Chastened, FL Ch. 03

"Oh, yeah," he said like a teenager being reminded to pick up after themselves and stooped over, pulled them off one by one, then trudged to the bathroom.

They heard him gag a minute later, and all three smothered their laughter not wanting to sour the mood since it was already pretty low.

"That SOB figured we'd clean his fuckin' boots for him, us being women and all," Bambi said with a scowl.

"Yeah, well fuck him!" Hannah added, and turned to Vince and said, "You were right to tell him to take them off. He may have money, but he's sure a jerk in other respects."

While Gilly struggled to clean the puke from his boots, Hannah and Bambi asked Vincent to show them his bedroom. Once inside they looked around and were obviously impressed.

"Jeez, you're a neat freak," Hannah sniggered.

"Thanks, I think, he said, as Bambi opened his closet. Oh shit, here we go! He said to himself.

Hannah!" Bambi whispered. "You gotta see this! Look at these!" She held two lovely evening gowns in her arms.

"Holy shit!" Hannah exclaimed, "They're gorgeous! You're wife, or ex-wife certainly knows how to dress."

"There's more! Just not evening wear! Look at these ... aren't they to die for?"

"Wow, they must have cost ..." Bambi realized she was running her mouth and shut up, not wanting to insult their host.

Now pale as a ghost, Vincent gave up and confessed. "They aren't my wife's. I've never been married. They're mine. I ... I like to wear woman's clothing. I don't know why, but I just do. I have since I was a teenager.

Bambi found herself even more mortified than Vincent was for having brought the whole thing up. "I ... I don't know what to say ..."

Hannah came to everyone's rescue and changed the subject for the moment by asking Vincent, "I always ask a male friend a simple question, Vincent."

"You do, do you?"

"Yeah, so tell me, which hand do you use when you pee?"

Vincent was taken aback by the sudden change of direction. One moment he was horrified that his secret had been discovered. In the next, he was fighting off a smile at the ludicrous question Hannah had put to him.

He decided to answer her accordingly, and said: "Both, I use either hand to fish my whatever you chose to call it—dong, dick, Willie, wang, cock, whatever from my pants, and then I usually balance it with my left hand. I do shake it with my right hand as a rule. That answer your question?"

"Mmmm," Hannah replied, managing to stifle a giggle by the merest chance.

"I have a question too," Bambi said.

Vincent, already weary of the abject humiliation his secret, now public knowledge was about to bring him, sighed and said, "Go on, ask away."

"What's your shoe size?"

"Why?"

"I want to borrow those red ones. I'd cram my feet into them if necessary, but you being a male, they might swim on me and that ... well that could prove to be a problem in that they'd keep falling off."

Now it was Vincent's turn to laugh and he opened his arms to both girls and hugged them to him. His secret was safe with them--he thought.

Bambi insisted on trying the shoes on. They fit! She was ecstatic about it. Then Hannah tried on a pair, but they were too tight on her left foot.

"Yeah--yeah, I have two different sized feet," she complained.

Bambi tittered at her admission. Hannah then admitted that her breasts were different sizes too. "I'm all fucked up—size-wise," and she winked at Vincent.

"What?" Vincent said, knowing she was up to something.

"You and me are gonna fuck," she said matter-of-factly.

"We are?" Vincent said, confused by the sudden turn of events.

"Yeah, but only if you let me wear that shiny green dress in your closet while we do the deed."

.

"That's possible," he said and turned to face Bambi.

"Oh, I need to see you in that blue clingy thing, Vinnie."

"Are you fucking kidding me? Gilly's out there! He'd never let me live it down."

"Fuck him, you put the dress and a few other things on, we'll take care of Gilly."

Just then they heard Gilly calling from the living room.

"Keep him occupied Hannah. I'm going to assist our lady friend here with some of the more difficult accoutrements females have to cope with on a daily basis."

Both Hannah and Bambi started to laugh, and were still laughing when Hannah left the room to 'entertain' Gilly.

"Tell me how you got started with your cross-dressing, Vincent," Bambi giggled. "I'll tell Hannah later.

"Hmmm, well, ever since I was a child I had always fantasized about being a girl. Every chance I got I would sneak into my mother's closet and try on her panties, slips, nylons and dresses. The feel of the sheer silks and nylons against my skin would drive me crazy."

He paused to see how Bambi was taking his story and saw that she was listening intently, and so he continued.

"When I hit puberty and discovered the joys of masturbation these two activities seemed to combine perfectly. So much so that while jacking off dressed as a girl I would fantasize about being sexually used by men. Eventually I felt I needed a real life person to place my desires onto. Not wanting to pick anyone that lived close by, for obviously getting caught would be awkward and that's putting it mildly. But then I was very young.

"Anyway, I happened to pick one of the only people I knew in real life that lived far away, my cousin Vaughn. For years I had fantasized about doing things with him while dressed as a girl. To my surprise, Vaughn was all for it. In fact, he let me fuck him up the ass after I sucked him off the second time. Of course, he did me there as well. We only were able to be together twice, that first time and then later that year during the Christmas holidays."

"What happened to prevent further experiences between the two of you?" Bambi asked with interest.

"I was never quite sure. I think he was found out by his parents and shipped off to a private school. He, um, joined the Navy on graduating high school and was killed during some war game maneuvers in the Pacific several months later."

"Oh ... I'm so sorry, Vincent."

"Thank you, but it was a long time ago."

"Still and all, you were very ... fond of him."

"Yes, that's true enough ..."

They both heard Gilly in the living room say: "I think it's time for my lap dance, Hannah. Look at my pole dancin' in my pants, c'mon baby, let's get the partay rolling!"

Both Bambi and Vincent went to the door and peeked out, Hannah was just sliding her chair out from the table. Gilly sheepishly got up and began to fumble around her in an awkward kind of hip thrusting, semi-dancing, stabbing motion. After a minute she grabbed his hips from behind and started grinding him and slapping his ass. This was more than he could take as he stopped 'dancing' and sat down.

"C'mon, Hannah, sit on my lap!"

"On that big thing? She said with a sexy smile.

"Yeah, that big thing. Let's see how far we can get it to go."

"Go where?" She innocently inquired.

"Show me that sweet pussy, baby. C'mon let me see it!"

Meanwhile Bambi was sorting out the various items needed to transform Vincent into a woman. "So what do you call yourself when you're all gussied up?"

"Vanessa, just Vanessa," he replied softly.

"Hmmm, I like it. It will suit you in this blonde wig," Bambi said with a laugh as she pulled the wig and some clothing out of the closet. As she decided on what he should wear, she gave him a bottle of lotion and told him to cover his entire body in it. They listened to Hannah and Gilly in the other room while waiting for the lotion to dry.

"Hannah is a trooper, taking all that shit from him," Vincent said.

"Don't be silly. Hannah needed to get laid. Look, since we know your secret we might as well share ours with you. We're both married and have kids. She's got two girls, one 6 and one 4. As for me, I have three kids, a boy 9, and two girls, one 6 and one 4. Our husbands are not as attuned to us as they once were. We think, but don't know for certain that both of them take the occasional night off and fuck a secretary or some other young thing. We're not totally okay with it, but that's life. So we do our little thing. That's how we came to know Gilly.

Hannah and he have gotten it on before. For that matter I've been with him once myself. So there, true confessions. Happier now?" She patted him on the ass, and said, "Lotion seems dry enough. Let's move to phase two."

Bambi pressed her breast against his arm and shoulder as she assisted him in putting on the white thigh high stockings.

Next he donned a pair of satiny white panties, before having to stand up while Bambi wrapped a white satin bustier on from behind and laced it up while Vincent tried not to complain other than making grimaces and other contorted expression with his face.

Suddenly, Bambi grabbed Vanessa and pulled him into her arms and kissed him while rubbing her groin against his crotch. Subconsciously Vanessa raised a leg off the floor just like girls do when they are kissing someone passionately. After more than a minute of torrid tongue swapping, Bambi broke the kiss.

"I notice you made me end the kiss. You're really a hot piece of ass, Vanessa." Then she winked at him and flicked the point where his nipple should have been in the bra and laughed again.

Vincent, AKA Vanessa, had a roaring hardon and despite his feminine attire, grabbed Bambi and groped her body from head to toe, spending an inordinate amount of time rubbing hand and fingers over her pussy until she begged him to stop for fear of flooding her panties.

"Oooh, baby, sure ... let me help you out," she said and reached under his dress and pried his erection out from under the panties and began to jerk him off.

"I'd have let you fuck me, but you're so horny you'd cum before I even put you inside me."

And she was proven right a moment later, when after a last tight fisted squeeze and stroke, Vincent came hard, spewing line after line of tumescent sperm on his bedroom carpeting.

She continued masturbating him until he was complexly finished, then cleaned his cock off and tucked it safely back inside the comfy confines of his silk panties.

Lust satisfied for the moment, they returned to the job at hand. Makeup came next, followed by the insertion of a pair of falsies.

"Don't want you to big up there. The idea is to have him go for the pussy. When he finds your cock instead ... well, we'll see what kind of guy he really is.

Then the dress went on and the stockings clipped to the garter belt, and finally the wig was adjusted until Bambi was satisfied with it and turned Vincent so he faced the mirror.

He couldn't believe his eyes. Staring back at him was this hot blond with a cute white cocktail dress, blond hair and come fuck me makeup on.

"Oh, my god," Vincent whispered. "I've never looked this good before. I ... I can't believe that's actually me!" He twirled around to get a better look from all angles while Bambi smiled content with what she had done to transform him to her.

"You're right, Vanessa, you're one hot bitch and I want a piece of you sometime tonight!" Bambi had an evil grin on her face as she giggled.

"Now you go touch up your makeup while I see what Hannah and Gilly are up too," Bambi said, before bestowing a gentle kiss on Vincent's lips.

He made his way to the mirror, managing quite well on the four-inch heels he had not yet become fully accustomed too.

Bambi peeked out the door. Gilly was sitting in a slouched position on the couch with Hannah on her knees in between his legs pointedly attempting to revive his flaccid penis.

"Suck it s'more!" he said, hoping to urge her to perform a miracle on his inert dick.

"I'm getting nothin' here, Gilly. Let's call it quits for the time being," Hannah said wistfully, and then more hopefully added, "We could try the strap-on. Remember, it worked the last time?"

"Yeah—yeah, it did, didn't it? Well okay let's give it a go then."

Then as a seeming afterthought, he asked, "Where the fuck are they?"

"You position yourself and I'll go see what's keepin' them, sweetie," she gave his rump a love slap and walked toward the bedroom only to have the door open and Bambi greet her before she entered the room.

"He's ready! Oh, my God, girl, you won't believe it!" Bambi whispered.

"Gilly can't get it up. I'm about to use the strap-on on him," Hannah confided quietly.

Bambi had an idea and asked, "How drunk is he?"

"Three sheets to the wind, you ask me," Hannah answered.

"Let's pretend Vince passed out, but that our 'girlfriend,' Vanessa just turned up. Um, like Rita called her and sent her over as her replacement. Now we have three girls and one guy. Think he'll buy it?"

"I think anything we try to get him hard, he'll buy. So what is it you want Vince, err, excuse me, Vanessa to do?"

"First get a gander of Vanessa," Bambi said happily, and stepped to one side of the doorway.

"Holy Shit!" Hannah gasped. "I—I see what you mean. Yeah, sure, in his state Gilly will believe he's a she. I'd bet a week's pay on it!"

"Let's have Vanessa fuck him up the ass, only she'll use her dick and not the strap-on. Show him the Strap-on first then sock it to him," Bambi said.

"It'll work!" Hannah said in agreement.

"Wait one minute, guys," Vince protested. "What if he ..."

"He won't. Don't you see, he can't get it up and he's been sodomized before ... when was it, Bambi?"

"Five, maybe six months back. I'm not sure exactly," Bambi replied.

"I'm going with it," Hannah said and returned to Gilly, who had his hands braced on the couch with his ass pointed out toward the bedroom door.

"Guess what, Gilly?" Hannah said.

"Wha ...?" he inquired drunkenly.

"When Rita couldn't make it to our little party here, she called a friend of her and she's just arrived. Her name's Vanessa and she wants to do the honors, so I'm giving her the strap-on."

"No, hey ... wait a minute!"

"What now, Gilly?"

"You can't let anybody do it!"

"She's not just anybody, she's Rita's friend. Hey, if Rita's good enough to fuck and suck, so is Vanessa. Now let's get it going or you'll never get hard for us and we got to get home at a decent hour. We're not rich like you with your oil bidness"

"The least you can do is say hi to Vanessa before she straps big boy on, Gilly," Bambi said.

Without turning his head, Gilly called out, "hey, Vanessa, welcome to our little partay. I hope you can get my dick up, these bitches ain't capable tonight.

Vincent realized that Gilly hadn't once mentioned his name, questioned his whereabouts, or made any comment other than that having to do with getting him reasonably hard again. He took that as a good sign as he approached the prone man from behind.

"Here's the strap-on, Vanna, Hannah said waving the black dildo under Gilly's nose and dropping it on the floor out of sight. To Vincent's eyes it was the largest he had ever seen. The cock was huge, black and beautiful, and for a moment he wanted to have Bambi or Hannah use it on him. But with only a slight hesitation, he hiked up the dress and tugged his semi-rigid cock from the silk panties her now wore.

"Lube, lease," he said in as feminine a voice as he could manage.

Bambi handed him the tube of KY jelly and he added a giant-sized dollop to his penis and then smeared the rest over Gilly's anus.

"Woo-Hoo! Feels good. I like a good ass poke every once in a while," he announced to all. Gilly had no compunctions about revealing his deep dark secrets to women, but would die before admitting to them to any man.

"Go fuckin' easy now," Gilly warned.

"It'll be okay," Bambi cooed. "She's really good at this. Take my word for it."

With that Bambi moved out of Gilly's line of vision and kissed Vincent/Vanessa passionately, while taking hold of his penis and giving it several rapid jerks to get him even harder.

Hannah, now also behind Gilly, placed the black dildo against his anus and applied the slightest of pressure.

"Ooooh, go easy ... go easy now," Gilly called out, raising his ass to aid in his penetration, but not bothering to look back.

Vanessa/Vincent was now prepared to try fucking Gilly's ass, and with a little work and some help from Hannah, who had dropped to her knees and was playing with Gilly's testicles to add pleasure and distraction to Vanessa's actual penetration.

Vincent had fucked several men anally previously, and so he kept nudging and withdrawing, until he felt Gilly relax and with one bold stroke he drove his cock past the sphincter, heard and felt it pass through at the same time and then waited for Gilly's reaction.

"Whoa, hurts like a motherfucker, but it'll pass. Keep going baby. I can feel my dick swelling up already."

The next few minutes were more cat and mouse than anal fucking. Vanessa would edge in, back out and forge ahead again, gaining an eighth of an inch or so each time.

"Try adding some lube," Hannah suggested, and Vincent pulled out, added a large glob of jelly to his cock and plunged back into Gilly's ass. The going was easier for both parties and soon Vincent was bottoming out.

"Oh, yeah!" cried Gilly, "Now we're cooking! Slam that black bastard into me!"

Vincent/Vanessa found a steady pace and held it, while Hannah and Bambi looked on, silently cheering Vanessa's sustained fucking.

"Yeah, I'm feeling it, Vanna! I'm really feeling that black dick!" Gilly crowed.

Vincent was feeling it too and slowed down, but resorted to slamming his cock into Gilly's ass as hard as he could.

Gilly groaned and yelled, "Fuck—Fuck—Fuck! I'm cumming!"

Bambi and Hannah watched, unable to take their eyes off the rutting couple. Bambi was squeezing her breasts through her top. Hannah's hand was gripping her pussy through the front of her dress.

"Yeah, yeah, take it all, motherfucker!" Vincent croaked as beads of sweat flew off his/her forehead while she/he pounded inexorably into Gilly's ass, not wanting to stop, but already caving in from the toll the relentless fucking was taking.

However, in his excitement, Vincent used his normal voice, although in his current state it was far from normal, but it was certainly not feminine.

"Wha ...?" Gilly gasped confused at first, but even in his inebriated state he was confronting the truth of his situation.

Hannah sighed and pulled Vincent away from Gilly and, using a kind of bear-hug, waltzed Vincent over to the nearest chair, sat him down and hiked up her dress, shucked her own panties and straddled Vincent's lap and began screwing away.

"He's trying to figure out who you are, Vanna," Hannah cooed in his ear.

"He knows--I'm sure he knows," Vincent responded.

"No, he's confused. He's drunk and he's had a cock up his ass. He's totally confused because he likes being fucked that way. I'm willing to bet you that he blows you before the night is over."

"That never happened in college. It was a one way street."

"That was then ... this is now, baby. Now give me what you've got left!"

As far as Vince was concerned, it felt like his dick was on fire. Hannah's pussy was that hot and that tight. He took hold of her waist and went at her with a vengeance.

"Ohhh, that's it! I knew you could fuck up a storm, Vanna!"

"I'm getting close, Hannah!"

"Just a little longer, baby I feel it too! It's gonna be a big one for me, baby. Can you go a little faster?"

In turn, Hannah leaned back and sent her legs up to rest on his shoulders. "That'll get you deep, baby! She yelled then moaning with pleasure she reached down and began rubbing her clit as he continued to hump away at her until they both came.

"Fuckin' Vince!" Gilly yelled.

"Is there a problem, Gilly?" Bambi asked innocently.

"The fucker raped ... no, he sodomized me!"

"You mean Vanessa?"

"I mean, Vinnie! That fag cocksucker stuffed his dick up my ass!"