Babysitting

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Dressing up after the kids are asleep.
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It had been so long since I used to babysit for my sister and dress up in her things. That's where my obsession had started. Then as I got older I stopped babysitting for her. There was little chance for me to do any dressing at home and I pushed the idea to the back of my mind.

One night when my little sister was already babysitting for my older sister I got an emergency call when my sister's friend's sitter suddenly cancelled. Just turned 18 I was only going to study for a test anyway so I agreed. I had no idea where it was going to lead me.

As you guessed already I ended up using her things to dress in. The new part for me was discovering make up, nail polish and how different it felt to remove the hair from my body after I saw how horrible my legs looked while covered with hair. I also discovered how much longer it took to remove the evidence of what I was doing. Not that mattered to me really.

Still it was wonderful and so relaxing to spend an hour or two or three dressed as a girl. I was now on the list of my sister's friends as a possible babysitter and soon enough I was busy every weekend. My make up skills improved and I started to learn how to style my hair as it grew out more. I learned how to keep my now completely hairless body from raising eyebrows in the gym showers, I joined the swim team!

Everything was going along nicely. I got my time alone after the kids were in bed to become as feminine as I wanted and no one was the wiser. If any of the women who were a bit smaller than me noticed that their dresses were stretched they never mentioned it to me or my sister.

Then came that fateful day when Rob and Shelly had a fight. He stormed home leaving her with their friends. I wish he'd called first so I would have known I should change.

I was studying in the living room when I heard the back door open and close. I felt my stomach drop thru the floor, panicked trying to jump up and hide but it was useless. I merely managed to stand and take one step then fall flat on my face. Rob rushed in to see what had happened.

Confused at first he came over to help me up as he asked who I was and where the hell Kevin had disappeared to! He saw what he expected to for all of a minute before he took a good look at me while I struggled to tug the very short skirt I had on back down.

Blushing deeply I still tried to get away as he finally comprehended who I was. "Kevin? Ha ha ha ha. Is that you? Oh migawd it is. I don't believe it."

I blushed even deeper and turned to get away but he grabbed my arm and easily stopped me.

"What are you doing? I mean why? Why are you wearing Shelly's things? Not that Shelly looks as good in them anymore. You look great in them, but why are you wearing them?"

I just stared at the floor as I tried to think of something, anything that would explain my appearance. My mind was blank and I started to cry as I envisioned the embarrassment and humiliation I'd soon face as my secret became common knowledge. I managed to free my arm and turned to go get changed, my body visibly shaking as my tears streamed down my face. Rob pulled me into an hug and tried to calm me.

I found myself sort of melting against him and began to sob harder, my life was over, nothing could possibly make things better.

"There, there calm down. Relax! I promise I won't mention a word of this to anyone. You have my word. I didn't mean to scare you or make you feel weird or embarrassed. This is strictly between us, I won't even mention it to Shelly. OK?"

My sobbing didn't stop but it did slow. His words helped but I still felt like the other shoe was going to drop, hard. Rob lifted my chin and he chuckled again as he looked at my face with my make up smeared and streaked across my face. He looked at his watch then picked up the phone to call Shelly at the lounge they'd been at.

In a contrite voice he apologised to her for storming out and told her he'd gone home and sent me away before he came to his senses. He encouraged her to stay with their friends and have a good time. Putting the phone down he kissed my forehead.

"There we go. It will be a couple of hours at least before Shelly comes home. That gives us enough time for you to repair your make up, me to find out how great you look as a girl and us to talk a bit about things. Go on, go fix your face now."

I did as told wondering what he had in mind. I had to start from scratch after I washed my face, but I was walking down the hall within twenty minutes. I stared around the corner, nervous about walking out openly before him, even if he had seen me before. He looked up and smiled as he took a sip of his drink.

"Don't be shy now. Relax and come sit beside me."

I tottered over in his wife's highest heels and sat beside him. He squeezed my hand reassuringly and asked me how long I'd been 'borrowing' his wife's things. Since the first night I'd babysat for them. Did I want to be a girl? I didn't know, had never thought about it really. Mostly it just seemed to be something I did when alone and there were females clothes I could wear but otherwise I was happy enough with my life.

"Ok. I'm just curious is all. I was a bit startled when I saw what I thought was a strange girl here and no sign of you. I only laughed because I was so relieved to find out you hadn't deserted the kids!

You do look very feminine, very female dressed like that you know. As I mentioned you look better in that skirt and blouse then Shelly ever did. I mean that. You have great legs... um... do you have a female name you prefer, it just feels wrong to keep calling you Kevin. "

"Maureen, yes Maureen," I replied after giving it a bit of thought.

"Well it's nice to meet you Maureen. Now that I know you'll be watching the kids when Shelly and I go out I'll make sure to call before we head home so we don't surprise you again.

There is one more thing I'd like to know, that is if it doesn't seem to be too personal or private to you."

"What is that Rob?"

Now he blushed a bit and stammered slightly as he asked me what type of things I liked to wear under the skirt and blouse. It was my turn to blush again but I smiled as I did.

"To be honest I've found that I prefer a garter belt and nylons to pantyhose for some reason. I learned to buy and bring along my own nylons after I ruined a pair one time. Bikini panties work better for me as they cover and conceal things better and I bring them along too as I might accidently stain them. Bras I just use what I find there and stuff the cups."

"So you like to feel sexy under whatever you have on? I don't blame you I would too if I was so inclined."

The next hour we spent just talking calmly and aimlessly before he glanced at his watch again and suggested I change back to Kevin. I smiled and stood up, regretting even more than usual the fact that soon I wouldn't look the least bit feminine. Rob paid me for the babysitting and I left before Shelly got home.

Three weeks later I was babysitting for them again. Rob gave me a different look when I got there and mumbled something about the bottom drawer of his dresser when Shelly was out of the room. I wasn't able to satisfy my curiosity for an hour till the kids were in bed and asleep.

I found a medium brown bag with a note pinned to it.

"Maureen,

Please accept this gift and wear these things for me tonight. I'll be thinking of how lovely you look in them all night, just as I have for the last three days since I bought them for you, just as I haven't been able to get rid of the mental one I got when you told me what you were wearing under the skirt and blouse I saw you in.

Now please don't be offended or repulsed by my next request. As mentioned I have pictured you in my mind wearing them. There is a camera with some film in this drawer as well and I'd be very interested in seeing if you look as good or better than I have pictured you mentally."

Looking inside the bag quickly I found a hot pink bra, garter belt and panty set with seamed pink nylons. My heart skipped a beat as I stared at them and another as the idea of someone seeing me wearing them hit home. I'd never considered that before. Never thought it would happen and the idea excited me more than anything else ever had. I wondered if Rob had thought of that? I started reading again.

"If you close the closet mirrored doors you should be able to get the pictures. If you hold the camera in front of your face no one will know it's you. I would prefer that you didn't, your much too pretty, but understand if you do.

Please do this for me, the thoughts and pictures in my mind are driving me crazy."

I glanced at the already closed closet doors and smiled knowing I had to do this for both of us. Hurriedly I stripped off my male things, hid them out of sight and carefully, lovingly set out the new things across the bed. As I ran my fingers over the lacy bra I discovered that the cups were fully padded, I wouldn't need to find anything to fill them.

I found the camera and my hands started to tremble as I became more excited. I tried to focus the camera but my hands were shaking too much. Then I remembered seeing a tripod inside the closet and brought it out. There was a remote button there as well that I hadn't noticed before. The tripod held it steady enough to focus properly. Now I just had to do my face, nails and hair then pose.

I was ready to take the first shot when I thought about my face showing. I didn't really want that. Not that I cared now if Rob saw it but what if Shelly found these somehow? I sat down, wanting so much to leave Rob these pics but afraid of anyone else seeing them until I spied the veil from Shelly's harem girl Halloween costume from last year still hanging from her dresser mirror.

Wearing just the veil I tucked my cock back and hid it for the first shot. Panties with me standing, kneeling, from front and back followed. A few of me rolling my new nylons on, attaching them to the garter belt, slipping on her highest white stiletto's again from front and back. Finally the padded bra and I was so proud of the way it added the final curves and changed my form to one more completely feminine.

Wearing the veil already was it any wonder that I hunted for and found the rest of the harem girl costume? Sheer black nylon pants, sheer black nylon top leaving my midriff bare and a small cap completed it. I felt so wanton, so wicked and so naughty as I added a few pictures of me wearing it, my lingerie clearly visible, practically glowing, thru it.

I'd taken more time to dress than ever before but that didn't stop me from enjoying it all for an hour and a half before Rob called to let me know it was time to change back. I let him know that the camera had been used and heard him smile as he replied, tho he wasn't able to acknowledge it as Shelly was close by.

A week later Rob asked me over to help him move some stuff in the garage. When we took a break he looked around carefully and motioned me over. As we looked at the pictures I noticed how amateurish they looked mostly. Somewhat out of focus, Somewhat stiff and forced. I'd done my best and been proud of them till now.

Rob was happy with them. He was glad I'd used the veil and hidden my face. He blushed a bit as he said he'd shown some of them to some guys at work and to one or two of the guys I babysat for now. None had guessed it wasn't a young girl he'd managed to talk into it. He was just so proud and pleased of having them that he'd had to show someone. He hoped I wasn't mad or angry at him.

He'd saved the ones he'd shown to them for last and I admit they were the best of the lot. A couple in the harem girl costume, full lingerie, then just the garter belt, nylons and panties, and just panties from the rear. That hid the fact that I was so flat chest wise.

I wasn't angry, didn't feel betrayed or disappointed. I found it sort of exhilarating really. He hastily shoved the pics out of sight as Shelly came to see how we were doing.

A month later I received a lace royal blue set with a matching mid thigh nitie and belted robe. Again I took about twenty shots and again he showed selected shots to those who'd seen the previous ones. This time a couple of them had chipped in to buy me more new outfits with the hope that I'd let Rob, who was a good photographer, take them.

Rob had the idea of taking me to a motel, if I was willing. I was!

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5 Comments
SteelasexappealSteelasexappeal6 months ago

Love this story! Hoping you will continue the tale!!!

88girfriend88girfriendabout 2 years ago

This was a cute story. Please keep going and develop the relationship between Rob and Kevin.

AnonymousAnonymousover 2 years ago

The beginning when Rob and Shelly had the fight that inevitably got Kevin caught was my favorite part. I like crossdressing…. Makeup, nail polish, and even shaved legs, arms, face, head…. the works! The thought of being walked in on, caught by a neighbor as I dress in front of a window, whatever, drives me insane. I would absolutely die if I were in Kevin’s place. Blissfully and erotically! God. I’d love it!!! Great job. I LOVE this story.

cdCindy1cdCindy1over 5 years ago
please continue

I can't wait to read what happens next. I'm like Maureen -- I love crossdressing and I love pleasing and servicing well-hung married men. Please continue with the next few chapters. I cant' wait.

AnonymousAnonymousabout 6 years ago
My favorite

This is the best type of senerio but we need the husband and the baby sitter to progress into sex!!

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