The Deal Ch. 12

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The Deal 12 – Sun, Sand and Skin


A Not So Brief Introduction by the author. Hi readers! Thanks for clicking this open. The Jamaican Chapter of the Deal is a special one and needs some explaining so please bear with me. At the time I had finished chapter two and was starting three I had a crazy idea. While I have only been writing here for a couple of months, I have been a big reading fan of Literotica since February 6th 2001. I know the date because when I discovered Lit the first story I read in the new story list hooked me big time, and I have never looked back. To this day I still love that first story. For me it is what Literotica should be – well written hot fiction with really likable characters. So I thought wouldn’t it be cool if Di and Matt actually witnessed that first story. So I built in the excuse to go to Jamaica to set it up. Now the author of that first story hadn’t written anything here since 2004 so I crossed my fingers and emailed her. What a rush it was when I got a response within twenty-four hours. Better yet she was incredible, funny and gracious and let me steal her story! So while Di, Matt and company are all mine the four college couples in this episode and what goes on with them (and I tried to stay as true to the original story as I could even to exact dialogue) come from another author’s story. So either before or after reading this story please read AmysCute2000’s story The Bet.

If the link I put here doesn’t work just click my name above and click the favorites tab. The Bet is in my favorite story list; while at it try the other stories as I think they are all incredible.

Amy, thank you so much for letting me use your story and for being so much fun to talk to and most importantly thanks for being such a great writer and sharing your gifts with me and all the others lucky enough to have found you.

Now while I have you I want to thank all you readers, especially the ones who have taken the time to comment or email to me both times I’ve published these stories!. I truly treasure my dialogues with all of you and look forward to more. Pete, thanks for being there right from the very first day. I believe you got your comment in when the Deal was only an hour old here and you’re still quick to get me after every chapter with incredibly gracious words. I am honored to call you friend. Di. I am embarrassed to say as a writer that the words fail me. So much for excessively fulsome praise! I am going to stick to the simplest two words, and believe me I have never meant so much in so few words – Thank you. And then there is the love of my life who I met here on Literotica as well – _slave.


And now welcome to Jamaica.

Diana rested her head on her seat and closed her eyes listening to the sounds of the flight. She honestly couldn’t remember her last vacation and here she was winging it to Jamaica. In the seat behind her she could hear the boys joke around clearly excited by the impending week of fun in the sun. Further down the plane she could hear a gang of college kids laughing and joking around adding to the buzz of excitement.

She smirked as she remembered her son admitting that he had originally picked Jamaica so he could get her nude on a clothing optional beach. She wondered if she could have done it. She was becoming quite comfortable being in the house naked all the time and even around her close personal friends again, but out in public among thousands of people was something totally different. No, she was quite content to keep the girls and the rest of her covered albeit scantily in bikinis, but covered nonetheless.

It was probably a good thing that Craig and Chip were coming along. While Diana and Matthew had settled into a wonderfully loving relationship since the deal started, being alone thousands of miles from home on a sunny beach resort might drive a wedge between any possibility of relationships with others for them especially now that Matt found someone he was quickly falling head over heels about that just might really be as great as he was thinking. What Diana heard about Cindy from Matt sounded very promising. She was looking forward to getting to know this girl.

The role of chaperone, den mother suited her just fine she decided as she fell asleep.

Day One.

Soon enough the plane landed and the quartet was headed for the hotel to check into their rooms. It turned out that it was four couples of college kids on the plane, and they were in the same hotel. Actually other than Diana and the three boys all the guests at the hotel looked like they were in college on spring break. While Diana was filling out the paper work she and the boys watched the group walk up to the man behind the counter next to them.

“Hi, does the beach next to this hotel allow full nudity,” one of the boys asked.

Matt, Craig and Chip all perked up and looked at the hotel man as well as the four nervous looking college girls.

The hotel clerk looked directly at the two striking thin blondes of the group smiled eryaman escort and said “Yes.”

“What about being nude walking from the beach through the lobby as well?” the boy continued smiling broadly.

The clerk kept the smile on his face as he responded “If you are going straight to beach or back to your room and not hanging around in the lobby then that is perfectly okay.”

The four boys laughed and gave high fives to each other as the girls looked stunned.

Matt, Craig and Chip as well as the hotel clerk stared appreciatively at the four dismayed girls.

As the group loudly passed on their way to their room, Diana smirked and looked at her three boys, “I will bet you anything that those four girls made a bet with those boys that they are really regretting now. You might have more eye candy than you were expecting. Just remember don’t mess around with college kids – you’re not in their league yet!”

The words sunk in but the teenagers couldn’t help staring at the incredibly gorgeous ass of one of the blondes.

Soon all the paperwork was finished and keys were given out and the four went up to their rooms.

Diana looked around the luxurious room with the open window view of the ocean. Man, did this beat snowy Pennsylvania.

Through the divider door she could hear the boys arguing.

Knocking she entered to find the three huddled around a bed hands on hips.

“What’s up boys?”

“None of us particularly want to share a bed as there are only two” Chip responded.

“Well, you could take turns” Diana pointed out “or…”

She looked back into her room. “Since I have two beds as well Matt could sleep on my spare bed; if he behaves!” she mock scolded him causing the boys to howl.

“You guys won’t get jealous of me sleeping with the girl would you?” Matt laughed actually excited by the idea.

“Yeah, your own Mom, big whoop. Try dealing with that if you get lucky some night,” Chip joked.

Craig just eyed his best friend suspiciously.

“Excuse me, but there will be no getting lucky while I am around mister. You think I want the wrath of your parents on me when we get home? I don’t think so.”

Diana stopped before reentering her room “Besides I am the only single full grown adult here so maybe I might get lucky and have to send Matt back to you two to continue to figure out bed arrangements.”

She went back into her room leaving behind the pleasant howl of their laughter. She had to admit that all three were really good kids; adults actually as the youngest, Chip, had turned eighteen a month ago.

This could be a very fun week if she could control the boy’s rampant hormones. She pitied the beach bunnies and those four college girls when the boys got to the beach. As long as they never figured out that they out numbered her three to one.

She opened her suitcase and started to put away her clothes as Matt knocked and entered her room closing the door behind him.

“Hey mom. Are you sure you don’t mind me sleeping in here.”

“You know Matt that I trust you completely. So no problem.”

“Well you know, I’ve been thinking about something that I know about you as well,” Matt sat on the bed.

“Oh?” Diana stopped unpacking.

“Right, well don’t get mad at me, okay?”

“Oh, I can’t wait to hear this one. Go ahead”

“Well, we are in Jamaica far away from home. And there are two adult males next door, and I remember how you said that you told dad that one of your biggest fantasies was to have two men at the same time, so … I could go for a long walk while you three…” Matt suddenly got very interested in the carpet between his feet.

Diana laughed raising his face with her hand. “I don’t know if I want to be pleased at your generosity and self-sacrifice or repulsed at the slight pimping feel of the whole idea.

Thanks but even the combined ages of those two so called adult males is around eight years younger than me. Yes we are in Jamaica, but I am supposed to be the responsible adult chaperone not the wanton sex-crazed woman that I appear to be at home. Some times keeping a fantasy as a fantasy can be more appealing. Reality can ruin a great dream some times. In a bizarre way it is a sweet thought though.” Diana kissed him on the top of his forehead.

“Now don’t you think it is time to hit the beach, or did you just want to stay in the hotel the whole time and look out the window?”

Diana watched as Matt continued to sit on the bed. Matt continued to get a little red faced.

“Actually, I was kind of hoping to watch you get into your bikini.”

Diana laughed, “Ah teenage hormones rage again.”

As Diana crossed her arms and pulled her T-shirt over her head she spoke to Matt, “Now we have to be careful with the boys right next door. I don’t want any stories getting back to Pennsylvania from Chip. He isn’t in on things yet, if ever”

She unhooked her bra and tossed it on her bed. Her breasts wobbled pleasantly, her pink nipples hardening slightly. She slid down escort eryaman her capris and panties together and walked nude over to the dresser. She took out a fairly modest yellow brown bikini and quickly slipped it on. Next she tied a wrap around her waist, slipped into a pair of sandals and put a pair of sunglasses on top of her head.

“Do you want to check on the boys since you know what it is like to have a woman walk in on you when your pants are down.”

“Gee thanks for reminding me,” Matt chuckled as he left.

Soon enough they were relaxing on the beach while Craig went to the juice bar.

The boys excitedly pointed out all the young girls parading around topless. Diana rolled her eyes and laughed.

Craig came running back, “Guys, I totally forgot, the drinking age is eighteen here. We can drink!”

Oh, crap thought Diana just what she needed – hormonal and drunk among half naked girls.

“Now boys this is day one of our vacation how about a little moderation.”

“Oh come on Mrs. Hughes. Booze and naked girls. We want to have some fun.” Chip looked practically depressed.

Diana laughed. “Alright how about one beer each to start, but you hang out here with me.”

The boys didn’t look convinced. They looked around at all the bare breasts surrounding them.

The boys were practically drooling.

“Tell you what boys. If you promise to keep to yourselves I’ll buy the beer this first time and entertain you myself,” she looked up at Matt.

“Come on Chip I need a second set of hands to carry four beers,” Matt said as he took the money from his mother.

Craig sat Indian style next to his best friend’s mother, “So Mrs. Hughes I hear you and Matt got my mother naked two weeks ago.”

Diana stared at the boy through her sunglasses. “Yep, it seemed she needed a jump start to get her out of a boring rut. Actually I believe it was you who gave the first push. Are you okay with things?”

Craig thought for a moment, “Well, I’ve never seen my parents so happy; they are actually giggling a lot, even my dad. It’s kinda creepy actually but I guess in a good way.”

Diana laughed “It must seem like a whole strange new world to you like you’re meeting them for the first time.”

“Yeah but they are so happy. I just can’t believe Matt has seen my own mom naked.”

“Well so have you, as well as more than just seeing or so I’m told,” Diana watched Craig redden.

“Yeah who would have ever believed it, but why couldn’t I have been there for the first time like Matt. I think you are the hottest of the moms by far, no offense to my mom.” Craig was getting even redder.

“Why thank you my charming young man. But your mom is a very attractive woman in her own right. I don’t know if you will believe me but that first night kind of just happened; it wasn’t planned by any means.”

“Well how did it happen?”

“Well you are in on things now so I guess it is alright to tell you. Just remember your mom and I haven’t talked to Chip’s mom yet so he doesn’t know anything and it needs to stay that way until Kim is comfortable with things if ever. Matt and I have been ah experimenting with our relationship for quite a few months now.”

“You mean you two have been having sex for months?”

“Geez, a little quieter, this is a public beach and a very private conversation. No things have progressed rather gradually for us, the touching part only started in the last week or so.”

Diana and Craig watched as two topless college girls in thongs walk by laughing.

“It’s kind of been like that for Matt the last couple months just without the thongs,” Diana pointed.

“Lucky guy.”

Diana laughed “And I believe you have been just as lucky if not more so faster. So anyways your mom kind of figured out that something was going on and confronted us and then she told me how you challenged her to strip poker and one thing just led to another. And here we are.”

“Well I guess that it is not so bad since it wasn’t Matt’s idea. But come on, when do I get to see you naked?”

Diana laughed “I’m sure if your mother has anything to say about it, it won’t be before long after we get back. Ask your mother nicely and who knows what will happen.”

Soon the others returned and the beer was passed around and the sun was enjoyed. The boys even enjoyed it more when Diana let them take turns spreading suntan lotion on her. They took a lot of time to rub it smoothly into every available inch of skin exposed and Diana never said a word other than a couple of quiet purrs.

After an incredible dinner and some mild bar hopping the troupe headed back to the hotel and bed so that they could have more time in the sun the next day.

The four stood in the hallway and bid their goodnights watching as college kids ran around far from ending their night.

Diana caught Craig giving Matt a look which was returned with a negative head shake. Craig grabbed Matt saying “Excuse us,” and walked down the hall. Di could just guess what they were saying. She eryaman escort bayan smiled and said good night to Chip as both walked into their rooms.

Diana from the bathroom watched Matt open the door and walk in and called out to Craig who was still shaking his head behind him “Good night.”

“Good night, Mrs. Hughes.” Craig called walking into his room.

Diana looked at her son and walked into his arms “So is he trying to goad you into something?”

“Oh he seems to think we should be at it like bunnies.”

“We? Like the three of us?” Diana looked into his eyes.

“Huh? No, no. Just you and me since we do and can.”

“And you told him no because why?”

“Well, I don’t mind doing some stuff, but I am sorry mom. I am starting to feel guilty about Cindy.”

Diana walked her son to the bed by the window and sat both of them down.

“You really are starting to fall for her aren’t you?”

Matt smiled, “Mom, she is incredible: funny, caring, easy to talk to, I want to see her every day.”

“I think you did all last week. So why on Earth are you feeling guilty?”

“Because I feel like I am cheating on her.”

“Ahh. Well if she loves you back then you are. Does she?”

“I think so. I don’t know. I need to make her understand about us first then I can ask her.”

“How are you going to do that?”

“I have no idea yet.”

“I told you before that if you find somebody I will gladly step aside. I guess it is time for me to do that.”

She started to stand but Matt held her and brought her back into his arms, “Mom, we are on vacation in a beautiful place. And even though I am starting to feel something for Cindy, I want this week to be special. She is not my girlfriend yet. Maybe no sex sex but let’s keep things as they are for one more week as a last time.”

“Are you sure? I don’t want you beating yourself up later with guilt.”

“I won’t feel any guiltier than for what we have already done. It is too beautiful here and so are you. Let’s enjoy it and each other just like we decided before we left.”

Before leaving for Jamaica Diana and Matt discussed what they wanted to do in Jamaica, both with the boys and privately between the two of them. They decided to be slightly daring and as a special treat for both sleep together while they were there if they could figure a way to explain why Matt needed to share a room with her. Other than that they decided any else goes except intercourse which was totally Matt’s decision.

Diana pushed them both over onto the bed, “Well then I guess I will be sleeping in this bed with you after all. Time for some enjoyment” And she kissed him long and hard.

The first night in Jamaica ended with a lot of cuddling, caressing, kissing and giggling in one room and a lot of snoring in the adjacent one. For the first time in his life and for the first time in over eight years for Diana, the Hughes both fell asleep with some one else in the bed .

Day two

Matt groaned. He felt a weight on his waist and a pulling feel. He opened his eyes to a stunning brightness as sunlight streamed through the nearby window. Disoriented he took in his surroundings and the huge lump down at this middle shaking covers he had never seen before. He shook his head and everything cleared.


With a smirk he lifted the covers to see his mother scrunched by his waist her mouth fully swallowing his quickly rising member. She pulled off it with a loud slurp and looked up from under the covers at him grinning, “Good morning sleepyhead. I figured this would wake you up. Time for my breakfast.” And she leaned back down and devoured him. Matt brought his hand down to caress her back.

Matt flopped his head back on his pillow, the cover softly laying back down on the form of his mother, moving up and down with the motions of her head on his cock. She surprised him with a sharp vibrating sucking inhale the sent vibrations through his entire aroused flesh. It was like she was squeezing every side of his penis at the same time. He groaned and after one more such inhale flooded his mother’s mouth.

Diana slowly slithered back up Matt’s body until her head popped out from underneath the covers. She stopped to kiss and lick his extended neck. His hand kept its swirl motion on her back.

“Shall we get going so we have more time for the sun?” Diana said as she rolled around Matt to stand between the beds. She leaned over and shook the cover on the unused bed.

When Matt looked at her curiously she responded, “Let’s not advertise our sleeping arrangements especially should the boys pay a visit.”

After Matt got the other two up and dressed they all went out for a more traditional Jamaican breakfast and shopping.

As the sun built up its strength and got hotter the family and friends decided to hit the beach again.

For the second day Diana had worn a tighter and smaller bright pink with white polka dots bikini. Since they got to the beach a little later after shopping all the lounge chairs where already used. There were a lot of college kids everywhere as well as some other people, but mostly college aged. A lot of the girls were topless and or were wearing thongs. No girl was totally naked. Only one or two men were comfortable enough with themselves to show the rest of the world what they had.

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