Walt and Ann

This is a story about Walter and Ann. This is part 2 of 3.

Delivering the altered goods back to the owner?

“Come on princess! Time to get you home. I’ll drive you. No slut walk of shame for you!” said Billy.

Considering that W had no “male” clothes to speak of. He was itching from crusted this and thats all over. He jumped at the offer and went flying down the stairs. Only wearing a very short dress and wobbling away on the heels from last night’s play. His make up was a mess. But all in all, the general perception was there goes Jackie Kennedy, whatta hot mess?!?

As they drove home, Billy kept silent and let Walt’s mind wander.

As they got to the front of Walt and Ann’s house, Billy said “You’ve got some big decisions ahead of you my feminine friend.” “Good luck today.”

Walt had to knock on the door as he had no keys. Ann opened it with a bemused smile and said “Yes? Princess? Welcome home?”

Walt burst into tears. The guilt, humiliation, everything from the last night consuming him, even as he felt another spurt of cum leak down his leg. He wanted an apology for the set-up, but felt that he’d enjoyed being in the play. He’d somehow claimed his feminine side on stage. What wasn’t said was anything about his outright slut behavior after the fact. That had been texted to Ann in a long thank you text from Billy and Paul earlier. She knew what had happened. She felt like she’d gotten her final revenge from the groupie situation. She had her husband’s balls in a glass jar and he didn’t know that was her doing. Now she’d gotten him fucked beyond her wildest dreams just because she could.

What was next was actually in his hands. She had controlled the packaging of this launch. Now what?

They ‘side’ hugged and she pulled him in the house. Lead him down the hall by his hands with the painted nails. Getting to the bathroom she pulled off his dress, surprised to find him completely nude underneath. Still not much of a penis. His legs were crusted with cum and his butt itched from the last night’s action. He looked like a slutted up whore with makeup all over the place and a musky smell of cum.

“Ok, you are a wreck, let’s clean you up. I, ah, I… I don’t see you as a man anymore. Let’s see what I can put you in today.

“What? Where are my clothes???”

“You won’t look right in a t shirt, honey, you’ve got boobs, serious boobs. I noticed the other day, you must be a C cup and that’s gotta start hurting. You do need support, and you’ve got some curves. Those jeans of yours are too tight. But first you really need a bra. Jump in the shower. Let me think about this.”

Walt looked down at his painted toe nails and didn’t speak immediately.

“Ok, I’ll shower.”

Polishing One’s Possessions.

While W showered, Ann ran out to the local Kohls. She approximated W’s size and bought several bras, shirts and some summer dresses. This was fun she thought, like dressing a daughter. In fact, that’s what she told the sales associate who gave her a face indicating that the clothing in her arms would no way fit her.

She dashed home with several hundred dollars of new clothing in the backseat of her car and a giant smile on her face.

When she got home, W was just getting out of the shower. She barged in on him with armfuls of various womans underwear.

The bras were a perfect fit. Wow, he had an impressive rack! The panties she had bought fit snugly on his rounded butt, pulling his penis in tight. When she had him in bra and panties, he looked hot!

“Well aren’t you a beauty? Let’s do some makeup. I didn’t buy you any, but we can use mine. I wasn’t sure what colors might work best.”

“I’m not so sure about this” he protested. But he let himself be pulled along and seated at her makeup mirror.

Ann did her magic and a beauty emerged from the wreckage formally known as Walt.

“What are we going to call you? Princess? That’s kinda wordy. Wanda? Wendy? Oh heck, what about just Sue?” said Ann. She kept the constant banter up while she dried his hair and pulled a nice summer dress over her head.

“I, I… I don’t know. I didn’t think I was going to be a woman for more than the play.”

“Sweetie, that ship has sailed. Those boobs, that butt, you’re not going back. And, that dick of yours? Well, it’s not going to keep me happy. Sorry honey.”

In spite of the emotional lift from the makeup and just feeling clean, W felt depressed. He thought about the ‘stuck’ position he was finding himself in. His mind was going in all sorts of directions. Part of it was saying yes, go for it, you’re gorgeous, the other part dreaded the idea of dealing with the icebreaker news to his band, parents, relatives, friends and the two groupies that started this monster life change.

Walt put the dress on, put the heels on from last night. He was getting good with them. He fluffed up his hair, checked his makeup one more time. Stood up and shrugged his shoulders. It was to be the first day of his life.

The Build Out.

Ann planned out a full day for the two of them. There was something so sexy about Walt, especially now, she still wanted him and since the rejection at the play, she wanted him desperately.

The first stop was Macy’s for a full facial make up session. They spent hundreds of dollars on makeup. They had a specially fun time selecting a special perfume for Walt that drew Ann in and made her swoon. only swinging past the local Walgreen’s for bunch of makeup remover, cotton swabs, and assorted other items. They went back to Kohl’s for more day to day ware. Buying tight woman’s styled jeans, some sweaters and shoes, several dozen pairs of shoes of all types. It was a great day for both of them and they felt in love all over again.

It was a very lesbian looking relationship. The went to dinner that night at their favorite restaurant. With a very muscular Dyke and a slender dark haired ravenous beauty sitting in the corner making small talk.

Owning One’s Self.

They slept the night in a sweet embrace, both in silky nighties. Their legs tangled together. They hadn’t made love, neither one wanting to repeat the frustration from the other night.

Around 6:30, W woke up and stretched his long legs over the end of the bed, looking down at his brightly colored toes. This could work he thought.

He got up, showered, trimmed his pubes again with the legs razor. Sat down at the mirror and proceeded to make an absolute mess of his makeup.

Two hours later, watching countless youtube makeup videos on his iPad, he gave it another shot and was satisfied that he didn’t go overboard this time. Figuring out daytime makeup vs club makeup vs clown makeup was going to take some time.

Ann got up and in a true “guy’s style” showered, and had her makeup, hair done for the day in 15 minutes. Beating him down the stairs to the kitchen where she started breakfast for the two of them.

Staying As A Couple.

“Honey, we need to resolve something.” she said as he entered the room. “I know you like getting fucked. My ‘boys’ told me you took it like a pro the other night. I was thinking there’s a toy out there that would work for us.”

“Huuuh???” Walt protested. “Wait! What are you talking about?”

“You’re an anal pro! You took 3 guys, very little foreplay, full loads and all. Did you enjoy it?” “You got good marks for a blowie too!”

“Ah, oh. Yeah, well, yeah, I was a bit over the top crazy that night.” “And I did like it. The prostate gives off a huge orgasm. I mean, wow, doesn’t compare to anything my penis has ever done.” “But, I love you.”

“Well, lets go look at that toy I was thinking about.” Ann replied.

Preparations For Plowing The Boy.

The toy Ann was thinking about was a Funfactory Share Dildo, in black. A fat monster that slipped into her vagina and gave her a big black cock. It wasn’t cheap at $109. It looked intimidating to Walt. But when she got the package, she immediately opened it and slid it in with a minimum of lube for her end. She spent the next hour or so prancing around the room with her cock swinging around in front of her. She was able to tweak it around with her vagina muscles like a real penis. And this was only 3 in the afternoon.

Walt, for his part felt an excited apprehensive nervousness about this. He was sober at the moment and this looked huge. This was bigger than Billy, Paul and all of his friends.

“Don’t worry sweetie, we’ll have fun tonight.”

A Couple With Friends.

Dinner that night was at the bar. Everyone was there. And Walt was there, en-fem. People were congratulating the new couple left and right. Billy and Paul were taking credit for the events of the day. They sat on either side of Walt, plying him with drinks, grabbing his thighs and slyly tweaking his breasts when ever they got the chance. There was a feeling of ownership between them. They’d taken W’s virgin butt. He was their project, forever. And he was breathing in their cologne and swooning on the lusty memories.

It was getting W horny again. And Ann could see that from across the table. But it was getting him horny for the two boys and she needed to stop that.

“Let’s go princess!” Ann said. She jumped up and grabbed his hands, slapping away Billy and Paul’s hands as they tried to pull him back.

Walt lurched up, falling over his heels, exposing his breasts to everyone at the table as they spilled out of the dress. His ass putting on a show to the people at the next table.

“One more thing for him to learn to take care of” Ann thought to herself. She pulled him up out of the seat and literally stood him up with her two arms out in front of her. “Good grief, he’s a lightweight anymore!”

The two of them lurched out of the bar with Ann doing most of the directing.

Orgasms

At home, Ann spun W around and easily slid him out of his dress. With an expert bit of handwork only a woman would have, his bra was off and it wasn’t long before the panties hit the floor. Here she was still dressed and Walt was completely nude. It took just a few moments later with a spurt of lube and she had W on his back with his legs in the air and she with 3 fingers up his ass.

“You want me to fuck you?” she asked.

The moan was a woman’s falsetto squeal, “Yes, yes, please, yes!”

It did not take Ann long to strip and have her toy in place. It didn’t take much longer for her to be in full rut with W’s legs in the air and the two of them merged together. Ann thrusting like a pro.

“I’m going to fuck you like every guy that’s ever fucked me. Hard, fast, slow, long. Backwards. Everything.”

And with that, W’s prostate exploded. Cum on both of their bellies. A high pitched groan from deep in Walt’s brain came forth.

Ann was a little disappointed. She plucked the toy out of her vagina and moved up to sit on W’s face. Come on princess. A girl’s gotta know how to eat pussy.

Lessons From A Pro

The next day, Ann reached out to one of her lesbian friends. Donna.

“Donna, the boy doesn’t know how to eat pussy. I’ve never eaten pussy. Help!”

“Well, I want to see this gurl of yours, so how about we do dinner?”

“The bar, at 6?”

“No, let’s do the place down the street, that’s our favorite place and I know it’s private and Billy and Paul will be all over Walt if we go to the bar. And W’s been there en-fem so he’s comfortable.”

“Deal. See you at 6.”

That night the three of them had the corner booth where Donna looked at Ann wistfully, Ann looked at Walt. Walt looked at the waiter in confusion. The woman plied Walt with drinks. Donna plied Ann with drinks and Donna drank soda all night.

Around 8, as all were done with dinner. Donna said “My Place!” and as she was the only sober one, she was the designated driver, she was choosing where the night would end up.

Donna’s condo was a huge glass fronted place that faced the city.

The girls were hanging on each other looking at W. Spinning him around, just like the other night, just like that, he was nude in front of the two women.

“Oh, he’s just the kind of boy I like!” said Donna. “I remember you telling us about his testicles, but I didn’t realize the hormone treatment would just devastate a penis like that!” “Why, he’s got nothing at all.”

“Walter, young man, err, lady, you are gorgeous, but even that said, honey, you’re going to need to learn to please a woman with your tongue.”

“Yes, Donna” he said, like a petulant preteen with her beautiful boobs sticking out in all directions and her legs crossed in front of her. He’d taken to sitting like that and tucking his penis under just because it bothered him that it was so small, it tucked so easily, and mostly having it stick out was embarrassingly non-feminine. All of this added to his dysphoria.

“Well” Donna got up and strode across the room at W. She pushed him back on the couch and with very little warning, pulled her skirt back up to reveal she hadn’t been wearing panties that night. And just sat on W’s face. Not hard or heavily, but lowering her clit straight to his mouth in such a way that Walt, or Ann for that matter had a clue this was her plan.

“Now, honey, just stick out your tongue and let me move my hips against it.”

Walter obliged her and she gravitated her hips in a small circle over his mouth.

“Now, I’m going to stop moving and you will do the motion that my hips were doing.”

This went on for several minutes before Donna looked over at Ann and crooked her finger for Ann to strip and to come over and take her place.

They swapped and after about 10 minutes Walt’s tongue was dying. He pleaded to stop.

“Ok, Ann, take Walter’s place.”

Ann slowly dismounted W’s head and laid down next to him. Donna, climbed up on top of Ann and lowered her clit to Ann’s face.

This was a first for Ann. and after 5 or so minutes, she was exhausted.

“What a bunch of pussies!” Donna said.

Donna slid down Ann’s body and went to town on Donna’s clit. This was easy! The year of Testosterone had made her clitoris huge. In fact, one might have thought it was the same size as Walt’s penis. It wasn’t but, Donna had seem many clitorises since her high school days and this one was big.

All said and done, Ann had a giant orgasm within minutes of Donna’s attack and had to plead for relief.

While Donna and Ann were at it, Walt sat up and studied the two woman. Their technique, their way of handling each other’s boobs and body. It was a feminine study of lovemaking.

Family Impaled Together.

“So Ann, what did you do to get Walt off?” asked Donna.

“Oh, I have a Share. I fucked his brains out.”

“Awesome! I have one but it’s only been used in vaginas. It’s their very large size. I don’t know if it would fit his butt.”

“Oh, I bet it would, he’s a butt slut for sure!” and she told Donna about Walt’s night with the boys.

Donna popped up and ran into the next room, rummaging around in the bathroom cabinet. She returned with a strap on dildo that was massive. Long and thick black rubber, strapped on to a harness. It stuck out at least a foot in front of her.

Both Ann and Walt’s eyes bulged looking at it. They didn’t see Donna anymore, they saw a giant black cock and the question in both of their minds, who would get it?

Donna walked over to Ann and sat down next to her with her legs slightingly under Ann’s.

“Ann, you’re my first victim, you can only do vagina then rectum in that order with a dildo. And I’m doing both of you tonight.”

“What should I do?”

“You dummy, you’re gonna get fucked, properly as they say. Walt sure hasn’t been doing the deed.”

It took a little preparation and a bit of lube to get the dildo into Ann. Soon she was making little groany noises with some squeals thrown in. All of the sudden, it was like something caught on fire and Ann got loud and spasmed up like a bucking horse. She came and collapsed all in one giant motion.

“Walter, it’s your turn now.” Donna said softly.

Walt looked at the dildo, mentally figured the angles and rolled onto his front. “I think doggie style might be best Donna.” “Go slow, please!”

Donna had a sly grin on her face as she moved up to his backside. She took the bottle of lube and just squeezed at least half of it straight into his anus.

“There’s no stopping me now little girl. You’re so lubed I could put a car up there!” and with that she pressed the head into him.

She did an inch or so, pulled it out, pushed back another inch, pulled out. When she got to about 4 inches, he groaned and slammed his butt back into her lap. Taking the entire thing at one pass. It wasn’t painful, it was exhilarating as he pushed and pulled his butt back and forth. Donna didn’t need to do much motion at all. Walt’s brain felt like it would short circuit with the sensations he was feeling.

Bang, and just like that, his prostate unloaded down his leg, onto the couch, his dress and just about everywhere else in a 3 foot circle.

“Oh! That’s something I usually don’t have to deal with. I mean I have squirter friends, but, cum, hasn’t seen my condo in years.”

The three of them, slowly, with a lot of wobbling, stood up. Donna’s big cock standing out in the middle of them while they made their way to the shower. Soon, everyone was scrubbing down everyone. Ann’s large boobs getting the most of the soap while both ladies made sure Walt’s little cock was clean and even several fingers made it up his butt. He was not sure whose.

They all climbed into Donna’s bed and it was a sprawling collection of legs and boobs and hair as they all fell straight to sleep.

Walter leaked lube all night. He wondered to himself? Am I always going to end up leaking something every time I have sex?

Bad Influences.

Billy and Paul, Paul and Billy, over and over their bodies floated through Walt’s brain like a song stuck in his brain. Flashes of penis’. The musky smells. The hard bodies pushing against him. The strong hands grabbing him and making him do things.

Ann was at work the following day when Walt, alone at home, decided to get outside and walk around. He threw on a dress figuring, that was the way to go and popped out the front door with no destination in mind. It didn’t take long but he found himself down the street at the bar that everyone always hung out at. When he walked in, no one there knew him. But within fifteen minutes, the waitress had figured out who Walt was and congratulated him on his transition. The bartender had given him a free drink and a raised eyebrow with a nod. Walt wasn’t sure what that meant, but as soon as his drink was empty, the waitress brought a second one over. ‘On the house!’

About one hour later and his phone buzzed, it was Ann, just checking in. When she learned that he was at the bar, she said ‘Be careful! You’re vulnerable!’

And then just as he clicked the call off, as if it was perfect timing, Billy and Paul walked in the door.

“Walt! Sweetie! How are you?” as they climbed into chairs on either side of him. “We’d say how’s it hanging? But we know you’ve got too little to hang.”

Walt blushed as he knew the waitress and bartender overheard all of that.

“I’ve got to hit the boys room. Wait, girls room. Oh hell?!?”

The waitress looked over at W and said “come with me sweetie, we girls should stay together”

Walt and the waitress, Jan, headed off to the ladies room, Jan pulling Walt along by his hand.

The bathroom was pretty clean for a bar bathroom. And empty. As Walt grabbed a stall and peed sitting down, Jan followed him into the stall.

“I need to see what you’ve got there lady, I’ve heard stories.” She began to kneel down in front of him. Stopping him from pulling up his panties, in fact, pulling them the other way to the floor. And making a beeline to his small penis/clit to suck it in.

“Wooo!” said W “What are you doing?”

“I love giving head and small head is fun. But I can’t get you hard!”

“Let me do this” W said, and he pushed back, pushing the waitress back to the row of sinks along the wall. With a quick move, he was on his knees pulling her jeans down. She had the sleekest of tiny panties. He pushed them aside and went straight to her pussy. The lessons from Donna came straight to his mind and it wasn’t two minutes before Jan began to let out small cries and push back with her hips.