The House Sitter

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House sitting just took an interesting turn for Francis.
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"Okay, that covers everything I think! Thanks so much for this, Francis. I know it was short notice but I really appreciate it," said Ms. Wilson. "And remember, please, please, please help yourself to anything in the house."

"Oh, it's not a problem. Just hope you have fun on your cruise!" I couldn't help but wonder why she was going on a singles-only cruise for a week. She was hardly someone who I would think of as having trouble in the dating department. A tall, skinny blonde with an ass that doesn't quit should've been snatched up the moment she hit the market again. Who knows though? Ever since her husband left her, her confidence may have been completely shot.

"I'll be back next Sunday but if you need me just text me. And Francis... please make yourself comfortable. You're helping me out so, so much." Out the window, I could see her car arrive.

"Okay, Ms. Wilson. I will. Looks like your ride's here." Helping her with her bags, I walked her to the black Lincoln and loaded it up. Once she got settled into the backseat, I gave her a wave and off she went searching for love.

Walking back inside, I couldn't help but marvel at the opulence of the house. We had always know the Wilsons were well off, but the first time you see their house is something else. Mr. Wilson was always seen as a good businessman and the 6,500 sq ft house seemed to confirm that. But during the divorce settlement, Ms. Wilson made sure the house was hers. She had poured too much effort in designing and furnishing it with her exquisite taste to let it go.

I let out a content sigh and sat down on the sofa. A week of television and doing nothing in a beautiful house was a great way to spend a week of summer while I was home from college. Plus, the pool in the back didn't hurt either. On top of everything, Ms. Wilson was going to pay me pretty well. I couldn't complain.

After an entire day of binge watching tv, I was getting tired. You can only watch so many hours of mind numbing television before it gets to be more of a chore than a pleasure. I figured turning in for the night was the best plan of action. Besides, I had a long day of more tv and doing nothing ahead of me. She was in the process of renovating the guest rooms, so she told me to stay in the master suite. She said the rooms had reminded her too much of her ex husband. It didn't bother me at all though. The bed in the master was twice the size of mine back at school and 5x as comfortable. Sleeping on that thing would be like sleeping on a giant cloud. The only problem was she left in quite a hurry and there were clothes everywhere. I guess when you book a last minute cruise, keeping your room clean for the house sitter isn't you're highest priority.

"It's going to take me an hour just to get all the clothes off this bed," I thought to myself. "I mean how many outfits did she decide between?" There were dresses, tops, and bikinis of all different colors sprawled across the bed; a few pairs on lingerie were sitting on the edge of the bed too. Boy, I bet a lot of guys would loved to have been me in that moment. Doing laundry and picking up clothes isn't fun, sure. But imagining a hot cougar in them made it tolerable. The more clothes I gathered off the bed, the hotter it felt. After what seemed like forever, I had cleared off the bed and scattered the clothes on the floor. I figured it wasn't my place to clean up for her; I was just supposed to watch the house. Finally snug under the sheets, I closed my eyes.

"Damn it." I had forgotten to take my contacts out. I trudged to her bathroom and got my contact case out of my backpack but I couldn't find my contact solution. Surely, Ms. Wilson has some. I looked in the cabinet above the sink and found some. I sat down at her vanity to take out my contacts. I was amazed at all the different types of makeup and perfumes she had. It was like looking at a mini Ulta. Different eyeshadows, powders, lipsticks. You name it and she probably had three of them. The amount of beauty products on the vanity cost more than I made in three months.

I had always been curious about makeup ever since middle school. My best friend in college was a makeup artist so she had shown me what to do with all of them. Most guys in college had no idea what finishing powder or blush was for but because of Teresa, I did. Picking up one of her lipsticks, I opened it and smelled the cherry sweetness. Something had come over me. More than anything in the world, I wanted to put it on.

"No, that's weird. Besides, it's an invasion of privacy," I told myself. But then I had remembered what she said earlier this morning...

"... help yourself to anything in the house."

I had taken that as eat any food she had but maybe I could stretch the meaning out to a more general interpretation. I reached for the lipstick and outlined my lips. Teresa had always joked that my lips were too plump to be a guy's mouth anyway. Puckering up and kissing like I'd seen Teresa do after she applied her lipstick, I looked at the finished product in the vanity mirror.

" Wow, not bad." The red popped with my light complexion and my lips looked good. I couldn't stop staring at my lips in the mirror. Then something crazy happened. For the first time ever, I had a sudden urge... no, more of a insatiable desire to keep going. The very thought of being feminine made me harder than I'd ever been. I reached under my boxers and started playing around. Overwhelmed with ecstasy, I knew what I had to do.

I stripped down and turned on the bath. Grabbing for her razor, I covered every square inch of my body in shaving cream and began to shave. After what seemed like an hour, I was smooth to the touch from head to toe. Except for my hair... I had been growing it out for a couple of years now and I was proud of my shoulder length locks. I reached for her shampoo and conditioner giving my hair a good scrub. Stepping out of the bath, I grabbed a towel hanging on the wall, dried myself off and put my hair up like I had seen Teresa do countless times. The mirror across the room showed off my now freshly shaven figure and the light illuminated my silky smooth skin. For a 19 year old guy, I had always had a shapely figure. The years of running track had kept me slender yet toned. I grabbed for a plush robe I saw hanging off the door. It had Ms. Wilson's monogrammed initials on it and made my body feel like a million bucks. Every movement came with a heavenly brush of fabric against my smooth body.

Sitting down at her vanity, I began to go to work. Luckily, she and I had the same complexion so her foundation fit me perfectly. I gave myself a smokey eye Teresa had shown me on one of her clients. The lines on my eyeliner would have made Teresa proud. Contouring had always made sense to me and after a little time, my already feminine face looked 100% girl. After reapplying the lipstick I had chosen earlier, I couldn't help but admire my handiwork. If my family had seen me in that moment, they would have taken me for my long lost twin sister.

I let my hair down from the towel and found Ms. Wilson's blow dryer. Fluffing up my hair and giving it some volume was something I had never done before but a quick YouTube tutorial made easy work of it. Twirling my new do, I saw that my nails were so plain and boring. I had seen nail polish that matched the lipstick on the vanity. After doing my fingernails, I did my toes next. While waiting for the polish to dry, I couldn't help but glance in the mirror again. Not only did I look like a girl, I was a cute one... a really cute one.

"Too bad she doesn't have a lot of clothes," I thought to myself sarcastically. I went to the piles of clothes on the bedroom floor and started sorting out the contents but then I stopped myself. What am I doing? Her and I are the same size since she's taller for a woman. Why limit my options when I could go straight to the source?

Her walk-in closet was bigger than my room back at school! It even had a sitting area and three massive floor to ceiling mirrors. The racks were filled with designer dresses and tops of every kind. In the middle of the wall was a stack of drawers, about four feet wide. Opening them up, I couldn't believe my eyes. There was more lingerie in here than a Victoria's Secret. Black, white, red... she had everything. There was even a drawer filled with costumes. The French maid uniform was surely something I'd get to.

The wall of designer shoes was every girl's fantasy. She had red bottom stilettos, sexy wedges and every other shoe in between that drove men crazy. It drove me crazy too. But this time it wasn't lust, it was envy. My dainty feet could slide into any pair she had. It was a match made in heaven.

After taking my own personal inventory, I picked out a black push-up bra and matching lace panties. The bra made it look like I was a B-cup but I found some of her breast enhancers and my skinny chest was now a sexy C.

I picked out a low cut red dress that highlighted my new "girls" and made my cute bubble butt really pop. Sliding into that dress was one of the happiest moments of my life. The red stilettos to match tied the entire outfit together. The pearl necklace lying on her vanity was the final touch. In that moment, I had forgotten who Francis was and was eager to find out more about this sexy women standing in the mirror.

"Heidi." I had always liked the name so why not?

I spun around and admired my ass poking out of the dress. The back was open so you could just barely see the outline of my lace panties. I gave it a smack and giggled. I walked around the house and admired my new found womanhood. It was late at night so I didn't have to worry about any of the neighbors seeing me. But a little part of me wished they had. I wanted someone to see me like this. Heidi needed friends.

I reached for my phone and downloaded Tinder. I had used Tinder as a guy but not with much success. Skinny guys aren't the rage these days. Maybe Heidi would have a little more luck. I snapped a profile pic but realized I needed more than just one photo. So back to the closet I went.

Stripping down, I picked out a cute pair of denim high waisted shorts and a white top. Some tall wedges caught my eye and completed the look. I was shocked at how good I... err, Heidi looked. Posing like I had seen so many girls at my college, I took a couple of flirty pictures. Heidi had a good profile to work with.

After finishing up the bio section, I began swiping. I swiped every guy on there for about thirty minutes. Nothing happened. I must not have been as pretty as I thought. But after thirty minutes, I looked at my phone and it was completely blowing up with messages.

"Heyyy." "What's up beautiful?" "Cutie"

Guys around really seemed to like the idea of Heidi. I messaged one of them back. His name was Brett and he was cuttt. His muscles had muscles and his bio said he was 6'4. Now, I'd never dated a guy before but to say I was at least curious would be accurate. Being dressed like this though, I was more than curious. The thought of Brett coming over and seeing me as Heidi made me wet.

"Heyy Brett. What's up?"

...

"Well, after seeing you, I am if you know what I mean😜"

We messaged back and forth until finally he asked what I was doing tonight. I told him that I was house sitting.

"Well maybe you could use a little company."

"... okay"

I couldn't believe I had just said that. I gave him the address to Ms. Wilson's house and he said he'd be over soon. What had I done? Was there really a guy coming over? My chest started pounding and I thought about cancelling but for some reason I didn't.

After about an hour, I heard a knock on the door. My heart beat faster then than during any race I had ever run. I walked into the foyer, took a deep breath and opened the door.

The pictures didn't do him justice. Brett looked like a model. He was a cowboy through and through. The big gold belt buckle made sure you knew he was.

"Hi Heidi. Nice to meet you." His big hand enveloped my own. I was awestruck at how rugged and manly he was.

"Hi Brett," I said. My voice had always been higher and with a little effort I sounded just like any other girl in my classes. "Come in and sit down."

We sat down on the couch and started talking about each other. He was a carpenter and had lived in the area for six months now. I got him a glass of wine and edged toward him. My lipstick made a sexy outline on the edge of my glass and he stared at it.

"Say, it looks like you got your glass dirty." He pointed at the half full wine glass.

"Yeah I guess so."

"Your kind of a dirty girl," he commented "Aren't you?" Just then, he caressed my lips with his finger. Instinctively, I took it in my mouth and gave it a light suck. This drove him crazy. He pulled my light frame onto his body and passionately kissed my neck. The feeling of his scruffy beard on my smooth face drove me wild.

"You're so beautiful." He stopped and stared into my eyes for what felt like an eternity spent in complete bliss. I got off his lap and down on my knees. His cock was throbbing under his jeans. I pulled off his belt buckle and unzipped his pants. It was the biggest cock I had ever seen. The girth and width of it made it look like it was fake. He shoved my face down near it and I took his big shaft in my hand. Stroking it, I put the tip in my mouth and licked the precum. Then he took my head and powerfully shoved me down on him. I gagged when the monster reached the back of my throat.

It was liberating. All those years of suppressing who I was supposed to be finally came rushing to the front. I knew Heidi was let free. I sucked him until he came and I swallowed it down.

His face was in a state of euphoria. I licked my lips and stared up at him with big doe eyes.

"How was that?" I asked him.

"Heidi you are something else. If I didn't have work tomorrow, I'd spend the entire night like that." He grabbed my chin and kissed me on the lips. "Say what are you doing tomorrow night?"

"Nothing." My heart lept out of my chest at the thought of two nights in a row with this sexy cowboy.

"Well maybe I can think of something." With that, he grabbed his coat and got into his pickup. I just sat there in the hallway shocked at what just happened. I could still taste his cum in my mouth.

I had just met Heidi but I liked her already.

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11 Comments
AnonymousAnonymousover 4 years ago
Please

Can we get a chapter 2 please, please, please?! With a cherry on top 😉

JoannePareJoannePareabout 5 years ago
So wonderful

Dear Vespiian,

such a wonderful story, i do hope that you plan on continuing it as I am sure that Brett and Ms. Wilson might have so much pleasure with Heidi.

Please continue this story.

XOXOXO

Lostboy11Lostboy11almost 6 years ago
Moooore!!

More please! I’m so he’s but it wasn’t enough ;p

AnonymousAnonymousabout 6 years ago
More, More, More-----

Hope you continue --- especially when Mrs. Wilson returns from her cruise!

AnonymousAnonymousabout 6 years ago
Very Hot

Loved it, want to read more. Ms. Wilson is going to have hot fun with Heidi when she returns.

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