The First Time

By Anita Cocktail

 

I had a typical childhood. My schooldays were filled with sports, friends and schoolwork, my summers were filled with friends, baseball, swimming and AM radio contests . . . and my little secret. From my earliest memories I can recal being fascinated with womens' clothes. Yes, I was a crossdresser. I would indulge this every chance I got.

By the time I was 13 I would anxiously await an opportunity to dress. Nylons, girdle, bra, slips, dresses & high heels were the objects of my fascination. Always alone and never, never going out!

I never really got to experience the total package I was 37. I had separated from my second wife and was living alone. I moved out and that afternoon I went shopping. I bought a wig, make-up, fingernails, two dresses, girdle, bra, waist chincher, pantyhose and 3 pairs of 5" Stiletto high heels. I went home and took everything out. I went in and showered and shaved . . . everywhere! My arms, chest, legs and face. I even shaped my eyebrows! I then went in and pulled on a pair of satin thong panties and arranged my 'boy-parts' so they would be firmly in place. I put on a pair of suntan pantyhose and the girdle. I got out my breastforms and sat them down on the bed. I put on my bra and slipped the breastforms in. I went to the table and got out the make-up I had purchased and for the next hour I carefully applied the foundation, blush, mascara, eyeliner, eyeshadow, and lipstick to my face copying from pages of Cosmo, Vogue and Vanity Fair to acheive the best look I could. I put on a pair of false eyelashes and stood back and admired the results. Not bad! I put on a pair of earrings and a necklace. Fingernails were next. I learned that they would stay on better if I clipped them on with clothespins and let the glue dry. I put my rings on and removed the dress from it's hanger. It had a back zipper and I struggled until I took an old coat hanger and with it's aid, zzzzzzip! I was in. The wig went on and I fussed with it. I sprayed on some "Poisen" perfume. I slipped into the 5" Stilettos . . . I took my first steps completely dressed. I felt fantastic. I walked around the house and just enjoyed the feeling of the clothes, hair, shoes, 'nails . . . all of it! I stayed dressed until 12:00 that night . . . I was ready for the next step, going out!

I went to a local bar where I knew Drag Queens hung out. I went in wearing my boy-clothes and sat and talked with them. They were so nice! I asked if I could join them Friday. One of the queens, Belle, suggested I come over to the house early and we'll help you get ready. I was thrilled.

Friday came and I left work early. I went home, gathered up my things and drove over to their home. The house was a whir of activity. People scurying about. Belle said "Ok, everyone, this is Anita and she's new. BRAND new. So gather around and let's help her get ready. Where are your clothes, hun?". I opened my suitcase and they looked over my dresses . . . "Sweetie, these are sweet but will never do. Janelle, go get the black low-cut cocktail dress and the patent belt." Belle said. "Don't get me wrong, hun. These are nice dresses and all but tonight we are gonna DRESS you!" Janelle re-emerged with a black ¾ sleeve number with DEEP neckline. I looked at it in awe. Then I looked at my flat chest. "We'll fix that later." Janelle said as she pulled me over to the bathroom. I had shaved already but they showed me how to REALLY shave! Two of them, Belle and Janelle, sat me down and applied my make-up. Janelle looked at my chest and asked "Hun? Have you ever taped before?" I said no and she said "Well then it's about time you did!" She pulled off two 15" long pieces of duct-tape and stuck them to my chest . . . VOILA'! I had cleavage! "See? Now that's better! Put on your bra and titties and let's have a look.". I put my waist chicher, girdle, bra and breastforms on, then the dress. "WOW!" Janelle said looking at my cleavage. "Am I good or what?" I had finished getting dressed but couldn't find my wig . . . Traci came out spraying it and holding it up and asked "Anita? Looking for this?" she had restyled it into a fantastic creation. "Bend over, hun." I did and she put it on my head. Then came the bobbie pins . . . MANY bobbie pins. "There" Bell said. "That ought to hold it! 'k, hun . . . turn around and look at her!" "OH-MI-GAWD!" I exclaimed as they all laughed. "not so fast. We need 'nails." Janelle said. I got out my packet of 'nails and Janelle shook her head saying "No-no-no-no-no . . these will NEVER do! Traci? Help please?". Traci came over and smiled. "Hun, let me give you a REAL set of 'nails!". I sat down and within 20 minutes Traci had put on a set of acrylics that were 1" past my finger tips! "Too long?" she asked. "No, I love them!" "Ok, but you'd best be careful!" she cautioned. I walked around in my 5" stilettos watching everything that they did. I learned so much.

Finally, Belle said "Ok girls. Time to go. Anita? Would you mind driving?" The four of us got into my Toronado and drove down to the same bar we had all met at. We went in and had dinner. When the check came I grabbed it. "My treat, ladies!" "You don't have to do that, hun. It's your first night out and we-" "Have helped me so much it is the very least I could do." They all thanked me and we moved into the bar. We stopped in the dressing room and Belle introduced me around. Janelle ollked at me and said "Sit, girl. I wanna fix that face a bit." She re-did my lips and eyes and smiled. "Much better! Nice titties, hun!" she said looking down my dress. We went out and got a table and I ordered a round of cocktails for us. I pulled the waitress aside and gave her my credit card. "This is all on me tonight, ok?" I said winking. She acknowledged this and I returned to the conversation.

Belle turned to me and said "Anita. You just look so pretty!" How do you feel? Do you like it?" "Oh, honey . . . I LOVE it! I am having so much fun! Thank you, thank you all so much!" Janelle raised her glass "To Anita! Happy Birthday, precious!".

The show was such fun. I really hated for the night to end! The girls and I got up to leave and asked for the check. "It's been taken care of." I said winking. "Oh come on now. What kind of friends do you think we are?" "The best, nicest friends I could have ever asked for." They all smiled. "Ok, babe. This time, ok. But TOMORROW." They all nodded. "We are gonna take you SHOPPING!" Belle exclaimed.

I spent the night at Belles' home and at 9:00am the next morning I awoke to the smell of breakfast. Belle stuck her head into my bedroom "C/mon, Anita. Get your crack outta the sack! We have a busy, busy day planned for you!". We ate breakfast and when I started to do the dishes Janelle grabbed my arm "C'mon, hun! The damn dishes will be there when we get back!". We piled into Tracis' van and off we went. They took me all over to stores I'd never even heard of. We bought make-up, false eyelashes, jewelry, 3 dresses, shoes with matching bags, two more wigs, 4 wig heads, a corset, pantyhose and two roles of duct tape.

We stopped for lunch and Belle grabbed the check "Put your money away, sister! Tonight's on US!". We returned to the house and they Janelle asked me a lot of questions. She nodded and told me that they all liked me and thought it would be so much fun to let them do EVERYTHING to me. I hesitated until she said "Relax, hun. The best to learn is through experience. We aren't gonna harm you. It'll be fun. Please?" I trusted her and agreed with no reservations.

They told me how to shave really close. Belle than asked me if I had ever 'tucked' . . . I said no and she said that if I felt ok she'd show me how. I couldn't wait. "First, we need to shave your uh . . ." "she said looking down at my crotch. "You'd better pee first." she suggested. "and don't drink too much. You're gonna be this way for a while." I nodded and went in and really pee'd. I shaved my 'uh, y'know' area and went in and layed down with my legs spread apart as far as I could. Belle took an ice pack and put on my genetals. She took the role of duct-tape and tore off 5 pieces. She starting taping at my rectum and proceeded to tape my gonads up into my groin. She said "So far-so good!". She then took another piece and pressed my maleness up into my groin, then quickly covered it securely with duct-tape. "Voila! Instant pussy!" she exclaimed. I stood up and Belle handed me my panties. "Put these on. You look like a science project!". I pulled the new red panties on and looked in the mirror . . . no bulge! "Fun, huh!" Belle remarked. Pantyhose next-two pairs. My chest was taped again . . . Janelle pulled the tape really tight! "Hello, girls!" she remarked as the cleavage popped up!. Then the red corset . . . Traci fastened the front and gave the 'go-ahead' sign to Janelle and Belle. OOPPP! The laces grew tighter. "Once more. Remember, Anita. Pain is beauty!" UNGH! "Let's measure her" Belle said. Janelle got out a measuring tape out. "Ok . . . 38", 27", 33"! ALLRIGHT! Walk for us, baby." I walked across the room in my Stilettos . . . clik-clik-clik. "Nice!" Janelle remarked "She's got that sashay." "It's the only she CAN walk!" Traci added. "True" Belle agreed. "Do you feel ok? Not too tight?" I was fine I told them. I was in heaven! I LOVED the way I was forced to move in the corset and the stilettos. Traci worked furiously on my Auburn wig as Janelle and Belle applied my make up & eyelashes. The eyelashes were longer than I'd ever seen, let alone wore! Belle said "Ok, hun. Close your eyes and hold your breath. I'm gonna set the make up!". She sprayed AquaNet on my face. They had also given me a 'face lift' courtesy of about 2' of surgical tape that would be hidden by my wig! "Hun? You really need to pierce your ears. There are just so many more earrings you can wear! We'll be gentle, ok?" she assured me. "Ok . . . " I said. I felt my lobe being punctured . . . not once but twice! Belle put in a pair of large gold hoops followed by a pair if faux diamond studs and put the earring backs on. "There, see? No big deal!" I felt the heavy earrings swing each time I moved my head. I loved it! Janelle inspected my ears "Looking good, Anita! No leakage!"

Traci handed me my new red dress. Belle and Janelle helped me into it so as to not muss my face. "Wow!" Janelle remarked. "The girls are looking good tonight!" she said looking down at the taped up mounds that were almost popping out of my dress. My 'nails were still fine but Janelle decided that they needed to be red also. Traci did a fast polish job that matched.

Belle put a necklace on me and Janelle put about 3 bracelets on each wrist. I got out my new, red patent 5.5" Stilettos and slipped my toes into them. A spray of "Poisen" and I was good to go.

I went out back to smoke while the rest finished getting ready, enjoying the feeling of my clothes moving against me. and the 'clik' sound my 5.5" Stilettos made as I walked.

I offered to drive again. After we were all in the car, Belle looked at the others and said "We're going somewhere different tonight. I'll direct you.". We pulled into a parking space in front of a Turquoise building with pink awnings. It had a neon sign that said "RENES' Fine food and entertainment". We exited the car and clik-clik-cliked our way in the front door. "Belle!" the rather flambouyant waiter exclaimed as we entered. "This way." We followed him to a table next to a stage. We talked and perused the menu. After we ordered I asked if there was a show tonight? They all laughed. "You'll see . . .".

Our dinner came and it was excellent. Finally the lights went down and the spotlight came up. "Ladies & Gentlemen . . . and those of you somewhere in between. Welcome to RENES' supperclub & showbar! Before we start, we have a newbie we'd like to acknowledge. Anita Celeste', Please stand up !" I looked at them all and slowly stood. "This her SECOND NIGHT OUT! Doesn't she look fantastic!". I stood up and teetered on my stilettos as the crowd was applauding. Belle, Traci and Janelle all smiled. I sat back down and the waiter brought over a bottle of champaign. He opened it and poured us all glasses. Belle smiled and raised her glass "Welcome, Anita! Here's to the second of many nights like this. Salute'!".

We watched the show and I thought back to all the times I was all dressed up and couldn't summon the courage to open the door. I looked around at my new friends and knew that from here on out my was just going to keep getting better.

It has!

 

SALUTE'!

THE END

  

  

  

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