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Chapter 29
by
DiveInstructorPlaya
What's next?
Goodbye - Part 1
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Warning
This memory includes a mix of, e.g., real feelings, creampie, breeding, gay, public sex, falling in love, femdom, cuckolding, and so on.
With Cindy I had the wildest sex of my life, including lots of experimenting, and you cannot change things from the past.
The story is based on true events.
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Tomorrow is Cindy's departure day from Playa del Carmen. I felt sad. We got intimate, even if we only had a sexual relationship. And how sexual it was! I even took a vacation to fuck her married slit two or three times a day. I was glad her husband was there to help me in the end, inserting my throbbing cock in his wife's fertile pussy, making sure she would get pregnant with my bastard baby. With our last breeding session, Cindy had ordered him to get a wedge pillow so her ass would be elevated once I filled her womb with my baby makers.
Of course, the last fuck sessions were all missionary. It is simply the best way to knock up a woman and keep most of the cum inside her. Cindy asked her husband a couple of times to lick my cum from her legs, but both times it was because we had fucked either doggystyle or standing. Her husband Steve got so good at licking my cum away in the last couple of days of their vacation that we didn't even stain the sheets anymore.
But, regarding the cum licking, as his wife ordered, he was not allowed to lick inside her jizz-filled pussy; her cunt lips were the border. She wanted to prevent at any cost the risk of not getting pregnant. But he was able, even in a dark bedroom, to clean up properly, being such a good cuckold, leaving a neat, clean area around her stretched cunt. The only grey area about the agreement was the cum on her cunt lips. I protested once because I wanted to be able to see something or have some proof of my successful drilling of his hot wife. At the end, his wife would tell him when he was allowed to lick up more cum than usual.
In the afterglow of our last fucking, as Cindy lay on her back again, having that wedge pillow handed over by her serving husband, assisting her in placing it below her butt, some cum leaked out before the pillow was in place. On one side, she was annoyed with her husband for being so slow. On the other side, the more extensive cum licking would sometimes make her so horny that she needed my cock right away again. For me, it was a very erotic sight, seeing so much white goo on her brown, tanned legs. The hilarious thing is that her husband would, while licking and swallowing my cum, always have a hard mini pecker.
In those days, I had never heard of terms such as "hotwife" or "cuckold." In Playa, I simply fucked any pretty married pussy, husband watching or not. Much later, as I started working for Anna, I learned a LOT of terms from the other male fuckstaff. I was amazed at how many wives cheat! Of course, it was much easier when the married sluts would come to the mansion, having a room already reserved for the cheating cunt, as opposed to having to do it secretly, trying to keep the husband oblivious. Still, it always had to be discreet, and sometimes we only had a time slot of one hour. Most of those married women were really pretty and well-kept, due to their riches. And Anna would always let us choose which woman we would pick.
Playa del Carmen would have been Sodom and Gomorra if the local Mexican police would not have been so keen on earning an extra buck for their own pockets. They were constantly patrolling areas where folks would probably fuck. But as a local, you learn where you can penetrate a pussy without too much risk. One of my favorite fuck spots was at the end of Fifth Avenue, where you could drill a babe, standing, against those metal gates of private properties. The only negative side effect was always the mosquito bites on your own naked butt cheeks while drilling the slut... "No pain no gain," right? Or should I better say, "No itch, no bitch?" :-)
Back to Cindy.
Since Kim moved in with me for the remainder of her stay, I decided to book a hotel room one more time at the Blue Parrot Hotel, because that's how it all started. I thought it would be good to have our last night there without Kim. At the end, Cindy was mine. Steve, her husband, was to sod off as well. I also booked a table for four at the Blue Lobster restaurant. I always book a bigger table to have some space. Cindy loved lobster. Or did she like the sucking? (All those male thoughts...) I did book lots of times for Cindy and me the Blue Parrot hotel, but thank God, her husband paid for it afterwards.
Cindy was so kind to tell her cuck how much he owed me for fucking her. As you know, I made between 1200 and 1500 USD a month as a dive instructor, and I was a well-paid one because I could sell in several languages (2% commission). So those 300 USD came from sales. So, her cuck gave me, through Cindy, 500 USD several times. On top of that, Cindy told her husband he owed me another 1000 USD for the breeding of his wife. I think Cindy sold me cheap. ;-)
That was probably my first whoring work I ever did. But for that one time, the 1000 bucks my unfaithful colleague Catherine gave me so I would plow her for one entire night back home in Holland. It all started when Catherine wanted me to give her some tips on how to get fit. She was married for a long time and was bored, so she decided to do something for her health. And as I flirted with her, standing next to the coffee machine, we agreed on one night and a thousand bucks. Well, at the end, I fucked her for free many times after that first night, but I'd like to keep the illusion I got 1 K for one night. (Memory not yet published here).
I never thought I would see a husband love licking my spent cum from his wife. But then again, in the mansion a lot of things went on that were unbelievable. Back in their resort, Cindy was looking forward to our dinner together and wanted to be extra sexy for me. She kept asking, as a true hotwife, her cuck what she should wear in order to get her player stud's cock as quickly as possible deep inside her. Just for me, she went lingerie shopping for our last night together.
"Steve," Cindy asked her husband in their hotel room as she was getting ready to be fucked by me, "Should I go without a thong? What do you think?"
"I think that's very wise." Her husband answered. "You want to give proper cunt access at all times to your bull, right?"
"Yes, I think so too," Cindy replied.
"Yes," Steve replied. "He should be able to have quick and easy penetrations, for example, when you are waiting in line to be seated or whenever you are enjoying your starters while sitting on his lap."
And then her husband added, "I am just worried that if you wear a short leather skirt, access to your fuck hole will not be smooth enough. "I really have my doubts about leather, Cindy. The fabric should be light and easy to fold. He really needs to have good access to both your poop hole and your baby tunnel."
"What about the beige skirt?" Cindy asked her husband.
"That's a no-go, honey. It reaches almost to your knees, and it is way too long. You cannot look like a slut with that skirt," Steve answered. "Just let me think; let's go through it again, from the head to toe."
"OK, I am listening," Cindy said.
"First, we need to define the look you are looking for," her husband said. "Now you want to look like a cheap slut in an expensive dress. A cheating whore who will suck any cock and swallow any cum once you have two fingers in her cunt, am I right?
"Yes!" Cindy happily agreed.
Steve went on, saying, "Take the same mascara and makeup as you used for that photoshoot with him. " Full, red lipstick so you can mark his cock when you suck it. It is important to leave red stains on it and mark your property. Some lipstick stains on the area around his zipper on his pants would be great too."
"Oh, I still love those pics with those red smearings on his cock!" Steve added and continued:
"How about you wearing that dark blue corset, with your tits out? You could perhaps cover them with a small dinner jacket? And matching that, to emphasize the corset, light beige stockings."
"Oh, that sounds so good!" Cindy almost cried. "You are such a thoughtful husband."
"Just trying to give your bull all the possibilities to fuck you deep, my dear," Steve answered proudly.
"Will you wear that same dress as at the photoshoot? It has these nice slits on the sides all the way up to your hips. That way, your pussy is easily available, you know what I mean?" he added.
"What about my other evening dress?" Cindy asked.
"Honey, just let me pick the clothes, OK? You need to give your bull the very best access to your cunt. Don't make it hard on him." Her husband answered, declining her request.
"Remember our vision," her husband said.
"Please focus, all right? We want everybody who sees you to want to fuck you, men, women, or couples, no matter who. Maybe we need to add an extra element, something like a walk of shame, you walking half-naked on Fifth Avenue to the restaurant, everybody knowing, smelling, that you are a breeding slut. I just wish we could show them that you are fertile."
"OK," Cindy replied to her knowing husband, "I understand."
"Don't you have like a transparent blazer? So, you could wear the pushed-up, open-tits corset, wear a blazer, and still show everybody the cum slut you are?"
"YES! Great idea! Let me check where it is." And Cindy started eagerly looking inside the already closed suitcases. She quickly found it, and it was not wrinkled too much. Some light ironing would do.
"Excellent!" Her husband shouted, "You are now all set to be the whore you are! I am so proud of you! I will arrange a taxi right now, at the resort gates, for you." As he dialed the reception desk.
The taxi will be there in thirty. So get dressed and off you go and get your pussy stretched until it hurts. I will pack the remaining stuff, so you don't have to worry. Just try to be back at noon tomorrow; our taxi to the airport will be waiting. "Her husband Steve added.
"And remember, no cum is no fun," her cuck said wisely.
And just like any good little mistress, she didn't say goodbye to her husband as she left to get her private big cock.
During the 15 min cab drive from the resort to the restaurant, Cindy decided to tease the driver by lifting her dress entirely up to her stomach and opening her legs wide as she was seated in the backseat, offering him a good look at her married slit. The first thing the driver did was to adjust his rearview mirror. He had heard wild stories from another cab driver but only believed half of them. But maybe... He thought it was all true?
Cindy decided to torment his growing dick a bit more and slowly rubbed her pussy with her middle finger, playing with her clit, while she kept looking at him in his mirror.
"Do you speak English?" She asked him.
"Yes, I do," he answered.
"I am a cheating wife," she told him self-assuredly. "I am about to fuck a local diver again and get a baby from him. And my husband knows about this."
"That's crazy, señora," he replied. "Why?"
"He is an alpha male," Cindy replied.
"I see," the driver answered. "Is he a good fuck?"
"The best."
"Then you go and let him fuck you. It is good," the driver said.
Two minutes later Cindy arrived two streets away from the Blue Lobster restaurant. The moment she stepped out, already several men were looking at her. Two English guys catcalled her from behind with "Foxy lady!"
Cindy smiled; it was a nice, typical English male compliment. She kept walking, turned around facing them, and showed a naked tit by opening one side of her blazer completely. Whistles everywhere. She turned around again and kept walking, smiling. This vacation was a life-changing trip. It all started as this local diver teased her by not asking for her name but for her friend's name. And she fell for him right away. And his little trap.
But something more happened; it was not only her unfaithfulness, which added so much spice to their sex. No, deep inside, she felt truly safe with him. As if she had found her destiny. Some call it "soulmates." But they both knew that their different worlds would never match; neither one would be able to live in the other's world. It would work for a certain time, until one of them would be longing for something that the chosen world could not provide. It made her sad, but she was happy to have met him. This, nobody could take from her.
And the sex. OMG the sex. She didn't know what to call it until the word "depraved" occurred to her. She had done it all, and more, in just two weeks. Being unfaithful, fucking him bareback, becoming fertile, Kim's fisting, the public sex, the cab ride, getting knocked up—you name it, she had done it all. And she never had felt so sexy in her entire life. Those two weeks gave her at least five years of beautiful memories. And a baby.
She felt happy being pregnant by him. She had no proof, but she knew. How would this affect their life back home? She didn't know. Perhaps they could be a little happy family with no more scandals. She for sure didn't want to hurt her husband Steve back home. He was a good man. Maybe a goof, but OK. He would provide for her and her baby. Instinctively she knew she would not fuck his colleagues; that was just an erotic fantasy, and some fantasies should stay like that, just a fantasy.
...
As I saw Cindy entering the almost empty restaurant, she truly looked amazing. As if she were glowing. She looked self-confident, radiant, happy, and fulfilled. Once again, she took my breath away, even more than when I first saw her, on that first night. She had that female charisma that would turn heads, especially the male ones. I still don't know what her race mix was, but it was very sexy, very appealing. It gave her a certain eroticism, mixed with her reserved, classy attitude.
"Hi," I said, as always. "Good to have here."
She smiled and gave me a kiss on my lips.
"Where would you like to sit, my love? I asked, showing the table with four chairs.
"Let's sit with our backs against the wall." She replied, "So we can have a nice view."
We sat down and I had to kiss her again. This time, her willing mouth opened for me, letting my tongue inside. I was lost in her scent and her delightful sucking on my protruding tongue. I would have gone on kissing her, as I noticed a movement to my left; it was the waitress, smiling at us, politely waiting for us to finish the French kissing.
"Hi." She introduced herself: "My name is Lucia, and I will be your waitress tonight."
"Hi, Lucia," Cindy replied. "Do you have some champagne for us and bread with garlic?" Cindy asked, looking at me for my approval, which I quickly gave her by nodding.
"Yes, of course," Lucia answered, smiling at the both of us, and left.
"She looks young, don't you think?" Cindy asked me.
"Mhh, I guess 18?" I answered. "But she looks nice. " I added.
"You mean fuckable, my love?" The cheating wife is teasing me.
"Only you are fuckable, my love," I replied, grinning.
We were flirting again, instead of being sad, which was nice.
The young waitress came back with the garlic bread, and at the same time a waiter served the champagne.
"If you want anything else, just tell me," Lucia said, looking at me meaningfully.
Cindy had to laugh. "Does she know you are already with a cheater?"
I quickly ignored the whole thing by raising my glass. "To you."
Cindy raised her glass and said, "To you."
"Do I have to kiss you once you smell like garlic?" I asked, putting on my best angel face.
"Well, my fish fillet never bothered you, so yes," Cindy teased back.
"Talking about fish, how about the lobster? Which variation would you like?" I asked.
"I go for the lobster with the hot pepper sauce." Cindy said, "But I will need lots of champagne with that to cool me down."
"I take the same. If my tongue is out from the hot, spicy sauce, just kiss me then."
"Honey, I am already hot for you; how will I cool you down?" Cindy replied, giving me that famous wanting look of hers.
Right then, Lucia appeared again, her timing just right, to prevent a possible fucking from us, right there.
"Did you see anything you like?" She asked with an angelic, flirting face.
"Yes, he did," Cindy answered her, looking at me. "We will both have the spicy lobster, another bottle of champagne, and your phone number."
"Cumming right up," Lucia answered, smiling at both of us.

Did I hear "cumming"? I wondered. "Are you setting me up, babe?"
"C'mon," Cindy smiled, "Nothing like a young pussy to replace me. Plus, she is local. That would be a change for you. Perhaps settle down?"
I smiled. What a great woman Cindy is! Too bad. We both know it ends tomorrow. We did speak about it once, and we quickly realized it was not meant to be.
"What about Kim?" I tried to defend myself.
"I think Kim will move on, which is OK. She is still young and needs to do some traveling, in my opinion," Cindy replied.
"Yea, I think you are right."
I then changed the conversation by asking, "Isn't that blazer a bit small for your beautiful breasts?"
As she opened her blazer for me, I could see her pushed-up naked tits.
"Just as you like it, honey." She answered, "Showing my tits to the world, knowing they belong to you."
Right then, Cindy still flashing her beautiful tits, our order arrived. Lucia liked what she saw; the young other waiter, 18 years old, looked at the floor, embarrassed. He carefully placed the lobster in front of Cindy, and as he was about to more or less run away, right then, Cindy asked him in a teasing voice:
"Do you like my titties, boy?"
His face went red as he nodded at her.
"Come here, boy, suck on one, please," Cindy dared him.
His face went even redder, but I have to say, he did not back down and approached Cindy's side of the table. Giving nervously a last look at Lucia, he didn't know what to do.
Lucia did.
"Let me help you, Guillermo." She said softly to him, holding the back of his head in her palm and gently pushing him towards Cindy's erect nipple. I was surprised by Lucia's determination, and at the same time, Guillermo reminded me of myself with Élodie, but I was four years younger than Guillermo, as Élodie made me from being a shy boy to a real man.
The way Lucia gently pushed his head towards Cindy's erect nipple gave me the impression that he was **** to suck a cock instead of a nipple. Perhaps he was gay, and he didn't like women, but he just didn't know it? Maybe we should offer him a hard cock right here and see how he reacts, I thought. My closest gay experience I ever had was on Coco Beach that one day, with Cindy and her husband. Cindy ordered Steve to cup my balls and lift and weigh them for her to check if they were heavy and full of cum. He also had to hold my cock straight in front of her mouth so she could blow me or hold it upright as I was lying on my back so his wife could sink her soppy cunt on my rod. And all that, besides the cum-licking duties he had. The memory of that beach session, where Steve finally gave the OK for his wife to fuck her bull, made me rock hard. That was a nice chance to test Guillermo, I thought, because I do not get hard from the idea of having sex with men.
Guillermo did suck on Cindy's teat for a couple of minutes, but he didn't give me an enthusiastic impression. I whispered to Cindy that he should try my cock without knowing and we should both watch if he liked cock more.
She whispered back, "OK," with a lewd grin and leaned over to whisper something in Lucia's ear.
Lucia nodded and gently pulled Guillermo away from Cindy's titties.
I signaled Lucia to come to me. As she leaned in, I whispered to her to check if Guillermo has a hard-on from the titty sucking. She understood the why and gently touched his crotch. She looked at me, moving her head from left to right, indicating a clear no.
Now Lucia took over, telling Guillermo to take off his T-shirt for a second, because Cindy wanted to take a sexy pic of him. Since we were the only guests at this hour, he still quickly looked around before doing so and then did as was requested. Cindy took her phone out and took some pics.
"Could you please sit on your knees for a second?" Cindy asked him, smiling. "That would be great for more pictures. You are very cute."
Guillermo complied, and Cindy took some more pics. Lucia stood behind him, caressing the back of his head, distracting him from her grabbing it with two hands. This was my cue. I stood up, walking in front of him, unzipping my very hard cock, having it out in the air in front of his face. I pulled back the foreskin to have it in its full glory. A blob of precum appeared, right on its top.
"Guillermo, why don't you kiss his cock for a second?" Cindy flirtedly asked him, "Just for me?"
Lucia stood ready with his head in both hands and very subtly pushed him slowly towards my big cockhead. Guillermo didn't notice at first, as he was looking up, at Cindy, who kept talking seductively to him, praising his good looks, until the big throbbing cock touched his lips. Due to the contact, the precum on my cock's slit was passed over to his lips, and the milky white glob stuck to them like glue.
Lucia asked Guillermo sweetly, "Guillermo, honey, did you drink something before? Because your lips are all wet. Shouldn't you quickly lick it away, my darling?"
Guillermo, without any further thought, opened his mouth halfway to be able to lick his lips with his tongue. His long tongue lashed out, wiping first his upper lip and then his lower lip, where my precum was waiting for him to be swallowed. The glob went into his mouth with no troubles, sending to his brain a mix between a slightly salty and a sweeter taste, which he didn't expect. He first thought it was the salted caramel he had in his coffee, but without the coffee taste. No, this is more liquid, waterier, he thought. Like a sweet nectar.
Cindy distracted him again by asking, "Do you like protein milkshakes, Guillermo?"
"Eh, yes, I do," he answered, looking up at Cindy again, opening his mouth wide as he said the word "I."
That was Lucia's prompt to push his head with both hands toward my ready cock's head. His mouth still open, the big mushroom went in without any trouble. I didn't have to do anything; Lucia took care of doing our little experiment.

"Good boy." Lucia praised him, "Just stay like this for Cindy's pictures. It will just take a moment."
Cindy joined in again and said to him, "Before I take any pics, is his cock nice and warm in your mouth?"
Guillermo could only nod, his mouth very full, since Lucia pushed his head a bit more on my cock, hitting his throat.
Cindy continued asking, "Can you feel it throb, Guillermo?"
Guillermo nodded, a bit too eager, if you ask me.
"Can you feel his balls against your chin, or do you have to get this beautiful cock deeper into your mouth?" Cindy teased him.
Guillermo grabbed with both his hands my butt and pushed me against his face, sinking my cock deeper, well within his throat.
Looking at Lucia, I asked her, "Can you check on Guillermo again?"
Lucia smiled, but both Cindy and I could already see his hard-on. As Lucia grabbed him through his pants, her eyes went big; she had just grabbed one of the biggest cocks she had ever felt. Now she understood, grinning, why he never tried anything with her. Because, just as she was, Guillermo was into big cocks!
As Lucia looked at my cock, she somehow got jealous that she was not the one sucking it. And she had more holes to offer than Guillermo, she thought. Well, he has my number. If I flirt a bit more with him tonight, he might already call me while the brunette is still in a cab on her way to the airport.
"Cindy," Lucia asked, do we have all the pictures we need?"
"Yes, you can let go now," Cindy replied.
She did, but Guillermo didn't. He held to my butt, trying to keep my cock for him.
"Guillermo," Cindy said to him in a very clear voice, "that is my cock."
He understood right away and took his mouth off it. Somehow, I was glad; I don't know where it would have led us. And tonight was Cindy's night.
As Cindy saw Lucia's longing look at my cock, she decided to thank her for her help, asking her, almost whispering, "Lucia, would you like to clean up my stud's cock for me?"
To be continued.

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Cindy M
Perhaps Cindy was neglected too long?
Do women cheat?
Updated on Jun 12, 2026
by DiveInstructorPlaya
Created on Apr 7, 2026
by DiveInstructorPlaya
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