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.