- 2 months ago
- 16 min read
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I got to the hotel after a long day of travel and quickly unpacked and showered and washed the grime of travel off. I shaved my legs and slowly washed the curves of my body while sipping a nice Rose from room service and got dressed. I was looking to make tonight special so I put on my red satin and lace panties, matching red satin bra, red lace garter belt and black nylons the ones with the line running up the back as they highlight my calves when wearing my 4 inch heels. I carefully did my makeup and styled my slightly longer than shoulder length brunette hair into a wavy modern style and put on my red lipstick. I stopped and stared at myself in the mirror and thought that my 5’ 6” frame which was athletic and toned looked good and said, “Still got it at 38!”
I put on a Navy Satin Blouse, Black pencil skirt, and white blazer. Sprayed my Santal 33 Eau De Parfum on my wrists and rubbed them onto my neck. Then squirted a small blast up my skirt, hoping it would be smelled later on by someone else! I packed up my small Louis Vuitton clutch with the essentials: makeup, credit cards, ID, condoms (you have to be prepared just in case), hotel key and lipstick. I zippered it closed and turned to see the mirror again, “Damn, you are looking good tonight!” And exited the hotel room.
I walked to the elevator and as I passed a young businessman in the hall, I could feel his eyes staring at my ass after I walked by. I didn’t even need to turn around. I got to the elevator and pressed “L” and hailed an Uber to take me to the restaurant. A few heads turned from the crowded lobby when I exited, my heels clicking on the marble floor as I strutted to the front door to catch an Uber. The doorman quickly pulling the door open, “Evening Miss”, he said, “Can I hail you a cab?” “No thanks”, I said, “I already called an Uber but thank you.” “My pleasure”, he replied.
The Uber came and I hopped in. “Angelo’s ma’am?”, said Carlos, the Uber driver. “Yes, please”, I said and off I went in his 2020 Black Chevy Tahoe.
I arrived at the restaurant and have been there many times to know that I caught it at just the right moment as there were few barstools left and in another 15 minutes, there would be none. I sat down at the bar and Marianna, a beautiful Brazilian bartender, asked me what I would like to drink. I asked for a Bombay Sapphire and Tonic and she whisked away to make it.
When she came back, she asked how I have been and I come to this restaurant every time I am in Albany and I replied with the usual chit chat that work was busy but overall things were good. She updated me with he same small talk and retreated to take care of another guest.
I sipped my drink and played with the straw in-between sips. I was looking for a nice businessman, someone who wasn't looking for an attachment, just a night of fun but obviously was not going to peruse the event, I would let it come to me. I was taking in the sights when a young businessman came up and wedged himself between me and another guest and ordered a martini. He was in a navy blue suit, white dress shirt and no tie. He was cute with his nicely styled hair and he looked at me and said, “Do I know you? You look very familiar.”
“I don’t think so but I do get that a lot”, I said. And he looked puzzled for a moment as if trying to figure out where he had seen me before. He collected his drink, paid and walked away without another word. I thought, “Damn, he was cute!” But wasn't about to look desperate, not with the night being this young so I took another sip on my drink.
A few minutes later, he came back and said, “Marriott? 7th Floor? About an hour or so ago?” And I laughed, it was the young businessman who walked past me in the hallway. “Yeah, that is me”, I said. He said, “I smelled your perfume as you walked by and it was very nice, I turned and hoped you would turn around so I could say ‘Hi’ but you kept walking.” “Oh, I could feel your eyes on my ass and didn’t want to come off too easy!” I said. He laughed at this and replied, “Well, when you didn’t turn around, I felt obligated to look at something and your ass was the next best thing to your pretty face.” I blushed a little at that comment and he said, “Mind if I join you?” And I replied, “Sure, by the way, I’m Amy.” He extended his hand and said, “Nice to meet you Amy, I’m Scott.” I lightly took his and and shook it. I replied, “Nice to meet you too!”
As there wasn’t yet a seat for him to join me at the bar, he stood behind me and I turned my seat to face him. We chatted about what brought us to town: He was there to give a presentation on a product he sold to a nearby chemical company and I was there to give a presentation to the NY State Engineering Department on a product I sold. We talked about our products and companies and the trials and tribulations of being a road warrior. The topic got personal and he asked if I was married, no, and neither was he. I asked if he was dating anyone serious, no, and neither was I. And we enjoyed each other’s company that when a seat did open up, he sat down and we ordered appetizers.
While enjoying some oysters and another cocktail, I admired his looks. He was very handsome and well put together in his suit. I could tell he was into me as he checked me out as I walked to the restroom and was fixated on me when I returned as if I was the only one in the restaurant. A few cocktails later, he leaned in an whispered, “You are the hottest one in this restaurant” while his hand felt my leg. I turned and looked at him and our eyes locked. We both leaned into a soft kiss and I could feel his tongue try to pry into my pursed lips. I pulled back slightly and whispered, “That was nice.”
We continued to talk and the restaurant was moving past its prime eating hours and was beginning to empty out. Scott asked if I wanted to head to this local English Pub for a nightcap and I begrudgingly accepted after saying I needed to get up early for work. As we walked to the Pub, he put his arm around me and said, “I am glad we met.” I leaned my head on his shoulder and interlocked my arm around his. We both enjoyed a nice Macallan 18 scotch, neat and enjoyed the pubs atmosphere.
When finished, we shared an Uber and Scott put his hand on my knee. His touch was soft and gentle and he stroked it slightly. I leaned into him and we kissed. I hugged him and whispered, “My room or yours?” And he said, “Makes no difference to me.” And I said, “Let’s go to my room.”
We got out of the Uber and walked arm in arm through the empty lobby and got into the elevator. Scott pressed 7 and turned toward me as the elevator doors shut and leaned in for a kiss. His hands cupped my ass and his touch sent waves of electricity to my groin. I wrapped my arms around his waist and pulled him closer to me.
We got off the elevator and he allowed me to exit first. The chivalry he exemplified made me want him even more. And I pulled up the App to unlock my door, as the lock unclicked, I opened it slightly, and stopped and gave him a kiss. I said, “I have a surprise for you, would you like it now?” Scott replied, “Sure!” And I asked him to wait there for a moment as it would take a few minutes for me to get ready. His intrigue growing by the minute.
I went in and got out of my clothes and picked up the clutter a bit and poured two bourbons. I went to the mirror and checked myself out again. Feeling confident in my red panties, bra, garter and nylons, I fixed my face a bit and sprayed a touch more perfume on me. I took a deep breath and walked to the door with the bourbons. I opened the door and peeked around the corner of the door, exposing just a bit of shoulder and my red bra strap and said, “Ready?” As I handed him his bourbon. He said, “As I will ever be!” And I opened the door and stepped back.
Scott was awestruck at my outfit and took a moment to soak it all in. He put his bourbon down and came in for a kiss. His hand grabbing my ass as I extended to my toes to reach up to him. He reached around front and stopped. He pushed back and had a puzzled look on his face as what he expected in front was not the warm inviting pussy he expected but a nice cock. He said, “Wow, I would have never guessed as you look so beautiful!” I said, “So, it doesn't scare you or freak you out?” “No, I am little shocked but I have enjoyed our conversation all night and love that we are here together and your outfit is amazing, a very nice surprise!”, he said. And I leaned in for a kiss and he lifted me off the ground to make up the difference in height that my heels made up for earlier.
He lowered me and I took his suit coat off and draped it over the couch back. As I walked away, he said, “I love that outfit, it is so sexy and your ass looks great!” I turned and walked back toward him and pulled his tie and guided him toward the bed. I pushed him back on it and jumped on top. As we were making out, I was working to take his belt and pants button down. He was rubbing my back trying to work my bra off and once successful, he marveled at the silicone inserts I used to give me a nice B cup and tossed them all aside and went back to grabbing my tits and sucking my nipples. I pushed him back and slowly worked his shirt off exposing a nice, athletic chest. I reciprocated the chest play and he enjoyed it as much as I did.
I kept kissing his chest, licking his nipples and working my way down to his six pack abs to his pants and got off the bed to pull them off. I exposed a nice pair of green trunks and wondered how many sit ups he did to gain that beautiful v-cut on his hips. I walked over and neatly folded his clothes and placed them by his suit coat on the couch. I walked back and Scott said, “I can see the outline of your cock in those satin panties and its very hot!” “Why thank you!”, I said as I jumped back on top of him for more make out.
I reached down and felt his cock growing in his trunks and I stroked him through the fabric with the palm of my hand. Feeling that he was rock hard, I slowly lowered myself down following the same licking, kissing and sucking motion on his chest on the way down. I lowered his trunks off and his cock sprang out of them as if it was a jack in the box. “Oh, somebody is excited!”, I said. And Scott got up and sat on the edge of the bed and asked me to come closer and looking me in the eyes, he said, “Amy, I am so turned on by you!” I kissed him on the tip of his nose and lowered myself to cock level and took him in my mouth.
Scott leaned back, knees still dangling off the side of the bed, I pulled his cock parallel to the floor and sucked him. Slurping spit onto his shaft as I took it in and out. Grinding it as I worked the tip and sucked his fish head strongly. Scott was moaning in pleasure. I stopped and motioned for him to stand and he complied. I went back to sucking his beautiful cock, allowing it to pop out of my mouth and spring vertical from its stiffness, then rising a bit as I licked his shaft, all while jerking him. His head was tilted backward and he reached down and directed my head to take him in deeper. I did as he felt my wig come loose and he tossed that aside and went back to my head, motioning it in and out on his shaft. I looked up at him, my eyes admiring the intense level of pleasure I was giving him.
I got to my feet and continued to stroke his cock and kissed him. He rubbed my cock through my panties and I asked Scott, “Have you ever done anal before?” And he replied, “No, but I’d like to try!” And I let loose of his cock and went to get the condom out of my purse. I returned with the Durex Ultra Thin and Scott said, “You came prepared!” And I responded, “Never know what kinda trouble a girl might get herself into. Now lay down.” Scott complied.
I unwrapped the condom and placed it in my mouth, but realized I forgot the lube I had int he bathroom, and motioned a Time Out signal as I ran to retrieve, placing it on the night stand. “The panty, garter and panty hose set is so awesome and you look so damn sexy in it, would you mind putting your bra back on?”, he asked. And with that he condom still in my mouth, I retrieved my bra and inserts quickly and put it back on. Voila! I had tits again! Scott began stroking his cock and got it hard again as the break in action caused him to get soft again.
I got back on the bed and took command of Scott’s cock from him and lowered myself to put the condom on. I saw a slick bead of pre-cum on his cock tip and took the condom out of my mouth so I could taste him. I licked the bead off and smiled up at Scott, he smiled as I returned the condom to my mouth and lowered my mouth around his cock, rolling the condom down his shaft. I pulled my head back and said, “Stand by the side of the bed.”, and he jumped out to assume the position.
I grabbed the lube and got on my knees near Scott and he lowered my panties down and off, leaving my panty hose and garter on. I undid the cap and poured a little lube down my ass crack. I reached down and lubed up my asshole with one and then two fingers pumping in and out a few times. I then poured a little more lube down my crack and as I was about to reach back and stretch my balloon knot just a bit wider to lube it better, I felt Scott stick his finger in my ass and he said, “Let me hello you out!” I coyly looked back and said, “Thanks for the help! That feels great!”, as the warming sensation of the lube began to take hold.
He pumped his fingers in and out of me a few times while keeping himself erect with his other hand. I got off all fours and put my feet on the ground and laid across the bed, exposing my ass to Scott and motioned for him to enter. He grabbed his shaft low by his balls and guided his cock to my ass. He slowly pressed against my resistant asshole but the more he pressed, the more it began to welcome him in. He slowly penetrated me, pushing all 8 inches into me and filling my ass with his cock. He pulled out slowly as I handed him the lube. He took the hint and drizzled a bit more on my ass crack and it quickly wrapped around his cock and slid into my asshole, providing a nice slick surface for both of us to enjoy.
Having the friction issue settled, Scott began building a rhythm, pumping my ass with a steady motion. I pushed against him as he inserted me and I was craving his cock to be deeper. The back and forth motion intensified and the slapping of his hips against my ass made be moan in pleasure. He pulled out and I could feel the cold rush of air fill the warmth of my ass and I climbed on the bed on all fours. Scott followed me and climbed onto his knees. He pressed his cock against my ass and it slid inside easily now and the coolness was erased by the warmth of the lube and his solid cock. The motion intensified and the slapping returned. My cock swinging back and forth and Scott enjoyed pounding my ass.
I reached under and began to stroke may cock. Pre-cum was oozing everywhere as my prostrate was getting a good workout from Scott’s cock and it provided a nice coating on my cock and I stroked away. I could feel an orgasm building and I closed my eyes and I jerked myself off and I released, spraying a large load of cum over the bedsheets. My asshole tightened with this release and I gets Scott tense up and release his own load. He shook a bit which vibrated through his hips and against my buttocks. I pulled forward as Scott’s limp cock slid out of me and I rolled over and motioned for Scott to come closer. My cum soaking into the sheets and gluing me to the bed.
As he straddled me, I pulled the cum filled condom off his retreating cock and he quivered with the intense sensations this created on his penis. I held the condom by the top, a big puddle of his cum trapped in the reservoir tip and above. I turned it on the side and spilled some on my chest just above my bra and then took the condom and emptied his batch in my mouth. Swallowing his man sauce in a gulp.
He leaned in and licked my chest clean of his cum and brought it up to me and we shared a long sticky kiss created by a hint of his cum. He said, “I have never been so turned on as I was tonight. You are amazing! I would never had guessed what was underneath your outfit earlier and was hoping to fuck you. And then the surprise you showed me, I somehow was even more turned on by the mystery of it all. I loved this time together and sorry if I came too quick but I was so turned on and then your ass clenched and I couldn’t help it. Can we do this again?” And i replied, “Sure, I loved meeting you and love to be ‘out’ in women’s clothes. I am sorry if you felt like I tricked you but often if I say something up front, I get blown off. I think relationships are built on a connection together and I think we got that connection tonight. Thank you for your openness and for staying with me. I really enjoyed our time and no worries on your quickness, we will have another opportunity to do this again.”