A New Life

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With Jess still sound asleep, Barbie decided to make her a special breakfast in bed. He cooked waffles, sausage, cut up some fresh fruit and poured maple syrup over the top. Pouring a glass of milk and orange juice, he added a flower in a glass of water as he carried it into the room.

The smell of breakfast woke her up, and she smiled as he set the try across her lap and set a napkin across her chest.

"Good morning sleepy head. How is the prettiest angel around feeling today?" He smiled and gave her a peck on the cheek to help her feel better for the new day.

"Oh I am feeling much better, thank you. What do I owe this special treatment too this morning?"

Barbie sat at her feet smiling, as he chewed on a piece of sausage. "Oh I just thought I would make breakfast in bed for a very deserving young woman I know who needed a little pampering in her life. Oh, before I forget, I called in for you and me both today."

Jessica looked at him, feeling tears try to well up, but wiped her eyes and began to eat like a wild woman who was eating her last meal. She looked so cute sitting in bed chomping down on waffles and sausage in her silk robe.

"So you called in also. What do you have planned that is sooo important for you to call in sick." She smiled with a mouth full of food and playfully shook her fork at him.

"Oh I have a very good friend who needs my company and a little cheering up. I cant let her go through her troubles all alone and not be able to get out and enjoy life too." He tickled her foot through the blanket and she laughed trying to get away.

"Stop it!!! I am so ticklish and hate to be tickled." She was laughing and kicking her feet at the same time almost knocking the tray off the bed. "See what you did, almost made me lose my breakfast. Now get out of here before I stab you with my fork."

"Ok, ok...I will go...but I set out a outfit for you to wear in the bathroom there for when you get out of the shower, I wont take no for an answer, so please wear it for me." Giving her a little peck on the cheek, and stealing a sausage from her plate, Barbie strode into the other room closing the door to give her some privacy.

About an hour after he walked out of the bedroom, Jessica appeared in the doorway, looking as beautiful as ever. He had put out a beautiful sun dress that was ¾ length, and was sleeveless. It had a somewhat low cut bodice and it flowed freely around her legs. He had also set out a bra and panty set that he really liked, that he thought would fit her perfect.

"So Bennie, what do you think? Am I Frankenstein in a dress enough for you and the world?" She looked down at the floor, wringing her hands so embarrassed she wanted to cry.

Walking up to her, taking her chin in his hands, he kissed her right on the lips and held that kiss for as long as he could. When he pulled away, he smiled, "Jessica you look beautiful." She looked into his eyes, lips trembling, and feeling like for the first time in her life, someone really meant what they said.

"Bennie, I don't know why I feel so comfortable around you, but I do. You just said something to me that I have heard a million times before, but until right now, I never believed it." She grabbed Barbie and give him the biggest hug she could manage, and kissed him on the lips right back.

Barbie took Jessica out for a day of pampering and total relaxation. It was his first time out in public as a female, and he was so nervous. Jessica helped him to stay calm, and reassured him no one knew any different. Together they helped each other have a wonderful day that they both needed so very much. They eat lunch on the boardwalk, fed the pigeons at the fountain and listened to a local band play on the beach.

After a wonderful day out in the sun, Jessica asked if Barbie would take her to get her clothes and help her get out of her boyfriends home. He agreed, and called Francine to see if she would help them. Francine happily joined them and they headed for the other side of town.

Once at her boyfriends apartment, she grabbed only what belonged to her, and stuffed it into trash bags and one single suitcase she owned. He was still at work or out banging his whore girlfriend, so they had no problems getting Jessica's stuff. Jessica left him a note telling him to "Burn in Hell!" Before they left, she looked in a secret place she kept all her money and valuables, and took everything putting it in her purse.

Francine, Jessica and Barbie hauled three trash bags and a suitcase to Barbie's car. After they were away from his apartment, Jessica called his cell phone telling him she was gone and would never be back. Jessica felt such a relief wash over her that she almost jumped out of her seat in joy. All three of them went back to Barbie's apartment and opened the bottle of rum he had bought over the weekend. In no time, they had drained the bottle, and started drinking the wine Francine had given him. By the time Francine walked across to her apartment, they were all tipsy and ready to crash for the night.

The next morning, Jessica and Barbie both got dressed and went to work in her car. They had decided to share the expense of driving to and from work since it was almost 15 miles one way each day. Jessica was back to her normal self, and Barbie was happy too. The day went without a problem, until someone walked in on him in the employee restroom.

Barbie was in a stall, his pants down and they saw his panties and stockings he had chosen to wore. He didn't know anything happened until his boss called him into his office at the end of the day.

"Thank you for stopping in Bennie. I am afraid that we have a little problem." John Fuller looked at Bennie across his desk with a stern gut wrenching expression that just said you are finished. "A fellow employee who I wont name, has informed me that you were wearing women's things under your work clothes."

Bennie blushed from head to toe, with embarrassment. "Umm, yes sir, I have been wearing them for several days now. I ensure you though Mr. Fuller, that my outer clothing is all male." Bennie hoped that would make somewhat of a difference in his bosses way of thinking.

"Well, as you well know, our employee handbook has a very strict dress code for it employees. It doesn't say you cant wear what you wish under your clothes, but I doubt it means you can go around dressing like a faggot or something on company time." Jim didn't flinch or seem to feel remorse for his harsh words. He was very mad that one of his best employees was found to be a cross-dresser.

"Excuse me sir, but I don't like that word. I am not a faggot, nor am I gay. I just enjoy female things, and I will not stand here and be talked to like this, not even by you." Bennie was getting irate, and wanted to punch his former boss right in the face.

"Well Bennie, you can pack up your things and get the hell out of my building. If I ever catch you on these premises again, I will personally kick your faggot ass and have you thrown in jail." Jim Fuller stood up and made a move towards Bennie, but he got up and walked out of the office before anything could be said or done.

Feeling very mad and upset, Bennie emptied his desk, and walked out of the building. He passed Jessica on the way out with tears in his eyes, and didn't want to stop for fear of getting her in trouble too.

Jessica ran out the door catching Bennie by the arm. "Hey! What the hell is going on? I just get a call from Mr. Fuller saying you have been terminated and are not allowed back in the building."

"Jess, I was just fired because someone saw me wearing panties and stockings in the restroom earlier today. I don't know who or what they told him but I was just accused of being a faggot and totally disrespected by Mr. Fuller." Bennie continued walking to his car, stuffing the box of his office belongings into the trunk and then sitting in the car crying his eyes out.

Before he could look up, his passenger door swung open and Jessica was sitting right beside him. "Fuck them all Bennie! He just called me into his office and threatened to fire me unless I sucked his dick." She too had tears in her eyes, and they both cried together before heading back to Bennie's apartment.

Sitting in the kitchen, finishing the bottle of wine from the night before, they discussed their situation. Between the two of them, they would make it. Bennie had a decent sized savings that had been left to him by a grandma. Jessica said she had a good amount of money saved up, and also had a trust fund she had never touched. Rent was paid up for the next four months, because Bennie had paid for the first 6 months on his lease.

Francine brought dinner over, and heard the both of their stories. She thought about what had happened, and made them an offer if they wanted to accept it.

"Barbie, you know I own my own advertising agency. I could always use a couple of extra people to help me with my big accounts. I cant pay you what you was probably making at the tele-center, but I should be able to make it worth you while."

"Oh Francine, I cant ask you to do that. Why don't you hire Jessica to work in your agency, and I will try to find something in computers. Maybe I could open my own web design business. I have a degree, and have been building websites for friends and others I know for a couple of years now."

They discussed it, and Jessica would work for Francine, and they would all help Barbie get his web design business up and going. Francine said she would give him free advertising in exchange for her own personal custom website.

Feeling a lot better, and much happier, all three of them went out to celebrate their new friendships and partnerships. Barbie bought dinner for all three of them at a local Italian café. As they sat eating and talking, Barbie realized she had probably made the best friends she could ever have. She was also beginning to think she might be falling for Jessica. They had not done anything close to sex, yet they felt so close, and slept together every night as if they were already a couple.

After a few drinks and dinner, they decided to go back home and take it easy. Francine invited them both over for a nightcap, and they both accepted. All she had to offer was bourbon, and between the three of them they finished a bottle. They were feeling very relaxed and very tipsy. Barbie and Jessica kept touching and tickling one another, while Francine scooted beside Barbie.

In just a few seconds, Barbie had two wonderful women on either side of him kissing and touching his body. He had often dreamed of a threesome, but never like this. Francine slid her hand under his skirt finding his throbbing cock inside his pantyhose. Jessica opened his blouse and began sucking and biting his nipples while she fondled his smooth balls.

"Oh wow, I don't believe this is happening." Francine had moved down and taken his cock into her mouth through his panties and pantyhose, which was driving him crazy with lust. Jessica had removed his top, and she had helped her out of her dress, and was now sucking on her puffy red nipples. Barbie had her hand inside Jess's panties rubbing and fingering her clit. He soon found out that Jessica made lots of noise during sex.

"Oh Barbie, your cock tastes so good. I cant wait to fill it spurting its creaminess down my throat." Francine had slipped off his skirt, panties and pantyhose, leaving him totally naked. She wiggled out of her jeans, blouse and panties leaving only her socks.

Laying down on her sofa, Barbie pulled Jessica on top of his face devouring her tight shaved pussy. His tongue went right into her center, making her squeal and cry out as she rode his face. Francine, not able to wait any longer, climbed over his waist, and set her pussy right down on Barbie's rock hard cock.

"Oh fuuuuckkk!!!! Use your tongue Barbie, yess yesss right there." Jessica was moaning and talking dirty the whole time Barbie tongue fucked her snatch making her beg for more.

Francine and Jessica kissed and fondled each others tits as they rode Barbie to their own intense orgasms. Jessica was first, as she scream into Francine's lips when her pussy gushed all over Barbie. Hearing and feeling her push over the edge, Francine joined her and her own loud cries of orgasm as she rode her first cock in a long time.

Covered in pussy juice by two beautiful women, Barbie lost all control and groaned out into Jessica's pussy as he exploded deep inside Francine's dripping wet pussy. He came for what seemed like five minutes, as both women continued to ride him through their own orgasms.

Switching places, Francine set her cum drenched cunt over Barbie's face making him lick and drink his own cum from her pussy. He didn't hesitate and went right to work on sucking their mixed juices from her horny hole. Jessica seeing Barbie's cock never went down, licked and sucked his and Francine's juices off his cock the climbed on for a ride of her own.

Loving the feeling of two women getting off on his face and cock, Barbie did his best to please both Francine and Jessica. They were in constant orgasm drowning him almost from head to toe. He could hear them both kissing and playing with each other as they ride him from both ends. Barbie thought if he had to die, this would be the way to go.

Just as soon as it started, it ended in a mind shattering orgasm for all three of them. They came all at the same time, as they screamed and hollered in the most intense sex of their lives. Francine's apartment smelled completely of sex and cum, and they were panting and shaking all over her sofa.

After they all calmed down, they snuggled together, kissing and touching one another with Barbie in the middle. Francine and Jessica were sleeping with their heads on his chest, and his arms around them both. He was for once in his life, happy and felt loved. He didn't know what the future held, but he hoped that Jessica and Francine would be a part of it in one way or another.

The next couple of days were spent busy getting Jessica settled into her new job with Francine. They were both like kids in a candy store as they went shopping to get Jessica things she would need for her adjoining office to Francine's. Barbie spent that time to get an office set up in his apartment so he could begin to work on his web design business.

He picked up his last pay from his old boss, and Francine let him use an office in her business to help get him going. They were becoming very close, and Jessica had permanently moved in with Barbie. Things were looking better as each day went on, and Barbie found no need to call Maya anymore.

Jessica helped Barbie with fashion choices as they both went clothes shopping. She was more open in her appearance and personality now that Barbie was there to encourage her. They were helping each other to come out of their shells and became very close in the process.

On a Friday night, on her birthday, with Francine and other friends present, Barbie proposed to Jessica at the Italian café they eat at their first night together. With tears of joy and happiness, Jessica said yes, and they all had a happy cry. Barbie would become the happiest girl he could ever imagine being, and Jessica would forever be in debt to her lover for helping her to see past her scars and fears.

Francine eventually moved away, having gotten bad in health. She left her business and a fair share of money to them both to keep them going. Jessica took over the advertising agency and Barbie kept his web design business going. Barbie kept in touch with Maya, with Jessica's permission, and even had her over a few times for old times sake. Jessica liked Maya, but it wasn't the same as it had been with her, Barbie and Francine.

This is only a one part story. If you would like to see more of it, or have any ideas you would like me to maybe write about, please let me know...this is only my second story I have ever written. You can read part 1, 2 & 3 of my first story called "A Summer Camp Adventure" under the same shemale/cross dresser genre here at Literotica.com

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14 Comments
AnonymousAnonymousover 3 years ago

Amazing. Read the whole thing as quick as I could. Amazing mix of sex and pure emotion.

Al3xxAl3xxover 5 years ago
Outstanding

Great story, wish there was more to read!

JKBigDaddyJKBigDaddyover 10 years agoAuthor
Thank you!

Thank you everyone for your comments. I would really like some help in getting my stories edited before I send them out. Can anyone tell me how I find an editor here in LIterotica that can do it for me. I plan to continue this story and my other story series very soon, but I could really use an editor.

AnonymousAnonymousover 10 years ago
Proof read and edit.

I loved the story and you should continue it some more. But you do need to proof read and edit it before it is submitted. The story seemed like it was too rushed. This had to many spelling errors and grammar errors. Some spelling errors made it hard to understand what you wanted to say. Also you had their boss Mr. Fuller's first name as John and further down called him Jim. This was on the last page and only two paragraphs apart. And you had that Jessica drove her car to work that day and you then had that it was Barbie's car when they went home from work that day they got fired. These kinds of errors mess up the flow of the story and make it less enjoyable. Take you time to develop your stories and do not rush them out like you are in a race to finish them. If you put the time and effort in your stories; you will find five star ratings on all of them.

LovinhoseLovinhoseover 10 years ago
Great story...until the end.

I thought it was a great story until the end. I did not care how Francine left the story. When you write a story, people identify with the characters, they fall in love with them, we feel like we know them, we feel like they are our own friends. I don't think a sex story was the correct genre of story to be writing off characters under sad circumstances. That was more appropriate for a fiction drama novel or short story. Otherwise, great imagination and content/context, I would just proofread more next time, there were many spelling and grammatical errors throughout.

I would love a sequel, and would especially like to see Barbie end up working for the escort agency where Maya works (actually thought you were going there when you mentioned that in the story but was disappointed it didn't happen...yet?). I think that would be a great angle, allowing Barbie to truly come out and discover what it's really like to be a woman! I'd also bring Francine back, all better, and re-introduce her into the mix. Hope to read a follow up to this story.

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