I was standing behind the desk checking a family in when I caught sight of my father in my peripheral vision making his way across the lobby floor with a very stern look on his face. Wonder what has his underwear in a knot. I finished up with the family and directed them toward the elevator as my father stepped up to the counter.
“We need to talk,” he told me
“I am relieving Michele while she is on lunch. She should be back in ten minutes. Want me to meet you in your office?”
“Yes and don’t forget either,” as he turned and walked away.
“What did you do now sis,” a deep voice said to my left, causing me to jump.
I turned and saw my older brother standing there, a grin splitting his face. He always seemed to enjoy it when I got in trouble although this time I had no clue what had gotten my father so bent out of shape. I was the baby of the family; a late baby as my older brothers were 15 and 12 when I came along.
“I have no clue what is up with him,” I answered back as I turned to greet the next guests walking up to the desk. “Welcome to the Windham Hotel,”
As I checked them in I could feel my brother staring daggers in my back. I wanted to turn around and slap the smirk off his face that I knew was there as it seemed to be a permanent part of his demeanor. Just as I finished, Michele came rushing behind the counter.
“Thanks,” she told me putting her stuff in her cubby hole under the desk.
“No problem,” I said as I moved out the other side in front of my brother, giving him the evil eye before I went to see what my father wanted.
When I reached his office, I tapped lightly on the door, waiting for him to tell me to enter. When he finally did, I stepped inside and shut the door behind me. When I turned around I was shocked to see someone else in the room. The man appeared to be in his fifties, dressed in a nice navy blue suit, his silver hair combed to the side as he eyed me up and down. The face looked familiar but I could not put a name to it.
“Bailey, this is Mr. Walker, the gentleman who wants to build a casino next to the hotel. You met him at a convention about a week ago.”
“Yes, I did. Glad to meet you again Mr. Walker,” I said holding out my hand for him to shake before I sat down, wondering what this had to do with me. I was never involved in the business dealings of the hotel.
“Mr. Walker here said that he approached you about the project and insists that you be the one that he talks to about his plans. I explained you didn’t deal with those things and he should talk to me, Peter, or Justin,”
I sat there in silence, wondering where this conversation was headed and why I was even summoned to his office but I soon found out.
“I told your father that if you did not work with me on the project, I would look elsewhere for a building site,” Mr. Walker explained before my father had a chance to say anything else. “I would like to take you to dinner tonight and discuss the plans. Will eight o’clock be okay? Classy dress,” as he stood up. “I will meet you at the reservation desk,”
I quickly looked at my father, who was sitting back in his chair, his hands clasped together on his chest, a look of displeasure on his face. This was going against all he believed in; a woman should not be involved in the business dealings of the hotel; that I would mess things up some way and cost them the contract.
“Ah…sure that will be fine. I’d like my father to join us as he knows all about those things.”
“Not this time. You and I or the deal is off. Your call Bailey,”
Knowing what a lucrative business offer this was and the amount of revenue a casino next door would bring in I had no choice but to agree to Mr. Walker’s terms. He stood up, took my hand in his, and kissed the back of it before he let himself out of the room, shutting the door behind him.
As I stood up to leave my father said, “I don’t know why the hell he wants to deal with a woman who has no clue about these things. I want a full report of what went on at the meeting Bailey in the morning, eight o’clock sharp. Understand?”
“Yes father,” I told him, letting myself out of the office and hoping to be able to escape to my little apartment in the hotel.
“What is going on sis?” Peter asked as soon as I came out of the office. “I saw that old man come out first so what did you do? Did you overcharge him for his stay? Did he not get any clean towels?”
“None of the above,” I said quietly, interrupting before he got another accusation in. “He mentioned a week ago at a convention he was attending how he would love to build a casino on either side of the hotel so I directed him to father. He does not want to deal with my father but with me,”
Peter started to laugh, “You have to be kidding me. No woman knows about those things. It should have been one of us,”
“I agree but he is insistent that I have supper with him tonight…alone,” and with that parting shot, I turned on my heel, leaving Peter just standing there staring at me.
Before I left my apartment, I gave myself one last look in the mirror. When he said classy, I just hoped that my little black dress was okay because that is as classy as I could get. I let my hair, which reaches to the middle of my back, hang loose, and topped my classy look with a pair of black three-inch heels. Grabbing my clutch, I made my way to the lobby.
Part of me was excited but the other part of me was scared to death. I could not believe that a man who wanted to build a casino to be part of the hotel insisted that I help him with the contract plans. My father and brother were right; I did not know that much about the Windham Hotel business but I did know some things, especially about contracts. I had been taking online classes to get a business degree for the past two years. When I graduated in a year, I planned to leave and worked for a company that would realize my worth.
As I made my way across the lobby, I saw my father stepping out of his office, looking my way. He just gave a slight nod and continued toward the elevators.
“Very classy,” Mr. Walker said when I walked up to him. “I was going to bring you flowers but didn’t want to make you go back to your apartment to put them in water but I have a special dessert planned,”
I figured that we would be going to the restaurant in the hotel but he took my arm and guided me out the front door, requesting his car. A few minutes later his BMW was delivered. He opened my door and helped me inside before going around to get in his side.
“Is Italian okay with you Bailey?” he asked. “I discovered this unique Italian restaurant on my last visit here,”
“You mean Mama Louisa’s. I love her food, Mr. Walker.”
Taking his hand off the wheel, he placed it on top of my knee saying, “Please call me Trent. Mr. Walker sounds too formal,”
“Alright Trent,” I said trying to subtly move my knee away from his hand. I was no virgin but I was still a bit uncomfortable with his touchy-feeling attitude. “Why were you insistent on talking with me Trent?” wanting to get that burning question off my mind.
“I am not chauvinistic like your father and find myself enjoy working with women on these types of projects. They seem to have more of an insight into what players want in a casino,”
“Alright,” I told him unsure if he was telling me the truth or not. I was glad to see the restaurant up ahead as I needed to get out of these tight quarters with him to give me a chance to breathe and think. I had a feeling I knew where he wanted this evening to end but I was not about to put out for a lucrative contract. I didn’t work that way…or so I thought.
When we walked into the restaurant, Trent gave his name and we were immediately escorted to a cozy corner table.
“What would you like to drink Bailey? White or red wine?”
I wanted to make sure I kept a clear head so said, “Just water. Sorry, but I am not a wine drinker. Hope you understand.”
We kept up small chatter while waiting for our food, saving the business talk until our dinner was served. After receiving our meals, the first few minutes were spent enjoying the delicious food, then Trent stated, “I have a confession to make. I do not need you working on the casino contract to award it to your father; I just want you to have sex with me. If you agree to do so, the contract for building the casino on the hotel property will be your father’s, or I will look elsewhere. Your move,”
I dropped my fork on my place, torn between throwing my plate of food in his face and walking out or, God forbid, considering his proposal. I had been propositioned many times since I turned eighteen but never for a business deal.
Straightening my spine, I looked him straight in the eyes and asked, “Are you serious?
“Go back to my hotel room with me tonight or I can go to your apartment?” Trent answered. “I promise you will not be disappointed,”
I forced myself to take a long drink of my water as I weighed the pros and cons of his proposal. I figured that he was in his forties, so that would put him at least 15 or so years older than me and I was not really into older men. It made it seem like I was having sex with my dad, which caused a shudder to go up and down my body. I felt him take my hand and give it a little squeeze. I knew he wanted an answer but was not sure what it would be.
Do I want to prostitute myself just to get a contract for a casino? But wait, that is not exactly the right word since I am not being paid for my services. Or am I with the promise of a contract?
“This will be just between us, right? No one else, especially my father and my brothers, will know how they got the contract?”
“This is just between us. A one-time deal and done unless you decide you want to continue,” Trent assured me.
“I want the contract signed and notarized first,” I told him.
“If you insist,” he replied. “I can have my attorney bring the contract here before we finish eating.”
Swallowing hard, I said, “Okay but if word gets out how we got the contract I will deny it and sue you for slander. Do I make myself clear?”
Trent nodded as he pulled out his phone and called his attorney. I had no more appetite but forced myself to eat a few more bites, not believing what I was about to do to get the contract but it would bring in more revenue, and maybe my father and brothers would stop thinking I was just a ditzy blonde that was only good for doing reservations. It never occurred to me that with their Neanderthal thinking they would probably think I got it by sleeping with him as that was the only thing a woman had to offer to get what they wanted.
As we were finishing up our meal, I looked up and saw a short, kind of dumpy, bald haired man power-walking across the restaurant toward us carrying a manila folder in his hand. Stopping in front of our table, he handed the folder to Trent.
Pulling out what I figured was the contract, he passed it over to me. With the lighting so dim, I pulled out my phone and turned on the flashlight to read it over. I was not signing anything without reading it. It was a simple contract so it did not take long for me to read it. Since everything seemed to be in order, I pulled out a pen and signed it.
“Here is a copy of the contract you just signed Bailey. You can also read it over if you want to make sure that it is the same. If you want we can notarize it also.”
I gave it a quick read over and then had it also signed and notarized. I put it in my clutch and said, “I am ready to leave if you are Trent,”
Turning to his lawyer Trent told him, “That will be all Harry. I will see you in the office in the morning and we will set up an appointment with Windham Hotels to go over everything. Thank you for making a special trip.”
“You are welcome sir,” as he turned and left.
Trent got the waitresses attention and paid the bill, then stood up and offered me his arm. All too soon we were back at his hotel room. I figured that it would be easier to sneak out of his room than it was for him to sneak out of my apartment since my father and brothers also lived on the same floor as I did.
As soon as we stepped into the room, Trent took my purse and laid it on the counter, then turned and pulled me into his arms before leaning down and capturing my lips with his. I could taste the combination of red wine and marinara sauce on his lips. I was a bit surprised to find that it was a strong kiss and not a soft one. I felt his hand travel down my back to cup my butt, pulling me closer to him.
As if my arms had a mind of their own, I wrapped them around his neck, kissing him back. Soon he pulled back, turning me around as he tugged the zipper down the back of my dress, slipping it off my shoulders to let it puddle on the floor, leaving me standing there in my lacy black bra with matching thong and thigh high stockings and heels.
Kissing my shoulder, Trent whispered in my ear, “Looks like you were wanting warm my bed with the sexy lingerie you are wearing,” as he cupped my breasts in his hands, his thumb rubbing over my nipples, sending a shiver through my body.
Trent continued to kiss me as he moved to pinch my nipples until they were hard little beads. I could feel his hardening shaft pressing against my backside and from what I could tell, it was impressive. I could not resist the urge to rub myself against his crotch, earning a moan in my ear. Stopping what he was doing, Trent reached around and unfastened my bra, moving it down my arms until it fell on top of my dress. Trent slowly turned me around to face him, kissing me hard, his tongue demanding entrance.
After several minutes Trent took a step backward and dropped to his knees, his hands on my waist, pulling me closer to his face. Inhaling deeply Trent whispered, “I love the smell of a woman in heat and your scent is so intoxicating,” as he kissed the front of my crotch, his hand moving between my legs, rubbing back and forth across my pussy as he kissed his way downward.
Trent gently pushed my legs apart to make it easier for him to kiss my pussy through the little strip that was covering, alternating between kissing and blowing hot air against me as both hands massaged my butt.
Very slowly he moved the material to the side so he could slide a finger, then another one deep inside of me, bending them so they touched my G-spot, making my legs feel weak and rubbery, I put my hands on his shoulders to balance myself. I could feel myself becoming wetter with each push of his fingers and the swipe of his tongue. I knew it was only a matter of time before I drenched his face with my juices.
Suddenly he pulled his fingers out and stood up before swooping me up in his arms and carrying me over to the bed, depositing me in the middle.
“Don’t move,” he ordered as he began to undress. I watched him slowly undress, becoming more and more impressed with each bit of his body that he uncovered. As he pushed down his boxers I could not help but let out a little gasp of surprise at the thickness and length of his cock; at least seven inches long and three or four inches thick. Just looking at his magnificent body was enough to make me rethink my feelings about having sex with an older man.
Trent must have heard my little gasp of surprise because when my eyes met his, he had a slight smirk on his face. I felt my face heat up as he walked toward the bed. Reaching down, Trent hooked his fingers in my thong and tugged it down and off my feet, tossing it over his back.
“Give me a minute and I will take my shoes off,” I told him when I realized I still had them on.
“No, I find it very sexy to have sex with a woman wearing thigh-highs and heels,” he said as he made a detour toward his bathroom.
When he came back out, he was carrying several small packets between his fingers. He put them on the nightstand and crawled on the bed between my knees, pushing my legs farther apart. I could feel him rubbing against my wetness. Leaning forward, his lips captured my nipple, his tongue flicking over the tip while his fingers played with the other, and then he switched. By the time he started kissing his way downward, I was dripping wet and on the verge of having an orgasm.
Trent’s hands went under my butt, raising me slightly upwards before his tongue swiped up and then down between my folds and then dipping inside. Find my clit, his tongue swiped over it sending waves and waves of pleasure up and down my spine. Within minutes I felt like I was coming apart at the seams as my orgasm ripped through my body causing me to twitch and wiggle all over the bed.
Laying there, recovering I watched Trent grab a packet off the nightstand, rip it open, and quickly cover himself. Settling between my legs, he guided himself slowly inside, his hands under my ass. I carefully wrapped my legs around his waist, being careful not to poke him with my heels. Having sex with my shoes on was a new experience for me.
Leaning forward, Trent kissed be hard, our tongues dancing as he moved in and out, slowly working toward his orgasm. As we both got closer I began to breathe heavier, the heat building up in my inner core. Without really thinking I pushed my heels into his ass as I started to tumble over the edge, Trent following me. When it was over, I let my legs fall to the bed. Trent pulled out and crawled off the bed slowly removing the condom.
When he turned around to go to the bathroom to dispose of it, I let out a small cry when I saw the indentations on his ass from my heels. “Oh my gosh, I am so sorry,” I said as I sat up and started looking for my clothes, finally giving up trying to find my thong.
When Trent came back out of the bathroom, he asked, “Sorry for what and what are you doing?”
I stopped, holding my dress in one hand, saying, “What does it look like I am doing? I am getting dressed. I cannot go back to my apartment naked. And I am sorry for putting marks on your ass from my heels. I knew it was a bad idea to keep them on,”
Trent reached out, took the dress out of my hands, and tossed it over his shoulder. “Stay…and you can take your heels off but keep the thigh-highs on,” giving me what I now considered his special smile. “And these are badges of honor; proof that I drove you so hard over the edge that you had to grip my ass to keep from falling to hard and fast,”
Despite how I came to be in his room I could not help but start laughing. Finally catching my breath, I managed to say, “You are so full of it Trent,”
He smiled and asked again, “Will you stay for a while longer. I know I agreed to a one and done deal but I had no idea how enjoyable making love with you would be so if you want to leave, I won’t stop you.”
Thinking for a moment, I said, “Sure,” as I sat down on the bed and removed my heels and then my bra. Standing up, I walked over to Trent, kneeling in front of him, taking him in my hand, kissing the head. Using my tongue I licked around the head and under the rim, then down the backside and up the front to the head. I could slowly feel him hardening in my hand.
I looked up at him watching his eyes and facial expressions as I wrapped my lips around him, slowly swallowing him until the head brushed the back of my throat, my lips almost against his pelvis. I gradually moved back to the head, my tongue swirling around and under it. I could hear Trent moan as I felt his hands entangle themselves in my hair.
“Damn Bailey, that feels so amazing,” Trent said softly. “Your lips and tongue feel like silk against my cock. Damn!”
I took him back in my mouth and then back out, my lips tight around his cock as my tongue worked its magic. I reached under his cock and gently squeezed his balls, massaging them gently with my hand. As he neared his orgasm, I could tasted his pre-cum on my tongue and feel his balls tightening.
I felt his hands on my shoulders, gently pushing me back. “I want to come inside of you Bailey. On your knees,”
I did as he requested, my fingers dipping down to rub my clit. I heard the packet rip and the bed dip as he joined me on the bed.
“So sexy,” he whispered as he rubbed the palms of his hands up and down my nylon-clad thighs. Positioning himself at my opening Trent softly pushed my fingers away, replacing them with his thumb as he rubbed circles on my clit, causing my juices to start to flow.
By the time he started to ease himself inside of me, I was a quivering mess and on the verge of another orgasm. Trent pushed inside, angling himself so he was brushing against my clit as he moved in and out, his hands gripping my hips tightly. Gradually he began to increase the speed and depth of his strokes, bringing me closer and closer to the edge.
I gripped the bedspread in my fists, pushing my face against the bed to muffle my screams as I came hard, my juices squirting all over his cock, dripping down my thighs, my inner muscles squeezing his cock tightly. Giving me little time to recover, Trent gripped my hips tighter as he began to move harder and faster. Trent gave out a low howl as he emptied himself deep inside of me. Finally, he collapsed on my back, pushing me into the bed. Planting a few light kisses on my shoulder first, he then slowly rolled off and laid beside me on his back, both of us breathing deeply.
“Wow!” was all I could mutter as I turned my head to face him. I wiggled closer and gave him a light kiss.
“Not bad for an old man,” Trent teased. “And you don’t have to say anything. I saw it in your eyes when I asked you to warm my bed but that is okay. Truthfully, I am not as old as you might think. The silver hair always throws people off,”
“How old are you?” I asked, curiosity getting the best of me.
“I am 35,” he stated matter-of-factly. “All the men in my family, for some reason or other, had their hair turn silver by the time they hit 25; it is some genetic thing.”
I propped my head upon the palms of my hands and looked at him, trying to see if he was teasing me or not but from the look on his face, I could see he was telling me the truth.
“Come here,” he told me stretching out his arm.
I wiggled over and curled up next to him, glad now that I had agreed to go back to his hotel room. It was some of the best sex I had ever had. And my father got his contract on top of it. I am not sure who got the better deal but liked to think I did. We laid there quietly, each lost in our thoughts. When I heard Trent lightly snoring, I decided it was time to head back to my apartment.
I quietly crawled out of bed and dressed. Grabbing my purse, I snuck out, shutting the door slowly and quietly until I heard it click. I no sooner made it into my apartment when I heard my phone go off, indicating a text. I looked and saw it was from my father.
Did you secure the contract Bailey or did you screw it up?
I quickly texted back, I have the signed contract. I will get it to you in the morning, and with that, I turned the phone off and went to take a shower to help relax the muscles I had not used in a long time, wondering if I would have a repeat with Trent sometime in the future or was it a one time fling.