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!