The New Girlfriends! - A Short Story

Hi, girls! Here's someting a little bit different. I hope you enjoy it! Kisses, Rita

"What's in this room, Joey?" My best friend Kenny and I had just come in the house after taking a swim in my pool. "Oh, that's my mom's studio where she does most of her designs and stuff", I replied. "Cool, let's check it out", he said as he pushed open the door. I knew this room very well and loved spending time in it. My mother made a very handsome living making dresses and stage apparel for Vegas showgirls, models and any woman interested in her much sought after designs. There were racks of the most feminine clothing imaginable. Drawers full of the most delicious lingerie and a shelf holding a long line of beautiful wigs. One corner of the room was set aside to photograph the models as the designs took shape. There was also a lighted vanity where they could apply or adjust their makeup. Yes, I knew this room very well. I sometimes modeled some of these clothes to help my mom out. But Kenny didn't know that. No one did but my mom and me.

At an early age I became enamored with the soft silky materials my mom used for her designs. I would play at her feet while she worked. The feel of taffeta, satin, silk and lace delighted me to no end. My mother and I would giggle as I rolled around in the beautiful fabrics. I didn't take long to actually start trying on some of those silky treasures. It was all just harmless fun. She even made panties for me in my size. By the time I turned fourteen I was dressing completely as a girl when the mood struck me and with my mother's blessing to boot. She loved having her daughter, Jessica, around on occasion.

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.