I teach a recent High School beauty about the glories of ass fucking.
Chapter 80:
ANAL TRAINING
I live aboard my boat full time and was docked at a marina on the St. John river in Florida. Looking at my captain’s log, I realized that it was time for some new bottom paint. I also wanted to have a leaky seacock replaced, and a few other maintenance items looked at. I made arrangements with a nearby repair yard for the work. I had her pulled out of the water and put “on the hard,” as we boaters say. With my floating sex palace in the shop, I needed somewhere to sleep. I rented a small flat with a basic “kitchenette” near the repair yard. The yard was in a rundown, industrial area of town and there was a dilapidated old motel nearby. The motel hadn’t had any maintenance or sprucing up in decades. But it was nearby, it was very affordable, and it was only for a short-term. I could put up with the substandard conditions for a couple of weeks.
The unit I was in was shabby and the first thing I did was go to Walmart and buy some new bedding and some cleaning supplies. No telling how many whores had been plundered on that bed. I spent the first two days scrubbing and cleaning every square inch of the unit until I was satisfied that I wasn’t going to catch any horrible diseases from touching things.
I also spent my breaks sitting in the lawn chair outside the door, smoking and watching the lowlifes who lived in the adjacent units come and go. It was a motley crew of scum I had as neighbors, some with beat up junker cars, a couple with bicycles and some who walked everywhere. Some were wizened up old men with bronze, creased lizard skin faces, their retirement packages insufficient to cover both rent and the never ending booze and cigarettes they consumed. Others were middle aged, military haircuts, appearing to be recent prison releases, looking for work. The only residents of any interest were two doors down: a forty-something man and his adorable daughter. She appeared to be about high school age, maybe first year of college. They seemed like the cream of the crop of all the residents in our little corner of the jungle.
One evening I was sitting outside taking in the evening breeze when the man came home from work. His daughter heard the car door slam and rushed out to greet him. Throwing her arms around his neck she said “Oh, Daddy, I’m so glad you’re home! I had just a horrible day. I got turned down for three jobs I applied for. I just don’t know what I’m going to do. I simply can’t waste away in this crummy place any longer.”
Hugging his daughter he replied “Something will turn up, Haley, I just know it will. We have to keep up hope. I’m certain that things will turn around soon.”
“I hope so, Daddy. I’m getting awfully bored just hanging out here all day and getting turned down for every job I apply for. When do you get paid again, Daddy? We’re running low on food.”
“Not until Friday, honey. Maybe I’ll stop at the food bank tomorrow. I hate to take handouts but we’re near the bottom. Come Sunday, I’m gonna visit that church down the road and say a mighty prayer.”
When they turned to go back inside their unit, they both looked in my direction. I smiled and waved; the man nodded to acknowledge my presence and they disappeared inside. My heart went out to them. I had no idea how they had gotten themselves into this situation, but their display had touched me. I wanted to do something to help if I could.
The next night, the same situation repeated. This time, however, I intervened. “Excuse me, neighbor. I’m Sailor and I couldn’t help but overhear your talking. Can I offer you a beer? Maybe we can talk a bit, and I can offer some guidance. I mean, look at me. I’ve been around the block a few times. I may be able to offer some suggestions.”
Surprisingly, they accepted my offer. “I’m Jake and this is my daughter Haley. I drive a forklift over at the big box warehouse down the street and Haley just graduated from high school. She’s having a tough time finding a job, especially with no transportation.”
They seemed like decent, honest folk and Haley was cheerleader good looking. They pulled over their lawn chairs, and I picked a few beers from the fridge. I grabbed a bag of chips which they instantly devoured. We talked for a while, and I shared some ideas for Haley to find work. I gave Jake a few pointers on how to find and get additional governmental assistance to help keep them afloat until things turned up for them. We had a nice evening, talking and drinking beer until they finally retired to their own room.
As I drifted off to sleep, I had visions of Haley in my head. Very pretty face, just right boobs, slender waist and silky thighs. She was adorable but her self-esteem was non-existent. She had told stories about being bullied in high school, and her inability to find a job was weighing heavily on her. She said she felt alone and ostracized.
The next day I visited my boat to assess the progress. The yard manager gave me an update, and all seemed to be progressing according to plan. As I left the repair yard, I instructed the Uber driver to take me to the local grocery store. I filled several bags with food and supplies, returning to the seedy motel which I now called home. I knocked at my neighbor’s door and Haley pulled back the curtain to see who was there. Seeing me she cracked the door open an inch or so.
“I brought this for you guys, Haley. I hope you can use it.” I looked down at the bags of groceries at my feet. Her eyes popped open wide. Without saying a word, she opened the door. I handed her bag after bag which she happily took.
When the exchange was over, she looked at me, her eyes welling up with tears. “Oh, Mr. Sailor, thank you. Thank you so much. I don’t know what to say. This is the nicest thing anyone’s done in, well, I don’t know how long.”
“Glad to lend a hand, Haley. It’s my pleasure.” That evening, Jake came over to thank me again. I explained to him that the law of the sea is that if you encounter another boater in trouble, you are obligated to assist if you can do so safely. I happen to live by that law on land as well.
The following day, mid-morning, there was a knock at my door. When I opened it there stood Haley, her laptop under her arm.
“Mr. Sailor, can you help me?”
“I hope so. What’s the problem, Haley?”
“I’ve been having trouble with my job applications. I must be doing something wrong because I’m not getting any responses or I’m getting turned down without even an interview. You seem wise. Can you give me some pointers?”
We settled in at the small table in my room and Haley deployed her laptop. She started showing me all the ins and outs of the various websites she was using to find and apply for jobs. I must admit that applying for jobs is much different today than way back in the dark ages when I had to do that. I stumbled along with her looking at one website after another. It was all very foreign to me.
Finally, I said “Haley, have you tried actually walking into a store, asking for the manager and inquiring if they have any openings? I mean, like face-to-face?” Her frown answered my question. “I thought so. Maybe you should try it and see what happens.”
“But Mr. Sailor, I have zero self-confidence. I wouldn’t be able to do that.”
“Let’s explore that for a minute, Haley. Have you ever had a boyfriend?”
“Not really. I mean lots of guys tease me. Some ask me out but all they want is back seat blowjobs or to feel me up. Some finger me and I’ve let a couple of them fuck me, but I haven’t gone any further than that.”
“Have you ever had a crush on a guy and asked him out?”
“Oh, hell no! Yes, I’ve had crushes but there’s no possible way I could ever ask a guy out.”
“Why not Haley?”
“Well, they’d think that all I wanted to do was sleep with them. I’ve only had sex twice and only given three blowjobs. The sex was just a quickie, missionary, 'wham-bam-thank-you-ma’am' kind. I’ve never done anything more than that.”
“Well, maybe if you had a bit more sexual experience, you’d have a bit more self-confidence. Here. Let me demonstrate. Come sit by me on the bed and I’ll show you.” We moved to the bed, and I put my arm around her shoulders. “Now, I’m going to kiss you, and I want you to respond and see what kind of response you get, okay?”
I leaned toward her pretty face and planted my lips on hers. At first, she was cold, more of a “movie” kiss. “Now respond as if you were in control, not me.” I kissed her again and she warmed up, passion began to rise, our tongues intertwined. She wrapped her arms around me. We broke for a breath, I nodded assent and she went back at it, giving me a wet, involved kiss.
“That’s more like it. Now, see my pants? Can you see the response you created in me?” My shorts were, of course, tented and a small dot of precum was visible.
“I did that? I made you get hard?”
“Of course you did, Haley. And the more you take control, the greater the response will be and the higher your self-esteem will rise.”
We ended up with her fishing my cock out and giving me an amateur blowjob. She wasn’t ready to take my cum in her mouth but it was marvelous to shoot it on her pretty face.
As she was wiping my cum off her face she said “You can’t breathe a word of this to my Dad. Promise?”
The next day, the Uber dropped me off outside my door. Haley heard the car door slam and came out. “Thanks for the lesson yesterday, Mr. Sailor. I felt a lot better afterward. Last night I relived it all and I felt much better about myself. This morning I even went to the fast food place down the block, but they weren’t hiring. But at least I tried.”
“Good work, Haley. Glad I could help.”
“Can you help me some more? Pleeeeaaase?”
How could I resist? Inside we talked more. She reiterated that, with yesterday’s tryst with me, she had now given four blowjobs, been fingered by five boys and let two boys fuck her pussy. “Mr. Sailor, I’m pretty inexperienced and I need to know more. Like, I’ve heard of girls letting guys fuck them in their ass but I’ve never, ever done that. They say that every guy wants to do that, like it’s their favorite thing. What’s it like? Does it hurt?”
“Alright, darling. It's time for some lessons on ass fucking. There are a few ground rules. First, you must visit the bath and poop. The results can be ugly if you don't.
“Next, lube is important. Your asshole is not like your pussy. It does not get wet and sloppy, like your cunt, on its own. Plus, it's incredibly tight initially. That's why guys like to fuck it so much. Now, your pussy is small and tight, too, but it expands and opens up readily. Your anus, at least until it's been fucked for years, doesn't open up quite so fast. That's another reason why guys like it so much. It's possible to fuck your back hole without lube, but it can be painful for both you and your partner.
“More about the lube. Either a gel or liquid works. Sometimes, a guy will fuck your cunt, pound it until it gets really sloppy, and your pussy juice acts as the lube. But lube is essential if the guy wants to hit your ass first. Make sure the guy uses the lube to coat his dick, then your tight little hole.
“If it’s me fucking your ass, when I'm getting your asshole lubed, I'll spread some around your hole, then insert one finger inside to get your inside ready too. I'll stroke my finger in and out, spreading the lube inside. Then I'll insert a second finger. Two fingers will be fucking your tiny hole, covered in lube, stroking in and out. Depending on how your hole responds to getting finger fucked with two fingers, or just my mood, I may use three fingers, sometimes four. We won't talk about fisting your ass until another time.
“Let's go over your position. I can take your ass in any position where I can fuck your cunt. Typically, you’ll either be on your hands and knees, doggy style, or on your back with your equipment at the edge of the bed, your legs up in the air. Sometimes, guys will fuck your ass in the spoon position, with your top leg held high or with you on top, cowgirl style. Initially, for these training sessions, I want you on your hands and knees, doggy style. This gives me optimum position to work on your puckered little hole of happiness easily. Once you're in position and before I've applied any lube, I will probably kiss and lick your backside. Running my tongue all around your sensitive hole will, I guarantee, bring you much delight. It will tickle and make you moan. You will want more.
“Next comes the magic moment. Your ass cheeks are small and your fuckbox is wide open, but you may want to reach your arms around and pull your cheeks apart. This helps but is optional unless you have fat ass cheeks. When I hold my cock and place it at your anus, you will flinch and clench your sphincter muscle closed tightly. "Not in here, big boy" you will say to yourself. Clenching your hole closed tightly is both good and bad. It's good because eventually my cock will force its way inside, giving me the tightest fuck on earth! It's bad because when my dick does pop inside, it can cause you more discomfort. It's best if you learn to consciously loosen your asshole and allow my prick entry.
“OK. So now you're on your hands and knees, your asshole is generously lubed up, you've pulled your ass cheeks apart for me and the head of my cock pops inside. Understand that in the doggy position, I can see and feel all this. I'm now in heaven, I'm cranked up, ready to fuck your ass into next Tuesday.
“Not so fast old man. This little fucktoy needs to get used to having something in her rectum going the wrong direction" you think to yourself. I'll grab your slender hips and push, gently at first, making the first couple of inches slide into your tight hole. Initially, it will feel weird to you, and you won't like it. I'll go slowly, stroking just a few inches in and out. The lube will make it slippery, and I will be talking to you.
"’Yes, Haley, that's it, doll. Yes, baby, let me fuck your nice ass, just like this. Oh, baby, you have no idea how good it feels to have my cock in your tight ass. Relax your muscles now, just breathe slowly and relax.’ The shock of having my cock in your butt will fade and the gentle strokes will begin to feel good. As you get comfortable with a fat dick in you, your hole will begin to loosen.
"I’ll keep talking to you. ’That's it slut. Open your hole. Give me your skanky ass, let me fuck it all I want. Just lay there until I'm done. I want to fuck your ass hard and deep. I want to fill you with my cum. Be my little ass whore now baby. Give me your sweet butt hole to fuck. Hold it up high now, show me how much you want this cock.’
“All the while I'm talking dirty to you, I'm stroking my dick in and out. I started with a few inches. Now I'm pushing him in deeper. Three inches, four inches, then five. I keep pushing him in deeper until finally my entire shaft is buried all the way up your ass.
“I'll quicken the pace. I'll stroke from the tip of my dick to my balls slapping on your pussy. I'll ram it in hard and fast, then I'll slow down and stroke very slowly. I'll be watching my cock slowly slide in and out, disappearing into your creased hole. Seeing this will drive me absolutely crazy. I might pull my dick out and admire your gaping hole, wide open. Put it back in and remove it, to gaze at your open hole, only to push my fat cock back into that pleasure pit. Then I'll pound fast again. Holding your hips, pulling them toward me, I'll ream your ass with abandon, eventually slamming him all the way in, holding him in deep, and unloading, pumping my semen into the bottom of your glory hole, the dark depths of your rectum.
“Haley, soon you'll be taking me in your ass like a pro. You'll beg for it. You'll learn to ride me like a cowgirl, my fat dick balls deep up your ass, you sitting down hard on my groin, me loving it and squeezing your boobs. Then you'll try reverse cowgirl so that I can watch your asshole swallow my staff. You'll let me alternate between your ass and your cunt, fucking your pussy, pulling out and ramming him up your ass, then back in your cunt. When I ask if my little ass whore is home, you'll smile sweetly and ask what position today, Mr. Sailor.
“Eventually, my tender young twat, you’ll buy yourself a butt plug. A small one at first, moving to ever fatter ones as you mature. You'll learn to insert it in the morning and wear it all day. For practice, you can lie on the bed and fuck your own ass with the handle of your hairbrush. I want you to try that, Haley. Start your lessons tonight. Fuck your own ass with your brush handle.”