Becoming Jessica Pt. 03


To recap: I came out to my wife Emma yesterday that I was a crossdresser and was considering transitioning into a woman. After some initial grief she became supportive and helped me fully dress as a woman for the first time. We even went on an impromptu ‘girls night out’ at a piano bar in a local hotel/resort in suburban Chicago where I met a man named Drake who was in town for a convention. I ended up giving my first blowjob and spending the night in his suite. Emma took Kirk the bartender home with her. After Drake flew home to San Francisco I took a waiting Town Car home.


After arriving at home I thanked my driver, gave him a tip, and helped myself out of the Town Car. As I walked up the driveway my neighbor, Jon Simmons, glanced over at me as he was fertilizing his lawn. He didn’t seem to pay much attention. I think he was more worried about keeping his lawn looking like Wrigley Field..

I walked into the kitchen and immediately bumped into Kirk who was getting a bottle of water.

“Hey now. Look who is just getting home.” Kirk said in a teasing manner.

“Ha ha.” I quipped back. And continued “Looks like you guys had a good time.”

As I glanced around the kitchen and living room there were bottles of booze, shakers, a blender, fruit, and remnants of Emma’s outfit from last night scattered everywhere.

“Yup. Good times. You missed out Jessica.” Kirk replied.

“Umm. Yeah. I was having a pretty good time of my own.” I said with a pompous wink.

I heard a car horn honking out front when Kirk said “Well it was nice running into you again. [winking] Maybe you can join us next time.”

“Ummm sure I guess.” I coyly replied.

Kirk ran off to the car waiting in the driveway.

I walked upstairs and found Emma in our bed. She was still wearing her red blouse [unbuttoned], black skirt, and one of her black stockings.

Emma moaned “Oh my, my head. Ugh.”

“Yeah, me too. I think the champagne did it for me. So it looks like you two had a good time.” I added.

“Too good.” Emma replied with a slight laugh. She added “Doesn’t help my pussy is sore from Kirk fucking me like 5 or 6 times. I could’ve used some help from you Jess.”

“Ha yeah right.” I replied blushing.

Still wearing my wrap dress, I kicked off my heels, removed my hair extensions, and hopped into bed as Emma removed her lone stocking while stripping off her garter belt.

“Oh and Kirk knows about you. He put two and two together when we got here last night and saw the crossdressing books on the kitchen table.” Emma said.

I replied “Oh that’s just great Em.”

“No big deal Jess. He doesn’t care. He actually thinks you’re hot. He’s a sex freak and talked about you in a kinky way when we fucking.” Emma explained.

My mind started racing. Was Emma suggesting we have a three way with Kirk? The thought sent a sexy shiver up my spine.

“Well he is pretty cute [blushing]. But don’t you like him?” I added.

“Not for a relationship, but to play around with, hell yes. He’s great in bed.” Emma cheerfully said.

Emma added “Maybe we can get together with him sometime. I started dating Kirk in college and one time we got it on with a sorority sister of mine. It’s a lot of fun. You need to explore your new identity and sexuality Jess.”

“Yeah, I guess. Sounds like it would be a pretty hot time. ” I replied with a slight smile. .

“Soooo, tell me about your night Jess.” Emma inquired.

I propped up in the bed and said “It was great. Drake was so nice. He was a perfect gentlemen. And we slept together. I loved it.”

“What? You slept with him?” Emma said with a puzzled look.

“Not like that Em. [laughing] No we fell asleep together in his bed.” I replied.

“So that’s it?” Emma inquired.

I replied “Well after a few dances and drinks we started kissing at his table. That carried on to the elevator, then the hallway, then in his suite. It got pretty hot and heavy.”

“NIce. And, then?” Emma quipped.

“We started to explore each others bodies. I had my hand up his shirt and he had a hand up my dress. I told him I wasn’t comfortable going all the way, but hinted I would suck his dick.” I explained.

“Wow girl! Look at you, so how did it go” Emma said enthusiastically.

I continued to explain “He had a pretty big cock. I worked it with my hands and mouth. Did everything I know I like. Made some moaning sounds suggested in one of the mags I read in the tub. It was actually fun and pleasurably for me.”

“Wowza, That’s pretty hot Jess.” Emma said with a huge smile.

“Yup. I liked it. Rewarding him for treating me like a lady and being a gentlemen. Oh, and tee he; I swallowed.” I said with a giggle while partially covering my mouth.

“Ha. See it doesn’t taste bad does it?” Emma inquired.

“No. Not really. Just a little salty, warm, and kind of sweet too. I liked the taste. Swallowing made me feel very womanly.” I replied with a big smile.

“Not to be rhetorical Jess, anime porno but did Drake enjoy himself?” Emma inquired.

“Ha! Yes. He cummed pretty hard in my mouth while calling me baby and stuff. He said I was really good.” I explained.

I added, “It was a nice night. I liked sleeping in his arms after pleasuring him.” I explained.

I went on to tell Emma about the note when I awoke and that he left me his phone number and had a car waiting for me to take me home. I also told her he lives in San Francisco.

“He sounds too good to be true. Sucks he lives in San Fran. I bet he’s married or something.” Emma added.

“Yeah, who knows.” I replied.

“So, Jessica, once these hangovers wear off I think we should go to the gym. We need to get you started on cardio routines to burn some of that tummy off. Also do some good exercises to help with your curves, waist, hips, butt, and trim up your arms.” Emma explained.

Emma continued “Then throw on some cute shopping outfits and hit the mall.”

“As Derek or Jessica?” I asked.

“As Jess silly. Look in the mirror. Even with just a little makeup and your hair primped up a bit, you still look feminine. It’s all in the way you carry yourself. You have it down girl.” Emma said enthusiastically.

“But I don’t have any girl workout clothes” I replied.

“I’ll take care of that. Don’t worry.” Emma quipped.

Emma and I took a few aspirin, guzzled some Powerade, and drifted off to sleep.

When I awoke it was 12:30 PM and Emma was gone. She left me a text which read:

“Going to Dicks.

Getting u some cute gym clothes.

“Be back by 1 or so.”

Still wearing my dress from last night I went down to the kitchen to get something to eat. I put on a pair of Emma’s fuzzy pink slippers to stay in girl mode. They were a little small but I was still able to prance around in them like a silly girl.

After I made some green tea I saw a note on the fridge which read:

“We need to get you on a better diet.

Eat some fruit, yogurt, flaxseed, and granola.

No more bacon or donuts.


I grabbed a bowl and mixed some plain greek yogurt, granola, blueberries, and strawberries together. I grounded up some flaxseed and added it into the mix as well.

I went over to the kitchen table wear the crossdressing books were laid out. I sipped my tea and ate my healthy concoction while flipping through “My Husband Betty” and “Alice in Genderland”. Both books dealt with how wives cope with husbands who crossdress. Emma said they were very helpful in her decision to support me.

Another book caught my eye. The book was titled “The Transgender Companion (Male To Female): The Complete Guide To Becoming The Woman You Want To Be.” It was meant for transexuals who wanted to have a full sex change and become a woman.

I wasn’t taking hormones yet, but the last 24 hours made me truly feel transgendered. I wanted to transition. I just didn’t know when I could. I knew I would have to go back to guy mode come Monday.

I sipped and munched away as I read a few short chapters which dealt with the steps you should take during the transitional period. Going to a therapist, coming out to family and friends, coming out at work, hair removal, breast implants, facial surgeries, and sexual reassignment surgery.

The book recommended living full time as a woman for one year before the final surgery and was full of good tips.

Hair removal didn’t sound fun, but the book said it’s definitely necessary and recommended laser treatments. I didn’t think I’d need any facial surgeries. Emma told me my cheekbones are high enough and my adam’s apple is not pronounced.

I also didn’t think I’d need breast implants. My breasts were already a little flabby and according to the book hormones would grow them to half the size of your mothers. My mother was at least a D cup so I felt mine could grow to at least a B and maybe a C. Perfect for my body type.

I really liked the chapter on how to look, act, and sound like a woman. Everything from how handshakes should be straightforward, firm, hand held higher, and more simpler than a guy’s handshake.

The chapter also explained how to place your hands on your hips with your fingers down and thumbs forward. The importance of proper posture with a straight back, sucked in stomach, chest out, and shoulders back.

Another tip was to always turn your wrists upward when you walked or sat with your hands on your lap. There were even tips on how to eat and drink such as taking small bites and sips and holding eating utensils more like a pencil, not a shovel. .

Voice tips included using better resonance while speaking. Avoid speaking from your chest, rather speak from your neck, mouth, and lips. They suggested practicing saying “mmmmm” and “nnnnnn” and notice how your mouth and lips vibrate, not your chest.

I spent a couple minutes tuning my voice with the “nnnnn’s” and “mmmm’s” and could feel anne porno a soft, feminine vibration coming from my lips.

I finished my healthy meal and tea, with a few small bites and sips of course, and went back upstairs to shave my face closely again and prepare to go to the gym.

I went into our master bath and turned on the shower. I grabbed my Venus razor and touched up any stubbles on my legs, arms, and chest. I lathered up my face and shaved twice to remove any traces of my beard shadow. I also used Emma’s face scrub and makeup remover.

As I rinsed off I practiced the voice tips “mmmm’s” and “nnnnn’s” again. I loved the soft feeling it set my voice at.

I heard the garage door opening as I stepped out of the shower and knew it was Emma coming back.

Emma came upstairs as I was rubbing lilac minty body lotion all over my body while also checking my nails.

Emma was already wearing her workout clothes. She had on a nice combination of stretchy workout leggings, sports bra, t-shirt, and hoodie.

“How do your nails look Jess?” Emma asked.

“My french tips look okay. My toes too.” I replied.

“Maybe at the mall later we will get professional manicures at the Saks Spa.” Emma added.

“Sounds good. I like having pretty nails. It really finishes my look and makes me feel more feminine.” I said with a big smile.

“Hmmm, you’ve been working on you voice haven’t you Jess?” Emma inquired.

“Yup. I read some of those books, picked up some nice tips.” I replied.

“See. I knew you needed a little guidance.” Emma added.

“Yeah, thanks for those books again Em. And for your support as well.” I replied as I went over and gave her a big hug.

Emma laid out a large bag from Dick’s Sporting Goods and said “Check out the cute workout outfits I got for ya.”

“Yeah, I Hope you didn’t have to spend too much.” I inquired.

[Laughing] Emma said “Well I used your new Discover Card. You know the one with zero balance.”

She continued, “And it’s interest free for the first year after the first purchase.”

“I guess that’s seem fair.” I replied

Emma bought me some workout leggings, tank tops and t-shirt, and workout briefs, thongs, and sports bras in black and white. Also in the bag was a zip sweatshirt with a hood and some running shoes in girly colors. .

“Ok, try some of this stuff on. Let’s go.” Emma enthusiastically said.

I first slipped on the white Under Armour workout thong after tucking away my boys. The thong was tight and stretchy and seemed to keep my bits well hidden. I put on the matching white sports bra and added my silicone enhancers which gave me a B cup look. The bra lifted my chest a little bit to show some cleavage.

Next was a pink Puma tank top and gray Nike capris leggings. Both were stretchy and hugged my body.

Lastly a pair of Brooks women’s running shoes in a size 10 along with a multi pack of women’s Under Armour no show liner socks in a variety of pretty colors. The workout shoes were a cute combination of colors. Light teal, gray, and black with a pink sole.

I looked in the mirror and saw a workout chick. My ass looked pretty good in the leggings. And my crotch area was smoothed with no hint of my boy parts. I just needed help with my hair and a little makeup to hide any masculinity.

I sat back down at the vanity where Emma pulled my hair back and took out a hair scrunchie thing and tied my hair into a ponytail. The scrunchie had fake hair attached to it and blended in with my hair much like the extensions did last night.

“We need to put some gym makeup on Jess.” Emma explained.

Emma applied some sweat proof cosmetics such as a tinted bronzer to my cheekbones, nose, and forehead, cover foundation to my beard shadow areas and under my eyes. Waterproof mascara and liquid eyeliner was next. Lastly some pink shimmery lip balm and a little bit of a soapy smelling body mist spray.

“There you go Jess. Perfect.” Emma said.

I looked in the mirror again. The subtle makeup and little ponytail worked. I looked like a cute girl I would check out at the gym.

“Put your shoes on and let’s go girl. It’s almost 2:30. We have a lot to do today.” Emma cheered.

I sat down on the floor and put on a pair of light pink Under Armour footie socks and my Brooks running shoes. They fit great and were really cute. Lastly I grabbed my black Adidas hoodie as it was still a little cool out. With my hoodie zipped up partially, my B cup poked through just enough to show my cleavage.

We jumped into Emma’s car and drove to Lifetime Fitness which was only 4 miles from our house.

I didn’t really lift weights much. Maybe a couple times a month. I went to the pool in the summer and probably swam laps more than anything. I did run a lot which gave me pretty toned legs and a firm butt. Emma was a gym rat. She went 4-5 times a week.

When we arrived at the gym we saw the place was packed. I was little nervous someone may recognize arap porno me.

“Wow, this place is busy today. Ummm.” I stuttered.

Emma replied, “No one will notice you Jess, at least as Derek or as a guy. You look pretty cute actually. I bet you’ll get some attention from some boys like you did last night.”

Emma packed away my gym I.D. in her bag. I decided not to bring a bag so I didn’t have to go into the women’s locker room. All I brought was my iphone, armband carrier, and a pink and blue Nike water bottle.

We walked into the lobby where we scanned our gym I.D.’s. The attendant was supposed to visually check it too but he was too busy talking to a couple younger girls.

As Emma went to lock her bag in the locker room I walked over to the treadmills to warm up. The gym was brimming with people of all ages and evenly divided up between men and women.

I found an open treadmill next to a woman in her 50’s on one side and a younger jock looking guy to my right. I placed my iphone into my armband, put on my ear buds, and picked out some Taylor Swift iTunes songs.

I listened to ‘Last Kiss’, ‘Red’, and ‘You Belong With Me’ while starting out slowly on the treadmill. I tried my best to keep my girly gait going and remembered to keep my elbows tucked in a bit and my wrists and palms turned slightly upward.

As I picked up my pace I started to watch a men’s pro golf tournament on the TV. I remembered that Drake was an avid golfer so I took an interest into watching it. I used to play golf in high school but stopped playing when I went away to college.

It was interesting and made the time fly. Since I stopped following golf I was surprised how athletic and attractive pro golfers were today.

The jock kid left his treadmill which allowed Emma to warm up next to me. We both watched the golf on TV and giggled every time they showed one of the hot golfers.

“We should start playing golf Jess.” Emma quipped as she removed one of her ear buds.

She added “Or at least go to TopGolf in Wood Dale. I went with my friends one night. It was a blast and there were a lot of hot guys there.”

Emma explained the place was more of bar/nightclub with a multi-tier driving range, bands, drinks, and food.

“Sounds like a fun girls night out” I replied.

After 25 minutes on the treadmill we went over to the aerobic area. I took off my hoodie and wrapped it around my waist. It hung down and covered my butt, and actually helped give me more girly curves because it cinched waist.

Emma and I did a bunch of booty exercises without weights. From basic squats to glute kickbacks and squat burpees.

Emma then worked on my flexibility saying “You need to be more limber, It will help with your female movements and elongate your muscles.”

Emma and I went through some yoga and pilates type stretches such as the ‘active pigeon’, ‘modified cobra’, and ‘warrior pose’.

After stretching we went to the free weights area to do some light circuit training for our arms and shoulders.

A trainer Emma knew came over and began talking to her. She introduced me to him.

“Hi I’m Danny. Never seen you here before.” He said in an inquisitive, but polite manner.

“Oh this is my first time here. I work with Emma downtown. I’m Jessica” I replied as I gave him a straightforward, higher handshake like was suggested in the book I read earlier.

“Well cool. I’m always here to help and give suggestions.” Danny said

Truth be told I’ve seen him before in my male mode at the gym. Not that I looked at him before as hot in my male mode, I definitely thought that in my female set of mind. Danny had his light brown hair in a cool pompadour style and had striking brown eyes.

“Hey Danny, Jessica and I are going to do a quick arms and shoulders circuit thing. Any suggestions?”

“Yeah sure. Grab some 10 pound dumbbells and do 4 sets of arm curls, shoulder presses, and chest presses.” Danny said as he demonstrated each exercise. He added “Rest one minute between each set.”

I liked watching Danny show us the workout circuit. Well I really liked looking at his cute butt on a his 6 foot plus athletic frame.

Emma and I began the routine. Danny assisted us with some of our movements. I guessed he was a little younger than us but he was very nice and professional.

It was nice having Danny hold my wrists and elbows when he guided me through the proper techniques. Again it was a wonderful feeling having a man looking after me.

After the circuit training we both thanked Danny as he ran off to help other patrons.

Emma gave me a quick nudge and said “I saw you checking him out. [laughing] You don’t stop do you.”

“Well you told me I need to explore my sexuality. I can’t help but look at guys I find attractive and interesting.” I replied.

“I’m just kidding you Jess. Buy you need to work on being a little more discreet. You’ll learn.” Emma explained.

We next went to the area where they have mats and those big exercise balls.

I suggested “So let’s do some abs.”

“Ok. Watch me.” Emma quipped.

Emma showed me how to properly do crunches on the exercise ball, some pilates and elbow planks, and then some flutter kicks with a resistance band.