Note: This story is part 3 in a series but reads just fine on its own without any knowledge of the previous stories. Enjoy!
Act 1:
There is a cool October afternoon from years ago that sticks out in my memory. I was walking home from school with a heavy backpack full of textbooks. I had just gotten out of a political science lecture – my last class of the day – and I was enjoying the autumn breeze against my face as I made the 15 minute walk back to my house from Woodbridge Community College.
As I walked I could feel my jeans, and my underwear rubbing up against my backside, and it was an unpleasant reminder of the previous day’s events. All day, in fact, I was self-conscious about the way I sat down – a little more gingerly than usual. I was prepared to tell anyone who might be curious that I was sore from the gym, but thankfully, nobody asked.
What I couldn’t say was that I had an embarrassing secret. In fact, it was more than embarrassing. I would have died of humiliation if anyone would have found out. I was a grown man of 19 years, but that didn’t stop my step-mom Ashely from taking her belt off and whipping my ass with it when she thought I needed it.
She actually had two items that she preferred to use. The belt was usually reserved for when she felt the need to discipline me in a more formal sort of way. She would tell me to go to my room, or to hers, and wait for her. Then she would come in the room holding the belt, and I would have to bend over – usually with my pants, and underwear around my ankles – and take it, or else I would face a more severe punishment. She also had a small, but thick wooden paddle – about the size and shape of a round handheld mirror. That was useful to her because she could lay it on me right over my jeans if she had to, and it would hurt like hell. Typically I got the paddle when she wanted to teach me a quick lesson, and then move on with her day.
It might seem bizarre to for a college-aged kid to be spanked, and trust me, I felt the same way when it all started. But there is a story behind it. The long version is in the first volume of this book, but I’m happy to give you the gist.
My dad had left Ashely for another woman when I was in high school, and that left us alone together until I moved out at 21. I was more than a handful as I was sneaking out all of the time, drinking, partying, not keeping up with school, or doing anything productive. I was getting into drugs, and I was having sex with multiple women.
It didn’t help that Ashely was young, and beautiful. She’s never actually told me her exact age, but she couldn’t have been over 40 when I was living in the house, although she looked like she could have been a lot younger. She had blonde hair that went down to the middle of her back, and bright piercing blue eyes. She was a part time yoga instructor, and had the kind of body that I’m sure brought more than the usual amount of men to her classes. That only made it harder for me to take her seriously as an authority figure.
I had had very little discipline in my life until Ashely became a part of it, and by the time I was 18, I was beyond the repair that simple things like grounding, or scolding could accomplish. My life was spiraling downward, and so she reasoned that desperate times call for desperate measures.
I had snuck out after being grounded one evening so I could buy pot from a friend a few blocks away. Somehow she knew what I was up to because when I came back home she was sitting on the front porch waiting for me. I tried to talk my way out of getting into more trouble, but I quickly found out that she had changed the locks, and wasn’t going to give me a key unless I agreed to her terms. And those terms were for me to submit to a new regime of corporal punishment. So that night I had to march myself up to her room and receive a spanking…and it was a doozy.
Surprisingly, it worked. Shortly after I started to shape up, and our relationship improved. She promised me she wouldn’t tell a single soul, and as far as I know she has always kept that promise. I promised to do the same, but I did get her permission to write about my experiences as long as I used nothing more than our first names. So that’s the back story.
On this particular day the paddle had been the proximate cause of my sore bottom. I had come home after doing some grocery shopping at Trader Joes. Ashely had asked me to pick up olive oil so she could cook dinner but in my carelessness I got canola oil instead. When she realized my mistake she raised her voice, and began scolding me. She was on a major health kick, and was reading a book on the “dangers of industrial seed oils” as she phrased it. She was getting kind of neurotic about only eating foods that were cooked in butter or olive oil. I got defensive, and told her to “get off my back.”
She wouldn’t have it.
“Go back, and go get what I asked,” she commanded.
I gave her a look of disbelief, but she stared me down until it became clear that she would not relent. I turned around, picked my keys up off the counter, and went for the door.
“You better make it quick too!” she snapped.
I reached for the door knob, and without even thinking about it I cursed her under my breath.
“Uhhh, what a bitch,” I muttered. I flung the door open, slammed it, and left.
While I was at the store I put the olive oil in my basket, and picked up a bottle of wine as well. My step-mom obviously needed something to calm her nerves I thought to myself. As I got in line I heard my text tone: a single high-pitched ping that pierced the noise of moving shopping carts, and conversation. I pulled my phone out from my back pocket, and it was a text from Ashely.
“I heard what you said,” it read.
Reading those five simple words were enough to make my palms start to sweat. I texted back a quick apology, hoping to diffuse her anger.
The clerk interrupted me just before I hit send, and called me forward. I sent off the text, and placed the wine and olive oil on the conveyer belt. He was friendly, and asked if I was gonna drink both the wine and the olive oil tonight, or just the wine. I wanted to tell him not to quit his day job, but I gave him my best attempt at a chuckle, paid for the items and left the store.
I heard the ping of my text tone once again.
“Paddle or belt?” her text read.
I called her right away. I had to try to smooth this over if I could. The call went straight to voicemail.
She texted again: “I’m waiting…. You have one minute to respond before you make this worse on yourself.”
“Fuck!” I said under my breath as I continued walking through the parking lot.
I quickly got to the car, opened up the passenger rear door, and set the bag down on the seat. I texted back as quickly as I could.
“Paddle.”
“Thank you” was her only response.
As I drove home I was a bundle of nerves, as I typically was when I was about to get spanked. What’s worse is I had no idea if it would happen as soon as I got back, or if she would make me wait for it.
When I walked through the door, I could hear the sink running. I placed the groceries on the kitchen counter, and removed my sunglasses. Ashely was at the sink washing a head of lettuce. The paddle was fit snugly into her left back pocket. I normally didn’t mind getting a quick glance at her ass, but seeing the instrument of my own destruction took the fun out of it. Well, some of it anyway.
“Did you get olive oil this time?” she asked, looking out the window above the sink.
“Yes,” I replied.
“Gooood,” she said, turning off the sink. She reached for a hand towel, and starting drying her hands as she turned to face me.
“Robby, I’m sorry that I snapped at you. I’m under a lot of stress today. But cursing at me is not ok. You know that.”
I looked at her sincerely, and let her see my pained expression.
“I’m sorry Ashely, I didn’t mean it. It was a mistake.”
“Good, I’m glad you’re sorry,” she said matter of factly. She finished drying her hands, and put the towel back on the metal ring above the sink. “Let’s make sure you never make that mistake again.” She pointed at the living room sofa just 10 feet behind me. “Now go bend over the arm of the couch. And I want your ass bare for this one.”
I wanted to protest, but I knew that would land me in even deeper trouble than I was already in. I swallowed my pride, turned around, and headed for the couch.
As I dropped my jeans, and got into the humiliating – yet all too familiar – position over the couch I could hear her getting dinner started. The normally pleasant smells and sounds of food being prepared was tainted by the anticipation of the painful chastisement I was about to receive.
The only other time I had received that paddle on my bare bottom was that very first spanking that Ashely gave me after I snuck out of the house. That was not something I was looking forward to feeling again, to put it mildly. I lay there over the arm of the sofa with my naked ass up in the air, and all I could do was listen to sound of sizzling olive oil, and boiling water knowing that my ass was also on the menu of things to be roasted that evening.
I looked up at the clock on the wall to my left. It was seven PM. I waited in agony, looking up at the clock every minute or so. Time seemed to slow to a crawl. I looked up once more and it was 7:05. I could hear Ashely’s footsteps. It was time.
She stood beside me, and I buried my head in the sofa seat. I felt the touch of the paddle on my left butt cheek. Then she spoke firmly.
“You’re getting ten. They’ll be hard, and you’ll count each one and say ‘I’ll never be disrespectful again’. Is that clear?”
“Yes Ma’am,” I replied.
I felt the sting of the first smack. It was nasty, but bearable. I let out a loud moan, and tried to exaggerate a bit so she would go a little easier.
“One! I’ll never be disrespectful again!”
She must have known I was faking it a little cause the second smack was one for the record books. I let out a silent gasp, and let out an “owwwwww” under my breath.
“Come on…let’s hear it,” she said.
“Two!” I replied as gathered my whits. “I’ll never be disrespectful again!!”
The next four strokes came just as hard, and I whimpered after each one before saying my line of repentance.
Smack number seven was more than I could take. I reached back and grabbed both of my butt cheeks, and howled. Ashely waited patiently for me to move my hands away and count the stroke.
“This can take 30 minutes, or it can be over in five. It’s up to you,” she said.
“Seven. I’ll never be disrespectful again!!” I muttered in a shaky voice.
I felt the weight of her hand on my lower back, and I knew the worst was coming. Number eight, and number nine may have been two of the hardest strokes I ever received during a spanking. I held still as best I could, and obediently muttered the count, and my scripted apology. I jerked up up, lifting myself off the couch, but Ashely firmed her hold on my back.
“Ok, last one,” she said. “Hold still cause it’s gonna be a good one.”
It wasn’t nearly as hard as the previous three, but my butt was in such poor shape that the pain of that spank was probably the worst of all. I broke just as it landed, and I began to cry softly as I said my penance.
“10. I’ll never be disrespectful again.”
“I hope those tears are a sign that I won’t be hearing you use language like that to speak to me ever again,” she said.
“Yes ma’am,” I replied as I sobbed. I lay there draped over the sofa and let my tears drip shamelessly onto the seat cushion. Ashely took pity on me, and knelt beside me. I felt her hand graze across my bottom.
“There, there sweetie. It’s all over. I know that really hurt, and it hurt me to have to do it to you, but I need you to learn respect for me, ok??”
I nodded in agreement.
“Well, dinner’s ready, so wash up, and I’ll make a plate for you.”
I lifted myself off the couch, and Ashely turned away so I could preserve some dignity while I pulled my pants back up. She placed the paddle on the coffee table that sat just in front of the couch.
“Make sure this gets back to the closet,” she ordered.
“Dinner’s in five minutes.”
I did as she told me. That evening the two of us had a delicious meal of chicken cacciatore with angel hair pasta.
It’s too bad I had to eat it standing up.
Act 2:
Perhaps one of the reasons that that October day stands out in my memory is that it was the day after the very last time I was ever punished by Ashely. After that evening with the paddle we started getting along well again, and then six months later I got a job as a personal trainer. Within only a couple of months I had enough clients to start looking for my own apartment.
Personal training was somewhat of a new thing for me. Once Ashely put a stop to my sneaking out and using drugs, I took up working out as a new hobby. Within a year I was in the shape of my life, and I was starting to train friends of mine who wanted to see the same results. I was feeling more confident than ever. I had washboard abs, and a v-shaped frame that was starting to make more than a few women take notice.
Surprisingly, Ashely seemed to be noticing me as well. It seemed that she was lighting up when she saw me, and she touched my biceps and teased me about my “big man muscles” at least once a day. At times her hands would linger for a second too long. I thought it was strange at first, but I was flattered. With my Dad out of the picture it didn’t really feel like Ashely was my step-mom. It was more like living with a very strict, yet affectionate landlord.
It wasn’t just my muscles that were getting stronger. I had become more responsible, and disciplined. Ashely looked at me, and spoke to me now as if I were her equal. That sudden sense of equality and closeness between us was confusing for me. At times, I found myself replaying some of the times she spanked me in my mind, and thinking on it almost fondly. Once while I was pleasuring myself I shot my biggest load ever thinking about one time when she called me a “bad boy” over and over again while she belted my bottom in the living room.
When my 21st birthday came we found ourselves alone in the house. It fell on a Monday, and so I had had a big party the Saturday prior. She was nice enough to let me go out with my five best friends, and she didn’t ask questions when I came home at 2am. I thought that the celebrating was all over after that but to my surprise when I came home on Monday evening from school I found two boxes covered in wrapping paper on top of the coffee table in the living room.
As I walked in I could hear Ashely working on something in the kitchen. She came into the living room holding a glass of red wine in one hand and what looked like a mixed drink of some sort in the other. She smiled as she saw me.
“Happy Birthday Robby!!”
“Thanks!” I replied. “You’re drinking hard tonight!”
She laughed. “No silly! This one’s for you. I made you a Jack and Coke. Your first legal drink.”
She handed me the glass and raised hers into the air.
“Here’s to being all grown up,” she said with a smile.
“And to never getting spanked again??”
We both laughed as she replied. “Deal.”
We touched our glasses together and took a sip of our drinks. Ashely turned toward the gifts she had placed on the table and gestured toward toward them.
“Speaking of which, I got you a little something, but before you open those I actually have another present for you.”
She went over to the boxes on the coffee table and tilted them to the side. From the bottom she pulled out her wooden paddle. She walked over to me with an embarrassed grin and handed it to me with the handle on my side.
“I’ve decided to grant your request,” she said as our eyes met and her smirk grew into a smile.
I took the paddle in my hand, and gave her a perplexed look. “But that was kind of a joke…I mean, sure I would love to get my revenge but I wasn’t actually suggesting that I should spank you.”
“I know,” she said. “But I thought about it and I think you actually had a point. I’m not sorry that I disciplined you the way that I have, but there have been times when I was too hard on you, and also times when I punished you for things you didn’t deserve to be punished for. So for your birthday I am giving you the once in a lifetime opportunity to get me back for all of those times. I trust you to be fair. If I can’t take it then I will simply ask you to back off or to stop if needed. But I promise to take my punishment to the best of my ability.”
I looked down at the paddle and stared at it for a moment. Spank my step-mom? Is it opposite day? I thought to myself. I took another sip of my Jack and Coke. The buzz was starting to set in already.
“Are you sure?” I asked
“Yup! Don’t worry honey, I’m a big girl. I can take it.”
“Wow…um…ok then! How did you want to start off?”
“Well,” she said. “I typically used the belt and the paddle on you when you were in the most trouble So I will let you give me a spanking with each one.”
“How many?” I asked.
“How many…strokes?” She said raising her eyebrows slightly.
“Yes, how many strokes,” I replied smirking in anticipation.
“Completely up to you. Position, clothing, how hard…You give me the punishment that you think is fair, and being fair is all I ask. Again, if it’s too much I will let you know. But, as you know, I never gave you that as an option so I will try my best to take it.”
I couldn’t help but smile from ear to ear as I began nodding slowly. I took one more sip of my drink, and handed it to her. She took it and looked at me, awaiting my first instructions. I leaned the paddle against the back of the sofa.
“I wanna use the belt first. Your belt,” I said.
Without hesitation she turned toward the coffee table and put down our drinks. She turned toward me and removed her belt just like she had done so many times since that fateful night that I snuck out to buy weed. But this time she folded it in half, and handed it to me.
“This is a once-in-a-lifetime opportunity you’re getting here, so make it count!” she said with a chuckle. She turned around, and bent over. Her bottom widened, and filled her blue jeans as they stretched across her cheeks.
She reached over and took a sip of her wine. She held the glass in her hand as she looked back at me.
“I’d put the drink down if I were you,” I said.
She placed it back on the coffee table. I wrapped the studded side of the belt around my right knuckles just like she did when she whipped me.
Ashely stood up, unbuttoned her jeans, and let them fall below her calves before bending over completely, and grabbing her ankles. Her panties were pink, and across them in gold letters they said “Happy Birthday!”
I was dumbfounded. Neither of us said a word. I drew the belt back and whipped it across her bottom.
“Owwww!!!” she cried under her breath as she lifted onto her toes. I stood there for a moment, and stared. I couldn’t figure out if I wanted to give her the rest of her punishment of just admire the sight of her beautiful backside so vulnerably on display for me. This was quite a thoughtful birthday present, indeed.
I laid another stroke across her panties and elicited the same reaction. I could feel my manhood beginning to swell. I delivered another. This time she let out an “ohhhh” that sounded every bit like an expression of pleasure as it may have been one of pain. Hearing her moan at crack of the belt was intoxicating.
I continued to punish her, now whipping her with vigor and feeling the tip of my dick becoming wet. I laid what must have been about 30 strokes across her bottom, three or four whips at a time. She hissed, “ooohed” and “ahhhhed” with each whip of her belt, but she never broke position. I decided I’d end that particular part of the punishment with three strokes, delivered with all my might.
“Hold still young lady. These are gonna be hard!” I warned her. She giggled and cleared her throat before replying, “Yes sir!”
Her laughter ended as soon as the first hard stroke whipped across her bottom. She yelped loudly, and came up on her toes. Before she could put her heels back down I striped the next two right across the gold lettering. She stayed there in position, silent, save for the sound of her breathing, now ragged and heavy.
“Alright, I think you’ve had enough of the belt” I declared as I unraveled the leather from my fist. “Go ahead and put yourself back together.”
She stood up, and turned around to face me as she pulled her pants back up. There were tears in her eyes, but she was still smiling. I handed her belt back to her. She took it, and our eyes met. Hers darted down for a second, and then came back up as she gave me a mischievous smirk.
“Sweetie? You’re…”
I raised my eyebrows as she paused mid sentence.
“You’re hard as a rock,” she observed as she chuckled into a wide grin.
“Wait, what?” I asked as if I hadn’t heard her.
I looked down and noticed that my dick was poking conspicuously out into the stretchy material of my gym shorts. I felt my face go completely red.
“It’s ok sweetie!” she assured me. “We’re not related, so I understand if seeing a woman bent over turns you on a little. Don’t even worry about it.”
I sighed a breath of relief, and smiled as I looked at the carpet. “Ok,” I said, feeling somewhat reassured.
She placed the belt on the coffee table, and zipped her pants. She let the top buttons remain undone. She stepped toward me, and leaned into my ear.
“Wanna know a secret?” she whispered.
“Sure!” I responded, smiling with excitement.
I felt her hands rest on my shoulder. She cleared her throat and whispered in my ear once more.
“Umm…sometimes…I get wet…”
“Yes?” I replied, still looking at the carpet.
“When I spank you,” she said..
As I heard her words, it was as if I was hearing a foreign language. The sounds she made were perfectly clear, but their meaning was lost on me until I gave them a few seconds for them to sink in. As they did, I stood there next to the sofa, still as a statue, unable to utter a word.
She stepped back, and buttoned her jeans. She swallowed, and looked down. Her face had a look of regret. She picked up her belt off the coffee table and began putting it back on. I decided to say something…anything to break the tension.
“Is that why you decided to start doing it?” I asked
“No! It’s not like that!” she snapped. “I mean it’s…you know what forget I said that. Let’s just get the rest of my punishment over with.”
“Well you noticed me getting hard from spanking your ass so I’d say we’re even now as far as embarrassing secrets are concerned,” I argued. “Tell me more. I’m curious.”
She buckled her belt, and took a deep breath. “Well, shall we have a seat for a minute?”
“Sure” I replied.
She turned toward the coffee table and picked up both of our drinks. She handed me mine. It was watered down now, but I was grateful to at least have something that would make the conversation we were about to have little bit easier. We both took a seat on the sofa. Ashely continued to explain.
“I definitely started disciplining you for all of the reasons that I gave you. But I did notice that sometimes my body responded to it in a certain way. I guess I didn’t realize that punishing you in such an intimate fashion might have some unintended consequences. But guessing by your reaction to spanking me it seems that you might relate.”
We each sipped our drinks as I thought for a second.
“Yes, I can relate,” I replied, feeling my heart begin to race at the sound of my own words.
“Good, I’m glad you feel that way,” Ashely said as she smiled and looked down at my crotch. She scooted closer to me. I could smell the same perfume on her that she typically wore when she went out on dates. The scent was intoxicating.
“Well, it seems we might need to do something about this…situation here, don’t you think?” she teased making a circular motion with her finger around my bulge, still protruding visibly.
“Well, I still live in your house, so you’re the boss.”
Her index finger continued its circular path around its target. I watched it as it descended slowly, like a spiral, closer and closer until, finally, she touched it – first with only her first finger, then with each of her fingertips. She began messaging the tip. I closed my eyes and let out a loud exhale.
“You are a bad boy, you know that?”
I nodded emphatically, my eyes still shut.
“It’s a shame I already agreed to stop spanking you…”
I reacted immediately. I crawled, as if by instinct, across her lap and pulled my shorts, as well as my boxers down to my thighs, exposing my bottom just as I had always had to do when Ashely punished me. Her hand remained on my cock until I positioned it against her thigh. I began to thrust up against it.
She responded with three sharp smacks to my exposed bottom. “Robby, how dare you do such a thing!”
“I can’t help it. You need to punish me!” I exclaimed, breathing heavily.
She continued spanking. Each smack of her hand was just hard enough to make me squirm. The pain only to drove me deeper into my arousal, and submission.
She laid about 10 smacks on my bottom, and then began to stroke her delicate fingers across my cheeks. I moaned, hoping that my sounds would encourage her to take things further. It wasn’t long before I felt her fingertips caressing my balls.
“My, my Robby, you have some very big balls,” she said with a girlish giggle. I giggled in turn.
“Thank you…you have some very delicate hands,” I replied as I continued to thrust against her thigh.
“Thaaaaaank you. Well….young man…”
“Yes?” I replied. My mind began to race thinking of every possible thing she could say next.
“Robby, I think you should get two things for your birthday that you have never had before. One is a good birthday spanking. The other is a thorough lesson in how to please a woman…”
I had no idea what either of those entailed in exact terms, and there was something about the playful tone of her voice that drove me wild with curiosity. I lifted my hips, and her hand moved to my shaft as she began to gently stroke it.
“What do you have in mind exactly?” I asked.
“Well, a birthday spanking for a naughty boy like yourself means that you get one spank for each year. But if you’re a really good boy for me, then I will make sure that spanking culminates in a very happy ending…”
“And what about the other part?”
“The other part is where you learn to pleasure me first. Think of it as a very fun sort of…right of passage.”
“That sounds like the best birthday present ever” I said, now thrusting slowly into her hand gripped gently around my erection.
“Ohhhhh does it now???” she said sounding both surprised, and amused. “I hope you realize that any failure to meet my expectations will result in the immediate thrashing of your bare little bottom.”
“Well…” I replied, now feeling the tip of my cock wetter than it had ever been. Ashely’s finger tips circled at the top, using my wetness as lubrication. I felt like I might come right then and there. Surely, soiling her jeans would earn me a spanking I’d never forget.
“Well, what young man? Cat got your tongue?”
“Well, I guess I…have to learn somehow right?”
“Yes, you do. Is there anything in particular you’d like to do to me? Or anything in particular you’d like me to do to you?”
“I want to do whatever you tell me Ashely. Just like when I get punished.”
“Good answer sweetie. Her voice suddenly went from playful to firm. “Now get your ass up off of my lap and go to my room. Clothes off. I want you on your knees.”
I lifted off from her lap. She pulled my shorts and boxers off and held them in her hands. She stood up with me and reached for my shirt. My hands went straight into the air as she pulled the shirt over my head. I stood there naked, my erect cock pointing up toward her. I bent down to take off my shoes.
“Oh no no no…” she snapped as she touched my chin and guided me to my feet. “I said clothes off. You keep your shoes on for now. You look rather silly being naked with your sneakers on. I think I like it.”
“Yes ma’am,” I replied. I stood there awaiting permission to proceed.
“Ok, now go!” she commanded giving me a sharp slap to my behind. I scurried up the stairs, and shut her bedroom door behind me.
As I waited for Ashely to come up my thoughts began to drift to all of the things she might have me do for her. I was fairly certain I would be required to bury my face between her legs and make good use of my tongue. Would she tie me up? Would she peg me with a big black dildo? Or maybe she’d have me suck on her nipples while she pleasured herself to orgasm. I was happy to try any of those things as long as I would get to come at the end of it all.
I didn’t have to wait for long. She came in only minutes after I knelt on the carpet. She was naked, and holding a black riding crop in her right hand. Just like the night that she spanked me for the first time the room was dark, but the moonlight came in through the window, and reflected on her skin beautifully. Her pussy was shaven save for a patch of brown hair that ended at the top of her lips. It looked freshly trimmed. I stared up at her in awe of her beauty.
“Close your eyes you little pervert! I didn’t give you permission to look at me with my clothes off now did I?”
“I’m sorry miss Ashely,” I replied as I shut my eyes. I felt three sharp strokes on the right side of my bottom from the riding crop. I winced, and lifted my butt up.
“If you open your eyes without my permission again you’ll get double that, is that understood?”
“Yes ma’am,” I replied.
She chuckled. You still have a throbbing erection, and I haven’t even been in the room. You must really like this sort of thing. Is this the kind of stuff you like to masturbate to on the internet young man?
“No Miss Ashely. I mostly watch lesbians. But I have thought about it before. And I think I like it…a lot.”
“Good boy. You may open your eyes, and crawl towards me. I want your mouth on my pussy. If I find myself getting bored at any point you will receive a stroke with my crop. If you remove your mouth without my permission you will receive a stroke as well. Now come here and get to work.”
I crawled as commanded. I knelt beneath her worshipfully, and placed my hands at her calves. I inched upward, feeling the silky skin of her legs. Finally I grabbed onto her butt cheeks and slowly kissed her thighs as I moved my mouth toward her sex. I felt a sharp sting on my behind.
“owwww!” I cried.
“You’re taking too long. I didn’t tell you to cop a feel. I told you to pleasure my pussy.” Her voice was a delicious mixture of firmness and gentle femininity. I placed my mouth directly over her sex and began to trace her opening with my tongue.
“ohhhhh you’re off to a good start…” she said breathing heavily.
“I continued along the same path until I felt the crop against my bottom once more. I went in a little deeper with my tongue and began licking up, and down.
“That’s better…” she said.
I continued to pleasure her until her pussy was a wet mess of her juices, now beginning to drip into my mouth. I began making circles around her clitoris. She moaned loudly and clenched the back of my head with her free hand.
“Ohhhh, good boy Robby. You’re learning so quickly!”
I continued for a while until I felt the sharp sting of the riding crop return to my now tender bottom.
“Faster!”
I obeyed.
“No faster! That’s not good enough!” she snapped as she whipped me twice more. I moaned, and moved my head away from her. I looked down for a second to see that my cock had not lost a bit of its stiffness. In fact it was glistening at the top with fresh cum.
She opened her eyes and looked down at me as our gazes met. “I did not give you permission to remove yourself,” she said, pointing her finger down at me. Quickly, I dug my face between her legs once more and went back to work, this time licking as fast as I could. I heard the crop fall to the floor as both of her hands now clasped the back of my head.
“Ohhhhh Robby!!!! Yes, that’s it!!!! Keep doing that!!!”
Her juices were dripping into my open mouth even more as I lapped her sex as fast as I could.
“Ohhhh that’s sooo good sweetie!” she said with labored breath as I continued to lick her. I continued as she moaned, and stroked the back of my head. After a few minutes her juices were dripping right off of my chin and onto the carpet.
She pulled away from me, and held my head in place as she caught her breath. She jumped onto the bed and lay on her back. She spread her legs and smiled at me as she made a come hither motion with her index finger. I stood up and walked over to join her on the bed. My cock was still stiff as a statue.
“I want you to fuck me while I beat you with the crop,” she said, locking her eyes with mine.
I stood there for a moment, transfixed by the beauty of her naked body.
“Don’t just stand there. Get it for me!” she snapped pointing down at the crop on the floor.
Startled out of my lustful stupor I bent down and picked up the crop. I crawled onto the bed and placed it beside her. She reached out and pulled me toward her. Our lips met and we began to kiss passionately. Her hands roamed hungrily across my body as she touched my back and then reached down to my butt. She squeezed my cheeks hard, and pulled me closer to her. I began to kiss her neck and inch in a little closer until I felt my cock touch up against her wetness. Thoughts began to race through my mind. What if I got her pregnant? What if someone found out about us? Yet the feeling of her soft skin on my lips, and the sound of her heavy breathing made it seem like nothing else mattered. I had to have her. Whatever the cost.
Just as I began to push into her I felt the sting of the crop.
“Ahhhhh!” I cried.
“You don’t get to go inside without my permission!” she said as she kissed my lips and put her nose against mine. And also, you’re the perfect height to suck on my nipples while you penetrate me. So get to it.”
I obeyed her, feeling like my cock might explode if she gave me another firm command to pleasure her. The sound of her voice when she scolded me was intoxicating. I started with her left nipple, making circles with my tongue. The crop whipped me twice.
“Suck it harder please.”
I sucked harder, and once again I felt her hands at the back of my head once more. I sucked until I thought I must have been hurting her. But her only response was to reach down to my ass and pull me in until my cock was finally buried inside her warm wet pussy. I had never penetrated a woman without protection, and it was every bit as wonderful as I imagined. I thrusted into her again, and again as I sucked on her nipple, now moving on to her right side. After a few minutes she could tell I was starting to lose control. I felt the hardest of the whips from crop on my right butt cheek. I pulled away from her breast and and cried out loudly.
“OWWWWW!!!” I said as I forced myself to continue thrusting.
The sharp, sudden sting of the crop had its intended effect, causing enough pain to keep my orgasm at bay. I pushed into her faster, feeling my erection coming back to life. I whispered into her ear.
“Ashely, you’re gonna have to whip me more than that to keep me from exploding inside of you.”
She gave me a sloppy kiss, making liberal use of her tongue. “It’s ok baby. It’s your birthday. I’ll let you come first only this once. After tonight, if you ever come before I do, I will whip your bottom every day for a week, is that clear?”
“Yesssss Miss Ashely,” I replied as my breathing became even more ragged.
“Good boy,” she said. “Now let’s give you your birthday spanking.”
I felt the crop once more. This time it was stingy, but bearable. Feeling the slippery inside of her pussy at the same time caused the sting to melt into pleasure.
“One,” I said, thrusting into her a little more aggressively.
The next stroke came quickly after.
“Two!” I said a raised voice.
“Three!!” I cried out as the third stroke landed on my left side, a little bit harder than the other two.
“Four…five….six!!!” I said, nearly screaming. I was now pushing into her forcefully and feeling the blood rush to my head.
The seventh stroke came down hard on my right side and I couldn’t hold back any longer. I pushed into her and it felt as if every fluid in my body rushed down and poured out from my cock as I came into Ashely and screamed at the top my of lungs, “Ohhhhhhh…seven!!!!”
I heard the crop fall to the carpet and Ashely pulled me in close to her. We embraced as I spurted the last of my come into her and trembled on top of her. We stayed there for several minutes without speaking a word.
“Happy Birthday sweetheart,” she said as she kissed my forehead.
“Ohhhh, thank you so much Ashely. That was the best birthday present I could have ever asked for.” I pulled out and rolled over to my back. She rolled onto her side and began rubbing my chest.
“You’re welcome Robby. And don’t worry, I’m on the pill. Do you want to do it again after dinner? Maybe you can be in charge, and you can finish the job you started.”
“Well,” I replied with a smile as I turned my head to face her. “I do still owe you a paddling.”
She kissed me and smiled back. “Whatever you want birthday boy. I made dinner already. Let’s wash up, and go eat.”
A Tender Moon 