The Switch Hitter

Story Info
His family helps him become the girl inside of him.
36.1k words
4.75
152.8k
150
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Biskit
Biskit
886 Followers

This love story could have been submitted in the Incest section but since for the most part its bisexual, transsexual and cross-dressing, I decided not to offend the incest purist and submit it here. All the characters are of course fictional. Not sure why I couldn't get one of the volunteer editors to help me, lord knows I needed one and I certainly did try finding one. All mistakes are mine so please forgive my grammar and my unintentional mangling of the English language.

*

"Jimmy," Ellen Cougar called from the bottom of the stairs. She quickly corrected herself. Her son had stopped using his Christian name months ago. "Jamie honey." She still had trouble mentally thinking of him as her daughter but it was getting easier with each passing day.

"Yes Mom." Nineteen year-old Jamie Cougar appeared at the top of the stairs. He had just stepped out of the shower. A large bath towel was wrapped loosely around his slim waist. Water beaded up on his smooth, feminine neck. Little droplets rolled down a flawless chest and over perfectly rounded breasts where they hung momentarily from coral tipped nipples before falling. He smiled down at his mother, cupped one of his new breasts, and naughtily toyed with his nipple. The simple act was meant to excite his mother.

"I, ah..." Ellen had to take a breath before she spoke. She still wasn't used to seeing her son with breasts. Her hand went to her breasts to reassure herself that hers were as real as his. "Your Aunt Lettzie just called dear. She said she'll be picking you up in an hour. Do you need help getting dressed? You don't want to keep her waiting."

"I'm fine Mom; I have plenty of time, stop worrying so much." Jamie dropped his towel and saucily tossed his hips. He couldn't resist a little laugh. He liked being naked in front of his mother. It was fun and he knew she felt the same way. Playfully cupping his breast, he thumbed an excited nipple and said, "I have everything under control." Playing with his nipples always made him hard and his cock began to stiffen and rise now. When his mother let out a little gasp, he threw her a playful kiss before turning his back to her. He gave his sexy bottom little shake before disappearing out of view. A soft feminine laugh escaped his lips. "I'll call you if I need any help."

"Such a flirt," Ellen said swallowing hard. Jamie's naked body, half female, half male never failed to turn her on. She felt the excitement building between her legs. Her hand lingered over her breasts. She enjoyed how hard her nipples suddenly were. "Let me know if you need help with your make-up or your hair dear. You want to look nice for Lettzie." Lettzie was her sister-in-law, married to her older brother Eddy. Lettzie was also her son's lover and mentor and you never wanted to disappoint her or keep her waiting.

Jamie couldn't resist teasing his mother a little more and stepped back into view. His pocket-sized penis was fully hard now. He reached for it and ran his small hand up down its delicate pink length. When he let it go, it bounced comically up and down. "I won't be late Mom." With his mother watching, he began to slowly masturbate. "But if you want to come up and make yourself useful, I wouldn't mind one of your fabulous blowjobs." He let out a sexy laugh, flipped his cock and smiled. "Just joking Mom, now relax will you. I'll be ready in plenty of time."

Ellen couldn't help laugh at her son's antics. "Jamie Cougar, behave yourself young lady and stop doing that. You know what it does to me. There'll be plenty of time for that later on."

Ellen Cougar was a sweet and bubbly, thirty-eight year old housewife with a more than an ample bosom and what her husband fondly called, a very nice 'caboose.' To the casual observer, she was just another attractive suburban housewife, but behind closed doors, she was a wild and adventurous woman that enjoyed incest with her son and brother. She was excited for Jamie tonight. In the next few hours she would be watching him fuck her brother and his father as well as his aunt. It made her nipples ach and moisture flow from between her legs as she thought about how wonderful it was going feel when his beautiful little penis was inside of her.

Just thinking about fucking him made Ellen's pussy begin to boil over. She didn't know what she loved more, Jamie's petite little cock or his mouthwatering breasts. She knew his body better now that when she was nursing him. She should, she'd been making love with him almost daily for months. Earlier today she'd helped him remove any trace of pubic hair from around his beautiful little cock and balls. She'd of course given him a blowjob afterwards and licked her lips now as she remembered her act of incest. Her husband fondly said Jamie's cock reminded him more of a large clitoris than a penis. She agreed. She was about five inches when hard, but for her; it was a perfect fit in either in her mouth or pussy. There was nothing she'd like more right now than to run upstairs and make love to him but she knew their time was short and Lettzie would hold her responsible if he wasn't ready...and hard when she arrived.

"Suit yourself mom," Jamie laughed as he temptingly stroked his cock. He loved teasing her but knew she was right about not fooling around right now. He still needed to moisturize his body and then dress. Giving his mother a playful wave of his cock, he hurried back to his room. "I'll call you if I need any help."

"Just remember not to go too heavy on the eye liner and use that camel brush to blend everything in evenly. Oh, and bring a hair brush and comb down when you're ready. I know your hair will need some help."

. "Yes mother." Jamie said. He thought about masturbating just to take the edge off of his sexual excitement but knew his aunt would be disappointed if he wasn't rock hard for her. He'd been her lover since the day she and his uncle had caught him at the adult movie theater. She'd gotten him to admit being bisexual as well as wanting to cross-dress. That same day he'd also learned that his bisexual uncle had been cross-dressing since he was a teenager. Until then, he'd had no idea that his mother and father were both bisexual and that his mother had been fucking her brother since they were teens. Over the past months, with his aunt's and mother's help, he'd become the girl he'd always dreamed of being.

Tonight was going to be special. Even though he'd been dressing as a girl at home, this would be the first time he would be leaving the house as one. In the past, either his aunt and uncle would come to their house or he would change at their home before having sex with them. He'd been taking hormone shots for months and his breasts were almost where he wanted them. They'd grown to and exciting 32B cup but he was going to continue with the treatments until they were at least a 34B, maybe a C cup. He looked at the clock. He had less than an hour to get ready.

Ellen excitedly looked over her transvestite son. "Let me see Jamie," she said when he finally came downstairs. She thought the outfit that Lettzie had picked out was perfect. He had on a very short, dark blue skirt that showed off his sleek and tawny legs and a matching blouse that was just sheer enough to reveal that he wasn't wearing a bra. His excited nipples were very obvious. She thought the hormone treatments he was taking had helped sculpt his body; changing it from a slim effeminate male body to very feminine and svelte young ladies. Ellen would have killed for a butt like his when she was his age.

She couldn't resist nibbling on her son's delicate neck as she combed out his long shimmering brown hair. "Very nice dear, you look so beautiful," she said as she kissed his ear lobe. It thrilled her that she was the mother of such a beautiful and sexy teenage girl.

"Thanks Mom," Jamie said.

Ellen was very supportive of her son's decision to live his life as a girl. She missed her baseball playing son, but she'd always wanted a daughter and now she had one. "Let me fix this," she said as she fussed with his hair. He'd let it grow out until it now hung just a little blow his neck line. To control her own excitement, Ellen busied her hands by combing out an imaginary flaw in his hair.

"You're the best mom, thanks."

"You're welcome dear. I want you to look beautiful for your aunt and uncle. Now stand still for just one more minute. I want to make sure you look perfect." The last thing she wanted was to disappoint her sister-in law. Lettzie was the reason she was fucking her son. Without her, the incest she now enjoyed so much probably would never have happened.

"Mom, please," Jamie said letting out an exaggerated teenage sigh. He knew she meant well but she was making her crazy. He handed her his hair brush. "Just fix the back."

"Stand still then."

"Yes mother." He really didn't mind how she fussed over him. He wanted to look perfect for his aunt. Lettzie had picked out everything he was wearing. Beneath his skirt, he had on a new pair of red thongs that his uncle had given him. He loved how they caressed his cock and balls and especially how the little string pressed up against his 'pussy.' His aunt had great taste, maybe a little over the top sometimes but he wore the sexy outfits she bought him without question. He loved being a girl and wearing pretty clothes but knew that once his aunt asked him to strip; he wouldn't be wearing them the rest of the night.

Lettzie had a thick German accent that made everyone laugh and he thought she sounded so sexy when she would say things like, "Jamie honey, vou have such a vonderful little clitty, vhy do you vant to hide it from me by veering da panties? Please take for me them off."

"Stop fidgeting. I don't want to snag your hair," Ellen Cougar warned. When she was satisfied, she checked his nails. The red polish was perfect and matched his toenails. She'd worked with him for over an hour to get them perfect. She sniffed his neck. "You smell so wonderful dear. That's the perfume Lettzie gave you isn't it" She inhaled deeper. "A hint of rose, I think." She couldn't resist nuzzling his neck. She slipped her tongue inside her ear and huskily said, "Be sure to thank her."

"I will mom and you better stop doing that, you're making me hard." He liked telling her things like that, knew it turned her on.

Ellen made love to his ear lobe and softly laughed and said, "That's what your mother is for honey, to make you hard so you can fuck me."

"You'll have to answer to Aunt Lettzie if I have an accident," Jamie laughed.

Ellen ran her hand down the front of his skirt and felt his hard cock. She sexily whispered into her ear, "Honey, it won't be an accident if your mother makes you cum, it will be intentional."

"You're so bad Mom." It was impossible to ignore what she was doing and he grew harder. He glanced at his refection in the mirror. He liked what he saw. He'd always wanted to be a girl and in his mind, he finally was.

Ellen pointed to the small floral gift bag on the table. "Don't you dare forget your uncle's present." Her brother's gift was wrapped in pretty pink paper. It was held together with a teased ribbons and a small bow. "He's just going to love the panty set that you picked out for him. He's always looked so good in pink." She started to get a little emotional thinking about her brother and son together. She thought it romantic that they were lovers. She'd fucked Eddy often enough to know what a wonderful lover he was and envied that her son was going to have his cock inside of him tonight.

She'd discovered Eddy's fetish for dressing as a girl when they still lived at home. It had oddly turned her on to see him wearing her bras and panties and instead of being outraged or disgusted, she ended up teaching him how to apply his make-up and shared her clothes with him. Incest came easy for them after that. She'd always been a little kinky and found that fucking her brother when he dressed as a girl very exciting. Except for the time when he was in the Army, they'd been lovers ever since.

Eddy had been stationed in Germany when he'd met Lettzie Von Stubben at a gay bar. He'd been in drag. Lettzie was there because she had a thing for handsome bisexual military men that also enjoyed cross-dressing. Her father, a colonel in the German Army was also a cross-dresser and she'd been having sex with him since she'd come of age. When she learned of Eddy's incestuous affair with his sister, she knew he was the one for her and had accepted her funny American soldier's proposal but insisted he ask her father for permission to marry her. Being a gentleman, Eddy had done just that but in a most unusual way. Knowing it would please Lettzie as well as his future father in-law he'd worn his sexiest silk teddy when he'd knelt and asked permission. To show his true intentions he'd sucked her father off in front of her whole family. Fritz Von Stubben had been impressed, not only with the quality of the blowjob but the sexy feminine clothes Eddy had worn. Lettzie and Eddy were married in Germany but came back to the states to live.

Upon returning to the states, Lettzie had insisted Eddy continue to fuck his sister. Ellen was grateful that her sister in-law was so understanding. That's why it had been so easy for her to allow Lettzie take her son under her wing and turn him into the beautiful young lady that was today.

Now as she helped her daughter, Ellen couldn't resist kneeling in front of him and resting her cheek against his swollen cock. "You feel so wonderfully hard Jamie." She lifted his skirt and cupped his bare bottom and pressed her face to his panties. She moved her hands over his legs and bare bottom. "You have such soft skin dear, I'm envious." She moved behind him, kissed each bare cheek. Inhaling deeply, she smelled the perfume he'd applied there. "I could just eat you up," she said as she smothered her son's firm cheeks with tiny kisses. Moving around in front of him, she caressed his cock and told him, "This reminds me of growing up. Eddy always got so hard when I helped him dress up." She kissed him through his panties and giggled and said, "I just love my little girl's clitty."

Jamie blushed. He didn't mind that he had a small cock or that everyone thought it the size of a large clitoris. It just made him feel all the more feminine. "Thanks mom, when you say things like that, it just makes me want to show you how much I love you." He pulled her up and covered her breasts with his hands. He wished his were as big and round. "You have such great boob's Mom. I wish mine were as nice."

Ellen smiled and allowed him to fondle her breasts. She put her hands over his and guided them all over her tits. "Yours are perfect honey and just as beautiful." He'd made her incredibly horny and now directed his hand under her dress and between her legs. "Touch me here honey." She wasn't wearing underwear and trembled when his finger slip between the moist folds of her pussy and rested against her clit. She urged his finger inside of her and let out a content sigh of pleasure when he found her hot spot. "If Lettzie wasn't picking you up in a few minutes, I'd show you exactly how much fun two girls can have together."

"I know how much fun we can have mom, you've shown me often enough," Jamie said as he fingered his mother's cunt. He loved how wet and tight she was, wished he had a pussy instead of a penis. Since he didn't, he pressed his cock against her and said, "I'm so lucky to have such beautiful and sexy mother that wants to make love to me all the time." His life had been an emotional rollercoaster for the last year. He'd gone from a shy and sexually confused boy that was jacking-off strange men in dark theaters to the transsexual young lady he was today. He pulled his mother's face to his and kissed her. "I love you so much mom, thank you for being you." He slipped his tongue between her lips and kissed her passionately.

He kisses just like a girl, Ellen thought. "And I love you so much honey." She kissed him back and softly told her, "Making love to you is so special, your father feels the same way and we're both so glad you feel the same way about incest as we do."

"You know I do mom. Fucking you and dad is so fantastic."

"And who is this beautiful young lady?" Hal Cougar asked as he came in from his study. He smiled when he saw his daughter and wife embracing. It was every father's fantasy come true to watch his daughter and wife making love. He put his arms around Jamie and lightly kissed him on the lips. "You look fantastic honey." He stood back and admired his daughter. "You look hot Jamie honey, really hot tonight." He could feel his cock grow.

"Thanks daddy. I'm glad you approve." She loved being her daddy's little girl.

Hal Cougar cupped his crotch and lewdly held his erection. "You give me a hard-on every time I see you honey."

Ellen Cougar playfully slapped at her husband's hand. "Hal, your awful, stop it now or you're going to get Jamie all excited."

"Too late," Hal said pointing at the little tent in the front of his son's skirt. He teasingly said, "I think you've already done that dear so don't blame me." He reached for his son's cock and lightly held him. "Nothing wrong with a father telling his daughter that she gives him a boner." He pressed his cock against his son and said, "Or telling her how much I love her little clitty."

Jamie blushed excitedly. "Be careful daddy or you're going to make me cum and Lettzie will kill me if I get my panties dirty." He reluctantly eased his father's hand away from his cock. He didn't trust him or himself. He gave out an effeminate laugh and leaned into his father and kissed his cheek and whispered dirtily into his ear, "There'll be plenty of time for us later on daddy." She pulled his arms around him and rested them on his butt cheeks. "I'm saving a very special place for you later on."

"You better sweetheart," Hal Cougar said as he excitedly jammed his cock against his son's pussy. "Your old dad can't wait to get between these gorgeous legs of yours and make love to you." He pulled up Jamie's skirt up and worked a finger between his taught cheeks and said, "And I'm going to put it right here sweetheart." He flicked his tongue inside his ear and whispered, "Daddy can't wait to fuck his little girl."

Jamie breathlessly told him, "Me either daddy. You make me feel so beautiful when you're inside of me." Jamie thought it every girl's fantasy to be fucked by their father, especially one that had such a huge dick. She kissed him lightly on the lips. "I love you daddy." This was incest at its best and it filled him with pride that he was having sex with his parents.

Hal continued to push his cock against Jamie as he fingered the moist area between his son's tight cheeks. "You are beautiful baby and daddy loves you so much."

"You two had better stop or you're going to be in so much trouble when Lettzie gets here," Ellen Cougar warned as she embraced both of them. "And by the way, you're making me extremely horny." She kissed her son's cheek and demurely reminded him, "Your father's not the only one that can't wait to make love to you. I just so happen to love it when a certain young lady fucks me."

"You know how much I love fucking you too, Mom" Jamie told her as he played with her big ripe breasts. He was glad she wasn't wearing a bra; it made teasing her nipples so much easier. He put his mouth to her breast and held a nipple between his teeth. "I just love your tits Mom."

Ellen's pussy came alive as her son nibbled on her breasts. "Jamie honey, you have no idea what that does to me."

"Can't help it mom, you turn me on."

"And you turn me on honey." Ellen giggled happily when he bit her nipple. "So naughty."

"Let's see what's under here," Hal Cougar said flipping up the hem of his skirt.

Biskit
Biskit
886 Followers