It was after two o’clock in the morning by the time we got back to Tiffany’s apartment.   Both of us were not wearing panties under our skirts and I was tingling from the cool night air on my well reamed ass.  Tiffany suggested we slip into some comfortable lingerie to sleep in.  She picked out a long sheer night gown for me.  I stripped down completely before pulling the gown over my head.  After peeing, I climbed in bed next to Tif, spooning her, as we both fell fast asleep.

It was late in the morning when we finally woke up as Tiffany asked, “How do you feel this morning, Sweetie?”

I responded, “Wonderful.  Last night was unbelievable.  I really felt like a woman.”

“Good.  Are you ready to move up another step?”

I couldn’t imagine what else there could possibly be as I cautiously asked, “What’s next?”

“You forgot what you promised me yesterday?  You said we could talk about getting your ears pierced.  Remember?  It’s not a huge step.  Even men get their ears pierced today.”

She was right.  It wasn’t a big thing and after last night I knew I wanted to move forward with my transformation.  I smiled as I told her, “Okay, Sweetie, anything for my BFF.  I can’t believe how far I’ve come in less than a week.”

“Let’s take a bath together and get cleaned up.”

She took my hand and led me into the bathroom.  She sat on the toilet and peed first, then I sat and peed as she started the bath water, adding some bubble bath.  We both took off our gowns and she sat in the tub first.  I got in on the other end facing her with my legs over top of hers.  She tossed me one of those sponge like things.  I dipped it into the water, then started rubbing my face and upper body.  As Tiffany worked her way down her body she switched to my legs and moved up them to my cock.  Putting one hand around my cock and the other hand around my balls she lifted my hips slightly pulling me into her lap.  I had to lean back on my hands to keep my head from falling under the water.

I could feel her cock begin to harden between my cheeks while at the same time my cock was hardening in her hand.  I pulled back a little until the tip of her dick was against my rosebud.  Then, I used my hands behind me to push my body forward forcing her cock into my ass.  She used her hands on my cock and balls to pull herself into me, also.  My feet were on both sides of her under her shoulders while my knees bent upward as I slid forward driving her cock deep into my ass.  I could feel the precum oozing from my dick as I savored the fullness inside me.

Our eyes locked as I began to let out a quiet moan and a smile ran across my face.  I wanted to sit up on her, but I was immobilized by her hold on my cock.  She started fucking me by pulling me back and forth by my dick while bucking her hips up a little.  I so wanted it to last, however, I felt like I was going to explode at any minute.  My only consolation was she looked like she was going to orgasm herself.

She declared, “Ohhhh Kat, I’m going to cum in your ass.  Is that okay?”

I answered with several pushes forward, “Oh yes Tif, cum inside me, shoot your load in me before I blow mine.”

She squeezed my cock tight and pulled hard as I could feel her cock pumping inside me.  Within seconds my dick erupted sending my cum straight up in the air two or three feet, then landing on my face, neck, and chest.  It was the furthest I’ve ever shot my load.  It was unbelievably hot everywhere it landed. I could taste some of it on my lips.  Only Tiffany can make me cum like this.  We both froze for a few minutes as our orgasms subsided. 

I pushed my body up into a sitting position in her lap.  She reached out her arms and pulled me into a hug and kissed my lips with hers.  Then she began to lick my lips and chin as she said, “I can taste your cum, Sweetie.  That was so quick and intense.  I hope you don’t mind that I came inside you.  I never expected to cum so quickly.”

“Of course not.  You’re my BFF.  I trust you.  Besides, I really wanted to get creamed in my ass eventually.  I guess we’re going to need to get cleaned up.”  We both laughed.

I put my hands on the side of the tub and lifted myself up as Tiffany’s cock pulled out of me.  I stood up in the tub.  I could feel a little of Tif’s cum between my cheeks.  She leaned forward and licked the remaining cum from my cock.  Then, I stepped out of the tub and sat on the toilet.  I could feel her cum run from my ass as I pushed it out like I was going to shit.  I wiped with some toilet paper before suggesting we use the shower this time to clean up.

Tiffany drained the tub, closed the curtains, and started the shower.  I stepped into the shower with her.  We washed each other with some fragrant body wash.  She wrapped her arms around me from behind as she said, “You have such a beautiful body, Sweetie.  You’re going to make such an amazing woman.  I hope you let your hair grow in right away.”

She spent the next few hours planning and convincing me the things I should do for my transformation as we dressed, ate, and drove to the mall.  I thought about my situation.  I lived alone, worked from home, my father left when I was only five years old, I haven’t spoken with my mother in a few years, and I now lived hundreds of miles from where I grew up.  There was only a handful of people that would ever know I transitioned and probably none that cared anyway.  Why would I hesitate?  The world has changed in the last few years.  It seems everything is acceptable.  I knew this is what I wanted and Tiffany had opened the door for me.  It was time for me to walk through it.

By the time we arrived at the mall, I was ready to continue my journey.  We went to a jewelry store where I got my ears pierced and bought some earrings, two bracelets, two necklaces, and an ankle bracelet.  It was so much fun shopping.  While the mall was more expensive, the selection was so much greater.  I bought a pair of friend’s bracelets with half a heart for Tiffany and myself at another store.  We bought some strappy high heels, spring dresses, and a few more bras.  However, I said no to the nail salon since it would require me to go en femme before my natural hair was long enough and I didn’t want to have to wear a wig all the time. 

After a lengthy discussion with Tiffany, I agreed to “come out” on my birthday in six months.  It seemed appropriate and I couldn’t think of anything I wanted more than to make the transition.  My hair would be long enough by then that I could have it styled.  It would also give me time to refine my walk, work on my voice, and continue to learn to be a woman.   Until then, I would have to settle for being a weekend gurl.

We went back to Tif’s apartment after having dinner near the mall.  We both tried on all of the things we bought while we were out.  Tif insisted that I wear one of her wigs home so that I could stay dressed in my skin tight jeans, shear blouse, and lace bra with breast forms.  It didn’t take much convincing as I really didn’t want to change into men’s clothes.  I was surprised that I filled two entire shopping bags with everything I purchased for myself over the weekend.

Tiffany walked me to my car carrying one of the bags.  She gave me a big hug and a kiss on the lips before giving me her phone number so I could call her, leaving both our numbers on our cell phones.  As I got into my car she said, “I hope we’re going to spend next weekend together, Sweetie.”

I replied, “Of course.  You know I like to spend as much time with my BFF as possible.”

It was almost dark when I pulled into my apartment parking lot.  There were no parking spots along the front of the building so I had to park on the other side.  I started putting my bags, shoes, and pocketbook on the front of the car.  Suddenly, I heard a voice, “Can I help you with some of that?”

I turned around to see an older man walking around my car as I answered, “I think I’ll be okay.” 

He replied, “Are you sure?  You look like you have too much for anyone to carry by themselves.  I promise I won’t bite you.”

I realized it was just my normal defense mechanism.  He was right, there was too much to carry in one trip.  Why shouldn’t a woman accept help from a man?  “Okay.  That is sweet of you, Thank you.”

He took both shopping bags leaving me to carry the shoes, pocket book, and small bag of my male clothes.  He walked beside me as he said, “If you come home past five or six, you can never get a close parking spot.”  Which apartment do you live in?”

I answered, “G24.”

“I live in G14,” he said as we neared the main entrance of the building.

Panic began to set in as I realized he lived in the apartment just below mine.  He probably knew that there was no woman living in my apartment.  What if he figured it out?  What would he think when he sees a man coming out tomorrow?  What would Tiffany do?  What am I going to do?  He was opening the front door for me.

As I stepped in and walked toward the steps to the second floor, he followed with my bags.  I was going to tell him it wasn’t necessary to carry the bags up, but it seemed senseless at this point.  At the top of the steps, I paused as I unlocked my door before opening it.  He followed me in and set the bags on the floor.

“Thank you so much, Sweetie,” I instinctively said.  “You are such a dear.”

“That’s quite alright.  It was my pleasure.  How long have you lived here?” he asked.

I knew I would eventually reach a point where my newly planned transformation would come face to face with reality, while maybe not this soon, it was as good as time as any.  I felt comfortable and safe with the situation, not to mention, the sudden thrill of what was possible, so I answered, “Going on three years now.  My name is Katrina.  Kat for short.”

With a slightly puzzled look, he said, “Wow, I thought a man lived here all this time.”

Tiffany’s influence came through as I couldn’t resist saying with a big smile, “Yes, well that’s changing.”

He smiled back with a look of understanding and acceptance, “Sounds like a change for the better.  My name is Gregg.  It is nice to meet you.”  He lifted my hand and kissed it gently. 

I was quite sure he knew what was going on.  Tiffany would have been so impressed with me I thought to myself.  But, she wouldn’t stop there.  So I pushed forward a little further.  “It’s nice to meet a gentleman.  Maybe we can have a cup of coffee one evening.  I’m home all week until Friday.”

“I might take you up on that offer.”

“Please do dear.”

As soon as he left, I locked the door and took my bags to my bedroom.  Spreading all my new clothing out on the bed, it became clear I needed some drawer space for much of it.  I looked through my bureau and decided to take some of my male clothes out to make room for my female clothes.  I packed up a large portion of my male clothes in some storage bags I had in the closet.  This left me one drawer for my panties, one for my bras, one for my lingerie, and a larger drawer for some of my shorts and blouses.  A thrill ran through me as I neatly folded and placed my gurl clothes in their new home.  It also became apparent to me that I couldn’t wait six months to complete my planned transformation.  Next weekend already seemed too far away.

I took off my jeans and blouse looking through my closet in just my bra and panties to find something to wear for the night.  I was debating whether to remove my breast forms.  They’re not supposed to be worn to bed, but they make me look and feel sexier.  They also have a tendency to shift through the night, sometimes falling out completely.  I thought how wonderful it must be to have real breasts like Tiffany.

In the meantime, I felt I needed better breast forms so I sat down in front of my computer and searched some sites.  It was amazing the variety that was available.  After researching for an hour or so, I settled for a pair of asymmetrical size 34 “C” cup forms that could be worn to bed, but required medical adhesive. Using my credit card, I ordered the forms, adhesive, and expedited delivery.   They claimed seven to ten day delivery in a plain box.  I decided to remove my breast forms for the night and wear a padded bra with a short teddy to bed. 

The next morning I woke up and took a shower before signing on to my computer for work.  Since I put most of my male clothes in storage bags, I decided to wear a thong, bra, shorts, and a pull over shirt.  The work day was so much more enjoyable and comfortable dressed as a woman.  After signing off in the afternoon I realized I was going to have to go food shopping.  I really didn’t want to change into male clothing.  I sat down in front of the mirror in my bedroom, put on Tif’s wig, and then went to work on my make-up.  While it took me some time and a few mistakes, I looked quite passable.

A week ago I was a nervous wreck about stepping out of my door wearing panties under my male clothes, now here I was getting ready to go food shopping completely dressed as a woman.  There was simply no going back.  The woman inside me could no longer be repressed.  It was an epiphany.

I put on a pair of flats that I purchased at the mall over the weekend with Tiffany, grabbed my pocketbook, and headed out to the car.  It was still light outside and my car was parked on the other side of the parking lot, but I didn’t care.  In fact, I was enjoying the walk to the car as I moved my ass like Tif had taught me.  While feeling quite liberated, I decided to go to a food store a little further away for just a little added insurance.

In addition to some needed food, I found myself picking out some women’s shampoo, conditioner, skin crème, and body wash.  Then, I spotted the nail polish.  In spite of telling Tiffany I wasn’t going to wear nail polish until I was a full time woman, I completely changed my mind selecting three different colors.  Well, it is a woman’s prerogative to change her mind.  Isn’t it?

The checkout girl filled four bags with my items as she gave me a smile.  I could sense a different attitude from women towards women than towards men.  She complimented me on my bracelet, which I picked out on a whim at the mall. 

When I returned home, again, there were no parking spaces so I had to park across the parking lot.  I somehow managed to carry all four bags to the front door.  The door opened magically as I approached it.  Apparently, Gregg had seen me coming from his window and came out into the hallway to open the door for me.

“It seems like you’re always carrying a lot of bags.”

I smiled, “I know, it seems that way this week.  Thank you for getting the door, Sweetie.” 

He took two of the bags from my hands and carried them up the steps to my door. 

I asked him, “Would you like that cup of coffee now?”

He answered, “Sure.”

“Have you eaten yet?  I’m going to make some dinner.”

“No. Actually, I was just getting ready to go out to get something when I saw you walking across the parking lot.”

“Well,” I said.  “That settles it.  I’ll make some dinner for both of us.”

I began unpacking and putting away my groceries as Gregg sat down.  He explained to me that he was divorced several years ago and lived by himself.  He had to give up his house as part of his divorce settlement.  We talked about our lives a little as I made dinner. 

After we ate, he offered to help with the dishes.  As I cleaned off the counter, I looked in the last bag of groceries.  It was the women’s items I bought.  I pulled out the three small bottles of nail polish and asked Gregg, “Which color do you like?”

“Pink.  I think it would look best on you.  Would you like me to paint your nails for you?  My wife always made me do hers.  She said she couldn’t do her nails on her right hand using her left hand.”

“I couldn’t ask you to do that,” I replied.

“You didn’t ask, I offered.”

He led me to my recliner, sat me down, and pushed it back so my feet were up in the air.  Then, he brought one of the kitchen chairs over, sat down, and removed my shoes.  After carefully painting my toenails, he moved to my fingernails placing a paper towel under each hand.  Of all of the feminizing things in the past week, this was the most prominent.  I couldn’t believe how good they made me look and feel.  It was like Christmas lights on a tree.  I was sorry I didn’t do this earlier.

“Well, how do they look Kat?”

“They look great.  You’re so wonderful.  I really like the pink, too.”

He asked with a surprised look, “Is this the first time you’ve worn nail polish?”

I answered, “This week has been the first time for many things for me.”

He smiled, “It will take a few minutes for them to dry,” as he took the chair back into the kitchen area.  “I should be going, it’s getting late.”

“Can I get you something before you have to leave?  Coffee?  Tea?  Me?”  I felt like such a slut after I said it and neither of us openly acknowledged my real gender as much as I was sure he knew.  Then, again, maybe he wasn’t interested in me or was nervous or uncomfortable with the situation.  When did I ever have sex with someone I only knew for two days?  Oh yeah, twice in the past week:  Ted and Tiffany.

Gregg quickly put my mind to rest as he walked over, put his arms around my waist, and said, “Number three sounds good,” followed by a tight hug and a kiss on my lips.

I think I took him by surprise with my boldness.  Hell, I was surprised with my boldness.  But I knew what I wanted, and I wanted him, now.  I felt like a naughty girl as I reached down and rubbed his crotch with my right hand as my left hand was on the back of his neck.  My newly painted fingernails added to the thrill as I watched my feminine hand probe the growing bulge in his pants.  His hands began to move from my waist up to my shoulders.  I moved my left hand down to his waist, then using both hands, I unbuckled his belt, pulled his zipper down, and unhooked his clasp.  His pants dropped to the floor.  I kneeled down and pulled his boxer shorts down.

His six or seven inch long cock hung downward slightly.  Using both hands, I stroked up and down his still-hardening shaft causing it to raise up to an almost level position.  I loved the look and the feel of his cock in my hands.  It is hard to describe, but it seems impossible to fully satisfy my desire for its intimacy. 

The kneading with my hands was beginning to develop some precum from his little slit.  I stuck out my tongue and licked the sweet syrup from the tip.  His hands tightened on my shoulders slightly as he let out a subdued moan along with some more precum.  I licked it, again, as I continued to use both my hands on the base of his shaft.  He continued to ooze an amazing amount of precum. 

I began to lick up and down his shaft paying particular attention to his prominent vein along the bottom.  I was wondering if that was an indication he was a heavy cummer.  His entire shaft was becoming wet from his precum and my saliva.  While I wanted to give him a slow and thorough blow job, I couldn’t resist any longer, I had to have his beautiful cock in my mouth.  I opened my mouth and slid my lips half way down his shaft.  Then, with a slight suction, I pulled up to just the tip and wagged my tongue on it.

He moaned, again, his hands still holding onto my shoulders, yet not forcing them in any direction. He was so gentle and loving.  I sensed that he was probably deprived of great sex with his ex-wife and may be shy with women.  I’ve been there myself.  One of the many lessons learned from Tiffany is that a woman does not have to be submissive.  Sex can be a two-way street.  Or in my case, it was becoming a boulevard.

I plunged back down his shaft with my tongue firmly against his vein.  Once, again, I withdrew with a steady suction finishing with licking his slit.  I repeated this for fifteen minutes until his shaft had a thick, heavy, and slippery coating.  Now I was ready to take it in my throat. 

My next plunge took it all the way, surprising Gregg, as I held it down for at least ten seconds.  He quite loudly proclaimed, “You’re unbelievable Kat!”  His hands were squeezing my shoulders like he was holding on a roller coaster ride.  I could feel the muscles in his thighs tense up where my hands were on them.  Finally, I had to pull up for some air.  Sometimes I wish I could hold a cock in my throat forever.  It’s like swallowing a favorite desert.  It tastes so good going down and you can’t get enough of it.

Until this past week, I always thought it was a chore for a woman to suck a man’s dick.  I figured they did it because they thought they had to.  Maybe it is for some women, but I really enjoy it.  It’s so sensual.  It’s so feminine.  It’s even controlling as I elevate his emotion, then lower it.

I moved up and down, again, with slow deliberate motions messaging his shaft and vein with my lips and tongue as I occasionally sucked at the same time before taking a deep breath and taking him into my throat until my lips were against his balls.  I felt a wave of satisfaction knowing the pleasure I was bringing to him.  He shifted his hands from my shoulders to my head as I held him in my throat for the longest duration so far.

As I pulled him out to get a breath of air, Gregg let out a long sigh as he said, “Ohhhh Kat, you’re going to make me cum.” 

I replied, “That’s what I’m trying to do Sweetie.”

“I don’t want to make a mess.”

He was confirming my suspicions that this might be the first “complete” blow job he’s ever had.  I wanted it to be the best and most memorable.  I answered him back, “Don’t worry, there won’t be any mess.”

With that, I increased my suction moving up and down his shaft several times in quick succession.  His hands moved to the back of my head.  He began to pant and almost groan.  I tightened my grip on the back of his thighs to assure him I didn’t want him to come out of my mouth.  He started crying out, “Oh…Oh…Oh… I’m gonna cum!”

I took a quick deep breath and pulled him into my throat.  He started to push my head back a little, but his reflexes took over and he pulled my head tight against his groin as he erupted.  I could feel his large vein pulsating as the cum began pumping into me.  It’s not possible to swallow nor taste when your throat is filled with a cock.  However, I could feel the warmth of his hot cum as it was being forced down the remainder of my throat on its way to my stomach.  As I pulled back for some air, I couldn’t believe he was still ejaculating.  I guess I was right about him being a big cummer.  Now, I could taste his cum and had to swallow it as he finished filling my mouth with his king sized load.  I kept my mouth firmly clamped on his member, holding still since I was sure he was probably quite sensitive.  He held my head tight while he began to soften.  His knees were bent a little and the muscles in his thighs began to relax.

He was still breathing heavy as he said, “I’m sorry I came in your mouth.  Are you okay?”

I slowly pulled my lips over his cock, stopping to lick the tip clean, before letting it out of my mouth.  I licked my lips and the inside of my mouth free of his cum and swallowed it as I stood up and looked into his eyes.  “Sweetie, I wanted you to cum in my mouth.  Didn’t you like it?”

“Yes, it was great.  I wasn’t sure if you were okay with it.”

“Oh you poor baby.  I think you’ve been deprived all of these years.  I’ll tell you if there’s something I don’t like.  And you tell me if there’s something you don’t like.  Deal?”

He smiled, “Deal.”

I reached down and pulled his boxers up, followed by his pants.  I hooked them, pulled the zipper up, and buckled his belt, still fascinated watching my hands with polished nails.  I felt so in charge.  I felt so thankful for my BFF’s influence. 

“Thank you for a beautiful night, Sweetie.  I hope to see more of you.”

He responded, “The pleasure is mine.  You’re amazing.”

After he left, I thought to myself, he is somewhat naïve.  I must make sure he knows I’m not a natural woman before moving forward.  I also have to rethink my transformation plans.  I never realized that a little nail polish could have such a profound effect.  It was going to be difficult sleeping tonight.  There was a lot on my mind.  This was a life changing week.