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.

New Friend, Old Friend

Ron and I were friends for a few years. We met through work and hit it off immediately as a result of common interests. I didn't have many friends, so I really did appreciate our friendship.

One day he came over to my apartment to help me fix my computer. As he was going through the file system, he came across a picture of me all dolled up in pantyhose, high heel pumps, and a skirt-suit. I was really embarrassed because I hadn't told anyone about my crossdressing, let alone my only friend.

He said "Wow, who's this? Is this an old flame? She's hot!" I blushed. While I could have lied and said it wasn't me, I didn't want to, especially since I really valued him as a friend and didn't want to be dishonest. So, I told him that it was actually me. He looked up at me, and then back at the picture, and asked "Are you serious?" I told him how I've been crossdressing for years in private. I thought we would be nonplussed and surprised, but he wasn't. Instead he seemed curious.

He asked about the dressing and I answered all of his questions. He then said that there was no way that I could be the 'girl' in the picture, and then asked me to prove it. I went in the bedroom, and for an hour, got dressed up. I put on black pantyhose, black bra with my breast forms, a charcoal fitted mini-dress, and black high heel pumps. I did my make-up and fixed my hair, and then emerged from my bedroom in my femme self. He smiled big and said "wow, you look awesome!". I blushed again and thanked him for the compliment.

He got up and circled me, and said I looked great again. He suggested that I stay all dressed up for the rest of the night. We went to our favorite sports bar and he pretended that I was his date for the night. All the men were staring at my legs and ass, and smiling at me. I think he liked the attention that I got, because he made sure they knew that I was supposed to be with him. After a few drinks, I felt his hand on my knee, and then I felt it slide up my hosed thigh, his fingertips touching the hem of my fitted mini-dress right at the upper thigh. He asked "You really look a lot like a real woman - do you know how much?" I shook my head. He took my hand and then slid it under the table and onto his crotch. I could feel a huge, hard shaft pulsating under his slacks. I was really turned on. I never felt this way towards a man before, but then again I never felt so much like a woman before either - that feeling would reach its ultimate climax later that night, little did I know.

We took a taxi back to my place. I walked up the stairs in front of him, and I could feel my tight dress sliding up the sides of my thighs and hips, the pantyhose sheering over my ass and crotch. By that time, after wearing pantyhose all night, and with being so turned on, my crotch was wet. I heard my heels on the stairs, and I purposely stuck my ass out a little, and walked up with a flirty saunter in the hips. I knew he was staring at my ass and legs. He reached up and felt my ass and gave it a nice grab. It startled me and I softly said "hey!". He smiled and laughed.

When I was trying to open the door to my apartment, I bent over slightly to slide the key in, and he came up behind me and pressed his crotch against my ass. I heard him groan "mmmmmm". I could feel his cock completely swollen under his slacks, and it was pressed up against between my ass cheeks, which was slightly visible due to the tightness of the dress I was wearing. He felt up my pantyhose legs and asked "Do you also taste like a woman down there?"

I then said "Ron, what do you think you're doing?", with a slightly flirty tone. He kneeled down behind me and hiked up my dress to expose my pantyhose covered ass. He pushed against my back with one hand, and with the other gently held my knees, making me bend over only at the waist, with my legs straight and my lower back curved to push out my ass. He smelled me and said I smelled like a woman ready for naughty sex. I told him he had too much to drink, and then he started to probe my crotch and butthole through the pantyhose, using his hands to spread my ass and caress my thighs.

I closed my eyes and moaned with sexual pleasure. He got up. and then we went into my apartment. I placed my purse and keys on the counter, and when I turned around, he was right in front of me smiling. He held me by the waist, and gently pushed me down onto my knees and said "I'll really make you feel like a woman tonight". I was then face to face with his crotch, staring at his zipped up slacks, with a tremendous bulge. "Unzip it and gently take it out". I unzipped his pants, and slid out his cock through the hole. I pulled gently on the shaft, and when it found the hole, it sprung out. I couldn't believe how big he was. It was huge, and it was incredibly hard - so much so that the shaft and head of his cock was throbbing and pulsating. "Now put it in your mouth gently." I did, and he moved my head gently with his hands, making me take his shaft in and out of my mouth with my lips stretched around it. Juices consisting of my saliva and his precum dribbled down the sides of my mouth and down my chin.

He moaned, and started to move his cock in and out of my mouth a little faster, like was getting impatient. He then looked down and pulled me up rather quickly. He took me by one arm and threw me against the back of the couch so that I was bent over, with my hands on the couch holding me up, and my crotch against the back of the couch. I let out a startle, and he came over and hiked up my skirt and pulled my pantyhose down enough to expose my asshole. He probed my hole with his tongue, and then got up. I felt his cock between my ass, the head of it throbbing right above my hole. "Let's see if you can be fucked like a real woman." I said "Wait, Ron, please...". He cut me off, saying "No waiting - if you're gonna look this much like a hot woman, get ready to be fucked like one...". "But..." I said, wanted to express my concern about never being taken in the ass before. "But what?" he asked, "I'm gonna fuck you like the woman you look like, and since you don't have a realy pussy, I'm gonna pump you in the only hole that you have." He slid it down and it found itself snuggly on the outside of my hole. He then pushed and slide his cock into me and let out a moan. "ooooh, that's real tight." He then just started fucking me, first with just small thrusts with just the head of his cock, to tease me and to tease his cock, and then finally with long strokes in and out. I moaned in ecstasy, and he said "You like being fucked like a woman, don't you. I always knew you were a little sissy faggot."

He ravaged me for hours that night. He kept telling me how good it felt putting his cock inside me, about how snug and tight it was, and how he loved feeling his balls touch mine and seeing my hard stick wave up and down in synchrony with his thrusts in and out of me. That night, an old friend became a new friend, both him and me.

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.

Neighbor

One day I was in my patio and I saw my neighbor sitting in his patio. We greeted each other and I asked how he was doing. He wasn't very happy because his wife had left him a few months ago. I told him that I was sorry to hear of the news. Eventually, I came over to his house to talk more. He told me that his wife left all her stuff behind and just up and left with another man.

I felt bad for him, but I was curious about what she had left behind. I was always curious about dressing in women's clothes. I asked him what he was going to do with her clothes and he said that they were in trash bags next to the door leading into the garage. I looked over at the garage door and saw the bags. I told him I could get rid of them for him and he said that that would be great.

He asked if I wanted to go to the movies and I said sure. The movie started in two hours, so I went back to my apartment with the bags. I had a little under two hours, so I decided to try on some of the clothes. I slipped out of clothes and slipped into some nude pantyhose and an ivory skirt suit. I slid my hosed feet into the high heels. I found some of make-up in the bag and put some on. I've had some experience putting on make-up on my sister, so I was able to do a pretty good job on myself. My hair is naturally long so I just curled it a little. I walked around the house and felt very sexy.

Right then I heard someone knocking at the door and I was scared. It was my neighbor. He was early! I told him that I had to get dressed. He said "That's ok. I saw you through the window - I know". I opened the door, very nervous, and he stepped in. He looked at me and said "Wow, you look great - those clothes fit you really good". He asked if I would go out to the movies dressed up like that. I was nervous but I said ok. He first took me to get some dinner, and he kept looking at me and was saying that he was amazed how much I looked like a woman. He would stare at my legs, my butt, and all over. After a glass of wine, he became a little flirty and started to treat me more like a woman, taking me in his arm and walking me out of the restaurant. During the movie, he put his hand on my knee and gently rubbed my nylon leg. I was really excited. We went back home and he asked if he could come in. We shared a few drinks while we sat at the couch. He asked me how long I was dressing and I told him that this was really the first time. He then asked if I was ever with a man, and I told him no. He looked at me and then asked if I ever fantasized about being with a man while dressed up like a woman. I was a bit embarrassed, and I told him that sometimes I did. The conversation went on like this for around twenty more minutes. His eyes most of the time were down at my crossed legs, but strangely I was liking it and feeling excited by it.

He stood up and came over in front of me while I was still sitting. His crotch was in front of me and he just stood there stretching, and said thanked me for being his sexy date for the night. We both laughed a little. There was a bit of an awkward silence, and he was looking down at me. I was looking down at his shoes, and then I looked up at his crotch and noticed a big bulge. I looked up at him and he smiled. Still sitting on the couch, I leaned over and put my hand gently on the bulge and looked up at him again. He smiled and closed his eyes, and then opened them. I could feel his manhood pulsating under his slacks. I was nervous and excited all at once. I thought about how the hardness I was feeling under his slacks could end up sliding in and out of my pantyhose covered bum that was sitting on this couch - the pantyhose covered bum that he was staring at all night.

I unzipped his slacks and reached in. I felt his shaft and it was really hard and really hot with it being all gorged. It was slightly bent in the pants, and I pulled it out of the zipper hole of his slacks. It sprung out straight and I started to stroke it. He said his wife never got that close to his manhood with her mouth. I then put my lips around the head of it, and I could taste him. He put his hands on my head, and then to my surprise he slowly moved forward and slid his shaft into my mouth. We did this for a few minutes, and then leaned me back onto the couch and then lifted my legs over his shoulder. He could see under my skirt now and saw that I was getting hard under my pantyhose. He asked if he could be my first. My red lips were still wet from his leaked juices, and I slightly nodded, scared that it would hurt. He tore a hole into my pantyhose, pushed my legs apart, and I slid down the couch and was now fully on my back, ready to receive him. I felt the strength of his arms grabbing my ankles as he held them with my legs spread. I could feel the cool air blowing against my exposed hole. He rubbed the tip of his wet cock against the hole and then slowly slid it in and out. It hurt at first but then it was heaven. We both moaned as he took me as a woman. I was surprised how easily it slid in and out. He was pretty well endowed, so I could feel him stretching my hole and going deep inside me. Each time he slid his shaft deep into me, I felt the tip of my cock swell, as if each thrust of his cock was pumping incredible pleasure into mine.

We did this all night, and he thanked me for helping him through such a rough time in his life. From then on, we became the best of neighbors!

School Friend Outing

When I was in high school I wasn't very popular. In fact, I was quite a loner. I had a few friends from the place I worked after school, but I usually chose to be alone when I wasn't working or in school. My escape from the loneliness of high school was to dress up like a woman in the few clothes I was able to buy with the money I saved up from working.

Sometimes, I liked to wear panties and pantyhose under my clothes when I went to school. One time my parents left for two weeks to go on a trip to Europe. So I had the whole house to myself. I decided to dress underneath my regular clothes in panties and pantyhose and go to school. Everything was great until an older class boy was sitting behind me in my math class, Jim, leaned over and asked me in a whisper if I was wearing pantyhose. I was nervous, but finally said "yes". He just said "nice" and didn't say anything else after that. I was scared that he would tell the other boys, since he was a jock and quite popular.

When I went home I put myself together, even putting some subtle curls in my naturally long hair. But when I came out of the bathroom, the doorbell rung. It was Jim. He said that he was curious about why I dressed up and just wanted to talk. I let him in and told him that I'll get dressed. He asked me to dress up for him because he always wondered why some boys dressed as girls.

I got dressed, put on my makeup, and made my naturally long hair. I came down and he looked at me and was really surprised. He said "Wow, you look like a girl". I just smiled. He asked me to walk around in front of him to see if I walked like a girl. He kept looking at my legs and my butt, and asked if I was wearing pantyhose. I told him I was.

I turned on the TV and he said to turn it to the sports channel. He said he wanted to watch the game, but that it would be fun if I pretended I was his girlfriend. He asked me to get him a drink and I did. We were having a lot of fun. I got up to pick up the empty glasses. Not really being aware, I bent over slightly in front of him to pick up the glasses and I heard him say "woah". I asked him what was wrong, and he told me that my skirt hiked up a little when I bent over, and stretched over my ass. He said I had a really nice butt and laughed. I was then surprised to notice that there was a growing bulge under his workout shorts. When I went to the kitchen and put the glasses in the sink, I was surprised to find him behind me.

He asked if I liked dressing like a woman and I said I did. Then he asked if I would ever like to feel like a girl. I didn't know what he meant, so I asked him what he means by feeling like a girl. He came over to me and then started to show what he meant. He kissed me and moved his hands all over my ass, and then under the skirt. He bent me over the counter and continued to kiss me from behind. I bent over some more and he knew that I understood his question, and that the answer was yes. He put his hand under my skirt and rubbed my crotch through the cotton gusset of my pantyhose. "You really look like a girl, and I bet you really feel like one too". He rubbed against me with his crotch and I could feel that he was really hard. "Are you sure you don't have a pussy under here?" he asked. I told him that I have something he could slide his manhood into, but that it's probably really tight since it's never been penetrated before. He tore a hole in my hose and I bent over even more so that I can really receive him. He positioned himself and pressed the head of his throbbing manhood against my hole. He said "Wow, it's really wet" and I told him that I put some lube there while I was getting dressed. The head popped into me and he slid in and out slow. I felt like a girl, and I really liked the way it felt. I felt so femininely vulnerable in the position I was in. It first hurt when he first put it in but it felt really good after that. I could feel him pumping in and out, deep inside my tight hole. He told me it felt better than a real pussy, and smelt better too.

The next two weeks, he came over every day after school and I tried on outfits for him. He continued to make me feel like a real girl, the way he would handle me. It was one of the best two weeks of my life.

Fantasy 1

We meet in a hotel room. You come in and we're both a little nervous. You're dressed in business attire, and I'm wearing a sexy skirt suit with pantyhose, heels, etc. We plan not on having actual intercourse, but just a little chat and maybe some touching fun. You come in and sit down. I offer you a glass a wine, and you say that you'll have a little. You sit down on the chair, and I sit opposite you at the table. We chit chat a little, and I tell you that it's okay for you to look at me, and that the 'eye contact' rule doesn't quite apply here. So you gladly look me up and down with slightly nervous but eager and lustful eyes.

I ask if there's anything I can do, and you ask me to stand up. I slowly stand up, and pull my skirt down a bit, since it was sliding up when I was sitting down on the chair. I can feel my pantyhose stretching over my legs and sheering around my crotch, and the skirt, too tight, is stretching over my pantyhose ass underneath. You ask me to turn around for you, and I do, slowly. You look at my hose clad legs propped up on high heels, and see my ass through the tight skirt stretching over it.

I ask you if you want more wine, and you say 'sure'. So I come over and get your glass, at which point you place your hand on my ass and move it downwards, gliding over the back of my thighs. As you're about to move upwards under my skirt, I walk away to the bottle of wine, which is sitting on the desk away from the table at which we're sitting. I bend over slightly to pour the wine, and you watch me. I can feel your lustful eyes all over my ass and my pantyhosed legs. You see the skirt hiking up a little, and you get turned on. You get up and walk over to me, and press against my ass. I can feel your cock getting hard through our clothes. I push my ass a little against your crotch, and your hard shaft comes to be positioned along the crack of my ass. We're doing this gently through the clothes. You tell me how much you want to fuck me. I ask if you really want to put your throbbing cock into my tight asshole and you moan 'mm-hmm' with obvious lust.

I turn around and go to the bed, and sit down at the foot of it, facing you as you're standing by the wine. I slowly spread my legs and hike up my skirt. You see my crotch through the pantyhose, and you can see my hard cock pressed down by the hose against me. I pull them down, and you see shapely nylon legs in heels spread out, the pantyhose pullled down a little to reveal a hard throbbing cock in-between. I see a huge bulge throbbing under the crotch of your pants. I pull my pantyhose back up and pull down my skirt, and reposition myself in a 'professional' way. I'm sitting on the edge of the bed with my legs together, in a 'proper' fashion, and you come over to me and stand in front of me, your bulging crotch right at my face. I look up at you and I rub your cock throgh your slacks, still sitting at the edge of the bed.

"Do you really want to fuck my tight tranny hole?" I ask you, looking up at you and still rubbing your cock through your slacks. You pull out some condoms from your pocket and say "I wouldnt' have brought these if I didn't want to". I unzip your slacks slowly, without unbuckling them. I reach in and pull out your hot cock, which is throbbing at this point. It's now completely sticking out of your slacks totally erect, pulsating and forming pre-cum at the tip. I take the condom, tear it open, and unroll the condom down your shaft methodically and slowly. I then look up at you while you are standing, and I grab your throbbing cock at its base, open my mouth, and slide it into my mouth. My mouth is small so my ruby red lips are stretched around your cock. You feel the wet and warm feeling of my mouth, and my lips pressing and stretching around the head of your cock. You slide it in half way, slowly - in, then out. You repeat, slowly, with broad strokes, in and out of my mouth. You look at the mirror and you can see yourself standing, and me sitting in front of you, and your cock sliding in and out of my mouth.

My legs are still pressed together, but there is a noticeabl bulge between my legs. You put your head back and continue to slide your cock in and out of my mouth. Then you pull out, and we both realize that we've crossed some boundaries. I look up at you and reach over to my purse. I pull out some sex lube and pour it on your cock and rub it all over it. My finger tips gliding on it and spreading the lube over your shaft drives you nuts. I get on all fours at the edge of the bed, ready to receive you. You hike up my skirt slowly, and then you expose my pantyhose covered ass. You tear a hole at the crotch of my pantyhose, exposing my tight hole and my throbbing tranny stick. Immediately you smell perfume, and the scent of the dirty sex you're about to do with a tranny. You pour some lube onto my hole, and it drips down from my asshole and down my tranny cock and balls. It glistens, inviting you to slip it in. You position yourself behind me, and then place the head of your cock against my asshole. My hole is incredibly wet, and incredibly small for your cock. You're not sure if it will fit. You then press it in, slowly, and watch it disappear into it as I moan. You see my hole stretch around the head of your cock, and then the head pops in. You feel my asshole, incredibly warm and incredibly tight around your cock. It's incredible and even a tad painful because it's so tight.

The head of your cock slowly pops inside me, and then you slide it in slowly. As you do so, my cock throbs uncontrollably and gets even harder. Again, you go in and out slowly, with nice long broad strokes of the shaft: in and out, in and out. You look over at the mirror, and you can see me doggy style, your cock going in and out, and my cock between my legs hard and bouncing up and down with each inward glide of your cock into my asshole. You can feel your balls gently bouncing against my tranny balls with slide inward. You can't believe how tight it is, and I can't believe how hard I am from being fucked. I could cum from your fucking my hole. You turn me over on my back and spread my legs. You push them slightly back so my ass raises upward. You position your cock at my tight hole, and again slide it in: popping in the head first and then the whole length of your shaft. You look down at my spread legs, covered in pantyhose that's been torn through by you at the crotch. YOu see see me grabbing my thighs to spread my legs open for you and to receive your cock even deeply in me. I can feel you going in and out of me. You can see my hard cock just above your shaft going in and out of my tranny hole.

We then proceed over the table and you bend me over a chair. I straighten out my legs and spread my legs slightly. You continue to fuck me from behind, both of us now standing. I'm moaning in ecstasy and your going wild with sexual excitement. You are about to cum, and you move a little faster, and then make long, slow strokes in and out of my tight asshole. You grab me by my waist as I'm bent over, and you cum, with incredible bursts of cum with each glide inwards. You cum so much it leaks out of the condom at the base of your cock and dribbles down our legs. You pull out and your legs are weak from your orgasm. You see that I've got cum all over my hosed legs and high heels because I came too from your slow, deep pumpings of my asshole. When you leave, you're satisfied and your cock aches a little from having fucked such a tight hole, and it ahs the taboo smell of hot sex with tgirl.

A Meeting To Cum For

There's been a man who has been really wanting to meet me. Again, I typically don't meet men but this one was particularly into pantyhose tgirls. Since I'm really into wearing pantyhose, I thought that this man might be fun to meet. It's one thing to meet a man who is into tgirls, but it's really quite another, I think, to meet one that appreciates pantyhose clad legs as much as I!

Anyway, after almost a year of correspondence, I decided to meet this man. Partly I decided to meet him because I had met him before at a t-club a couple years back. I had no idea at that time that he had a thing for tgirls in pantyhose. It was not until he sent me a picture that I recognized him. He is an older man, which is a plus in my book, since I would prefer meeting older men on the rare occasions I do meet them. (There have been a few exceptions ;)).

I dressed in a long-sleeve turtle-neck tube-dress, asphalt gray in color. It fits very tight and it is a very short dress. I wore black sheer-to-waist pantyhose (with no panties ;)), black open-toe ankle-strap high heels, and a black fitted blazer. The clothes fit my body perfectly, hugging me in the right places in just the right way. The only thing is that when I would walk, the dress would stretch at the legs and, because it's cut so short, it would hike up my legs! It was sexy for sure - but boy did I get some attention! I filled up for some gas at the corner of SM Blvd. and Highland, and I got lots of whistles and looks. That was hot - I made sure I bent over slightly to show off my legs and to make the dress stretch over my pantyhose covered ass and 'express' it to the cars passing by (many of which seemed to enjoy).

I met this man at his place. (I make sure that I play it safe and so took some measures to ensure as much as possible that no harm would befall me). When he saw me, I could tell he was satisfied - his eyes were hardly meeting my eyes, but instead scanning my legs and ass, and my body. When I walked in front of him, I could feel his eyes all over my ass and legs. I walked with a nice sway to my hips so that he can see my ass moving as the dress stretched over my ass and thighs as I walked. I went into his place and he looked at me, giving me compliments. He touched me nervously, and I told him that we could play it slow - so no touching for now - just looking.

I sat down on a chair and he stood away from me asking me if I'd like anything to drink. I sat and crossed my legs, feeling the dress sheer all over my body with every move, and the hose sheering and stretching over my legs, ass and even my crotch area. He was staring at my legs and when I crossed them, I could see his eyes move up my hosed legs and peer between my nylon thighs, hoping to get a glimpse under the skirt.

We started by taking pictures. I posed for him in various positions. First, it was just me sitting and standing, posing in sexy but not at all too revealing ways. I could sort of see that he was getting aroused but it wasn't entirely clear. Then I started to pose more provocatively - bending over in front of him, laying on the bed with my legs spread but scissor-crossed so that he can't exactly see up my dress. Then I bent over, and slowly pulled up my dress to reveal the bulging cotton gusset of my pantyhose. I slowly pulled the dress up more, feeling it stretch over my pantyhose ass. He continued to take pictures and then moaned "Oh, ursie - I want to fuck you!" I looked over and I could see that he was really hard rock hard. His shorts had an enormous bulge in it.

I went over to the bed, got on all fours, bent over doggy style, and then hiked up my dress to expose my pantyhose covered ass. He took pictures while moaning again in lust. I turned over on my back and then spread my legs in front of him. He looked at my pantyhose covered legs and crotch with a look that was just completely consumed with one thing - zoning on my crotch, thighs, and legs. His shorts had a small wet spot on them, which I gather was from his pre-cum. He pulled down his shorts, saying again how much he wanted to fuck me. His cock must have been around 8 to 9 inches, and it was seriously throbbing and pulsating. It took me aback. He went between my legs as if to give me oral through the pantyhose - his hands on my thighs as if to spread them. I pushed him back and said that I am not into oral even through the pantyhose. Then I got back on all fours and bent over at the edge of the bed doggy style. He buried his face in my ass and started to really eat my hole through the pantyhose, telling me he wanted to smell my butthole and put his dick into it. I couldn't believe it.

I got off the bed and stood at the edge of it, bent over. He rubbed his cock against my thighs and crotch. He rubbed against me hard and I could feel his throbbing cock (which by this time had a condom on it) rubbing against my ass and crotch. His eyes rolled back into his head and he came. I could see the condom swell with each squirt of his cum.

What was particularly nice about this meeting is that the man was really into pantyhose clad legs - you could see it in his eyes. I could tell that sexual lust was filling up within him and that he was barely able to restrain himself.