I was working a large bid opportunity out of town and arranged for the consultant that I hired to meet me in San Antonio for a series of strategy meetings with the technical team. I arrived at the hotel early evening after a rather lengthy delay in air travel due to weather in the Dallas area. As I was unpacking I received a text from Kathy, my consultant, letting me know that she will be arriving late that evening as her flight was delayed due to the same weather system.
After doing the typical travel stuff, checking work email, catching up on the news and sports, I looked at my watch and saw that it was almost midnight. I text Kathy to see if she ever made it and immediately received a reply that she is stuck in Dallas and will not be getting in until 2:30 in the morning. I told her to text me when she arrived and to plan on meeting for breakfast in the lobby at 8. With that I laid in bed and fell off to sleep only to be awakened by my phone.
I blearily looked at the clock, 2:45, picking up my phone I saw Kathy's name on the caller ID. Upon answering Kathy tells me how she just arrived and that the airline lost her luggage. "Do you think you can give me a t-shirt of yours to sleep in" she asks.
"Sure, I am in room 1603, come on over" I reply.
I get out of bed and grab a t-shirt, throw on a pair of workout shorts and soon I hear a quiet knock on my hotel room door. I look through the peep hole to see Kathy, as if anyone else would be knocking at 3am. I open the door to let her in . . .
"Thank you so much, and I am so sorry for bothering you this late" she says as she enters my room.
"No problem, here's the shirt. Will your bags show up in time for our meeting?" I ask.
"The airline is hopeful, they told me they are sending the bag to the hotel when it arrives, meanwhile I am going to hang these clothes up in case I have to wear them to the meeting" Kathy said.
"Well keep me posted in the morning, we have a long day ahead of us" I replied as I walked her to the door.
"Thanks again for the shirt" Kathy added as she gave me a hug, adding "Goodnight."
The door shut and took off my shorts and crawled back into bed. Soon my phone vibrated with a message from Kathy.
"Here's me in your shirt, looks pretty good, thanks again" read the message with a selfie of Kathy in my t-shirt.
I got to admit that it did look good on her and sort of sexy too. It was evident that she was braless as her nipples were hard and poking at the t-shirt material. "Looks good indeed, you may have to model it for me" I text back.
"Come on down, room 1510 - c for yourself" Kathy text back.
"Now" I replied
"Sure, I am wound up from the travel" Kathy replied.
"OK, on my way" I replied and grabbed my shorts and threw on my own t-shirt, grabbing my key as I headed out the door.
I took the stairs down one flight and was at her door in a minute. Quietly knocked and Kathy opened and welcomed me in. "Well" she said as she opened her arms and slowly did a 360 "does your shirt look good on me" she asked with a cute smile.
"Looks great. Is that the only thing you have on?" I jokingly asked.
"Just me and your shirt, had to wash out my bra and panties in case I need to wear them again tomorrow" she added.
"Very nice" I said as my eyes wandered down her body. Her nipples were hard and the t-shirt laid about mid-thigh, causing my cock to squirm in my shorts. Not wearing underwear myself I am sure Kathy noticed as I caught her looking at my growing bulge.
I had worked with Kathy for almost two years, using her as a part-time consultant for large business opportunities that I pursued. I always found her to be attractive and her personality makes her a fun person to spend countless work hours with. Seeing her in this light I had a new view of her, one of a sexy middle-aged woman with lots of sex appeal.
"Come here" she said as she hugged me again "thanks again for the shirt". I could feel her breasts against me and I rubbed her back "no problem, wouldn't want you to have to sleep naked" I jokingly added.
Kathy held the embrace and I am sure she felt my cock against her as my cock grew larger in my shorts. "I like that" she whispered.
"What" I asked
"The bulge in your pants. It's been a while since I have felt that, and I am glad to see that I have that effect on a man" she said.
"Here, give me your hand" I said as I reached for her hand. Kathy looked at me as I took her hand and placed it on my shorts. "Like I said, you look great in my shirt".
"Oh my, you really do" "Kathy said as she rubbed my cock through the shorts.
"You keep that up and you are going to be in trouble young lady" I playfully said.
"You keep that up and you are going to have to fuck me with that cock" Kathy said as she looked into my eyes.
It didn't take long for our lips to meet. Her open mouth met mine and soon our tongues intertwined as she continued rubbing my cock. My hands worked their way from her hips to her tits, squeezing them through the shirt and rubbing her erect nipples between my thumb and index fingers.
"Let me make it easier for you" I said as I slid my shorts down, my hard cock springing out standing at attention.
"Oh my" Kathy said as she looked down, wrapping her hand around my hard shaft.
"I love the big head" she said as her fingers traced the mushroom head of my cock. "I bet that would feel good inside me"
I reached down and pulled my t-shirt up over her head. Looking down to see her perky tits and hard nipples. For a woman in her early 50s Kathy kept herself in great shape. Toned body, flat tummy and a great ass. My hands found her tits and as I pinched her nipples our kissed became more passionate.
Kathy was stroking my cock faster "Fuck me, right here, right now" she whispered in my ear.
In one move I turned her body around, pushing her upper body over "spread your legs" I said, as Kathy moved her legs apart and pushed her ass towards me.
"Guide me inside you" I instructed. Kathy reached back and led my cock to her pussy. My cock slid into her wet opening as I grabbed her shoulders and slowly pushed into her. She gently moaned as I my cock slid in. I reached down to grab her hips and began to rhythmically thrust in and out of her.
"You feel great" she said, adding "I have been wanting this and needing this for a while"
"You feel awesome" I said as I began thrusting harder. From the side I could see Kathy's tits swaying with each thrust, which for some reason really turn me on. "I am not going to be able to last long in this position" I said as my thrusts grew harder and faster.
"It's ok, I want you to cum inside me. I want to feel you explode" Kathy said as she looked back at me.
That sent me over the edge and soon I was pumping my hot cum deep inside her pussy. As I slowly gained composure I reached around, cupping her tits with my cock still inside her.
"That was hot" I said "but we really need to get some sleep if we are going to be worth anything at the meetings"
Kathy moved her ass away from me as my cock slipped out, glistening with cum and her pussy juice. She turned around and got on her knees, and took my cock into her mouth while looking up at me.
"I thought you needed to be cleaned up a bit" she said with a smile then licked some cum off her hands, my balls and cock.
"Wow" I exhaled "you are really really hot"
"Glad you think so. We have a long few days ahead and we can help each other unwind . . . if that is ok with you" "she said.
"No argument from me, but for now I should go back to my room. The alarm will be going off in a few hours" "I said as I reached for my shorts.
"You can spend the night with me if you like, I am calmed down now" Kathy said as she walked to the bed and crawled in.
"I better go to my room so we can both get some sleep, but thanks for the offer. See you at 8:30 for breakfast?" I said as I got dressed.
"Sounds like a plan" Kathy said as she followed me to the door. She bent towards me and gave me a kiss "hope you sleep well"
I made my way back up to my room and went off to sleep. The 7 am alarm seemed to sound way too soon. As I got out of bed I looked at my phone and saw a message from Kathy that read "Call me when you wake up, I some stimulation this morning before we head to the office"
I sent a text back "I just woke up, you know my room number, come on up" . . . "Be there in 5" the text reply read.
I raced to the bathroom to shave and brush my teeth, and soon there was a knock on my door, opening it I see Kathy in the same dress as last night, holding her bra, panties and my s-shirt in her had. "Still no luggage" she said as she made her way into my room.
I locked the door and as I turned around Kathy was removing her dress, revealing her toned body once again. I never bothered getting any clothes on and Kathy's eyes made their way to my semi-hard cock.
"Looks like you are ready for some fun" she said as she walked towards me, reaching for my cock with her hand. I puled her closer and kissed her. "So you need stimulation this morning huh"
"Yes, do you know where I can get some" Kathy sexily said
I walked her towards the bed, and gently pushed her back. She playfully fell onto the bed as I got on top of her. I began to kiss her neck, while my hands massaged her breasts. Working my way down, my tongue circled her left nipple as I rolled her right nipple in my fingers. I slowly moved across to her right nipple, licking, sucking and nibbling. Kathy moaned as I went back and forth between her breasts.
I slowly made my way down her belly as my hands pinched her nipples and soon I was between her legs staring at her shaven pussy. I ran my tongues between her pussy and thigh and then between her lips. She slid her hand down and spread her lips, my tongue circled her clit while I moved a hand down and inserted a finger into her pussy.
I finger fucked her as I sucked on her clit. Kathy grabbed the back of my head, pulling me into her pussy "Oh fuck, I am going to cum" she moaned. Soon she began squirting her juices as I continued licking and fingering her. Kathy's body writhed on the bed and she twitched as she came rather forcefully.
I stopped licking and slowly removed my finger then worked my way back up her body. My now rock hard cock pushed against her lower abdomen. We kissed like tow teenagers and I moved my cock down and slid inside her pussy. I grabbed her and rolled both of us over so she was now straddling me.
With my cock inside her she began to gyrate her hips, grinding her pussy on my cock. I reached up and played with her tits and nipples. She put her hands on my chest and soon began moaning "oh fuck, fuck me . . . I'm cumming again"
"Wow, that really took a lot out of me" she said as she looked down at me and kissed me "I needed that"
"Do you want to cum inside me again or would you like to watch as I swallow you" Kathy asked with a sexy grin.
"Hmmm, both options are good but I will choose option 2" I replied.
Kathy pulled herself off me and made her way down to my cock. Grabbing my cock with one hand she took it in her mouth as she looked up at me. She began stroking me as her head bobbed up and down on my cock.
I grabbed her hair and enjoyed as she gave me one of the best blowjobs I have ever had. After a few minutes I knew I was about to explode "I am going to cum" I said passionately.
"Let me taste you, cum in my mouth I want to swallow your load" She said then resumed sucking me
I grabbed her head and thrust into her mouth as I began shooting streams of cum into her mouth and down her throat. She continued sucking me until every last drop was out then slowly ran her tongue around my head before raising up and laying next to me on the bed.
"That did the trick for me, I think I will be good for the meetings today" Kathy said as she stood, grabbed her clothes and walked into the bathroom. "I am going to shower to get this sex smell off of me, then we can grab coffee before we head out . . . you should join me, you have ‘sex' hair" she playfully added.
I heard her enter the shower as I gathered my clothes and made my way into the bathroom. I couldn't help but think to myself that this is going to be a pleasurable business trip, and fun few days in San Antonio.
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