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Miss Madeline

When I was in high school in the late sixties, there were two things that I craved the most. The first was to have sex with the most beautiful woman in the world. Her name? Madeline. She also happened to be one of my teachers. The second, was to see Madeline in her long leg panty girdle. There was something about a nice round, firm ass packed into a girdle that turned me on to no end. Even seeing just the cuffs of hers peaking out from beneath her skirt aroused me. Now Madeline was a full figured lady, not fat mind you. Imagine the figure of a cheerleader with a little more of everything and all of it perfectly rounded. I later found out that there was a third thing that I craved and Madeline showed me the way.

It all started one day in school when she asked me to carry some books for her down to her car so she could take them home. After placing them on the back seat, she then asked if I had enough time to go with her to her house to carry them inside. I said sure, I had plenty of time as I currently wasn't on a team and had nothing to do after school. After arriving at her house, I followed her in and upstairs to her bedroom where she said she wanted them. After setting the books down on a table I asked if there was anything else. Madeline said there was one other thing I could help her with and said to come into the bathroom. I followed her in and she reached behind the door and produced an enema bag and hose. Handing me the hose she said hold this while she turned on the water in the sink and tested it's temperature. After adjusting the hot water she started to fill the bag. It was the hot water bottle type and a dark red in color. I could hear the funny sounds it made as the water was splashing into it. I stood there in amazement as she kept adjusting the bag and lifting it to make sure that it was absolutely full of water and contained no air. When water started to run out the top, Madeline said to give her the hose which she promptly turned the end into the top of the bag. I guess I was still in a state of shock and wondering what this beautiful woman was going to do. However, watching her with this full bag in her hand, I could feel the pressure of my cock against my pants and started imagining all sorts of things. As long as I wasn't going to be the recipient of the enema, I was game for anything she had in mind.

Now Madeline walked out to the bedroom and hung the bag on a small hook that was attached to the top of one of the bed's posts. She then turned around to me and said to take off my clothes. I hesitated and informed her that the bag wasn't for me, no way. Madeline smiled and said that no, it was for her and I was going to help her take it. My cock pulsed again and I realized the third thing that I craved. I not only wanted this woman and her lovely ass, I now knew I wanted to give her an enema. Madeline then started to remove her clothes beginning with her blouse that produced the most amazing pair of tits I'd ever seen in a smooth, white bra that I estimated sized out to a 38C. She then unzipped the back of her skirt and dropped it along with her slip to the floor. Standing in front of me was the woman I had longed for in her bra and the long leg panty girdle that had enticed me over the years. Madeline then turned around and backed up to me till her ass was up against my pants and it was obvious to her that I was excited. Then she said to get out of my clothes which took 3 seconds. Pushing her girdled butt up against my now horizontal cock sent feelings through my whole body that I'd never felt before. She asked if that felt good and did I like to feel my member pushing against her rearend. I told her that it was the best feeling I'd ever imagined and she said it was the way she really enjoyed sex. Madeline then went into how she got started with anal sex, first reading a book that described it and how she got her husband to try it with her although he didn't care for it all the while she craved a cock in her ass. I guess it's like anything that you really enjoy---you can't get enough of it.

Now Madeline stepped away and removed her bra revealing those beautiful tits, what a sight. Then she slowly pulled down her girdle watching me for a reaction which by now was wide eyed. She then moved towards the bed and bent over it slightly. I was now to take the nozzle of the hose and gently insert it in her ass with a slight pressure and to turn it a little. Standing there with that hose in hand and staring at that beautiful butt I could breathe but followed my orders. Her asshole resisted a little but soon received the nozzle. I then asked if I was to turn it on but she said not yet and to get up on the bed in front of her on my knees and sitting on the backs of my legs. My dick was now directly in front of her face as she grabbed it with one hand and slid her warm mouth over it. I'd had blowjobs from schoolgirls before and some of them were pretty good but none could compare with this woman's talented tongue and firm lips. Watching her head move up and down was enough to make me blow my wad in no time flat filling her mouth with hot stuff which she swallowed just as fast. Madeline continued to move her experienced head up and down without slowing up. My dick never went limp and soon I could feel the excitement building again. Suddenly she lifted her mouth away from me and said that for a man to enter a woman's ass his cock has to be as hard as a baseball bat. I was to now start the enema and to lean forward and turn it on. Madeline now resumed sucking my dick as I bent and leaned forward to get the water flowing. As I moved, my cock slid deeper down her throat till her nose touched my belly. I was now all the way in without so much as a gag or a gurgle from her. When I unpinched the clasp and it made a click, I heard her make a little whimpering sound. After a few seconds of the warm water rushing into her ass, she made a moaning sound now. I asked if she was alright and she just nodded without removing her mouth from it's task. This woman whom I had long admired and had just taken what I thought was my biggest wad ever was now making me harder than I could imagine. Watching the bag slowly empty and knowing that she was taking all of it just made me even more anxious to get around behind her and just pound her butt. By now the bag was about half empty and Madeline was starting to make whimpering sounds indicating that she was beginning to reach her limit. She lifted her head and said to stop the flow but I quickly pulled her mouth back down on me and told her that she wasn't finished yet. She started in with the whimpering again and reached around behind her ass to try and pinch off the hose. I grabbed her arm and kept it away then held both of them so she couldn't turn off the water. I wanted to make sure that that great looking ass was going to take the whole bag and nothing was going to stop me now. Holding both of her wrists with one hand and her head down on me with the other, Madeline continued with the whimpering sounds which turned me on to no end. I was determined to get the whole bag into her. Now that the bag was emptying the last of it's load into her gorgeous ass, her moans became louder. Finally it flattened out showing not a drop of water left in it but she continued making the moaning and whimpering sounds. I told her that the bag was now empty and that I was going to pinch off the clasp and remove the hose. She quickly lifted her head and said not to take it out. I was now a little confused as I thought that she had had enough of this and wanted to get as far away from it as she could so I asked her what she wanted me to do now. To my surprise, Madeline said that she had taken the bag rather easily and her sounds had just helped me to get as hard as I could get for the back door action that was coming up soon. She then told me to remove the hose from the bag without taking the nozzle out of her ass and to go fill it up again only this time with warmer water. I questioned her about how much to put in and she said to fill it up the way I'd seen her fill it the first time and to make sure the water was very warm, almost hot. The water was practically steaming as it poured in and topped off. Walking back into the bedroom I could see that Madeline was still in the same position as I had left her. Before I could reconnect the bag and hose she said to let her feel the temperature and she dipped one finger in. She said that it was perfect and to hook it back up. After I hung the bag up on the hook, Madeline told me to go ahead and start the water flowing and to get back on the bed. My cock at this point was rock hard and standing straight out. Back in position now she began sucking on me and taking her second bag. I was truely amazed at this woman who loved to suck a cock and do it so well and at the same time relish having an enema of not one bag but two, one on top of the other. All the time the second bag emptied into her she made those moans which turned me on still more. When it was about halfway empty she paused from sucking and said that one and a half bags was the most she'd ever had and that she was full and couldn't take one more drop. Well, that was a challenge to me and I didn't turn off the clasp. Madeline said that she wasn't kidding and that she couldn't take two whole bags but I was determined to finish the job by again holding her wrists with one hand and her head with the other. Now the whimpering started in again only this time I knew it was real. She started bucking her hips and moving them from side to side trying to get the nozzle to fall out of her ass but luck was with me. I told her that all this commotion wasn't doing her any good as the enema was still going into her. When the bag finally went flat indicating it's emptiness, I quickly pinched off the clasp, pulled my cock from her mouth and got around behind her. I was determined to go all the way with her before she could change her mind. I pulled the nozzle out with one hand and guided my swollen dick up to her tight asshole with the other. As I touched her little opening Madeline said that she couldn't possibly take me in after having all that water in there. I told her that she didn't know she could take two whole bags either and now I would show her she could also take my cock, all 10 inches of it. Madeline was rather receptive as my member, still wet with her saliva, popped it's head in and she just let out the biggest moan I'd heard all afternoon. Knowing that I'd gotten what I wanted all these years, my cock up her ass, I was very excited and about to let go with a load. Not knowing if I'd ever be in this position again after the way I had treated her, I quickly slid the rest of it in. Immediately after reaching bottom, I began with the stroking and she started in with the whimpering. I asked her how did it feel and to my surprise Madeline said that it was the best cock she'd ever had, in any hole. This made me want to pick up the pace as I fucked her ass with long and fast strokes. When I came, it must have been a quart's worth. I'd never had an orgasm like that before or since. As I pulled out of her, Madeline turned and smiled. She told me that for the two times I came, she had come four times, more than ever before. We continued our little sessions for several months after but none were as good as the first. Madeline eventually moved away from the area and I've never seen her again. However to this day I'll bet she's still going at it and there's some lucky guy out there somewhere at the "end" of it. Thanks for the memories Maddie, David.