Sex Resort for Rich Gentlemen Ch. 02

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Shy, inexperienced Susan gets enough nerve to go outside.
10.7k words
4.64
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Part 2 of the 4 part series

Updated 12/19/2023
Created 03/26/2019
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KissedMany
KissedMany
1,780 Followers

Hi, my names Amanda. Let me tell you about my adventure at a sex resort for rich men. None of my family or friends would ever believe I'd have gone here to service strange men for sex. That's except for my best girlfriend Riley, that got me into it. Read my story of the first night I came to this luxury resort on sunny, beautiful, Turks and Cacaos Island. I even got to fly in a private jet with many pretty, young ladies.

Let me describe myself. I'm nineteen and recently graduated high school. I live in a small city in a mid-western state. Boys say I'm pretty. I'm petite at 5'2" and my measurements are 34B-23-32. I was a gymnast until I was a freshman in high school but gave it up when I needed to study more to keep my grades up. I really wanted to go to university to become a history teacher. I still do yoga to stay toned and flexible. I have long naturally blonde hair almost down to my bum that I brush a hundred times every night just like mom taught me. I do date but haven't had a steady boyfriend for a while. I just didn't have the time. I'm not a virgin. Last year, I went out with an older guy that was a junior in college. We had sex a few times when he was on summer vacation, but we lost touch when he went back to school. We were both kind of new at sex.

Last night I had two very different erotic experiences. One was a bit kinky but harmless with an older gentleman. The other was with a handsome, rich, executive type about my father's age, named Edward. We had sex that was so great. He's so together. That's the only word to describe him. He is the total package. I got an instant crush and tried to stay with him, but he has a deal with his wife about girls at the resort that nixed that.

I've been very surprised at the type of male clients that are here. I expected them to be rich losers who couldn't find girlfriends, but they are mainly powerful, successful businessmen that any woman would find attractive. Their busy lives give them no time for mistresses, so they come here for sexual adventures and a needed break. Then there seems to be some younger, fun-loving men who likely inherited their wealth and want to spend it on pleasure.

After my erotic session with Edward last night, I went to bed right away. The traveling and the nervousness around the new experiences made me so tired. It was a long day. I feel great this morning. I found a note pushed under my door from management that said Edward had tipped me a thousand dollars and the older gentleman was even more generous. Wow, it looks like I'll be able to pay for college by the end of my week here.

I can see out the window that it'll be a sunny day. I've showered and put on some nice shorts and bright colored T-shirt. There were so many choices of beautiful clothes and swimwear in the closet and dressers that the management provides. The people that organize this are so thorough. When I was deciding what to wear, I was torn between being embarrassed by knowing men who are strangers would be checking out my body with lust on their minds and wanting to attract good clients. With a nervous feeling in the pit of my stomach, I chose to best advertise my physical assets. Under the short-shorts, I decided to wear a thong instead of panties so there wouldn't be a panty-line showing. I'll also go bra-less. My breasts are very perky and Riley, my girlfriend who told me about this place, said they were my best feature. I should show them off to attract more clients. After seeing what these rich men tip, I want to be wanted. White, platform sandals finish the summery look. They make my legs look good and my bum too. Let me take a few moments to steel up my courage and then go out to see what today brings.

Wow, I must be too early. There's only one man by the pool sleeping on a long, flat, lounging chair. He's nude, bum-side up with his arms hanging down, totally conked out. Looks like he's slept there, hungover overnight. I guess the partying went on until the wee hours. Oh great, there's a big breakfast buffet. I'll get some breakfast.

A feminine soft voice behind me says, "Hi. Is it okay if I join you?"

I turn and there is a drop-dead gorgeous young lady with a nervous look in her eyes. I was told not to mix with the other girls, but this girl has a Mid-West accent like me and there's no men about to compete for.

"Sure, my name's Amanda."

"Mine's Susan. Nice to meet you."

She's tall about five nine with long auburn hair down to her shoulders. She has a beautiful face in a cute, innocent way with luscious lips that I would die to have. She's the image of a perfect Mid-Western college home-coming queen, sexy but sweet. She's dressed in khaki shorts and a conservative, light green blouse. I can see she's wearing a bra under it.

I say, "I guess we're the early birds"

"Yes, I got to bed real early last night. After the lineup, when we girls were introduced to the gentlemen, I got panicky and stayed in my room."

"Oh no, you poor girl."

"Yes, seeing all those men looking me up and down with hungry looks in their eyes was unsettling. I thought I'd prepared myself for it. But I just panicked."

This girl seems inexperienced around men like I am. She felt like I did before last night. But I screwed up my courage and went out and made a lot of money. Plus, I met a nice man who made me discover how good sex can be. I don't want to look weak, so I'll act like I'm confident with her.

"I hear you but we're here for the money and we know what we need to do to earn it. I had an iffy experience and a good one last night and got over two thousand dollars in tips. These men are so rich, money's nothing to them."

'Jeez, good for you. Even if I get the nerve to be with some man, I don't think I'll do that well. I hardly know anything about sex. My parents are strict religious people. I was going to wait until I was married to have sex but had one slip-up with my boyfriend before I went off to university. Then we broke up when he started dating someone else. I'm not exactly a virgin but as close as you can be."

"Don't worry about that. My girlfriend who told me about this place, didn't have hardly any experience either. She made lots of money here, more than enough for first year university." I don't want to say I'm a novice too.

She responds, "I'm going into my junior year. I borrowed student loans for my freshman year, but doing that every year until I graduate will be a killer. Somehow, I've got to earn some money here. Maybe you can help me? Would you?"

She is so pretty that it's hard to look at her. Her beauty is intimidating. If she put herself out there, the men would line up to be with her. But I pity her insecurity. What the hell, I'll give her a hand. Maybe she'll be like honey and attract men for both of us to be with.

"Sure, I'll help you out." She gives me a big hug in glee. What a sweetie.

"I have an idea that might be a good way for you to start out here. There's a nice man that I was with last night who may be great for your first date. Why don't we go and meet him?"

Susan's Viewpoint

Go to meet him? Oh my, I didn't expect this to happen so quickly. Thank goodness Amanda is with me. She sounds like she knows what's she's doing. What if he doesn't want me. I'll die. Maybe when he sees I don't know anything about love-making he'll tell me to leave.

"Amanda, do you think I should change first. Your clothes are so much nicer than the ones I picked. You have a better eye for what men want."

"No, Susan, you look great. Let's just go over to his cabin and knock. You'll be fine."

Edward's Viewpoint

I should get up soon, the sun has risen. Hell no, I jump out of bed every day. Fuck it, this is vacation time. I'll roll over and sleep another hour. Hey, a knock at the door. I should have put a do not disturb sign on the door for the maids. I'll go and tell her to come back. Should I put on something? Hell no, half the folks walk around nude here. I wouldn't doubt the maid is naked.

"Hi Edward, it's me Amanda."

What's this? This is the young girl with the natural bush I fucked last night. And she's with a stunning young lady.

"Hi Amanda. Nice to see you. You lady's out for an early morning stroll?"

This new girl seems to be shy about me standing here in the buff with my dick hanging low. Can't be too innocent working at this sex resort. Then again, Amanda here hasn't had a lot of experience in bed. Her buddy's looking down and holding her hands together in front of her shorts. Nice legs. She's a good deal taller than Amanda and her breasts look very full. Nice set.

Susan

This man is so masculine standing there confidently naked. I got a glimpse of his hairy chest and his private parts. I feel too shy to keep looking. He may think I'm staring. I'll just look down and wait for Amanda to tell me what to do.

Amanda says, "Say hello to Edward, Susan."

"Hi, sir. Nice to meet you." I reach up and shake his hand. That was so dumb. I feel so awkward and childish. My goodness, Susan, you're twenty-one, not a kid. Look at him. Oh jeez, he's looking at my body. Why do I want to put my hands in front of my breasts and crotch? I'll make a fist and keep them by my side. I hope he likes what he sees. He is so handsome. I think of all the men here, he might be a good one to be with. He's taking so long, looking me up and down. I can see his penis getting thicker. I just got a shot of adrenaline through me.

Amanda explains, "Susan is a bit shy and didn't participate last night. I met her this morning. She's a real sweetie and I thought you would be a perfect gentleman to help her get started."

"Thanks Amanda. It'll be an honor. Why don't you ladies come in?"

"Should I leave you two together?"

"Hell no, come on in, the both of you."

Thank goodness Amanda will be here in case I go wrong somehow. My heart is beating fast as I go inside. I guess there's no turning back now.

His masculine voice says to the girl next to me, "Come here Amanda and give me a big hug." He hugs her and massages her bum with a big open hand. "That's the sweet ass I remember from last night." He's looking over her shoulder at me while he gropes her bottom. I bite my lip knowing what's next, me.

"Let me give your friend a nice hug too."

Edward

This girl's body is so lush and perfect. She stiffened up when I cupped her ass-cheeks. Ummm. Nice womanly ass for a girl so young. I like a bit of baby fat.

Amanda says, "Susan, you should feel Edwards nice bum too."

She hesitates but I can feel the tentative, light touch of her soft hands. Fuck, where does this place find these innocent girls. I love the fresh ones. This is going to be fun."

"How does my ass feel, Susan?"

I can hear her gulp, "Very good, sir."

I like that 'sir' stuff. I look down into her beautiful face, "How would you like to spend some quality time with me?"

"Thank you, sir."

She lets go of my ass. "Hey, girl, I didn't say to let go of my ass."

She grips it again, firmer this time, "Sorry sir." I smile and wink over at Amanda and mouth the words 'thank you' silently to her.

"Quite alright, quite alright." I like Susan's attitude, eager to please and respectful. I'm getting an erection holding on to such a gorgeous girl and knowing I'll be balls deep in her tight, young pussy, soon. "I'm going to have a shower. You girls wait here." No rush. Best to take a piss and a shower to freshen up for the new, young thing.

Amanda pipes up, "Do you want us to take our clothes off?"

"Thanks, but no sweetie." That Amanda is really something. I might have to fuck her again. No, better not. My wife might have spies here. We have an iron-clad deal, no fucking the same girl again after that first day.

Amanda's Viewpoint

I got a twinge of jealousy when Edward was holding Susan. He's such a hunk. I know it's crazy, but I've got a crush on him. He was so wonderful last night. It would be so perfect to learn more about sex with him. I can hear the shower in the bathroom. It's such a drag that he has a deal with his wife.

I say to Susan, "What do you think of Edward?"

"He's a very handsome man. So much more mature than my ex-boyfriend. He has an attractive body even though I tried not to stare. Amanda I'm so nervous, I think I'm going to faint. I can't believe I'm really going to do this. My friends would never believe I'd do anything like this. Thank goodness you're here or I'd likely bolt out that door."

Boy, she really is innocent. With her looks, it's a wonder the boys weren't all over her since puberty. Her religious family must have kept her on a very short leash.

"He's a good one. So just do everything he says, and all will be just fine. Hey, I just heard the shower stop. I have some lipstick in my purse. Here put it on. Yes, good, a very sexy shade of pink. You look good, very desirable. Don't worry."

Susan.

Butterflies are flying in my stomach as I wait for Edward. This is such a big cabin. I must cost a fortune. We are sitting on the sofa waiting. I hear noises in the bathroom and a man humming. Oh, here he comes, still nude but with wet, dark hair combed back. He's so unbelievably at ease around nudity.

"Susan, why don't you stand up and let me sit beside Amanda. That's a good girl."

I stand up. He throws a casual arm over Amanda's shoulder and looks up at me. His legs are in a 'man spread' and I can see his relaxed penis and his scrotum hanging below. I wait for instructions.

"Turn around sweetie. I'd love to take a good look at you. Nice, very nice. You have a very nice body. Congratulation."

"Thank you, sir"

"Now this time, stop so I can take a good look at your nice ass. I'm kind of an ass-man. Yes, just like that. Now bend over a bit. Not that much. Yes, just like that. Hmmm, very nice."

I look over my shoulder at the two and I see Amanda slowly stroking his now erect penis as his eyes are drilled hungrily into my bottom. The look of lust on his face sends a thrill and some fear through me. Even from this far away, his erect penis looks very large.

"Okay love stand up and turn around. Unbutton your blouse for me. Not too fast. Yes, just like that. Great. Okay, just toss it over that chair."

I see Amanda has removed her t-shirt and Edward is casually fondling her bare breast. Her eyes are closed, and a smile of pleasure is on her lips as she continues to stroke his manhood at the same time. What a sexy sight.

He says to her, "Amanda, stop stroking me and just hold my balls. I want to cum in Susan's young pussy, not in your hand."

I knew sex is going to happen, but for him to say it so brazenly and confidently just took my breath away. I can feel a hot blush on my cheeks.

Ed

This girl is magnificent. If I'm not mistaken, I think she just blushed when I said I'll be fucking her. Such a sweetie. I love having her strip for me. It gets her mind right.

"Okay, Susan, now the bra." She is biting her lip and hesitating. Maybe she'll run to her room like she did last night. She looks over at Amanda with a questioning look on her face.

Amanda helps out, "Susan, go ahead. It's all okay. Just like we talked about. You can do it."

A determined look crosses Susan's face and she reaches behind her back and undoes her bra. She holds the cups with both hands, closes her eyes and lowers them revealing herself. Her breasts are incredible, firm, perky and full. My guess about a 36C. My stiff dick twitches at the sight not just because they are so beautiful but mainly because I now know I will be mounting and fucking her soon. She's made her mind up to do it.

Best to keep up the momentum. "Okay Susan, the shorts. Put them on the chair with your blouse. Yes, there. No, sweetheart, don't be shy. Take your hand away from your crotch. Good. Yes, very nice. Pull your panties up. Yes, that's very good." I can see the outline of her camel-toe notch in the Y where her legs meet at her crotch. Oh, I love her panties. They have pink flowers all over. Very cute and girlish. These are the Brazilian style that is somewhat full. There is a small pink bow at the middle of the waistband. It's like a Christmas present I get to open. Aha, the little minx beside me is taking her shorts off and showing off her dark beaver. No panties. What a slut. Ummm, I smell pussy.

"Turn around Susan. Good. Just like that with your bottom towards me. Your bum is even nicer just in panties. Very nice. Bend a bit. Good. Actually, bend right over and spread your legs. Perfect."

She has a perfect butt, womanly not boyish. I can see the folds of her pussy lips in the crotch of her panties when she's bent far over like this with her legs spread. What's this, a little damp spot. Fuck, what a horny view.

"Now pull your panties down slowly so I can see your pussy. Not too fast." I'm speechless. Holy fuck, what a horny, fucking sight. A perfect ass with the slit of her pussy and clean-shaven pussy lips clearly now in sight. I can't help grunting, animal grunts as her fertile, young pussy comes into view. It's all I can do not to pull her down onto my hard dick.

Susan

My face is so hot. Oh my god, my breath is coming in pants noisily through my nostrils. It was all I could do to put a finger on each side of my panties and pull them down slowly. I feel like such a tart. Thank goodness, I shaved all my pubic hair before coming down here. I can hear him make animal sounds when they were halfway down my thighs. I'm too embarrassed to look back at him. My private parts are starting to throb like never before. I've never felt this horny. Oh no, I just realized he can see my anus when I bend this deep. I'll die. Oh no.

"Susan, don't cover your asshole with your hand. I love the carnal, base look of a woman's asshole. Take it away. In fact, spread your ass-cheeks with both hands so I can get a good look. That's better. Nice. Very nice. Now come and sit with me."

He says to Amanda, "Why don't you go and sit in that armchair while Susan and I get to know each other better."

I sit beside him. He is a good head taller than me. That's good. He pulls me to his naked body. My boyfriend and I were in the dark when we had sex that one time. Being next to a mature naked man in a lit room is such a different experience. His male equipment seems so dangerous. The feel of his bare leg and the side of his chest against mine is so erotic, so natural.

He looks down at me, smiles and says, "How are we doing, Susan?"

I answer truthfully, "I'm a bit nervous sir. Sorry, but I don't have a lot of experience at this."

"That's quite alright, my dear."

He hugs me to his muscular, hairy chest. That feels so nice against my breasts. Hands go to my bottom and gloriously massage it deeply. Oh lord, that feels so sinfully good. I peek over and see Amanda is sitting spread legged and rubbing her private parts as she watches us. What an erotic sight. I close my eyes and throw my hands behind his neck, snuzzling my face under his ear to give him free access to my body. Gee, I'm so happy he likes me.

He whispers huskily in my ear, "Hold my cock, baby." I slip my hand down to his waist and find his stiff, thick erection. It feels like velvet over granite. My crotch throbs. It almost vibrates as lust is filling my brain. I kiss his neck and shift my pelvis to his hip and rub my crotch there for some friction, for some needed relief on my pussy. His one hand goes from my bum down to my thigh. My knees instinctively snap together at his electric touch.

Ed

This girl is in heat. A minute ago she was humping my leg, she's so horny. Now she's clamped her legs together. Well, sister, it's time a real man felt you down there.

"Open your legs, dear. I want to feel your pussy." She whimpers meekly in my ear. "I said, spread your legs." They open slowly. "That's better."

I run my hand up to the promised land and I hear a squeal of shock in my ear as my palm slides over her sex. I feel a shit-ass grin on my face as she kisses my neck in submission. I probe her sensitive areas.

KissedMany
KissedMany
1,780 Followers