Becoming Jessica Pt. 04

Quick synopsis: My understanding wife, Emma, is helping me start to live part time as Jessica. After going to the gym we venture out to the mall for shopping and fun times.

We got home and marched upstairs to clean up and change. Emma suggested I start putting my 'Jessica' things in one of the guest bedrooms and use the guest bathroom to shower.

"I need some privacy and it's better we start to move on. Plus It's just easier when we're both getting ready to go out. And you can always come back here if you need help with your makeup or something." Emma explained.

I understood. Afterall I was responsible for ending our current situation. I was so lucky she was supportive and understanding.

Our house had three guest rooms. One had wood toys and a bunk bed. One was really basic with blue walls, a double bed, and black bedroom furniture.

The 3rd guestroom was perfect for me. It had very light pink walls with a flowery border, neutral carpet, off white bedroom furniture, and a queen bed with pink sheets and a purple dotted bedspread. It also had a walk in closet which contained some of Emma's formal dresses, off season clothes, and her wedding dress.

I happily put away my clothes from the past 24 hours in the dresser, laundry hamper, and closet. I couldn't wait to fill up my bedroom with more Jessica stuff.

I had an interesting revelation about myself as I settled into my new bedroom. The exhilaration and thrill I felt crossdressing or shopping for women's clothing as a guy was kind of gone. I was confused because I felt more natural and comfortable dressing, shopping, and just being Jessica. I ultimately determined it was no longer the rush of feeling girly I wanted, it was the comfort of just being a girl.

Emma broke me from my inner trance when she yelled down the hallway "Jess, just use the products in the basket in the guest bathroom to clean up."

The basket was full of manly and girly soaps, shampoos, lotions, mists, and other products. Emma was always insistent on buying matching scents. I liked learning these little tips from her.

The guest bathroom had a jetted bath tub shower combination. I didn't have the time to take a nice soaking warm bath so I decided to take a quick shower and practice my 'Jessica" getting ready in a hurry routine.

Trust me, I so wanted to take a bath. I never took baths as a guy, but as a girl it felt so feminine, so right, and a huge part of getting ready as a girl. I always thought and fantasized that half the fun about going out on a 'GNO' (Girls Night Out) or a hot date was the 'getting ready' part.

As I warmed up the shower I disrobed, took off my fake ponytail thing, and hopped into the shower tub. I squirted some juniper berry liquid soap into a body loofah, cleansed my body, and rinsed.

I remembered reading in one of my girly magazines the best way to prep your face and lips was to proper exfoliate them in the shower. I washed my face with some oatmeal soap and applied a minty balm to my lips before I gently scrubbed both with a small facial loofah.

I skipped washing my hair because Emma mentioned getting our hair shampooed and styled at the Saks spa and salon.

After my shower I continued with my new girly routine of lotion, pat dry with a towel, powder, and mist in my new juniper berry scent.

Next I put on my new lingerie set. I started with my Nubra breast enhancers. I was able to stick on and attach both sets properly and push my chest tissue together. Then my Commando push up bra and silicone enhancer inserts. Finally I did my hide and tuck thing [again it was beginning to be like second habit] and pulled on the matching high waist thong.

The thong had a tall band of stretchy firm fabric which was really comfy and held in my tummy while boosting my butt. It gave me a more feminine shape.

I pulled my hair back up into the stretchy hair band fake ponytail thing and applied my beard cover and blended it in with my foundation.

I threw on a light blue robe hanging in the guest room bath and pranced down to Emma's room to finish my makeup.

Emma was already dressed and applying her lipstick. She was wearing a gray v neck sweater, skinny jeans, and ankle boots with a medium heel. Cute look I thought. And I wanted it.

"I need that look Em, so cute, and some skinny jeans." I told Emma as I walked into her bedroom.

"Oh my God Jess. You're not ready yet." Emma said.

"Come on Em, I don't have this makeup thing down yet. I did get my foundation applied." I replied.

"Okay, sit down. Let's do this. Going for a simple look tonight. Sometimes less is more. Now watch." Emma explained.

Emma layered a champagne and dark brown eyeshadow above my eyes and lined my eyes with a jet black eyeliner. Emma curled my eyelashes and finished them with a midnight blue mascara.

"Okay now I think you can do your own cheeks and lips." Emma said as she finished doing her lips.

I looked at my face and remembered reading in Elle magazine about how to balance your face from the colorwheel. I decided a peachy pink blush would look well on my cheekbones and a dark rose liner followed by a shimmery taupe lipstick.

I loved applying makeup to my face. With Emma's help I was definitely learning the proper techniques and colors. Coloring my cheeks and lips was beyond heavenly. I hoped to master making sexy eyes next.

"Hey you're learning. Darker lip liner than your lipstick. Nice. Sexy. Now go get dressed. We need to get a move on." Emma quipped as I finished applying a second coat of reddish taupe lipstick.

I scampered back to my room and quickly squirted on some juniper berry perfume before putting on my outfit.

I rolled up my black Hue leggings, put on the white DKNY tee which had a pretty deep v neck and layered it under the button down chambray shirt. I loosened the top buttons on the shirt to reveal some cleavage. I then put on my brown belt over the shirt and wrapped it around my upper waist.

I liked how the my butt booster thong, high waist leggings, and belt cinched my waist and helped accentuate my curves. The white tee and chambray top just barely covered my plumped up ass.

I slipped on my knee high boots, pulled up the side zippers, and returned to Emma's room.

"Here put on this emerald bracelet and hoop, clip on earrings Jess." Emma said as she handed me the jewelry. She added, "You need to get more jewelry and have your ears pierced soon."

I just kind of agreed by shrugging my shoulders and giving a little tilted head, shy smile.

Before heading downstairs I swapped my Burberry purse from last night with a larger brown leather satchel purse from Fossil. Just as Emma reminded I checked to make sure I had all my essentials inside.

I gave myself one last check in the full length mirror.

I loved everything about my outfit. The leggings showed off my toned thighs. The Commando undies made my butt more round and plump. The belt gave me some sexy curves. The stretchy tee and chambray shirt revealed a little bit of cleavage. And the boots and purse completed my cute look.

As I continued to check myself out in the mirror Emma threw her hip into mine and said, [laughing] "Okay MIssy, don't get too vain on me. Come on now. We have a 5:45 appointment at the Saks salon."

-

"I'd like to drive tonight Em." I said as we headed to our garage.

"Sure. Just don't get pulled over. Don't want to go there." Emma said giggling.

Emma and I got into my red BMW X3 SUV and headed to the Oakbrook Center Mall. Women get a bad wrap as being terrible drivers. I found it's just the opposite. I drove slower, paid careful attention to my hand positions on the wheel, and used the mirrors more. We listened to Selena Gomez as we sort of danced in our seats. It was fun driving as a girl for the first time.

"So you think you'd ever want to hook up with 'Mr. Goodbar' again?" Emma asked as we drove to the mall.

"Oh geeze, I don't know. Maybe. Maybe if I fully transitioned. Even then he may freak out." I relied.

"Well you have his number. You should call him sometime. Long distance relationships can be kind of fun and romantic. Emma explained.

"Ya. We'll see. Might be something to think about." I said with a wry, cheeky smile.

We got to the mall and decided to self park outside Saks. We scurried through the department store heading to the salon. I couldn't help but stop a few times as we passed the shoes and admire some sexy pumps. I was a girl now, I wanted more heels.

"Unless you want to pay $900 or more for those, we can go to DSW later and get some bargains." Emma said on the way.

We arrived at the salon and a nice gay guy checked us in and took us to the back where they did mani's and pedi's. Emma and I sat side by side and drank some red wine as the nail girls went to work on our feet and hands. It was so relaxing getting professional French gel tips and nail finishes.

To let our pedi's dry, we slipped on complimentary flips flops and scampered over to the hair side where a stylist shampooed and styled our hair.

"You should think about adding some auburn highlights." my stylist named Kristina told me.

Emma quipped, "Yeah I know. That's what I tried to tell her."

I gave in and agreed to make an appointment to have my hair colored soon, though I was a tiny bit concerned how that would be received in my boy mode at work.

Emma had her long brown hair straightened, primped, and styled into a Jessica Biel bangs style hairdo.

Kristina attached my extensions and curled them with my light brown hair into some cute locks which fell to my shoulders. It looked so natural and was excited to grow out my natural hair in the coming months.

At the salon I picked up some hair styling and hand/foot care tips from the girls. They were so nice. Emma said they had no clue I was a boy.

We left the salon and walked through the mall to Nordstrom's to catch their big Saturday sales. I felt so sexy with my girly hairdo and fun shopping outfit. Emma's hair and outfit looked great too. We turned some heads, but mainly from older guys getting dragged around by their wives and daughters or from rambunctious teenagers hanging out at the mall.

On the way to Nordstrom we popped into one of my favorite stores, Victoria's Secret.

Emma bought some new PJ's and a camisole/panty set. I purchased some lacy 'Bombshell' [2 cup boost] push up bras with matching thongs, boy shorts, and garter belts in pink and red. On sale I got a 'Dream Angels' lace bustier in a black/nude lace with matching hipster briefs and a 'Very Sexy' gift set containing spicy/fruity perfume, candles, body soap & mist, lotion,and powder.

I really loved the 'Very Sexy' scent and the 'Bombshell' bras which gave me a solid C cup without any assistance from my cleavage enhancing Nubra.

Lastly at Victoria's Secret I selected two pairs of cute pajamas with a silky top, top pants, and a matching robe.

Near the entrance to Nordstrom we passed The Limited, another one of my favorite stores. They were having a 2 for 1 sale.

"They always have great wrap dresses and cute skirts." I told Emma.

We walked in and Emma immediately helped me pick out a blue wrap dress in a very stretchy viscose fabric. I also found two pencil skirts I liked in black and heather gray, a red blazer, three tops, and a pair of gray leggings.

I loved the blue wrap dress. When I tried it on and came out where they have all the mirrors a clerk said I almost looked like Kate Middleton from the Royal Family. Emma said I was about the same height as her and that we both had slim hips and athletic bodies.

I took it as a huge compliment and gleamed. But I knew I needed to trim 20-30 pounds from my frame to look like the Duchess of Cambridge. I loved her style, clothes, and look. She was a role model for me.

Finally we made it to Nordstrom. It was a mad house. My arms were already tired from carrying the bags from our previous stops.

"This is when we could use a strong guy or two to carry out bags." Emma said with a giggle.

I replied sarcastically, "No kidding. Where is Danny when we need him."

"Ha! He's a bad boy Jess. Don't get your hopes up." Emma replied.

As a guy I knew the whole 'good guy' versus 'bad boy' argument with women. It always felt natural to be a 'good guy' around girls. But as 'Jessica' I felt an attraction to both 'good' and 'bad' boys.

Emma and I decided to split up at first. She went to the work wear department and I hit the shoes. I wanted some leopard print pumps damn it.

I was like a pyro in a fireworks store. Nordstrom has to have the biggest shoe department anywhere. I wanted to try on and buy every sexy pump I saw.

I wandered through all the displays. It was a maze of shoe ecstasy. Then I saw them. Christian Louboutin leopard print pointy toe heels with a red sole. I had to have them.

A younger sales guy with short brown hair named Evan came over and asked if I needed help.

"Yes. Do you have these in a size 10?" I asked.

"Let me measure your foot first. These run a little small and are in European sizes." Evan replied.

I sat down and removed my right boot as Evan brought over a foot scale and measured my foot.

"Looks like you're a true size 10. I'll see if we have a 40 and 40 ½ in these." Evan said as he went into the storage room.

Evan was not strikingly handsome, just a cute, average looking guy and very polite. He reminded me of a younger, taller version of Matt Damon.

Evan came back with 2 boxes and said "Let's try the 40 first. You have somewhat narrow feet. I think these will fit."

I took off my boot sock and put on a little nylon footie. Evan slipped the shoe on as I stood up.

"Feels pretty good." I said and made a mental note on how I loved the way Evan handled my foot. He had very well kept and strong hands.

"Great. Let's try the other foot." Evan replied enthusiastically.

I sat back down, crossed my legs, unzipped my left boot, and removed my sock. From the corner of my eye I could sense Evan was kind of scanning my feet and newly manicured toes. It made sense, a guy with a mild foot fetish selling women's shoes.

I put on another nylon footie and slipped on the second heel. They heels were about 1 inch higher than I was used to. I took a couple short steps remembering in my head 'heel to toe, heel to toe' as I took them for a test run.

In no time I picked up my girly gait and strutted about 8 paces back and forth in the leopard print Louie's. They fit great and I loved them. At one point during my strutting I caught Evan wryly checking me out in one of the mirrors.

After the last strut I went back to Evan and said "I love them. But there's no price. What are these going to cost me?"

Evan replied "They retail for $875, but they're on sale today for $675."

"Ugh." I stuttered as I took them off. And added "I thought all shoes were half off."

"No. Not these. But we have special financing available, or I could, ummm." He said.

"Or you could what?" I asked.

"I could use the storewide 40% coupon. But please don't say anything. I need this job. I'm in the National Guard and going to med school next year." Evan said.

Evan suggested using a storewide 40% off coupon, even though Christian Louboutin were excluded.

"Oh geeze. I don't want you to do that. Sticking your neck out. You're already serving us." I replied.

Evan looked a little nervous so I went up to him, got on my tippy toes, kissed him on the cheek, and said "Thank you for your service, I'll take them at the retail price."

Evan said [blushing] "Errr, yeah okay. And thanks."

Evan was a sweetheart and a service member. I couldn't take advantage of him.

Evan boxed and bagged my Louie's as I put my boots back on. I then handed him my Discover Card for payment.

"Ummm, so is Derek available to authorize this?" Evan inquired.

I had made several purchases today on my guy mode's credit card without anyone saying a thing. Now Evan was questioning me. I wondered if he knew or something. Maybe because I was buying high end shoes.

"Derek's my husband, he's at home." I replied.

"Okay, I just need to see your I.D. and verify last names and addresses. It's required for any purchase over $500" Evan explained.

I was so embarrassed and didn't know what to do. I wanted these shoes. They were on sale. Had I been in guy mode it would be no big deal.

I murmured "Look Evan. This is embarrassing for me. But I'm actually Derek. I'm beginning my transition but haven't changed my name, obviously." as I handed Evan my I.D.

Evan lightly laughed and said "Ha. You're kidding right. You're playing with me."

I gave him a stern look and nodded after he asked if I was serious.

"Ohh, ummm, yeah let's ring this up I guess." as Evan looked more confused than ever.

Evan scanned the shoe box, scanned another card he took from his pocket, and ran 'Derek's' Discover Card through. The register kicked out the receipt and I signed it.

After signing it Evan gave me a copy and said "Thank you for your purchase at Nordstrom, ummm, errr Der err ek; We hope to see you again."

I replied "It's Jessica actually. And thank you." as I gave Evan a little wink and dashed off to go find Emma.

As I left the shoe department I noticed on my receipt a 15% 'employee discount' and that I only paid $608, not over $700. I realized Evan had given me a discount, even after he knew.

I pranced back to the shoe department and found Evan helping out a lady in her 50's. I slinked up to him from behind, gave a wink to the lady he was assisting, and quickly gave him a peck on the cheek from my tippy toes.

"Thank you again." I said as I smiled at Evan and the lady.

"No problem." Evan replied as he turned and smiled at me. He added, "Oh you forgot this ma'am."

Evan handed me a small shopping bag with a little red 'Christian Louboutin' coin purse in it.

"It's an exclusive Nordstrom freebie with every 'Louie' purchase over $500." Evan explained.

I blushed, gave a little girly wave, and silently mouthed a "Thank you" to Evan before finally leaving. .

-

I headed up the escalators to the women's department to find Emma and brag about my haul.

"Hey Em look what I got free." I snickered while Emma looked at 'Theory' skirt suits in the work wear department.

"Whoa. Whatcha got there." Emma inquired after she saw the Nordstrom bags.

"Well I know they were expensive, but I had to have them." I said while pulling out the leopard print 'Louie' pumps. I added, "Oh and this little handbag was free."

"Those are so so hot. Wow!" Emma excitedly quipped. She continued, "They're on your credit card I assume."

"Of course Emma. All in my plans. And I met a nice shoe guy. Evan. He's in the Army. Going to be a doctor I guess." I responded.

Emma replied, "Was that the sales clerk you were flirting with?"

"I wasn't flirting, or, or, umm, well; yeah that was probably him. He was very nice. I even told him I was trans." I told Emma.

Emma replied [laughing] "Oh my god, I didn't see you. I was just kidding, But that's cool." She added "So really. It didn't bother him. I guess you're just plain hot Jess. Guys beware." Emma quipped.

"Ha ha. Evan's just a nice guy. I like him." I replied.

"Okay. You know you need some killer outfits to go with those heels, right Jess?" Emma said with a questioning look on her face. She added, "You need a cute LBD and some skinnies."

"You mean a little black dress and skinny jeans right?" I asked.

"Yup. Let's check out the dresses after I try on this skirt suit." Emma said.

Emma marched to the dressing room and came back wearing a Navy pinstripe skirt suit from 'Theory'.

"I likey. Looks great on you. Very professional." I said as I complimented her.