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 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, 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 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?”
I picked up my pants, excuse me, jeans, that I wore from home, and took my wallet out of the back pocket. Tiffany told me to give her my credit card, driver’s license, and some cash. She put them in the purse along with lipstick and make-up before handing it back to me. We finished our drinks, she brushed her hair, picked up her purse, and we went out to her car.
“I’ll drive. I think it will make you feel a little better,” she said to me.
The thrill of walking outside dressed as a woman overshadowed any apprehension I originally had. Tiffany patted me on the ass saying, “Gurl, you gotta learn to sway that booty a little. Watch and learn from me and other women. Remember what I told you about watching women.”
We got into the car and drove to the same store I met her in a few days ago. I walked a few steps behind her in the parking lot so I could watch her walk as I tried to copy her. She took a shopping cart as we walked in the entrance. I couldn’t believe she talked me into this. I kept watching everybody around us to see if anyone was staring at me. Fortunately, the store wasn’t too crowded and no one seemed to pay any attention to me. We walked directly to the women’s department.
I felt a thrill come over me and a sudden appreciation that I came tonight as we walked into territory that was previously forbidden to me. It was similar to the first time I rode a bike successfully when the thrill of riding overcame the fear of falling. We picked out a few bras, skirts, blouses, and jeans. Then, Tif said, “Let’s go try them on in the dressing room.”
I guess this was going to be another step in my transition. We walked to the dressing room where Tiffany said to the attendant, “Six items, sweetie.” She left the bras in the cart. I admired the way she understood the women’s world and expected to be part of it. We went into the dressing room together.
She helped me try on the various clothes we picked out. I truly felt like BFF’s as she helped me change, then looked me over each time, commenting on how the clothes fit. It was the first time I ever wore a skirt. My eyes lit up when I put it on. There was no hiding how it made me feel. We both smiled and giggled at my response in the mirror.
When we were done, she got everything together, carrying it to the cart. As we passed the attendant, Tif said, “We’re going to take them all.” That drew a smile, but no remark.
Then, we went to the cosmetics department. This was definitely uncharted territory to me. Tif picked out a handful of items, placing them in the cart. In the next aisle, she took a small bottle of lotion from the shelf as she said, “This is a little treat for tonight,” giving me one of her devilish smiles. We went to the normal checkout aisle where a girl scanned everything, removing the hangers from the clothing, and neatly folding them before placing them in a bag. Tiffany instructed me to get out my credit card. As I removed it from my purse I realized my first name, Shawn, was on it. Thankfully, all I had to do was insert it into the reader so no one saw it.
On the way back to Tif’s apartment, she asked if I had to be home at a certain time tonight. I told her I didn’t. She invited me to stay overnight if I wanted to. I leaned over and gave her a little kiss on the cheek acknowledging her invitation. I was having so much fun being with her.
Once back at the apartment, she poured us both a drink. “Let’s go in the bedroom and watch some television while I pick out some comfortable nightwear, sweetie.” We took our drinks to the bedroom where she turned on the flat-screen television on the wall over her dresser. She selected a porn channel as she set her drink on the night table before going into the walk-in closet. I sat on the end of the bed watching as a well-hung man was anally fucking some slut.
When Tiffany came out of the closet (no pun intended), I said, “Can I ask you a question?”
“Of course you can, you’re my BFF.”
A little embarrassed, but desperate to know, I asked, “How come they look so clean when they have anal sex on porno flicks?”
“Well, most of the time, the woman has an enema to clean herself out before sex. If the man has a short dick, it probably won’t matter. But if he is like that stud on the screen, she must be clean or it won’t be very pretty. I always clean myself out. The only problem is you shouldn’t have an enema more than once a week. That can limit anal sex a little for me. Of course, that hasn’t been a problem, lately. Would you like to try an enema tonight, sweetie? I’ll make it worth your while.”
As usual, she didn’t give me much time to answer. She took my hand and led me to the bathroom. Then, she instructed me to take off my jeans and panties. She opened her bathroom closet and took a red bag with a hose on it that was hanging on the door. She took a bottle from the shelf and emptied some of it in the bag before filling it with some water from the sink. Hanging it on the top of the door, she stood behind me, and probed between my cheeks with the end of the hose until she found my entrance, then she pushed it into me.
“Ready or not, here it comes,” she announced.
There was a sudden warmth as the liquid began to fill my ass. My cock began to harden and pre-cum started leaking from it. She asked, “How does that feel?”
I answered, “Strange, but good.”
After a few minutes, I felt like I was going to explode. She pulled the hose out and told me to sit on the toilet. As I sat down, I couldn’t hold it any longer and relieved my bowels in front of her with a little embarrassment and a lot of noise. She handed me a wad of toilet paper. “Wipe, sweetie, You should be clean as a whistle now.”
She walked back to her closet for a minute and returned with a beautiful shear negligee and a matching pair of lace panties. “Here, put these on. They’ll make you feel good.”
I pulled the negligee on over my head. She was right. It felt wonderful. Then, I went to put on the panties, but there was something strange about them. I realized they were crotchless. My dick was still somewhat hard, so it stuck out tenting the teddy. Tiffany handed me my drink as she said, “Let’s lay on the bed and watch television.”
She laid on one side of the bed on her stomach facing the television. I laid next to her, also on my stomach. The earlier porn flick had finished and a new one had just started. This time there were two men and a woman. She started off by sucking one of the men’s dick as he sat at the head of a bed. He was huge and she was struggling to get it in her mouth. I was fascinated by his size. I was even more fascinated when she actually managed to take him into her throat. The camera focused on her neck where you could see his monstrous shaft bulging inside her.
Just when I thought it couldn’t get any better, the camera panned back to show the second man pushing his oversized cock into her pussy from behind. She made a muffled noise as he filled her pussy. Then, she raised her head freeing the cock from her throat. She took a breath and began to moan, before putting the cock back in her mouth. The man in the back was pounding away when his dick sprung free. He pushed it back in her pussy, then withdrew. He did this several times as his dick became covered with her juices.
Then, he put his dick against her rosebud. She grunted as he began to force his enormous shaft into her ass. I let out a moan myself as I became quite excited. Tiffany rolled off the bed saying, “I guess it’s time for that treat I promised you.”
Before I could think about it, she was on her knees behind me. My legs were open a little. I could feel her put something between my cheeks. There was a sudden wet feeling as she squeezed some liquid into my asshole. “Watch the movie, sweetie,” she instructed.
I’m not sure she understood how difficult that was going to be, but I was excited about what I was watching before I was distracted. I watched as the man was pushing his oversized cock into what seemed an impossible little hole.
Suddenly, I could feel my own rosebud being violated. For a moment, I felt like I was in the movie as I was simultaneously being penetrated at the same time. When I felt Tiffany’s hip bones on my cheeks I realized she was fucking my ass. I let out a long moan of both satisfaction and encouragement to continue. She began with long slow strokes. I began to feel the temperature increasing inside me. It was becoming intense.
“How do you like the warming lotion in your ass? I know I love it. I hope you like my treat.”
I answered with a girlish moan that surprised myself, “Ohhhhhh, Tif. It feels absolutely wonderful. I think I’m in heaven.” She continued to move in and out in long strokes that drew a chorus of moaning from me. The excitement of watching the movie, the sensation and warmth inside me, and the compression of my cock between my pelvis and the bed were reaching an explosion point. I warned, “I’m going to cum on your bed.”
She answered, “Go ahead, sweetie. Let it go. I know I’m going to cum in you any minute now.”
She increased her pace and intensity. I lost all control and, in a convulsion, shot my load into her blanket-covered mattress. It was the most intense orgasm I had ever experienced. I felt so much like a woman, letting everything that built up in me out in one massive flood. My heart was beating a mile a minute. My arms were stretched out in front of me, my face buried in the blanket.
Tiffany was still pumping me as my climax began to subside. Her upper body propped on her elbows, the weight of her hip bones on my ass cheeks, she pushed one last thrust into me and held it as she let out a prolonged moan. Then, she bucked her hips in a few short jerks before collapsing on top of me.
We both laid still, content, and quiet. My ass was still warm inside. The front of me was wet and sticky. I had a few small spasms or aftershocks from the occasional pulsing of her cock inside my colon. Finally, she began to raise her body off of me. I could feel her softened cock pulling from my ass leaving me empty. She rolled off the bed standing next to me with her bare cum covered cock close to my face.
“Do you want to clean it off, Sweetie?” I was still in a state of euphoria and feeling like a woman still lusting for a man, my inhibitions still broken down by my feminine desires. I moved my head to the edge of the bed, stuck out my tongue, and licked a little of the thick semen from the tip of her dick. She responded by pushing it into my lips. I intuitively opened my mouth receiving it. Her semen was a little milder than my own that I tasted on her lips and tongue a few days ago. Tasting it gave me a feeling of surrender and an ultimate commitment of a woman to a man.
After licking her cock clean, I pushed myself up and sat on the edge of the bed. I apologized, “I’m sorry about the mess on your bed.”
“No problem. We can clean it up in the morning if you don’t mind sleeping in the puddle tonight. I find it so sexy. Let me get us another drink.”
When she returned I told her, “That was so good, Tif. You know the three best orgasms of my life were this week. All, thanks to you. How can I repay you?”
She answered, “You just did, sweetie. Let’s finish our drinks and go to bed. This is just the beginning.”
As I laid back down on the bed, Tiffany put her hand behind me and pulled a condom out of my ass. “Your ass is as tight as mine. You know we could be sisters. We’re so much alike.” She laid next to me and we both fell asleep. I couldn’t wait for the next adventure with my BFF.
