The Adult Sissy

I’d kept in touch with Tommy while I was away, but he didn’t text me much, so I was not really expecting him to see him after my appointment that Wednesday. I had texted him and told him my appointment would be a little longer, might last for a couple of hours. He was pretty noncommittal. I didn’t tell him I was dumping the curls and going with a more adult style, shorter and, I thought, more sophisticated, straight, like European girls wore. And I didn’t tell him about my new boobs. I decided to keep the platinum blonde color.

I wore a t-shirt without a bra, so he and everybody else could see my new tits. Blue shorts and sandals and a huge white leather purse completed my outfit. I guess it’s repetitive to say I looked sensational, but I did, so why not tell the truth about it?

My hair came out great. It was cut in sort of a pageboy and it tumbled into my face as I bent my head. I loved it and I looked great, more sophisticated and mature.

It sort of surprised me to see Tommy there. But I acted like I expected it and I waved cheerily and joined him, and spent the time telling him all I’d done in Europe, except the operation, I didn’t tell him about the operation. It didn’t take him long to start staring at my legs and feet, again. I’d gotten blue nail polish and sequins and I flashed him every time I could, he obviously liked them so much and he felt like he’d been neglected. I bent my torso a couple of times so he could see my new tits, but I acted like it was perfectly natural, and he didn’t seem to notice anything different. Which was good, I think. I told him I had finished high school and was deciding what to do about college. He said he was graduating in June, and had a scholarship to the biggest private school in the state that, evidently, had a continuous need for football players. I acted like I was interested, but football? I was more interested in him ogling my legs. Mom was a little late, and she greeted Tommy warmly.

When we were walking away, Mom said, “Look back over my shoulder to see if Tommy is watching”. I did and he was. Mom said, “Good, smile.” I smiled.

We talked about Tommy in the car and when we got home. “Do you like him? We can hatch a plan, girls do this sort of thing all the time.”

I was skeptical, “What plan?”

“You have to find out you know, I mean whether Tommy would still be interested in you considering you were born a boy.”

I cringed. Heck, I didn’t think of myself as a boy often. “How in the world?”

Mom said, “It’s a little risky and, if the worst happens, we might have to change a couple of things, but we could find out.”

“How?”

“I think about this sort of thing, it’s fun. What I came up with was getting a t-shirt made for you with a great big lollipop on it, with a ribbon tied in a bow on the stick. Across the top, ‘I’m an All Day” and across the bottom, ‘Sucker’.”

My jaw dropped. “That’s vulgar.”

Mom continued, adjusting my shirt keeping her hands on my shoulders, “You could wear another shirt on top of it to Babe’s, then take off your top shirt when Tommy meets you at the ice cream shop. Tell him you found it in Europe. Ask him if he likes it. I suspect he’ll be speechless and staring at your chest. Think of all the fun things you can say, think of being flirty. I could come up early this time and walk up to you and act like I’m angry, and grab you by your arm, and say something like, ‘Young man I told you never, never to wear that out of the house, I never should have let you keep it’, and drag you away. You can look over my shoulder to see if he’s watching, I think he probably will be, just give him that big smile while I march you away. That’ll bring things to a climax. He has your phone number, right? What do you think?”

“Mom. Mom. Mom. You’re a genius. Make the lollipop red. I look good in red, and have it shaped like a heart. I could wear my red wedges and that red shirt over it and my short red skirt, and get my nails all done fire engine red. What an idea. It will certainly bring things to a climax.”

“Always remember Sissy, once you get your lips around his dick, you own him. You may have trouble getting rid of him, but that can be fun too.”

I was shocked, “Mom, what would keep him from spreading that all over the place?”

“Nothing really, but after he thinks about it a bit, I think he’d be a little hesitant about doing that, since he would become the butt of the joke. After all, he was attracted to you and I’m sure he’s told all his friends about you. If he calls you, then you can take the next steps. If he never calls you again, you will have found out without wasting a lot of time on him.”

“You’re a genius, Mom. An absolute certified genius.”

Mom smiled, and said, “I have my days. I want my little Sissy to be happy. It’s about time you had a sex life besides your hand,” and she pinched my chin.

I wore the clothes as advertised the next Wednesday. The day was beautiful and I wore a button up shirt on top of my very, very vulgar t-shirt.

It went pretty much as Mom planned it, except that I couldn’t resist looking back as we were leaving and smiling and mouthing, “call me” while being marched away.

He did text me the next day:

Tommy: Well, is it true?

Me: Yep. I knew Mom would ground me if she saw it. I’m grounded for a week, but it will be worth it if you liked the shirt. Did you?

I knew that wasn’t what he was asking, but it advanced the conversation.

Then after a few minutes I got another text.

Tommy: Grounded. Oh. That wasn’t what I meant.

Me: What in the world did you mean? The t-shirt?

Another few minutes passed before he answered.

Tommy: That you are a young man.

Me: Sure, you never asked, and you obviously liked me, so I thought it didn’t matter to you.

Another few minutes passed.

Tommy: You are very pretty. You don’t lose your phone when you’re grounded?

Me: I’ve never been grounded before. I’ve never done anything like that before. Mom and I are rookies. I think she only grounded me because she saw it on TV.

Tommy: Can I come over then?

Me: Come over? Why not? When?

Tommy: Now.

Me: Not now, maybe in a couple of hours?

Tommy: OK, at 7?

Me: Sure. I won’t tell Mom, so she won’t tell me no. 😉

Tommy: See you then.

Me: I’ll look forward to it.

Of course I ran and told Mom immediately. I was suddenly nervous.

“Well, Sissy, he’s going to think he has a chance to get some sex.”

“Oh Mom, no. What’ll I do? I’ve got to get ready, come up with me,” I wailed.

Mom laughed and followed me up to my room. At her suggestion I wore shorts to show off my legs and a tube top to show off my breasts and flat sandals. She talked to me the whole time I was fixing my makeup.

“What will we do?” I was panicky.

“Stay cool. Just assume the answer to all your questions is yes, don’t ask for his agreement at all on any subject. Ask him if he wants to watch a movie and without waiting for his answer, go to the kitchen and start making a mountain of popcorn, at least a couple of bags. Grab cokes and go to the media room. Don’t ask his opinion. Just choose one of those romantic comedies to watch. After he sits down, when he makes his play, tell him that you can’t do anything on the sofa because I might walk in. Have him wait for you while you come back to the kitchen and get one of those big paper bowls and cut a hole in it. Sit back down beside him and put it in his lap. Pull his dick, believe me, it’ll be hard, up through the hole and pour the popcorn over everything up to the top of the bowl. Make sure you cover his dick. Then just start eating popcorn casually. Feed him a kernel every once in a while. I think he’ll be a little hesitant to put his hand in the bowl anyway. It’ll be fun. I’ll check on you all after a little while and, while I’m there, and you all are talking to me, start stroking his dick. I’ll keep talking. You can probably get him off right then. When you do, pick up a kernel with cum on it, pop it in his mouth and then do the same to yourself. Look at him. If he’s coming over he’ll love it. In any case, he won’t dare react because I’ll be there. A couple of seconds after I see you put that kernel in his mouth, I’ll have to go do something and I’ll leave you two alone. Beat him off as many times as he’ll let you, but make sure his hand brushes your penis through your shorts, at least. If he wants to beat you off, let him. Kiss him if he wants. Just be sweet like you see in the movies. You’ll have fun. If he doesn’t get you off, just forget about him. We still have the device.”

She walked away grinning and left me standing there with my mouth open marveling at her brilliance and an erection I had to calm down. “You’d better hurry, he’ll be here in a while”, were her last words as she headed down the hall. I stood there for what seemed like a long time, thinking of that scene, then continued getting ready in a panic. Thank God, I did look cute. I knew I was going to have to look cute if I were going to pull this off. I heard the doorbell and I still wasn’t ready, but I finished quickly and went downstairs to find Tommy talking to Mom.

Mom immediately asked, “Did you invite Tommy over?”

“I did. I’m bored. Hi Tommy.”

Mom managed to look confused and asked me, “What are you going to do?”

I answered, “Watch a movie.”

Mom thought about it then said, “Oh. OK.”

She just walked away and I led Tommy to the kitchen where we made three bags of popcorn and got a two-liter soda and took to the fridge in the media room.

I poured us a couple of cokes over and ice and, like Mom suggested, didn’t even ask him what he wanted to watch, went up to the cabinet and just plopped a “Single Girl Looking For Love” into the DVD and went back and sat down beside him. I put my leg up against his leg and he didn’t move.