Sissy Story Chapter 03
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.”
“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?
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. He immediately put his arm around me and asked, “Are you going to suck me?”
I acted offended, “Is that what you think?” I scooted away from him. “Besides Mom could walk in on us at any time. Wait a minute.”
Mom was in the kitchen, I rolled my eyes and took the paper bowl from her, with the hole in it she’d already cut out, rolled my eyes again and walked back to the media room.
I scooted up to Tommy, put the bowl in his lap and he watched with his eyes big while I opened his fly and pulled his hard dick through the hole. He watched everything open-mouthed like it was the most amazing thing he had ever seen. I then leaned up and got the popcorn we’d made and dumped as much popcorn that would fit into the bowl in his lap. His eyes kept getting bigger. I used the remote to turn on the DVD, turned down the lights and started watching the movie, barely looking at Tommy. I brushed his dick every now and again as I was getting popcorn. I gave him an occasional kernel, just like Mom suggested. We hardly spoke. I put my leg over his leg and kept eating popcorn.
Mom came in and I took my leg off his as she sat down, and sat up straight, like I’d be expected to do when Mom came in, obviously to check on us. Tommy sat up and started to put the bowl on the table, looked confused as he realized his dick was out and it had a hole in the bottom. He was really cute. He sat up straight and tried to figure out what to do while Mom and I chatted for a couple of seconds before Mom began questioning Tommy about his life. I sat there with my hand in the popcorn and started stroking his now soft penis, which, I might say, got hard immediately. Poor Tommy was as confused as I’ve ever seen anyone. I stroked and watched the movie. He kept talking to Mom, trying to concentrate on his answers, he stuttered and repeated himself. He was so damned cute. Hardly any time passed before he came. He tried not to show it, but it was so obvious it was comical. Mom and I pretended not to notice. I giggled and pointed to the screen like I was enjoying the movie during all this. As soon as he finished and went a little soft again, I stopped looking at the screen and looked in the popcorn bowl and selected one of the kernels dripping with cum and plopped it in his mouth, then selected another one for me and did the same, looking right in his eyes. Mom said something about having something to do upstairs and left. Tommy looked at me as I put my leg over his knees so my foot was in the air, and started stroking him again. He was speechless. He came again and I fed him several cum-soaked kernels one at a time, “Do you think it has enough salt, Tommy”, I asked in my most innocent voice. He shook his head and I deliberately led his hand to my crotch where he felt my erection.
He left his hand there for a second, and looked at my leg and feet and answered, “God, maybe not” and started stroking me while I kept stroking him. He French-kissed me, and thrust his tongue aggressively into my mouth. I just opened wider and accepted it. We both came and ate a few more kernels, but we were finished with the popcorn. I put his greasy soft dick back in his pants, pulled up his zipper and patted him. He didn’t get hard again, and neither did I, but I did make sure he felt my breasts anyway.
All in all, my first sexual experience was a success. While it was with another boy, and like nothing I’d imagined in my wildest dream, it was still fun. And I enjoyed the orgasm. Tommy went home right after, I gave him a kiss at the door, and he said, “Will your Mom let me come over again tomorrow?”
I giggled and said, “I hope so,” and he was on his way home. What a night that was. I had admired Mom my whole life and that was before I decided she was definitely a genius.
Mom had me tell Tommy not to come over the next day, but he constantly texted me and asked if she were mad, and tried to set up another visit to the house. Mom and I talked it over and she finally suggested I tell him that he could come over when I wasn’t grounded anymore for wearing that vulgar t-shirt.
Tommy was so sweet Wednesday, which was my last night grounded. Mom and I talked about what to do next a lot, and I thought I could handle it most of it. I invited Tommy over on Thursday and maneuvered him into my room, which looked fabulous. We started playing video games and texting on our phones when I asked if he’d like to see me in high heels. He was enthusiastic, so I put on some five-inch heels I had, black leather pumps with lots of straps, close-toed, and some black nylons with elastic tops. I walked around for him for a few minutes and crashed on the bed. He was still seated on the end of the bed looking at me, lying down. I put my foot in his lap and said, “Take off my shoes for me, these hurt my feet, I don’t think I wear them enough.” He did take it off. I put my leg in the air and took the nylon off and threw it on the floor. He was going crazy. I gave him my other foot and said, “Now the other one,” and we repeated everything. We sat there a couple of seconds with my bare feet in his lap without saying anything. After the dramatic pause, I slowly lifted my foot to his face and said, “Kiss my poor toes and make them better.” He did it. “Use your hand to support my heel, Tommy, and kiss the toes until they are all well.” He did that too. “Now the other one”, and we repeated everything with my other foot. His dick was completely erect, straining against his jeans. I sat up and pulled him by his neck down to my legs and rubbed them against his cheek. “Oh, that feels better.” Then I grabbed ears and pulled his head and pulled it to my crotch.
“Wait, you don’t want me to suck you, do you,” he whispered in a loud voice with his lips inches from my dick.
“You want me to suck you, don’t you Tommy?”
“Well, show me how much.” I gave him my prettiest smile.
He hesitated then pulled down my panties and after only a little hesitation took my dick in his mouth. I put my hands behind his ears and thrust into his mouth until I came. There was semen everywhere. I giggled and got up and threw him on his back, slipped down between his legs and crossing my legs and kicking them in the air behind me, sucked his dick until he came in a gush. I caught a lot of his cum in my mouth so climbed up and caught him by surprise and gave him a “snowball”. I saw that on the Internet. We both had cum all over our faces, all over the floor, all over the pretty white lace bedspread. I didn’t stop though. I asked him if he wanted me to wear my high heels and suck him off again. He groaned pretty loud, so I stopped until he controlled himself. This time, I showed him the snowball before I swallowed it. He went crazy kissing me, so I sucked him off for the last time that night. There was cum everywhere, I was going to have to do some clean up, but we had fun, even though we’d never been out on a date. Not bad for a second sexual experience, not bad at all.
He went home before midnight, we kissed at my front door and we promised to text. I knew he’d keep his promise.
Mom was in the media room. “Well, Sissy, do you want to see it blow by blow, so to speak,” she smirked.
She put in a DVD and there we were, Tommy and me doing our little romantic number. Mom had captured it all on video. It was great, full color, zoom, everything. I loved it.
Mom said, “Tell him I caught it on computer camera. Tell him I’m not going to do anything with it, but let him know I have it. That will keep any information on you getting out into the world, because there he is undeniably. Sweet.”
She gave me a high five and I just shook my head. “Do I get a copy?” and grinned. “Now I’ve got cum to clean off every surface in and around my bed, the maids are not going to be particularly pleased.”
“Not as pleased as you are, at any rate”, Mom said. “Let’s just wait and see what happens.”
I texted Tommy:
Me: Mom got us on tape!
Me: In my bedroom, the whole thing.
Me: Do you want a copy?
Me: OK, if you change your mind let me know. I’ve got it on my phone.
Tommy: Can you recognize me?
Tommy: OMG she isn’t going to show it anywhere is she?
Me: ROFLMAO Think, think real hard. I’m on that video with you. We’re in this together.
After a significant pause,
Tommy: Oh. Yeah. We are both in it.
Me: It is so cool. If I’d known she was going to tape it, I would have had you wearing is black dress socks and a mask
Tommy: SISSY! It’s not that funny.
Tommy: I don’t think.
Me: I think it is. I like watching it, but not just because it’s funny, cutie.
After anther significant pause,
Tommy: My Mom checks my phone.
Me: Poor baby, my Mom is cool she doesn’t, I think. Delete this text after it’s over.
Me: Maybe next time you come over we can make some popcorn and watch it in the media room.
Tommy: Tomorrow night?
Me: Sure, why not, you’re fun, if a little messy.
Me: I’ll try not to watch it too many times before then. I’ve got to go, I have a major cleanup, all because of you.
Tommy: Love you
Me: You’re sweet. We don’t know each other very well. I like you an awful lot, though.
Until June, Tommy and I kept up what could best be described, I think, as our summer romance. I went to his prom with him. I looked spectacular. I met his parents, they weren’t sure of me. They spent as much time questioning me as Mom did Tommy. For a time, we were a couple, and I didn’t spend as much time with Mom. I missed it, but Tommy was exciting. He went away to school in July, though. It wasn’t football season, but it was football season practice. We phoned for a while and spent a couple of weekends together, but he always had something to do at college, and when he came home I had to compete with his parents for his time. I spent more time with Mom, again. It seemed a little tame, but I still loved fashion, and I loved looking my best and Mom and I loved talking about it.
Mom and I discussed college, but I wasn’t much interested. I was never really interested in school, except when Mom was fixing my hair every day.
I got a red convertible sports car, and was quite the sensation, but I didn’t find a boy who interested me. Mom and I had long talks again. She told me she really enjoyed the Internet, and friends she made on it. I wasn’t really a fan of social media. For a while we sort of drifted along, shopping, going out to eat, going to the beauty shop, re-decorating. I was a little bored.
The device just sat on my closet shelf. I didn’t wear it to get used to it, but it popped into my mind every once in a while. One day I talked to Mom about it. I complained because it was so uncomfortable, and it just didn’t seem like it would be fun. Mom explained everything isn’t for everybody. She started showing me some of the things she did on the Internet, and I was surprised to learn she was really into some kinky things, lots of websites with lesbians, lots with female dominance, lots of stories and pictures and really interesting porn. I really got interested in the subject of mothers with sissies. There were all sorts of pictures, websites, discussions and other ways that people with like interests communicated. I had thought myself unique. Mom showed me we were really part of a large group, when the whole world was considered. That opened up a whole new world to me. The Internet, which I had grown up with and used really for school and not much else, since Mom was my world, became a playground. Oh, we still shopped and I was still careful about my appearance but the Internet opened up a whole new world of possibilities. One day, after I had learned a lot more, I typed “Moms with sissies wearing chastity devices” in Google. The stories kept me occupied for quite a while. Mom mentioned a club she’d like to go to, but it was for Moms with Sissies and they didn’t accept singles. They required we go together. We talked about it a lot before one Thursday when we were looking around on the Internet, out of the blue I just asked her why we didn’t go.
“Because you never seemed to want to participate socially. One of the things I enjoy most is showing you off, which I do when we’re shopping. Nobody knows though, you were born a boy. At this club everybody there will be Moms with their sissy boys. It’s one of those things that either appeals to you, or doesn’t. It appeals to me, if it doesn’t appeal to you, it wouldn’t be any fun though.”
That put the ball in my court. I considered it for a minute and answered, “It is sort of appealing why don’t we go and try it out?”
Mom smiled, “Sure. It’ll be fun seeing live what everyone else is doing, what other families like ours are like. I talk to some of the Moms sometimes, and I have pictures, but seeing it live will be fun.”
“I don’t have to wear the chastity device, do I,” I asked?
She laughed, “Nope, not unless you want to, as far as I know there’s only the one rule, Moms and their sissies only.”
“Mom, it’ll be fun.”
“I think so, Sissy,” she smiled and pinched my cheek, like she did when I was a kid. It brought back a flood of memories I loved, of me taking lessons with Mom fixing my hair and agreeing for the first time to go out with ribbons and then nail polish.
“Mom”, I said, “Let’s get really dolled up and go out tonight.”
She laughed, “There is a lesbian dance club I’ve read about that I’d like to go to.”
“OK, let’s do it!” We helped each other get ready.
The club was just another dance club like the ones Tommy had taken me to. The difference was the lack of men. Oh, there were a few mannish people, all right, and they sort of acted like men, and so they were fun, but the huge majority of customers were women, attractive women that could have been found at any club anywhere. Mom and I had a couple of drinks, and accepted a couple of invitations to dance and even danced together a few times. People took us for a couple though, so politely didn’t intrude. If some gentleman had taken me to a club like this, as soon as I was alone, when he went to the bathroom or to fetch drinks or something, the boys swarmed around with their cute little lines and very eager faces. The same thing would have happened to Mom if I’d left her. It’s one reason why women go to the bathroom together.
All in all it was a different experience and Mom and I had fun. When we got home, we fixed sandwiches, got some wine and watched a movie together. It was really a great evening.
We went together to Mom’s Mothers and their sissies club, but really didn’t have that good a time. Both Mom and I looked spectacular, of course and that made some Moms and sissies obviously jealous. The boys were, for the most part, much younger than I and in petticoats and ruffles and bonnets with lace and aprons, costumes I found a little ridiculous on the one hand, and very, very cute on the other. I told all of them they looked adorable, but secretly I was glad Mom hadn’t been inclined in the way these mothers were. Some asked questions. Some poor boys came over alone, embarrassed, to ask me questions, which I tried to answer the best I could. For the most part though, Mom and I ended up, not through choice, sitting alone and just watching the people. It was fun and Mom enjoyed meeting her Internet friends in the flesh, but some of them were a little unfriendly. Mom and I speculated on the way home that some of them looked little like the pictures they’d exchanged and that, perhaps, they didn’t expect me to be so spectacular. Mom had the nicest way of making me feel good.
This became sort of a new routine, Mom and I going out together, only we went to bars and clubs with men mostly. Mom enjoyed herself more than I did. She laughingly complained that nobody paid any attention to her except to get information about me. We started playing on the Internet more, visiting more interesting sites. We visited Femdom, and Gay sites of all kinds, Beastality (ugh!), fisting (ugh!), and a thousand variations on each of these. I became quite familiar with fetishes. The only very intriguing ones were Femdom, though. That sort of described Mom, but she had never raised a hand to me, or even threatened to. I really never did anything at all for anyone’s benefit but mine. I started to wonder if I seemed that self-centered to other people. The intriguing part about Mom had nothing to do with punishment, but authority. I realized Mom loved being in charge, and getting her way and she had taught me to be the same way. I considered the chastity device again. Not wearing it, understand, but would it be much fun to get some boy to wear it and voluntarily give me the key? That sounded fun, like something I could enjoy.
I started doing phone sex on one of the big Internet sites. It wasn’t for the money; I only charged a dollar a minute; it was for the experiences, the fun. I was amazed at what I could get boys to do, merely by talking to them and sending them pictures of some model I bought on the Internet. Even though they begged to meet me, I declined and, instead, had them do all sorts of things for me so they’d feel like we were participating together in something. I had them cum in their own mouth, had them buy and wear panties to work, had them put on makeup for the calls, had them remove all the hair from their bodies from the eyebrows down. I ordered them to buy cameras for their PC’s, and trained them to be dogs and watched them eat dog food, and watched them use all sorts of instruments on their ass. My favorites were a couple of different guys who each bought spanking machines and would make their rears so red with me watching and not saying anything, only commenting on spots they might have missed and having them start it again. I liked it, but it got old, the same thing over and over, really. And the boys got so dependent.
I told Mom all about it, and what interested me, of course. The first time Mom raised her eyebrows. “Thinking about uses for that chastity belt, huh? Well, waste not, want not”. Our conversations became about her and what she liked, which I’m not going to relate, since this is about me, but they were a little surprising, I guess. Of course she liked me, and she liked getting me to do things I didn’t want to do at first and which she had decided were for my own good. We talked about where we could meet people like that and everything. Mom, as usual, had a ton of wisdom. “Guys come up to you all the time, just turn them down by telling them you’re sorry but you don’t think they are the kind of boy you’d like. Most of these guys will be older, but don’t use “man”, use “boy” and see who stays interested, and play it by ear.”
That changed the dynamic of our trips out. We both started getting in more conversations with men who tried everything. Nobody really interested me. I politely turned down a black guy who was cute because I didn’t want to call him ‘boy’. He might have thought I was a racist, and I sort of felt bad, but what could I do? We were victims of Political Correctness.
Mom and I bought throwaway phones and every time we got asked for our phone number, we’d ask the guy for his and, if he gave his number, call him and save his number when his phone rang in front of us. He had our number and we had his. It was effective, cheap, and it made the guys feel like they’d accomplished something.
Mom and I trolled everywhere. My favorite, and Mom’s, was going over to the adult bookstore downtown and looking at DVD’s in the ‘Femdom’ section. Guys looked us up and down, but we never got approached. We actually did better in the upscale bars downtown, after work, during Happy Hour. That’s where I met Johnny.
Meeting him is a cool story in itself. After a couple of months of this activity, guys were calling my phone all the time and I started texting some of them back, asking their name, doing little get acquainted things. They invariably started asking me out, so I’d ask for a picture to refresh my memory. If they sent a dick picture, they were blocked. Those that didn’t send a picture were blocked. Of the few left, I blocked those whose looks didn’t appeal to me. I texted back those who did, whether I remembered them or not, “Oh yeah, I remember you,” and the conversation in text would start. These were fun. Mom and I read them and laughed and laughed. We looked at her texts and the gentlemen were a lot more polite. Every once in a while, we’d agree to meet one for a drink and, with a hired cop, the other would go to the place and sit away from the bar and watch. We felt like real intelligence operatives, and we met a few of cute cops who loved us for the effortless payday as much as anything. They really didn’t hit on us that much after we made sure those that did never escorted us again. It was all pretty harmless, just an abundance of caution. Mom or I, depending on who had the engagement, would sit at the bar, wait for whoever we were meeting and have a couple of drinks and have a conversation. After a while we’d excuse ourselves and give the high sign to the one with the cop and go home, the three of us. It was simple and pretty foolproof for meeting strangers. The cops would take us home and that was that. This went on for a couple of months and it was fun in itself. The guy who provided the cops asked if women were OK, they wanted in on the payday, $50 an hour for sitting in a bar was pretty good work. Mom and I had no problem with that and the male cops became even politer. Mom suggested it was because they were afraid they might lose their cushy jobs to the women and laughed and laughed. It was pretty funny, which, to be fair, people are. It was the new routine, and I liked it.
After a few weeks of this, I was sitting at the bar, with all my experience talking to guys on the phone and Internet and in physical proximity. I got a little nibble. “Well, John, to be honest, while you are attractive, you just don’t seem to have what I’m looking for in a boy”. That speech usually turned the conversation cold and all but the most persistent left after finishing their drink, with a vague, “I’ll call you”. With the more persistent I simply became friendly but impersonal, volunteering little or nothing. This guy though was a little different, he didn’t seem to have enough confidence to be really persistent, but he didn’t quake.
“I like boys who do what they’re told, when they’re told to do it”. I looked him square in the eyes when I said it.
John looked at me and swallowed and said, “I’ll do what I’m told.”
I replied, “When you’re told to do it?”
John answered correctly, “Yes, I’ll do what I’m told when I’m told to do it.”
“That’s my boy. Meet me at Luigi’s Monday at Eight o’clock sharp.” And I got up, not even finishing my drink, not looking back and walked out. Mom and her cop followed quickly and we went home together. I told Mom it worked and I started making plans for Monday, what I was going to wear, especially. John deserved the best possible show. I made a Monday beauty shop appointment.
Luigi’s was a neighborhood Italian place that wasn’t busy on Monday’s at all. Monday wasn’t a good day for restaurants, and the food was good and it was casual.
I got my nails done and hair fixed. I wore a short red skirt, red t-strap heels with little hearts on the them, bare legs, a red necklace with a big heart pendant, earrings with hearts dangling from them. I carried a big red leather purse. My blouse was great. It was white trimmed in red lace with ‘I know what boys like’ tastefully (hah!) embroidered in smallish script to frame the bodice. Red, red lipstick but a little eye shadow and mascara finished off my look. John was going to get a treat and, if I might say, incentive.
Mom and her cop got there at 7:50 and were immediately seated. I sat in the car and watched John pace up and down and look at his phone. I examined him as he paced. He had blondish hair and a slender build and was of medium height. Objectively he wasn’t much to look at, to tell the truth. He dressed expensively, if not precisely in the best or latest fashion. In fact, he looked as if all his clothes had been selected for him by the sales staff in an upscale department store. Give him credit though. He tried.
At precisely 7:58, I turned off the car and air-conditioning and walked straight to the door of Luigi’s. I waited in front of it without saying anything until John caught on and opened it with a shy, “Hi”. I waited while John said “two.”
What passed for a maitre‘d in that place said, “A booth in the corner, OK?”
John didn’t say anything. I stepped in, “that table there, in the center, will be fine.” I didn’t dress this cute not to be seen.
The guy seated us and offered a wine list.
John asked me, “Is a Chianti OK?”
“No. We’d like A dry Lambrusco perhaps one from Emilia Romagna?”
The Maitre‘d look at me, then John and turned back to me, “Very good Madam,” in one of those fake upper-class accents and scurried away.
John swallowed and tried conversation “You left before I could get your phone number, I didn’t have a way to call you and confirm. I thought you might not come.”
I gave him my best smile, “John I told you to meet me here tonight at 8. I don’t really care if you’re disappointed in what you might think is proper behavior. I am not your property.” I kept smiling and left the obvious an open point.
John audibly gulped, a caricature of a swallow.
The wine came the Waiter hesitated, then poured a small amount in my glass and put the cork on the table. I expertly tasted the wine, but I didn’t practice the affectation of smelling the cork. “This is good.” And the waiter filled our glasses and left. I kept smiling at John.
“You’re beautiful,” he finally said.
“Why thank you John,” I responded with my best smile. His eyes were fixated on my bodice. I really liked guys looking at my tits, so I pivoted around to give him the best show, and turned back to him, with my most dazzling smile. I loved the scene. John was visibly squirming in his chair.
The waiter saved him. John tried one last time asking if I wanted him to order for me. I cut him short. “You hardly know me, John, so you can’t expect to know what I prefer. You ordering for me would be a little much, don’t you think?”
John examined the menu with his head down, so I continued, “I ordering for you would be more appropriate.”
When the waiter came back I ordered a complete dinner, and then, as an afterthought, “He’ll have the spaghetti and meatballs.” The waiter scurried away to the kitchen.
John looked at me, and I smiled back.
He finally said, “This is a nice place.”
I looked at him, “Small talk isn’t your specialty is it, John?” I tempered that statement with, “That’s not all that bad.”
Encouraged, he ventured, “What do you like to talk about?”
I gave him another dazzling smile, and looked at him while he squirmed. After a minute or so, “Me. I like to talk about me, and how I look and what I’m wearing.”
I swear John’s eyes almost bugged out of his head. “Those are pretty earrings.”
I kept the smile going, he was going to get the full treatment, “Do you like them?” I turned my head and put my fingers behind the hearts and framed them.
“Yes. They’re very beautiful.”
“Thank you, John.”
After a couple of seconds he continued, “I like the necklace, too.”
“Oh, do you like me wearing hearts?” I smiled.
He hesitated a second and finally came up with a good one, “I think I’d like whatever you’re wearing.”
I gave him my best smile. I finished my wine and left the glass there for a second. “Well, John, are you going to fill my glass?” I cut the smile.
He fell all over himself filling it. He didn’t pour it right and he was so awkward. But he didn’t spill any.
“We’ll have to work on that John.”
I smiled, “It’s a mistake to expect perfection in the beginning though, don’t you think John?”
“Yes. I don’t know….”
“That’s painfully obvious, John, you simply don’t know. That’s all right though, ignorance is curable by direction and study.” I gave him an encouraging smile.
“You’re welcome, John. Improving things makes me happy. I like being happy. Give me your phone.”
He gave it to me and I put my throwaway number in it and named the contact “Beautiful Bitch”. I gave him his phone back. “I don’t like boys who look at their phones instead of me John.” He had started to look at it, stopped, thought better of it, and put it up. I smiled at him.
Dinner came and we ate with the same type awkward conversation. John was trying so hard to please, but I found fault with everything he did. He squirmed constantly. It was enjoyable watching him be uncomfortable and trying so hard. He was going to be fun.
Mom and her cop left the place and I announced to John I was ready to go. He looked confused I said, with a sigh, “My chair, John.” He was pretty cute running around to hold my chair out for me, and get the door on the way out. We stood on the sidewalk for an awkward couple of seconds before he volunteered, “I had a good time.”
“I had a good time, too, John, thanks for asking.”
He looked totally crushed but managed, “Do you want to go out again?”
“Thursday at Campbell’s. Happy Hour starts at five, I like to sit in those high chairs at the little round tables. People get there early to claim them.”
With that, I walked off, leaving him standing.
I was in a good mood all the rest of the evening. Lying in bed I thought about everything and resolved, right then and there, John was going to have more fun than he ever had before, more than he had ever dreamed of. Once he got my dick in his mouth, I’d own him, I smiled to myself.