Walt and Ann

This is a story about Walter and Ann.

Ann, 48, was a well built woman that looked like she could wrestle livestock. Although pretty, she was not slender, not exactly feminine, she was, as they say “Fit.” She worked at a doctor’s office as a tech and had a clutch of childhood girlfriends and boyfriends that were all involved with the local theater group and all gay as they come. Ann was the outlier, having the only ‘normal’ relationship and was frequently teased about her ‘Walt.’ Two of them, Billy and Paul proclaimed their attraction to Walt.

Walt, 45, was a former high school track star. Not tall, but still lean and slender with long dark hair that frequently was up in a pony tail, except when he was playing drums with his small rock group.

Life goes on for this couple. They had married years ago. Never had children. They seemed to be a great couple, but even Ann’s friends could tell she was envious of Walt’s attraction to the several groupies that always were at the band’s functions. She always told him “you cheat, I’ll have your balls removed!”

When Ann was 45, a major health issue hit Ann as she went prematurely menopausal. She felt like hell, gained a lot of weight, sweated constantly, and lastly, lost interest in sex. She developed a chip on her shoulder about everything. So, her doctor prescribed estrogen and progesterone and she while she took them for a year. She finally said, no, the side effects aren’t worth it, this therapy is over. In an interesting twist of fate, the insurance company and the pharmacy kept shipping the drugs for over a year. She threw them into the garage fridge where they piled up in a box. Hundreds of doses.

The trigger event.

Walt, spent more time with the band as being home was miserable. Two young groupies were always there and always chatting him up. He was almost always happy to spend time with them. And that lead to one night, his spending the entire night with them.

Ann was waiting by the door when he got home. They argued. They fought. But, in the end, both declared their love for each other. Walt was extremely distraught. Ann though, had other plans.

The trigger pulled.

That night when they went to bed, Ann gave Walt one of her Ambien. Then when he got a little sleepy and bit confused, she gave him another. Finally as he was almost totally out, she slipped him a third.

As Walt slept deeply that night, Ann pulled his legs apart and pulled his testicles and scrotum gently down and back. She then twisted them twice clockwise and then gently put his legs back together in such a matter that his testicles were showing behind his legs. Then finally, she put a heavy blanket over him so that he would not move through the night.

The shot fired.

The next morning, she got up early and looked over at her sleeping husband. He would be out for several more hours that morning. She looked at his testicles and smiled when she saw they were dark blue in color. They were twisted for sure. Just had to wait till he woke up.

It was around 10:30 while Ann was downstairs reading the paper over her cup of coffee when she heard the groans upstairs. Someone was in agony!

So she slowly made her way upstairs with a oh-so-concerned look on her face to find Walt in a fetal position on the floor clutching his groin.

When she was able to pull his hands away and look at his groin, she saw his testicles were black! Gangrenous necrosis black!

Her plan was a success!!

She bundled Walt up in her arms and carried his slender body down to the garage and into the backseat of the car. Off to the local hospital with him clutching his groin the entire way.

The visit went exactly as expected. Both testicles were in extreme necrosis and after a fast surgery, both were removed.

Ann asked for and received both testicles in a jar with formaldehyde as her small orchidectomy trophy.

It gets better.

Walt’s orchidectomy left him with a world of side effects, confusion and totally killed any interest in sex. Wife, groupies, masturbation, all sex, no interest. His music suffered, he was depressed. It just wasn’t a life he envisioned.

So that spring, his family doctor prescribed Testosterone injections.

Ann’s friends set a plan.

Billy and Paul, trouble makers that could talk anyone into anything, had lusty thoughts about Walt. While six of them sat at a bar one night discussing Ann’s life, they first tried to get Ann to just inject saline solution. You don’t want him horny! You don’t want him chasing groupies, it would be like the testicles were still there. Plus he’d never bother Ann for sex again.

Ann laughed and glibly replied “Ha! She’d just use her stock pile of hormones that sat in the fridge in the garage!”

Everyone just sat back and let that sink in. They all thought, in silence, in unison… wow, he could easily be turned to a woman. A cute one at that! And with that Ann would have the exotic different relationship that they sought for her.

Revenge served by the victim to the victim.

The next morning, Ann went into Walt’s bathroom drawer where he kept his miscellaneous toiletries. Right there on the top was a brand new vial of testosterone cypionate with the thick needles to withdraw the drug from the vial and the long thin needles to inject into his buttocks. Ann quickly assessed the look of the ingredients, went to the garage and grabbed both an estrogen and a progesterone vial. She drew a needle of testosterone and gave her self a shot. Then, she said, heck with it, and drew all of the testosterone out of Walt’s vial and spayed the contents into the sink. She then replaced the missing testosterone with a mixture of her drugs. Put it all back in the little box and straighted out the drawer.

Because the injection needed to go into the buttocks, Walt frequently asked Ann to please do the shot for him. She obliqued him, upping his dosage of counterfeit drugs of to almost twice what the doctor had prescribed for the original.

And as any drug therapy, the doctor called for tests every month to monitor Walt’s T levels. Imagine the doctor’s concern and surprise when Walt’s levels were nowhere to be found. The result was a request to do more frequent injections with a larger dose.

Ann started herself on a regiment of testosterone. Stealing Walt’s via of fresh T each time it arrived, swapping it out for the estrogen a/progesterone cocktail from the garage.

Results start to show.

A common side effect of testosterone injections are “man boobs.” So no surprise when Walt’s estrogen/progesterone cocktail started to produce, quickly, breasts that were close to B cups. Another common effect is the gender dysphoria that any hormones produce. Estrogen can produce a calming effect on a person that is suffering from the lack of testosterone. Skin started to get soft. Walt’s hair grew lush and thick. With no testicles, his ‘package’ felt smaller and smaller. Some nights, it would invert to a small nub. But, Walt could not understand that anything was wrong. He was just confused.

Walt’s feminine side was definitely coming out. He would sheepishly cling to Ann while his confidence was waining. Ann’s, on the other hand, was soaring with her use of Walt’s T. She grew stronger and lost a bit of stomach fat that brought out her breasts.

On nights where they would go out to dinner with Ann’s friends, the guys would flirt with him. The women would flirt with Ann.

Billy and Paul, trouble makers, were constantly running their hands over him and through his hair. They would make a point of sitting on both sides of Walt and having conversations over his lap. Where they would nudge his thigh or whisper in his ear their side of the argument. Both men wore seductive colognes that were slightly feminine in scent.

Ann would look over in amusement at Walt’s bewilderment. In her head, a next step started to ferment.

Grand plans.

One night, Ann, Billy and Paul, found themselves at the bar early. Billy was asking about Walt’s whereabouts and Paul just blurted out “Stop it Billy, you’ve got the hots for him. Leave it be.” Ann snapped her head to Billy and looked at him with her mouth open.

“Hots?”

“He likes the gurlie boy type” said Paul.

“Well, what’s his butt worth to you?” she joked back at him.

“OH MY GOD! Yes!” said both of them in unison. “How would you like to be in our next play? Not a lead, mind you, but on stage front and center. We can make that happen!”

“Walt would be jealous, he’s the performer type.”

“Ha! Both of you on stage, but…”

“Yes?”

“It’s a couple of women type role. He’d have to dress as a woman.”

All of them sat back for a moment and realized, that wouldn’t be a problem. It would just take convincing him to do it and that didn’t sound hard to do.

“I’ll need some tickets for the show too” said Ann.

“Deal!”

Grand plans are approved.

Walt arrived a little later and the three of them presented their play and how they really needed two women quickly as two had backed out and that Walt with a little makeup and costume, and Ann, also with a bit of costume help would really fill the bill. And that the play was this Saturday. Walt looked back and forth and at Ann’s pleading eyes and finally said “Sure!”

Base Preparation.

The next day, Ann followed Walt into the bathroom to view her husband nude for the first time in several months. She hadn’t seen him nude since the morning of his testicle “accident.” She was surprised at the transformation. Walt had breasts that he tried to cover with his hands. He had ‘no dick’ to speak of. It was a flaccid lump of nothing that he was trying to cover whit his other hand. His hips looked like they’d filled out from the scrawny track star of the past. And he had a little belly, that looked cute, like an adolescent girl’s. And he was almost hairless!

“What, what are you looking at?!?! he exclaimed.

“Well the boys wanted me to check you out to see if you needed your legs shaved. I guess not. Other than cleaning up a few pubes, I’d say you’re good to go. Those hormones are doing a job on you aren’t they? Here, take this razor and shape that bush. It looks unruly.”

With that, she turned her back to him and stepped out of the bathroom, barely concealing her giant smile.

With the door closed, Walt turned to his dismal penis and shaved everything off. He felt more feminine that way he told himself. Then he said “What the hell?”

Preparation 1.

There was a dress rehearsal that Friday. It was the first time on stage for Ann and the first as an Actor for Walt.

They both arrived at 4:30 and were lead into different parts of the dressing area. A flamboyant little man whirled around Walt. Quickly trimming his eyebrows from a masculine neglected state to a beautiful graceful arc. Another woman grabbed his hands and started on his nails. Another grabbed his shoes, pulled them off and eeeked as she saw his ‘man toes.’ Quickly all nails were painted a bright red. “Must be visible from a distance” they said.

Walt just acquiesced to all of it, slightly loving all of the attention.

The costume person came in with a pile of very short dresses over his arm. He had Walt strip down to his boxes right there in front of everyone and just threw dress after dress against his chest. “This one!” he gushed and tried to throw it over Walt’s head. It didn’t fit over the boxers. “Lose ’em!” and just like that Walt was completely nude in front of a growing crowd of strangers that were all working him over. The costume person pulled a tight gaff from his apron pocket and tried to put that one but Walt grabbed it from him and pulled it on his legs. The costume person then just grabbed his penis and yanked it back and tucked it expertly as Walt jumped in shock. Billy and Paul were snickering from the doorway.

He was then handed a pair of sleek heels in place of his sneakers. He had all of 5 feet of practice, wobbling like a new born baby deer as he was lead out of the room.

The next step was makeup and W was lead into a long room with a counter and mirror, where, probably the first woman, and the first person that wasn’t gay, sat him down and put a white collar around him.

It was the first time W had seen himself since all of the preparation had started. the first time in 2 hours. Probably the first time in a month that he’d even noticed a mirror.

Across the counter in the mirror, he saw a beautiful, almost young Jacqueline Kennedy-esk woman staring back at him. She was beautiful. Then he noticed the unmistakably feminine eyebrows. That wouldn’t go away soon. That and his budding breasts, oh boy, he was going to be confused for being a woman for a while. While he hid an inner laugh he put his hand up to his mouth and noticed his nail color. They had used jells, good for a month of color. That wasn’t going away soon either, as the colored toe nails would last too.

After 20 minutes, the stylist had added foundation, eyelashes, eyeliner, lipstick, blush, and a little bit of a hair trim. It was that last touch that W noted would add another month of his femininity to the package.

Billy and Paul were waiting at the door for him and greeted him with pecks to each cheek. Plus Billy sprayed W with a little woman’s perfume to ‘seal the deal’ as he said.

Walt’s mental state at this point was complete gender confusion. He felt humiliated. He was wobbly from the heels. He did feel feminine. He missed Ann. The attention was beginning to nag at him like the feeling a beautiful woman might feel if everyone in a room was checking her out. He felt needy. And he was a feeling a little ‘sugar low’ and dizzy from that.

The Counter.

Ann had it easier. Her costume was to be a military officers dress blues. Yes, female, but still a pressed uniform with a row of metals across the front. Her newly masculine self carried it perfectly. Her hair was slicked back, a minimal amount of makeup and she was good to go. She exited the dressing room like a military person might, striding to the back stage in her black boots like she was in control.

That rehearsal went smoothly. The director had W playing a woman that was trying to avoid the officer’s advances. Ann would make advances and W would rebuff them. Pushing her away. It felt awful for W to push Ann away. He wanted to melt into her masculine arms, it had been so long. She looked so strong and protective. So attractive in her presentation of masculinity.

Ann had a similar inner conflict. She didn’t want W in this state. But was so attracted to his femininity that it left her wanting. Wanting a woman in her strong arms.

They left the rehearsal that night with W getting admonishments from the make up people to keep the makeup on, to not mess with the nails or other makeup additions.

After one drink each, they both were a bit drunk and headed home where they tried to have sex, but it was the most frustrating act ever. W could not get hard and Ann thought maybe she should have had the dick in this relationship.

The Presentation to the World.

The next day at 4:30, they both headed to the theater. W in his androgynous state with a sort of dress and Ann looking so serious in a pant suit.

The makeup and dressing was so much easier this time.

As they gathered back stage, Walt and Ann discovered their full names had been included in the program.

When they took their positions on stage, W looked out at the crowd, hoping to not see anyone he knew.

It was at a moment when the lights were down on stage, that W saw the two groupies from his dalliance months ago in the front row. Then he noticed several of the band members along side the groupies. And the second row was Ann’s collection of gay friends from the bar!

He had been humiliated, outed and exposed by Ann!

His acting that day was inspired, he wanted nothing to do with Ann. Pushing her away with a vengeance. She on the other, hand pursued him mercilessly, leering at him.

The Turn.

At the end of the night, Billy and Paul were right there at Walt’s side. Explaining that they thought that it might have been thoughtless for Ann to treat him that way.

“Let’s leave. You can stay with us tonight! We’re going out. Keep the makeup and dress. You don’t have clothes to change into here” they pressed him. “We’ll get you home for your clothes later.”

Billy gave Walt a giant sympathetic hug that W found himself melting into.

“Ok, sure, let’s go.”

The evening lead from one gay bar to another. Walt having drinks at each getting drunker and drunker at each turn. Men were hitting on him at each bar and it became harder to not push away the attention. At one bar, Billy pulled W onto the dance floor for a long slow dance. At the end of the dance they kissed.

Walt’s brain was in turmoil, did he kiss Billy or did Billy kiss him? Did it matter? It felt good to be kissed. It felt good to be held!

Billy leered over at Paul. “We got him” he mouthed silently.

The Gotten.

Billy and Paul lead the way out of the bar with Walt stumbling between them. They poured him into the backseat of their car and while Paul drove them home Billy texted Ann “THX! We’ll give him back in the morning. He also texted another couple of the gay guys from the bar to come over in an hour or so.

When they got home, Walt was sobering up a little. Billy pulled the dress off him and both Billy and Paul stood back to admire his capture for the night. Before them stood a long slender woman with a tiny penis, breasts and not a stitch of hair. Or clothing.

“Where did his underwear go???”

“Hah!” said Walt, “I got rid of that stuff at the second bar.”

Billy couldn’t stand it and said “Excuse me guys! I’ve just gotta go there” as he slid down in front of W and proceeded to suck on Walt’s tiny penis.

Walt just melted back into the sofa behind him.

Paul, slid onto the couch next to W and proceeded to nibble on his neck and breasts and then kissing Walt fully on the lips.

W was in heaven. He’d been so celibate and so lonely, so – so – so… wanting a connection that was stirred up by his horrible attempt with Ann the other day that anything would do.

Billy slyly slipped his hand between W’s legs and started stroking and pressing against W’s anus.

It was almost a natural reflex when W lifted his hips to let Billy go where Billy wanted to go.

With a little saliva and a gentle push, Billy had his index and second finger up W’s butt and was doing gentle circles around W’s prostate.

At this point, W was a puppet in Billy’s hands. He was making out with Paul, swapping tongues and biting each other’s necks like passionate lovers. His small penis was leaking sweet pre-cum like crazy in Billy’s mouth and his hips were grinding back and forth like a man possessed.

At this point, Billy’s jaw as getting tired and although W was as big as he got, it wasn’t filling Billy’s mouth. Billy realized he wasn’t going to get this “formally” straight boy to fuck him, that size made it pointless. W was always going to be a bottom. Billy would be fucking W tonight. “Hah!” he thought, “Paul should fuck him too!”

Billy reached under the couch and pulled out a big tube of lube that just happened to be there from previous “orgies.”

Billy tapped Paul on the knee, showed him the lube. Paul nodded, and within seconds, both men had shed their clothes.

The skin on skin contact drove everyone to another level.

Walt’s brain was on fire. He wasn’t gay but he just felt so good. The skin on skin felt just like as with a woman but the hairy bodies coming at him with the musky smells, and hard muscles had a new fire to it that was a totally new experience that made W giddy.

So when Billy tugged W’s hips down to the end of the couch and rolled him over so his soft ass was in the air, W just went with the flow, rolled over and let his ass in the air.

Billy mounted him first. Almost immediately exploding into W’s ass with a build up of cum that had been itching to shoot since the kiss at the bar.