Date: Sat, 21 Oct 2017 04:21:29 +0000 From: John Edwards Subject: Oh, Those Cupid Lips Oh, Those Cupid Lips Another Fiction by John G. Edwards Copyright 2017 All Rights Reserved ((This story is being shared with Nifty Archive, and if you like it please donate to the site so that stories like this can be preserved.)) I was going on fourteen years old and puberty was nowhere in sight. This was a part of my life that I was so looking forward to because I know that once my voice changed and you started growing hair in the nether regions and on your face, girls would start to look you over. Yeah, mother had me go out with some girls that were daughters of her friends, but the dates always turned out awful. Probably due to my awkwardness in the situation. Today, though, it was raining and I was home alone with mother. She was in the kitchen baking something, it smelled like cookies and I was in my room doing some cleanup because I do like a clean and neat room. Mother had taught me this many years ago and it wasn't unusual for me to spend a couple hours at a time cleaning and arranging things as I liked. My father always thought this was kind of strange. He was from a rather large family, and from what I hear, it was chaos most of the time and his room wasn't so damn neat and tidy. This one time, I had gone over to see one of my few friends for a couple of hours and when I came back, dad had wrecked my room to see if he could get a rise out of me. He didn't, I simply started picking thing up and putting them away. So much for him trying to bully me. My room was covered with posters of leading ladies from the 20's, 30's and early 40's. I just loved the way they looked with their hair all done up and their, by todays standards, glaring makeup that was both colorful and artfully applied. Mother would wear her makeup in this style every once in a while, but father was not such a fan, unlike me. This one time she went to the beauty parlor and got her hair cut and curled like a 1920's flapper, along with a pair of those red-red cupid lips and sort of a modern twist on her eye makeup. Mother had her eyes rimmed with black eye liner and the outer edges were drawn out about half an inch beyond the corners of her eyes, kind of cat-like. Rather than apply a dark eye shadow, she had a deep dark purple allied to her eyelids. The look was quite striking, I know that I really liked it. The almost porcelain foundation she was wearing complimented the whole look. I took several pictures of her that afternoon when she got home, one of which I had blown up, and it too was also hanging on my wall. I had pretty much everything put away when I sat down on the side of me bed. I was staring intently at one of my posters when mother came into my room with a plate of, just out of the oven, cookies and a glass of milk. "Sweetheart, I brought you some cookies and milk." She spoke so softly that my eyes were still transfixed on the woman in the print. My back was facing away from mother, and then I turned around, "Thanks mom, you're the best." I got up and came around to the other side of the bed where she was standing. "You look like you were pretty deep in thought sweetie. What is it about those posters that appeals to you so much, anyway?" I had just taken a bite of my cookie, "The way the women look. Their hair and makeup are just so different than what women wear today. The hair styles are short and wavy. I'm really enamored with their makeup, especially how they painted their lips. It makes their mouth seem so small. Eye makeup back then seems so simple as compared to what I see some women wear today. I guess they didn't have the color choices that women do, now." I took another bite of the still warm cookie, "Their dresses were pretty conservative back then, you didn't see a lot of boobies hanging out all over the place." I had to laugh and so did mother. "I don't know, there is just something that calls to me. Does this make any sense?" "It's starting to. You are right about the women dressing a lot more conservatively back then, but during the roaring twenties, the hem lines did get a few inches above the knee. As for the makeup, you are also right, there wasn't that many eye colors to choose from, and most of the flappers, as they were called, wore mostly black. There wasn't robin's egg blue, plum purple, or anything like that. Interesting how you have zeroed in on their lip shape and all. That's a style that was called cupid lips. Small and well stylized lips were the rage of the day. A lot of women had naturally shaped cupid lips and they would just follow their natural lip lines and color them in. Some women had to create their own cupid lips and would apply their lipstick to create the illusion of having them. If you take a look at my lips, they have a natural cupid lip shape, and by the way... you have the same mouth as me. That's part of the Harris family (mother's maiden name) looks." "Really, I have cupid lips?" "Yes sweetheart, you do." I went to my dresser mirror and took a look, sure enough, I had a pair of very well defined cupid lips. "Mom, why don't men wear makeup like women do? I mean, I think it would make them look a lot better if they did." "Social norms. Society has put men and women into separate boxes. Women are expected to wear makeup some times, no make that most of the time. I usually don't wear a lot during the day, but as you know, I can put on a pretty decent face at times." She pointed to her picture on the wall. "I think it would be pretty cool to see men wear makeup once in a while, myself. When your father and I were dating, I kind of forced him into letting me put some makeup on him one night when he had had too much to drink." "Really?" "Yes, but don't say anything about that to him, please..." "How, I mean, what did you put on him?" "Everything I had. I started with foundation to even out his skin color and tone, that was the worst part for him. He had a day or two's worth of beard stubble and I made him go shave until his face until it was as smooth as a baby's butt." She laughed. "Then I started with a really wild combination of eye shadows, but mostly greens, blues, and a little bit of yellow. I put upper and lower false eyelashes on him and then rimmed each eye with a fairly heavy coat of black liner. He really hated it when I colored his lash-line with some neon-blue liner, but he did look kind of cute. After several coats of black mascara his eyes were done to my satisfaction." "Wow, how long did all this take?" "About an hour buy the time everything was in place. The rose-red colored blush that I applied to his cheeks really did make him look very fetching." "What about his lips?" "That was the easy part, I put on some really bright red lipstick. As you probably know, he doesn't have our cupid lips." She laughed again. "I spent a little time tweezing his brow and gave them a slight arch and colored them with a black eye pencil. For the finishing touch, I put a black birthmark on his right cheek, just about half an inch from his eye." "I've never seen you wear one of those mom." "They are not for everyday wear, only when you get really decked out and you are going to a party or some very special occasion." "Oh..." "I used to have a black bob-cut wig and I put that on him along with a pair of clip-on diamond chandelier earrings that hung down about three inches. He looked like a hot chick that you would run into, at a bar or something." "Wow, I wish I could have seen him. I bet he would have looked really good in a dress with a pair of tights and heels, huh?" I said jokingly. Mother burst out laughing hysterically, "Yes, he did." "What, you made him wear a dress too?" I sat there on my bed with a most incredulous look on my face. Mom just smiled, "Yes I did. It was a red mini-dress that I had back then. He looked really good with the black opaque tights and the pair of black platform heels with ankle straps, but that's only half of it. I made him put on a girdle and a bra that I stuffed a pair of his sox into to give him a feminine shape." "Did you take any pictures of him, and can I see them?" "I did, but I think I threw them out a long time ago, sorry sweetie." She knew exactly where the photos were but did not want me to see them because if I said anything to dad, he would have blown his stack. I definitely didn't want to be on the receiving end of that! "Oh, I would have really would have liked to seen them." Mom actually used the pictures to kind of keep dad in line once in a while. I knew that she didn't like to see him go out drinking with his buddies. I guess I can kind of see why they would be so effective on him, you see, dad was kind of a macho man. "Honey, would you like it if I dressed you up. sometime?" "What?" I could hardly believe my ears. "I have a couple of things that I think you would look really good in, or maybe I can just do your makeup. It's up to you, but I would be happy to do it sometime if you want." "Really mom?" "Of course darling. I think you might make a pretty good looking girl, I always wanted a daughter," she said as she gave me a hug and kiss. I blushed. "When?" I said excitedly and almost peed my pants. "Anytime you want, we can do it now, or later, it's up to you. We can even style you hair a bit, I know it's been a while since you went to the barber and your hair is getting pretty long, you know." I sat there blinking my eyes. I wonder what I will look like dressed as a girl? What dress will she have me wear? Will I get to put on a bra??? Oh there are so many questions racing thru my head right now!!! "How about tomorrow, mom?" "If that suits you. That will give me some time to get things ready. Terrific!" With that, she gave me another kiss and a big hug before she left. The rest of the afternoon was spent thinking and dreaming about tomorrow. That afternoon I rode my bike to the mall to go window shopping and look at what women were wearing and how they had their faces made up. This was like going on a field trip at school, only now it was something that I was really interested in. I wouldn't have to take notes or anything, but I would file away the images that were important to me in my head. As I walked around and looked in the display windows, the styles were all evening and party dresses because it was near the holiday season. The dresses were long and fully fitted. A lot of them were long sleeve, but then there were the sleeveless dresses as well. There was this one dress that I really liked, it was a silver material that had sort of a low sheen to it. It had long sleeves and a fitted bodice with a scoop neckline. The skirt was kind of full, which I was kind of liking. The mannequin was wearing black fishnet stocking and a pair of shinny black stilettos with dainty straps that went around the ankles. The model was also carrying a small silver leather purse with a silver chain carrying strap. I fell in love with the outfit right there on the spot! As I continued my walk around the mall, I slowed down when I walked by the makeup store to see what the display pictures were showing. One of the pictures was showing a young woman with a dark evening pallet. The dark blue eye shadow that feathered out to black was really something to look at. Just then I got a text from mother, Please get me some navy-blue mascara while you are at the mall. Thanx sweetie... Mom. If she only knew that I was at the makeup store, ha... I went in and sort of looked around a bit, it wasn't too long before a lady in her early thirties came over and asked with a drop-dead gorgeous smile, "May I help you with something today?" "Uhh... Yes, my mother wants me to pick up some... Let me look at the text again... Oh yeah, some navy-blue mascara?" I said as I showed her the message on my phone. I must have had the deer in the headlights look on my face, at this point. "Right over here, I'll show you what we have," she said as I followed her to one of the counters. "This is our most popular." She held out the tube and opened it so I could see the color. "Is this kind of what she wants?" She said with a curious smile. "May I take a picture of it and send to her?" Again with that smile, "Of course." I took a picture and sent it to mother, about two minutes later, she responded, Yes, that's perfect! I showed the message to the woman and she smiled and nodded her head. "Sorry for the confused look I must have given you, we get a fairly large number of crossdressers in the store." She laughed. I guess the fact that mother had sent me the text and I was able to re-text her made the difference in the woman's opinion here that this wasn't for me, personally. Of course, it really was as I was to find out later. I paid for my purchase and was about to continued my browsing, but before I did, I plucked up the courage and asked the woman what crossdressers were. She chuckled, "Well, they are men who dress as women." "They do it all the time?" Once again she laughed and smiled at me, "Sometimes. Crossdressers are generally in two or three camps, so to speak. There are those men who do it in the privacy of their own homes and never go out. Then, there are those men who dress and do go out into public. Some even go to work dressed enfeme." "Excuse me, but what does that mean?" "Ah, enfeme means that they dress like a woman and go to work like that." "But doesn't their bosses kind of get upset about that, or something?" "The ones I've met don't seem to have a problem with that. But, you can just imagine if you showed up at school one day out of the blue wearing a dress and makeup, the principal might have something to say about that. Anyway, there are also drag queens who wear the most outrageous clothes and makeup and dress to impress their friends. Do you know Rue Paul? He's a female impersonator of the highest level." I did know about him, but not much other than he was a guy dressed like a woman, albeit a very beautiful woman. "We have quite a few of all three types that visit our store here at the mall. I have even assisted several young people, younger than you are, to develop their feminine alter ego, so to speak. They are a lot of fun to work with because they are so eager to learn about makeup and how they should look, age appropriate. I have several mothers who dress their sons for womanless beauty pageants that come in. One of you young boys is only about seven years old and he has won several local pageants and is going to a national level event after the first of the year." "I never knew..." "Well, you might want to come in sometime for a makeover. I promise it will be a lot of fun. Here's your sales slip. Give this to your mother, she will need it in case this is the wrong product and wants to return it. By the way, what's your name?" "Brandon, but mom calls me Brandy." "Well, it's been a pleasure to make your acquaintance Brandy, I hope to see you in the near future. Bye..." As I left, I wondered if I should tell mother about the invitation go and get a makeover? But for right now, I folded the small bag and put it into my pocket so no one would know that I had been shopping at the makeup store. The next store I stopped to look in the window was the shoe store. I started by looking at the men's shoes and snuck a glance the ladies footwear. Women have way more choices when it comes to shoes, guys either get dress shoes, casual shoes, or sneakers with choices of black or brown, mostly. The ladies have as many colors as there are in the rainbow and the choice of sandals, flats, boots, pumps, and high heels. Now add to that, open or closed toes, straps that are either dainty or kind of wide. The choices are endless. I don't know how they make up their mind when they go shopping for shoes, I guess that's why most women have so many pairs of shoes. I had to laugh to myself. I was just about ready to leave when I got another text from mother, Can you get me a pair of black 200 denier opaque tights? I asked which store, The big department store on the south side of the mall. Ok, here I go... I found the store and went to the second floor to the Hosiery Department. There I found nylons in every color imaginable and some I never knew existed. I went over to get some assistance because I had no idea what a denier was. "Hi, I just got a text from my mom and she wants a pair of," I looked at my phone, "200 denier black opaque tights?" I held the phone up so the woman could read the text. "I can help you with that, do you know what size she needs?" "Size? Doesn't one size fit all?" The woman tried not to laugh, "Not exactly, why don't you call or text her and ask what size she needs?" I dialed home and put the call on speaker, "Mom, the woman wants to know what size you want." "Something that will fit a person of your size, sweetie. Probably Average fit will be just fine." I turned every shade of red you can imagine! The woman smiled and asked me to follow her to the bin where the 200 denier tights were located. She gave me a look-over and decided that the tights should be as size Petite instead of average and picked out a pair for me. "Excuse me, but what is this denier thing?" "You don't know? It's how we describe the opaqueness of the pantyhose. These, the 200 denier, will give you excellent coverage and you won't be able to see your skin thru them. Shear nylons are generally a 10 to 25 denier, you need that so you can see your skin thru them. The higher the number, the more opaque they become. Most pantyhose are in the 50-60 denier range, but tights are around 125, or higher, range." "Oh, I see... Thank you for your help and for my education.," I smiled. Now it was time to get going, but I got another text, Honey I need you to get one more thing, go to the Lingerie Department and get a black Leading Lady Bra, size 34A. Thanx, mom. Off for my next assignment. I wonder why she just didn't come to the mall with me if she needed all this stuff? Well, at least she gave me all the information I needed, at least I hoped. The woman in the lingerie department was very nice and gave me exactly what mother had requested with now drama at all. "Well aren't you just the best son, to come to the lingerie department and get something for your mother. Bravo to you young man!" On the ride home I was getting sort of confused at how mother had stated her question to the woman in the department store. My size? What the heck did that mean! When I got home mother was waiting for me. "Get everything ok?" "Yes..." I handed her the three packages. "Swell, thank you dear heart!" She took the bra out of the bag and held it up to my chest, "This should be about right." She smiled, "Oh are we going to have so much fun!" I gave her a curious look and then went to my room to think about crossdressing. I can't believe I'm thinking about this, I'm going to get dressed up as a female. Oh shit... When I thought about it that way, it made a difference, somehow. That evening mother was all kind of giddy, "Brandy, your father had to go out of town for the rest of the week for work, I guess there's some sort of problem back east that he has to go and fix. So it looks like we are here by ourselves for a few days. Do you what to get dressed and do your makeup after dinner tonight?" My eyes were blinking rapidly, "Uhh, sure... ok..." "Great, let's go to my bedroom for a minute." I followed her to her bedroom, there on her bed lay the bra and a pair of black lace panties. "Take your shirt off, I want you to try on the bra to see if it fits ok." I gulped, but started removing my shirt. Just as quick as the shirt was off, mother strapped me into the bra. The somewhat tight fitting garment felt like nothing I had ever worn before. There was a sort of comforting feeling as she fastened it around my chest. The elastic gave it enough tightness, but it wasn't discomforting at all. Mother told me that I was an underwire bra and asked if the wires were uncomfortable, I shook my head, no. I ran my hands over my bra covered chest and the feeling was much more than electric! I'm sure I had a huge smile on my face. Mother was still behind me and put her hands around me to cop a feel. When she did, she pulled me close to her and I could feel her breasts against my back. Her hands were warm and she was very gentle as she cupped what the bra could conjure up for my breasts. She knew exactly how to hold me and I was in heavenly bliss. She whispered, "Nice tits, honey..." She let go and then told me to put the panties on. I held up the panties to have a look, they were high-cut, but there would maybe be enough material to cover my privates, but not by much, by the looks of it. "First, put on your tights, then the panties. I find that your panties will hold them up better. That's always a problem with pantyhose, they want to slip down all the time. Sit down and I will show you how to put them on." After a couple of minutes, I was wearing the black 200 denier tights and just like the woman had said, you couldn't see my skin thru them. I couldn't believe how easy the panties slid up my legs! Mother gave the tights a pull so that they fit me perfectly, again the woman was right about the Petite size. Mother pulled the panties into place and adjusted them so that they fit correctly. I put my hand on my leg and it slid effortlessly. As I rubbed my leg I felt this tinglely feeling between my legs and all of a sudden there was a wet spot starting to develop. I turned so mother couldn't see it and I put my pants back on. The feeling of the denim sliding over my legs was heaven on earth. My blue jeans felt slightly cold as I pulled and buttoned them into place. I put my white tee shirt back on, but you could see the bra's outline and some of the color thru it. It was kind of sexy. Mother handed me a pair of her black leather flats to wear. They were just slightly big, but they looked nice with my jeans. As I walked back to the kitchen, I found the shoes much more comfortable than my sneakers. Imagine that! Walking with my new underwear was an entirely new experience. The bra wrapped itself around me and gave me the most sumptuous squeeze, the tights and panties were like wearing something very slippery under my pants, and the shoes... They are so comfortable that I never wanted to take them off my feet! I helped mother with dinner and she kept asking me if everything was comfortable and felt ok. I replied that everything felt wonderful, especially the shoes! She smiled. After dinner was over and the dishes put into the dish washer, we went back to her bedroom bath and she had me sit on the commode. "How about we do something with your hair first? Let's get you shampooed and dried off then I'll do something that won't look too girly tomorrow, ok?" "Ok..." Mother washed my hair and did a conditioning rinse to give my hair some body. Her scissors were clipping like they were possessed, then came the blow dryer and some more clipping, and then some combing. When she was thru, she had layered my hair into a near chin-length style that looked rather fetching, in a girly sort of way. "I'm going to give your eyebrows a bit of definition while I'm at it. God knows you got that Greer set of eyebrows." I held my head back and mother went to work. The plucking wasn't so bad, in fact it kind of tickled. When she was thru, I now had a rather feminine looking pair of eyebrows! Nice! "I'm going to apply some foundation and then some powder, a little lighter than your skin tone. How do you like your eyebrows, now? Hold your head up." "I like them a lot mom, you did a great job!" Then, she applied an astringent to clean my face before she applied the foundation. It took her several minutes to get my whole face and neck covered with the foundation. Once she was done, my skin looked just like a models face would look. A quick powder puff and my face was ready for the next step. "Honey, I'm just going to do a simple makeup tonight, just some eyeliner, mascara, and lipstick. I want you to pay attention because I'm expecting you to do this by yourself, ok?" I shook my head, yes, but wondered about having to do this by myself, thing. True to her words, she just applied some black eyeliner and mascara. After choosing a vivid red lipstick, she painted the most luscious pair of cupid lips on me that you could ever imagine! As I looked into the mirror, I did look just like a young woman, but with a childish sort of bent. Oh, those red cupid lips, they were simply divine! Mother took great care to explain each step as she applied my makeup and asked if I understood. I did, I was like a sponge absorbing everything she said. "Like the look?" "Oh mother, yes I do! I look... so girly." "Yes, you do sweetheart, indeed. Let's get you dressed now." "How does your bra feel? Is it digging in or anything?" "No mom, I told you, it fits really good. I like the way if hugs my body. Too bad men don't get to wear a bra." "Well honey, if you guys had breasts, you probably would, but you don't." "Yeah, but you could wear one if you wanted to, couldn't you?" "Social norms, again. Men are not expected to wear women's underwear, but if it makes you feel good, I don't see any reason why you couldn't. You could certainly wear panties and no one would ever be the wiser because they don't show, or anything. A bra would be more of a challenge. As you can see, you can see it thru your tee shirt. I wouldn't say anything, but your father would. Same goes for school. The kids would give you hell about wearing a bra and I don't know if you could handle or like that. I've got a cobalt blue mini dress that I think you are going to look just darling in. It doesn't fit me anymore, but I think it might fit you just about right." Now I was getting more excited. "Slip out of your things and I'll go get it." A minute later she returned with the blue dress on a hanger and held it up to me to check it for size. She removed it from the hanger, unzipped it, and then had me step into it. She went around to my back and zipped the dress up from the my waist up to my neckline. "Turn around so I can see how it fits." When I did, she got this big smile on her face, "Well, it almost fits. You are a bit small on top for it, but I've got a solution for that! Be back in a minute." When she came back, she was holding a box and when she opened it, there were a pair of small silicone breast forms laying within. She took one out and held it up for me to see and then handed one of them to me. It felt all soft and jiggley. "Let me get you unzipped and I'll show you how to wear these." "Where did these come from, mom?" "From the lingerie shop over on Fulton, I picked them up today while you were at the mall." She pulled the cups of my bra out so she could insert the forms. Once they were in, my bra got a lot tighter, but I now had a pair of breasts what any girl my same age would be very proud of. "How does your bra feel now?" "A lot tighter, but not too uncomfortable." "Alright then, let's get you all zipped up and have another look at you." When she was thru, the cobalt blue mini dress fit me perfectly, well almost. My hips were a tad bit small, but overall, I looked stupendous! I could feel the rear of the short dress as it sat across my back side. It was a bit drafty back there! "Oh sweetheart, you look fabulous! That V-neck is just perfect on you. Turn around." As I turned around mother placed a necklace around my neck, There was a small faire hanging at the bottom of the chain and it was just the perfect length with this dress. "Shoes, you need some shoes now. I've got a new pair of black patent leather Mary-Jane platforms that I've never worn yet and I think they will complete this outfit perfectly. Sit down." Mother went to her closet and pulled out the shoe box. When she opened it, there were the exact same shoes I had looked at, at the mall! Wow! Mother knelt down to put the shoes on my feet, this time the shoes fit perfectly. I couldn't believe how my foot just glided into them. Mother did the buckles and I was ready for my first solo in high heels! She helped me stand up so I could get my bearings, so to speak. I now stood a few inches taller than my mother in the 5" platform shoes. Mother held my hand as I took my first couple of steps. To my surprise, I wasn't wobbly at all, thanks in part to the blocky heels. My steps were steady and true. Mother let go of my hand and I was off like a shot walking around the house. Mother was all smiles when she caught up with me in the living room. "I've got to get a few pictures of you honey, I'll get my camera." I walked into the kitchen and found the tile floor more to my liking as a walking surface. The low-cut pile rug was ok, but this was certainly much better. I felt my new breasts and I threw my head back in ecstasy. The feeling of my tits thru the velveteen dress materials was just this side of heaven! As I squeezed them together, I had a bit of cleavage form. That picture would forever be imprinted in my brain for as long as I lived. Of course mother came into the kitchen when I was feeling myself up and snapped a couple of pictures. "Honey, do that again, but bend over at the waist a little bit so I can take another picture and give me a big smile." As I bent over and repeated the move, my cleavage amped up, and it looked like a had a whole bunch when I looked at the picture! We went back into the living room and I had to strike several poses for her. Mom is not the greatest photographer, but I have to admit, all those pictures were pretty damn good. I couldn't believe how much older I looked dressed like this. I guess clothes and makeup make the woman, and how! I couldn't believe that mother had suggested that she would dress me and do my makeup. For a teenager, it was like I had died and gone to heaven. I suppose I could have done something like this on the sly once in a while, but I would have never gotten so done up, due to my lack of experience and naiveté. But, now that I had a teeny bit of experience and some things of my own, it was certainly not going to be the last time...