Better than a pussy

Johnny came out in the parking lot of the nightclub, disappointed that his girlfriend couldn't see him. He was horny as hell and now, his hopes for making love to his girlfriend all night long were dashed. Despite his disappointment, his horniness was still there, and it's no surprise that he heard the clacking of women's high heels coming down the street. He lit up and saw a super hot woman wearing a sexy blouse, a short miniskirt, and black pumps. She was walking his way and he couldn't help but stare at her. All he wanted was a vagina - a tight, wet vagina to squeeze his hard cock into and pump until he came.

She came over to him and asked him if he knew what time it was. Strange, women aren't so brave at this time of night, he thought to himself. They chitchatted for a little bit but all he could do was stare at her legs and mouth. He thought about how those legs came together under that skirt, leading up to her pussy, which he surmised was incredibly tight given her thin and small frame.

She said she had to go, and then turned around, only to drop her purse. She bent down to gather her things, and Johnny got a nice view of her legs and ass. Her skirt hiked up enough for him to see that she was wearing nude pantyhose, which he hardly saw women wearing ever. He wondered about how the pantyhose were hugging her crotch, and he just wanted to dive in there and taste her pussy.

He couldn't resist, so asked if she'd like to go to his place. She hesitated but then after telling her that he meant nothing but to have a pleasant evening, and reassuring her that he was a nice and open-minded guy, she gave in.

Small talk over some drinks eventually led to heavy petting on the edge of his bed. Johnny was incredibly hard, and all advances to move his hand up her nylon legs and under her skirt were blocked by her hand. This happened a few times and he was wondering if she perhaps just didn't want to go there. When he asked if she didn't want to do it, she bit her lip, and told him to stand up. She unzipped him, pulled out his throbbing cock, and just engulfed it. Her small lips and mouth stretched around his hard shaft and her head went back and out, steadily and in moderate speed. He didn't have to move, her mouth was fucking his cock like no other!

But he wanted to fuck her. He liked getting his dick sucked - and boy could she suck his dick like no other - not even his girlfriend! But the feeling of sliding his hard cock into a tight wet pussy was what he always loved doing: thrusting in and out in nice, slow and even glides, feeling the wet pussy tightly wrapped around his shaft, holding the woman's waist while he fucked her pussy nice and good. He couldn't take it anymore and said he wanted to fuck her.

She then got off the bed and on her knees, starting to pump his hard shaft with her mouth, but this time quicker, like she wanted him to cum. He knew he wouldn't cum that way, even though it felt incredible. He stopped her and repeated himself: I want to fuck your pussy. She looked up at him, her mouth dribbling with saliva and his pre-cum. She told him that she was sorry, but that she didn't have a pussy. He looked down and saw that there was a bulge under her skirt!

Instead of being shocked in negative way, he was overcome with an urge to fuck. He was too horny. She apologized again, and said that he could fuck her mouth. He stood there and didn't know what to say. She got up, and then onto the bed, and got on all fours, bending over in front of him. She said again 'I'm sorry, I just don't have a pussy...I'm not built that way. But maybe you can fuck me this way. I'm a virgin still'.

He obliged. He couldn't help himself. When she was bent over ready for doggy style on the bed, an incredible feeling of lust went through him and into his cock. She slid up her skirt and he could see her rectum through her sheer nude pantyhose. When the scent of her wet, sweaty, virgin hole hit him, he went wild.

He positioned the head of his cock against her asshole and pressed. It didn't go it, but she pushed back and impaled herself onto his long shaft like a piece of meat on a skewer. His cock slid in with a little effort, but when it did, he couldn't believe the sensation. He couldn't believe how better it felt than a real pussy! He told her that her ass felt better than his girlfriend's pussy. It was so tight that his shaft was being strangled in a way that was delightful that he was moaning with ecstasy with each stride in and out. She was moaning with incredible delight. With each thrust in, he could feel her tighten up her already-incredibly-tight hole. It was better than a vagina.

Hot "Chick"

Ben and Carl weren't very popular at school. They were sometimes picked on but for the most part they were just invisible. They were grateful that they found each other since otherwise each would have been a complete loner, both at school and also away from school.

Every weekend Ben would come over to Carl's place to play video games. That, in addition to reading comic books and computer and gaming magazines, was all they pretty much did.

Ben often talked about how great it would be if they found some "hot chicks". Ben longed for that kind of intimacy with a woman and wondered, as a virgin (which Carl was, too), what it would be like to kiss the head cheerleader, say, or just to be with a girl in an intimate way. Carl longed for intimacy too but it was a little more complex for him. See, Carl had a secret - a secret going by the name of "Karly". Karly loved to dress in his older sister's pretty things. Carl couldn't get the girls but he, too, wanted to be with a girl just as much as Ben. However, Carl found a way to remedy the feminine lacuna in his life: he could dress up and be the girl to whom he could do whatever his lusting heart desired! But, because Karly looked so hot and sexy, which was completely contrary to the skinny, dorky, long-haired gamer Carl, the whole sex thing became entwined with Karly: it was Karly who wanted to experience what it was like to have sex...as Karly!

One Friday night, when Carl's family were up at the Lake House, Ben came over to stay the night. He was going off again about how he just wanted to meet a "hot chick" and to make love to her all night while they were both surfing on the internet on their laptops. Carl could see from the bedroom mirror that Ben was looking at porn on his laptop, and that Ben was noticeably hard under his pants.

Carl told Ben that he could dress up as a girl just for fun. Ben laughed and said "whatever, you're weird". Carl went into his sister's bedroom and came back out as Karly an hour later, wearing thigh-his, high heels, a frilly skirt, tube top, and some make-up. Ben looked up and his jaw dropped!

Karly brought Ben over to the bed and said "Just pretend that I'm a girl, then you can live out you fantasy". Ben was hesitant but intrigued. He couldn't believe how hot Karly (Carl!) looked all gussied up as a girl! He checked out Karly became really hard. He finally gave in. "Okay, we're just experimenting - doing this since this is the next best thing, er, well, you know what I mean". "Yes, of course!" Karly responded.

Karly was sitting at the edge of the bed and Ben was still standing. She hopped on the bed on all fours and turned around to see Ben. "What do you think of this?" Ben was slightly trembling, and his pants had a incredible bulge. "Uh, yeah, that's hot". "How about this?" Karly laid on her back and spread her legs, holding her thighs to help lift up her ass a little and bring her ankles by her ears. Karly's panties shifted a little and showed her tight butthole. "Yeah, that's nice" Ben said, with a quiver in his voice.

Karly got up. "You want me to suck your cock?" Ben hesitated and then replied "Um, sure". Karly came back to the edge of the bed where Ben was standing, unzipped his pants, and pulled out his cock. She couldn't believe how big it was. He had never seen his friend's cock, and and she couldn't believe that she was looking at it, holding it, about to suck it! While on all fours on the bed, engulfed his cock. She had never done this before so she took it in too quickly, gagging a little. Ben couldn't believe it. The feeling of the cool air caressing his exposed, rock hard cock, and then being sucked by a hot, wet mouth, was enough to make him cum, so he immediately said "Wait...you're gonna make me...". Karly just sucked really hard, thinking that that's what you're supposed to do. She sucked on Ben's cock like it was a large straw. Ben said "Wait, stop...just keep your lips wrapped around it and hold still". She complied, and Ben just slowly moved his cock in and out of Karly's mouth. "Oh my god, that feels so good", Ben said. He was slowly fucking Karly's mouth.

Karly was really hard now and was able to loosen up her throat. She loved the way it felt on her tongue and her throat as Ben slid his shaft in and out, gently holding the back of her head, knees bent, moaning, "Oh my god, I can't believe it...Ooooh". But Karly wanted more. She at that point really wanted a pussy so that Ben could really fuck her. That's when Karly thought that maybe she could use the only hole she has down there as a sort of 'make-shift' pussy.

She pulled back and Ben looked at her. "Why'd you stop? That was feeling so good. What's wrong?" Karly looked at him, "Do you want to try fucking me?" Ben looked at her, puzzled. "How? you mean like pretend fucking like rubbing against you?" Karly felt too embarrassed to ask him to put his cock into her hole, so she just said "yeah". Ben said, "Okay, but, shouldn't we get a condom or something?" Luckily, she had brought one from her sister's room, expecting something like this to happen. She slid it onto his cock, and he moaned and trembled and she slid it on. Then she turned around and bent over in front of Ben. He stared at her ass and hosed legs in heels, her slender body, and her ass just propped up waiting to receive him. "Oh my god, I can't believe I'm doing this..." Ben said under his quivering breath.

He came up behind her and started to rub his shaft against her panties as she was bent over. Upon first contact he was shaking with ecstasy. They looked at each other through the bedroom window, which was reflecting their taboo sex on the bed. He started to rub his cock against the crack of her panty-covered ass. He grabbed her by the waist and ass as he dry-humped her.  Karly then pulled down her panties. Ben asked "Wait, what are you doing?" "It'll feel better if you don't rub on the panties".

He started up again and she was right, to feel his cock, still wet from Karly's mouth, was gliding nicely along the top of her ass crack. Karly gently pushed back with each thrust made by Ben. "Do you have any lotion?" Ben asked "This feels awesome but I want it to glide more". Karly told Ben that the lotion was next to the bed. He reached over, pumped a bunch lotion onto his cock and then started rubbing it on top of Karly's ass crack. He couldn't believe that he was finally experiencing what it was like (perhaps) to have sex with a hot chick. He couldn't believe the moment he was in.

Karly then asked for more lotion, and when he started to apply it, she reached back, grabbed Ben's hand with lotion in it, and directed him to rub it all over her crack, even over her hole. The feeling of his hand gliding over her tight hole made Karly tremble with sexual excitement.

Ben started to rub his hard cock again, but Karly was getting impatient. She wanted his cock inside her tight butthole, but didn't know how to tell Ben. So she hatched a plan. She moved forward a little more than usual so that Ben's cock would fall away from her ass crack, and then moved back, so that the head of his cock came flush against her pussy hole. "Whoa, hold on, that was close...", said Ben, not even thinking that that was an intentional maneuver by Karly. He didn't even think about penetrating her - it didn't even cross his mind. He just thought that this was as good as it gets with a "hot chick" without a pussy.

Before he could move it up and place it on the crack of her ass, Karly pushed back so that her hole stretched to engulf the head of Ben's cock, wrapping tightly around it, popping in and sliding in with a majestic glide. "Aaaaaahhh!" she cried out, and her knees trembled, feeling him fill her tight hole. "Ooooh noooo.....my gaaaaa" Ben said.

"Fuck me, Ben. Fuck me like I'm a girl", she said. He couldn't believe how amazing it felt: tight, hot, wet, and oh the sensation! She couldn't believe the sensation. He couldn't help himself now. He was looking down at his cock sliding in and out of her hole. It was so tight that each slide out of her hole, he could see it pulling back the sides of her pussy because it was so tightly wrapped around his hard shaft. He looked at her, his cock pumping her butthole, and the reflection in the mirror of them fucking. He saw himself fucking an incredibly hot chick. He could smell the floral scent of the lotion mixed with the scent of her ass pussy. He was completely possessed with sexual desire.

It had only been 4 minutes since they began, and 1 minute since they started fucking. But he felt like he was going to cum - big time. He slowed down to slow, long strides in and out. He then realized he was without a doubt going to cum. So, he continued with his long strides in and out, drilling her and ramming her ass to make sure he was deep in her. She screamed in ecstasy each time he pounded her like that. Her cock would bounce up and down each time, and first she came. Her cum went squirting everywhere, on the bed, on her stomach, and on her chin even! "Aaah, Ahh, I'm cumming..." Then, Ben came. He couldn't believe it. "Oh my god, I'm cumming! Ohhhh". He came so much that it started to leak at the edges of his condom. They both collapsed trembling.

Karly stayed Karly the rest of the night. They continued to 'explore' their fantasies the entire weekend. But after that, things were awkward between Ben and Carl. But they found  solution: whenever Karly came out, the awkwardness went away and Ben and Karly had nothing but a lot of fun!

Taught a Lesson

The neighbor of some of my relatives found out that I crossdress. He lives alone in the next door house in a suburban track-home community. I was house-sitting for my relatives when he found out. He said that he always wanted to "fuck a sissy fag while all dolled up" in order to "teach him a lesson". I found out what lesson that was very quickly. Anyway, he said that if I didn't come over to be taught this lesson, then he'd tell my relatives and all of my family members, apparently having photos of me all dressed up and strutting around in the backyard.

He wanted me stay over at his house for a few nights to be his young, tranny wife the next couple days. I was supposed to be dolled up by six in the morning in the clothes that he laid out for me the night before and had to make him breakfast, prepare his lunch, and have dinner ready for him when he got home from work (in addition to having the house cleaned and the laundry finished).

He said that if I was going to look like a woman, I'd have to be all wrapped up nicely in all the feminine things that a "proper woman" wears all day: panties, pantyhose, bra, dress, etc. (Clearly he, being thirty years older than me, had an old-fashioned conception of a woman). He even required that I make sure my "pussy" was kept wet all day, giving me a bottle of lubrication and a tampon in order to keep myself "decent and clean". I really didn't want to - a tampon? I did it anyway, since I didn't want anyone in my family to find out. In sum, he demanded that I dress up and look like a really young suburban housewife, from dress, hair, makeup, to clothes and underwear (even feminine hygiene!)

I made him breakfast and served him. He stared at me the whole time, as if he were inspecting me. I could tell he was pleased because of the large bulge in his slacks and the smile on his face. Throughout the day he called to check up on me to make sure I was acting according to our agreement. By the time the day was over, my legs and feet ached from being in high heels, my crotch was moist from being covered in panties and pantyhose, and my hole was juicy wet and feeling softly stuffed from having squirted a bunch of lube inside of it and kept it plugged up with a gently expanding tampon. 

I had dinner prepared for him that night. Afterward, I gave him a beer and proceeded to do the dishes. He came over after a few minutes and stood behind me. I was really nervous - even if I were really his wife, I'd, for one, be a virgin, and two, thirty years his junior! I thought he just wanted someone to cook and clean for him but oh, that wasn't the case. I had no idea that he wanted to, as he said, "consummate the marriage". He really wanted to show me what the consequences were of dressing up like a woman.

I could feel his hard shaft through his slacks against my dress and pantyhose-/panty-clad ass. I was really nervous! He slid up his hand under my dress, and reached into my pantyhose and panties from behind, and then pulled out the tampon, which was dripping with lubrication. He whispered "Good girl" in my ear. I turned around, nervous about what he was planning on doing to me. He then quickly said "Ah, ah, ah, I didn't say to turn around - you be a good wife now". He then pushed me down onto my knees and my face was right at the bulge in his slacks. He unzipped, at which point his huge, throbbing, pulsating cock sprung out. "Open your mouth, now. Be a good wife and open your mouth, open your..." My lips were trembling, and I opened. "That's a good girl. He then stuffed my mouth, and I could barely wrap my lips around it. My mouth was stretching at the corners, and I could feel the intense heat and throbbing of his shaft on my tongue, sliding down into my throat. He slowly slid his cock in and out, and told me to look up at him. "That's a good girl. See? This is what you have to do if you're going to insist on being a sissy-faggot. You understand?"

He pulled out his cock and stood me up. He made me rub more lube on his cock. My hands looked so small compared to his enormous cock. I couldn't believe how hot it felt in my hands, and how much it was throbbing. It looked like a sausage about to burst in its casing. Before I could even put away the lube, he grabbed me and ravaged my neck, roughly moving his hand up my dress and groping my ass like he wanted to spread it open. The whole time I could feel his hard, pulsating, dripping wet cock against my thighs and between my legs, at times jabbing into my stomach. He then threw me against the table, lifted my dress and slightly pulled down my panties and pantyhose, just enough to peel it open and expose my ass, which was squeezed together because of the waistband of the pantyhose and panties. He then firmly spread open my ass and exposed my "pussy", and I immediately felt the cool air against its wetness. He didn't take his time: he pressed the throbbing head of his cock against my pussy hole, stretching it ever so slightly. I was startled to feel his cock there - again, it felt so hot, and it felt like a ball was being pressed up against my butthole. He pressed harder and my hole stretched to engulf the head of his cock, wrapping very snugly around his shaft. He slid his cock right in and I immediately gasped and moaned out loud. My cock had been not entirely hard yet because I was so scared and nervous. But when he slid his huge, hard cock into my pussy, it was like it pushed all my insides into my cock, and, instantly, my cock became throbbing hard.

I moaned and said "please", and he whispered while pumping me slowly "no no, you need this  - you have to do this, you understand?" I bit my lower lip and moaned in incredible ecstasy. I had never new what it was to be not only fucked like a woman (at least as much as anyone like me could), but to be fucked into a woman. He said "Yeah, that's right, you want to be a little housewife? Well then, here's your first lesson". His strokes in and out of my hole were slow and steady, and they felt like the stroking of a violin: a smooth glide in and a smooth glide out with a seamless transition between the in and out.

He then started to pump me a little more quickly, grunting and grabbing my ass tighter, and pushing down on my lower back a little harder. I gripped the table, my mouth was agape, head slightly turned to his direction. I felt so dirty - filthy for not wanting it to stop. I felt my pussy stretching for his cock, and the scent of sex permeated the air. "Damn you're really tight, aren't you? Looks like I'm gonna have to do this nice and steady, just in and out" he would say. He lifted me and carried me to the couch. My hole was dripping with juice. He laid me on my back on the couch and continued to fuck me. 

"See, if you had a real pussy, I'd fuck that. But since you don't - since you're just a sissy fag - I'm fucking you in the only tight, stinky pussy you've got". He finally came inside me. With each ejaculating pump inside my hole, his cum would squirt out because his cock was so big and my hole was so tight. He then told me that I wasn't allowed to orgasm, that I had to remain 'wanting more' like any good housewife should. Then he ordered me to clean up all the sex juices.

But then while I was cleaning it up, he came back and fucked me more! I was on all fours wiping and cleaning the floor, and then the next thing I know he's grabbing me from behind, lifting up my dress, saying "That's it, honey, just stay like that and take care of me". All I could do was stay there, bent over, on my hands and knees, knees gently put together, head slightly turned towards him and up, mouth open.

It was like that all night, and the next day it was the same. Needless to say, I think I learned my lesson.

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 justcan'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.