tagFirst TimeLisa’s Summer Vacation Ch. 01

Lisa’s Summer Vacation Ch. 01


Try as she might she couldn't make the phone stop ringing by force of will. It was the third time in the last 15 minutes that it had droned on insistently so she assumed it was probably her mother and that the only way she could get it to stop would be to answer it. She picked up the beastly instrument.

"What now, Mother?"

"However did you know it was me?"

"Because you're the only one I know who wouldn't be satisfied until she robbed me of any shot at a decent night's sleep."

"Be fair, Darling, I did wait until after breakfast!"

"Yes you did Mother but being as how you're in London and you're six hours ahead of me that doesn't help much. It's only four AM in dear old Connecticut."

"Oh, I forgot, but it's just that I wanted you to know that it's not my fault! Your father just won't budge and besides since it is business I suppose we'll just have to forgive him."

Lisa rolled over and rubbed some of the sleep from her eyes. In the middle of a yawn she said, "I'm really pleased that at least one of us knows what you're talking about."

"Your father's scheduled some meetings with Jack Maroni, something to do with his family's holdings in Italy. Anyway we'll be staying at his family's place in Bellagio for the entire month of July."

Lisa sat up like a shot. "Mother I hereby retract every bad thing I've said about you for the last three weeks. When I had to give up on going to Cozumel with all my friends just so I could do the family thing to celebrate my 18th birthday at the cabin I really wanted to trade you in for another mother but to summer in the most beautiful city on Lake Como? Trust me, all is forgiven!"

"Sweetheart that's the problem! The invitation extended to your father and me only, so you'll have to stay in the states this year. I'll make it up to you and we'll do Aspen for the Christmas holidays, all right? You've always loved it there, haven't you?"

Lisa couldn't have been more disappointed. She found she had no desire to scream at her mother so rather than continue the conversation toward that inevitable outcome, she just gently hung up and unplugged the phone. It took her about a half hour to get back to sleep... she really was starting to believe that you can't fall asleep if your tears are still wet.

Four hours later she was in that half awake state laying on her back weighing the pros and cons of sleeping away the entire summer when her roommate Sally rolled in after spending the night in her boyfriend's dorm. She took one look at Lisa and said, "Wow, you look shittier than I feel and I'm the one who's hung over!"

Lisa looked at her roommate, "That's because my summer's fucked! It's too late to book Cozumel, no Bellagio, not even the family cabin in the Finger Lakes fishing with my brother and Dad! About a half hour ago I decided I might as well sign up for a few summer session classes and pick up a few credits."

"No, no, no, no, girl, if ever I knew a girl who needs an injection of serious partying besides myself, you're her." Sally sat on Lisa's bed, pushed the sheet down to her waist and started massaging the girl's bare back and neck. After about three minutes she said, "Remember about when we were planning for Cozumel? I got the impression that you'd pretty much decided that you were going to lose your cherry down there, right?"

"I guess so. Actually that was to have been one of the highlights of my trip. I'm not sure who was going to get it yet, but someone was going to be offered the first chance to fuck me!"

"Okay, then I know what you should do! Talk to Marjorie Mantzer!"

Lisa barely knew the girl Sally had referred to. They shared one class, Organic Chemistry, so Lisa would probably never would have spoken to her except that they were paired up for one lab assignment. Lisa recalled her impressions of the girl; very bright, 4.0 grade point, blonde, 5'7" tall, serious rack of 34D's, pretty face, slim figure, pretty much any campus hound's wet dream except she always politely blew of every attempt to hit on her, whether coming from male or female. The class had always referred to her by a nickname... "You mean Brainiac?"

"The very same! You should try to hook up with her for the summer. I think it'd be good for you."

Lisa tilted her head and looked at her roommate.

"A, I didn't know you even knew the girl.

B, although I could see getting together with her if I was studying, since she's almost as smart as I am, but she always seemed kind of stand-offish to me.

But C, why would I want to be around a girl who shoots down every guy who approaches her if my goal is to get laid?

Where's she going for the summer, anyway?"

"I have no idea and neither does she and by the way she might even be smarter than you."

Lisa smiled at that. Sally continued, "Okay this is 'roommate secret' stuff. Marj is kind of a private person, all right?

We got to know each other last year in ground school when I was studying for my Private Pilot's exam. Since then we try to stay in touch on at least a weekly basis, sort of a Starbuck's relationship. Her family has zero money but she's on a full academic scholarship and because she doesn't want work to interfere with her studies she earns all her year's pocket money at her summer job."

Lisa rolled over and sat up straight, her large breasts temporarily distracting Sally. Lisa said, "You want me to work this summer? Hello! In case it escaped your notice I don't really need the money and..."

"Shut up and let me talk, okay?" Sally reached out and tweaked one of Lisa's nipples. "Where was I? Oh yeah, she works a ten week contract for an entertainment service every summer. Last year she didn't have any idea where they'd send her but she wound up spending time in Costa Rica, Hydra, off the coast of Greece, three weeks on a yacht in the Seychelles, and some other places I've forgotten."

Lisa was suspicious but still curious. "What kind of entertainment service?"

"Don't be dense, Lisa. She spends her summer partying. She's a professional party girl. The only difference between what you were going to do in Cozumel and what she'll be doing all over the world is that the service picks out which parties she attends and she never says no!"

Lisa's mind was in overdrive trying to process all the information she'd just been given. She looked at Sally for more than a minute before saying, "Are you sure they're still hiring?"

"That's what Marj said yesterday."

Lisa giggled. "Sally I think I want to do this! I can't believe I'm saying it but I think it might be cool to be a whore for the summer, especially since no one I know will know about it! Call her and set it up!"

The next few weeks disappeared in a flash. Lisa had met with Marjorie twice, once that same evening that Sally had told her about Marj's summer job and once when Marj accompanied her into The City to interview and get some promotional shots taken for the agency. She'd received a call telling her when she and Margie were expected in New York right after their last classes were over but other than being told that they'd be flying to Miami as their first stop, she still had no idea where she was going after that.

Marjorie had finished her last class that morning and Lisa was sure that her one o'clock comparative lit. class was going to be dismissed as soon as she turned in her final paper.

A car service had picked them up and drove the two girls to LaGuardia for the first leg of their journey. Marjorie reached over and squeezed Lisa's hand. "Nervous?"

"Big time! I'm glad I didn't eat much this morning 'cause I'm afraid I might've barfed it up on the plane!"

"Want me to tell the driver to turn around and take you back?"

Lisa squeezed back. "No, I'm going to do this thing. I don't back down!"

"Well if it makes you feel any better I thought I'd mention your 'issue' to our host so he can treat it accordingly."

"What issue?"

"You know, the virginity thing."

"Oh that issue! What difference would telling him make?"

"Most young guys treat a cherry as if it were a scalp to be hung on their lodge pole. Most mature men will probably treat you with the tenderness you deserve... unless you wind up with some asshole. Talking to our host will steer you away from the assholes."

"So you figure we'll be in action tonight?"

Marjorie smiled, "Trust me, Lisa, you won't be a virgin when you wake up tomorrow morning."

Lisa said, to no one in particular, "Ohmygod, this is really going to happen!"

In the drop-off lane at the airport the limo driver gave their luggage to a skycap. He leaned in and kissed Lisa's cheek saying, "Don't worry sweetheart you'll do fine. I only wish it was going to be me tonight!"

Lisa looked back at him for a few seconds before throwing her arms around him and kissing him back with a lot of tongue. "Me too! Let's get back in the car."

The driver gently brushed some stray hairs out of her face and pointed at a sign. "Sorry but it says loading and unloading only." He gave her one last kiss on her forehead and drove away.

Lisa hooked Marjorie's arm and began walking into the terminal. "I feel good! He really relaxed me and maybe even made me a little horny! Let's do this thing."

They were met at the airport and driven to a pier where the largest boat Lisa had ever seen was moored. Her Dad kept a cruiser at Stuyvesant Yacht Club on City Island so she knew a little about boats. She tugged on Marjorie's sleeve. "This is unbelievable!"

"Big, isn't it?"

"Big? I have no idea how big this behemoth is but see those tenders hanging on davits on either side of the stern? I know what those are 'cause my dad has one. Those are 41 foot Bertrams! You could hook Moby Dick from one of those!"

Two stewards took their bags and the two girls were led to their staterooms. "Ladies my name is Andrew and I'm the Head Steward assigned to all the young ladies on board for this cruise. If I might suggest it, you may want to clean up from your trip and get changed for cocktails. You'll find cocktail dresses, shoes and hose in the correct sizes in your rooms. Underwear will not be necessary. I'll be back at 6:30 to lead you to the lounge. Have either of you any questions?"

Lisa asked, "Andrew, just how many 'young ladies' are on board?"

"The Captain's wife Mrs. Dianne Raymer, Mrs. Elizabeth Denton, Mrs. Linda Rice, and six of you 'unattached' staff members."

Marjorie then asked, "Whose boat is this, Andrew, or perhaps I might be better off asking whom I should make a special request of?"

"Your host is Mr. Denton, Marjorie, but all guest/staff issues go through me. What can I do for you?"

"Well I just wanted to bring it to his attention that this is Lisa's first time and I was hoping she might be handled with kid gloves this evening."

Andrew looked at Lisa and asked, "Do you mean first time as a commercial transaction or..."

Lisa blushed as she looked at the floor. "I'm still a virgin."

Andrew didn't look as if the news in any way surprised him. "I see. Thank you for bringing that to my attention. I'll make sure Mr. Denton is made aware of that fact."

After Lisa got out of the shower she slipped on a garter belt and put on the stockings which had been left for her. She had never dressed without any underwear before but all thoughts of that flew out of her mind when she donned the cobalt blue dress. She slipped her feet into the matching shoes and went next door to Marjorie's room. She burst in and exclaimed, "This is undoubtedly the most beautiful dress I've ever seen before. I feel like royalty!"

Marjorie looked her up and down. "You should, it's an Armani."

At 6:30 Andrew arrived at Lisa's open stateroom door with two other girls in tow. One was an overwhelming brunette beauty built along the lines of Catherine Zeta Jones and the other was a true 'spinner' as the guys liked to say; a statuesque figure on a blonde standing barely 4'9" tall. Andrew led them all to the lounge and introduced them all to their host. A steward took their drink orders and as the other girls became involved in conversations with various guests Mr. Denton leaned over and whispered in Lisa's ear. "Mingle, meet the guests, but if anyone wants to enjoy your charms just tell them that you've promised yourself to me this evening. I've got to play host for a while longer but to be honest I can't wait to show you my cabin!" He squeezed her ass before patting it to send her into the crowd.

It turned out to be a good thing Mr. Denton had forewarned Lisa because at least six men had offered to take her back to their staterooms to "get better acquainted". She'd had three Orange Crushes, was feeling an appropriate buzz and at this point she felt like the Belle of the Ball whose ultimate duty was to give sex to everyone on board. An imposing redhead in a translucent gray sheath came over to her. "Hello Lisa, I'm Elizabeth Denton but please just call me Liz. My husband asked me to escort you to our cabin if you're free right now?"

Lisa extended her hand as she said, "Pleased to meet you Liz. I've been waiting for his summons so just lead the way." As they walked down a hallway toward the upper deck staterooms Lisa had to ask. "So I guess if you're fetching me then it must be all right with you?"

Liz looked at her and asked, "Then what's all right dear?"

"All right for he and I... for the two of us to... you know!"

Liz laughed, "Oh that 'he and I'. Yes of course it's all right. In fact if you don't mind, I'll be joining you. You really do have a delicious looking body."

Lisa almost purred as she replied, "Oh I don't mind one little bit!" As they continued to walk Lisa unzipped the dress under her left arm so Liz could get a good look at her as she swung her arm.

The stateroom was palatial but Lisa barely had time to see it before Liz had swept her into her arms and was kissing her lips as she slid Lisa's frock to the floor. Liz just had to shrug her shoulders and her own dress joined Lisa's. Lisa had never been with a woman before but it seemed totally natural as she slipped to her knees and began running her tongue over her hostess's labia. Liz' knees almost buckled when Lisa exposed and then began sucking her clit, so she took the young girl by the arms and led her to the bed.

At that point Mr. Denton came into the room wearing a gold colored flocked robe. "I'm sorry to be late, Lisa, but as I see Liz has been entertaining you I suppose it wasn't so terribly bad.

Can I fix either of you anything?"

Liz responded. "Something sticky that goes well with breasts! Grand Marnier I think might fill the order."

"Excellent choice since GM goes equally well with both breasts and pussy! While you're concentrating on Lisa's magnificent tits I think I'll pour some over that soon-to-be-shaved bush of hers." The next thing Lisa knew they were pouring the sweet liqueur over her breasts, down her belly and between her legs. The feast had begun and Lisa was the main course.

Maybe it was because she'd been drinking. Perhaps Mr. Denton was just particularly skilled at eating pussy or it could just have been the idea of having these two use her as a sex toy, but Lisa came more quickly than she had ever done before. She arched her back into a wrestler's bridge and jammed her pussy into Mr. Denton's face as he slurped up what seemed to be pints of Lisa's ejaculate. Liz clapped her hands together in mock applause as Lisa half rolled over and grabbed the GM bottle.

Lisa pushed Mr. Denton onto his back and poured some of the amber liquid over his genitals. She then turned so as to offer her pussy to her hostess and lowered her face to her Master's cock. She took each ball into her mouth and scrubbed them clean with her tongue before moving to the 7" member which was tapping her cheek as it throbbed. While she was working on his testicles she'd decided that she wanted to try to deep throat him on her first blowjob so she opened wide and kept sliding the sticky rod in until it hit the entrance to her throat. She only paused for a moment and then she continued pushing and Denton's cock slid all the way down her throat until her face was buried in his pubic hair. She was sure she was going to be able to continue but the aromatic alcohol's fumes filled her nostrils and made her pull back. At this point she began sucking the liqueur from the bed of hair just as Liz' tongue assaulted her clit.

Lisa couldn't count how many orgasms she'd had. Likewise she couldn't believe her pussy was already sore just from the workout given it by the Dentons' tongues, but it didn't really matter now because the moment had at last arrived. Liz had gone back to sucking Lisa's breasts as her husband started rubbing his cock up and down Lisa's slit. Before she knew it the head had entered her and Denton began 'shallow fucking' her, making sure that each stroke stopped short of her hymen.

At first Lisa was apprehensive about the coming pain, but it just didn't arrive. Denton seemed content to just keep pounding her with the same short strokes. Finally Lisa just couldn't take it anymore. All nervousness gone, she began arching her hips to meet every thrust of Denton's, forcing his cock deeper into her with every stroke. Finally he burst through and fully buried his cock into her. He stopped fucking her, waiting for Lisa to take the initiative. She didn't need to be asked. She reached behind him, grabbed his ass, and began driving him into her as hard as she could. Happily Denton took over and resumed his relentless pounding of her pussy. Lisa locked her ankles over the small of his back, dug her nails into his shoulders and kept slamming her pelvis into him. She was thoroughly enjoying her first fuck.

Lisa was vaguely aware that Liz had gotten up and left the room but was enjoying the sex so much it occupied one hundred percent of her attention. Every time it seemed that Denton was about to cum she slowed the pace down so as to make the fucking to go on forever. She flashed on Audrey Hepburn's Eliza Doolittle singing "I could have fucked... all night, I could have sucked... all night... and still have fucked... some more!" Well at least she should have sung it that way!

Lisa heard Liz come back into the room but she didn't care. She could feel Denton getting close to his climax and as much as she wanted the fucking to go on and on, she also wanted to give him the most powerful orgasm he'd ever had. She tightened her vaginal muscles around his cock and dug her nails into the cheeks of his ass driving him as deeply into her as the position would allow. Her legs were trapped against his chest and her toes were pointing at the ceiling as her hips rotated to give him an added dimension to the fuck. She had no idea how long she could continue squeezing his cock with her vagina's muscles but in her heart she vowed it would be long enough. Just when it seemed Denton was ready to explode Lisa stuck her finger into his asshole.

Denton roared as he came. Lisa loved the feeling as each burst of semen exploded into her. Finally, thoroughly exhausted, Denton allowed his weight to fall onto Lisa's body. He rolled her so they were on their sides, still locked in a tight embrace. They were both giggling. Lisa started showering his face with kisses saying, "Thank you, thank you so much. This was so better than anything I could have choreographed."

Denton kissed her nose. "I should be thanking you for one of the most intense fucks I've ever had! I would never have expected it from a virgin effort! I also was completely bowled over by the way you controlled the end. I was completely aware that you didn't want it to end then but you were willing to forgo your own pleasure so you could add to mine. It's the least I can do to let the fucking continue."

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