I had recently moved in with my Mother-In-Law (she is 70 and I am 50) due to financial pressures and, the wife had taken a job in another State. We got along very well, I would help her around the house, with cooking and cleaning. She thought it would be fun to teach me to sew and the lessons were going well.
My background, for as long as I can remember I was in touch with my feminine side. There was an old photo of me about age 2 wearing one of my Mom's petticoats with powder on my face. I had gotten into her things. I can remember playing house with the neighborhood girls, we would take turns playing mommy, daddy or, little sister. Which meant I got to dress for mommy role or sister role often as I would volunteer.
Back to the present.
One day it was cold and snowy, I had been out shoveling off the walk and came in cold and wet. My Mother-In-Law advised me to get out of the wet clothes and take a hot shower. I took a shower and when getting out she was standing outside the closed bathroom door telling me supper was ready. I said I needed some dry clothes, she said just put on my robe hanging on the hook. There was a large fluffy pink robe with little off yellow flowers embroidered on it on the hook. I put it on, came out of the bathroom and headed to the kitchen. She remarked that my barefeet might get cold, left the kitchen and returned with a pair of fluffy pink house slippers. I was in heaven.
After supper we were sitting around the fire when she remarked some hot chocolate would be nice. I said I would fix it. I returned with the chocolate and sat down and started working on a crochet scarf I was making. She was doing some embroidery work. I offhandedly, without thinking, remarked look at us a couple of old maids. She looked up and smiled and said well if you are an old maid you need to work on yourself. I grinned back and asked how so. She said you haven't shaved those legs and you need a pedicure. I wasn't sure how to respond to that and just blankly stared at her. She said well scoot back in the shower, you can use my razor. This was now getting interesting and, I wasn't quite sure if she was serious. She then said what are you waiting for, get going.
I got back in the shower, found her shaving gel and razor and shaved myself smooth. It was a wonderful feeling. I got off and toweled off. I could here her moving around in her bedroom as she had her own separate bathroom. She called from outside the door, told me there was some body spritz on the counter and I should use it. I spritzed myself all over when the door partially opened. She put her hand in and was holding a pink knee length silk nightgown with matching panties. She said you need these too. I couldn't believed this was really happening. I didn't said a word not wanting to spoil the moment and in fear she would stop. I put the panties and night gown on then the robe and fluffy slippers and stepped out.
She looked at me and said not bad, come sit at my vanity. I walked over and sat down. She proceeded to put a wig on my head, then said let's fix those eyebrows. She plucked happily away at my eyebrows with me wincing. She then scrubbed my face and put on a light coat of makeup. She stepped back to look at her work and said almost there, don't move. She left the room and returned with a needle and some ice. She put the ice on my earlobe for a bit, then jabbed the lobe with the needle and pushed in an earring, then followed suit with the other ear. She sat in a chair next to me, took my hands and applied fake nails and red nail polish. She than lifted a foot up and painted my toenails the same red.
After the nails dried we returned to the living room, sat down by the fire where she started working on her embroidery. She looked up and said I am so happy to have another old maid with me rather than a man. I had tears in my eyes, she said oh dear you are happy too. I was. Later, we headed off for our separate bedrooms, I fell asleep content in my nightie and panties.
I woke up the next morning, got up to dress and realized my clothes were gone. I went to the kitchen, she gave me a peck on the cheek and said good morning Clara. I looked at her confused, she said her best friend in school was named Clara and since we were best friends thought that fit me. I asked her about my clothes, she said my dear two old maids live here now. You can borrow something of mine till we shop for you.
We finished breakfast and she led me to her room, sat me down at the vanity and applied my makeup. She went to her closet and picked out a gray below the knee skirt, a pink blouse with lace at the neck and wrists, and a pair of black two inch heel pumps. She went to her dresser pulled out a girdle with garter straps, a black lace padded bra, black lace panties and, black hose. She said put these on, I stood there waiting for her to leave or turn around. Sensing my modesty, she said don't worry this is just us girls. I took the robe and night gown off, then blushingly pulled off the panties. I slipped into the new panties and tucked myself back. She laughed at that, said wait a minute and returned with a Kotex pad. She showed me how to put it in the panties, then I readjusted everything. I finished with the undergarments and my mind was numb and giddy, it all felt so good and right. She handed me two breast forms for the bra to complete the 36c look. Next came the blouse, skirt and shoes.
I felt so good, she asked me to walk for her. I did and she instructed me in holding my arms, moving my hips and in taking smaller steps. We walked back to the living room, she handed me a purse and a soft gray coat. She said ok Clara let's go shopping. I stopped in my tracks and said in public. She said you ninny, you look fine. I looked in mirror at a mature woman with slightly gray hair and sighed. She took my hand and walked me out to the car.
The first stop was Dress Barn, she looked the dresses over, picked out a couple and led me to the dressing room. She said try these in, when you have one on let me know so I can look, I will be looking at more things. I tried on one dress, it was dark blue with little polka dots and came mid calf. I opened the curtain and called for her, Joyce. She said I am over here by the pantsuits, come here and let me see. I was nervous with a half dozen women in the store. I gingerly walked over and found her, she had me twirl for her then said yes that is perfect. We were there for an hour with me trying on dresses, skirts, blouses and pantsuits. She picked out three dresses, including the polka dot, three skirts, three blouses, and two pantsuits.
Next stop was a lingerie shop for older women. I hesitated but, she took my hand and led me in. She picked out some bras, panties, hose, girdles and corset and hand me try them on. She bought me a pink bra and panty set, a light blue set, a white set and a black set with red roses on them. Also came several pair of hose, thigh highs and panty hose all in different colors. Then we headed for a shoe store, I felt awkward having a man handle my hose clad feet trying on different shoes. She was grinning the whole time. We then headed to a jewelry store where she picked out rings, earrings, bracelets and necklaces for me. When we left she announced it was time for lunch.
We went to a small local restaurant, walked in and I noticed other ladies here age seated at a large round table. The ladies called her over. I gulped, she took my hand and walked us over. Slowly she introduced her friends to me and told them I was her old school friend Clara. The ladies all hugged me, gave me a kiss on the cheek. I could not believe they did not notice I was a man. We sat down, they were hitting me with questions about where I was from, had I ever been married, did I have kids etc. Clara did most of the talking, interrupting them so I never had to answer. We had a light lunch, talked about sewing and they about how nasty there men were. We left with hugs and kisses all around and headed home.
Joyce then laid out her plans for me. How we would attend and have tea parties, attend sewing circles. I finally broke down in tears, thanking Joyce for all she had done and how I was happy with this. I then asked her how we could pull this off with my wife. She said not to worry as she found another man when she moved out of State and then told me she knew about my dressing as she had found some of her clothes out of place and knew it had to be me trying them on. I cried some more with her hugging me. She then told me there would be more to this transition, that I was to let my own hair grow out and we would get it styled at a salon. Then she announced we would be seeing her gynecologist tomorrow to get me started on hormones and a breast enhancement. I could not believe this was happening.
We went to bed that night, in the same bed, me in a powder blue, lace nighty with matching lace panties. We lay next to each other and had girl talk till we fell asleep. In the morning we work up, dressed for the day, I in the polka dot dress. She said today we need to work on your girl skills, as an older mature woman. She said we would be going to a seniors dance that night. All day we worked on talking, walking, sitting, grace and manners. We went to get ready for the dance. Hanging up for me was a beautiful floor length dark blue evening gown with matching blue strap two inch heel sandals. We changed into our evening attire. I remarked over and over how nervous I was and asked what if someone asks to dance with me. She put on some music and taught me how to dance with the man leading. She then said, don't get any ideas on picking up a man as you are mine.
We arrived at the dance there were 100 people there, the music was from the 40's. We sat a table with three of her friends, who were all remarking how gorgeous I was and that I better watch out for all the widowers. I just giggled and blushed and said not to worry. Joyce and I danced to a couple of songs, which was not out of place because many of the older ladies were dancing together. A slow song started when a distinguished older man took my hand and asked me to dance, I looked at Joyce, she nodded approvingly. He took me in his arms and the room went dim, it was pure bliss. He held one of my hands with the other placed on the lower part of my back. As we danced I sensed he was pulling me in closer till soon my head was resting on his shoulder and I could feel his hand had slipped farther down till it was on the upper part of my ass. The song ended but, I stayed in his embrace. I finally, gently pulled back and softly said I should join the others. We moved back to the table, they were gone. I found them on the dance floor with other men. My suitor put his hand around my waist pulled me close and kissed my cheek, I melted and sighed. We sat down at the table to wait for the others. He had one hand on my knee, which kept sliding up till it was on my thigh. The others came back and sat down. Joyce looked at me, grinned and winked. My suitor kept himself up close to me and bought drinks for the table. The last song started, he stood up, took my hand and led me to the floor. This time he pulled me close, my head on his shoulder and we slowly swayed. I became startled when I could feel his manhood grow and was pressing against my belly. But he had a firm gently hold on me. The song ended, he took a hand and lifted my chin toward him, I looked into his eyes and he kissed me, sweetly, gently on the lips. My body went limp, my mind was reeling. I whispered I had to get back to my friends. He put his arm around me held me close and walked us back to the table. Joyce was smiling and said well dear, we have had enough excitement for the night for two old ladies. I nodded, she took my hand and we started walking out. My suitor took hold of my other hand and walked out with us. We got to the car, he opened my car down, as I started to get in he kissed me again. Then asked me out. I looked at Joyce, she spoke up and gave my suitor her number and told him to call.
We got home, changed into nighties and bathrobes and had tea before bed. She said it is too late tonight to discuss men but, we will tomorrow. We climbed into bed, she snuggled up close to me, I laid my head on her breast and drifted off to sleep dreaming of dancing and kisses.
The next morning she suggested I put on the pant suit as I had a doctor appointment. We arrived at her gynecologist, a nurse took me back to an exam room, told me to undress and put on this flimsy paper thing and get on the table. I did so. The doctor came in, talked to me, telling me he and Joyce had already discussed my case. He pulled the top part of the paper thing down, took some measurements and pictures then pulled it back up. He then put my feet into the stirrups on the table, pulled them apart and lifted the paper thing again. He examined my ass and manhood. He then told me to get up and start getting dressed and he would be right back. He returned with a shot and pill bottles, he gave me the shot in my ass. Then told me to take two pills a day, one morning and one night. We left the doctors office and headed for the ladies lunch circle.
The ladies were all giggling and talking about me and my suitor at the dance. One of the ladies then remarked, by the way Joyce has told us all about you. We think it is wonderful you being an older woman as most men are gross. We continued the lunch with talk of sewing and flowers and fashion.
At home Joyce told me, we needed to talk about men. She told me not to get involved in an ongoing relationship as men would only disappointment. That it was ok for me to have a couple of dates to experience what every woman goes through but, to remember I was hers and only hers. I told her I would follow her advise and to remember I was only hers. We had supper, sewed and then headed for bed. Tonight would be different.
I had on a white lace nightie with matching panties, Joyce had went into the bathroom and came out with nothing on. I pretended not to notice and climbed into bed, she got into bed next to me. She then put an arm around me, pulled me close and kissed me. She said we are old maids but, I still have needs. I wasn't sure what to do. She guided me head to her breasts I started kissing and sucking on them, she was moaning. She then guided my hand between her legs and using her hand had me rubbing her. Soon she was pushing my head down to between her legs and told me to pleasure her. I began pleasuring her with her giving me instructions on what she wanted. She let out a moan and gasp and said OOOOOOO I am cumming. Then she pulled my head away, told me to freshen up my face. I came back she was in a long flannel nightgown, kissed me and said good night dear Clara.