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'Failure is not an option.' pt 2. by DLC's alyssa
A 25 William Holt had gotten used to people calling him ‘Billy’ despite his age. Barely making his way through the college curriculum it had taken him 7 years to get a degree. Like many a male his age his immaturity was an ever present undercurrent in the choices he made. So many of the girls he’d gone to school with now had jobs in the corporate world while he was left taking menial jobs like passing out pamphlets for the new car wash in town.
Never one to work out much his thin frame appeared less threatening then some males his age. He rode his bike and locked it up on the street sign with the name Deer Lane on it. Swinging the back-pack in front a quick brush back to his shoulder length blond hair he checked to see if he had all the fliers he was to pass out. Bashful at times he’d been told to hand deliver the pieces.
Kurt Belmont happened to look out the upstairs bedroom window fresh out of the shower he held the pair of panties in his hand using them to stroke his cock. At 41 a life long closeted Cd he had been lucky to have parents that left him a sizable trust fund enough he really didn’t need a job. The office he rented in town was more for appearances then actual work.
“Oh who is that cutie…what’s he doing …handing out fliers? He’ll be at my house soon I wonder…just wonder…maybe.”
Quick thinking he slipped a pair of ‘Speedo’s’ on giving a tug round his waist before moving down stairs to the kitchen. Writing it on a note the sign read ‘please use back door’. The app on his phone open he programmed the water sprinkler for the lawn making the adjustment. The sheer fabric of the living room curtain liner let him track the movement of Billy as he neared.
Walking up the flagstone to the luxurious home Billy read the note and moved around the corner. Kurt answered the door pulling it open with a smile on his face.
“Step in for a moment…I’m Kurt, what have you got there?”
"Hi Kurt I’m Billy…I’m passing out fliers for that new car wash in town.”
Kurt lit the vaping pipe fairly sure that Billy would partake in getting high.
“Here have a seat…. take a hit while I read it…let me get you a coke or something.”
3 hits in Billy could feel his buzz.
“Say would you give me a hand. I need to move some of the lawn furniture to water the grass.”
Holding out a twenty he let Billy see him slip it in his back-pack.
“Gee thanks …sure thing Kurt.”
The spouts of water sprinkled the yard out back walking outside Kurt had Billy on the end of the table as they moved.
“This can get tricky lets slide it slowly.”
Holding still a moment he gave a push just at the right time. Billy rolled down the sloping grass wet with water and dirt.
“Oh geez I’m sorry.”
Kurt walked down the grassy slope before slipping himself. The two had a laugh at being made dirty drenched with a spout of water spitting in their direction.
“Ok lets get inside….so sorry about that.”
“No its alright Kurt its not your fault I slipped…boy I’m soaked…..look my shirt and shorts they’re filthy.”
In the kitchen the two realized just how dirty and wet they were.
There was something commanding about Kurt’s voice when he said it after taking the weed pipe back from Billy for another hit.
“Follow me, I know what to do…did you wipe your feet?”
“Yea…Kurt…what a mess I’ll take off my running shoes.”
Outside the bathroom door Kurt spoke up.
“You use this one…gunna need some towels though.”
Stepping inside Kurt turned on the water.
“I think the blue one is body wash, no maybe the red…you’ll figure it out.’
Kurt left leaving the door ajar slightly. The hot water felt nice cascading down his body as Billy took in the size of the large shower with tier seating. His hand slid down and cupped his balls as he acted on the urge to stroke his 5” penis.
“Here are some towels…I’ll leave them on …”
Billy heard Kurt’s voice as the shower door opened. Kurt looked down to see Billy’s hard penis. It was enough for him to step in and join Billy. Frozen still Billy watched as the slightly taller Kurt approached.
“Kurt....but I’ve never been with a…..”
The seasoned hand of the Cd felt nice as he took hold of Billy’s hard penis. Slipping next to him Kurt lifted Billy’s chin. The two kissed wrapping their arms around each other.
“Baby slip my bikini bottom off.”
Just saying it like that made it sound feminine. A pair of small a-cups developing Kurt was proud of the thin body he maintained. It allowed him to dress in a number of feminine pieces of clothing creating the look he wanted when dressed en-femme.
As Billy lowered the bottom he saw the single strip of hair on Kurt’s mound. The cock started to grow firm freed of the bathing suit.
“Your hands they feel so soft they remind me of a girls.”
Billy smiled nervously holding the suit he lowered to the floor for Kurt to be able to kick it off. He found himself on his knees looking at a male body free of hair. His hand ran along the leg of Kurt looking up his face so close to the cock he smiled once more seeing Kurt undo his hair band. Shaking it loose his long hair fell to his shoulders.
Kurt caressed Billy’s blond hair while he knelt.
“This hair of yours is lovely….what’s your favorite girls name?”
“I always liked Natalie.”
“Very nice, very pretty …Natalie honey pout your lips I need to feel your mouth on my cock.”
“Natalie? But I’ve never sucked a cock before.“
“Yes Natalie now be a good girl and do what you are told.’
Overcome with the urge Billy obediently slid his mouth onto the hard cock. Kurt knew once a male sucks on a cock his thoughts concerning his sexuality are in play. In Billy’s case being given a girls name made it even more so.
A few minutes in the point being made Kurt pulled Billy up to sit on the tiered seating. He found himself legs spread on either side of Kurt’s thighs.
“Natalie sweetie lift up lets slip this inside you.”
His hands resting on the shoulders his body lifted as Kurt slid a vibrator slick with lube inside past his rosebud entrance. As Kurt shifted Billy detected the movement of his a-cup breasts as they gave off a slight jiggle. The pair of feminine looking nipples begged to be kissed.
‘Natalie’ lowered his head taking one in with his mouth.
“Call me Suzanne…oh Natalie that feels so nice.”
A few minutes later Kurt took out the vibrator carefully guiding his cock into place ready to replace it. A glob of lube in his hand slicking the piece up he next had Natalie slide his rosebud onto the hard cock. So thin he easily could rotate his pelvis back and forth Natalie took to riding a cock for the first time as he bounced up and down.
“That feels good …you like being called Suzanne you say.”
“Yes Baby…you do that nice girl. I have so much to teach and show you…have you ever worn panties before?...your mothers perhaps or maybe a girlfriends?”
Biting his lip the two words came out.
“My mom’s.”
He added after his moan.
“Ewww….I think she knew it....she always wears the prettiest kind."
Edging close yet not coming ‘Suzanne’ decided to stop since they had all day. It was time he introduced Natalie to the world of woman’s clothing and the delight it often can be when done right especially when put in the lingerie to go with it.
Billy held still as Kurt lathered the hair removal crème on his body caressing his skin 12 minutes later or so the two looked to see it fall off his frame swirling down the drain with the water.
The pair of c-cup breast forms pushed out the material of the bra top of his bathing suit Natalie was put in. The matching bottom felt sensual as well as his smooth hairless legs. A unique thong piece underneath tucked his bits away while leaving behind the look of a vagina. His hair awash in curlers he held still as Suzanne made his face up.
“I feel like such a girl Ms. Suzanne.”
“Wait until we brush out these curls darling.”
Having seen his mother do it Billy took a tissue and blotted his lips.
“Hold still I want to get your eyebrows just right…..you are in need of a mentor girl.”
One by one the hairs had been pulled out maybe it was that he was still high yet he would later realize just how feminine they made his face look. The gentle slope of the tapered eyebrows added the right touch. Light red blush on his cheeks he looked on as the false eyelashes took on a lifted curl from the mascara wand being used by Suzanne. The nail extensions soon were covered in red varnish to match his toes.
Fully made up the two looked like a pair of women sunning themselves at Kurt’s pool. A shake to his blond curls near his shoulders it amazed Natalie to see how much of a camel-toe look the piece under his bathing suit bottom made it appear like he had a vagina.
By the time the afternoon sun gave way to the evening they each would have a lovely set of feminine tan lines.
“I called the car wash …..told them you had an accident and we’d drop off the fliers later.”
“Were they cool about it?”
“Yes but then again like so many companies that use them…. minimum wage workers are a dime a dozen and paid nearly that anyway. I don’t want my girl to worry about money, something tells me were going to have the kind of relationship we both have always wanted.”
“You know I knew a friend from highschool who turned trans he moved to New York I think he is a model now…to be honest it kind of turned me on….I mean the idea that a guy can become a gurl….It made me wonder what it would be like to do it.”
Knees together Natalie pivoted at the hips lifting up to lean over and slow kiss ‘Suzanne’.
Laying back nearly naked on the bed Natalie watched as his arms stretched out were put in binders at the wrist. It felt natural to spread his legs before seeing them too secured at the ankles. The koala swimwear camel toe piece made him look like his dick was never on his body and instead a pussy was between his legs.
The seams of the breast forms being covered in foundation made them appear as though he’d been born with them all along. Arching his back he shook them delighting in the sensations.
“Suzanne I can hardly move.”
“I want you feel totally helpless…for you to be the kind of girl I know you can be you have to release any sense of control.”
He bent down an lovingly kissed Natalie
“You look so fucking hot…those tan lines your makeup and hairdo….now let go of that feeling you have to control what’s going to happen to you. Put your mind in that place you are just a sexy submissive girl who needs to be with her dominant lover…go ahead beg me to fuck you and convince me……you are about to find out what it’s like to be bred by a cock.”
Natalie never felt hornier the pretty nail polish the sexy tan lines the feeling of his long hair and makeup he looked on as Suzanne slid onto the bed stroking his cock. It went in so easily after the large anal plug was removed.
To see it move in and out with no hint of a penis on his frame was taking him to that feminine place that had been awakened within. He tried testing the restraints yet gave up realizing the futility of it. Natalie let his body relax and take the fucking. So real in their movement the breast forms took on a life of their own as they slid back and forth.
“Natalie you’re becoming a woman tonight once you feel me breeding you with my cream it’s likely you’ll always want more of the same.”
Kurt’s hand clutched at the breasts
“Fuck I love a girl who has nice tits.”
Natalie arched his back feeling girlish as he did so.
“You know I can give you some of your own…would my girl like that? Would pretty Natalie like to have to wear a bra every day? Ohhhh fuck your pussy feels so nice…that can be made to happen too….tonight when you sleep picture yourself with a lovely pussy.”
The words were driving Natalie to the edge he could feel his masculinity disappearing. His head tilted back near breathless his mouth pouted open as he thought about the offer.
“But what would I do…my job…I don’t have any womens clothing or stuff…could I really have a pussy…they’re so pretty they look like a flower between a girls legs….my breasts could I have some like the breast forms I have on…..Oh fuck your cock feels so nice Daddy.’
Kurt smiled down
“You’d become a kept women…you’ve heard of those haven’t you….your days are filled with femininity doing things a woman does to keep herself looking pretty…you won’t be taken seriously no you’ll be looked on as a tart of a t-girl too caught up in her girl world of feminine vanity to care about other things deemed more important.”
“Your cock Daddy …..it’s starting to swell I can feel it….a kept woman…one who does the housework and goes shopping and stuff…..and gets her hair done and things and takes care of her lover…oh fuck me, oh fuck me, oh fuck me.”
“See you’re already sounding like a pretty trophy wife.”
“Your boobies look pretty the way they bounce.”
“I’ve told you in the morning I can give you the pills that will put you on the path to have your own. I’ve been thinking of transitioning too yet I like having a foot in both worlds male and female so it’s likely I’ll stay as a Cd.”
Natalie closed his eyes on feeling Kurt’s cock pulsate.
“Your going to do it….your going to breed me like a woman with your seed. Oh dear goddess….ohhhhhh yesssssss.’
Natalie looked down to see his cream had wet the tight little tucking thong.
“Daddy you just made me get wet….look…..oh I want it….everything you said.”
Kurt reached back undoing the Velcro on his ankles. Moments later he did the same to the ones at the wrists of Natalie.
Natalie let his legs lift up holding along the sides of Kurt’s hips. His arms went to hold him in an embrace
“Ohhh your cream….it’s so hot…oh yessss….it feels so different to have you come inside me.”
End of part 2….