Company Xmas Party Ch. 08

We continued to dance for awhile longer, and then decided to call it a night. We returned to the hotel, and I asked her if she wanted to grab a drink at the bar, and relax out by the pool with it. She agreed, and we got our drinks, and headed that way. It was dark, and quiet. They had placed chairs, and chaise lounges under canopies, with three sides covered. I led Diane to one of these, and we sat in our chairs, and sipped our drinks.

We chatted idly for some time, even when our drinks were done. I slipped from my chair, and knelt before Diane. I ran my hands up her legs, to her hips, and rested my head on her thigh. She ran her fingers through my hair, and I thanked her again for inviting me along. We remained like that for a few moments, and I began to smell her arousal.

"Ms. Diane, are you getting horny again?" I asked her.

"I am in a skirt with no panties. My bare ass is on this chair, and you are rubbing your fingers over my bare skin, which should normally be covered. I think I need you to take me upstairs."

Wrapping my fingers around her hips, I pulled her to the edge of the chair. "You know, it has been far too long since I tasted you." I nuzzled my nose between her thighs. I looked up at her in time to see her roll her head back, and she lifted her feet up, placing them over my shoulders. With access now given, I moved my mouth down to her pussy, and ran my tongue over her lips. She began instantly moaning, and her legs locked a little tighter.

Deciding to not waste any time, I pressed my tongue as far inside of her as I could, and began thrusting it in and out. With a yelp, she grabbed my head, and almost painfully pulled me tighter to her. Very quickly, she began clawing at the back of my head and neck, and her juices began flowing. I kept up the best I could as I reached a hand for my glass. Finding it, I grabbed what I was searching for. I moved up, and found her clit, and attacked it mercilessly, and placed my fingers, now holding an ice cube against her opening. I pressed it against her, and she let out a low scream, but never relinquished her grip on me. I pushed the small piece of ice inside of her, and move my tongue back down. I inserted my tongue again, and pressed the ice in a little further. She had become extraordinary wet, and I took that to mean she was enjoying this new sensation.

I pressed my thumb against her clit while continuing the tongue fuck her pussy, and she began bucking her hips off the chair, and making far too much noise. I was becoming concerned that someone might come to investigate. I decided that it would be best to continue this in the room, rather than risking getting caught, and kicked out of the hotel. I pulled my face away, and she tried to pull me back. "No, no, no, don't stop." she pleaded. I told her we needed to leave before someone came. "Ung, I almost came! Please, don't stop." I slipped from between her legs, and no sooner did I stand up did I hear voices coming towards the pool. I reached for Diane's hand. She took it, and I pulled her to me, about to tell her someone was coming this way, but she pushed me hard. A quick look at her as I lost my balance was all I got, and I could see mischief and frustration, and then I felt into the pool.

The splash brought the voices to us even quicker. There were a couple of hotel employees there to help me out of the pool, once I managed to get my feet under me. I moved to the edge and glared up at Diane. She had a hand over her mouth, and was doing a very bad job of stifling her giggles. The two employees offered a hand getting me out of the pool. They asked if everything was OK, and I explained that I was talking to the lady, and lost track of the edge of the pool, and fell in. This brought another round of snickers from Diane. I laughed it off as well, and we started to head into the hotel, me making squishing noises with each step.

As we started to head to the elevators, one of the employees said that they needed me to fill out a form quick, an incident report. Diane began giggling all over again. I gave her a stern look and the key to the room, telling her that I would be up shortly. I followed the men to the office, and they did a quick form, explaining that this was a waiver stating that I would not sue the hotel for what happened. No harm, no foul, so I signed their waver, and told them that it was ok, that they could laugh in front of me for my stupidity. One did, the other just smiled. On the way out, I asked the man if their gift store was still open, as I needed to get a couple of things that we ran out of. They said that it was, and had all the things needed, like deodorant and toothpaste, and they also had a vending machine that had a variety of items as well for when the store was closed.

I walked into the shop, but did not see what I was looking for, and I was not going to ask for it. I went to the vending machine. Looking through the glass, I saw that it had more of the discretional items, and I did find what I was looking for. It was pricey, but the machine took credit cards, and I would be paying Diane back for my impromptu dip.

Once I reached the room, I noticed that she left the lock outside the door so that I could get in. I loudly let the door shut, and secured the locks, and said that I had returned. She was on the balcony, and looked at me over her shoulder with a bright smile. She watched me take a step, and the resulting squish caused her to begin laughing all over again. I noticed that she was in one of the robes. She turned back to look over the scenery at night, and I began to remove my wet clothes. She never looked back, and I heard her giggling still. I started to hatch a plan. Either she would enjoy it, or she would be upset. I was not upset with her for pushing me, but I could not let that go unpunished.

I got completely undressed, and went into the bedroom. Once there, I took my purchase out, and opened the small bottle of K-Y personal lubricant. I generously applied it to my cock, and wiped my hands. Grabbing the bottle, I moved back into the main room. She was still on the balcony, leaning on the rail, sipping on a can of soda. I must have made a noise, because she started to giggle again. She said that the look on my face was priceless as I fell into the pool. I stepped up behind her, and reached my hand down to rub up the back of her thighs. She let out a low moan, saying that she expected something different. I moved a hand to her inner thigh, and she spread her legs to allow me access. I rubbed my fingers over the lips of her pussy, feeling the wetness that was gathering. This was it.

I quickly stood up, using my hands to spread her cheeks apart, and told her that it would be different. My next motion happened perfectly as I lined up my cock and pressed it straight against her ass, and it began to slide in. Once my cock started to slide into Diane's ass, I put my arms around her, and held her tightly. She let out a long surprised gasp as she felt her ass being invaded. As soon as I felt I would not be dislodged, I stopped moving, and held her there. It was then that I began to enjoy the sensation of her ass grabbing my cock from all sides, and squeezing it evenly all around. I pulled Diane back to me, trying not to move inside of her. Once I got her face close to mine I could hear her mantra of "Oh my god!" over and over again. Her eyes were wide, but looked more surprised than shocked.

I reached a hand inside of her robe, and began rubbing it over her breast, feeling her hard nipple. I rubbed the palm over her nipple, and I could feel her ass contract around my cock. I nibbled her earlobe, and whispered to her, asking if she was alright.

"It stings, but oh my God, I think I came."

I reached my other hand downwards, and I must have moved inside of her. She gasped before my fingers reached her pussy. She was very wet. Maybe she did have an orgasm.

"What do you think? Should I keep going, or do you want me to stop?" I asked her while still continuing to play with her pussy, and rub her nipple with my palm.

In response, she began to push against me, and I could feel my cock sliding deeper into her asshole. We both gasped in unison as the sensation of our first anal fuck swept over us. Soon, I was all the way inside of her, and I began to slowly pull out. She stopped me.

"Hold still for a minute. Let me get used to it."

I brought both of my hands up, and pulled the shoulders of the robe off of her, and down her arms. She let the robe slip from her entirely, and I tossed it to the side. I returned my hands to their former locations, and could feel her ass grabbing at my dick.

I brought my mouth to her ear and whispered "This is kind of like the dance club, but only we are both completely naked, outside, and I am fucking your ass." She put her hand over mine between her legs, and began frigging herself. Her fingers were moving quickly, directing my finger's contact with her clit. With my other hand, I pinched her nipple, and she started rotating her hips. I slowly started to pull my cock out of her ass. Once I was almost out, without stopping, I started to slowly slide it back in. The caress of her ass was exquisite.

I began a slow motion, and she slowed her fingers, but she continued to make constant mewling noises. If she was faking it, she was really good. I moved my hand from her tit, and brought it to her mouth. She locked onto my index finger, and bit down on the tip. I asked her if she was ok, and she nodded her head, and pressed back against me. I moved my hand from between her legs, and brought it up to fondle her other breast, and gave the nipple a firm pinch during a thrust into her ass. She released her bite on my finger and groaned. I grabbed her other nipple, and pinched them both. She started moving her hips, swaying them enticingly while I fucked my cock in and out of her ass.

Getting to know Diane's naughty streak, I decided to feed it some more. "Just think, anyone could be walking below us, and look up and see what we are doing. I think that the light from the room would let them see." She let her head loll forward, her hair falling in front of her face. "If anyone was in the room next to us, they could sit on their balcony and watch me fuck your ass for the first time." With that, she leaned over, her breasts hanging over the rail, allowing me to get a little deeper in her ass. Every time I pushed in, I could feel how wet her thighs had become. She was really getting off on this.

"You want anyone to look up, and see your beautiful tits while I fuck you? You want them to see the pleasure on your face while you are getting fucked in the ass?" She nodded her head, and mumbled something. I leaned over a little. "What did you say, my dear?"

She cried out. "Faster! Oh God, do it faster!"

I started moving my cock faster inside of her, and she responded.

"OH OH OH OH OH OH OH" she yelped with each thrust. Then she got even more vocal.

"Oh, fuck my ass! God it's good, you are so deep in my asshole! I never knew it could be so good!"

Soon, I began to moan. Sensing I was close, Diane, with her head still down, said "Are you going to cum in my ass? I want to feel your shoot your cum deep in my ass." As she said this, she squeezed down on my cock, and I could not take any more. I pushed as far into her ass as I could, and began shooting inside of her. As soon as it started, Diane tensed up, and her body began shaking. "I'm cumming!" she shrieked. I reached over, and pinched her nipples, causing her to groan. I continued to cum inside of her ass, and she continued to shake. Soon, I started to grow soft inside of her. I pulled her up to me, and began kissing the back of her neck, and her shoulders. I pulled myself from her completely, and she turned around, and kissed me furiously.

Her kisses were insistent. I would swear by her kisses that we were just getting started. With one hand on the small of her back, and the other in her hair, I pulled back from her, and looked in her eyes. There was a hunger still there. I felt a little guilty for what I did, even though she seemed to love it.

"Are you ok with what I did?"

"I will say that I did not expect that tonight. If asked, I don't think I would have been ready. Oh, God it was great though. It did sting pretty bad at first, but you pushed all the right buttons. At one point, I could not stop cumming. I never would have thought I could have multiple orgasms."

"You look like you still want more."

"I do! I feel like I am on fire."

"Well, let me see what I can do." I kneeled on the balcony in front of her, and ran my hand up her leg. Her thighs were a sticky mess, but her pussy was still wet. Diane leaned against the rail, and spread he legs some more. I began running my fingers over her clit, and then slipped two inside of her. Using a twisting motion, I began sliding them in and out. She felt loose, or relaxed, so I added a third finger.

Spying the tube of K-Y, I removed my fingers, and lubed my hand up. Diane looked down at me, and seeing what I was doing, cast a dubious look at me. I slid three fingers back inside of her, and she watched me push them in and out. This would be a first for me. I pressed the three fingers as deep as I could, and Diane began to quiver.

"Do you want to try it? You can tell me to stop, and I will." I said while rubbing my thumb over her clit. She rolled her head back, and I took that to mean proceed. I brought all four fingers and my thumb together, and began to slowly work them inside. Once my thumb started, I could feel her getting very tight. Diane let a breath out. I moved my other hand up, and lightly rubbed her clit while I began pressing again. She clamped down on my hand tightly, and when she relaxed, my hand slid inside of her.

Diane's head came back up, her eyes wide, and her mouth opened, but no sound coming out. She did not look like she was breathing. Her stomach was undulating wildly. I did not know if this was good or not. I had never seen this before. I had never done this before.

"Are you ok?" She took in a loud gasping breath, and she shut her eyes, and I could feel her muscles wilding spasming. Quickly, she relaxed a little, and my hand slid inside a little more. She came back to earth.

"Fuck fuck fuck fuck" was all she could say at first. I felt that it might have been good, but still did not know. Finally, she looked at me and said "You were pressing right against my g-spot. I thought I was going to die, it felt so good."

I relaxed at that, and started moving my hand.

"Ohhhhhhhh, I think you put my fire out."

I pulled my hand back a little, and pressed my thumb against the wall of her pussy. I then started to move my hand around, pressing up.

She reached a hand down, and grabbed my hair, nearly pulling it out as she let out a yell.

"OHHHHHHHHH FUCKKKKKKK!!" she wailed. Her body began convulsing again, and she nearly doubled over. "Oh, please! No more, no more!"

Flattening my hand out as best I could, I began to slowly pull it out. Once it slipped out, I noticed that my cum had run out of her ass, and was streaming down her leg. She needed me to help her into a chair on the balcony. I told her I would be right back, and I ran into the bedroom to start filling the tub with water. She would need this after tonight's fun. Once the water was at the right temp, I walked back to the balcony. She had a hand resting on her stomach, and the other on her pubic area, running her fingers over her pubic hair. She looked up at me dreamily. I leaned down, and she brought a hand to my cheek. I gave her a kiss, and picked her up in my arms. She wrapped her arms around me, and I carried her to the tub, and gently set her on the edge. She slid into the water with an appreciative sigh.

I slid into the tub beside her, and started the jets running. She leaned to me, laying her head on my chest. I caressed her hair, and we relaxed silently in the tub. After about 15 minutes of soaking in the warm water, the jets turned off, and I managed to get myself out of the tub. Diane managed to sit on the side, but could not get herself out. I picked her up, and carried her to the bed. I turned off all the lights, and crawled into bed beside her. We faced each other. She put a hand on my cheek again, and caressed it. In the dim light, I could tell that she was smiling, and had a dreamy look on her face.

Without even thinking, I said "I know what our relationship is, but I do not think I could ever want anyone but you."