The Billy becomes Billie Story

Billie smiled back and pulled Sally into her arms and kissed her lips tenderly. They held and caressed each other until sleep came for both of them. The next morning they smiled at each other. Billie said, "That was so beautiful last night, I loved it and I love you."

"Oh, Billie I love you too!"

Billie enjoyed the clothes they were wearing to classes now, jeans and tops, shorts and Ts, and as the weather cooled they often wore miniskirts with cropped tops. She loved the fashionable suits they wore from time to time. Her favorite was a black pin striped suit with an above the knee pencil skirt, a white blouse and stockings and black three inch heels. Once or twice a week after the freshman year they could chose their own outfits. She had a very cute ass and her breasts constantly drew stares from the males. She loved wearing tight pants and skirts and showing a little cleavage or a touch of lace.

She was a stunning young woman now and the scrawny little boy was gone forever. The sophomore and junior years refined the social skills and reinforced the feminine behavior and appearance of the 'girls'. Billie was a perfect student and was always at the top of her class; Sally was always close behind her. They were very fond of each other and enjoyed sex with each other.

Billie was usually the instigator in their loving. She would gently grab Sally from behind and cup her breasts, holding her while she planted soft moist kisses on the back of her neck. Sally would soon twist around until their lips met and their bodies were pressed tightly together.

Billie would slide a hand up under her skirt and down into Sally's panties. Billie gently caressed Sally's ass and slipped a finger down to slip up and down the crack in her ass. Sally would help Billie work Sally's little panties down until they dropped to the floor. Sally would kneel on the bed and flip her skirt up over her back.

Billie lifted her skirt and dropped her panties, then Billie would drop her panties to the floor and kneel on the floor so she could press her face between Sally's ass cheeks and lick them up and down. Sally loved that because she knew Billie would soon have her tongue up Sally's asshole and lubricate it with her saliva. Billie then worked her fingers deep into Sally's little puckered hole.

When Sally's boy pussy was juicy enough Billie would slowly and carefully work his cock inside her. Sally loved how that felt. Sally adored Billie's long slow strokes. The first few strokes hurt a little but soon changed to a sensation she loved.

Billie was in heaven too and she always added a few drops of Astro Glide Lubricant from time to time, she hated it if Sally yelped from the pain of not being slippery enough. It hurt Billie too but usually hurt Sally first. Billie would pull out and squirt some of the liquid up in Sally's gaping hole. Sally knew when Billie was about to cum, she got faster and harder with her thrusts. Sally would feel her stiffen as she shot her load up inside her and the slipperiness increased, usually making her cum too. Next time she would fuck Billie.

The summer before the senior year they were permitted to go home if they desired. Sally invited Billie to stay with her and her family. Billie was accepted as part of the family and loved it. She had no experience with a close, loving, and supportive family. Sally's mother and father were obviously very much in love with each other. They were an average blue collar family and both parents worked and Sally and her two sisters and three brothers pitched in and did most of the house work without being told. Sally and Billy were gently teased about their transformations. Sally, born Salvador, was dearly loved by all her siblings who viewed his change as a sacrifice she was making so the others could have a better chance at college.

Their senior year found them busier than ever when they returned with a month to go before classes started. Both Billie and Sally were part of the instruction team welcoming new students. They taught the new 'girls' what they had learned and refined over the past three years. The two were indistinguishable from real females and were actually much more feminine than many genetic females. Both girls now had their own long hair they could style many ways. They no longer had to wear the corsets because their figures were permanently trained in a feminine shape with the slim waist and girlish hips. They were expert in styling their own hair and doing their own make-up for any occasion. They no longer had to obey the 'numbered' selections for what they wore to classes or anywhere. They both had graduated with two degrees and were working part time. Sally worked in a large commercial real estate office. Billie was employed in an investment company. No one in either company suspected they were anything but what they appeared to be, beautiful, intelligent, stylish, hard working young interns.

Billie and Sally dated a few young men as part of their training. They had enjoyed sex up to the point of intercourse with many of them, but would go no further. Both of them would give head but declined to receive it. They enjoyed oral sex and anal intercourse with each other. They were both aware that sex with males could lead to disclosure and ruin their chances for the careers they had worked so hard for.

Billy and Sally enjoyed the sex but not wanting anal sex from their dates they became very proficient at giving head. They practiced on each other. They were easily the best cock suckers in the college. Knowing how it feels from both sides was a big advantage.

Billie earned a degree in psychology as well as degrees in business and marketing. They were reviewing job offers from many companies. There was one possibility that intrigued both of them, the company wanted to hire both of the girls and was aware that they were both shemales.

The company was located in Miami and had an extremely good record and while the salaries were among the best, the perks were great, including a clothing allowance because the dress code required the ladies wear suits or similar dresses at work. They discussed the offer and decided to take it. They would only be three hours or so from home and the two girls could share an apartment. Both of the girls saved every dime they could and they were able to afford a small apartment in a complex not too far from work that was recommended by their new employers.

Sally's family had given her an old but reliable Honda Civic. Her brothers also helped them move to Miami because the Civic was too small to carry all their clothes and things. They agreed that the first priority was to get a larger, newer vehicle as soon as they could. The company was very helpful in getting them settled in Miami.

The girls went through an orientation class before they were assigned to their new jobs. Sally was assigned as the assistant to the Chief Financial Officer. Billie was happily surprised to find she was the new Administrative Assistant to the GEO of the company. Both girls were sent to meet the CEO when they were all settled in with the Company. Thompson Enterprises was a large company providing services primarily for the South American trade.

The CEO was a lovely woman who greeted them warmly. She smiled and said, "My name is Mrs. Charlene Bennett, I am happy to finally meet the two of you in person, I have been following the progress of both of you ever since you enrolled at Wintergreen School, I am an Alumnae of Wintergreen too! We have a total of eight members of the 'Wintergreen School for Women Alumnae Association' working here now. I know we will be happy with your work. You will each be working with one of us. Each of you is being groomed for a high position in this company, we need you and I know you won't let us down." She grinned, "Now that the business is taken care of, are both of you settled in, and is everything OK. Any problems at all? We are very well established in this community and have agreements with businesses of all sorts. Anything you need from cars to shoes, you check with Human Resources first, we will get you what you need at ridiculous prices. We are the agent for thousands of buyers from South and Central America and are now expanding into the Asian markets. If you want to buy American goods we are the people to see, if you want to sell goods to American markets we are the people to see. We are the official buyers for over 47 countries now."

Billie said, "I think we are fine for now, we need a new car but it took all of our savings to get in an apartment. When we save some money we'll let you know."

"Don't be silly, Girl. What kind of car do you want?"

"We are not locked into anything except that we want a mid-sized 4-door sedan."

Mrs. Bennett picked up a phone from her desk, she pressed a button and paused before she said, "Betty, get me our best price on a mid-sized 4-door sedan for two employees. Fine, call me right back."

She smiled, "Our very best prices are with Chrysler right now. She will find one for you in a few minutes. We will buy it and sell it to you. We take the interest free payments from your pay. Do each of you want one?"

Sally and Billie looked at each other. They each thought for a moment. Billie said, "Depending on the payment, that would seem to be the best way to go."

The phone on the desk rang. Mrs. Bennett answered, and listened. Then she said, "If you want immediate delivery, we can get two Chrysler Sebring Convertibles, loaded, one white, one silver gray, both with gray interiors, Retail Price $31,200.00, you get it for $205.56 a month for 72 months, with a $14,800.00 total price. They are on hold for two days so you can go to any dealer and look at them and compare prices. How does that sound? This is a great deal and only available because we are loading a ship with a full load of Chrysler, and Dodge cars and trucks. We simply ordered some extras at a huge discount."

The girls looked at each other and smiled. They both said, "Yes."

Mrs. Bennett laughed, "Each of you will get a raise bigger than that at the end of your 90 day probation period. Oh! Were you told about your clothing allowance? If you shop at one of our customers you get at least fifty percent off retail and they are some of the best shops in Miami. Get a list from the HR Lady. No, tell her I want her to give you the pamphlet. That lists every place you can get a discount on anything. You girls are starting out in the 'Management' category and are expected to be very well dressed and perfectly made-up at all times. You are entitled to use the executive salon on the top floor. The operators up there are some of the best in town. Use it, it's free. I don't want you to get big headed but you are the two most beautiful girls we have ever seen come out of Wintergreen, or anywhere else for that matter."

Billie said, "I just want you to know that Sally is beautiful inside and out."

Sally said, "Mrs. Bennett, you are very lovely too, are there many girls like us who are married to a man?"

"We don't have accurate figures on that, of the 1782 graduates we have lost track of almost twenty. As best we can tell 1639 of them are still living as women. Over half of those are married to men. Many have genetic women as wives and most of the rest are with shemales. Several have had children."

After the girls were settled in their jobs and past the probation period they became involved with social invitations. Most of the customers were Latin and the blondes were constantly being asked out. They usually double dated and rarely accepted a second date.

Billie was very fond of her boss, Mrs. Bennett. Mrs. Bennett was very impressed with Billie, and told Billie she was by far the best assistant she had ever had. The two roommates were invited to the Bennett home on Star Island, near Miami Beach. The estate was magnificent with tennis courts and an Olympic pool overlooking Biscayne Bay.

A huge yacht was moored beside the large house. Mr. Bennett was a charming host and their son David Jr. was a handsome 28 year old young man. He was very polite with both girls but he was very shy around Billie. He seemed more relaxed and friendly with Sally. They had a grand time and Billie was declared the all-time Champion Tennis player of the Island. She handily whipped all comers and often it was no contest. Davey, as his family called him, was not able to take his eyes off of Billie, especially when she changed from her tennis outfit into her tiny Bikini. Sally smiled to herself, because Davey asked so many questions about Billie, how old she was, did she date much, did she have a boyfriend, where was she from, did she like to dance?

Sally picked up Dave's hand in hers, "Davey, she is as free as a bird; she is a very sweet and caring person and is lots of fun to be around. You should be asking her these questions. She is very real and nice. Go talk to her."

Davey looked at Sally, "Thanks for talking to me, I am afraid I'll stutter if I try and talk to her, she is so damned beautiful."

"Davey, that girl doesn't know how beautiful she is, she is very friendly and will never reject anyone who treats her as a lady."

Davey looked at Sally and stood up. He walked over and sat beside Billie who was talking with his mother and father. He smiled, "Hi Mom, hi Dad, please introduce me to this lovely lady."

Mrs. Bennett laughed, "Davey this sweet girl is my Administrative Assistant, Miss Billie Johnston. Billie, this young man is our son David Jr., We all call him Davey. What is all this formality about, son, we introduced everyone earlier."

"Momma, I just wanted to make a good impression on her before I ask her if she would like to go water skiing."

Billie laughed, "You don't need to do that, I would love to go, but I have never done it before."

Mr. Bennett said, "Don't worry about that, little girl, Davey is an excellent teacher." Davey took Billie's hand and led her over to where Sally was talking to another young man.

Sally looked up and smiled, Davey said, "Hey you guys, Billie wants to learn to water ski, I need someone to run the boat, Sally do you want to try it too?"

Sally grinned, "I learned to ski at school a couple of years ago, but I would love to go."

"Great, Mike and I will go get the skis and the boat keys, we'll be right back."

When the guys left Sally said, "What are you up to? You were the best skier in our class."

"Well he's so damned cute I wanted to be with him for a while, I thought you had him hooked."

"No Sweetie, all he did was talk about you. He was afraid to talk to you because you are so beautiful he was afraid he would stutter or drool all over himself."

"Really? He said that?"

"Yes he did, except for the drool part, I made that up." They hushed as the guys returned and led them to the boat. They motored slowly out to a sandbar in the bay. Davey helped Billie out of the boat; the water was only about three feet deep. He helped Billie put the skis on and held her while he put a pair on too. He showed her how to squat down in the water and extend the skis with the tips above the water while she held the tow rope between the tips of the skis. He had a firm grip on her arm as he nodded to Mike.

Mike applied the power to the boat and it surged ahead. When both Davey and Billie started to rise out of the water on their skis, Davey yelled, "Pull yourself up." Billie wobbled about some at first, then was fine. Mike started a slow turn back toward the sandbar. They went past it and made another lap. When they approached the sandbar again Davey told Billie he was going to drop off and she could try it alone. She made another lap, gingerly grossing the wake several times. Mike made another lap and Billie dropped off and settled into the water next to Davey. He grinned and told her she did great for a novice. She looked at him, "Davey, I fibbed to you, I have skied before, but I wanted very much to be with you. Please forgive me."

Davey laughed, "You sure put on a good act. I was thinking I was really a great teacher. Come on get in the boat and we can let your friend have a try. He lifted her easily into the boat. Sally and Mike got in the water; they each wore a single Slalom ski. They were both good skiers and had fun cutting back and forth across the boat wake. They finally signaled that they wanted to stop. Davey headed back to the sand bar and they dropped off. When they were back aboard Sally turned to Billie and said, "Why don't you put on those wake skis and show us how to do it?"

Davey smiled at Billy, "Are you that good?"

"No, not really, but I would like a couple of solo runs on your 'wake skis' if nobody minds."

Davey chuckled, "Get ready babe, show us what ya gots."

Billie got ready and gave Davey a thumbs up, he slammed the throttle forward and the boat leaped ahead. Billie immediately leaned away from the tow line and swept out to the right, reversed course and cut across the wake leaping into a full twist before she hit the water again, reversed again, crossed the wake and did a single flip. Back and forth she went flipping and twisting. She did a last flip with a half twist and landed backwards. She skied backwards for a bit cutting back and forth and still flipping, then twisted back forward. She signaled she was through and Davie headed for the sandbar. When she hit the water Sandy yelped, "Something's wrong, hurry back!"

Davey spun the wheel and chopped the throttle. Only Billie's head was above water when they pulled up near her. Sally screamed, "Are you OK."

Billie shook her head, "I lost my top, see if you can find it, Please."

Mike yelled, "There it is, right over there."

Billie looked where he was pointing and swam that way. She found it and waved them over. Billie threw the top to Sally, "I can't see what is wrong, can you fix it? She handed the skis to Mike."

Sally looked at it. "Billie, the clasp is broken. I can't fix it." Davey motored the boat over to her, when it was beside her she yelled, "Davey, pull me out."

Davey ran to the side of the boat and grabbed her hands and lifted her aboard. She calmly took a towel from Sally and dried her face while her gorgeous breasts jiggled. She sat in one of the seats and took the Bikini top from Sally and carefully examined it, "You are right, it's broken. Take off your top and we'll both go topless."

Sally giggled and removed her top. "There, now we are even." They both stood and walked to each other and hugged. Sally looked at Mike, she smiled, "That feels good, you should try it."

Mike started toward her, his arms extended. Sally laughed, "No Mike, try it with Dave."

Dave hooted, "No damned way buddy." He picked up his T-shirt and handed it to Billie. "Here girl, I don't need it."

Billie giggled, "My hero, thank you kind Sir. You are a true gentleman. She looked at her hands, "I know better than to ski bare handed. My hands hurt."

"Bullcrap!" moaned Mike, "We have them both topless and dumbhead gives her a shirt."

Billie smiled and before she pulled the shirt on she put a hand on each side of Davey's face, "I reward my heroes." and pulled him down for a sweet kiss,, her breasts pressed against his bare chest. She whispered, "Thanks, babe, I appreciate that." She watched him as she raised her arms and pulled the shirt on. His eyes never left hers. Dave turned and patted the seat beside him. She sat and he turned the boat and headed for home. Sally had her top back on and smiled at Billie with a wink.

When they got back to the mansion they were warmly greeted and Dave's Mom and Dad wanted to know if they a good time. Everybody said that they did. Mr. and Mrs. Bennett said they were invited to a party that evening and were going to have to excuse themselves so they could get ready. Billie hugged Mr. Bennett and told him she had had a super good time, and then she kissed him on the cheek. She turned to Mrs. Bennett and kissed her too. "I'll see you in the morning boss." Davey took Billie's hand and led her aside, "Will you let me take you out to dinner tonight?" He looked soulfully at his shoes, "I'll have to eat all alone tonight. I hate to eat alone." His lower lip was in a full pout. Billie patted the back of his hand that still held hers. "Poor Baby, They are going to leave you at home all alone aren't they." She looked as if she was going to cry, then she brightened, "What a crock of Bull. NO! I will not go out to dinner with you!" She smiled gently, "But I would love it if you would come home and have dinner with Sally and I. We have a frozen Lasagna, some bread sticks and salad. You can stop on the way and pick up a bottle of nice Italian Wine."