Nevertheless, I couldn’t stop myself from doing this. I began by putting on the panties. They slid up nicely along my legs. The pair fit nicely between my ass cheeks. The gusset had some room to support my cock.
The bra was much trickier. I had experience unhooking them but putting the clasp together was new to me. With a bit of trial and error, I managed to hook it around my back. That left another problem. Amanda was a well-endowed woman but I was a flat-chested man. I decided to take a pair of socks, roll them up, and put them in my bra. It did the trick and puffed up to create a respectable bust line.
I followed up by wrapping the garter belt around myself. It was easy putting on the tight stockings and attaching them to the belt. They really brought out the muscle tone of my legs. Next, I examined Amanda’s collection of cosmetics at the dresser.
I didn’t bother putting on stuff like lipstick. I didn’t know the first thing about how eyeshadow or lip gloss worked. Chances were that I’d make myself look like some clown from a circus. Nonetheless, I did dab a bit of blush on my cheeks.
The dresser had some jewelry which I helped myself to. My ears weren’t pierced but a nice pearl necklace made my neck look positively swanlike. Finally, I took out a pair of heels that looked to be in my size. They added a good deal of height to my short body.
I picked up the dress but then I decided to look at my body first. Using the closet door’s body mirror, I was shocked to see how good I looked. The undergarments worked well with my lithe frame. My old clothes were a size too big. I wasn’t willing to go into the teenage boy’s section to get something in my size.
This, however, was perfect.
I went back to put on the dress and returned to the mirror. It was just as formfitting as anything else. It was starting to come together. However, my hair was still the same short cut with trimmed sideburns. It looked more appropriate for a football player than for a woman.
That gave an idea.
I went back to the closet and retrieved a brunette wig. I didn’t know why Amanda kept so many damn wigs in her closet. Nevertheless, I put on the wig and returned to the mirror. “Looking sharp.”
It was pretty damn convincing. I didn’t see Mark the underachieving convenience store employee in the mirror. I hadn’t worn much makeup at all. This was just the feminine attire bringing out my natural look. Hell, I would go as far as to say that I looked hot.
I decided to see what else was in Amanda’s closet. I didn’t want to make too much of a mess. I could try out a few other shoes. I just needed to remember to put them back in the right place.
That’s when I noticed a loose floorboard under the shoe rack.
Curious, I lifted up the floorboard which revealed a box. It was the size of two shoeboxes put together. I took the lid off and did a double-take when I saw what was inside.
It held a cornucopia of kinky toys and fetish wear. I saw a full set of dominatrix gear next to a large dildo. It looked like the prim and proper Ms. Williams had another side to her.
I knew I should’ve put the box back where I found it. Amanda would definitely know if I had messed around with this secret compartment. However, I felt the same compulsion I had experienced a moment ago.
I wanted to play with the dildo.
I gingerly reached out for the phallus and discovered that it was made of high quality material. It was firm but had a little give to it. I had seen dildos before but this was really fancy. It could vibrate and even heat up to body temperature with a flick of a button.
Amanda had spared no expense in this beauty. I guessed she needed to have a way to relieve herself after the divorce. Or maybe things had been chilly for years and this dildo was her trusty friend.
For that matter, I needed to relieve myself as well.
Throwing caution to the wind, I took the dildo and went back to the bed. Undoing my garter belts, I took off my panties and lied on the bed. Something about dressing like a woman made stroking myself feel mundane. I needed to do something kinkier to get myself off.
After lubing it with my saliva, I gripped the base of the dildo and guided it to my ass. I gently pressed it against my rosebud so it would get used to this feeling. The dildo was warm after switching on its heating function. This helped me to prepare for penetration.
Soon, I began slowly sliding it into my ass. I gritted my teeth as the dildo stretched my asshole. Once I got used to it, I began gently thrusting it in and out. It was moving inside of me with surprising ease. My cock was growing as rigid as the one fucking my ass.
I started pumping the dildo even faster. Once I was satisfied with its depth, I turned on its vibration function. It immediately sprang to life and compounded the pleasure I was feeling. I moaned as bliss spread through every pore of my skin.
With my free hand, I began stroking my erection. I had never seen or felt it become so hard in my life. Something about dressing like a woman and using a dildo was pushing all the right buttons. The friction between my prick and my hand was unbearable.
The vibrating dildo throbbed in my ass. It felt like it was running on a trip hammer. Likewise, my cock was twitching as well. I was on the cusp of a colossal orgasm.
Within seconds, I climaxed with a powerful burst. I couldn’t remember the last time I went off this fast and with so much intensity. I immediately let go of the dildo and let it vibrate inside of me. I used both hands to milk my cock for all that it was worth. When I finished, I saw the mess I had made on the bed.
“Fuck!” I groaned, taking the dildo out of my ass. Surveying the damage, I knew it didn’t look good. The sheets were sticky with my semen. I had also gotten some on my stockings and socks. “I’ve got to get this cleaned up.”
Not bothering to dress in my regular clothes, I gathered up the bedsheets and went down to the laundry room in the basement. Reading the instructions for both the bedsheets and my cum-stained clothing, I ended up putting both loads in a separate washing machines. I could make up a believable excuse about having to clean the sheets. The spin cycle on the machines gave me plenty of time to go over what had happened.
I didn’t know what had possessed me to dress up as a woman and fuck my ass with a dildo. Something about seeing Amanda’s wardrobe had awoken something deep within me. Feeling her clothes and touching her secret S&M gear had done a real number on my psyche.
I went upstairs to change back into my old clothes and check anything I missed. I even cleaned the dildo in the bathroom sink before placing it back in storage with the other naughty toys. It gave me a chance to examine Amanda’s tools of the trade. She had everything from domino masks to riding crops. I wouldn’t want to get on the receiving end of the latter but I still had this perverse curiosity about this hidden cache.
Of course, I was reluctant to experiment any further with Amanda’s hidden naughty toys. I had already gone off the deep end with this little adventure. If I wasn’t careful, then she could find out what I had done. I didn’t need to get in any more trouble than I was already in.
However, my old clothes chaffed against my skin. It was like wearing a straightjacket in comparison to Amanda’s soft clothing. Maybe I could split the different. I could wear her clothing while avoiding her fetish gear. Her clothes were easy to clean and place back in the closet. She would never suspect a thing.
If she got suspicious, then I could make up the excuse that I went through her closet looking for towels. I made my decision and picked out a nice, silky nightgown from the closet. I would sleep in it once the laundry was done.
Chapter 3
“Hmmm… what should I wear today?”
I couldn’t remember the last time I had such a blissful sleep. Usually, I tossed and turned throughout the night. Sure, the bed was nice but the nightgown was like wearing nothing at all.
I glanced at Amanda’s closet as I went into the bathroom. I didn’t get to have my bath yesterday so now was as good of a time as any. After brushing my teeth, I drew a hot bath and climbed in.
It
beat having a quick and cold shower at my apartment any day of the week.
I helped myself to Amanda’s various body lotions. I wanted my skin to be as soft and smooth as possible. Strangely enough, I was beginning to think of myself as a woman instead of some freak with a fetish.
Amanda’s collection of clothing, makeup, and wigs fascinated me. I was curious to how the soft cloth and cool jewelry would feel against my skin. There were so many dresses, lingerie, and shoes to wear. If I was careful, then Amanda wouldn’t suspect that I had been trying them on.
I relaxed in the warm water and thought of a plan. I had the house to myself for the next few days. I could rotate in different outfits and clean them the next day. On the last day, I’d do a final check to cover up my tracks. I needed to put back everything where it was originally.
Yes, that could work.
Finally, I drained the tub and dried myself with a towel. Then, I walked nude towards Amanda’s wardrobe and opened it. I didn’t feel the same anxiety I had experienced the last time I did this. I thumbed through the various clothing hangers until I found something to my liking.
I decided upon a blouse and skirt combination. The power blue color of the blouse made me think I was preparing for a real job in an office. I may not have been a fan of working in an office building but I liked office clothing colors such as pink, baby blue, and steel grey.
As for the undergarments, I decided on something simple and comfortable. I found a tasteful set of snow white bra and panties. After stuffing the bra, I put on my blouse and skirt. I unbuttoned the top of my blouse to reveal a bit of fake cleavage. Then, I finished up the look with a blonde wig.
It was a different look than the sexy evening dress I wore yesterday. Nevertheless, there was something appealing about this prim and proper look. I selected out a pair of pumps that looked to be my size. They added some height while being more manageable in the house than high heels.
I decided to try my hand at makeup. Looking up instructional videos on YouTube, I started easy by carefully applying lipstick. The cherry color made my lips look plump and regal. I followed up with some blush and a bit of eyeliner.
I wolf-whistled at my reflection. “Looking like a total babe!”
I opened up Amanda’s jewelry collection. First, I wrote a map of where everything was originally located. I knew she would be able to tell if something was misplaced.
I picked out a nice gold necklace and a set of matching bracelets. I also picked out a small wristwatch. Between her fetish gear and her jewelry, Amanda certainly had money to burn.
Once I finished, I went downstairs and lounged around in the living room. It was oddly comfortable walking around in pumps while dressed as a woman. These clothes felt as natural as a second skin. The shoes didn’t hurt once I got used to walking in them.
I started acting more like a woman. I walked more daintily. I straightened out my skirt whenever I sat. It came with surprising ease. I even avoided the typical activities I did as a man, such watching action movies or playing videogames. Instead, I sat down with a book and drank come hot cocoa.
Time flew by as I cross-dressed as a woman. It was almost like peeling off my skin when I had to take them off for the night. Nevertheless, I had to clean my manly odor off of them.
Thankfully, Amanda had a selection of evening wear for me to choose. I selected a nice, silky robe that was perfect for a private dinner. While her liquor cabinet was off limits, Amanda had a few open bottles of wine in storage. I was sure she wouldn’t notice if I helped myself to a glass.
I sipped wine and watched a tacky romance movie on Netflix. Something about dressing like this was bringing out my feminine side. With a platter of gourmet cheese and wine, I had a wonderful time. This was even better than watching TV on a slow day at the convenience store.
When the laundry cycle finished, I decided it was time to retire for the night. I carefully placed back the clothes where I found them in the closet. I put the wig back on its stand in the closet before going to sleep.
It was another night of pleasant dreams.
The previous day of experimentation had only emboldened me. I was completely drunk on cross-dressing. I needed to kick it up a notch like a junkie chasing a high.
Rummaging through Amanda’s wardrobe, I came across a maid outfit. It was dark and frilly with sheer white stockings. I didn’t know whether it was part of a uniform for a cleaning service or a personal fetish of Mrs. Williams. In any case, it looked to be my size.
As luck would have it, the bra for the maid outfit came with a set of gel molds. They were like shoe inserts for bras. I put the molds under my bra and gave it a test run. They were much more believable than a pair of rolled up socks.
I began into stepping into the trimmed skirt. Its short length made me think this was one of Amanda’s slutty outfits. I put on the rest of the outfit before tying the apron around my waist. Finally, I stepped into a pair of dark heels with clasps on them.
I looked like one of those French maids you found on fetish websites. It got me into the cleaning mood and I began cleaning up the house. After all, I was here to look after the house and water the plants.
Room by room, I made sure every surface was spotless. Something about this outfit was making me roleplay as a maid. I paid extra attention to the guestroom. Amanda would give that room extra scrutiny when she came back. It had her secret treasure after all.
I wasn’t looking forward to her coming back. It had nothing to do with losing this easy job. Instead, I was concerned with losing access to Amanda’s wardrobe. It was a treasure trove of different outfits for me to wear.
I could always start to cross-dress on my own. However, I never had much money on account of being a perpetual slacker. I would have to build it up one outfit at a time.
I’d just have to enjoy myself until Amanda arrived.
Over the next few days, I fell into a familiar pattern. I picked out an outfit, spent the day in it, and cleaned it after I was done. Each dress made me discover my body again. Stockings and pantyhose made me realize I had a pair of beautiful, toned legs. Tight clothing, such as a workout outfit, made me appreciate my natural curves.
On the last day, I treated myself to a rather scandalous set of clothing. I picked out a denim miniskirt and a way too small shirt. The skirt needed to be tied up and revealed my bare midriff. I looked like a backup dancer in a Britney Spears video. I figured I might as well go for broke with Amanda arriving tomorrow.
I selected a skimpy thong to wear under the skirt. Its waistband could be easily seen above the skirt. The thong rode up my ass but it wasn’t uncomfortable. Finally, I picked the tallest heels in Amanda’s shoe collection.
I gasped when I saw my reflection in the mirror. I looked like some prostitute. No, not a classy escort hired by billionaires. I was more like a street walker you saw on the bad side of town.
I was almost tempted to go outside dressed like this. I knew that it was a stupid idea. I could attract a lot of unwanted attention. That went double in a prim and proper neighborhood like this one. There was probably some public ordinance about cross-dressing in public. Amanda would have my head if I got thrown in jail for public indecency.
Nevertheless, I enjoyed my last day as a woman. I spend the day reading books and eating a nice dinner in this trashy outfit. Before I went to bed, I made sure every single piece of clothing, jewelry, and shoes were cleaned and properly stored in the right place.
I was going to miss dressing up like this.
Chapter 4
“Thank you so much, Mark,” Amanda said as we brought her luggage inside. Well, it was mostly me since I carried in the heavy stuff. “Did Mrs. Henson give you any trouble? That batty woman really has it out for me.”
“I’m fine,” I answered with an anxious smile. I placed her luggage inside and closed the door. “None of the neighbors bothered me. How was the trip, Amanda?”
“I feel completely refreshed,” she said, stifling a yawn. It w
as good that she was too tired to notice how nervous I was. “Although that flight back home took the wind out of me. How about you?”
I kept smiling like an idiot. “I’ll be lying if I didn’t enjoy looking after the house.”
Amanda sat down. “Glad to hear it.”
“I kept my nose clean,” I answered, trying to look like a boy scout. “The plants are watered and everything is right where you left it.”
Suddenly, Amanda stopped and scanned the room. She let out a murmur. “Hmmm…”
That made my spine tingle. “What’s wrong, Amanda?”
I wondered what I had missed. I made sure to put all the clothes back where I found them. I had cleaned up stains left by the makeup I had worn. I didn’t know what had given me away.
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