Becoming Jessica Pt. 05

Story Info
Jessica has an erotic evening after shopping.
5.5k words
4.64
25.3k
29

Part 5 of the 5 part series

Updated 06/08/2023
Created 01/09/2017
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Quick synopsis: I am a crossdresser and transgender. My wife Emma is supportive and wants to help with my transition. After coming out to her we are having our 2nd girls night out with shopping, movies, and a late bar stop. This part begins as we leave the mall at closing time.

"Oh shit, it's almost 9. Hurry. We need to get back to Saks!" Emma said as she pulled me down one more flight on the escalator.

By the time we got to lower level it was 9:05 PM and the gates to the mall were closed.

We heard from some other patrons the mall enacted a new regulation where they required all stores with outside entrances to close their gates at 9 PM in accordance with their new anti-protest and teenage hooligan policy.

Emma and I made our way to a Nordstrom side entrance and noticed it had started to rain pretty hard.

"Great. This pretty much sucks Em. We're parked all the way on the other side of the mall" I said with a dismay while standing near the Nordstrom customer service area.

As Emma and I debated how to get back to my car a familiar voice chimed in.

"Sorry girls. Mall's closed. Moose should've told you out front." The voice said in a weirdly, contrived voice.

After we turned around I noticed it was Evan, the cute shoes sales guy.

Emma replied with a stammered look on her face "Wha what? Wait, what."

I immediately started to laugh. I knew Evan was joking. He was ad-libbing the line from 'Vacation' where the John Candy security guard character told Clark Griswold (Chevy Chase) Walley World was closed.

I jokingly added, "Listen here, we're on a public relations, err fall inspection, ummm personal visit thing."

Evan began to almost howl in laughter. Emma too, but she didn't know what the gig was all about.

After Emma caught up to the joke Evan insisted on driving us and our bags to the other side of the mall.

"He's cute, and nice." Emma said as we waited for Evan to bring around his vehicle.

Like a gentleman Evan pulled up underneath the Nordstrom entrance overhang and helped us load our bags into the back of his Jeep Cherokee.

Evan was clearing up his front passenger seat when Emma received a phone call. Evan had his National Guard duty bag strapped in the seat and started to apologize while trying to remove it.

"Thanks. But don't mess with it Evan. We'll just scoot in the back." I told him as Emma was distracted by her phone call.

Evan drove us around the mall to my car while Emma chatted to someone on her phone.

"Did you guys get everything you were looking for?" Evan asked while glancing at me in the rearview mirror.

"Yeah totally, I love Nordstroms, great buys and really nice people there. Thanks again Evan." I replied with a little wink as he smiled back at me in the mirror.

With Emma giggling on her phone in the background I added "Of course the girls upstairs were very helpful and understanding as well."

"That's great to hear. And to be honest, I; I would never have known you were, err, umm; you know what I mean. I bet they didn't either." Evan replied.

"Well I think the girls in the jeans department kind of knew. With my slimmer hips and all." as I gave him a smile and wink back.

Before Evan could reply Emma ended the call and said [Giggling] "Danny wants to know your status."

"Oh really" I replied bellowing.

[Danny was the hot personal trainer from Lifetime Fitness who seemed to be checking me out earlier today.]

"Yup. And he wants to meet us at the Tilted Kilt later after the movies." Emma added.

"Oh Geeze." I quipped as I as told Evan where my car was.

Evan pulled next to my car and got out to transfer our bags as the rain started to subside. I assisted him while Emma was busy texting on her phone.

As Evan transferred our bags I couldn't help but notice his rather lean and sexy body. He wasn't really muscular, but appeared to had a nicely toned body peaking out from his fitted oxford shirt and black front flat pants which were slightly drenched from the rain.

"Well, there you go." Evan said is a shy manner.

"Thank you so much Evan, really nice of you". I said as I smiled and glanced up at him.

Evan was a few inches taller than me. He had nice brown eyes and a very caring presence. I felt a special attractiveness to him. Like I wanted to kiss him, but it felt so strange.

We both kind of stood there for what seemed like 5 minutes just glancing around and smiling when Evan bluntly said, "Look, I'm not gay but I'd like to ask you out on a date. I don't look at you as a guy. I look at you as a really pretty, feminine girl. There's just something about you I find so sexy, alluring, and erotic."

I wasn't offended at all. I was of course flattered and started to blush and said "Yes."

I didn't have any other words or a chance to respond further when Evan moved in, lightly caressed my shoulders, stared into my eyes, and gave me a very brief, but passionate kiss on my lips.

I was briefly lost in the moment. It felt surreal. I was captivated and caught off guard in a good way. I had never felt more feminine and desired. I liked how Evan just went with the moment and could tell I wanted to kiss him as well.

We were shaken from our embrace by a loud HONKING.

"Kids. Really. Am I your chaperone?" Emma said laughing from the car.

Evan and I laughed as we gave each other a final hug, another kiss, and exchanged phone numbers. Evan had 2 weeks of National Guard training and was leaving in the morning.

As I was about to get into my car Evan drove back around and said "Have fun at the movies and the bar later."

"Thanks. And you be safe in training sir." I replied as I practically threw myself through his drivers door window and gave him a quick kiss on the cheek before he drove away.

As I got back into my car Emma giggled "Haha. Look at you. Soldiers girl."

"Oh geez, whatever. It's just a date. He's really nice and understanding." I replied.

"Well you're single now Jess. Have fun and enjoy being a girl. You're already making strides." Emma said in a chuckle. She added, "So let's hit the movies!"

Emma and I drove to the Emagine theatre and scampered into the lobby. It was 9:25PM and the only movies starting in the next 30 minutes or so were a bunch of action, science fiction, or horror movies like 'The Transporter Refueled' or 'The Visit'.

We then noticed one romance movie 'Carol' started at 9:20 and we could probably pop in and not miss much.

Emma and I bought our tickets, some popcorn, and two huge margaritas before sneaking into theatre # 8 just as the previews were ending.

'Where do you want to sit Em?" I whispered while munching on some popcorn.

"I can't see." Emma giggled as we scurried up the stairs.

As the movie began we were able to see plenty of seats open in the front middle area and settled down next to each other in their nicely sized recliner seats.

It was kind of funny, as a guy I never thought much of the big stadium style recliner seats. I always thought it was pretty cool and comfortable. But settling in as Jessica, with tight leggings, chambray top, riding boots, and figure hugging lingerie, I felt so small and girly. It felt so right.

Emma and I munched away on popcorn and sipped on our margaritas watching the movie 'Carol' set in New York City in the 1950's.

Cate Blanchett played 'Carol' the lead actress. She was a glamorous woman going through a divorce during the Christmas season when she met another woman named Theresa who was a sales clerk in a major department store.

Theresa was also a photographer. They struck up a friendship when Theresa offered to take candid photos of Carol in order to add to her Manhattan lifestyle portfolio.

Well one thing led to another and Carol and Theresa began a taboo relationship which started after a sexy photography session when Carol modeled assorted lingerie.

During the movie I couldn't help but feel my boys parts start to stir under my tight leggings and 'Commando' thong briefs. I was starting to become really horny. I glanced over to Emma and she gave me a coy look with a sexy, pouty smile.

I won't give away the ending but it was an erotic 2 hour movie with some nice drama, romance, sensual lesbian scenes, and suspense.

"Wow." I told Emma as we walked out of the theatre. I added "I liked it. I was missing out not watching chick flicks."

"Yeah. Umm. Cate Blanchett was really good. And sexy. Yeah wow." Emma lightly giggled.

"I'm starving. I hope Tilted Kilt is still serving food." I told Emma as we left the theatre parking lot.

After checking her phone Emma replied, "Yup. Bar menu until 1 PM."

"Cool. It's always fun there too." I replied.

-

Emma and I scurried through parking lot heading to my car. I felt a little chilly and vulnerable. It was in the 60's. And I didn't have a coat. But I felt very feminine gliding in my riding boots while swaying my hips somewhat frantically in a girly way. I tried not to to notice, but it was thrilling seeing wolfpacks of guys checking us out. I liked the attention.

On the drive to Tilted Kilt I asked Emma if she ever fooled around with other girls before we married.

"Yup. A few times outside of the wild threesome I had with Kirk and a sorority sister." Emma replied.

"Well as Jessica I'm totally into guys, but I'm still attracted to girls too. Very confusing." I explained.

"That's totally natural Jess. We all want to have fun. And as a girl that means sex. Might be with a boy or a girl." Emma bluntly said and added more sternly "But eventually, for me, I want a man, a man and a family with kids. I want babies."

"Oh geez, I know, my bad; I want you to be happy Em. In fact I can now see why you want to have babies. These past 24 hours have made me rethink things. I can see myself as a wife and a mommie someday." I said in a serious voice.

"Ok, really, let's drop this for now. I think we're on the same page. You're getting girl emotions now Jessica. And that is fine. I'm here for you." Emma said as she patted me on my shoulder.

"I am as well. I'm so grateful I have you Emma." I replied as I pulled into the Tilted Kilt parking lot.

After we found a parking spot near the front entrance Emma and I headed inside. There was no hostess or anyone at the door so Emma and I just walked into the bar area unopposed.

The place was fairly packed. A simple variety of men, a few women, and some couples. The Notre Dame vs USC football game was just finishing up so there were large groups of rowdy men filling the bar area. There was also a 2 piece Irish folk band setting up to play.

Emma guided me through the maze of testosterone to a small pub table for two in the corner. I fully understood now how women felt in a so called 'meat market'. Don't get me wrong, I so so loved guys rubbernecking and checking us out as we scampered through the bar, but it was a bit overwhelming and almost creepy.

"You did good girl, this place is a little crazy" Emma said as we sat down.

"Ha, yeah, these guys here are everywhere; I like the attention, but it's, it's too much I guess." I stammered.

"Well let's have some fun. Ian Tom Leahy band is playing here tonight." Emma said.

The waitress came over and we ordered 2 spinach chicken salads, the appetizer sampler, and 2 Guinness draughts.

After the waitress brought us our Guinness, Danny the trainer from Lifetime Fitness surprised us with 2 shots of Tullamore Dew irish whiskey shots.

"Hey there. Looking fine you two." Danny said as he pranced to our table with the two little snifters full of whiskey.

Emma gave Danny a big hug and kiss. Danny then came over to me and kissed me on the cheek and lightly patted my butt.

Danny pulled up a pub stool next to me and chatted us up. I daintily scooted up on a stool and crossed my legs while paying attention to my girly posture. I felt so sexy in my tight leggings and chambray top. I made sure my cleavage was visible as I playfully flirted with Danny by stroking my hair locks and pursing my peachy stained lips.

"So what the heck have you two been up? Shopping I assume." Danny inquired.

"Yeah, of course, Jessica needed a night out. Shopping, a movie, and stuff. She's been cooped up for way too long. Oh and she's single." Emma coyly said while winking at Danny.

I immediately kicked Emma under the table with my riding boots as Danny lightly laughed and said "Oh really. Nice."

He was obviously drunk. Again I liked the attention, but his machismo was a little bit of a turnoff.

Emma and I slowly drank our Guinness and took tiny sips of the whiskey. We both gave funny, girly faces after each sip.

Danny, Emma, and I chatted about working out, sports, and music while listening to the Irish band.

"Are you guys hockey fans? Love the Blackhawks." Danny stated while discussing the upcoming NHL season.

"Yeah. Of course. I've been to a few games, but in the nosebleed sections." I replied laughing.

Emma added, "My soon to be ex wasn't much of a fan. But it's pretty exciting I think."

I gave Emma a grimacing look and she tried to lampoon my male self. She was such a little devil sometimes.

Danny excused himself and went back to his buddies after our food arrived.

Emma and I munched away on our salads and appetizers. We were both pretty starving, but I concentrated on taking smaller bites and to eat slower. Girls like to pick away at food. I kind of liked being finicky, made me feel more feminine.

Danny returned after 15 minutes or so and said "Oh, my God. You two are still eating?"

Emma replied giggling "Dig in Danny. You're a growing boy."

Danny didn't need an invitation and devoured the remainder of the appetizers. Guys are such pigs sometimes.

"Eat much?" I asked Danny in a funny inquisitive manner.

"Ha, sorry, my metabolism, I did a 90 minute Cross Fit class tonight; you guys should try it. Lifetime (Lifetime Fitness) just started classes in one of the gyms. Great workout." Danny said.

"Sounds tough." I replied.

"Nah, not really tough, just intense, and kind of fun." Danny replied.

Emma added "Yeah, maybe next weekend. I need to get Jess and I in shape."

"You guys look great, are kidding me." Danny said while choking down the last chicken wing. He added "Hey let's go over to the bar with my buddies."

"Ok. We'll be over there in a minute after we pay our waitress." Emma said.

While Danny sauntered back to the bar I asked another waitress if our bill could be brought over. I then glanced over at the bar where Danny was and there were at least 5 or 6 other guys with him.

Emma could tell I was nervous about being around that many guys and said "Don't worry, we'll go over there and have one drink. Those are all guys from Lifetime."

"Yeah, I know, I'm just nervous one may recognize me." I replied.

"Ha. no way." Emma said laughing. She added "Trust me, they won't."

After we paid our bill Emma and I headed over to the bar area and joined Danny and his friends. We ordered two more Guinness and listened to Irish folk music while trying to talk to the guys. It was pretty loud so we were content on just telling them we were having a good time and liked the band.

Danny tried to introduce us to the group of guys. I couldn't really hear their names, but I learned later the one Emma started talking to was a Lifetime Fitness sales guy named Brett.

Danny stood by my side and seemed to shield me from the other male bar patrons. It was kind of nice to feel protected. He was a big guy, very fit. I felt safe next to him.

"Having fun?" Danny voiced politely me in my ear.

"Yeah cool band, fun." I replied.

"So what do you like to do outside of work and stuff?" Danny asked.

[Giggling] "Shopping." I replied.

"Come on, seriously Jessica. Danny said. He added, "Do you want to go a Hawks game sometime?"

I replied "Ummm, sure, you know I like hockey silly."

"Cool. I can get great suite tickets." Danny said as he went to order a drink at last call. He added "Another?" As he held up his glass while asking me if I wanted another drink.

"No thanks. We're leaving after this one." I replied.

I was a bit taken off guard. I knew Danny liked me. Being asked out on a date by two different guys on the same night was a lot to comprehend. As a guy I was more monogamous. But as a girl I felt the need to explore my new femininity. Going on dates with attractive guys felt right. Maybe it was mind playing catchup or something.

Emma squirted back over to me and said "What's up."

"Danny asked me on a date." I said with a slight smile.

"Ha!" Emma replied and gave me a shoulder nudge. She added with a chuckle "You're too easy Jess. Word will get out."

"Again it's just a date. It could be fun. He asked me to go to a Blackhawks game." I replied.

"I'm just kidding you. I know it's innocent, but" Emma said as she was distracted by Brett at the end of her sentence.

Danny came back over to me and handed me a cocktail napkin while yelling "Need your number."

I pulled a pen out of my purse and carefully wrote my number on the napkin. Emma borrowed my pen and gave Brett her number. We then finished our Guinnesses and gave our new beauxs a quick hug and kiss on the cheek.

Emma and I scampered out of the bar almost arm in arm lightly laughing. It was excited as a girl to meet guys who were interesting and attractive. It was more innocent than anything.

We got back into my car to drive home when Emma said " So, to finish an earlier thought; umm at one point you need to tell these boys you're trans. I know Evan knows, but Danny might have a problem with it."

On the drive home we continued our conversation.

"Yeah, I know. I just think if a guy falls for me, he won't mind; well maybe he won't mind. That's why I want to date guys and get to know them before any intimacy. If it goes well and they seem understanding, I'll tell him." I explained.

"Ummm, Drake, last night; that went pretty fast." Emma said laughing. She added "You didn't tell him."

I replied "Well it was late, dark, we were drunk, caught up in the moment; and I trusted him. Besides I was only giving him a BJ."

We pulled into our garage as Emma said "Just be careful Jessica. I don't want to see you get hurt or something."

After we got out of the car I thanked Emma again and gave her a big hug. It was nice still being close to her.

"Hey let's grab some ice cream, a bottle of port, and try on some of our outfits and stuff" Emma said.

"Heck yes." I replied as we gathered our bags and headed upstairs.

I carried my bags up to my room after two trips of course. It was lovely hanging up and putting away my new girly clothes, shoes, lingerie, cosmetics, and products. I absolutely loved the smell of everything. It was a wonderful mix of feminine scents from everything I bought. It was heavenly to say the least.

"I'll get the ice cream and wine." Emma yelled out and she marched downstairs. She added "Put on your new PJ's Jess."

I sorted through my Victoria's Secret bag and found my sets of silky and lacy camisole and romper sets. I removed my low heeled riding boots, chambray top, t-shirt, and leggings and slid on a purple lace romper set and matching knee length robe.

I left on my Commando bra and thong to help keep my girly curves and boys bits at place. I lastly sprayed on some of my new 'Very Sexy' perfume and lit one of the candles included in the gift set for giggles.

I tiptoed into Emma's room and found her prancing around in her new pink VS camisole tap pant set sipping on some port wine. She scooped out some ice cream and turned on the bedside Bose stereo.

"Wow. You look cute Jess. I like purple on you. Sexy color." Emma said as she put in a Rihanna CD into the Bose system.

12