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.