Saturday, May 23

eSubbie Tampaxed and Bikini Bottomed

You will no doubt remember one of my eSubbies, jessica. I first introduced you to jessica in my post A new eSubbie!, and then again in eSubbie Waxed!. In the first he was sent shopping to Victoria's Secret for panties. In the second she was sent for a full Brazillian waxing. I know many of you have asked about jessica, so I'll catch you up with two of the tasks I set for her.

jessica sent me an email saying how he had received a text from a woman he has a crush on:
She sent me a teasing text about my feminine dressing which made my day.
But she also told me she's not coming home for a bit.
Anything I should do while I wait?
 I wanted to respond quickly, so I shot back with one of my standard dares for a "young woman".
Hi jessica,
Yes, there is something you can do while you wait. I believe your period is coming on.
Go to the drugstore and buy a box of tampons, a box of pads, and some lube. Checkout with those three articles only, nothing more. Then I want a tampon in your boy pussy continuously for the next week. You'll have to carry a couple extra with you at all times in case you need to use the restroom and have to change your tampon. Your flow will be particularly heavy for the the first 3 days, so double up with a sanitary pad in your panties as well. Use your lube while inserting your tampon, and while removing it.

And no complaining about how tight your little boy pussy is and how hard it will be to insert a tampon. Young teenaged girls have been saying them same thing ever since tampons were invented and somehow have managed.
Make sure it's all the way in with only the string hanging out. It's designed to be safe that way.
And send me a photo of your pretty little bottom with the string dangling out between your cheeks as proof that you are doing it.
This exercise will get you much more in touch with your feminine side. You'll be able to tell your "girlfriend" all about it the next time you see her.
As you can see, jessica did as she was told.


And here is her story:
I wanted to really get into it, so i wore leggings so i could look super girly. like, you know how small i am so i don't have a bulge or anything! I saw one ladies eyes glance down at me for a second. like that "what is that?" sort of look/ or "is that a boy" look. i guess i have a fairly fem body. except of course my legs which have regrown their hair....
But i bought what you said. The cash girl asked me, a bit quizzing like, if i'd found everything okay. 
I said, "I think so."
There was an awkward silence.
I chirped up, "that time of the month, you know?"
She nodded. "your girlfriend must really need these, sending you in. You'd better hurry on back to her before she gets upset with you."
I think madam cash girl thought i was pussy whipped by my gf.
"Oh, i don't have a girlfriend. I wish i did."
This cash girl was about 5 years older than me by the looks of it.
"what? are you on your period then?"
she was clearly just joking, but i blushed.
"Oh my gosh. are you one of those fairy boys?"
I couldn't handle this Ms Julie. I panicked. "I'm just kidding, i have a girlfriend. I just thought you were hot and i thought maybe i'd flirt with you."
she laughed and shook her head "hun, buying tampons and flirting is not a great combo."
I still felt flushed.
"here's your tampons, sir. now run along. your girlfriend must really need those if she sent you running out of the house in her leggings."
I wrote back,
What a wonderful femdommy experience for you. Just goes to show, most women relish the chance to put a boy in his place! Us women especially love it when we find out that a sister has her boy well whipped!
and jessica replied,
Yes Ms. Julie. It really was. I'm surprised though, I thought you'd yell at me for not staying shaved. But it's a hassle to put such efforts in. Does david stay shaved?
And, you know my girl friend, well, she asked me if I wanted to go swimming with her this summer. What should I do? I mean, do you think she expects me to...? Be publicly feminine...?
me,
Yes, I know it's a burden jessica, but shaving and waxing is part of what being a girl is all about. Shame on you for neglecting that! If you were mine, you'd be due for quite a spanking.
And yes, of course you should find a cute little bikini bottom to use as your swimsuit. The tinier the better. I'm thinking yellow. Make sure it's cut so that your lower cheeks are exposed. You can then "kid around" with her that it's like that to make it easier for her to give you a smack on your bottom if she feels you need it.
A few weeks later jessie emailed me back that "she" had bought her bikini bottom. I immediately demanded photos and the full story. Here is her purchase,

and her story,
I went to forever 21 up in the mall. They have so much clothes its intoxicating! But i went looking through their suits. They had a deal, mix and match top and bottoms too. But of all they had, nothing in yellow that was in my size! Can you believe it?
There was a girl, younger than me, who asked if i needed any help. I blushed 3 shades of red and said no. A few minutes later i went over to her. i literally stuttered my heart was beating so fast. i said, "i can't find any yellow swimsuits." "your girlfriend wants yellow?" "i was specifically told" i answered. so she came to help me look. she bent down to scan the racks and i saw her green panty peaking out of her skinny pants. while i was oogleing she turned around. "here's a cute one in yellow. what size was your girlfriend again?" "oh um she's about my size" i blabbed. the young girl grinned. she held them up to me. not touching me, but close to me. she held these yellow bikini bottoms up to my crotch. i was wearing tight womens jeans. "oh, no. These are much too big." My penis stirred in my panties, but i looked down and sighed in relief because it didnt make the slightest bulge, not even in my low rise jeans. "what size are those?" i asked. "a large. you need a small." my penis hardened. but again, no sign of its existence in my pants.
she looked awhile and finally said "nope you're right. no yellows in small. I've got a top in medium though." She handed me a string bikini top. "why don't you just mix and match, that's what everyone's doing nowadays. Do you like floral?" she held up a black bikini bottom in a pink floral print.
I know you told me yellow Ms. Julie, and i tried to get yellow, but they didn't have it, and i loved the one she found. i just had to take it. i hope you like it too. please tell me your honest opinion. i won't wear it if you don't think its good.
she really pressured me into getting the top too. but i just couldn't. i mean i cant wear a top. it would look ridiculous, wouldn't it? i mean, maybe i'm delusional, but i think i actually look good in the bottom. i don't really want to go in public trying to make a blatant scene or offend people or look wrong. i want to look good.
so i told her no and just bought the bottoms. she says "we have a deal though, mix and match, you'll be losing money if you just buy the bottoms." "i know but i... i don't need it...i wouldn't even know what size." "what?" she teased "your girlfriend's not the same size as you up top?" i blushed. i dont know what i did. i froze. "guess we can't measure you then" she laughed. "let me know if you need anything else."
Well I for one can't wait for swimming season now!

34 comments:

  1. I just adore these posts about jessica! And the pictures make it so very real!

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    Replies
    1. Yes, I know that jessica has some real fans!

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  2. hmmmm maybe jessica should have to go back for the top in order to get some sissy tan lanes. Hopefully she scores some bras maybe at victoria's secrets during the sales this weekend. I know they will have their semi annual sale starting the 25th through june 8th

    Katie

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    1. By refusing to buy the top it was so very blatant he was buying the bottoms for himself! But yes, a "man" with tan lines around her boobs would be great fun!

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    2. maybe something for david to get as well ;-)

      Katie

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    3. You know, Miss Julie, Jessica really should bring that very helpful sales-girl a thank you card.

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    4. What a fantastic idea!!!

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    5. Keep us posted, Ma'am. :)

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  3. A girl has her period every month. Cramps and bloating are a normal part of a girl having her period. Jessica should give herself warm water enemas to experience cramps and bloating.

    No girl would wear just a bikini bottom. Jessica should be sent back for the matching top.

    And no girl would go shopping without her purse and at least a little makeup. Girl's jeans are fine but under those jeans should be panties, a bra and pantyhose and a panty girdle. All girls understand these important points.

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    Replies
    1. jessica's kink, I believe, is "Questioning", not full on Tranvestite!

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  4. String bikinis are fabulous. They look so super girly and they are widely adjustable. Mine is hot pink and I love it. Our pool is fairly private and my wife makes me wear it all summer - enough that I get classic bikini tan lines and have to avoid the gym for the summer.

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  5. Miss Julie,
    Are You interested in taking on any additional e-Subbies? If so, how does one apply?

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    Replies
    1. The more the merrier. Send me an email (see "About Me" top right). A quick return email from me, a world of hurt and humiliation for you!

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  6. Do you think his penis really looks that small in those bikini bottoms?

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    Replies
    1. I imagine it does. Some "men" are just very tiny.

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  7. Once again I'm in awe of you and applaud you for helping a little boi and putting her in her place!!!! You are exquisite Ms Julie!!

    Respectfully,
    doc

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    Replies
    1. It's such a pleasure and so little trouble for me.

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  8. looks like jessica needs to schedule another waxing. ick hairy legs

    Emily

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  9. Having retired from being an HR manager for a major retail company that saw its share of cross-dressing and transgendered clients, I would point out that both sales people mentioned acted inappropriately. The Forever21 clerk would be scheduled for some coaching and the drug store clerk strongly reprimanded, or possibly fired. Regardless of a client's dress, orientation, or honesty about their reasons for purchases, it is not the place of a salesperson to make insinuations .......or worse, insulting remarks.

    I don't know where Jessica shops, but in going to just two places and being treated this way in both indicates either a backward area, or extreme bad luck in coincidentally finding the two most ill-trained salespeople around.

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    Replies
    1. I have to agree. My personal experiences have all had the sales ladies act in a very professional way (maybe a little smirk, or am I imagining even that?)

      Perhaps jessica embellished a little, imagining the "inner dialog" of the sales lady? Not beyond the realm of possibility.

      jessica?

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  10. Now that Jessica has tamponed her virgin boi pussy, maybe it's time for a sweet and gurly butt plug like this one? It comes complete with a pretty rosebud (how appropriate!!)
    https://www.etsy.com/ca/listing/202202725/mature-glass-butt-plug-anal-clear-pink?ref=market

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    Replies
    1. How appropriate! And at 1.5" in diameter, not without its challenges.

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  11. does binki bottom have lot protection when person wearing them getting a Spanking or does it hurt more

    i wouldnt mind wearing binki bottom when iam getting spanked by female might make it more embrassing

    i alway dream of being spanked by female wearing binki or binki top and jean shorts or jeans

    Mike
    Madison

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    1. My own experience spanking david with him wearing bikini bottoms was that they tend to ride up the ass and give me a nice expanse of lower butt cheek for me to have my way with. I do admit to tugging up a little to expose even more. What's even more fun, though, is having him walk around at the beach in front of other women with those rosy lower cheeks on display. When they see that, with me holding his hand, they know who's in charge!

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  12. She seems very obedient. Are you going to meet her in person? That would be fun!

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    1. Perhaps if she were to ever visit Toronto - maybe anonymously in a hotel room for a good spanking! She seems VERY harmless.

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  13. Didn't you first tell her to get a bra? You ought to demand she goes back to Victoria's Secret and gets measured for one!

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  14. Oh my gosh!! How did i miss this delicious post!? Hee hee (shopping blush).. sara

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    Replies
    1. Don't want to miss any jessica posts!

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  15. Public humiliation is tricky. Finding a participant who is willing to drop the professional facade and play along can be a lucky find, but more often it requires a "partner in crime" and some careful planning. When it all comes together to provide a blushing, crushing experience...oh!

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