First Crossdresser Experience

I remember the first time I fucked a crossdresser. I never even had any inclination or thought of fucking a cd. I was at the supermarket and saw a woman dressed in a very sexy outfit, wearing pantyhose and high heels, big hair, etc. She looked hot. She bent over and that's when I just had to go up and talk to her. I typically have no trouble talking to women, so I walked up to her to get her number. She looked at me and said that she wouldn't be a good match. I asked her why, and she told me that she was a crossdresser. I couldn't believe it. Anyway, we talked for a while and then the next thing I know I went to her place.

We chatted, but I couldn't help but to keep staring at her legs and ass. I was getting turned on, and I couldn't believe it. She was so fuckable. That's when it really hit me that she has a cock just like me. After a few drinks, I asked her if she has sex with men while dressed. She said that she did, but not that often. It dawned on me right then that if she's got a cock, then she doesn't have a pussy, and if she doesn't have a pussy, there's only two places by which I could fuck her: her mouth or her ass. I instantly got rock hard - I mean throbbing to the point of serious pain.

She got up and spilled some of the juice she was having, and it spilled right on my crotch. She knelt down on her knees with a towel and started to rub my crotch. It was clear that I was already rock hard. She stopped, surprised, and looked up at me. The next thing you know, I'm standing with my throbbing cock sticking out of the zipper hole of my slacks, and she's on her knees sucking and swallowing it. Her lips were stretched around the shaft of my cock it felt incredible just pumping her throat. I couldn't take it anymore, so I stood her up. I saw that there was a bulge under her dress. I hiked it up, and her cock was hard under her pantyhose, stretching it like it was just aching to rip through. Right then an overwhelming desire to penetrate the only other hole she has overcame me. I pushed her against the couch, and lifted her legs up over my shoulders. I pulled her panties and pantyhose down a little over her ass, just enough to reveal her tight fuckhole. I pressed the head of my cock against it, and it was wet and slick. She was breathing heavy, saying "I'm really tight". That just did me in. I couldn't take it. I slide it in, and as I did, her mouth opened and she moaned. I couldn't believe how fucking tight it was. Her asshole was just strangling and hugging my shaft in the best fucking way. I could smell her pussy, and I was just pumping steadily in and out of her tight asshole. She came first, all over her pantyhose, and her cum dripped down her cock and ballsack, down her crotch and right to her asshole as I was just impaling her with my throbbing shaft. Her cum lubricated her tight hole even more, and I just couldn't take it anymore. I came in her, filling her incredibly tight rectum with so much cum that it started to squirt out with the last few inward pumps of my cock.

Country Bumpkin

Billy grew up on a farm pretty much his whole life, but felt like he had to leave. He decided to leave for the city to meet new people and have new experiences. He moved into an apartment complex that was full of sexy women. However, none of them were interested in him, for they saw him as a country bumpkin - a farm boy with no money.

He did, however, meet a friend. It was the boy who lived across from him named Kerry. They met for meals at times, and he expressed his loneliness to him. Billy told Kerry about his strikeouts with the ladies in the building and in the city. Finding so many sexy women around him only made his lustful desires grow. But not being able to satisfy his desires made him incredibly frustrated. Kerry told him that he felt the same way, but that he had found a way to satisfy his desires to some extent. At first, Billy thought that Kerry would tell him about prostitutes. When Billy asked what Kerry's way to satisfaction was, Kerry told him that it was all about masturbating in the right way. Billy didn't know what masturbating was, despite being in his late 20s. Kerry was surprised, but awkwardly explained what masturbation was. Both were a bit uncomfortable. You see, Kerry and Billy were both heterosexual, or at least found themselves incredibly and sexually attracted to sexy, feminine women, and women only. Billy was nevertheless intrigued. He then said what this special way of masturbating was. It seemed like all masturbating involved was stroking one's hard cock until ejaculation - simple. Kerry explained, a bit hesitantly, that he had bought women's clothing and lingerie - dresses, wig, makeup, heels, etc. - so that he could dress up like the sexy women in the building. He would then have "his way" with himself.

Billy laughed in surprise. "You put on a dress and do this thing called masturbation and pretend that you're one of the ladies? HA!" he laughed. He thought he had seen it all. Kerry was a bit tussled by Billy's scoffing, so told him that he would show him. He went into his bedroom and got all dresssed up. He put on some charcoal patterned pantyhose, put one makeup and a wig, and then some jewelry. He topped it off with a body-con short mini dress. He slipped into some high heels, and he completed becoming a she!

When Kerry came out, she said "Check it out! Not bad, huh?" Billy couldn't believe his eyes. She looked just like one of the hot women in the building. He was silent, wide-eyed. He got up and walked around Kerry. Kerry just stood there mockingly doing feminine poses with a lighthearted, self-satisfied smile, like she had proved Billy wrong. What she didn't know, though, was that Billy was getting a lot more interested than Kerry would have ever thought. You see, Billy was starting to see Kerry as a woman, and Kerry had not yet realized this yet. To her, they were still guy friends, buddy neighbors. 

"Wow, turn around", Billy said to Kerry. Kerry obliged. After Billy stared at her pantyhose legs and ass, he asked "So you just stand there and do this mastur-thing?" Kerry said that she didn't, and proceeded to the couch. She got on the couch on both knees, facing the couch back. She bent over and said that she likes to do "this" and watch her ass while she masturbates. Billy watched her bend over listening to the dress stretch around Kerry's ass and creep up her pantyhose covered thighs. He walked over behind Kerry as she was bent over, and placed his hands on her ass.

"Ummm...what are you doing Billy?" Kerry asked. You see, she wasn't trying to turn Billy on, or in any way seduce him. That thought didn't even cross her mind. For all she knew, she was just teaching Billy how she satisfies her frustrations, only so that Billy, if he should so please, can do so himself with his own clothes. But now she felt Billy's hands fondling her ass, thighs, between her legs, etc. She was surprised to find that she liked the feeling. They were both silent, Billy fondling her and Kerry feeling his caresses. She turned around and saw that Billy's slacks had a huge bulge in it in the crotch. She bent over slightly more, and pushed her ass back a little to lightly touch Billy's crotch, just enough to gently feel something hard and throbbing.

His hands moved up her legs and ass, and found her waist. He gently put his hands around her at the waist, and then moved forward, pressing a little more slightly his crotch to the crevice that had formed by the dress stretching over Kerry's ass. As he did that, she could feel her pantyhose slightly stretching where he pressed around her ass crevice, but she suddenly felt a hard throbbing stretch in her pantyhose right around her crotch. She was turned on. She not only was looking like one of the women in the building, but was starting to feeling like one.

"Ow, my goodness, ow" moaned Billy. Kerry asked him what was wrong, and he said that his dick hurt because it was so big. "Should I do this mastur-what thing now?" he asked. Something came over Kerry, and she said "I have a better idea. Slide up my dress". Billy did so, slowly, with trembling hands, exposing Kerry's pantyhose clad ass. He could feel the heat and moisture from Kerry's hot crotch come up to his face as soon as he exposed it. He stared at her ass through the sheer tights, and could faintly make out her butthole. Remaining in position, she looked back at Billy, and unzipped his slacks. "Pull it out" she softly ordered. Billy barely had to do anything, for with the slightest move, his hard shaft sprung out, like a fleshy pole engorged with a lustful throbbing that he had never experienced before. "Ow, it really hurts" he said. It just stuck out in the air, pulsating and engorged, hard as a lead pipe. He grabbed it like a bat and started to stroke. Kerry saw him stroking as she had instructed earlier before. "How's that?" she asked. Billy had a look of pain and impatience in his face. "It's making it worse. It really hurts. It's hurting more every time I look at you. You look too much like a woman". Kerry then suggested using the lotion next to him. Billy pumped a generous portion on this hand, and began gliding it along his shaft. "How's it now?" Kerry asked, still bent over. "It's making it worse, Kerry, I don't know what to do. I think I'm too turned on"

Seeing how much Billy was turned by her femininity was turning on Kerry. Her own 'clit' was rock hard and throbbing, and her crotch was glistening with anal sweat and juices from her hole under the pantyhose. Billy could smell her juices. He could smell her hole, and for reasons he didn't know, he was getting incredibly turned on by the scent. 

Kerry finally reached around and tore a hole in the back of her pantyhose. The tear made a rip sound, and her was totally exposed. She could feel the cooler air kissing her ass and especially her butthole. The heat and smell hit Billy, and he became dizzy with wild lust. "Slide it in" she said softly. Billy didn't know what she was talking about. "Slide what in where?" he asked. "Ow, it really hurts. "Slide in your cock into my butt." 

Billy was shocked, but then grabbed his throbbing, sensitive shaft and positioned the engorged head against the wet, glistening anus. He pushed slightly, but it didn't go it. "I don't think it's going to fit". But before he could finish, she pushed back, and the engorged head popped in and the rest of his pole just slid in smoothly. "Oooooohhhhhh myyyyy..." Billy moaned. She gasped and moaned. "Ooh, yes, that feels so good - that feels toooo good" he moaned, as he slid his pole slowly in and out. "How did you know....oooh...that this would help....oh my goooooodneesssss!!! How did you know your butthole.......ohhhhhh....would....help....." He looked down and he could see her wet anus stretched around his fleshy pole, making it glisten with the juices in her ass, pulling ever so slightly when he slid out, and pushing in ever so slightly when we would slide in. He kept pumping her. He couldn't believe the sensation. Her as was so tight around his hard shaft that it was mixing the throbbing pain he felt with an incredible ecstasy. "Yesss, that's it. Just like that" Kerry said. "Does it feel good now? Does it still hurt?" "Oh, it feels too good. This is what I needed...Ooooh" Billy moaned. Kerry's rock hard clit was bouncing in the air with every pump of Billy's cock. Her cock was dripping and oozing with cum, sprinkling it all over the couch. Billy's cock was so hard and so big, and it was gliding in and out of her anus with such grace, that eventually she squirted all over the back of the couch. Billy kept going and then became frantic. "Oooh my....something is going to happen! something is going to happen! something...is...oooh". He kept pumping, and now, with each pump in, his cum oozed out of the stretched sides of anus. Billy came with an explosion inside of Kerry.

Billy never would have thought that Kerry's secret trick in satisfying frustrated desires would have worked so well. He was puzzled how Kerry could have thought that sliding his pole into her butt would have made the pain go away and make things good - very good. What an experience for a country farm boy like Billy. It looks like Billy will never be going back to the country again.

Confessions of a Straight Man #2

To the author of this blog:

I must say that you capture the very essence to the thrill that I experience in desiring, playing and having my way with 'girls' like you. I remember the first time I ever fucked a t-girl was when I was in my twenties. I really didn't know she was a t-girl. She was just way too hot, so I thought, to be a t-girl. She was an asian chick. Her voice was a bit androgynous but she was incredibly hot: super slim body, gorgeous face, and ass and legs clad in hose that would put many genetic women to shame.

In any case, she thought I knew but I didn't, at least not consciously. She first sucked on my dick, bobbing on it like there was no tomorrow. My raging hard on hurt because it was so hard, especially feeling her lips around the shaft and watching her head go back and forth as she knelt before me. Anyway, I couldn't take it anymore and wanted to fuck her pussy. I sort of roughly bent her over the table and hiked up her skirt. Underneath, she was wearing pantyhose without any panties. I didn't really think much about the bulge in the cotton crotch area of her pantyhose because I was so turned on. When I felt her crotch, I was shocked to feel her cock and jewel sack tightly packed under her pantyhose. I stepped back and thought "what the fuck?" She turned around, propping herself on the table, looking at me. I remember her wine-red lips were still glistening from sucking my cock. She laid back on her elbows with one leg propped up on the table and the other leg hanging off. I can see under her skirt.

There wasn't a single word exchanged. I don't know what came over me but I just stepped forward, grabbed her ankles, pulled her towards me so her ass was aligned perfectly with my cock. Her legs were on my shoulders now, and I peeled off her pantyhose just enough to expose her tight pussy. At that point she reached over into her purse (which thankfully was on he table), and then pulled out what looked like a bottle of hand sanitizer. It was actually KY jelly, or something like it. She squirted a generous amount on her hand, and stroked my shaft with it while staring in to my eyes. I was so raging hard. I wasn't thinking - I was just in the moment. She then slathered the left over on her ass. Before she could even move her hand away from her hole, I remember pressing the apple of my cock against her butthole and feeling it stretch tightly. Her eyes were still staring in to mine, and as I pressed more, her mouth started to open. Fuck, I still remember that feeling of my cock just sliding into her tight hole. It went from feeling cool from being exposed to the air covered in gel, to just sliding into a snug, tight warmth. My cock was being squeezed in the hottest way. I can smell her hole, and it smelt like sex - but a sex that was so lustfully dirty my legs and even body were shaking in ecstasy. I fucked her like dog in heat. I loved the way her cock got hard, clearly expressing that she was loving every centimeter of my shaft gorging and pumping her butthole. It bounced up and down as I fucked her. It was super hot. Her butthole was so tight that I could see the rim of it stretching and moving inward and outward with every pump of my dick in and out. She didn't say a word, just moaned and panted like she was enjoying every minute of being fucked like a slut, like she deserved to be fucked like one for tricking a guy into thinking she was a girl!

That was the point of no return for me. We fucked something like 7 times that night, and the last three times I squirted my juice deep inside her ass with long, slow, deep final pumps.

I've been living in the deep south for some time and mostly the women around these parts tend to be overweight, if not obese. This girl, though, man, was like the girl of every guy's fantasy. And it turns out that she was really a he!

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!