Ready for Anything?

Anal

Ready for Anything?”Pick one.” Those two words started everything. Those two words werethe innocent drink that led to my addiction. They’re responsible formy current situation, and the nerves racing through my mind as Iapproach the hotel lobby bar dressed as no man does, at least not onewho expects society’s approval. I hear my high heels click on themarble of the lobby floor. I adjust my little black dress and playidly with my long dangling earrings. As I’m nearing the bar, my mindgoes back to that first choice …”Pick one.” That’s what my girlfriend said, as she stood two tubes oflipstick on their ends. They were the same brand, both in a darkplastic case. They looked identical, except for the name, which wasconcealed on the bottom of the tube. One of the tubes was a deep redlipstick that I somehow convinced her to buy earlier that day. Theother was a neutral shade that she preferred. But they looked the samewhen they were standing up in front of me like that.”Pick one,” she repeated. “If you pick the bright red one, I’ll put iton and suck little Jimmy so much it will make your head spin.”I hesitated.”Come on,” she continued, “an offer like this doesn’t come around veryoften. That blowjob you always want is just one touch away. You havea 50/50 shot. All you have to do is tell me which one is the sluttylipstick you begged me to buy.”Still, I hesitated. I was obsessed with the thought of that blowjob.Michelle doesn’t like to give me blowjobs. She says it doesn’t tastegood, that it’s smelly and that she hates to swallow my cum. (Otherthan that, I guess it’s great.) But here she is, giving me chance.All I have to do is pick the right color lipstick.I reach out to pick, my heartbeat racing. I stop. It must be a trap.”If I pick the red one, you’ll wear it?””Yes, and I’ll wrap those red lips around your cock just like you want.You’ll have the best orgasm you’ve ever had — maybe several.”OK, she had repeated the positive a few times. “And if I pick theother one?””That would be fine with me. I’ll wear that one, and you will treat meto dinner at a place of my choice. But little Jimmy won’t get anythingtonight. Not even your own hand.”This whole discussion has gotten me excited. Jimmy is full-sized andhard right now. My heartbeat must be at 130 at this point. I canvisualize the reward I’ll get if I pick correctly. It will be sosweet. But if I pick incorrectly, I’ll get nothing. I see thegambler’s dilemma. I understand the rush of the wager. I reach out,again, toward the lipstick on the left. God I hope I’m correct. Ipause, then lunge and touch it.”The left it is,” she declares. “Now let’s see what’s in store for youtonight. Will it be pleasure? Or will you be the pain of lostopportunities all through our meal?” With that, she holds the lipstickup. I can’t tell what I picked, nor can I read the name on the bottom.Lipsticks have those ambiguous names anyway. It’s always somethingsultry like “Seductive” or “Kissable” or “Goddess.” Why can’t it justsay “Red”? Whatever, just please let it be red.She pulls off the cap, still concealing the contents. My heartbeat isat 150 now. She slowly twists the bottom, bringing the lipstick up.When I see the red tip, I jump up. YES, I think. I knew it!!Michelle smiles. She’s enjoying this, too. Before she paints herlips, she takes my hand and guides it to her vagina. I begin rubbingher with my fingers, but she’s already soaking wet. “See what you cando to me?” she whispers. “Now you’ll see what I can do to you.”Needless to say, that experience was one of the best we both had everfelt. I couldn’t believe the way Michelle acted. But more thananything, I couldn’t forget the rush of the gamble. The risk-reward ofthe choice was enticing.After that night, we had many more experiences involving game playing.Michelle always set up the choice. For the first few times, itinvolved that red lipstick. When I got that, it meant success. But ifI got something else, it meant disappointment for me. I won about asthe odds would predict — about half of the time. But the thrill of”victory” was oh so savory that it made up for the disappointments ofthe losses.Soon, the games migrated to a series of dares. If I won, she would dosomething I wanted, or something mildly embarrassing. If I lost, herchoice usually was to have me naked and at her direction. One time,she even took me out at midnight, wearing only my windbreaker while shedrove us through a fast-food pickup window.After a while, Michelle changed the stakes. It was after a dinner outat a restaurant. Fittingly, it involved those two lipsticks again. Wewere sitting at the back of the restaurant. It was late, so most ofthe crowd had finished and we were one of the last couples in the place(until the after-hours crowd would arrive). Michelle took out the twotubes, shuffled them and stood them up on the table.”Jim, its time for another of our adventures. I hope you’re up for thechallenge this time.” Hearing her say that, and seeing the array, Iquickly “rose” to the occasion, you might say.”I have your favorite red lipstick here. I also have that neutralshade. The red of course is bold and attention-grabbing. The neutralis so light, so subtle, you can hardly tell I’m wearing it. Now, likebefore, if you select the red one, that’s what I’m going to wear. Wewill head home immediately and I’ll pleasure you like you so adore.All you have to do is select the right color.”Thinking we’re playing the same old game, I start to reach out.Michelle grabs my wrist and stops me.”Wait a minute there, big boy. We’re not done. You see, this time,there’s a little more to the wager. If you select the red one, I’llwear it and do the things I said. And if you select the neutral one,I’ll wear that, too. But here’s the difference: YOU have to wear theother lipstick. If you pick the red for me, no problem. You get allthe benefits I said, and no one will even be able to tell that you’rewearing anything. However, if you pick the neutral for me, I get tosee what your lips look like in this red color. You will have to walkout of the restaurant, to the car and wear it all the way home.”So, pick one. One for me, and one for you.”I try to talk her out of this. “That’s not balanced at all,” Iprotest. “The stakes are very different. If you’re wearing the red,no one thinks differently of you. But if I wear it, I’ll be humiliatedby anyone that sees. I think it’s more fair if I only have to wear theneutral one — and only if I don’t pick the red color for you.””No, there will be no negotiation on the stakes. I get to set them. Iwant to see you in the red lipstick — right here, in public — if youlose. That’s the bet. If you don’t want to play, you can forfeit.But forfeitting will have a cost, too.” I don’t bother to ask whatthat is; I can see her mind racing already. Quickly, she continues, “Iknow. I bought some nail polish at the store this afternoon. It’s inmy purse. I haven’t shown you it yet. It could be bright, it could besoft. It could be one of those that only shows a color when exposed tothe sun. Or, it could be the new clear topcoat I’ve been meaning tobuy. If you choose to forfeit, I will paint your fingernails with thatnew polish, whatever it is.””So there it is, take your chances with the red lipstick, or take achance on the nail polish I have in my purse. What do you want to do?Are you going to be bold and pick a lipstick? Or, are you too wimpy torisk it and would you rather that I give you a manicure with whateverbottle I have with me? The choice is up to you.”I couldn’t believe what she was saying. Where had these new downsidescome from? Why did she want to embarrass me? Despite my confusion, Iknow she is serious. I’m also consumed by the rush of the gamble. Iponder my chioces. I can’t choose the nail polish. It’s mostcertainly a set-up. Yes, she did remark this morning that her topcoatwas getting old, but did she really buy a clear polish? I doubt it.This is like those sucker bets in the middle of the craps table: theysound appealing (“8 the hard way”), but they’re really bad odds. No,I’m certain that the nail polish is colored. It’s a hot pink orsomething. There’s no way I’m falling for that bet.Besides, I couldn’t back out like that. I’d feel embarrassed abouthaving wimped out of the real challenge, and I might end up with hotpink nails anyway. No, I had to pick the lipsticks. (Go for thegusto, I tell myself. Go big or go home.) I reach out, choosing theleft one again. It was lucky that first night, why not now?But it wasn’t. The lipstick on the left was the neutral color.Michelle painted her lips with it quickly. Then, she took the redlipstick and outlined my lips generously. She offered me a mirror tosee, but I refused. I didn’t want to know what it looked like. I’msure it was ridiculous. As we got up, our waitress returned to thetable. She noticed my red lips. She smiled, and said, “Ready for anight on the town now? Have a great time!” As we walked out of therestaurant, Michelle held my hand and made me walk slowly. My palmswere sweating, and I could hear my heartbeat. I was thrilled andmortified at the same time. Worst of all, this feeling showed in thebulge in my jeans as we walked to the car. Luckily, other than thewaitress, we did not encounter anyone else. Thank God.Our lovemaking that night was fantastic. Little Jimmy was Big Jim thewhole night. Michelle liked having me put lip prints all over herbody, and enjoyed the taste of my lipstick when we kissed.We continued this way for another two weeks. My penalties for losingnow involved some form of feminine feature — lipstick, paintedtoenails, panties, even a bra once. Unfortunately, after a couple ofweeks, Michelle lost interest in these games. She didn’t really sayanything about it. At first, Michelle didn’t initiate the gambles asoften. When she did, it was with less imagination, almost mechanicallyrepeating the “if you lose, you’ll wear red lipstick” downside. I’mnot one to force confrontation, so I didn’t really question herdwindling enthusiasm for the games. I just tried to go with the flow,figuring maybe she would find that enthusiasm again. My only hint asto her true feelings was a side comment one time, when she said, “can’twe just try something normal tonight?”After that comment, our lovemaking continued, but moved back to themore traditional, passionate lovemaking between two consenting adults.The kind that is satisfiying but they don’t usually write storiesabout. I was accepting of this change. After all, we were in lovestill. So, everything was OK, I guess. No, it was good, I toldmyself. Really. It was good. Better than good … great.The Addiction GrowsI should have said something, of course. But I didn’t. Instead, oneday, I just succumbed to my unsatisfied desire. My work involvesregular business trips, typically 2-3 days at a time. About a coupleof months after our lovemaking returned to “normal,” I was packing fora trip when I spotted the neutral lipstick of our gameplay. It hadfallen over, tucked in the back of our bathroom closet, next to sometravel size toothpaste. Discarded, like our gameplay had been.Impulsively, I took the tube and hid it among my toiletries. Twenty-four hours later, I found myself in a hotel room all alone. I began tothink about our games. Any gambler will tell you what comes next. Imissed the thrill. I missed the excitement, the wonder, thenervousness. So, I dug out the lipstick from my bag. I put it on. Icould taste the color on my lips, even though I couldn’t really see it.I kept the lipstick on for about an hour. I didn’t go anywhere, butthe feeling was thrilling.The next night, the feeling returned. I put the lipstick on again.But this time, I needed more. Like the gambler, I guess, I needed therush of higher stakes. So, I walked to the ice machine on my floor.No one saw me, but I was on guard the whole two minutes of the trip. Ipleasured myself back in the room, tasting the lipstick the whole time.An hour later, the feeling returned again. I painted my lips once moreand headed toward the lobby. It was 11 pm. No one was downstairsexcept the night clerk. He didn’t pay much attention to me. Cravingmore, I walked up to him and asked him where a d**gstore was. Lookingbored, he said, “Outside, to the left. It’s open all night.” Hedidn’t even look me in the face, much less take note of my paintedlips.Taking a deep breath, I exited the hotel and turned left. I’m not surewhat I’m going to do at the d**gstore, but I head there anyway. I lookleft and right, but don’t see anyone on the street. I get to thed**gstore without incident and enter. I could have gone anywhere inthe store, but the cosmetics aisle was right up front. I went there.There was a young woman selecting something. I don’t think she evenpaid me a second thought. It made me nervous anyway. When she left, Imigrated to the nail polish section. They had a huge display from OPI.It’s the brand Michelle uses. I stand there for a moment, trying todecide what to do. My eyes scan the various colors. I don’t daretouch any — that’s too obvious. I’m thinking about my excuse: mygirlfriend sent me to get a color for her. Her nails were chipped orsomething. No, that’s pretty lame, I think. It’s 11 pm; what woman isfixing her nails at 11 at night? The only other thing I can think ofis that it’s a dare. Still lame, and it draws attention to me anyway.Finally, I decide that it doesn’t matter. Who’s going to quiz meanyway? You don’t need to justify your purchases. I’ll just grabsomething and go. So, I reach out to pick a red one. They’re so closein color that I almost pick one at random. Out of curiosity, I glanceat the name. Redy for Anything. Cute. Almost appropriate, I think.I head to the counter to pay. As I get there, I realize this was adumb thing to do. Here I am at 11 pm, buying just one item — red nailpolish. I’ll go with the chipped nail thing, I tell myself. But theclerk, a 20-something girl with three piercings in her ear and a tatooof a dove on her wrist, doesn’t ask. Instead, she says to me, “I lovethis color. It’s more conventional than I usually wear, but when myMom insists on something respectable, I use this.” I start to mumblesome form of “thanks,” but she looks me in the face. Her eyes go to mylips. She must see the shine. Then, in a softer voice, she says, “Youprobably want some remover too, honey. It’s right in aisle 2. We havetravel sizes, so you don’t waste any.” I don’t respond, and she addsmore. “Do you have a topcoat? It really makes the nail polish shine.I recommend the Sally Hansen topcoat. It shines more and it’s cheaper.No sense paying top price for the OPI, you know?”Now’s my chance to use the chipped nails excuse. But I don’t.Surprisingly, this thrill is even more intense than at the restaurant.A woman I don’t know just outed me. I could lie, and she probablywould let it go. But she won’t believe me even if she let it go. No,she definitely would be telling her girlfriends (and maybe herboyfriend) later about the guy who came in to purchase nail polish forhimself.Instead of lying, I mumble thanks and I turn to pick up the remover andtopcoat like she recommended. When I return, I can’t even look her inthe eye. My hands are sweaty. Without even looking, I can imagine hersmiling face. I hear it in her voice, too, when she says, “Have funtonight! We’re open all night, if you want to show me how it looks.”I’m mortified, but strangely excited at the same time.I don’t paint my nails, however. It’s too late and I have an importantmeeting tuzla escort tomorrow. I can’t afford to be reckless. But I set the nailpolish out on the desk, in plain view. The rest of the night, I keptrunning the experience through my mind. Over and over again, each timethinking about those two minutes with the clerk. I even gave her aname: Katherine. Katie, for short. That sounded right to me. It wasfun and flirty, but firm and traditional at the same time.From then on, I was hooked. I was hooked on the adrenaline rush of thegamble. I couldn’t wait for the next business trip, and the nextadventure. Over my next few trips, I purchased a complete outfit formyself. Buying a dress was intimidating for me, but probably was theeasiest of my purchases. I did a little online research before I went,then headed right to the department I needed. I selected “my” dress:a red, 3/4 sleeve dress with a ruffle in the front (it was called a”rouched” front online). I guessed at the size, using themeasurements from the online site. It looked like the dress was longenough to reach my knees. My only indulgence was, after glancing leftand right to make sure no one was in the area, I quickly held the dressin front of me. Not up to me (that was too much), but at body leveland in close. Yes, the length would be fine. I headed quickly to thecheckout. I asked for a box, so the clerk would assume it was a gift.It must have worked, as the clerk commented how sweet I was to buy adress for my wife. Little did she know.Buying heels was embarrassing. I selected basic black pumps, with afour inch heel and peep toes. I didn’t try it on or anything. Onceagain, I had checked sizes using the size charts online. But there isno hiding who you’re buying heels for. No man that I know buys heelsfor his wife/girlfriend. And the clerk knew it too, of course. Shesuggested I buy some of the tights, which they had at the register.They were two for one, so she gave me black and nude ones.Finally, thinking of no way around it, I went to a department store forundergarments. I bought a bra, panties and shapewear. I waited andwandered until there was no line at the register. I handed the clerkthe items, and had my cash in hand. (I always selected the line with afemale clerk.) I couldn’t make any eye contact at all. Luckily, shedidn’t delay, didn’t ask me to join their bra club or anything. Ipractically ran out of the store, my pretty underthings in tow.The DiscoveryMy big opportunity came a month later. It was much longer than usualbetween business trips, and I was really anxious to get going. I wasgoing to be at an educational conference. One with lots of lecturesduring the day but no obligations at night. It would last four days,Monday through Thursday midday. Since I wouldn’t know anyone, Ithought I could try on my dress and heels in my hotel room. I’d justwear them in the room, maybe on the balcony if I was daring. I eventold myself that I would hang the dress in my closet and leave theheels out on the floor. It thrilled me to imagine what the maid wouldthink. With only one outfit and none of the makeup and all, it wouldbe clear that there wasn’t a woman staying in the room. I smiledthinking of the small but very safe humiliation of that plan.On Sunday morning, I packed for my trip. I secretly put the dress andundergarments in a small bag and placed it inside my suitcase. Theheels were nestled in the bottom of my luggage. I would put the nailpolish in with my toiletries. I was planning to carry the beigelipstick with me on the plane. I’m all set.Right after I packed, Michelle surprised me. “Honey, I have somethingspecial for your trip,” she announced. “It’s something you might like,I believe. You see, I recently got another of those gift bags of mycosmetics. It has a lipstick in it. It’s a duplicate of one of myfavorites. A cute soft pink. One of the ones you’ve liked when I woreit. ” She leaned in to kiss me, and slid the lipstick into my handwhile we exchanged affections. “Take this with you on your trip. Whenwe talk, you’ll be able to imagine me more vividly than normal, seeingthe lipstick and hearing me on the phone.” Then she winked and said,”who knows, I might even want us to be ‘twins’ one night this week!”The image got a quick rush out of me. Perhaps my playful and daringgirlfriend was back.I quickly put the lipstick in my pocket, with the beige one (thoughMichelle didn’t know that). She then headed out for her lunch withfriends. I don’t have to leave for my flight for an hour. AfterMichelle left, I started running through my plan again. It would beperfect. Running through everything, I remembered “Katie,” the clerkat the d**gstore. Impulsively, I dug the nail polish out of my bag. Ihave time to do my toes now, I think. I’ll be wearing socks at theairport, but still — I’ll know my toes are painted. So, for the firsttime ever, I sit down and paint my own toenails. (You should know,however, that, during our “adventurous period,” I had paintedMichelle’s toes a few times. So, I wasn’t half bad, even if I wasrunning the brush in the opposite direction this time.)Soon, my toes were a bright red. Redy for Anything. Definitely, Ithought. I packed my bag, put Michelle’s pink lipstick in with mytoiletries and headed out. The airport security went smoothly. Thescreeners don’t really care whose bag has heels or a dress in it;they’re legal for travel, so what does it matter? My neutral lipstickeven went through with my keys and change no problem. If anyonenoticed, they didn’t care.My flight had a stopover where I had to change planes. The layover wasan hour and forty five minutes. Not too long, but it would give metime to get some food if I got hungry. During my first flight, I gotbold. I had an aisle seat, and at one point, I adjusted my positionand felt my tube of lipstick. Impulsively, I thought I would wear itfor the rest of my flight. It was a neutral shade and, except forKatie, no one had ever noticed when I wore it. Besides, the lady in myrow was sleeping. She probably would never even look.I went to the lavatory to put on my lipstick. I did my business andthen, getting ready to get out, I pulled out my neutral lipstick.Except there was one problem. It wasn’t my neutral shade at all. Itinstead was the soft pink that Michelle had handed me. (I must havegotten them mixed up when I repacked.) I could have stopped. And if Idid, I wouldn’t be walking down to the hotel bar in this black dressand four inch peep toe heels. But, the gambler in me took over.”Don’t be a wimp,” he said, “No guts, no glory.” So I put the pink onmy lips — lightly. Just a light coat would do. I had to steady myhand, but I painted in the lines, so to speak. There, I thought.Looks good. No one will notice, I told myself. It’s almost thenatural pink of moist lips. Yes, absolutely.Heart reacing again, I return to my seat. The cabin lights are off,and no one can really see. I’m fine. Even the lady next to me isstill asleep. But I can’t really concentrate the final 20 minutes ofthe flight. When we land, I plan to make a quick exit. Luckily, I’min one of the premium rows, so there is no waiting. My exit goessmoothly, except for the flight attendant in front. She sees me andstarts to wish me a nice day. She does a double take, ever soslightly. Does she see?, I wonder. But she continues on as normal.Having exited the plane, and entered the mass of travelers, I regain myconfidence. Everything is OK. I’m anonymous again. Everyone is toohurried to care about other travelers anyway. I’ll leave it on untilmy meal, I decide. Then I will wipe my lips and see the pink on mynapkin.I find my gate, enjoying the safe thrill of the moment. I’m shakenfrom my state by a familiar voice. “Hizzonor?” I hear. I immediatelyknow who it is. It’s Lizzy, Michelle’s roommate in college. Lizzy isoutspoken, bold and uninhibited. She is quite attractive, too. Incollege, I remember being a bit too enamored of Lizzy. I tried to denyit, but Lizzy and Michelle used to tease me about it, saying theyalways wanted to try a threesome, if I was up for it. They weren’tserious (I think); they just liked seeing me turn red every time theyplayfully suggested having sex together.Lizzy teased me about how pretentious my name sounded. James HamiltonMadison Walker, III. She said it definitely was upper crust, whatwith two middle names that really were last names, and with my namebeing “the third.” She said I was destined to be a judge or mayor orsomething — hence “Hizzonor.”When Lizzy called my name, I knew I couldn’t escape. She came right upto me. “Hey, Jimmy! Funny meeting you here!” She came up from behindme. “I almost didn’t recognize you, with your shaggy hair. It almostcovers your ears. Not respectable for a judge, you know.””Michelle likes it longer,” I say, glad she’s distracted by my hair.”I bet she does,” she replies. “I love it, too. It would give mesomething to grab onto when you’re fucking me and I have an orgasm.Your buzz cut in college would have offered me nothing to grab holdof.” Yes, she just commented out of the blue about having sex with me.That was Lizzy.”I’m sorry, I have to catch my flight to Denver,” I say, feigning arush.”Denver?” she says, “Small freaking world! That’s where I’m heading.Are you on flight 2415?” I am, I say. “Well that doesn’t leave for anhour and a half,” she says.Then it happens. Lizzy finally notices my face. “Jimmy,” shewhispers, “Are you wearing lipstick?” I quickly deny it. “You sureseem like it. Your lips are a pinkish … and a little shiny.”Without warning, she reaches out with her left hand. She swipes my lipbefore I can even react. My lipstick smeared onto her finger.”That’s definitely lipstick, Mr. Walker.” She smiles broadly. “OMG!You and Michelle are playing some sex game, aren’t you? I knew youwere kinky. You should have tried that threesome back in college.”She reaches for her phone, probably to text Michelle.”No, wait!” I say, hurriedly. “Don’t text Michelle! She doesn’tknow.” My fear made it impossible to lie. Interrogators say that. Ascared man doesn’t have the time or the wits to craft a good lie.”Oh. Sneaky, are you? Naughty and sneaky. No, naughty, sneaky andkinky. I’m intrigued, your honor.”She pulls me to a seat at the far end of a gate. “If you don’t want meto tell Michelle, you better be honest with me.””Are you wearing anything else?”I nod.”Panties?”I nod again.”What color?””Red,” I whisper.”Naturally. No sense in going with white. They’re satin, aren’tthey?” I don’t even answer, before she goes on, “A bra?””No. In the bag,” I say.”Do you have other clothes in the bag?””A dress and some stuff.””Sweet. And are we wearing anything else girly? Pantyhose?Eyeshadow? Perfume?”I shake my head no. “Only nail polish,” I say, “On my toes.””Show me!” But I can’t. Instead, I reach into my bag and hand her thebottle. She inspects it. “That’s a bright red. I bet it looks sexy.”Then she looks closely at the bottle. “Redy for Anything,” she says,”I hope you are — ready, that is. This trip just got very interestingfor me.”Under Liz’s Control”Give me your suitcase,” she says. “OK, I’m going to go inspect yourgoodie bag. Stay here with mine. … And hold my purse while I’mgone.”Lizzy’s suitcase is a pink and yellow floral design. Her purse is pinkleather. She makes me sit with it on my lap. (“It’s too expensive tolay on a dirty airport seat,” she says.) I sit for at least fiveminutes, waiting for Lizzy to come back. I’m staring straight ahead,trying to pay attention to the TV monitor. If someone is laughing atme, I don’t want to know.Finally, Lizzy returns. “Your dress is very cute. And I love theheels. Four inches. I’m impressed, your honor. And they have a peeptoe, so they will show off that pedicure well.””But your dress is not appropriate for the occasion. It’s summertimenow. You packed a winter dress. One that’s a touch formal. You know,it’s the holiday party type. We’re going to have to fix that while inDenver. We can find you a nice sleeveless dress. Maybe a little blackdress. You don’t have one of those, do you?”I shake my head no. “Goody. Every girl needs one in her closet. Itis very versatile and goes with just about any heel.” Then, Lizzycontinued. “OK, here’s the deal. I like your little game, but I wantto play too. So I’ll play dress up with you. I get to be the boss. Imake the rules, and you, my cute little puppy, are going to followalong. Right?”I nod. She continues. “I thought so. OK, here’s your first rule.For the trip, I’m going to call you, ‘Jamie’ when I want. That’ssometimes a man’s nickname for James, but of course it’s girly too.Just like you: a man, but girly, apparently.””Second, you are going to have to take this up a notch. You obviouslywanted to be noticed, so I’m going to make you do more. Embrace yourgirliness. I will expect you to trust me. And I will demand that youcomply. Otherwise, I’ll just stop and let my friend know what you’redoing behind her back.”We’re going to start right now. I want you to go into the men’s roomand put on your bra. A girl shouldn’t wear panties and not a bra,don’t you agree? Going braless was a thing in the seventies, but it’sfrowned upon now. So, go put your bra on. You can leave your lightjacket on if you like. Just so I know that you’re wearing your properundies. And, freshen your lipstick. It’s starting to wear off.””While you do that, I’m taking your nail polish and going to get amanicure at the 10 Minute Manicure shop right there. Meet me at theshop when you finish.” When I didn’t move, she said, “You betterhurry. If I finish my manicure before you come back, I’m going to tellthe manicurist that they match your toes. And I’ll make you show her.You know better than to doubt me on that.”Confused and scared, I hurried to the mens room. I took over thehandicapped stall — I didn’t care. I can’t believe what justhappened. I’m dead, I think. Lizzy won’t let go of this. What am Igoing to do? What if she tells Michelle? Then I’m really screwed.Not because I’m crossdressing (I think she would be OK), but definitelyfor hiding things from her. No, I have to find a way out of this andfigure out how to tell Michelle myself later. For now, I need to buytime. Better to go along for a while, while Michelle is not around.Secretly, the tasks are exciting me. I can’t believe I’m going to weara bra in public — and do so at the request of a woman.So, I take off my jacket, unbutton my shirt, and pull out my bra. Itis red satin, just like my panties. Yes, the red is cliche but I’m notthat original, I figure. I quickly fasten the bra, reaching behind melike an expert. I put my shirt back on, noticing that the red shows asa dark shadow under my shirt. Better put the jacket back on. I startto leave, and remember the lipstick. Lizzy said to freshen up. I’mnot doing it out there, so I try in the stall. I don’t have a mirror;I hope this is close.Having hurried, I make it out and to the manicure table just as thewoman is putting a clear topcoat on Lizzy’s nails. “Hey, honey! Thereyou are! Do you like my color?” she says, holding her nails toward me.They look beautiful. And with the top coat, her nails are shinier thanmy toes are (at the moment, at least). It was then that I also noticedthe wedding ring on Lizzy’s finger. She’s not actually married, Iknow. We would have been in the wedding. It’s just for show, I guess.After mumbling the “husband-like,” “sure, they look fine,” Lizzycontinues the game. “Dear,” she says, “Remember when you picked up mylipstick after it tuzla escort bayan fell out at security? I’d like it now.” I didn’tpick up on her clue quickly enough. “You know … the pink one thatyou think is so cute? I want that one. Can you get it out of yourpocket?”Turning to the manicurist, she said, “He’s so cute. I sometimes havehim holding a virtual array of cosmetics for me. Maybe I should gethim his own purse to carry them. haha.”Lizzy’s nails were sufficiently dry, so she carefully took the lipstickand covered her lips with them. Then, she pulled me close, leaving herleft arm dangling in front of my shoulder. With her right, she took aselfie of the two of us. A selfie, I realized, that not only showedthe red nail polish I secretly was wearing, but also showed ourmatching pink lips. How am I going to get that from Lizzy?On the flight, Lizzy has arranged to have us seated together. She’s abigwig frequent flyer with this airline, so the attendant dideverything they could to accommodate her. When we’re on the plane,Lizzy raises the armrest between us, lays a blanket over the two of us(she had that from one of her trips) and snuggles close to me. We looklike the loving husband and wife. Just the kind that wear matchinglipstick.After we’re in the air, Lizzy whispers into my ear. “Jamie, time foryou to unzip your pants and show your panties. I would do it myself,but it might ruin this manicure.”I comply. Lizzy takes my left hand and places it on top of my penis.I’m hard already. Then, she puts her right hand on top of mine andbegins rubbing me back and forth. Lizzy is stroking me, but notactually touching my cock. Lizzy extends her left hand forward, towhere I can see it. In my ear, my loving “wife,” begins to whisper.”Jamie, this is such a darling color you have. I’m wet thinking abouthow it matches your toes. And I can’t wait to see it on your fingers.You’ll paint your own fingernails for me, won’t you? Of course youwill. You don’t want poor Michelle to find out how you’ve beensneaking around on your business trips, so you’re going to do whateverI say. Besides, I think you like it. You’re so naughty. Such anaughty boy. Or should I say naughty girl? Yes, you’re a naughty boywho wishes to be girly. Well, for this trip, I’m going to make yougirly. Very girly. You might even be pretty — pretty enough for meto have sex with. I like my boys on the effeminate side. If youcooperate, maybe we can experiment. Or maybe we can have thatthreesome. We three girls, all dressed alike.”Lizzy did not have to go any further. I came all in my red satinpanties. I could feel the wetness for the rest of the flight. Lizzydidn’t do anything more that flight. But she did lay out her ordersfor me. She took three pair of her own panties and gave them to me.Each day, I’m to wear them under my business clothes. I also have towear my beige lipstick daily, “fixing” my lips every two hours. Eachnight, I’m to meet her at a place she designates. And do what shewants, of course.I finally make it to my hotel room late. I check in with Michelle, butI’m exhausted. She playfully asked if I kept her lipstick in my pocketthrough the flight. I tell her yes, but she doesn’t know the wholestory, not by a long shot. She wants to have phone sex, but I tell herI can’t tonight. I think she’s a little annoyed with me over it. Ohman, this week is going to be difficult.MondayMonday goes fairly well. I’m wearing yellow lace panties from Lizzy.I carry my neutral lipstick with me all day. I don’t think anyone cantell I’m wearing it, but I try to keep from close contact with anyonejust in case. Lizzy texts me twice, both times saying, “Time tofreshen up, Jamie!”As instructed, I meet Lizzy at a downtown shopping area that night.Our first stop is “Heel Heaven,” a massive shoe warehouse. It’s twicethe size of the place I bought my four inch heels from.”Your peep toes will work for the dress,” she declares. “But I wantyou to have some business appropriate shoes as well. We can’t have youwearing stilettos to class, can we?”I’m not ready for this. I don’t want to do this, I say. But Lizzytells me to relax. “I’m not going to make you try them on here.Unlike high heels, a lower heeled shoe is more uniform. So we can getaway without trying them on.” I start to relax, until she says, “Ijust want to measure you properly.” With that, she makes me take offmy shoes and socks right in the store. My red toes are shiningbrightly, visible to anyone who might be in the vicinity. I quicklyput my foot on the sizer, but Lizzy makes me stand up. An older womanturns the aisle as I do this, and sees me and my painted toes.”Pretty,” she says, and laughs.Thankfully, the woman’s comment is the only one I endure in that store.Lizzy let me put my shoes and socks back on, and we spend a few minutespicking out “loafers.” They’re more narrow than a typical men’s shoe,and the heel is shaped differently. It’s a block style, but with a twoand a half inch heel, rather than the typical half inch of a men’sshoe, so there is more “air” visible beneath the toe and heel. Womendefinitely will know it’s a woman’s shoe if they pay attention. Menprobably won’t notice.But Lizzy had more in store. Much more. Our next stop was a lingeriestore. We appeared to be the loving couple, shopping for a littlespice in our lives. Lizzy took me to the corset section. A woman cameup to us to help. Everything went smoothly, as Lizzy and the womandiscussed types of corsets, colors, and other elements. It turned badwhen the woman asked what size Lizzy wanted.When Lizzy said “30,” the woman stopped. “We size our corsets based onthe waist, ma’am. We usually recommend that you select a waist sizefour inches below your natural waist. You’ll probably need a 22, maybe20.””I know,” Lizzy said, “The corset is for him. I think a 30 will workright, but you can measure if you like.” When Lizzy said this, Iwanted to just run away. But I couldn’t. The woman turned and,without missing a beat, looked me up and down. She agreed that a 30would work.”Great,” Lizzy replied, “Can you show him how to tighten it? He’s beendying to wear a corset. If he gets one, I think he should know how toput it on by himself, don’t you think?” So the woman took us to adressing room. It was large, clearly big enough for two.”Leave your pants on, sir, and you will need an undershirt. Since youdon’t have one, I’ll get you a camisole. Company policy.” I took offmy shirt and we waited for the woman to return with my camisole. Itwas a white, satin camisole. She slipped it over my head and startedto reach for my corset. Unfortunately, she saw my growing member.”I’ll give you a minute,” she said, with a slight undertone of disgust,as she looked at both of us. “When you two are done, come find me.””Holy crap!,” Lizzy shrieked. “You freaked her out! I can’t believeyou’re so naughty! Getting excited about your first corset, are you?You should show more restraint, Jamie. I think she expects me to giveyou a blowjob or something.””I’m sorry,” I say. “I’ll settle down in a moment.””No, you have to finish the job. Drop your pants and give little Jimmya hand job. But don’t wet my panties. I like those ones.” Followingher instruction, I unzipped my pants and pulled out my penis. I beganstroking it, right there in front of Lizzy.Lizzy liked the show. She unbuttoned her own blouse and unhooked herfront-hook bra. She slowly began caressing her breasts. “I reallylove to have my breasts touched like this,” she said. “But for thisweek, the hands doing so must have this sexy nail polish on them. Doyou want to touch my breasts, Jamie? Tell me that you do. Tell me howmuch you want to paint your fingernails and rub my breasts, Jamie. Iknow you do.”She didn’t go further, as I quickly reached my climax. I stuck my handin front of my penis to capture my load. Thankfully, the room hadtissues, so I was able to clean my hands before Lizzy went to retrievethe sales lady.The sales lady was very professional the whole time. She showed me howto tighten “my” corset, contrasting the procedures when I would havehelp, and “when wanted to wear it on my own.” I could tell thatshe didn’t approve of me, and she was constantly on guard to see if Igot another erection. This wager, I thought to myself, definitely wasa loss.Lizzy made me wear the corset home, under my shirt. As soon as I gotto my room, my cell phone rang. It was Michelle. I had to take this.”Hey, dear! How’s it going?””Mmmm. Nice. I miss you, though. In fact, I’m sitting here in ourbed, with no clothes on. I started thinking of you, wishing you werehere.””Really? And what is on your mind?” I try to be excited, but inreality, I’m worn out by Lizzy. Plus, I can hardly move with my corseton.Michelle switches to the video app on her phone. She makes me do thesame. Although the light is dim, I can see her naked body. She holdsup her lipstick. “Do you have yours, Jimmy?” I do, and I reach forthe pink lipstick on the dresser. In my corset, my movements arerestricted, and I wince slightly while reaching for the makeup.”Jimmy, what’s wrong? You seem stiff.””Oh … I just tweaked my back a little tonight. I’ll be fine.””You poor boy. I wish I was there to massage it. I’d give you a fullbody massage. You definitely would like it, don’t you think?”Michelle’s flirty tone is making me excited. And she’s not done.”Jimmy, you’re overdressed. Why don’t you get more comfortable?””I’m good, baby,” I lie, “Besides, I like to watch sometimes.””But I don’t get to watch, then.””I’m sorry. Maybe later,” I offer. Michelle is a bit disappointed,but she persists.”OK, I guess,” she says. “Anyway, I have this pretty lipstick with me.It matches what you have in your hands. Open it up and visualize,while I do my lips.” She painted her lips with the pink. That’s thethird pair of lips I’ve seen with that color on them in 24 hours. Ilaugh at this slightly.”What’s so funny, honey?” she asked.”Nothing. I was thinking about our games when I picked a lipstick foryou.””Did you like that? If you picked right, you got some great actionwith these lips, didn’t you? I’d like to do that right now, takeJimmy in my mouth with these pink lips.” Then, she started touchingherself. She whispered to me, “touch yourself, Jimmy. I want to see.”Carefully, I unzipped my pants. Suddenly remembering that I’m wearingLizzy’s panties, I drop the phone briefly. Before I pick it up, Islide the panties off and slip my pants back up. Michelle thinks I’vegone commando today.Despite my fears, it didn’t take long for both of us to orgasm. Allthe while, I kept worrying about whether Michelle could see theoutlines of my corset. Man, if she did, I was in big trouble. No easyway to explain that. Luckily, if she saw, she did not say anything.Tired and scared, I ended our session a bit earlier than Michellewanted. I pled fatigue, and promised more later. Michelle reluctantlywent along. I’m in trouble, I know. But I’ll figure that out later.TuesdayI made the mistake of telling Lizzy that I talked to Michelle lastnight. “Did you show her your pretty corset, Jamie?” she cooed.”Maybe I can watch next time. That would make me hot.””Don’t you dare,” I say. “I’m in enough trouble without Michellediscovering you watching us.””Now don’t be silly. I bet Michelle would love that I helped you pickout your corset.”During the day, I wore another pair of Lizzy’s panties, my new heelsand my beige lipstick. My heels terrified me. For one, I could hearthem on the hard floors. I tried to walk slowly, so as not to drawmuch attention. Plus, I’m almost certain that every woman at trainingnoticed my heels. There was a knowing glance I saw that convinced methey knew. I avoided conversation as much as possible, afraid of wherethe topic might turn. Yet, as you might guess, the fear of beingcaught kept me excited most of the day.I spoke with Michelle after training and before dinner. She was againin a playful mood. We again used the video app. This time, Michellehad her tablet, so she could stand it up while talking to me. Sheasked me to strip naked, which I did. I conveniently “dropped” thephone again, just as my panties would have been exposed. I strippedthem off and then recovered the phone so she could see.”Do you still have that lipstick?” Michelle asked. Yes, of course Idid, I say.”I was thinking about your comment last night — how we used to playgames with these tubes. Do you remember?”Well, anyway, I came across the red lipstick this morning. Rememberthe times I would wear that color and suck you off? I’m sure you do.Those certainly were exciting, and you seemed to enjoy the thrill of itall. Well, I thought of that today, but I also remembered the time inthe restaurant, when YOU ended up with sexy red lips. Remember? Thatwaitress had such a laugh at you.””Yes, I remember,” I say, thinking of how many time since then I’verisked detection in one form or another. “Why?”That was a dumb thing to say. It led Michelle exactly where she wantedto go. “I think it’s time to play that game again, that’s why.””I want you to put on the pink lipstick I gave you, and order roomservice for dinner. After it arrives, you can call me and tell me allabout your encounter with the delivery person.””I can’t,” I say, not thinking things through entirely. “I’m havingdinner with Lizzy tonight.”Michelle looked puzzled and then a bit concerned. “Lizzy? My collegeroommate? The one you not-so-secretly lusted after while we were inschool? You didn’t tell me that Lizzy was there.” Her tone gotaccusatory with that last statement. This was starting to turn in abad way. I had to do something quickly.”I’m sorry,” I say, “it was a very short encounter. I saw her at theairport after I landed. It turns out she has business here this week.She just called me this afternoon, saying that her plans fell throughtonight and wanting to see if I had time to catch up. It was reallycasual, you know. I was going to tell you on this call, but thingsstarted going in a different direction quickly, and I didn’t want tointerrupt the flow.” If I were John Belushi, this is where I wouldhave done the sincere eyebrow thing he was so good at. I settled on abit of the lost puppy dog thing. Michelle backed down — a little.”Well, OK,” she started. “You shouldn’t be hiding things from me. Idon’t like the thought that you’re not being honest with me.””I am being honest, baby,” I said, “I’m sorry that I didn’t mention itearlier. I just didn’t want to worry you.” After a pause, I added,”You know I wouldn’t do anything with Lizzy. She’s one of your bestfriends. I’m just being nice.”Michelle said that she understood, but I could tell I was still in thedoghouse. She backed down on the lipstick threat, suddenly saying thatshe wasn’t interested in “my thing” any longer. (When did this become”my thing”? I wondered. But I knew better than to push it now.)Instead, I apologized again and promised to talk to her later tonight,after dinner.I’m now late, so I have to hurry along to meet Lizzy. I’m not actuallymeeting Lizzy for dinner. I’m supposed to meet Lizzy at the downtownshopping area for more shopping. Lizzy told me to wear my corsetagain, so I hurry to try to put it on, following the instructions Ireceived last night. It’s not easy, but I manage after a few minutes.I put a button-down shirt on over the corset, quickly change into myjeans, and slip into my loafer heels. I tell myself that I still lookmasculine, but I’m not really sure. From a distance, I say, I’m just aguy in skinny jeans and a button down. I’ll just have escort tuzla to avoid tooclose contact, so as not to expose my corset or my women’s heel shoes.When I arrive, Lizzy is impatient. “You’re late. I don’t like boyswho are late.” I explain that I was talking to Michelle and thatcaused me to be late. I even told her that Michelle wanted me to playthe lipstick game (as I called it) but I had to decline. Lizzy saidshe was pleased I declined, because I should only take orders from herthis week. “There will be a consequence for being late,” she warned.Suddenly, I’m not so sure I like playing Lizzy’s games.”Your corset also is too loose,” she declared. “We’re going to have tofix that. Follow me.” The shopping area has a set of restrooms at oneend. Lizzy takes me by the hand and leads me to the family restroom.Lizzy is a step or two ahead of me, and I’m being pulled by her towardthe restrooms. I feel like a small c***d, being dragged by mommy fromplace to place. Inside, Lizzy has me remove my shirt and grab thehandicapped handrail inside the room. She pulls on the corset’sstrings, tightening it several times. “Breathe in,” she directs, asshe makes the last tug on my corset. When she’s finished, my waist isseveral inches smaller than my chest and hips, giving me a distincthourglass appearance. I put my male shirt back on, but that doesn’tadequately conceal my new figure. The shirt is more tapered than itseemed just a few minutes ago, and my corset (which is black) shows aslight shadow under my shirt. One would have to be looking closely,but if one did, you could discern the corset I’m wearing.”OK, Jamie,” she pronounced, “now you are ready for the rest of ouradventure. I’m going to buy you a cute dress tonight. Let’s go.” Ifollow. (Thankfully, she’s no longer leading me by the hand as we go.)Our first stop is not for a dress, however. We casually walk into acostume jewelery store. Lizzy looks at several earrings, holding themup to her own ears each time. I look around, trying to look distractedas she does this. The store clerk is a teenager, maybe 17. She ismildly interested in us, probably because there isn’t much going on inthe store. I’m doing my best to minimize this whole situation, butLizzy isn’t about to cooperate. She picks up a pair of large hoopearrings. They are gold, with a thick band, about three inches indiameter. Rather than holding them to herself, however, she reachesout and holds them next to my ears. I should move back, but I don’t.The clerk doesn’t say anything but I’m sure she saw.”They’re cute, aren’t they?” Lizzy asks me. “They’re not your style,though. Hoops don’t look good with shorter hair, do they?” I saidthat I agreed. Lizzy picked up some of the dangling earrings instead.She handed Lizzy a pair of silver dangling earrings. They had a fauxpearl center, with three strands of different length dangling below.”Something like this compliments short hair, drawing attention but notlooking boyish,” she said. Lizzy loved the earrings, so she boughtthat, along with the complementary necklace and bracelet.Our next stop was less eventful. Lizzy bought a purse — for me. It’sa small black bag, with a silver chain. Pretty standard fare, but”large enough to hold what you need,” Lizzy says. “And, it will gowith your little black dress, which we’re getting next.” The store putthe purse into a small bag with their logo on it. Lizzy makes me carryit. While I’m paying for the purse (in cash), I catch Lizzy texting onher phone. “It’s just work,” she claims.We next went into a store called “LBD.” Lizzy walked right up to thesales lady to ask for help. “We’re looking for a basic black cocktaildress,” Lizzy declared, “we want something versatile, not too short,preferably sleeveless.””We have several that would fit the bill,” she responded, “what sizeare you?” Then, with a slight glance at me first, Lizzy said, “Oh,it’s not for me. We’re buying it for a friend.””I see,” the sales lady responded, “What size is your … friend?” Iswear the sales lady looked at me first, but maybe I was imaginingthings.Lizzy was not about to let me go, however. If I had been at theblackjack table, this would have been when the dealer improbably pullsa 5 to her 16. “I’m not sure,” Lizzy responds. She turned to me andsaid, “what size do you think we need?” The sales lady turned to mealso.I’m stuck now. I try to stall and deflect. “I don’t really know,Lizzy. … Probably a ten, I guess.” The sales lady starks to smirk.Then, I add, “It’s for my sister.””Wow, you two must be close,” she replied. “I have three brothers, andI’m sure none of them know my dress size. You sister is very lucky tohave someone like you.” Clearly, I had not fooled her one bit.”Is your sister about your height too?” she asked me. “We wouldn’twant anything that’s too short.” Then, she continued. “We also needmake sure it fits up top. Do you know your sister’s bra size?”Lizzy jumped in on that one. “She’s my best friend. She’s a 38, Bcup.”With that, the sales lady took us to a few different choices. Lizzypicked out one that was sleeveless and had a boat neck. It had a smalleye hole in the chest area, just above the cleavage. The sales ladyagreed that it was beautiful. “But keep the receipt. If your, um,sister has any problem, she can come in to exchange it. I’d recommendthat she try on a few, to see the style.” Finally, to nail the point,she said to me, “tell your sister that we’re usually not very busy inthe last half hour we’re open. She’ll be able to get the mostattention if she stops by then.”After we paid, Lizzy asked the sales lady to hold it for a littlewhile. “We’ll pick it up on our way out. We have another stop or twoto make.” Again, however, Lizzy is texting someone while I gather mythings.We did indeed have one more stop. It was the department store at thefar end of the mall. Lizzy drags me to women’s suits and jackets. Ithought I had all the clothes I needed. “Not at all, Jamie,” Lizzyexplains, “You can’t wear a dress every day. I want to get yousomething that’s versatile. Something that can go from work to acasual night on the town. This one will be my treat.”When we arrive in the section, Lizzy gives the sales girl a hug.Apparently, Lizzy visits here more regularly than I thought. Lizzyintroduces me to Beth. “Beth will take care of you. I’m going to sithere while she finds a cute blazer for you, Jamie.” Lizzy sits on thecouch in the department (“where are these couches in the men’ssection?” I think momentarily). She picks up her texting conversationagain.I have a decision to make. Lizzy just clearly told Beth to help mepurchase women’s clothing for me. Do I go along with this? Unlike therest of our purchases tonight, if I go forward, there is no pretendingthat the purchase is not for me. Even with my weak “sister” excuse atLBD, I at least maintained a pretense of non-involvemnt. This would bedifferent.I see Beth looking at me. She’s waiting patiently for me to me. I runthe pros and cons through my mind quickly. But in the end, I knowthere’s no choice. I’m at the blackjack table, and I’m letting my bigbet ride.So, I let Beth help me find a “cute blazer” for me. Beth is wonderfuland very professional. Unlike that lady in the lingerie shop, Bethmakes me at ease about buying a women’s garment. She shows me severaldifferent styles, but recommends a navy three-quarter sleeve blazer.It has a single button, but is designed to be worn open. The sleeveslook rolled up, and show a white with polka dots pattern. (“Thesleeves can roll down to full length if you need it,” Beth explains.)It only falls to my hips, however. Much shorter than a men’s blazer.It’s definitely not passable as a men’s garment.After I purchase my blazer, I look for Lizzy, but I cannot find her.She’s not at the couches like she said. Where did she go? Then, I geta text. “Put on all your purchases, Jamie. I want to see how cute youlook.” Then, another text, “Meet me at LBD’s in 10.”Puzzled, I look around. I don’t see Lizzy, but Beth is still standingnext to me. For some reason, I tell her what Lizzy said. Beth triesto reassure me. “Go ahead,” she says, “You don’t have anything toworry about. Everyone out there is so consumed in their own world.They probably won’t even look at you. With your heels, your femininebody shape and the jacket and all, you’ll look like a woman. If you’dlike, I can give you a little makeup to finish the job. I worked inthat department for two years before moving over here.”For once, I made my own decision. And I didn’t make it out of fear.There was something genuine about Beth, something that gave meconfidence. If I’m going to keep playing this game, this time, I wantto try to be a woman, not a man wearing women’s things. So, I put onmy earrings, and my blazer, and I take out my purse. And, I ask Bethto make me up. Yes, I asked her; I didn’t let her. I text back toLizzy that I’ll meet her at LBD’s, but I have my own errand, so I’ll bethere in 20, not 10. That will confuse her.My next 15 minutes with Beth at the makeup counter is amazing. Foronce, I’m not nervous, I’m not sweating. I am enjoying this strangeand foreign experience. Beth is amazingly talented. When she’sfinished, I have smokey eyes, defined cheekbones and shimmery, sexylips. She gives me all of my makeup as samples. She even puts a smallclip on one side of my hair, making it more feminine and showing off myearring more. She gently pushes me toward the door and off on my way.”Be strong, be proud, Jamie,” she says to me. “You’re beautiful.”When I get to LBD’s, I’m changed. Lizzy loves my new look. “Sexy,”she says, “I want to get in bed with you right now.” I boldly pick upmy “sister’s” dress. I tell the lady there — the one who tried toembarrass me — that it is for me and that I would try it on first. Ieven walked out of the dressing room in my bare feet to show Lizzy. Ididn’t care.WednesdayThat bold girl didn’t last. When the morning came, I skipped my lastday of classes. I spent the whole morning in my room with the Do NotDisturb sign on. I couldn’t stop thinking about tonight. Tonight issupposed to be the night when I wear my new dress and we go to a fancydinner. It would be my first appearance other than in a shoppingcontext. I would have to present as female — or worse, as a man inwomen’s clothing. I won’t have the cover of shopping, where the clerkseither don’t care because a commission is a commission or they are paidto be professional. Tonight, none of that would be the case. I couldbe pointed out, ridiculed, or even abused. Suddenly, I’m genuinelyfearful. The fact that I could be in danger keeps me nestled in mybed.Lizzy texts me around noon, telling me to take a selfie. I tell herthat I’m in my room and not playing, and she quickly calls.”What’s going on, Jamie? Last night worked out so well, especiallyafter Beth helped you out. You were such a sexy babe.”I explain to her that I’m tired of this game. “I don’t want it anylonger, Lizzy. I’m just going to sit here the rest of my trip andorder room service.””Oh no you’re not,” she replied, “We have a date. You’re not standingme up — or coming in your blah clothing.” I tell her that I won’t bebossed around on this, that I don’t care if she tells Michelle. I’mgoing to tell her when I return, I vow.”Jamie, last night changed things. I saw you after your visit withBeth. I’m not ‘forcing’ you to do anything. No, little timid Jimmychanged last night. You’re still a man, but I saw a new side to you.Everyone has a bit of both male and female in them. Your female cameout last night, and she was bold, self-assured and pretty. I justloved the face on that ratty old hag at LBD’s when you told her youwanted to try on your dress before taking it home. THAT’s the personinside of you. The one who is going to have dinner with me tonight.The one that — someday, and if Michelle will approve — I’m going tobe lucky enough to have sex with. I’ve wanted you since college.Michelle knows that.”I’m really confused at this point. I don’t know what to say to Lizzy.On the one hand, she just gave me a pep talk. It was an odd “you gogirl” kind of pep talk, but a pep talk nonetheless. At the same time,she revealed something about herself and about Michelle that I hadn’tknown. Did she proposition me? Most certainly, she did.”Here’s what I’m going to do,” Lizzy continued, “I’m going to callBeth. She will come over before dinner and help you get ready. Bethwill show you. You’re ready.”I sort of agree. More like I agreed to think about agreeing. ButLizzy wouldn’t have it. “No. There’s no halfway here, Jamie. From thesecond I caught you in pink lipstick, I knew you wanted this. Tell methis: why did you keep pushing the envelope of public exposure? Whydid you wear noticeable lipstick in a crowded airport?”I’ll tell you why,” she continued, “Because you want this. You wantedto be caught. The thrill you experienced was your inner desire to gofurther. Getting ‘caught’ was a way for you to go further withoutguilt. Well, now you got what you wished for.”You’re just lucky that I’m the one that caught you. I’m not judging;I’m not abusing you. But I am pushing you. So, here’s my final order– and I mean this. You will paint your fingernails right now. Paintthem that hot red. Reddy for Anything. The same color I’m wearingtoo. You will paint them so you can’t chicken out later.”I hesitated. “Did you hear me?” Lizzy asked. “Yes,” I responded.”Good, then tell me.””I … I will paint my nails.””Paint them what?””I will paint them bright red.” “With the nail polish that I bought,”I added.”Good. And?””And I will wear it the rest of the day.””To dinner?””To dinner,” I vowed.”That’s right, Jamie. You will wear it to dinner with me and withBeth. I just want you to do one more thing, Jamie.””What?” I ask.”So there’s no going back. So you don’t lose your nerve. Pour outyour nail polish remover right now. Pour it down the drain. Don’tworry — I’ll bring you more tonight, so you can clean your nails afterdinner. But I want you to commit to Jamie for the day.”After a long pause, I agree. Lizzy says on the line while I pour outmy small bottle of remover (the same remover I bought from “Katie” wayback when). Lizzy then instructs me to paint my fingernails and sendher a text showing them off.I did what she asked, of course. But first I put on my corset. Icouldn’t tighten that with newly polished nails. I wore the jeans, thetop and the blazer that I purchased only a day before. My toes wereexposed, showing off the red I was about to put on my fingers. Andthen I did it. Sitting at the sofa in my suite, I slowly painted myown fingernails. One by one, I watched them transform into thebeautiful long nails that Lizzy had — the nails that Michellefrequently wore. I was painting my own nails. Voluntarily. Yes,Lizzy asked me to, but it was my own choice.Strangely, with each stroke, with each finger transforming, myconfidence grew. I felt thrilled, but in a different way now. I wasno longer fearful of the consequences of being caught. No longergetting adrenaline from the idea that something bad could happen. Iwas no longer the gambler, looking for a rush from the risk.My excitement now was in the transformation. In the idea that I couldtake on this new persona; that James could become Jamie. I felt a rushof excitement in making myself pretty. I was looking forward towearing a light, flowing dress, to elevating myself four inches in myheels, and to showing myself off to an old girlfriend.Three hours later, after Beth did her magic and I changed into mylittle black dress, I made the approach to the lobby bar. Lizzy andBeth were waiting for me. Clutching my purse, my mind ran througheverything that got me here. Was I ready? Yes. Reddy for anything.

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