Author’s Note: This story was written by a friend named Randy Rob. He sent it to me on Saturday, September 10, 2016 and asked me to post it for him.
Sis and I go pretty far back; at least all the way to last Tuesday. I can’t remember what day today is, so you’ll have to do the math. Yesterday, as we spoke of cabbages and kings, surprise, surprise, our conversation turned to sex. Or more precisely, the lack of it in each of our lives currently. Her husband traveled, so she was left alone a lot. Like this whole month alone. I had no ‘significant other’ at the time, so I was pretty much living hand-to-cock, so to speak.
Did I mention how pretty Sis is/was? Or that she had a flawless body? I won’t go into bra size and all of that; just know that she is/was smoking fucking hot. Sizzling. Had legs that went clear up to her cunt. A leg man’s dream girl.
I ask her if she ever had or ever would cheat on her man. She pronounced that her cunt was his and his alone and that was that. Letting any other man win her treasure was off the table. Not in the cards. Ain’t gonna happen. I admired her faithfulness and told her so, and then I guess I kinda went mental because I heard my mouth say, “Well, you do have a couple of more holes that, personally, I would love to fuck. Are they off-limits too? You could take it in that beautiful ass of yours or you could use that intriguing mouth to suck cock, both of which would keep your cunt faithful and untouched.”
Damn. There it was. Out there. I’d said what I was thinking and there was no taking it back. All I could do is brace myself for the slap that I knew was coming. Only, it didn’t come! Instead, after about a year long period of silence, she dropped a bombshell that nearly exploded my brain.
“You know”, she said, “that’s an intriguing idea and I must confess, I have thought about it before. I actually would like to experience being fucked in my ass. I heard that it hurts at first, so I’m a little hesitant about that part of it. But yes. Yes, I do. I do want to try it at least once in my life, and I think the perfect time to be ass fucked is ... today. Here at my house. I want my virgin butt hole sensibly fucked but as gently as possible to see if I like it, and I want you to be the one to fuck me. What do we do? Do you just walk up behind me and stick it in, or what? You’ll do it, won’t you? Be my hero? Take my anal cherry and still treat me like a lady? How do we start?”
“Well, I guess if you’re serious about losing your ass cherry, I’m you man. I do have some experience at this and I’m certain we can do this with a very limited amount of pain. If I do my part right, you might even have a totally painless experience,” I told her. “The key to a successful anal experience is preparation. And the most important thing to do to prepare for your ass to be fucked, is to be given an enema. If you find that me seeing you naked and giving you an enema is too embarrassing, then we need go no further. Your bowels need to be empty and clean. An enema is the first and most important step in your having a painless experience. Do we keep going?”
Instead of answering me, she stripped naked and reached for my hand. “Come on. I’ll show you to the bathroom and I’ll get my enema bag out of the cabinet where I keep it. How do you want me?” I told her the best place to be is in the bathtub in case she can’t hold her water. She stepped into the tub and I directed her to put the side of her face on the bottom of the tub and to have her ass as far up in the air as she could get it. I had her spread her knees till they touched the sides of the tub. This had nothing to do with her enema, it was just sexy to look at. Gave me a lovely view of her pussy. God, that woman had a fine looking cunt.
I filled the enema bag with a mild soap and water solution and hung the bag from the curtain rod. I slowly inserted the tip end of the hose in her ass hole. Then I took it out and put it back in several times. Again, not really a part of giving her an enema, but sexy as all fuck.
I adjusted the clip valve on the hose to let her enema water slowly flow into her colon. I didn’t want her to feel any of the discomfort deep in her belly that would happen if I filled her bowels too fast. I wanted this to be a rather pleasant experience for her. I reached between her legs and gently tugged on her labia to distract her and, yes, to arouse her sexually if I could. She must have liked my playing with her cunt lips while her belly filled owing to the way she tried to hump my hand. The sound of her sexy moaning was a delight. God that woman was turning me on.
She obviously was into this whole scene because her pussy drooled a continual flow of its delicious thin syrup. It was literally flowing down the insides of both of her thighs. She knew good and well the reason why she’s getting an enema, and the whole idea of cleaning her out to be fucked in her back door obviously appealed to her wild side. Mine too. She doesn’t know I intend to give her a surprise deep tongue fucking before she feels my long hard cock slide past her sphincter. There won’t be any pain. Her butt sealing muscle will still be relaxed and open after my tongue’s deep probing. Just thinking about ass fucking her, my mouth was almost drooling as much as her cunt was. Your big sister is one smoking hot lady. Who knew she has such a wild side ... The bag emptied its cleansing solution, so I slowly removed the nozzle from Sis’s butt hole and washed it and the water bag with hot water while she struggled with art of ‘holding her water’. Too bad I didn’t have a butt plug to put in her to hold her water in for her. Sis held her water like a champ while she sat up in the tub for the prescribed fifteen minutes’ wait before evacuating her bowels. Next, there were two ‘rinses’ using clear water to insure there was no soap residue in her.
However, as we waited for that fifteen-minute lull to pass, we just talked about life and the pursuit of happiness. During our chat, I brought up the subject of you, her ‘little’ brother. I told her, “From talking to your Bro, I know that he would like very much to watch you being bent over and butt fucked, and I was wondering how you would feel about that. I certainly don’t object. As a matter of fact, I find the idea sexually very exciting. The question is, how do you feel about him watching? Would his presence freak you out? Turn you on? Turn you off? We’ll drop the idea fast if you disapprove of him ‘voyeuring’. He only wants to watch if you find the idea appealing and maybe even outright sexy. What say you, Sis?”
I already knew what her answer was likely to be even before she said a word. I had seen the flash of excitement sparkle in her eyes, and the little shudder her body made. Oh, she was interested in having him watch, all right. She was visibly excited about the prospect. I knew, even though she played coy, appearing to be thinking the situation over. He and she were very close, but nothing overtly sexual had ever happened between them before. It could happen now if I had my way.