Taking Sis’s Cherry (and More)

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Sibling Sex from St. Augustine to Key West

I have been ogling my younger sister, Andrea, for as long as I can remember. I’m Dave, twenty- eight and she has just turned nineteen; we share the house our family has lived in since our parents bought the place years before either of us were even thought of. They died in the crash of a commercial airliner during their annual tour of Europe a few years back and left us with the house, their two autos and a good chunk of cash.

Andy is a small gal, not more than five feet two, and can’t weigh more than a little over one hundred pounds. She is pretty enough but doesn’t have much of a figure to speak of. She must have been on a break when tits were handed out for hers aren’t any larger than tennis balls so it’s not her overwhelming good shape that makes her so attractive to me. She just has a way about her, a smile, a toss of the head while looking back over her shoulder at me, a smile that knocks me out and some facial expressions that have me wanting to ravish her sweet little body.

We have lived alone in this house together for over four years and neither of us have made any kind of move on the other but I damn sure have been tempted. Last night she got up from her chair to do something to the VCR, bending at the waist to do it. My mind flipped out at the sight of her tight little ass staring me in the face. It wasn’t more than a half dozen feet from me and I could just imagine holding her hips while I slipped my cock into her pussy from the rear. Whew, what a mental picture I was painting.

I came home a week ago and yelled, “I’m tired of this fucking snow. Who wants to go to Key West with me?”

Andy came roaring down the stairs from her room saying, “Well, if you can’t find anyone else to accompany your ugly ass, I guess I will.”

Winter was now upon us and both of us hate the cold weather it brings. Snow can make me want to curl up with a few good books and not get up until the first flowers of spring show themselves. We would move to a warmer climate except for the fact I have a great job and she wants to attend a college only a few miles from the house so we are more or less stuck where we are.

We both roared and I swatted her ass as she pranced past me.

“Andy, I’m really thinking of taking a month off and driving down. There are a few things to see along the way; neither of us has ever been to the Keys, and I think they would be a fun place to visit. No kidding, would you like to join me?”

“I’d love it, Bro. I am also tired of this damn cold weather and could use a change. Why do you want to drive, rather than fly into Miami and rent a car there for the drive out to Key West?”

“Well, as I said, there are a few things to see along the way and we couldn’t do that playing hopscotch with airplanes. We will have to go right past Charleston and everyone says the city with its harbor is a fun place to see. St. Augustine at the top of Florida is a city I have always wanted to visit and the hard packed sands of Daytona seems as if they would be fun to see. They are just a few of the things that would be interesting. We could return up through the center of Florida and stop off to take a peek at what Disney World has to offer. I don’t know, Andy, I just think that driving gives us more flexibility to explore.”

“Sold. Driving it will be.”

“It will be a solid week getting there and then I figured a week in the Keys and then a week getting home so a month will give us more than enough time.”

We got the house ready for our absence and loaded my car on a Sunday night. We were off and running first thing on Monday morning.

We hadn’t talked about our rooming situation on the trip so I thought we ought to get that out of the way first.

“Andy, as you are well aware, we each have our own rooms and baths at home and that will not be the case on the trip. I have no intention of paying for separate rooms in the middle of their high season so the best we can do is to get a room with two beds and then share a bath. Can you get along with that?”

Smart-ass Sis came back with, “Oh, hell, yes, if you get scared at night you can jump into my bed with me. I won’t let the boogie man get you.”

“Damnit, Andy, you know damn well what I’m talking about. There will be little or no privacy in our sleeping quarters. Now, will that present a problem for you or not?”

She slid over as close as she could get to me with the center arm rest blocking her from coming all the way over and in the most theatrical voice purred, ” I’m not sure I will be able to keep my hands off you but I’ll try.”

I laughed but responded with, “You know, you can be a big pain in the ass when you try. I asked you a simple straightforward question and you come up with your bullshit. I’ll take it that you are not objecting and let it go at that.”

We got into Charleston early afternoon and visiting the place turned out to be a great idea. We got a room in a motel chain with two queen size bursa escort beds and then toured the old city on one of the tram tours that run every hour or so. Southerners still seem to be living in the days of Gone with the Wind but that’s okay, we enjoyed the tour guide’s commentary. We got chatting with a couple of locals who gave us the name of a fantastic seafood restaurant that turned out to be a true gem; it was out of the way and one frequented by locals rather than the tourist crowd. We enjoyed a feast.

We finished off dinner with a couple of cognacs out on a deck the place had overhanging the water and it was great watching the small boats coming back from their day of fishing. Okay, the drinks were over and it was time to hit the sack. The moment is here; this will be the first test of our sleeping in the same room and sharing one bath.

As we were going through the lobby of the motel, she asked, “Who’s going first?”

“Well, knowing how much time you spend in your bathroom at home, I think I’ll go first or it will be breakfast before I get in to brush my teeth.”

I sleep in my skivvies so I don’t have a major get-ready-for-bed problem. All I had to do was strip, use the toilet and then brush my teeth and I was ready. I came out of the bathroom hung up my pants and dumped my dirty shirt in a laundry bag and got into bed.

“Your turn, sweet thing.”

She hardly took any time at all. She showered and I could hear the toilet flush and she must have brushed her teeth. The next thing I knew she was back out into the bedroom area….nude.

That had me stuttering big time. “Andy, what the hell are you doing? Get some clothes on.”

“Dave, I sleep this way every night. Get used to it,” as she pranced over to her bed.

Oh, my God. I can’t imagine that I’ll be able to get any sleep knowing she is over in the next bed bare ass naked. I’d love to fuck her but I damn sure am not going to rape her. Then I thought of all of the times we were in our own rooms at home without me knowing she was lying there naked just a very few feet away from me.

I wasn’t sure if she was just being a cock-teaser or not but she sure went into some poses that looked awfully tempting.

Sometime during the night I got up to use the toilet and with the light coming through the curtains could see she had kicked the covers off and was lying there on her side, nude and in a position just made for rear entry fucking. Her ass was aimed back at my bed and I could just picture myself sliding onto the bed behind her and slipping my cock in deep. Whew! We are either going to have to get involved with some serious sexual activity or this trip is going to be pure torture for me.

I awakened first and showered and dressed while she was still asleep. I finally yelled at her to get up and ready for the road and she did while rubbing her eyes and moaning about it still being in the middle of the night. Shit, it was eight AM.

We had an early breakfast and were on the road by nine-thirty. Our next stop was going to be St. Augustine and fortunately, it wasn’t going to be too long of a drive.

We arrived there in mid-afternoon. Andy spotted the signs for the Flagler Hotel and we were able to get a large suite with two queen size beds. There was no way I was going to share a king- size bed with her.

It is a quaint little town and the history of the place is fascinating. A walk through the old restored section and then over to the fort had us both enthralled with the sights and sounds of the place. We took a touristy trolley ride through the old city and enjoyed the guy’s commentary. Some of it sounded like so much bullshit but it had us laughing in any case.

Dinner was in a real tourist mecca. There was a restaurant that hung out over the water of the harbor and you could drop food to the fish swarming below. We were there before five so we were way ahead of the crowds. I called the waitress over and explained something to her.

“Honey, as you have probably guessed we are tourists and know nothing about this place. However because of it’s location I think that most of your clientele are tourists and will only be with you for the meal and you, the owner and the kitchen aren’t worried about repeat business from them.”

She looked at me and was nodding affirmatively to almost everything I said.

“Now, here is what I propose. We are each going to order a rather simple dish of shrimp scampi with a couple of sides. If our meal is memorable, I will tip you better than you have ever been tipped before. If it isn’t, I will leave you one dollar to remember me by. It’s your choice but if you make the one I hope you will, we will have a nice meal and you will be very happy. You can share a part of the tip with the cook if you think it will help insure we get the meal we are hoping for.”

“One great meal coming up,” She said with a huge smile. “The cook is my boyfriend and if he screws up your meal, he won’t be getting a nickel or anything else bursa escort bayan from me!” Great it was. The shrimp were cooked to perfection and there were so many they were falling out of the little scampi dish they were cooked in. The asparagus and onion ring sides were perfect. We had a couple of drinks to accompany the meal and all in all it was very nice.

I motioned to her for the check and she brought it over standing at the side of the table expectantly.

“Okay, honey. Let’s try this a different way. You tell me what you think would be a very nice tip.”

That had her stuttering and stammering. She was facing a big dilemma. She didn’t want to go too low in case I had a higher figure in mind but on the other hand she didn’t want to appear to be a glutton.

“Sir, I have never received a tip of twenty five percent in all the time I have worked here.”

“Then I guess I am safe in assuming you haven’t received one of forty percent either. And, it will be all cash so the boss won’t hit you up for his share of a credit card bite.”

Looking at Andy, she said, “God, forgive me Ma’am, but I have just fallen in love with your husband.” She was grinning from ear to ear as she took the money and left our table.

Andy just smiled and said, “You really are a nice guy, aren’t you? My husband. Mmmmm.”

“Nah, it’s just a bad rumor.”

We walked through that section of town, stopping off for drinks in a few places that seemed interesting. It was still early so we didn’t want to get back to the hotel too soon as we strolled like newlyweds … hand in hand, laughing at almost everything.

We had one more drink when we got back to the hotel and then went up to the room and were faced with the same problem … her sweet little bare ass just a few feet away from me.

The bathroom ritual was about the same as the one from the previous night. I went first and she followed me, returning to the bedroom bare ass naked.

Instead of getting into her bed she sat on the edge of mine, saying, “Dave, as soon as I heard you invite me on this trip I knew my long held dreams had come true. I have wanted to sleep with you for years but knew it would be a problem for me to break the ice. I was afraid of your reaction and what you would have thought of me. But, when I agreed to come on the trip, I knew that all bets were off and I was going to go on the make for you full time.”

“Why have you waited all of these years?” I asked.

“Well, I thought for a while I was way too young for you and then I would never have felt right about doing it in our parents’ house. It would have seemed to me to dishonor their memory.”

She was looking at the lower part of my bed and said, “Oooh, lookie here. Davie has a hard-on.”

Sure enough, my rod was harder than steel and making a tent out of the covers.

That was all it took. She whipped the covers back and slipped in beside me.

“Are you sure this is what you want, Andy?” I asked.

“Oh, yes, I’m more than sure,” as she lowered her hand down to my crotch. “In case you are wondering, Dave, I am only a part-way virgin.”

I laughed and asked, “How the hell can you be a part-way virgin?”

“Well, I was going out with this guy and he tried to get in my pants. He got a hard-on and when he went to put it in me his dick went soft and that was it. He only had it in me an inch or so when he stopped.”

“Well, that’s it. You are still whole and now more than ever we shouldn’t be doing anything like this. Save it for the guy you are going to marry.”

“Geez, will you get real and come into the world. You are talking about shit that used to go on fifty years ago. I want to get laid and you are the one I want to do it with.” As she was saying that, she had fingers wrapped around my rock hard shaft and was starting a slow up and down movement.

“Andy, it has been some time since I had any sex and you have me turned on so much I am going to have an orgasm before we even get started. How about if we just use our hands on each other until I do and then, after I recharge, we can get down to some real fucking?”

“Whatever you say, Bro. I am just a little ole gal who is at the mercy of big ole you,” she said in her pretty good imitation of a Southern Belle.

I let my hand drop to her crotch and used a couple of fingers to open the lips of her pussy wide. I couldn’t help but notice she was soaked as I let my fingers wander up to uncover her clit. That caused a deep gasp and she started to breathe a lot faster and toss her head from side to side. I leaned forward and took one of her hard nipples between my lips, and had my tongue flicking back and forth over it. She lowered a hand behind my neck and pulled me to her breast even harder.

“Dave, that feels awesome.”

I was holding her clit between two fingers and letting my other hand go up and down the sides of it and then letting it slide up and down the lips of her pussy. That was it. She exploded and let out escort bursa a small howl with the pressure release of her orgasm.

“Oh, Dave, you are wonderful.”

“Reach down and use your hand on me, honey.” I swung around a little bit to make it easier for her and she was soon jacking me off like she had done it a million times before. It took about two minutes of that and I was spraying my come all over her.

“Whew, that was something else again. Where the hell did you learn to do that if you are, as you call it, still a part-time virgin?” I asked.

“I think I’ve read ever sex book ever written and have at least a dozen videos at home showing every possible position. I wanted to be ready for you.”

We lay around just chatting for a while with her fingers roaming up and down my shaft. I guess she wanted to be the first to feel the signs of new life in it. It really didn’t take very long before the pulsing started deep at the base of my shaft and the heat and pressure rose up to the head of it. She was soon stroking it lightly when I told her to roll over onto her back.

Deep down I had some hope this situation would present itself but like an idiot, I completely forgot to get condoms. We would have to ride bareback and pull out at the last minute.

The head of my cock was soon positioned between the lips of her tight little pussy, getting ready to make its grand entrance. I leaned forward and then gave a little pressure and it opened her pussy lips just a little. I then reached down and held her hip and exerted more pressure and I slid in her about half way. Her gasps were loud and her breaths were coming a lot faster. I gave one more huge thrust and I was buried to the point where my balls were slapping against the cheeks of her ass and I could hear her crying,

“Dave, you are tearing me apart. Your cock is so big and my pussy is too small for you.”

“We’ll just go very slowly, honey. Your pussy will stretch to be able to take me okay and everything will be fine.”

I lay perfectly still for a few minutes with my cock buried and my hands cupping her breasts. Her nipples were as hard as my cock and, as I massaged them lightly, I could hear her purr and then felt her pushing her hips back at me hard. I started a slow thrusting, first pulling all the way out and then driving in to the hilt. Her pussy was so tight it was holding my cock tighter than her hand had earlier before we started to fuck.

“Oh, God, Dave. That feels terrific. Fuck me hard.”

That was all I needed to hear before I started some hard and deep thrusting into her tight pussy. I could feel her pulse rate through the shaft of my cock in her vaginal canal. It was racing full steam ahead.

As I was thrusting, she was throwing herself up to meet my every thrust. We were in perfect sync with her own thrusts coming at me so hard they were almost throwing me off. Uh, oh. I could feel the pressure start deep in my balls as my orgasm was building. I pulled out immediately and jacked off and shot my load all over her smooth white stomach. She still hadn’t had her own orgasm yet and I slid down and placed my face where my cock had been and then began to use my tongue on her clit. It didn’t take much of that before she was bucking like a bronco and holding the back of my head with her two hands.

“Yes, Dave, YES. Oh, dear God, Yes!”

We lay intertwined in each other’s arms and legs for what seemed like an eternity before I rolled off and made my way into the bathroom. I took a leak and she was right behind me wanting her place on the stool. I gave it to her and went over to the sink to brush my teeth again.

“Well, Sis. You are no longer a part-time virgin. How does that make you feel?”

“Just like a woman,” she answered somewhat confidently as we scrambled back into the bed.

Some new thoughts came rolling over me. It wasn’t much more than a day ago and I was worried about how the two of us were going to get along sharing a room and a single bath and here we were just coming down from the first fuck of her life. God, I know it was wrong but I damn sure couldn’t stop it.

“Dave, I read about a guy using his mouth on the girl but never realized just how wonderful that would feel. My clit is very sensitive and your tongue touched every spot on it that would arouse me. The feeling was indescribable.” As she was saying this, she nestled her face close into my shoulder and draped her leg across my midsection.

I awoke a half dozen hours later and neither of us had moved one inch in all of that time. I slipped out from under her and let her fall face down on the bed with my cock starting to rise as I looked at her naked body alongside of me. I rolled on top of her and let the head of my cock slip between the luscious cheeks of her ass and into her pussy from the rear. One long thrust and I was buried and that awakened her in a hurry.

“Wow, what an alarm clock,” she cooed.

I was holding myself off her while resting my body weight on one forearm and used my other hand to reach down and pull her hips up to me. For some reason I was thrusting harder than I did the night before and as far as I could remember harder than I had with any other woman.

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