Author: Anal Al

Chad wandered into WalMart looking for a video for the evening. He found a semi- recent James Bond movie, although having already seen it once at the theaters decided to purchase it anyway. After getting a few other items he proceeded to the checkout line. Upon arrival at the checkout lanes a very pretty but also very young Hispanic girl was standing by her register trying to gather customers. She hurried behind her register and he placed his goods on the conveyer belt. Noticing her name tag it said "Esmerelda" and she had a ‘trainee' tag below it. She had a very slender figure and Chad figured she couldn't be more than 18. Certainly not old enough for his 40 years but still he wished. She had a pretty smile and a very large mouth. Chad remembered reading something about girls with a large mouth also had a large anus and he daydreamed of taking her. She couldn't have been more than 100 pounds and was very skinny.

"That'll be 45.66 sir." She said politely and smiled at him. Had she noticed his admiring glances, well stares, at her? Chad quietly pulled out some fantastic plastic and slid it through the reader and pressed the credit button.

"Thank you sir." She said and smiled again. No one else was in line. Should he risk a casual comment? He thought about it and twisted within himself. Wasn't a chance in hell that he could get such a young and pretty girl for a date was there? Even if she said yes how would he treat her? He was, after all 40 years old and such a young girl was bound to be trouble.

"Thank you Esmerelda." Chad said, having long ago learned that service people like waitresses and checkers lite up if you noticed their name. It set them apart from the rest of the crowd. Actually taking the time to know someone's name meant that you noticed the effort they put into servicing you. Having practiced this for years at restaurants he was seldom disappointed in the service and certainly had had his share of waitress girlfriends. She returned the gesture with a very wide smile and looked into his eyes. They locked eyes for a few moments.

"You are certainly a very pretty girl Esmerelda. I wish I was younger." He said and picked up his bag.

"Thank you." She said and handed him the receipt. Then she added, "And thank you for telling me I'm pretty."

"You're welcome. Your boyfriend should tell you everyday."

"I don't have one."

"That is too bad. I'm sure you'll have no trouble finding one. A girl as pretty as you could have her choice."

"Not me." She said and broke eye contact with him and looked down. "No one wants a cripple." And she held up her leg. Chad hadn't noticed it but the girl was an amputee. Her right leg was prosthetic. Although she had on the regulation pants he could see the bulges of the intersection between her stump and the leg. And the leg did not bend at the knee as a real leg would have.

"As I said, too bad I'm not younger. I would love to be your boyfriend. It doesn't bother me." He nodded towards her leg.

"Really?" she asked surprised.

"Really."

She looked contemplative for a moment then said, "I get off at 9."

Still no one was in her checkout line. "Don't you think I'm too old for you?"

"No."

"What will your parents think?"

"They're dead."

"I'm sorry." Chad said, sensing a very lonely young girl. "Well if you really think you want to go out with me I can be back at 9 and we can go somewhere and talk."

"Thank you." She said with sincerity.

"Where should I meet you?"

"Can you pick me up here?"

"Sure. I'll be waiting for you in the snack bar."

"Ok." She chirped happily.

"Bye for now." Chad said and walked away.

"Bye."

At 8:45 he returned and waited in the snack bar. At 9:15 Esmerelda appeared and sat at the table with him. "Hi."

"Hello sweet Esmerelda. My name is Chad."

"Hi Chad. I've been thinking. I guess you are surprised that such a young girl would be interested in you. I think you are a very nice looking man who really knows how to be tender and kind to a woman."

"I'm 40 years old, bald and a Gringo."

She laughed a little. "I don't get many offers." She said and thumped her leg.

"That is sad. You are such a wonderful girl."

They went on for nearly an hour talking and getting to know the basics of each other. Her parents had been killed in a car crash and she lived alone. She was 19 years old and barely making ends meet. She had several boyfriends, nothing long term, and wasn't a virgin. However she admitted that she still hadn't had too many men since most Hispanic guys weren't interested in cripples. From what Chad could tell she also seemed to be considered damaged merchandise since she had had an abortion when she was 16, before the accident that killed her parents and siblings and left her minus a leg.

They eventually agreed to go to Chad's place that was less than 5 miles away. As Chad predicted having such a young girl in the sack was a dream come true. Esmerelda could suck him long and hard and she adored his balls. The next day she went to her apartment and changed and then back to work. Saturday night was a repeat of Friday night and Chad and his new girlfriend spent the whole day Sunday together. Her leg was amputated just below the knee so taking her doggie style wasn't a problem.

After several months of dating Esmerelda moved in with Chad and let her lease on her apartment go since it was time to renew anyway. Chad's place was closer to Wal-Mart anyway. Chad & Esmerelda's relationship flourished. After showing her the pleasures of oral sex she happily shaved her small delicious twat. It itched at first and eventually she got used to it. Chad would eat her for hours. Savoring in her now 20 year old pussy he would exhaust both himself and her with multiple oral orgasms.

For Chad's 41st birthday she started seeing a electrologist and had her pussy hair completely removed. Chad was delighted, smooth pussy all the time.

As they began to get very comfortable with each other Esmerelda broached the subject of children. Her abortion had been botched and she couldn't have any more. Yet another reason why she wasn't a sought after young woman. Chad was delighted since he had had a vasectomy years earlier and had 3 boys by his first wife. Chad's second wife had tired of him when she finally figured out that he wasn't going to have the vasectomy reversed. Esmerelda was so relieved that he wanted her and didn't care, nay, didn't want children. She happily enjoyed his three sons even if they weren't but 5 years younger than her.

After 11 months of courtship Esmerelda broached the subject of marriage. Since she was already moved in with him it was merely a formality. Chad didn't mind but he had one condition – that she accept him anally. He carefully explained to her that his two previous wives had never, ever allowed him to enter them anally. This was his goal in life.

Esmerelda thought it over long and hard. She was afraid that it would hurt and had always heard a lot of rumors that it caused cancer, that it was painful that she would never shit normally again. She shared her concerns with Chad and he carefully explained each of them in very scientific terms. He agreed that he would happily and eagerly marry her if she would share herself anally with him. Since she shared everything else with him she finally decided that she would tell him of her plan.

"Chad, I want to try it up the butt but I am very, very scared. I've thought about it and decided that if I were very, very drunk that it might be easier. I thought about if I were drugged but decided that I didn't want that since I wouldn't be able to tell you to stop if it hurt."

"If you were drugged it wouldn't hurt. However, it would be like making love to a corpse and I'm not sure I'm into that. However I do have a solution for you."

"What?" she asked.

"Well, you know how you let me give you an enema when you have overeaten and you feel bloated?"

"Yes."

"Well, I could give you a little alcohol that way and you wouldn't mind it. I know you don't like to drink but this is different. Alcohol is absorbed very quickly when it is given in an enema. It burns a little but if you give it a little and the more and then more, stopping each time until the burning passes it works. Also using something that is not acidic in pH helps. Captain Morgan's spiced rum, believe it or not, is an excellent way to get drunk with an enema and have a really good time."

"I don't know."

"You don't mind the full bagfulls of warm, soapy enemas that I give you now. In fact I think you actually look for an excuse to ask me to give you one. You know I like seeing your butt and you certainly enjoy the orgasm plenty when you have a full bag flowing into you at the same time that I eat you. I know you don't really want to admit it but you do enjoy it. It is ok to admit your sexuality. Remember all of the wonderful things I have taught you. I know that you trust me and that I would never do anything to break that trust so please think about it. I could give you an alcohol enema and you would be very relaxed. Then I could put in some butt plugs. Remember the red tail butt plug you found one day? Remember that I have two sizes and you have already said that the small one doesn't hurt. After an alcohol enema for 20 minutes the large one wouldn't hurt. I would stop then and there if you told me to."

Esmerelda thought it over carefully. True enough that she enjoyed the soapy enemas. Even if they did burn a bit she like the full feeling she got while her love ate her bare pussy. Then the exhilarating experience of letting it all out! Chad had never allowed her to get hurt yet. Even though some of his ideas seemed pretty strange at the time. The clips on her nipples had hurt plenty but she had to admit that the orgasm was much stronger afterwards. Now she actually looked forward to the nipple clamps. And the strong soapy enemas really did hurt but, boy, did she feel good afterwards.

"Ok, I'll let you put some alcohol in an enema but NO anal sex. I want to try it first and then see how getting drunk is."

"Of course my love. Tomorrow morning is Sunday and you don't have to work. You said you were full from the dinner tonight and you did eat 3 fajitas instead of your usual 2. If I give you a half a bag of plain water and you get some of the shit out then the next one I'll put in some alcohol. We'll get you a little this time and in a few days we'll try some more. In fact I'll say that you need to try the alcohol at least three times before you decide that it is worth doing."

"You're just being patient because you want my butt!"

"NO my dear, I want all of you. However you butt does interest me!"

After an hour of watching TV she announced she was ready for her enema. Chad went to the bathroom and warmed the water. He carefully put in about a teaspoon of the peppermint castille soap that Esmerelda loved so much. After her 2 quart enema she was left to let it out by herself. Chad let her rest for nearly an hour before announcing that it was time for her to have some real fun. He mixed in about 1/3 of a fifth bottle of Captain Morgan's spiced rum. She appresenhesively lay down on the towel on the floor and awaited her fate. Chad lubricated her anus and inserted the changeable nozzle tip into her that she liked. He allowed a few seconds of water to flow and then shut it off and watched her face. Her wide eyes told him that she felt the effects. After two minutes he squirted her again, more this time. Then he allowed over half the bag to flow on the third squirt. Esmerelda squirmed a bit but said she was ok. He kissed her deeply and told her how good she was doing.

Then the remainder of the bag in one long flow. She started panting in short breathes as she had the full two quarts into her now. She always did this at two quarts and so didn't act surprised at the fullness. However after a few minutes she relaxed and smiled at him. "This isn't too bad. Certainly not as bad as I thought it would be. Actually, I feel kinda good."

"I'm glad you are enjoying it my love. Now easy while I remove the tip." Chad said and eased the tip out of Esmerelda's anus while she struggled to hold it all in.

"Now if you can manage to hold that for ten minutes you will begin to feel sort of weird. A good weird."

"I already do love." She said and reached for his crotch. Chad obliged by removing his clothes. Esmerelda gave him a first class blowjob while holding the two quarts of enema inside.

"I feel good she announced as she slurped the last of his jizz."

"Good. You've been holding it for nearly thirty minutes now. You should be at the full effect."

"I feel sort of sleepy. It isn't bad. I know that I'm full but it is enjoyable."

"Good, I'm glad you like it."

"I do my love but I have to pee!"

"Go ahead and pee, but if you don't allow any out of your ass then you will continue to enjoy the effects. Don't worry, I'll take care of you." He said.

Esmerelda peed and then got off the toilet clenching her asscheeks together. "Oh Chad, this does feel good!"

"Now get ready because I'm going to give you a soapy bagfull to rinse that out. Then we'll have a plain water rinse to take care of the soap."

"Ok," she said, in a delirious state.

Chad gave Esmerelda several more alcohol enemas during the next few weeks and got her up to holding two quarts of alcohol laden enema in while wearing a small butt plug. Then he worked up to the medium sized butt plug which was 1 ¼' inches in diameter, the same size as his dick. After three weeks of this he showed her the diameter of the butt plug while his dick was hard. She readily agreed that she thought she should be able to take him.

On the destined night he gave her a two quart bag enema with nearly a half a bottle of rum. He let her soak for an hour with that inside. Then after she had let it out he greased her good. She was very relaxed and he pushed himself into her easily. "Baby, I'm in." he said simply as his groin bottomed out against her small ass.

"Really? Are you sure? I mean it doesn't hurt."

"Of course not. As I told you if you aren't afraid it won't." he said and moved very slowly in and out a few times. "No relax and enjoy. If you think about it you'll have an orgasm."

Esmerelda did. She relaxed and enjoyed the feeling of Chad stretching her anus to the limit. It didn't really hurt, just a feeling of pressure. No worse than a bag and a half which she had done a lot of lately. The alcohol numbed her asshole to where it felt as if she was about to … about to… she had her first anal orgasm!

The next time, several days later, Chad decreased the alcohol in the first enema and then rinsed her good. He went slow and Esmerelda, not knowing that there was less alcohol, accepted him as before. "Oh Chad, I can feel every bump entering me! It feels so good." Chad obliged by rubbing her love button and she quickly had an orgasm.

This continued for several weeks, about once a week, until Chad had the alcohol down to less than a quarter of a bottle of rum in the alcohol enema. The strong peppermint soap still produced cramps in his little love toy but she gladly accepted his dick when it eased it into her.

After nearly two months he could take her anally without a cleansing enema. Esmerelda accepted the fact that she could take Chad anally without any pain. He was always careful to dilate her first with either his fingers or dildos and she never clenched up when he pushed into her.

"Chad, I love you!" she said one night when he went into her without so much as a cleansing enema first.

"I love you too Esmerelda!"

The following week they flew to Las Vegas and were married. Chad, 42 and Esmerelda 22. On their honeymoon night in Las Vegas Esmerelda allowed Chad to enter her anus dry. It hurt a bit but she was sure that she could take the pain. He stroked a few times and then squirted some lubricant from a carefully pre-placed tube and continued. "My love, you are the first and hopefully the last girl who will let me do this."

"Chad, I love you and I never want anyone else!"

"You won't have any other my sweet."

Chad and Esmerelda fucked happily in every way imaginable for the next 40 years until Chad died at the age of 80. Now some 62, Esmerelda felt very lonely without her husband. She tried giving herself enemas and sitting on large diodes but nothing compared to having her lover reaming her willing asshole.