!" Mark smiled at me and replied in an authoritative voice, "Nothing but the best - this girl's very fussy, you know." "And so she SHOULD be - but she picked y'all, so that proves it, right?" Before either of us could respond, Chelsea expertly changed the subject. "Now, then - are we here for an evening of fine dining, or shall I just keep the daiquiris comin'?" Mark answered since my face was buried in my cool, tasty drink again. "Uh, both I guess. But I think Sandra has a few questions for you, too." "Oh, y'all are goin' by Sandra now?" she squealed. "Ah just love that name! Mah favorite actress ever was Sandra Dee. But y'know, her real name was Alexandra ..." "Mine too!" I piped up before I could wipe my mouth. 'Well, close enough,' I thought. "Well, Lord love a duck - ain't that SPECIAL! An' ah suppose you're gonna tell me you're an actress too?" "Right again!" Mark answered. "She was in 'Fiddler on the Roof' at our high school. Not only that, she also sings and dances." "MARK!" I jumped in, shaking my head, "You're making it sound like I'm some kind of pro ... Chelsea, I only study those things in school, or in my spare time." "Well, ah'm sure you'll be a star, hon - you've certainly got the look, an' ah KNOW you've got the talent!" Chelsea stole a quick glance at the other tables, then focused on us once again. "So, why don't ah tell you about our chef's specials first, then when ah come back y'all can fire away?" We nodded and she described four different dishes in delicious detail - I could almost taste each and every one - and asked if we needed some extra time to decide. With her graphic descriptions we didn't, so she took our orders without writing them down and headed off to the kitchen, stopping momentarily at another table on the way. I looked at Mark shook my head. "See what I mean? She's AMAZING. Like, she makes you feel SO special! And she really likes her job, don't you think?" "No argument there," he agreed, shaking his head. "If you were a cynic you might say she was just doing it for bigger tips, but I don't think so. She seems pretty genuine to me." "I'LL say." I was silent for a moment while I thought about why I'd come to see Chelsea. Then I looked at Mark and said, "I'd love to try waitressing ... but I don't think I could ever be THAT good at it. And you know me ..." Mark laughed, "Do I ever! You always have to be the best at everything! But take it from me - you have nothing to worry about. You seem to be good at connecting with everyone you meet. Okay, maybe you're a bit on the shy side, but that only makes you MORE interesting. Sure attracted me!" I reached over and took one of his hands in mine as I felt my eyes begin to moisten. "You're so good to me," I told him sincerely. "What would I do without you?" Mark looked me in the eyes for a moment, then leaned across the table and gave me a soft kiss on the lips. My eyes became a little wetter as I realized how deeply I was in love with this amazing guy. Our tender moment was interrupted by Chelsea's return. As she placed a plate of appetizers in front of us she said, "Wow - ah'll have to tell the owner his romantic atmosphere's workin' ovetime!" Mark and I laughed out loud. "Sorry," I said, "we didn't mean to cause a scene ..." "Oh no, hon, that's the kind of scene we LIKE to have - but if y'all are havin' a fight please do it in the place across the street." That got me giggling like a little girl, and I couldn't stop. Chelsea picked up my daiquiri and, sniffing it, shook her head and said, "Ah thought ah told the bartender VIRGIN." The way she said that, with her wonderful southern-belle accent, it was just too much for me. I was giggling so much that tears were streaming down my face, carrying my carefully-applied eye makeup with them! Chelsea quickly offered me a napkin and crouched down to dab my streaked face. "Cain't have mah favorite customer lookin' like Alice Cooper ..." she deadpanned. "Mark, tell her to STOP!" I pleaded. But he wasn't much help - tears were running down his face too. It was Chelsea who finally put things back on an even keel. "So you had some questions for me?" she inquired innocently. "I think you already answered one of them," Mark said while I tried to regain my composure. "Sandra wanted to know what it's like to be a waitress. Now we know it's just like being a stand-up comic." It was Chelsea's turn to laugh. "Oh no, honey, ah'm just being little ol' me ..." Then she looked at me and asked "So you're thinking about a new career?" "Well, kind of," I replied. "But I just wanted to get your take on it ... and like, I don't know if I'd be any good ..." She gave me a big smile and said, "Why don't ah let you go get freshened up and we'll talk about it. And hon? Remember to use the right door!" Mark and I both chuckled at that amusing memory, and I excused myself, grabbing my purse as I left. When I returned there was a basket of fresh chips on the table, and Mark was already busy nibbling on them. "Aw, I was just getting used to having Alice Cooper for a girlfriend!" he kidded. "Not exactly MY style, hon," I was beginning to say, but then Chelsea reappeared, crouching beside our table. "So d'y'all have any serving experience?" "I've been working part-time for a catering company for the past three years - you know, waiting tables, serving coffee, cleaning up, that kind of thing. But I've never worked in a restaurant." "How was it? I mean, did y'all enjoy the work, get along with the customers?" "Oh yes! I love serving people. And I think they like how I treat them ..." "Take it from me," Mark interjected, "Sandra's the best ... I mean, after you, of course!" "Oh no, honey," Chelsea laughed, shaking her head. "Your girlfriend's ALWAYS the best! But thanks anyhow for the nice thought." She gave him a wink and turned back to me. "Ah love serving people too. That's 'cause ah just plain love people - an' ah love my job here! Ah get to meet lots of real nice folks, like y'all ... kibbitz with 'em, help 'em have a fun time ..." "But aren't some people kind of annoying?" I asked. "How do you handle them?" She shrugged, as if that sort of thing was only a minor annoyance. "You learn how to soften 'em up. You just appeal to their good side - everybody has one ... humor's your best weapon!" I was feeling even more impressed with Chelsea than I did before. "That's so cool - it must take a lot of practice ..." "No, it doesn't - remember, you just have to be the kind of person who loves people - then treatin' them well just comes naturally. That's why ah love this job - ah get to do that all the time!" I nodded my understanding. "You get to wear nice clothes too," I blurted without thinking. Chelsea's eyes sparkled as she laughed and gave me a dazzling smile. "Oh, so THAT's why y'all want my job!" "She's got YOUR number!" laughed Mark, pointing his finger at me for effect. "You're so right, Chelsea - she has a major clothing obsession. You should see some of the stuff she's got ..." "Ah can just IMAGINE," she nodded, glancing at my outfit. "But y'all do a dress proud, y'know ... and ah'd love to see you in one of our outfits, too." "HERE?" I asked, surprised by what Chelsea had just said. "You think I could get a job here?" "Uh-huh," she nodded. "Ah think we're hiring right now - one of our girls just left to have a baby. So why don't y'all fill out an application an' ah'll put in a good word for you." Chelsea had been glancing around her section the entire time she was visiting with us, and I think she noticed another customer trying to catch her eye because she immediately excused herself and went to their table. I made a mental note to try being that attentive if I got to be a waitress. "So what do you think?" Mark asked me. "Are you going to apply here?" "Gosh, I don't know - wouldn't that be kind of like jumping into the big leagues for my first real job?" "You'd do a lot better than most people, and you know it," he replied in his usual reassuring way. We talked about the possibilities for a few more minutes, and then Chelsea showed up with two plates of food, which she expertly placed in front of us - the right way around, I noted. "Fresh ground pepper?" she asked, and went to retrieve it when Mark nodded. As she was grinding some onto his food, she asked me, "So what d'you think, Sandy - are you gonna come work here with me?" I looked at Mark and he just smiled and shrugged his shoulders. So I turned back to Chelsea and said, "I'll be back in school next month for my senior year, so I can only do part-time - but, like, if you think I'd have a chance I'd love to apply ..." "We're all part-timers here," she said. "Some do more hours than others. Why don't y'all give it a try and see how you like it?" "Okay, then I will - I mean, I'll apply. Can you get me the application form?" "Ah'll do better than that - when y'all are done eating ah'll send the owner over to see you, if you like." I wasn't expecting that. "Oh - are you sure? Uh, I don't know if I'm ready for that, so soon ..." "No worries, hon - ah already spoke to him an' he's dyin' to meet you!" 'Oh my God,' I thought - no pressure! "Uh, okay, I guess if he doesn't mind ..." "'Course not!" Chelsea called out as she made her way back to the bar. "What have I gotten myself into?" I fretted to Mark. When we were finished our meals and Chelsea had cleared the plates, a slightly balding mid-fortyish man of about five-foot-eight appeared at our table. Mark and I both rose to greet him, and I noticed that his eyes darted quickly from my head to my toes, pausing momentarily at my bust line, then the hemline of my short dress, and then returning to scan my face. "I'm Miles Crawford", he said, smiling and extending his hand. I had a momentary attack of shyness, but Mark quickly grabbed his hand and introduced himself, then me. I managed to find my wits and shook Miles' hand. "I'm very pleased to meet you, sir." Miles drew another chair alongside and got right down to business. "I understand you're looking for a job as a waitress. What kind of experience do you have?" I explained what I'd been doing previously, adding in a few extra comments about how much I loved serving others, while Miles peppered me with more questions - how old I was, where I lived, did I have a car, how many hours could I commit to. I answered truthfully, except maybe for the hours where I was probably a little optimistic. But I really wanted to make some serious money! Miles then excused himself but quickly returned with a sheet of paper. "Well, seventeen is a bit on the young side, but you seem to be a very mature young woman and you're definitely the kind of girl we like to have with us here at Milestones," he said sincerely. "Why don't you take this home with you and fill it out for me. Can you bring it back Thursday afternoon?" "Sure, that would be great," I said excitedly. We agreed on a time, then Miles rose from the table and wished us both a good evening. I looked back at Mark, and as usual he was smiling at me, but his face had a wry look on it. "I thought you promised me you weren't doing business with any guys?" he whispered as Miles departed. "MARK!" I laughed, "How was I supposed to know I'd get an interview so soon?" "So what do you think? Are you going for it?" "I dunno - I guess I should see how much it pays first ... but Mark, I really think it's time for me to like, move on from my job with the Taylors." "Sounds like the job's yours if you want it ..." "I know - that's the feeling I got too. Kinda scary though ..." Chelsea was back a few minutes later with a huge plate of dessert, which we hadn't even ordered - strawberry shortcake and vanilla ice cream, heaped with fresh strawberries. "On the house!" she proclaimed as she placed it between us. "Ah figured, seeing as you like strawberries an' all ..." "Chelsea, this looks fabulous! You shouldn't have!" I exclaimed. "The boss told me to do it, hon," she said innocently, handing each of us a long-handled dessert spoon. "Miles must want to hire you real bad!" Mark jumped in: "If I convince Sandy to come work here, can I get another one of these next time?" He was already shoving a big spoonful of berries and ice cream into his mouth. "As many as you like, honey. Ah'd LOVE to have her work here!" "THAT settles it, sweetheart," he said, fixing me with a no-arguments stare. "You gotta take this job!" I didn't know what to say, so I just made out like I shouldn't speak with my mouth full. The idea of working with Chelsea at her restaurant was way more than I could have hoped for, I thought. But what an opportunity! And I was sure I could earn decent money - if I could get enough hours in, that is. It would all depend on school work and other activities. I decided I'd talk it over with Mom when she got home the next day. And maybe my wise friend Kath too! We were just finishing up the last of the shortcake when I felt a chill come over my body. Was it the idea of starting my first REAL job, the air conditioning - or just the ice cream? Whatever, Mark noticed the goose bumps on my arms and slid his chair around so it was next to mine, then he put a warm, furry arm around my bare shoulders. I automatically snuggled into him. "You're so nice and warm," I purred. "How come I feel so cold?" "Couldn't have anything to do with the skimpy dress, could it?" "Maybe that's it. I should probably have worn something a bit more substantial ..." Mark's face got a pained look. "No, I kind of like how you're dressed right now. How about we sit next to each other from now on. I could just keep an arm around you ... hold you nice and tight ..." I couldn't help myself - he deserved a nice long kiss and that's exactly what he got. Of course, when I opened my eyes Chelsea was standing there with her arms crossed, shaking her head. "Tsk, tsk ... ah can't leave you two alone for two seconds, can ah?" "You DID say something about the romantic atmosphere," Mark replied with a grin. "Yeah, and what's with the temperature in here?" I added with a wink. "You keep it so low, like, I have to snuggle up to keep from freezing to death!" "Dontcha worry, hon - when you're workin' here, you'll wish it was even colder! Now, can ah get you two lovebirds anything else?" We glanced at each other and Mark answered, "No thanks - just the check I guess." "Coming right up, darlin'. Now y'all can go back to what you were doin' ..." I didn't need a second invitation. I loved kissing Mark and any excuse was a good one. He had one hand wrapped around my shoulder and the other on my upper leg, which was also covered in goose bumps. "We should go someplace else," he said softly. Mark paid the bill with cash, which he simply put on the table, and I looked after the tip. I think I left about fifty percent. But what happened next made me wish I'd made it a hundred. As we got up to leave, Chelsea came over to say goodbye. I knew I had to tell her something. But I didn't quite know how to put it, so I just took her aside and blurted it out in a low voice. "Chelsea ... thank you SO much for what you've done for me. You, uh ... like, you know I'm not really a girl ... and ..." She immediately put a finger against my lips and looked at me with both eyebrows raised. "Oh NO, hon - y'all are a VERY beautiful girl, just like all the other beautiful girls who work here. An' don't you EVER forget that now, y'hear?" I just gave Chelsea a great big hug in reply, and tears began to fill my eyes once again. I couldn't believe it - yet another wonderfully supportive female in my life. If I didn't think I was leading a charmed existence before, I certainly did now! I grabbed hold of Mark's outstretched hand and we walked out of the restaurant, with me trying my best to retain my balance and composure. The moment we stepped out the door I felt more comfortable - it was another beautiful evening, almost eighty and dead calm. My goose bumps disappeared immediately. I was still in a bit of a daze when Mark stopped the car in a park. He came around and opened my door and I took the hand he offered me. We strolled down a short path in the trees to a spot where you could see the city lights stretching out for miles around. And we embraced and began to kiss passionately. In no time, Mark's hands were all over me! He caressed my shoulders, my arms, my face, my hair, and my hands. I loved it so much, and wanted more than anything for him to keep going. "I love your skin, Sandra," he whispered. "I love how it feels to touch you ..." "And I love being touched by you," I replied between kisses. "I wore this dress just for you ... I wanted you to touch me all over ..." Mark interpreted that as permission to expand his explorations, which I guess it was. Now his hands were down on my ass, squeezing my cheeks through the soft material of my dress and panties. But then he lifted the skirt and only my panty was between his hands and my skin. I automatically pushed my body even tighter to his, and I immediately felt his warm hands slip under the thin fabric, sliding smoothly over my round bottom, gripping and pulling me even tighter against his body. All I could think of was how deliciously female he made me feel - and how rock-hard HE felt against my tummy! I managed to work one of my hands between us, onto the front of his pants, grasping him, stroking him and marveling at how he could get such a huge erection over ME! It was obvious from his movements that Mark was getting desperate for me to touch him for real, and I didn't want to disappoint, so in no time a manicured hand was forcing its way into the snug space behind his belt, groping for its prize! But there was no room to manoeuver, so I solved the problem by undoing his belt, fastener and zipper, all the while still kissing him passionately. When I finally tugged his shorts down a VERY stiff penis literally popped out at full attention! It felt so long, it needed both my hands to hold it! At that moment, right in mid-kiss, Mark let out a huge sigh and his whole body seemed to tremble. For a brief second I thought Mark was going to explode on the spot - but luckily he didn't, so I got my wish and was able to totally enjoy the thrill of bringing him to orgasm with my hand. A moment before the big event, an odd thought entered my mind and stuck there: how lucky I was to really be a male, to know precisely how to do what I was doing and how to give my lover maximum pleasure; how and where to grip him, how fast to go and exactly when to speed up. The thought was interrupted a few seconds later - Mark's back arched, his whole body stiffened, and I felt his cock pulsate wildly as he let go with what might have been a very loud cry if my lips weren't still locked tightly to his. Thick warm liquid was all over my hand, and I just let it lubricate me as I continued to pump him until he pleaded with me to stop. 'WOW!' I thought - 'this is so AMAZING!!!' And it struck me at that very moment that being with a man was the most wonderful thing in the world. You can probably guess what was going through my mind as I pulled my white satin nightie over my head later that night. That momentary feeling I had - of enjoying being male so I could make love with another male - was real, powerful and very erotic. But what did it all mean? Was I really just an effeminate gay guy who happens to like wearing girl's clothing? I recalled telling Julia I wasn't gay, but maybe I just didn't know the truth at the time. Or maybe I was really bisexual - after all, hadn't I enjoyed sex every bit as much with a girl too? Looking back, it's obvious I was at a point in my young life where I was confused and unsure about who I really was inside, probably not unlike most teens. But I had some extra-special issues, no doubt about it! ***** Phil and I went to the airport to pick Mom up the next afternoon. She'd phoned home twice, on the previous two evenings - both times I missed her call because I was out with Mark - and she'd told Phil that things were going well for her down in Tampa. During the drive I realized that this was the first time I'd been alone with him in a car since I began dressing as a girl. On that particular morning I'd put on a bra, pink tank top and jean skirt - more out of habit than anything - and sitting next to him in the passenger seat I was acutely aware of the obvious differences between us two brothers: my long hair fastened up with a big pink clip, the protrusions on my chest, the outline of my padded bra, my smooth tanned legs showing below the hem of my skirt, and all twenty painted nails plainly on display. Phil, on the other hand, looked like a regular guy, hairy legs and all. I tried to bury the uneasy feeling I had by making small talk. "So what did Mom say about the relatives?" I asked, my girlish voice not helping me feel more at ease. "Not much - she just said she's got three half-brothers, no sisters. I guess they treated her okay. She promised to fill in the blanks when she got home." "She must have a stepmom too." "Probably. Didn't say." "It's really sad that she never got to see her Dad before he died." "Yeah." Our small talk definitely felt TOO small. "Phil?" "Yeah?" "I'm, uh ... I mean, like, are you, um ... what I'm trying to say is, uh ..." "Sandy, just spit it out!" "I'm TRYING to. I, uh, just wanted to know if you're, you know ... okay with, like, what's happening with me." As you can tell, that was SO tough for me to say - Phil and I had never enjoyed a close relationship, because we were always so different. It must have been the first time I'd ever asked him how he felt about something that was touchy-feely. Why did it have to be this? "What do you mean?" "PHIL ... you know what I mean. Like, all this ..." I gestured with both hands in the general direction of my body, my long pink nails adding unnecessary emphasis. He chuckled softly and shook his head. "Oh, c'mon Sandy ..." "C'mon? What do you mean?" "Nothing." Phil shook his head, and he was silent for a moment. Then he chuckled again and said, "You just reminded me of Nat - she's always wanting me to talk about my feelings. Is that all girls ever think about - emotions and stuff?" "Uh ... I dunno." His question caught me off guard. But then I thought, 'That's interesting - Phil seems to be lumping me in with girls in general. Does that mean he already thinks of me as a girl?' There was a minute of awkward silence. I was staring at him and from his expression he seemed to be deep in thought. Finally he said, "I guess I'm okay with you like this ... but it's taking a lot of getting used to. I think I was just starting to get cool with everything, and then you got a boyfriend. And it was kind of like, back to square one." Now I felt even more uncomfortable. "Uh ... what does Natalie think about it?" "Oh, she's cool with everything you do. You must have her wrapped around your little finger or something." That made me laugh, and for a second I felt more relaxed. 'That's what we need,' I thought - 'more humor!' "Maybe I'll show you how to do that sometime," I joked, hoping Phil would go along with me. "THAT would be awesome!" He did! "So did Mom tell you what my plans were?" "If you mean like, wearing dresses for the rest of your life ... yeah, she told me." "I'll probably still wear pants once in a while ..." "Just don't try that on your wedding day, kid." 'Did my brother just say what I heard him say?' I wondered. Whatever, it made me feel a little bolder. "I'm sorry, Phil - I guess I didn't do a very good job of being your brother. Maybe I can do better as, like ... you know ..." He glanced over at me. "As my sister?" I looked at him and nodded, feeling tears well up in my eyes. "Aw ... I think you'll do a good job. Anyway, you already cook, clean up after me - stuff like that. Like I always say ..." "I know, I know, don't say it. I'll make someone a good wife one day, right?" "Yup." I almost burst out giggling at the way he drawled 'Yup', like a drunken cowboy. And if it wasn't for the simple fact that I wanted very badly to become a certain someone's wife one day, I wouldn't have been able to stop myself. "Thanks, Phil. You're the best." "Sure, no worries. But, since you've got Nat wrapped around your finger, maybe you could do me a favor and tell HER that." "PHIL - I'm sure she already KNOWS. But I'll be sure to put in a good word for you anyway. Anything for my big brother." "And anything for my little sister." I was still dabbing tears from my eyes and cheeks when we pulled into the airport parkade. I had to flip down the sun visor and check my eye makeup to make sure I still looked presentable. I felt like giving Phil a big hug as we got out of the car, but I was still a little unsure of how much the poor guy could handle in one day, so I just followed him as he took off at a jog for the arrivals area. Mom was descending the escalator and her face lit up like a Christmas tree when she caught sight of us. "Oh, I'm so happy you both came to meet me!" she squealed. We did a big three-way hug and got lots of kisses too. "I love you kids so much!" "Wow, what's all that about?" Phil demanded. "I'm just so happy to see you! You have no idea how much I missed you." Then I got a stern look. "And you, young lady - you must have been out every night. I never got to talk to you once." "I was home all day Sunday - all night too," I countered. "Why didn't you call then?" "I was at the Blacklocks' house that day," Mom replied. "I had dinner with them, and we must have talked until midnight. I guess I lost track of time, and when I finally had a chance to call I thought it would be way too late here." "Okay, you're forgiven," I told her, happy to have successfully shifted the 'bad guy' label away from myself. By then, Phil had grabbed Mom's suitcase from the carousel and we started heading for the car. For a brief moment I thought of the amazing sexual encounters I'd enjoyed with Mark while Mom was away, but then I started feeling guilty so I switched gears and asked Mom to tell us all about her newly-found family. "There isn't much to tell," she began. "They're regular people, I suppose. Except they're a lot better off than most regular people. My father worked as a stock broker in New York most of his life, and I guess he did well at it. He'd been retired in Florida for quite a few years when he passed away." "How did he die?" I inquired. "He had inoperable skin cancer. He had very fair skin, but he spent a lot of time in the outdoors, playing golf mostly - before sunscreen was invented. When they moved to Florida he spent a lot more time out in the sun." Hearing that made me even more committed to using sunscreen, even with my darker skin. "Did he have a wife?" asked Phil. "Yes, two actually, and I met them both. Gwen is the mother of their three boys - my step-brothers. She and my father were divorced about twenty years ago. The current wife is a lot younger. Her name is Heather." "What are the boys' names?" I asked. "Bill junior - he's the eldest, then Daniel, and then Peter. They're all married with kids. I think Bill's in his early forties." By now we were climbing into the car. I offered to relinquish the front passenger seat to Mom, but she insisted on sitting in the back. "So what are they all like?" I pressed. "Oh, a little different ..." I knew my Mom - she never had a bad thing to say about anyone. 'A little different' was her way of saying they weren't her type of people. Phil spoke up. "So you didn't like them." He apparently knew her too! "Oh Philip - that's not what I meant ..." Phil and I smiled at each other. "Whatever you say, Mom," he chuckled. "I'm thinking they're kind of into money," I ventured. Mom confirmed my suspicion. "I suppose you could say that." "So how much money have they got?" Phil asked. "Or should I say, how much did they inherit?" A brief thought went through my mind: 'How much did WE inherit?' "I have no idea, because the estate still has to be sorted out. But if the house is any indication, my father was pretty well off. It's huge - it's on a small private island with about five or six other properties. It has its own boathouse, a swimming pool, tennis court ..." "Sounds like a real live mansion," I said. "You could say that too," Mom agreed. "All this time, while we were suffering in poverty," Phil mused, "and there was big money in the family. If we'd only known!" "To be perfectly honest," Mom replied, "I'm glad we didn't know. I think we've done very well, and I wouldn't have had it any other way. Well, except that I wish I could have known my Dad." Phil and I were silent for a few seconds, and I wondered if that last statement resonated with him, like it did with me. Then he spoke up again. "So they must have read the will. Were you named in it?" "Yes, I was. I'm supposed to get an equal share with my step-brothers." That revelation hit me like a ton of bricks. Mom could end up a millionaire - or is that a millionairess? Whatever, she'd probably have enough to retire on! But Phil saw the fly in the ointment. "Let me guess - they're none too happy about that, are they?" "You could also say THAT. I have a feeling they're going to contest the will." 'Oh dear,' I thought. Would Mom have to hire a lawyer and go to court to get her fair share? I didn't think she was the kind to put up a fight, especially when she didn't seem to care much about the money. But there was a principle at stake here! And I knew that Phil and I would be there for her every step of the way. ***** I was looking forward to Friday, because that would mean another super- fabulous day of hiking and hanging out as a foursome with Kath and Ben - probably the last one of the season, though. I'd been kind of ignoring Kath for much of the summer, on account of having a steady boyfriend monopolizing all my evenings and weekends. With my full cooperation, mind you. But I don't think Kath even noticed, because the exact same thing was occupying her life. We did get together in her backyard for sun- worshipping sessions once or twice a week, and all we seemed to ever talk about were boyfriend issues. Well, that and clothes, and makeup, and friends, and whatnot. Okay ... I should clarify that I was usually the one talking clothes and makeup, since Kath was still having trouble getting with the program. But I was doing my best to get a few simple concepts through her thick red-headed skull. Our Thursday session was typical. I was doing her toenails in preparation for the next day's events, and she was being her usual uncooperative self. "I don't know why you have to keep harping at me about this," she was saying. "Why can't I just be me?" "And why are you so against sprucing yourself up a little?" "'Cause I don't want to be a phony. With me it's what you see is what you get. Ben likes who I am inside - he's not that fussy about window- dressing." "How do you know?" "'Cause he told me so, that's how." "Earth to Kathleen: guys tell you what you want to hear, not what they're thinking." "And what makes YOU such an expert on guys?" "Uh ... like, maybe 'cause I AM one?" "Oh yeah - I keep forgetting. Can you blame me? You look like Catherine Zeta-Jones with that face and hair." "Who's Catherine Zeta-Jones?" "That girl we saw in the Zorro movie last month, remember? The main actress." I certainly DID remember. Who could forget? And if Kath thought I looked like her, that was a huge compliment! "Well, it's very nice of you to say that, but the fact is, I'm the only phony here. You, my dear friend, are the real deal. And I still think you should try to look the part. That's why I'm helping you." I was now on the final coat of gloss sealer. "Thanks, anyway - but I really don't need help. I just need to be who I am." "And what makes you think a little nail polish will change that?" "Well, okay, maybe it won't change who I AM, but I DO think it can send the wrong signals." "What do you mean?" "Like, that I'm too easy - you know, like I'm a flirt or something." "And you're not?" I couldn't resist. "SANDY!" Kath protested. "Well, okay, I'll admit I kind of flirted with Ben ..." "At least now you're being honest. And when we went out with the guys after that first hike, and we got you all dolled up, you were flirting with him then, too - weren't you?" "I guess so ..." "And it worked, didn't it?" "How do you know it wasn't my personality he liked? Maybe it wouldn't have mattered WHAT I was wearing." "And maybe it WOULD have. What did I tell you about guys?" "That they're visual," Kath replied, looking a little defeated. "But why should that matter? I don't get it." "That's 'cause you're a girl, my dear friend. It's not your job to understand. You just have to know what the rules are to play the game." I removed the blocks from between her toes. Her nails looked fabulously flashy - bright red and very glossy. "So what do you think?" I prompted. Kath raised her leg slightly and flexed her feet back and forth, checking out the way her nails gleamed in the bright sunshine. Then she pointed both her feet and I was amazed at how they could flex so far beyond a straight line. And the way she did that, with her perfectly finished nails, her legs and feet looked ultra-feminine. "Let me try that," I said. But I couldn't even get mine to straighten completely, let alone go past that point. How disappointing! "Ha - first it was your fingers, now your feet," Kath taunted. "You might look and sound like a hot chick, but you're still lacking in the essentials." Then, before I could react, she quickly recanted: "Oh Sandy - I'm so sorry. That was an awful thing to say ..." "That's okay - I deserved it after that nasty thing I said to you before - you know, the tomboy comment." "I forgot about it. But I guess neither one of us is perfect, right?" "You're perfect for me, Kathleen," I told her as sincerely as I could. "And you are for me, my darling Alexandra," Kath rejoined. With that, we embraced and she kissed me right on the lips again! "And we're very frank with each other, aren't we?" she added before giving me another kiss. ***** I was back in my house getting tidied up around two o'clock. Kath had got permission to borrow a vehicle so she could give me a lift to Milestones for my job interview at three. I was going over the whole thing in my mind, particularly the discussions Mom and I had the night before when I told her about my new job aspirations. Mom was supportive of my plans, but then she'd reminded me that my Social Security registration was in my given male name of Alexander, so I needed to be prepared to explain that to my new employer or his payroll person. I'd already filled out the job application form with 'Alexandra,' and my middle name Rene (the name of my maternal grandmother's father) was close enough to a feminine name to stick with. Only my sex posed a real problem, but I'd gone ahead and checked the 'female' box anyway. No point in asking for trouble, I thought, and if I was ever challenged on it I felt that I could BS my way out. For the interview I wanted to look as much like one of their other waitresses as possible, to make sure it would be easy for Miles to imagine me in that role. Fortunately I owned a short black skirt that was similar to what they wore, and for my legs I even had a new pair of nude pantyhose in one of my drawers. I didn't own a black top, so instead I wore a fitted, satiny royal blue one with a button-up front and very short sleeves, which I'd picked up on one of my outings with Natalie. Leaving it overhanging the top of the skirt, it reached about six or eight inches below my waist. That would do fine. But my shoe collection didn't offer a suitable substitute for black patent close- toed heels, so I went into Mom's room to try my luck. She had a few pairs of possibilities, and I tried on each shoe until I found a pair I could barely squeeze my feet into. But when I tried to walk in them they were very uncomfortable, so I made a mental note, 'Need to go shoe shopping.' Returning to my room, I looked myself over in the big mirror while I was brushing out my hair. I have to admit, I loved wearing heels. They made my legs look like they went on forever (especially with a short skirt!) and with the hose they made me feel so sexy! Now if I could just get used to walking in them. But while I was admiring my reflection, I turned to get a side profile and realized that my little bust wasn't doing justice to that top. Off it came so I could swap bras for one that could hold the gel inserts properly. 'This is WAY better,' I thought - some outfits just demand big boobs, don't they! But something was still missing, so it was back to Mom's room to check out her belt collection. A minute later I was in front of my mirror again, this time with a wide black patent leather belt that matched the shoes perfectly. It had a prominent silver buckle in front, which in turn sent me over to my jewelry drawer for my biggest pair of silver hoop earrings. The final result was much better than I could ever have hoped for. Now I could pass for twenty-one and my boobs were definitely quite impressive with the added volume and the snug belt directly below them. If only they were real, and then I could leave a couple more buttons undone! 'Some day,' I promised myself. Finally, after fifteen minutes spent on makeup, I felt ready for my big meeting with Miles. But I had to steal one last item from Mom's room - a black patent handbag with a short shoulder strap, into which went my ID, some cash, and my house keys as I closed and locked the front door behind me. Slipping it over my shoulder, I turned around to see if Kath was outside yet. There she was but Mrs. Thomas was with her, probably delivering a lecture on the importance of returning the car in one piece. Kath smiled at me and waved, but not her Mom. "Hello, Sandy," she greeted me with an all-too-familiar tone of suspicion in her voice. I never quite knew where the new me stood with that woman, but on this occasion I had the impression she wasn't overly pleased. "Hi Mrs. Thomas," I replied. "Thanks for letting Kath drive me to my interview." "I thought you were applying for a restaurant job - you look like you're off to audition for a Las Vegas revue." That comment made me feel rather uneasy. "Oh no, it's just for a serving position. But the other staff wear clothes like these, so I was just trying to look like I'd fit in." Mrs. Thomas glanced at her daughter. "Remind me never to take your father to THAT restaurant," she commented flatly. While driving to Milestones, Kath and I discussed her parent issues. I found out that she was getting sick of their restrictions on her freedom, and that she always felt embarrassed when they ordered her around like a child in front of her friends. I tried to assure her that, because she was an only child, they were probably just being a little over-protective. "Yeah, but it's MY life they're messing with," Kath stated. Soon we were pulling into the restaurant parking lot. Considerate as always, Kath stopped close to the front door so I wouldn't have far to go in my uncomfortable heels. "Thanks!" I told her as I got out. "Wish me luck!" As I made my way along the sidewalk to the door, my heels made that same wonderful clicking sound I'd always liked whenever chic, well- dressed women walked by, and it reminded me how far I'd already come in my transition from boyhood. I was about to interview for a coveted position only offered to select young women who possessed the right genetic traits - well, mainly one trait, namely physical beauty. Sure, you also had to have a great sense of humor and a very outgoing personality, not to mention the right servant attitude, but if you weren't 'model material,' as Mark had put it, you need not apply. On this day, I felt reasonably confident that I had the 'right stuff'. I was greeted by none other than Miles himself, who, I couldn't help but notice, scanned me carefully from head to toe, pausing as before at my bustline. His big smile told me that I'd passed inspection! "Hello Sandra," he began, "how are you doing today?" "Oh, I'm well, thank you. How are you?" "Fine, thanks. Let's go back to my office." I followed him across the stone tile floor, my heels echoing through the half-empty restaurant and announcing my presence to everyone. I had the feeling that all eyes were on me! Miles had a small round table in his office with two chairs next to it, and he asked me to sit in one of them as he took the other. I guessed that this was where he did all his interviews, because we were facing each other with nothing in between us and he got to look at all of me, not just above my waist. Without thinking I immediately crossed my legs! "Have you got the application form?" he asked. "Oh, yes - I almost forgot," I replied as I opened the snap on my purse and handed over the folded document. He scanned it for a minute, nodding a few times, apparently satisfied that everything it said about me was in order. Miles then queried me on how I felt about people in general - did I enjoy being around people I didn't know, did I like serving them, did I consider myself an outgoing person - that sort of thing. Luckily I'd been able to do my pre-interview with Chelsea, so I knew exactly what the right answers were! Other than that, for the most part the interview was a repeat of the one the other evening, although being more private he did ask me a few 'personal' questions like, had I ever taken drugs, been married, gotten pregnant, that sort of thing. At least I could be sure he didn't know everything Chelsea knew about me! The interview only lasted about fifteen minutes and I thought it went as well as I could have hoped. My feeling was confirmed when Miles looked me square in the face and said, "Well, I'm satisfied that you'd fit in well here and I'd love you have you come and work for us. Do you have any questions for me?" His question caught me a little off guard. "Uh, I guess I should know what the job pays ..." Miles chuckled, "That's good - you should always follow the money. Well, to be honest with you, the hourly pay isn't great - ten an hour. But we expect our girls to make that and a lot more in tips. If you're doing your job well, believe me, you'll be very happy with how much you earn. And you get to keep all your tips." I smiled and nodded. "That's great, thank you. Um, and what about clothes - everyone seems to wear the same kind of thing here." "Oh - sorry, I should have explained that. We don't have a uniform - call it a dress code. You can personalize your outfit a little, but try to think of it as variations on a theme. No pants - short black skirts are mandatory. Your blouse is where you can change it up, but we do like our girls to show a little skin. Not excessively, mind you ..." "Do I buy my own clothes?" "Yes you do - but we provide a clothing allowance." "Oh, that sounds perfect. Um, I guess I don't have any other questions." "Then you'll take the job?" "Oh yes, thank you - I'd love to." "Then we have a deal," he said with a smile, and as he rose from his chair he held out his hand. I rose as well and we shook hands. "When can you start?" I realized that with my heels on I was at least an inch taller than Miles. "As soon as you want me - oh sorry, but I can't work tomorrow ..." He laughed, "I'd be shocked if you were available that soon. But it would be best if you started on a weekday when we're not as busy. Can you come on Tuesday next week - you could work the lunch crowd and stay for the evening?" "Sure, that sounds great," I agreed, hoping it would be. ***** The next morning found four friends sharing breakfast at the same IHOP that Mark and I had visited the month before. Kath and I were amazed at how much the two guys could put away in one sitting, without putting on extra weight. Girls always had to be extra-careful around food. After all, clothes were pricey and you didn't want to be shopping for bigger outfits all the time! Well, the shopping part is always fun - it's the buying that tends to get expensive. But I digress. The hike was almost a carbon-copy of our first one in July, except for the milder temperatures, the lower humidity and lack of annoying insects. Oh yes - there was also that other difference: the original four friends were now two committed couples. But that didn't get in the way of us having a great time as a group, and we all had tons of laughs. Kath and I agreed that doing this kind of activity together with two super guys was as good as it gets. We even got to dangle our feet in the lake during our lunch break, and as I'd predicted, Ben made a big deal over Kath's gorgeous feet. I'd made her promise not to tell that they were my handiwork - I wanted him to think she did it just for him! The evening was a lot like the other one too. There we were, two very pretty girls (if you don't mind me saying so) enjoying a nice romantic dinner with two very eligible guys. Every other male in the restaurant must have checked Kath and me out, and I'm sure our men were checked out by all the females! As before, though, the only downer was when we got back home. Kath's overbearing parents must have been camped out at the living room window, just waiting for our return to pounce. And that's just what happened - no sooner did we pull into the driveway, than both of them were standing at the door ordering her inside, complaining about how late she was. 'For heaven's sake,' I thought - 'it's only half past eleven and it's still summer holidays!' The guys felt embarrassed too. And I felt really bad for Ben, whom I knew was as good a guy as a girl could ever hope for. I couldn't believe how stupid Kath's parents were - didn't they realize how many losers were out there? They should have been counting their lucky stars that Kath was going out with Ben. But they seemed to completely ignore him in their quest to annoy their daughter. I tried to make up for some of the crap by giving Ben a big hug and telling him how much I appreciated the way he treated my best friend. And how I was sure her parents would eventually come around. He just shrugged and said it was no big deal. For the first time, I began to feel worried for Kath. She had such an independent spirit - how much longer would she be willing to put up with that nonsense? To be continued ....