tagTranssexuals & CrossdressersDiscovering Amber Ch. 03

Discovering Amber Ch. 03


Ms. Allison's note: Again thank you to all those who have had such wonderful things to say about amber's story. Yes, these are true and yes amber is a very lucky girl. Those of you following these stories will notice that amber refers to her body parts in female terms, her penis is now called a clitty, her testicles are tessies and her ass is now her pussy. Keeping her thinking of herself in female terms is very important to her training. Feel free to comment positively or negatively but most of all enjoy.

Ms. Allison


There have been very few times in my life I have been terrified and today was definitely the tops on that list. Ms drove us to the mall and as I watched she walked around the front of the car and opened the door for me. I looked up to see her hand extended toward me.

"Practice getting out like I told you sweetie." She said as I took her hand. I swung my feet out with my knees together and slipped out of the car as elegantly as possible. "Very nicely done," Ms spoke, "now come on it won't be that bad."

Ms Allison took my arm into hers and walked us toward the mall entrance. It was a small gesture but for me it was definitely a sign that I was the girl in this relationship. What was also a big indicator of that was the fact that Ms Allison had dressed me from head to toe. Today I was wearing my white Rykaa sneakers, faded blue women's jeans which sat about an inch or two below where my normal jeans would have, a navy blue women's shirt, a pale pink demi bra and matching thong and a pink ankle sock with white lace ruffle edging. No one would really notice these little things. The jeans rode a bit lower but were the color of normal jeans. The shirt only buttoned from the opposite side but looked normal as well. I had a light jacket over the shirt so the bra was not noticeable and the length of the jeans covered my socks. Ms even took the cage off my clitty and tucked them underneath with a gaffe to make the jeans fit just a bit better. In any case the fact that we were out and about at the mall like this, even on a Monday morning, scared me terribly. Ms. Allison had taken us to a mall over an hour from our house so at least my being seen by someone I knew was very slim.

"See sweetie," Ms said escorting me inside, "nothing but little old couples that won't notice you."

"Yes Ms." I answered softly.

She set the pace and led me around the mall slowly. Eventually my heart rate slowed back down to normal. A couple of quaint smiles from couples we passed and I really began to relax. Ms led us up the escalator and then to a sissy's promise land, Victoria's Secret! I felt my clitty instantly stir but knew it wouldn't be moving soon. Ms picked up some new lingerie for me with little fanfare and then headed to the nightgowns.

"What do you think?" Ms asked a little louder than I had wished.

"That one is very pretty." I replied softly.

The one I was looking at was long with thin spaghetti straps and lots of lace at the top and down one side. There was also a slit that went up one leg to where my hip would sit.

"Oh that is very nice indeed." Ms said excitedly. "I think that soft yellow color would look lovely on you." Ms pulled the nightgown down from the hanger and held it up in front of me. "Oh yes baby," Ms said with a big grin, "that will look stellar on you!"

"Can I help you find anything?" The young salesgirl asked.

"Oh I think we found everything we need," Ms said hanging the nightgown up again, "I just need to check the size."

"Well what size are you?" The girl asked politely.

"Oh it's not for me," Ms Allison said handing me the lingerie she had picked up already, "it's for my friend here." Ms untucked the back of my shirt and flipped the thong out of the top of my jeans. "She's an extra large." Ms said loud enough for the world to hear.

The sales girl suppressed a giggle and started looking through the rack for my size. When she found it she handed it to Ms Allison who then held it up in front of me. I stood still and blushed hoping no one else would see me.

"Oh that is perfect." Ms Allison said happily.

"It comes with a matching robe as well." The sales girl said pointing to long partly sheer and lace robe.

"I'm sure she will love that too," Ms said handing me the nightgown, "do you have one in her size?"

"Of course!" The sales guy said with a big smile.

With the robe in hand I followed the two ladies to the sales counter. If it were possible my clit and tessies had now retracted into my body but the thought of wearing all the lovely items I had in my hands was still very exciting. At the register the girl scanned all the items occasionally looking up at me. I began to wonder if she were picturing me in some of the items.

"I grabbed your wallet for you sweetie." Ms Allison said handing me a leather wallet that was not mine.

The dark red leather wallet was more of a clutch with a leather strap that snapped over the top. I opened it and sure enough my wallet and credit cards were in it. When the cashier gave me the total I diligently handed her my credit card. She smiled and thanked me as she took it. A few moments later I was walking out of Victoria's Secret on Ms Allison's arm with two bags in my other hand. Prominently displayed in the hand through Ms' arm was my dark red leather wallet.

Ms. Allison then led us to Fredericks of Hollywood. There we purchased a number of pairs of stockings, some short nighties that left little covered, and two pairs of heels. One pair was clear plastic 2" platforms and the other were black patent leather 5 ½" heels with a silver metal spike heel and a thick ankle strap. Ms pointed out to the sales girl that neither pair was for her and that they were far too slutty for her tastes. With the bags in tow I walked with Ms Allison out of Fredericks and down to the food court. Ms and I got our food and went to a table. As I knew I should I crossed my legs and got lost in the conversation with Ms Allison.

Our conversation was about how she thought I'd look in the new purchases, particularly the long nightgown. All I could think of was how it would feel against my body and how it would feel when I walked. I couldn't wait to wear it later and began to wonder what I would wear under it. Eventually I came out of my little day dream to notice two college age girls sitting off to Ms Allison's right. Ms turned to look at them and then back at me but ignored them. Instead she continued our conversation. When the girls started to giggle I couldn't help but wonder if I had something to do with it. That's when I noticed what the girls were looking at. With my legs crossed my foot and the ruffled pink sock was completely noticeable under my jeans. I quickly tucked my legs under the table much to the delight of the two girls.

"Just relax sweetie," Ms said calmly, "you'll never see those two women again."

The two girls giggled uncontrollably for a bit and then went back to their own conversation. I started to relax just before the two of them started to get up and clean up their table. As they walked toward us I really started to panic and wanted nothing more than to become part of the chair I was sitting in.

"Your socks are adorable." The first girl said with a giggle.

"Thank you." I replied weakly.

"I didn't know guys wore socks like that." The second girl said laughingly.

"Oh they don't." Ms Allison said firmly. "Real men do not wear pink socks with white lace or women's sneakers."

"You've got women's sneakers on too!?!" The first girl exclaimed rather loudly.

"Oh my God that's amazing!" The second girl chimed in just as loudly.

"Well she does like to be comfortable when she shops," Ms said tidying up her plate and signaling for me to do the same, "and heels just wouldn't work today." I picked up my plate but Ms took it from me. "Don't forget to pick up your purchases muffin." Ms said as she stood up.

I gathered my bags and my wallet and followed Ms excusing myself politely as I did. As I walked closely behind Ms Allison I heard the girls laughing loudly. Ms took me to one more store. It was a little accessory store called Claire's Boutique where she had me pick out bracelets, a few necklaces, and some dangly earrings. The two girls walked by the store as I was looking at some bracelets and waved through the store window. Ms nudged me to wave back and had me purchase three pairs of earrings and 6 bracelets. I was very happy to leave the mall.

Ms drove us to another store; this one specialized in clothing for exotic dancers. In there it was a bit darker and there was only one sales woman so I was able to relax. Ms had me purchase a pair of thigh high boots, a pair of bright red heels with a 1" platform and a satin French maid's dress. I knew the heels would eventually hurt but I also knew they would look sexy as hell and I couldn't wait to wear them! Finally Ms had the sales girl fit me for 2 wigs, one was a long blond wig that had straight hair that came down below my shoulders and the other was a shorter strawberry blond wig that curled out a bit and barely touched the top of my shoulders. Ms had me look at the wigs in the mirror and I loved the look of both of them. The idea of wearing all these things was getting more and more exciting.

"Only 2 more stops muffin." Ms said as we walked out of the store. "Are you enjoying our field trip?"

"Yes Ms I am," I replied honestly, "it was a little scary at first but I am having so much fun with you."

"Good," Ms replied pinching my bottom, "I'm very glad to hear that." Ms opened the trunk which was slowly filling with all kinds of goodies for me. "Let's go muffin," Ms said closing the trunk lid, "time to indulge just a bit."

Ms drove us to a salon about 10 miles away. When we walked in she confirmed that she had appointments for two for manicures and pedicures. I was more than happy to take off my sneakers and socks while the woman started on my pedicure. Next to me was a woman in her 60's who was also having a pedicure.

"I think it's wonderful that men are getting pedicures." She started. "You'll feel wonderful when she's all done too."

"Thank you." I replied thankfully that an exchange with someone wasn't leading to a humiliating experience.

"I always try to get my husband to get one," she continued, "he's just too set in his ways at this point."

"This one is my first." I replied enjoying the pampering my feet were getting.

Our conversation continued for a bit. She told me about her grandchildren and children and was very sweet the entire time. When she was done with her pedicure she patted my shoulder and wished me good luck.

"Time for your polish." The pedicurist said.

"I think that cherry red will work best Judy." Ms Allison said from beside me.

"Cherry red?" The girl said quizzically.

"Yes please Judy." Ms said reassuring her.

While Judy started to paint my toe nails another woman started to give me a manicure. She worked quickly and in no time I was done with a fresh layer of clear polish on my fingernails. Judy returned and put a pair of paper slippers for me to wear next to my feet on the floor. Ms Allison already had her pair on and had both of our shoes in a bag. Once again she walked us out to the car but she retrieved the long blond wig from the trunk first.

"Slip this on sweetie." She said handing me the wig as she got into the car. I flipped down the vanity mirror and put the wig on. It fit perfectly to my head and framed my face nicely. "Good," Ms said looking over at me, "now open the glove compartment I have makeup for you in there."

She didn't have to say anymore. I put the make up on being careful with the mascara brush as Ms drove. It took quite a bit of coordination to do but I was able to pull it of and Ms said she was pleased with the results. Ms Allison then handed me a mirror.

"Take a look at yourself." Ms said as she continued to drive. "Tell me what you see."

"I see a woman looking back at me." I said as I looked in the mirror.

"So do I sweetie," she said pulling into a parking lot, "you can actually pass for a woman you just need to be less nervous." I shook my head unable to look away from my reflection. "You are quite a stunning woman too." Ms continued. "With a little work you and I will be able to go shopping without girls making comments about why you're wearing frilly socks."

"Yes Ms." I replied knowing she was making sense.

"We're going to try something," she said touching my arm, "the lighting in there will be dark enough. We just need to do a couple more things first before you go in."

Ms got out of the car and opened the trunk. When I put the mirror down I looked up to see that she had parked at an adult bookstore. Panic hit again momentarily but I did trust Ms. Allison completely. I tentatively got out of the car and walked to the trunk where Ms was waiting for me.

"First it's time to lose the paper slippers." Ms said putting a pair of baby blue flip flops on the ground in front of me.

"Yes Ms Allison." I said dutifully putting them on.

"Open up your jacket amber." Ms said with a hint of authority. I knew she was in charge and did as I was told. "Unbutton a couple buttons too." She continued.

As soon as I opened my top enough Ms pulled it back and stuffed at least 4 pairs of panties into one of the bra cups. She did the same to the other cup as well. Ms added a few more pairs to each cup until she was satisfied with the fullness of my chest.

"Just one more thing." Ms said sounding quite pleased with herself. Ms tied a pink scarf around my neck to hide my adam's apple. "You look amazing!" Ms said gleaming with pride. "Do you trust me?" She asked.

"Yes Ms I do." I answered.

"Then let's go." Ms said taking me by the arm again and leading me into the adult store.

The lighting was a bit dark. Inside there were racks of magazines and a long hallway on the left that looked like it had little TV monitors in them. On the right was a big counter with a rather large man behind it. We were the only two females in the store, there was one other customer and the man behind the counter. Ms took me by the arm and led me through the magazine racks. I was far too nervous to concentrate on where we were and didn't start to pay attention until Ms handed me an open magazine. I looked down to see a male wearing a dress, stockings and heels sucking another guys massive cock. I couldn't help but gasp out loud and then felt my face flush from embarrassment.

"Like what you see?" Ms asked teasingly.

I flipped a couple pages to see that same sissy bent over a couch with the well hung man behind her fucking her from behind. It was impossible to deny how my cock tingled inside my thong.

"I can tell you are getting excited by that," Ms whispered in my ear, "there's no denying it is there?"

"No Ms." I whispered back.

She picked up a number of other magazines including one on forced feminization and another on strapon sex. I couldn't wait to look through them and see what the possibilities were. It was an amazing thing to see such high resolution pictures of what I so desperately wanted. I had never considered myself gay and the idea of being with a man as a man was still disgusting to me but somehow my body was excited by the idea of a sissy being fucked by a man.

"I called earlier," Ms said to the gentleman behind the counter, "there should be a package for Amber."

It dawned on me that while I had been lost in my little dream state Ms had guided me up to the counter! How could I not have realized we were even walking? I put the magazines down on the counter and tried not to make eye contact with the gentleman behind the counter. He was more fat than muscle and not very attractive.

"Here you go." He said gruffly. "Just that and the magazines?"

"No," Ms said with a very relaxed tone, "she needs seven of those 7" suction cup base dildos, two of the 8" realistic looking ones, one of the blue big suction cup base ones and the four pack of butt plugs."

My mouth hung wide open at the shopping list Ms had just rattled off. What was I going to do with 4 butt plugs and 10 dildos!?!?!?! She simply patted my hand and pulled out my credit card. The guy didn't bat an eye at the name Robert on the card and rang it up along with the magazines. He placed all the new toys and reading material in two paper bags and sent us on our way. Ms led me back to the car and put the two bags in the trunk.

"I can't have you getting all excited before we get home!" Ms joked. "Lord knows what you'll do now that you know what really turns you on!" I simply blushed and got into the car. "Want to try one more thing?" Ms asked looking straight into my eyes.

"After everything we've done already," I replied looking into her wonderful green eyes, "what else is left?"

"Short of a boob job not much!" Ms said laughing and starting her car. "Seriously though," she said pulling out of the parking lot, "are you up for one more stop?"

"Okay." I replied more out of curiosity to see how she could top off such an eventful day.

She drove us closer to home which started to make me a bit nervous. We were now close to 30 miles from where we lived and the idea that I would be seen by someone I knew was making me a bit nervous. Ms drove to a strip mall and parked with the front of the car facing the street.

"Are you ready?" She asked.

"I think so." I replied not wanting to look at the stores to see what may be in my future.

"Just one thing," Ms said, "you're going to need to work on your voice. To start talk softer until we find a good pitch for you."

"Okay." I said barely above a whisper.

"Let's go." Ms said rolling her eyes as she got out.

She walked around and met me on my side of the car then took me by the arm towards the strip mall. There were a number of stores but the way Ms was winding through the parking lot it was tough to tell where she was bringing me. We got to the sidewalk and walked down it past a few stores until Ms finally turned and opened a door. It was the last place I had considered.

"A tattoo parlor?" I asked trying to keep my voice low but not doing a good job of it.

"You can get more than tattoos here silly," Ms said taking my hand, "now quiet down a bit and relax."

She led us inside and walked to the counter. I had never pictured myself getting a tattoo and if that was what she had in mind what exactly was she thinking of getting for me? How would I ever explain a tramp stamp to a guy at work? No this was going to be crazy if she made me go through with it.

"Amber." Ms called. "Amber!" It took me a second to remember that was me. "Come here sweetie," she said waving me over, "you have to look at this paperwork."

"What's this for?" I asked as I walked to the counter.

"For your belly button ring silly." Ms said as if I had a clue.

I briefly looked at the form and thought about it. A belly button ring would be temporary and could be removed leaving barely anything behind. It was easier to hide from work and as I didn't go to a public gym anymore the only person who saw me change was Ms. Allison and my Doctor.

"Just sign right here Amber!" Ms said reminding me not to sign the form Robert.

I signed it as naturally as I could and then waited in the seats nearby. Ms Allison sat with me and held my hand tightly. She could tell I was nervous and did her best to help me relax. She reminded me of our purchases at the mall and how cute my toe color looked. It worked for a bit until a tattooed biker looking guy came out from behind a curtain.

"You Amber?" He said gruffly. I just shook my head unable to speak. "Come on." He waved.

I walked quickly in the flip flops holding Ms. Allison's hand even tighter. He looked at me half checking me out and half questioning me. If I spoke I knew he'd know I wasn't Amber and he'd probably beat me senseless. The idea of going to jail or the hospital dressed like this was all the motivation I needed to keep my mouth shut!

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byMs_Allison© 18 comments/ 104829 views/ 46 favorites

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