This is a true story that happened to me in the early 80's. The names are changed to protect the innocent.
I was married at the time, out of work, was sitting in the apartment reading a magazine. It was two days before Halloween. There was a knock at the door, I answered it to find a friend of ours Greg. I invited him, he took a seat and we exchanged small talk. Greg asked "The Holiday Inn bar is having a costume party for Halloween. Do you and Lisa want to go with us?" I replied "I will have to ask Lisa but, I am sure we would." Greg said "What now that your home are you the housewife and she wears the pants in the family that you would have to ask?" I said " Ha ha funny. No just with her working long hours that would only be the polite thing to do." He said "Just funnin' you do get mad." We talked a little, then he had to leave. I said "Wait what are you going as?" He said "A woman track athlete and Sharon (his wife) will be my male track coach." I replied "Not sure what we will go as." Greg said "Go as a woman and your wife as the man like us." I said "Well I don't have anything to wear so will have to think on that." He said "Go by the salon today and talk to Sharon." I nodded and he left.
Sharon was the manager of a small salon, currently it was her and another girl Jill working in the place. I waited an hour after Greg left and drove to the Salon. My mind was racing as this would be the perfect opportunity to dress en femme. I had been a closet dresser for several years, no one knew. As I drove up to the Salon my heart was racing, my mind reeling, and my palms were sweaty. I had also been playing over the scenario as to how I would get Lisa to go along with this. Would she be mad, would she think it fun or would she not want to go.
I walked in the door of the Salon, Sharon was finishing up styling a client, Jill was sitting in her stylist chair. There was no one else around. We said our hello's and I picked up a magazine. The client paid and left, Sharon sat down in her chair. Sharon said "Greg says you and Lisa are going with us to the Halloween party." I said "Probably, just not sure what costume to pick." Sharon replied "Oh I thought Greg said you would go as a woman like him." I replied "Don't have anything to wear." Which was a lie as I had my secret stash. Sharon said "Go to a store and pick something." I said "Money is tight right now with me being out of work." Sharon replied "Well maybe we an think of something." She sat for what seemed an eternity but, was only a few minutes.
Sharon looked over at Jill. Jill is very attractive, short blonde hair, about 6' tall, not overweight but well built. Jill looked back at Sharon and said "What?". Sharon said to Jill "you two are about the same height and he doesn't weigh much more than you. You are single and have those come get flirty clothes." Jill looked at me for a bit, then looked back at Sharon, then back at me. Jill said to me "Be at my apartment first thing in the morning, I don't have any clients until afternoon." I looked incredulous. Could this be happening, was a woman going to help feminize me? I nodded my head yes, since my head was spinning and I couldn't talk. Sharon said "This is great. After you get fitted with the right clothes you can come to the Salon before the party and we will give you a makeover. Greg will be here getting one too." Again I nodded ok. I got my wits enough about me to say I better go and left. The girls were sitting there with big grins on their face.
I had supper waiting for Lisa after she got off work. She came in and said "Thank you dear for supper and thank you for doing the housework so well while you're home all the time." I said "It's the least I can do." I asked about her day, she said it was killer. We made small talk with me pondering how to broach the subject of Halloween. Finally I said "Greg came by and asked if we would go with he and Sharon to a Halloween party at the Holiday Inn bar." Lisa said "That would be fun. Do you mind if I go get a bath and head to bed? I am beat." I said "That's fine." She left for her bath and I cleaned up the kitchen. I finished my work and went to check on her. She was already asleep. Guess the costumes will have to wait till tomorrow.
I had Lisa's coffee ready in a go cup the next morning, along with breakfast. She was scurrying around getting ready for work. She walked into the kitchen, I handed her the coffee and she said "No time for breakfast, gotta run." She gave me a peck on the cheek and was out the door. I cleaned up the kitchen thinking when and how am I going to tell her about the costumes. I grabbed a quick shower, changed clothes and headed out the door.
On the drive over to Jill's my mind was in overdrive. When can I tell Lisa, should I even do this, I could just turn around and call it off. But I didn't the thrill of being dressed by a woman and going out in public was pushing me on.
I knocked on Jill's apartment door. She came to the door wearing a short black night gown. "Morning princess." Jill said. I was taken aback at princess. "Don't just stand there babe, come in we have a lot to do." I walked in and she said "follow me to my bedroom." Now I was nervous, a woman inviting me to her bedroom dressed in a short night gown who was intending on helping me get enfemme. We walked into the bedroom, there were 3 dresses hanging up, some shoes on the floor and lingerie on the bed. Lingerie! Was that hers or for me?
"Ok princess, take off those clothes." A lumped formed in my throat and I gave her a confused look. "Look, we don't have all day and I have seen naked men before. I need to see what I have to work with." I nodded ok and started undressing. I was standing before her in only my briefs. "Off with the briefs too. Those aren't feminine." I turned red and took off the briefs. My penis started to twitch and Jill grinned. "Relax honey, this will be fun. Now turn around." I turned around with her looking me up and down. "Ok babe, follow me to the bathroom." I followed trying to control my reaction to being naked in front of her. Jill turned on the shower and said "Get in." I got in the shower and immediately my penile reaction shriveled, she had it on cold water only. Jill laughed and said "Fixed that problem huh." She handed me a Lady Gillette razor and a can of shaving foam. "Shave all the hair off that body." Jill said. I gave her a questioning look, speech was still hard for me. "To be lady like you have to look lady like, hair is not lady like. You can turn the hot water on when I leave. Shave slow and close dear." She left the room and me to my task.
I had shaved all the hair off my body, legs, underarms and what little chest hair there was. I stepped out of the shower and started toweling off. Jill came back in and said "Not like that, pat yourself dry." I started patting dry. Somewhere in this process, she had me in a spell and I started obliging her directions. I started to wrap the towel around my waist, Jill reached out took the towel and handed me a bottle of Nair. "Your not quite done princess. Put this on all over your body, let it set 10 minutes then rinse off using a washcloth." I nodded ok and Jill walked out again. I put the Nair on, after a couple minutes it was burning. I didn't know if I could stand it. Jill called out "10 minutes are up rinse off then come back to the bedroom." I rinsed off the Nair, I couldn't believe the wonderful sensation of being silky smooth. Jill yelled out "Need you in here." I was enjoying the moment of soft smooth skin.
I came back to the bedroom with the towel around my waist. Jill reached out and took the towel off. Again my penis started twitching, Jill laughed and said "Someone is enjoying this isn't she." Isn't SHE! Uh. She grabbed a black thong off the bed and told me to step into it as she held it out. I steadied myself on her shoulders and stepped into the thong. She started pulling it up and came face to face with my penis. Jill grinned and said "Gotta fix that." She pulled something out of towel on the floor and then I felt the cold of a piece of ice hit my penis. I shriveled up and Jill said "That looks more like a lady's clit should." She pulled the thong up higher grabbed my package and pulled everything back, way back. Then pulled the thong up tight. I looked down at a flat crotch. Jill said "This is called a gaff, it belongs to a TV friend of mine who left it here." She has TV friends? Now my mind is racing and heart is thumping. This could be a good friendship.
She then held out a black lace corset that had underwire supports for the breasts. Jill had me step into it. She said "This is going to be a tight fit but, it will help give you the right shape." The corset actually gave my chest the look of little boobs. She produced some thigh high black hose, showed me how to roll them up and put them on my legs, then clipped the hose to the suspenders on the corset. Jill stood back to look, "Not bad she said, a little tape on the boobies and they will look real." She had me sit down at the chair to her makeup table. She had me take off the hose. She sat on the floor at my feet, took one foot and started giving me a pedicure. I was transfixed in time, I didn't want this to end. Jill painted each toe with a bright red polish. She stood up went to her closet and produced an auburn colored wig, it was shoulder length with soft curls. Jill positioned the wig on my head and fixed it in place. "Perfect" she said.
"Now for makeup." Jill applied a light face cream, then concealer, then a foundation. She explained to me what she was doing and using at a each step. Then blush, she then stopped and said "hmmm. Eyebrows." Before I knew she had tweezers and was painfully plucking away at my eyebrows. "Not much" she said "Just enough to create the illusion." She finished, thankfully, then started with mascara and eyeliner and eye shadow. Next the lips were outlined with a pencil and filled in with lipstick. She stood back and said "Perfect."
She had me put the hose back on, watching me closely. "Now princess, do we want a hooker like? Trashy? No, we want a high class call girl look." She took a dress off a hanger and instructed me to lift my arms. On went a little black dress, that fell just below mid thigh, it had a low plunging neckline and little straps. Jill stepped back and said "No, that's not it." She took down another dress, I took off the other. This next one was floor length, except there was a slit on the right side that came up to my upper thigh. The neck was a deep V which was trying to show off what little cleavage I had. "Hmmm." She said with a finger on her chin. She looked at the shoes on the floor and picked up a pair of strappy sandals, they had an ankle strap and a good 3 inch spike heel. Jill said "good thing our feet are about the same size." She had me sit down and placed a shoe on each foot. "Stand up princess." Jill said. I stood up, well I teetered up. She took my hand and helped me. She looked me over, "spin around princess." Jill said. I tried to spin, it was more of a totter. Jill laughed and said "We will work on the walk." "This is it. It's perfect." I asked Jill "Can I see?" She replied "Just a minute." Jill got a gold necklace and found some clip on earrings and a couple of bracelets. She fussed with the wig then said "Ok let me close the bedroom door, there is a full length mirror on the back." She closed the door, I looked in the mirror and got light headed. I couldn't believe it, I had never looked this good when I dressed myself. Jill laughed and said "Princess you like this don't know." I just dumbly nodded yes as a little tear started forming in each eye. Jill hugged me and said "It's ok babe, I won't tell that you are having such an emotional reaction."
Jill looked at the time and said "I hate to break up this party but, I am going to have to get ready." "Let's take off this dress and lingerie and pack them neatly." I started to softly cry, I didn't want it to end. Jill hugged me again and said "Don't worry princess I have a surprise for you." I took the clothes off, again standing naked in front of her. We packed the clothes. Jill went to her dresser and handed me a pink lace bra with matching panties. I looked at her, "Put these on princess, you have to practice for tomorrow." I put them on. She than handed me a pair of tan panty hose and told me to put those on. Jill went to her closet and produced a dark brown pleated skirt, a pull over sweater that was a dark orange and fuzzy. I put them on without being told to. She then pulled out a dark brown pair of pumps with a 2 inch which I slipped on.
Jill said "You can wear those today." "Stay here while I get ready, watch everything I do. When we leave follow me to the Salon so I can give you more instructions." I hugged Jill, softly sobbing a happy cry and said "Thank You so much!" Jill said "I think we have released a princess that has been hidden and that makes me happy."
Jill got ready to go the Salon. Me I watched every move. How she put on her make up and clothes, the motions she made, how she walked and talked. We hugged again and stepped out the door of her apartment. I froze. Jill looked at me and said "What's wrong sweetie?" I said "I can't go out like this." She softly smiled and said "You look gorgeous princess, just take little steps, mimic my movements. Think you are a woman." She took my hand and we walked to my car. She said "Remember you are a lady, swing your legs and think and be feminine." I nodded and got into my car. I waited for her to get into her call then followed her to the Salon.