The Long Awaited Vacation - Day 04

Day four

I awoke before sunrise the next morning. I just couldn't sleep, and my mind wouldn't turn off. So, I get up and make some coffee trying to be quiet, as to let Heather sleep.

Coffee in hand I head out on the balcony where to my surprise I see Sylvia with herself bent over her balcony railing with one leg thrown up on the railing just going to town on herself with the vibrator. This is the same position Heather was in when she first saw us.

I sat quietly and enjoyed the show. Sylvia was an attractive older lady. Maybe 5 foot 2 with shoulder length silver hair. Wide round hips with a nice round ass and what appeared to be breast implants. She had a bit of a tummy but was by no means fat.

She moaned and trembled as she came and collapsed onto the floor. This startled me and I was worried, I jumped up and asked if she was ok. She was fine and extremely embarrassed.

She put her robe on and laid her vibrator down on the side table and said she would be right back. I refilled my coffee and she return with a cup of her own.

We spoke for about an hour just small get to know you talk as we watched the sun rise. Heather joined us with her own coffee. I excused myself to get in the shower and when I returned the two of them where giggling like schoolgirls.

Heather and I had another full day of excursions planned and we were soon off for the day. Heather told me that they had made plans to have dinner and drinks tonight once we returned to the resort.

Today we went on a snorkeling trip to some reefs off Key Largo. The water was beautiful, and you could see forever. We had purchased a few disposable underwater cameras for this trip.

Instead of taking pictures of the reef or fish, I ended up taking a bunch of pictures of my wife flashing me. She was fast become voyeuristic, and I loved it.

Back on the boat several other people pulled me aside to say they got a few pictures of Heather as well and that I was an extremely lucky man. A few college age guys came up and asked if we wanted to join them at a frat party in Miami later this week.

Back at the resort, we were getting ready to meet Bob and Sylvia for dinner. I told Heather about the frat party, and she tells me that although it could be fun let's not push things too far. She doesn't want to be passed around for a bunch of college age boys to do with what they want.

I understood what she was say and this brought about more conversation about Steve and Sylvia. Heather was ok with what was happening at the resort because she knew that she could stop it at any moment if she became uncomfortable.

Dinner was great and the conversation really flowed. Besides the fact they had watched Heather and I have sex, and I watched Sylvia fuck herself silly we really had a lot in common with them.

After dinner at the resort club, we were sat in the same corner U shaped booth as we were in before. Bob was starting to loosen up and talk a bit. We were all having a great time and decided to dance.

Heather and I were dancing together when Bob asked if he could cut in. Heather said of course so now I ended up dancing with Sylvia.

During the slow song she started rubbing her pelvis against me and whispered in my ear asking if I enjoyed the show this morning. My mind started recalling the scene of this sexy older lady fucking herself on her balcony. With this picture in my head and her pressing her whole body against me I started getting hard.

I looked over at Heather and her and Bob where dancing very closely and lost in conversation. Sylvia reached down in between us and took a hold of my penis through my slacks and by the look on her face she was very impressed. She said, "Heather was right...that is a whole lot of dick."

I was worried about Heather being mad at me or if this was a test. I told her "We probably shouldn't be doing this." Sylvia told me that Bob had seen how excited watching us made her and had given her permission to take it as far as Heather and I were willing to go.

A fast club song came on and I could see Bob and Heather continuing to dance. Bob really had some moves and was a much better dancer than me.

Sylvia continued to squeeze my dick as we were now dirty dancing. After several songs and grinding against Sylvia from all different angles all four of us returned to the booth. Bob was on one side of Heather I was on the other then Sylvia. My dick was still as solid as ever, standing at full attention.

Heather looks at me and says, "remember what happened last time we were in this both." I said, "I could never forget it." She reached across me and took Sylvia's hand and placed it on my still hard dick. This reassures me that Heather is at least ok with some heavy petting between Sylvia and me.

Sylvia started squeezing and rubbing again but nothing more happened. We sat there for what seemed like hours and I was in desperate need to cum.

I had one hand on Heather's thigh and the other on Sylvia's. Heather kept looking down at Sylvia's hand on my dick and then slowly spreads her legs for me.

I get my hand as far as her pussy and she motioned to me about my other hand. As if to say, "Don't forget our new friend." I started to move it up Sylvia's thigh and she just slowly and steadily spread her legs apart until they were wide open while pressing her pelvis forward. She says to me and Heather, "I'm yours to use anyway y'all want, nothing is off limits."

Heather looks at Bob and he says, "Please make my wife happy." Just as my hand reached Sylvia's soaked through panties Heather said, "it is getting late, and we should go to our room."

I didn't argue because I didn't care if I had to jerk off or if Heather was going to give me some, I was getting some relief. Before we even get the door closed Heather is on her knees in front of me with my dick in her mouth.

She would suck two to three times then pull off and say, "oh my god my pussy is so wet." Suck a few more times and ask, "Do you want to fuck Sylvia?" Dick back in her mouth, then say, "I might be ok with it but I'm still not sure." A few more sucks and, "would you let me fuck Steve while you are fucking Sylvia?"

It takes me less than a minute at that point to fill her mouth to overflowing with cum. She wipes it from her chin and says make us some drinks we are going back on the balcony.

Out on the balcony Heather walks straight to the railing looking across the courtyard. Steve was nowhere to be seen. She returns to me sitting on the lounger take a big sip of her drink and opens her robe.

She is naked beneath it she straddles me and takes my shirt off. She looks back out over her shoulder and says, "I was kind of hoping for an audience tonight." I knew she was talking about Steve, but just at that time Sylvia says, "well don't be disappointed I would love to watch."

Heather asks will Bob be joining the show. Sylvia said he was exhausted and went to bed but told her to enjoy herself and gave her the permission they had talked about earlier. Heather invited her to climb over to our balcony but to bring her vibrator with her as she could watch and enjoy from a closer view.

Soon I had my beautiful wife going down on me while I sat in the lounge chair and another very attractive older women sitting next to us robe wide open with no bra and her hand in her panties rubbing herself. Sylvia is looking straight at Heather's mouth engulfing my penis.

She reached down and took a hold of my dick at the base and held it there gently squeezing while Heather sucked on it. When Heather would stop to catch her breath Sylvia would stroke it long and slow.

Heather decides that she needs to be attended to as well and stands up, lays my lounger flat then sits her beautiful ass down on my face. A few moments later and she has my dick back in her mouth in the 69 position.

Now I can no longer see Sylvia and I am extremely busy with a mouthful of pussy enjoying every moment and although I'm not 100% positive I swear Heather pulled her mouth off my dick and it was soon replaced by Sylvia's mouth.

The tongue was suddenly on the bottom side of my penis and the technique although good was much different than Heathers. Soon Heather was Cuming all over me as she ground her hips into my face.

From the way Heather was Cuming on my face and now sitting straight up grinding her pussy into me, I could now be certain. My Dick was in Sylvia's mouth.

By the time she was done with her orgasm Sylvia had released my dick and pulled the second lounge chair right beside mine. Heather climbed off my face and turned around to lower herself onto my dick.

She starts to ride and looks next to us, and Sylvia is trying to mimic our actions by riding her vibrator. Heather tells me, "Hold it for her" which I gladly do.

So, I have one woman riding a vibrator that I'm holding in an upright position while my wife is riding me. Watching Sylvia ride the vibrator and moan my name was a big turn on for both Heather and me.

We switched to doggy style, and Sylvia move right along with us. Heather is working her hips on my dick while I'm fucking our new friend on her knees with a vibrator.

Sylvia was multi orgasmic and seemed like she could cum at will. At several points she would sit up and kiss me deeply and passionately. She would rub Heathers ass a bit and even once wrapped her hand around to play with Heather's clit.

As Heather started to cum, Sylvia reached down and turned her head sideways. She gave her the most erotic kiss I have ever seen. Heather kisses her right back while grinding her hips into me.

We had sex in several other positions with each one being copied by Sylvia and her vibrator. After a few orgasms and hours, we were exhausted. We talked for a little bit and then all turned in.