Helping A Friend On Leave

My wife is a beautiful but shy redhead. We met in college during a time in my life when I didn't know what I wanted to do or what kind of woman I wanted to be with. At the time we met I was going out with my wife's friend and she was dating someone else. Through a long string of events we became friends, fell in love and eventually married. We are now both in our middle twenties and at a place in our lives were we are not ready for a family. I have been with wilder women but there is something about Ana that drives me wild. Even in the passion of sex she seems shy. It is this shyness that has possibly attracted me to her but it seems like behind that shyness a great sexual power is trying to come out. There are many stories to share about her but I will start with something that happened last winter:

I walked into the bathroom of the hotel room and looked into the shower. Ana was washing her red hair that falls to just around her shoulders. Her back was to me and a white stream of soap was running down over creamy skin and disappearing between her ass.

I told her that we needed to leave in 45 minutes. She turned her head around and nodded.

We were in town to see my friend Bill. He was home on leave from fighting in the sand box in the Middle East. Bill had 5 days of leave, I considered myself lucky that he was spending a day or two of it with me. He spent his first night home with his family. His wife's flight was canceled yesterday evening and she was supposed to be able to make in today. Bill, his wife Susan, Ana and I were going to have dinner and then go out to a comedy club.

I finished getting ready and tied my black dress shoes. We had decided to dress up a little to make the occasion a little more special. Ana walked out of the bathroom with a gush of steam behind her. She said she had to do her hair and then she would get dressed. After collecting somethings from her bags she walked back into the bathroom. I asked her how she was going to do her hair.

"I was thinking of leaving it curly tonight but I was going to put some stuff in to give it that wet look, is that okay?," she said.

I told her that was fine by me. I always thought it made her look some how more mischievous and natural at the same time. When I asked her what she was going to wear tonight she said she didn't know yet.

I walked into the bathroom to see what she was doing and her towel was fallen around her ankles. Both of her arms were raised above her shoulders as she was working in the hair product she mentioned earlier. Her breasts lifted up and down each time she moved her arms and shifted side to side when she would move her hands about. Ana's tits were my favorite part of her body. While I normally like larger breast, her C cups were wonderful in my hands. Her entire body was like fresh cream. I noticed that her two pink nipples were a little hard. I walked behind her and cupped her breasts. From my new vantage point I noticed that she had freshly shaved the area around her vagina. There was a small area right above her clit where she left her red pubic hair in a small strip. When she shaved like that it always turned me on. She let out a impatient sigh and promptly informed me that I if I got in the way we would be late. She was right so I let go of her and watched as her breast resumed their slight motion as she finished her hair. Seeing her get ready always excited me and touching her had caused me to get a little hard. She pushed me away with her ass reminding me didn't have time. As I walked out of the bathroom she looked over at me and smiled while saying.

"You did feel good though and since we got this hotel room, you might get lucky tonight."

I went back into the room and turned on the television but there was nothing on. Ana asked me how warm it was supposed to be tonight. I told I thought it wasn't supposed to get below 70. She that was good because she bought a new skirt and wanted to wear it tonight. I sat back in the chair and closed my eyes as I was tired from driving in that day.

I woke up a short time later to Ana moving something about on the bed. She was pulling out a light sweater that covered up her shoulders. I looked over and she was wearing a rather short white skirt for her. It came down enough that it covered up everything but it kind of puffed out so that it seemed her bottom would flash if she spun around. She had on a black top with string straps that showed off a lot of cleavage, at least while she was bent over. She asked if I was ready and I said yes. I glanced down at my watch and I realized we needed to leave very soon. I stood up and stretched and looked over at Ana. She was particularly sexy tonight. Her red curly hair was shiny from the hair product she used and the contrast between the black top and white skirt was stunning on her. She sat down on he bed and pulled a black stocking up her right leg. I moved over in front of her to see what she was wearing underneath. She had on a very sheer white thong. After putting on her left stocking she pushed me aside to look in the mirror. She lifted her skirt up to make sure her stockings were up all the way. As I admired her reflection in the mirror I could see the pubic hair she, left like a hazy fire right above her vagina. She dropped her skirt and slide on the black sweater over her shoulder. I was little disappointed when I noticed it covered up much of her cleavage. I asked her why she had put on the stockings since she hardly ever wore them. She smiled and said we don't get a chance to go out much and wanted to look nice. She mentioned as an afterthought.

"I imagine Bill wouldn't want to hang out with someone hard on the eyes after being over there for 6 months" and laughed.

We hurried out to the car and doubled checked to make sure we had everything. She gave me here ID since she didn't want to carry a purse and I slid my phone in my pocket and we were off.

The restaurant we picked wasn't too fancy but served good steaks. Bill said he wanted to go somewhere he could get a cold beer and nice steak. When we got there Bill hadn't arrived yet. We put our name on the list and sat at the bar. I ordered a beer and Ana said she wanted Cosmo. Ana doesn't drink much so I was a little surprised. We sat with our backs to the bar so we would notice when Bill and his wife came in. I look down and noticed Ana had on a pair of very expensive looking black high-heeled shoes. She saw me looking at them said she felt like splurging the other day. Her long black stocking covered legs looked great siting next to me. Her skirt fell so that it covered the tops of the stockings but the way she was sitting made it look like the skirt was shorter than it really was. A man walk past us and dropped his phone. He wasn't very concerned about being noticed checking out my wife's legs. I wonder how much of an accident it was that he dropped his phone. On his way up from reaching down for his phone Ana uncrossed her legs and sat a hand in her lap. It looked like her cheeks were a little flushed but I couldn't tell because just then Bill walked in. He came over to us and I gave him a big hug. He looked good but a little skinny. Ana jumped off the stool she was sitting on and Bill gave her a bear hug. I noticed as he set her down that I was right about her skirt. It furled out a bit and I caught a glimpse of the bottom of her ass.

Dinner was uneventful but Bill was a little upset since his wife still wasn't in town. Apparently there was a wild-cat pilot strike at the airline she was to fly on and only about half the flights were get out of her airport. She was supposed to be here in the morning. I could tell he was upset since he hadn't seen her in six months. On our way out Ana went to the bathroom and Bill told me he was really looking forward to having sex with his wife and the delay wasn't helping anything. We decided to drive together to the comedy club.

While we were in line to get tickets Bill leaned over to me and said,

"No disrespect man but Ana looks so hot tonight."

I nodded and said she does. I wasn't worried about Bill, we had been friend since middle school and he was always respectful towards Ana.

The club had a two drink minimum so when the waitress came around before the first act Ana order another Cosmo. Bill said if he wasn't going to be with his wife tonight he might as well get drunk while he could. He ordered a couple shots and told the waitress to keep them coming. I ordered a beer since I figured I would need to drive Bill home. The first act was okay but you could tell he was new. Ana ordered another Cosmo when the waitress came and got up to go to the bathroom. Bill was starting to get a little drunk and said rather loudly that he couldn't believe the way Ana looked. The bathroom was on the other side of the club and Ana had to walk just within the brightly lit area around the stage. Her skirt had become rather transparent in the strong light and you could clearly see her white thong as she walked away. We talked a bit while Ana was in the restroom and Bill told me that his wife never dressed like as she was raised very conservatively. I informed Bill that Ana hardly ever dressed like that herself.

Bill said, "Luck me" with a wink.

Ana came back right before the next act. I could tell she was getting a little drunk and when she sat down next to me she laughed as she saw on my face that I could tell the drinks were getting to her. The next act was must better and the waitress came in the middle of the act to see if we wanted more drinks. Bill switched to beer but first demanded that we all drink one last shot with him. By the end of the act we were all feeling good and Ana's white cheeks had turned a rose color from the warmth of the club, the drinks and laughing. While the last act was getting ready Ana took off her black sweater that was covering her shoulders. I watched Bill eyes follow her cleavage as she sat down. His eye caught mine and he smiled at me. The last act was off a bit but we all felt very much like continuing the evening afterwards.

We walked across the street to a bar that was full but not packed. When we got close to being inside Ana exclaimed that she had lost her sweater. Bill nudged her a little and said she didn't need it. The bar was much warmer than the club so he was right but I am not sure that's what he meant. Just inside the bar two large men were checking ID. It seemed they were checking only half heartedly. Ana was the first to be stopped. Bill was between Ana and I and before I could get her ID out of my wallet she had got past the bouncers. In what I could only say shocked me she asked the bouncers if she had to have her ID. One of the bouncers mumble yeah but the other looked interested in what she meant. Telling she had the attention of one of them she spun around and lifted up her skirt very quickly. The uninterested bouncer become much more interested. Bill shouted in excitement and before the now interested bouncer could say anything she quickly grabbed Bill's hand and hurried inside. The bouncer checked my ID and said the fee was ten bucks. Wanting to get inside quickly I paid. Bill and Ana were standing next to a tall table near the dance floor. Bill looked a little worried that I would be mad but also looked very happy. After worrying about him being in a war zone for 6 months seeing him happy was well worth it. He slipped away to the bathroom.

Ana whispered in my ear that she was sorry and that she was just having fun. I told her to not worry about it and I thought it was hot what she did and that Bill needed some attention. She whispered again that she was getting very horny and couldn't wait to get back to the room with me. Bill came back with 3 shots which we all downed together. Ana said that she wanted to dance and took me out on the floor. There wasn't much room and it was an older slow song that nobody was really into. I told her that she should dance a couple songs with Bill since he was alone and it was kind of his night. She said that was fine with her. We went back to where Bill was. I told him to go dance with my wife as a new song came on. He looked at me to make certain it was okay. I nodded and off they went. At first Bill and Ana looked a little awkward together but more people came onto the floor and the were pushed together a little. They were dancing face to face and Bill was looking down her top a lot. I figured it was no big deal and I was just happy he was home for a bit. They slowly became more comfortable dancing together and Ana put her arms on his waist. The floor wasn't that far away and I could tell she was enjoying Bill's attention. A really popular rap song came on and I could tell Ana got excited. She moved around so her back was facing Bill and started to grind into him.

I started to think about one time Ana I were in bed together when we first started dating and getting ready to have sex. Some how we got talking about the night before and I started teasing her about how much it looked like she enjoyed dancing with another guy at a party we were at. She said very shyly that he had gotten really hard. I asked her if she liked it and she nodded. That got us both turned on and I slide into her warm pussy. She was really getting into it and I asked if she liked to feel a hard dick next to her. She sighed yes. I asked her had it happened before and she nodded. I begged her to tell me about it and she start off slowly.

She said that she had been at a party with some of her college friend in another town. There were a bunch of people dancing and a big guy came up her behind and start grinding. At first she said she was a little nervous since he was a bit rough but decided to dance a little. As soon as she pushed back against him he got hard. She then told me how she danced with him for about 10 minutes teasing him by alternating between grinding into him with her ass and rubbing against him with her pussy.

After hearing that I couldn't hold out any longer and put out to cum on her stomach.

I snapped myself out of my memory and saw my wife bent over at a 90 degree angle up against my best friend's crotch. Bill was staring down and I saw that Ana's skirt had folded over on top of itself on her ass. He must have been getting a great view of her thong. The song was really rocking and all kinds of girls around Bill and Ana were doing much nastier things. Ana looked over at me with a worried look and I smiled back at her. What she was doing was turning me on and my thoughts about the time she had whimpered in my ear about how much she liked teasing while dancing only made my dick grow harder. I looked down at my drink and the song came to a stop. Bill looked over at me with a worried but happy expression. I gave him a thumbs up and shrugged. I could tell he was getting very drunk. Another song came on and they danced again. I imagine since Bill could tell I saw him, they didn't get so wild this time. Ana had spun around and was rubbing up into him and ever so often up and down Bill's leg. After the song was over they both came back to the table and Ana quickly excused herself to get more drinks. Bill was as drunk as I thought he was and said he was sorry but that was the first time he been close to a woman in along time. He then asked me if I or Ana would tell his wife that they had danced like that. I shook my head no. Ana came back stumbling a bit with the drinks but said she was too hot and wanted to leave. We all agreed to go and finished the drinks.

There was no way Bill was going to drive home and I was getting to feel a little buzzed. Ana said she wasn't able to drive. Bill said that he might walk home in a drunken stupor. I laughed and said no way. He then asked if we would mind him staying in our room, that way I didn't have to drive him across town to his family's house. I said that's fine. He added he didn't mind sleeping on the floor. Ana said we would work something out.

We got to the car and Ana climbed in back seat so that Bill wouldn't have to maneuver in and out. We started chatting and she leaned between the front seats to hear. Her legs were spread wide open and her breasts were about to fall out of her tight top she was leaning forward so far. Bill also saw this and was taking in the view. This was very much unlike Ana but I figured the dancing and drinks had relaxed her, maybe too much. Bill kept up a conversation with her so that he could keep his eye on her. At the first red light I looked over to see her right nipple about to slip out the top. She leaned into my seat and whispered.

"What will it hurt to give Bill a little show, he needs something to think about before his wife gets here tomorrow."

I started thinking that she wasn't as drunk as I thought or yet again she was. My mind was racing between my best friend ogling my wife and my raging hard because of the way she was acting. We pulled into the parking lot of the hotel. I hit one of the speed bumps harder than I should have I heard Bill exhale. I looked over and Ana's right nipple as pouring over her top. I didn't know if I should say something. Did she know or not know. Either way I didn't want to embarrass my wife by drawing attention. I pulled into a parking place and the street light from the lot illuminated the cab of car. Ana said "oops" and after we both looked she pulled her top back over her breast. I had the first chance to look down further and between Ana's legs. The light was enough that I could see the hint of her red pubic hair and more surprisingly her thong was wrapped tightly against her vagina and the transparent white material was soaking wet. I wondered how much Ana knew she had shown in her harmless backseat show. Bill announced that he had to piss and quickly opened the door. Ana looked at me and smiled with a glazed look in her eye. We got out of the car. Bill was on the other side of a tree pissing. My wife came close to me and asked.

"Do you trust me?"

"Of course but you're acting kind of crazy tonight."

"Well I am a little drunk and besides I haven't done anything too bad." She said as she squeezed my half erect cock.

"When we get upstairs to the room pretend to fall asleep. I want to help Bill with his 'problem'. I won't cheat, I just want to show off a little and maybe let him jack off while I do it. I promise after he passes out you can fuck me."

I didn't know what to say or even think. My mind was swimming with alcohol, arousal and a worry. Before I could say anything Bill was back and Ana walked ahead to the door. I opened with the pass key and Ana hurried ahead. Bill was having trouble walking and he kept telling me how good of a friend I was. As we walked up the stairs Bill and I could see the tops of Ana's stocking and nearly the bottom of her ass. When I got to our room a rush of cool air hit us. I had forgot I turned off the air conditioner I turned on to cut the heat and steam from Ana's shower. She hurried over to the unit and bent over at the waist to turn it off. We both got a great view all the way up Ana's skirt.

Bill flung himself into the chair and Ana said she was going to go the bathroom. Bill seemed a little more sober than before and I could tell he had a huge erection in his pants. I thought about the time had spent away from his family, wife and country and decided what to do. I told Ana through the door I was feeling sick and that I was going to bed. She said that was okay and she would be going to bed as soon as she finished talking to Bill. Bill seemed to be beginning to pass out in the chair. I pulled the cover down and stripped to my boxers. I got in bed, turned out the light by the bed and faced Bill. The only light in the room was coming from the light near Bill. Ana opened the bathroom door and the room filled with more light. The light in the bathroom switched off and she came into my view. She was still dressed and I thought she had changed her mind. Bill had looked up when the bathroom light came into the room. He seemed happy to see Ana again. She sat on the edge of the bed so that her back was facing me and she was facing Bill. I could tell from the reflection in the mirror that her legs were open. The sight of my wife's pussy woke Bill up some. She started talking to him and leaned over like she had done in the car. Once she had Bill's attention again she stood up. She walked over to Bill and sat on his lap so that she was still facing him. Her breast were very close to his face and I couldn't tell but she had to feel his erection. I was about to get up and stop her when she said something in a sort of whisper. It was in hushed voice but loud enough for me to her.