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.
Tuesday, March 2, 2010
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!
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.
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.
Subscribe to:
Posts (Atom)