tagTranssexuals & CrossdressersAm I Who I Think I Am?

Am I Who I Think I Am?


I was strolling around the mall today wearing one of my favorite girly toe rings with my girly-boy shorts and sandals. I was in one of those moods. I wasn't feeling very manly today and haven't been for quite awhile, but not sure how to feel. When I feel like this. I try to be as feminine as I dare, especially since I'm not sure just what I am right now! I really wish I had to courage to be both!

I like visiting the mall and getting as close to feminine as I dare without being "noticed" as anything other than an unusual dresser. That's why I like to wear toe rings, sandals, ladies shorts, and a shirt with a feminine logo and anything else I think I can get away with. There is a certain cut to the clothes that are unisex at a casual glance, but draw looks from men who probably don't know exactly what drew their glance to "that guy" over there. Designers spend millions to get that glance to "that girl," so why not me? I want to be noticed, but not seen, as I look at the lingerie (Why are baby dolls so hard to find now a days!), the panties (A thong, or something with harder seams that will show through?), shorts (how daring am I this time?), and of course the thin tops that work for my style (Shall I darken my areola's to draw Interested glances, I muse?). Girls have all the fun!

I'm really hoping someday to meet a Mr. Right who knows what to do with a girly boy like me. I need someone who knows what I want because I sure don't! I'm too shy to actually hit on a guy. I never have had sex with one and I probably wouldn't do it right anyway. The guys that did hit on me made me too nervous to welcome their advances. I guess I am doomed to a life of half measures!

In my mall excursion today, I notice a nice looking guy at a jewelry place that sells anklets, toe rings, etc., and decided to sashay over and see what they had. (And gauge his reaction, of course. I need to find someone who is cool, understanding, can read my mind, knows I am scared spitless and on the make at the same time, non-judgmental, gay or bi, holds hands with Jesus, and thinks I am just "normal." Oh yes, and he has to be attractive, strong, and handsome!).

This guy was really cute, and looked me right in the eyes. I was mesmerized for a second when he asked, "May I help you?"

Breaking myself out of my trance, I stammered and blurted out, "Yes, do you have toe rings in size 6?"

When I realized I was blushing I blushed even more! I felt so exposed! (Wow, if he only knew what I was thinking!).

"Yes, but I am going on break soon. I'd be glad to stay and help you if you'd like."

He introduced himself as "Gary," and shook my hand. (I gave him my most feminine, soft handshake!).

"I'm Chris," I replied sweetly.

He saw the toe ring I was wearing and asked if I was shopping for myself. I said I was and I was looking for another one. He commented that he doesn't see very many guys in toe rings!

I blushed and blurted out "Some guys like them!"

He smiled and said he was only commenting, and that we are all friends here, and that I was exceptional and that I needn't blush, and I would be a compliment to his toe rings, and please stop blushing! Which made be blush brighter! Then he smiled a warm and welcome smile, and asked me what size I wore, and I told him a size 6. He asked me if I would mind him sizing it.

To my surprise, when I sat down and bent down to take it off, he said "Oh no, I'll do it if it is ok with you, it's part of my job!"

He squirted some Windex on my toe (wow, it tickled!) and off it came. He put it on the measuring thingy and said "You were right honey, a perfect 6! Oops, sorry, umm, sir, I meant, umm.."

He was blushing so I quipped: "You can call me honey just this once."

"Thanks...honey!" He says again with a little smirk.

He started showing me a tray of rings similar to I was wearing, and asked me if he could check the fit. (I couldn't pass up a flirt as cute as him!), so I said "Sure!"

He said he wanted to try a 5, so he got some Windex and squirted it on my toes (Oh, that feeling again!) I jumped & my heart leaped! "Is it too cold" He asked?

"N-N-No, It just feels ...very...very nice," breathlessly trying to remain in control of my emotions, and not give anything away.

He finally worked the ring onto my toe and it was just too tight. And then didn't want to come off. It was stuck. He apologized and he said he had to really work it to get it off again and would I be more comfortable doing it myself or would I like him to?

"I'd like it if you would," I cooed...

Gently he takes my foot in his hands. Resting my sole in his palm, he dabs the Windex purposefully, gently lifts my foot, and then rubs the Windex between and around my toes lubing everything up. (trying too look up my short's leg, I hope? God, what if he sees my panties!). I had a seriously excited boy-clittie, my heart was pounding out of my chest! His hands were tickling my feet everywhere - I was trying not to giggle!

Finally, after some effort, he got it off and said, "Oh, we've got to do that again!"

"I hope it was as good for you as it was for me!" I chirped.

And then I realized what I said, and started blushing again!

"That's ok" he replies. And teasingly adds, "I think blushing is cute!"

And then he slowly proceeded to spray my other foot with the Windex, getting between my toes again, holding the sole of my foot in the palm of his hand, blowing softly to let it dry. Ohhh...He was smiling and blushing a little, too....

"Was that ok too?"

I was speechless! I'm sure he could hear my heart beating! This guy has a foot thing, and I'm loving that!

"Very OK," I stammered.

God I hope this is real, I'm thinking...If he's straight I'm going to curl up and die!

Finally, (before I had a heart attack), he started showing me some trays of toe rings and asked me what I thought. I said they were nice.

"But what do you think looks best?" I asked.

He showed me some plain bands, then some two-tone bands, and then asked my opinion again.

"Do you have something, you know, less masculine?" I replied.

He smiled. "Hmm, less masculine? Or do you mean more feminine?"

He was just drawing the truth right out of me! Things I have never admitted to myself, let alone to a male store clerk I didn't even know! I didn't know whether to run and hide, or simply shut up and be a nice girl and accept what life delivers! Besides, I was hot. My clittle was getting hard. I was having fun. Maybe he was too!

I was kind of unsure what to say, so he looked directly into my eyes and said "Well, lets try some really girly styles! You'll love them! If they are too girly, let me know and we'll go from there."

I'm thinking, too girly? Not a chance! I am so hot I could grab him right here!

Thank God he took charge, my heart was racing, I was sweating, trying to calm down, hide my clittie, hide my panties, hide my heartbeat, maybe just hide! He shows me a wider band with pink and blue round stones in it. "Is this feminine enough?" He asks?

"I think so." I replied stupidly.

"How about this one?" He says, and shows me an ultra-feminine string of hearts made with multi-colored stones.

"I think that one is really nice!"

"Here's another style I'd like to see on you."

He puts on a nice purple, yellow, orange, blue affair that has a thin gold chain running up to an anklet with a string of similar stones. "Wow! That's pretty! What do you think?" He asks.

"I don't know if I have the legs for it!" I said, teasingly.

"Oh, I think you do! It looks really sexy!"

Then he says, "How about this one on the other foot?" He showed me a cute but fairly wide gold band with intertwined nudes, 14K!

"I can't really afford that!" I replied.

"Yes you can" As he slips it on he says, "I'll give you my cost of $ 24. Think about it! Besides, I think one on each foot is just perfect for you. Would you like to try it out for awhile and join me on break?" He asked. (Is he just being nice, or hitting on me? Hmmm.)

I agreed and we walked around talking and smiling - just like a real first date!

I boldly took him with me into a ladies' shop and bought a pair of women's shorts that might pass for men's. (Upping the ante a little, testing the waters.)

"I just don't fill out men's shorts well. I suppose no one notices. Now you know my secret!" I explained.

"They fit you very well, they make you look...well, sexy! They probably look better than men's anyway. They seem to conform better to your shape! And I mean that in a good way! I think they are kind of hot!"

I gushed "Really? Thank You, you are so sweet to say that!" I began to feel my inhibitions slipping away as I realized he really liked me for who I was. He didn't seem like a weirdo, and even seemed pleased to be seen with me.

"Here, try on this belt!" He says. It was wide metal, with shiny oval rings laced together with a part hanging down in front, definitely a woman's belt. It was shiny, bright and dangly.

"Its pretty" I replied, "but I think it may be too feminine. I might embarrass you!"

"Not a chance" he said. He took my hand, and gave me a little peck on the cheek, and said "I like you as sweet as you can be, is that OK with you?"

I replied, (Upping the ante, and my courage, just testing...)

"I think so. Am I, like, your girl for today?"

He replied, "Only if you want to be!" I squeezed his hand back in reassurance. I was one happy boy!

We wandered back to his shop and played around with more toe rings and the Windex (and my feelings - I was soooo hot!) Finally it was closing time.

"Well, I suppose I should get going, I guess." (I'm thinking...please say: "No, don't go!")

He replied, "Are you in a rush?" "I really wish you would stay." "I've had lots of fun today, you are welcome to stay while I close up!" (Thank you! There is a God!) He started dropping the gate and said "In or out?"

The moment of truth. "In or out." Where have we heard that before? Hesitating, and thinking a thousand thoughts about what I meant to do today, versus what I am doing now, versus what I might end up doing. I hesitated, seemingly watching my life pass before my eyes, frozen in time for a moment, I replied "In!" I felt like I had somehow entered into a pact with my feminine self and would be forever changed. As I watched the gate fall as he lowered it, I could swear I saw my old boy-self standing out side motionless and inert. I think my hormones just switched gears.

He smiled and then invited me into the tiny little office where he had to count the money, and offered to let me in to change into my new shorts and belt. I had pink panties with lace trim and bows on since I didn't expect to undress in front of a man!

"Please don't be shy, I promise not to look, maybe!"

I though it over and let out a little giggle (What the hell, you've come a long way baby!) and replied, "Well, maybe just a peek, but please don't laugh or you might make me cry!"

"I won't" He offered, "I just hope your new shorts and belt are as sexy as you are!"

So, as we finally wiggle past each other in the tiny office, trying politely not to touch too much, which is impossible in the tiny room. (Did he just drag something hard across my butt? His manhood maybe? I did that to him? Oh My Gawd!)

So he sat down and I turned around modestly and began removing my shorts and stepping out of them revealing my pink panties.

"Those are really pretty! If I had known, I would have bought you some in the store! Turn around so I can see them!" (Whew! Past that hurdle!). And then he pulls me to him and gives me a little kiss on the stomach!

"Oh, you like? I was afraid you were going to laugh or make fun of me!"

He guides me down onto his lap, and looks me in the eyes and gives me a 24 karat kiss right on the lips! I fell into his embrace as if was the most natural thing in the world. I began kissing him back. He began caressing my cheeks through the satiny fabric, my erection and precome beyond hiding. I could feel him hardening further under me.

(Being faced with the timeless question asked by an eternal string of high school virgins, I'm thinking, "God, what do I do now!") I started kissing his neck, as he began to run his hands up the back of my blouse, then rubbing his hands gently back down inside the back of my panties.

"You feel so nice, honey!"

"Oh baby, I like that. You make me feel so good!" I purred.

As his hands moved to my nipples, (God I love that! How could he know!) I gradually slid down off of his lap, guided by the needs within me. With that thought I gently undid his belt, then carefully unzipped his fly, hoping for a glimpse of what lay hidden. I began to work his pants down, and he lifted his hips. (Finally! A sign, a signal, a green light! No chance of rejection now! Thank you!) With his pants finally down, as I peered and poked for an opening in his boxers, to my relief, he pulled them down displaying his wonderfully erect cock! It was beautiful! It was thick, about 7" long and had a slight upward curve like a little ski slope. I was fascinated! It was a much better specimen than mine could ever hope to be! I hope I do everything right!

As he played with my nipples I began to slowly lick up and down my first cock, savoring the moment. I started at the bottom, and slowly ran my tongue up to the tip where I circled the helmet with my tongue. I peeked up at Gary, and his eyes were closed in the eternal dream of ecstasy! (I must be doing this right, I'm thinking!) Finally, I began to take him into my mouth, one inch in, one-half inch out, two in, one out, gradually and slowly matching my movements to his breathing until I finally had him all in my mouth.

This wonderful man continues to lovingly fondle my nipples as his cock celebrates in the festival of my longing. He begins to lightly moan and work his hips gently up and down into my mouth. I tighten and relax my lips varying the pressure on him as he slides in and out of my mouth pussy. I drag my tongue over the sensuous underside of his shaft. I pleasure him with skills I never knew I had! As his breathing gets quicker and more desperate, I vary the pace trying to slow things down. I start licking the underside again in a circular motion, moving down and back up again, finally letting him slide back into my mouth again. As I moved my head and dragged my tongue and lips over the most sensitive spots, I began to taste his juices as they begin oozing out slowly. I could feel his penis getting harder, and harder, and then begin to almost vibrate. And then it begin to twitch...And then, like a breaking dam his seed rushed into my mouth with a force to match my emotions, and I swallowed, and swallowed, and swallowed his seed as if it were pure love itself!

As I was sucking, I had been rocking my hips so sensually as I serviced him my clittie was ready to burst! And burst it did! I came in my panties like I have never, ever come before! I held his cock in my mouth as he slowly softened, his breathing slowly coming back to normal. I was in heaven!

(Sort of. Wondering what to say now. Is he like most guys, yelling "next!" or his he really "my" special guy? Do I dare take my lips off of him and let him go, leaving me to face the truth alone? Damn, this is gonna hurt!)

My question was soon answered. He says "Oh sweetie, that was wonderful" (I'm thinking: And...?) "I have never felt so good as you made me feel! I didn't know I could go to heaven and then come back to my angel!" (I'm thinking: please God, make him want me still! Please, before he sees my tears!) He says, "You are so very, very sweet!" "Will you come home with me tonight!" He adds.

"Yes" I replied with relief, and tears beginning in my eyes.

He cooed into my ear, "Will you be my girl?" With those words, my life has forever changed.

Chapter 2

After everything was locked up and it was time to go, Chris walked me to his car-a nice red mustang convertible-, wow was it bright! He opens the door for me just like a regular guy on a regular date! I was so happy!

Then I realized that I don't have any fresh clothes to wear! "Gary, can we stop by my place so I can get a change of clothes?"

"Sure, honey." he replied.

So we stopped at my place and I offered him a beer, and went to start packing.

"Sweetie?" he called out, "Be sure to be your most sexy self for me!"

"Oh, I can't wait to sweep you off your feet with my charms!"

So I grabbed some panties, garter belt, stockings, and a thin wispy see through top. And of course, a baby doll nightgown I thought I would never need! I gathered up some cosmetics I keep hidden, and my douche bag and perfume. ("Passion" by Liz Taylor- a bit out of style but unmistakably boy-bait!) I felt like I was packing for a week!

"Ok, I'm ready! Are you?" I responded as I entered the living room.

He replied by gathering me up in his arms and giving me a juicy kiss, and a sweet suckle on my ear lobe!

"I'm ready when you are, honey!" He says.

I was shivering with lust. I hope he couldn't tell! I don't want to look too eager!

We soon arrived at his condo, a nice two-story affair. He showed me in and asked me if I'd like a drink.

"I'd love one!"

I sat down with both hands in my lap, and my knees together. I felt like I was trying to be as small as possible. I guess I was pretty nervous. Most of my feminine mannerisms were coming quite naturally, but others I was remembering from watching other girls. I really hadn't expected to move so far so fast. In fact, I am farther that I ever thought I ever would have been! He poured me a rum and Coke and sat down beside me with his arm behind my shoulders. He looked over at me, smiled and asked, "Are you still my girl?"

"Un huh!" I replied with uncertainty.

Then he leaned over and kissed me!

"Will you spend the night here with me? You can sleep on the couch if you are shy!"

"I'd like that, except the couch part" I giggled.

Gary replied, "I'd like to take a shower and get comfortable in front of the TV. Would you like to get sexy for me and we'll watch a movie together and have a little wine? There is a second bathroom in the hall for you to use."

I went into the bathroom with my overnight bag and slipped off my clothes, turned on the bath and looked around the bathroom. There was a fresh razor and some Channel body oil on the sink. I poured some sexy smelling bubbly bath into the tub and turned on the water. I got in and started to relax and enjoy the luxury, wondering what my role in this romance was to be. Could this be really happening?

Then, almost as if guided by an invisible hand, I began to lather up my legs and underarms and began to shave myself smooth as baby. I shaved my legs, my underarms, my boy-pussy, and my pubic hair. I felt really great!

I got out of the shower and brushed and teased my hair to make it as big as possible. I got out my makeup kit and applied a little light red lipstick with gloss. I blushed my cheeks, and highlighted my eyes. I curled my eyelashes and used some mascara to lengthen them. I dabbed some perfume on some strategic places. I put on my powder blue baby doll that has a thin panel to hide my little breasts, and augmented that with a matching pair of "boyshorts" (which let just enough butt cheek show to be sexy!). Next, I put on a pair of powder blue nylons with the band on top to keep them up without a garter belt. I completed my outfit with a pair of blue fluffy slippers! A quick shot of Passion perfume and I was ready to make my grand entrance to greet my new boyfriend.

I looked at myself in the mirror for a final check. Hair, ok…muss it up just a little, done! Make up, good! Baby doll, fine…need the panties a little higher to show more butt cheek, done! Breasts, a little too small but can't do much about that right now. I'll tweak them a little to make them pointy. Good. Hands are clean. Shit! Polish! Quickly I sat down and carefully painted my fingernails a hot red with a slight pink hue, and did the same to my toenails. Brushed my teeth, flossed, done! Damn, so much to remember.

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byClintdear© 0 comments/ 143024 views/ 45 favorites

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