My Brief Career As A Streetwalker!

I couldn't believe my heavily made up eyes! Monica was a vision I hardly recognized. She was decked out in a shimmering white satin skirt and blouse. Her legs adorned with seamed stockings with little black heart patterns sewn in. Her open toed white heels were to die for. Her blouse was very transparent leaving nothing of her gorgeous breasts to the imagination. Her face was so artfully made up it just had to be done professionally. "Monica", I breathed, "You are absolutely stunning! Your eyebrows! Did you..."? "Yes, Rita, I had them waxed", she smiled. Her hair was pulled up in a french braid and she was wearing the most adorable white satin pillbox hat with a flirty veil hanging over her eyes. A strand of big pearls adorned her neck with matching earrings. As Laura and I gazed in wonder at our girlfriend she just laughed. "You didn't think I was going to let you two little sissy whores steal all the spotlight, did you"? Shaking her head and giggling Laura went off to pour us all a glass of champagne. As we toasted each other the doorbell rang yet again. "That has to be Danny", I said. "Or the vice squad", Laura added. I ran to get the door. When I opened it there stood my man. Oh, he looked adorable in his white sailor suit. He was a bit stunned at my appearance. "Close your mouth, sailor boy, you might swallow a fly", I told him. He looked over my shoulder and his eyes grew even wider as he took in the two other extremely feminine people in the room. I made the introductions. I noticed that Monica held on to his hand longer then I thought necessary. He was still kind of shell shocked. "Are you okay, hun?", I whispered. He just nodded and said he was. As we gathered our coats and purses (all three of us in short fur coats, rabbit for Laura and I and what looked to be real mink for Monica) I heard Danny mutter, "What have I gotten myself into"? He was smiling though as he said it. We piled ourselves (arranged would be a better word) into his car and headed into Manhattan. I, of course, sitting in the front close to my honey. We all made small talk as we waited to get into the tunnel. Usual stuff. "Rita's told us soooo much about you, Danny. She's a very lucky girl"...etc. etc. Monica was particularly flirty with him, touching him on the shoulder a few times. I didn't mind too much. I knew where his loyalties lie! We found the place quickly as it was very close to the tunnel in the West Village. Finding a parking garage only a block away we headed towards the building where the party was held. It was such a thrill to be dressed the way we were hearing three pairs of heels clicking along a city street! We were getting some looks but not anything outrageous. After all this was lower Manhattan on Halloween. As we passed the gallery where Monica had been earlier we learned just where she got the inspiration for her costume. It was an exhibit of pinup art. Laura was thrilled as she's a collector. We all checked out some of the prints in the window vowing to come back and take in the full exhibit. We entered the building and a doorman directed us to the 27th floor. When we emerged we found ourselves in a huge party space that took up the whole floor. The place was packed with some of the strangest people I had ever seen! I made that comment to Monica over the loud music. "Have you looked in the mirror recently, sweety?, was her laughing reply. We carved out a space for us to sit and get comfortable and soaked it all in. We certainly weren't the only "hookers" present that was for sure. It was hard to determine the sex of a lot of people but who cared. There were plenty of dominatrix' with their "slaves", sexy vampires, cowboys, goths, togas, and a few more sailors. We managed to get a round of drinks going and chatted with our neighbors, as best we could. There was a terrace open to the roof for smokers. Everyone was complementing everyone on their costume choices. Monica was getting plenty of compliments. I felt so proud of her.

Soon we were all dancing and drinking and having a great time. I dragged Danny out on the dance floor a lot. When the drinks kicked in I was getting bolder grinding myself into him. He was having fun. I was worried that this might be too much for him. I must learn to never underestimate him in future. I made sure he danced with both Monica and Laura. I was asked to dance by other guys and in the spirit of having a good time I did. During a smoke break with Laura we compared notes. "If another guy asks me how much I charge for a blowjob I think I might just tell him", she said. I gazed inside and watched as Danny danced with Monica. She was leaning a little too close I thought. I told Laura about it. "Oh, you know Monica, Rita! She's just having a good time. She feels like a star tonight. She'd never do anything to hurt you. Let her have her fun. She deserves it". I thought about it and had to agree. Monica and I had become very close friends and she's done so much for me. The least of which was to introduce me to Laura. We went back inside, refreshed our drinks and rejoined the party. We had a blast!

Around 3 AM things were beginning to wind down. We collected our coats and began to head home. Traffic near the Holland Tunnel was so backed up that we decided to head uptown to the Lincoln. I don't know who came up with the idea but soon Laura and I wanted Danny to pull over so we could experience life as actual streetwalkers. "Just drop us off and drive around the block and pick us up again", Laura asked him. Maybe it was the drinks, but I thought that would be such a rush! We asked Monica to come with us but she didn't want to. "Live out your twisted little fantasies, ladies"! So Laura and I hit the street. It was a deserted street but that didn't matter. I just hoped a cop didn't come along. We sashayed and wiggled our asses up and down for a bit. Finally, bored, we found a doorway and lit up a cigarette. "It shouldn't be taking this long to just drive around the block, should it"?, I asked. We were beginning to worry. It had been about 15 minutes now. Finally a car did come by. But not Danny. It was a gypsy cab driver asking us if we needed a lift. From the way he was looking at us we could tell he had more than a ride on his mind. Couldn't blame him though. I mean under the circumstances. We told him we were waiting for our pimp to pick us up. We were off duty. When he heard the word "pimp" he quickly took off. Finally after about 25 minutes I saw Danny's car turn the corner. When we got back in I asked what had happened. Monica was laughing. Laura and I were shaking. "Tenth avenue is all torn up", Danny said. "They're replacing a water main or something. We got stuck behind a cement mixer. Sorry". I was so relieved. I thought Monica talked him into leaving us behind. I remonished myself for thinking that. Shame on me! Anyway, Laura and I got that out of our system for what it was worth.

We dropped everyone off and Danny drove me home. Mom was still in work so I invited him in. "Just how much do you charge for a blowjob", he laughed. "Fifty but since you're in the service I'll do you on the house. It's my patriotic duty"! Well, I didn't dress like a hooker for nothing so after a long slow blowjob on the couch we sat and reviewed the evening. He told me he really liked my friends. They were a lot of fun. "How about Monica"?, I asked. "She's very nice, she thinks the world of you, you know? And by the way, so do I". Awwwwww...soooo sweet. "I just love a man in uniform", I said as I lay my hand on his crotch. "Take me around the world, sailor boy, we have just enough time."

It had been a very intense evening. I'd have to tone it down next year. Maybe a nun? Oh, that's right, they don't wear heels!

Through The Looking Glass...Darkly

The afternoon of the party, we were all to meet at Laura's to get ready. I was the first to arrive. When I asked Laura where Monica was she told me that she had called and would be by later as she had some things to do. Danny would pick us up at 8. "I'm so looking forward to finally meeting him, Rita, and I know that Monica is as well". We had about 6 hours to turn ourselves from "respectable" girls into slutty, wanton, cock hungry whores. Laura put on some music, poured some wine and we began our transformation by adding long nail extensions. We both agreed that this would be time consuming and it would be best if we got it over and done with first. It might make dressing a bit more cumbersome but the both of us were quite used to working with longer nails. After mine were painted a deep glossy shade of red and Laura's were similarly done in hot pink we stripped and headed to the shower. After we were thoroughly clean and smooth (with a bit of clitty and nipple play) we powdered each other off with a sweet smelling scent. Pedicures were both done the night before. It was time to enhance our figures a bit. Although Laura was pretty well endowed in the breast department I needed some help. She had me lay flat on her bed as she attached my breast forms. When my breasts were firmly attached to my chest I slipped into a low cut black demi bra that was trimmed with red lace. Laura excused herself telling me she had a little surprise for me. While she was gone I admired my new shape in the mirror. I loved the way my nipples would poke into the top I was planning to wear. The extra weight and bounce were just dreamy! She returned holding an assortment of what appeared to be vagina's! "We need to wear a gaff anyway so I thought these might be a bit more fun", she said. "Oh, they are so cool", I gushed. We picked out ones which closely matched our skin tones and helped each other slip them on. Standing together at the mirror we both stared in fascination at our new pussies! It was surreal. I was all giggly while Laura had a wistful look on her face. I added an open bottom girdle with padding for my hips and fanny. Laura added a similar girdle with a bit more padding. Her figure was stunning. We slipped into short silky robes and headed for her vanity. This was going to be the most important makeup session of my life. Things had to be absolutely perfect. We each helped each other smoothing on our foundation and setting it with loose powder. When our complexions were perfect canvases we began the long task of making up our eyes into sexy, smokey, long lashed attention grabbers. We both opted for long false lashes and plenty of eye liner. Dark sultry shades of shadow had our lids practically drooping under the weight. We each took turns sculpting our cheekbones to perfection. When we were satisfied with the results we clipped on our hair nets and brushed out our wigs. Sitting at the vanity again Laura ceremoniously fitted my long bouffant blond wig to my head. It gave me goosebumps. I returned the favor transforming my pretty blond girlfriend into a sexy red headed siren! We sat in silence for a few seconds just taking it all in. "This never gets old for girls like us, does it Rita"? She must have been reading my mind. I hadn't had so much fun dressing since those early days alone in my old boy's (yuck!) bedroom. My clitty was beginning to squirm in my new pussy pantie. To prove that Laura was in fact reading my mind she slid to the floor and pulled the pantie down. My hard clit sprang forth and Laura engulfed it entirely in her mouth. As she was hungrily bobbing her head up and down I just gazed at my reflection in the mirror. She was giving me so much pleasure. Batting my long black lashes at myself I came in buckets (or so it seemed) into her eager mouth. She then stood and french kissed me full on my unyet painted lips. Both Laura and I share the view that the absolute last thing we do is apply our lipstick. Good thing! After our cummy kiss I returned the favor. With the edge taken off a bit we were able to finish dressing. Lingerie was next. All black and lacy for me and all pink and lacy for her. We slipped into our heels and dresses, applied our perfume in all the strategic spots and sat together to transform our full lips into cocksucking perfection. As we were applying a shiny layer of gloss over our lipstick, (Revlon Certainly Red for me and Gentlemen Prefer Pink for her) the doorbell rang. Glancing at the clock we realized it was almost 7:30! Where had the time gone? Laura got up to answer it. I was still glued to the mirror, fussing with my hair and earrings. I was startled to hear Laura say...."Oh, my God! Monica is that you??!!

Where's A Real Man When You Really Need One?

The following Friday as Danny and I lay in post-orgasmic bliss I brought up the subject of Halloween. Monica had found, what seemed to us, a really cool party to go to. It was located in the same building where she attended the art exhibition. It was billed as a kind of "anything goes" affair targeted to the GLBT community. At first Danny was skeptical about going. I was able to convince him with a long drawn out blowjob. (Oh, the power we girls have!) I explained that the girls and I would be dressed as hookers and he would be our "sailor boy", plus he would be our designated driver. He was happy with that.

The next night Monica, Laura and I hammered out the details. Outfits, hair, makeup etc. Monica sort of balked at the idea of dressing as a hooker. "That might be okay for you two sissy girls to live out your fantasies but I'm leaning towards something different. Something retro". When we pressed her for details she said she'd surprise us. She said she got the idea from the exhibition she'd seen the past weekend and left it at that. She did however give Laura and I plenty of input as to how we should look, the feminizing vixen that she is. When I asked how I should wear my hair she just looked at me and said, "It's Halloween, honey, wear a wig, a big mane of whore hair". Upon mentioning that Laura jumped up and said she had the perfect look for me. She came back holding a big round box. When she opened it she pulled out a big bouffant blond wig. It was amazing. She came behind me and slipped it onto my head. It was perfect. Looking at myself I could envision the makeup I would need to put the whole look together. Laura then produced another box and took out a wig in shimmering red ringlets and waves. She also showed us the dress she would wear. A very tight electric pink spandex dress that would look like it was literally spray painted on her. With a pair of matching 6 inch platform heels she would look luscious. I thought, and we all agreed, that I should be all in black. I had a couple of ideas. I saw a two piece skirt and top that I thought would be perfect along with a pair of 6 inch black stiletto platforms. The shoes I had in mind had little rhinestone lips on them. What could be more perfect for me! With the hard work out of the way we settled in for a little girly loving.

Monica was laying naked on her back fingering her pussy as she watched Laura and I in a delightful 69. My clitty was very hard and excited when Monica asked me to service her dripping cunt. I dove between her legs and began giving her a good tongue bath. "No", she said, "put it in me". I looked up at her and then glanced over to Laura. She just shrugged and said, "go ahead, expand your horizons. That's what these nights are all about". I was a bit scared and I could feel myself softening a bit. Monica just took hold and guided me to her wet entrance. I gasped when I felt my clitty enter her outer lips. As I slowly sank in she began playing with my nipples. That helped alot. It felt warm, wet and cozy. Monica moaned. "Oh, Rita, that feels so nice! Now move it in and out, honey, but do it slowly". I did as she asked. I was still nervous. This was very surreal for me. I could feel myself starting to soften again. Still playing with my breasts Monica asked me to describe, in detail, Danny's cock. Thinking about the night before and his wonderful hunk of man meat I told her about how heavenly it felt to be impaled by his hard, hot 7 inches. It was helping. I was getting very turned on again as I continued to fuck Monica. (Yes, me, fucking a vagina!) It was then I felt something hard being pressed against my rosebud. Laura, that little minx, was slowly inserting a small dildo into my pussy. Monica was really getting into it. The more I described the sensations of having his big cock in me the more she wiggled under me. She gave out a low scream and I knew she had cum. Meanwhile Laura was giving me a proper fucking with her little plastic friend. It was an amazing feeling to be buried in Monica's steaming cunt and being fucked myself. The whole texture of her cunt changed the second she came. It was much more wet and warm. It felt just incredible. I could feel my own orgasm building in my tummy. When I felt the point of no return I pulled out of her and sprayed my girly juice all over her breasts. I immediately began licking them clean while Laura continued to plow my pussy. I could feel the heat continuing to build in my midsection. I was headed towards a major belly-gasim. When it hit me I must have screamed. I may even have passed out for a few seconds. That had happened to me before with Danny. Monica got up to clean off and I snuggled with Laura to thank her for such a wonderful cum. As I was searching Laura's mouth with my tongue for her tonsils Monica rejoined us. "So", I asked her coyly, "was it good for you"? "Not bad, honey, for your first time, that is. But where's a real man when you really need one"? I knew exactly where one was!