Pantsed and spanked by my former babysitter and her mom

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Status: In Progress  |  Genre: Non-Fiction  |  House: Stripping and Humiliation

Spanked by my mom's best friend and her daughter, my old babysitter.

This took place the summer of 1979, just after my senior year in high school. I was raised by my single mother who had me when she was just 19 years old. We lived in a big apartment complex and her best friend, Jacqui had a house just a few blocks away from us. She was at our apartment all of the time. Both my mom and Jacqui were just in their thirties. My mother was very attractive and youthful in appearance, but Jacqui was crazy hot. Since she was around the house all of the time and often wearing skimpy outfits, I used to fantasize about her all the time. 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 thought 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 kind of a love/hate relationship with her daughter, Robin.  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 kind of a bully - used to flash a little hint of cleavage now and then, and laugh when she caught me gawking.  When I was 13, and just beginning to get my growth spurt, she teased me all the time because my voice was changing.  I also 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 swimming in her mom's back yard along with her and a couple of other of her girlfriends.  Her mom had left her in charge of me, and she enjoyed bossing me around.  I made the mistake of saying I was too big to need a babysitter, and that she couldn't tell me what to do...  She laughed at me, and said that I wasn't too big for her to spank me, like she did when I was a little kid.  I blushed, remembering how she'd done that years before.  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 and laughing.  After the initial shock, I struggled, but she was bigger than me, and managed to put one muscular leg over my thighs, so I squirmed helplessly while she reddened my naked ass...  It took several swats before I managed to get free, and pull my trunks up over my semi-erect penis...

Cut back to 1979.  I'm 19, taller, and much stronger than I used to be.  I'd spent most of the morning at the apartmen pool, 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 up to the apartment, I saw my mom exit the apartment, 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 out on our fenced-in patio, and were finishing up a pitcher of margaritas.  Turns out my mom had left to get more tequila...

I wanted to hurry upstairs and start wanking, but I couldn't resist 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, black suit that was cut dangerously low in front and equally high at the hips...

Jacqui called me over, and 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 at the pool, but the sight of her boobs glistening in the sunshine was...inspirational.  She said that my mom had just gone to the store, and would be back soon.  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 gonna 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 baby sitter.'

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 all the time, standing right between her bare thighs, looking down her cleavage, but, honestly, I thought 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 sort 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 finger tips to retrieve the drawstring.  My cock had already been half hard from just spending time at the pool 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 thought 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 going to 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 olf friend. I was now sure that Robin would indeed pull my shorts down. I saw her last statement to her mother as sort 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 waist band out a little and peered down my shorts at my hard cock. 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 going to 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 do 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.

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. Her mon then said something to the effect of, “Damn this boy has a nice ass.” She stepped near and swatted my  ass a couple of times.

Robin then said, “That’s right, spank his ass!  He wanted to be naked in front of us- spank him good.”

She took me over her knee, and the two women proceeded tp spank me much harder than the first two swats.  They each used a hand to hold me down and I was too shocked to do more that wail and squirm...

I  don’t know how many swats they actually gave me, but it seemed go on on for a couple of minutes, at least.  After that, they 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!"

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 got home?


Submitted: November 09, 2020

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Add Your Comments:

Comments

Storywriterx

He was probably thinking about their tits when he came imagining he was cumming on them. Think he enjoyed them spanking his ass as much as they enjoyed doing it.

Tue, November 10th, 2020 6:06am

LBS

Great story. Just the right pace to nicely highlight what everyone was thinking and expressing.

Tue, November 10th, 2020 3:08pm

Author
Reply

Very kind comment. Always appreciated...

Tue, November 10th, 2020 8:54am

qwertpoint

very good

Tue, November 10th, 2020 8:31pm

Igor

If the mother comes back with more Tequila and she's already drunk, I think she's going to want us to replay the scene ;-)
Bravo

Tue, November 17th, 2020 9:37am

Author
Reply

Many thanks...

Hmmm...there just might be room for a sequel!

Tue, November 17th, 2020 8:16pm

VanillaEssence

Nicely written
I think that the lesson learned here is to only take ONE woman at a time on.

Sat, July 10th, 2021 1:17am

Author
Reply

I'd hoped that having her mom there would keep her from doing anything.

I was wrong...

Thu, July 22nd, 2021 12:25pm

luvs2spin78

Hard to believe this is 'non-fiction' but what an awesome story. What 19 year old guy wouldn't want his 23-yr old, hot former babysitter and boyhood crush to pull his swim trunks down, place him over her firm, athletic bare thighs and give him a bare bottom spanking (!) in front of her hot mom to boot!! I can't imagine him just standing there clueless in front of her as she fidgets with the draw-cord holding his shorts up, and thinking "I dont think she'll pull my shorts down'.... I mean 'duh' of course she will (!!) but I imagine what was going through his head was more like "I cant believe I'm going to let her pants me like this... but she's SO friggin hot and as embarrassing as it is, I so WANT her to see my boner.. and I so WANT to be SPANKED by her... in front of her mom!!...
yet I cant believe this is happening and I'm actually going to let her do it... how emBARE ASSing.. and HOT!" I'm all about spanking lovely female bare rear ends, but I found myself rooting for your babysitter, living vicariously through you, and WANTING her and her mom to spank you while smirking, laughing and relishing in your embarrassment and your spanking. Lucky guy ... I think I'd have involuntarily orgasmed over her thighs while being spanked or finished myself off right there in front of them after my spanking and looking into their smiling eyes as I shot load after load.. with some hopefully landing on their feet, legs and swim suits. Maybe get a 2nd spanking from the mom for staining their pretty suits.

Mon, October 4th, 2021 8:02pm

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