Saturday, January 9

Update on Baby jessica's Halloween

One of my pen pals is a youngling named jessie. You can read about jessie in some earlier blog posts, the last one being this one where I sent "her" to buy and use some feminine hygiene products.

After a time, jessie wrote me back...
Anything else I can do Ms. Julie?
I think it's time for a bra, sweetie. Off you go to a lingerie store to get fitted. Ask for breast forms and a bra. They are to wear in private, not out in public at all, but I do want you wearing it in private to get that "real girl" feeling you can carry around with you all day.
You're.. you're probably right I guess Do I have to get fitted? They'll know it's for me! And no breast forms or bra in public right?
Of course you'll be fitted and of course they'll know it's for you. You will have to try it on, especially the breast forms. I can assure you the salesladies are quite used to cross-dressing males and even seem to enjoy the interaction. They even have a policy at Victoria's Secret and at Nordstrom's of being tolerant. So they have fun with it as a result. And no, not in public (except I will want a photo, of course, for my private enjoyment!)
I'll get right on that bra shopping. I'm actually getting excited since I've had to wait. And I was even considering asking my girlfriend to come with. Is that a bad idea?
No, that's a great idea! I think it eases things if you have a woman helping you shop.
After a bit of a delay, jessica finally got back to me.
Sorry it's taken me so long. I did go though with it, Ms. Julie. And actually I told my friend I wanted to get a bra. And we talked about it a bit, and then she came with me. And... then... I lost my nerve. We walked right by Victoria's Secret. Didn't go in at all. She was a bit annoyed, and I felt bad. I made her waste her time with me and we didn't even go in. That was a few weeks ago. Since then I went by myself. Not to VS. I'm just too afraid. My friend told me I have to get measured but I'm scared of that too. So I just went to Target and bought what I assumed would fit me. It does fit I think. This story doesn't have the same drama as my other shopping trips, though. The check-out woman didn't comment on my selection. I just bought one set.
Bad boy! you apologize to your friend, tell her you deserve a spanking from her, and then SWEAR to do it next time if she will only take you. I assure you they are very welcoming at VS. It is a store policy to be sensitive on matters such as these.
We had some more back and forths that I don't want to bore you guys with. jessica was worried she had alienated her friend for good. For some reason, jessica never asked her friend for that spanking. I think she's terrified of the very well deserved fanny pain she would be forced to endure, bare bum across her friend's knee. I understand the friend is quite strong and fit. Some type of athlete. I might have to make her do that.

At a certain point jessie requested another assignment from me. I told her to insert something into her bumhole as she had never done that before, and send me a photo. She sent me a photo of her in panties (!) with something sticking a little out... maybe a pencil? You be the judge.


My response...
You need to buy a suitable ass toy, jessica. Who don't you get yourself over to a sex shop. Have a conversation with the lady there over something suitable to go into your bum. Tell her you want the experience of being fucked like a woman, but you are very tight back there. She'll find something suitable for you (maybe even test it for fit ;-)
And then jessie came up with an unexpected twist
So my girlfriend...the one I said I thought I lost... well I decided to text her because I remember she said she liked plugs. And I thought I could be in for a legit femdom experience. Like your scenes with david except not a scene. I mean she was mad at me at first and didn't want to text. But when I said I just wanted advice on ass toys... well she opened up. She told me she could, quote, "show me some of hers." We've set up a time to meet, so it's happening. Am I reading too much into this? It seems like this might be my first (pretty much ever) sexual experience with someone else. I'm excited and terrified.
Well that's an exciting development! I emailed jessie a week later asking if there were any further developments. I'll let jessica bring it home...

Oh yes Ms. Julie! A lot of developments! I'll embellish a tad little bit with a quote or two but hardly at all. This REALLY HAPPENED and I CANT EVEN I just CANT EVEN BELIEVE IT. I didn't think something like this would ever happen to me.

I went over to her house wearing my leggings and a T-shirt. (I almost exclusively wear leggings now...all the college girls around me do so I wanted to too).

We went into her room, had a little bit of small talk, or girl talk. We talked about boys... she seems to always have a new boyfriend every time I talk to her. She never keeps them very long. Then she brought up why I was there: ass toys.

She said "these always come in handy when I'm between boyfriends. I'm sure they could help you too." she smiled at me.

I looked...wide eyed... at her collection. I've never seen this sort of stuff in real life Ms. Julie. She had a number of butt plugs and a dildo. I told her I had no idea what I was doing.

She smiled again and said "I can help you. Shut the door though. My parents are home."

(oh and I forgot to mention Ms. Julie, she was home for this weekend, which was Halloween weekend, because there was some party she wanted to go to with her high school friends. So she came home instead of having Halloween with her college friends as usual. This was Friday night that I was at her house.)

I went to shut the door. "Damn jessie. Your ass looks alright in those."

jessica sent me a photo after the fact of what she was wearing

I blushed.

"Let's see it a bit better, though. Bend over the bed."

I just looked at her. I don't know why I didn't bend over right away.

"What? Do you want me to show you my toys or not?"

I didn't say anything. but I bent forward on her bed. She put a hand on my ass. All of a sudden she seemed hesitant too.

"Are you sure you want me to do this?"

"Yes," I said.

She put her other hand on my ass and pulled my leggings down, just a little bit to my thighs.

"ahaha" she softly chuckled. "You do look cute in these." She snapped my panties.

ditto for the panties

She hasn't really seen me in them before, but she's seen the tag when she checked and she saw them in my room when she came over before... remember Ms. Julie?

She showed me her dildo. I gulped. I'm not gay.... and... it was so big...

"Anything smaller?" I asked.

"Sure," she grabbed what I think was her smallest pink butt plug. "Let me lube this up. I don't want to touch your ass, but I don't want to hurt you either. It probably will hurt a little, it's your first time."

She lubed up the plug and came behind me.

"Eww! jess!" she cried when she pulled down my panties. "You better shave this little bum of yours! That's the last thing I'd expect to see from a boy like you." The way she said 'boy' made me think she didn't think I was much of a real one...

She started to slide the plug in me. At first... it felt so good... like... oh my I really felt tingly... But then she pushed more. It started to hurt. And like it really hurt. I held quiet. I didn't say a thing. But then I was crying. It hurt so bad. She stopped.

"Jeez jessie. I didn't even get it all the way in yet."

I looked back at her, tears running down my face.

"Okay you've had enough," she started to put the plug away.

"No please!" I begged her to try again.

"Okay. Stop being such a baby then."

I swallowed hard.

She put it in me again. Not far this time. Just poking it slowly in and out. I felt a tingling again. I reached for my penis and flipped it up so I could hump the bed. She laughed and started going harder. It hurt. I kept humping. But soon I was crying again too.

"Will you man up already?" She stopped again.

I whimpered.

"That's probably not the right phrase now that I think about it," she shook her head. "Suck it up maybe."

She handed me a tissue and put the butt plug away.

"It hurts," I said.

"Well if that's the way you want to have sex, then put your big girl panties on and deal with it."

I stood up.

"Oh my God! Don't show me your dick! I don't want to see that!"

I quickly pulled up my panties. Honestly I don't think she saw it much. Not for more than a split second. I pulled my leggings up. I was still sniffling. She sat down on her bed and said I could sit down too.

"It's okay," she said.

Somehow we shared a touching moment then sitting on her bed. Tears in my eyes and her hand on my shoulder. We talked about why she got mad at me before. The biggest thing was when she (really kindly) took me bra shopping when I asked her to and I refused when we finally got there. I apologized. I cried a little more trying to explain how hard it was to buy a bra. Eventually we hugged.

Before I left she started telling me about the Halloween party she was going to (which was tomorrow). She said I should come with her because she had seen the perfect costume for me when she was out buying hers. She wouldn't tell me what it was. She just told me to come back to her house tomorrow morning and we would go out and buy it together.

Well I did just that. We drove to the store. She went and found it and just started cracking up as she held it out to show me. It was a leotard with puffy sleeves and on the chest it read CRY BABY and it came with a head piece and a binky. I got super embarrassed. I tried to say no but she asked me why not? She said isn't this perfectly fitting for you? What could I say? I shrugged. Eventually, I nodded.

We went back to her house. She helped me put it on (it was a little tough to slip in to).

Wow. Not a lot in the "package" is there?

She laughed so hard!

I protested. I mean I was really not happy with this. I would've rather been something else but she just put the little binky in my mouth. I let her and she laughed so so hard. But then she said I did look kind of sexy. And I guess I did. It's a leotard so it's not really babyish, at least not below the chest. That made me happy. But I was absolutely petrified about what would happen at the party. I've never been publicly humiliated before, Ms. Julie. I mean not unless you count my shopping experiences... which arguably do count... but I wasn't dressed in a cry baby suit and that's more embarrassing than just being feminine. You can imagine my inner fear when I went home afterwards to wait for the party later that night.

She came to pick me up. She insisted on driving. We made our way to the party. At least no one here would know me. These were her friends that I didn't really know. Oh and just to say, my friend was dressed as a pirate. A sexy pirate but not slutty in any way. If anything it made her look more powerful, at least to me, compared to me.

We walk in. She hugs one of her girlfriends, and the the girl sees me. She laughs out loud. I blush.

"Who's this?"

"Oh this is my friend, jessie. He wanted to come, I hope that's okay."

"Oh sure! He's cute. This has to be a girl's costume..." she looked at my leotard. Its tightness and my little bulge.

"Yeah I actually picked it out for him. It's very fitting."

"What he's a cry baby or something?"

"Oh yeah." She looks at me and asks, "should I tell her the story?"  I shake my head. "Oh alright, I'll tell you later" she says to her friend.

So we go in. I meet people. It's more of the same. But not always. Some people don't even remark on my costume. I mean it is Halloween after all. People are the most open minded on Halloween it seems. It was a normal party. Eventually I felt comfortable and it was actually really cool because like I said none of the people knew me. I could be the real me. And it didn't even matter that I was wearing a baby costume. Soon I was sitting legs crossed, martini in hand, and laughing with three or four girls.

The first girl I met actually spent the most time with me. She and my pirate friend did humiliate me some. I mean they teased me. My friend said, "Does baby want some yummy appetizer?" I just smiled and shook my head as if to shake her comment off. But she kept going, "Come on. sit on my lap. I'll feed you." I hesitated. The other girl said "yeah come on!" and grabbed me by the arm and pulled me towards my friend. My leotard clad ass plumped right onto her lap. "Here comes the train." teased my friend and shoved a spoonful into my mouth. "I want to feed her," the other girl said, and gave me a bite of her brownie.

All of a sudden I was a 'her'. And all of a sudden we were drawing a crowd. I started to pull against my friend but she held me tight. You know I'm small Ms. Julie. She is stronger than me. One of the onlookers asked if there was any baby food in the house. Thankfully there wasn't. And the feeding stopped. But my friend held me on her lap for the next while. I admit to enjoying it. The humiliation. But I also enjoyed before the humiliation when I felt like a girl.

Afterwards, when my friend drove me home, we talked a little bit.

"You liked that everyone starting calling you 'she' after a while right?"

I said, "I guess. I mean. Yes. I think I did."

"What do you mean you guess? You don't wear anything from the the men's department. Ever. I saw your room, remember? Girls clothes all over floor."

"Okay. yeah. But the whole baby thing..."

"I treated you like who you are. No, you're nothing like a man. But you weren't much of a woman either. Crying like a baby when I stuck a little plug in your pussy."

That was my Halloween. And it was a crazy, awesome experience.

37 comments:

  1. wow hopefully we get to hear more from Jessie. You should send have her get some diapers from rearz https://www.rearz.ca/ or abu space diapers http://www.abuniverse.com/Space_p_71.html

    Emily

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    1. When the girls asked if there was any babyfood in the house, I thought surely the next question would be... "and have you got anything we can use to diaper her with?"

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    2. When I saw the baby costume I would have thought for sure she would have grabbed some real quick as well. maybe your hubbie would like to train in a costume like that

      or maybe in something from here - http://thesissystore.com/

      Emily

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    3. He's less into the baby thing... But maybe that's why I should make him???

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  2. Some very exciting experiences for Jessica, even if she hasn't had the spanking she so deserves.

    My wife calls me a girl sometimes, or her panty maid. We haven't taken my cross dressing too far beyond panties and slips and a bit of lipstick. I'd like to go further sometime but it feels silly since I am tall and strong. She's made a few hints about putting me in a bra. I've though about buying a red nylon nightgown from shadowline. I sometimes wear nylon pant liners around the neighborhood - they feel very sexy and naughty.


    Irene took immediately to spanking me and fucking my bottom with her toys. Bondage and girly clothing have come more slowly into our world but have become exciting parts of it.

    - Rosco

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    1. I think you boys obsess overly about your body images when dressed in women's clothing. If it feels naughty, and humbling, then that's surely what it's all about? Let us women worry about whether we accept the aesthetics of it. Having my man looking ridiculous is part of the fun for me!

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    2. Plus I hope its mandated now that he go bra shopping with her she might insist on him getting a training bra too. I am actually surprised with the way it sounds that they haven't gone out on a mani pedi girls day yet.

      Emily

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    3. Bra shopping needs to happen now, I agree.

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  3. YIKES!! That's some serious humiliation. Time for Jessie to get some real cock in her mouth!

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    1. Maybe she can ask her ever-dating "girlfriend" to set that up?

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  4. Wow. That is am awsome read Ma'am. All the not-as-scripted stuff is just a reminder that its a real experience not a made up scene. The humiliation in the costume, being treated like a baby, and being called by a gurl name. Well, you know me Ma'am: I'm gone with that stuff. Thankyou Ms Julie and thanks Jessica.

    lill (Ms Julie's punished sketch slut) jo

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    1. I thought you'd like this adventure!

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  5. I told my wife about the bra fitting I read about, and how "he" couldn't bring himself to go into VS. I said I could never do that either. Our conversation went like this:
    "If I told you to do it, you'd do it."
    "But you wouldn't, would you?"
    "That's not the point. Is it?"
    "No. I'm just wondering what would happen if you told me to and I just couldn't."
    "You tell me."
    "Punished?" (My face got red)
    "The blister stick, and then you'd get a second chance to obey."
    (She smiled her pretty smile. I was having another attack of trouser arousal.)
    "Yes, Ma'am."

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    1. Oh pish posh! Grow a pair already. You want to play at being submissive without really playing at being submissive? What nonsense.

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  6. i wonder if jessica female friend had ever felt intrested in spankin her or not or least has intrested in spanking make me wonder never even then ask for the spanking again

    seem like the female frend forgave her was willing her do her share with the toys for the butt as you order

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    1. I think spanking is still unexplored territory...

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  7. one thing i want say is hahaahaha Jessica got the punishment he she desver if ask me fit the crime if ask me

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  8. There are some days i just can't get myself into the VS... but I MAKE myself go right back in, the next day... no delaying!
    i like jessica's little VPL!
    That baby outfit certainly would be embarrassing. Whew, glad i've dodged that one... so far! sara

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  9. What an amazing costume. I can't stop imagining a Strict Julie's party where all the boys were wearing that outfit or something similar.

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  10. I was just waiting for them to offer breastfeeding...Although it probably wouldn't have fit...

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    1. Breastfeeding is a funny one. In there anything more babyish? And yet grown men crave it...

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  11. Ms. StrictJulie:

    I commented already, but this story had me going all weekend and is still on my mind. I like the realism - usually present at strictjuliespanks - as well as the cool, aloof and mocking attitude of Jessie's friends.

    The story also reminds me of one of my most powerful fantasies - all of which are derived from real life stories that could have turned into something truly special, and maybe would have turned out differently if only I had said or done the right thing:

    A few years ago, my wife Irene and I went to a Halloween party thrown by two female colleagues - Julie (yes, Julie!) and Karen. We arrived early as they were helping Karen's sister Laura with her very sexy French maid's costume by stuffing her bra. The fun they were having doing it was a bit of a turn on. I thought Laura looked great in the short black dress, and hoped to get a peek under it to see what panties she was wearing. I never did, but not for lack of trying.

    We stayed late and were chatting in the living room with Julie and Karen, as well as an attractive young female public interest attorney named Theresa as the party came to a close. Laura then came of of one of the bedrooms, having changed out of her French maid outfit and carrying it in her arms.

    Somebody commented that she had changed and I blurted out that it was too bad since I had hoped that she would be serving us all tea in the costume.

    Karen quickly replied that she had taken it off so I could put it on and serve tea. She asked the other women if they thought that would be a good idea. They agreed, and my wife Irene said "definitely" in a very clear tone.

    I tried to laugh it off, and said I would be happy to but I was sure the dress would be too small and would not fit. Karen replied that it was "one size fits all", that she was sure I could "shimmy" into it. Then she said it might be a little short (it was short on her, and I am 6'4"), but that the ruffled panties would preserve my dignity.

    I must have turned 50 shades of red. I looked at Irene who sternly motioned for me to take the outfit, and go to the bedroom to change into it.

    When I came out, I felt my hard penis straining against the tight ruffled panties. I did not know whether I wanted them to see it our not. They instructed me to twirl and then to bend over. I was then dispatched to prepare tea for all.

    As you might guess, I spilled the tea and made quite a mess when I tried to serve it. That earned me a spanking - and each of the five women seemed to try to outdo the others with Karen's hairbrush and then Julie's belt. They left the ruffled panties on, but pulled them up tight to my bottom was vulnerable. I tried to pretend it didn't hurt, but was soon kicking and crying out. They told me to be quiet and that I knew I deserved it. Julie said she needed to teach me to improve my behavior at the office.

    I had thought the whole thing might make Irene jealous, but she took me home, made me lick her pussy then fucked my lights out.

    The next morning Irene put me back into the French maid's outfit and marched me back to Julie and Karen's apartment to clean up after the party. I've been cleaning their apartment once a week as French maid ever since. Irene's only stipulation is that they spank me soundly each time I visit.

    -Rosco


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    1. I like you're story Rosco. I wish you had got to experience all this. Kisses. jo

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    2. I'm trying to pick out the bits of it that actually happened... m guessing you made that comment about having her serve tea and she said "no you" and then it got laughed off?

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    3. Yes that's right - I've got a bunch of fantasies of this sort in a few cases I was actually threatened with a spanking.

      I'm not complaining at all. My wife Irene creates all kinds of role play that is intense and wonderful for us both.

      -Rosco

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    4. well! You deserve a spanking !!

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  12. Wow....fun read thank you
    Always
    Ron

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  13. hot story........................

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  14. Is jessie a real man? I mean i literally can't tell in that picture

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  15. He said he wears leggings all the time?!? I can only imagine what all the girls who see him around must think....

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