Rachel’s Crossdressing Daddy

May 1, 2024 // By:analsex // No Comment

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Editor’s note: this story contains scenes of incest or incest content.


Hey, my name’s Rachel and my story is a bit of an unusual one. Let’s just say that one spring day, my whole world was turned upside down, but I loved every second of it.

Just a little about my family: to this day, my parents are happily married. Mum is a loving woman, generally supportive, pretty, and lots of fun to talk to. She’s gotten a bit chubby over the last few years, but I guess that’s understandable when you’re 56 years old. Dad has always been a bit of a “manly man” cliche; he’s able to fix anything around the house, likes a beer or two at the end of the week, and loves his football. He’s still quite thin, perhaps not as much these days, but looking at his body, you’d never guess he was 58. Sure, he’s got a fair bit of salt with his pepper, but his hair is till thick and full, and the fact he keeps it short helps hide the greys. As for me, I’m a 19-year old girl and I still live with my parents, at least until I save enough to move out into a place with my friends. Because I’m the only child, I know my parents are really not looking forward to me moving away. As for our appearances, Like Dad, I’m quite thin, and I’ve been “cursed” with good genes that make me look about 3 years younger than I am. Of course, part of my youthful looks can also be attributed to the fact that I don’t smoke or drink, and love my beauty sleep.

But enough about that. Let’s get to the actual story, shall we?

It was a nice, sunny Saturday afternoon and I’d just been out catching up and window-shopping with friends downtown. After catching the bus back home, I let myself in, and the place was empty. Mum was at work, as usual (working retail full-time, you take the shifts you’re given), and I assumed Dad must have gone to the shops. So I headed to my room to change into something more casual and most likely waste time online. When I got to my room, though, my plans went completely out the window. I opened my bedroom door, and got the shock of my life.

My dad stood there facing the mirror in my wardrobe, wearing a lacy red bra and matching bikini briefs, rubbing his erection through the panties. My panties.

He didn’t see me right away, so I quietly locked the door behind me; there was no way he was going to escape this. Plus, even though she wasn’t due back until after 8 that night, I knew I didn’t want mum to walk in on whatever the fuck was happening here. When I spoke, I’m sure he got the fright of his life. “Dad? What the hell is this?”

Naturally, he jumped. Any bigger and he would’ve hit the ceiling. He turned around, and I saw that my underwear was clearly not made to accommodate his erection, more than half of which was poking out the top of the tight red briefs. On him, my C-cup bra looked empty and deflated.

Dad started to stammer, “Rachel, when- Oh fuck. I’m sorry.” I’d never seen him embarrassed before; it was actually quite startling. A bright red grew from his cheeks and soon covered Dad’s entire face and most of his neck. Based on how it was barely even visible any more, I’d say that most of the blood from his erection was redirected to his blushing face.

“You need to tell me what you’re doing. Right now, Dad.”

“Oh God… okay. I, um, I get turned on by wearing lingerie. I choose yours because your mother, she’s a bit bigger than me, as you know, so I don’t really fit in hers… and yes, I know this’ll probably stretch yours out too, but-” Stretching was the furthest thing from my mind at that moment and I told him so.

“But I just want to stress that I don’t have any, um, any sexual feelings for you or anything; it’s just about the clothes, I swear. And, I don’t know what you know about cross dressing, but I’ve never wanted to be a girl or anything like that. I just- the underwear, it really feels good, and I’m ashamed to say, it really does turn me on.”

That was probably the most I’d ever heard my father talk earnestly about his feelings about anything. Shit, he didn’t even cry at the funerals for either of his parents. Seeing him there, humiliated, almost completely naked, totally vulnerable – this entirely new side to my dad really intrigued me. Actually, screw that; stories are meant to be about the truth and honesty. I was more than a little turned on by the situation. The massive contrast to his public persona, his hairy chest, his once-massive erection, his rugged face softened by embarrassment, his actual display of emotion – it all combined to make me realise just how much I loved my Dad, and how I’d been a little bit in love with him for a fair while but had never been willing to admit it to myself. Why else would I have found Gary Oldman so incredibly sexy throughout high school? My dad was a spitting image of him. So I decided that now was as good a time as any to act on my unearthed, unconscious feelings.

“Does anyone else know about this?”

“No, nobody does. Not even your Mum.” A horrifying thought crossed his Kurtköy Öğrenci Escort mind. “You won’t tell her, will you? Oh God, it’d destroy both of us.”

I took my time, pretending to think it over. “Okay, I won’t tell anyone, but on one condition.”

“Anything, Rachel.”

“Tell me the truth. Do you ever think about me when you’re, um, dressing up?”

He looked down, mumbling, “Only about how they’re your clothes I’m trying on.” His redness had started to fade, but now it had come back with a vengeance.

I stepped closer to him, and now there was less than 2 feet between us. “Dad, look me in the eye and tell the truth. When you’re dressed in my underwear, and you’re all turned on and touching yourself, do you think about me?” I still can’t believe I was as blunt as I was. So unlike me. I’m usually so shy and passive, but I guess that day it would’ve been hard to be more reserved than Dad.

“Fine, okay. I admit, from time to time, I have had, um, dirty thoughts about you while I’ve been wearing your things. But I’d never thought to act on it, swear to God. And they were only passing thoughts, never uh, full-blown fantasies or anything twisted like that. But yes, I have had unfatherly thoughts about you, Rachel. I’m sor-“

Fuck apologies. Before he could complete the word, I kissed Dad on his mouth. His mouth was so warm, but incredibly dry from all the talking (rambling) he’d been doing. He resisted the kiss at first, but when he realised I wasn’t letting up, he soon started kissing back. His soft, warm, slightly-chapped lips pressed into my own, his breath warm on my pale skin. I embraced my father, lingerie and all, and marvelled at just how much I enjoyed the feel of my bra on his body as I rubbed his back. Running my hands over the rough hair on his back and then over the soft, satiny material of one of my favourite bras, down to the small of his back, his still-firm ass, and the soft, lacy briefs that made both Dad’s and my own butt look springy and toned. I could feel his erection pumping up again, growing out of the top of the briefs Dad was wearing, pressing into my stomach, only serving to intensify my incestuous desire to feel it inside me. Dad also embraced me tightly, his hands beginning their exploration of my body, especially focusing on massaging and squeezing my bum.

I opened my mouth and Dad followed almost instantly. Our tongues, hot and wet, danced back and forth, up and down, all around. He moaned and I moaned. It was unlike any kiss I’d ever experienced in my brief time as a non-virgin. Intense, weird, incestuous, surreal, passionate, emotional, sexy, and just generally amazing. I’d never felt such a strong desire for sex, and I thought I had it bad my first time! Trying not to break our otherworldly first kiss, I started shuffle-walking Dad backwards towards my bed. When he reached the edge, I broke the kiss and softly pushed him down until he was lying flat on his back.

My father’s cock was practically screaming for me to jump onto it. It was beautiful, thick, circumcised, with a dark purple head that looked oh-so tasty. There it was, with more than half of his shaft poking out the top of my panties out as it stretched the soft, red fabric. His balls were slightly more covered by my underwear, but I could still see them and his dark, curly, wiry pubic hair peeking out the sides of the panties. Restraining my desire as much as I could, I climbed onto the bed beside him, knelt over and, leaning with my arms either side of his body, resumed making out with him.

His hands reached up and started caressing my back and stroking my curly, long brown hair. He’d always stroked my hair when I was growing up, but this was different; I could tell he was now finally seeing me as more than his daughter. Finally, Dad could see that I was a mature young woman, with needs and wants and apparently very strange fetishes. And so he stroked my hair with affection and desire rather than any sort of paternal nurturing feeling. That’s what I tell myself, at least.

Our mouths were wide as our tongues did their dances. We moaned in unison and in response to each other’s moans of passion. Dad’s hands got more adventurous and started squeezing my breasts. They were so warm, and they grabbed me with such purpose, I could tell that Dad liked my boobs a lot more than he liked my ass, which was fine by me; I’ve never really liked my butt too much. I moaned into his mouth as a way of letting him know I was enjoying his breast massages. In fact, I’d never liked it when guys would play with my boobs before that moment; I guess “Daddy knows best” applies to sexual techniques too, huh?

Dad eventually got too adventurous with his big, rough hands, because soon after the tit-grabbing started, he found the zipper at the back of my dress and started to undo it. It killed me to once again remove my lips from Dad’s, but I needed to.

“Oh no, Dad, not yet,” I reached behind and zipped my dress back up properly. “Good Kurtköy Çıtır Escort things to those who wait. Remember who told me that?” Of course he did. “Now, I think you and I have waited long enough for things to progress though, don’t worry…”

I leant back over, and started kissing his neck. He moaned my name; clearly it was a good move. God, he smelled so good. I think his deodorant is just Old Spice, but somehow Dad’s body made it smell incredible. Maybe it’s just his natural pheromones, but whatever it was kicked my arousal up another level.

In between neck-kisses, I informed him “You smell fucking amazing” in a sexy voice I didn’t even realise I was capable of. I soon moved down towards his muscular, hairy chest and unfilled lacy red bra. Don’t ask me what convinced me to do this, because I still have no clue. Once I’d kissed my way down to the bra, I started licking his nipples through the bra cups. Even though I knew he wouldn’t actually feel my tongue through the bra’s lace and padding, I just kept licking and sucking, tasting the satiny synthetic material of my own lingerie and smelling Dad’s sweet-but-masculine scent. I played with both nipples this way, and Dad appeared to love it just as much as I did. Eventually, I decided I had to move on to the “main course” of my father’s crossdressing body.

I kissed and licked my way down his belly, past his navel, to his cock – amazingly thick, long, hot and hard. It strained against the skimpy, lacy bikini briefs, the red material contrasting with his deep purple cock-head beautifully. A trail of delicious clear precum ran from his cock-head to the spot on his stomach where it was pressed when we embraced. His unkempt pubic hair shot out from around every edge of the sexy, feminine underpants. Dad’s balls and scrotum bulged and stretched the material in the lower area of the briefs’ crotch. I’d probably say that was the moment I knew I was in love with my father. Words will never be able to adequately explain why, but it was just something about the fact that here, mere centimetres from my face, was the very penis to which I owe my very existence, encased in one of my sexiest pairs of underwear; seeing Dad’s essence of manliness straining to fit into one of the most delicate and feminine clothing articles available really highlighted just how layered and amazing my father really was. I guess that was the missing element that kept me from realising my true feelings for him all that time. But now that I knew Dad wasn’t just a caricature, I guess I let myself fall in love with him. Plus, the cross dressing aspect overshadowed the whole incest taboo for the better.

So, there I was, admiring my Dad’s mammoth erection, when I realised I should probably do something with it. We both wanted it, so what was stopping me? Nothing, I decided. So I started out rubbing it with my right hand, once again admiring the feeling of the feminine fabric when compared to the ultra-masculine body that was wearing it. I stroked the base of Dad’s cock for 30 seconds, staring at it and loving the sounds of his soft moans of pleasure. I knew that wasn’t enough for either of us, so I leaned my head down and started licking his cock through my panties. My tongue glided up and down the base of his shaft while my right hand gently stroked his thick purple head, which was now glistening with Dad’s precum. This time I could taste his skin more than when I was licking the bra, and it was worth the wait. His manly, musky scent filled my nostrils and amplified the sweet taste that was dancing up and down my tongue as it ran over the outline of Dad’s 8-inch erection through the lacy red underwear. God, how I wanted it inside me. For now, I settled for it in my mouth.

I moved closer to Dad’s cock-head and eagerly took it into my mouth. I tasted the delicious precum, sweet-yet-salty, and felt every square inch of Dad’s hot, thick manhood that I could fit into my mouth. It tasted just as good without my panties. My right hand kept his cock steady while I played with Dad’s nipples using my left hand. I didn’t want to spend too much time giving Dad a blow job, in case he came before I could feel him inside me where it mattered. But I didn’t want to tease him, either, so I slowly bobbed my head up and down on his cock a few times, savouring his taste. After probably 10 more seconds, I released my father’s cock from my mouth and hand and stood up next to the bed again.

Looking down at my lust filled Dad, still wearing my skimpy red lingerie, I reached behind my back and found the zipper that Dad had impatiently tried to undo earlier, and slowly pulled it down. Before I let the dress drop, I kicked off my ballet flats and let them go wherever they landed. Slowly, with what I felt was my most seductive look on my face, I slid the strap off my left shoulder, then my right. I let the dress fall, and asked Dad, “Like what I’m wearing, Daddy?” Because I didn’t want to feel too self-absorbed, I did a silly ballerina spin just to lighten Kurtköy Elit Escort the mood (and if it helped Dad check out my ass a bit more, all the better).

Dad looked me up and down, clearly enjoying the show I was putting on for him. I was wearing a black balconette bra with a red rose print, matching hipster panties, and seamless black hold-up stockings with lace bands. When I dressed that morning, it was really just for fashion; boy, am I glad I wore something sexy instead of my “everyday” cotton bikini briefs and t-shirt bras. “Holy fuck, Rachel, you look even more sexy that I could ever have dreamed.”

I giggled and asked something I knew would make him do that sexy blush again. “So, have you ever tried on this outfit?”

Just as I predicted, his face once again lit up like a tomato. “No, not that particular pair. But I doubt I’d be able to pull it off the way you do, honey. I’ll say it again: You look so fucking sexy, Rachel my dear.”

“Thanks for saying so, Dad. Now…” I unhooked my bra and watched Dad’s face light up as he watched what he calls my “perky young tits” bounce and jiggle when I set them free from the bra. Next, I slid off the hipsters using only my thumbs. Once they were off and I’d stepped out of them, I stood with my legs slightly apart and let Dad ogle my pussy from afar for a little while. I normally just like to keep my pubic hair trimmed, but with summer coming up in about 2 months, I had started getting Brazilian waxes done again, so I was freshly waxed the first time my father saw my naked adult body. The way Dad’s cock twitched in his panties as he stared at my body proved he liked my look. Once I thought he’d ogled my bits enough, I reached down to start taking my stockings off, but Dad immediately objected.

“Rachel, leave them on? Your stockings, they make your legs look so great, can you please leave them on for Dad? At least this first time…”

“Crossdressing, incest and now a stocking fetish? What have I gotten myself into here, Dad?” I teased. “Alright, fine, the stockings stay for today.” I came back to my bed, this time climbing on top of my father’s body, straddling him, my wet pussy hovering inches above my father’s big, hard, panty-wearing cock, both aching to finally join with the other. My stockinged legs rested against the outside of Dad’s hairy, naked legs. Supporting my weight, I leant on my hands as they pressed into Dad’s bra, my fingers pressing firmly into the soft material. I leant down and once again began making out with my manly, crossdressing father. His hands caressed my back, exploring my body, squeezing and playing with my ass and my breasts. Our tongues flicked into each other’s mouth with unprecedented passion and speed. I wanted him, and I knew he wanted me. Oh fuck, how I wanted him! He tweaked my nipples, getting them hard. I started to do the same with his, squeezing them through the soft, padded fabric of his bra.

Dad started grinding his hips, his cock making brief, teasing, tantalising contact with my pussy lips.

He was searching for me.

I wanted him to find me, to penetrate me and while he wore my sexy red underwear.

I wanted him, lacy feminine panties and all.

But most of all, I wanted him to want me.

I wanted to hear him say the words I was longing to hear.

I broke the kiss and shifted my position so my pussy was just south of his big, wanting cock. I leant back and used my feet to support my weight, and reached for his cock, stroking it with both hands. “Fuck, Daddy, you have such a nice, thick dick, and I love the way it looks in my girly underwear. Honestly, I do, I’m not teasing. I can’t believe I’m playing with the same cock that made me. Oh God, it’s so hot and hard in my hands… you must be about ready to burst!”

“Oooh shit, I am, Rachel, swear to God. But I don’t wanna cum until I’ve been inside my daughter’s lovely smooth pussy. I’ve never wanted anything more than I want you, Rachel. God, I need you and your beautiful young body, honey.”

“Mmm, that’s what I wanted to hear, Dad.” Still holding his thick dick in my right hand, I shifted position once again, my pussy once again hovering right above my father’s penis. I’d never been so wet in my life, but I still had trouble fitting Dad’s dick inside me on the first try. I was so tight and he was so thick, but with a small amount of wriggling and easing up and down on his cock, I was soon able to feel my Dad’s rock hard cock inside me, filling me up. I gasped when I realised I could feel each throb of his cock in my pussy; the handful of guys I’d slept with before Dad were nowhere near this big. Dad groaned and moaned as I slid down his cock, all the way down to the base, where I could still feel the panties he was wearing bunched just above his balls.

“Fuck me, Rachel,” he practically begged. Lucky for him, I’m not a girl who needs to be told something twice. Leaning on Dad’s chest for leverage, I moved myself up off his cock until I could feel it almost about to slip out of me, then let gravity take me back down to the base of my father’s dick. I steadily increased my rhythm, trying to ignore my body’s screams for harder and faster fucking. I let myself moan with each down-thrust, while Dad grunted with pleasure when I slid both up and down.

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