My latest business trip started like any other. I'm Michael. I am an executive for a large I/T company and often travel to New York on business. As a bit of background on me, I am 49 and have been happily married for 22 years. I have two kids in college and have lived in the Midwest for most of my life. I live a very active life and have always felt it important that I take care of myself, eat right and workout regularly. I guess you can say that I work hard and I play hard. I have Salt and pepper hair, 6'1" and fairly muscular build. When not biking, jogging or at the gym you will usually find me in a dark blue or gray Brooks Brothers suit. Like most men my age I often find myself fantasizing about sex. Fortunately, in my business I often have the opportunity to live some of those fantasies. The story I am about to tell you is about one of my most recent experiences.
I landed at La Guardia right in the middle of rush hour traffic and took the first taxi I could find to my regular Hilton in the city. After checking in I decided to take a stroll down to the restaurant as I hadn't had anything to eat since breakfast. My plan was to have a nice steak dinner and a few martinis before hitting the sack early as I had an important meeting in the morning. The food at this establishment is good but to be honest, the real reason I keep coming back is because of the location as it is right in the hotel and of course because of the minor fact that they always seem to have some of the hottest waitresses in the city. In the past however, the girls were simply to admire and to fantasize about as I always felt that they were too young. After all, what cute twenty something girl would be interested in a middle aged man like me. My original plan however began to change the second I saw her. My mind began to spin. I couldn't take my eyes off of her. She was adorably cute and extremely sexy. Shoulder length auburn hair, beautiful blue eyes, smooth creamy skin and the most luscious lips I have ever seen.
She walked up to my table in her waitress uniform, short black skirt which accented a pair of incredibly long shapely legs and a white low cut blouse with puffy sleeves.
"Hi, my name is Tina and I will be your server this evening, Can I start you off with something to drink?"
She smiled as she caught me staring first at her beautiful face, then at those gorgeous breasts and incredible legs.
"Oh yes," I replied, "sorry I have a lot on my mind tonight".
"I am sure you do," she giggled softly.
"I will have a very dry gray goose martini with a twist of lime please".
Throughout the evening Tina would drop by my table every chance she had. We began with the typical small talk and I learned that she was older than most of the girls that worked their. She was married and had a 7 year old boy. When she mentioned her husband there was a touch of disappointment in my voice which she instantly sensed. Nevertheless, there is a reason I have been successful in my career. I can be aggressive when I need to be and I tend to get what I want.
After several martinis I built up the courage to ask her when she was off work and if she would be interested in meeting me in the bar for a nightcap. Her first response was that she probably needed to get home. Since that was not a definite no I decided not to give up yet. I paid my bill leaving her a very generous tip. As I stood up I gently grabbed her hand and told her it was an absolute pleasure to meet her.
"And oh, by the way," I said, "I will be sitting right over there at the bar. I do not plan on leaving until you get off of work". It was a Monday evening so the restaurant began to thin out earlier than normal. On several occasions I caught her looking over checking to see if I was still there. Finally around 10:30 pm she came by the bar where I was sitting and asked me for my room number. She whispered that she did not want anyone in the hotel or restaurant to know what she was about to do. Tina then instructed me to head up to my room assuring me that she would be there within 30 minutes. Of course my first reaction was that Tina was blowing me off but I sensed sincerity in her voice and a bit of nervousness. Besides, I had nothing to lose. It was getting late and I had already had more than I needed to drink.
Upon reaching my room, I undid my tie and chilled a bottle of champagne that the hotel provides me for being a regular. I was filled with nervousness and anticipation. Gazing at my watch, 20 minutes passed, 30 minutes, 40 minutes. What the hell was I thinking? Did I really think this chic would actually come up to my room? Suddenly I hear a soft knock at my door. Wow, there she was nervously smiling back at me.
"I am so happy you really came," I said.
She smiled as she walked into the room. I opened up the champagne and poured each of us a glass. I was still feeling the effects of the martinis so I sipped, not really drinking much of it.Tina however quickly finished her glass and tells me that she doesn't have much time. She had called her husband earlier and told him she was going to be working later than normal. I took that as my queue. I walked up to her and grabbed her by the hips, kissing her gently on the lips. My second kiss was stronger and more passionate with our tongues swirling as my hand caressed down her hips and over her perfect ass.
As we continued kissing, she could feel my bulge as it pressed against her belly. Her hands caressed my shoulders and my pecs. Her touch was sending tingles down my spine. We finally broke away from our kiss and she immediately began to undo my shirt and unbuckle my pants. We were both loosing control. I removed my shirt, shoes and socks as I watch her kick off her shoes and drop her skirt. As I imagined, she had adorable toes with red toe nail polish. She was wearing a white silk thong. As she pulled her blouse over her head I noticed a very sexy belly ring and a white bra that she quickly released from behind. Her breasts were perky, perfectly proportioned and milky white. I would guess a B, maybe a C cup. Then again, what do I know about women's bra sizes.
I gazed at this incredibly sexy creature standing in front of me wearing nothing but a pair of white thongs. She gazed down at the tent in my boxers and giggled as she pulled them off and pushed me back on to the edge of the bed. She leaned over and gave me a very wet passionate kiss as her hand slid down to caress my shaft. Tina then got on to her knees between my legs and began to lightly lick the tip of my cock as she looked up into my eyes. She first swirled her tongue across the tip and licked up and down my shaft finally taking my cock fully into her mouth. The feeling of her soft lips and warm mouth was almost more than I can bare.
Tina then began to move up and down on my thick 8 inch cock as her hand stroked my shaft and caressed my shaved balls. I moved Tina's hair away from her face so that I could watch one of the most erotic scenes I have ever experienced. A few minutes into this I began to sense that I would not last much longer. I soon blurted out, "Oh God Tina, you better stop or I am going to cum". This only encouraged Tina as her mouth went up and down on my cock faster and faster, lightly moaning as her mouth was making slurping sounds. She was now sucking harder and harder.
My breathing was becoming very heavy. My hand cupped her head as I let out a loud "AAAAAAH" and began exploding my cum down Tina's throat. Tina continued to stroke my cock as she sucked on the head taking in every bit of cum that I could feed her. I collapsed back onto the bed to catch my breath. Tina then crawled up next to me and we began kissing. My hands began to caress her tits as we continued kissing. I rolled her onto her back as I kissed her neck and ears, whispering into her ears how fucking hot she was and how I wanted to fuck her all night long.
Tina responded to my whispers by moaning, "Yesss please, fuck me, yes Michael I want you inside of me". I moved down to her tits as I took her left nipple into my mouth sucking and twirling my tongue around, then moving to her right tit as my hand slid down her body finally reach her thong. As my hand lightly caressed her mound I felt the wetness of her panties. I continued to kiss down Tina's body from her tits down to her belly, licking and twirling my tongue around her navel, kissing softly, licking lightly. I finally took both of my hands and slid Tina's panties off her thighs and down her legs.
Tina was completely shaved except a small mound of lightly colored pubic hair over some beautiful wet pink lips. As my tongue began to lick her inner thighs, I heard Tina gasp. My tongue then ran up and down her pussy lips and over her clit. I lightly sucked on Tina's clit as she bent her knees, opened up wider and began to moan,
"OOOH GOD YESSS, OOH right there baby,yesss, eat my pussy Michael, mmmmm!"
I slid one finger then two into her pussy as I continued to suck her clit. Tina raised her hips to meet my tongue as she grabbed my head, burying my tongue into her wet cunt. Tina's body began to shiver as she screamed out,
"OOOH GOD YESSSS, I am cumming!" I continued to eat Tina's pussy but the intensity was too much. She pulled me away and started to beg me to fuck her. By this time I was once again rock hard. I moved up as Tina spread her legs wide. I took my cock and rubbed it up and down Tina's pussy.
"You want this don't you baby? You want this rock hard cock inside that tight little pussy don't you?" I said.
"OOH yesss Michael please fuck me!"
I then slid my cock inside of her. She lifted her legs up high to feel every inch of me. I began to move slowly as Tina moaned aah, aah ,aah. I took Tina's legs and placed them over my shoulders and started to pound her harder and harder. My balls were slapping against her ass as I was giving Tina the fuck of her life.
After a period of thrusting into Tina's pussy I yelled, "OH baby I am going to cum". Tina responded by begging me to cum inside of her. I found myself completely turned on by hearing this sweet sexy milf talk like a hot slut. Minutes later, I began to explode into her hot wet pussy.
We cuddled naked in bed as we both dozed off. Suddenly I heard Tina yell, "Oh shit, what time is it?"
"It's a little past 2 am," I replied.
"Jason is going to really be pissed," she stated as she jumped out of the bed.
Seeing this sexy married woman naked in front of me began to get me aroused again. There is no way I could let this one go before I got it one more time. I followed her into the bathroom where I watched a naked Tina in front of the mirror brushing her hair and fixing her makeup. I walked up behind her and pressed my cock up against her back and began to kiss her neck.
"Oh Michael, please don't do that, it drives me crazy."
She felt my cock getting harder. She smiled into the mirror as she tilted her head responding to my kisses. I reached over from behind and begin to caress her tits, rolling my fingers across her nipples.
"Oh baby, that feels good but it's late, I need to go."
My right hand then moved down her hips across her belly and down to her pussy. I started to run my finger over her clit. She let out a soft purr as she reached behind her and started to stroke my cock. My finger slid inside her pussy feeling her wetness. She then took my hand and moved it up to her mouth where she proceeds to suck on my fingers tasting herself as she gazed into the mirror with a very seductive naughty look on her face.
"Damn you are a fucking hot little slut," I whispered into her ear.
She then bent over the counter, got up on her toes and pushed her ass against me. I bent my knees and slid my cock into her pussy from behind. I began to move in and out. The feel of her tight little pussy wrapped around my cock and the sight of that incredible ass is a memory I will never forget. I began to move a bit faster and began thrusting harder and harder into her pussy. I could see her face in the mirror. Her eyes closed, her mouth open as if she was gasping for air.
"Ah, aah , aaah, God yes I love the feel of your big cock inside of me!"
She opened her eyes and looked into the mirror at me.
"You like that baby. Is my pussy tight enough for you Michael?"
"Oh fuck yea Tina!"
As my cock continued to penetrate that tight pussy, I pressed my thumb against her little asshole and pulled back on her hair.
Tina let out a gasp when I touched her there.
"Yes Michael, do it baby, put your finger in there."
As I slid my wet finger into her ass she screamed, "Fuck me Michael, Fuck me! I want to be your little whore baby!"
I started to pound her harder and harder until I couldn't take it any longer. The incredible sight, the feeling of her pussy clinching tightly on my cock and the naughty sounds coming out of her mouth were more than I could take. I let out a loud grunt and explode deep into her pussy for the third and final time.
As we were both catching our breaths and my cock began to soften inside her pussy, we heard her cell phone ring.
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