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A couple of months later, Carlos asked if I'd be able to help him with a snorkeling tour the next day. Apparently, a family of three from Australia had booked a tour but they didn't speak any Spanish and he had a lot of trouble understanding their accent. I had tentative plans for the day but when he told me he'd scored some good dark rum, I figured I might as well go with him.
When I got to the boat the next morning, he introduced me to Frank and Amanda, a couple in their early forties and her daughter Samantha from a previous marriage who quickly told me just to call her either Sam or Sammie. If I hadn't known they were mother and daughter, I'd have thought that Amanda was just an older sister because she looked about 25 where Sammie had already told me that the trip was for her 21st birthday. Both had long, blonde hair, a decent tan with some sexy tan lines and their boobs were barely contained by the bikinis tops that they were wearing. I was no expert but I figured that Amanda was likely a D-cup where Sammie was likely a size or two smaller. Their bottoms didn't cover much more, with a nice view of their ass cheeks and from the way they fit, I was pretty sure they were both shaved smooth or at least very well trimmed.
Their accent was definitely strong but after a few minutes of conversation, we weren't having any issues understanding each other, so I just translated back and forth between them and Carlos. I was definitely hoping to see even more skin from either Amanda or Sammie before the end of the day but it was sooner than I'd expected. We'd gotten to the snorkeling spot and I'd dove in to grab the mooring line when Amanda jumped in for a quick swim before we started. I looked over just in time to see her trying to pull her top back down over a very nice pair of tits but when she pointed down, I could see her sunglasses at the bottom, about 15' down. I certainly wasn't up to some of the free-divers, but 15' wasn't a problem and when I came up with them, she was hanging onto the boat waiting for me. When I handed them to her, she gave me a smile and said, "Thank you! I guess we're even for that flash you got a few minutes ago."
She didn't seem to be particularly embarrassed so I just said, "Then feel free to drop your sunglasses any time you like!"
Before we could say any more; her, Frank and Sammie joined us in the water with Carlos coming in last. Between Carlos and I, we made sure they saw as much as we could and after an hour or so, we got back on the boat for a snack before going to another spot. As we ate, they told us how much they'd loved it and how glad they were that they'd chosen Carlos. The other spot was only about 15 minutes away so we chatted and I found that Sammie had an older brother but he'd already gotten married and his wife was due with their first child so he couldn't make it. She was taking a year off from university and was studying Marine Biology which explained why she was so eager to go snorkeling. I told them I'd grown up in the Dominican, moved to Texas, gotten married/divorced, moved back and had a condo overlooking the beach so I was able to enjoy a fair bit of beach and water time.
Once we were in the water at the second spot, we saw even more fish than at the first spot and there were even a few small eels and a couple of rays that got Amanda and Sammie excited. My excitement was the view of Amanda's tits as well as the way hers and Sammie's suits barely covered their asses whenever I looked over as we snorkeled. Amanda had gotten a bit cold on the first dive so she'd thrown a t-shirt on over her top for the second dive. On the ride back, it was a lot hotter so she peeled it off and as she did, one boob popped out of her suit and the view was even better than when she'd been in the water. With a quick, "oops!" she tucked it back in and I don't think Frank noticed but Sammie did and I noticed her roll her eyes a bit.
When we got back to the beach, Frank gave Carlos a good tip before they headed up the beach. I stayed to help Carlos put things away and grab the rum he'd promised me as well as some of the tip money. As we cleaned up, Carlos noticed one of the women had left their wrap behind but they were already gone. He had a contact number for them so I called to let Frank know and found that they were staying right beside my condo building. I told him I'd bring it back with me and one of them could grab it there which was fine by him.
I'd only been back a few minutes when Sammie came over to me. As I handed her the wrap, she said, "I'll bet you were hoping mom would come down and give you another flash for bringing it back."
I decided to play dumb and said, "Flash?"
"She enjoyes flashing guys sometimes, so I'm pretty sure that her boob popping out on the boat wasn't accidental and neither was her top coming off when she jumped into the water. Yesterday she 'forgot' to tie her top when she rolled over at the beach and gave a couple of college guys a quick view of her tits. I also know that a couple of delivery guys at home have gotten a good look when she answered the door in just a robe and she's had more than one 'accident' around the pool at home when we've had friends over."
"Well, accidental or not, it was a nice view! Does your dad know or care?"
"She only does it when he's not around or can't see so I don't think he knows. As far as I know, she's never done more than show her boobs and I think it turns her on."
That made both of us chuckle and before she left, we chatted for a few minutes and along the way, I pointed out my balcony. When she saw it, she said, "It's likely a good thing we don't overlook the beach like that or I'm pretty sure mom would be 'accidently' showing her boobs to people on the beach."
Of course, that made me picture Amanda on the balcony flashing people while I was there to watch and hopefully touch but figured it likely wouldn't happen. The next day, I was just heading out for a walk down the beach when Frank came up to me.
"Hey Brian, I was wondering if you could do me a favour?"
"Possibly, what?"
"Well, Amanda and Sammie want to do some shopping today but I was hoping to get in a round of golf so I'd happily pay you to go with them plus you speak Spanish so that would help too."
Hmmm, get paid to spend the day with Amanda and Sammie plus a chance at another flash from Amanda sounded good so we finally agreed on $100 plus they'd cover any food or drinks while we were out. An hour or so later, the two of them met me at the beach and they looked great. Both were wearing shorts with Amanda wearing a tube-top that showed nipples instead of a bra-line so I was pretty she was braless and Sammie was wearing a light top with a thin sports-bra under it. From there, we grabbed an Uber to where most of the shops were and I pretty much followed along with wherever they wanted to go and did a bit of negotiating for anything they wanted.
At one shop, Amanda had gone behind a divider to try on a different top and asked me to see what I thought. When I shifted so I could see, she had on an even smaller bikini top than she'd been wearing that barely contained her tits. I quickly decided it would be a good time to see if the flashes the day before were accidental or not so I said, "It looks great but what will happen if you walk or turn?"
With a grin, she did both and as I'd figured, as soon as she turned too quickly, both tits popped out of place and I got a great view before she casually tucked them back in and with a sexy smile she said, "Hmmm, maybe not this one!"
When I turned around, Sammie was close enough to have seen too and just whispered, "See... she knew that was going to happen!"
A few shops later, Sammie was looking at some souvenirs while Amanda was looking at t-shirts. I was fairly close when she reached up to get one off the top shelf. That just pulled her top higher, letting both tits pop free from the bottom. Quickly remembering what Sammie had said about her mom never doing more than just showing her tits, I took a chance and quickly said, "Let me help..." and made sure that I ran my hands gently but quickly over both boobs as I reached for the bottom edge of her top and then a slower feel as I pulled it down to cover them.
I figured there were only a few options; she'd get pissed and tell me off but didn't think she'd make a scene in the store, believe that I'd been innocently trying to help or realize what I'd done and enjoy it. When she turned, her face was slightly flushed and her nipples were so hard they showed beautifully through her top. Thankfully, instead of being mad, she just grinned and said, "Thanks for the hand!" with emphasis on the word "hand".
Then, as she moved behind me, I felt her pressing her tits against my back and at the same time, ran her hand lightly over my hip and across my ass. After a bit more shopping, we stopped for lunch before hitting another run of shops. Along with the food, we had a few rounds of drinks which made the afternoon even better. Whenever possible, either I'd move behind Amanda so I could grab her hips and press against her ass or she'd move behind me and press or slide her tits across my back. At the very last shop we stopped at, Amanda wanted to try on one last top and just as she had before, she wanted me to take a look and see what I thought. This one was a very thin, silky material that left no doubt that she was braless under it.
With a smile, she asked, "Do you think my nipples show too much through it?"
They were already showing nicely but I pretended to think about it for a second or two before saying, "They show a little bit but it just makes you look even sexier but I'm not sure how it would look if they got any harder."
While looking straight at me, Amanda undid the top few buttons, opened the shirt and said, "Why don't you find out?"
That was a pretty clear invitation so I reached forward to gently touch and squeeze both nipples and then just in case I didn't get another chance, I leaned forward and sucked one between my lips so I could lick and suck it at the same time. She must not have been expecting that because she let out a soft, "Ohhhh!"
Still smiling, I backed up and said, "There, let's see now."
When she did the top back up, her nipples were even more clearly visible through the thin fabric so I said, "Well, if it was up to me, I'd say buy it because you look fucking awesome like that!"
After looking down and then giving both nipples a quick squeeze of her own, with a clear reference to Frank, she said, "I would, but someone wouldn't think it was appropriate" and while I was still standing there, she took it off and put her original top back on, giving me an even longer view of her tits than I'd had so far. Once it was on, she reached forward to give my stiffening cock a slight squeeze and said, "Mmm... I think you liked what you saw!"
With a quick, "And touched too!", I slid back around and tried to look relaxed as Sammie came over to see what was taking her mom so long.
I was pretty sure that Sammie noticed some of the flashes through the day but other than a bit of a smile a couple of times, she didn't say anything else about it. When they were done shopping, we went for a couple more drinks before heading back. While Sammie was using the bathroom, Amanda said, "I've enjoyed the shopping much more than I was hoping for and I think you did too. Sammie's mentioned that you've got a great view from your balcony, maybe I could come over and check it out sometime while we're here?"
"I'd love to show you the view, what about after supper tonight?"
"Sounds good, I'll bet that Frank will be tired and maybe a bit drunk from golf so how about 7ish?"
"Perfect, see you then!"
At almost the same time, Sammie got back so we got another Uber and headed back to the resort area. When we got there, Amanda gave me $200 saying, "$100 really doesn't cover how much I enjoyed today!"
When I got upstairs, I grabbed some supper then a quick shower and shortly after 7, there was a knock on the door. Opening it, I was totally surprised to find Sammie standing there instead of Amanda. She was wearing the same shorts she'd had on when we went shopping but had changed into a fairly tight t-shirt and judging from how easy I could see her nipples, I was pretty sure she'd ditched the bra. When she saw the look on my face, she smiled and said, "How about I explain inside?"
I was really wondering what was happening, so after letting her in, she said, "I noticed mom flashed you quite a few times today and I'm pretty sure you had a feel or two as well which I've never seen her do before. Mom doesn't know, but I overheard the two of you talking about getting together tonight. She was right though, Frank had a few drinks during the day and by the time they were done supper, so had mom. Frank always gets really frisky when he's had a few drinks and mom must have been thinking about coming here because as I was coming back from the bathroom, they were fooling around in the kitchen and I heard Frank tell her that she felt really wet so she must be as horny as he was. When he suggested they go for a 'nap' after supper, she really couldn't say 'no' and it wasn't long before they'd headed to their bedroom. I know from experience that they'll be at it for a while and likely fairly loud before they're done, they both of them will likely pass out from the booze. I really didn't want to listen to the two of them having sex so I yelled that I was going for a walk along the beach. Even though it's my mom and stepdad, listening to two people having sex still turns me on, especially seeing as I broke up with my boyfriend a couple of weeks before coming down here so...."
After stopping to take a deep breath, instead of saying anything else, she reached down, grabbed the bottom and peeled the t-shirt up and off.
When her smaller but firmer tits came into view, I couldn't hold back a, "Damn you look great!"
As soon as I said that, I could see her relax as she said, "Good, I was afraid I'd just made an ass of myself because you wouldn't be interested."
"Not interested in seeing a great looking lady topless and maybe more? I hope when that happens, they're measuring me for a coffin!"
Her laugh took away the rest of her nervousness and tension so I moved close enough that I could reach out and cup both of them. Having held Amanda's tits earlier, it confirmed what I'd already thought; that while they were smaller, they were also firmer and when I gave her nipples a gentle squeeze, I also found they were just as sensitive as her mom's. After a quick look up to make sure she was still ok with things, I bent my head down so I could take one nipple into my mouth and after sucking and kissing it for a few seconds, I switched to the other one. Whichever one I wasn't sucking was being gently touched, teased and squeezed between my fingers. I was a little surprised when she brought my head up so we could kiss but once our lips were together and our tongues were getting acquainted, the surprise quickly went away and I started kissing her back. When we stopped to catch our breath, Sammie said, "Wow, it's nice to find a guy who doesn't think my boobs are stress balls for squeezing."
"Not at all and guess what, I'm also more interested in you enjoying yourself than me!"
"Mmmm, so does that mean you'd be willing to use your tongue on more than just my nipples?"
"Certainly! How many times has a guy made you cum with his tongue before?"
"Actually cum? Never, usually they just give me a few licks until I'm wet enough for more or until I agree to suck them."
"Well, I'd love to give you your first oral orgasm and with any luck, your first two or three!"
With a big smile she said, "One would be amazing but I definitely wouldn't say 'no' to more either."
"Then let's get rid of those shorts so I can enjoy seeing the rest of you naked and make you cum at least once with my tongue!"
As she took her shorts off, I pulled off my shirt and shorts showing my already stiff cock which got a, "Mmmm, now I'm even happier that I'm here instead of mom!" from Sammie.
After leading her to the bedroom, I had her lay on her back near the edge of the bed so I could kneel and get easy access to her pussy. Knowing she'd never had a guy make her cum with his tongue made it hotter as I started licking and kissing around her pussy, getting closer and closer until I made the first slow, gentle pass with my tongue from the bottom of her slit to the top. It wasn't long before she was moaning softly and I intentionally focused on just her pussy, with only an occasional light lick near her clit. Eventually, her moans of 'Yes!" or "That's good!" were getting louder and closer until she finally yelled, "Yes! Fucking YES!" as her body quivered in orgasm.
After she caught her breath, she said, "That was better than even some sex I've had!"
"Good! That was long and slow, the next one or maybe two are going to be quick and fast!"
Without giving her time to answer, I went back to licking her pussy but started spending as much time on her clit as her pussy. Sometimes I'd lick it, sometimes I'd suck gently on it and sometimes I'd do both. As I'd told her, it wasn't long before her hips were arching up against my mouth and I heard, "Oh shit, I'm cumming again!"
As soon as that orgasm tapered off, I started thrusting a couple of fingers in and out of her pussy while flicking my tongue back and forth over the tip of her clit. I don't think it was even a minute before she was cumming again and it was intense and long. It started with a moan of, "Damn, that's..." then changed to, "FUCK YES!" as she her hips arched up, her pussy got noticeably wetter and I could feel it repeatedly contracting and releasing around my fingers.
When she finally stopped cumming, she looked at me with a slightly dazed expression and simply said, "WOW!"
The combination of the way she said it and the look on her face made me laugh which got a drunken looking grin from her. When she'd relaxed a bit, she looked at me and said, "If you'd like, I'll happily give you some oral too."
As much as I'd have loved to feel her lips around my cock, it had been a while since I'd had sex and a lot longer since I'd had sex with someone less than half my age so just to make sure I was able to enjoy the feel of my cock in her pussy and hopefully filling her with cum, I suggested, "How about we hold on to that thought until after we have sex?"
"Hmmm, sounds good to me!"
Without moving her, I just stood, gently lifted each leg and pressed the head of my cock against the slick entrance to her pussy. She'd said she'd never had a guy give her good oral and as my cock started to slide in, I wondered what size cock she'd been used to because she felt incredibly tight. As my full length finally slid into her, she confirmed what I'd been thinking by saying, "Damn, I don't think I've ever been this full before. At first, I wasn't sure that all of you would fit!"
"And now that I have?"
"I love it!"
"Good, then let's see how it feels once I start moving."
Initially, I pulled back and then pushed forward slowly and gently but as I felt her pussy stretching and relaxing to take me in, I sped up until I was thrusting in and out with a reasonable speed and force. The look on her face told me that she was enjoying every stroke and after a few minutes, she said, "I think I'm going to cum again!"
As soon as I heard that, the next time I pulled out, I only thrust back in a couple of inches and then started thrusting in and out faster but staying shallow. As I figured, that seemed to keep her right at the "I'm ready to cum" line without letting her cross it. After a minute or two of that, I asked, "Are you ready to cum really hard?"
"YES!"
"Ok, let's get you there!"
On my next thrust, instead of quick thrusts with just the first couple of inches, I went full depth and then fucked her just as quickly but only pulled back a couple of inches before thrusting back in again and at the same time, I reached down and started rubbing around and across her clit.
I wish I'd had a camera to catch the expression on her face when she came. Her mouth and eyes were wide open and the only sound I heard was a long, low, "Ahhhhhhhhh!" as her pussy convulsed around my cock. I'd been doing my best to hold back but feeling her already tight pussy clenching as she came, I couldn't hold back and started filling her pussy with cum. Then suddenly, she yelled, "Fuck, it's not stopping!" and her entire body quivered and shook with her orgasm.
When it finally ended, she was breathing heavily and as we lay on the bed, she finally said, "I've never cum that hard from sex or even masturbating! Do you think you can get hard again?"
"It might take a bit but I'm sure I can."
"Good! I don't know when I'll ever get fucked like that again so I'd love to go again. What'll get you hard the fastest?"
After thinking for a few seconds, I said, "I'd love to see you play with yourself."
Almost shyly, she said, "I've never done that with anyone watching before but I'll try."
She was a bit hesitant at first but after slowly fingering her pussy with one hand while she teased her clit with another, she quickly got into it and by the time I was hard again, she'd had a small but satisfying orgasm.
As she stroked my re-hardened cock, I asked "Are there any positions you really like?"
"Well, I like the angle and depth when I'm kneeling on the bed or bent over it."
"Then let's try that."
After she'd rolled over and shifted into position, I took a few seconds to enjoy the view of her puffy pussy with some of my cum still oozing out, beautifully framed by her ass cheeks with an equally nice view of her asshole topping it all off. As I slid my cock back into her pussy, I couldn't help but wonder if she enjoyed any anal play or if she'd even tried it before. As I fucked her slow but deeply from behind, I could hear, "Yes... just... like... that... oh fuck... yes!" each word in time with a new thrust.
As she built toward another orgasm, I started running my fingers lightly down her back, across her ass cheeks and down her thighs. Every so often, I'd let a finger drift close to or across her pucker and at first, she'd tense slightly but didn't tell me to stop. After a few minutes of it, I was pretty sure I felt her push back slightly each time my finger teased her asshole.
On the next pass, I let my finger linger on her pucker and asked, "Do you like your ass being touched?"
"It's different and feels a bit weird but good at the same time. A couple of guys have wanted to put their cock in my ass and a few have tried pushing a finger in but they weren't as gentle as you're being so I always stopped them."
"Oh, so you wouldn't stop me?"
"I'm not sure but I'd be willing to try a bit more."
"That's the thing with ass play, you don't need to just be willing, you have to want it."
"I'm not sure I'd ever actually want it."
"Shall we see?"
"What do you mean?"
"Well, if you say 'yes', I'm going to do something that I'm pretty sure no one's ever done with you before and when or if you decide you want more, just let me know."
I could tell she wasn't totally sure but after a few seconds she said, "Yes!"
With that, I had her stand up and bend over the bed so I could go back to lightly running my fingers over her ass cheeks as kneeled behind her so I could slide my tongue into, then up and down her pussy. Then instead of running a finger over her asshole, I kept going with my tongue until she felt it glide over her pucker.
"Holy shit! What was..." and then as she realized what I'd done she said, "you just licked my asshole!"
"I did! So now you have to tell me whether it's something you'd be willing to try again or something you want me to do again."
"I want it, I definitely want it!"
"Want what?"
After only a brief hesitation, she blurted out, "I want you to lick my asshole again!"
She couldn't see my smile as I ran my tongue from her pussy to her ass and back several more times before sliding a couple of fingers into her pussy. For the next couple of minutes, I kept tonguing her pussy as I ran my tongue around and over her asshole.
When I stopped, she knew what I wanted to hear and said, "It feels really good, I want you to keep licking my ass!"
I did exactly what she asked as well as pushing the tip of my tongue against it until it slid slightly inside. It was something I'd done occasionally with Diane and if she'd been drinking, she loved it but sober, she'd say it was nasty and tell me to stop.
Sammie didn't tell me to stop, instead she blurted out, "I like that, do it again!"
I did it a few more times just to make sure she liked it and at the same time, I took one of the fingers that had been in her pussy and in between licks, I pressed it against her pucker. I repeated that a few times and then stopped. After a few seconds, I heard a soft, "Your finger felt good, I want to feel more of it."
After getting her used to just the tip sliding in and out, I reached for some cherry lube beside the bed and after getting my finger nice and slick, I eased it back into her ass but only as far as the first knuckle. In between licks up and down her pussy, I asked, "Do you want me to push it in further?"
"Yes, damn it, I want to feel more of it, slide it into my ass!"
I could tell she was getting into it when I slid my finger further in and she said, "I like it, it doesn't hurt and it feels good in a weird way."
I kept licking her pussy as I fingered her ass and as much as I wanted to suggest adding another finger, I decided to wait and see if she suggested it. Sure enough, a minute or so later, she said, "Let's see what two fingers feels like."
It was noticeably tighter but with a bit more lube, I was able to add a second finger to the first and slide them in and out in sync with my tongue going back and forth over her clit. When she asked for three fingers, I added one more and less than a minute later, she came. I think it caught her by surprise because just in the middle of saying, "Your tongue and fingers feel really good!", she stopped, tensed, moaned "Oh fuuuucckk!" and then she relaxed again before finishing the "feel really good" part.
When I stopped licking her and pulled my fingers out of her ass, she looked back at me and for a few seconds she looked confused and then after licking her lips, she said, "I don't know if I'll get another chance before we leave so I'd like to try.... no, I want to feel your cock in my bum!"
Those were the words I'd been waiting to hear so I gave her pussy and ass one last lick before I stood up and got my cock nice and slick with lube. When she said, "I know you will anyway but please go slow and be gentle."
"Don't worry, it'll be you controlling things, not me" and with that, I lay on the bed and motioned for her to straddle me.
At first, I didn't think she'd understood because she lowered her pussy onto my cock and gave it a few good thrusts but just as I was going to say something, she lifted all the way off, shifted a bit and then holding my cock where she wanted it, she lowered back down. I watched the look on her face as she felt a cock going into her ass for the very first time and while it didn't go in nearly as easily as my fingers, with a look of determination, she kept trying. Bit by bit, I felt her ass opening to accept the head of my cock and when it finally popped inside, she stopped and said, "Holy shit, you feel even bigger in my ass than in my pussy!"
Over the next minute or so, she took more and more of my cock into her ass until she was basically sitting on my legs with no space between us. When she started to lift back up, I stopped her before reaching between her legs to gently rub her clit. "Do you like the feel of my cock in your bum?"
"It hurt a bit at first but it feels good."
"Do you like me touching your clit?"
"Fuck yes!"
"Could you cum just from my finger on your clit?"
"Yes, I think so!"
"Then just think how hard you're going to cum once you start feeling my cock going in and out of your ass at the same time that I'm touching your clit!"
Just hearing that seemed to put a slight tremor through her body and then as I teased her clit, she started moving up and down on my cock. At first, she went very slowly to get used to the feeling but once she had, she sped up a bit. It took a few minutes but then she said, "I'm... I'm close. I'm gonna cum soon!"
That was my cue to move my hand so I could slide a couple of fingers into her pussy and use my thumb to rub her clit. Like a firecracker going off, she pretty much exploded in orgasm and the feeling of her ass clenching around my cock as she came was intense but somehow, I managed to not cum. As her orgasm tapered off, she was pretty much laying against my chest and whispered, "Even if I'm sore tomorrow, I want to feel you cum in my ass."
I'd been hoping to keep going and she'd said she liked it 'doggy' so after getting her in position, and easing the head of my cock back into her slightly open but well lubed ass, I said, "Let's see how you like it this way."
From her moan as I slid the rest of the way in and then pulled back, I guessed that she was enjoying it so I kept thrusting in and out. The different position made it easier to slide in and out so I was able to go a bit faster than when she'd been riding me. I knew from experience that I'd cum faster in this position and when I got close, I told her to reach down and play with her pussy. I was hoping that she'd be able to cum one more time before I did. When I felt her fingers brushing my cock, I knew she was doing what I'd told her but it wasn't long before I couldn't hold back and started cumming in what had been her virgin ass. As it turned out, that was the extra 'push' she needed to cum and just after the second or third spurt of cum, her ass clenched so tightly around my cock that I could hardly move and she let out almost a wail of, "Oh fuck that feels amazing!" as she came.
Her ass had clenched so tight that it was actually holding my cum back but as soon as she relaxed a bit, I felt the rest of if explode into her ass. As I slowly slid out, there was a bit of a 'pop' and a trickle of cum onto the bed but any laundry I'd have to do was well worth the pleasure I'd had.
Laying on the bed, Sammie looked at me and gave me a hot, long kiss before saying, "You took more time just getting me ready for anal than a lot of guys take to have sex. Thank you, it felt really good!"
When she looked over at the clock, she said, "Holy shit, it's almost 10. I'd better get back just in case mom's still up.
As she slowly got dressed, I poured a couple of shots of tequila and handed her one. "What's that for?"
With a smile, I said, "Well partly to celebrate your first anal but more so if anyone asks, you can tell them you had a few drinks at a beach bar before coming back."
Smiling back, she said, "Good idea!"
After downing the shot, she gave me one more kiss before heading back. After she left, I grabbed a shower and headed for bed, thinking that it had been an amazing evening and wondering if I'd still be able to connect with Amanda before they left.
That thought got answered about 10am the next morning when I noticed Amanda and Sammie walking down the beach, walking like they were looking for shells. When Amanda saw me, she waved and once they were closer, after a bit of casual conversation, she said, "Are any of the condo's in your building rentable?"
"Yes, some are. Why?"
"Well, we're really enjoying staying here but the resort is fairly expensive. I thought maybe if we rented a condo next time then it would be cheaper, so I was wondering if I could take a look at yours to see if one like it would work."
"Sure, why don't both of you come up and have a look?"
Thankfully, that's when Sammie said, "You go look if you want mom, maybe it was something I ate yesterday but I'm not feeling that well. I'll either be at the pool or back in our room" then without her mom seeing, she gave me a grin and a wink.
I noticed a flash of excitement on Amanda's face before saying to Sammie, "Sorry you're feeling a bit off. I'll look at the room and maybe check out a few of the other shops before I come back."
"Ok, what about Frank?"
"Today was the day he booked the fishing with Carlos, remember?"
"Oh right! Okay, I'll see you when you get back."
As Sammie headed back down the beach, Amanda and I went to the condo. As soon as we were inside, Amanda said, "I wasn't sure you'd want to talk to me after I didn't show last night."
Knowing exactly why she wasn't there, I couldn't help but ask, "Did you have a bit of whatever Sammie's got today?"
Realizing that was a good excuse, Amanda said, "It could have been. I just thought maybe it was the heat, the drinks or both but I went to bed almost right after supper."
"I understand. You seem to be feeling better today so I'm hoping that you'd like to catch up on what you missed last night."
"That's what I'm hoping too! You've likely guessed that I enjoy flashing guys and seeing their reactions turns me on but there was something about the way you looked at me that made me want to do more than just flash you. Frank's a great husband and certainly looks after me in bed but my first husband, John, was a lot more... adventurous, and I really miss that since he passed away. Any time I flashed him, he'd have been touching me right away and it felt just like it did when you touched me when we were shopping. If I flashed Frank, there's a good chance he'd just tell me to hang on until the game was over."
As she finished, while looking straight at me, she reached behind her, untied her top and let it drop to the floor. Immediately, my eyes went to her chest and especially her nipples that were already starting to harden.
"See, that's what I mean! You're looking at my tits like you want to eat them. That really turns me on and makes me think of how much fun we could have."
Moving closer, I cupped each of her larger tits with my hands and traced gentle circles around her nipples with my thumbs. They were already slightly hard when her top came off but as they quickly hardened even more, Amanda said, "That feels great!"
"Then how about this?" and I leaned forward to take on nipple between my lips so I could suck and tease it with my tongue.
Unlike the first time when we were shopping, there was no risk of anyone seeing us and no rush, so I took my time and went back and forth from nipple to nipple a few times until both nipples were long, hard and swollen. After pulling my head back to admire the result, I said, "They're beautifully hard now!"
Moving closer, Amanda ran her hand up my leg until she was holding my cock through my bathing suit then said, "You're pretty hard too, do you think you'll get harder if I do the same thing?"
"There's only one way to find out for sure!"
Once we were in the bedroom, we both got fully undressed and as I lay back on the bed, Amanda wrapped her fingers around my cock and said, "You get hard a lot faster than Frank but let's see if I can get you even harder!"
That's when I realized that I never did get to feel Sammie's lips around my cock but that thought was quickly pushed aside as Amanda started licking and sucking my cock. It didn't take long to realize that not only did she enjoy what she was doing, she was damn good at it! After a few minutes, she stopped long enough to ask, "If I keep going until you cum, will you be able to get hard enough again to fuck me?"
"I'm sure I'll be 'up to it' again, especially with a bit of help from your fingers or tongue."
"Perfect! Frank's always good for one big cum but seldom for two so I don't get to taste his cum as much as I'd like because I also enjoy him filling my pussy."
As her lips went back around my shaft, she started gently massaging the spot right behind my balls and then bit by bit, I felt her finger working further back until I felt the tip brush over my asshole. When I moaned instead of pulling away, Amanda looked up, smiled and said, "That's exactly what John would have done but Frank thinks anything ass related is weird, dirty and not normal, whether it's his ass or mine."
Knowing I was fine with it, her finger continued to tease my ass while she kept doing amazing things to my cock with her lips and tongue."
She must have noticed the lube because she reached for it and then a few seconds later, I felt a much slipperier finger pressing against, and then sliding into my ass. It had been years since anyone had done that to me and my increased moaning told her I was enjoying it. Shortly, one finger turned to two and was soon thrusting them in and out in sync with her mouth going up and own my shaft. My next surprise was when she turned her hand slightly so she could rub my prostate and it felt like a small electrical shock from her fingers right to the head of my cock and back. I must have flinched a little because she stopped and asked, "Okay?"
The smile on my face plus my answer of "Mmm, very okay!" was all she needed to go back to what she'd been doing.
It wasn't long before I knew I was close to cumming but seeing as she'd already said she enjoyed tasting cum, I just relaxed and let it happen. The extra sensation of her finger in my ass certainly did the trick and my orgasm was both long and hard. After swallowing, she smiled and said, "Damn, that was a lot and tasty too!"
On an impulse, I brought my mouth to hers and as we kissed, I could taste a slight trace of my cum. When I moved back again, she looked at me and said, "John used to do that but Frank won't even kiss me after I've had his cock in my mouth. Would you have kissed me before I swallowed?"
Thinking back to some of the things Diane and I had done early in our relationship, I just grinned and said, "Maybe you'll find out another time but for now, how about you move up here so I can give you a nice licking while I recuperate a bit?"
"YES! That's something I love but don't get near as often as I'd like."
I hadn't gotten a really good look at her pussy yet but as she moved up over my face, I could see that like Sammie, she was shaved smooth but her lips were larger and puffier than her daughters and were already shiny with arousal. Initially, I had trouble finding her clit with my tongue but the more I licked, the harder and longer it got until it was showing like a fingertip.
I loved giving oral to a woman and even more when she moaned and moved the way Amanda was. Knowing that she enjoyed some anal fun as well, I let my tongue roam further back until it was teasing her ass as well as her pussy. That got an even louder moan followed by, "Mmmm yes, it's been way too long since anyone's done that!"
That gave me the incentive to give her ass an even harder, longer tonguing each time my tongue went there from her pussy and by the time I'd gone back and forth for at least 10-minutes, she'd already cum once and I was pretty sure she was getting close to a second one. While I licked and sucked her clit, I'd been sliding a couple of fingers in and out of her pussy so when I moved my tongue to her pussy, I decided to move my slippery fingers to her ass. The first finger went in much easier than it had with her daughter so I added a second one which got me an "Oh fuck yes! I love what your tongue and fingers are doing!"
Instead of shifting my tongue to her ass like I had been, I kept sliding my fingers in and out of it as I moved my tongue back to her clit. When I started sucking and licking it, I heard, "YES! I'm going to cum and it's going..." but that was as far as she got before her orgasm hit.
She'd been wet when I started and had gotten noticeably wetter when she came the first time but I wasn't quite prepared for the sudden gush of fluids in my mouth and running down my face. There were at least three separate, long squirts followed by a couple of smaller ones before she moved to the side and said, "I'm sorry, I tried to warn you but it was too late!"
For an answer, I grabbed pulled her to me and gave her a long, hot kiss while sharing some of what was still in my mouth. After kissing for a bit, I let go of her face and as she moved back, I said, "I loved it and you taste amazing!"
I could tell from the look on her face that she was both relieved but also turned on even more by hearing what I'd said. When her fingers wrapped around my semi-hard cock, she said, "Hmm, I don't think it'll take too long to get you ready for more!" and with that, she shifted so she could take me into her mouth.
Knowing I was fine with her playing with my ass, even before she'd taken my full length into her mouth, I felt her finger pressing against my ass and then sliding back in. After sliding it in and out a few times, she stopped and just as I was wondering what she was doing, I felt it going back in again except this time there was a second, freshly lubed finger with it.
When I said, "Hang on for a sec", she must have thought I didn't like what she was doing but when I suggested that we '69 so I could do the same to her she said, "I'd love to!"
Soon her mouth was back on my cock with two fingers in my ass while I licked her pussy and fingered her ass at the same time. It didn't take too long before I was hard again but when she started to move away, I just held her in place with my free arm and sped up with both my tongue and fingers until she moaned, "YES!" and came again. Even though this squirting wasn't as much as the first time, there was fresh wet spot on the bed around my head when I moved.
When I asked what position she liked, she quickly said, "Doggy, I love it from behind!"
My first thought was "Like mother, like daughter" but instead of saying anything, I just moved behind her and slid my cock into her pussy.
When I was in full depth, Amanda looked back and said, "I love it deep and slow at first and then give it to me harder!"
That was fine by me so I started with the deep, slow thrusts she'd asked for and at the same time, I grabbed the lube so I could slide a slick finger back into her ass. By the time I started going harder, I had two fingers in her ass and when I tried a third, I was surprised at how easily all three of them slipped in.
With a moan of pleasure, she said, "Damn, that feels so much better than one of my toys!"
Okay, that explained why she was taking three fingers so easily! "Damn, it would be hot to watch you fucking your ass with a toy or maybe one in your pussy and one in your ass at the same time."
I could feel her pussy clenching around my cock when I said it and then she said, "Mmmm... I'd love to have you watch; it would make me cum even harder!"
Then with a bit of a grin, she flexed her cheeks a few times before saying, "Even if you have any toys, I'd still prefer to have your cock sliding in and out of my ass!"
Damn, a woman that not only enjoyed anal but was pretty much asking for it! Pulling out of her pussy, I added some lube to my cock and pressed the head against her back entry. Even though three fingers had gone in fairly easily, it took a bit of time and lots of gentle pushing before the head finally popped in. As soon as it did, she pushed back and took the rest of my length in one long, slow, push. She started moaning as soon as she started pushing back and didn't stop until I was all the way in her ass.
"Damn, I've missed that! Now fuck me until we both cum again."
That was fine by me so with a hand on each hip, I pulled back before thrusting in again. When she started pushing back with each thrust, I knew she wanted it harder and a few times she told me to go faster or slower but regardless of how I was fucking her, it felt great. From her moans, Amanda was enjoying it as well and after only a few minutes, I felt her ass squeezing my cock like a fist so tight that I couldn't move. At the same time, she started shaking, moaning even louder and I felt at least one splash of fluid against my legs. As soon as she relaxed, I went back to thrusting in and out of her ass. The 'clench/shake/moan/squirt' sequence repeated two more times before it was my turn. With a loud moan of my own, I thrust as deep as I could into her ass and started cumming. Even having cum earlier, it was still a long orgasm and I could feel spurt after spurt of cum shooting into her ass.
Apparently, Amanda could feel it too because she said, "Fuck yes! I can feel it... I can feel your hot cum in my ass!"
Rolling, over, she looked at me and said, "I had a feeling you'd give me what I needed but damn, that was amazing!"
After giving her a quick kiss of agreement, she got dressed and said, "We leave tomorrow but if I can get away, I'd love to do it all again!"
Later that evening when there was a soft knock on my door, I opened it expecting to see Amanda there but instead, it was Sammie. After letting her in, she said, "I hope you don't mind me coming by. I've been thinking about it all day and I really want to feel your tongue on my pussy again and hopefully get fucked again before I go."
That sounded great to me so without any delay, both of us got undressed and we headed for the bedroom. As soon as Sammie lay back on the bed, I moved between her legs and started giving her pussy the oral attention she wanted. Judging by how wet she was, I could tell she'd definitely been thinking about it for a while. With her moans encouraging me, I licked and sucked both her pussy and clit until she came and even as her orgasm was ending, she blurted out, "Fuck me, fuck me now!"
Moving higher on the bed, I lifted her legs slightly and as I slid my cock into her, she moaned, "Yes, nice and deep!"
After fucking her that way for a few minutes, she blurted out, "Go harder! I'm going to cum soon!"
I liked that thought, so I lifted her legs a bit higher and started thrusting harder and faster until her orgasm hit and even though she got even tighter, I did my best to keep thrusting deep and hard until she'd stopped cumming and relaxed a bit. When I finally stopped, she looked at me and said, "I never did get to feel you in my mouth the last time."
That was all the hint I needed so I pulled out of her pussy and both of us switched so I was laying on the bed and she started licking my cock. From her expression, I don't think she'd realized she'd be tasting her own juices as well but she quickly got into it and was soon sucking me with enthusiasm. Whatever lack of experience with giving oral and getting anal she had, it obviously didn't apply to giving oral because she knew exactly how to use her lips and tongue, the amount of suction and when to speed up or slow down to make me last longer and feel best.
If I hadn't just been fucking her, I would likely have lasted longer but as it was, she must have sensed I was getting close because she only stopped long enough to say, "I want to taste it!"
That was pretty much the end of me holding back and I was quickly emptying my cum in her mouth. I think there was more than she expected, but she swallowed all of it before saying, "I usually don't swallow but you've made me cum so hard and so often that I wanted to and I'm glad I did!"
After gathering up her clothes, she gave me one last hug and a passionate kiss before saying, "I still can't believe everything that we did, especially you fucking my bum but I loved all of it and you definitely set a new standard for great sex!"
Once she was gone, as I grabbed a shower before bed, I couldn't help but think about how good her mouth, pussy and ass had felt and wished that they were staying longer.
The next morning, I was still in my boxers and just finishing breakfast when there was a knock and I was quite surprised to see Amanda there. After letting her in, she said, "I don't have long, I told Frank that I wanted to take one last walk on the beach before we left. How fast do you think you could cum if I sucked you?"
"The way you sucked me before, pretty quickly, especially if you use a finger in my ass again."
Her grin told me she'd already planned on that and we didn't make it any further than the couch before my boxers were off and I was sitting with her kneeling in front of me. After having me slide forward enough that she had access to my ass as well, she started licking and sucking me even harder and faster than she had the last time. Between that and her spit-slicked finger sliding in and out of my ass, I think it was less than 5 minutes before I was cumming in her mouth. As soon as I finished, she got up and as she moved her face closer to mine, I was pretty sure she hadn't swallowed. Right away, my mind went back to my previous, "Maybe you'll find out another time" and I knew what she was thinking.
It had been years since I'd done it but I happily brought my face to hers as we kissed and shared my cum back and forth until none was left. To my surprise, by the time we finally moved apart, I was already getting harder again. Looking down, Amanda said, "Damn, I'd love a quickie but I already showered and don't want to be oozing cum on the ride to the airport!"
Thinking quickly, I said, "What if I offered to lick you clean afterwards?"
You'd have thought I just bought her a car or something because with a quick, "Oh fuck yes!" she was back on her knees, sucking and stroking me until I was fully hard again.
Leading her to the bedroom, I said, "Ride my cock hard and fast until I cum then you can just move up onto my face."
As she rode me, my mind briefly went back to years ago when Diane would straddle my face after we'd fucked so I could lick her clean and how much we'd both enjoyed it. Amanda was riding me like her life depended on it and then suddenly she slowed down and as she ground herself back and forth with my cock fully inside her, she was using her pussy muscles to squeeze and massage my cock. It wasn't much longer before she got the result she wanted and I was emptying my second load of the morning into her pussy. As soon as I was done, she looked at me to make sure I hadn't changed my mind and when I smiled and nodded, she smiled back and shifted up toward my face. As I licked her, I was a bit surprised at how much cum oozed out of her so just for fun, I got a couple of fingers slick with that cum and slid them into her ass.
The result was almost immediate, as she pushed her pussy even harder against my face, I could feel her quivering and then my face was getting soaked with a mixture of my cum and hers as she squirted several times. When she started to lift up, I just wrapped my other arm around her waist and held her in place so I could keep licking until she finally came again. This time, she didn't squirt but I'm pretty sure my neighbours would have heard her loud, "Oh fuck yes! You make me cum so hard!"
When I finally let her go, she pretty much fell to the side and then through barely open eyes she said, "I guess I'd better grab another shower before I head back anyway, even Frank might notice that I smell like sex!"
As she headed to the bathroom, I got up to follow but she just stopped me with a hand and with a big grin said, "Oh no you don't! If you get in the shower with me, we'll be fucking some more and then I'll be late!"
I'd have argued except I knew she was right so I just relaxed until she got out of the shower. As we kissed one last time, she gave me a card and said, "Shoot me a quick text asking about something really weird like pony rentals for a kids party. That way I can say it's a wrong number but just in case we ever come back, I'll be able to let you know!"
With that, she was gone and I was left thinking that not only had the last few days been some of the hottest sex I'd had in years, it was the first time I'd not only had sex with a mother and her daughter but anal with both as well!
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(All characters are adults and all actions depicted in this story are consensual.)
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