This is a true story that happened several years ago and changed my life. You see, I have been crossdressing for years, since my teens. I started in the usual way, with mom's nylons and lingerie. Eventually I got the nerve to start buying my own clothes, especially pantyhose...my favorite. After a while I had quite the collection of dresses and shoes, bras and panties. I would wear my things around the house, and as an only child my house was very often empty. My parents passed away in an accident when I was 22, and left me a decent sized inheritance. This allowed me to buy a nice condo and only work when I wanted, always taking summers off. I continued to dress in private, but always wore hose under my clothes and kept my legs shaved. Now let me begin my story.
When I was around 25 or so I used to hang around a friend's house, Dan. We would listen to music, maybe smoke a little pot and watch movies. He was a very generous person and whenever he had to eat dinner or go do an errand, he would tell me to relax until he returned. This is where the fun began.
In the back room of the basement his mom had all sorts of clothes hanging on the pipes. Nurses uniforms (she used to be a nurse), and other dresses and undergarments. Mrs. Davis was a rather attractive widow in her early fifties and always dressed smartly. In the bathroom was an old dresser that was full of pantyhose, Sheer Energy.... my brand...there was a drawer full of bras and panties, too. I was in heaven. If time allowed, I would pull on a pair of nylons and maybe a dress and take care of myself.
One night, Dan said he had to go out for an hour or so, and did I want to wait. Of course I said okay. I waited a few minutes and went to work. I started with a pair of lace cotton panties and matching bra. Next a pair of Sheer Energy suntan pantyhose. I pulled out a little black dress, with three-quarter sleeves and a high collar neckline. Then I pulled the rubberband out of my ponytail and shook my hair loose. It was then that I saw a basket full of her shoes...I couldn't believe my eyes. There was a pair of black pumps with an ankle strap, and like her dresses, they were my size. Size eight dress, size nine shoe. I sat on a box as I strapped the shoes on, first one, then as I was putting on the second, it happened.
"Aha...So it was you!"
It was Mrs. Davis.
"I knew someone was moving my clothes around, I thought it was my son. What the heck are you doing?" she demanded.
I was petrified. I had no idea anyone was there as she came out of the laundry room.
"I...I'm sorry Mrs. Davis, I just like to wear these clothes that's all.... It really doesn't mean anything" was all I could respond.
She looked me up and down and said "Are you gay?...are you and my son gay?"
"Oh no", I shot back, "it's not like that at all...Dan doesn't know at all. No one knows I do this...except you, now"
She just stood there for a second with her hand on her chin, looking me over. "I've heard of men who like to do this
But I don't see why. Can you explain it to me?"
"I have been wearing women's clothes for years, ma'am. I just like the fit and feel of these things" I just lowered my head in shame. Then I started to tear at the dress.
"Hold on a minute", she said "I must say you look rather good in that dress...like it was made for you. And your legs, they look so nice in those nylons. I guess you have had practice doing this"
"Mrs. Davis, please don't tell Dan. Please don't tell anyone, I beg you!" I was pleading at this point.
She didn't say a word for almost a minute.
"I have and idea, Paul. I won't say a word to a soul if you agree on one condition."
"Anything...I promise"
"Okay", she began, "You come back here Monday and work for me this summer. You know my son is going to Spain for the summer, and I really need the help."
I thought this might not be too bad. She runs a design company out of her home office.
"I guess that would be alright, ma'am."
"Good. It will be nice to have another girl in the house for a while. I never had a daughter and it gets rather lonely here by myself" she replied.
"Another girl?" I asked.
"Of course, Paul. I can help you dress up and show you things about hair and makeup. I think it will be fun."
I was stunned. There seemed to be no other way.
"Alright. I'll do it. When do I come back?"
"On Monday, bright and early. Now take off my clothes and be careful with those nylons."
She walked upstairs and left me in shocked silence.
All weekend I though about my dilemma. If I didn't show up, what would she do?. If I did, what would she do?
I thought long and hard about it and decided to give it my best shot.
On Monday morning I shaved my legs and arms. I painted my toes pink and put on a new pair of taupe pantyhose.
I wore my regular clothes and drove over. I was breathing heavily as I knocked on the door.
"Good morning, Paul, so glad you showed up, come in" She was acting in an unusually friendly manner.
She was dressed nicely, in a beige dress with a sweater and nice high heels. She motioned me to sit on the couch.
"Paul, I have thought a lot about today and I have several ideas for you. I would like to help you with a new hairstyle and makeup, and then pick out an outfit for you to wear today, okay?"
"I guess so" was all I could answer, though not very convincingly.
Once upstairs, we went into her room.
"Slip off those clothes and put this on", she said, throwing me a robe. I did as I was told.
"And you wore nylons, how sweet! I'm serious; your legs are beautiful, Paul. Wait a minute. I f we are to do this,
I think I should call you by a real name, like Sue.... How's that Sue?"
"Very good, Mrs. Davis" I answered.
"Now, now Sue. My name is Ruth. Please, If we are going to be friends, call me Ruth"
"Fine...Ruth...what now?" I said
"We'll start with your hair. It's so long and nice but you need a trim and a little color"
She began to comb out my hair, which was about four inches past my shoulders. Next she cut bangs just above my eyebrows and shaped the ends to just at shoulder level. She brushed in some light auburn color and wrapped me in a towel.
"That will take twenty minutes, Sue, time enough for makeup" I could tell she was enjoying this.
She applied liquid to my skin, shadow to my eyes and brushed out my lashes. With a pencil she did some liner, too.
For lipstick she outlined my lips with a brush and filled in with a crimson color. Next she asked me about my fingernails. "Let's put these on...they will look great" She had a set of false nails which she glued into place and painted a similar pink as my toes.
"You look so nice, my dear lets finish your hair"
The towel was removed from my head and she began to blow dry my hair. It looked different already. It seemed so full and lighter in color. As she brushed it, she asked me many questions about my life, especially my love life.
I answered her but was really mesmerized by the look she was creating.
She took some hair from the top of my head and pulled it back, fastening it with a clip. Then she curled the bottom upward with a curling iron. It looked really nice.
"Lets get you dressed" she said. "With that shade of nylon, I suggest a gray suit. I have just the thing"
Out of her closet she pulled a two piece suit and a cream colored blouse.
"These should fit nicely, Sue. Careful with your makeup when you put the blouse on."
She was right. The suit fit snugly, with the skirt rising above my knees a few inches.
For shoe she picked a pair of plain gray pumps, with a two and a half inch heel.
"Stand up, dear and let me look at you. You are so sweet, Sue. I hope you enjoy this as much as I do, it's like dressing up a doll for me. Now I have to ask you something personal, dear"
"Yes, Ruth, anything" I was in heaven now. I could not believe the way I looked.
"Sue, I know you aren't gay, at least now. Would you consider me attractive? I haven't been with a man for years, but I've got to tell you, I would love to have you kiss me right now" She uttered these words so sexily.
"Oh yes. Ruth. I think you are a very attractive woman. Please let me kiss you" I don't know where these words were coming from.
We sat on the bed and she leaned into me. She kissed me softly, a passionate kiss. Her face was hot as fire, and the kiss became more intense. She had the lust of a horny teenager. Her hands were stroking my legs and I could tell where this was going.
"Make love to me, Sue. Right now" she cooed in a whisper.
She rolled me over on the bed and climbed on top. This woman was alive with lust, tearing at the skirt I was wearing. I attempted to remove the skirt, the pantyhose.
"Stop, Sue, let me do this" She was in control now, so I went along for the ride.
She raised the skirt and slightly rolled down my nylons. I have never had a harder, larger erection than then. She raised her dress and then I noticed she had stockings on, but no panties. She knew all along what she was doing.
Her passion had her soaking wet, and she slid on to me slowly. I think she came instantly. I was determined to last as long as possible convinced that I was dreaming. She reached back and caressed my thighs, scratching at my nylons. Once again she shivered in orgasm. I drove upward into her as hard as possible, while she felt my legs and began to bite my neck. After twenty or so minutes I knew I couldn't go much longer, but she kept after it. Finally as she came once more, she told me it was my time. I held her stocking covered legs as I pushed up, again and again, until I came in an explosion that started her to cry softly. She showered me with kisses, me tasting her lipstick with every one.
"Oh, my God Sue, that was incredible. I knew it would be. Thank you...Thank you" She was crying now.
"Don't thank me, Ruth. I loved it too"
"You know, Sue, you don't have to come back if you don't want to. I won't tell anyone our secret" she said and kissed me one more time.
"Oh...I want to if its okay with you!" I was almost begging. This was too special to let go.
"Well...we could get your ears pierced and maybe go shopping once in a while, is that alright, girlfriend?"
Girlfriend. I felt so wanted at that moment.
"Ruth, we are going to have some fun this summer" I answered with a smile.
And did we ever!
Part 2 someday!