Taking Sis's Cherry (and More)


It took all of my power to rush her out of the place and, when we exited the building, she collapsed against the wall in hysterics.

"If you posted your phone number on the wall by that gold bar your phone would ring off the hook for a week," she said through her tears of laughter. had to laugh along with her for it sure did create some disturbance in the quiet sedate museum.

We saw a few more things and then went back to the motel where we actually went in for a swim. There were a number of other bathers nearby and Andy couldn't let it be but just had to say, "These waters are great for childless couples. Some women had even conceived while swimming here." I could have choked her.

I ushered her out of the pool and back to the room where we both collapsed on the bed with laughter. I was upset with her crap but had to agree it was funnier than hell.

"Well, Andy, I got the tube of KY jelly. Do you still want to try my cock up your ass?"

Oh, yes. But you have to promise to go very easy. If it is hurting me too much you have to stop as soon as I tell you to.

"Of course, Sis. The last thing I want to do is to hurt you."

I lubed up the fingers on one hand and then had her lay on her stomach as I smeared some more all around her puckered asshole. I slowly inserted first one and then two fingers part way in her ass. While I was doing that I had my lips locked on hers and carefully kept up the pressure and soon had both fingers buried. "Andy, I am going to take these two fingers out and replace them with three."

"Whatever you think is best, Dave. It burns a little but doesn't feel bad at all right now."

I did the same thing with three as I had with two and soon had all three all the way in. I sort of did a little finger fucking of her ass with them and she didn't respond negatively so I took them out saying, "Honey, I am going to lube up my cock and try it."

The KY was smeared all over my cock with the majority on the head and the first few inches of my shaft. I figured if we got that far the rest would be a snap.

"Andy, get up on your hands and knees and we'll do it that way. You will keep your chest and head on the bed with just your ass in the air," I instructed.

The head of my cock, as I looked down at it against her puckered asshole, looked much too big for her tiny orifice to take in but we would try.

I pushed a little and her asshole simply retreated from the pressure. I grabbed her hips and pulled back on them as I gave another push. This time the head popped in with her sphincter ring clamped around it.

"Of God, Davie. I can't take any more than that," she whimpered.

"Andy, I only have the head of it in you. Nothing more."

"Oh, God. I'll try a little more but go slow and easy."

I did just that. I held her hips and pulled her back as I pushed a little more forward and soon had about four inches up her sweet little ass. "Andy, how are you doing?"

There wasn't an answer.

"Andy, are you okay?"

I didn't hear a word but could feel her body wracked with her sobs. I pulled out instantly and moved around to kiss and hold her.

"Oh, Dave, I tried so hard. I'm sorry I couldn't do more for you."

"Andy, it was you who wanted to do this. Not me. I am happier than hell you at least tried it for both of us but let's forget about ever trying it again. Okay?"

" Okay, King of the Atocha," she yelled and I just about smacked her.

I used my mouth on her for most of the rest of the night and she had one of her biggest orgasms of the trip.

The next morning we had plans to drive out to some of the neighboring islands to take a look at them but when we went out for the car we were greeted with a big empty space where I had parked it a few days earlier. We hadn't used it the day before so we hadn't seen it for two days. The damn thing was stolen!

Well, we went though all the usual shit with the local police but since we hadn't seen the car for a few days they didn't have much hope of finding it on Key West. If it was off the Keys, Lord only knew how far the thieves had gotten with it. Big deal, that's what insurance is for ...isn't it?

The police asked if we could stay around for at least another day and we agreed. At the same time I made flight arrangements out of Key West back north. Our planned stopover at Disney World on the way home was going to be trashed and I could have rented a car in the Keys for the return trip but I thought 'the hell with it, let's get home and deal with the problem on familiar grounds.' That still left us with another day in Key West and all of the fun to be had there.

"Dave, here is what I would like to do if you would like to listen," Andy volunteered.

"Shoot, sweet thing"

"It is near noon and I think we ought to go back to that restaurant where we had the great lobster dinner and see if we can get a nice lobster salad for our lunch and accompany it with a couple of glasses of a nice white wine. After lunch, there is a marvelous huge sailing vessel that takes tourists out to cruise the harbor. I think we ought to enjoy that. That should get us back here around four at which time we ought to retire to this lovely king sized bed where you will get your wonderful cock in gear and fuck my tight little pussy. Does that sound like a workable plan?"

"Have you called for a cab to the restaurant?" I replied not entirely jokingly.

Lunch was fine, the cruise was very interesting and then we got back to the motel!

"Andy, there is one position we haven't tried and that is with you riding my cock on top of me. Let me get stripped and get a condom on and you can work your magic on my cock and get it ready for you".

She rode my cock as if it were a thorobred horse. She used her knees on the mattress to rise and fall with each of my thrusts except when she was near having an orgasm she went a little wild. "Davie, fuck me. Fuck me hard."

Hearing that I drove my cock as hard and as deep as I could but there was a problem. I had forgotten to put on a condom. Shit, piss, fuck. (Or SPF, as I would normally say). I had to pull out and begin to jack off at the last moment. No problem ... she moved her mouth down to my cock and sucked it for all it was worth. This gal can suck some mean cock and is going to make some lucky fellow very happy.

I used my mouth on her to give her the pleasure she so richly deserved and we both fell into a deep nap only to awake around nine PM. There was a lovely restaurant almost next door to the Best Western and we enjoyed a wonderful prime rib dinner with a couple of bottles of Merlot.

Key West really doesn't have a beach per se but there is a waterfront walk across the street from the motel and the restaurant and we walked that for another hour or so. When we got back we had a nightcap at the Tiki bar where our stolen car was the topic of conversation among all of those at the bar. They couldn't get over our lack of concern about the problem. I tried to explain that insurance covers shit like this and we weren't going to let it spoil our trip. Everyone wanted to buy us a drink and I guess we each had a few more than we should have for when we got back to the room we collapsed into the bed and guess what? We missed the wake up call for the morning flight out of Key West. Aw, what a shame ... another day of great food and superb sex.

We had a little bit of a problem with our hotel reservations since we were supposed to leave that day until I threatened to call their worldwide reservations number and explain how our personal automobile was stolen right under their security agent's nose. All of a sudden the problem went away.

We did make the flight the next morning and arrived home safe and sound. The insurance company was going to wait a bit before they reimbursed me for the value of the car but they did agree to rent one for me while they were waiting. Andy and I had some serious discussions as to what was going to happen between us. They haven't been resolved yet but we are sure thinking about it. In the meantime we are fucking our eyes out.

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