High atop a hill the classic vintage Victorian house often called a painted Lady had been in such disrepair it wasn’t even listed. West of 65 past Spring Hill it was down an abandoned path once called old Hatley road. Named for a Union soldier promoted on the battlefield that had been wounded in his chest and a leg losing the limb yet winning the skirmish staying at the front with his boys in blue Iowa troops.
Madeline’s real estate agent Hilda met her at the open gate twirling the key round her finger as she smoked a cigarette with her free hand. The woman had come recommended by an online network of LGBTQ friendly businesses.
“You sure you still want to take this on Maddy….you’ll have to have teams of construction guys blitz it to get it up and running and functional.”
The lesbian agent took another hit off her smoke before stamping it out with her foot.
“Yes I like it especially the wrap-around front porch….they don’t build them like that anymore. I spoke with the owner of Acme construction and home builders…they’re prepared to have it looking good fairly quick since I added incentives. ”
“High enough it will avoid the occasional flooding that occurs I must tell you legend has it that it may be haunted.”
Madeline smiled at her.
“You’ve never seen me in the morning…some days I’d scare any ghosts dumb enough to stick around.”
“Being north of town you’re not far from Des Moines…..there is a nice gay bar called Blazing Saddles you may want to check out…a couple others there too.”
“Lovely nobody parties quite like gays and lesbians….I trust they have no bias against t-girl’s.”
“Nope not that I know off in fact they have drag nights and some fundraisers where they break out a pole dance competition as part of a beauty pageant…I’ve often wondered why that’s the case with some places….I mean discrimination… Here we’ve been treated as outcasts for so long even after the Stonewall uprising 50 years ago….yet some bars choose to discriminate as though there is something wrong with males turned trans.”
The rolling lawn in front set off the structure with the same in back near a stable and small barn she plan on converting. Down a tree lined path once in the clearing a collection of over-grown shrubbery mingled with evergreen trees on three sides providing privacy not found in a bustling city.
The home officially hers Madeline stood in the living room looking around like she’d found a buried treasure. Using her lovely looking nails as part of her thought process they gently ran across her cheek as she lightly scratched it.
“I really could use a maid once things get finished.”
Mark looked at his list of items he’d been told to acquire from Mistress DLC. It had taken a few months free of any pressure on Dominatrix Camille’s part he decided that once accepted he wanted to see what it was all about to be under her guidance.
Emailing it Mark had written a letter to her where he went into his past history. DLC addressed his curiosity knowing many had come to her with the same concerns. The woman wasn’t the type to rush initiates aware the process often involved moving past any fears they may have at the unknown.
8 months to the day he’d first found her site he stood alone in his bedroom taking the required photos she’d asked of him.
Called ‘body-shot’ pictures Mistress Darklady had all potential DLC gurls do it knowing it was a way of monitoring their development while getting them used to being photographed. Two other pieces of equipment he needed was a Pc video camera and a tripod to go with a wooden paddle christened with the letters DLC, a chastity cage and a butt-plug.
Every few weeks or so he sent in new pictures. A BDSM collar on wearing his first ever pair of 4” heels Mark stood naked taking a front and back picture with two side profiles. Looking down at it he’d felt awkward wearing the chastity cage.
Getting used to taking the photos he was glad the dieting had taken off near 60 pounds giving him a noticeably thinner frame. He couldn’t explain why yet on many days he felt a gentle nature coming out. Jostling his balls playing with the chastity cage lock there was part of him that was scared he may not be able to get it off even though he held the only key.
He’d let her know just starting out that he wasn’t able to remove all his body hair as he had work concerns being employed at a company that was very conservative.
Madeline had developed their time together keeping him at bay with the occasional make-out session where both kept their clothing on. The many months seem to fly by yet one thing was clear to Mark the woman was the one in charge of their platonic relationship that he hoped would turn into a love affair.
There was no better example of that then when a few months in she told him she wanted him to grow his hair out. By springtime they’d been together for near 10 months and his hair was touching his shoulders worn back in a male-styled ponytail.
Deep inside he had always been curious about what it would be like to truly be in a Female Led Relationship. Now he had two an online one with Mistress Darklady and another with Madeline. So often being told what to do and when they’d be going out near always obeying her Mark came to accept Madeline as his loving female authority figure.
It was a DLC requirement along with regularly applying body softening moisturizer every day. One troubling thought he had was should they get to the point Madeline would see it how would he explain that his pubic hair had been trimmed to a puff of hair look many a female enjoyed having.
It spoke to the power Dominatrix Camille had over Mark and the others under her guidance that he complied.
Mistress DLC was pushing his boundaries too he’d gone from just taking pictures of his thin frame naked wearing the heels and chastity cage to others that included him spanking himself with paddle and sliding a dildo inside his anal canal. Each week went by until the only hair in his body was on his arms. She next had him occasionally wearing a pair of panties all day long at work with his chastity cage on.
As way of verifying Mark received a random email instructing him to take a few pictures outside in a remote location. Easy enough to do living in a town like Indianola he drove out route 65 and pulled off out of the way.
Looking at his watch to see he still had an hour before meeting Madeline at her newly refurbished home he made his way through the brush of the forest until he found a clearing.
Setting up the tripod he turned this way and that to see if anyone was near. Slipping off his cargo shorts and running shoes he removed his t-shirt with the Hawkeye logo on it setting them near his back-pack. Unaware it was called an estrogen rush he felt a wave of femininity flowing throughout his body.
He could feel himself consciously doing it pitch-forking his nails into it he fanned out his long hair letting it spill over his shoulders as he posed pulling a girlish blush up on his face. The lace panties looked pretty as he leaned on a tree looking over his shoulder seductively smiling at his I-phone on the tripod.
Nervously he open the backpack and removed the red 4” high heels with an ankle strap running along the back. Once more he made sure he was alone. Slipping the ankle strap through the eyelets he stood up with knees together. He felt so girlish doing it smiling at the camera put on time delay.
Taking three with his panties at his knees chastity cage on Mark finished up by bending on the waist, spreading his ass cheeks to show off the anal plug that was a DLC staple for her gurls.
His body had been feeling so different the past months. He had always had large areolas for a man yet some-how they seemed to be taking on greater circumference. Mark tried to convince himself that the looseness he felt in his breast area was just part of not doing weights any longer. Truth was he no longer felt strong enough to lift yet enjoyed the softer feeling of the absence of musculature as his arms thinned out.
Mark counted up near 18 pictures that he sent on to Mistress DLC before slipping on a brushed cotton ‘camisole’ top and adjusting his panties returning to his car.
Madeline smiled when she read the email from Mistress DLC. Succinctly short it merely said ‘in panties he’s wearing it’. Out loud she spoke to her self…’Game on lover-boi’.
“Hello Ms. Madeline…are you upstairs?”
Checking his hairband with it back in its usual look of a male ponytail he said it again standing inside past her front door.
“Hello Ms. Madeline?”
Seconds later he heard ‘I’ll be right down’.
The woman had done an amazing job the Victorian house looked as good as it did when it was first built in 1890. Gliding down the stairs her milky breasts bouncing on every step Madeline liked the idea she was in long pants in the pair of her blue-jeans while he wore shorts.
“Hi Baby…hmmm you smell nice…is that lavender?”
He knew he shouldn’t have picked up the scented body lotion when he bought it along with the Dove body-wash and women’s razors.
“Yea…I must have grabbed the wrong one at Meiers….I hope its ok but I’ve been moisturizing lately.”
Kissing him her hand slipped under his t-shirt feeling the softness of a brushed cotton camisole next to his smooth skin.
“Honey you feel so smooth…I’m always so cautious the first few months yet I realize we’ve not had real sex yet and I haven’t seen you without clothing off but it feels like your hairless…”
Nuzzling his neck with short kisses giving a quick flick or two at his firm nipple pulling her hand out she added.
“….hmm I like it.”
It had been some time since he saw her new home and liked getting the tour now that it was filled with furniture.
Sitting around the island counter in the kitchen he grew nervous watching Madeline absentmindedly play with his phone. A glance at the laundry basket half-filled with clean lingerie Mark made the off-handed comment as he took a pull on the bottle of water.
“Looks like you’re going to need a cleaning lady soon.”
Her feminist sensibilities rose to the surface.
“What?...you mean cleaning a home is women’s work?”
Back-pedaling he stammered out.
“Hummm no not really I was just saying…..I mean men don’t do housework…that didn’t come out right…I mean males can clean too…it’s not just for females…I mean women…weren’t they meant to clean….no wait I didn’t mean to put it like that…”
Her timing was perfect hitting the icon she lifted his phone up.
“I had no idea that you liked wearing woman’s panties…”
Her thumb and finger expanded the picture out.
“What is that around your penis?…is that some kind of lock?…and you’re in high heels too…hold on a second you have the same outfit on you’re wearing now…did you just take these? It looks like you emailed them…the hair on your mound…it’s a thin single line….why I have more hair on mine than you do…..take it off….everything I want to see you in the panties and cami-top.”
Mark stunned at being caught meekly undressed in the kitchen watching as Madeline collected the items. The outline of the chastity cage pushed against the lace trimmed thong pantie.
“I can see the imprint left by your high heels ankle straps….and you’re near as hairless as a fashion model posing the same way too.”
Giving him the once over she stood back taking it all in.
“Tell me…does a real man wear a chastity cage?...not to mention panties and a camisole.”
“No Ma’am… a real man would never allow such a thing to be put on him.”
“So if you admit you’re not a real man then where does that leave us besides doing as you call it women’s work. I see a growth opportunity that may provide you a lesson in humility. You will now learn how to keep a home clean…remember I like things a certain way....to make things interesting go and get your high heels….every time you fail to live up to my standards another item of feminine expression will be given you…..say yes Ma’am.”
It was a crossroad moment he could just leave and things would be over or stay and reinforce his obedience to her having his life now be completely guided by a dominant woman.
A few minutes later standing in camisole, panties and heels Mark could feel himself being inspected before beginning his chores.
“I’m afraid Mark won’t do…no I think perhaps Marcie is more appropriate.’
Perhaps it was the estrogen yet something inside Mark had him like being given his new feminine name Marcie.
Her sleeveless top revealed Madeline’s muscled arms as she heaved the axe high before bring it down with force to split the wood.
Marcie stood broom in hand looking out the kitchen window amazed to see the power Madeline possessed using the tool. She lifted the cut wood stacking it in neat rows.
Later that night alone in his bed Mark had the same dream. It was coming a little bit more into focus. He saw a woman in bed with long hair flowing down along-side her plain pajama top held closed with buttons. Next to her was what he thought was a nurse.
At 46 Jasper Jenkins had lived a life of growing up on farms. Manly in his down to earth appearance one never would have known he’d made a small fortune of 14 million dollars selling off acreage he’d inherited so that it could be fracked by companies in search of natural gas.
The man retained his landscaping and lawn care services company he’d started before he became rich. Serving Des Moines and other towns in a 100 mile area he felt as free a cowboy riding the open range sitting on his mobile ‘John Deere’ lawn mower leaving swaths of cut grass behind him.
Free-spirited and open-minded headphones on the Bi-sexual man would listen to his ‘Grateful Dead’ songs and Country and Western favorites while getting high just as he had in the days of his youth. Leaving clean lawns and pleased customers from his low rates behind he traveled the area happy as a priest in ‘Boys-town’.
What he also enjoyed was finding a youthful 25 year old or so farmgirl or boy who liked sucking cock.
A job outside of Ames Jasper’s finely tuned ‘Gaydar’ was working just right. The hay on the barn floor seemed to cushion the hands and knees of the 26 year old lad named Timothy. The two had played a cat and mouse game as Jasper drove his lawnmower while Timmy stretched out on a towel near the above-ground swimming pool every so often taking a dip.
The buzz of the lawnmower a little loud as it sat idled Timmy offered a drink of lemonade.
“You going to ask your mom…you say your name is Tim huh?”
‘No its just me around...some people call me Timmy…..my parents went to ‘Dollywood’ for a few days..”
“Always did love Dolly Parton.”
“Say you want a swim to cool off Jasper? It might feel nice on all those big sweaty muscles of yours.”
“I didn’t bring my bathing suit.”
“I could always take mine off if it would make you feel more comfortable.”
“Just so you know who is the alpha take yours off then you can undress me.’
The boy of 25 had been right the cool water felt nice on Japer’s muscular body. A good 6” shorter and thinned framed Timmy liked being in the embrace of the older man as they kissed in the pool.
A few minutes later his arms out-stretched along the top edge of the pool Jasper looked down at Timmy on the grass while he sucked his cock. Slowly running his mouth along the shaft he next slid his lips over the head of the hard dick. Jasper eased the boy’s shoulders back spreading his legs he dipped down ‘tea-bagging’ his balls in and out of the youthful mouth liking how his cock lightly slapped Timmy’s face.
The two found themselves in the loft of the barn the twin doors opens showing off the spacious view Jasper slid in behind Timmy. On hands and knees the lad felt so submissive playing the role of a bottom-boi.
Jasper’s cock thick with lust took a few moments to adjust to before they moved as one. Sliding in and out the well lubed piece ignited a passion in Timmy. He liked how Jasper would give off ‘fanny-spanks’ on his butt too cute for boy his age.
“Push back boi…show me how much you want my cock.”
Jasper let fly with the hardest tushy spank of the afternoon.
Timmy doing as he was told eased his body back and forth when suddenly he felt the hard dick begin to pulsate. Closing his eyes he lifted his head hoping he’d be filled with cream.
Jasper slowed his pace gently humping holding his hands tight to the hips of Timmy he let out the first blast of hot cum. He kept the cock all the way in letting himself be drained as Timmy squeezed his butt-cheeks with all his might.
30 minutes later Timmy looked on as Jasper closed the back of his open bed truck.
He read the slogan underneath ‘Jenkins Lanscaping’ on the side of the truck…’if that grass is greener on the other side of the street maybe it’s time you water your own lawn’.
“Timmy you might like a place in Des Moines…it’s a bar called Blazing Saddles.”
A right-wing Christian conservative Gus Johnson his boss at work left a message for Mark to stop and see him in his office. Despite the seeming incongruity of it a 12” cross was next to a picture of the president that many thought merely paid lip-service to the religion’s tenants as a way to merely please his base.
Standing in front while Gus his employer sat Mark felt certain he wouldn’t notice his long hair had been put in a man-bun under his hat. It had been a choice either show off the length of his hair or give it an upsweep of the bun and display that his ears had been pierced with gold studs.
Mark had been assigned the regular task of doing housework at Madeline’s home on Tuesday and Thursday afternoons and Saturday mornings. Called ‘Marcie’ when cleaning aided by the HRT he could feel himself losing his tenuous grip on his masculinity.
It was a simple process do the things on the list that Madeline made. Any screw-ups and he’d be taught a lesson in feminine vanity.
Mark soon realized his respect for women that clean a home was increasing as he discovered it took diligence to do it properly. Panties and cami’s became his daywear as did the high heels he’d worn the first day he accepted his duties as her part-time maid.
Two weeks earlier forgetting to clean the oven found him having his nails done by Madeline. Looking at the clear varnish on their oval contour he now knew why she had him grow them out.
A week before that he held still sitting on a stool after not dusting the book cases.
Madeline spoke about how she planned on having him learn how to handwash her intimate wear while she plucked his eyebrows to a thinner look.
On finishing her hand ran across the smoothness of his face seeing a look of admiration in his smile. Eflora crème being used on his complexion was eliminating the need to shave his face slowing the regrowth of what had once been light sparse masculine facial hair.
“There are days I think you’re getting better Marcie and others where it seems you’ve forgotten what you’ve learned about cleaning a home.”
Bending down Madeline kissed him leaving behind some of the plum color of her lipstick. It wasn’t the first time yet he was developing an appreciation for the light taste it left.
“Should your mistakes continue we’ll next move into the area of makeup. I want you to plan on helping me put on my face. I expect to see you improve your skills it will give me a reason to let you spend some time out of your chastity cage….tell me are you staying in touch with Mistress DLC? I don’t need all the details I just want to know you’re absorbing what it is she has in her curriculum for you.”
“Yes Ms. Madeline we communicate on a regular basis…the other day she spoke about maybe having a page put up of me…I would guess as one of her male sub’s.”
Madeline having gotten to know Dominatrix Camille better knew she had no male subs only male slaves or DLC t-girls some of whom were slaves.
“Let’s have you collect my lingerie Marcie and I’ll show you how I like them laid out in my intimate wear drawer.”
Mark’s boss gave him the once over as he held his hands behind his back afraid he’d notice his lengthened nails with clear polish.
“The Jones account called and let me know they want to order more…so get on that…is it me or are you still losing weight….did you stop drinking beer or something…my wife has been on me to do that too.”
Standing rigid at attention like a private in front of a drill-sargent Mark replied.
“Yes sir I’ll call on the Jones account and yes I have stopped drinking.”
“Very well you’re dismissed….you can leave…and call the Jones account in the morning….by the way I like your thin look just don’t lose too much….you’re almost as thin as my wife.”
Turning to walk out he could feel the slight movement on his chest. Mark half thought his pantie lines could be seen as he left the office. A look over his shoulders he saw his boss staring at his pretty butt in some ways it felt like he was being leered at by someone he'd always thought was straight.