Daryl's wife, Jessica, always said he had a big ass. Her own ass was big full and round and she would make fun of the fact that he could wear her jeans and fill them out. It didn't occur to her that something else was going on until she caught him in her panties. He said he liked the material, but the truth was pretty obvious. he liked to wear women's clothing and she figured he liked other things that girls liked.
It was Jessica's fault, one drunken night she insisted they 'dress up' and Daryl's plump ass filled out her panties and looked extremely feminine in her stockings. Daryl had a soft jawline and a wig and make-up and a bra made him more than a passable female -- he/she was pretty Hot. After a night of intense 'lesbo' lovemaking, when Daryl reluctantly took her smallest vibrator, he had changed. He wore her underwear. He started cleaning the creampies he deposited in her. She wondered why the batteries in her vibrators were always dead. He was truthful when he said he had never been with a man, but she wasn't sure she believed him after she caught him checking out TS websites. Daryl insisted it could be just another part of their relationship, but Jessica wasn't sure. She left on an extended business trip so Daryl could figure it out.
That meant Daryl would be at home to take care of their son who had just turned 18 and was a senior in high school. Daryl felt bad for his son, Jack, who was a cute enough young man with an athletic body, but sadly was stuck in a small religious town where the girls were so strict with their chastity belt panties, the high school boys were pretty much forced to marry to get any sex at all.
Daryl's true journey began when he was taking out the trash late one friday night to notice Jack's car parked in the driveway. He heard a moan and realized that his son and his virginal girlfriend, Tiffany, were making out in the car. It wasn't going well from the tones of their voices, but Daryl moved closer to hear what was going on, kneeling in the bushes beside the car...
"Jack! I told you not to touch my boobs. You're only allowed to put your hands on my back while we kiss." Jack was getting frustrated, "I try, baby, but you're just so hot! At least let me touch you, through the clothes." They kissed for a while longer and suddenly Tiffany screamed, "Ewww... That's gross! I'm not touching your penis!"
Jack was frustrated, "Not even a little? I took you to dinner, movie and even dessert." "I kissed you. That's payment enough!" Daryl winced, being a teenager in this town, sucked.
Tiffany threw open the car door and stormed down the driveway -- she lived just down the street, so it wasn't a long walk. Jack scrambled out of the car after her and that was when Daryl was lost... As Jack stood up, his erect cock was also proudly standing at attention and bobbing out of the front of his jeans.
There in the moonlight, Daryl saw his son's perfect eight inch cock, circumsized and smooth like polished wood. It was out and visible for only a moment, but it seemed to last an eternity -- the soft highlight on the head, each throbbing vein, the tuft of hair and the bulging balls beneath were burned into Daryl's mind. Time returned to normal Jack chased Tiffany down the drive, shoving his cock back in his pants while trying and failing to get her to return.
In a daze, Daryl snuck back into the house and immediately went upstairs. As he climbed into the large lonely king sized bed, he noticed his own cock, an average six inches was hard as rock and straining uncomfortably in his wife's panties. He laid back and played back the image of his son's cock... damn... he wanted it and yet... it was wrong. He began to stroke his cock as he replayed the image again and again. A drop of precum oozed out and he wasted no time scooping it with his finger and feeding it to his asshole as lube. He moaned like a girl as his finger penetrated and he began to cum, harder than he had in months, all over his belly and chest.
As he lay there, he wiped up the cum, licking it off his fingers. He felt warm all over and noticed something -- his finger was still deep in his ass and he liked it there. Problem was, it was waaay too small. He had to have his son's cock and he knew the only way he was gonna get it would be to become a woman. As he drifted off, a plan began to form in his head...
The next week, Daryl heard the buzzer on the dryer and realized he had left a lot of Jessica's underwear in there. Jack was unloading the dryer when he got there and saw the underwear, lacey g-strings, stockings, bras.
Daryl tried to cover, "Oh, I was washing that stuff for your mom." Jack avoided eye contact, "Right. You know Mom said you're into dressing in chick clothes." Daryl turned red, "She told you that?" Jack made sure he kept his personal space as he put his clothes in the washer, "Yeah... she said you were working it out. So what's up with that?"
"I guess I like it," Daryl admitted, "Does it bother you?"
Jack shrugged, "Probably would if my friends ever saw it. But it's really none of my business. You guys always say live and let live. There is one thing..."
Darly gulped, "What?"
Jack shrugged, "Why do you do it?"
Daryl smiled, realizing honesty would pay off as he collected the clothes, "I like pretending I'm someone else. Every one has fantasies about being a football player or a rock star. I like pretending to be a girl. The clothes are nice and soft, the make-up makes me look pretty. You can become an entirely different person. You ever wonder what it's like?"
Jack shook his head and started the washer, "No. Way. But I guess I can see what you mean, like, why you do it. Have fun..."
Daryl shrugged, he had laid it all out and Jack knew what the score was. He wasn't exactly open, but tolerance is the first step to acceptance. And then hopefully... participation. Friday night Daryl knew that Jack would be out with Tiffany and he'd come home frustrated. This time he would be ready.
Daryl took friday off and got the hair waxed off everywhere. He laughed when the wax girl squeezed his butt, she liked it too. Then he picked up a sexy bra with synthetic breasts. Then tanned with a bathing suit bottom -- the tan line of a bikini always accentuating a nice round ass and when he was done, his butt looked like one of those models from the Coppertone ads.
He had practiced doing the make-up all week and checking Jack's internet history gave him a good idea of the women he liked -- big tits, big assed, dark hair. Black stockings, black high heels, a special pair of underwear, a short ass-hugging skirt, the push up 'filled' bra, he went with the 36 Ds that he had ordered weeks ago and some jewelry and some long nails. Probably a little too much make-up, lipstick, eye shadow and mascara, but the realistic wig with the shoulder length full black hair seemed to complete the whole package.
Daryl didn't recognize himself in the mirror, but there was someone he had been dreaming about. She heard a female voice come from somewhere deep within her...
"Well, hello Darla."
Daryl had been practicing his voice for weeks, actually more like months... he'd listened to female authors read their books-on-tape romance novels on the way to work and found he could deliver a nice feminine voice after a couple months practice.
Tonight would be the night to see if it paid off for... Darla.
"That's the last fucking time." is all Jack could think as he parked his car in the driveway. He'd spent all week kissing Tiffany's ass to 'earn' another date with her and she yelled at him for touching her tits, even threatening to tell her dad this time. Jack drank two beers with his buddy Manuel just to blow off steam -- but going home early on Friday night with blue balls was becoming a sad habit that he desperately wanted to break. At least he could jack off to some internet porn.
He came in the house, there was a smell he didn't recognize, sweet, flowery -- kind of perfume. He sat down on the living room couch, noticed candles were lit. What the hell? He heard the blender grind to life in the kitchen and figured his Dad was up to some of his antics. As that thought set in, he figured maybe he better leave. He started to get up when he saw "her" silhouetted in the doorway:
Shoulder length black hair draped around the shoulders and a black blouse tightly hugging some pretty nicely curving breasts and hips before the dress ended mid-thigh in stockings that flowed into the some think strapped high heels. He could make out vague facial features -- but all he saw strongly was the red lipstick and green eye shadow. Jack asked, "Hello?"
"Oh, hi Jackie." Darla responded with the feminine voice she'd been practicing. She moved out of the doorway and Jack saw this extremely sexy woman approach him, then realized as she approached, "Dad? Is that you?"
"Darla. I'd appreciate it if you called me Darla when I'm dressed like this." she purred as she approached, a hefty glass full of margarita. He recoiled a bit, feeling weird, "Uhh...Okay." She immediately filled the awkward silence that followed "I thought you had a date tonight. I expected you later. Hope you don't mind."
Jack, "Uhh...No, it's fine. Just gotta get used to it, I guess. My date didn't work out. Tiffany is a fucking bitch."
Darla put the drink in Jack's hand, "Here... this'll help. Come in, sit down... tell me what happened?" They sat down on the couch and Jack took a big swig of the drink, it was fruity but the tequila was strong. Tequila always got him buzzed quick and made him horny -- he probably shouldn't be drinking, but it tasted great. Speaking of great, Dad--uhh--Darla smelled really good. Stripper good.
"Same old Friday night. I take her out, spend money on her and get NOTHING in return. Don't get me started..." "That's what I'm here for." Darla sat back on the couch, nodding as Jack diatribed about what a useless cunt Tiffany was. Yeah, she was pretty and popular and could be fun at movies and bowling -- but when it came to making out, she was a prude.
When his drink got low, Darla produced a pitcher of Margaritas she made and refilled it. As Jack drank, his voice slurred and Darla caught him staring at her tits -- her cleavage was full and round and pushed together. The size he'd asked for was a 34C, but they felt like 36D... heavy and grapfruit sized.
Darla noticed, "So, what set her off tonight?" Jack ranted, "We're kissing and I put my hand on her tit. And she moaned while I kissed her, I know she liked it. Then as soon as I start to squeeze, she freaks out, practically breaks my hand!" Jack immediately leered at Darla's cleavage again.
Darla realized now was the time and took Jack's hand and put it to 'her' breast, "Go ahead, feel it. I know you want to." Jack started to pull away, but Darla wouldn't let go. He finally let her pull his hand to her breast, "Okay, I am curious."
Jack palmed Darla's breast, feeling under it and getting a full handful "What the heck -- feels real. Or at least, I think it feels real."
Darla giggled, "Well it's as real as money can buy. They're fake." Jack laughed, but didn't remove his hand, "Feel real to me. Tiffany never let me squeeze... but I always imagined they felt like this." Jack continued to feel Darla's tits, he liked it. It made him think of the chicks on the internet. Uh-oh! He was getting an erection. Disturbed, he immediately let go of her.
Darla noticed his erection and brought his hand back to her boob, "It's okay... Let me show you..." She took a big risk and put her hand on his chest, feeling his pecs. Darla rubbed his nipple between her long nails, she realized it was now or never-- time to put her plan into motion...
"I thought you should know how to touch a woman's breasts. How to please her.... so the next time you get the chance, you'll know what you do." Jack had never thought it of it that way, "Shit! You can show me?" Darla smiled, "Sure, you can practice on me. But if we're going to pretend, I'm going to practice too... practice being a real woman and how she would react. Okay?" Jack shrugged, "Okay."
Darla pulled him to his feet. Jack followed, adjusting his cock so it was against his belly and not sticking out so visibly -- although it was still obvious. Darla hugged Jack, "Let's dance to start with."
Darla swayed against him and he felt awkward and put his hands on her shoulders. "Okay, that's a start, but you have to show a woman that you want her." She pushed herself against him, he could feel her breast against his chest and his cock against her thigh. Jack avoided face to face and put his face beside 'hers'. This was weird for him, but god she felt great.... "She?" What was happening to him?
Darla had been careful and taped her cock down so there wouldn't be any boner on boner action to disturb him. She grabbed Jack under his arms and hugged him, pressed her face onto his shoulder, "Jack... pretend I'm a woman." Jack exhaled and hugged her, moving his hands down to her waist. "Good." she encouraged, "You say more with your body than you can with your mouth."
Darla's education continued, "However... while you are trying to move on a woman's body with your own, you have to talk to her to keep yer mind stimulated too. Compliment her."
Jack shrugged, the whole experience was surreal and yet he was turned on. Darla was subtly rubbing her thigh against his cock as they danced to keep him turned on. He put his face in her hair, "Well... your hair smells great. Reminds me of Tiffany's."
Darla, "Thank you, Jack. But never compare one woman to another." Jack winced, "Okay, Da--DARLA. Sorry." He shrugged, "Uh... you look really great tonight. Your skirt is nice."
Darla smiled and gave Jack a reward, lowering his hands from her waist to her hips. "Really?" Darla purred, "It's not too tight? Doesn't make my butt look fat?" Jack continued as he moved his hands down onto Darla's ass as if to check, "No. Wow. You're ass, ur, BUTT is like... perfect." Jack squeezed Darla's ass top down to bottom, each hand filled with a meaty round cheek.
Darla was starting to get turned on by Jack's squeezing of her ass. This in conjunction with his stiff cock rubbing against her thigh was giving her an erection of her own. She felt her cock start to pull away from the tape! She hadn't figured it would get so hard! About to spring her boner right into him, Darla abruptly spun around in his arms, hitting him in the face with her hair as she turned her back too him. Just in time too, her cock was hard and loose and pushing out the front of her skirt.
Jack was puzzled by Darla's sudden move, unsure of where to put his hands, which were still about waist level. Darla moved his hands up to her breasts as she backed into him, covering with a giggle, "Since you like my ass so much, here you go."
Jack smiled he like this, always fantasized about this position. Darla manuevered her hips to trap Jack's erect cock in her ass cleavage. She humped backward a little, grinding against him. "Hold me and tell me what else you like about me." Jack moaned as her ass flesh pinned his cock between their bodies, "Uhhhh..." Jack was getting worried he might cum, but he gathered himself. "Well, yer hips are really, uh, sexy too." She dragged his hands away from her breasts down to her hips, "Feel them. Hang on to them."
She continued to grind her ass against him, essentially jacking his cock with her ass cheeks. She felt him start to push against her, he was dry humping her!!! Darla was now just as hard as her son was and his meaty pole between her ass cheeks totally turned her on. Her asshole fluttered under his hot cock sliding above it. She wanted him inside her so bad, but she had to contain her lust. She leaned her upper body back to him and put her head on his shoulder, "What else do you like?"
He was buzzed and horny, "Well, I like your hair. And your lips. They're really nice."
Darla turned around and smiled, face to face with Jack, "Well... let me show you what I can do with my lips." Jack closed his eyes and winced, afraid his shemale dad was gonna kiss him. Darla knew better than that. While Jack's eyes were closed, she dropped to her knees in front of him. Jack felt the tug of his zipper and barely got his wits and his eyes open by the time Darla had his pants at his thighs, boxers and all.
For Darla, it unfolded in slow motion. In the light of the candles, Darla's prize was freed -- Jack's virginal eight inch cock bounced out in front of her. She paused as the realization of her success hit her. The plan had worked...
But this was the moment of truth for Darla. She had of course fantasized about sucking cocks and being fucked by cocks, but had never had one in her mouth... or even in her hand besides her own. As if reading her mind, a nervous Jack managed to utter, "I've never done this before..." Darla slowly wrapped her hand around it, feeling the soft warmth of the skin contrasted by the stiff throbbing power within it. "Neither have I, baby." Darla's response relaxed Jack, he wasn't the only virgin here.
Darla pushed her pursed lips onto the head of her son's cock. The heat of his skin surprised her. Her lips parted ever so slowly, she wanted to savor this moment as she flattened her tongue and his head popped inside her lips. Jack groaned, "Oh god."
Gripping his cock, Darla jacked it, pushing more blood into the head, which swelled in her mouth. "Mm-mmm," she moaned as she tasted him, waiting as she tightened the seal her lips had on his pole as she increased the suction to suck on the head. Darla wasn't going to do anything else, though. She wanted him to show her he wanted it. He sensed it, because almost immediately she felt him push his pelvis forward... pushing his cock deeper into her mouth! She relaxed her lips and let him push three more inches in... and his cock stopped at the back of her mouth. She held it there, savoring the fleshy taste, letting it own her. Jack felt the wet heat of Darla's mouth on his cock and he was in heaven. His first blow job was everything he fantastized about for the last few teenage years.. but it had only just begun.
Darla slowly pulled back and pushed forward as she began her first blow job as well. One thing that surprised Darla was the amount of saliva she was generating. She was drooling all over her son's cock and she pushed in and out of her mouth. Sure, she started out with a basic in and out, but soon utilized all the usual tricks 'her' wife had used on 'him'; opening her mouth wider than the rod and pulling in cool air, swirling the tongue under the head, etc... It wasn't long before Jack groaned in a way that meant he would be coming soon. Darla didn't want that yet.
Darla pulled offf and jacked the top of his cock as she licked all the way down the shaft. She licked up and down it like an ice cream cone. Her goal was to tattoo her tongue on every square millimeter of this beautiful piece of meat before it fed her -- just in case she never got it again. "Do you like that, Jackie?"
Jack nodded, his mouth couldn't form words, "mmm-hmmm." Jack noticed Darla had her other hand on his thigh, using it to steady herself. As Darla nibbled the head of his cock, she looked up at him, "A woman likes to know how to please her man. She likes him to be in charge... show her what he wants." Darla took her free hand and moved it to Jack's hand, bringing it to the top of her head. She took the head of his cock into her mouth and waited. Jack's hand tightened on her head and he pulled her mouth onto his cock. Darla smiled as her son filled her mouth with his cock and she thought, "Gotcha."
Jack was now an active participant as he controlled Darla, pulling and pushing her volcanic mouth onto his meat. He savored the alternate cool air on the outside, warm wet mouth on the inside. The tight velvety seal her mouth made around his cock was heaven and she was driving him crazy with the occasional tickle from her tongue stimulating the area under the head. He was surprised, Darla seemed to be really good for her first time.