CHAPTER 8 - A double date

Once safely secreted in their room, George could not wait to strip off his suit and free his little man, discarding the cellophane between his legs. He nibbled on what was left of their fruit and eventually pulled the shades and crawled into bed and fell into a troubled sleep.

Ellen looked for Heather at the pool. Not finding him there, she headed for the only other place he could be their room. Quietly opening the door, she marched over to George. Shaking him, she woke him up with an impish smile.

Once his eyes were open, she demanded that he hand over his wedding band. A still drowsy George was in a confused stupor and he slipped the ring off his finger and handed it to Ellen who promised to explain later. She suggested that George return to his nap, implying that it was going to be a late night. She checked her makeup and gaily skipped out the door, leaving a bewildered George behind in the dark. With nothing better to do, he went back to sleep.

@ @ @ @

Several hours later, George woke with a jolt as Ellen stormed into the room burdened with two armfuls of packages. Dropping them on the floor, she sat on the bed and told George to get up.

"What’s going on El?" he yawned.

Not waiting for an answer, he pointed at the packages and questioned, "Where did the money come from for all this?"

"I’ll get to that. We have a lot to discuss," she said as she got up and took a seat across from her husband. "Well," she went on with quiet enthusiasm, "I was at the business center, I sent an email to your sister to see if it was alright to come home, tomorrow we can expect a reply. I passed through the bar on the way back to the pool and I met this guy who was really friendly and insisted on buying me a drink."

George was immediately suspicious and commented, "With you in that bikini, a man would have to be blind not to be friendly."

She favored him with a loving smirk and replied, "Don’t be a jerk, let me tell you about him. He is a businessman down here on his yacht for a fishing vacation. He is tall, and you could really tell that he works out. He has dreamy grey eyes, a strong face, and large hands. And you know what large hands mean?" She gave him a smile and a knowing nod.

She got a dreamy look on her face and chuckled throatily, "He bought me a drink and found us one of those little intimate booths along the wall. The music wasn't loud and the bar was nearly empty, so we were able to talk. He was wearing a short-sleeve shirt and those muscular arms of his looked like they would burst the seams. I mean, not powerlifter arms. Just the kind you'd love to run your hands over.

"I'll tell you, girlfriend, he was trying to work me right from the start. He was so classy and subtle that it wasn't just like some regular guy trying to get into my panties. I mean, any red-blooded woman would want him to get there, but he was so nice. He invited me to have drinks and dinner. I told him I was here with my girlfriend. I described you and he said he had a fishing buddy with him and he was sure he would love to meet you."

"He invited us both out. We’ll have a rral dinner isn’t that exciting?" Ellen was talking quickly, which she only did when she got excited.

"Umm..well…I don't know?" George sputtered. "You can’t be serious!"

"Of course, I am! First off, I'm tired of eating nothing but junk food, it isn’t healthy for our baby! If we play our cards right, we can get a five-star meal on their dime. If it makes you feel better think of it as us going on a double date."

George still in shock said, "So it won’t cost us anything?"

Ellen grinned, "I didn’t say that exactly. Whenever a man spends money on a girl there is an expectation of….well. I don’t have to spell it out for you."

The smile on her face faded as she became serious.

"People around here are starting to talk about the two girls doing nothing but holding up in their room. This is a resort, if we want to blend in, we need to do the things two single woman would do at a beach resort. One of those is to let men wine and dine them, so that is exactly what we are going to do."

George was close to tears now, with a fear that consumed him. "But my voice will give me away. I can say a few things but no way can I carry on a conversation."

Ellen placed a hand on his knee in a patronizing way to calm him.

"I’ve thought about that; these guys are Americans. With your swarthy complexion, you could certainly pass for being Hispanic. I’ll tell them that you don’t speak English. If by some chance they speak Spanish, we’ll stick with our story that you are a Cherokee and only speak pigeon Spanish. We've worked on a few words of Spanish you can say with a girly voice, just stick to them and you’ll get by."

Trying to think up any reason not to go. The best he could come up with was, "I don’t know how to act as a woman on a date."

"Oh, come on you have been on lots of dates before."

"I wouldn’t say a lot. When I did date, it was as a kid, I doubt a woman acts the same way a high school or college girl acted."

Ellen totally dismissed his concern with a wave of her hand, "I will be your mentor. Just watch me and do as I do."

Pointing to the pile of bags on the floor she said, "If you’re wondering where all that came from, I’m sorry to tell you but I sold our wedding bands to pay for the stuff we need for tonight."

She could see the sorrowful look on George’s face. "Honey, they are only things, lumps of gold. Jewelry can always be replaced. Now let’s get started we have a lot to do."

George was sent off for a quick refreshing shower. Ellen took the opportunity to work on the wig that had been tossed aside.

After drying, blushing furiously he stepped into a red silk thong Ellen handed him. He arranged and tucked himself in for concealment. To his astonishment, it proved strong enough to hold his man marbles up out of the way and his pee-pee under control.

He moved nervously into the room.

Aiming an over exaggerated wink at her husband, Ellen held out his dress for him to step into. George got a quick peek at the price tag and paled and stood frozen like a statue.

Seeing his reaction, Ellen tittered, "Don’t worry about the cost. I left the price tag on, so as long as you don’t spill or drool something on it, I can return it in the morning. That’s a trick all of us girls learn early in life."

George looked at her as if she had lost her mind. Before stepping into the dress, he realized something was missing. "Where’s the rest of my underwear?" asked a bewildered Heather.

Ellen replied in a confident tone, "Don’t be silly, the climate is too hot and humid for those things. Women around here don’t wear nylons or bras and I bet no panties either. I was tempted but since you need something to control your secret. You can’t let everything hang loose between your legs tonight. But that doesn’t preclude letting your breasts just hanging out. Besides it will be sexier that way with our girls bobbling all over the place. You should know better than most, guys love that sort of thing."

"Okay," George replied halfheartedly, reconciled to his fate. He didn't want to think about guys ogling his assets at close range, but he trusted Ellen.

She told him to stop stalling and step into his dress she had selected for his first date. She pulled the red spandex form-fitting dress up and zipped it close. The tight-fitting bodice really emphasized his slim waist and prominent bust, while the short skirt brought attention his long womanly looking legs. He looked divine in it, Ellen knew it was the right outfit for his first date. He would be so busy fighting off his date she would be free to explore her options.

George caught just a glimpse of himself in the mirror. He actually, rolled his eyes in an ‘I don't believe this’ expression.

He turned to Ellen who was sorting a pile of cosmetics, "Excuse me dear, I'm new at all this girly stuff but isn’t this too small? It’s skin tight." George had never worn a corset but thought this is what it must feel like. The dress was keeping him from taking a deep breath.

"Nonsense. That is how it is designed. It hugs your figure in all the right places. It accentuates your best assets; the firm plumpness of your derrière, your slim waist, and thanks to the magic of modern science your magnificent fun bags. The guys will love it. The tight thigh length dress will help you keep your knees together."

She had laid out a smorgasbord of makeup and spent the next twenty minutes using them on his face. She started on his eyes going for a smoky eye look believing it would add a bit of sophisticated drama to his face. She lined the upper and lower lashes and diffused the color with a fluffy eye-shadow brush and cotton swabs until the shade turned into a very subtle gray that went up to the crease. She curled the lashes and coated the outer corners with mascara, while a dusting of powder set everything and ensured the makeup stayed ladylike.

The end result was far better than she had hoped for. A little rouge on the cheeks and then she turned her attention to Heather’s lips. They were puffy from an evening of lesbian love making. He scowled at wife who ignored it and kept up a professional demeanor in the face of his petulance. “I am going to put on your lips to plump them up. I think that will really help your look. Everyone loves big, pouty lips. Don't worry they won't be over the top, just sexy."

Then Ellen used a lip pencil to draw and outline around his lips. He could sense that the line was different from the natural shape of his lips. Ellen explained; "I want your lips to make a real statement. I am making them quite full and am using a bright red color." She outlined them in dark red then applied a glossy ruby red lipstick. Ellen then did his nails they were painted red to match his, now very sexy, lipstick.

Ellen stood back and admired her work. "Honey, your makeup makes a real difference. You know George, the greatest makeup artists in the world are men. Maybe when this is all over you could become one! Since you were fired you will need to do something for a living."

"Sheesh, what a ridiculous thing to say! Let’s just get this over worth." He wasn't interested in thinking about his future right now, not when he was standing here looking like a high-priced call girl.

Finally, she retrieved the wig and fitted it snugly on his head. She fashioned it, securing it with bobby pins. Its soft shoulder length hair hanging freely, bangs off to one side. She would have killed for a curling iron, without it, the hair hung straight. She adjusted it a bit, fluffed it out and was delighted with the final outcome.

Once she had securely pinned his wig in place, he could see his 'female self' emerging in the mirror. But this time he looked sultrier.

She went to a box among the pile and withdrew some bling for Heather. She had a cat that ate the canary smile as she looked him in the eye and told Heather to try on the necklace, earrings, rings and bracelets she had brought. After they were on, she announced, "You’re ready to go baby. Let's finish up here."

She knelt and shoved his footwear for the night on his feet, a pair of red stilettos.

She and George were the same height, but she always wore heels when they went out because George thought they were so sexy. She was going to enjoy watching him suffer in those stilettos so he will know what she goes through just to please him.

Unnerved by the height of the heels George whined, "Why do I have to wear heels this high, they must be five inches? I can't wear these! I'll break my neck!"

"These aren't even that high, they just seem tall. They're not quite four inches. I wear higher than that all the time. Like tonight I’ll be wearing a pair of gorgeous designers five-inch pumps."

George’s feet were on fire, "That might not be high for you! From my perspective they’re stilts and they must be two sizes too small."

Wearing his outrageous hooker heels. His mind was racing and he felt his heart beating like a drum inside his chest. "Ellen, no man should wear something like this and still call himself a man."

"Don't be such a crybaby. They are your size, all heels hurt. Get used to it that is what you are wearing tonight whether you like it or not. You'll get used to them. You just need practice. By the time tonight is over you will be an expert. I taught you to walk in heels, maybe not this high but those lessons will come back in no time."

"If you say so," he said skeptically.

She smiled as she thought that her husband was such a drama queen. "I know how much it bothers you when I wear heels and tower over you. Tonight, we’ll be almost the same height. I’ll admit they are darned uncomfortable, but they are outrageously sexy. Just the thing for our double date."

George never compromised with Ellen. He always went right to surrender because it saves time. He knew he would be wearing the damned skyscraper heels. But the word ‘date’ is what sent a shiver through him.

She secured the heels on his feet with straps and directed, "Walk for me! I want to get the full effect. Remember all we learned about the way woman walk. Put it to practice."

Ellen thought to herself, he learned that sexy feminine gate to walk out of jail, now he will be using it to try and get into some guys pants. The ultimate cosmic joke.

He reluctantly entered the forbidden territory of high fashion. Despite his earlier sessions in high heels. His first steps were comical, having to reach out for Ellen to keep from falling. Ellen joked, "Easy there, sugar. I guess you need to practice with those. We have several hours to practice."

He'd worn heels before, during Ellen’s training in prison. But these were way higher and had a slimmer heel than those. He tried to walk in the stilts his wife had fastened on his feet and found his feet were in agony, his toes were being crushed in the tip of the tight shoes. The heels were so high they forced him to stand practically on his tiptoes. He found that he needed to move in small, precise steps. Ellen couldn’t but help to notice his ample boobs always seemed to be in motion, as he swayed in the heels.

The stilettos were too high to be functional, but function wasn’t what Ellen had in mind for her husband tonight. For the next hour, he tottered back and forth the length of the room, his attempts to balance providing his only distraction from the discomfort in his feet. Ellen directed him, giving him sharp critiques on his walking style and giggling heavily at his efforts all the while. She ignored his insistent complaints about the shoes hurting his feet.

Ellen examined her creation. She saw a slim over endowed woman. In fact, Heather had what could only be described as a 'boyish figure'. However, that did not in any way detract from his femininity. This was one classy woman! Thought Ellen. Attractive but not over the top, just the look she was going for.

Ellen observed, "Your appearance is the embodiment of a professional working girl!"

George wondered at the term ‘working girl’ it held a number of possible alternative meanings none of which he was crazy about. He rolled his eyes and mumbled, "Great, that was what I was going for. Thanks for your help."

"I may look like one but I don't want to be a girl, even for one night." George retorted, unable to believe he was having a conversation about feminizing himself with his wife.

He covered his discomfort by saying, "I would prefer a girl next door look. This all feels very uncomfortable, these heels pinch my feet, I can only take small, mincing steps in them. And this skirt, it's very constricting and makes my ass sway back and forth when I walk. It's kind of short too; I feel like my legs are on display to the world."

To her amusement what he was missing was the way his unencumbered breasts bounced in a shameless hussy manner. She thought that element alone would make tonight’s double date a roaring success.

She could see how nervous he was about going out in public and making a fool of himself. In an attempt to lighten the mood, Ellen jokingly commented, "Heather, don’t quite your day job. You’ll never make it as a runway model."

To Ellen’s delight, Heather was starting to look more natural as she crossed the room and she advised, "Do it again, but this time walk with one foot ahead of the other. It will tend to sway your hips and give you a more feminine movement."

It was his first time in a tight-fitting skirt and stilettos, the heels selected by Ellen stretched his calves painfully. He started to object; but she put her finger on his lips and shushed him and said, "Girls have to suffer to be pretty." She had heard that as a teenager and it had sounded just as stupid then as when she was spouting it to her husband now, but it quieted him down.

Ellen smiled it had taken a lot of effort but eventually Heather's walk turned from an ungainly stumble to almost a smooth and polished feminine sway. There was now a realistic fluid motion to his unconfined supple breasts as he moved. She couldn’t help but chuckle as they even realistically jiggled with each step.

Going braless walking around the room, they bobbed like he was topless. It made him feel naked. By the time they left for their dates, George was quite familiar with how a "liberated woman" felt.

Earlier she had wondered if perhaps she was turning into a lesbian. Tonight, she was going to be with a ‘woman’ who she considered sexy. She also was going to be with a real handsome stud of a man. This night might well decide her future sexual orientation. Would her sexual compass point to the pink or blue side? She would know which way when she saw who she ended up spending the night with.

After watching him prance around the room for a few minutes she said, "That's it, you're doing better. Now keep practicing."

"Honey," Ellen lectured, "With that body you’re so cute, all you have to do is smile at a guy and he will be all over you. Your date's just going to eat you up."

A look of horror appeared on his face as George replied, "That's what I'm afraid of."

"Relax I’m just teasing. It’s essential that your date see you as a believable female and as an available one. If we are going to get them to pay for everything. Keep in mind this is mostly about your physical heath. It’s not intended to be some nefarious outing. Think of the meal we’ll be getting. If we have a decadent desert, I bet, we can get 3 or 4 thousand calories in us tonight. We both really need that."

Ellen did her own war paint a little more dramatic than George was comfortable with. Thus, making sure they were both cosmetically alluring. Then she added her prowling scent as she called her perfume.

George had to ask, "You’re doing all this for a man you just met. Is there something you’re not telling me?"

"I’m not talking about establishing a relationship with these guys. Just use them for our purposes. You for a decent meal."

"What are you getting out of it?"

Unwilling to tell the entire truth she simple said, "Well I get the meal too; our baby could use some protein. Plus, I get to socialize and maybe flirt with a real man for a change."

George flinched at that. It really hurt his pride.

Ellen bubbled on, oblivious to the damage she was doing to her husband's self-respect, "It will be just one night to re-create old times. I used to get guys to spend a ton of money on me. After all I have done to get you home, you can’t deny me that, can you?"

Satisfied that the issue was closed she directed, "Now pipe down and let me have my fun."

He could only suck it up. Ellen was determined for him not to put a damper on her night. So, he pasted a smile on his face and decided to soldier on and see where tonight went. He had to admit the thought of a good free meal was mouthwatering. All it would cost him was his dignity and that pot was almost empty anyway. A little more will never be missed.

Suddenly out of nowhere, panic gripped him. Fear coursed through his body. His smile was not genuine. He spoke from his heart and put thoughts of his stomach aside, "I am not sure Heather is ready for a date, couldn’t you just bring me something back in a doggie bag?"

Ellen pouted and sternly asserted, "That is the dumbest idea I ever heard. Dear I’m going on a date, with or without you. Wouldn’t you feel more comfortable being there with me? Think of it like you are my chaperone, you will be there to keep me out of trouble."

Then laughing, "If you can."

He jumped up and frantically grappled with the zip on the back of his dress, trying to rip it off.

Ellen screamed, "What the hell do you think you’re doing?"

George screeched hysterically, "I can’t fucking do this."

Ellen plopped herself on the bed and pulled Heather down next to her with surprising strength. She clung to Heather's bicep in a vice like grip and announced in no uncertain terms, "Yes you can. More than that you must! Now stop this juvenile tantrum or I will slap some sense into you."

He tried to pull free. Ellen effortlessly held his arm firm. "Ellen you wouldn’t do that!"

Ellen snickered. "Just try me buster."

"You saw how effortlessly I dispatched those two behemoths on the beach. A 95-pound weakling like you wouldn’t present any problem at all."

"Oh El, what am I going to do?"

Ellen released his arm and in a consolatory tone lectured. "I will tell you exactly what you’re going to do! George is going to suck it up and as Heather go on this date. Trust me when I tell you that can do this. Now stand up and walk for me."

She scrutinized him as he walked and with her trademark bemused smile advised, "Do it again, but this time put more sway in your hips."

After watching him prance around the room for a few minutes she said, "That's it, you're doing much better. Now keep practicing until it’s time for us to leave."

"But the shoes are starting to really hurt my feet."

"Damn it, stop whining and grow a pair! It’s something every woman has to endure so surely you can do it for one night."

In no time at all Ellen was dressed to the nines, a tight black pencil skirt and a very low-cut blouse, revealing her cleavage in a seductive kind of way. Her nipples poked out prominently, and when she bent over even a hint of areolae showed above the material.

Ellen brought Heather over to her and they stood side by side in front of the mirror. "You look gorgeous, we will be the two prettiest women there tonight!" she said, kissing his cheek.

The image that he struck in his feminine guise was totally believable.

He felt a sudden, dizzying loss of identity.

What Ellen saw in the mirror made her smile inwardly. She casually mentioned, "Not only am I hot but Heather you are going to be some serious competition tonight."

He had to admit that she was right. The one saving grace was when anyone looked at them, they would certainly pay more attention to Ellen than Heather.

"Thanks, but I thought we were to blend into the background," he articulated.

"Not tonight. We’re going to be in the spotlight. Now that I think about it. I don't know if I like my new girlfriend looking so sexy. You might be too much competition for me, I want my date hunting me not drooling over you."

"Oh, please," he said, taking a hold of her hand." We’re both off the market."

Grabbing his left hand and holding it up next to hers, showing their ring fingers was empty, "That’s to be seen! We both might get lucky tonight."