Cathy FL Pt. 01

Cathy was a little fireball of a woman that I worked with. Feisty at about 5'1" she and I had some fun times with her over a couple of years that started with an out of town assignment for the company.

Cathy had transferred into the office about six months before we had been assigned to work together. She was about 5'1" tall with the tight body of a gymnast with small 32A tits and a wide ass.

I had met her in the office a couple of times and at some happy hours but had never spent any real time with her. We had been assigned a client engagement in the western part of Texas.

We got to our hotel the first night, a wonderful Holiday Inn, and checked in. They gave us adjoining rooms with a connecting door. We were going to get settled in and go out to dinner. After about 15 minutes I heard a knock on the adjoining door. Opening the door Cathy was there having changed into jeans and tshirt.

"Ready to eat? I'm starving."

"Sure."

We headed over to a sports bar we had seen nearby. Ordered drinks and dinner. Scotch rocks for me, scotch and Dr. Pepper for her. Interesting drink combo and in my estimation a complete waste of scotch. Though still somewhat impressed, I had not met many women who liked scotch.

Over dinner we got to know each other better. She had gone to school in Florida and had transferred from a Miami area office to Dallas to get some more exposure to additional industries. She had a boyfriend and lived in an apartment with her dog. Told her about the wife and our infant son.

Enjoyed talking with her and getting to know her but it sounded like there was not going to be any sleeping with coworkers on this trip. On the way back to the hotel we stopped and picked up a bottle of scotch and some Dr. Pepper for the week. Settled back in my room, made some drinks and settled on a movie to watch. We both laid on the bed watching the movie but kept our distance. When the movie was over, she went to her room through the adjoining door and interestingly enough did not close hers all of the way.

Pretty uneventful first week, we wound up working about 12 hours a day and flew home late Friday afternoon. Each night was more or less like the first. One week down, three to go.

The next week started off the same, work, eat, hotel, movie. She was still leaving the door open which I found interesting. On Wednesday morning I got a glimpse of her in shorts pajamas and top.

When we got back from dinner Wednesday night she went to call her boyfriend. They usually chatted every night. When she got done she came back to my room and headed straight to refill her drink with more scotch than Dr. Pepper.

"Everything okay?", I asked.

"Boyfriend is being an ass. He does not like that I travel and that I am with another guy."

"Tell him nothing is happening?"

"Yeah but he does not believe it. He thinks it puts me in a tempting position to be out like this."

"Not very trusting of you. Clearly does not understand that you have a professional life."

"Yeah, not sure what I am going to do about it."

She got kinda quiet after that and had quite a bit to drink while we watched a movie.

When she went to her room she stopped and looked back, "Thanks for being understanding. Don't want to drag you into my personal life."

"No problem, we have to look out for each other when we are on the road. Really not fair of him to treat you like that. Probably not something you want to deal with since we all travel a lot."

"Yeah, good night."

"Good night."

Got up to piss and as I passed the adjoining doors I noticed she had left hers wide open. I could see her bed, but not her. She was in the bathroom.

I sleep naked so I stripped down, turned off the lights and went to bed. After a few minutes her lights went out too.

The next morning I got up and the doors were still open, she was still asleep, I saw her in the bed as I passed the adjoining doors. Went into the bathroom, showed, shaved and got ready to get dressed. Turning the lights off to not disturb her I went naked back into my room to get dressed. As I passed by the adjoining doors I heard her say "Good morning."

"How are you?", I replied as I stepped past the door to get out of her sight.

"I didn't sleep well."

"Why?" , I asked as I stood there naked talking to her through the wall.

"I could not stop thinking about what an ass he is being and it's not the first time."

Her voice sounded closer, looking around she was standing in the door in the pajamas I had seen her in before. She had known I was naked but moved to the door anyway, interesting. If she wanted to see me naked then fine.

She stood talking about her boyfriend and the other times he had been an ass, all while watching me. I began to get dressed, but my cock was definitely getting aroused and I am sure she noticed.

I was just about finished dressing when she said, "Thanks for listening, I appreciate it. See you downstairs for breakfast in a bit."

She went back in her room, partially closing the door this time. Maybe this was not going to be so bad after all.

We went to the client. Meetings kept us apart most of the day, but when we were around she was very quiet, kinda sad. About 6 pm we headed back to the hotel.

"I don't really feel like going out to eat," she said as we drove back.

"Want to just pick something up?"

"No, I'm not hungry. Why don't you just drop me off at the hotel."

"Okay, be glad to bring you something."

"No thanks, just need some quiet time."

"Sure."

I dropped her off and went to a bar nearby that had great hamburgers. Ate at the bar and had a couple of drinks.

When I got back up to my room the desk light was the only light on. The adjoining doors were wide open and I could not see Cathy in my room.

"You here?"

"Yeah," I heard her say from her darkened room.

"You okay?"

"No, I'm not."

"Can I do anything?"

"Not right now, just going to sit here in the dark for a bit."

"Okay, let me know if you need anything."

I walked over to the desk and noticed that the ice bucket was about 1/2 full and there was a good amount of scotch gone. I made myself a drink and changed into gym shorts and a tee shirt. Falling into bed, I turned the tv on.

"This going to bother you? Want me to close the door?"

"No, it's fine."

I watched tv for a few minutes. Cathy poked her head in the door, "Can I come in?"

"Sure."

She came through the door, went to the scotch and poured herself a drink. Her makeup was smeared on her face from crying and she was wearing her pajamas.

Looking at me she said, "He broke up with me. Said he could not handle me being out of town so much with other guys. He thinks I am fucking you every night."

"Sorry he is being such an ass."

"Thanks, can I hang out here with you? Just need some company."

"Yeah, no problem, whatever you need."

Cathy moved onto the bed next to me, closer than she had sat before.

We silently watched the movie for a while. I got up a couple of times to refill my drink and hers. I could tell she was getting pretty tipsy, especially since she had not eaten anything.

The movie ended and I turned the TV off. It was getting a little late. We laid there quietly for a couple of minutes.

"Ever sleep with one of your staff," she asked, breaking the silence.

I looked at her, "Yes I have."

"Your wife knows?"

"Not to my knowledge."

"I really do not want to be alone tonight. Can I stay with you? Not looking to fuck, just do not want to be alone."

I was still looking at her and my cock was starting to stir a bit, "Sure, we can do that."

"You sleep naked, don't you? I saw you a couple of times when you got up in the morning."

"Yes I do, but I can skip that tonite if you like."

"No, do what you normally do."

"Ok, that works for me."

I got up and went to the bathroom and she did the same. Cathy came back into my room and got into bed. She had cleaned up her makeup. I went over and turned the light off and walked back to the bed, slipped my gym shorts and tee shirt off.

"Can I get you to hold me for a bit?"

I rolled to the middle of the bed holding my arms out, "Sure."

Cathy rolled over and met me in the middle. We held each other in our arms lying quietly in the darkness. Our upper bodies were touching as were our legs, but no middle contact. My cock had gotten hard and was throbbing between us. After a couple of minutes Cathy pulled away a bit, edged up and started kissing me. As she did we pulled closer and my cock pressed up against her pajama covered pussy. I reached down and adjusted my cock to rub against her pussy as we continued kissing. My cock pressing on her pussy made her start to hump me slightly.

Moaning lightly she broke away from our kiss and rested her head on my shoulder. Sliding down caused my cock to push harder against her covered pussy. Moving my hand over her ass to pull her closer I could feel that she was not wearing panties under her pajama shorts. She moaned as I began to slowly hump her.

"I've never slept with a boss before," she said.

"You okay?"

"I don't know. Always said I would not do this. But it feels so good right now."

"Need me to stop?"

"I can't let you fuck me, I am not on the pill and did not bring my diaphragm."

"We can do whatever you are comfortable with," I answered.

"Thank you," she said as she pulled away from me.

"No problem." I said as I thought I would have to go jerkoff in the bathroom.

"I will be right back," she said as she hopped off the bed.

She went into her room and the bathroom light came on. Heard her rummaging around then the light went out and she headed back to my room. Stopping at the side of the bed, I could see she had something in her hand. She laid it on the bed and unbuttoned and removed her top then slid her pajama bottoms off. She got back in bed and slid her now naked body over to mine. Reaching out she grabbed my cock touching it for the first time. It had lost a little of its hardness but sprang back to life as her hand squeezed it. I reached between her legs touching her trimmed pussy at last. My finger slid across her soaked pussy, she was very wet. Cathy sucked in her breath and trembled as I made contact with her pussy. I rubbed my fingers over her clit and then slid two fingers into her soaked pussy. She pushed her pussy against my fingers and started humping my hand as she stroked my cock.

Her pussy was almost flowing and soaked my hand as I fingered her. She continued to hump my hand as I slid a third finger into her and rubbed her clit with my thumb. Suddenly she let go of my cock and pushed me onto my back, my hand pulling away from her pussy as I rolled over. Cathy then straddled me and began to slide her pussy up and down the length of my cock. I could see her small tits now, her hard nipples standing up on her chest. She was rubbing faster on my cock, but her well lubricated pussy made sliding over my cock very smooth.

Her breathing was becoming very labored and she collapsed on top of me as an orgasm slammed into her causing her body to tremble. I could feel juices from her pussy soaking my cock and balls. As the orgasm was subsiding I slid her up my body a bit, my cock lining up with her pussy. I was pushing gently against her pussy moving my cock around her slit.

Cathy must have sensed what was coming as she looked right in my eyes as I rammed my cock all the way into her soaked pussy in one stroke. She gasped as I entered her unprotected pussy. I felt her pussy clench and pulse around my cock and small tremors shook her body.

"No we can't," she whispered, laying her head back on my chest, not making any move to get off of my impaling cock.

I did not move, just laid there with my cock in her pussy. After a minute or so she pushed herself up and slowly slid off of my cock. She rolled to my side and with one hand began to slowly stroke my cock.

"Thank you, I just needed something to relieve the stress. I'm sorry you cannot fuck me."

"I understand. What you are doing feels nice," I said

"You ever fuck someones ass crack?"

"Yes I have. Do you like that?"

"Oh yes, feeling your slick cock sliding in my crack then hot cum on my ass and back. Feels so nasty."

She reached over me grabbing the tube she had brought into the room. I could see now that it was a hand lotion. Opening the tube she squirted some lotion on her hand and rubbed it on my cock. Then getting up on her hands and knees she squirted more in the crack of her ass.

I moved behind her and she grabbed my cock and placed it in the crack of her ass. With her still holding my cock, I began to rock back and forth like I was fucking her ass as she squeezed my cock. I always referred to this as simulated anal sex. My wife did not like getting her ass fucked but would do this for me. After a couple of minutes of this I had Cathy lie down with a pillow under her hips. In this position I could control things a little better and Cathy could relax. I squirted more lotion in her ass crack. Smearing it around with my hand, I f pressed a finger against her asshole. Cathy flinched but did not say anything. Maybe fuck her ass?

I laid on top of her and began to slide my cock in the crack of her ass. It was very slick and felt wonderful. Rising up a bit my cock slid further down her crack towards her asshole. Cathy had moved a hand under her and was playing with her pussy as I continued to ride her ass. I could feel my cock beginning to fill with cum. Cathy was fixated on playing with her pussy. Sliding my cock down her ass I got near her asshole and pushed my cock forward. Hitting her asshole I began to push forward. Cathy's body tensed as the tip of my cock started to push into her ass. She tried to pull away from me but I kept moving forward and when she stopped my cock popped past her sphincter and into her ass. Air rushed from her lungs as she yelped and then groaned. I was all the way in her ass and began to fuck it. I was close and her ass was so tight and hot.

I had only gotten a few strokes in when I felt the cum racing up my cock. My cock swelled and I started cumming in her ass. Cathy was trying to get out from under me, but I had her pinned down and my cock all the way in her ass. I am sure she could feel me pulsing deep in her ass. When I finished I raised up off of her a bit. This allowed her to rotate her hips and my cock slid out of her ass.

I rolled off of her and she turned to face me.

"I can't believe you fucked my ass!"

"It just kinda slipped in there," I said.

"Yeah and when it "slipped in" you just kept fucking me. It hurts when you ram it in like that."

"That the first time you ever had a cock in your ass?"

"No, but you could ask, give someone some warning. I don't do it very often and when I do I need to go slow with it."

"I will remember that next time, sorry."

"You think there will be a next time?"

"I certainly hope so. Your pussy felt so hot and juicy and your ass is perfect for fucking."

Pretty certain she smiled when I said that.

Getting up off the bed she said, "I need to clean up a little. Can I sleep in here tonight?"

"Yes, I would like that."

Cathy went into the bathroom and cleaned the lotion off of her ass. She brought a warm washcloth in and cleaned my cock and balls. She then kissed me and said, "Thank you."

"Believe me it was my pleasure."

"I am still not sure about this fucking a boss thing."

"Let's take it slow and see where it goes. I think it can be fun, but I am not holding you to anything."

"Thanks, that helps."

We got under the covers spooning and fell asleep together naked.

Maybe this will be a good trip after all I thought as I went to sleep.