Wednesday morning I woke up and took a shower before going back to my bedroom to pick out some clothes to wear. Although I was starting to accumulate a small wardrobe, I still had a long way to go and found myself with little choice for the day. Also, most of my clothes were now in need of being washed. I put on a pair of lacy pink panties, a matching padded bra, and the only clean pair of shorts and blouse remaining. It had been five days since I wore any male clothes.
I thought about shopping for some clothes online, but I really like being able to see them first and trying them on before buying them. I sent a text to Tiffany asking if she would like to go shopping one night. She responded a few hours later while I was signed on my computer for work for the day, suggesting we go tomorrow night. That was perfect since it allowed me to wash all of my clothes tonight. I messaged back that I would pick her up at seven.
Promptly at five o’clock I signed off my worksite and headed for the bedroom to put on the wig Tiffany gave me last weekend. I still had my new starter earrings on since they said I should keep them in for at least thirty days to keep the new piercings open. Then, I put on some make-up so I was comfortably passable enough to go to the laundry room a few buildings away in the apartment complex. I grabbed my basket of dirty clothes and headed to the laundry room.
There was no one in the laundry room when I went in. There was one empty basket on top of a running dryer. Memories of finding a pair of panties left in that dryer a few weeks ago brought a smile to my face. It was really what caused me to go to the store where I first met Tiffany. I put my clothes in one of the washing machines, along with six quarters and some detergent, before starting the cycle and walking back to my apartment.
I made a salad for dinner and ate it before going back to the laundry room. Losing weight suddenly became a priority and part of my plan to look more feminine. I took a magazine back with me as I wanted to stay in the laundry room while my clothes were drying. My timing was perfect. The washing machine was in its final spin cycle when I walked in. I put the clothes in the dryer, sat down, and paged through the magazine. I felt so much like a woman. It’s amazing the little things that have thrilled me as a crossdresser. Tiffany was so right about studying women closely.
My confidence exceeded any expectation I previously had, so when I heard someone entering the laundry room, I calmly continued reading. It was a middle-aged woman. She smiled at me and said hello. I smiled back. All through the past week or so, it was women who scared me, more so than men, when I was dressed. I felt they could see through me and sense I’m not one of their own. In my mind, I just passed a true test of my passability as a woman. As she loaded her laundry in one of the machines, another woman came in and emptied the dryer with the basket on top. I didn’t hesitate to stand up and empty my dryer at the same time. I even stood there and folded my ladies laundry in their presence.
As I carried my basket into my building lobby, I stopped to check my mailbox. I heard a door open behind me and turned around. It was Gregg coming in the front door. He immediately said hello as he walked toward me. I set my basket on the floor and gave him a hug.
“How are you tonight?” I asked. “Got time for a cup of coffee?”
He answered in a playful tone, “I always have time for you, Kat. I just got done work. Let me take a shower and I’ll be up in thirty minutes. Have you eaten dinner yet?”
“Yes, I have,” I replied.
“So have I. How about I bring up a bottle of wine, unless you really want coffee.”
I was pleasantly surprised with his forward attitude as I said, “Wine sounds better. I’m not much of a coffee drinker anyway. I’m going to put away my clothes and change into something more comfortable while you shower. I’ll leave the door unlocked. See you shortly.”
I could hardly contain my excitement as I walked up the stairs to my apartment. First, I put my clothes away while I thought about what I would wear. I wanted to look sexy, yet not slutty, showing some skin, but not exposing my genitals in any way. I didn’t want to scare him off and I was becoming quite nervous. How do I make sure he knows I’m not a real woman? Where do I start?
I chose to keep my panties and bra on, taking off my blouse and shorts, and pulling on a long oversized short sleeve white shirt. Looking in the mirror, I could see the color and contour of my panties and bra through the light fabric. It seemed so perfect. I felt like an innocent, playful young woman. My pink nails lit up in contrast to the plain white shirt. The hair of my dark wig laying on my shoulders against the white background just added to the “girl next door” look. I combed my hair and touched up my make-up as Tiffany had taught me. Before I knew it, Gregg was yelling in, “I’m here!” as he walked in the front door.
I yelled back, “I’ll be right out, Sweetie,” as I looked over myself one last time before walking out to the living room.
He held up a bottle of wine and smiled, “Do you have a corkscrew?”
At first, I thought he said: “Do you want a cockscrew.” It was obvious where my mind was. As I snapped out of it, I replied, “Yes, it’s in the top drawer of the counter.”
He opened the wine and filled the two glasses I gave him. Then, he clicked his glass against mine in a toast as he said, “Here’s to the most beautiful girl in the world.”
Now I was really confused. While it was such a nice thing to say, I was more unsure than ever if Gregg realized I wasn’t a real woman. I knew he was naïve, but maybe he was delusional, also. I knew I couldn’t be that convincing yet. Maybe he was just role-playing.
I thought to myself, what would my BFF, Tiffany, do? I knew what she would do: she would just get it out in the open and face the consequences.
I set my glass on the counter, took Gregg’s glass from his hand, and set it on the counter. I put both of my arms around his neck. He responded by wrapping his arms around my waist. I moved my head in and whispered quietly into his ear, “That was so sweet, but you do know I’m not a real woman, don’t you?”
He turned his head and whispered back, “You are to me.”
Tiffany is so right with her unwavering honesty. I felt like a weight was lifted off my shoulders. My comfort level shot back up and I responded, whispering into his ear, “You’re getting laid tonight, Sweetie.”
He squeezed me in a tight hug, then gave me a kiss on the lips. Kissing a man was becoming more natural and enjoyable to me. I sat down on one of the stools at the kitchen counter. We spent the next twenty minutes sipping wine as he gently stroked my hair, rubbed my shoulders, and kissed the back of my neck. Then, I swiveled my stool around facing him as I began to rub my hands on his waist, butt, and thighs, working my way to his crotch. I could feel him starting to harden from my attention.
“I think someone wants to come out and play,” I said as I looked up into his eyes. “Would you like to retire to the bedroom?”
Without waiting for his answer, I stood up, took his hand, and led him to my bedroom. There I slowly stripped off all of his clothes, folding each item as I removed them. I patted my hand on the bed motioning him to lay on it. Still standing alongside the bed, I bent over and took his semi-hard cock in my left hand, moving it up and down. As he began to harden more, a large drop of precum began to form on his tip. I leaned in further and licked it off.
I cupped his balls with my right hand while still working his shaft with my left hand. More precum replaced what I had licked off. I took another lick before putting my lips around his tip. Instinctively, I took more into my mouth. He was becoming rock hard. I bobbed my head up and down, taking him into my throat a few times very briefly. However, I wanted to be careful not to make him cum yet.
When he seemed to be as hard as possible, I stopped and got a condom out of my night table, rolling it over and down his cock. Then, I squeezed some lubrication over the top of the condom. I climbed up on the bed and straddled him, reverse cowgirl, dropping to my knees, before pulling my panties down in the back. Leaning back a little, I reached around and guided his shaft to my rosebud. I could feel the tip of his dick against my waiting hole. I sat straight up, and using my knees, lowered my body down. His cock began to push into my sphincter. The lubrication was cold and wet. My anal ring began to stretch open as his cock started to enter me. My tight, yet sensitive ass could feel the nubs of the condom sliding along inside of my sphincter wall as he began to fill my colon.
Gregg put his hands on my waist. I took my time lowering my body down so I could savor the wonderful feeling of the initial penetration. It's like when eating something really good, the taste is strongest on the first bite. But, like all good things, it eventually reached its limit. My ass cheeks were sitting on his thighs. His entire cock was completely buried in my ass and he had no more left to give me.
I rocked my body back and forth, grinding it downward at the same time. Gregg let out a deep long groan. Then, I used my legs to bounce up and down on him like I was riding a horse. I chose to sit backward on him to keep my own cock from his view. I wanted to keep up the illusion of being a woman to make him as comfortable as possible. While this position offered maximum penetration, I couldn’t see his face behind my back. I had to rely on his sounds and actions to assure his satisfaction. Thus far, it was apparent that I was satisfying him. His grip on my waist tightened, he was pushing me backward and forward with his arms, and he was grunting and groaning almost continually now.
I started moving up and down in longer motions increasing the friction of his cock in my anal ring. He responded by pulling harder when I bottomed out on him and thrusting his pelvis upward. I could feel my anal ring being pulled inward and outward as the lubrication began to dry up. The increased friction was building up heat inside me. He must have thought his meat was in an oven. I paused for a minute and contracted my inner muscles in the opposite direction of a bowel movement like I was sucking it in instead of pushing it out.
Gregg immediately cried out, “Ohhhh shit Kat, you’re incredible.”
I continued to milk his cock with my inner muscles for a few minutes. It was also stimulating me, as well as, him. I could feel an anal orgasm building up in me. Gregg’s grip on my waist was tightening. He pushed his pelvis up and held it there. I pulled my muscles tight, clamping on his cock with my ass. Gregg finally surrendered, “Ohhhhhhhh nooooo. Here it comes, Kat. Ohhhhhhhhh!!!”
His cock pulsated inside me as it pumped his cum into the condom. Seconds later my cock started shooting my cum into the front of my panties and my colon began to spasm uncontrollably. This prompted him to buck his hips. I raised my hands over my head as I let out a moan, “Ohhhh Gregg.” My whole body was tingling. His body finally relaxed back into the bed.
It took a few minutes before the spasms diminished completely and my cock relaxed. I could feel an occasional twitch of Gregg’s cock in my colon. His grip on my waist relaxed, allowing me to lean back on his stomach. He wrapped his arms around me before I rolled both of us onto our sides as he spooned me with his cock still well into my ass. I felt so contented.
We stayed like that for a long while. My panties were still down in the back and soaked in the front. I actually liked the feeling as it extended the experience for me. Gregg was still inside me despite his softened and shrunken state. He finally slipped out of me when he repositioned himself slightly. I reached behind me and pulled my panties up. I kept my back to him so I didn’t rub my cum soaked panties in the front against him. It was so important to me to be a woman to him, despite his acknowledgement of my true gender.
It was almost midnight when we got out of bed. We both had to work in the morning. After going to the bathroom and getting dressed, Gregg kissed me before going down to his apartment. “You’re the most incredible woman I’ve ever known, Kat. Thank you for such a wonderful night.”
I responded, “Thank you, Sweetie. You really know how to treat a woman.” I closed and locked the door and went to the bathroom to pee. I left my wet panties on and went to bed. There were at least two wet spots on the bed, but it didn’t bother me. I couldn’t wait to see Tiffany tomorrow evening to tell her about tonight. I knew she was going to be so proud of me. My desires to live as a woman were getting stronger every day and I knew it was only a matter of time before I would throw away my male clothing
