by John Dylena
Mark whimpered as he wrapped his lips around her fake dick. Anne crawled behind him and played with his ass before pressing the head of her cock against his opening and slowly pushing it in.
He moaned through the cock in his mouth as Anne gently buried herself deeper and deeper into him. Each time she thrust, she pulled out to the tip, then slowly inched her way back inside until his ass clamped down around her hilt. She moaned at the sensation of fucking him and how it pressed her strap-on against her clit.
The two women continued their assault on Mark, filling him from both ends, giggling and groaning as he hungrily slobbered all over Lisa’s dick. His thighs quivered as Anne picked up the pace behind him, bucking her hips in a wild frenzy, desperate to ramp up the friction on her clit. He knew she was close.
He was close, too. The curved tip of her thick strap-on was prodding at his sweet spot, filling his own dick with a thick, hot load. Mark closed his eyes and deepthroated Lisa again and again, forcing his face against her hips and swaying his head so her cock grazed her slit.
“Fuck!” Lisa moaned just as all three of them climaxed.
Mark moaned loudly as he blew his load onto the bed, seeing stars as Anne frantically pummeled his prostate. Both the women cried out as they went over the edge, Lisa rubbing her mound all over his face as she tickled the back of his throat with her dick. He could smell her lust on the other side of the fake cock, filling his nostrils with the heady aroma of her sweetness.
With their lust sated, they pulled out of Mark and left him on the bed, empty and exhausted.
Lisa and Anne hugged, said their goodbyes, and Anne left.
“And cut!” Ricardo shouted. “Nicely done, ladies, and way to go Mark! You did a great job.”
Anne returned with a jacket, wrapped it around Mark, and sat down next to him.
“I’m proud of you, Mark. It takes a lot of guts to do what you just did,” Lisa said, hugging him. She kissed him on the cheek and left the set.
“Mark,” Anne said, rubbing his back.
“Yeah?”
“I’m sorry for breaking up with you. But if it’s all right with you, I think I can give it another shot.” She turned her head and whispered into his ear. “Seeing you all dressed like this is incredibly hot. I hope Malinda can come by my apartment sometime. I have some lingerie I’d love to see her wear.”
Mark faced Anne and smiled. “I think that can be arranged.”
THE HOUSE SITTER
I sat quietly in the driver seat of my car, staring down at the phone in my hands. I was nervous, a slight quiver in my hands giving it away. A quick swig of my water bottle to rid myself of dry mouth; I looked down at my watch: noon. I opened the car door and stepped out into the summer heat.
The neighborhood was spacious and affluent. Many of the homes were large two-story mansions, with two- to three-car garages and manicured lawns and gardens. Tall fences of wood, brick, or stone surrounded the back of each home, giving their ample backyards plenty of privacy.
I walked up the cobblestone path to the large double front doors made from a dark brown wood. I rang the gold-colored doorbell and waited. A gentle breeze blew past.
“Ahh, good afternoon, John!” the homeowner said as the door flew open. She was dressed in business attire: a black skirt suit with an ivory blouse and pantyhose. Her perfume was noticeable but not overpowering, and her gold and gem-inlaid jewelry shone brightly in the sunlight.
I jerked back slightly, startled by her boisterous enthusiasm. “Good afternoon, Ms. Stevenson.”
She motioned for me to come inside. “Oh please, call me Janet. Come on in. I’ll show you around.”
I nodded and stepped onto the light gray granite of the entryway, looking up at the vaulted ceilings as Janet walked past me, her high heels clicking on the stone floor.
Ms. Janet Stevenson, a wealthy thirty-year-old, gorgeous blonde, used to be my family’s neighbor. We lived in a nice enough neighborhood, but when she got a major promotion, she packed up and moved out into a gated community with the round-the-clock armed guard. She was only our neighbor for a couple of years, and I house-sat for her then, but only once.
That was, however, before I developed my secret hobby.
I was once again house-sitting for her because she was embarking on an extended business trip. She would be gone for about six days, and even though she lived in a well-protected neighborhood, she didn’t like leaving her place empty for that long. So she managed to find me and give me a call. I was glad to accept her offer to house-sit, not only because she had one hell of a house, but because the pay wasn’t too shabby, either.
“Come on!” she said, waving me over. “I wanna give you the grand tour.”
“Right,” I said, shaken from my reverie. “Sorry.”
She led me on a tour of her house, and frankly, it fit the mansion description. The whole place was well-furnished, with expensive-looking rugs, paintings, framed movie posters, pictures, and other ornate accoutrements.
Leaving the entryway, we came into the living room. It had a giant, comfortable-looking couch and a massive flatscreen TV, complete with 7.1 surround sound. One thing I always liked about Janet her was that she had superb taste in movies, and next to her TV was a giant DVD collection. As tall as a bookshelf, it was full to the brim of movies and boxed TV sets.
Connected to the living room were the kitchen and dining room. The kitchen was large and open by design, with lots of counter space and expensive granite counter-tops. With all the shiny stainless steel appliances and fully-stocked fridge, it reminded me of a kitchen a celebrity chef on The Food Network would have.
“I went shopping yesterday and stocked the fridge for you,” Janet said as we passed through. “You’re welcome to use anything in here to eat and cook what you like.”
“Cool.”
She stopped. “Can you cook?”
“Nothing fancy, but I’m learning.”
“Really? Nothing beats a guy who can cook.” She gave me a sly wink.
I continued following her and she led me into the dining room. A large wooden table with eight chairs sat atop a rug in the middle of the room. Against the wall was a liquor cabinet and wine fridge.
“You’re twenty-one, right?” she asked me.
“Twenty-four, almost twenty-five,” I replied.
Janet raised an eyebrow. “Really now? You look so young. You’re welcome to the bar. I also just restocked it too – just don’t go drinking all of it!” she said as she laughed.
“Thanks,” I said with a smile.
I followed her out of the dining room, across the living room, and up the stairs to the bedrooms.
“This house has three bedrooms and two bathrooms. This one is the office.” She opened the door and we walked in.
Inside was a massive wooden computer desk with a very expensive iMac. There were filling cabinets flanking it, and an all-in-one printer situated at the top. The office was decorated with pictures, plants, a coffee maker, and a micro fridge.
“There is WiFi throughout the whole house. You’re welcome to use it, if you want. It's very fast.”
“Thanks.”
She led me out of the office and back into the hallway. She opened up another door, and awe-struck, I walked in.
“This is the master bedroom.”
“Wow!” I breathed.
That was an understatement. The room was huge. It had a gargantuan bed, nice wooden furniture, and another flat screen TV that wasn’t quite not as big as the one in the living room.
“All the TVs are connected to the satellite and have DVR capabilities,” she pointed out. Then she moved across the room. “Over here!”
I walked over to the doorway where she was standing. Inside was a massive bathroom. It was outfitted with a had large, glass-walled shower, a whirlpool bathtub, a high-powered flush toilet, and a sizeable vanity.
“What's that?” I asked as we were walking out of the room, pointing at two large sliding doors.
“Oh yeah, I forgot about that.” She walked over and opened them up. “This is my walk-in closet.”
“Closet?!” I said as I stared into it. There were floor to ceiling clothing racks, a myriad of designer shoes, a chest of drawers, a full length mirror, and a couple of wigs on the top shelf. “This is like a small bedroom!”
“Yes, this is my sanctuary,” she said with a smile.
We left and she showed me the spare room. It was moderately furnished, but still looked very nice and clean. The bedroom and bathroom combined were probably the size of the master bedroom.
“You’re welcome to sleep in either room. However, if you do sleep in my room, make sure you make the bed. Got it?”
“Yes, ma’am!” I replied.
“Good. Now, there is one room in this house that is completely off limits…” She hesitated. “Well, sorta.”
I frowned. “Which room is that?”
“The garage.”
We walked downstairs and into the garage. She had two cars and a motorbike. One was an SUV, which was probably her everyday car. The other one was an Aston Martin, which just happened to be my dream car. The bike was a ‘super bike’ and had a nice color scheme, but all my attention was on the Aston.
“I have the keys locked away and hidden,” Janet said. “You can look all you want, but no touchy! If you do manage to find the keys and drive the car, well, just know there is a special place in hell waiting for you.” She grinned wickedly.
“Don’t worry, Ms. Stevenson. I highly respect these cars and will not drive them, but may I at least sit in them and pretend?”
She laughed. “Sure! Just don’t dirty the interior.” A honking outside signaled the arrival of her ride to the airport. “Crap, that's my taxi! Okay, I left a very detailed instruction packet in the kitchen. There you will find your parking permit and clicker so you can get in through the gate without having to go through security. You’re not allowed any guests, and you do not have to stay here the whole time. Feel free to come and go as you please.”
I smiled at her reassuringly. “No worries. I’ve got a lot of work I have to do, so I might just hunker down here for a while.”
Janet nodded. “All right. Thanks again, John! You’re a life saver!” Then she gave me a big hug and a kiss on the cheek, grabbed her luggage and ran outside to the cab. She waved goodbye as it sped off.
Goddamn, she is so hot, I said thought to myself with a sigh of relief. Not only does she look sexy, but she dresses sexy, too!
The images of her and her outfit filled my mind as I unpacked my car and brought my luggage into her house. Locking the door behind me, I moved my stuff out of the entryway into the living room. I took out my laptop and set it on the coffee table, then took the rest of my stuff upstairs. I walked down the hall to the bedrooms and was about to open the door to the guest room when I thought about it for a second.
Wait, the guest room? No, no, no. I’m staying in the master bedroom!
I turned around and opened the door to the master bedroom. I set my stuff down and jumped onto the bed. I rolled over and saw the time. It was close to three-p.m. Ms. Stevenson had an evening flight to Japan, but in the company’s first-class private jet. Looking at my watch, I figured she was still on her way to the airport.
I headed downstairs and turned on the TV. Time flew by, and my rumbling stomach reminded me that it was time for dinner. After a quick meal, I headed back to the master bedroom.
Aw yeah, I'm gonna take a whirlpool bath! I decided. I’ve always wanted to take one of those!
I stripped and got the bath ready. I had read through her instructions while eating, so I knew where the towels she set aside for me were located. When the bath was ready, I climbed in and was instantly relaxed. I helped myself to the fancy-smelling, super-cleaning shampoos, conditioners, and soaps. I was inspecting all the other stuff she had when I found it: a bottle of shave-less body hair remover. I couldn’t help but think of my secret hobby.
Over the past few years, I’d grown more and more interested in women’s clothing. I’d fantasized about dressing up in various outfits, putting on makeup, and having long hair. I’d always wondered what it would like to wear women’s clothes, high heels, lingerie, makeup, and jewelry. And when I grabbed that bottle, the urge to indulge those desires hit me like a truck.
Now is the perfect time.
I had this nice house all to myself for six days. The owner was a drop-dead gorgeous blonde who had a massive closet with who knows how many different types of outfits. This was the chance I’d been looking for.
I took a deep breath, meditated on it for a good minute in the nice relaxing tub, and then decided to go through with it. But I would have to be very discreet and make sure everything was put back exactly where it was. I wouldn’t want Janet to think that anything had been disturbed.
I smiled as I looked down at my arms and legs. I was lucky; I had never been very hairy. My younger brother got all those genes.
I followed the instructions on the bottle, and within minutes, my arms and legs were free of body hair. I got out of the tub and dried off.
“Oh, wow,” I murmured aloud. The feel of the soft towel on my now hairless body sent a slight chill up my spine.
I drained the tub, wrapped the towel around my waist, and headed towards the walk-in closet. I took a deep breath and opened the sliding doors. My hands were shaking with nervous energy as I walked around the closet, my fingers feeling the fabrics of the clothes Janet had hanging up on the racks.
First things first: underwear. I walked up to the drawers and browsed through them. I found the bras and took out a pink one. Then I searched some more and found a matching pair of panties.
I set them aside and continued searching. After a couple seconds, I found a garter belt and a pair of white stockings, and I set them next to the rest.
I removed the towel and put the bra on first, clipping it behind me. Then I put on the panties and the garter belt afterward. I sat down on the drawer and slid up the stockings. The feel of the fabric on my smooth legs sent another chill up my spine. When I had both of them on, I stood up and attached the tops to the garter belt.
I trembled with anticipation as I walked over to the shoes and looked through them. I found the pair I was looking for: matching pink, five-inch heels. I prayed as I slid them on that they would fit, and while they were a little tight, the stockings helped to slide them on more easily. I stood up and walked over to the mirror.
Damn, this is so awesome! I thought, admiring my reflection. But I'm not done yet.
I walked over and grabbed one of the shoulder-length brunette wigs from the top shelf of the closet. I put it on and looked at myself again. Almost there.
I left the closet and headed for the bathroom vanity, my heels clicking on the wooden floor. I looked down at my groin as I walked and saw the growing bulge in my panties. Hoping that I wouldn’t get too excited too quickly, I sat down at the vanity and began the process of applying makeup to my face.
It took a while, but when I was finished applying the mascara, eye shadow, eye liner, blush, lipstick, and lip liner, I took a step back and admired my handiwork.
“Not bad,” I said to myself. Looking back at me in the mirror was a woman—not the best-looking woman I’d ever seen, but I was convincing enough to be mistaken as one.
I put the makeup away and returned to the bedroom. There I had some fun posing in front of the mirror. All the while, I was getting more and more turned on.
Shit. Looks like I need to go “relieve” myself.
I went into the bathroom and fumbled around the shelves. I found some lotion and tissues, but I decided to look through one more drawer before I began touching myself. Inside, I found something intriguing. I slowly reached into the drawer and removed the object. It was a dildo. I was fascinated by the object; it was the first one I’d seen.
“Oh my,” I said, further inspecting it. Curious, I set the stuff down on the counter-top and fum
bled around with the dildo. My curiosity peaked as I slid down my panties and set them aside. I placed the dildo near my anus and took a deep breath. I pushed it in slightly and it penetrated my hole. It entered smoothly despite the lack of lube and I was quickly overcome by the sensation.
I slid it in further as my penis got harder and harder. I started sliding it in and out, faster and faster. Girlish moans escaped my lips and I was now taking the whole thing in.
My dick was fully erect and I started masturbating. My fingers fumbled around the base of the dildo and accidentally switched on the vibrator. The vibrations heightened the pleasure exponentially, as my moans grew louder.
I felt my dick twitch as I climaxed and shot a load off into my hands, the shock of it all bringing me out of the erotic haze. I immediately removed the dildo and tossed it aside, turning it off in the process. Gasping for air, I looked down at my right hand. It was covered in my man-juice.
What just happened? I wondered in between labored breaths.
Exhausted, I washed off the sperm in the sink and cleaned off the dildo and put it away. Then I inspected the bathroom for any drops that I might’ve missed.
I stood there, looking at myself in the mirror and at the outfit I was wearing. God damn, I'm a fucking slut, I thought. But that was very, very… weird.
Even though I’d just unexpectedly fucked myself in the ass with a dildo, I still wanted to wear Ms. Stevenson’s clothes. But now that I knew what that felt like, I vowed to stay away from her dildos.
I removed her clothes and put them back, then put on some PJs and passed out. It was near midnight, and I had a lot of work to do in the morning.
“Ugh,” I grumbled as I climbed out of bed the next day. It was so comfortable that I didn’t want to leave it. I sat up at the end of the bed and planned out my day.
“Let's see… oh yeah, I have all those data sheets that I need to type up today… balls!”
I got up and went into the bathroom. While relieving my bladder, I remembered what Ms. Stevenson wore yesterday, and that's when it hit me.
Damn, she was so sexy. Maybe today I’ll do my work in a similar get-up. I mean, all I’ll be doing is typing… so pretty much all I'm doing is secretarial work. Why not dress like one?