Cancun

After both of us regain our composure we realize that we have been screwing for over 2 hours and decide to shower up and go down to the beach. As we enter the shower we are very content and clean each other up and discuss the plans for what we will do that evening. Diane of course has some ideas.

Chapter 3

After Diane and I had had an afternoon of all sorts of deviant and wild sex we cleaned ourselves up and went to the beach for the afternoon. After lying out and relaxing for a few hours we decided to go back to the room clean up and get some dinner. We had dinner at the hotel restaurant and a few drinks and really enjoyed ourselves. Now Diane has some ideas about what she wants in the perfect man. Some strange list of things that she feels is the perfect guy that probably doesn't exist. The problem with all of this is that I want to be that guy and try my best to make her happy. Sometimes I succeed and sometimes I don't but on this little vacation I have decided that I want to do what I can to fulfill her needs as woman both emotionally and sexually. So I know that Diane's big hot button is dancing. It's not really my deal but I also know that if it keeps her happy she will keep me happy. I had spoken with the concierge and I was told that there was a pretty good club not to far from the hotel and told her that we were going out. We hopped into a cab and went to the club. Diane and I are both 43 so we were definitely the on the older side of the spectrum. The club had a lot of younger people and most of them were clearly wasted. I went to the bar and ordered a shot and a beer for me and tropical mai thai for Diane. If I was going to go out on the dance floor I needed a little buzz but also couldn't get drunk. Drunk and sex is fine but I wanted to be able to perform perfectly for Diane later that evening. Diane drank her cocktail and I drank my shot and started feeling pretty good. We made our way out to the floor mixed in with a swarm of younger people and started dancing. The girls were all young and tan and wore revealing outfits and it was hard not to look. Diane was a little buzzed from the drinks earlier and the new cocktail in her system along with the beat of the music and all the sexuality that was oozing in the club was working in my favor. Diane started grinding on me and in no time I was hard as a rock again. The heat from all the people in club was making us both sweat and it didn't take long before Diane and I were making out on the dance floor along with all the young college students. After about an hour of dancing I was ready to take Diane back to the room and fuck her silly again. Diane and I made our way back to the bar and I ordered her another drink and a bottle of water. We drank up and we were standing real close to each other and kind of talking about things and inevitably we started talking dirty to each other. We moved over into a corner of the bar and out of everybody's way and started making out again and Diane moved her hand down to my crotch and started rubbing on me and as usual she got me ready again, while Diane was rubbing me hard my hand wandered down the back of her dress and stared rubbing her pussy over her dress. Both of us came up for air and noticed that all the young college students and the security people in the bar were watching the horny 40 something couple practically maul each other in public. Little did all these young girls know that they might be hooking up with some dude and even had some idea that they knew how to screw but they had no idea about what fucking was about. I didn't really know until I hooked up with Diane and wouldn't trade her for any of the young girls in the bar. Diane was as much as I could handle and I was happy with what I had.

We decided to leave the bar and go back to the room for some more fun and hopped into a cab to take us back to the hotel. During the short ride back to the room Diane slid up next to me and started rubbing on my cock and whispering in my ear about how I was going to suck her off when we got back into the room and how she was going to blow me even better than before. When we got out of the cab my cock was fully engorged and I actually had a wet spot on my pants from all the precum that had leaked out of my head. We made it back to the room without anyone noticing the stiff dick and wet spot in my pants and immediately tore each others clothes off. I took her into the bathroom to shower up again. If I was going to get really nasty I wanted us both to be clean so we got into the shower and lathered up just like we did earlier but this time I didn't want to wait. I wanted my cock in her pussy right then and there in the shower and wasn't going to be denied. I spun her around and bent her over against the wall in the shower and grabbed my hard spear and slid it into her steaming hot cunt. As I slid in my meat I could feel the tightness of her little cave and Diane tensed up again. I don't know why but I love the reactions from Diane when I pound on her tight little hole so I slammed my cock inside of her a couple of times just to hear her whimper a little bit and she did not disappoint. After a few rough strokes to her hole I settled into a nice stroking rhythm massaging her pussy with my hard cock and Diane and started bouncing her ass in time with my strokes. I was starting to feel the tingle in my balls that was forewarning me of yet another hot load being sent to the surface and was trying to decide whether I wanted to give it to her there or make her work for it. The night was getting late but not so late that I was going to chance ending it early with cumming so soon. I decided to pull my cock out of her and delay shooting my load until she had been satisfied.

I turned off the shower head and dragged her out of the shower and tongue dried her from toe to ears. Although Diane and I have not done any S&M I know she still gets turned on by both being dominated and by my submission and I don't mind pleasing her at all in a submissive state as long as I get to be dominate as well when it suites me. So I played submissive and tongue dried Diane thoroughly. When we were both dry we went back into the bedroom and I know Diane was ready for a serious tongue fucking. Diane lay down on the bed with her legs spread exposing her gorgeous pussy for me and I told her to play with her box for a few minutes and get it nice and wet for me. I pulled on a pair of shorts and ran to the ice machine outside and filled up an ice bucket and was back in the room within a few minutes. When I returned Diane had inserted a vibrator into her ass and was working her clit with another vibrator. I placed the bucket down and buried the rest of the toys into the bottom of the bucket and decided to get to work. As much as I wanted to watch her get herself off I wanted to feast on her and wanted to get her squirting as quickly as possible. I let her play with herself a little longer and started using the toy in her ass to fuck her little hole. My face was only inches away from her mound and watching her rub it with the tool and hearing her pleasure filled moans was more than I could handle and I pushed the vibrator away and started eating her juicy pussy and lapping up her wetness. Diane immediately responded to my tongue lashing and started gently tugging my hair to get my face as close as possible to her hole. I got lost in the job at hand and started working her little clit like it was the last time I would ever suck on a clit and was almost crazed with desire to get this little bitch to squirt on my face. I was fucking Diane's ass with the toy and working her clit and pussy with my tongue when the signs I know so well started happening and I knew it was only a matter of seconds before I could get her off. I pulled the toy out of her ass and stopped sucking her clit and started gently slapping her clit and asking her to cum on my face and as usual Diane didn't disappoint. She began shooting streams of her cum all over my face and chest while I told her what a good girl she was. What a huge turn on it was for me to have this beautiful woman in bed squirting stream after stream of cum all over me and knowing that I was the guy that could get her off so easily. After she had shot 5 or 6 shots of her cum all over me I went back to work on her little pussy. I cleaned her up a little and slid the vibrator back into her ass and deposited a handful of nice sized ice cubes into her tight little pussy that I had fucked with my cock only twenty minutes earlier and began sucking her off again. I love the taste of her cunt and was lapping up her juices like a man possessed hoping I could get her off again and again. We repeated this pattern for close to an hour I would guess but who knows. We got lost in time and repeated the pattern for quite a while but at some point my cock started calling out for his turn and I could not deny him his prize.

Diane had had several orgasms and I crawled up next to her and told her it was my turn to get off and Diane said she was ready to take care of me. I lie back to relax and Diane started working on my nipples and told me that I had neglected hers and I would have to be punished. My nipples are very sensitive and Diane has a cruel streak in her and knows that she can hurt me if she is not careful. Knowing this she seems to get some perverse pleasure in not being careful and really giving my titties a rough twist. After yelping a few times I finally relaxed and let her play knowing if my cock was going to get any love she would have to get her way. Diane climbed up on my cowgirl style and started rubbing her snatch against my stiff cock and I could feel her soaking lips wrap around my cock as she slowly dry humped me. While she was teasing my cock she continued playing with my nipples and asking me if I liked it and scolding me for not making my nipples tough as she had told me to do. I knew if I showed any pain she was going to continue my punishment and my cock would further be teased so I did what I could to enjoy the twisting of my nipples. Finally Diane realized she needed my meat in her pussy as much as I need to fuck her and allowed my cock to slide quickly inside of her. After all the teasing she had done the sensation of her tight little box swallowing my cock was all I could take. Diane started riding my cock slowly and it felt great. I am so lucky that I usually cum quicker when I am in a dominate position so I was content to let Diane ride my cock as long as she wanted and she was having a great time riding my thickness. She started picking up speed and bouncing on my cock while her wonderful tits were moving in unison with her movements. I was enjoying the ride and allowing myself to just relax and enjoy Diane fucking me and working to control myself from spewing my seed deep into her pussy. Finally Diane looked at me and said "I want you to fuck my pussy now" and I complied with her request. I grabbed her and without allowing myself to pop out of her tight little hole rolled her over and got her into the missionary position and started stroking her hole with my thick cock. I slowly pumped my head in and out of her pussy and immediately began to feel stirrings inside of my cum factory. I wanted to give her my load but hoped I could wait for a while and knew if I shot my load I was going to be done for the night so I pulled my cock out of her pussy and slid down and started to tongue fuck her again. I could taste myself mixed in with her juices. As much as I loved eating Diane's pussy this move was a clear defensive posture on my part. Diane's pussy was trying to suck my cum out of my cock to soon and I needed to give my cock a moment to recuperate and this was the best strategy to use. Once my cock was under control I moved back up and again attached my swollen red meat past her swollen lips and into her gushing tunnel. I watched as my engorged cock head disappeared into her hole and started pumping on Diane again. It was no use and I was going to cum at any second. Because I had shot my load already inside of Diane's mouth and ass early I really wanted to plant my flag into Diane's pussy but knew that Diane also wanted me to shoot on her tits. We had all week for that and nothing would turn me on more than to pump load after load of my thick white cum inside of her pussy and decided I was going to let her milk me dry this one time. I had earned it by sucking her off countless times. As I started pumping on her faster and faster I could tell that it was only going to take a few more pumps until my hose shot its payload into Diane's honey hole. I started to feel the tingle in my balls get more and more intense and my cock constrict until I could take it no longer. I slammed my cock as deep as I could inside Diane and let loose a strong stream of my white hot lava inside my naught little girl. My body was tense and my heart was pounding as the third orgasm of the day squirted inside of her. I finally was done and dropped down to rest.

Diane looked at me as told me she loved feeling me cum inside of her but that she told me since I was supposed to at the very least ask her if I could I was to be punished. I responded that I had paid for the trip but was quickly cut off and told that if I wanted to fuck her pussy again I would need to clean it up. I knew this would turn her on and loved the fact that I could give her my cum once I sucked my seed out of her pussy decided to go down and clean up the cream pie I had given her. I went down and saw the white cum oozing out of her swollen and red pussy and started sucking out the mess I had left inside of her. I wasn't really sucking out my cum but more of a mixture of "our cum" mixed together. When I had a mouthful I brought it up to her and she was waiting for me to share with her. She told me to only giver a small amount and save some for her tits. I started kissing her mindful to keep the lions share in my mouth and when Diane got her fill I moved down and started sucking on her tits with a mouthful of our cum. When I had left an ample amount I moved over to her other breast and repeated the process. She immediately started rubbing our juices into her tits and I just sat there and watched her work the salty brine into her skin. When she was done we both collapsed into the bed and started sleepily talking about what we would do the next day. I hope I can make it for a full week.

Chapter 4

The next morning we got up and decided to go get some breakfast. Diane was acting strange all morning and after breakfast got up said she needed to check for something at the front desk. The plans for the day were to let Diane hang out by the pool and for me to go play golf at noon. I was really excited about playing golf and was counting the minutes until I could go and tee it up. I decided to go back up to the room and relax a little bit. When I returned to the room I turned on the TV and plopped down on the bed. I was involved in watching some Mexican show and trying to figure out why the man in the bumblebee outfit was yelling at the hot Mexican chick and was about to turn the channel when Diane came bursting into the room with a package wrapped in brown paper. I figured she bought something in the gift shop and asked her what it was and she said it was a gift she bought for one of her girlfriends and I quickly lost interest. Diane went into the bathroom with the package and came out a few minutes later in her panties and no bra and jumped into bed with me. I, of course was turned on and latched on to Diane and we started kissing and roughly fondling her nipples. The night before Diane was really rough on my nipples because I forgot about hers and I was in no mood to be punished again for being thoughtless. Diane pulled me up and with her mischievous face told me she was going to tie me up and fuck me really hard. I told her that was fine with me but reminded her that the safe word for my nipples was blue. I really need a day or two to allow them to heal and she said she was sorry about that and promised she would be gentle if she did touch them. Apprehensive about the nipples I was still excited about getting fucked by Diane before my golf match and told her to tie me up. After Diane tied me up she took off my pants and again my hard cock popped straight up in the air. Diane was still wearing her panties and I was expecting them to come off at any moment. We started kissing and she got up on her knees and started grinding her pussy against my face and dry fucking my mouth, chin and nose. After a few moments she stopped this and told me that it was just not turning her on that much. I suggested that she take her panties off and let me do my thing and she responded:

"OK your right but I am going to wear something really sexy for you that I bought just for today and I have been planning on wearing this for you for a long time"

With this said Diane left the room and went into the bathroom. I laid there on the bed with my cock desperately needing some attention and a bit annoyed with the situation. All I really wanted was a good solid blow job and to suck her off a few times. I also only had an hour or so to get ready to go play golf. About 10 minutes go by and I start to get a little pissed off and start yelling at Diane to come back. She kept calling from the bathroom that this outfit is complicated but to trust her that it will be worth it. I start thinking couldn't this have waited until tonight? Payback is definitely a bitch and her ass was going to get fucked really hard later that night if I miss my tee time. About 5 minutes later Diane finally appears from the bathroom and at this point my cock has shriveled up back into its natural state. I am more irritated than turned on at this point and when I see her I feel like I was slapped in the face. Diane does not have anything sexy on at all. In fact it's the least sexy thing I have ever seen in my life. I tell Diane;

"NO! we have discussed this and I told you what the rules are on this"

Diane responds;

"Oh? I am sorry but I told you how I feel about golf and how much I hate it. You want to play golf fine but your going to be punished, yet again, for not being more thoughtful about what I want"

I am screwed. I know Diane and her little freak side. We have discussed this and I had agreed to maybe allow this to happen but hoped if this ever did happen it would be on my terms. Not like this. I also knew Diane was a little pissed about golf so I knew I was in big trouble.

"OK Diane, seriously, you have made your point...I wont play golf today, we can go do something else just don't do this OK?"

"Sorry, but you had your chance. It's your vacation and I understand why you might want to play golf but I also have some things I want to do. If you want to go after I am done that's fine but for now your ass is mine!"

In the past few months Diane had been watching a lot of porn and been asking me to do some really crazy stuff. I told her that I would do some things for her if we were in a committed monogamous relationship but until then some things were off limits. I kind of hoped that maybe this was her way of telling me that the days of me being worried about our future would be over after this trip and realized maybe in her way this was the way of telling me. I asked her;

"Does this mean that we are together like we discussed?"

"No. This is about golf"

Diane hopped on the bed in front of me wearing a strap on dildo with a tube of lube in her hand.

Now I love Diane. I would do just about anything for her. Just about. This was something we discussed and there were some boundaries I had set and she was breaking the rules I made. This was fucking rape. I was going to be Diane's prison bitch.

Diane hopped on my chest again and told me that the package she shipped from Vegas to the hotel was just in case I had any bright ideas about playing golf. She said I was the one that was being a dick and because of that she was going to teach me a lesson. I wanted to plead with her to not do this but realized that there were only two outcomes other than Diane fucking me with that strap on. Either she would get pissed off and say I was not fun and the entire day would be wrecked or she would think I was a liar and not serious when I told her I would do anything for her. If I let her have her way she would know I was serious and wanted to make her happy. I understand this sounds a little like I am pussy whipped and some of my friends tell me that I am. Well guilty as charged. Most of the guys who say this don't have girlfriends or wives like Diane and haven't had there cocks sucked or fucked in months much less had them squirt on them. So I decide to take one for the team and hope for the best.