What Kind Of A Guy Do You Think I Am?

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This is a 21-page follow-up to my first two stories in my series about a 16 year old boy who envies his mother and gets the chance to live the life of an older woman over the summer. The first two stories are: "Not That Kind of Guy" and "What Kind Of A Guy Am I?" Like the first two stories, this one stands alone, but if you like this kind of stuff, you'd probably enjoy reading the other two stories first.

"Today is pay day," Helen said as she lit one of her Winstons and stuffed the pack and lighter inside her apron pocket.

"I've been here for two weeks, so that means I'll get a check today. Right?" I asked as I lit a cigarette of my own.

"That's the way it works," Helen said. "You're always one week behind so that way you'll get a final check the week after you quit."

I nodded and arched against the back of the booth. My back and feet were killing me. I'd been working as a waitress for Doris for the last two weeks and I was finally going to get my first paycheck. I knew it wouldn't be much, most of what I earned was in the form of tips, but the tips kept getting away from me. Now that I was living as a woman, there were so many things I had to buy.

I had hoped to save some of the money I made at the diner for myself or at least spend it on myself. My parents on the other hand felt that I should pay my way. It was a part of the punishment they'd handed down to me for getting caught smoking and wearing my mother's clothes.

Having a paper check might be different than picking up cash off the tables, I thought. Maybe I can open a checking account.

I'd forgotten how much the check was supposed to be for so I asked Helen.

"Mine is more than yours since I've been here longer, but I think Doris starts the new girls at $5 an hour. You've been working close to 40 hours a week so I reckon your take before taxes should be a couple hundred."

I nodded. $200 would have seemed like a lot of money two weeks ago, but now that I was paying for so much of my own stuff, I realized it wasn't very much. The worst part was buying my own cigarettes. It added up fast at $2.00 a pack. Is that how much I'm spending every day?

"I probably haven't mentioned this before," Helen said as she trimmed the ash off her Winston. "but I'm glad you came to work here. I've been here almost ten years and these girls are like a family to me. You fit in real good."

I thanked Helen for saying so and told her I felt the same about her and the other waitresses. I also told her that what she had said meant a lot to me, about fitting in, but I didn't tell her why.

Helen looked past me toward the front door and I followed her eyes.

"That crew coming in is yours," Helen said. "The young'ns are cute, but they're not much for tipping."

My heart jumped and I thought I was going to die as I watched the three boys take a seat in my section.

"Didn't you say you'd take the next customer that came in," I asked?

"I did," Helen said. "but I have seniority and that's one of the perks. I can change my mind but you can't change my mind."

Helen laughed at her joke as I put out my cigarette and thought about how I was going to handle waiting on my three best friends. I'd known them for years. Surely they'd recognize me! I stood up from the booth and centered the glasses on the bridge of my nose.

I dropped my cigarette case into my apron and picked up my order pad. This is it, I thought as I walked over to take my friends' lunch order. Its do or die and I hope its not die.

Skip Peterson was on the left. He was the biggest of my friends. Frank Bledsoe was in the middle and Tony Skidmore was on the right. Frank and Tony were on my baseball team. All three of them thought I was catching shrimp on a boat.

"Hey boys! How's it going today?" I asked in the sweetest drawl I could muster. "Can I start you off with some ice tea or a Coke while you look at the menu?"

Skip and Frank asked for Tea and Tony said he'd have a Coke. I wrote down their orders on my pad and retreated to the drink station.

I can fill a glass in two seconds flat but I took much longer than that as I filled the glasses with ice and drink. I bolstered my confidence by reminding myself that they had given me their drink orders. I was sure they would have said something if they had recognized me.

I caught a glimpse of myself in the mirror as I put the glasses on a tray. The woman looking back at me looked nothing like their friend who was supposed to be trolling for shrimp. Stay calm and you'll be okay, I thought as I carried the tray of drinks over to their table.

"By the way, my name is Joan," I said as I put their drinks in front of them. I reached into my apron and took out three straws and placed them on the table. "Do you gentlemen know what you want to order, or do you still need some time?"

"I know what I want," Tony said as he laid his menu on the table. "I'll take a hamburger and fries."

"How do you want your hamburger cooked," I asked even though I knew what his answer would be.

Tony grinned at me and said he didn't want it cooked. "Just put a scoop of meat on a bun and I'll be cool with it," he said.

"Seriously?" I asked, even though I knew damn well that he was serious.

Skip and Frank laughed while Tony nodded.

"He's not kidding," Skip said. "Just kill a cow and drag it to the table. He's like that."

I wrote down Tony's order and took the other two orders. "I'll put your orders in a right away," I said. "Just be sure to let me know if you need a refill on your drinks."

I was about to turn tail and run with their orders when I decided to press my luck instead. I thought that by initiating some more conversation it might give me more confidence in my appearance and demeanor. Who know, I thought, maybe they'll even give me a bigger tip if I play nice. On the other hand, they might drag me out on the street and beat me senseless.

I turned my attention to Frank and asked what the three of them had been up to before they got here.

"We were just hitting some ball down at the batting cages," Frank said.

Skip interjected, "Baseball sucks!"

"No dude. You suck," Frank said. "He's not a baseball player. He's a football player."

"Can't you be both," I asked innocently?

"One of our friends is," Tony said. "But he's not with us. He's spending the summer on a shrimp boat."

I told them I knew.

"You know John Butler," Skip asked excitedly.

I told Skip that I was John's aunt. "I'm staying with his family over the summer while he's away. As a matter of fact, my sister gave me his room."

"No shit...I mean no kidding," Tony asked? "Your John Butler's aunt?"

"His mother is my sister. She and her husband were kind enough to let me stay with them until I can get back on my feet."

"So are you from around here," Frank asked?

I told him I wasn't but I was familiar with the town. "I'm from Knoxville."

"Tennessee," Skip asked?

"Go Vols," I said.

"Fulmer is a cheater and the Volunteers suck," Skip said. "We're all Dawgs."

The table erupted in barks and woofs until Skip ended it by shouting "Go Dawgs!" Everyone in the restaurant turned and looked, including Doris.

"Okay then," I said. "I'll just go and turn your orders into the cook, and if you play your cards right, I might just bring the three of you back a bone to gnaw on."

They all laughed and told me how cool I was.

Doris grabbed me by the elbow as I was walking to the kitchen.

"What was all that about," she asked? "Do you know those boys?"

"Yeah, and it's a good thing they don't know me. They're my best friends from school. They'd kick my ass from here to tomorrow if they found who I really am."

"But didn't I hear you say something to them about John? I thought I heard you tell them that you're his aunt."

"Its not like this is a big town so they'll probably see me again," I said. "And I bet it happens when I'm with my parents. I thought I'd head te problem off at the pass by saying something about it."

Doris smiled and nodded. "Smart and brave," she said. "And by the way, I think the big one is cute."

"Skip?"

Doris shrugged. "Is he the big one?"

I said that he was.

"Then yes. He's cute. Do you have a crush on him?"

I squeezed the order pad and sighed with disgust. "I told you Doris. I'm not that kind of guy."

"If you're worried about the age difference, of course I know there really isn't one, but Skip does. Anyway, you shouldn't let that worry you. Younger guys go for older gals."

I told her I knew that.

"You do? How's that, Honey?"

I wanted to tell her how I knew. I knew younger guys liked older women because I liked Doris. But I couldn't tell her that, at least not now- maybe never, but definitely not now. "I just do," I said. "I'm really guy, aren't I? All guys know that."

Doris laughed and pinched my cheek. "You're so cute when you try to be a boy," she said. "Stop by my office after you clock out. I'll give you your check and we can talk a bit."

"Okay," I said. "I better go turn this order into to the kitchen now."

I thought about Doris and the thing she wanted to talk to me about as I went through my day. Business had picked up and I had gotten five new tables by the time my friends finished their lunch.

My friends seemed happy and why shouldn't they be? None of them were working their asses off like I was. They were spending their summer goofing off at the batting cages and the pool.

I thought about what Doris said about younger guys getting the hots for older women as I refilled my friends' drinks and made chit-chat with them. All three of them, especially Skip, were trying to make me laugh and talk. If they had their way, I'd join them at their table rather than wait on my other customers.

Their appreciation for me became tangibly apparent when I checked for tips after they left. Tony and Frank had each left me five dollars. There was a ten dollar bill under Skip's plate. I knew these guys weren't big spenders, so what was up with this? I thought about Doris and what she had said as I folded the tip money and placed it in my apron.

**

After clocking out, I stopped by the office for my chat with Doris.

I poked my head inside to get her attention and said, "Hey Doris. I'm done for the day. You said you wanted me to stop."

Doris smiled warmly and told me come in and close the door behind me. I took a seat and watched as she lit one of her skinny brown More cigarettes. I was thankful that the gaffe between my legs and her desk were preventing her from seeing my erection.

She told me to make myself comfortable and have a cigarette. I reached inside my purse for my cigarette case as she slid my check across the desk. She was so radiant that I thought I was going to melt in her presence.

Being in the same room caused me to try to piece together the puzzle of my life. I adored her much the way I adored my own mother. The difference being that I thought about having sex with Doris.

And what exactly is sex, I wondered as Doris gave me acclimations for the work I'd done over the past two weeks. I knew what sex was because I'd had sex, but I was fixated on the intimacy.

Presenting myself as a woman to my mother and Doris allowed for a kind of intimacy with them that I hadn't experienced while having sex with my past girlfriends. Being a woman had made me one with my mother and one with Doris. If only I could achieve that feeling of intimacy by having sex.

Being dressed as a woman and smoking a cigarette in front of Doris was like some kind of emotional and psychological intercourse for me. I loved it. If only I could take it farther, I thought. Wouldn't it be great if I could be Doris' boyfriend and her girlfriend at the same time?

I had been so preoccupied with watching Doris and thinking about her that I hadn't heard much of what she said. Judging by how she seemed to be waiting for an answer, I was fairly certain she had asked a question and I had missed it.

"I'm sorry. What did you say?" I asked.

"I was asking if you're happy here," Doris said. "I know I can't pay much, but hopefully the tips are making up for it."

"Its good," I said. "I love it here."

"Earlier, when I stopped you at the drink station, I was going to suggest you might want to trade your sandals in for a pair of high heels," Doris said.

"Heels? Why?"

Doris laughed. "Because higher heels equal bigger tips! Didn't you notice you're the only waitress on the floor wearing sandals and tennis shoes?"

I had noticed it, but I hadn't thought much of if. It wasn't as if my feet didn't hurt enough as it was. "But I don't know how to walk in heels. And its got to hurt," I said.

Doris took a puff from her More and nodded. "It does," she said, "but you'll get used to it, and you'll thank me when your tips start getting bigger. Heels have a way of shaping the legs and men like shapely legs. I was thinking maybe you could buy some with your first pay check."

I told her that I knew she was probably right. "But I've already spent so much on girl stuff," I said. I told her about the video game for my computer that I wanted.

Doris looked at me as if I'd lost my mind. "You're kidding. Aren't you?" she asked. "I thought you wanted to be a woman like your mother."

I told her I did, or at least I thought I did.

"Does your mother play video games?"

"No."

"That's right. She doesn't," Doris said. "Your mother is too busy keeping up the house and looking after her family to waste her time playing video games."

"I know, but I don't have a family and the house isn't mine."

"But you live there. Don't you?" asked Doris. "Its your family too. Right?"

I agreed that it was.

"I know you're working as a woman, Honey," Doris said. "But there's more to being a woman than just going to work. Men work too, so you can't say its just about work and looking good. Your mother wants you to really appreciate what its like to being a woman. If all she wanted was for you to have a summer job, I could have hired you as a cook."

"So what should I do?" I asked?

"Well for starters you can buy a pair of nice high heels with the check I'm giving you," Doris said. "And then you can ask your mother what you can do to help her around the house. And last but not least, I think you should get a social life."

"A social life?" I asked.

"You know," Doris said. "Dating! I've seen the way men flirt with you. Flirt back. And if one of them asks for your number, then maybe you should give it to him. I'm not saying you shouldn't be picky because you should. You're a nice looking woman Joan, and you can have your pick of the men."

I was angry, embarrassed, and humiliated, and I made up my mind to put an end to all the gay nonsense about me that had been flying around. "I told you before Doris. I'm not gay. I don't like guys. I like girls."

"Seriously?" Doris asked.

"Well yeah," I said adamantly. "As a matter of fact, if I was going to go out on a date with anyone around here, it wouldn't be some guy or even one of the other waitresses. It would be you."

"Me?" Doris asked. "You're kidding. Right?"

I told her that I'd had a crush on her ever since I was I in middle school.

Doris shook her head sadly. "I think you're very confused," she said. "First of all, I'm flattered that you think you have a crush on me. And if you'd said something like that to me before all this happened, I might have believed it, even though nothing ever would have come of it. Your mother is my best friend so even if I thought you were the best looking manliest man on the planet; I wouldn't have a romantic relationship with you.

"But the point I'm trying to make is that you're not the manliest man on the planet. If you were, you wouldn't be sitting in my office dressed in a waitress uniform and smoking Virginia Slims. I don't want to hurt your feelings, but there's nothing manly about you. A real man would have been hanging out with his friends today instead of taking their lunch orders and flirting for bigger tips.

"Its not an age-gap thing either. I told you earlier that I'm attracted to younger men, but I'm not attracted to you because I'm not attracted to women. I think you're gorgeous and if I was a man, I'd go for you in a heartbeat. But it's not like that. Don't you see?"

I couldn't answer her. I wanted to but I couldn't. My ego was bruised and my heart was bleeding.

"Please don't be upset with me honey," Doris said. "I'm not trying to hurt your feelings or make you feel bad about your self. I'm only trying to help and so is your mother. We talk about you a lot.

"I have to admit I didn't think this was a good idea when you first came to work for me. I was just going along with your father's punishment. But in these last two weeks you've shown me so much of who you really are.

"Its not as if I didn't like you as a boy, because I did. But I like you a hundred times better as a woman, because it just seems so right. And I think you like yourself better this way too. I probably shouldn't say this but I think you need to hear the truth. Your mother and I were talking about it and she feels the same way."

"She does?" I asked. The idea of my mother saying something about it either way threw me for a loop. She had always been so neutral.

"She says she's never seen you happier than you are now," Doris said. "And she's happy too! You're the sister she never had."

"Really?" I asked. "My mother said that to you?"

Doris made a gesture with her hands and said, "Cross my heart and hope to die. But I'll deny every word of it if you tell her I told you."

I didn't respond because I was too busy processing the things Doris had said about my mother.

"What? You don't believe me?" Doris asked?

"No. It's not that. It's more like I don't know what to think about it," I said.

"Don't tell me you're not enjoying this?" Doris asked.

"I am. But that doesn't make it right."

"And it doesn't make it wrong either," Doris said. "Don't you see, Honey. This doesn't have anything to do with right or wrong. It's not like your robbing banks or killing people. This is about feeling good or bad. And if being a woman feels good to you then it doesn't get any more right than that. Take the check and talk to your mom about getting some heels, but don't tell her what I said about her liking you this way. If you don't believe me, you can figure it out by watching her."

I picked up the check and put it in my purse.

"You better go now," Doris said. "You're not on the schedule for tomorrow so I'll see you Wednesday."

**

I saw my mom waiting for me in the car when I walked out of the diner. I had my license and could drive myself to work, but Mom and Dad didn't want to tie up the car, so they opted to drop me off and pick me up. Things would be so much easier if I had a car of my own, I thought as I opened the door and stepped inside.

"How was work?" my mother asked. "Did you get paid?"

"185 dollars and 73 cents," I said. "I made more in tips."

"But it all adds up," my mother said as she lit a cigarette and pulled out of the parking lot. "What's wrong? You look bothered."

I told her what Doris said about buying heels and why she had said it.

"I think she's right. If you want, since you're not working tomorrow, we can go shoe shopping. We can also open an account for you at the bank. Is there anything else bothering you?"

"Not really," I said as I took out my cigarette case and lit a Virginia Slim. I looked for a disapproving expression from my mother but didn't see one. "I was wondering though. Do you miss the old me?"

"Of course I do," my mother said. "I think about it all the time, but that doesn't mean I'm not enjoying the new you, because I am. What about you?"

I told her about my friends coming into the diner and how I waited on them. "They'd just come from the batting cages," I said. "They were having fun. I could be hanging out with them doing the same things, but I'm doing this."

"So what are you trying to say?" my mother asked. "The grass on this side of the fence isn't as green as you thought it would be?"

"No, not really," I said. "It's not like that. This is what I've always wanted in so many ways, so I'm not going to lie to you about it. I love being like you. I love everything about it- the age and the clothes and the smoking. And I love how close we've gotten."

"I love that too," my mother said.

"But there's a lot about my old life that I miss too," I said. "And I've been doing this for a couple weeks. I've still got two and half more months of summer to deal with."

"Two and a half months is a long time or a short time, depending on how you feel about what you're doing," my mother said. "That's why I've been telling you to make the most out of it."

I told her I was trying to do that.

"You could have fooled me," my mother said. "All you do is go to work and come home. If I were you, I'd be looking forward to going to the bank and looking for shoes. Aren't you just a little bit stir crazy?"

"Maybe a little," I said.

"You could take George to the pool tomorrow," my mother said. "He's like a fish and he wants to go every day, but your father and I don't have the time. Its not like you don't have a new bathing suit. And getting some sun would be good for you."

I told her I couldn't go swimming. "The latex, remember? Carol said it would get all gummy."

"You don't have to get wet. Just get a lounge chair and read some of my magazines. You said you were going to read them anyway, and this would be like killing two birds with one stone. Your brother will love you for it."

I laughed and said, "You mean my nephew, right?"

"That's right Sis," my mother said. "Your nephew will love you for it."

**
The next morning, after getting dressed, my mother and I hit the bank. I'd never opened up a checking account, but how hard could it be? After waiting for several minutes in the lobby, a bespeckled man calling himself Aaron Chilsen introduced his self to my mother and I and invited us into his office.

"So how can I help you two ladies this morning?" Mr. Chilsen asked.

"Joan would like to open a checking account," my mother said.

I could tell by his expression that Mr. Chilsen thought it odd that my sister, or whoever he thought she was, would speak on my behalf.

"Not a problem," Mr. Chilsen said. "I can help you with that." He looked at me and said, "I'll need your driver's license and your social security number Ms. Rogers."

I felt as if I'd just had the rug pulled out from under me. What was I going to do? I couldn't give him my driver's license!

Sensing my discomfort, Mr. Chilsen asked if there was a problem.

"There's no problem," my mother said. "Its just that the picture on Joan's license doesn't look like her."

Mr. Chilsen laughed. "I understand. My wife says the same thing about hers, but I'll still need to see it."

Mom nodded for me to go ahead so I grudgingly removed my license from my wallet and handed it to Mr. Chilsen. I watched as the smile on his face turned into a frown as he looked down at the license and then back at me.

"Is this some kind of joke?" Mr. Chilsen asked. "This driver's license is for a 16 year old boy named John Butler."

I dug my nails into the back of my hand in hopes of staving off the nausea. I was humiliated as it was. Throwing up on Mr. Chilsen's desk would only make things worse.

"It's not a joke," my mother said. "John is my son and he's decided to live as a woman this summer. He looks older because of the make-up and the gray and his wig." She told me to take my wig off.

Mr. Chilsen shook his head when he saw me without my wig. "You can put it back on now," he said. "Is this checking account for John or Joan?"

"My check is made out to Joan Rogers," I said, "so Joan would be better."

"And the last name on your driver's license is Butler," Mr. Chilsen said. "Its not that I have a problem with what you're doing. Besides, our bank doesn't discriminate on the basis of gender. But with that said, we do have strict rules and guidelines in terms of establishing the identity of our customers."

"What about a D/B/A account?" my mother asked?

"Doing business as?" Mr. Chilsen asked.

"Yes! John Butler doing business as Joan Rogers. Could you open an account like that?" my mother asked.

Mr. Chilsen smiled and scratched his head. "I suppose we could and we wouldn't even have to put his real name on the checks. There is however a $15.00 per month service charge for having a business account."

"That's okay," my mother said. "We'll take one of those."

**

After leaving the bank, my mother and I drove to a Payless shoe store to look for some heels. We talked about Mr. Chilsen and look on his face when he saw my driver's license.

"Forget about Mr. Chilsen," my mom said. "The look on your face was priceless!"

Buying high heels was a yawn after my experience in the bank, but walking in them was another matter.

"You don't have to wear them tomorrow," my mother said. "You can practice at home until you feel up to it."

On the way home, Mom talked me into taking George to the pool.

My mother was right about George being excited by a trip to our pool. We left our house around a quarter after eleven with a pool bag full of necessities and a cooler.

Our neighborhood pool is about a hundred yards away from our house, so it's a short walk. George, being the noble boy that he is, offered to carry the cooler since it was the heaviest thing we had brought. I could see he was struggling with it so I talked him into trading with me.

The walk to the pool was one of few times I'd been alone with George and he seized the opportunity to talk with me brother to brother- man to man, even though I was wearing a cute one piece blue bathing suit.

"Do you like being like mom," George asked? "Or are you just doing it because Dad is making you?"

It was an honest question so I gave him an honest answer. I told him it was kind of both. I also told him that it was confusing to me so I knew it must be confusing to him.

"You look really pretty," George said. "What about being grown-up? Do you like that?" he asked.

I told him that was one of the things I was confused about. "I think I forgot how fun and cool it is to be a kid," I said.

"But its fun being a grown-up too. Isn't it?" he asked.

"Yes it is," I said as I opened the gate to the pool with our key.

George immediately took off for the pool and jumped in feet first. He popped up from the bottom and shook his head like a wet dog. "Aunt Joan!" he yelled. "The water is warm! You got to get in!"

"Maybe later, Honey," I said as lugged the cooler and the beach bag to the less populated corner of the pool. I nodded to the neighbors I'd grown up with as they looked up and smiled as I passed. I even had a brief conversation with Mrs. Toombs about my relationship to George. Between the impromptu conversations and greetings, it took nearly two minutes before I reached my destination and could drape a towel over one of the chairs. So far so good, I thought as I sat down on the chair and reached into the pool bag for my cigarettes and magazine.

I was reading an article about eye shadow when George ran up to my chair for his towel. He asked if he could have something to eat.

I gave him a bag of potato chips and he sat down beside me. He told me a about swimming underwater with his eyes open and asked if I had seen him do it.

I acted like I had. "Didn't it hurt?" I asked.

Without answering me, he jumped from his chair and dropped the bag of potato chips on my lap. "Mark! Over here," he screamed.

I looked up to see Mark Kilgore and his father walking through the pool gate. Mark started running toward us while his father yelled for him to slow down.

The two boys began talking excitedly. George told Mark about swimming underwater with his eyes open.

"Cool! I got to try that," Mark shouted, even though George was less than four inches away from him. "Dad! I'm going swimming with George now. Okay?"

"Have fun but drown any one," Mark's father said. And then the man who is Mark's father turned his attention to me and stretched out his hand and said, "Hi. "I'm Doug Kilgore, Mark's father."

I nervously shook the older man's hand. "Joan Rogers," I said. "I'm George's aunt."

"Mark told me about you," Doug said. "And you're even prettier than he said." He motioned to the chair that had been vacated by George. "Would you like some company or did you come here to be by your self? I see you're reading."

I felt vulnerable and naked. As a matter of fact, I was actually covering my chest with my magazine. The safe answer came to me immediately. Doug had given me a way out and I should take it. But how would that look, I wondered. He'd think I was a stuck up bitch and I'm not. I'm just scared, but his smile is so warm and disarming. But what will he think if I say yes? I don't want to sound horny or desperate. Besides, the last thing I want is a middle-aged boyfriend. Screw the age! I don't want any kind of boyfriend. But maybe he didn't want to be my boyfriend. Maybe he just wants to pass the time with someone while Mark and George play in the pool. Talking wouldn't be so bad.

I pointed to the cigarette between my fingers. "Is this going to bother you?" I asked. "I can put it out if it does."

Doug grinned and pulled a pack of unfiltered Camel cigarettes and a lighter from the pocket in his swimming trunks. "I don't think it will be a problem," he said as he sat down and lit one up. "I keep telling myself I'll quit one of these days, but I'm sure you know what I'm talking about."

I wanted to tell him how stressed I was about quitting before football season started, but chose to agree without giving an explanation.

"George is a really good kid," Doug said. "And so is John. Mark said something about him going on a fishing trip this summer."

I told Doug that John was working on a shrimp boat.

Doug nodded and said that it would be the experience of a lifetime. "I bet John will never forget this summer," Doug said.

"You're probably right about that," I said. I tried to think of something adult-like to say to him. After all, I'd been reading the newspaper and watching the news just in case a situation like this arose. "So what do you think about the Middle East?" I asked.

Doug exhaled a lung full of smoke as his expression became curious. "To tell you the truth, I haven't given it much thought lately, at least since the hostage crisis. I guess I'm okay with it as long as the gas stays cheap. So tell me about yourself Joan. Where are you from? How long are you staying?"

I would have cringed at such questions if they had been asked weeks earlier, but I had studied and rehearsed my fictitious life story. I gave him enough but not too much. I told him that I was visiting from Knoxville and was trying to start a new life for myself. "I'll probably stay for the summer," I said. "And if things work out, I'll get a place of my own, and if they don't, I can always move back." My answer seemed to placate him.

"I didn't see a ring on your finger," Doug said. "Divorced?"

I told him that I had never married and asked about his marital status, even though I already knew the answer.

"My wife died five years ago," Doug said. "Its been just Mark and I ever since."

We spent the next two hours talking about Mark and George while interjecting stories about ourselves. Every now and then the boys would come over for a drink or a snack.

I found myself enjoying our conversation, not because it was stimulating, but because I discovered that I actually like Doug Kilgore as a person. I'd known him most of my life, but not like this. He'd always been just a neighbor to me, not that he wasn't now, but sitting with him at the pool, talking to him like this, I felt more like his peer. I was also seeing him in a way I'd never seen him before. I guess you could say I was looking at him through my woman eyes.

While growing up, I'd heard my mother and her friends gossiping about him. They always talked about how good-looking he was. I'd never given it much thought back then but now I think I understood what they were talking about.

His dark hair was peppered with gray, especially by his temples. There were lines in his face that gave him character and a rugged appearance. His belly on the other hand had seen a few too many beers, but I forgave him that. Compared to most men his age, he looked pretty good. The neatest thing about Doug Kilgore is that he made me laugh for the first time in three weeks. He was genuinely funny and very nice.

He was telling me a story about a guy from his office that had gotten his hand stuck in a vending machine when he paused to load his lip with one of his unfiltered Camel cigarettes. Seeing him do that reminded me that I was overdue for my own nicotine fix. I removed a cigarette from my case and was about to light it when Doug leaned forward with his own lighter.

"May I?" he asked.

His gesture both surprised me and thrilled me. A man was offering to light my cigarette for me! Thank god for my gaffe, I thought as I felt my penis stir between my thighs. "Please," I said.

Doug moved uncomfortably in his chair as he lit my cigarette and then I noticed why. He could have used a gaffe himself! Oh my god, I thought. He's getting an erection too! I did the polite thing and pretended not to notice.

I thanked him as he pulled away.

"My pleasure," he said.

"So what happened to that guy in your office?" I asked.

"Oh yeah," Dough said, as he picked up where he left off.

**

When I got home, I told my mom about meeting Doug Kilgore at the pool as Joan.

"He's cute," my mother said enthusiastically. "Do you like him?"

"Sure I do. I've always liked Mr. Kilgore. He's a great guy."

"No silly! Not like that," my mother said. "Do you think he's cute? Did he ask you out?"

"Mom! Why would you even say something like that," I asked? "What is it with you and Doris? I'm not gay. I don't like guys the way girls like guys. I just like being like you."

My mother placed her hand on my shoulder and asked, "Haven't you ever wondered what it would be like? You know, to go out with a man, not as a homosexual, but as a woman?"

I tried to say no but my mother looked right through me to the truth. "But I'm not a real woman," I said softly.

"Doug doesn't know that," Mom said. "And what he doesn't know can't hurt him."

"Why do you want me to start dating men? Do you want me to be gay?" I asked.

"This has nothing to do with anyone being gay," my mom said. "This is about you experiencing life as a woman to the fullest and I don't think you can do that without dating."

I told her the whole conversation was pointless because he didn't ask me out.

"That's okay," Mom said. "All I want is for you to think about saying yes if a nice man asks you out. Don't automatically say no just because you have a penis. Forget about your penis and try to remember you're a woman for the summer."

"Okay Mom. I'll think about it."

**

I told my mother I'd think about dating men to get her to drop the subject. The problem was that I was thinking about it and I couldn't stop thinking about it. And when I thought about dating men, I thought about dating Doug Kilgore.

Doug Kilgore is my father's age and I'm just 16, but he thinks I'm a lot older. He probably thinks I'm as old as my mother.

I'd be in so much trouble if anyone ever found. But its not like anyone could go to jail. It would just be embarrassing and isn't that a good enough reason not to do something? It was a good enough reason but it wasn't a good enough reason to keep me from thinking about it.

He is nice looking for a man, I thought. Ah geeze! Why am I even thinking that? But thinking about it can't hurt. As a matter of fact, thinking about it feels quite nice. And that's when I noticed my erection.

I touched my erect penis and wondered what Doug would think if he saw it. And then I thought about Doug's penis and I wondered what it would like. What does a 45-year-old man's penis look like, I wondered? Is it big like mine or is it even bigger? If I saw it, would I be brave enough to touch it or maybe even more?

I sat up in bed and lit a cigarette. My penis poked up through my nightgown making a tent over my lap. I watched as my breasts rose and fell with every inhale and exhale. I pictured Doug's face and I thought about his smile.

I remembered what my mom said about experiencing life as a woman. She had told me it was okay to date men. She had given me her permission and her blessing. What would it really be like, I wondered?

I imagined going on a date with Doug. Where would he take me? Dinner and a movie? Probably. Would we go back to my house or his? I thought about my father and what he might think and decided it would definitely be best to go back to Doug's house. But he'd probably take me back home and walk me to the door.

I wondered if he'd try to kiss me good night. What would it be like- to kiss a man? I remembered that he smokes. I've never kissed a smoker before, but I've wanted to. However all the smokers I've thought about kissing are women. It turned me on to think that I was like those women now.

I thought about my mother and just how much I'd become like her. Comparing myself to her made my erection grow even larger and harder. I finished my cigarette and put it out. I knew I should try to get some sleep because I was scheduled to work the morning shift, but I was too excited to go to sleep.

I picked up the soft brown leather cigarette case my mother had given to me. It meant so much to me and I loved it so much because it reminded me of how similar we were now. It had been hers and now it was mine just like the nightgown I was wearing used to be hers but now it was mine. Most every thing in my closet and my dresser used to belong to my mother at one time or another and now they were mine and I absolutely loved them.

Comparing myself to my mother had thrown me into a sexual frenzy. I knew there was no way I'd ever be able to go to sleep without relieving my pent up sexual frustration.

I lit a cigarette and laid back down in my bed and found my penis with my hand. My parents don't like for me to smoke in bed but they do. I imagined my father making love to my mother and them both having a cigarette afterwards. How romantic and satisfying that must feel, I thought as I pulled on my penis and puffed on my cigarette.

Even though it went against everything I stood for, I substituted Doug and myself in place of my mother and father. I imagined him on top of me penetrating me with his big manly penis, making me more and more like my mother with every thrust of his powerful hips.

Is that why my mother wants me to date men, I wondered? Does she want a man to make a woman out of me? How could I ever go back to being a boy if that happened? Would I even want to?

My orgasm was intense. It was probably the most intense orgasm I've experience in my life! And the guilt that came with it was every bit as intense as the orgasm itself.

I put out my cigarette and sat up in bed. I felt depressed when I saw the huge stain on my mother's nightgown that now belonged to me. What had I done?

Logically speaking, I knew I'd done nothing wrong. It wasn't the first time I'd masturbated in my mother's clothes and I knew it wouldn't be the last. But I'd never fantasized about a man making love to me before and I'd done that this time. I felt dirty and disgusting as I pulled the gown over my head and threw it in the corner of my room. The flopping of my breast forms against my chest made me sick to my stomach.

I laid back down and closed my eyes. The orgasm had left me whooped. I tried not to think about what I'd done as I drifted off to sleep.

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Comments

As always

I've found myself really enjoying the flavor and tone of the story. There is a lot of great potential here I think for a killer series. I'd love to see this through the summer and after school will he have changed his/her mind by then about living as a woman or try it as a teenaged girl? The older guy or the younger guy both?
But I really like the sisterly closeness the mother ans Joan are making, if they can make it closer more like sisters then there's an amazing chemistry you can achieve. I like the idea of them helping out with the stuff at home. How much didn't we know about bills and other stuff our parents went through as teenagers, how much wouldn't they tell us because we'd be facing it soon enough. It'd be cool to have Joan do something nice and unexpected, especially in regards to her "brother in law".

Keep up the great job.

Bailey Summers

What Kind of Guy

littlerocksilver's picture

This is a very interesting, in depth look at an unusual situation. I wonder how long it will take her to realize what's happening to her? When will she realize what she truly wants, and when will she achieve the younger version of that?

Portia

Portia

What Kind Of A Guy Do You Think I Am?

Is an interesting variation of the author's original story. Me, I like the differences between them as that's what makes each one unique.

    Stanman
May Your Light Forever Shine
    Stanman
May Your Light Forever Shine

What kind of a guy do you think I am?

I love this! As a person who is going through some similar issues, it feels very relevant to me (except that I AM that old). I can't wait to see the next chapter! Thank you very much. This is well written, and fun to read. I look forward to seeing how all of the questions get answered. I'm working on a story myself, and I can only hope I can do somewhere near as well.

Wren