Fifties Housewife The Next Day

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Gerry goes to work and is confronted by his coworkers.
4.8k words
4.65
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Part 3 of the 3 part series

Updated 09/23/2022
Created 06/30/2008
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Gerilynn69
Gerilynn69
59 Followers

This is a story about Gerry's life. You can read more about Gerry in the story Fifties Housewife.

I have been working in a small accounting office as a bookkeeper. I work with three women in the office. Sarah is the CPA who owns the firm. She always seems to know whenever anything is going on. Jane works as our receptionist. She knows all the latest gossip and is a real sweetheart. Sam or Samantha works with me as a bookkeeper and tax preparer. She is a wild woman hiding as a bookkeeper.

The whole office knows about my long-term relationship with Darren. We are treated as just another couple and we are often invited to office dinner parties or outings. At these parties inevitably I end up hanging with the office crowd while Darren drinks with the other significant others.

I had taken a personal day the day before and Sarah was the first person I met in the office the day I returned to work. She had coffee started and was holding a cup in the reception area as I walked in. I was a few minutes later than usual. I was usually the one to get the coffee going and be catching up on email before everyone arrived.

"So fun night last night?" Sarah said.

I blushed and mumbled something unintelligible. I could not believe she had asked me that so quickly.

"You did have fun last night! You are going to have to tell everyone or find a way to hide that look of satisfaction."

"I, umm. Yes we had a nice night in." I said trying to imagine how she could have guessed.

She asked me to follow her into her office. She told me to grab some coffee and a muffin on the way in. Following her instructions I sat across from her and she smiled again as I sipped my coffee.

"So what have you and Darren been up to?" She said fishing for details.

"Oh just a quiet night in. Why do you ask?"

"Well for one I have not seen you this late into the office since you started here. For the second I haven't seen you wear make-up before."

"Makeup? I'm not wearing makeup." I said weakly. I know I had removed the makeup just as Sheila had told me.

Sarah smiled "The long wearing lipsticks are so hard to get off completely. I always wear something to cover it."

I must have looked terrified "Calm down I don't think anyone would know if they didn't know you well. It's very faint but when you came in the door the light was just right. Your lips are just a little fuller and redder than normal. So what gives?"

A little relieved I decided to fill her in on the changes I had been going through. "Do you know the shop Timeless Fashions?"

She nodded and I went on "Well Darren and I were invited to a Halloween party at his office. We decided it would be fun to go as Sandy and Danny from Grease. I stopped in thinking I could find something fun there."

Sarah nodded smiling. "Did you find something?"

"Oh yes! Sheila fixed me all up. She insisted I look the part and she had me come in yesterday. We spent a few hours together and I was shocked at how much fun it was and how good I looked when we were done. Sheila insisted I could go out and do some grocery shopping without changing clothes."

"So you actually put some effort into looking good this time?" Said Sarah.

I had gone to a office costume party as a cheerleader once. The girls all told me how I should try to look good and not just as a guy in drag. I was a little shocked by the reactions of my co-workers and had not tried it again.

"Yes, Sheila helped me so much. She pick me out a dress for the party then she helped me with a few outfits to practice in."

"So you have a dress for the party?"

"It is a yellow print dress with full skirts. I will have to wear petticoats under it!"

Sarah looked a little surprised by my enthusiasm. "Do you have this dress at home already?"

"No I have to have another fitting next week." I said smiling.

"What kind of outfits did she give you to practice in?"

I described the shirtwaist dress, and the sheath dress. I told her about the swing skirt and blouse outfit with the petticoats that was my favorite so far. I told her about the lingerie and foundation garments that made me feel so feminine. We talked for almost an hour until everyone else was hard at work. Sarah finally said we should get to work as well and sent me out to my computer.

All day I was self conscious of my lips and tried to keep a to my computer although I did not get much work done. I thought of the night before. I couldn't help getting excited. I kept seeing Darren's face when he had first seen me. I kept feeling his hands on my body and the unmistakable pressure of his hard cock on my hip.

Darren works until six every night. I usually get home, come up with a plan for dinner, and our evening before he comes through the door. That night I called for our favorite take out. I picked it up and a six-pack of our favorite beer and picked out a movie from the rental shop.

Darren arrived right on time I had the movie ready to go and a beer on the tray along with his dinner. He stopped just inside the door. He looked almost puzzled.

"Hey, how was work? Are you hungry?" I asked.

"Yes." He said flatly.

This got my attention he was always upbeat. I jumped up. "Is something wrong?"

"Well I was expecting a little more." He said. "Maybe I misunderstood yesterday but I know that you made an impression."

Suddenly I realized I had let him down. I was sitting in a comfortable t-shirt and baggy shorts.

"I am sorry! Oh!" I stuttered.

"No. No. Lets have dinner. What's the movie?" He smiled

We watched the movie and ate dinner. Darren said nothing about the impression I had made. We went to bed and I knew I had to make some gesture. I had sat at work thinking about him all day and he was lying on his side facing away from me. I knew he was not asleep. I slipped out of bed and went to the spare room. I had put the other things Sheila had sold me. I found the nightgown at the bottom of the lingerie bag.

It was pink rayon. I had not thought I needed a nightgown but Sheila insisted. I was learning she knew her business. The gown was gathered at the waist. It had lace net gathered at the bodice with pretty pink bows. It was modest but sexy and just what I needed. I stopped put on a dab of perfume and some lipstick, then I fluffed my hair free of its ponytail and slipped back into bed.

I ran my hand over his broad shoulder and down to his neck. I felt him stir then I pushed my body against him. He rolled onto his back and I felt his hands touching me. One hand sliding slowly over my neck pulled me to his lips. The other on my hip pulled my body onto his.

"Gerilynn your home." He whispered.

I knew what he needed. I slid my body down his, kissing his sensitive nipples. I could feel his cock growing under me. I continued down his body biting and kissing him, very slowly. Finally I reached his crotch.

His hands played in my hair pushing me down to his hard cock. I resisted, knowing he loves to be teased I mouthed his pubes. Running them through my lips and burying my nose in them as I licked the sensitive skin between his thighs and cock.

He pushed his cock against my cheek and I could feel the wetness at the tip. Still I took the time to take his hot balls into my mouth. My hands held his thighs open I only used my mouth the make him want me. I gently suck first one then the other hot testy into my mouth. I licked him everywhere but his hot ready cock.

He kept up a quiet monolog. "Oh yes. Gerilynn please. Oh that's hot. Take my cock please!"

I realized he was getting the message. He kept rubbing his feet and calves over my silky nightgown. I looked up at him. It may have been dark but I could see the light in his eyes looking at me. I took the tip of his cock and traced my lips with it. The wet pre cum slipping over my lips just made me want to take him into my mouth.

Once more I looked into his eyes as I took his cock into my mouth. His hands pulled me down over his cock. I felt it slide past my tongue and into my throat. I felt his sweet pubes on my face and I swallowed.

He moaned "Gerilynn I am coming!"

I pulled his cock out until just his head was in my lips and I felt splash after splash of hot sweet cum in my mouth. I could feel it on my lips trying to escape my mouth. I swallowed quickly. I licked him slowly like a long hot ice cream cone chasing the melting drips with my tongue. After too short a time he became too sensitive and pulled me up to kiss me.

"So Gerilynn were you working late?" He said.

"Darren, I was here all the time hiding in the closet." I whispered.

"Well, I think we will need to talk about some things in the morning." He said cuddling me.

Sarah again had the coffee going when I arrived at work the next day. She smiled saying. "Another long night?"

I again blushed and mumbled as I got my first cup of coffee and moved for my desk hoping she would not want to have another talk. I had a lot on my mind including that I had gushed about wearing a dress to my boss just yesterday. I logged in and sifted through emails and mulling over the last few days.

Around ten o'clock I was brought back to the office by Sam sitting on my desk.

She said. "What are you thinking about honey?"

That was when I realized everyone in the office was looking at me. I mumbled something about Darren and I.

"So we were thinking of going out to brunch how about it?" Jane speaks up. "Come on we are all going get your purse!"

I got my briefcase and followed the ladies out to Sarah's Range Rover. Jane sat next to me in the back seat.

"So what's going on with you and Darren?" Jane pushed me.

"Oh everything is fine. Really we are great." I glare at Jane.

"Well you may not want to talk honey. We are doing an intervention! You are going to come clean or we are going to go right to Darren." Sam pipes up.

Next thing I know we are in front of Timeless Fashions and Sheila is standing in the door. She waved us all in and I knew Sarah had told the girls. Sheila confirmed it when she pulled out the dress.

"I don't have my things. Is the dress ready?" I burst out.

Sarah laughs. "Like Sam said this is an intervention. You are going to tell us all and we are going to help you. I guessed yesterday but when I called Darren and Sheila today I knew. You want to be one of the girls! Sheila said the dress was ready for another fitting so while you ignored us we made all the arrangements."

The look on my face must have scared them because they all tried to comfort me. Sheila grabbed me by the arm and pulled me back to the changing room. There on the bench was the same robe and a choice of panties, stockings, shapers, girdles and things that looks like corsets.

"Get out of those clothes Geri and we can start." She said. "Don't you worry this will be fun."

I picked a pair of bubble gum pink panties with lace all over the front and around the legs. I found an open bottom all in one with garters. I wiggled into it and attached taupe stockings to the garters. In a white box I found breast forms. They were much nicer than the ones she had sold me before. I slipped them into the cups of the bra and pulled my chest up into the cups to add to the effect. I pulled on the robe and discovered some slippers with three-inch heels.

Feeling feminine and ready to face my co-workers I stepped out into the fitting room. The girls were all in various stages of undress or trying on outfits. I was shocked. I had never been out shopping with women before and was amazed at how they interacted.

Sheila noticed me standing quietly and came to me. She held my elbow and pulled me into the center of the room. Sarah was holding a waist nipper that laced up the back. It was peach colored satin. She handed it to Sheila who wrapped it around my waist. Sheila had me close the front busk. Then she had Sam hold my hands as she began tightening the laces.

Just as before I felt my body conforming to the shape of a slender shapely woman. I was giggling and flush when she was done. Sam supported me as I walked around the room catching my breath. I was feeling so many emotions I didn't know whether to laugh or cry.

Sheila had pulled the dress out and held it for me as I stepped into it. Once it was settled on my shoulders Jane zipped it up. It fit like another layer of skin from my waist to my now ample breasts. It hung limply from my hips to about my ankles. Sheila stood back looking critically telling me to turn and stop. Running her hands over the lines and seams of the bodice.

Then she told Jane to unzip me. I was deflated by the almost business way it was being done. The dress slid from my body and I stepped out of it.

Jane said. "Now its time for petticoats!"

I turned and she was holding a mass of lace and crinolines. She held open the satin waist and I gingerly stepped into it. It had an under slip of satin and a layer of crinolines. She tied it as Sam held open another layer. Both layers snugly fit my hips.

Now Sarah held my dress out. I did not see how I could get into it with the layers of petticoats around my waist. Then I realized she was holding it up so I could put it on over my head. The dress slid down my body and Sarah even helped settle it over the petticoats.

I was again zipped into my dress. The petticoats brought the hem of the dress to mid-calf. Looking in the mirror I could see it was longer than the petticoats. Sheila stood back and then pointed to a low platform.

"Stand right here." She patted the platform.

"Wait! Doesn't she need the right shoes?" Jane asked.

"Oh, yes I have them right here." Sheila reached for a shoebox.

She pulled out three inch yellow pumps. I slid them onto my feet and stepped up onto the platform. I wobbled a little and Jane steadied me. They all looked astonished as Sheila pinned the hem up. Slowly turning I finally caught sight of myself in the mirrors. Sheila threatened to stick me with a pin if I didn't listen but I was astonished. The petticoats made the dress.

Unfortunately in a very short time it was time to remove the dress. I again felt a little sad as I stepped out of the dress. That's when Sarah said "Now for some more everyday wear."

Sheila smiled as she hung my dress saying. "I have a few things picked out already I don't have any slacks though."

"Oh she won't need any for a while yet." Sarah said as she held up a suit. She turned to me and said. "This is the intervention part Gerilynn. I talked to Darren and he agreed that you, my dear, should now dress more appropriately for work and home."

I now realized how much the girls already knew. I also realized I didn't care and wanted nothing more than to spend time as a woman.

"I can't wait!"

Well we spent the better part of the day getting me into outfits. I found out I needed work clothes, dresses for home, dresses for nights and lingerie. When Sheila was finished with me we went to a department store and I had a make over and bought makeup. We had to stop at shoe stores, a few more modern ladies shops for dresses and lingerie. When we were done we stopped at a bar and grill for a late lunch.

I was overjoyed by my day and I wanted to celebrate. Sarah bought the first round of margaritas. Before I knew it I was telling the girls about what had happened the last two nights.

Jane was incredibly loud when she said. "He did it right there in the kitchen while you were fully dressed!"

I must have blushed deeply because Sarah spoke up. "Jane honey control yourself everyone here will thing Geri is a slut or something."

"I am no slut, but, I will tell you Darren really loves the June Cleaver look!" I said as I stood and spread my arms in my best impression of a model. I was wearing a blue practical suit. The skirt tapered to an end just below my knee. The jacket belted tightly around my waist and covered my white lacy blouse with a ribbon as a bow tie. I was wearing the all in one with the waist nipper and stockings. My shoes were practical 3-inch Cuban heels.

"Well he is going to love those baby dolls Sheila sold you. I don't think I have seen anything like that since I was a little girl." Sam said.

"Well I am jealous Gerilynn. You are going home to a man that really loves you!" Sarah said. "You had him so confused and excited at the same time. He didn't know what to say when I called."

"I would love to be a fly on the wall or better a camera in the closet tonight!" Sam laughed. "It is about time you came out girl. We have been waiting for this for quite a while."

"After the cheerleader incident I thought it was going to happen!' Jane laughed. "If you had called I would have loved to help you pull that off!"

"Yes I have been waiting to see you come out of that old suit and tie." Sarah said quietly.

I realized then how well I had fit into this office full of women. After lunch we went back to the office and Sarah sent us all home to our men. I was more than ready to see Darren. But it was only three. I had time to get ready and to rearrange my closet. I had only come home with four dresses, three skirts and four blouses. I had come home with petticoats and negligees. I also had the other outfits I had brought home earlier.

It only took a few minutes to settle the closet and the drawers. I moved all my boy clothes to the spare bedroom closet. Then I thought about dinner. I changed into a housedress. It was pleated in the front with a belt and tea length. Simple but feminine, it was very much a June Cleaver housewife dress.

Darren arrived home and I greeted him at the door with a rum and coke. I took his briefcase while I kissed him. The table was set and I went to serve dinner. He went to his seat at the table and as I put his dinner plate down I felt his hand slide across my butt. I sighed and slowly moved to my place.

I first felt his foot on my calf. I was a little startled but quickly started enjoying the feel of his sock covered foot exploring my leg. He ate slowly. I slipped my foot from my shoe and joined the game under the table.

That was when Ella Fitzgerald began a sultry Bewitched Bothered and Bewildered on the stereo. I looked him in the eye as she sang, "thank God, I can be over sexed again." I blushed and he smiled like I had never seen him smile. The look of lust, love, and wanting raced over his face. I looked down at my plate shyly trying to cover the same thoughts that had rushed through me.

He stood and came to my chair and placed his hands on it. I instinctively rose as he held my chair. I turned and looked directly in his eyes and put my arms around his neck and stood on my tiptoes and kissed him. His hands moved to my waist then my butt as he held me tightly to his chest. His hands roamed over me. He explored my new garments. His fingers found my flesh between the stocking tops and my girdle. He fingered my garters. His fingers traced the laces of my corset. He pushed my breasts up and kissed my flesh. That lit a fire in me.

I found his belt and quickly loosened his slacks. The fell to his ankles and I almost tore the buttons off his shirt trying to get it off of him. He was kissing my neck and ear as I pushed his shirt off his shoulders. The fabric of his shirt covered his buttoned cuffs and I decided to take him to the bedroom. I grabbed the fabric of his shirt and pulled it over his head then I pulled him towards the bedroom.

He stumbled over his slacks but quickly gained his feet. He followed me saying. "Well Miss Gerilynn you seem to have me at a disadvantage."

I pushed him backwards onto the bed. "Well you seem excited to see me." I said as I pulled his boxers down his legs. "Mm! You look good enough to eat. I am so hungry for you." I took his hard cock into my mouth. I got him wet and slick running my tongue all around his cock. I felt his hands in my hair. He gently pushed me onto it but I pulled free of him.

Gerilynn69
Gerilynn69
59 Followers
12