Caribbean Vacation

That triggered Dave to cum and I could easily feel his cock pulsing against mine through the membrane that separated us. I'm not sure who came next but it could have been either Barb or I because I felt her ass clench on my cock as she came just as I erupted into her ass. Dave and I were still hard enough to keep thrusting until she moaned, "Fuck that's awesome!" and came again.

There wasn't any 'neat' order to how we lay down, in fact we pretty much collapsed into a pile and then slowly separated. We relaxed for a bit, then I grabbed drinks so we could rehydrate and we chatted about how great the last few days had been. Dave said that they tried to keep their adventures to either vacations or a small group of friends and wondered if we were interested in being part of that group. Before I could say anything, Barb somewhat surprised me with a "Sure!".

Unfortunately, Dave and Gail had an early flight out the next morning so reluctantly we called it a night and after a few last minute hugs and kisses they headed back so they could get everything packed and we got ready for bed. It wasn't long before Barb and I were asleep either and as we slowly woke up the next morning Barb said, "Have the last few days felt kind of like a dream to you?"

I chuckled a bit and said "They have - but a very good dream."

"It's certainly been an amazing few days. I've done and seen things I never thought I would and enjoyed it all, how about you?"

"Me too. It's going to feel a bit weird going back to a 'normal' vacation now that they're gone."

"I know, I was thinking about that but just because they're gone doesn't mean it has to be totally normal. We can still do some of the things with each other that we enjoyed with them and I'm really looking forward to getting together with them again sometime once we're back home."

I rolled over and pulled her close for a nice long kiss and said, "So... just what kind of things do you want to keep doing?"

"Well, for today I was thinking of just enjoying a day together - grab some sun, a few drinks, do some snorkeling and go out for a nice supper. For tomorrow.... you'll just have to wait and see."

"That sounds like a plan for today and tomorrow - how about for right now we start with some sex?"

She smiled and said, "I like that idea too!"

Nothing more needed to be said and we spent the next hour or so making love - nothing different, nothing kinky, just good old-fashioned sex until both of us were totally satisfied and happily exhausted. The rest of the day went exactly as planned and we were nicely tired that evening so after a bit of tv, we curled up in bed holding each other and went to sleep. When I woke up, I looked over at Barb and found she was already looking at me with a sexy smile. "So, seeing as you're already awake, how about you tell me what you were thinking of for today that you weren't going to tell me about before?"

With that her smile got even bigger and she said, "Well, among other things I was thinking of maybe a little ass play to start our day."

"Mmmm.... I like how you're thinking - why don't you roll over onto your belly and I'll start with some nice kisses and we ca go from there?"

"Well" and she stopped for a couple of seconds, "I was actually thinking of playing with your ass, not you playing with mine."

That wasn't exactly what I was thinking but I'd seen how much she enjoyed using a toy on Dave so I wasn't totally surprised and said "sure, let's try it".

When she heard me agree, she rolled me over, climbed on top of me and spent the next few minutes kissing me and grinding against my hardening cock. After I was nicely hard, she pulled away and grabbed a bit of lube and a toy that I sometimes used to warm her up. When she came back to the bed she started kissing and licking my cock and at the same time she started sucking on it, I felt a well lubed finger pressing against my pucker. She was gentle but it still took me a minute or two to relax enough that she could slide the whole finger inside me. When I got used to that, she went to two fingers and when they slid in and out easily she looked up and said, "Ready?"

Some things you're just never 'ready' for and I think this was one of them but I nodded anyway and her fingers were replaced by the head of the vibrator pressing against my rear entry and the vibrations felt weird and yet really good at the same time. Even with the fingers and the lube it wasn't easy and I had to get her to slow down a couple of times until I could relax enough to take a bit more. Just when I felt the head pop in and thought everything was good, it only went in another inch or so before it stopped moving and there was a bit of pain. When I pulled away, Barb stopped pushing and asked if I was ok. I said it hurt a little and suggested she use a bit more lube. She put some more on the toy and some more on my ass and that seemed to do the trick because when the head went back in, the whole toy slid in with little difficulty so she went back to licking and sucking my cock while she fucked my ass with the toy. When she bent forward to take my cock back into her mouth, the angle must have changed because the next time she slid it in, I got what felt like a mild electric shock from where it touched inside me right to the tip of my cock. It was way more intense than when I'd felt one of Gail's fingers hit my prostate before and the "Yesssss" I let out told Barb to try it again.

With a bit of trial and error, she found exactly the right angle to hold it at so that it touched on every in stroke and when it did both Barb and I could feel my cock twitch. I wasn't in a hurry to cum and she was enjoying trying something new with me so we kept going like that for a bit.

When my whole body stiffened suddenly, she looked up and the look on my face must have told her something was up and when she followed to where I was looking, there was a very shocked looking maid standing in our bedroom doorway. Apparently, we were having so much fun we didn't hear her knock and now she'd been standing there watching my wife fuck my ass with a vibrator at the same time her mouth was bobbing up and down my shaft.

That brought everything to a screeching halt and both of us were stammering apologies. We'd talked with her a few times before - once when she came in to clean and a few more in the hall or the elevator. Her name was Tessara but she said it was easier to call her Tess. Whenever we'd had really hot sex (either by ourselves or with Dave and Gail) and the sheets really needed changing we'd left her a nice tip and the next time we'd see her we always got a smile and a wink. She wasn't really young, I'd guess in her mid to late 30's, spoke fairly good English and her dark hair and eyes gave her a very sexy look. Of course, having a nice sized but firm ass and a either a thin bra or maybe no bra covering her B cup breasts certainly added to the sexiness.

As her shock wore off, so did our embarrassment and finally Barb said, "I'd imagine you've seen things like this before."

"Yes, I've seen quite a few people having sex but never this."

"I hope you're not upset."

She smiled and said, "no, not upset. Maybe I shouldn't say but it actually looks hot. Now I'll be...how do you say 'horny' for the rest of the day."

Even with the darker skin we could see she was a bit flushed and her nipples were showing beautifully through her top.

Before I could say anything else, Barb said "Well, if you'd like you could watch for a bit, or instead of being horny all day I'm sure Chris would enjoy doing whatever would take care of your horniness - or maybe even give him a few strokes with the vibrator yourself."

"I should get back to my cleaning but..."

"Hey, don't I get a say in this?"

With a big smile Barb looked at me and said, "No" and without waiting for a decision from Tess she took my cock back into her mouth and using the toy on my ass again as Tess watched with obvious interest.

After a minute or so of watching she obviously made her decision saying, "I guess I have a few minutes. What I think you call 'going down' on a woman is not usual with the men around here. Would you make me cum with your tongue?"

"I'd love to... just put your pussy on my face and I'll show you."

Somewhat shyly, she pulled her uniform pants off and her underwear with them and then with a smile she pulled her top over her head and took off her bra as well. She looked even sexier naked than she had dressed - her nipples and areolas were even darker than her tits and her nipples weren't quite as long as Barb's but looked fatter and totally hard. Unlike Barb, she wasn't shaved smooth but she was nicely trimmed and as her pussy got closer to my face I could see that her lips were already slightly puffy with anticipation.

I love giving oral to a woman and the first taste of her pussy plus Barb's mouth on my cock and the feeling of the vibrator in my ass was almost enough to put me over the edge so I tried to focus as much as I could on giving her the best oral I could and that helped me hold back the orgasm that I'd felt building.

This wasn't a 'I'm going to tease you as long as I can' kind of oral it was a 'I want to make you cum now' kind of oral so I licked and sucked on her lips, tongued her pussy and sucked and licked her clit as she moaned in pleasure on my face. I'm not sure how long she'd been watching or how quickly she normally came but it was definitely less than 5 minutes before she let out a burst of Spanish that I couldn't understand followed by a moaning and body quivering that didn't need explanation or translation.

When she'd finished cumming, she moved off my face and Barb said, "Do you want to take over here while I enjoy his tongue for a bit?"

I'm not sure if she fully understood what Barb meant but as Barb moved away and gestured at the vibrator she smiled and said, "I've never done something like this before, are you sure it's ok?"

When Barb nodded and moved up towards my face, I felt Tess hesitantly take the vibrator and start moving it in and out of my ass. The angle, speed and force were different than Barb's but it felt just as good and possibly better just knowing it was someone new doing it. What I wasn't expecting was to feel her lips close over the head of my cock and slowly suck it into her mouth. There was very little licking or building up to it - she just took the whole length into her mouth and then backed off again until just the head was inside and then repeating the whole thing without releasing the suction until she finally had to breathe and then she started all over again.

While I was certainly enjoying the taste and feel of Barb's pussy on my face, now I was focused more on the feeling from Tess's mouth on my cock and the orgasm that I'd been holding back came screaming back my whole body tensed up. Seeing what was happening and knowing with her on my face I couldn't say much, I heard Barb whisper to her "he's almost ready to cum".

I felt more than heard her "mmmmmm" but she didn't stop so with a slightly muffled groan of "Yesssss" I started cumming.

Later, Barb told me that Tess looked a bit surprised when my cum started shooting into her mouth but she didn't let any escape and when I stopped cumming she looked at Barb, smiled and swallowed. I wished I could have seen it but shortly after I came, so did Barb and she must have been excited because she seemed to squirt more than usual as she came.

I kept licking Barb through my orgasm and after I felt Tess let my cock slide out of her mouth I heard her say, "Wow, now I see why sheets are so wet sometimes. I must get back to work but if I leave your room until last I will have more time, likely around 3 - if you would like me to stay for some more fun."

We both assured her we'd love to have her return later and with a smile she said she'd be looking forward to it. Originally Barb and I had planned to spend most of the day relaxing and maybe spending a bit of time at the beach but knowing that Tess would be back later, we decided to grab a shower, get an early lunch and spend some time at the beach so we could be back to the room when she got there.

We'd just rinsed off in the shower and put on our robes when there was a knock at the door and when I opened it, there was Tess with a smile on her face. I'm sure just in case someone was listening she said, "Is it ok if I clean your room now or should I come back later?"

"Now would be fine." and as she came in and the door shut she put down her cleaning things and gave each one of us a quick hug and a kiss. "Lots of guys want me to come to their room for sex and I say 'no' but you are the first couple that have wanted me to join them and I find that a lot more exciting."

When she heard that, I couldn't resist asking, "Why, because you like to watch another couple have sex or because you like to play with a lady too?"

We could tell she wasn't sure how she should answer because she didn't say anything right away but after a bit of a pause she said kind of nervously, "Well yes to the first part and maybe to the second part. I have only been with one other woman but sometime I would like to try it again" then looked at us to see if we were ok with her answer.

"Well," I said, "We're both ok with you enjoying either or both with us. Barb just had her first sex with another woman a couple of days ago and could likely be convinced to try it again" and when I looked over at Barb she nodded which brought a big smile to Tess's face.

"I was still horny all day thinking of coming back. I want to have your cock in me but would like to feel your tongue on me again first. As I said, not many of the men here enjoy that and you made me feel so good that way."

"I'd love to - why don't you get undressed and lay down so I can just relax and enjoy my tongue."

She quickly undressed and as she took her thong off I could tell by the wet spot on the crotch that she had indeed been horny all day. When she lay back, I couldn't resist taking one nipple into my mouth and sucking on it. Her eyes were soon closing with pleasure but they quickly re-opened when she felt Barb's tongue and lips on her other nipple. When she saw what was happening she lay back and was soon softly moaning. I left Barb to look after her nipples and I moved further down her body until I was able to tease her outer lips with my tongue.

This time there was no rush and we were both able to enjoy me tasting and teasing her as I learned how and where she liked to be nibbled and licked. At one point I looked up and instead of Barb sucking on Tess's nipples, she'd moved up a bit and now Tess was sucking on hers. I wasn't sure if both of them would be open to it but figured I'd ask anyway, "Hey Barb - wanna switch?"

Barb nodded and slowly and somewhat relucantly pulled her nipples away from Tess's mouth. As I shifted up the bed, Barb shifted down and for the next little bit, I had the best view of all - I could watch as Tess sucked and tongued my cock and when I looked down, I could see my wife licking and sucking on Tess's pussy. I was doing ok holding back until I saw Tess grab at Barb's head, pull it against her pussy, her whole body started shaking and I could feel her "MMMMMMaaaaahHHH" vibrate through my cock.

I was really close to cumming but didn't want to yet so I reluctantly pulled away from her mouth and just watched Barb continue to tease her with her tongue until she was done cumming. Then, I motioned for Barb so shift out of the way and moved so I could raise Tess's legs and slide my cock slowly into her pussy. She was far snugger than either Barb or Gail but nicely lubed so I was able to slide in relatively easily. When the head slid inside she moaned a bit and by the time I was all the way inside her she was muttering things in that I couldn't understand. Most of it was Spanish with the occasional 'yes' or 'very good' thrown in. Barb had gone back to teasing and sucking on Tess's nipples as she watched the two of us fuck.

Apparently, Tess was either was the kind of lady who would cum very easily or she was extremely aroused because it wasn't long before she was cumming again and I was trying to hold back my own orgasm. I managed to hold on through 2 more of her orgasms but on the third I couldn't stop it and started cumming in her pussy. The contractions of her pussy on my cock at the same time really added to my orgasm and I'm pretty sure I shot more than usual.

I kept myself inside her as long as I could but eventually I softened enough to slide out with a trickle of my cum following my cock. I could see Barb watching my cum ooze from Tess's pussy but before I could suggest it, Barb shifted again until her face was right over Tess's crotch and then she tentatively licked up some of my cum from her slit. Obviously she enjoyed it and she continued licking the length of her slit and occasionally sliding her tongue inside. Each time she did, a slight moan came from Tess. I was so distracted watching Barb licking my cum from Tess's pussy that it wasn't until Barb moaned as well that I realized Tess had guided her over so that she could lick Barb's pussy at the same time.

Now it was Barb's turn to cum and cum she did - squirt after squirt of cum all over Tess and the bed but Tess kept going until Barb came again a few minutes later. I wasn't sure if Tess had cum again but after we were done she said she'd actually came twice - once just from Barb squirting on her face and the second from Barb sucking on her clit.

While we rested, Tess said that she was going to be off the next few days but would love to join us again the next day she was working and we said we'd love to have her 'cleanup' the next time she was over which got a smile and a "I'd like that too!" from her before she dresssed, changed the sheets and left.

All by ourselves again, I looked at Barb and said, "Wow, that wasn't how I was expecting today to go but I enjoyed all of it."

"All of it? Even me using the toy in your ass?"

"Not at first - but once you got it in, it felt great."

"So, you'd be ok to do it again?"

I didn't think I'd ever be telling anyone I enjoyed something up my ass but I found myself saying, "Yes I'd definitely be ok to do it again."

"Any thoughts of finding out what a real cock would feel like?"

"Thought about yes but not interested in actually doing it, I'll stick to a finger or toy instead."

"That's fine, in fact before Gail left she said she was pretty sure we'd both enjoy it and was telling me she had a harness at home that would hold one of her vibrators so she could actually fuck Dave that way - I think she called it 'pegging'.

Tess was able to join us a couple more times before we had to leave and each time was just as hot as the first. I did my best to make up for the local guys not liking to give their partner oral because I ate her at least once and sometimes two or more times each time she came over. The last time we got together they had just taken turns using the vibrator on my ass again when Tess mentioned that it looked like it felt really good.

When I asked if she wanted to try anal she said she wasn't sure she wanted something the size of my cock in her ass but thought maybe the vibrator would be ok because it was a bit smaller. I would have loved to try it on her but knowing that Barb had used it on me several times she said she'd feel better with her being the one to use it on her. Tess lay on her back and Barb did exactly what she'd done with me the first time - first one well lubed finger, then two, then when Tess was good and ready she slowly started sliding the vibrator inside her ass. I was enjoying watching but didn't want to just watch so while Barb was fingering her ass, I was sucking on her wonderful dark nipples and playing with her pussy. When Barb started easing the vibrator into her, I moved so I could lick and kiss her clit at the same time which really increased how much she was moaning.