Saturday, March 21

Anal training in front of wife and friend

Had some fun the other day!! I was getting a bit bored so I thought I would spice things up by exposing david to another woman in the most humiliating way I could think of: anal training followed by a good old fashioned DP!

I'm running out of fresh "regular" ladies, so I decided to open up my purse and hire a new lady. I went online and found a very pretty and self-possessed Dominatrix in her late twenties. I contacted her and told her what I was looking for. We met over coffee, and we set things up. david did not know I was planning this at all. Her job was to pretend to be an acqaintance of mine to whom I was exposing david's little secret.

The backstory we came up with is that she was someone I tutored when I was a grad student, and we just reconnected recently as she was networking looking for a new job. We went for after-work drinks, and as we talked about our relationships it came out that we were both dommy. Me with my husband, she with her boyfriends. I asked if she would like to have some fun with me with my hubby and she readily agreed. But even that backstory david would not be told directly about. It would come out over the course of things. He would only be introduced to her in our living room as a girl I tutored many years ago who is visiting me.

It went off really well, couldn't have gone better, in fact, and david is still in disbelief that I would have involved a former student of mine in our play. Ha! Sucker!

I took off work a bit early, picked her up, paid her in advance, and drove her to our place. We were sitting in the living room and talking. david was expected any moment and he did not disappoint, coming in right on time after work.

I introduced her as Kimberley, a girl I tutored when I was a grad student and with whom I just re-connected. david was very charming and said how nice it was to meet her. After a bit of smalltalk, she started off the proceedings.

"So david, Julie tells me that you two have a very 'interesting' relationship?"

Poor david didn't know what to say. She watched him twist for a little while on that question and then went on.

"Julie tells me that she disciplines you. Is that true?"

She was relentless! david stammered and turned red, but eventually said "ahhh, yes Miss."

"Julie also tells me that she makes you bend over and take it up the ass from her strap-on? And suck on it first?"

"Aww, Julie!" said david, by now looking very embarrassed indeed.

I then said, "It turns out Kimberley also uses a strap-on on all her boyfriends, and spanks them first."

"I do!" She said enthusiastically. "It's what men need and what I like. But I haven't really had a boyfriend I could do that with for six months at least. So Julie was kind enough to offer up your ass for the evening, david."

She turned to me and I to her and we gave each other a quick peck on the lips. david's face was priceless! He was not expecting this AT ALL. And Kimberley is definitely cute to boot.

Kimberley reached down to her bag and pulled out a very large and thick black dildo. It was even a bit bigger than "Adam", but also a bit more soft and yielding.

"This is the only dildo I ever use. I hate those little pencil dick dildos!" She said.

"Oh dear! That looks pretty big, doesn't it david?" I said.

"yeah... too big..." he said, definitely sounding scared.

"Well I'm not going to disappoint Kimberley now that she's come all this way." I said. "You will be taking it, taking every last inch, down your throat AND up your ass. And Kimberley will go as hard, as deep, as fast, and for as long as she wants to."

"Ant that's pretty hard and pretty long." chimed in the charming Kimberley.

At this point I was so incredibly delighted with Kimberley's performance. She was playing her agreed upon part to a tee! A really great actress.

"But I know," said Kimberley, "that my boyfriends always have trouble with this dildo as well. I get them to stretch themselves beforehand, Julie, have you got anything he can use to stretch himself out for me?"

"Sure we do!" I said. "It's so true. If I go straight in with my biggest dildo, we call him 'Adam', it's pure punishment. But if I work him up to it, then he can more or less take it, and without the screams."

"I always made my boyfriends do that to themselves. I mean it's their assholes. They should be motivated."

"What a great idea," I said. "In fact, why don't we get him to do it right here in front of us, so you can check if he's doing it properly?"

"no.... please!" said david.

"Sure!" Said Kimberley. "Happy to. Tell you what, Julie, you go get whatever toys you think he needs to stretch his butt and bring them over here. As for you, butt boy [YES! She actually called him 'butt boy'! Ha Ha!], take these gloves, I brought some with me, go to the toilet and take a crap, and use your fingers to scoop out any shit you have up there. I want you clean and empty. It's the only way it'll be safe for you to take my bad boy up your ass. And you better do a good job. If we see any mess when you pull out your little dildos you'll get a spanking; and if I think I need to I'll stick a finger up there myself to pull out your shit, don't think I won't, and then you're really going to catch a butt whupping if I have to do that!"

[WOW! That's pretty much what she said. Wasn't she amazing! Talk about H U M I L I A T I O N for my boy!]

david, blushing furiously (!), went off to the bathroom to do his thing, and I went to get a selection of his butt toys, some toilet paper and paper towels, a whole lot of lube, some more latex gloves, a couple of towels, and a yoga strap. For the butt toys I got a thin and long dildo, a medium sized butt plug, my largest dildo Adam, and my Hitachi with the anal attachment.

Kimberley and I moved the coffee table to the side of the room and laid everything out on it. We then put a towel down in the centre of the living room, directly facing the couch we were sitting on. We would have a great view!

david came back looking sheepish. Kimberley quizzed him, and david told us that he had done as he had been told and was as clean as he could get it up there. He looked over at the array of sex toys I had out on the coffee table. It was definitely dawning on him that we would be making him fuck himself with these things while we watched.

"Please," he said, "I can do this in private."

"Oh no!" We both said at the same time. "Right here in front of us." Said Kimberley. "So Kimberley can see if you're doing it properly" I added.

I told him to strip down to his "underwear". Even Kimberley would be in for a surprise. I had given david a spanking the night before, and "noticed" hairs in his bum crack. I told him to shave himself thoroughly, front and back, bald as a baby, and that he was then to wear panties for an entire week, 24x7, as punishment for failing to keep himself properly shaved for me up his butt crack. Naturally I knew that tonight with Kimberley was planned (though he didn't) so that's why I did it. The long and short of it was that he was in panties and totally bald on his genitals!

david began removing his clothes. "Just to your underwear!" I warned him, sensing he was going to strip down both his pants and panties at once. Once he was nude except for his pants we made him face us. His hands were crossed in front of his panty-covered genitals.

Kimberley clapped her hands and said "How wonderful! What pretty panties you keep him in!"

"Don't cover up your pretty panties, baby. Hands at your sides!" I said.

david moved his hands to his sides which showed a very considerable erection barely contained by his light blue lacy panties.

"Oh My!" Said Kimberley in mock surprise at his erection. "What a naughty boy! You would think he actually wants me to fuck his ass. Get over here! You need a spanking to shrink that erection of yours."

david walked over and Kimberley pulled my husband across her lap. "Put your face in your wife's lap!" She ordered him. david's head was nuzzled high in my lap, between my legs. His arms encircled me, one hand on my butt, the other on my waist. Kimberley then started spanking him across the seat of his panties. Fairly light smacks, but I could feel his humiliation as he squirmed against me. Kimberley then adjusted his panties into his butt crack, and proceeded to smack his now bare cheeks. david squirmed against me even more in mortification and sexual excitement.

While my husband really does enjoy this type of play, he also genuinely gets very embarrassed during it, which is what actually is the turn on for him. So there was no doubt at all that he was very embarrassed to be spanked across the knee of "my young student" while dressed in only panties.

"Let's see if that's done anything." Said Kimberley, getting david to stand. "Nothing at all! It's even worse if that's possible!" She said examining the front of his panties. "And oh my God, fix yourself!" She told him. His balls were hanging out the side of his panties. Ha Ha! He turned away from us and fixed the front of his panties.

"Let me give it a try!" I said, and pulled him across my lap, causing his head to now fall right square onto Kimberley's lap, right at pussy level. I started in with considerably harder smacks than Kimberley had done. I don't think she was calibrated as to how hard david has come to need his spankings. During this hand spanking, midway through I pulled the backs of his panties down and spanked him on the bare. david squirmed across my lap, and I could feel his erection very clearly against my leg and very clearly not subsiding despite the strength of my hand spanks. From my earlier experience, I knew that his head was bouncing around on top of Kimberley's lap, causing some little pussy excitement. It's very much the position he would be in were he giving cunnilingus. And I know that a writhing humiliated male always makes my pussy wet itself!

I quickly pulled his panties back up and made him stand. He stood and fixed himself again.  His erection had not subsided.

"Fine, david," I said in an exasperated tone, "I can see that erection is here to stay. Let's get on with your stretching despite it. Take your panties off."

david turned away from us and removed his panties. He turned back to facing us, now fully nude, with his hands again covering his privates.

"Do you let him cover himself?" Asked Kimberley of me.

"Absolutely not." I said. "david, take your hands away from your penis. I won't have you touching yourself and masturbating it in front of Kimberley. If I see you touching it again, you'll get the belt."

david moved his hands to his sides, and out sprung his giant erection.

"Oh my!" Said Kimberley. "He's so hard! And I absolutely love how you keep him shaved bald like that. Just like a little boy. But let's see if we can't do something more about that erection."

We have a stout little wooden box in the living room. About three feet wide, two feet high, and two feet across. Kimberley had him move the box towards the centre of the room and then drape himself over it. She made him spread his legs as well. His penis and balls were dangling between them. Then she bent over, put a hand on his lower back, and used her other hand to smack his bare cheeks some more.

After a bit of a spanking that further pinkened up his cheeks, he was made to stand and his penis was inspected anew. Still erect! Kimberley "gave up" too at this point of trying to spank it away.

Now it was time to really start the proceedings.

Kimberley began: "Now david. Go put a latex glove on your hand, stick your middle finger up your ass, and give yourself a good finger fucking."

david, still looking very sheapish, put on a glove, lubed his finger and then his asshole, faced us, and started putting his finger up his ass.

"No no. Turn around. Bend over. We want to see it going in." Said Kimberley.

With a very resigned look, david turned around and bent over and again started inserting his finger.

"Spread your cheek with the other hand so we can see it going in. That's good, now turn a tiny bit sideways so we get a good view. There. Perfect!"

From this angle, with him bending over, and with him spreading a cheek, we got a very clear view of his finger penetrating his asshole.

Kimberley kept going: "Good. Now in and out. Fuck yourself nicely. Get it in nice and deep. Good. Now swizzle it around in there. Good. Now back to the fucking motion. In and out. Ok. Good boy. Now let's see two fingers in there. Go on now. You can do it. Good Boy! There you go! Now fuck yourself. Go on, harder. Remember, the more you do now the less my big dildo is going to hurt you later."

It was a priceless tableau. There was david, bent over, giving himself what I can only describe as a vigorous fucking in the ass with his own two fingers buried up there to the hilt. Each time his fingers went in deep he grunted and moaned a little bit. Ha Ha!

"Ok, that'll do," said Kimberley, "I think you're enjoying yourself a little too much. Now take your fingers out and show us your hand. There had better not be any mess on that glove or Julie and I will have to clean you up and then give you a good hard spanking..."

Looking away, david pulled his gloved hand out and showed it to us. He could not bear to watch. Thw glove was, fortunately, clean.

I got up and went to the coffee table and selected the long skinny dildo and handed it to him.
"Let's have him get in a little deeper with this one." I said.

We again made david face mostly away from us and bend over so that we could watch the full insertion. He managed to get it right in practically right up to the hilt the first time.

"Give yourself a good fucking now." Said Kimberley.

david started sliding the dildo in and out. As he shoved it all the way home he gave out a little cry of pain, but he kept going. It was no longer than the thicker dildos, though. He would have to deal with it and he knew it.

"Turn and face us." Said Kimberley.

david turned and we saw him from the front. His penis was still hard, and he was sort of doubled over giving himself a good hard fucking with that slim dildo!

"Ok. Let's move on to something thicker now. Pull it out david, and let's see if you've been a good boy."

He pulled out the dildo and again, looking away, held it out to us for our inspection.

"Ooooh!" We both said at once. There was a tiny spot of poo on the very tip of the dildo. "Look at it david! Just look at it!" Kimberley told him.

david looked at the messy dildo. He looked absolutely, completely, mortified.

Kimberley jumped up and took the dildo from his hand. She wrapped it up in toilet paper and handed it back to him and told him to go clean it up.

david went away to do that. When he came back we made him remove his glove, bend over and put his hands on the sofa armrest. I used more toilet paper to clean up his asshole. It was more luby than dirty, but a bit dirty. Poor baby was getting his bum cleaned right in front of Kimberley!

When he was clean again, Kimberley said, "He needs a spanking now!"

"He sure does." I said. I kept him bent over and took his leather belt out from around his discarded pants. I then stood back and gave him a nice hard ass whipping with that belt doubled up. From mid ass down to mid thighs. He yelled out as he got his whipping. I handed the belt to Kimberley and she picked up where I left off, matching my pace and strength.

By the time we were done he was quite red and he had some welted belt stripes sizzled across his ass cheeks. I whip hard or not at all. Kimberley was inspired by that, and matched me, just like a true pro would, adding some stripes and welts of her own.

With his punishment dealt with we moved on to the next toy: the butt plug.

We made david bend over and insert that plug into himself. He had a bit of trouble at its thickest part, but then drove it all the way home, at which point his asshole just seemed to suck that plug right in!

"Now pull it out and shove it back in again." Said Kimberley.

"no! please!" said david. "It's got the thick part and I just got it in!" He had struggled with it a fair bit.

"Are you back talking me, butt boy?" Asked Kimberley of david.

"no ma'am" answered david, which was wise considering the sorry state of his ass already, and he started fucking himself with the plug. It was fun watching his anus distend to meet the thickest part of the plug each time. david said "Ouch. Ouch. Ouch." each time the thick part came out and went back in, but like a good little subby he kept the fucking going.

"Can I borrow that belt again?" Asked Kimberley. I handed it to her.

"Shove that in, bend over and touch your toes." She ordered him. "I'll teach you to back talk me."

david bent over, plug full in, crying out "no no no no" even as he did so. Kimberley ignored him and started whipping his ass with nice loud CRACKS of the belt. I think she targeted the base of the plug, which made him jump and wince. As she whipped, we could start to see the plug coming out of his butt. She grabbed the base and pushed it back in, and none too gently! "Keep it in!" She said.

She ended up his belt whipping with a fierce and loud volley, which further marked him up. He would not be sitting comfortably for a while. That'll learn him to back talk a woman! She tossed the belt carelessly on the floor and came back to the couch to sit down with me. She was totally in control of this scene and I was loving it.

"I think you need to learn how to keep that plug in there. Stand and face us. Put your arms out to the sides, and give us 10 nice deep squats. If that plug comes out, Julie and I will whip you bloody with that belt!"

Oh dear. Hope she was not serious!

david looked very scared though, and started doing the squats. He did two and then had to reach behind him to push the plug back in. Kimberley let that go. "Squeeze it in!" we exhorted him. He kept going until he had done the full ten squats. His form was very nice. We both commented on it. Mags would have been proud. He was still, unbelievably, quite erect.

Kimberley made him turn around again and bend over. She made him spread his legs. "I want to see your cock and balls too," she said.  She then told him to push them back between his legs and to trap them there. She made him waddle backwards towards us until he was within reach of our feet. With her bare toes she started kicking lightly at the tip of his penis. I used my foot to push deeper on the plug. Kimberley then used her toes to crush his balls against his legs. We both alternated playing footsie with his plug and private parts! What fun! david was so hard he looked ready to squirt.

"Pull that plug out and show it to us." I said.

david did, and this time it came out clean. the plug was not as long and did not delve as deeply.

"Now let's get him to loosen himself up with that Hitachi." I suggested to Kimberley. I fitted the end piece on, plugged it in, and tested it. Kimberley was fascinated with the attachment. She had never seen one before. Though it did come out in the conversation that we were both Hitachi girls!

I handed it to david, and Kimberley and I both went back to sit on the couch. He lubed it and re-lubed his asshole. We had him turn away from us so we could see the insertion. He bent forward at the waist and stuck it between his legs from the front, handle facing down, and hooked it into his asshole. It slid in easily. He flipped it on. Poor baby went right to high and gave himself quite the jolt! It was very funny. We could see his ass cheeks jiggling with the vibrations.

Kimberley told him to fuck himself with it and to swizzle it around up there, which he did. david was all "ohhhhh ahhhhhh ohhhhh ahhhhhh ohhhhh" as it vibrated vigorously and fucked him. This would loosen up that hole for sure if anything would!

I called a stop to the amusing spectacle. We made him show us the tip, and it was clean again. Good boy!

"Time for Adam!" I said, and david groaned.

Adam is really quite long and quite thick. david elected to kneel over the wooden box and push it in that way. He looked like such a little slut with his ass up high like that, wiggling in the wind as he went to shove that thick dildo in. While it was not a total picnic, it did go in with the minimal amount of drama, and practically right up to the hilt.

"You know what to do..." Said Kimberley.

david stayed bent over and began fucking himself with the dildo. It's so long! Very impressive. All the way in and practically all the way back out again. Over and over.

I then told him to stand. david stood back up holding the dildo in there. I got out the Yoga strap.

I wrapped it around the base of the dildo in back, and down under his cock and balls in front and cinched it tight in an attempt to provide a mechanism to keep that dildo in tight. Kimberley jumped up and said she had a better idea. She moved the back of the strap up around his waist, also moving the buckle to his mid back. Then she took the left over end and wrapped it down and then back up again between his legs. She pulled hard and david gasped as the dildo was shoved in deeper. That's better. She then tied off the loose end of the strap in front, right under his balls. Naturally, there was much  touching of his cock and balls during this operation by Kimberley. She did not even seem to notice. I am quite sure david did!

We went back to the couch and david was made to stand facing us, the dildo deep deep up his anus, the Yoga strap harness holding it in tight, and also pushing up on his balls and cock.

"What gigantic balls he has!" Said Kimberley. They did look disproportionately huge, pushed out and up as they were by the Yoga strap. As well, his penis had shrunk (not an uncommon occurrence when he has Adam up there) but was still sticking straight out from his body, pushed up and held in place by his balls. I mean, the tip of his cock barely passed the edge of his balls!

I felt a little sorry for the poor little thing and rubbed his cock gently with my hand, bringing some life back into it as he moaned in pleasure and his knees shook.

"Give us a little walk back and forth across the room. It will help stretch you." Said Kimberley.

david started walking.

"Not like that!" Said Kimberley. "Sway your hips. Sashay. You have a cock up your ass, you may as well play the part." david blushed but did as he was told, crossing one foot in front of the other as he walked, swaying his hips.

When we had our fun with that, Kimberley asked if he thought he was ready for his fucking now? As she asked, she held out her giant dildo for him to see again.

"I don't know..." wailed david, looking very scared at that big black dildo.

"I guess there's only one way to find out," said Kimberley. "Where shall we fuck him?" Asked Kimberley of me.

I led them both up to our bedroom. He would receive his fucking from Kimberley and I on the marital bed.

I moved david over to our wooden stool and made him sit on it. His feet dangle on this stool, and his full body weight on the dildo really pushes it up deeply into him. He used his hands to try to relieve some of the pressure, but he would not be able to keep that up for long. He whined and complained as the stool forced the dildo deepeer and deeper up his ass. He started sweating in fact, and lost all signs of his previously proud erection. He wiggled side to side and back and forth to try to relieve more of the pressure, but it was really quite futile. In the end I made him take his hands away and place them on top of his head. He groaned in pain as the dildo penetrated him deep as could be. He grimaced and clenched his teeth as the dildo stretched him wider and deeper. There were even honest to goodness tears in his eyes and literally rolling down his cheeks. Kimberley looked at these in fascination and, quite cruelly I thought, only said "Suck it up Princess. My dildo's going to be worse."

[Continued in part 2]


  1. Sounds like great fun! I am so jealous and excited right now! I wish i can be part of it!

    1. Me too. I would love to give this experience to all males. good for 'em!

  2. WOW you are sure giving David a workout with Kimberly and I bet Megs would love to have been part of it. Kimberly's dildo looks very big and I know what David felt when it entered him stretching his hole wide open. Can't wait for part II

    1. Posted now.
      The stretching was very effective...

  3. Oh my Ms. Julie! I can't even imagine how Your princess felt after that humiliating experience!! I am so happy that You You made him wear his pretty panties for his meeting with Your "student". Have You thought about feminizing him further in the future for another meeting?? Oh how I love Your postings! Thank You!!
    Submissive curtsy,
    sissy jennifer

    1. Indeed. We'll have to play with her again. maybe I'll dress him all up en femme and have him do the housework as punishment for something, and then Kimberley can just "drop in". Ha Ha!

  4. Most honorable StrictJulie

    Jeez Louise - YOU may have met your match!


  5. Omfg! Lordy that was hot! You are the best, Julie! Can't wait till the next installment -- Y'know, I'd be happy to kick in a couple bucks for expenses, (hmm, also too maybe several women? what would make david's eyes roll up in his head? ) -- I'm sure others would too -- and also a nice massage / whatever for david -- he's provided us all with so much vicarious pleasure;)

    1. That's an idea. A "party" where I hire several professional girls all masquerading as "normal women".

    2. Yes, what a great idea !!!

    3. Love the party idea...........

    4. I shall have to work on that then!

    5. Goody goody!!

  6. So well set up and sexy... you are an ingenious crafter of scenes.

    But how dare you break it into 2 parts?!?!? I can't manage that degree of delayed satisfaction! ;)

    This would be a great one for that book if you decide to write it...

  7. Wow, Julie you are peerless, looking forward to part 2. I'm changing my name to david.


  8. You are amazing!!

  9. sissy jamieanne24 April 2015 at 05:50

    Wow! Wow! And, Wow! What total humiliation for david and such fun for Miss Julie and Miss Kimberley! His humiliation must have been complete...being spanked by and sodomized in front of a total (and younger) stranger! The tears make this tale all the more delightful, Ma'am! You are truly a Lady in charge and Your david seems to know that Your word is law!

  10. You are the best☺️

  11. I found that once a woman knows you like toys and sees the ones that you have collected she easily puts 2+2 together and starts using them on you. I was a great leather worker and made my own paddles, whips, straps as well as harnesses that would make women’s eyes light up and immediately want to try them out. I came home from a date with a cute coed and she spied my harness and dildo and told me she wanted to try them out of my ass. She claimed she never fucked a guy in the ass before but quickly got naked strapped on the dildo pushed me over the bed and fucked me like a pro for 30 minutes. When I came home with a razor strap my wife immediately told me to get into the bedroom and get naked and in less than five minutes I was getting the whipping of my life strapped across my bare ass over pillows on our bed. My wife is a strong lady from swimming with muscular arms to give me a strapping I’ll never forget. I made another lady a wooden. paddle with nylon spikes and she put the fear of the goddess in me pulling me over her lap and blistering my bare ass. The spikes were in round it off but it doubled the pain of the paddle and it became my most feared toy. I love having my cock sucked by a woman that knows the art of fellatio and my wife is the best. yeah I know in the back of my mind as I struggle to hold off from coming when she finally sucks me off I’m going to get the real intimate kiss when she feeds me the entire load forcing me to swallow every last sperm cell. I took a lady friend to the beach and we went over to where the cane was growing and she told me to snap off a switch. She whipped me right there on the beach giving me a wild caning striping my ass right there in the open where anyone could’ve seen. She made me walk back through the field Barenaked showing off my stripes until finally people were coming and I was forced to get dressed. I made a nasty cock and ball chain the same as used on a dogs neck and my girlfriend loved to pull it when I was driving or we were out in public.