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Ashley D - Part Two

The continuing affair between Ashley D and her older lover.
Note: You are advised to read each part of this story in order to understand references.

Most often things between Ashley and I went on as usual. I mean, life does goes on as they say. It’s not like in a porn movie where all you do from that point forward is get together for long, drawn out fuck sessions and no other aspects of life are visible. Like I said, more often than not when we saw each other, it was on an every other day frequency and consisted of her delivering and/or picking up items at my house. We would always talk with more affection than on a professional level unless I had a client, friend or neighbor with me. Sometimes when Ashley had an hour or two between stops, she had called in and told the base dispatcher she was taking a long lunch break.

Once, she pulled her car inside my garage and unknowing to me began undressing right there. I went out to see what she was doing and found she had stripped off her shirt, boots and uniform pants. I was so overcome with lust for this hot teen; I simply couldn’t wait to get her inside and onto a bed. She allowed me to pull the scrunchie from her hair, as she knew how I loved her long locks to fall about her innocent looking face. She then dropped to her knees and yanked my jeans and briefs to the concrete, capturing my thick cock in her small hands. While looking up into my eyes she said,

“Please Mister, please can I suck your cock. I’ll be a good little girl and make you cum really fast…I promise.”

I knew she was experimenting with an idea she had in her pretty little head and let’s be honest; all I could do is nod and give her the permission she wasn’t really waiting for anyways, as she was already on her knees.

I saw her slowly but steadily suck and slurp on my prick as she pulled every inch of it inside her mouth and throat. It amazed me that a girl who said she had so little experience could suck cock so well, but as I watched her throat expand to take me all in, and felt the tip of my rod sliding down into the top of it without her even gagging, I knew she’d previously made some teenage boys very happy this way. She was simultaneously swishing her tongue around, creating a strong suction and humming…yes, humming as she slid my shaft in and out of her face, all the while playfully tickling my full sack.

In no time at all I felt my balls getting ready to fire and she withdrew me until just the fat cock-head was inside her hungry mouth. She slid the finger on her left hand inside her dripping snatch and coated it with her vaginal juice, and as I began to unload my spunk past her clenched lips, she pushed it up into my puckered asshole! My cock jump and spurt even more than I was used to. I came like I hadn’t in many weeks of jacking off!

Even before I’d completely emptied myself inside her gulping mouth, I grabbed her curly locks and pulled myself from her lips, forcefully guiding her to stand up. I spun her around, pushed her backwards against the hood of her little car and bent her over it. Keeping my right fist around a bunch of her blond tresses, I used my left to place my fat prick against her slippery hole and quickly slide in to the hilt! She could only groan out loud and yell,

“YES! Fuck me baby, fuck your little girl!”

As if I had any other idea, I pounded her from behind like I was obsessed…and in some ways I very much was. At one point I was tugging on her hair, while I had reached my left hand beneath her glorious chest to pinch and twist her nipples, taking turns until she began to pull on them herself. After a few minutes she was panting with lust as she came hard, sending her juices running down her legs as I shot off again and again. She was so freak’n hot I couldn’t believe this was real sometimes!!

In short notice, our time together had passed and she redressed to go back to work. She didn’t even want a shower, referring to the seed she held within her tight pussy, by saying she was taking me with her. Then the day would continue as any other.

Our favorite times were the ones where we planned out a meeting to fulfill one of our fantasies, one of the perverted things she’d heard or read about and wanted to experience, or just to get together for some great sex. I too, developed a real thirst for the erotic, kinky and sometimes dangerous sex Ashley and I had come to cherish and often times…crave. Of course we both got more and more trusting of each other as time passed, but I’m getting way ahead of myself here. I want to tell you about the time we got together after that first night together, where she’d wanted to be taken and fucked out on my deck.


She had told me that I was to come up with some sexy and exciting way for the two of us to have sex, preferably something she hadn’t done before. I decided not to be too extreme right away, so as not to upset the apple cart and blow what could be a long-term and very hot relationship with a gorgeous younger woman. I came up with an idea one day while I was stuck in traffic on the freeway. I was idling next to a private school’s bus while the authorities cleared an accident a quarter mile ahead of us…traffic was at a standstill. On the bus were about fifteen to twenty students, all girls about sixteen years old. I’m sure they were just bored and looking for a way to kill some time and just having fun with the guy in the car next to them, as they continued to flirt and tease me for nearly a dozen minutes. While I more or less tried to ignore them, one young girl caught my eye and by the time I pulled away from them I had gotten quite the hard-on thinking about her, and so my plan was hatched.

Later I wrote down instructions for Ashley; where she should be, what she should wear, and the direction of the evening. Not every detail mind you, just start things off and let it progress on its own from there. I even gave her a safe-word to use if things went further than she was comfortable with; she could stop things without feeling pressured to continue. I gave her the note one afternoon as she picked up a delivery at my house and later that night she called me and told me how pleased she was after reading it. She was so excited in fact that she and I had phone sex, getting ourselves off with our own hands, imaginations and of course our voices.


It was about four pm on Friday afternoon as I drove along the downtown street. It was a fairly drab day as it had been raining since last night and even now the skies were threatening to downpour again at any second. Up ahead at one of the bus stops I could see Ashley standing there, waiting as I had instructed her to do. She was wearing shiny black four inch spike heels without stockings which showed off her long, tanned legs in a naturally sexy way; a short, dark blue skirt that was clearly much shorter than any private school would allow their girls to wear; a crisp white button down blouse that not only did nothing to hide her breasts that sat high on her thin frame, but in fact accentuated them. She had a dark blue matching sweater tied loosely around her shoulders and hanging down her back, while her long blond hair was neatly brushed and bound in to two ponytails that dangled from each side of the back of her head, which not only showed off her facial beauty but nearly touched her shoulders too. She looked every bit like a girl of seventeen with the body of a woman in her mid-twenties.

I could see the attention she was attracting, as she seemed to be waiting for a bus, even now she was shaking her head ‘no’ to a gentleman, that must’ve stopped and offered her a ride. I could see the outline of her silhouette from my vantage point as I slowly approached; her magnificent ass thrust out and the swell from the way her breasts hung as she bent over and disappointed the man behind the wheel of the car. The other male students who were waiting at the bus stop were obviously enjoying the way she shot down each one as they tried to pick her up.

I rolled to a gentle stop before her and said through the passenger side window, “Need a lift, sweetheart?”

She just stood, silently waiting. I could see the boys smiling as I stepped out of my vehicle and walked around the front to stand directly in front of her smoldering gaze. “I asked you if you needed a lift. The least you could do is be polite enough to respond.”

“Why would I want a ride from an old guy like you?” she said in a very stuck-up tone of voice, much to the delight of her admirers.

“I didn’t ask you if you wanted a ride, only if you wanted a lift,” I went on without hesitation, “but maybe a long, hard ride is exactly what a little bitch like you needs. A ride on top of my dick, that is!”

The look of shock on the boys’ faces was priceless as Ashley played her part. She said back to me, “How, how dare you!” and slapped my face!

I quickly grabbed her by the back of the neck and embraced her, kissing her hard while she struggled at first but quickly gave in to the kiss, even offering me her open mouth and tongue as the boys jaws dropped to the sidewalk. I pulled our lips apart and told her, “Now get in and I’ll give you that ride you obviously need so badly!”

I returned to the drivers seat and said loudly, “Don’t keep me waiting, little lady.”

I’d have given a month’s pay to see those boys reaction when Ashley stepped off the curb, opened my door and slid in next to me. Before she pulled the door closed, I could tell she had flashed the panties she wore beneath her short skirt to them. Leaning over, she kissed my cheek as I pulled into traffic and disappeared around the corner.

“God, that was so cool! Those guys first hit on me…then they watched as I turned down each guy who offered me a ride. It was a lot of fun, and it made me so wet as I waited for you, just like you said it would.” She was rattling on at fifty miles an hour, as I got out of the city and headed back towards my place. She told me about all the people, mostly men twice her age that went way out of their way to try and help her, when all they really wanted to do was get their paws on her supple, young body. As she went on I was glad I had decided on the idea of involving the public atmosphere, one that we’d use again in the future.

I drove into the garage, turned off the car and reached for her. She eagerly allowed me to take her into my arms. Looking into her bright blue eyes…we softly kissed, our tongues probing each other as we fought for control. Kissing her was such a treat; the way she’d bite my lower lip and gently suck it inside her mouth sent shivers up my back!

I placed my right hand on her left breast, gently but firmly kneading it like bread dough as I quickly felt her thick nipple rise and harden in response to the stimulation. I saw how she’d worn nothing underneath the blouse, letting everyone on that street corner see her large knobs when they outlined against the fabric. I abruptly pulled away and got out of the car. “Get in the house, little girl.”

She mocked surprise, but got out and did as she was told. You see, according to my instructions it said that at this point we were to go inside and make love, but that is where this night’s fantasy was taking a turn; a darker turn indeed. This was where she may or may not want to remember that safe word I’d given her before.

I walked into my house with her close at my heels, following me into the kitchen where I suddenly turned and said, “Is my little school girl excited?” She only nodded as she’d been told to do, her hair bobbing to the motion of her head.

“Does Daddy’s little girl wish to please me?” Again the enthusiastic nod and her ponytails bobbing along.

“Then why didn’t you follow the instructions?” She stared back in confusion for a few seconds before I snapped at her, “You aren’t wearing the pink lace bra I told you to wear!”

“I thought it would be more exciting to have my tits bare against the shirt…you see how my nipples are visible to everyone? I could see those boys drooling over them!”

I looked at her for a half a minute before saying in a sinister voice, “It is not your place to think! When you’re given a direction, you will follow it without question, understand?”

The silent affirmative of her head, only this time her lower lip trembled in that pouty way she knew melted my heart. She had a somewhat relieved look in her eyes as she thought it was over…ah, but not just yet, my dear. “Of course you’ll need to be punished for your disobedience,” I told her.

She looked surprised but I got the response I was hoping for. She simply lowered her head and said, “Yes Sir. I was wrong and deserve to be taught a lesson.”

I walked behind her and gently raised the short skirt that did little to cover her rounded ass cheeks, and could see the pink thong I had told her to wear. Unfortunately for her it left her globes very exposed and a great target for punishment. In a moment of improvised excitement I slipped two fingers inside the small band of material and slid them forward, feeling how wet and slick her pussy was already before sliding them back over her pink asshole. She was enjoying this attention as she sucked in air through clenched teeth and moaned. Suddenly I yanked hard, tearing the thong completely off her shapely body and pushing her forward harshly, tossing it on the floor. She instinctively reached out to break her fall, grabbing the edge of the kitchen counter as I put my hand in the middle of her back and held her there.

I sidestepped slightly to give myself a good angle, flipping her skirt up onto the small of her back. Without waiting for her to recover, I raised my right hand and brought it down hard against her left cheek, bringing forth a very loud ‘slap’ that echoed off the solid wood cabinets around us! She gasped in surprise, but before she could say a word she felt one stinging her right buttock as well. I held her firmly and asked her,” How many do you think you deserve for disobeying me Ashley?”

While she registered what I meant and formed a response, I delivered two more hard slaps to each side of her stupendous ass that was bent before me. Then she stuttered, “I…I don’t know. M, maybe ten, Sir?” Well, she was willing to go along so far, and I didn’t want to push her too far, too soon, so I said, “Then ten it is. Ten to both sides! You count off, ‘ya hear?”

I reached into a nearby drawer and withdrew a wide, wooden spatula from it, giving her right side and then the left a practice swat, lightly …so it wouldn’t hurt that much. She squirmed a bit, but probably figured it wasn’t that bad. “Now count, bitch,” I growled at her.

The next thing we heard was the swoosh of the spatula as it cut through the air and then the cracking sound as it connected with her skin, followed immediately by the sensation of pain as her nerve endings sent messages to her brain…messages of pain! “One,” she yelped! Then again as the tool striped the other cheek; “Two!”

“No,” I told her. “Not ‘two’. You see each side gets equal punishment. You need to count each pair as One, just don’t lose count or else I’ll start over.”

I gave each of her sides a good swat as she counted off ten, one for each side. As we got closer to the end I smacked her bottom harder and harder, until she was screaming out the numbers and pulling away from the sound of the wooden spoon as it whistled through the air just before making contact with her young teenaged flesh! The spanking left her backside a fiery shade of red and I could feel the heat rising from it. I walked around to the opposite side of the counter and tilted her face up to mine. Here eyes were moist, but she wasn’t crying. Mostly I saw a look that intrigued me in them…it was a look of unbridled lust. That little punishment had only turned this young woman on even more than she had been!


According to the Harley Davidson clock above the basement bar, ten minutes later found the two of us down their with the next part of my plans falling into place. I had led Ashley down to the rec room and told her to lean against the bar. I went around and then brought out a pair of wrist restraints, much to the surprise that shown in her wide eyes. But she made no move to resist as I clamped them to her wrists and then to two chrome beer tappers in the center of the bar.

I reached for a handful of ice and returned to stand behind her. I put the frozen, dripping ice to her ass and heard her squeal as she jumped from the contact it made against her reddened butt. I saw her shiver as I worked the ice over the area of her punishment, letting the water run down her legs towards the floor. Goose bumps rose along her supple flesh and try as she may, turning around was no longer an option. When I only had a couple cubes left, I rubbed them forward along her now wet and puffy slit, even pushing a piece of ice inside her pussy and telling her to hold it there until it melted. I felt her clamping down on it as I withdrew my digits from her slippery gash. My cock, straining to tear free from my own pants, would soon be freed. I placed the last piece if clear frozen water against her asshole and slid it inside. She did as she was told, probably more aware than I how another spanking would feel with her ass all wet. Even though I didn’t exactly expect her to get the cube inside her rear hole, it was nice to see she didn’t resist as it quickly shrank from her inner heat. She certainly must have felt the tip of my finger as it passed into her anal passage, but she hadn’t reacted negatively to that.

After instructing her to remain where she was, I stood behind her and quickly took off my shoes and clothing. Finally some relief for my confined cock! Next I went around to the bar, watching her watching me, and my raging hard on as it bobbed before me. I took a pair of scissors and returned to admire her from behind, knowing how her eyes had widened at the sight of the instrument. I slowly drew the edge up from her ankle, along her slender right leg. Cutting her small skirt from her body; the blouse found a similar demise on the floor beside it. She was now nude, except for her tall heels, which I decided to leave on her feet as they increased her height to match my own.

I leaned over her from behind, asking, but more or less telling her…”You’re going to fuck me now little girl,” as I placed the head of my cock against her opening and waited for her to understand. It didn’t take long before she pushed back against me, sliding herself onto my hard pipe and taking me inch by inch inside of her pussy until she buried me to the hilt. She slowly leaned forward and began a rhythmic motion as she fucked my large cock in and out of her overly excited young pussy. She loved the control I had over her, yet being in control of our fucking pace, too. I let her drive herself back onto me for a few minutes, while I distracted myself by either playing with her puckered little asshole and dreaming of the day I’d deflower this, her most private of openings.

For now I reached around to roughly play with her sprite, natural tits and pinch those long, rosy nipples until they were nice and stiff. Grabbing a pair of nipple clamps that I had placed inside an ashtray on the bar, I held her right breast and snapped it onto her nipple. The steel teeth firmly bit into her flesh, causing Ashley to whimper loudly, but not ask for me to stop. As I grabbed the opposite side of her chest she knew a clamp would soon be fastened there as well! Hearing her gasp and seeing Ashley biting her lower lip but not missing a beat as she thrust back onto my cock was something else!

I listened to her grunting and groaning; her aching pussy finally being given the attention it had needed since she stepped out in public dressed for tonight’s game. I figured as she walked in public displayed like a tramp, her inner-slut would make her horny and primed for sex. She had gotten off on it, as I hoped she would. Yes, I thanked God again for bringing this little girl into my life as Ashley slowed to a stop and began screeching, “Oh fuck, oh fuck, oh fuck, Jon” as the walls of her cunt clamped down on my cock! We rode the orgasmic wave together as my dick throbbed even more inside of her, and suddenly I decided to take over for her.

I grabbed onto her; no, not by her narrow waist but I held in each hand one of her blond ponytails as I began to encourage her to pick up the pace, even though she sounded pretty worn out. I really became machine-like as I pushed her towards the wood rail and then back onto my cock, feeling her insides stretching to take the pounding within. Ashley was verbally beyond coherency as she could only repeat herself, “Oh yeah, oh fuck yeah, yeah. Oh fuck yeah, oh shit, yeah, fuck yeah.”

“You’re being a very good little girl, Ashley,” I taunted into her ear, only to have her give me the perfect response: “Thank you, Daddy.”

Oh Christ, this babe knew how to push my buttons! Reaching beneath her once more, I held both nipple clamps in my fingers. Then I squeezed and released the pair simultaneously, tossing them onto the bar. The blood flowed back into her perky knobs, causing her to loudly squeal with erotic pleasure. With my fingers rubbing them roughly, I only prolonged the pleasure as her brain went into a state of euphoric bliss. While the fat head atop my hardened steel pole battered her cervix, even I was surprised when Ashley began to squirt!

Sliding out of her body completely, I stepped to the side as I watched her nectar spit from deep within her body like the fountains in front of the Bellagio! Her sexual system was in overdrive as she had had two powerful orgasms in less than ten minutes. Seeing her so turned on, quickly bought me over the edge as well. All I could do was step nearer to her, grab her by those pony tails and thrust my pulsing prick towards her mouth. Ashley tried to fasten her lips about the flared cap of my mushroom and swallow my gushing load, but nearly half of those spurts splashed across her face! The eruption so powerful, that it physically hurt as my sap shot up my root, exploding like a repeating shotgun as I sprayed her with it.

I released her restraints after I had stop cuming and pulled her onto my lap in one of the more comfortable chairs near the fireplace. Our subsiding passions took over; our breathing began to return to normal. We shared many kisses as we began to calm and realize what the two of us had just experienced together. Soon after, I took her hand and lead her towards the steam shower that was here in the basement of my home. We sat on the large bench as the room filled with steam; a warm spray of water gently raining down from the shower heads above.

While I was still in ‘recovery mode’, sweet Ashley’s youthful energy allowed her to bounce back much quicker. She stood before me and then bent over and began to toy with my penis as we slowly French kissed. Never really going completely soft enabled me to recover quickly. In a few minutes I was hard once again and not about to complain when she straddled my legs, sitting herself down as she stuffed me back up her hole.

At first she rode me slowly, but then began to increase the tempo as she whispered in my ear, “Pinch my nipples hard, Jon!”

She really seemed to like it when I’d done that before. With my fetish for long, hard twin peaks, who was I not to grant her wish? Then she started using a term which I had first heard earlier today, but one she would begin to use a lot in our future. With her blue eyes shut tight, head tilting back, she said, “Yes, Daddy…oh fuck! Oh!”

I felt my way to her clit and began manipulating it with my fingers. Even I was amazed my cock was getting harder still as she rode my prick and called me ‘daddy’ while talking so dirty. Reaching up, I turned the water off but left the hot steamer on, as my teeth latched onto one her taught nipples, making her moan as I bit and tugged until we shared another mutual orgasm as we held each other up.


Afterwards, we both collapsed on the sofa back upstairs, catching our breath as we cuddled and caressed each other softly. She told me she was so happy that she and I had met, and that this was just the start of something very hot! I couldn’t have agreed more, telling her how incredible she was. She said she was surprised, but pleasantly so when I’d slipped a finger up her ass while we fucked earlier, because no one had ever even done anything like that before.

We drifted off to sleep like that and I woke up around midnight to the sight of her contently sleeping in my arms. Carefully picking her up in my arms, she was carried to my bedroom and tucked beneath the quilt and sheets. She had already told her Father she was staying the night with a friend and would be home the next day. As I slipped in beside her and held her close, I heard Ashley whisper, ‘Thanks Daddy Jon.”


The next morning after breakfast, Ashley’s phone wouldn’t stop ringing. It was her father telling her he needed her home right away, so I drove her to within a block of where she lived and dropped her off. She still wouldn’t let anyone at home know about us. It temporarily upset me, but soon I realized I wanted to show her off more than she did me. After all, I was nailing a chick almost young enough to be my daughter.

We spent a good part of that afternoon texting and talking on the phone, when she could do so. The remainder of the weekend would slip by silently and we’d soon find ourselves immersed in another work week. One day not long after, I returned from the grocery store and found a simple note taped to my front door that said:

Dearest Jon,

I hope you haven’t any plans for next weekend. I most certainly do, for I believe it’s my turn to pick the next fantasy! Details to follow,



Part 2 of 3

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