It was midnight by the time I got home from Tiffany’s. I took off my shirt and pants and put on the silk nightie she gave me over the bra and panties I wore home. The feeling was exquisite. It felt so comfortable when I got in bed that I fell asleep within minutes.When I woke up the next morning, I reluctantly took my lingerie off so I could take my morning shower before starting my workday. I work at home on my computer taking and entering sales orders and customer assistance for an office supply company. Since no one can see me on the computer, I often wear a pair of panties under my pants. After spending a few hours with Tif last night, I was becoming bolder. If no one can see, why wear pants at all. I could wear my bra and a pair of panties all day. I picked out another new pair of panties from the shopping bag, put them on along with the bra, and a long pullover shirt with short sleeves. They were my work clothes for the entire day.As I sat at my computer working, I started practicing being a woman. I crossed my legs at my knees with my feet to one side while I sat more straight than usual. Tif was right, I was beginning to feel like a woman. At five o’clock, I logged off my work site and decided to surf the net a little. I typed in “T-girls” and found many sites. One of them had an assortment of short videos. I watched several of them. They all showed T-girls sucking cock and getting it up the ass. Then, I found one where a T-girl was using a dildo in her ass.Suddenly, I remembered the vibrator Tif gave me last night. I went to my bedroom and took it out of the shopping bag, removing it from the box. I turned the knob on the one end and it began to vibrate. It was adjustable, turning the knob further increased the intensity. I was still hard from watching the videos and wanted to experience the anal sex I had watched. I went to the bathroom, getting some baby oil, which I rubbed on the vibrator after turning it off.In the bedroom, I got on the bed on all fours, like a dog. I pulled my panties down to my knees. Reaching behind me, I fumbled around trying to line up the tip with my asshole. It was a little difficult at first. I had to direct it by feeling it near my entrance. Finally, I could feel it centered in my mushy hole. There was some minor pain as I began to push it in. Between my visions of the video and the feeling in my ass, my cock was rock hard. The pain subsided as I pushed it further into myself. I pictured Tiffany last night as she delighted in being penetrated by my cock. I was beginning to appreciate how she must have felt. When most of it was in me, I started rotating the knob. Oh, what a feeling. I sat up on my knees, then leaned back into a position where my ass cheeks were resting on the back of my legs. I could isvecbahis see my cock was oozing pre-cum like never before. I turned the knob up completely. My insides were tingling and I could feel an orgasm building. My balls were tightening. Losing complete control, I began pumping cum three or four feet across the bed. I never even touched my cock.It took me a few minutes to regain my composure. I reached back and turned the knob off. Sitting back up on my knees I began to pull the vibrator from my ass. It was almost as difficult pulling it out as it was pushing it in. It was a strange feeling, a little like taking a shit, but being pulled, rather than pushed out. When it was completely out, I felt somewhat empty. I wanted to push it back in.As I pulled my arm back around in front of me, I could see some feces smeared on the tip of the vibrator. I hobbled to the bathroom with my panties around my knees, turned the water on in the sink, and rinsed off the vibrator. It freaked me out a little bit. It was a bitter-sweet experience. It felt so good and it was one of the two best orgasms I ever had, the other being last night with Tif. But, I wasn’t prepared for the mess. It wasn’t anything like that on the videos or with Tiffany. I wiped my ass with toilet paper before pulling my panties back up.After eating dinner, I thought about this coming Friday night with Tiffany. She didn’t give me a time or tell me what she expected. She didn’t even give me her phone number. Maybe she didn’t really expect me to come back or, worse yet, maybe she didn’t want me to come back. At one point, I began to think it was only a dream, but it couldn’t have been. I was sitting in the bra and panties she gave me. I spent the rest of the night thinking about how I would dress, what I would take with me, and what time I would go.The next morning, Friday, I took my shower, put on my bra and another pair of panties from my bag. I ate breakfast, lunch, and worked all day on my computer wearing just the bra and panties. When I logged off work in the afternoon, I started to plan for my night. I decided I would go to her apartment at eight o’clock since it would be dark and that was about the time I met her in the store so she should be home from work.It was important that I showed her I was progressing toward a feminine look and attitude so I took a bath in some scented Epsom salts that I had. I shaved my legs, chest, and arms. No one would really notice, I figured. Then, in a spur-of-the-moment thought, I decided to trim my pubic hair into the shape of a heart. There was little else I could do. I didn’t have perfume, make-up, or other feminine products.After getting out of the bathtub, I put on another pair of panties from the bag, the bra, along with the breast forms, jeans, isveçbahis giriş and a tight nylon shirt. While it wasn’t the sexiest outfit, it was the best I had, and it left no doubt I was wearing a bra. I put on a pair of light brown canvas loafers to complete my ensemble. I decided I wasn’t going to bring anything with me. It was almost seven-thirty and it was dark outside so I put on a jacket and went out to my car.On the drive over to her apartment, a million things went through my mind including she would not be home, someone else would answer the door, she changed her mind about seeing me, and a host of others. I forgot the apartment number and was relieved when I saw her familiar car. At least, she should be home anyway. I parked in the empty space next to her, walked to her door, and nervously knocked lightly. She opened the door with a vibrant greeting, “Hello, sweetie.”A wave of relief and happiness swept over me. I responded, “It’s so good to see you, again, Tif.” We both reached for each other in a hug.She stepped back and said, “I see you wore that beautiful bra. It looks good with your blouse. But I think we need to work on your wardrobe a little.” Her smile was melting me. “Let’s sit down for a few minutes. Scotch okay, again?”I nodded yes as she went into the kitchen and made two drinks for us. When she returned, she handed me my drink as she sat down next to me on the couch asking, “Well did you use the present I gave you?”Thinking of the negligee, I responded, “Yes, I’ve slept in it both nights. I love it.”“Silly gurl. I meant the other present.”She could still make me blush. I also knew she was expecting an answer, so I stuttered, “Yes. Yes I did”“Well. How did you like it? It’s not for everyone, you know. You either like it or you don’t. Some people actually get an orgasm from anal sex.” She looked into my eyes waiting for me to answer. I’m not sure what gave me away, but she can read me like a book. I think maybe I smiled slightly. “You didn’t!” Her face lit up as she coyly asked, “You had an orgasm from the vibrator? Did you touch your cock at all?”The look on my face must have been an obvious answer. She hugged me tightly. “Oh, we’re going to get along so well. We have so much in common, girlfriend. Grab your drink, let’s have some gurl time.” She took my hand and led me to her bedroom.We went into her walk-in closet and she picked out a pair of stretch jeans and a sheer white blouse. “Here put these on, Sweetie.”I pulled the shirt off over my head, then undid and wiggled out of my jeans. Tiffany looked at my legs, “You shaved your legs. They look good. You have beautiful legs.”I put on the stretch jeans. They hugged my legs, ass cheeks, and crotch. The blouse was a pullover with a partially buttoned isveçbahis yeni giriş top. After pulling it on I tried to button the first button, but it was backward. I said, “I didn’t know they made left-handed clothing. Are you left-handed, Tif?”She gave me a weird look, then answered, “You silly gurl. Women’s clothing always buttons the opposite of men’s. I don’t know why, but that’s the way it is. Let me button the first few for you. Leave the top unbuttoned. It looks sexy. What do you think?”“It looks good and I love the way the pants feel on me.”She immediately corrected me, “Jeans!!! Women don’t wear pants. They wear pantsuits, slacks, capris, and jeans. You have to work on your vocabulary.”I gave her a little pout, “Sorry, dear.”She gave me a big smile and then pulled me to one of the chairs in front of her vanity. Then, she went into her closet and came back with a brunette wig. She put it on my head, carefully pulling it into place all around. Using a brush with little white ball-like tips on the bristles, she brushed the hair on the wig down to my shoulders for several minutes as I watched in the mirror.“Time to make the big difference,” she said as she sat in the other chair and swiveled me so I was face to face with her. First, she brushed on some make-up, followed by two more shades on my nose and cheekbones. Next, she reshaped my eyebrows with a pencil, darkened my eyelashes with a small brush, finishing with some eyeliner on my eyelids. I couldn’t really see exactly how she was doing everything, although she was explaining it to me since I was facing her instead of the mirror. Finally, she began to put lipstick on my lips as she told me to watch how she moved her lips and do the same.When she was finished, she swiveled my chair so I was facing the mirror, again. I couldn’t believe it was me. I not only looked like a woman, I looked hot. I turned to Tiffany and exclaimed, “You’re amazing. I can’t believe how convincing you made me look. This is a game-changer, girlfriend.”“Would you like to go out for a short while? Maybe do a little clothes shopping before the stores close? Practice walking, maybe talking?” She handed me a pair of black open flat shoes.I replied, “Gee, I don’t know. That’s quite a big step. It was only a few days ago that I was terrified to even walk in the women’s wear.”She taunted me, “I’m sorry, I guess I didn’t do a very good job on your make-up.”“Of course, you did. I just don’t know if I’m ready yet.”She gave me a disappointed look as she said, “We’re not going to waste all that time I spent on you, now are we? You said yourself how good you look. You don’t have to talk to anyone, but me. I’ll do the talking if anyone talks to us. Come on, pleeeeeeease.”What could I say? With a little mocking her I replied, “Okay, sweetie. Let’s go.” I put on the shoes.She did a few finishing touches on my hair and got a small purse from her closet and gave it to me. “Here, let’s put some important things in your purse. Do you have a wallet?”