Crossing The Line free porn video

Crossing The Line, by Sydney Black Introduction My relationship with my beautiful, feminine mother was unusual, to put it mildly. I was a gentle, slight, attractive boy, almost pretty in my own right, and I was completely in her thrall. I was in love with my mother, but she was also my idol. Kept hidden under my mattress, in a way that I naively thought went undetected, was my little treasure trove of trinkets related to her - a lipstick that she had discarded, a pair of panties that I hoped she would not notice was missing, and best of all, a photo of her which was taken right before she got pregnant with me. In the photo, Mother had jet-black, long hair, which was worn way up in the back of her head in a high ponytail; big gold hoop earrings, almost like a gypsy; and red lipstick. With her high cheek bones and large brown eyes, accented by mascara and liquid eyeliner, she looked like a young movie star. At night, alone in my bed, I would slip under the covers, and quietly slip the panties on; I would turn on my flashlight, and take out the photo, and gaze at it, imagining that it was me...... Mother knew I was in love with her; I don't know if she knew I actually wanted to also be her. In any event, she had a way of both flirting with me and feminizing me at the same time. It was an intoxicating combination. When done in private, which it usually was, it was bad enough. But when done in public, it had the effect of both arousing me and mortifying me. As it was, I was completely under her spell. I thought about her day and night. I was powerless to resist any request she made of me. And every time she did something in public that made me seem like her sissy son, it just strengthened that hold on me. Did I enjoy being embarrassed? Well, not in the traditional sense of pleasure, like eating an ice cream sundae. But the embarrassment always seemed to reinforce the submissiveness I felt towards her. And that submissiveness had an erotic quality to it, which was intensely pleasurable. So, I would end up both mortified and aroused. But usually not at the same time. When an incident occurred, I would be mortified. But when I lay in bed that night, wearing her panties and clutching her photo, replaying the event in my mind, and especially thinking about how it clearly gave her pleasure, I would become tremendously aroused. I would become hard, and I would press myself up against my blanket, rubbing back and forth, creating friction, and close my eyes, replaying the scene, and soon enough, I would have my release.... Chapter One Over the years, Mother had transformed from the girlie ingenue in the photo, into a graceful and elegant woman. She loved fashion and makeup. And with her being a single parent, and me being her only child, she loved to share these interests with me. Granted, I did not resist. I loved fashion and makeup too, although I tried to hide it. And I loved how this was something that could bind us together. I know that she sometimes wished she had a daughter, and sometimes I wished I had been born her daughter, and it all seemed innocent enough for us to sometimes quietly pretend that that was the case. My favorite time of the day was when I came home from school. Mother would almost always be waiting for me. Many times, it looked like she had just put something pretty on, or freshened up her makeup, right before I walked in. Was she freshening up her makeup for me? That thought sent shivers of pleasure down my spine. I loved to imagine her sitting at her vanity just before I got home, reapplying her lipstick. It was almost as if she were getting ready for a date - a date with me! So, for example, on a typical day I would come home from school. And I would run to her and give her a big hug. I loved that moment of physical contact, when I would bury my head in her chest, and I would close my eyes and inhale her perfume. It was heavenly! Eyes closed, I would tilt my head back towards her face, a little like a girl would do who was in the arms of her man. I would feel her kiss me lightly on the lips, lingering for just a moment. And then, I would hear her giggle as she said, "Oh, my, it looks like some of my lipstick got on your lips. Here, let's see how it looks", and I would feel her pinky on my lips as she spread the transferred lipstick. She said, "Oh, pretty!" At such moments, I would feel weak, as if my knees were literally going to buckle. But the moment would pass, I would stand up, and we would begin chatting. Although I was shy about expressing my interest in feminine things, I was not shy about telling mother how beautiful she was. I loved how she would ask me questions, with her knowing the answers I would give in advance. It was almost like a game we would play. She would say, "How was your day, Honey?" And I would say "Fine, Mommie, but I missed you! How was yours?" I always called her Mommie. I had done it since I was a toddler. Once, when I had gotten a little older, and was in front of some other boys, I had tried to switch to "Mom", like a big kid, but she told me she wanted me to call her Mommie, and that was the last time I called her Mom. In truth, "Mommie" was more appropriate, because I loved how I could be like a little boy with her, how I could come home from school and tell her that I missed her, instead of having to try to act 'tough', like the other boys I knew. Anyway, I asked her how her day was, and she said, "It was great! Bergdorf's was having a sale, and I bought these new shoes! Ferragamo!" She took a step back from me, and twirled around a bit in her cute navy pleated skirt. The shoes were a high heeled, open toed pump. I knew the question game would now start. She said, "How do you like them?" "Oh, Mommie, I love them!" Mother smiled. "How do you think they make my legs look?" "Oh, they make your legs look even longer and even more beautiful than normal! Mommie, you have the legs of a model. Or a dancer! And those heels are so flattering!" The game was on. "You don't think the heels are too high for daytime, do you? " She asked, as if a twelve year old boy would know the answer to that question! Of course we both knew that Mother was not looking for an objective opinion from me. The more unabashedly worshipful my answers were, the more she glowed with approval. And I was happy to oblige. "No Mommie, they are beautiful, and sexy, just like you! I think they are fine for daytime!" "You think Mommie is sexy, do you?" I gathered up my courage and looked at her. "Mommie, I think you are the sexiest, most beautiful lady in the world!" "Oh, you are the sweetest thing! I could just eat you up!" Then she gave me another hug and a kiss. "Mmmm I never kissed a boy who was wearing lipstick before!" I blushed and said, "Mommie, I'm not wearing lipstick!" Mother giggled, took out her compact and showed me where she had left a little lipstick on my lips, and said, "Oh yes, you are!" Mother wiggled her toes in the shoes. They were painted a raspberry pink. "How do my toes look? I couldn't resist getting a pedi after I bought these shoes!" "Your toes look so pretty! What is the name of the nail polish?" I loved the fun names that the nail polish companies gave their nail polishes! "Thank you Honey, the name of the color is California Raspberry!" And then the conversation would take a little turn. She said, "Look, I bought a bottle from the nail salon and brought it home. Do you know why I did that?" I could feel my face getting flushed. I thought I knew the answer she was looking for, but that was not the answer I was going to give. I said, "So you could touch up your toes if the polish chips?" Mother smiled a knowing smile. She knew I knew the answer, and that was not it. "No, silly, that's not why. Guess again!" I looked down and squirmed, shifting my feet back and forth. "I don't know, Mommie." "Oh, I think you do, Honey. Now guess again!" Mother said it sweetly, but this time there was the tiniest edge to her voice. I said, in a voice barely above a whisper, "In case someone else wants their toes the same color?" Mother smiled. This was the game she loved. It started with her showing me her girly things, and continued with me telling her how beautiful she was, and ended with me asking her to make me girlie, like her. All along the way she rewarded me with flirtatious touches, kisses and hugs. I knew my role. It was not enough for me to simply admire her femininity, or to even LET her make me feminine. No, ultimately I had to ASK for it. I had to let her know that I wanted to be like her. This just reinforced her power over me, and my submissiveness to her. We were not quite there yet. The game continued. "That's right Sweetie. I brought it home in case somebody is a good girl and wants his toes painted just like Mommie's. Do you know anyone who might want that?" I noticed that Mother had referred to someone being a good girl. When she referred to me that way, it was of course humiliating, but in a way I could not explain, it was also exciting. Is that what I really wanted, to be her good girl? I responded, "Oh Mommie, I love your new shoes, and I love your toes. I, I wish my toes could look like yours. Could you please paint my toenails, Mommie?" There it was - what she had been waiting for. Mother hugged me. "Of course I can paint your toes, Sweetie. This will be so much fun!" I was excited to have Mother paint my toes, but I was nervous that anyone else would see it, or would find out. I knew from previous experience that Mother sometimes liked to embarrass me in public with girlie things. So, I said, "Mommie, I would love to have my toes pretty just like yours, but I know that boys are not supposed to have their toes painted. Do you think that this can be our secret?" Mother smiled. Me asking her to keep it secret was yet more power she would have over me. She said, "Well, Sweetie, I can't PROMISE you that no one will know, but I don't see any reason why this can't be just between us!" So, she was conditionally agreeing to keep it quiet. But if for some reason she was not happy with me, I could envision my pretty raspberry toes being exposed in public.... She continued. "Anyway, I wouldn't worry your pretty little head about it. If anyone did find out, I'm sure they would understand why a boy like you would like to have his toes painted just like Mommie's!" "A boy like you." I did not ask her what she meant by that; I did not need to. Chapter Two Mother and I were snuggled up on the couch together, paging through her latest issue of Vogue. My feet were propped up on a footstool. I was wearing a pair of baggy shorts. My toes had little balls of cotton in between them. My toenails were painted California Raspberry, and they looked gorgeous! The polish was almost dry. Basically, I was in heaven! Mother said, "Oh, I knew that would be a good color for both of us! Your toes look adorable! Are you sure you don't want people seeing how pretty they look? Such a shame to keep them hidden!" With that remark, a little warning light went off in my brain. For some reason, I had a feeling that Mother and I would not be the only ones to see my toenails! Suddenly, the doorbell rang. Mother got up to open the door. It was her best friend Jeanie. Jeanie could have been Mother's sister. She was a real girlie girl, just like Mother. If it were any other person in the world, I would have been terribly embarrassed sitting there with my toes painted a pretty color. But Jeanie's only reaction was to say, "Oh, fun! What a pretty color! I'm next!" Mother laughed and said, "Of course! You know, we should teach Sydney how to do this, so he can give us pedis!" I have to say, the idea of me sitting submissively at Mother's feet, was incredibly erotic. Even though Mother may have been joking with her remark about teaching me to give her pedis, I said, "Oh, Mommie, I would love to do that! " Mother said, "OK, Honey, we will teach you! And maybe we can get you a special outfit to wear - maybe a pretty little smock like the girls in the nail salon!" I loved the idea of wearing a pretty smock. I pictured myself wearing shorts with it, with the smock reaching down past the shorts, so that it looked like I was wearing a short dress, all the while sitting at Mother's feet, painting her toes..... After Mother finished Jeanie's toes, Jeanie said the reason why she had stopped by was because she had heard there was a makeup sale at Bloomindales and she was going over to check it out. Did Mother want to come? Mother jumped up, said, "Of course I do! You know I never met a cosmetics sale I didn't like!" Jeanie said to me, "Come on, Sidney, let's go buy some makeup!" Yes, it was embarrassing to be talked to that way. I mean, I was a boy! But it was hard to argue that point too strenuously while I was sitting there with my toes painted California Raspberry. And anyway, the truth is, I loved being 'one of the girls.' So, off we went.... The cosmetics area at Bloomingdales was, for a twelve year old boy, like entering a forbidden world. It was a fantasyland of makeup, and pretty ladies working at all the counters, applying the makeup to customers, spraying fragrances on the passers-by. I felt like I was in a dream. We made our way over to the Chanel counter. Well, they had more than a counter; it was a whole private section on the floor. Like everything else Chanel, it was classy and expensive! Mother and Jeanie were regulars there. The woman helping them knew she was not dealing with two young girls, but with two experienced customers. She tried to be helpful but not pushy. Mother and Jeanie were having a great time trying on various eyeshadows, blushes, etc. I was just kind of standing there, trying not to appear too interested. Of course, that was difficult, because every time Mother tried something on, she asked me what I thought! The truth is, even though it was embarrassing to me, I loved having Mother ask me my opinion of her different makeup choices. Finally, they got to the lipsticks. Mother tried on a beautiful color called Mauritius. Naturally, the first thing she did was turn to me and ask me what I thought. Her lips looked perfect, so sensual, so prettily painted. I had the simultaneous desire of wanting to kiss them and wanting my lips to look just like hers. I said, "Oh Mommie, it's beautiful!" Mother was very pleased. And then she called me over to her. "Honey, I'll bet it would look very pretty on you too. Don't you think?" Did she really just say that? It was almost as if she had read my mind! I felt my face flush and I started to sweat. I nervously said, "Oh, I don't know Mommie. Lipstick is for ladies, not boys!" Mother smiled and said, "Well, that's true. But you are such a pretty boy, and I think you would look even prettier with a little lipstick on. She turned to the sales girl and said, "Don't you think so?" The sales girl was not about to disagree with Mother. She said, "Oh, yes, such a pretty boy should try on a little lipstick!" Mother said, "Come here, Sweetie." I was kind of glued to the floor, but I managed to take a couple of steps towards her. She grabbed my wrist and pulled me to her. She sat me down on one of the stools, and slowly began applying the lipstick to my lips! It was an indescribable sensation, one of the most sensuous things I had ever experienced. I felt that I was literally being transformed into a pretty girl, just by her applying the lipstick. Of course, this was not occurring in the privacy of our home, but right there out in the open, in the middle of a department store! There were other customers in the area, and everyone stopped to watch the pretty lady put lipstick on her son! When I opened my eyes, and looked around, the spell was broken. OMG, I was totally mortified! This was not like Mommie putting nail polish on my toes in the privacy of our house! It only got worse when I noticed that some of the women who were watching were with their young daughters, one of whom said loudly, "Mommie, why are they putting lipstick on that boy?" Her Mother told her to shush. I was really close to tears. I said, "Please Mommie, can we stop?" In the privacy of my room, alone in my bed at night, I had fantasized many times about Mother putting lipstick on me. But the reality, as we sat there in public, with people staring at me, was much more frightening. But Mother was unmoved by my plight. Mother said, "Don't be silly Honey, you look gorgeous. Doesn't he Jeanie?" She had me look in the mirror, and the truth is, I was captivated by what I saw. I loved how my lips looked with the lipstick! Jeanie chimed in, "Oh Sydney, you look totally adorable wearing that lipstick! I am going to buy it for you! My present!" Mother and Jeanie paid for their purchases, and I sat there, wearing my lipstick. When they were done, I whispered, "Mommie, can I please wipe it off now?" And Mother said, "Most certainly not! You look precious!" We slowly made our way through the store, stopping to browse along the way. I could see people whispering and pointing at me. I had never been so embarrassed in my life. The odd thing was, the more embarrassed I was at Mother's publicly feminizing me, it seemed that the more animated and happy she became. Well, it was more than happy; it was almost as if she had taken a drug that made her euphoric. And of course, as with any drug, when a little makes you feel good, your first response is to want more..... Needless to say, we were not done. Mother said, "Sydney, why don't we swing by the shoe department. Maybe we can find you something." I thought back to earlier in the day when Mother had painted my toes. Now I knew why she did not promise that no one would find out! The last thing in the world I wanted at this moment was to go to the shoe department and have someone see my painted toenails!! Combine that with the lipstick I was wearing, and, OMG. And, even though I was delicate, and pretty for a boy, with my short hair, lack of any other feminine items like earrings, girls clothes, etc., it was very clear that I was a boy. A boy wearing lipstick, with painted toenails. And of course, there was one more question. When Mother said we should go to the shoe department, did she mean the Girls department, or the Boys department? I was afraid to ask the question, although to be honest, I was not sure which would be worse. I was about to ask the question when Mother brought it up. "Sydney, because you have been so good, I am going to give you the choice. Would you like to go to the Girls department or the Boys department? The choice is yours!" Hmmm. This was some choice! Would I rather face the firing squad, or the electric chair?! Which would be more embarrassing - a boy in the Girls Shoe Department, or a boy who was wearing lipstick and nail polish in the Boys Department? I decided that they were both totally embarrassing, but I thought that the odds were higher that I would have a female sales person in the Girls Department, and that there would be mostly women and girls there. And as bad as that would be, I thought it would be much worse to walk into the Boys Department, where I might actually know someone, wearing lipstick. And to take my shoe off for the sales person, who would undoubtedly be a man, and have him see my pretty toes. The bottom line was, I would rather be seen as a sissy by the girls, than by the boys. Of course, Mother had to know this. But this way, rather than her suggesting she get me a pair of girl's shoes, it was ME asking for it!! So devious! When I said I would like to go to the Girls Department, Mother fairly glowed with pleasure. An infusion of the drug! She said, "Well, Sydney, if that's what you want! But young lady, I hope you do not have any big ideas! I know you loved my Ferragamos, but they are not appropriate for a girl your age. But I'm sure we can find something nice for you." I looked at her in shock! I was hoping to find something gender neutral, like a pair of penny loafers! Not a pump with a four inch stiletto heel! But I played along with the game and tried to look a little disappointed and said, "I understand, Mommie. " We walked into shoe the department. There were racks of shoes. Mother would walk over, pick one up, hand it to me and say, "What do you think of this one, Honey?" All of the shoes she handed me were very pretty, and perfect for a young lady. Some of them were flats, and some had a little kitten heel. Some were black patent leather. One had a very pretty bow in the front. I was very self-conscious because I was the only boy in the whole department. People were staring at me. Finally a sales girl came over to Mother and said, "Can I help you?" Mother said, "Yes, thank you. I am looking for shoes for my son." I could see that the sales girl was about to say, "You are in the wrong department," when she saw that a) I was wearing lipstick, and b) Mother already had picked out some shoes for me to try on. A knowing look came across her face and she said, "Oh those are all lovely." She turned to me and said, "Why don't we check your size and I can see what I can find for you!" I sat down and the girl measured my foot. I can't say she seemed totally surprised when she saw my toenails. She looked at me with a nice smile and said, "Oh, so pretty! That is a great color for you!" Mother drifted off with Jeanie to look at other shoes. The sales girl chatted quietly with me while she helped me to try on the shoes that Mother had selected. She said, "I know you are a little embarrassed. But you are really a lucky boy. " I looked at her questioningly. She continued, "When I was younger, my mother caught my brother trying on my clothes. She was so mad! He really got punished! You should be glad that your mother is helping you to be pretty. It's what you want, isn't it?" I hadn't thought about it that way, but I knew the answer. I was glad that she was helping me to be pretty - I just wished it was in private! I smiled back and thanked her. We left with two pairs of adorable shoes. I had no idea when I would wear them! It had been quite a day. What started out as a normal day ended with me getting my toenails painted, having lipstick put on me in a big department store, and buying shoes in the Girls Department. I was full of all kinds of confusing emotions. On the one hand, I had never been so embarrassed in my entire life. And really, I should have been mad at Mother for putting me in these positions. But when I got into bed that night, I did what I always did - I put on my panties and I clutched my photo of Mother. But this time, I shined the flashlight all the way down to my feet, and I wiggled my pretty, painted toes! And then I replayed the day's events back in my mind. In particular, I thought back to the Chanel makeup counter, where Mother was putting the lipstick on me. The image in my mind made me as hard and aroused as I had ever been. I pictured Mother smiling as she put the lipstick on me, and I came with a tremendous shudder. Chapter Three After our day at Bloomingdales, I was more obsessed with Mother than ever, and she knew it. A few days later, I came home from school to find her not home yet. When I walked into my bedroom, I found a small box sitting on my bed. On top of the box was a note. The note said, "My Darling, Sweet Boy, I think you are wearing out 'your' panties. So here are a few more pairs. I didn't know if you would like your own new ones, or if you prefer wearing mine, so I gave you a few pairs of each. By the way, you didn't really think that I didn't know about your little stash, did you? Mommie knows everything! And shame on you, Naughty Boy, for stealing Mommie's panties! Anyway, you should feel free to wear these during the day, not just when you go to sleep. And please, Sydney, put them in the hamper after you have worn them! It's gross for a girl to wear panties more than once! In the box I left another picture of me. I think it is the sweetest thing that you sleep with my picture! Mmmm, that makes Mommie feel so good! But it looks like the one you have is getting a little beaten up, so here is another one. I hope you like this one just as much! With ALL my love, Mommie Right over her name was a lipstick print of her mouth, lips slightly parted. It was incredibly sexy, something you would leave for your lover, not your son. Once again, I was mortified to know that she knew of my secrets, but also incredibly aroused that she was, well, flirting with me like this! I took off my pants and underwear. I took out a pair of the panties - not a new one, but one of hers - black lacy hip huggers - and put them on. I laid down on my bed, clutching the new picture, rubbing myself against my blanket. I did not last long..... A few days later, on a Friday, I came home after school and Mother told me that she had plans for a "girls' night out" with Jeanie. This was very unusual. Mother rarely went out, and almost never to do something that sounded vaguely wild. The truth was, I did not like the sound of a girl's night out one bit. Were they going to a bar to pick up guys? The thought of Mother kissing a man made me very upset. When I asked her exactly what she and Jeanie were doing, she grabbed me and started tickling me. "Oh, is my little man jealous?" She giggled and said, "Don't worry Sidney. You know you are the love of my life!" With that she planted a big kiss right on my lips. That definitely calmed me down. Then she said, "Would you be my helper tonight, and help me get ready? Maybe you can help me with my makeup. Would you like to do that?" Oh, my. Coming right after her telling me I was the love of her life, and kissing me on the lips, the idea of helping Mother with her makeup almost sent me right over the edge. I was trembling with anticipation. Mother went up to her bedroom to shower and get dressed. An hour later, she called me up to her bedroom so I could help her with her makeup. She was seated at her vanity. She was wearing a short, Japanese-style silk kimono that she wore while applying her makeup, so she would not get any on her clothes. The next half hour was one of the most special of my life. Mother really took her time with her makeup; for her it was a sensual experience, and one not to be rushed. She patiently explained every little thing she was doing. A few times she actually let me help her apply something, like her blush with her big blush brush. Well, she guided my hand, but I helped. And a few times she actually put some things on me. For example, she was telling me how she could actually feel when she had the right amount of mascara on, without even looking. And she put some mascara on me and said, "Here Honey, see how you can feel it on your lashes? And look how they make your eyes pop!" I could really feel the mascara on my lashes, especially when I blinked. OMG - it was amazing! I could only watch as she applied her eyeliner and eye shadow - it was way too advanced for me - but I loved to watch her transform herself. She was wearing dramatic eye shadow in several shades of blue, black liquid eyeliner, and lots of black mascara. When she got to her lips, she told me that because her eyes were so dramatic, her lips would be pale so as not to compete. Still, she ended up using a lip liner, lipstick, a lighter, frosted lipstick in the middle of her lips for a little pout, and then a clear lip gloss over everything. Her lips might not have been competing with her eyes, but they looked amazingly sexy! I loved this so much - doing feminine things with Mother, feeling close to her, but not having her embarrass me in public. I thought back to what the sales girl in the shoe department had said, and I realized she was right - I was lucky! Still, I wished she were not going out, that she and I could just sit at her vanity and play with her makeup all night. Finally, she was done. And then I got a surprise! She stood up right in front of me and took off her kimono! She was wearing black lace bra and panties. I mean, I guess it was not that different from her wearing a swim bikini, but still, I was shocked! I could not remember the last time I had seen Mother in her underwear. I had never really focused on Mother's body before. I had usually only thought of her beautiful face. But now that she was standing in front of me in her bra and panties, I was awestruck by her voluptuous body. There was nothing boyish about Mother's figure. It was all sensuous curves, especially her hips and her behind. She giggled at my expression and said, "It's ok Sydney, it's just us girls!" I both hated and loved it when she called me a girl! Then she said, "You like?" And she put her arms straight up and did a little dance, turning around and wiggling her behind at me! Mother was shamelessly teasing me, and I was breathless! Mother put on a short, royal blue cashmere sweater dress that came up to mid-thigh, and black boots with a stiletto heel. The cashmere clung perfectly to that round behind and curved hips. She looked absolutely ravishing. Like everything else about her, her outfit was elegant and sexy at the same time! Although she had done everything possible to make me feel better about her going out, I was still feeling jealous and pouting. I knew that any guy who saw her was bound to fall head over heels for her. As she stepped out the door, she gave me an air kiss - she did not want to muss her lipstick - and said I should not wait up for her. I gave her a sad look and said, "You know I will! Do not have too much fun!" And with that, she was out the door. Chapter Four I did wait up for her. And she did not get home til 1 a.m. The whole time, I was picturing her at some bar, dancing with and then kissing some strange man. This was the opposite of the feeling I had while sitting with her at her vanity. I was unhappy. More than that, I was jealous. I knew it was crazy for a boy to be jealous that his mother might be out having fun with a man, but I didn't care. I felt the way I felt. When she walked in the door, she could see that I was not happy. Well, it was a little worse than that. I had decided to put on her kimono. And well, I couldn't help it, but I had cried a little, and I had forgotten that I was wearing mascara, so I had raccoon eyes. Mother saw me and started laughing uncontrollably. That did not make me feel any better! She tried to stop, and said, "I'm sorry, Sweetie! But.." and she started laughing again..."Well, you are quite a sight in my kimono, with your mascara running!" I realized she was right, and I started laughing too. Mother always made me feel better. But then I realized something else. Mother was a little drunk. I had never seen her that way! But I could tell. She was swaying a little, and her words were a little slurred. She took me by the hand and said, "Come on Honey, let's take our makeup off together." And we went upstairs to her bedroom and did just that. Mother and I were sitting next to each other at her vanity. We weren't really talking, we were just sitting there. The truth is, I did not really want to hear about her evening. Finally, she looked at me and said, "You know Sydney, it is not appropriate for boys your age to sleep in the same bed as their mothers." I looked at her wide-eyed. I had not said a word about sleeping in her bed, but the truth was, after being left alone that night, there was nothing I wanted more, and the thought occurred to me, but I just pushed it out of my head. And now she was mentioning it as if we had discussed it! How was it possible for her to know me that well?? I said, "I know, Mommie." And then she continued. "But, Sydney, you know, girls sleep with their mommies in the same bed all the time. And well, if you were my daughter, then it would be ok!" I could not imagine where she was going with this. I mean, I was not her daughter, I was her son! She said, "Well, Honey I was thinking, maybe if I gave you one of my nighties, you know, maybe we could pretend that you are my daughter, not my son. And then you could sleep in my bed, and we could cuddle. You know, just for tonight. Would you like that?" Now I knew Mother was a little drunk. But I was not about to lose this opportunity. I said, "Mommie, I would love to be your little girl. And I would love to cuddle with you in your bed." Mother got up, went into her closet, and came out with a little Cosa Bella Baby doll nightie for me. It was pink, and sheer, and frilly, and incredibly feminine, and that was how it made me feel. She said, "Put this on, Little Girl." I took off the kimono and slipped the nightie over my head. Then I got onto her bed, slipped under the covers, and snuggled up next to Mother. We were laying on our sides, facing each other. We embraced, and one of my legs slipped between hers. She started giving me lots of little kisses, all over my face and neck. And then, perhaps sensing the danger of the situation, she rolled over, back to me. Now, I was kind of spooning up against her, and what I was afraid would happen, did happen. In about two seconds, I was as hard as could be. I knew this was wrong, that I should not be in bed with my mother, and I knew that if I were, I certainly should not be getting hard. But I was. And I was very nervous about what would happen next. I guess I expected her to tell me I should go back down to my bedroom. But that was not what happened. Instead, I almost felt her pushing her beautiful round behind back into me, offering the resistance I normally got from my blanket. This was almost too much for me. We held that position, and it took everything I had not to push into her; I knew that the slightest movement, and it would all be over. But I didn't move, and in that state of arousal and bliss, we both fell asleep. We woke up in the morning, entangled in each other's arms. Now that she was not drunk, how would she react? I was afraid that she would be upset. But my fears were unfounded. She stretched out like a big cat on her bed, smiled, and then gave me a little kiss on my lips. Then, at the same time, we both noticed that there was a stain on the sheets. OMG, that must have happened while I was asleep! I was horrified! But Mother just smiled and said, "It looks like somebody made a mess!" I apologized profusely, but Mother was nonchalant. She said, "That's ok, Honey, accidents happen." And that was it. We got up, got out of bed, walked downstairs together, and had breakfast. That day, everything seemed normal with Mother, which I was very relieved about. I mean, I knew our whole relationship was not normal. I knew I was not normal. That my love of femininity was not normal, and my attachment to Mother, which lately had an erotic element to it, was also not normal. And on some level, I knew she was not normal. Not only because she loved feminizing and flirting with her son, but because she seemed to love publicly embarrassing him with that feminization. And I couldn't say for sure, but it felt like the pleasure she got from my embarrassment had an erotic element to it as well. For some reason, I had this feeling that the incident at the Chanel counter was somehow related to what happened later - that her putting lipstick on me had gotten her so aroused that she wanted me in her bed. So, even before that night, I knew things with us were, well, let's say, unusual. But those other things at least had a public element to it. But sharing a bed was something neither of us would admit to, even to Jeanie. Would it be a one-time event? I was dying to know what Mother was thinking. Finally, at dinner, Mother brought up the subject. She said, "You know Sydney, I'm not sure I would have let what happened, happen if I had not been a little drunk last night. Still, I'd be lying if I said it didn't feel good after all these years alone, to have someone just to cuddle with in bed. And, well, you might have had an accident while you were sleeping, but you were asleep, and I don't think we did anything terribly wrong. Still, you understand that what we did is not considered acceptable right? It has to stay our little secret, ok?" I told her that I did understand. Then she giggled and said slyly, "It was while you were asleep, right?" I nodded my head vigorously. And then, I had never seen Mother act shyly before, but she quietly said to me, "Do you think you want to be my little girl again tonight, and cuddle with me in bed?" I told her I was hoping she would ask me that, and that I would love to! And then she said, "OK, well, you can't keep making a mess in my bed. I'll be right back." She went into the hallway closet and came out with a supermarket bag. Inside was a package of Pampers Girls Under Jams Absorbent Bedwetting Pants. Diapers, but certainly not made for the purpose for which I would be using them! I looked up at Mother, wide-eyed. She smiled, and said, "Well, we did decide that the only way for you to share my bed is to be my little girl! And this way I will not have to worry about you making a mess when we fall asleep! Ok?" It was more than ok! I hugged Mother tight, closed my eyes, and looked forward to bedtime. I really was a lucky boy! The End.