This is the continuation of my first story, "Friend's Mom". Thanks to all for the nice comments and requests to continue.
After my day with Mrs. Wilson, I was dizzy with delight. I finally had someone to share my secret with, someone who also was interested in helping me become who I am today. Sue was born that day, and a whole new world of dressing in my favorite clothes had begun.
Ruth was so kind that day, after we made love, she helped me dress again after we showered. She let me wear her prettiest dress,
A black silky number that felt so nice I almost came when I put it on. She set and curled my hair and redid my makeup too.
"I must say you look adorable!" she said. And I did actually!. My hair was down and curled, my legs wrapped in shiny tan pantyhose, my shoes sexy but comfortable.
"What now?" was all I could ask. We talked for a long time about how I was going to work in her home office that summer,
so why didn't I just stay there too. "I really have to go slow, Ruth, this is all so sudden"
"Sue, my dear, you can either go home dressed like you are now, you can change if you'd like or Ill take you anywhere you want to go."
I decided to try passing in public for the first time. Something I'd just dreamed about.
"I'd like to go back to my place & pick up a few things, and stay here for a while if that's okay" I asked shyly.
She was so excited. "That would be divine my dear!" she smiled as she said. "But let's change your outfit, you are far too dressed to go out in the daytime like that"
With that I was led again to her bedroom and asked what I wanted to wear. This was heaven!. I picked out a skirt and sweater, and she suggested some wedgie type sandals to go with them. Here I was now, a cute girl. Dressed in her friend's mom clothes, and just so happy I could burst.
We went to my condo, with my eyes darting back and forth constantly, and Ruth just giddy about my nervousness.
Once inside, I realized that no one even looked twice at the mother and daughter we appeared to be.
She marveled at the amount of female clothing I had amassed, and my taste in clothing was mentioned more than once.
"Lets get you packed Sue" she said as we went through my dresser and closet, picking out panties, nylons, bras and various other items. From my closet I picked out several dresses and some skirts and put them in my case.
Once again she just beamed, "My little darling is so pretty, and she has the cutest clothes too! I know we are going to have a ball this summer and I cant wait to get started!"
Yes, it was all like a dream, but I swear it was real. She led me to a spare room at her place and I soon settled in.
I knew I would not live fulltime as a woman, at least not yet, so I did bring some guy clothes too. But I was feeling so brave that all I wanted to do was to go out and just yell out loud how excited I was. That night Ruth told me she had to visit a sick friend so
She would be gone for several hours. "Come along if you like, but I understand if you don't". she kindly asked.
"No, I'll stay here and I do have to go out for a bit myself to pick up a few things for my stay"
"Fine dear, just be careful" Mrs. Wilson was acting just like my mother!. But I loved it.
So an hour later, there I was in a pair of jeans and a t-shirt, hair in a ponytail and a baseball cap, ready to go out to the local department store for several things. As I drove I still was dizzy with excitement. I finally had the chance to dress and be who I wanted, what made me so comfortable. Once at the store I started my errand, but ended up looking at a pretty dress that was on sale. It was light blue with a faint flower pattern and looked so pretty I had to have it. So once at the counter, I began to take the items from my cart, a new toothbrush, deoderant, just regular things. Then I put some pantyhose, my dress and hair spray on the counter. The sales girl was a cute thirty year old or so, and she smiled at me and said, "I hope this is your size!" as she held up the dress.
With my newfound bravery I just smiled and replied, "It certainly is, size 8 and I have just the shoes to match"
She looked stunned. "Are you serious?" she asked in a puzzled way. "Why yes I am, why are you so surprised?" I said.
"I've heard about guys like you , but I just don't believe you. I'd like to see that!" She had thrown down the challenge.
"Tell you what, how long are you going to be here. I'll go home and change and meet you back here". Now let's see who's surprised.
"If you are serious, I get off work in 2 hours and I'd love to see you in that dress!"
"Then I'll be back in two hours, it's a date" I answered back. Now I was so excited I was almost shaking.
Back at Ruth's house I stripped and showered. I wanted to look so pretty I really took my time, shaving my entire body, applying lotion, spraying on some scented after shower perfume. First I slipped on a pair of light blue lacey cotton panties. Next the matching bra and my falsies, 34b because I'm not that big anyway. I chose a light pink polish and did my toes and fingers. Very nice. Opening a fresh pair of my Sheer Energy pantyhose always get me going and I soon slowly slid them up my legs, making sure they were snug and just so. I need a slip and didn't have one, thanks Ruth! As I borrowed a little white slip from her room. The dress was a perfect fit too as it dropped over my shoulders, lightly brushing my slip and stockings. I sat at the makeup table and did my best . First some foundation, powder and started on my eyes. Liner and mascara and just a little shadow. I used the curling iron on my hair and did it like Ruth had done earlier that day. All I needed was a little jewelry and a purse and I was ready. She had a little bracelet and earrings that were gold and so dainty but perfect for me. Finally I had some shoes I had brought from my place that were perfect for my outfit. Two and a half inch heel and camel colored strap pumps.
Now I was ready. I entered the store and looked around hesitantly, again realizing that nobody even paid attention to me.
Then I saw her. As I walked toward her she looked at me first, then her hand went to her mouth and she just whispered,"Oh my God!". So I just smiled and calmly said,"Can you show me where to find the shocked salesgirl", and she started to laugh.
"I cat believe it, you're so pretty in that dress! Turn around and let me see. Look at those legs...why...how...oh my!"
All she could do was murmur and her eyes were popping out.
"Would you care to go out for coffee or something?" just came out of my mouth, I don't know why.
"Well, uh, sure...wait out front for me" she replied.
While waiting in my car I once again wondered how and why this was all happening. I guess it was meant to be.
We drove to a nearby little restaurant and ordered coffee and a piece of pie.
"I'm absolutely floored by this, I mean I cant imagine why you would do this but you look so pretty I guess its natural for you.
You seem so comfortable and I have so many questions..."she was now looking at me like a sad puppy.
I started at the beginning and explained everything about my love of women's clothing, my long hair and nails, my pierced ears.
How I wanted to dress and look like a woman but actually didn't want to be a woman. Very confusing, I agree.
We eventually got to discussing sex. She was now very interested in how I dressed when I was having sex, which role I like to play. "Wouldn't you like to know"I coyly answered.
"Actually...I would", she said with lowered eyes.
So twice within 48 hours here I was, at a woman's home, about to make love while dressed in my pretty things.
We sat on the couch and she scooted closer...she began to touch my leg as we kissed...she felt my breasts...smelled my hair...lifted my dress to see...
I was so hard now, she felt me through my nylons. Her tongue in my mouth, she pulled off her blouse and directed my mouth to her nipples. They were harder than I was as I sucked and sucked. I went to take my dress off and she asked me to leave it on. She got under me and worked my dick out of my panties, pulling me to her, pulling me by the top of my pantyhose. Now she was on fire , sucking and pulling me toward her, guiding my into her soaking pussy, grabbing my hair as we rammed into each other.
This was a total fantasy come to life. We came together in a huge buzz of lust before we calmed down to more kissing and sucking.
I don't know how much more I can take. I never though being a woman was so hard!
Some other time I'll relate more of my crazy stories, all in the name of just trying to look pretty!