Lessons

[LatinLady]

(OOC: This is for Jushorny and Myself ... enjoy!)

It was mid day and I was having a little sport with my next door neighbor. Ronald and I had been messing around off and on for going on 6 months. We saw each other whenever he felt like he needed some punishment. This particular day I had him bent over a chair in my bedroom and I was pounding away at his ass with a 6" strapon.

He loved it when I treated him like my bitch. It made him feel special.

So, there I stood, all 5'10" of me in stilettos reaming out a 6' man who had welts and marks all over his body. My house faces the ocean so I never bother to close my blinds and I completely forgot the pool guy was supposed to come over.

Ronald was panting and moaning, begging me to give it to him harder "Oh yes ... ..... fuck me ..... I've been a bad boy ...." and I of course was going to comply. "Take my cock bitch ... cum all over that chair!"

Three or four well placed smacks to his ass and some deep strokes and he just about painted the chair white. he slumped over the chair, breathing hard and shaking all over.

I looked up only to see the pool boy not really cleaning the pool. He was standing there open mouthed and shocked.

Ronald's phone rang while all this was going on and he said his office called that he had to go. I stood there, still wearing a harness and 6" dong while he got dressed and ran off, leaving me still wanting someone to torture.

I looked back out at the pool boy, watching him pretend to clean the pool. This one was new, he must be filling in for the regular guy.....

I slip out of the harness and completely naked open the sliding glass door of my bedroom.

"Hello .... did you enjoy the show?"

 

[jushorny]

I was pissed all morning long. I had been cleaning pools while going to college for 2 years now, even had my own route. That was until today when some other punk decided not to come in to work. So, I had finished my regular route and was now working on his. The only thing keeping me going was the fact that this would be the last one for today. Then its beach and beverage time for me, I couldn't wait.

I had already been in the pool and finished scrubbing the sides. I was just getting out to begin the chemical changes when I heard the noise. It sounded like someone was being hurt. I stood there lsitening for a moment. I wasn't sure if it was two people having sex or if someone was in fact getting hurt. I decided I had better check. We have strict rules about watching our customers and I never violated that rule, but if someone was really getting hurt, weel, then I should step in.

I quietly moved over towards the slding glass doors. With the sun shining I had to get right next up to them in order to see inside. I could not believe what I saw. This guy was naked and bent over a chair while the lady was fucking him with a strap-on. Holy shit, I had never seen anything like that before. My sex life apparently is apparently pretty status quo as it were. They were both really getting into it. Damn, he lost a huge load. I found it hard to believe something like that could turn a guy on so much.

My attention turning towards the lady, damn she had a body that wouldn't stop. She did look a little queer to me with the strap on. But, hell, if she took that off I'd fuck her in a second.


before I realized what was happening she was standing by the sliding glass door, having removed the strap on, asking me if I enjoyed the show.

"Uh, I'm really sorry ma'am. I didn't mean to be watching. It's.... it's just that.........well...............I heard noises..........I.........uh......thought someone was getting hurt."

 

[LatinLady]

Uh, I'm really sorry ma'am. I didn't mean to be watching. It's.... it's just that.........well...............I heard noises..........I.........uh......thought someone was getting hurt

I looked him up and down, taking my time to reply. I reclined back against the molding on the sliding glass door and crossed my arms, causing my breasts to protrude forward.

"Someone was getting hurt, and he was enjoying it immensely. Too bad we had to cut it short....."

I could see my nakedness was making him uncomfortable and a secret smile spread across my face. I wondered what he would look like tied to my bed while I spanked him...

"You aren't my regular pool guy. Are you going to give me the same services he did? I would hate to have to cancel my contract...."

The regular pool guy had never been one of my victims, but I wanted this one to believe he was. Maybe he would do what I wanted.

 

[jushorny]

I knew I could get into big trouble, maybe lose my job if I was caught watching any of our customers. I also knew we were strictly forbidden to have any sexual contact with any customer, although, I had heard it did happen from time to time. I wondered what she meant about services the othe guy provided.

"Uh...no ma'am..your regular called in sick today, I'm filling in on his route for him. Look, I..........uh........... am really sorry.........I really thought something wrong was happening..........I will just finish up here and be on my way."

I was so totally flustered, this hot lady I had just seen fucking some dude, and here she was standing right in fornt of me naked. Damn she had a body that wouldn't quit too.

 

[LatinLady]

Uh...no ma'am..your regular called in sick today, I'm filling in on his route for him. Look, I..........uh........... am really sorry.........I really thought something wrong was happening..........I will just finish up here and be on my way

I almost laughed at the nervous way he was fidgeting. He looked like he might bolt and run away. I uncossed my arms, running them through my hair as I stared him down. If I could manage to get him into the house I knew I could have him whimpering and begging under me in no time.

"I didn't ask you to apologize. Nor am I asking you to leave. I was simply making sure that I am going to get the same service as my regular guy."

I could tell I was making him uncomfortable standing here holding a conversation with him completely nude, but I didn't really care. I steeped closer to him, standing my full height. I stopped when I was mere inches from his face and my breasts were almost touching his chest.

"You know ... you never answered my original question. I am not a woman who likes to be ignored" I step really close, my face almost touching his, my breasts against his chest as I look into his eyes, "Did you........ like ...........the show?"

 

[jushorny]

I could feel the sweat on my body as she came closer. My eyes staring at her breasts, I tried not to, but could not help it.

"Uh...yes ma'am, I do the same cleaning on your pool the other guy does.............uh...........if that's what you meant."

She suddenly moved even closer. Her face at eye level with mine, her stilettos..........I oculd feel her nipples rubbing my chest. Even though I felt extremely uncomfortable, my cock felt the nipples and nothing else. I tried to will it down but was not having much luck.

"Well.........uh..........to tell you the truth ma'am...........and uh........this is not anything against how you look or anything..........but.........uh...........no..........I don't thing I did......uh.........enjoy the..........uh show..........as you called it."

Feeling the heat of her stare, I looked down to the ground, hoping against all hope, she would let me be to finish my work and get out of there. I was scared for my job.

 

[LatinLady]

Well.........uh..........to tell you the truth ma'am...........and uh........this is not anything against how you look or anything..........but.........uh...........no..........I don't thing I did......uh.........enjoy the..........uh show..........as you called it.

I was loving the reaction I was causing on him. He looked genuinely scared of me. I could almost feel his heart pounding in his chest and I could feel his growing erection.

"Well, that's a shame that you didn't like the show. Tell me ... what about it didn't you like? Because, I can asure you my adorable pool boy, everything that was going on in there felt good for both parties"

 

[jushorny]

Sweat was running from my forehead down my face. I had no idea how to answer her. I mean, I have had plenty of sex in my life, always can find pussy, and never had a girl complain. But, shit, it was all pretty vanilla stuff compared to this. I'm not even sure I could say the words to describe what I didn't like.

"Well...........uh...........it looked like that dude's ass was hurting him bad.......it was all red..........and..........uh.........then.....when you were.........were...........uh.........well..........you were sticking..........that thing up..........up.....his........."

Damn how the fuck was I going to get out of this. If she looked she could tell I was plenty turned on. I had already violated company policy, my mind was not thinking straight. I had to figure a way out.

"well........you know what you were doing..........it...it too looked.............painful" My eyes never looking at her, alwasy staring at the ground.

 

[LatinLady]

well........you know what you were doing..........it...it too looked.............painful

I laughed in his face, causing my breasts to jiggle against his chest. He wouldn't look me in the eyes and I wanted to watch him squirm some more so I grabbed his chin, tilting his eyes up so he could look me in the face.

"Appearances may be decieveing little one. You quite obviously saw that he was having a good time. I am sure you heard him begging me for more and you saw him cum all over the chair he was bent over. "

He started to turn his head down again and I held his chin,
forcing him to look me in the face,

"Do you honestly think that if it was really hurting him, he would have enjoyed it to the point of orgasm? I mean, I didn't just ram it in his ass and have at it, as much fun as that sounds, he was properly prepped and completely prepared for the experience."

I continued to look at him, probing his eyes for the smallest spark of interest in what I was describing.

"I would be willing to bet you three week's pay, that if you give me an hour of your time, you would beg me to fuck you."

I was getting bolder, but at this point, I wanted him to either agree for some fun or get the fuck out so I could find another victim.

 

[jushorny]

I listened as you spoke, being forced to look in your eyes. Remembering the guy and how much cum he shot out over the chair, its still probably puddled there, too much to soak in.

What was you talking about, properly prepped? How could any guy be prepared to get that thing stuck up his ass?

So far, I was still nervous and not in the least bit interested. Sure, if you wanted to suck my cock or let me fuck you pussy, that would spark my interest, but I didn't think that was what you were thinking.

It was when you mentioned three weeks pay, that my interest was sparked. Shit, I thought ot myself, 3 weeks pay for an hours time?? An hour with this gorgeous body? I felt pretty confident that it would take much more than an hour for me to beg to get fucked. I never had any thoughts of wanting to try it before, I was so totally straight. How in the hell would she be able to convince me in a short hours time? Plus the money, shit could I use the money.

"Just an hour right? If I'm not begging for you to fuck me in an hour then I get three weeks pay and can leave, no questions asked, right?"

 

[LatinLady]

Just an hour right? If I'm not begging for you to fuck me in an hour then I get three weeks pay and can leave, no questions asked, right?

A slow wicked smile crossed my face. I had him just where I wanted him. I let my lips barely touch his, feeling the heat come off his body before whispering

"One hour .... no questions asked. But you have to submit yourself to me completely. I say, you do. ...." I kissed him then, hard, letting my tongue flick inside his mouth. he stood there, a little dumbfounded when I grabbed his hand and led him inside the bedroom.

Once inside the bedroom I led him over next to the bed. I took off his shirt, depositing a kiss and a nibble on each nipple. Then I moved to his shorts, pulling them down, underwear, shoes and all came off at once. I could see his cock was rock hard and I couldn't hide my smile.

"First things first...I want to get a really good look at you. Start turning slowly. I want to see every inch of your body" He began to turn, slowly and timidly. When his back was to me I have his ass a playful slap *slap* he jumped as my hand stung him a little "That was just a love tap .... keep turning" He was facing me again, his cock still at full attention. I grabbed it and squeezed, using it to pull him roughly against me "I am going to start by putting a little color on that ass of yours...I don't like to see undecorated skin. Lie down, face first on the bed"

 

[jushorny]

Damn I had never been treated like this before. Her lips and tongue felt so delicious, my cock was fully hard now.

I had to admit I felt really sexy as you began to undress me, your hands touching my skin. I felt like I was being treated like a sex object and what red blooded male wouldn't enjoy that.

Standing there naked in front of you. I was not ashamed, I knew I had a hot body and I knew my cock was nothing to be ashamed of.

I slowly turned around feeling your eyes cover every inch of my body. I didn't expect you to slap my butt and it did kind of sting. I jumped feeling the slap. But I also knew my cock jerked and I could tell it turned me on.

It was when you asked me to lay down on the bed, wanting to "color" my skin that I began to worry. What had I gotten myself into, was I ready for this? Hell yeah, you can do it I told myself, its only an hour, so what if I had a red ass when it was over. How hard could a beautiful thing like you slap anyway.

I wanted to give no clue to you that I might be the least bit scared. I obediently walked over to the bed laying down face first. I moved so my hard on was between my legs, not being pinched between me and the bed. Then I folded my arms placing my hands under my face as if I was expecting a back rub. Wondering...........anticipating what was to come next.

 

[LatinLady]

I stood there for a moment, admiring his hard lean body sprawled on my bed. I started by kneading and pinching his flesh, leaving little pink marks all over his back, ass, and legs. This was nothing painful and I could tell he was enjoying it. Then, I started to use my nails some, leaving pink lines all over his body that disappeared quickly. This also didn't hurt, but I wanted him to get used to the feeling of my hands all over his body.

I began scratching harder, the marks not disappearing so quickly now, in combination with a few little smacks, nothing too hard, again, still getting him used to the sensation. I leaned my entire body on top of his, bringing my lips right next to his ear

"mmmm now that I have warmed up, lets start"

I bring my hand down between our bodies and grab his ass roughly kneading and massaging it before I get up and walk over to the dresser. I pick up a bottle of lube and a leather padle.

I throw the lube on the bed next to him for later use and begin to smack his legs and ass. Soft at first, letting him get used to the sound then a little harder. "SMACK SMACK SMACK* I could see him bounce on the bed every time I smacked him it was such a pretty sight. "mmmmm positively delectable" *SMACK SMACK SMACK* I could tell it was stinging by the way he jumped every time I hit him and as I ran my hand along the skin it felt hot to the touch.

I continued smacking, making his ass and the back of his legs a rosy color. "mmmm nice and decorated, just how I like it. Reach back, feel how hot your skin is .."

I grabbed one of his hands, forcing it back and letting him feel what I feel every time I touch him...heat.

I started running my hands all over his ass and legs, massaging the welts and pinching them, causing him to suck in a breath. I let my hands wander up to his ass, giving it a few more smacks with my bare hand and spreading his cheeks to look at his little pucker. I bent down, letting my tongue dart out and lick around it. "mmmmmm"

 

[jushorny]

The beginning was a piece of cake. I knew you would get somewhat rougher, but I was totally enjoying it so far. Especially the nails against me, not too deep, but for some reason it made me squirm.

As you became more rough, more aggressive, I was trying to concentrate on the money and not the slapping of my ass.

My body began responding to your hitting. It hurt like hell but I was trying not to let on. My body jumping with every hit was probably giving me away, but I was determined not to yell out.

I could not believe how hot my skin felt when you forced me to feel. Never knew the spanking and scratching could cause such heat.

The pinching and scratching of the welts was becoming difficult to endure. As much as I hated it, your hand massaging my ass felt good, giving me relief from the pain.

When I felt your tongue on my hole I knew I was going to be in trouble. I would never admit it to you, but it was turning me on. I had never felt anything like it before. This is what i was going to have to fight off I told myself. I tried squeezing my ass cheeks together, but you smiply slapped me and pulled them apart with your hands.

When your tongue pushed in slightly I let out a moan and was immediatley regretful I did.

 

[LatinLady]

I could feel him moaning under me as I explored his ass with my tongue. So, just like I thought, he does like it! I delved deeper, tongue fucking his ass while my hands continued their assault on his skin. I could still feel the heat coming from his skin, but I don't think it was just from the spanking anymore. I could tell he was aroused and ready for the next step.

I reached over, grabbing the bottle of lube and putting a little on my index finger. I rubbed my finger along the hole softly, while leaving little bites on his ass. The first little push into his ass and he jumps. I hold his ass down with my other hand, letting my finger slide in a little farther and then back out. Slowly I work my finger in and out until I can slide it all the way in with little or no resistance. By this time he is panting and moaning. I can tell he is enjoying, but not yet ready to beg me to fuck his ass with my strap-on.

"mmmm such a tight little asshole"

I apply a little more lube, starting to bring in a second finger. He sucks in a breath, as the second finger slides in more easily than the first. I can feel his breath is now ragged, and his cock is straining against the sheets

"mmmmm you like that don't you ...dirty little boy"

 

[jushorny]

"Oh fuck........." I yell out when I feel you push a second finger in. It was hurting and causing pleasure all at the same time.

"Nooo........please.............." I begged with my voice but my ass was wiggling giving you the wrong signal.

I would hear myself yelping when you bit down on my ass causing more pain to the welts.

I could feel my cock leaking precum. It was all so weird, I wanted you to stop and I wanted to to continue. I wondered how I ever got myself into this and how I was going to get out of it.

My sense trying to return. I lifted myself up on one hand, trying to roll myself over and to get your fingers out of my ass. Reaching back in an attempt to pull your fingers out. I couldn't let you fuck me I told myself, I just couldn't let you turn me into a slut.

 

[LatinLady]

He pulled up onto his knees, trying to dislodge my fingers fom his ass. I knew his body was responding with passion to my fingers, it's his mind that was getting in the way. I had to override his mind and fast. As he got up on his knees his cock was suspended for a moment, completely exposed. I wrapped my fingers around it and he froze. The sensation of my fingers still in his ass and my hand now on his hard rod caused him to stop a moment and it gave me exactly what I wanted. The power to make him lose control. I worked my fingers in tandem with my hand, stroking his cock at the same time that my two fingers slid in and out of his ass.

He lost it there for a moment, he stopped fighting me and just stayed there on all fours, letting me stroke and finger him.
"mmmm feels good doesn't it ... I told you, pleasure." I stroked him a little more, letting him enjoy my hands. "let me sweeten the deal for you little one. Don't disobey me any more and I will let you stick that nice hard cock in my ass ..... that is ... if you beg me to fuck yours first."

 

[jushorny]

I thought I was almost successful, that is until you wrapped your hand around my cock. I moaned out feeling both your hand teasing my cock and your fingers inside my ass. I wasn't sure which was providing more pleasure, but I wanted neither to stop.

As hard as I willed myself to continue to roll over I couldn't. I stayed there, now on all fours, letting your hand work my cock and your fingers work my hole. My breathing becoming more ragged, my hips moving trying to fuck your hand. I was afraid I had reached the point where my cock was thinking, not my brain.

I felt my cock twitch when you offered to let me fuck you. My thoughts returned to your naked body, how beautiful it was, how I very much could enjoy fucking you. Then you dropped the bomb, first I would have to let you fuck me and beg for it no less. I had never begged for it ever in my life. I always got what I wanted.

Then I felt your grip tighten on my cock, your fingers probing deeper. Suddenly your hand let go of my cock and you pushed your fingers in moving them around, finding that special spot inside of me. I yelled out moaning "Oh shit.........please......keep your hand on meeee.............please............"

Before I realized it I was pushing back, trying to get your fingers back to the spot that had so turned me on, needing to feel you there. My cock begging for attention.

 

[LatinLady]

I could tell I had him with the promise of letting him fuck me. I let go of his cock and I could tell he didn't want me to. I began fingering his ass with my two fingers, deep. I bumped his prostate a couple of times, not really wanting to massage it and make him cum. That really got him going Oh shit......... please...... keep your hand on meeee............. please............

I pumped his ass a little harder, sliding a third finger in there slowly. I reached under the matress where I kept a small anal plug ... it was time to step things up a little bit. I didn't let him see the plug, but in order to make it easier, I grabbed his cock again, letting my fingers slip from his ass.

"mmmm little one ... I think it's time for the next step. "

I brought the plug to his ass, sliding it in slowly as I caressed and coaxed his hard throbbing cock, not hard enough to make him cum, but hard enough to make sure he is relaxed. Slowly, inch buy inch I slide it in until it is firmly lodged in his ass.

"now that looks sexy, mmmmm"

 

[jushorny]

My head fell to the pillow when I felt your third finger pushing in. It hurt some but I couldn't help but wiggle my ass. I looked back and felt shamed. I was laying there my ass sticking up in the air with this ladies fingers sliding in and out.

"No... pleaseeeeeeeee............don't..............don't make me........do.........this............" My brain finally taking control over my cock, at least for a moment. I wondered how much time was left on the hour. I thought I had succeeded when you pulled your fingers out.

Then I heard you say something about the next step. Your hand returned to my cock sending a shiver down my spine. I felt something sliding back into my ass.

"UGhhhhhhhhhhhhh" I screamed out grabbing the edge of the bed and it slid in deeper and ever so slowly.

I heard you say how sexy it looked. I looked back and all I could see was my ass sticking up with you behind me. Damn was she really turning me into her sub toy to play with? Could it be possible. I tried to fight it, I wanted to, but I wasn't sure how storngly I could fight anymore.

 

[LatinLady]

I admired his ass for a moment, with the anal plug firmly in place. I could see him straining with his own mind, his own fears about what was going on.

I looked him straight in the face and smiled, smacking his ass as he kneeled there, ass in the air.

"you skin is cooling some .. can't let that happen little one"

I spanked him a few times, as his ass danced around under my hands. The anal plug tugged and pulled at his ass, stretching it every time he moved. I toyed with his cock some more, tugging and pulling at it, making precum leak even more . I ran my fingers around the edge of the anal plug

"mmmm your skin is so hot ... and you ass is adorable. "

I pushed at the plug, forcing it to wiggle in his ass, causing his cock to bounce

"Are you ready to beg me to fuck you yet?" I looked at the clock, we had only been at this for half an hour.

 

[jushorny]

The plug you pushed in my ass was sending wild sensations through my body. Every move sent a different feeling in my ass. It was totally turning me on even as I tried to fight it.

I heard you say how my skin was cooling and before I knew it your hand was smacking down hard on my ass. It caused my ass to shift forcing the plug to send more sensations. "Owww............shitttttttttt."

The plug felt like it was stretching my hole more with each slap. I felt your finger tracing around my hole. "Ohhh godd....yesss....." I moaned out.

You hand then going back to my cock, pulling and tugging at it. Squeezing precum out. Your fingers now at my mouth telling me to lick off the precum or you would spank my ass good. I stuck my tongue out licking your finger, tasting my own precum.

Your hand returning to my ass making the plug move more. Shit I was so close to letting you do anythning you wanted to me. I wanted to scream out, go ahead fuck me, fuck me hard and get me off.

You asked if I was ready to beg for you to fuck me. Your hands rubbing and spanking together, each time hitting the plug. I looked over and saw it had only been 30 minutes. I bent my head back, my body arching, causing the plug to move again. How was I ever going to make it the entire hour. No, I told myself, don't give it, not yet, don't let her fuck your virgin ass.

"Fuck no, bitch, get that out of my ass" I yelled, hopefully in a convincing tone. I pushed up with my arms to get into a kneeling position. That caused my ass to clamp down tighter on the plug.

 

[LatinLady]

Fuck no, bitch, get that out of my ass"

My eyes opened wide, not believeing the words that had just come out of his mouth. And yet, he could have reached back at any time and taken it out himself. I mocked indigation for his benefit and brought my hand down hard on his ass, leavingmy entire palm marked.

"Bitch eh? You are the only bitch I see here." *SMACK* again my hand on his other cheeck* "I am not the one with an anal plug stuffed in my ass, on all fours on a bed, you are, and you are enjoying it. " *SMACK* another one. I grabbed the plug ans started to pull it out, and then slammed it back in, causing him to moan loudly.

"You see that .. you like your ass filled with my fingers, and this plug, and pretty soon a hard dildo." I continued to play with the plug in his ass, taking it out almost all the way and then slamming it back in.. every time causing him to moan louder and louder.

I reached under the bed, grabbing the harness that I had used earlier. I continued smacking his ass, all the while putting the harness on and tightening it. Ocassionaly wiggling and slamming the plug in his ass.

The cock attached to the harness was too big for a beginer. I took it off, leaving only the clip section. I reached next to me into the nightstand and pulled out a slender 5" dildo.

"Even with your impertinence, I wouldn't just ram a 9" dong in your ass. I should, for calling me a bitch, but I won't. You are gonna beg me to stick this one in ... and once I am done, you are going to get to cum in my ass.

I stroked the strap-on as if it was a real cock, lubing it and slapping it against his ass.

"Come on little one .. beg me to fuck you."

I reached up .. grabbing my own nipple and licking it while looking at him ...
"Come on ..... beg me "

 

[jushorny]

I knew as soon as I finshed calling you a bitch that I shouldn't have. You began to be relentless. Smacking my ass harder then before, pulling and pushing the plug in my hole.

Then you began berating me about how I liked having your fingers and the plug up my ass. All the time hitting me, my ass becoming sore, hotter, and redder.

Every time you pulled the plug almost out I could feel the need I felt to have it pushed back in. I knew I was losing all control. I knew I wanted it as much as you wanted to give it to me.

I turned to look back and saw the dildo attached to you, saw you stroking it, smacking it on my ass. I saw you licking your tit, wishing it was me licking it.

Looking under me I saw my cock rock hard, leaking precum, a string of it from the tip of my cock to the bed.

You slid the plug out and rammed it back in. I knew I was through. I knew I had to have you fuck me.

"Yes......." I whimpered "do it............."

Not able to say the words, but wanting it none the less.

 

[LatinLady]

Yes.......do it............."
I knew I had what I wanted from him but I needed to hear him say it. I needed him to beg me to slam my strap-on in his ass.

I took the anal plug out ... admiring the nice open asshole. I positioned myself behind him, letting the head of my dildo rest against his ass.

"Beg me ..... I want to hear you beg me to fuck you ...... say it ..." I let the head of the dildo rub up and down the crack of his ass, lubing up even more of his ass "Come on .... beg me to ram this cock in you. "