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.
