All of my life from the time I was young to now at twenty-five, I have had an obsession with women. It is not that I like them (which I most certainly do) but more that I want to be like them, act like them, and most importantly dress like them.
It started when I was very young and developed an interest in the legs and nylons of women which I found fascinating. The sheer and soft material was incredible to look at and to touch. I was entranced with the way girls' legs would look with them on and often was frustrated by not being able to wear them openly like most girls did.
I would often "borrow" my mother's nylons and wear them on my young slender smooth legs, pretending I was a girl and crossing my legs like a girl. This progressed to shoes, heels to be exact which I started wearing along with the hose. I would prance around the house (when no one was around of course) and marvel at how pretty my legs looked in high heels and hose. I was fascinated at why nylons and high heels were only worn by women and they wore them only to attract guys.
Next came the dresses, which really completed my obsession (at least at a younger age). Pretty skirts, mini-dresses, flirty dresses, little black dresses, off-white girly dresses (my favorite), were all worn by me. It was wonderful and I felt like a real girly girl when dressed this way.
Sometimes I wish I could explain this obession to someone and be cured of it, maybe it is like an addiction. I often sit at the computer and just look for girls clothes online. I peruse all the shoe sites, especially ebay which has load of cute heels at great prices. I love to go shopping and look for pretty dresses, nylons, stocking, tights, panties, and especially shoes....high heeled sandals are my absolute favorite. I walk in to the stores (dressed like a guy) and have no problem looking at all the girls clothes.
I have such an attraction to girls clothes that it dominates my thinking. I often feel it is totally unfair that the beautiful girls I see get to look and dress like they do...and I don't like them for that reason, but at the same time I am in awe of their femininity and their clothes.
I am in awe of how pretty girls can be when dressed in beautiful clothes. Sometimes when I see a poorly dressed girl or one that is dressed grunge, I want to scream at them and tell them to go get pretty...you are a girl and should look like one. Mostly I get jealous of how lucky girls are, to able to dress the way they do, sheer, silky, cute, flirty, girly, pretty, tight, sexy, which are all meant to attract guys and certainly do.
After college I had gone to work doing consulting jobs for a couple of years and got some great experience working one-on-one with clients. I had decided to try and go at it on my own with a couple of my key accounts, and it had worked out well. I would spend a week or two at different client sites helping them with their computer systems and had all the work I could handle and was getting paid quite well.
Now that I was on my own I had stepped up my dressing habits with a nice collection of heels, dresses, lingerie, skirts, hosiery, makeup, etc. I kept my hair long and pulled back; and had maintained a very lean weight at 140 lbs and I stood 5'-7" tall. I still never ventured out while dressed but was getting a bit bolder as time went on.
I had just completed work with one client and was to see a new potential client in the same city. I have been traveling here numerous times before and during an off day decided to get my first manicure and pedicure. I really enjoyed the pampering and loved how nice my nails looked when covered with a shiny clear top coat. They made my toes look really cute when I got back to my room and slipped into some strappy high heeled sandals (I always traveled with an extra suitcase filled with my girly things).
I went out immediately and bought some pretty pink nail polish as well as some polish remover and sat down to paint my toes just like a girl. It was wonderful and I felt very feminine doing so. I messed up a lot but after two or three tries I got a pretty good result. My feet looked very pretty with the polish and they looked even better with the sandals on. I was totally hooked on this and went out to get additional colors (reds, hot pinks, bronze, light pink). I was really excited to get my next mani/pedi and decided I would ask for some color next time.
Before the next trip to the nail salon, I put on some very light pink polish on my toes. It had a very subtle shimmer and the nail girl would surely know that I had more than clear polish on my toes. I was extremely nervous but also very excited by the prospect that someone would be seeing my feet with real polish on them. She proceeded to give me my pedicure and started out by removing the polish that was on my toes, she definitely knew.
When she finished with the pedicure she put on a clear coat and asked if I wanted to pick out a color, oh this was heaven. The owner of the salon noticed this and came over to suggest some colors, it was so much fun. She picked a really nice pinky purple color that look really cute and the girl started to paint my toes in front of everyone in the salon. I was really embarrassed, but kept on reading my book and tried to not die of freight.
Once complete she asked if I wanted my finger nails done as well, but I declined (from sheer terror). My toes dried while I got the manicure done with a clear polish. I was wearing flat open toes slides (men's) that showed my toes clearly and walked right out of the salon feeling really girly but also very nervous about people noticing.
The next trip to the salon I would go all the way, manicure and pedicure with full polish on both hands and feet. While I have smallish hands they don't look too feminine especially with short nails, so I began to grow them longer in anticipation of my salon visit. By the time my trip began they were nice and long extending about a half inch beyond my finger tips. Because they were so long I developed the very feminine habit of looking and worrying about my nails. I was constantly cleaning the underside of them and would file them to a nice shape.
I was very excited for my next visit to the salon with my nails looking much more girly than ever before. I walked in and said hello to the girls (who now knew me and my little fetish) and was brought over to the station to begin. The girl doing my nails was Ally; she was very nice (and pretty) and treated me just like a girl while she began work. She cleaned my toe nails, shaped them nicely and made my feet really soft and smooth.
We chit chatted a bit and she helped me pick out a nice pearly color polish and began to put it on my toes. After a bit of silence she said, "Can I ask you a question?" I nervously agreed.
"Why do you come in here and get your nails painted?"
I confessed, "Well, it is hard to explain, but I really enjoy the whole process of getting them done.....I love how it looks when they are painted...aaannnnddd I am kind of obsessed with girly things."
Wow I never told anybody this stuff before. She looked at me kind of sweetly. "And what do you do after you have your nail painted?"
"Well, I usually go back to my hotel room, open a bottle of white wine, and get dressed up."
"Dressed up??? In what?" she asked.
"I have some pretty girls clothes....dresses, heels, nylons."
"What happens after you look all girly?" she mocked but in a cute way.
"I drink my wine, look at myself in the mirror and act like a girl....and then I uuuhhhh...pleasure myself," I responded very quietly.
She smiled, "I know lots of girls that do that all the time and it sounds like a fun way to spend an evening, like a girl's night."
Then to my complete shock she asked, "Would you like to have a girl's night with me tonight?"
I turned bright red but got very excited and stammered out, "Uuummmm ok, but you have to promise not to laugh at me to much."
Ally looked into my eyes sexily and said, "I don't think we will be laughing too much," as she winked.
"What will you be wearing tonight?"
"I have a pretty off-white dress, with some strappy high heel sandals."
"That sounds very cute, I will be sure to dress appropriately for you."
I was trembling at the anticipation of tonight and was getting very aroused. Ally noticed and smiled at my eagerness. She completed my toes, which looked great, and then started on my hands. "Your finger nails are nice and long....they will look really pretty with the polish on."
"Thanks....I have been growing them out for the last 3 weeks, hoping they would look good with my manicure." She spent a long time on the manicure making sure my nails and cuticles were perfect. She then coated them with a clear polish, then two coats of the pearly polish.
My hands looked beautiful and I thanked Ally for the wonderful job. She smiled and gave me a kiss on the cheek whispering, "See you tonight...girlfriend."
With my manicure and pedicure completed in a nice pearly white color that matched my beautiful dress and heels I raced back to the hotel to get ready for Ally who was arriving in an a couple of hours. I chilled two bottles of white wine and started to get ready. A took a nice hot bath and shaved my legs and other "hairy areas" very closely.
I made sure to clean out my backside well using an enema wash several times. Once clean and smooth inside and out, I put on a nice body lotion all over. I slipped into a thong panty and slid my girly legs into off-white stay up stocking.
They were very sheer and I could see my beautifully painted toes thru them clearly. I then slipped into my dress which was an off-white cocktail dress that cupped my "breasts", hugged my hips and fell to a flirty hem that ended six inches above my knees.
I then put on my favorite heeled sandals. They were off-white strappy shoes with thin straps around the ankles and a pretty ornate wider strap that went up the instep to the ankle strap, easily the sexiest shoes I have ever worn (or seen).
I then did my hair, which was long for a guy, styling it in a feminine manner. Finally I put on some make-up, foundation, eye shadow, liner, blush and lip stick and felt I looked as girly as I could. I felt very pretty, very girly and very excited for Ally to arrive.
I poured myself a glass of wine and quickly drank most of the glass to calm my nerves a bit. I heard a knock at the door and looked thru the peep hole to see Ally smiling.
I took a very deep breath and slowly opened the door and let Ally inside the room. She looked really cute and as promised dressed appropriately. She wore a beautiful spaghetti strap red dress that flared out at the waist and had a very flirty hem that was well above the knees. She had on very sheer off-white hose that blended into her skin and was wearing some very sexy black sandal heels which had really thin straps that also wrapped around her ankles.
Her nails were perfect and matched her dress color very well, I could see her toes thru her hose also and they looked good enough to eat. She walked in with a big smile and we kissed on the cheek, "Wow you look fabulous," she told me,
"I cannot believe what a girly body you have especially those legs, they are precious."
I blushed and smiled replying, "Thank you so much for saying that it makes me feel really good inside......and I am totally jealous of how pretty you are and how great you look in that dress and those shoes....I must get a pair of those shoes before I leave."
We sat down on the couch and I poured us both some white wine. We sat and talked like girl friends do, touching each other and commenting on our outfits. "We picked the right color for your nails, they look perfect for the dress," Ally commented, "and your shoes are very sexy."
"Thanks, I hoped the color was right and it turns out it was."
After another glass of wine we settled down a bit. "Ally," I asked, "what do you think about my girly activities?"
"Well...you are different than most guys, but I think exploring your feminine side makes you a better partner to a girl and I think that is very appealing, girls are also generally more open to other girls sexually and you make for an interesting dynamic because you offer both sides in one pretty package."
Wow was I hot after that statement; I looked into her eyes and kissed her softly on the lips. She returned the kiss and our lipstick painted lips mixed together and our tongues intertwined. We touched and kissed each other for a long while savoring the moments and allowing us to caress each other softly.
Ally lay back on the couch and I slide my hands along the hose of her perfect legs, parting them slowly and revealing her pretty panties. I moved them to one side and began my first "lesbian" experience.
Ally bucked, squirmed, and moaned as I used my tongue and lips to treat her pussy to several orgasms. I had done this before to several girls, but doing this while looking and feeling like a girl was a huge turn on for me. She then asked me to lie back as she would return the favor. Expecting a blow job I was pleasantly surprised as Ally began by removing my panties and spreading my legs wide apart.
Lifting my balls to one side she began licking my hole like a pussy. I began moaning at the wonderful feel of this new experience and truly felt more feminine because of it. She then inserted her middle finger into me and continued the tongue treatment. I was in heaven and felt wonderfully filled as she inserted another finger deep into me. Then Ally's third finger entered me and I felt myself begin to orgasm but not like normal.
It was deep in my body and slowly made its way from my painted toes to the top of my head. Ally sensed my moment and pressed her fingers deep into my hole. She also took my very hard cock into her mouth for the first time, going down all the way to the base. I screamed out, "OOOHHH, I am going to cccuuummm." Ally pulled back off of my cock a bit as I let go of the best orgasm I have ever experienced.
Ally's fingers continued moving inside me as I let out stream after stream of hot cum into Ally's mouth. After the last of my eruptions Ally came up and kissed me deeply, allowing my cream to slip into my mouth with her tongue. I was feeling so feminine that I did not even react and hungrily accepted my cum, swallowing it down eagerly. We continued kissing and cuddling as our initial passions calmed a bit.
We poured ourselves some more wine, smoked a cigarette together and felt very relaxed. Ally played with my hair and was telling me how pretty I looked. This was definitely the best experience I have ever had.
Ally then suggested we touch up our makeup and pulled out her bag of cosmetics. She fixed me up nicely and gave me some good tips on how to make myself look better. I sat and watched her as she fixed herself and sighed at how lucky she was to be able to do this all the time and go out in public looking as pretty as she did.
"Have you ever gone outside while dressed?" asked Ally.
"Not where anyone could see me, but I have been a bit daring like when I paint my nails at a salon and walk back to the hotel......I also usually put on a very light pink polish on my fingers and toes regularly."
"Have you ever been with guy?"
"Nooooo.....but it has crossed my mind." "
"What crossed your mind......sucking a nice big cock and making a man cum or being treated like a real women and taking a man deep and feeling him cum inside you?"
"Both....but I would be way to scared to go through with something like that since I don't think I can pass as a girl."
"Oh yes you can girl!!!" screamed Ally.
"And I would like to prove it to you right now!"
"NO WAY! Everyone would certainly know I was really a guy."
"How about we go down to the bar and sit in a nice quite corner and I will call a friend of mine to join us....we won't tell him anything unless he can tell."
"I will only agree if you redo my makeup and hair AAANNNDDD I am convinced by looking in the mirror."
"OK.....let's get to work making you look like a total girly girl."
She called her friend who agreed to meet us at the hotel bar in an hour. Then she began to redo my face. She used more makeup than I usually used convincing me that I need an evening look and a bit more foundation. She spent a lot of time on my eyes and lips and I was thoroughly enjoying the makeover.
Next she got some hair extensions out and incorporated them into my hair making it much longer and fuller. After putting on some shiny lip gloss she said I was done and I stood and walked over to the mirror. I was a bit shocked at the new me....I was really pretty and looked very feminine.
I softly touched my face and hair to make sure it was me underneath, then I turned to Ally and hugged her and thanked her for making me look so good.
She smiled and said, "I told you so," in a cute mocking manner, "now let's go meet your man."
I had some confidence in my look after seeing myself in the mirror, but I was still extremely nervous as we waited for the elevator. As the doors opened we walked into the elevator with clicking heels and noticed two handsome business men heading down stairs. They looked us over wantingly and one guy said, "I want to go wherever you two are going".
This made us both smile and Ally quickly responded, "That maybe arranged for another night, but tonight we are meeting a friend for a drink."
"Too bad, but we will be looking for you two tomorrow!" said one of the guys as we walked out of the elevator toward the bar area.
I was feely very good after that exchange because of the confidence boost of being "hit on" on my first time out. It also felt really great to be out and about, hearing the click of my heels, feeling the bounce of my skirt, and the swish of my nylons rubbing together. It was invigorating seeing people notice you, glance at your legs, and turning heads because of how pretty you look. As we walked into the hotel bar a waiter quickly sat us at our chosen table and commented on how beautiful we looked. We ordered champagne and sat back on the cushy chairs, crossing our legs and chatted a bit. "I told you.....you're passing not only for a girl, but a hot girl.....did you notice those guys on the elevator, there jaws dropped when we walked in."
"I have to admit you were right.....I am just loving this and I feel so right with everything."
The champagne arrived and we toasted and sipped. I noticed the lipstick mark left on the glass and smiled to myself that I had made that mark. We drank and talked a bit more when a handsome looking guy approached us and sat down between Ally and me. Ally reached over and hugged and kissed Steve, and introduced me to him. "Steve this is my friend Jaime who is in town for a few nights on business."