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."
