I knew a bit about Shane. I'd seen him dozens of times before. He had accompanied one of my Mom's "special" clients once for a fitting. Since that client was either a drag performer or a crossdresser I figured he might be gay or something. He was in his early twenties I suppose and had those Southern California surfer looks. Sun bleached blond hair that he usually kept in a pontail and a tight, but not overly muscular, build. He was pleasant enough and very personable. My Mom liked him from the get go and hired him to do odd jobs for us including cleaning our pool. As I was doing some very unplanned weeding I heard him greet me. "Hi, Joey! Keeping busy I see". "Yeah, I figured I'd get it out of the way so I could spend the day just swimming and soaking up some sun". I had my back to him bending over to pull a stray dandilion. I looked over my shoulder and noticed his eyes were locked onto the round globes of my ass. I got another tingle. He started in working and making small talk all the time, asking about my summer, my Mom, etc. All the while I got the strangest feeling he was watching me closely. After about 15 minutes he asked me if he could have a bottle of water. "Sure, not a problem, be right back". As I walked towards the house I could still feel his eyes burning into my back. I noticed a figure behind the sheer curtains on the back patio doors. It had to be Karen. She stood aside as I came into the house. "Is he almost done?", she whispered. I momentarily forgot about Shane when I looked at her in a skimpy lime green bikini. "Oh, honey, you look good enough to eat!", I gushed. "Thank's!", she said shyly. I could tell she was working on her makeup skills. "Not bad, but needs a little work. Especially the eyes.", I thought. "He should be done in about half an hour but something weird is going on!", I said as I bent into the fridge to get a cold bottle of water for him. I heard a gasp behind me and turned to see Karen with her hand covering her lipsticked lips. "Jessica, oh my God!", she whispered pointing to my shorts. I looked down and to my utter dismay saw about half an inch of red lacy from the bottom of my panties. It never occured to me to take them off figuring my shorts would hide them. "Oh, shit! No wonder he was looking at me like that! What am I going to do?", I pleaded. Karen started to giggle and then to laugh a little too loud. "Well, you can take them off but he can't unsee what he already saw! You said he was gay, so why not just go with it. He is kinda cute!", she said, batting her long lashes. "Easy for you too say! You're all safe and cozy in here with your bikini and tits and I'm out there making small talk with these damn sweaty gloves on!, I retorted. "Sorry. Just do the best you can not to bend over too much. Maybe he didn't notice.", she said giving me a quick peck on the lips. "I'll try.", I replied, heading back outside. He was busy at work when he heard me coming. He turned to look at me as I handed him the water. I noticed a quzical look on his face as I handed it to him. When he grabbed the bottle out of my hand he also managed to pull of my glove. I gasped as I saw the water bottle and glove in his hand. I quickly tried to hide my gleaming red nails behind my back. Taking a long sip he looked at me. "Nice shade of red. They match your panties!", he smiled. I was so busted!! "Playing a little dress up while Mommie's away"? I stared at the ground feeling the blood rush to my face. I felt his hand on my shoulder. "It's okay Joey. I'm not judging you. It's just a surprise, that's all. You have nothing to be embarrased about. I'm no stranger to this kind of thing.", he softly said. I looked up into his smiling sympathetic face. He reached down and took the other glove off my hand. My red nails shown in the bright sunlight. "Very good job! Did you do them yourself ?", he gently said. I nodded. "Come, let's sit and talk a bit". We sat at the patio in the shade. "Who is here with you, hon"? I looked up yet again shocked. "Ummm...n..no.."! He put a finger to my lips and swiped them. Holding the finger in front of my eyes I saw traces of Karen's lipstick from when she pecked me on the lips. "Unless I'm mistaken this is a shade called "Love That Pink" and it looks like it came from a kiss and not an application. You certainly weren't wearing it when I first came by". I didn't know what to say. I didn't want to get Karen involved. "Look, Joey, I said I'm not judging you. I won't tell anyone. In fact I can probably help you"! For the next ten minutes he opened up about himself. He was an up and coming drag performer on the Vegas strip. Still not a headliner but was paying his dues and perfecting his look. I stared silently in disbelief. "You need proof? Wait right here"! With that he got up and went to his car. I turned to see Karen peeking through the curtains. When he returned he was holdin a folder. He pulled ot a picture and showed it to me. The picture was of a very pretty, but obviously a drag artist. I stared in awe. "Now do you belive me?", he said. "Yes, you look very good!", I said beginnig to relax a bit. "And I bet you do too. Now who gave you the kiss. You don't have to tell me if you really don't want but I'm just curious, that's all. "Umm...", I said turning to look towrds the back door, "my friend...ummm...Karen. "Karen? Can I meet her"? Umm...I'll see". I got up and walked to the kitchen. Karen was sitting on a stool looking into a compact mirror. "So vain", I thought. "What's happening out there!", she asked. "He wants to meet you". "What! What did you say? I can't go out there like this"! I pulled her up into my arms. "It's okay...he..he's ..one of us!", I told her kissing her on the fore head. "Come on, it's going to be alright. Karen slowly followed behind me as we made our way back to the patio. Shane was smiling. Well, hello Karen, you look very pretty in that bikini", He said holding out a hand. Karen reached over a dainily shook his hand. We all sat and spent the next hour or so going over our weekend so far. We didn't mention the sex but Shane was not stupid. The kiss on the lips that Katen had given me was all the proof he needed that we weren't just getting dressed and made up. Oh well!
Yes, this room was full of feminine memories! "Wow, look at all this stuff!", Kenny exclaimed as he walked around the room fingering the gorgeous outfits. I was startled out of my daydreams when he took down one of the wig blocks and examined the long brunette hair that was pinned to it. A devilish idea struck me. I went over to him and took it from his hands. Removing the wig I slipped it onto his head before he knew what was going on. I giggled as he stood staring at me with a shocked expression on his face. "Hey, Ken, you look like a rock star!", I said as I pointed at him. "Let me see", he replied as he walked over to a full length mirror. While he was staring at his reflection I took the opportunity to take down another wig. This one was ash blond and very feminine with masses of curls. One of my favorites. I slipped it on and went to stand next to him by the mirror. He laughed when he saw me. "You look like a girl"! "So do you", I replied. "You said I looked like a rock star", he pouted. "I lied". He continued staring at himself. "I guess I kinda do, but not as much as you do"! I started to tease him even more. "Oh, no I think you look very pretty, Karen. I'm jealous. All the boys will be looking at you and not me", I said as I slipped into my girl persona using my hands in a feminine manner and speaking in my well practiced breathy girl voice. "Karen? Are you nuts?", he said reaching up to remove the wig. "I'm just busting your chops....sweety pie!", I chirped. "But seriously with a little makeup I think you'd be quite convincing as a girl. He looked at me like I was crazy as he stood there with the wig in his hand. "No way!", he said. "Yes, way!", I replied. I had made no move to remove my long tresses. My eyes drifted over to the vanity with its full array of makeup and I felt my cock begin to harden. What was I thinking? Suddenly the urge to dress up was overwhelming but I tried to keep my cool. "Look, we have the whole house to ourselves for the weekend. Who's gonna know? It might be fun and it's better than playing the same old boring video games." "I don't know....", he mumbled. "Look, I'll do it too", I said trying to sound convincing. "I did it once before for a Halloween party and it felt kinda neat"!, I added. "You did? I don't remember that.", he said still not sounding convinced. Suddenly he looked at me and asked what we had to do. I knew I had him right where I wanted him. "Well", I wistfully replied, "if we do this then we have to do it right." Although my body was totally hair free below the eyebrows I detected some fuzz on his legs. "Bubble bath. It will help set the mood. "Mood? What mood?", he asked. I just smiled and led him by the hand out of the room.
We went up to the master bathroom where my mom's huge sunken tub was. I ran the water adding in a large dose of sweet smelling jasmine bath beads. I stripped off my swim trunks and hiding my half erection slipped into the water. I motioned for him to join me. He modestly turned around, slipped off his trunks and rushed into the tub. "Feels nice, doesn't it and it just smells so divine. "Divine?", he asked. "Oh, Kenny, loosen up and have some fun, will you?" "Joey, I...." Don't call me Joey, call me Jessica, okay Karen"? "Jessica? Okay, okay," He giggled. I smiled to myself as I realized he was getting into it. I handed him a pink razor. "Karen, honey, I think you'll feel alot better if you take the fuzz of your bod", I said in my most feminine voice, batting my eyelashes at him. He took the razor from my hand, lifted his leg up and began to glide the razor up and down. "You have such pretty legs, hon, I don't know why you let yourself go like that". He giggled all the time he was shaving. I picked up another razor and secretly shaved my pubes under the water in a more feminine shape. It wasn't easy with a raging hardon. As I watched him perform this simple girlish task my hand could not help but stroke myself. Carefully controlling my breathing I brought myself off to a delicious cum. His full attention was on his right leg as I scooped up some of my cum and tasted it for the first time. I'd never done that before and it felt like such a naughty thing to do. It tasted....interesting. After we were finished bathing I handed him a towel for modesty. I, on the other hand, boldly stepped completely nude out of the tub, dried off and slipped on a long white satin dressing gown that was hanging by the door. Quickly tying it up in a big bow at the side I scurried from the room. I returned with a similar gown in a fetching scarlet and motioned for him to slip it on. He hesitated for a second but when he put it on I detected a knowing smile playing on his lips. I pictured those lips in a color similar to his gown and felt those familiar stirrings again. Luckily he broke the spell when he asked what comes next. "Nails, Karen darling, nails. We'll go down to the studio. Everything we need is down there. I found matching bedroom pumps to match our gowns. They only had a slight heel that I knew I wouldn't have a problem with but I was pleasantly surprised to see he didn't have much difficulty with either. Putting a little extra sway to my hips I led the way down to the studio. I could feel his eyes on me as we went. "You walk like a girl!", he said with surprise in his voice. I just smiled and kept right on walking. "Soon you will be too!", I thought to myself.
When we arrived I sat him at a small table and went to one of the many drawers in the room. Finding what I was looking for I walked back to him and handed him his very first pair of panties. They were bright red matching his gown. "Here, slip into these, hon", I said as I quickly drew mine up my smooth legs and adjusted them around my hips. "Wow, Joey, these are..." "Jessica...not Joey!, I admonished him. "Oh, yeah, right...Jessica...uh...these are.." "Pretty, Karen..you think your panties are pretty"? He didn't reply as he gingerly slid them up his now very smooth legs. I heard a very audible intake of air from him and saw his face get flushed. "You haven't felt anything yet, honey!", I wickedly thought. Going to the vanity I quickly found what I was looking for. Base coat, color, top coat and extensions along with the tools needed for lovely nails. He was in a daze as I began working on his toes. When both our feet were just perfect feminine perfection with our shiny red tootsies. I sat across from him applying the one inch extensions. "How come you're so good at this. How did you learn how to do nails like this?", he asked in barely a whisper never taking his eyes off my handy (!) work. I mumbled something about watching my mom do hers. No, Joe....ah Jessica, it's more than that. I looked at him and sighed. Over the next hour or so as I finished up our manicures I told him about my other life as Jessica. He never said a word. When our nails were dry I smiled at him. Holding out my newly polished talons I asked him what he thought. Looking at his own he smiled and told me that they looked very pretty. "Ready for the next step, honey?", I asked. "And that would be...?", he said still beaming at his new shiny red nails. "Undies, doll face", I cooed. He giggled at that. "I like that", he shyly said. "What?" "Being called doll face.", he whispered. I smiled at him as I slipped off my dressing gown. Standing there in just my white lacy panties I watched as he slid his off. He was excited. Very excited. His cock was poking through his panties. Mine was just as hard. Time stood still as we gazed at each others cocks. Finally I held out my long nailed hand and said, "Come with me". I led him over to a raised platform and had him stand on it. I found a matching lacy garter belt and he gasped as I hooked it on to his thin body. I explained that the garter straps go inside the panties in case he needed to pee. "Or get fucked!", I whispered in his ear. He let out a low moan as I ran a long nail up the side of his swollen prick. Sheer stockings soon followed and I could tell his brain was in overload. There was pre cum oozing out of the head of his cock like a running faucet. He just had to have some relief before we continued. I gently stoked it through his silk panties gently encouraging him to cum for me. "Cum for me, baby, cum for Jessica.....that's a good girl...Jessica is going to make you so pretty....your going to adore being a girl, honey...sweet Karen...pretty dresses....beautiful makeup....high, high heels.....that's it doll face, give Jess all your sweet juices". He was mewing like a kitten and then his face scrunched up as he shot rope after rope of cum across the room. I had to hold him up and some of his cream landed on my arm. I scooped it on to my finger and looking into his eyes as I slowly brought it to my mouth. "Your cum is yummy, doll face, here, taste...." I fed it to him. He was hesitant at first but quickly ate it up. He leaned over and softly kissed me on the lips. "Thank you, Jessica". "Your very welcome, Karen." We were silent for a minute. Both of us absorbing how our friendship had changed since this morning. He sat while I slipped a pair of four inch heels on his feet. While he practiced walking around and getting used to the new height I dressed in my garter belt and stockings. Slipping on an even higher pair of heels I went to get the next items we would need. He was adapting quickly to walking in stilettos and I praised him. "You're a natural, Karen, honey"! He giggled as he strutted back and forth adding more and more wiggle and sway to his hips. He was really getting into it now. All previous inhibitions just seemed to fly out the window. What's next, Jessica!" "Tits, honey, all girls need them and so do we. He continued to practice his walking skills as I affixed my breast forms to my smooth chest. After the allotted time I stood up and admired my pretty titties in the mirror. "Wow.......holy....wow", was all he said. "Your turn, doll face!" He couldn't lay on the table quick enough. Fifteen minutes later we were both admiring our new tits in the mirror. We were also both rock hard again. Slipping back on our dressing gowns we sat side by side at the vanity. "We're going to go for a very glamorous look", I told him. I went in stages. First doing my foundation and then his explaining every step of the way. I penciled in his brows giving them a gentle arch. I tweezed where necessary. He watched in awe as I transformed his eyes using alluring shades of eyeshadow, liner, mascara and false eyelashes. When I was done with both of us we looked like showgirls. I finished with blusher to define our cheek bones. Karen looked gorgeous, just as I suspected she would when we first started. "The rest can wait until we get dressed", I told her. I could no longer think of her as a him. He was gone, for the time being anyway. We each donned a shimmery satin full length slip. Hers in red and mine in white. We spent the better part of an hour deciding on which gowns to wear. She settled on a stunning red gown in soft organza while I selected a body hugging white beaded gown. We still looked rather silly wearing such exquisite dresses with short boy hair. Our makeup done up like showgirls. Returning to the wigs that had started this whole day off we helped each other with our tresses. Karen just couldn't take her eyes off her stunning appearance. I guided her back to the vanity showing her how to sweep her skirt under her to sit. I extracted a red lipstick from the table and slowly applied the color to my lips. "Karen, darling, a woman holds off putting on her lipstick until last. It is the finishing touch. Handing her the lipstick I watched with pride as my new girlfriend applied her own lipstick for the very first time. Next we adorned ourselves with jewelry. Long pendant earrings, faux diamond necklaces, rings and a few bracelets. We sat awhile admiring our transformations. I spritzed us both with Chanel #5 and finding matching clutch purses we left the studio.
The sun was setting as we made our way into the living room. "Now what do we do?", Karen asked me. "Enjoy each other's company, doll face. Are you hungry"? "A little. Do we have to eat? I don't want to ruin my lipstick!", she whined. "You are such a girly-girl, you know that, honey"? "Thanks to you I am!", she giggled and batted her long lashes at me. I made us up a tray of finger foods and found a bottle of good white wine. We sat in the waning light of day on the patio and talked for hours. "It would be nice to go for a swim but I don't want to ever get changed.", she said. "Well, there are alot of cute bikinis in the house. Maybe tomorrow?", I said with a raised arched eyebrow. She thought that was a fantastic idea. When we weren't talking we were checking our makeup in our compacts that were in our clutch purses. We imagined we were waiting for our handsome men to pick us up and take us out for a night of dancing and romance. The talk soon turned to how we would repay our gentleman for treating us like ladies. "Hmmmm...I'd let him just bend me over and fuck me. After I sucked his cock of course!", she said dreamily. By now we were both very worked up. My poor cock was straining in my panties under the tight gown. We both looked at each other in silence for a minute. "You're beautiful", I said, "lets go slip into something more comfortable".
Twenty minutes later we were both in short revealing babydolls snuggled together in my mom's bed. We were so hard for each other we didn't hesitate on taking our first taste of each other's cocks. We sucked each other off over and over again only stopping to apply more lipstick. What a day it had been. Going from best friends to lesbian lovers in less than a day was mind blowing. Speaking of blowing my new girlfriend is getting hard again.
