Seths Crazy Vacation

It seemed like such a harmless offer when my friend Benny invited me out to his family's timeshare one summer. It was supposed to be just Benny and his girl along with me and mine. I had never had any obsession with older women. I had never had any desire to submit to a woman. And, at first at least, my girl Kitty was to be my only sexual partner for the summer, and if things went well, then for the rest of my life.

I had been looking forward to the trip, a chance to take a break between high school and college, a chance to unwind, hang out with friends, but mostly to spend time with my girl before I popped the really important question.

I know they say not to make commitments like that too young, that kids are not wise enough to make decisions like that, but I knew she was the one I was meant to spend the rest of my life with.

It took me by surprise when Kitty dumped me the week before we were to leave. She had been cheating on me, had fallen in love, and had never intended on making the trip.

"Seth, I'm sorry. If it's any consolation I was supposed to break up with you months ago, but I really couldn't give up on the sex."

Of course, that was no consultation at all. At least I didn't think those words were at the time. I tried to drop out of the trip myself but Benny was not having it.

Benny was a little guy and prematurely bald, but he had this ridiculous force of personality that people just couldn't say no to. The women he dated were testimony to this. I hadn't met his date for the trip yet, but I would be shocked if she wasn't an aspiring model or some such ridiculousness.

It took a few days, but in the end I folded. He said his girl, Jenny, felt nothing but sympathy for me and anger at Kitty (whom Jenny knew through going to the same school), so she was bringing her busty and "fun" friend Nichole in my exes place in the hopes that we hit it off and fuck each other senseless all summer. He pulled up a pic of Jenny and Nicole. They were hot...

I mean, hanging with a bud and two hot chics was still a lot better than working all summer. Right?

The drive down went perfectly. I decided to treat Nicole and Jenny like old friends, in order to bypass any awkwardness. I mean an entire summer together is one hell of a long blind date.

And I am not going to lie either, I was more than a little nervous. The girls were both gorgeous, and while sexually confident I had never been overly charismatic. I needn't have worried. Benny was more than capable of carrying the conversation for everyone.

At first I sat up front with Benny but by nightfall I was sitting comfortably in the back with my arm around Nicole while she slept soundly on my shoulder. I am normally a leg guy, not a breast guy, so normally I would have gravitated more towards Jenny than Nicole, but Benny assured me that there was nothing for rebound sex like a round ass and a nice full set of tits. Nicole definitely qualified.

Nicole had three or four years on me, but she didn't seem to care. She was short, blonde, blue eyed and had plenty of curves. She wasn't fat by anyone's reckoning, and I couldn't imagine she could sit at a bar without men tripping over each other to buy her drinks, but my eyes couldn't help but wonder over to Jenny's long legs and short shorts.

Jenny was tall with long auburn hair. She was a little small in the chest maybe, but she was absolutely my type. Tall, tanned, long hair, unbelievable legs, and she was, as I expected, an actual model. She wasn't a famous one or anything, appearing only in local magazines, ads, and maybe the occasional car mag, but she had a confidence about her that said she was going places.

We got to the beach after dark. Benny and the girls hit the beach straight away, while I was left to carry things in from the car. The time share, which was really a condo on the beach, had only two bedrooms, a single bathroom, a kitchenette, and a small living room with a small sofa table, and no TV.

I was getting along fairly well with Nicole, but sharing a bed seemed a little bit rushed. I hesitated when it came to putting our things away, but I had little choice with where to put our bags. Jenny and Benny got the main room, while I sat Nicole and I up in the smaller room, then changed into a pair of trunks.

The girls passed me as I finally made my way down the beach, promising to return in their swimwear. I was glad that the two of them would be in there alone, as it would let them talk about the sleeping arrangements more privately.

By the time things wound down at the beach, Nicole found some time to talk to me about it. Jenny took Benny out into the dark surf alone, giving Nicole a meaningful look. I enjoyed watching Nicole step slowly out onto the sand, the moonlight highlighting her sexy figure as it kissed off of the ocean water. My erection was incredibly curious to find out where things might be leading.

I didn't think I was ready for a full blown relationship or anything just yet, but I am man, here me roar, and I'll be damned if I wouldn't make a move on this beauty if she gave me half an invitation.

She dropped next to me in the sand, and told me that she saw the bed, and that she knew that I was a guest long before she was, so she was not going to ask that I sleep on the couch or anything. She was comfortable sharing a bed with me, but she wanted to make sure that I was could handle being a gentleman.

"I think I can handle that," She looked at me doubtfully. As I mentioned, I was male, which hurt my credibility. I went for humor. "for the first night at least." I amended. She laughed. It sent electric jolts down her sizable breasts and magically through the air and down my cock.

"We can take things one day at a time." she told me. "I am going to shower and unpack. Why don't you head up with me and give those two some privacy?"

My jaw dropped as she stood and her fantastic ass popped up in front of me. God bless the man who invented thongs. "There are other people on the beach." I said. Which was true, I doubted Benny was going to be scoring out there in the water.

Nicole arched an eyebrow at me in a way that implied that I might be a little slow. "You would be surprised what lovers can get away with in the ocean at night. Most who notice will look away. Well... let me re-word this. You can come up and flirt with me for a bit, or stay here alone and watch your buddy make out with his girl."

I followed the girl. See? I am not that dumb after all.

That first night, Nicole laid with her back to me. I lay on my back. Neither of us were falling asleep. An hour passed that way, wondering if I should spoon with her or stay on my side. Eventually I got up and grabbed a pair of trunks.

"Can't sleep?" she asked me.

I thought about my answer for a second. "It turns out being a gentleman can be harder than I thought." She didn't turn to look at me, so I was hoping that I sounded more flirty than creepy. I was not very charismatic. "I am going to go on a run and burn off a little energy. I will be back by morning."

She didn't say anything. I could only hope that she was smiling. She was asleep by the time I returned, showered the sand off of me, and climbed into bed. When I laid down she didn't wake, but she backed up against me. As tired as I was, I reacted on instinct, turning into her and wrapping my arm around her. She had on a white night shirt and based on the way her breasts felt against my forearm I guessed that she had decided to remove her bra after I left. It still took me a bit to get to sleep, but knowing the girl was already asleep took all of the challenge out of being a gentleman.

I woke when Nicole got out of bed. I watched her put on her bra in that way women do without actually taking off their shirt. She changed panties, which gave me a fantastic view of her ass. She knew that I was awake and watching. She even winked at me when she bent down to pull on the other pair. The view of her cunt from behind made my mouth water. After the shorts came up the shirt was next, and she made no effort to face away from me as she pulled off her sleep shirt and put on her fresh top. I know that technically a bra covers every bit as much as a bikini top, but trust me, the two are completely different animals.

She closed the door behind her when she left, and I head Jenny and Benny talking in the front room. I hadn't gotten very much sleep the night before, so I rolled over to get a little more while I had the chance.

I didn't wake up until just after noon.

The condo was empty, and I had no idea where everyone was. A quick look around the condo for a note provided no clues as to where everyone went either. I knew Benny's aunt and uncle lived somewhere close by, and that we were all expected to go see them this morning. Perhaps they had all gone over there without me?

I was not one for breakfast, so I decided to head down to the beach and check out the area by the light of day. I stripped down and into a pair of trunks before stepping out through the sliding glass door and out onto the back deck.

The condo was connected to the one next door, so the two shared a wall and a deck. There was a dividing fence between the two properties down the middle of the deck, but it was low enough that someone tall like myself would have little trouble stepping over it. The stairs down to the beach were shared, and there was a hose at the top with which you could wash off your feet.

That space was occupied by a rather normal looking man in his late thirties and his fantastic looking wife that I guessed to be thirty one or two at the oldest. I gave her a 9 in passing. She was a tall blonde with shoulder length hair. Her breasts were large for her very slender frame, enough so that I guessed them fake. Maybe a large C on her tiny body. I didn't doubt for an instant that they would look just as firm and gorgeous outside of the tiny bikini top.

As I mentioned before, I am a leg man, so I was immediately drawn to the blonde's long legs and slender hips. They had just the right amount of muscle on them to make a man want to feel them wrapped around his head or hips.

The husband caught me looking. I decide to play it off, and he let me. I walked up, as they were in my way, and offered my hand. They introduced themselves as the Campbells, and asked if I was Benny.

It turns out Benny's aunt and uncle, Dan and Anna Johnson, were the ones who owned the actual property, and that they owned most of the condos on the block. The Campbell's owned a portion of the one next door to ours and when they were not using it it would get rented out and the profits would be split evenly between the families.

While they were using it they paid Dan and Anna what amounted to a rent payment in compensation for the time the time share was occupied. It wasn't much, maybe twenty percent of its actual vacation rental value. I was guessing that it was a similar arrangement between Benny's parents and aunt and uncle.

The Campbell's asked if I would mind taking the Johnsons their payment whenever I went to meet them. I agreed, and Mrs. Campbell went inside to presumably fetch it. I couldn't help but watch her go.

A long moment passed in silence. "So which of those pretty young women are yours." Mr. Campbell asked pointedly. At least he was smiling.

"Oh, um, neither technically. My girl dumped me a month ago. The tall one is Benny's girl and the shorter one is her friend. I only met her yesterday."

"Ahh. Well I am sorry to hear that." He said, giving me a look of understanding.

"Sorry to here what?" Mrs. Campbell asked when she came back out. Mr. Campbell told her what we had said, pretty much verbatim. Mrs. Campbell expressed her sympathies. "But don't worry, I am sure a handsome young man like yourself will find plenty of pretty young girls to help you get over her." She touched my arm when she spoke, and Mr. Campbell coughed disapprovingly.

They gave me the cash in an envelope, and as I didn't have any where to put it (I was only in my trunks) I took it back into the condo and put it on the dresser in my room, under my own wallet. I made sure to lock up on my way down to the beach, and set out on another long run.

I guessed it was about ten miles to the peer and back. I took my time. I was gone for over an hour, probably closer to two. I even chatted with a few pretty girls, which was a very brazen thing for me to do. I had no idea how to get to the Johnson's, so I figured I had plenty of time to kill on the beach. I was not about to spend that time sitting patiently on the couch.

When I got back, people were in the condo. I had assumed that it was my companions up until I opened the sliding glass door. Yeah, I know it is glass and that I should have known before I opened it, but I didn't look, so shoot me.

A woman I had never met sat on the couch. She was in her mid to late fifties, wearing a long grey T shirt and a pair of denim shorts. The shirt had a wide enough opening at the neck so that it was actually draped over one shoulder, and I could see she had on a zebra striped bikini top underneath.

Mrs. Campbell was in the kitchen area, which was only blocked off from where I stood by a counter/bar. She was apparently making a pair of mixed drinks using our booze. She had changed tops, now wearing a thin orange bikini top that covered more of her breasts but was so thin it did nothing to disguise the position or firmness of her nipples beneath it.

I was pretty sure a splash of water would render it transparent.

"For a bunch of kids fresh out of high school you all certainly brought a lot of alcohol." she said. She smiled and winked at me.

"Nicole and Jenny were old enough to buy. How did you get in here?" I asked a little less than politely. I know, stupid right? Why be upset to come home and find two unexpected MILFs in your condo? Well, I was curious how they got there, and I felt slightly uncomfortable with the idea that someone could just let themselves in to our place.

"I let her in." said the brunette on the couch. "I guess you could say that I am your hostess this trip. My name is Anna Johnson, Benny's aunt. And of course I have a key darling." her eyes were smiling, but she wasn't. I have never been charismatic, but I have always been good at reading people. Too good in fact. As I knew she wasn't truly displeased with my words of greeting, I almost missed that she expected me to think she was.

I mumbled my apology and introduced myself. "Of course I know who you are dear. I heard all about you from Jenny and Nicole." She left an amused pause hang in the air, giving me time I guess to wonder what the two girls would have said about me.

"Dan and I wanted to take the four of you kids out on the yacht. You were not here, obviously. Cindy and Randy said that they saw you go out for a stroll. We waited for quite a bit." At this Mrs. Johnson motioned to Mrs. Campbell. Which was good, as I hadn't learned her or her husband's first names.

"Dan ended up inviting Randy to take your place, and he jumped at the idea. I have no love of Cindy's husband, as Dan well knew, and as Cindy had not been invited I volunteered to stay behind with her and have a girl's night out. We were going to spend the cash Cindy had set aside for our timeshare payment, and apparently she gave that to you. Does that adequately explain what we are doing here, wasting away the afternoon waiting on you?"

This time I couldn't have missed the sharpness in her voice. It made me flinch, to which Anna and Cindy exchanged a smile. I apologized and offered to fetch it.

Only when I got to the bedroom there sat my wallet, but the envelope was gone.

Had Nicole hid it as a gag? I had no concept of how much money was in it, so I frantically went looking thru Nicole's things. Then I looked though my own. Growing frantic, I lifted the mattress. No luck. I got down on the floor to check under the bed when Anna came to stand in the doorway.

It wasn't under the bed. I rolled over onto my back, a desperate apology on my face. "Having trouble?" Anna asked, casually taking a sip from her mixed drink.

I was abashed. I struggled, trying to find words to explain what had happened. I stammered out that the money wasn't where I had left it, and my guess that Nicole must have hidden it.

"When?" asked pretty Cindy, stepping into view. "When everyone came looking for you, we invited everyone over to our place. No one but Anna and I have been in here since you left." The two women stared at me expectantly.

It was a mistake, giving me time to think and all. "If no one has been in here but the two of you," I said, sitting up, "then one of you two already found the money. What type of game are you two playing at?"

This time Mrs. Campbell was the one to stutter. Her poker face shattered as she struggled to respond. Anna Johnson turned and gave her a less than friendly stare and said only "Smooth." Cindy turned, cheeks glowing red from apparent embarrassment, and walked back to the living area.

"Well so much for our little game. But you being intelligent should hardly be a deterrent." she said giving my body such an open and overt appraisal that I grew self-conscious. Of course I had checked her out, she was hot, but not so hot that I couldn't tell she was ten years older than my mother. "It would take more than that for me to give up on my plans this evening. I guess I will try honesty."

I moved to stand, but she lifted her enticingly long and deeply tanned leg and placed her bare foot on my abs, pushing me back down into my back. "Now don't get up on my account young man." she commanded. Oddly, I obeyed, staying when she removed her leg.

I am normally not that bright.

"Here is the truth. Benny and the girls came over to my place this morning. I got to meet them. Dan asked about you. Benny mentioned how you had stayed up late, probably trying to get over your ex."

"Once Dan and Benny went outside, however, Jenny grilled Nicole in front of me about what happened last night. I heard all about what a sweetheart you were, and how you respected her wishes even though she secretly wished that you wouldn't. The girls told me how handsome you were, and all about the break up. You don't know this from me, but Jenny called your ex and asked for more details about the break up last week. She said she wanted to hook you up with a friend of hers, and asked for your ex's honest opinion about you."

I hadn't had any idea that Jenny had ever spoken to my ex. Anna gave me a moment to soak in what she had said. Once I was lost in thought I tried again to sit up, but she lifted the other incredibly sexy leg of hers and pressed her other foot to my chest, pushing me back down onto my back. It was impossible to hide my erection in my trunks. I am not the smartest man in the world, but I had a strong intuition that I didn't need to.

Anna continued, leaving her bare foot on my chest. "Your ex gave you a glowing review. She said you were the sweetest, most masculine boyfriend she had ever had. That your cock was huge and always ready when she needs it, that you were talented with it as well as with your tongue, and that you could go for hours. She said whoever you had your break up sex with was in for a treat."

Then why cheat on me, I wanted to ask. Anna saw my unasked question and replied with a shrug. "Apparently the girl just fell out of love. It happens."

Anna took her foot off of my chest and stood with her legs straddling my hips. This let me see into the hall, and I realized Cindy had returned to the doorway, watching us silently.

Anna waited until my eyes crawled back up her sexy body before she started up again. "So then we came here. I had been looking forward to meeting you after the fascinating description the girls had given you.