Housekeeping

Housekeeping

Sometimes I get lucky and sometimes not.

I travel a lot for work and stay at various hotels and motels here and around the world. While staying at the more posh hotels was nice, I like staying at some of the lesser posh ones. Especially at some small ones where the maids are a bit more in need.

You see, I love being "accidentally" caught naked while masturbating in bed while watching porn. The majority of the maids are embarrassed and leave after apologizing while some don't. Some just watch while others join in. Those that do receive a nice tip (no pun intended).

I was at one small town motel for a meeting the next morning. It had only twenty rooms so there was only one maid who I saw in the morning before I left. She was about five-five with okay boobs and a nice big ass. I later found out she was called Sara; an Albanian recent immigrant who needed the work to survive. Perfect.

I had the next morning all planned. Drapes were drawn and bed linen down. After I checked to see that Sara would be doing my room next. I laid naked on the bed; hard cock in hand with porn playing on my tablet and headphones on. The head phones are noise canceling but in these cases, I keep it turned off.

"Knock... Knock." I heard. "Housekeeping!"

No matter how many times I had done this, I always got butterflies in my belly. The anticipation made my heart pound. I watched as the door knob rattled and turned. Sara used her beautiful big bum to pushed the door open and entering the room backwards. She used her cart to prop the door open before she turned and spotted me jerking off. "Oh! I'm sorry! I'm sorry!"

I pretended to be embarrassed while Sara turned to leave but I called out. "Wait! It's okay!"

Sara hesitated. She stayed. She looked out the door to see if anyone else was watching. I beckoned her in. Again, she hesitated but ended up pulling in her cart and closing the door behind her.

"I'm sorry I didn't hear you knock. I can't hear anything with these noise cancelling headphones." I explained while I still stroked. "Would you like to come closer and watch?"

Sara nodded her head and approached. She sat at the edge of the bed. Her dark brown eyes stared intently at my cock. Pre-cum flowed over my fist. I nodded as I took her hand and wrapped her fingers around my shaft. Automatically, her warm hand moved up and down. I watched her face as she bit her lips. "Go ahead if you want to suck it."

She looked around and lowered her head. She hesitated with her mouth a mere half inch from my tip. Carefully, Sara extended her tongue and lick my oozing pee hole. She smiled at the taste from the savoury nectar. She opened her mouth and took me inside. Her mouth was wet and warm.

"Oh my gawd!"I groaned. "Fuck! Yes!"

Sara took her time. For sure, it wasn't her first time sucking dick. She shifted around so she could take my entire, six inch length. She licked her palm and played with my sack. She squeezed my balls and made me come instantly. I spasmed hard with each wad. It was a big load but she expertly sealed her lips around my shaft. Nothing leaked out. She swallowed it all.

"Wow! That was fantastic!" I managed to tell her after I recovered slightly. "Honestly, the best blow job I've ever had!"

"I come back later!" Sara smiled as she prepared to leave. I handed her a C-note. "Thank you!"

Later that evening, there was a knock on my door. I opened it to see Sara smiling at me. I invited her in and fucked her hard all night.

+++

Did I mention when I travel that I like to dress up? My other fetish was wearing women's underthings; panties, bras, stockings, garters and the like. When I drive or take a train, I would wear a bra under my shirt and jacket while I usually have on panties under my pants. I wore stockings and garters too. I love to play with my attire during the journey.

Flying was a bit different due to security screening. After the first time I found out that the imaging machine or the metal detector would rat me out. Rather than an obvious bra, I put on a silky camisole with spaghetti straps. It looked more like an undershirt and the soft cups are easy to hide under my jacket. Panties of course but rather than a garter belt with metal clips that would be detected, I wore some gartered pantyhose. At least they felt close to wearing actual garters. I hated regular pantyhose.

I ended up at this one hotel and decided to dress up and be caught. I do this sometimes because. Sometimes the maids chuckle and leave, while some stay and watch.

The drive would be a boring eight hours from home. I dressed for the trip. I attached my self-adhering, G-cup breast plate to my chest and supported them with a plain, black bra with mesh cups. The over-sized cranberry nipples protruded through. I stepped into some tiny, bikini, mesh thong panties and pulled the back up hard into my ass crack. The front triangle was large enough to cradle my balls but not hold my shaft. I slid my legs into some sheer black, nylons and attached the welts to the dangling straps from the black garter belt I wore. I adjusted each of the eight strap so they were taut against my skin. I loved wearing stockings and garters.

Since I was driving and no one would see me, I slipped on a white silk blouse. The buttons were on the left and I left the top four buttons undone. The pants were made from linen and would easily show the bumps from my straps. I opted to drive in my four inch, stiletto heels. I had practiced and done it many times so I was used to them.

My heels clacked as I walked to my driveway. I threw my luggage and jacket into the car before I started on my way. The drive was very boring so it was fortunate that I was able to play with my straps and boobs as I drove.

I knew the hotel had underground parking. I found a spot on the third level basement. I undid my blouse, reluctantly removed my forms and stored them in my luggage along with my heels. I donned some loafers while I covered up my top with my jacket and went to check in.

The room was fairly nice. Two queen sized beds, a small table and couch with a Korean made, big screen attached to the wall.

Unfortunately, the meeting the next day was canceled. It was also unfortunate that I had no chance to check out the maid but since I had the day off...

The next morning, I started my prep. Room service had delivered my favourite eggs Benedict breakfast. I was covered up with a robe so the male delivery person couldn't see my nightly I wore beneath. Although he did give a strange look at my fuzzy pink slippers I wore.

I knew I had time before housekeeping would arrive, so I took a long, warm bath with a peach bath bomb. I made sure my body was properly hairless (not that I had much body hair anyways). I rinsed off and washed my hair. My hair was shiny, thick and black that I usually wore in a ponytail for business. It was long enough to reach in between my shoulder blades but I usually hid it under my business jacket.

Today, I dried it and gave myself some nice, soft waves. I applies some light, barely there make-up with a bit of mascara. Lippy was a very light pink.

My dick was already achingly hard and demanded attention. It was hard (pun intended) to ignore but somehow I did.

I attached my breast forms. These were custom made and matched my skin tone perfectly. The breasts were slightly closer together to create a deep cleavage even without a bra (which I always wore anyways). They were firm but bounced as I walked. The areolae were about three inches in diameter and as I mentioned, the hard nipples were the size of cranberries. Other than a bullet bra, they would always poke through any bra I wore. The plate was secured by tabs that extended up to my shoulders and under my arms.

I hooked my white lace trimmed, light pink bra around my back and adjusted my boobs into the soft satin cups. The outfit included matching bikini panties that didn't quite come up to my hips. I managed to find some pink satin garters that closely matched and would hold up some coral tinted RHT stockings. There was a darker coral seam that ran up the back and the welts were six inch wide and lacy. I attached and adjusted each of the ten straps.

I tied the baby doll cape around me and slid my tootsies into some stripper CFM's. The acrylic stiletto heels were six inches high and made it difficult to walk in. Thank goodness for the inch and a half clear platform sole.

I clipped on some cheap dangly ear rings and wore some wrist bangles that would jingle as I jerked. I set up a hidden camera that would capture the entire room. I pulled out my personal PC (don't use your work one!) and set it on the bed. I laid back on the bed, propped up by some pillows, pulled up some shemale porn and waited.... And waited... And waited.

As nervous as I was, my cock remained hard. I rubbed it through the panties and watched the dark, wet spot grow bigger and bigger. "Shit! I forgot!"

I jumped off the bed and clomped my way to my bag. I reached in and pulled out my jeweled butt plug. It wasn't big but it was hard and noticeable when I wore it. I pulled my panties down over my butt and using my spit as lube, I managed to pop it into my hole with a grunt. "Uh!"

Panties back in place, I returned to my bed position and place the head phones on my head. I decided to put the noise canceling on so I had no idea when I might be found. I found my favourite Chanel Santini videos to play as I pushed down my panties a bit to release my dick. She so beautiful.

Watching her and trying not to stroke myself too fast was difficult. The amount of pre-cum soaking my fist made an extremely efficient lube.

Something caught the corner of my eyes. I looked up to see the housekeeping maid standing there watching. In actual shock, I stopped stroking. I removed my headset to apologize but nothing came out from my gaping mouth.

Her name tag read Ana. She was five-ten or eleven, a number of inches taller than me with a body similar to Ivanka. My eyes darted to her chest which was heaving. She wasn't as big as me; maybe a good sized D or double-D. She had a pretty face with shoulder length brown hair with blond streaks. Ana looked at me and smiled. It was more of a wicked smile. "Don't move!"

Ana moved behind the wall. I heard her shut my door before she reappeared. She had started unbuttoning her light pink smock and let it drop to the floor. She wore a plain white bra that squished her mounds together. Her matching pants were just held up by an elastic waist. She hooked her thumbs inside and pushed them to her feet. Her panties were also plain white but there was a bump inside.

I looked at her crotch and then at her smiling face and then her crotch again.

"That's not a cock!" She nodded her head towards my solid six incher.

Ana pulled hers from the top of her panties. It was still flaccid but the same size as mine. I stared at it as she took it in her hand and grew harder and harder. My eyes widened as it grew bigger and bigger. It was uncut and about the length and thickness of a good sized banana; about nine inches. She finished her statement of fact aping Crocodile Dundee. "Now this is a cock!"

Ana moved to the side of the bed. She grabbed a hank of my hair and pulled my head towards her crotch. She pressed her knob against my lips. I opened my mouth to protest but got a mouthful of hard cock instead. My lips were stretched around her girth and she pushed it inside me. I estimated I had taken in about three-quarters of it as it bumped the back of my throat. Ana used two hands behind my head to hold it as she thrusted her hips forward. She easily slipped into my throat.

I coughed once slightly from the surprise shove but then found it pleasant. I guess Ana did too and complemented. "Good one little sissy. Not a lot of others can take all of me."

She continued to hold my head steady as her hips rocked back and forth. My face smashed against her each and every time. Trying to time my breath was becoming difficult. The lack of oxygen to my brain gave me a slight euphoric feeling.

Finally, Ana let me go and I flopped back on my bed. Her throbbing cock was slick with my saliva and dripped pre-cum. She spun me so my ass was at the edge. She lifted my legs onto her shoulders and yanked my panties aside. She gave me a smirk at seeing my jeweled asshole. "Cute!"

She grabbed hold of the base and slowly pulled it out with a pop. She looked to see where to put it and then decided to stick it into my mouth. "Hold this!"

Ana pushed my knees to my chest. Without using her hands, she positioned her tip against my hole and slowly pushed herself into me. Holding the plug between my lips, I could only take a deep gasp through my nose as her knob popped through. My saliva proved to be an excellent lube as the rest of her length pushed inside me until her hips pressed against my bubble ass. "Fuck you're hole is tight!"

Somehow, I was pleased and just loved the feeling of her inside of me. Slowly at first, Ana pulled out slightly and gently shoved herself back in. Her breathing became heavier as her thrusts became faster and harder. She pressed her body forward so my knees were beside my head. My own hard cock pointed directly at my face.

Ana's thrusts became hard slams. Her knob crashed against my prostate. My own pre-cum was a constant flow as my breathing became a ragged pant. I could tell Ana was about to cum. Me too. I spat out the plug and cried. "Fuck me! Come inside me! I want your cum!"

"Ugh! Ugh! Ugh!" Ana groaned as I felt her huge wads spray inside of me.

"Yes! I'm C...u...u...m...m..ing!" I screamed out. Spurts of my white, hot cum splashed all over my face.

Ana was still firing her load into me as my orgasm shook me uncontrollably. Four hard final thrusts and Ana was spent. She collapsed atop of me as I locked my nylon legs around her torso. I wanted her inside me forever.

"You're a good little fuck!" Ana managed to say after regaining enough to lift herself off of me. Slowly she pulled out her wilting, dripping cock. She grabbed the plug, had me mouth it and popped it back into my aching hole so her cum would remain inside of me. With my legs hanging off the side of the bed, Ana got herself dressed. "I'll be back later. Wear something pretty for me."