I was sound asleep and dreaming of being in a six-nine position with a man when I was awakened by my alarm.  Rolling over, I put the alarm on snooze and laid on my back for a few minutes thinking about my dream.  As I replayed it in my mind, I remember that I had a vagina, rather than a cock.  However, my hard and throbbing cock let me know it was only a dream.  My panties were hard in the front with the dried cum from last night.  There was a slight stickiness between my ass cheeks from the residual lubrication.  I felt relaxed and satisfied as I thought of my experience with Gregg. 

The alarm sounded again as the snooze time expired.  I rolled out of bed and walked to the bathroom.  Pulling down my panties, I sat on the toilet and peed which was becoming natural for me now.  Then, I stood and pulled my panties up stepping in front of the full-size mirror on the bathroom wall.  My red panties and bra were quite visible through my white nightshirt maintaining my feminine look and feel.  I turned on the shower to let the water warm as I stripped down.  My womanhood disappeared with my clothes.  I hated being naked. 

I stepped into the shower wishing I was really a woman.  My short hair, flat chest, and hanging cock made that wish seem impossible.  My bright pink toenails and fingernails were the only feminine trace remaining.  I was so glad that Gregg painted them for me earlier in the week.  Knowing I would be shopping with Tiffany tonight also brought a smile to my face.  I washed my hair with shampoo and conditioner using body wash on my skin.  As I stepped out of the shower, I dried off with a large oversized towel before wrapping it around my body.

Walking into the bedroom, I was thankful that I washed my women’s clothes last night.  It would have been a huge disappointment if I had to put on men’s clothes today.  I opened my drawers and picked out a pair of bikini panties, a full coverage bra, a pull-over blouse, and tight jeans.  Dressing, along with my breast forms, restored much of my feminine feeling.  Brushing my hair, I decided to experiment a little with it.  Not all women have long hair I thought to myself.  Sure enough, I could brush some bangs across the front.  While not the most feminine style, I felt like it was close to passable, at least enough for around the apartment. 

After eating a quick breakfast, I sat down at my computer and logged on to the company site to start my workday.  I also logged onto the department store site so I could look at their clothing when my work was slow to get some ideas for shopping tonight.  Unfortunately, being Thursday, my work activity only left a few minutes here and there.  I stayed on the sight after logging out of work and had twenty uninterrupted minutes to look before getting ready for dinner.

I could hardly eat thinking about going shopping for clothes with Tiffany.  I couldn’t believe how much I was starting to think like a woman.  Since I was going out in public, I put on my wig and did a thorough job of applying my make-up.  This was going to be tricky.  I had to and wanted to be dressed to shop, yet I knew I was going to have to use my credit card for the amount I was planning on spending.   They surely wouldn’t risk losing a large sale because of a little gender confusion with the name on the credit card, would they?  Besides, I didn’t have any problem at the food store.  I almost panicked when I couldn’t find my credit card at first.  Then, I realized it was still in my pocketbook.

After stopping for a minute to think straight, I headed out the door to the car.  I wanted to be at Tiffany’s by 7:00 like I told her I would.  When I arrived she greeted me with her contagious and reassuring smile along with a tight hug and passionate kiss.  We got back into my car and I drove us to the store.  On the way, I filled her in on my activities during the week with Gregg. 

She responded, “Way to go, Kat.  I’m so proud of you girlfriend.”

I took her hand in mine as I said, “Thank you so much for being my BFF.  You have been such an inspiration in the short time I’ve known you.  I can’t believe how much I’ve changed.  I really know what I want and I’m not ashamed of it.”  I squeezed her hand tighter prompting her to lean over and kiss me on the cheek.

She chuckled, “Better keep your eyes on the road.”

Although I noticed the parking lot was quite full as we pulled in, it didn’t bother me as it might have in the past.  I was becoming very comfortable in public.  However, I still studied Tiffany’s walk heeding her original advice.  Walking definitely makes the woman.

In another departure from the past, we walked directly to the outerwear.  It would be the basis of the remaining purchases.  It was so exciting looking at blouses, jeans, skirts, and dresses.  We had to restrict our selection to the six-item limit, for each, allowed in the dressing room at a time.   Of course, we went into the same dressing room together.  The attendant didn’t object. 

I was so glad I didn’t try buying clothes online.  The fit, feel, and look must be experienced to make a good purchase.  We kept eight of the twelve items I tried on.  The attendant not only complimented me on our purchases, she made a few suggestions after looking at my likes and dislikes.  She actually walked us to a few racks to pick out some things.  I tried on and kept all of her suggestions.  Women are so much different than men.

Next, we looked at shoes to go with the clothes we selected, including pantyhose and thigh highs.  Then, we picked out two bras and a half dozen panties.  Tif commented, “You remember doing this before?”

I replied, “Of course I do.  It changed my life forever.”

We finished my shopping spree in the cosmetics department.  When we got to the register I couldn’t believe I spent almost six hundred dollars and three hours on clothes.  I scribbled my signature on the paper.  The cashier never looked at it.

On the way back to Tiffany’s I commented, “That was more than I spent for clothes, as a man, in the last two years.”

Tif answered, “I wouldn’t know.  I don’t think I ever bought men’s clothes.  Are you bragging or complaining?”

I questioned her, “How could that be?  You must have bought men’s clothes before you started cross-dressing.”

“My mother bought my clothes when I was in high school.  I started closet dressing in my junior year with clothing I procured from neighborhood clotheslines.  It became clear to me early that I wanted to live as a woman.  My father already thought there was something wrong with me because I didn’t have a girlfriend.  He would never understand, so I spent my senior year in high school getting accepted to a college where I could get away from home.  I went to college dressed as a girl on my first day.”

“Wow,” I stated.  “You were really committed to this.  I can’t imagine doing that by myself.  Have you thought about going all the way?”

Tiffany suggested we continue the conversation over a drink at her apartment since we were almost there.  Although it was getting late and I had to work in the morning, I couldn’t wait to talk about this.  After arriving at her apartment, I went in with her and sat on the sofa as she poured us both a scotch.  She handed me my drink and sat on the other end with a serious look. 

“I assume ‘all the way’ means having my cock removed?”

After hesitating a moment to think about it, I said, “Yes it does.  I’m confused that there are so many cross-dressers, many who have had breast augmentation, that do not complete the transition.  I also don’t understand the large amount of them that are so well endowed.”

“Why does that confuse you, Kat?”

I answered, “I think of a cross-dresser or T-gurl as a man that feels inadequate or, in my case, a man that would rather be a woman.  Either way, I would think that having a cock stands in the way.  Don’t you think?”

“I don’t think either of us know how many men fully transition since we would not recognize them if they stood in front of us completely naked.  I think many T-gurls want the best of both worlds.  Me, I’m worried I wouldn’t be able to have an orgasm after the removal.  I don’t think I’m alone on that.”

Tif continued, “I have thought about it many times.  It’s scary.  I guess when it comes down to it, I know what I got right now and I’m comfortable with it.  What do you think?”

I took a long sip of my drink.  “I’m not sure what to think.  I had a dream before I woke up this morning that I had a pussy.  It felt so good to be free of a cock between my legs.  Ironically, I woke up with a hard-on.  Talk about confusion.”

“Kat, we’ll just have to continue this journey together and see where it brings us.  I hope it’s not causing you too much stress.  It is so comforting to me to have you as my BFF.”

I slid over on the couch, sitting tight against her, I put my arm around her neck.  “That goes both ways sister.  You’re the wind beneath my skirt.   We are lucky to have each other.”  I kissed her on the lips.  “I couldn’t have done this without you.”

She responded back with a kiss before asking, “Do we have plans for the weekend Sweetie?  Maybe we can go to that bar, again.  I don’t think you’ll be as nervous as the first time”

“You’re right about that.  How about Saturday night?  I have a lot to do tomorrow.  I’ll come over around noon on Saturday.”  I couldn’t believe I put Tiffany off for a night, but I wanted to work on my hair.  I didn’t feel natural wearing a wig so often and I was encouraged with the results this morning.  I finished my drink and gave Tif a reassuring hug before going home.

A few minutes after getting home and carrying my bags in, there was a quiet knock on the door.  It was Gregg.  I opened the door and let him in.

“I hope you don’t mind me knocking so late, but I know you work during the day and you’re usually away on the weekend.  I heard you walking up the steps so I thought I’d take a chance catching you before you went to bed.”

“That’s okay Gregg.  Is everything alright?” 

“Yeah.  I just wanted to thank you for last night and give you something.  I hope you don’t think I’m some kind of creepy weirdo, but you’ve been such a friend when I needed somebody.  I’ve been so screwed up since my divorce and you’re helping me out of it.”  He handed me a small box.

I removed the lid.  It was a beautiful necklace and earrings. 

“Gregg, these look expensive.  You shouldn’t have bought these for me.”

“Let me explain, Kat.  I purchased these for my ex-wife a few days before she told me she wanted a divorce.  I never gave them to her.  I’m thinking I probably kept them, at first, because I thought she might change her mind.  As time went by, I realized it was over, so they sat in a box with other memories of her.  I can’t think of anyone I would rather see wear them than you.  Please, take them, no strings attached.  They will look so good on you and I can move forward as a man while you move forward as a beautiful woman.”

It took me a few minutes to get over the initial surprise and think about it.  Finally, I responded, “Okay, Gregg, bring them back tomorrow night, have dinner with me, and put them on me yourself.  Then, I will accept them.” 

I gave him a big hug and he kissed me on my lips as I said, “Good night, Sweetie.”

After closing the door, I leaned back against it, suddenly having a vision of a movie somewhere in my past where the young innocent girl sighs after her first kiss from a man.  Then, I thought, now I have even more to do before Saturday with Tiffany, and I better not tell her about tomorrow night.  She’ll probably be mad or hurt even though I wasn’t expecting this.   

I took everything I bought at the store and started putting it away.  As I began to run out of space I thought about what Gregg said about moving forward as a woman.  Each bag I emptied of my women’s wear, I filled back up with my men’s wear.  Then, I took off my blouse and jeans replacing them with a sheer baby doll negligee over my bra and panties before taking a pee and going to bed.

The alarm woke me up in the morning since I set it early.  Today was going to be a busy day.  Friday’s are always a heavy order day for work.  I wanted to work on my hair this morning and now I had to make dinner for Gregg.  Before taking a shower, I went on the internet and looked at women’s hairstyles so I could try one when I dried my hair.  While I was looking, I saw I received an email notifying me that the breast forms I ordered last week would be delivered today, perfect timing for tonight.  I picked out a short hairstyle that didn’t appear to need any special accessories since I didn’t have anything except a blow dryer and a round hairbrush.

After showering, I styled my hair with the blow dryer and brush.  I used a pair of scissors to cautiously trim the front along my forehead and then down each side a little.  For my first time, with only some pictures downloaded from my computer, I thought it looked pretty good.  I probably looked a little more like a tomboy than a diva, but with a slightly mischievous look.  With a towel still wrapped around me, I went into the bedroom and picked out some clothes.  I put on a thong, padded bra, loose shorts, and a short sleeve V-necked pullover blouse.  The outfit was both comfortable and sexy.

My day was moving along quickly, as Fridays usually do.  Around one o'clock, the doorbell rang so I opened my door and went downstairs to the inside foyer.  The mailman left a package on the floor under the mailboxes.  I took it upstairs and opened it right away.  It was the breast forms.  Although I couldn’t wait to try them on, I had to wait until it was time to log off my work site.  The next few hours dragged a little with the anticipation.

By the time I logged off I was like a little kid on Christmas.  I opened the three packages.  There was a small pamphlet with the adhesive, which I started to read when I realized I was running out of time.  I decided to order dinner from the Italian restaurant down the street and have it delivered.  This would give me some extra time to try out the new breast forms.

 After finishing with the instructions, I went into my bedroom and took off my blouse and bra.  Next, I went in the bathroom and cleaned my chest with alcohol, before spraying the adhesive on the back of the asymmetrical breast forms.   Then, I put my bra back on pulling the cups down with the straps halfway on my arms.  It took me a few minutes to make sure I had the forms in the proper orientation to place them on correctly.  I carefully set the left one in place.  I could see it wasn’t going to stay in place very long so I quickly set the right one in place and pulled my bra straps up on my shoulders. 

I adjusted them slightly inside my bra using both hands.  They looked really good on me.  The padded bra not only held them in place, but it also pushed them out a little.  The instructions indicated that it would take fifteen or twenty minutes for the adhesive to take full effect.  I didn’t want to take a chance with them shifting so I laid on my back in my bed.  As I lay there the forms warmed to my body temperature and seemed to soften slightly causing them to flatten a little like the real thing.

The feeling was absolutely exquisite as I sat up.  They sagged ever so little against the bottom of the bra cups.  I could feel the support on them from my bra imagining what a real woman must feel.  Choosing the size when I ordered them was somewhat of a dilemma.  My initial thought was a larger size, but the description stated it was possible to go braless or use a more open cup with a smaller size.  The extra diligence was worth the effort.  My breasts were well proportioned to my body.  Now, the moment of truth.  I reached behind me and unclasped the bra, letting it slide down my arms onto the bed.  The breast forms were still firmly attached, yet sagging a little, just as real breasts.  I could feel the weight of them by pulling down on my chest. 

Following one of the suggestions in the instructions, I applied some light make-up powder around the edge of the forms to blend with my real skin.  I knew at that moment that I would have to look into breast enhancement.  This was another game-changer.  Suddenly, the doorbell rang.  I thought, “Oh shit!  It must be the delivery man.  Gregg would have knocked on my door.”

I quickly put my bra and blouse back on.  Still, in my bare feet, I grabbed my purse from the kitchen table, and headed down the stairs yelling, “Here I come, Sweetie.” 

There was a young man standing in the foyer holding a bag.  As he saw me he smiled and said, “Delivery for Shawn.  It’s forty-one ninety-nine.”

I fished out fifty dollars from my purse and gave it to him, “Keep the change, Dear.”

He handed me the bag, “Thank you.”

I went back upstairs, turned on the oven to ‘warm’, and placed the aluminum foil pans in it.  Then, I hurried into my bedroom and began to change.  I took off my shorts and blouse before carefully removing my bra.  I put on a three quarter cup light push-up bra that I bought with Tiffany the night before in anticipation of using my new breast forms.  I couldn’t have made a better choice.   I changed my thong to a black lacy high cut panty and put on black thigh highs, followed by a one-piece short black dress, also purchased last night.  I wanted a sexy outfit and this hit the mark. 

Knowing I was running out of time, I quickly did my face and touched up my new hairstyle before looking into the mirror.  Although I didn’t expect to be leaving the apartment, I wanted to complete my ensemble with the new high heels I bought last night, just for this dress.  This was a good chance to spend a little time on heels since I could take them off anytime I wanted.  Suddenly, I understood why so many cross-dressers wore heels, in spite of it making some of them look ridiculous.  My entire posture was affected by them. They forced me to stand straight with my chest out.  My stocking-covered pink toenails were slightly visible through the open front of the shoe.  I was never more satisfied with my look.  But more than that, I never felt more like a woman.

I walked to the kitchen carefully moving like so many women I studied.  Each step was deliberate while still maintaining the hip sway I was developing.  The feel of the dress rubbing my panty-clad ass was sending a shiver through my body.  I practiced bending and moving around the kitchen as I got ready for dinner when I heard Gregg knock lightly on the door as he announced himself, “It’s me, Kat.”

As he entered the kitchen, he stopped and stood still, gazing at me. “Kat, do you know how amazing you are?” Setting the box in his hand on the table, he walked a few more steps toward me, gave me a big hug and a kiss on the lips like never before.  He took my hands in his and backed up a step, looking up and down me once, then stared directly into my eyes as he declared, “There is not a more beautiful woman in the world than you.”

It was probably the first time in my life that I blushed.  I could see and feel his desire for me, yet I felt like I had this power over him.  This was far more than I ever expected from cross-dressing.  With my hands still in his, I pulled them behind me prompting him to hold me tight around my waist.  Then, I wrapped my arms around his neck and slowly began to French kiss him until my tongue couldn’t get any further into his mouth.  My new store brought breasts that felt so real against his chest.  There was a slight coolness in the opening under my dress in contrast to the heat of his body against mine.  It was almost intoxicating.

Finally, he broke our embrace and reached for the box on the table.  “Kat, you must let me put these on you.”

He removed the gold studs that were in my ears since they were pierced last week and put in the earrings from the box.  Then, he draped the necklace in front of me as he pulled it from behind closing the clasp.  I took his hand and walked to the mirror in my bedroom.  He held me from behind while I looked at myself in the mirror.  My appreciation for jewelry instantly increased.  The ruby and small diamonds sparkled on me.  After admiring it for a minute or two, I playfully pushed my butt into his crotch.  He tightened his arms around me as I could see him smiling in the mirror.

I broke the mood for a minute.  “We better eat dinner.  It’s going to get cold.”

Gregg walked a few steps behind me.  I realized that it was so he could watch my ass as I was learning how to display it so well.  He opened the wine as I dished out some food from the pans on the counter.  The dinner and wine were a good idea.  I felt so relaxed.  After eating, we continued to drink the wine until it the bottle was empty.   After taking the last sip, we looked into each other’s eyes.  There was no need to talk.  We both knew what we were going to do next.  I stood up and took his hand, as we walked to the bedroom.

Standing face to face, I reached down and unbuckled his belt, pulled down his fly, and undid his button.  I lifted each of my feet pulling off my heels and tossing them aside.  Then, I slowly dropped to my knees pulling his pants down to the floor.  His cock was pushing his boxer shorts out.  I pulled them down, freeing it, as I wrapped both my hands around his shaft.  My pink nails, erotically moving up and down, was probably making both of us hot.  I used my fingertips to lightly rub along his bulging vein, tip, and under his balls.  He responded with a series of quiet groans.

When he started to ooze some precum from his little slit, I gave it a playful lick.  I continued my slow methodical message to produce more precum as I began to spread it around his shaft with my tongue. I wanted a slippery coating to lubricate my throat so I could take all of him when I was ready. 

I knew he was ready and probably dying for it when he put both of his hands on my head.  However, I wasn’t quite ready and wanted to assert my control that I was beginning to understand.  His grip and groans were beginning to show his anxiousness.  He gave a big sigh when I finally took him into my mouth.  I moved up and down his shaft holding my tongue against his vein stopping short of entering my throat.  When his cock was well coated, I took a breath and forced him down my throat.  I could feel his grip tighten on my head as he let out a loud groan.

After keeping it in my throat a few seconds, I pulled up until just the tip was in my mouth.  I wanted to get him hot and hard, but I didn’t want him to cum.  I moved my head down pushing him back into my throat, again, this time a little longer than the first.  Each time I went down on him, I held him in a little longer as my throat adjusted to the intrusion and his precum lubricated his cock. 

I didn’t want to push my luck too far and I was getting wet myself so I pulled him out of my mouth, stood up, and said, “Get on your back up on the bed lover,” as I pulled my dress up over my head, tossing it on the floor.  I reached in my dresser drawer and grabbed a condom.  I ripped open the wrapper, took out the condom, and rolled it down his cock as quickly as I could before climbing up on the bed straddling him.

I pulled down the back of my panties and lowered myself down lining up his cock with my rosebud.  Without the usual poking to let my sphincter adjust, I just sat down on him driving his cock deep into my ass.  Although I felt a twinge of pain from the aggressive entry, I had to have him in me.  It was a good thing it was a lubricated condom.  The pain disappeared almost immediately as the sudden fulfillment took over.  I used my hips to move back and forth sliding his cock around inside me.  I was afraid I was going to climax before him, but I was losing control as I could feel it building up. 

Gregg now had his hands on my hips and I had mine on his shoulders as we gazed into each other’s eyes, while fucking our brains out.  My breast forms were bouncing slightly adding to my ecstasy.  I could see myself in the wall mirror.  It was beautiful and erotic as we began to reach that wonderful moment.  I could feel my wetness as my precum started oozing out against my panties. 

Gregg began bucking hard as he started gasping and then into a long “Ahhh!”  I could feel his cock pulsing inside me triggering my colon to spasm.  I was having an anal orgasm, which in turn, sent him further over the edge.  He gripped my waist tightly and pushed his crotch upward babbling incoherently.  We were feeding each other’s orgasm.  My panties were soaked in front, my heart was pounding, and we both sounded like we just ran a marathon. 

As I started to calm a little, he pulled me down tight against him kissing me hard on my lips.  I could feel my shriveled little wet cock against his abdomen.  I whispered in his ear, “I’m sorry Sweetie, I’m making a mess on you.”

He replied, “That’s alright Kat.  You feel so hot.”

After a few minutes, I lifted my body up letting his softening cock gently slide out of me.  It’s so much better pulling it out when it’s soft since it doesn’t leave a sudden emptiness.  However, it does often result in the condom staying in me and this was no exception.  As I climbed off Greg and onto the floor, my panties moved back up my cheeks.  I leaned over him and licked his condom less cum covered cock clean.  Now there’s another good reason for pulling it out soft.

When I finished licking his cock, I licked my own cum off the front of him.  I couldn’t believe how much of a mess I made on him.  It was quite unladylike and I was so afraid it might turn him off in the future.   He sat up on the bed, pulled me down to him, and kissed me, again, on my lips.  “I think you’re the most wonderful woman in the world.  I’m so glad you accepted my gift.”

It was a relief and a thrill to hear him say that.  He brought out the woman inside me.  Standing there in my bra, panties, and thigh highs, I debated whether I should put something over myself or just stay like I was.  Although I was quite comfortable with so little on, my feminine instincts took over.  I went to my closet and put on a silky robe tying it with the little lacy string attached to it. 

I went into the bathroom and pushed my panties down to my knees before reaching behind me and pulling the condom out of my ass, discarding it in the toilet.  Then, I sat and peed.  My crotch was covered with cum.  I pushed my panties down to the floor and stepped out of them when I stood up.  I took a washcloth, wet it, and wiped myself clean.  My robe was just long enough to cover my ass and genitals so I picked up my wet panties off the floor and went back into the bedroom.  Gregg had already put his pants back on and was slipping into his shoes while I took a clean pair of bikini-cut panties from my drawer and put them on. 

We walked into the living room together.  He turned me toward him before hugging me tightly and, once again, kissing me passionately.  My mouth still had the strong taste of his cum.  I sensed this was his way of assuring me it was okay.  When we finished kissing like teenagers, he whispered in my ear, “Good night, Kat.  Maybe we can have dinner, again, next week.”

I responded with a big smile as I opened the front door, “As long as we have dessert afterward.”  He gave me a final kiss as he left. 

I took off my necklace and earrings, putting them back in the box, so I didn’t damage them sleeping.  Then I cleaned up the kitchen, thinking to myself, this must be more of the woman coming out of me.  In the past, I would have left it for later.  When I was done, I took off my robe and thigh highs and went to bed in just my bra and panties, along with my breast forms.  They felt so much a part of me that I had to leave them on. 

I couldn’t wait to see my BFF tomorrow.  It was sure to be another orgasmic adventure.