Sarah Helps Clean Out a Garage

Story Info
Sarah helps a friend and ends-up going out dressed.
2.4k words
4.58
19k
5
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
SarahCD
SarahCD
402 Followers

A friend of mine, Sandy, asked me if I would come over next Saturday and help her clean-out her garage. I had known her for several years and her husband had just left her and so, when she asked me for help, I could hardly refuse. In addition, she is cute and I cannot imagine why her husband would leave her.

On Saturday, I went to her house. I only ever wear girls panties and girls jeans but, at a casual glance, I look like a guy. I thought that Sandy had no-idea about my crossdressing, it's not exactly a secret but I do not flaunt it either.

We set to work; it was quite a challenge. Sandy had a small dumpster in the driveway for us to throw-out stuff and an area allocated for donating. I think that her husband had taken what he wanted and then just dumped the rest of his stuff in the garage. Mostly old clothes and just plain junk but a few things were good enough to give to charity.

I carried out things to the driveway where Sandy separated them into three piles, throw, donate and keep. I transferred the throw stuff to the dumpster. Some things, tools, Christmas decorations, etc., I did not bring out, no point in taking them out only to have to put them back.

I swept out the garage and then put back the things to keep. She could now actually get her car into her garage. The dumpster was almost full and the 'donate things' easily fitted into her car trunk.

Sandy said that we should go and relax for a bit. She would make us dinner, after all we're done, we deserved it. She gave me a glass of white wine while she prepared dinner. She could see that I was dirty from the work and suggested that I take a shower while dinner was cooking. I felt grimy and I knew I needed a wash. She told me to put my dirty clothes outside the bathroom door; she would wash them for me and put some clean clothes in their place.

When I was getting undressed, I remembered what I had put on that morning. I am so used to wearing girls clothes, I often forget about it. Oh well, too late now. I put my t-shirt, girls jeans and panties in a pile outside the door. I had a nice hot shower; I certainly needed it. She knocked on the door, called out that she had my dirty clothes and the clean stuff was outside. Well, there had been no cries of outrage at what she had found and so it must be cool with her.

I dried off and then went to retrieve the clean stuff. I had expected something left over by her husband but what I found, instead, made my heart jump. She had left me a pair of very sissy panties, a knee-length pleated skirt and a t-shirt but even the t-shirt was clearly a girls. The neckline and pastel blue color was unmistakably girls. I loved it all. My cock started to stiffen as I dressed. Her panties did nothing to hide an erection.

When I re-entered the kitchen, I was sure that it was showing at the front of my skirt (well her skirt but I had it on). She smiled at me and said that I looked good. She definitely intended a double entendre. I was clean and brushed but I was also wearing her clothes. They did look good on me. I blushed a little and sat down at the table to hide my now very hard cock.

She came straight out and asked me how long I had been dressing as a girl. I explained about how I love being Sarah and how much I enjoyed wearing girls clothes whenever I can. I asked her what had made her suspect that I was a crossdresser. She said that there had been a number of little things over the years.

She said that for one thing, "You only ever ware girls jeans."

I said, "It's true but aren't all jeans the same."

To which she listed some off the differences:-

•The zipper only goes halfway down compared to mens

•The pockets are shallower

•The back pockets are often decorated with embroidery. I often wear a pair that actually has sequins on them

•Quite often, the seams use a colored cotton

•The look and style is distinctively girls.

Also, sometimes I had failed to completely remove my nail polish. I had left a trace of color under my cuticles. The same with my mascara, sometimes, a little still showed on my eyelashes. Oh and I wore white & pink trainers, carried a shoulder purse, my clothes were always bright colors and my hair was longish and blond. When she collected my dirty clothes and saw my panties there was no question left, I was a crossdresser. Just some of these clues would have given me away.

All I could do was to blush and admit that it was all true.

She seemed so comfortable with the idea; I suspected that she had encountered crossdressing before. Not her husband, I was sure, but maybe a past boyfriend.

She had me stand up and turn around. I had to lift up my skirt to show her my panties. Now, there was no doubt that I had an erection but she did not comment on it, she just smiled at me. She said that I was halfway a girl but I needed a few finishing touches. I could hardly concentrate on the food and wine. I was so excited just sitting there wearing girls clothes and thinking about what more she had in mind.

We both had a couple more glasses of wine. I was happy to open a second bottle to keep things going. It was wonderful sitting there as a girl. Finally, I said that I really had to go but she said, "No, you can stay in the spare room. You've had too much to drink to drive." I, of course, agreed. She said that she would find something for me to wear to bed.

Since I was staying, we had another glass of wine but tiredness finally caught up with us. We went upstairs to the bedrooms. She told me to hold-on a minute; while she went into her room and returned with a red baby-doll nightie. Well, I just smiled. She said, "We'll have fun tomorrow." I went to bed with a massive erection but decided to wait and see what would happen the following day. What did she have in mind for me?

Next morning, she woke me up with a cup of coffee. I sat up in bed feeling a little embarrassed. The night before, she had seen me dressed but several glasses of wine had loosened my inhibitions. Now it was broad daylight and I was wearing a red baby-doll nightie.

It got worse, well actually better, when she held out a bra for me. It matched the panties she had given me the night before. She told me to get dressed. I expected her to leave me to it but she just leaned back on the bed and smiled at me.

I had to get out of bed and take off the nightie. I was standing in front of her stake naked. She stared at my erection as it came to life. I'd always thought she was attractive but when her husband was around, I just kept it secret. I got dressed; I put on the bra she had brought for me, with the matching panties, a top and a red pleased skirt.

After breakfast, she grabbed my hand and dragged me up to her bedroom. She pushed me over to her dressing table and sat me down in-front of the mirror. She proceeded to do my make-up; I was told to watch her careful so that I could do it myself in the future. I liked the sound of 'in the future'.

She started with a light touch of foundation. Just enough to give me a smooth looking skin. Next came my eye shadow. She used a dark blue on the inner edges and moved to a lighter shade for the outer edges. She blurred the two shades together to give a nice smooth transition. Then came black eyeliner. Since it was daytime, she only did my upper eyelids. For mascara, she used a bodybuilding black.

She then showed me a trick that I still use today. For blush, she put a streak of lipstick on each cheek and then smoothed it in. I think it looks more natural than powder and it matches my lips. She did my lips and then a slightly darker lip liner on just the top lip.

When she was done with makeup, she did the best she could with my hair. It was shoulder length and blonde. She gave me bangs, brushed it over my ears, and curled it around my neck. I still use this style today. She had me stand up and do a twirl for her. Shoes were a problem; my feet were bigger than hers but she found a pair of flip-flops I could just about walk-in. A liberal spray of perfume and she was done.

She said, 'Come on, let's get going." I froze, where were we going? I often go out dressed but always alone. However, I was getting used to having her seeing me dressed. It was always fun to have complete strangers see me as a girl but someone I knew was a new experience for me. She hung a purse over my shoulder and pushed me towards the stairs.

She drove us to a local strip mall and parked outside a beautician. Inside, she introduced me as her friend, Sarah, and said that we needed to get our nails done. I had to go first. I sat in the chair while the manicurist held my hands and did my nails. Now, I just love the attention but the first time was intoxicating. I remember sitting there with my fingers in a bowl of warm water while other customers came by me and just nodded. She did my nails in a red to match my lips. While my nails were hardening under the ultraviolet light, Sandy got hers done too.

I thought that was it but Sandy said that I needed to get my ears pierced as well. It really didn't hurt. I probably had so much adrenaline flowing in my blood stream that nothing would have hurt me. She put in little diamond studs and told me to keep them in 24/7 for a month and rotate them regularly before I could start changing them out. She gave me a bottle of antiseptic to bath them.

I was really a girl now, or so I thought, but Sandy had other ideas. We still needed to get me some better shoes. We went to a shoe-shop and picked out a pair of lowish sandals, there was a cute strap with a gold buckle around the ankles. They were obviously girls but did not add too much to my height. Finally, I was a girl.

She said, "I'll take you for a late lunch but first there is something we need to take care of."

When we were back in the car, she slid her hand up under my skirt and stroked the front of my panties. My cock was hard and I guessed what 'it' was that 'heeded to be taken care of'. I put my hand on her knee and stroked the inside of her thigh. Leaning over we kissed as our excitement was building. As our tongues met my heart was pounding and she could feel how excited I was.

She drove us back to her place and nearly dragged me up the stairs to her bedroom. Falling on her knees, in front of me, she lifted up my shirt and started licking my cock though my panties. She held my butt to push it hard against her face. By putting her head to one side, she was able to rub both lips along my shaft and tickle it with her tongue. I rested my hands on her shoulders and had to work hard not to cum.

She pulled my panties to one side, kissed the head of my cock and then ran her tongue around it. She smiled up at me and played with my balls. I learnt a lot from her about giving head. In fact, she taught me a lot about being a girl in general, how to dress, do my make-up and please a man. These lessons helped a lot when I was trained professionally to be a girl.

She lowered her head back onto my cock and slowly slid it right into her mouth. She rubbed the underside with her tongue as she went down. I could feel her face against my pubic hair. I didn't want to cum just yet and so I pulled away and steered her to the bed. She laid down and I lifter her skirt. She didn't have any panties on and I could see how excited her pussy was; it was glistening and puffed out.

It was my turn to give her oral. I licked along her pussy lips and then slowly slid my tongue into her cunt. I found her clit and gently sucked on it. It was already very excited. This time, she put her hands on my head and pulled my face hard against her. My nose was buried in her pubic hair.

I could tell that she wanted us to cum together and so I moved up her body. Spreading her thighs as I went. I kissed and licked her breasts on the way. When I got to her head, we kissed, she could taste her pussy in my mouth. She put her hand down between us and guided me in. I started moving in-and-out. She ran her nails up-and-down my back and then gripped my hair for another deep kiss. My tongue was in her mouth and my cock was in her pussy. She groaned and raised her hips to push me deeper into her.

We came together and collapsed in each other's arms. It took us a while to recover, I had the whole dressing-up experience to process and I think it had been a while since she last made real love. Eventually, we realized that the excitement had made us hungry. She took me, still dressed as Sarah, out for a late lunch, well early dinner by now. I was really getting used to being out dressed as a girl. I had a feeling that I would be going out a lot in the future.

SarahCD
SarahCD
402 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousabout 5 years ago
oh dear!

Are girls jeans that easy to spot? I often worried about pantie line but the list of zip length stitching colour and embroidery on pockets - looks like I am busted! But guess what I don't care anymore - be what you think you are, giggle

Share this Story

Similar Stories

Room Service Cum Eating Daphne eats cum from a wife’s freshly fucked pussy.in Group Sex
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
Rage Against the Latrine Ch. 01 A female singer urinates over a fan on stage.in Fetish
Naked Maid (Naked Hubby) I serve as wife's maid and entertain her friends.in Exhibitionist & Voyeur
More Stories