After Work

After work at the office, Ben and I came over to my place to unwind. He began talking about how he loved to see women all dolled up in pantyhose, heels, and a sexy outfit, and complaining how women nowadays don't dress up the way they used to in the professional environment. The way he was talking about all of this made me think that maybe all he was into was a sort of man's traditional understanding of what femininity should look like in a woman. I was interested because I had been into dressing up in pantyhose, heels, and sexy outfits for years, but always in secret. I've always wanted to come out and present myself to someone all dolled-up to see what they thought. I started to think that this may be an opportunity to do so.

"It seems like you're just into a certain feminine look, Ben," I said to him, with a little hesitation. He looked at me curiously, and responded "What do you mean by that?"

"Well, it seems that it doesn't matter who you're talking about as long as the 'who' is wearing pantyhose, heels, and some sexy outfit, am I right?"

He looked at me like I'm crazy and retorted "Are you insane? You're telling me that It wouldn't matter if it was a guy or a girl under the clothes? Hell it doesn't! I'd be disgusted if it were a guy under there!"

Right then, I saw an opportunity, and I took it. "Okay, how much do you want to make a bet? I'll bet you a hundred bucks that if I got all dolled up and looked feminine and sexy, then you'd find yourself attracted to my look." I knew he was uncomfortable with the thought of being with anything that had a penis, so I qualified my statement: "You won't be attracted to me, but you'll find the look attractive."

"Seriously? A hundred bucks? If I have your word, let's do it!" He was laughing, and thought that I was kidding. I told him I had a bag of clothes and other feminine stuff that my ex-girlfriend left hidden away in a closet, and proceeded upstairs.

"Wait, you're serious?" he asked, completely surprised.

I became nervous, but incredibly excited, and responded, "Yeah, I can use the money for bills!"

So, I went upstairs while he waited downstairs. My body was already smooth, and my hair was already naturally long. So, I stripped down. I was incredibly excited - and immediately I became hard as I opened the bag of feminine goodies. I didn't know what to expect, but I prepared for the best! I squirted a little sex lubricant inside of my hole, and then slid on some black panties. My toes were already painted red, but not my hands. I decided to do that last.

I remembered he complained that no woman ever wore nude pantyhose anymore, so I slipped carefully into a pair of nude pantyhose. It felt incredibly exhilarating feeling the hose slide and stretch up my legs, knowing that my nylon clad legs would be seen by him. After pulling it up to my waist, I felt it sheering all over my ass and crotch, and it felt wonderful and sexy hugging me all over. I then put on my breast forms and bra, and then slipped on a silk cream blouse. I decided that a sexy office suit would be appropriate with a short black skirt. After all, he always loved to see sexy lawyers clad in hose and wearing heels, with a sexy skirt suit to boot. The feeling of the black skirt sliding up my pantyhose covered legs, and then stretching over my thighs and hugging my ass as it completed its journey up my legs. I slid into some black high heels pumps, and I indulged in the feeling of my foot easily slipping into them from being encased in hose. I then did my make-up and hair, and looked in the mirror. I was turned on by what I saw, and I became incredibly excited and nervous at the same time, for I was about to show myself for the first time.

"Are you ready? Man, you're taking a long time. Is this some sort of stupid joke?" he called out from downstairs.

"I'm coming down. Now, you have to be totally honest about how you feel."

I walked down, and the first thing that appeared in his field of vision was my legs propped up on heels and clad in pantyhose walking down the stairs. "Holy shit - you were serious!"

I came down, and stood about ten feet in front of him. "What do you think?"

He got up and couldn't believe that it was me he was seeing. He kept looking me up and down, and circling me, mostly looking and staring at my legs and ass. "So, you find yourself attracted to my look?"

When I asked that, he became a little uncomfortable. "You kidding? Of course not!" Despite what he said, I could see that he was sweating a little. So I started to walk to the kitchen to get a drink, and told him that I'm certain that he will, and that he hasn't won the bet until the night was over. As I walked into the kitchen, I saw in the reflection of the window that he was checking out my legs and ass. I walked over to the refrigerator and looked inside, bending over with my legs together and straight. He was silent, but I know that he was staring. I turned around, and caught his eyes looking down, and his mouth was open. I walked over and handed him a beer. He took it and looked at me and my breasts. "Man, this is weird." He then gave a nervous laugh.

"This isn't turning you on?" I asked. "No", he replied nervously. I sat down on the stool in front of him, and crossed my legs. "This?" He shook his head. I got off the stool, and slowly hiked up my skirt to reveal my pantyhose covered legs. "How about this?" He was sweating, but he shook his head "Definitely not". I then walked over to the couch and bent over in front of him, "how about this?" He shook his head. I started to hike up my skirt, and he still shook his head.

I then walked over to him, took his hand, and placed it on my pantyhose covered leg, and moved it up. As I moved his hand up my skirt, he took it away and gasped "It's not working". But he didn't move away. I turned around, and then bent over, propping myself against the arm of the couch. I pinned him against the wall with my ass at his crotch, and asked "what about this?" He didn't say anything. I could feel that he was throbbing hard. His cock was a throbbing shaft, and I never thought a cock could be so hard. It was perfectly lined up with the crack of my ass, and I could feel it throbbing even though he still had on his slacks and I still had on my skirt, hose and panties.

I turned around and held his collar, "It's okay, I knew I would win". He didn't say anything. He was still sweating. He then grabbed me and pulled me closer to him. He started smelling my hair and perfume scented neck, and then started ravaging me. I then felt his hand on my shoulder, pressing down. So I got down on my knees and stared up at him. He was overcome with lust. I unzipped his slacks, and pulled out his throbbing cock. It was huge, and it kind of scared me. I placed my hands on his lap, and his cock was right in front of my mouth. He placed his hand on the back of my head, and slowly nudged it down to his cock. I relented and slowly engulfed his throbbing shaft. He let out a long, sustained grown. He moved his throbbing cock in and out of my mouth, and I could feel the head of it throbbing when it reached the back of my throat. I wiggled my tongue along the underside of the shaft with every slide in and out. This went on for a few minutes until he pulled me up gently and said "I really need something tighter."

I turned around and spread my legs a little. I could feel the pantyhose stretching over my ass and thighs. I arched my back, and thereby propped my ass up towards him, ready to receive. He slid up the skirt and felt my pantyhose ass and crotch with his hands. "I can't believe I'm doing this" he said, with a quiver of lustful excitement in his voice. He then started to probe my hole through the pantyhose and panties. I felt his tongue stretch the hose and touch my tight hole. He got up impatiently and said "I need to slip it in". He pulled my pantyhose down and pushed aside my panties, and positioned the head of his gorged cock against my hole. He hesitated, not knowing if he wanted to penetrate me. I helped him by slowly pushing back against his cock. My hole slowly stretched over the head of his cock, hugging it. It hurt at first, but then the head popped in, and the shaft of his cock slid into my hole easily. We both moaned in utter pleasure. He started to pump me with long slow strides in and out. The bottom of his cock was lightly rubbing the top of my pantyhose, which were pulled own slightly over my ass.

"Ohh, it's so damn tight" he said, fucking my tight hole. The room filled with the scent of tranny sex as we moaned with pleasure and he fucked me the only way I could be fucked. We moved onto the couch and tried all sorts of positions, but I kept my clothes and hose on, because he liked it that way. He sat down on the couch, and I positioned myself above him, slowly sitting down on his still-throbbing cock, now glistening with his pre-cum and my anal juices from the lube. He held my ass, spread the cheeks, and lowered me onto his cock. I felt his shaft slide inside and fill me.

He then laid me on my back on the table, raised my legs in the air with his hands grabbing my ankles, and slid his cock into me while he stood. He was getting impatient. He fucked me, and he was taking his time. Needless to say, I won the bet.

At The Office

One day at work I noticed that the history on my web browser had some tranny porn sites. I was surprised because I don't look at tranny porn or any porn while at work. I stood up from my cubicle and looked around to see if anyone was looking. Nobody. I erased the history and went about my business. The next day the same thing happened. I was really curious who was looking at tranny porn at my desk. Did someone know that I sometimes wear pantyhose under my slacks? Does someone know that I am a secret crossdresser? I was ridden with anxious excitement and curiosity.

The next day was a Friday, and so I knew for certain that nobody would be at the office after hours. I fantasized about being dressed up all sexy at my desk late at night. I was trembling a little because I was so nervous and excited by the thought. I've never dressed outside of my apartment before. Finally, I decided to do it. It was my fantasy to be dressed like a sexy professional woman at the office. Maybe I can pretend to be taken in the copy room.

I wore pantyhose to work on Friday. When everyone left, I went to the ladies' room with a small bag filled with my stuff. I stripped down naked and then I painted my nails red. Lucky for me my legs were naturally smooth, so I slipped on a pair of pantyhose, then bra with some silicon breast forms, and then put on a very sexy skirt suit that consisted of a fitted stretchy gray mini-skirt, a tight turtleneck white top that was long-sleeved, and a fitted blazer that matched the skirt. I put on my earrings and necklace, and bracelet. I then put on my make-up and did my hair. I looked in the mirror and I was turned on by what I saw: a very sexy looking professional woman. I checked myself, and then packed my purse with lipstick, eyeliner, and then powder. I walked out of the restroom and it felt so exciting to feel my heels clacking on the tile floor and echoing in the room and even in the halls. I went to my cubicle and sat at the computer. I did some work, printed out some documents, etc.

I then walked over to the copy room to get my printouts. As I stood there looking at them, I heard the elevator ding and then open. Anxiety and worry rushed over me, because the copy room entrance was right next to the elevator hall. I heard something roll out of the elevator and down the short hall into the room right outside the copy room. A man came into the copy room and was about to turn off the light when he saw me. "Oh, hi. Sorry, I didn't know anyone was here". During most of his speaking, he was staring at my pantyhose legs. I stood there silent because I was scared. I didn't want to give myself away for sure with my voice. The night custodian has caught me! "I'm John - the custodian for these offices". I mustered up some courage and said to him softly "I'm Samantha". He looked at me and a grin came on his face. "Pleased to meet you Samantha". I realized that he knew that I was crossdressed, so I fumbled to make up some story. He said "No, it's okay, I'm totally fine with this" with a smile on his face, while walking towards me. "Can I get a look at you?" I nodded and slowly turned around 360 degrees. "Wow, you look great - and your body is very feminine". I was only 5'7" and weighed 115 lbs., and I was excited that he liked what he saw.

I realized then that he was probably the one that was looking at tranny porn on my computer. He could tell I was nervous so he was very gentle with how he interacted with me. He told me that I looked like a sexy woman, and that any man would be lucky to have me. He asked me to turn around again and so I did. He then asked me to bend over and put my hands on the small cutting table next to the copy machine. I was really nervous, but I did as he asked. I looked over at the glass wall and through its reflection I could see that he was checking me out while rubbing his manhood through his pants. I got scared and turned around and he came over to me and said "it's okay, I'm just admiring you". He put his hands on my shoulders and I looked down at his crotch and could tell he was really hard. I became instantly excited, and I don't know why but knowing that he was turned on by looking at my ass made me tingle with sexual excitement. I couldn't believe it - I never was with a man before.

He stepped back and he just continued to stare at me - my legs, my body, my face. He broke the silence finally started asking me questions: how long I've been dressing, whether I've ever gone out, whether I've ever been with a man, if I was curious, etc. When I said that I was kind of curious, he just looked at me silently. He stepped closer and asked if I knew how much I turned him on. I said "no" and then he unzipped his pants and pulled out his hard, pulsating shaft. My lipstick lips parted a little from my total surprise - I've never seen another man's hard penis before, and I couldn't believe that it was hard for me.

He came over to me and I didn't have to say a word. He gently guided me down on my knees and showed me what it meant to be his woman. He slid his shaft into my mouth and told me that I was doing a great job, and that I was such a sexy woman. He kept staring at our reflection in the glass. We spent a few hours in the office that night and he was gentle with me, and I felt so much like a woman - like I've never felt before. He would gently lean me against the copy machine and have me bend over with my back arched. He felt my pantyhosed but under the skirt and I felt so vulnerable but so turned on. He then positioned himself behind me and told me that I would now really feel like the sexy woman I was trying to be. I stood up and said softly "but I'm not sure if..." and he interrupted me and quietted me and told me that if I wanted to dress and look like such a sexy woman, then I would have to be taken like one. So I bent over again. I was scared but so excited. I asked him what he was going to do and he said that he would gently put it inside me. He had some lube that he used to masturbate with while watching tranny porn. He poured it on his shaft and oiled it up, and then he tore a small hole in my pantyhose and pressed the bottle against my trannyhole and squirted some lube inside me. He then positioned himself behind me and pressed the head of his shaft against my tight hole. I tightened up and he told me that he wouldn't hurt me, that he just wanted me to feel like a woman, and wanted to feel me as a woman. He pressed harder, and then it popped in and penetrated my tight hole. He slid his huge throbbing manhood in and out of me and I was quivering. My legs started shaking. My head cocked back and my mouth was open. I was at first moaning with a little pain, and then it quickly turned to a moaning of incredible ecstasy. I could feel his balls bouncing at the bottom of my pantyhose covered balls. I could feel it and hear it sliding in and out. We did this for hours, in the copy room, at my desk, on the chair, in the board room. By the time we finished my pantyhose was wet with the lube and his cum, and when I went home, I went home dressed because I felt for the first time like a total woman. When I walked to the elevator, my hole a little sore, but really wet. I could feel his man juices leaking out of my tight hole. He said that he wanted to do it again, to take me and make me his woman, his sexy secretary, and show me what it feels like to be a woman with a man. I was looking forward to next Friday.