Becoming Jessica

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It all started after I told Emma I no longer wanted to have children one day after work on a Friday evening. Over the past few months we were actively trying to procreate after 5 years of marriage. We originally never wanted children, but that apparently changed after her proverbial “baby clock” starting ticking. Don’t get me wrong the sex was great and we were both very sexual people, but I could no longer live with a lie. I had to tell her I was a crossdresser and have had thoughts on transitioning.

I texted Emma earlier in the day “We should talk when I get home from work. I have something I need to get off my chest.”

Emma replied “Ok Derek. But please tell me you’re not impotent or something.”

I replied “No. LOL. It’s not that. See you when I get home.”

Emma replied with a simple heart and smile emoji.

After coming home I found Emma in the kitchen. Emma was a Marketing/PR executive in Chicago and was dressed in one of her favorite red skirt suits from Ann Taylor. She called it her “power suit.” She had on her go to 4 inch Nine West tan heels and and a sexy low cut white blouse. Emma was wearing tan nylons which I assumed were stockings but I couldn’t detect any hint of garter straps showing through her tight skirt.

Emma had a slim 5’7″ build and always had a way of not revealing what type of sexy lingerie she was wearing under her work or date night outfits. She said it made her feel sexy and gave her an extra degree of confidence knowing she was the only one who knew what alluring undergarments she was wearing.

I walked and immediately noticed Emma had a worried look in her eye. She gave me a stern look and said “So what’s up?”

I bluntly said “Emma I love you but I have to tell you something I’ve been keeping a secret. I’m a crossdresser, I love dressing up as a girl; and I also think I want to transition and become a woman.”

Emma started to laugh and said “Oh my God, did you stop at the bar on the way home? Good one funny man! So seriously what is on your mind?”

I repeated what I said and told her I no longer wanted to have children because I wanted to further explore my desires to crossdress and live as a woman.

Emma stood there, began to process what I said; and waited for me to start laughing as if this was a continued joke. After I looked away and started to tear up, Emma bursted into tears and said “How could you deceive me all these years Derek. Why? How? When?”

I told her I have been secretly wearing women’s clothes off and on for the past 5 years of our marriage, and prior in life after I graduated from college. I told her I purged after we moved in together and got married, but the urge and erotism of wearing women’s lingerie, panties, garter belts, stockings, skirts and dresses never went away.

I said ” I started to wear some of your loose and stretchy skirts and dresses as well as your panty and garter belt sets. I also wore your stockings too. It just felt so right. It’s who I am, I think”

She snapped back “I always wondered why some of my things started to loosen up and how you had such great taste in women’s clothing and stuff: [weeping] now I know why”.

Emma was right. I loved buying her new suits, dresses, skirts, sexy heels, lingerie, and hosiery for birthdays, holidays, and special occasions. My favorite stores to shop for her in person and on the Internet were Macy’s, Nordstroms, Ann Taylor, Nine West, Banana Republic, J Crew, Saks, The Limited, Gap, Wolford, Stockings HQ, DSW, Bare Necessities, Figleaves, Sephora, and of course Victoria’s Secret. I also love to find bargains in discount stores such as Marshalls, TJ Maxx, and Filene’s Basement.

Even though I was 3 inches taller and a few sizes larger, I was in heaven shopping for Emma in women’s stores. I was vicariously living through her, almost pretending I was shopping for myself.

I eventually ended up envying Emma more than anything and often fantasized what it would be like to be her in an corporate environment wearing sexy lingerie under sexy skirt suits or wearing cute outfits during her numerous “girls night out” excursions. Sometimes I would put on her lingerie when she was out and masturbate to incredible orgasms.

Continuing the dialogue with Emma I said “I’m so sorry, but my urge to fully dress as a woman isn’t something I can keep down anymore. I need to explore this further.”

I told her as the urge to dress more grew I purchased some of my own girly things, stockings, heels, etc. but I never had the chance to fully dress with full body hair removal, makeup, jewelry, and perfume. I said the feeling of just wearing some girly things was enough to send me over the edge as I would masturbate and have mind blowing orgasms. And unlike other crossdressers, the urge to stay dressed didn’t go away. I often stayed dressed and have multiple orgasms as I fantasized what it would be like to actually be a girl dressed in sexy lingerie pleasuring herself over and over.

I explained “When we anime porno started to try and have children I threw everything away to give our marriage one last shot, But I just can’t; I just can’t live this lie anymore.”

Emma still sobbing, “Derek how could you. How? Were the orgasms better than when we had sex?”

I replied. “I’m so sorry Emma, but it felt so natural, so right.”

Emma became a little angry and said “So you’re gay. Right Derek?”.

I said “No Emma I’m not gay and I’m not attracted to men… well at least not as Derek”.

Emma said in a loud voice “WHAT!”

I told her sometimes when I was dressed I often wondered what it would be like to be a woman and be intimate with a man.

“So you are gay!” Emma screamed.

I replied in my softest semi-feminine voice to add effect “No. In my fantasies I am a straight woman with a straight man.”

Fagot!” Emma screamed louder and added “what else have you done? Have you been with a boy? How many times? What’s your girly name?” As she continued to yell and mock me.

I told her no, I have not been with a boy, but in my feminine voice, “Well when I’m Jessica, and get dressed up, I have watched straight porn; and I emulate what the girl does in a scene with a guy.”

I also told her I have played with a realistic dildo, both orally and anally, and also watched videos on YouTube on how to walk in heels, practice feminine movements, and how to speaking in a female voice.

This was obviously too much as Emma stormed out of the kitchen, marched upstairs, and locked herself in our bedroom.

I decided to take a drive and give Emma a few hours to let this set in and decide where we go from here.

When I returned, her car was gone and I began to panic she packed her things and left me. When I walked in the kitchen there was a note on the counter.

The note read “Derek, I tried calling you but you didn’t answer. I am going to the park. I need to think. Maybe go read. I’ll be back in a few hours, I hope.”

I recalled I left my phone in our mudroom before I left. “Stupid me” I said in my head. I was worried she thought I was blowing her off.

I decided to open a bottle of Pinot Noir and try to relax a bit. And relax I did, I ended up dozing off on the couch.

I awoke to the garage door opening and Emma walking in carrying a few shopping bags. Emma had changed and was wearing a sweater, leggings, and riding boots. The leggings really showed off her athletic legs and cute butt.

Emma pulled out a few books from a Barnes and Noble bag and said “I found a few books on how women deal with being married to a crossdresser.”

Emma seemed calm which surprised me and put me at ease.

Emma continued “This book, Alice in Genderland, was pretty interesting and kind of sexually graphic. This guy in California lived with his wife who allowed him to have relationships with men, but only while en femme. They even have kids who lived with them. I have to ask you again, are you gay and do you want to have sex with men?”

I replied “I’m not gay. Geez! Quit saying that, but I like said; I feel sexually aroused and attracted to men while I’m dressed. I guess it’s something I want to further explore. I don’t think it will ever go away”

Surprisingly in a calm voice Emma said “Ok, that is fine. But you know I want kids so we’re getting a divorce. That’s going to happen eventually.”

I then began to cry. I muttered “I’m scared Emma, did I make a mistake telling you? My life is going to completely change now isn’t it?”

“Derek, err I mean Jessica, Look I read these books, and as you know I’m pretty socially liberal and open minded, so I want to help you through this.” Emma said in an attempt to calm me.

I replied “how” as I continued to cry in a soft, feminine manner.

Emma said the books highly recommend I see a gender therapist to see if I truly want to transition into a woman. Emma stressed she wants to help me and said “I’m worried you won’t be able to go through with this alone and afraid you will back out without a friend.”

Emma saying “friend” brought me to reality that our marriage was going to be over. I looked down, I was depressed and afraid.

Emma could tell I was depressed and said “when I say friend, I mean girlfriends. And what do girlfriends do when they are sad?”

“What?” I said in an inquisitive manner.

“They give each other makeovers silly.” Emma blurted out.

Emma pulled out a few bags from TJ Maxx and Target which contained some cosmetics, girly products, lingerie, a dress, and heels.

Emma said enthusiastically “Let’s head upstairs and get started, this will be kind of fun.”

I knew Emma was serious. In college she worked part time as a makeup specialist at Macy’s so I knew I was in good hands.

As Emma and I headed upstairs my mind began racing. I can’t believe I’m going through with this. I felt so guilty, but at the anne porno same time felt so excited. I could hardly contain my excitement and Emma noticed.

Emma blurted out “Umm you need to take of that boner before we get started. Even though It’s kind of small, I can’t have that thing poking at me when I’m turning you into Jessica.”

We walked into our master bathroom carrying the Target bags containing the products Emma bought.

Emma handed me a bottle of Nair for Men and said “Use this to remove all of your body hair. Go into the shower and just lather everywhere you have hair and wait a few minutes. After, rinse off with a wet wash cloth. And here’s some of my lube, take care of that boner.”

I was hard as a rock. I wish Emma could’ve just gave me one of her epic blowjobs. But I guess she was moving on already as far as sex goes.

I stepped into the shower and got all wet. I took gobs of the Nair product and lathered my arms, chest, legs, and everywhere else I could reach. The stuff tingled my skin and I could feel it working into my follicles.

As I waited I read the product’s instructions more carefully. It read “Don’t use on armpits or other sensitive areas.”

“What about my armpits and other sensitive areas Emma? The bottle says not to use on sensitive areas.” I yelled out from the shower.

“Don’t use my razor silly girl. Here I got you your own. You’ll need it for your armpits, around your nipples, your pubic area, and around your asshole” Emma jokingly said.

Emma threw the package over the shower door. It was a “Gillette Venus” razor for women. It was pink and sort of similar to my razors, but was designed to be used on legs and armpits.

After few minutes I started rinsing myself with a washcloth and the shower sprayer. I was amazed how quickly the hairs on my arms, chest, and legs washed completely away leaving my body almost completely hairless. I used my new girly razor along with some of Emma’s scented shaving cream on my underarm, nipple areas, and crotch. I trimmed my pubic area into a girly triangle and also around my asshole as much as I could. Last, I used the razor to touch up all the areas where the Nair stuff missed.

“Don’t forget about your face Jess. Here’s some shaving butter. Use it after you use your regular shaving stuff.” Emma said as she threw another package over the door.

First I lathered my face with my regular men’s shaving cream and used my men’s razor. Next I coated my beard areas with the shaving butter. “Shemoisture Coconut & Hibiscus Shave Butter Creme” the package read. It felt wonderful on my face and I loved the scent. I decided to use to my Venus razor for the closest shave as possible. The butter seemed to do it’s thing as my new razor removed all the stubbles and hint of a beard from my face.

“Hey Jess I’m going downstairs to get a few things. Should give you enough time to take care of that boner you still got” Emma said with a chuckle.

I looked down and I was still rock hard. I started to feel more aroused as I felt my smooth skin and trimmed pubic area. I took my bath mirror down from the showerhead and began to admire my new girly smooth body. I loved it.

Feeling extremely horny I coated my cock with Emma’s lube. I was slightly below average in length I guess, but it never prevented me from pleasing my sexual partners in the past.

I slowly began to stroke my dick after I squirted lube onto the tip of my head and shaft. The lube felt so good as it allowed my right hand to easily glide over my head and stroke my shaft up and down. I began to pick up the pace and stroked my dick harder and harder. I squirted some lube on my left hand and fingertips. I felt the need to masturbate like a girl and finger my asshole. I pretended my dick was just a large clitoris. I let my left middle finger explore and enter my anus. The dual stimulation of jerking off and fingering myself was electric. I sent my body into mini shivers just thinking about my smooth body and face as a guy ate me out.. I imagined myself as a girl taking a shower with her hot boyfriend. Exploring each others bodies as we kissed passionately. Feeling his strong hands trace down my breasts, my nipples, and eventually to my pussy. He gently places me on the shower bench and begins to insert one, two fingers into my pussy as his tongue works up and down my clitoris. This is how I imagined being intimate with a guy in the shower. Romantic and sexy as hell.

I was now starting to moan in the feminine way I had practiced in the past. I sat on the shower bench as I jerked my clitty cock while still imagining my shower fantasy. My left hand left my anus area and started to massage my smallish man boobs. I whispered “Oh Austin, oh that feels so good. Oh baby, don’t stop. Don’t stop.”

In my fantasies I always imagined my male lover was a hot guy named Austin. I just think it’s a sexy name for a guy. I always envisioned him to be tall, athletic, handsome, with a nice arap porno package.

With every stroke of my dick and rubbing of my nipples. I continued the shower fantasy in my head and imagined Austin feverishly working up and down on my clitty. I felt my precum start to ooze out. My body convulsed as I whispered louder “Oh, oh, I’m going to cum Austin. Please don’t stop. Oh my god.”

I wanted to cum so bad. My body slid down the bench, only my shoulders and legs supported my body as I arched my back. The incredible convulsions peaked and an orgamsic rush took over my entire body. My whispering ended with me shouting “Oh my fucking God. Oh fuck. Oh my. Oh Austin! Oh my God. [Intense cumming] Oh. oh!”

It seemed like the orgasm took a full minute. I cummed all over my stomach chest, It was more powerful than anything I have ever experienced. My orgasms as a guy were always good, but this almost blinded me. Was this how orgasms were supposed? I hoped so. I wanted more than ever to be a woman.

As I cleaned up my mess in the shower I heard Emma lighting something.

Emma shyly giggled “So who’s Austin?”

“Oh geeze” I replied. I guess Emma heard me well enough in the shower. “Just a fantasy I have Emma.” I said embarrassingly.

Emma continued to giggle and said “Well that sounded pretty hot. I hope you find him someday.”

“Ha ha, very funny.” I said as I stepped out of the shower.

I was shivering. Maybe it was being hairless. Maybe it was feeling feminine. Nevertheless I welcomed the vulnerability. I was glad to see Emma had prepared the spa tub.

“Time for you to get pampered Jessica. Hope in here girl. We have a lot of work to get you pretty.” Emma enthusiastically said.

I stepped into the tub which was surrounded by beautiful candles, a glass of red wine, and several women’s magazines.

Emma said “Sit back, relax, sip some wine, and read some mags. Oh you have to read the articles in Elle on how to look and feel feminine and sexy. These are things you are going to need to know Jess.”

I used Emma’s Bath and Body Works cooling lilac and mint body soap. Emma had bought me my own pink body scrubber. I squirted some of the body soap into it and gently lathered, scrubbed, and rinsed my smooth body. I loved how it left my legs shimmery and clean.

It was a heavenly feeling taking a girly bath with jetted bubbles, flowery scents, candles, and a few sips of red wine. I began to feel more comfortable and feminine. I opened Glamour and read several pages on makeup tips, new hairstyles, leg and glute workouts, and how to flirt with guys at the grocery store.

As I reached for another sip of wine Emma came from behind me and began applying a mud mask to my face. She also placed a light amount of wax around my eyebrows.

Emma said “Time for a facial and we need to thin those brows a bit. But don’t worry I won’t get too carried away Jess, I promise.” We both giggled, gave me a mischievous look, and applied the mask and wax.

As the mask dried I read articles in Elle on how to be sexy and confident in all aspects of life. I loved reading about the tips and little things a woman can do to smell lovely and look sexy and confident at work and in her private life. Elle also had some tips on being intimate with your man and the little things you can do during a blowjob to send him over the moon.

I really liked the section on where they asked guys what they liked about a woman’s sex appeal and confidence. Each response featured a photo, first name, location, and career. One really attractive guy named Brendan was from Philadelphia and a finance officer. He said he loves a woman’s eyes and the way a woman carry themselves out in the public. He said “Confidence carries, buy eyes kill.” After that he said {laughing} he checks out her ass and legs, “oh and you have to love a girl with nice stems and cute tush”.

Emma was nearby and I pointed to Brendan and said “Wish we lived in Philly” as we both giggled loudly.

Emma added “Oh he is a looker, meow”.

Emma removed the mask from my face and wax from my brows. I won’t lie, the wax hurt but luckily Emma had some ice cubes on hand which she used to cool the waxed areas. But my face felt solt and feminine.

Emma joked “Next we can wax your new girly and backside areas”.

I knew she wasn’t kidding but told her I wasn’t ready for that tonight as I felt I was did a good job clearing those areas with the Nair product earlier and my new razor.

Emma grabbed her lilac shampoo and conditioner and said “Let’s see what I can do with your hair. It’s shaggy enough I think I can style it into a cute wavy updo and attach some matching brown extensions to give it more volume.”

Emma shampooed my hair, rinsed, and rubbed conditioner into my scalp. I could feel the conditioner working. It made my hair feel fuller.

I knew at that time she was actually enjoying this. I was now just her girlfriend Jessica.

Emma said “See. This is fun. This is what girlfriends do for each other.” as she giggled.

“I love being pampered Emma,” I said as I relaxed in the tub. “Now I know why you love going to the spa to get your hair or nails done. It’s so relaxing and makes me feel so feminine.”

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