I'd Like To Get A Spanking Like This. Warning Contains Sexual Activity

Debi, Jenny, and Bob

Debi had promised me a sound spanking for my naughty behavior. I was both excited and apprehensive at the same time.

As the time approached, I went down to the lounge to await her arrival. She walked in and to my surprise; some other lady was with her. Debi introduced her as Jenny, and they both sat down with me in the middle. I was trapped between them. Debi said, “It has been so long since your last spanking that I thought I’d bring someone to help me take care of your naughty bare bottom. Jenny this is Bob, Bob say Hi to Jenny.”

“Hello Jenny,” I said in a soft voice.

Jenny put her hand on my knee and whispered “Are you excited to see us”? Jenny ran her hand up my leg to my groin area and discovered that I was as hard as a rock. “Oh, it feels like you are. Debi, check out how excited he is to see us.” I felt Jenny remove her hand only to have it replaced by Debi’s.

“Hmmm. It seems that you are right. He is excited to see us.” Debi rubbed her hand all over my penis. Even through my pants, her rubbing caused me to become harder – if that was possible.

“I showed Jenny a picture of your naughty bare bottom and asked if she would like to help me give this naughty bottom a well deserved spanking. She was kind enough to say yes. Wasn’t that very nice of her?” Debi asked.

“I guess.” I hesitantly responded.

“You guess?” Debi looked shocked. “I think that it was wonderful of her so I don’t wear out my hand on that naughty bottom of yours and so should you. Now tell her how grateful you are for her to help me to spank you as you deserve!”

“Thank you Jenny for offering to help Debi spank my naughty bare bottom.” I replied with some trepidation.

“Oh you are welcome Bob. I have a lot of experience taking care of naughty men and I am sure that I will be able to give your naughty bottom all the attention it deserves.” Jenny stated.

We went to dinner and chatted about almost everything including my upcoming spanking. Both Debi and Jenny described in detail what they were going to do to my naughty bottom. This part of the conversation was in subdued tones but not whispering. As the waitress came over to bring me the bill, Debi said just loud enough for her to hear “Bob, you really deserve a sound spanking on your naughty bare bottom for your bad behavior. And we are going to make sure that you get one tonight.” I blushed as the waitress got a smug smile on her face.
We then went to my hotel room and Jenny informed me “Your naughty bottom is really going to burn tonight and I’m going to enjoy every single spank I give you, and I guarantee there will be a lot more than one time my hand meets your bottom.”

Jenny told me to drop my pants and ask Debi for my spanking. There was definitely a bulge in my underwear as my pants come down. Jenny remarked, "Well at least your front side is enjoying the thought of being spanked by us even if your back side won’t".

Debi sat down and pulled up her dress so her bare thighs come into view. “I don’t want you wrinkling my dress, so you will be across my bare lap. Jen, why don’t you pull down his underwear, as they will just get in the way?”

Jen called me over to her, grabbed my underwear by the waistband and slowly pulled them down to my knees.

My penis sprang out from my underwear. “Just look at this Debi. You’d think that he was expecting to have some fun tonight.” she said as she grabbed my penis. Jen then informed me, “Your bottom will be bare for a long while since all proper spankings are given on the bare bottom. Now walk over to Debi so she can start your spanking.” Jenny informed me.

I shuffled over to Debi since my underwear was impeding my walking.

Debi said, “This is one of the nice things about spanking a guy. You men come equipped with your own built in handle”. Grabbing me by my hard penis, she pulled me over her knee.

With my bottom sticking up over her knee, Debi started patting and rubbing my bottom and said, “Listen Bob, you have two jobs and two jobs only tonight, and the first is to keep this naughty bare bottom in whatever position we put it or tell you to put it, and the second is to thank us for your spanking any way we see fit. Is that clear?”

SMACK!! She spanked me for emphasis.

“Yes ma’am”, I quickly replied.

“Good. I’m glad that we understand each other”. She continued to rub and pat my bottom occasionally pulling my bottom cheeks apart, telling me all the time what the two of you were going to do to my bottom and scolding me for my poor behavior, causing me further embarrassment. Debi pulled my bottom cheeks apart again and said “What a cute little hole you have here”. She slid her finger down my crack and pushed gently on my anus. “We just might find a use for this hole a little later”.

“Well Bobby, are you ready for your spanking to begin”?

“Yes Ma’am”

“I’m glad, because I am ready to really heat up this naughty bottom of yours”.

The patting and stroking stopped. Debi raised her hand above her head and brought it down on my left cheek. SPANK! Right cheek WACK! Center, SMACK!

She got into a pace of warming my bottom. SPANK WHACK SWAT, SMACK. SPANK WHACK SWAT, SMACK SPANK WHACK SWAT, SMACK SPANK WHACK SWAT, SMACK, spanking all over my naughty bottom including that really sensitive area where my thighs meet my bottom.

“OUCH, YEEOOO, WWWOOOOO, Hey, that hurts, that stings really bad”.

“Well Bob, that is what a spanking is supposed to do. It’s meant to sting that naughty bottom of yours. Your bottom is supposed to be hurting, hot, and red by the time we finish. We are just getting started, so you better just keep that bottom of yours properly presented so I can spank it as much as I desire. And don’t forget, Jenny is next”.


“OOOOOO, OOUUCCHH, YYYEEEEOOOOOWWWWWW”, I began to wail as the heat built up in my bottom. “Are you finished yet? This RREEAALLYY hurts. Aren’t you done? “

“Listen you cry baby, I’ll decide when I’m done, not you. I’m not anywhere close to done with this naughty bottom of yours. Jenny hasn’t even started. I sure that she intends to spank you as much, if not more than I will. And besides, your bottom is only a little bit pink and I want it RED before the night is over.”

After another flurry of spanks, you said, “O.K. Bob, go stand in the corner for a while so I can rest my hand. Leave your pants down. Just shuffle over there and keep your hands away from your bottom. Hold your shirt up so we can see my ‘handy’ work”. They both chuckled at the really bad pun.

I got off her lap and started towards the corner, when Debi stopped me and said, “Bob. Turn around. I want to see what the front part of you looks like now. Is it still hard?”

I turn around and Debi noticed that my penis is hard, though not as hard as before she started spanking me. “Well, well. Perhaps we should make it hard for you while you stand in the corner. Come back here”.

I walk back to Debi and she grabbed my penis in one hand and my bottom with the other. Debi inserted her finger in my rear hole wiggling her finger and moving it in and out of me and gently stroked my penis with her other hand until it got hard again,

“There now off to the corner with you”. She swatted my bottom as I shuffle over to the corner.

After about 5 minutes in the corner Jenny called me over to her. She had me bend over for a minute, right in front of her. She wanted to inspect my bottom for a while.

She ran her hands all over my bottom for several minutes, squeezing and pinching both of my tender cheeks and then said “Kneel down on the bed and spread those knees of yours apart. I want to completely inspect you.”

“Let’s spread those cheeks wide apart. I want a good view of your hole. I also might have some plans for it tonight”. She said as she moved in for a closer look. She reached under me and pulled at my penis. She started moving her hand up and down my shaft keeping me hard. Jenny then let go of me and said, “Just stay there for a while so we can see you totally exposed.”

After another 5 minutes in this very embarrassing position Jenny told me to take off my pants and underwear, as I will not need them for some time. I do as she said and she told me that I may have a cigarette. She then informed me what is in store for me and my naughty bottom the rest of the evening.

“Bob, Debi and I are going to have a lot of fun with your bottom tonight. Since it has cooled down I want you over my knee right now so I can warm it up some more. You will have a hot bottom for the rest of the night”.

I laid over Jenny’s knee and got a viscous volley of spanks designed to hurt while Debi looked on. With my bottom already tender, it didn’t take many spanks to really have me squirming over her knee.

“BOB. Didn’t we tell you that your job was to keep your bottom presented in the position we put it in? Stop wiggling. Hold that bottom still if you know what is good for you”.


“OOOWWWW, OOUUCCHH, PPLLEEAASSEE stop spanking me. This hurts toooooo much.”

“I” spank, “said”, spank, “stop”, spank, “that”, spank, “wiggling”, spank.

I couldn’t help myself. Those spanks hurt so much; I almost wiggled off her lap.

“Now you’ve done it. I’m really going to use this bottom for other things besides spanking. Get off my lap. I want you to properly thank me for taking the time to spank you and correct your behavior”.
Jenny stood up and lifted up her dress. “OK Bob. I want you to take off my panties”. I got down on my knees and pulled off her panties. After I got them off she turned around, bent over and said, “Now I want you to kiss my bottom to thank me for spanking you. Kiss my bottom all over. You should even lick my bottom and use your fingers on my **** to bring me to an ******. It better be one of the best ones I’ve ever had or your bottom will pay even more”.

I did exactly as she said. My mouth and tongue were all over her bottom. My fingers were gently massaging her **** and I even dipped my fingers into her very wet *****. After several minutes she exploded into an ******.

Debi then said. “OK, now it’s my turn.” She pulled up her dress and said, “Get that tongue of yours working on my bottom. And I want a GREAT ******”. Again I found my tongue licking a female’s bottom. My tongue went up and down her butt crack and even tickled her cute little rosebud hole.

My fingers again were buried in a very moist ***** and I lightly rubbed her clitoris. She also came very quickly.

After she calmed down Debi announced, “OK Bob it’s time to finish your punishment. Bend over and let me touch your bottom. Oh my, it is so cool now and we promised you a hot bottom for the rest of the night. Get over my lap right now so I can warm up that naughty bottom of yours”.

I again went over her lap and she spanked me some more until she felt the heat in my bottom was sufficient, despite my pleas to stop.

“Remember when I told you that I had some other intentions for your bottom tonight?
Well I’m ready for those other intentions. Get off my lap”.


“Go into the bathroom and kneel down on the floor. We’re going to give you an enema to clean you out and then we’ve got a real surprise for you and that cute little butt hole of yours.”

I did as she said and presented my bottom for the enema. Debi and Jenny walked in and Debi filled up the enema bag. She got the KY and put some on her finger. She rubbed the KY all over my anus and even stuck her finger into my bottom hole. She then lubricated the nozzle of the enema bag.

She slowly inserted the nozzle into me and then allowed the whole bag of water to slowly enter me. After the bag was empty both Debi and Jenny rubbed their hands all over my hot bare cheeks. Debi then required me to hold it for a full 5 minutes before I was allowed to expel the water.

I got up off the toilet and Jenny told me to get onto the bed on my hands and knees. I did so and Debi told me to put my head down and put my knees wide apart. I did as she said.

“Now that is the way a naughty boy should be. Hot red bottom up in the air displayed for our pleasure. Bob you stay just like that and I’ll be right back. Don’t touch your bottom or it will mean more spankings”. Debi and Jenny left for a moment to put on strap-on ******. I just couldn’t stand it any more and while they were gone I rubbed my bottom a little, hoping to relieve some of the sting.

Debi returned, finding me rubbing my bottom; “Didn’t I say no rubbing. I meant NO rubbing”. SMACK. WHACK, SWAT, SPANK, SMACK. WHACK, SWAT, SPANK, SMACK, WHACK, SWAT, SPANK, SMACK, WHACK, SWAT, SPANK. You spanked my up thrust bottom several times very hard. “Listen to me when I tell you to do something”!

“OUCH! YYEEOOWW! WWWOOOO! OOWW! Hey that really hurts. Stop spanking me. I will do as you say. Honest, only stop spanking me. My bottom really hurts now”.

“Jenny, it seems that Bob needs a lesson in how to follow directions. Why don’t you get Fred and we will see if Fred can show him the error of his ways.” Debi exclaimed.

I had no idea what she was talking about. I really hoped that she had not invited someone else, especially a male, to join in spanking me.

Jenny came in carrying a paddle. “Bob, this is Fred and your bottom is going to become acquainted with him right now. Let’s give him 3 swats each with Fred and see if that doesn’t encourage him to listen to us?”

“That’s a good idea Jenny,” Debi said. “I’ll give him my 3 and you finish getting ready. OK Bob. Bend over and arch your back. Stick that bottom out and up high. I want a good target for Fred.”

SWAT!! “YYEEOOWW” I yelled. I immediately stood up and grabbed both my cheeks with my hands as the pain was almost unbearable on my already well spanked bottom.

“Don’t you dare get out of position again or I will add more swats.”

I quickly bent over again.

SWAT!! SMACK!! Both were delivered in Quick succession.

“OOOOOOUUUCCCCHHHHH!!!!!!” Was all that I was able to say.

Jenny walked back in just then wearing her strap-on and said “Give me that paddle. I really want to watch him wiggle that cute little naughty bottom of his as I give him my 3 swats. OK Bend over. Bottom up.”
She rubs her hand over my bare cheeks and said “Debi, we are doing a nice job here. This naughty boy’s bottom is very warm to the touch. Ready Bob”


All 3 fell immediately on my poor sensitive bare cheeks.

“YYYYEEEEEEEEOOOOOOOWWWWWWWWWW”!!!!!!!!! Escaped from my lips. “Please don’t paddle me any more. I don’t think that I can take another swat from Fred.”

“Then just do as we say and you won’t have to worry about your bottom meeting Fred again. We will just keep your bottom nice and warm. We’ll just keep it warm for the rest of the evening like we promised if you behave. Get back kneeling on the bed as you were before you met Fred. You just keep your bottom up like this with your knees wide spread so I can use this cute little hole of yours for a while”. Debi said.

Debi put a large glob of KY on her finger and rub it all over and in my hole, letting her finger slide in and out a little bit. “What are you going to do now”? I ask frightened.

“Why I’m going to put this ***** right in this cute little hole of yours and **** you in the ***. What did you think I was going to do with it”? Debi put some more jelly on the ***** and put it right at the entrance to my butt hole. “Now hold still and I will do this slowly. Don’t move or I’ll spank you again and just ram it in”. She slowly slid the ***** into my hole, easing it in a little bit at a time. Once she was completely in she started moving her hips back and forth. Every so often she lunged all the way in and reached around and grabbed my **** stroking it several times.

This went on for several minutes. Each time she stroked my penis, I almost came, however Debi stopped just before I did. She continued pumping in and out of me for what felt like an hour, however I’m sure that it was only about 5 minutes. All the while, they both kept scolding me and telling me what a naughty man I was and how I deserved everything that was happening to me and my bottom.

Debi finally stopped thrusting and pulled out of me. “I really liked ******* your *** Bob. I might just have to do that again sometime soon.” She told me.

“OK,” Jenny said, “It’s my turn. Bob, I want you on your back with your legs up in the air and spread real wide.” I rolled over onto my back and winced as my very well punished bottom came into contact with the bed spread.

“Spread ‘em wide for me.” Jenny informed me. I spread my legs as wide as I could and felt really exposed in this position. Jenny put her hand on my bottom and started running her fingers up and down my butt crack. She then inserted one of her fingers into my bottom hole and slowly moved it in and out, wiggling it back and forth at the same time. As exposed and embarrassed as I was, this felt good.
Jenny then knelt between my legs and positioned her strap-on right at the entrance to my bottom. She inserted the tip and slowly pushed it into me until I felt so full of the ***** I could hardly stand it. Jenny looked over at Debi and said “Next time we will use the large ones on him so he can really feel us inside of him.”

Debi agreed wholeheartedly.

Once it is all the way Jenny grabbed my hard **** and started rubbing it. “I’m going to keep moving this ***** in and out of your butt and stroke your **** until you ***, so I suggest that you just lay here and enjoy it”.

She started moving her hips faster and faster, all the time stroking me. She could feel the heat of my bottom on her naked thighs every time she plunged the ***** into me.

After several minutes I felt myself stiffen and I came, shooting all over everything.

“Now that wasn’t so bad was it? I know I enjoyed it very much.”

“Let me feel how warm your bottom is now. Ooh, it’s a little bit cool. Come over my knee for just a slight warm up”.

Jenny sat down and as I went over her knee, my **** was very soft now. “Well looky here Debi, this **** is not hard any more. What a shame? Oh well I’ll just spank this naughty bare bottom to get it warm and we won’t worry about the condition of his penis”.

Jenny again spanked my bottom as Debi held my legs to keep me from squirming too much.

Jenny finished this last installment of my bottom spanking and told me to get up. I rose to my feet and immediately put both hands on my bottom, trying to rub out some of the sting.

Debi said “And just what do you think that you are doing young man. Who told you, you could touch your bottom? Nobody!! Get back over my knee right now so I can remind you through your naughty bare bottom to follow instructions. You’re just lucky we don’t use Fred on you again.”

I lowered myself over her knees. “Now thank me for spanking you with my hand and not paddling your bottom as I probably should.” Debi told me.

I almost whispered “Thank you Debi for just spanking me with your hand.”

SMACK!!! Debi’s hand came in swift contact with my upturned bottom. “Say it louder. Say it like you mean it.”

“Thank you for spanking my naughty bottom with just your hand and not using the paddle as my bottom deserves for not following your instructions better.” I quickly said out loud.

“That’s much better. And don’t you worry TOO much, your bottom is tender enough by now and my hand is hard enough so you will feel every spank that I decide to give to you.”

With that she started spanking my bottom with all her might. SMACK!! SPANK!! WHAP!! CRACK!! Each time her hand came in contact with my bare cheeks, it felt like I was sitting on a HOT stove. SMACK!! SPANK!! WHAP!! CRACK!! Again I was clenching and unclenching my bottom cheeks. SMACK!! SPANK!! WHAP!! CRACK!! By now I was squirming all over her lap, trying desperately to avoid her spanks.

“Keep your bottom still while I’m spanking you.” Debi said.

She continued spanking my naughty bare bottom until I felt a thousand bees had stung each cheek. I was sure that my bottom had swollen to at least twice it’s original size.

SMACK!! SPANK!! WHAP!! CRACK!! “OK Bob, you can get up now, however I want you to bend over and spread those cute cheeks of yours once more. I’ve got just the thing to remind you to follow directions.”

I bent over and tried to pull my cheeks apart, however they were too sore for me to even touch. Jenny came over and grabbed each cheek in her hands and pulled them so far apart I thought I was going to split. Debi produced a butt plug and after putting a little KY on it, she inserted it right up my rectum.

“Now hold that in there for a while” Debi instructed me.

OK Bob, now you may clean up and put your pants on. We will go have an after dinner drink. We can watch you squirm around while you are sitting down on your well spanked bottom with that butt plug inside of you. You can tell us all about what a good job we did tonight spanking your naughty bottom for you. Don’t forget that the night is not over yet and you still might get another spanking or two before we leave, or we might just spend the night and start your day off tomorrow with a nice hot bottom for you to think about us all day.”
THE END, for now………

naughtybob46 naughtybob46
61-65, M
3 Responses Nov 21, 2010

So what would you have done differeently scottishnudistguy

yes for not editing the story properly

Actually yes I did. So long ago though. My naughty bare bottom needs some OTK hand attention