Author’s Note: All the characters in the story are 18 or above.

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My name is Dave and this took place in the summer of 1999 in the modest town of Willowbrook. I was raised by my single mother who had me when she was just 19 years old. We lived in our family’s big house and her best friend, Jacqui, had a house just a few blocks away from us. She frequently spent time at our place.

My mom and Jacqui were just in their early forties, but didn’t look their age. My mother was very attractive and youthful in appearance, but Jacqui was crazy hot. Since she was around the house alot and often wearing skimpy outfits, I used to fantasize about her at all times. Once I got into my mid teens and started working out, she used to jokingly flirt with me all of the time. She would even do this in front of my mother. Most of it was nothing more than just some harmless flirting, I even wondered at that time that she was just doing this to make me feel good about myself. And I seldom said anything in response, just laughed it all off.

I had sort of a love/hate relationship with her daughter, Robin. Our mothers had her babysit me growing up. She was a stunner like her mom – tall, athletic, with great legs, an amazing ass, and big boobs. I’d had a crush on her forever. She was four years older than I was, and developed sooner. But she was sort of a bully – used to flash a little hint of cleavage now and then, and laugh when she caught me gawking. Once I turned 18, she teased me at all times because I had a hard-on most of the time, which she found hilarious, and she’d joke about how much I was ‘growing,’ while staring at my crotch.

The most exciting and embarrassing time came when I was hanging by her pool in her backyard along with her and a couple of other of her girlfriends. It was days before I was gonna move away to another state for university. Robin was enjoying bossing me around. I made the mistake of saying that she couldn’t tell me what to do… She laughed at me, and said that I still wasn’t too big for her to spank me. I blushed, remembering how she had done so years ago. She said that she would do it right then and there if I didn’t behave, and the other girls just egged her on. But then I scoffed, and before I knew what had happened, she’d knocked me down on the grass, and had me over her knee. Down came my trunks, and she started spanking my ass there in the sunshine, with her girlfriends looking on with wide eyes and amusement, laughter bubbling up from their open mouths.

“That’s for being mouthy. And that’s for thinking you’re too good for me.” After the initial shock, I struggled, but she was stronger than me, and managed to put one muscular leg over me, so I squirmed helplessly while she slapped my ass red. She commented, “Looks like you’re not too tough after all.” I blushed, trying my best to free myself and cover up. But she was having none of it.

“Are you done being a smartass yet?” She asked me sternly between spanks. “Yes!” I managed to choke out through gritted teeth as embarrassment washed over me.

Finally, what felt like an eternity later, she was done. She gave me one more swift swat and announced, “Alright we’re done here”, then getting up and standing in front of me with her arms crossed as I sheepishly stood up while trying to cover myself. Her friends still snickered from their spot by the pool while Robin just watched quietly with a satisfied smirk upon her face. Just as I was pulling my shorts over my semi-erect penis, Robin noticed my hard-on, she laughed at me again and called to her friends, “Guys, I found a cock!” One of the girls, Jessica, asked, “How big is it?” and Robin replied walking back to them, “Don’t worry, it’s not too big.” I blushed furiously at “it’s not too big”. Those were the last words I heard as I ran the hell out of there.

I don’t know how many more people got to hear about the spanking. I worried if my mom or Jacqui ever found out about it, but I was glad that I was on my way to university a couple of days after. Yet it bothered me very much when I realized that Robin saw my everything before I left and I never got to see anything of her.

Her and her mom’s memories kept appearing in my mind all through my first year of school life, to which I jacked off to every now and then. Only by my second year, after I got a girlfriend and fooled around a little bit, did they slowly start to fade away from my memory.

Cut back to the summer of 1999, I’m 23, and much stronger than I used to be. A handsome young man standing at 6’1. I had just finished school a week ago and moved back in town with my mom. I remember I’d spent most of the morning that day, at the town beach, checking out the pretty girls in their little swimsuits, and I was ready to head home, rinse off in the shower, and have a wank. As I walked back home with my t-shirt and towel over my shoulder, I saw my mom exit, get in her car, and drive off. I waved, but she didn’t see me.

When I walked in, I saw that Jacqui and Robin were visiting. They were sitting out on our fenced-in patio, and were finishing up a pitcher of margaritas. I wanted to hurry upstairs and begin wanking, but I couldn’t withstand the chance to catch a closeup look at both women in their swimsuits.

Jacqui was wearing a yellow bikini that would have gotten stares on any beach, and Robin was wearing a one piece, body-hugging black suit that was cut dangerously low in front and equally high at the hips. Their legs glistened like they had been dipped in oil.

Jacqui spotted me and called me over. I threw my t-shirt and towel on the couch in the living room before I walked outside, I think I wanted to impress them with my physique. I was happy to lean over and give her a kiss on the cheek. Especially since I could look right down her cleavage as I did so. I was still semi-erect from staring at girls on the beach, but the sight of her boobs glistening in the sunshine was… inspirational. She said that my mom had just gone to get tequila, and would be back soon.

Jacqui ran her hands on my chest and shoulders, saying, “Oooh, look at you! Big chest, broad shoulders, someone’s been busy working out.” I just blushed and awkwardly chuckled along. Then she commented on how cute I looked in my short little trunks, and how I’d have to be careful, or I’d get a sunburn. “And that wouldn’t look good next to your cute little candy-white ass!”

I blushed, and said that it didn’t matter, as no one was going to see my ass, candy-white or not, anytime soon. She laughed as Robin said, “Don’t be so sure! I might just pull down those trunks and spank your lily-white ass, like I did when I was your babysitter.”

It was then that I made my big mistake. I was trying to act tough, so I smirked, and said, “You wouldn’t dare.”

Jacqui, who seemed a little tipsy, whooped, and said, “Tell me you didn’t just say that!”

Robin laughed hard enough to spit part of her drink all over her (impressive) boobs, and, while wiping them off with a towel, said, “You didn’t just dare me did you? You think I won’t pull down your trunks? Bring your pretty little ass over here!”

Remember, I was young and cocky, and I seriously didn’t think she’d pull my trunks down with her mom right there. I didn’t want her to think she could still bully me, so I walked over, and stood before her. As I got close to her, she leaned forward from the chair and actually pulled me right up to her. I was getting harder at all times, standing right between her bare thighs, looking down at her cleavage. I could see her hard nipples poking through the fabric, and a cameltoe peeked through in between her legs. But honestly, I wondered she’d just laugh and push me away. I almost couldn’t wait for all this joking around to end so I could head for the shower and give myself a long overdue jack off session. Just as Robin pulled me close, she looked up at me and said, “Do you really dare me, because I’ll do it. Dare me one more time”.

I was kind of looking at Jacqui to see how she was responding to things. As I looked at her, she grinned, and said, “Don’t look for me to help you – you got yourself into this.”

I didn’t see a good way out of this predicament, but I was still sure she wouldn’t do anything with her mom right there. Well, 90% sure. Maybe 80%.

Just as I told Robin, “I dare you,” her mom just started shaking her head from side to side and said, “You should have never dared her, I don’t think you know what you’ve gotten yourself into.” As she said this, I felt Robin grab the top of my waist band. The drawstring was just barely visible at the top of my shorts, but the string was actually tucked into my trunks. My former babysitter then took both hands and actually pulled out at the waist band while reaching down with just her fingertips to retrieve the drawstring. My cock had already been half hard from just spending time on the beach checking out pretty girls, but by this point it was raging, and standing at full attention.

While Robin was fishing out the drawstring, she actually brushed my dick with her finger tips a couple of times. She never said anything about feeling my cock, but I now wondered she might really go through with her threat. After she retrieved the drawstring, she started fumbling with the knot.

It seemed like it was taking an eternity for her to untie the knot. I was actually starting to hope that she was just gonna untie the knot and push me away at any moment, everyone would have a good laugh, and it would all be over. But I was really starting to get worried. What if she did actually pull my shorts down? I could imagine how humiliating this would be! I could only imagine how embarrassing it would be to stand completely naked in front of them with a raging hard on! What would they think?

Just as she was in the final stages of getting the knot untied, she turned her head towards her mom, and said, “Remember, he dared me.” Jacqui just grinned and said, “Oh I know – he dared you, do it!” Once again, I would have never expected this out of my mom’s old friend. I was now sure that Robin would indeed pull my shorts down. I saw her last statement to her mother as kind of making sure she was comfortable with everything. And Jacqui certainly gave her the green light.

Just as the words came out of Jacqui’s mouth, Robin leaned towards my torso, pulled the waistband out a little and peered down my shorts at my hard cock. I too looked down and saw that she was having a clear unrestricted view of my penis. Her mom just died laughing at this. This was just as humiliating as I expected it would be, but I was relieved that all she was gonna do was just peer down my shorts for a brief glimpse. That was bad enough, but not nearly as bad as it could have been.

Just as she finished looking at my erection, she leaned back a little and looked at her mom, and said, “You have got to see how hard this boy is!”

And with that, she grabbed both sides of my waist band and pulled my trunks down with one swift motion. My nightmare was coming true. I couldn’t have been more embarrassed as I looked down and saw that my entire package was now fully exposed to these women. My dick was standing straight up as she pulled the trunks down to my calves. Jacqui just roared with laughter and leaned back on the chair- and even clapped a few times! Robin leaned back and smiled with a wickedly sexy smile on her face. It was even more humiliating than I ever imagined. I just stood there for a moment not really knowing what to do. Each second seemed like an eternity. I knew I should cover myself, but I was paralyzed… I couldn’t even look the two women in the eye anymore. I just stood there for a couple of moments just looking down at my hard dick.

Finally, Jacqui broke the silence by saying “Well I think we can all agree that this young man is certainly excited to see us!” To which Robin responded with, “He definitely looks ready for something.”

Probably only a few seconds had passed when I started to lean over to pull my shorts back up. I still didn’t want to appear to be too embarrassed to the women, and hoped I could play this off without making it seem like a big deal.

Just as I started to pull my shorts up, Robin stopped me and said, “Oh hell no. You wanted us to see you naked, I want to see that cute little white ass.” She then took me by the hips and turned me around. I felt a little relief as my dick wasn’t still on full display, but it was still embarrassing just standing there with my ass exposed to both of them. Thank goodness there was no longer any eye contact going on.

There had been no touching at this point, but Robin was now grabbing my ass with both hands. I had forgotten the touch of her fingers and palms on my butt, and now the sensation returned to me. I was starting to get more worried that I’d get spanked, but I guess I was resigned to that possibility at this point. Her mom then said something to the effect of, “Damn this boy has a nice ass.” She came close and grabbed a handful of my butt.

At one point, Robin even stretched my both cheeks, revealing my asshole. I couldn’t see them, but I could hear them giggle. When Jacqui slapped my ass a couple times, Robin said, “That’s right, spank his ass! He wanted to be naked in front of us, spank him good.”

Robin then held me by hips and turned me around again. She was treating me like the times she used to babysit me. She took me over her knee, and proceeded to spank me much harder than I expected. My cock was now resting on her bare thighs. I couldn’t believe what was happening. I had a feeling of Deja Vu, this was just like 5 years ago. My heart thumped with a confusing mix of fear and excitement, my body tingling with anticipation as Robin’s hand came down hard on my exposed ass again and again. Each strike reverberated through me, causing me to groan and moan despite myself.

-Plea.. SMACK..Ooh!

-SMACK

-Aao, please stop!

-SMACK

-Ohh, Robin, don’t!

-SMACK

Jacqui watched the scene unfold with amusement. I could feel my cheeks burn hotter with each swat as all the surrounding sensations built to a crescendo, until finally Jacqui said, “Let me spank his ass!”

I shuddered at the wondered of both women taking turns spanking me but I couldn’t deny the intense arousal that was building within me. Unbeknownst to them, I eagerly got off Robin’s knee and moved towards Jacqui. My trunks were around my feet and made it difficult to walk, Jacqui noticed it and said, “Let me help you”, she bent forward and had me first kick apart my flip flops, then had me step out of the shorts, then threw them apart. Rendering me completely nude from head to toe.

As I positioned myself to lay down on her knees, she rubbed her hand on the outside of my thigh and just looked at my erect penis. I realized that although Robin had seen my dick a few times before, it was a first for Jacqui. Her tentalizing lips were literally inches away from my cockhead, I could feel her breath on it. Jacqui then proceeded to spank my ass the same way Robin had done and she too kept at it for a while before finally finishing up with a few softer swats. When it was over Jacqui turned to Robin, “Your turn”.

Robin smiled and gestured to her mom to send me over to her. I felt completely emasculated with the way I was being sent back and forth to have my ass spanked.

Now it was Jacqui’s turn to laugh as Robin positioned me to lie down in her lap again. Yet before I could rest my body on her knees, she stopped me and opened her legs aside. “I want that here”, she said pointing to my cock and the space between her legs. She glanced back at her mom and whispered to me that I was leaking. I looked at my dick and I was indeed leaking pre-cum, I guess she didn’t want me to dirty her, so this time my cock and balls were resting in between Robin’s thighs as I got back in position.

From there on end, Robin spanked me hard and fast with a renewed vigor. I could feel my body getting hotter with each slap. After every couple of spanks, Robin would lay her hand over my butt and softly caress it like if I were a little baby or something. I don’t know how many swats in total they actually gave me, but this whole thing seemed to go on for a couple of minutes, at least.

After that, Robin let me up, and laughed at the fact that I was still erect. “I don’t think he minded too much…Let that be a lesson to you!”

Jacqui said. She flicked my cock with her finger, sending a jolt of electricity through me. When she did, Robin playfully smacked her mom’s thigh with an open mouth and Jacqui shrugged.

I was mortified, and had to leave. I couldn’t believe this shit was happening. I never imagined that I’d become such a joke to these women.

Jacqui smiled at me and said, “Now, he didn’t expect all of this, did he?”

I must have just stood there for a while in shock, as I’m sure they were expecting me to put my shorts on and run for the hills. But instead, I was gonna walk out of their lives, having spent the afternoon with nothing less than complete humiliation.

Robin told me to pick up my trunks off the floor and bring them to her. I picked them up and as I got close, Robin grabbed me by my wrist and pulled me up to her. As I stood facing her, she took the shorts from me and showed them in front of my legs, indicating to put my legs in, and I did. She reached around and pulled the top of my shorts back up and said, “This is the last time that you’ll ever dare me again.” Her mom just said, “Oh shit!”

They both laughed.

I tried to back off, but Robin held me in place by the back of my thighs. While tying the drawstring of my shorts, she said, “You’ll be thinking about it for a long time.” She let that statement sit there for a couple seconds before she said, “And when you do think about it, I want you to remember the fact that you had me right here and could have stopped me at any time.” She turned to her mom and added, “But he didn’t, did he?” Jacqui turned to me and said, “You wanted it – you got it.”

Robin tied my drawstring and tucked it back inside like before. She slapped me on my thigh and said, “Go back inside and think about it.” As I walked away from them with my tail between my legs, I heard Robin say to her mom, “I never thought it would work. I can’t believe that little bastard stayed hard the whole time we spanked him!” I could hear Jacqui say, “I think he’s gonna have a real problem beating that hard on.”

I didn’t hear the rest of their conversation, but I guess they were just talking about the whole situation. I had just stepped inside the house but Jacqui called my name saying, “Dave! You forgot your flip flops honey.” Robin and Jacqui were all smiles as I had to walk back outside to get them.

Utterly stunned and humiliated, I ran inside to the shower, when I masturbated furiously, and came in a matter of moments. As I leaned against the shower wall, I started to wonder…what would they tell my mom when she will get home?