CHAPTER 13 - The Prince looked down at the prisoner, Who's this dirty slut? Off with his nuts! Off with his nuts!

Ellen finally received an email from her husband’s sister, saying the weather had cooled at home. Ellen began her plan to cross the border. She notified the resort they were leaving and they that would be losing their gringa maid. Ellen was pleased when the hotel manager said he would be happy to give Heather a positive recommendation.

Her next stop was to find Heather and give him the good news. She found him on his hands and knees scrubbing a bathroom floor. Ellen was sure he would be delighted to hear that he had cleaned his last toilet. He insisted upon finishing his current assignment, if he didn’t one of his friends would have to do it. Together, they went to the hotel manager and told him Heather was quitting immediately. They returned to their room and tried to decide what they were taking and what was going to be left behind. They went to bed early determined to be rested for tomorrow.

First thing in the morning, Ellen went out to buy food for breakfast, she had a spring in her step knowing this would be their last day in Mexico. She bought some fruit to get them by until lunch. She had their train tickets safely tucked in her purse. If all went smoothly, they would be at the border by lunch. She could already taste what would be her first meal in the States, a Big Mac with fries and a large diet coke.

As she was about to return to their room, a roadside vendor caught her eye. He had a large selection of hand carved items for sale or barter. She spent several minutes perusing the carvings. One phallic shaped carving caught her attention. On close examination, it was a piece of hard wood carved to replicate the male genital. A very naughty thought popped into her head. They had several hours to kill before their train. She now knew how they were going to spend them. The barter session was done in no time. Ellen spent the last of her Mexican cash on the souvenir. They had to get across the border today or go hungry.

She skipped back to their room in a hurry to show her prized memento to her hubby. As she entered their room, she had a smirk on her face.

George was laying on the bed enjoying his morning off and resting for the trip home. Seeing Ellen’s smile, he was immediately wary, "What’s up El?"

She kissed him sweetly and put the shopping bag she was holding down. She looked at him and gave him a sexually charged smile.

"Nothing really. I bought you a present. Open it up." she said excitedly, presenting with the bag. "The workmanship is exquisite. I know you’ll like it?" She said with excitement and anticipation in her voice.

Grabbing the bag, he asked, "What is it?"

"It’s what I refer to as a girl’s best friend."

He opened the bag carefully, not sure what he would find inside. With trembling fingers. He cautiously peeled away layers of wrapping paper to reveal his present. With his heart racing, he carefully withdrew the contents. To his embarrassment he found an anatomically correct carved wooden penis. George had to admit the detail and workmanship was incredible.

"Just what the hell I am to do with this? I’m not a girl! I can only assume you want me to use this on you."

"You are half right."

Involuntarily he started to hyperventilate.

"Do you trust me? " she asked.

He cautiously replied, "I am not sure anymore. Why do you ask?"

"Don’t be naïve! I have heard that it can be unhealthy for fluid to build up in a man’s prostate. I am not trying to emasculate you. This is a tool to help you with that problem. Listen to me George, I have done research on the subject. The hormones have affected your ability to ejaculate. Two weeks ago, you climaxed but I found no signs of any ejaculate. In order to keep your prostate healthy, you will have to be milked at least once each month. From what I have been told, this is a method of milking. You will find that there will be no projectile ejaculation, just an oozing of your fluids. But it is necessary for your health."

She said holding up the wooden penis. "I think this is the solution on how to deal with that. We have time to kill let’s give it a test run." Then she reached into her purse and withdrew a condom. "I think we should put a rubber on it first, for sanitation purposes. You do it. I suspect you have had more practice than little old me."

George flat-out refused to let Ellen put it inside him. He figured that enough was enough. He had gone along with everything his wife had wanted up to now, but he wasn't going to let her penetrate him with a wooden lifelike cock. With tightly clutched cheeks, he was making a stand.

"My toenails may be painted red, but I am putting my foot down, nonetheless. You’re not going to stick that up my asshole."

"No of course not! If it makes you feel better, we can call it your manly vagina. I am not trying to turn you into a female. This is something that must be done to insure your physical health."

"This is like killing two birds with one stone. Over the past few months, you’ve become a believable looking girl. You have endured a lot of the negatives of womanhood and I thought it was time you got to experience one of the joys associated with being a female."

Laughing at the way he tensed up, she went on, "Now relax. I think in the end you will enjoy this. Look at you sitting there in pretty lingerie with your nails painted in girly fashion."

Ellen very patiently explained, "I’ve read that a man's ass could be a very powerful erogenous zone. Gay men seem to enjoy it, from what I have heard."

George replied, "I’m not so sure. I have always viewed that as a one-way portal strictly limited to outgoing traffic."

She countered, "Don’t be so conventional. Open your mind to the possibilities of new experiences. In a loving situation, I am sure the feeling of penetration will be very erotic. It has nothing to do with being gay." She assured him.

"While you were taking math classes, I was in biology class. I learned that the anus has as many nerve endings as my genitalia. The tickling of the prostate gland has the possibility of triggering extremely intense orgasms in men. You might be surprised to know the prostate has the same density of nerves as the penis and, in some cases, even the penis glands. I heard It's exceptionally sensitive. To quote my male teacher, ‘If you've never had a prostate orgasm your missing out on a major life gift. It's the holy grail of orgasms to gay men.’ Honey, let’s just give it a try. I want to do this for you. If you don’t like it, we can stop at any time. Please let’s attempt it one time."

The two climbed into bed. Actually, George was pushed. Ellen climbed on him and cuddled for a while. She decided to take her seduction slow. She waited for a while to let George relax, then let her hand nonchalantly wander between his legs. Stopping there for a while, she eventually let her fingers lightly tease the area around his testes and slowly moved to his anus.

She wet her fingers with spittle. Her delicate touch revealed to George that his anus was in fact a sensuous area. He thought she just might be right about the other things she told him about enjoying this experience and decided to surrender himself to her ministrations. What did he have to lose other than his virginity?

Ellen slowly began by inserting two of her slim fingers in his long dark virgin hole. He grimaced at the invasion. His whole consciousness fixated on her actions. Her two fingers sunk deeper and into his ass. She felt the walnut-sized gland located between the bladder and the penis and adjacent to his rectum. With her fingertips, she gently massaged his prostate. After a while, he found he was moving to help her and was uttering little sighs. She inserted another finger and then another. His back gateway was now opened and relaxed. Ellen replaced her fingers with the wooden girl’s best friend encased in a lubricated condom. He felt a momentarily increase in pressure as she slid just the tip inside him to gage his reaction. When he didn’t object, she felt his sphincter muscle relax as it became accustomed to the foreign object. She firmly but slowly pushed the rest of the slender phallus up into Heather’s back door.

To George buried his face in a pillow, the pain was horrible and exquisite all at the same time. His first reaction was yelling "Stop"; but there was something terribly intimate about his wife violating his bodily waste escape hatch. He was completely overwhelmed by the barrage of sensations he was feeling. He lifted his face and tried to look at his wife.

He winced as she eased her wooden cock into him bit by bit. Ellen could tell from his expression that it hurt like hell. In response, she pulled it out a little before pushing it in again slowly, and a little further each time. He grimaced again. Ellen was patient. She repeated this pulling-out-and-pushing-in motion a couple of times until she finally managed to get the faux cock all the way in to the hilt. She held on to him tightly whispering sweet loving words as she slowly began to establish a steady rhythm. He was getting used to the size, and the pain of a few minutes earlier was slowly turning into toe-curling pleasure which was taking control of his entire body and mind.

As she pumped her little friend in and out, she found that she was also becoming more and more aroused, but in a different, more fundamental way than she normally felt during sex.

After an unmeasurable time, the pumping of the fax penis became the focus of George’s world. Finally, the tidal wave of pleasure crested and broke, sending a tingling spasm through every nerve of his being, and he was dimly aware of a liquid being discharged from his man thing as he climaxed. After Ellen finished milking her husband with the aid of her wooden dildo she asked, "So how was your first womanly orgasm? Of course, it isn’t exactly like us real women enjoy. It is as close as you will get unless you decide to turn your manly pole into a woman’s hole."

His pride wouldn’t let him answer truthfully. "I could get used to this if I had to. But I can’t ever see myself enjoying it," George lied. The smug shit-eating grin on his face told Ellen all she needed to know.

"Honey, that’s why I call this a girl’s best friend. It gives a woman pleasure and will never leave the toilet seat up or piss on the floor by mistake."

After their bedroom gymnastics, they both showered and got dressed for the trip home.

Ellen went to her closet and knelt to pull out the dress she was saving for Heather’s trip home. With his now immature breast development, the dress had to have a plunging neckline, to expose a demure amount of cleavage on Heather. Once he had it on, she knew this was the perfect outfit. With it on, his elegant décolletage was timidly displayed. Then she found the shoes that went with the dress, a pair of sexy, spike pumps in the exact shade of blue as the dress.

As expected, George griped about the towering toe cramping shoes.

She attempted a bit of levity to relive his anxiety, "Dear, Cinderella showed us girls a new pair of shoes can change our lives. These are the epitome of girlishness. Think of these as your glass slippers. That will get you through emigration and take you home."

Ellen sat him down and, with the skill of a surgeon and the talent of a renaissance artist, did his makeup. Once satisfied with her creation, she moved on to his hair. She had borrowed a hot curling iron from the hotel. After it was hot, she had recently bought she worked to wrap his hair and form large cylindrical curls all around his head from the crown to the neck line. As soon as she put the curling iron down, she started with a brush, pick and a can of hair spray. His face was framed by curls which fell to below his ears. His bangs consisted of one large half cylinder of curls.

Satisfied with his hair, she went to work on his face. She began dusting his face with powder to take off the shine, then a few brush strokes of blush finished the look. She penciled in some darkness on his eyebrows, further shaping them; she outlined his eyes with black eyeliner and feathered in color on the lids to accentuate his eyes. Then she outlined his lips with a dark plumb-red lipstick and filled it in with another redder color. She blotted his lips and pronounced. "Okay, I’m finished."

George gasped at his look, "Isn’t it a bit over the top?"

"Nonsense, when we get to the border, we don’t want some curious agent wondering about your gender. You are unquestionably looking like a hot tourist. No one would ever think there is a man under all that powder and paint."

George gathered up his toiletries, some lipstick and a hairbrush, and handed them to Ellen. "I don’t know. What happens if I get stopped at the border? Maybe I can just stay here until the man hunt is over."

"Don't tell me you're chickening out?"

"Logically, I know I am locked into this masquerade until we get home. I’m sorry, I am just scared. I need to pee before I have an accident."

"It’s probably best we both use the restroom now. You go first. I want to make a final sweep of the room to ensure we haven’t forgotten anything."

Ellen’s case was filled to overflowing, to make room for her makeup she impishly took her ‘girl’s best friend’ out of her purse along with a partially used box of lubricated condoms and hid then in the bottom of her protégés shoulder bag.

Ellen looked at her husband as he left the bathroom. "You know honey, I wouldn’t mind having my girlfriend Heather visit occasionally once we get home. I can always use a maid. To clean the house."

George was shocked at her attitude. "DON’T even think about me becoming your Suzy homemaker."

"No dear, of course not. I was thinking more along the lines of Heather being a kept woman and doing housework to fill her days.

“The way my business is going, I intend to get a full-time housekeeper to take care of the cleaning chores. Since you no longer have a job, you’re free to apply for the position. The pay isn’t much, but you will clean up on the benefits."