Airing Out

Tina thought that it would be fun for Tony to go to the cocktail party all dressed up as a woman. Tina thought that he had a very slim, feminine figure for it. Since it was supposed to be a formal affair, Tina gave him some nude pantyhose, some red satin panties, and a vibrantly red dress with matching satin heels. Tony became complete as Toni when Tina did Toni's hair, makeup, and completed it all by putting on her a sparkling collar necklace and matching earrings.

At the party, everyone was convinced that Toni was an elegant woman, and Tina and Toni were thrilled with their secret. Toni started to feel the sensual feeling of being so elegantly and femininely dressed up as a woman. The way her hosed feet slid into the heels, and the way the heels felt as she walked. The sheering and stretching of the pantyhose over her crotch, ass, and legs was amazing, and especially the way the dress rubbed against her hosed ass and legs.

At one point she became very hot, and she discovered first-hand that pantyhose does a great job at keeping you warm. Unfortunately, after being indoors at the party for a couple of hours, her crotch started getting very hot and wet. So, she walked over into the study, which was empty. She sat down on the leather couch and lifted her dress, spread her legs, felt the cool air wafting upon her pantyhosed crotch. It felt so good that she slid off her panties so the air could more directly cool her hosed crotch. It started to turn her on, and it was at that point that she realized that she wasn't alone in the room. There was a man sitting in the shadows, wearing a black suit and sipping on some brandy. She pretended not to see him, and continued to make a show for him, in a very sensual way. He got up, and came over to her. You know what happens next!

Too Feminine

When he told Tom that he crossdressed, Tom didn't believe it and just laughed. Tom wanted to see for himself if it were true. So, he dressed up and showed Janey to Tom. Tom couldn't believe his eyes. He told Janey that he looked too much like a hot woman that it was scary. Tom got confused, because he was totally straight, but he wanted to fuck Janey. He couldn't believe that under that skirt was a cock. He was excited.

Later that night, after a few drinks, his curiosity became total lust. Janey was too feminine to be a man, even if she had a cock. He started to become sexually forward, pushing his body against Janey and rubbing his crotch against her ass so she could feel how hard his shaft was through their clothes. She didn't say anything, but instead just bent over the chair and turned to look at him with total submission. He unzipped his pants, and pulled out his rock hard cock, pulsating so much it hurt. He lifted her skirt, and saw the tops of stockings. He could smell her tight pussy through her sheer panties, inviting him to squeeze in his hard shaft and pump it slowly with long, slow strokes in and out. He popped the head of his cock into her, and she moaned with pleasure. He couldn't believe how tight it was. She was way too womanly to be a man. He made love to her all night.

Confessions of a Straight Man

Dear ----,

I'd like to confess a recent encounter that I had that initially had me wondering about my sexuality. I should say from the outset that I am, consider myself to be, a straight man. I come from a liberal upbringing and have members within my extended family who are openly gay. They are fully accepted by the rest of the family, so if I were gay, I know that I would be the first to admit it.

Recently I was at an office costume party, which is customarily held every weekend before Halloween. I typically do not dress up, except for maybe a black mask that covers only my eyes. I do this to avoid the hassle and expense of buying an entire outfit, and for the reason that it makes it easier for me to go to the party straight out of my office: I just take out the mask from my drawer and I'm dressed for the party wearing the shirt, tie, and slacks I was wearing during the regular work hours.

I was having a somewhat dull time at the party until I saw someone who appeared to me to be a young woman who, like me, did not dress up in a costume. She was very attractive and looked incredibly sexy in her gray skirt suit. Her pencil skirt hugged her slender figure, and she appeared fairly tall for a woman, especially in her high heel pumps. I walked over and introduced myself, and she introduced herself as "Sam". When I heard her voice, I became a bit puzzled, because everything about her was screaming 'sexy woman', and her voice was somewhat androgynous. We chatted a little and she told me that she worked over in accounts receivable. I was surprised I had never seen her before, and when I expressed that to her, she said that that's probably because she's normally dressed in a suit just like me! I couldn't believe it - though I registered what she had said, I couldn't help but see her as an incredibly attractive woman. I then started to wonder if she would 'move' like a woman in bed as much as she looked like a woman at the party. I started to get hard, and there was a noticeable outline of my stiff shaft in my slacks. I couldn't stop thinking of what it would be like to feel her with my hands and to slide up her skirt. I wanted to know what she had under that pencil skirt, under those pantyhose, and what it would feel like to fuck her. I couldn't help it - my mind was going wild. I couldn't keep my eyes off her legs, and at one point I was able to get a good look at her ass. I was instantly mesmerized with lust.

She asked where I worked, and I pointed over to my office. I asked if she wanted to see it, and she hesitated a bit and said okay. We went into my office, with her going ahead of me. I couldn't keep my eyes off her ass, her hosed legs, and her waist and hair. I wanted to fuck her so bad my legs were trembling. I couldn't believe what I was thinking - what I was desiring! She walked in and I closed the the door behind us. We talked for a little bit and it turned out that she dressed regularly, but in private. I asked her if she had ever been with a man and she said no. I was surprised. Anyway, we talked like this for a little bit, and I was really turned  on throughout our conversation. I just couldn't keep my eyes off her and imagining hiking up her skirt and tearing through her pantyhose. The conversation trickled to a sort of light one, and she asked what I was doing on Halloween, which was a few days away. I wasn't doing anything, and so she invited me to another costume party in LA. I said that I'd go only if she was dressed like this. We both laughed (I was dead serious), and she said she'd try to dress 'like' it but not exactly the same outfit. I agreed, and we exchanged numbers.

The next few days I actually tried to look for her at the office, and couldn't figure out who she was! When Halloween night came, she called me and I went to pick her up. She was wearing an ivory dress that hugged her body nicely. It stopped at the knees. It wasn't tight, but it did stretch over her body when she'd bend and move. She looked super hot, and I couldn't get over her ass! She was dressed to the T: pearl necklace, a whitish/nude color hose, and heels that matched her outfit. The whole night at the party I must have been rock hard just staring at her. At one point she bent over for something and I was mesmerized by her ass: I was drawn to it and just wanted to fuck her so badly. I composed myself.

Later, I dropped her off and she asked if I wanted to come up. I nervously said yes and walked behind her up the stairs. That was in itself enough to make me cum all over in my pants: I could almost see up her skirt, her nylon thighs rubbing against each other, hear her heels hitting the stair with each step up, her ass moving back and forth as if to entice me to fuck it. In her apartment, we had some wine and talked for an hour. Eventually it turned to the party and then I found myself commenting on how great she looked. She was shy about it, but smiled and took the compliments graciously. She then said that it was clear that I liked the way she was dressed, and then She looked down at my crotch and probably saw that I was rock hard through the slacks. She was sitting there, smiling and biting her lower lip. An awkward silence filled the room, and I just looked at her up and down, and she stood there leaning against the table biting her lower lip. I was embarrassed but confessed that yes, I was quite excited by her.

She turned around and looked at the things on the table. I commented on how great she looked, and that's when she bent over with her legs together. Again, another awkward silence. She broke it by getting up and going over to the table to pour some wine. She was in clear view of me, and she bent slightly over the table so I got a good glimpse of her hosed legs, slightly parted, her dress stretching over and slowly slinking up her pantyhosed thighs and ass. I couldn't help myself. I walked over to her and pressed my crotch against her ass crack, which was visible through the skirt stretching over her ass. I slid my hands down her thin waist, and then to the arch of her lower back, and then down to her ass. Her ass was incredibly tight, and the synthetic stretch material of her skirt stretched over it and rubbed against her pantyhose covered ass. She said "Ummm, what are you doing?" and I just said 'i don't know'. She didn't stop me. Instead, she pushed back her ass into my crotch, and then turned around and walked around the table and sat down on an armchair. I walked over to her side, and my crotch was right at the level of her face. She rubbed my hard cock through the slacks, looked up at me with her mouth slightly agape, and that's when she unzipped my slacks and pulled out my throbbing cock. I saw the head of it pulsating, just inches from her mouth. She parted her lips and I couldn't help myself...I gently slid my cock down her throat. I couldnt' believe what was happening. She sucked on my cock like no other. I looked down at her taking my steady thrusts in and out of her mouth, sitting with her legs crossed. I just had to fuck her. I wanted to feel what it felt like to fuck her tight asshole. I could hear her sucking on my cock. This went on for a few minutes. I couldn't wait anymore, so I pulled her up, and I slid my hand up her legs and under her skirt. I felt her crotch and ass through her pantyhose. I told her that i wanted to fuck her. She just looked at me with her mouth slightly agape and still biting her lower lip. Then she propped one leg onto the chair, and I knelt down and started to lick her crotch through her pantyhose.

She told me again that she had never done this before, and she sounded nervous and excited. That's when I told her that I could really make her feel like a woman. She said that maybe we should wait, and I told her that she looks too good, and that anything that looks that good will instill the desire to fuck in anyone. She turned around as if to tell me that she understood what must happen if she's going to look that good dressed as a woman. She turned around and slightly bent over. One knee was on the arm of the chair, and the other leg was straight, holding her up from the floor. I bent her over the chair and she told me that she was a little nervous. I said I would stop if she wanted to, but she slowly shook her head and bit her lower lip again, as if to contain the excitement and nerves. She bent over and I started to probe her asshole with my tongue. I could see her cock and ballsack pressed against her crotch from the tight pantyhose she was wearing. I could taste and smell her asshole, and it wanted me to slide my cock into it and pump it nice and slow with long, slow and steady strides in and out. The smell is what really drove me crazy - it was taboo, it was hot raunchy sex I was about to undertake: I wanted to fuck her in her tight asshole and she was willing to let me do it.

I pulled down her pantyhose just below her ass and continued to lick her hole. That's when I noticed that she was rock hard too. Pulling down her pantyhose just below her crotch made her hard cock spring out. That drove me crazy, and I felt sexually excited and also the need to be more of a man - perhaps to make up for feeling like I've been so sexually seduced by such a girly boy. I got up and she turned her head to look at me. I positioned the head of my cock against her anus and pressed lightly. I gently pushed her against the back of the armchair. I couldn't help myself, and then she said "wait..." and right then I pushed enough for the head of my cock to penetrate her hole. She let out a moan, and I could feel her ass trembling as my throbbing hard cock glided into her incredibly tight butthole. It was incredible: super tight and warm, and really wet. I slid it in and out, and I couldn't believe how tight it was. Everything was incredible, and I have to say that it started to smell like hot anal sex, and I began to tremble with anticipation and excitement. The sounds, the sights, the smells, and the feeling was all just wrapped into an incredibly hot, sexy experience. I could hear her moaning with every thrust. I saw our reflection in the window: her pantyhose legs, long, propping up her hot body, bent over my desk, her hard cock bouncing up and down with each thrust I made into her.I could see my cock sliding in and out, and it was so tight it almost hurt a little. It was so tight that I could see the rim of her hole go in an out as it hugged my shaft. I could see that my slacks were wet around the zipper hole. I tried to pace myself, but even though I pumped her slow and nice, with long slow strides in and out, I was about to cum. And I did. At first I came inside of her, then I pulled out in mid-squirt and came on her ass and pantyhose. I couldn't believe the intense feeling. That night when I went home, I kept wanting to smell her ass juice on my cock, and I must have masturbated about five times when I got home, getting excited just by her smell and the memory of her tight body and even tighter ass pussy.

Anyway, we still continue to meet from time to time. I don't even really notice her when she's dressed normally at work. But boy when she gets all dolled up, I just can't wait to fuck her.

Thanks for these stories - I hope this story shows my gratitude for them.

Straight Man

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.