Bra and Panties for him

I recently sent a pen pal shopping for panties and a bra for himself at Victoria’s Secret with lots of sales help. Just imagine how embarrassing that must have been!

Well, no need to imagine, the full story is right here.

I am sharing with you our private correspondence, with his permission. It might give you an insight into the wonderful email exchanges I have with my fans, and insight into a fellow kinster’s intellect and emotions as they are put through their paces by me. I never publish anything without approval, of course.

This is the same pen pal I corresponded with in the steamy summer of 2017. It culminated in a post called Ranch House Justice which was a bit of fiction I wrote as a reward for him. We had not corresponded for a bit, but he had been lurking along. He renewed his correspondence recently, sending me a “peace offering”.

Hello Ms. Julie:

It’s been quite a while, over a year now, since I last corresponded with you. You may not remember me, I’m the fellow who wrote to you about the video shoots I’ve done with Domme Karin. You posted a great blog about it and also included an amazing story based upon my fantasies. I’ve still been following your blog, reading almost every day. Ms. Julie, it truly just keeps getting better and better! In gratitude and recognition, I humbly present a certificate for your consideration.

Is this certificate not just the sweetest thing?

You absolutely deserve the recognition. The Classy Lady part certainly applies (well, the perv part too).

I’m really loving the current, most recent post!! It speaks to me on a few levels. Maybe causes some funny feelings? And yes, thinking more about my hottie niece! (yes!)

The post he was referring to is Would you do it? where I recounted the tale of a different gentleman, obsessed and very conflicted by his desires to be dominated by his grown-up pretty niece. I made him go to Victoria’s Secret to purchase panties, and am insisting that he have a sexual “experience” with a male. I am still waiting for that to play out. There has been some progress…

I wrote back regarding him and this man.

[…]
You cannot control your fantasies, and your fantasies do not make you a bad man. I am still insisting that he endure a panty spanking, a belt licking, deep oral sex, and a good hard ass fucking from a man as “punishment” to truly cleanse him. Ha ha! I want him to repeat to himself “I’m sorry for being such a pervy uncle!” in his mind, imagining he is speaking to his niece, as he receives his punishment fucking.

Have you ever been required to receive sex from a man (or just naturally did so?)

And he responded

I absolutely agree with you. Our fantasies are a very real and true part of ourselves, not something bad or something to be ashamed of.

Speaking of which, I did get to see my niece at a get-together this past week. She actually is quite stunning and on this occasion wore a fairly short, snug party dress. Such pretty legs, crossing and uncrossing…… and I did enjoy getting a couple of those wonderful hugs. I sort of think she enjoys them too. And she’s always playful, kidding with me, etc. I agree with you that she must be aware. As you say though, she’s in the driver’s seat and I’m not to forget it. She always calls me her favorite uncle and she knows she’s my favorite niece. I won’t do anything to ruin that or her trust in me. But oh my thoughts and fantasies! They are a very real and true part of me, and actually, I’m not ashamed about it.

So, is your e-subby having any luck finding that cock to take? Also, I was wondering if he made it back to Victoria’s Secret for his bra fitting.

As I said before, thinking about both these things gives me “funny” feelings. I can’t help but think of them as wrong in the sense of being “unmanly”. But they cause confliction as well.

As far as taking cock, the intensity of the experience would be huge (not unlike that formidable dick your e-subby was looking at!). The thoughts of such excessive submission, humiliation, the physical pain….well, they also bring on feelings of arousal. But part of me says it’s not right to admit it. I’d have to use the words, scary and stomach churning as well, when thinking about it. And is that a bad type of anxiety necessarily? Are my above thoughts, in your experience, odd, different, typical? To answer your question, Ms. Julie, no I have never taken a man’s cock in either orifice, on my own or required to. Actually, I haven’t been penetrated by means of a store-bought phallus by a woman either.

I have done some anal activities on myself this past year though. I bought a set of three butt plugs and also an average sized dildo. I have used them a number of times though the largest plug and dildo only twice, as they are quite challenging for me. They all do feel good however – very unique sensation. So, like your e-subby, I’ve had toys up in there.

To touch on his Victoria’s Secret excursions, thoughts of those give me the same conflicting feelings. I’ve never purchased or even put on women’s panties. It’s always been, in my mind, a worrisome thing to think about (slippery slope toward becoming a sissy?). But I run across it so often in various blogs and do find myself also aroused by it, though purchasing them would be especially terrifying. But maybe I could/should?

I would very much appreciate your input/thoughts, even direction if you’re so inclined. If I’m imposing too much please just say so.

So another man who’s thoughts are very naughty about his hot young niece! I find that very sexy, to be that object of adoration (and know it).

I also love how he is so open and sharing with me about his private thoughts and feelings.  I was also thinking, as I was reading it, that he is crying out to be told what to do. My specialty! So I thought I would give him a gentle little push. I wrote back.

Thank you for the nice note.

Your niece sounds like a plum. It puts a smile on my face that you so respectfully lust for her. I think all women enjoy being respectfully lusted after, though not always the overt expression of same!

I think you have a fascination with women’s panties. I really want you to go out and buy a pair for yourself from a real shop. A pretty young girl around your niece’s age will no doubt ask you if she can help you in a nice perky voice. I want you to say, “gee, this is embarrassing, and I’m really sorry to bother you, but they’re for me. What size do you think?” I predict she will get a big smile on her face, and start asking you all sorts of very normal questions that you will be incredibly embarrassed by, such as size, and style and colour, number of pairs, and so on. She will try upselling you, probably. You should consider it. I’m imagining the sweet blush on your face already…

Go do it and tell me about it after.

Imagine how tummy churning that must have been for him to receive that note. He really had to obey. It would be such a missed opportunity otherwise. I knew he would.

Hi again Ms. Julie:

I’m thinking you’re right about a fascination with women’s panties. Thank you. And yes, I WILL do it, though I’m truly nervous. It will be this coming Thursday when I can, and I will write to you afterward. I’m sure I’ll be thinking about it a lot until then.

Isn’t that wonderful? He will put himself through this extreme experience. It was so sexy for me reading that he would do it. As the date approached, I sent him an encouraging email.

Thursday is now just 2 sleeps away!!!

Are you getting nervous? You won’t chicken out on me, now will you? No, you won’t. Not based on what I know about you!

Can you imagine how much your face will be blushing as you stammer out your ask? The good thing will be that there will be so much blood in your face there will be none left over for your cock.

After you get your panties we’ll be doing some nice girly things with them…

He wrote back right away.

Hi Ms. Julie

It’s always so nice to hear from you.

Yes, not much longer, it’s getting real now 😟!  No ma’am, I will not chicken out, I will do it as you’ve directed and told me to. I’ll head to town Thursday AM. There’s a Victoria’s Secret there at the mall. Oh jeez, I’m really going in. Yes, yes, this IS HAPPENING!!

I’ve been trying to put it out of my head the past few days, with limited success. I’ve been practicing the words so that even with stammering (I do anticipate it too) I’ll be able to get them out.

Yes, I’m so nervous, even scared (It’s crazy, I’m a grown man), never done anything like this!! Oh my, oh my, Ms. Julie!

Thank you.

Isn’t that just a perfect picture of excitement and angst? I love that I can have this effect on men from afar. I do it because I really do love my pen pal, and I have fun experiencing it vicariously through him, and for you all to share in it as well.

Well, he DID IT! I asked him to go back and collect some photos of the store after, and to send photographs of himself. So these are the actual photos I’ve embedded.

Hello Ms. Julie!

Well, I did it! The way you told me to. I now own 3 pairs of women’s panties (well, they were having a sale), and they are nice looking ones I think.

I bought them at the Victoria’s Secret as I said I would in my email on Tuesday. Sorry I couldn’t do it sooner but I did pay for the delay with extra days of nervous (at the least) anticipation. And since Tuesday, you’ve also made me start wondering about what “doing some nice girly things” means.

Here’s how it went:

My heart was just pounding when I entered the store, praying I wouldn’t see anyone I know. My stomach was doing the twisties big time. I was so embarrassed just being in there, never have been in one before.

I looked around and located one of the panty sections.

I picked up a pair, my hands were shaking. A young salesgirl did come over. I started shaking more. She was in her mid-twenties probably, and tall and black and beautiful. She asked if I needed help. I looked at her, took a breath and I said my lines!! The first part – “gee this is embarrassing” then another deep breath, then – “I’m really sorry to bother you but they’re for me what size do you think” – pretty much as a single sentence. But I did get it out, the words you told me to say! 

She gave me just a slight smile and said, “That’s perfectly fine, I’ll be glad to help you”. She asked me about what styles I liked. I told her I’d like something somewhat fancy. She showed me several pairs pointing out differences in rise, leg cut, seat, etc. She suggested size medium. I was feeling so hot during this, which made me more embarrassed, which made me even hotter. And I felt my cock tingling and stirring as well. Hopefully there was nothing noticeable there to her.

She then told me about the sale price on 3 pairs and left me to pick out, but said to let her know if I had any other questions.

I took a little time to pick out three pairs. I have to admit that quite a few of the styles and colors caught my eye. I’m still trying to sort out what that might mean. I didn’t take too long, but tried to make good choices.

Though trying my best to look cool and calm, I’m sure there were customers who caught on to me. I noticed a couple of young gals giving each other a look as I carried the panties, now my panties, to the checkout. It made me feel more embarrassed and hot again. The same sales gal was thankfully at the register and maybe noticed because she said, “Come back any time, you never need to feel uncomfortable here”. I think I probably always would though. After leaving the store and calming a bit I noticed feeling a little precum wetness in my underwear.

It was a very emotionally intense experience, several different and differing thoughts and feelings going on. I’m still trying to get my head around them. Maybe it’s better not to overthink?

I do want to thank you very very much Ms. Julie for taking me in hand and for, in a clear straightforward manner, telling me to do this.

p.s. I also wanted to thank you for your kind words about my niece earlier (yes, she is a peach) and about my relationship with her.

Isn’t that just a marvelous experience? Really, those girls are there to sell panties. They will very happily sell to anybody who wishes to buy, and will get a big kick out of a very nervous and shaky older harmless man!

I wrote back.

Yay! Way to go!

A tall, black, beautiful, mid-twenties, salesgirl with a slight smile asking you if you needed help. And then a nice long discussion on sizes and cuts and colours that made your cheeks burn and your cock leak. Perfect! As you say, very emotionally intense for you, business (mostly) as usual for her (you are not her first, I’d wager). I like that she acknowledged how uncomfortable you appeared. VS does have a store policy about selling to “your kind”. You are to be welcomed. Your dollars are good there. Realize that EVERYONE’S purpose for going to VS is sexual. It’s like a sex shop that way. Monkey business will ensue!

Regarding girly experiences, your reward for going to VS is… drum roll please… to go to the drugstore and buy nothing but a box of tampons. Human checkout please! Then, using some lube, insert one into your butt then pull your panties on. If you can send me a photo of that, it would make my day. In fact, send me three, one of you modeling each of your panties. Make sure that tampon is in there. And for the grand finale, you pull those panties down and take a photo showing your little string dangling out of your butt, Little Miss Cottontail. I want to see those cheeks spread and the tampon part all the way in. Those little strings are tough and will not break when you extract it. Though do lube it before putting it in. And don’t throw it in the toilet after or you’ll bugger up your plumbing!

He later sent me the requested photos. Let’s ALL have a look now, shall we. First, let’s make sure that tampon is stuck up in there nice and snug…

Oh my goody goodness! He really did that, didn’t he? That’s one big girly step right there I’d say. And look how small and tight her balls are, and from this angle her penis tip looks for all the world like an engorged clitty, no?

With that tampon in place, the modelling show could begin.

Aren’t they all just darling? The one on the right is very sexy, but the one in the middle is the most feminine I think. I just don’t think he can carry off the looks on the far sides, you know? He’s not quite that pretty. A little high on his horse, don’t you think? I think the middle panties are all a girl like him can manage. [ha ha! just teassssing!).

He recounted his tampon shopping and the thoughts his panties brought to mind.

I picked up the tampons at the drug store this morning. The cashier was an older lady and the transaction was uneventful but still felt embarrassing. I just sort of kept my eyes down. I had no idea how to insert a tampon but found a helpful You Tube video. It’s definitely a strange feeling having a tampon up there. Not awful or painful but you do know it’s there.

The panties are fancy, do you think?

The material even just in my hands feels nice. And especially nice when wearing them, feeling that smoothness against my hips, belly, ass, cock…… My cock definitely came to life in contact with my panties for a while at first then settled down somewhat. So different!

They do feel very different from my usual underwear in terms of fit as well. That is, where they contact the skin and where they don’t. Especially true of the beige pair (thong. Yes, I did buy a thong pair, I was just in that headspace at that moment.) I know they’re not made for my “body type” but I did my best to fit my parts in politely for the photos.

Overall, I guess I have conflicted feelings when wearing them. Yes they feel great and stimulate me mentally as well as physically, but they are so frilly and fancy and are women’s panties, which makes me feel very much less than manly, which is to say definitely girlie, and a little embarrassed. Screw the conflict, I think I’m thinking too much again.

Best I just enjoy the ride… and I am definitely enjoying it. Would you concur with that strategy?

A tampon in one’s ass definitely knocks a guy down a peg or two as well.

I did have the tampon inserted properly in my ass throughout all the photos, and in the picture above I display between my cheeks (squirmy moment, it’s uncomfortable exposing this part of me) showing you the evidence as directed. All the way in. The things I’m doing for you Ms. Julie!

Oh yes. The things.

I continued on with his girly challenges.

But you know what the REAL VS experience is? Bra shopping! Wear a tight fitting T-shirt under your regular shirt. Be sure to have your tampon inserted and your panties on as well, even though nobody will see it. They have to involve the lady with the measuring tape. They have to take you back to the change areas. They have to watch as you try it on over your shirt. A bra fitting is much harder and more labour intensive than simple panties. If you buy the silicone inserts the $ signs ring in their greedy little eyes! They will have to help you sort those out, as the inserts for each breast come in two pieces that must be inserted correctly. Can you imagine your beautiful black “girlfriend” adjusting those for you under your new bra? Bra shopping is when the fun really starts. When I took my husband, they were quite cavalier about opening and closing the changing room door, and multiple women waiting nearby for a change room caught an eyefull of my husband in his brassiere. I think they did it on purpose to add to “the thrill”. Are you up for that?

I was on a roll. He needed that bra!

Hi Ms. Julie:

I’m so glad you’re pleased with my accomplishment today. And you know, actually, I am too! And I realize that after today’s excursion I do qualify as “you people”.

It will be next week before I can get back to VS. There is so much more to a bra fitting as you describe than what I did today, so very much. But I think I can be up for it.

Bra fitting would be a HUGE thing (step?) for me. So much more to it, so much embarrassment, humiliation, laying ones self out there, all in a very personal and sexual context. And in a way many would consider distasteful and unacceptable. Though as you say and from my experience so far, VS is very good about things. And the fitting process, including the inserts as you describe will take quite a while to accomplish. I would expect the intensity to be 10x that of my panty shopping.

I’ve definitely begun this journey though. And in addition to the above “anxieties” there has also been much excitement, lots of sexy fun, arousal and maybe I’m also beginning to discover and/or acknowledge some things.

Have I mentioned how amazing you are!? I would never have gotten even this far it weren’t for you.

So, I think I can be up for the bra fitting, with panties and tampon of course. It will have to be next week, probably Wednesday. I will let you know for sure by Monday.

So do you like my selection of panties? And I hope the pictures are what you were looking for.

Hope your day has been going well.

I responded.

Lovely!

I particularly like the middle fuller cut burgundy ones. A little less slutty and more feminine and practical for you. You did well with your tamponing as well. Imagine how you’ll feel. Bra shopping with that tampon up you and those panties on? Ha ha!

He then sent me a couple of emails.

Thank you!

Well, Ms. Julie it looks like it will for sure be next Wednesday when I can get back to VS for my bra fitting.

So……, I’m going to be measured and fit with a bra and inserts, while wearing my panties, and with a tampon stuffed up inside my ass. Oh Ms. Julie! Holy crap!!

Can’t you feel that tension building…

Hello Ms. Julie:

I just wanted to verify one more time that my return to Victoria’s Secret is on for tomorrow (Wed.). Maybe my “girlfriend” will be working again. Nervous!

Also, I wore a pair of my panties a little yesterday. Hope that was ok.

 I responded.

Very exciting!
You may wear your panties whenever you wish.
Let me know how it goes!

Well, Wednesday came and went, and he did it again (I knew he would, I just knew it!)

I did it! I again completed your directed task, Ms. Julie. And again it was very emotional for me.

I was so nervous again going in the store. Pantied and tamponed as you directed. I chose the burgundy panties. I agree with you that they’re the most tastefully feminine, which I felt appropriate for the occasion. My heart was pounding and my hands shaking again. I still feel uneasy. What might they think of me here? I mean, regardless of the company’s welcoming policy, do at least some of the sales clerks think of me as a freak or pervert even though they’re required to be accommodating?

Once in I found some bras and picked one up.

Imagine standing there, as a man, looking at those bras, knowing that in mere moments a pretty young salesgirl will be taking you in for your very embarrassing fitting…

I was glancing around. There were a lot more customers than last time. Like last time it didn’t take long for a sales lady to come over. She was not the same as my “girlfriend” last time but about the same age and very nice and pretty and helpful. It was so embarrassing even just getting my first words out, which I had rehearsed.

I started out with how the sales lady last week when I was buying panties, for myself, said I should never feel uncomfortable in here. Then: “I want to buy a bra and inserts and I’ll need to have a fitting please.” My face was getting hot and I was really feeling the tampon. Maybe I was clenching. My cock was tingling and stirring too. And I could feel myself leaking a little already.

She led me to an area by the fitting rooms, fairly private but I know people were looking as I followed her.

I said I was a bit nervous, I know lots of people don’t approve. She said “That’s their problem”. Very nice.

She measured me to be a 36 and recommended a C cup because of my fairly slender frame. Regarding inserts, she said they didn’t have them but instead sold bras with varying degrees of padding to get to the desired fullness. So I just went with that, Ms. Julie, I truly hope that’s ok.

I told her I’d like something a little fancy and she went and brought back a few for me to try on. She also brought a t-shirt to put on over the bra so I could see how I would look when dressed.

We went into a dressing room and she helped me try one on, adjusted the straps for me, etc. She had pretty, small, delicate hands and it felt nice when she touched me. The first time looking at myself in the mirror there were so many emotions going on in my mind. My God, is this really me? What’s happening? Good/nice? Bad? And I could feel my cock stirring and leakage coming on again. It just kept happening off and on the whole time I was there.

She then left me to try on the other ones myself and said to push the button when I needed her. The one I liked best was sort of purple so I asked her if it came in burgundy to match the panties I’d bought. And I actually pulled the front of my pants down a little and was able to lift my panty waistband up enough to show her! As she had the door open again to go out to search a girl walked by from another fitting room and saw me there wearing the bra. There’s nowhere to hide in those dressing rooms! We made eye contact for just a couple seconds, her expression was neutral – neither approving nor disapproving. But my face became very hot standing there in my bra and being pantied and tamponed and it made me feel so very emasculated Ms. Julie. Mortified. I just cringed.

And that tampon! It just causes such a constant, uncomfortable, invasive and, I’ll admit, a little sexually stimulating feeling the whole time it’s in me.

My sales lady couldn’t find a bra to match so she suggested getting a new pair of panties to match the bra. So that’s what I did. It’s a nice set. It was embarrassing carrying my items to the checkout and there was a line there. I tried to cover them up with my hands while waiting to be rung up but I know people saw.

When I got home I took out the tampon (yay) then stripped and tried on both my new things.

As I looked in the full length mirror I thought “I don’t look too bad” Then I masturbated, shot my load there on the floor.

I hope you’re having a good day today. And I hope I did well for you, Ms. Julie.

Was that not a great nerve wracking experience? Masturbated and shot his load on the floor? TMI!

Boys, I want you to have a good look at this man in his bra. There are some men who enjoy dressing as women, or somehow feel fulfilled doing so. There are other men who consider it be a deeply embarrassing, emasculating thing. If you belong to the latter class, then a brassiering can be a perfect punishment for you, as determined by your wife or by another woman in your life. My husband certainly lives there.

I did a post called Summertime – Wandering Eyes – Hot Bottom! where I caught my husband blatantly staring at the breasts of a young woman on the street. As a consequence I sentenced him to bra punishment in front of his trainer at the time, a young woman named Mags who was really into spanking him. Poor david really did not wish this particular young lady to see him in his bra and he put up quite a fight. But he obeyed in the end.

He got scolded by me in front of her, as she ogled his big bouncy breasts.

My pen pal ‘lil joe did a drawing for me under my direction. I liked it so well I used it as the cover for my e-book.

After the scolding, where he was threatened with a chastity cage if he did not learn to behave around women in the street, he was draped across the couch, still in his bra, and got his backside SIZZLED by my belt while Mags looked on and helped hold him down. After that, I allowed him to put on a T-shirt over his bra, but insisted he exercise under Mag’s guidance with his bra and breasts on. A little feminine empathy training.

So, in short, an excellent way to knock a man down a peg or two.

Back to the gentleman at hand, I had to write him back right away.

OMG! Amazing experience again!!! Quite the adrenaline rush I guess. I even got an adrenaline rush shopping with David. Very similar experience to ours, right down to the salesgirl leaving the dressing room door open so other women could peak in. I’m sure her expression was neutral, but boy will she have a story to share.

I would love a photo of you decked out in your matching bra and panties.

Also, I would love to be able to share your experience (with the various photos you sent) on my blog. Would that be ok?

Also, if not too much trouble, can you go back and discretely take a few photos of the VS? Would be better than using stock photos! You might have to buy something else for cover. How about stockings and a suspender belt? I do so love how it frames up a bottom so perfectly for play.

The photos I received I’ve already mixed in above.

Oh yes, Ms. Julie. It was a huge adrenaline rush for me, and with a wonderful sexual bent! Definitely another amazing experience, and I thank you again.

I suspect you’re right about my salesgirl yesterday having the fitting room door open just a little longer at that particular moment, very “accidentally”. As you said, monkey business will ensue!

Yes of course I will get a picture in my new matching set to you. It may be tomorrow or even maybe the next day but I will send it I promise.

Yes, absolutely feel free to utilize anything in our letters- words and pictures- for a blog post. I will go back to VS to get a few pics of the place, it’s no problem. And you’re right, I’ll most likely need to purchase something so will opt for suspender and stockings per your recommendation. As usual it will be next week before I can do that. I always have to wait for my day off to get to town. I’ll be in touch again soon with that picture for you of me in my finery.

I was very excited to get permission to publish! I wrote back,

Wonderful!!! 👏👏👏👏
Thank you!

He got me those VS pics (above), and told me about his garter and stockings experience.

I looked for garters and nylons per your suggestion. A sales lady did come up, she said they don’t carry garters, or nylons(!?) and actually I didn’t see any around. There’s another women’s fashion store in the same mall that does have them in their “naughty” dept. So I was able to find some there.

You’ve always asked for pictures modeling my purchases so I took it upon myself to take some. I hope that was OK and that I wasn’t just assuming.

I took one wearing them with my matching bra and panties, front and back.

I also took one from the back with no panties. I see what you mean about framing the bottom for play! I humbly submit this photo such as it is, along with all the others, to you Ms. Julie. And again, as with the previous ones, of course feel free to use as you wish, have use for.

Oh I do like a nice pair of stockings with a garter belt on a man. It brings out the absolute worst in me! I think I have a strong desire to dominate a woman, and the lingerie brings it out, even on a guy. Even more on a guy, you little sissy bitch! You will come across my knees and kick those pretty little legs while I blister your bum with my paddle, young lady. You will then bend over, stick that little bum up, and taste a long hard dose of the strap. Once you’ve been thoroughly paddled and strapped, you will beg to have me fuck your tight little asshole until you squeal, little one. Squeal.

Ready for a fucking

So that is this episode. I hope you enjoyed it and were able to live vicariously through another of my wonderful pen pals. You can see why some only write to me once a year! Intense!

Source: Strict Julie

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