Oh Brother! Pt. 02

Oh Brother part 2

I was at the office of Doctor Carter, my psychiatrist, for my weekly session. It was now over a year that I had been seeing her. At first I went to her just so I could get hormones to begin my transition. She helped me do that as well as get an official name change. My drivers licence now read Molly instead of Marty and listed me as female in the gender column. I learned that the sessions were more than a means to an end for me. Talking about my life and my relations really helped me be comfortable with who I was.

A lot had changed with my appearance since that first session more than a year ago. My blonde hair had grown long enough that I didn't need to wear extensions. I had electrolysis treatments to permanently remove my facial hair. Hormones had changed my body shape. I was already a slim and somewhat feminine build before I started. Now I had serious girl curves. Unwilling to wait for my own boobs to grow, I had implant surgery to give me a big B or small C cup bust. They turned out perfectly. They were the best that money could buy. Not my money but my brother Doug's. The same doctor also did a minor job on my nose and upper lip, again on Doug's dime. Those surgeries were done about nine months ago and the scars were almost unnoticeable. I had good skin for that.

My skin was different that Doug's. We were certain that neither of us was fathered by our actual father. Our mother got around and we are pretty sure that Doug's natural father was Mister Kyprios from across the street of our old house where we grew up in. Doug had swarthy looks with black hair, dark brown eyes and olive skin. I resembled Mister Shultz, the TV repairman who lived next door. I had fair skin, blonde hair and hazel eyes. Our younger sister looked a lot like me too. We are also pretty sure that she was also sired by Mister Shultz. Only our oldest brother, David actually resembled our Dad who had pasty skin, freckles, chestnut hair and light blue eyes.

My parents and siblings were often the focus of my conversations with Doctor Carter. I liked her. She was in her mid forties and had long silver hair, a slim figure, glasses, and always dressed sharp in skirt suits. She was a feminine icon to me and made me always want to present myself with confidence. I had dressed up too for my session. I wore a peach coloured spring dress that came down to my knees and had a low plunging neck line that showed off my outstanding cleavage. I also wore nylon stockings and high heel shoes that matched my dress. I had on a single string of pearls that hung down between my boobs. I now had pierced ears with dangling pearl earrings and I had a fresh manicure with clear polish on my long nails. My hair was fresh styled and my makeup was soft and peachy.

"Molly, good to see you. You look stylish and pretty today. Have a seat," the Doctor said. She sat in her leather chair and put her notebook on her lap and drew out a pen from her breast pocket.

"Thank you Doctor Carter. You look beautiful too, as always," I complimented back. I sat on the comfortable leather couch with my knees together, very lady like. She smiled at my comment and I smiled back.

"Let's get started, shall we? Last week you were talking more about your job transition. How is that going?" the Doctor asked.

"So far, so good. As I told you last time, I felt that I had to leave my last job at the cable company because coming out as a trans woman was too much for me, having worked there for five years. The company would have been accommodating I am sure but the co workers are another story. I felt that I wasn't going anywhere with them anyway. I needed a change, transition or not. The new company that hired me must have had some history or law suits with LGBTQ staff or work place harassment because I told their HR people upfront about being a trans woman in the interview and they were eager to hire me. Their mandatory harassment training was a full day long and every employee has to certify once a year. It is still an electronics engineering position. I showed up on my first day as a woman and no one has even looked sideways at me. It pays better than my old job too. I like it there," I told her.

"And your other job? The restaurant? How is that working out?" she quickly shifted, knowing about my partnership ties with my brother in the business.

"Well, I am pretty hands off in that. I get my thirteen percent but Doug runs everything. The two of us meet with Reggie once a month for meetings but it is all Doug. I still bartend when needed but I do it as a girl now. The staff turns over so often there and I only work occasionally so no one is the wiser. I haven't had to tell any awkward coming out stories anyway. Besides, Doug is always there when I work. That makes it easier," I explained.

"So, you feel safer when your brother is around?" Doctor Carter asked.

"I guess. I am still getting used to explaining this transition to people. At least at the restaurant, I know Doug has my back if anybody were to give me grief and the employees are all scared shitless of him," I told her.

"And has anybody given you grief?" she pried.

"Actually, no. I am pretty sure at least one or two waitresses have made me but they haven't said anything and are quite nice to me," I said.

"What about costumers? They could get nasty and you don't have as much protection as you have from the other employees," the Doctor suggested.

"Actually, one guy tried to pick me up one night, just two weeks ago," I stated and giggled.

Doctor Carter laughed along with me showing her radiant smile. "I won't ask how that went. I am more interested in your coming out. So far, you have only came out to the person who hired you at your new job, and your brother and sister-in-law who helped you begin your transition anyway. What about friends and family? Anybody else?" she asked.

"I came out to my birth mother. She was stoned when I saw her and she seemed confused and perhaps disappointed but she said that it was my life to do what I wanted with it. It honestly didn't seem to be a big deal to her. She never called me Molly though. She kept calling me Marty. In all, it was a bit of a let down for me. She is the most liberal person I know so that not's a good sign.

"Okay, anybody else?" she asked after a sigh and a lot of note taking.

"Well, there is Reggie of course. He was the first one to fuck me as a woman but you know that. His manager too. I have a few other friends from the club and the gaybourhood who also know my story. There is Jane, Jeff, Kevin, Marcus, Bill, Andrea and Faith. I don't have any other friends to speak of outside of that," I informed her.

"What about the rest of your family? Are you still too apprehensive to tell them?" Doctor Carter inquired. "After all, you couldn't fake being male again with them. With that boob job and facial surgery, the genie is definitely out of the bottle."

"True. You got me there. Doug is the only sibling I have been close to since I got out of the Air Force. I have nothing in common with my oldest brother or my sister. Both have families and multiple kids and are a lot like my parents, conservative and religious. I only ever see any of them a couple times a year. I skipped my Dad's birthday a month ago. I mailed him a card and called him over the phone. I did the same for David and Jeannie a couple of weeks ago when their birthdays came around," I confessed.

"That's right. You and all your siblings were all born in the same month, all one year apart. I remember you telling me. So what about yours and Doug's birthdays?" she shifted.

"My birthday is on the last day of the month. Doug's was this past Sunday night," I said with a blush. That made Doctor Carter giggle. "So, you seem embarrassed. Is there a story there?" she pried with a wry smile.

Truth was that I loved telling her my seedier stories. I think they turned her on. She always shifted in her seat and adjusted her skirt. I caught her biting her lip once or twice and even caught the faint scent of feminine arousal on occasion. She crossed her legs tight and bent forward in anticipation.

With a coy smile, I began telling her the story of Doug's birthday night...

Doug wanted a fancy night out with his wife, Jill and me. I didn't want to be a third wheel and often felt that their hospitality toward me was out of pity despite the threesomes we had together. Both have them continued to reassure me that it was not the case. They genuinely wanted me in their lives including their sex lives. Jill coxed me until I agreed. She said that she wanted us to give him what he always wanted, a "Yes" night.

A "Yes" night is an evening out where anytime the birthday person makes a request, the answer is always "Yes", no matter what. I know my brother is pretty devious and agreeing to such a thing could be dangerous but it sounded like a hell of a lot of fun. Jill had already agreed to it. The pressure was on me. My curiosity out fought my fears so I gave in too.

Doug had already picked the restaurant, a fine dining establishment. His first request involved our looks for the evening. Doug has always had a bit of a golden age nostalgia fetish. He liked older movies, like forties and fifties films and the stars of that era. He had Marilyn Monroe memorabilia all over his house, office and restaurants in particular. That explained his attraction to his wife Jill, who gave off a bit of a Marilyn vibe, with blonde hair, big blue eyes, bombshell figure and feminine confidence. Since they got married, she had cut her hair and styled it in the early fifties Marilyn fashion. He also had a big attraction for the mysterious Veronica Lake. She was more alike to me. My hair style was not that far off and we had the same facial shape. My hazel eyes were the same shape as hers too. Even my newly shaped nose looked a bit like the iconic silver screen star. So Doug requested that he would be escorted to dinner by his two favourite stars, Marilyn and Veronica. We would have to answer to the names Marilyn Monroe and Veronica Lake, act in character, and dress the roles in vintage gowns, garters, stockings, high heels, the works.

Jill had already picked me out a gown, a silky, champagne coloured full length number with a side slit up to my hip. The slit would show off my stocking top and some upper thigh when I walked or crossed my legs which made it sexier. The neck line was low and plunged deep into my cleavage making it impossible to wear a bra. Luckily, my new boobs were firm and self supporting. I didn't need a bra any more for support normally, just for modesty. Although I went braless at home most of the time, I always wore one at work or in public so this would be a first for me. Jill's dress was white, more like Marilyn's "Seven Year Itch" dress. It was backless but she could and would wear a bustier under her dress unexposed.

Jill booked us appointments at the salon where we got our nails and makeup done and they did our hair styles to match the iconic actresses. After that we went back to their place and got fixed up in out costumes for the night. Doug was wearing a full tuxedo with black vest and bow tie in a vintage cut. He slicked his hair back with a little oil which actually suited his swarthy looks. The three of us definitely had a retro glam vibe going. We had a drink to get the night the night started while we waited for our ride. I offered a toast to Doug's birthday. We got picked up in a hired town car so we all could drink as much as we wanted. Actually, more like how much he wanted. The driver held our door and gave both Jill and myself the eye. He was a tall mid thirties guy, fit, sandy coloured hair, blue eyes and good looking. I smiled back at him. The three of us cozzied up in the back seat with Doug in the middle. There were some light kisses and lots of hands feeling up each other's expensive clothing and body parts. Doug reached into my dress and played with my nipple for a while. He exposed my ample breast which the driver may or may not have witnessed in the rear view mirror. I didn't care. I hoped he caught a look.

Jill and I each took an arm of Doug's as we paraded into the restaurant to many heads turning. While waiting for the hostess to seat us, Doug instructed, "Marilyn, Veronica, grab my ass while we wait." Since it was "Yes" night, we both nodded and slipped our hands down to his backside and took a cheek each. We massaged his butt while other guests stared. I heard a few gasps.

When the pretty hostess arrived she said, "Doug, table for three, right this way please," with a courteous smile.

Doug turned to us and said, "Hold each other's hand." We smiled and obeyed. Jill and I locked fingers as we walked to our table, again drawing a lot of attention. We had a nice booth table and again sat Doug in the middle of us on the semi circular bench. We all skimmed through the menus deciding on what to order. Doug made Jill and I flip the pages for him. His hands were busy under the table, feeling up our legs. Once we had decided, we closed up the menus. The waiter came around promptly and Doug placed our order for all three of us. The waiter was young, good looking and polite. He smiled at me as I was checking him out.

Just before the waiter was due to return with our wine, Doug sat up and told me, "Switch seats. I should be on the outside, closest to the waiter for the wine tasting." It sounded very snobbish but it was "Yes" day so I did as he wanted, putting myself in the middle. Jill instinctively started massaging my thigh through the silky material of my dress. I returned the favour, running a hand up her nylon clad leg.

As Doug saw the waiter approach with the wine bottle in hand, he quickly turned to us and instructed, "Okay. Start making out with each other. Don't stop until I say." It was a shock but I felt Jill's hands on my chin, turning my face to her own. Her ruby red lips were pursed and she leaned forward. I realized that Doug wanted us to put on a show for the young man. I pressed my painted lips into the mouth of my sister-in-law. Our tongues touched. She pulled my face deeper into hers. I could hear the waiter uncomfortably stammer as he tried to stay professional. Doug acted completely casual as he went through the douchy drawn out ritual of smelling the cork, swilling the glass, teasing his palette, all in an effort to keep the waiter at the table as long as possible while Jill and I made out like school girls at a slumber party. When Doug was finished the tasting, he had the waiter pour out three glasses. I was enjoying our little game, knowing we were being watched. I grabbed Jill's tit in my hand and gave it a big squeeze. I could hear the waiter clear his throat. Jill tried not to giggle with her mouth locked to mine.

After an eternity, Doug finally said, "Okay, you two can stop now. He's gone." I moaned a little as I took one more long suck on Jill's tongue. Instinctively, both she and I pulled out our compact mirrors and started fixing out lipstick. The thrill was getting to me, my cock was stiff and straining to escape my panties. Both Doug and Jill were still feeling up my legs under the table. The table cloth was large and hid everything from public view, Doug had flipped my dress open at the slit and was feeling up my stocking tops and bare thighs. Jill's hand slid up to my silk panties. "Take it out," Doug instructed his wife.

Jill reached into my knickers and tried to grab my erection. I had to sit up a little for it to come out. Her hand grasped my throbbing meat and stroked it. Doug giggled as I groaned and sighed. Doug leaned over and kissed my neck. My brother then told Jill, "Marilyn, go down on Veronica and make sure you swallow her load when she comes."

Jill licked her lips and dropped her head under the view of the table cloth. I felt her hot, wet mouth encircle my raging hard on. She started sucking right away. Her head bobbed up and down. I moaned and tried to not make any visible sign of my ecstasy while getting my cock sucked. Doug ran his fingers through his wife's blonde hair while he continued placing soft kisses on my neck.

After a few minutes, I saw the waiter returning with our first courses. "Doug, the waiters coming!" I stated in panic.

"Keep going," he ordered. I bit my lip, trying to contain myself. Jill was still sucking me like a vacuum cleaner. I tried to compose myself and stay cool.

The waiter looked around, noticing that one of us was missing. He smiled and said, "Here are your oysters." He was looking right at me as I tried to keep it together. He grinned. I forced a smile back.

"Is everything okay, Miss?" he asked me directly. Jill had my entire cock deep in her throat and was licking my balls with her extended tongue.

"Hum, what?.. Oh, oh, yes. Everything is fine. This just looks so fucking good. Mmmmm!" I squeaked out.

"Alright then, enjoy!" he declared and turned away. I couldn't hold back any longer and unloaded my pent up orgasm into Jill's throat. She backed up as I filled her stomach with a flood of semen. I could hear her gag and choke as she attempted to swallow my load of sperm. Once I finished pumping my baby batter into Jill's mouth, she gave my penis one last lick and resurfaced above the table. She made a display of swallowing down the last bits of my cum before taking a drink of wine to wash it down. I fumbled with trying to tuck my spent dick away again into the silk trappings. I looked at Doug who was grinning devilishly as he sucked back oysters from the shell.

He swallowed down a mollusc before saying, "Marilyn, you've got some cum on your chin. Help her with that Veronica." I licked the drizzle of white cream from Jill's chin and we kissed, sharing the salty treat. After our short kiss, we tucked into the fresh oysters before the birthday boy devoured them all.

Doug's next little exhibitionist trick took place when the main courses arrived. The waiter had a helper to bring out all the plates at once. Doug had pulled the strap of my dress to the edge of my shoulder. He instructed me before hand, "When they are putting out the plates, make sure that strap falls away and your boob falls out. Pretend not to notice it either."

Once the waiters arrived and started placing the meals, I took a drink of wine and as I leaned forward to place my glass down, I let the strap slide down my arm. I leaned back and I felt the cool air on my exposed nipple. As instructed, I pretended not to notice that my boob was out on display. I was proud of my perfectly shaped, hand crafted augmentations and could see both waiters turn beet red as they tried to avert their eyes. "Okay, enjoy those meals," the young man stammered.

"Oh waiter, can we get some fresh cracked pepper please?" Doug interjected before he could scurry away.

The nervous waiter smiled and said, "Of course." He returned with the pepper grinder and my breast was still hanging out. He served Doug first and then looked at me, hesitating on what to say.

"Yes please," I said to break the silence. His hands shook as he gathered up his courage and leaned forward, breaking peppercorns over my food.

Leaning in closer, he whispered, "Miss, your dress. The strap has slipped down. I am sorry but you are a bit exposed."

I pretended to be shocked. I looked down and acted embarrassed. I made a slow display of pulling the strap back up and tucking my boob back into my dress. I thrust my chest out. "There, how's that?" I asked while showing off my cleavage.

'Uhm, ya. They are perfect. All good. Sorry about that," he stammered nervously. After finishing his chores, I could see him sweating. I smiled at him politely and winked.

We enjoyed our meals after that and drank more wine. Doug made his wife and I make out again after dinner was finished until the cheque came. We certainly left our impression on that establishment.