Pageant Playmates free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
My wife Joan died two years ago when our son Joey was only four years old. It's been extremely difficult for him and nearly impossible for me to get over the loss. Joan's mom and Susan, her sister, along with my parents have done their best to spoil Joey to try to help him over the loss of his mom. It seems to help, Joey's typically a happy little camper, but I'm still a basket case. Joan and I were high-school sweethearts; we got married soon after college and were married for five years when Joey was born. Four years later, an aneurysm in Joan's brain burst and she died instantly. Joey and I have struggled on since then, but we've both been so very lonely. The neighborhood we live in is quiet and peaceful; actually, it's too quiet. Joan and I thought a nice, peaceful neighborhood populated mostly by retirees would be a wonderful place to raise our family. We didn't realize that boys need to run, climb, and jump, and that they need to do these things with other boys. Joey was the only kid under sixteen for nearly a mile, limiting his playtime with other kids to recess and lunch at school. I'd take him his friend's homes on weekends or bring them to our house, but it wasn't enough. Joey spent most of his time sitting around, reading books and playing video games. I was thrilled when I heard that a widowed woman with a son Joey's age was moving into the neighborhood. Finally, Joey could be a normal boy. The idea of having an available woman living nearby wasn't so bad either. I didn't waste any time introducing myself and Joey to Linda and her son Bobby. I'll be the first to admit that my motives were not purely altruistic; Joey needed a friend but Linda was a walking wet dream! Tall, with brown hair, and a smile that could cause a man to climax, Linda seemed totally unaware of the effect she had on men. How could she not realize that she was one of the most beautiful women in the world? She invited me in for coffee and donuts and we spent an hour just talking about our kids and our lives. After a few minutes, it was like talking to my sister; Linda's personality completely overshadowed her beauty, revealing a wonderful human being. When Joey and I finally left, I was sure we'd made new friends. Things were working out so well with our new neighbors that I couldn't believe my luck. The boys had so much in common such as being the same age and in the same class at school. Linda and I worked different shifts so we divided getting them to and from their bus stop and keeping them entertained after school. I made sure they got to school and she took charge after school and evenings. Linda and I also became good friends; she enjoyed watching baseball, was an avid reader of Tom Clancy novels, and was a frequent visitor to Urban Legend web sites. The fact that she was she was beautiful wasn't lost on me but Linda would've been worth getting to know even if she didn't take my breath away. One Saturday afternoon the boys were playing at Linda's. I was taking a break from cutting my grass and happened to glance over and see Joey apparently having a tea party with a girl who looked like she could be related to Linda. I waved and they waved back; I didn't have time to stop to see who the little girl was. Later, I asked Joey who the little girl was and was puzzled when Joey said that he hadn't been playing with any stinky girl. I knew Joey was going through that stage where he didn't like girls so I thought that he might have taken a liking to a cousin of Bobby's and didn't want to admit it. Weeks went by and the system Linda and I had implanted was working without a hitch; Joey was having a great time with his new friend, and Linda, and I seemed to be getting closer. Every now and then, I'd see Joey playing with his new friend but to avoid embarrassing him, I never asked about her. Months passed and I finally got up the nerve to ask Linda out. When she said yes, I wanted to jump up and down and tell the world that I had a date with the most beautiful, most intelligent, woman alive! Linda arranged for her sister-in-law Christine to watch the boys while she and I had dinner and took in a movie. It was a memorable evening and one I couldn't wait to repeat. I asked Linda out again several weeks later and happily agreed. One thing led to another and soon Linda and I were somewhat of a couple. We started taking the boys to baseball games, movies, and Chuck E. Cheese where people often complimented us on our sons, mistaking us for husband and wife. The first time it happened, I was about to set the record straight, fearing that Linda might feel uncomfortable. Linda seemed to read my mind; as soon as I opened my mouth, she put her hand on my leg to distract me and thanked the woman for her compliments. After the woman left, I turned to ask Linda why she had let the woman think the boys were brothers and was met by her warm lips. I'll admit that I was surprised but I'm not one to object to a woman like Linda kissing me. I returned her kiss and felt my pulse race as I took her hand in mine. "I hope that wasn't too pushy of me," she apologized after our kiss. I was still holding her hand and she didn't seem in any hurry to take it back. "No, I like woman who knows what she wants," I teased and gave her hand a squeeze. "Bernie, I've wanted you to kiss me the first time we met." She laughed. "A girl can only wait so long." Our dates became more frequent after that with the boys often spending weekends at each other's home. It was after one of these weekends that I noticed a problem. After bringing Joey home, I told him to take a shower for school the next day. While he was in the shower, I walked in to take his dirty clothes to the laundry room. Like many little boys, Joey had a habit of taking his briefs and pants off together leaving me to separate them for the laundry. When I went to separate his pants and briefs though, I found a pair of very frilly, blue nylon panties instead of his G.I. Joe briefs. Not sure how a pair of panties could get mixed in with Joey's pants, I checked again but his briefs were just not there. I took the panties back to Joey's room and waited for him to finish his shower. "Where did these come from?" I asked, showing him the panties. "And where are your underpants?" "Oh, Bobby lent me those," he said as he slipped into his bed. "I forgot I had them on, I must've left my underpants at his house." "Why would Bobby lend you girl's underwear and why were you wearing them?" "They're his panties," Joey explained in that way little kids have when they think something's very obvious. "He let me wear them so I could see how nice they felt." "Did you like them?" I did my best to act as though my son wearing girl's panties was no big deal. I didn't want to scold him and make him wonder why wearing panties was wrong; kids often rush for the very thing their parents forbid them from doing. "Uh huh," he said as he pulled his blankets up to his neck and yawned. "They feel really neat!" With that, he closed his eyes and drifted off to dreamland. Several days passed before I got a chance to see Linda again. As soon as the boys ran off to play in Bobby's room, I took the panties out of my pocket. I explained the whole bizarre story of Joey admitting to wearing them but claiming that they were Bobby's. I expected Linda to be upset; after all, her son must have stolen a pair of panties from some little girl. She shook her head and began to cry. "I'm sorry John; I guess I owe you an explanation. I'll understand if you decide to leave. "The whole thing is pretty odd but please believe me, it's all true. Years ago, I married a guy I had known for years. Ray seemed like the answer to my prayers, kind, considerate, nothing at all like the type of guys I had always attracted. We hit it off right away and were married before we were through college. "Everything was great for a few years but shortly after I got pregnant, Ray broke down and told me that he had been living a lie. Our love, our marriage, had all been feeble attempts on his part to deny an overwhelming feeling that he should have been a woman!" "Holy hell," I gasped. "How do you deal with something like that?" "I did my best but there was no point in continuing on; we parted as friends and Ray still stays involved in Bobby's life." How do you walk away from a story like that? No matter how goofy it seemed, I had to hear the whole thing. "Did Ray, uh," I stammered. "Is he..." "He started hormones and even lived as a woman for a year before we divorced. He had the final surgery a few years ago and is now a happy, well adjusted lady." I wanted to kick myself for asking; morbid curiosity got the better of me. "Does he or I guess it's she now, does she look like a woman? Can you tell that she used to be a guy?" Linda called out to see where the boys were before continuing. "You've met her several times; she baby-sits for me when we go out." I wonder how silly I looked with my jaw dropping down. "Your sister-in- law Christine is a guy?" I couldn't believe it; I'd met Christine several times and although she was no match for Linda, she was still very pretty. We'd talked a few times and had often been standing within inches of each other and I never guessed her secret. "Does Bobby know?" "No, he thinks his dad died before he was born; that's close enough to the truth. Aunt Chrissie is always happy to take baby-sit; it lets her stay close to Bobby and he loves his aunt." My head was spinning as I tried to understand why a guy who was married to a woman like Linda would rather be a woman. I'd try to sort it out later; I still needed to know why my son was wearing a pair of panties. "That's all very strange, but why was Joey wearing panties that he claims he got from Bobby?" Linda called for the boys to come down from Bobby's room. "I have an idea, but let's go straight to the source." She showed the panties to Bobby. "Did you give these to Joey?" "Sort of," Bobby answered. "We were playing dress-up and I guess he forgot to take them off." "Haven't I warned you not to play dress-up?" Linda asked sternly. "Now Mr. Lucas might not let Joey play with you anymore." "I'm sorry Mr. Lucas," Bobby quickly apologized. "We got bored; we played every single one of our games. And there wasn't anything good to watch on TV." It seemed odd that Linda was more concerned that Bobby had played dress- up with Joey than that he actually owned girls panties. "You let Bobby dress up like a girl?" I guess it was easy to figure that I was lost so Linda told the boys to go play and explained everything to me. "Ray, my ex, began wearing girl's clothes as a little boy. He said that he always knew that he should have been a girl and therefore his wearing a dress was perfectly normal. "I felt so bad for him; he was a prisoner in his own body. Unless he got help, he'd almost certainly go mad. I badgered him into seeing a therapist and then to follow through on the recommendation for a sex change. It cost every cent we could get our hands on but today, Chrissie is a happy lady. "We were broke from the thousands of dollars it took to turn Ray into Chrissie. It was then that I remembered hearing about pageants that little girls compete in with frilly dresses, dance, and talent competition. "Well these pageants were actually designed for little girls but that was discriminatory so they had to admit any boys that wanted to compete." "You're losing me," I told her. "What has all of this got to do with the panties I found?" "I'm getting there," she promised. "Just be patient for a little while longer." "So now boys are allowed to enter these pageants but they have to dress and compete just like the girls. There's a lot of prize money to be won; I mean fifth place can take home a couple of hundred dollars. Well, everyone was always mistaking Bobby for a pretty little girl so..." "You entered your son into a girl's beauty pageant?" What kind of monster was I involved with? "I had just been laid off, the bills were piling up, and I had nowhere to turn," she cried. "I hated myself for doing it but I got Bobby all dressed up in a party dress, petticoat, ruffled panties, the whole works. I brushed his long hair, and entered him into one of the contests." "So these were the panties he wore for that contest?" I thought I was starting to get a handle on the matter. "No, those are his everyday panties," Linda gulped. "His contest clothes are much prettier." "You're still entering him in those contests? Give it up, he's a cute kid, but no one would ever mistake him for a girl. You're going to make him just like his dad if you keep this nonsense up." Linda suddenly seemed to be mad at me. She got all red in the face, was about to say something but suddenly calmed down, and pulled a picture album from a bookcase. "Renee Lynn won fourth place in her first pageant," Linda said proudly as she showed me a picture of a cute little girl. "She's won several contests and has never scored lower than third place since!" I looked at the girl in the pictures. In some, she was all decked out just like little girls get for those pageants; a frilly dress, ankle socks, patent leather shoes, her hair curled and a touch of makeup. Other pictures showed the little girl in a cowgirl outfit, as a majorette twirling a baton, and a cheerleader. "Satisfied?" she demanded as she handed me another album. "Renee is a doll and she has the ribbons to prove it!" The new album showed the same girl wearing pageant dresses and receiving blue ribbons from the contest judges. Linda handed me a plaque with the ribbons attached. "You don't expect me to believe that this is Bobby; do you?" I thought it was time to get Joey and leave this crazy woman. "Bobby, come here please," Linda called out. "Mr. Lucas doesn't believe that this is you in these pictures," she said very calmly. "So I want you to pick one of these pictures, go to your room and get ready as if you were going to a pageant. When you're all dressed, call me and I'll fix your hair; we're going to show Mr. Lucas and Joey how pretty you can look!" "C'mon Joey," Bobby said. "Watch me turn into Renee Lynn!" "Cool!" Joey laughed as he ran after Bobby. Soon, Bobby called for Linda and she rushed off. A few minutes later, she walked back into the room, followed by Joey and the girl in the pictures. The girl was wearing an emerald green pageant dress with white lace ruffles down the front, around the hem and the short, puffy sleeves. She wore green ankle socks with white lace trim of course, and a pair of green, patent leather shoes. She had blonde hair styled in a flip and held in place by green barrettes, and her pretty face showed just a hint of makeup. "Hi Mr. Lucas," she said in a sweet voice. "I'm Renee Lynn Carlson." "Check it out dad," Joey laughed. "Bobby's a girl." "She's so pretty," I said without thinking. "Apology accepted," Linda grinned. "You can go back to playing now Renee, be careful if you keep that dress on though." "Can Joey play dress-up Mr. Carlson?" Bobby asked. "Dress-up, Joey?" I was still too confused to understand. "Sure, just be careful not to break anything." Renee, I couldn't very well call her Bobby when she was so pretty, and Joey ran off to play, leaving me to mumble a real apology to Linda. "Linda, I don't know what to say. It just isn't right to dress your son up like a little girl and enter him into those pageants." "I'm not forcing him," Linda insisted. "He enjoys it; you see how many contests he's won. Why make him stop something he likes to do, isn't hurting him, and he's good at?" "Because it's wrong for boys to dress that way!" I shouted just as the boys walked back into the room. Renee was still wearing his pageant dress and was accompanied by another girl in a red and blue plaid school dress with red knee socks, and saddle shoes. I lowered my voice until I realized that the second little girl was Joey! "What the hell are you doing in a dress?" I screamed. "Get changed and let's go home." Turning to Linda, I shouted, "I ought to call the Child Welfare department on you; I can't believe you're this sick and twisted!" When Joey came back in his own clothes, I practically dragged him to the car. Linda was crying and begging for another chance but there was no turning back. She was some sort of pervert and I wasn't getting involved in her sick little charade! I spent the next several days wondering what to do about Linda. Except for the matter of Bobby, it was as if we were made for each other. No other woman has had that effect on me since Joan; was it worth overlooking what she'd done to Bobby? Then again, if I continued our relationship, the same thing might happen to Joey. He'd already been playing dress-up with Bobby and seemed to enjoy it. Could I risk my son getting engrossed in that sort of thing? A week after I had stormed out of her house, Linda called and asked if we could talk. Still unsure of what to do, I thought it might be a good idea to see what she could possibly have to say. "How about I get a cold beer for you?" Linda offered. "You like Coor's, don't you?" I nodded and Linda turned on some music before getting my beer. I settled back and tried to make a decision but couldn't. It seemed like only a few moments but the clock said half an hour had passed since Linda offered me the drink. "You must have fallen asleep," she said as she handed me a can. "Have you made any decision yet?" "You mean about you and Bobby? I'm sorry about the whole thing." The world flowed without my thinking. "You're right, no one's being hurt, and it's just a harmless little game." Just then, Joey came in wearing a grey pleated skirt, white blouse, a pink sweater tied around his neck, white knee socks, and black patent leather shoes. "Look at me dad," he laughed. "I'm a girl!" "A pretty girl too," I laughed. "You're just as pretty as your mom was. She always wanted to have a daughter too; it looks like she got her wish." "Now that you and my mom have made up, can Joey sleep over?" Bobby asked. I looked at Linda and knew Joey would be fine. "Sure, I'll pick you up tomorrow. Maybe the four of us can catch that new movie that's opening?" "That sounds like fun," Linda smiled and I felt as though I was the luckiest guy in the world. "Be careful, don't mess up any of Renee's pretty things," I called as Linda walked me to the door. I briefly wondered why I'd told Joey to be careful with Renee's things. Wasn't he always neat and careful with his own clothes? I guess it was just the standard warning parents give; I'm sure that Linda would supervise and make sure all was well. "I'll keep an eye on them," Linda promised as we kissed goodbye. "Don't worry about a thing." "Thanks for forgiving me," I told her as I held her tight. "I'm really sorry for going off half cocked like that." "I understand," she smiled. "It's not an easy thing to deal with; everything will be fine from now on though." "I don't doubt it," I smiled and gave her a squeeze. "You're right about being hard to understand though; I was just having problems trying to understand how a boy could compete with girls in a pageant." I smiled, gave her another kiss and walked home. I was cleaning up a few dishes when I started to think about Linda's ex- husband. I'd met Chrissie a few times but had never suspected that she used to be a man. Her looks, speech, and mannerisms all pointed to her being a woman. What could have driven him to that point? I couldn't figure the whole mess out so I thought I'd just forget about it. Unfortunately, fate had other plans. As I sat and watched TV, I happened on a special called "He's a Lady". I read the description of the program in my TV guide but couldn't believe it - Weekly challenges for the competitors will include learning how to behave like a lady, followed by going out in public to find out how convincing they are; being trained how to be a supermodel; planning a real wedding and then being asked to serve as the bridesmaids; and, finally, completing a multi-tasking challenge back in their hometowns where the guys must remain in character in front of family and friends. I knew there was a game on but I couldn't force myself to change the channel. Not only that, I programmed my VCR to record every single episode in the weeks to come. Normally, I wouldn't even have bothered with a show like that but I found myself glued to the set, fascinated by watching men being turned into women. That was crazy enough but what really was crazy was that I wondered how I'd look as a woman! I thought it would be fun to put on satin panties and a bra; pantyhose seemed to make a guy's legs look as sexy as a woman's, and with a dress and wig, I could probably be pretty convincing as a woman. Joey looked so cute earlier in a skirt and blouse; if he looked good why wouldn't I? Everyone said that he looked just like me when I was younger so why wouldn't I look as cute as he did? What's wrong with me? I suddenly came to my senses; why would I even think about dressing like a woman? That's what I get for spending so much time with Linda and her sweet daughter, I mean son. However, what's wrong with spending time with a woman like Linda? We have so much in common, and did I mention how pretty she is? If Bobby can get away with dressing like a darling little girl and winning contests, why should anyone care? The next morning, I called Linda's and asked if she could help me surprise the girls, I mean boys. She loved my idea and promised to have everything ready when I got there. "Hi dad!" a cute little girl in a white sundress and sandals, her shoulder length, dark brown hair, held in a ponytail. "Guess who I am?" "That's a tough question," I teased as I walked around the pretty girl. "You sound like someone I know but I can't seem to tell who you are." "It's me Joey!" "No, Joey was a boy and you're a girl. Renee's mom told me that Renee had a girlfriend named Julie who was staying over, are you Julie?" "No dad, I'm Joey!" It was so cute seeing him all flustered. "No, I'm sure I'd recognize my own son." "I am too Joey," he insisted even more. "Bobby and his mom turned me into a girl!" "But if you're a girl, then you can't be my son Joey. Which one are you, a boy named Joey, or a girl named Julie who's going to a movie today?" It took all of two seconds for my son to switch gears and announce that he was definitely a little girl named Julie! I picked him up, gave him a hug and a kiss, and then swung him around, causing his skirt to flare and exposing the slip and panties he was wearing. "Mrs. Carlson and Renee certainly did a good job of turning you into a girl," I said as I put my new daughter Julie back down. "Are you having fun?" "Uh huh," she was quick to answer. "I always like playing pretend and these clothes make me feel all funny." "That's okay," I told her. "Just remember that you have to be really good at playing pretend while we're out today. You have to be a very good little girl all day." "I will, I promise," she said as he fluffed his skirt. "See, Renee is teaching me how to pretend to be a girl." I gave her another hug and kiss then Linda handed each of the girls a purse to match their dresses. "See Julie," Renee said as she dangled his purse from her wrist. "This is how girls hold purses." Julie quickly slid her purse onto hers wrist just as Renee did. "Since we're wearing dresses, we can't run or anything," Renee continued. "We're girls and girls don't do that stuff when they're dressed up." "Julie, when you have to go to the bathroom, just tell me and I'll take you to the girl's bathroom, okay?" Linda asked. "Why do I have to use the girl's bathroom?" Julie asked. "Because you're a girl, you dummy!" Renee teased. "Girls go to the girl's bathroom!" "Okay," Julie nodded. "I didn't want to get into trouble for going into the girl's bathroom." "Don't worry honey," Linda told her. "Just watch Renee and do what she does." Julie was a very fast learner; she carefully scooped her skirt as he got into the car and brushed out any wrinkles as she got out at the theatre. The way the girls stood and held their purses set them apart from other girls waiting in line. It was obvious from the smiles of the women who saw them that they were every mom's dream of how her little girl should behave. The girls were perfect little angels during the movie; at intermission, they politely asked for the popcorn and candy, much to the delight of the woman working the refreshment counter. "You two are so pretty," she told them. "Are you sisters?" "No, this is my girlfriend Julie, my name's Renee," Renee smiled. "You're certainly look enough alike to be sisters," the woman smiled. "Your parents must be very proud of such well behaved young ladies." "Thank you," Julie blushed and giggled. "Wouldn't it be cool to really be sisters?" she asked Renee. Linda and I had been standing off to the side, watching the girls. We turned and smiled at each other at the same moment. After the movie, we took the girls out for burgers. Watching Julie, it was as though she'd always been a girl. She carefully swept her skirt and then demurely tugged it back down as he got into the car. "Good girl Julie," I smiled. "Thank you daddy," she smiled back. I could get used to having such an adorable little girl for my daughter, and Daddy sounded so nice coming from her. It was surprising how quickly she was picking things up; she really seemed to enjoy being a girl. Joey wasn't a troublemaker by any means but there was a clear difference between him and Julie. Julie was quiet and calm while Joey was a typical boy, running and shouting. I liked both and thought that it was wonderful to have such a sweet daughter and a son in one package. The girls both got Happy Meals with girl's toys. They seemed to be having a lot of fun playing with their new "Dora the Explorer" dolls; making them talk to each other and carefully walking them over their food trays. I couldn't imagine Joey being so calm; any toy he got would be climbing the back of the booth or trying to dive into his drink by now. "Julie seems to be enjoying herself," Linda whispered as we watched the girls play. "It's hard to tell that she's a boy." "Yes, Renee seems to be quickly rubbing off on her." I smiled and found myself wishing I were the one in the pretty dress. "It's quite a change." "There's an even bigger change between Bobby and Renee when Renee's competing in a pageant. She's a sweet girl now but when she's competing, she's such an elegant little lady." "An elegant little lady," what a picture that brought to mind. I could picture myself in one of Renee's pageant dresses, my hair all curled and pretty, singing a song for the audience. It must be so exciting to be standing there and knowing that you're prettier and more of a little lady than many real girls! "You seem lost in thought," Linda asked. "Care to talk about it?" I looked around the crowded restaurant; this would not be a good place to confide that I had spent a great deal of time as a pretty little girl. "Not now," I told her. "Maybe we'll talk about it later." She seemed satisfied and didn't press for more details. I felt very relaxed and comfortable around Linda; so relaxed that I didn't feel the least bit worried about telling her what I'd been thinking. I felt certain that she'd understand; after all, she'd been through it with her ex-husband Chrissie and was going through it with Renee now. I might just mention my thoughts to her later. We finished eating and drove back to Linda's where the girls rushed off to play dress-up, leaving me alone with Linda. "I don't mean to be insulting." She smiled and took my hand. "But there's such a resemblance between you and Julie." "She is my kid," I laughed. "I imagine there would be a resemblance." "No," she said softly as she squeezed my hand. "I meant as far as how you look. She's such a pretty girl and I thought you must have been just as pretty at her age." "I was often mistaken for a girl when I was little," I laughed. "I kept telling people that I was a boy but they just laughed and said that I was a tomboy. They said that I was so pretty and should wear pretty dresses instead of jeans." "Did you ever dress up?" "When I was seven, my mom dressed me in a party dress she borrowed from a neighbor." I never told this to anyone before, I thought. Yet, I feel a need to confide in this person. "I wore a blue dress with sparkles sewn into the skirt; they caught the light and reflected back with every step I took. I remember thinking that it was such a pretty dress." "Most boys wouldn't think of a dress as pretty," Linda laughed. "You must have been very secure in your masculinity." "I never thought of being secure," I smiled as I remembered how nice the dress felt. "I just thought the dress was so pretty. I mean, boys can appreciate pretty things; it's often drummed out of them but mom and dad were never like that. Sex roles were not rigid in my family; dad cooked, did laundry, and cleaned house just like mom. Mom helped with the yard work and fixed things when she could. They never told me that boys didn't like pretty things so when mom got me all dressed for Halloween, I didn't mind at all." Linda never even mentioned my blowing up over seeing Joey in a dress; it was an old wound, no point in picking at it. "Did you have to get completely dressed?" "Sure, mom never took half measures. If I was going to dress like a girl, I was going to wear everything a girl would wear. She said it would make my costume more realistic if I wore silky girl's underwear. She bought me panties, a slip, but borrowed shoes and socks for me. I even had a little purse just like the girls carried this afternoon. Mom brushed my hair and put a little makeup on me to make me look pretty. I got a lot of candy that year." "Did you ever dress up again?" Linda seemed hesitant to press the point. "Sure, a lot of times," I readily admitted. "Don't worry, you're not embarrassing me; it was fun." "You're sure you don't mind?" "Not at all, I didn't do anything wrong so there's nothing to be ashamed of." I squeezed her hand and felt a closeness I'd missed since Joan died. "Mom had to give the dress and stuff back but she'd bought me other clothes that I used to wear them at home when the weather was bad and I couldn't go out to play." "Your father must have been very understanding." "Let me tell you how understanding dad was," I laughed. "Remember I told you that sex roles weren't cast in stone in my family? Well mom was worried that I might feel bad because of peer pressure. She was afraid that my friends would tease me about wearing a dress, even if it were Halloween. She talked dad into dressing up at home for a couple of weeks just so I wouldn't feel uncomfortable." "He didn't mind? That's amazing!" "That was my dad; a great guy. For a whole month, he was my Aunt Suzie. As soon as he got home from work, he'd change into a dress and everything and stay that way until he went to work the next day. He had soft features just like I do and mom fixed him so well that you'd never suspect he was a guy." "Why did your mom have to fix him up; I thought he was just doing it to keep you from feeling bad?" "Once they saw how cute he looked, they decided to go for broke. Since he and mom still had to do things like grocery shopping, paying bills, and stuff, mom showed him how to do his own makeup, they got a wig for him, and they would do what they usually did. Mom told everyone that Aunt Suzie was dad's younger sister; no one ever figured out who she really was." "Did you ever go out with your mom and aunt?" "Sure, sometimes Aunt Suzie would take me shopping with her. We'd got to places where we always went but no one ever recognized us." Linda looked at me strangely. "Would you be upset with me if I asked something a little, well different?" "I don't know if it's possible to be upset with you," I told her as I brought her hand to my lips and kissed it. "I think I've gotten past being upset with you. Go ahead, ask anything you want." "Why not do for Julie what your dad did for you?" "You mean dress up like a woman?" I wondered if she could feel my heart racing. "I don't think that's necessary," I tried to laugh but it sounded so nervous, she had to know what I was thinking. "Julie seems to have adjusted very well." "I'm serious," Linda gripped my hand tightly. "If not for Julie, would you do it for me?" "Why would you want me to do something like that; aren't you happy with me as a guy?" Why couldn't I just say what I was really thinking, that I'd love to put on some silky lingerie and a dress and be Julie's aunt? "I don't know," she laughed. "I guess I've got this thing for pretty guys. I'll bet you'd be a doll; I promise not to laugh." "Why would you laugh?" I asked, feeling very insulted. "I'd be so damned pretty men would get hard two blocks away!" I saw the grin spread across Linda's face and realized I'd screwed up. "I guess that was the wrong thing to say?" "You weren't fooling me; I could feel your hand getting all sweaty," she laughed. "Do I at least get to know what you're going to do to me?" I joked. "You know sort of a condemned man's last request type of thing." "I'm going to turn you into a sex crazed slut and drop you off at the nearest construction site." "Don't make promises you don't intend to keep," I told her. "Seriously, I'd love to go places with my girlfriend and her daughter, if you think you can handle it." "I really don't know Linda," I tried to explain. "I haven't done that sort of thing in a while; I'm not sure I can pull it off anymore." "Trust me, please?" She asked. "You're going to look great." "Looking like a woman is one thing, acting like one is a whole different ball game though. I haven't done this in years and even then it was only for a short time." "I taught Chrissie to act like a lady, did you ever doubt her?" I shook my head. "Not for a second." "No one will doubt you either," she promised. I should have grabbed Julie and run away but I couldn't tear myself away from Linda; I felt sure that she was a keeper, no doubt about that. "I need to think about this; it's a lot to ask." I needed to get her to forget about the whole damned thing; maybe a little time would help. "You're afraid, aren't you?" "Let's just say it's something I'd rather not get into." That was a lot of nonsense; nothing would make me happier than getting into something pretty. "I understand," she shrugged. "I don't want to upset you. You really mean a lot to me." I looked into her eyes and knew I wanted to spend the rest of my life with her but something held me back from asking her to marry me. For weeks afterwards, I found myself wondering what it would be like to wear a dress again. Every time I saw Julie and Renee playing house, I thought back to my experiences in dresses. I spent many nights thinking about how I'd enjoyed growing up as Kerri and decided to take Linda up on her suggestion to become Kerri again. I sat down at my PC and spent several hours browsing the latest fashions and placing a few orders. My orders arrived just in time for a pageant that Renee was to be in. Linda had asked if it Joey and I would come along as sort of a cheering section and I couldn't wait to see the look on Linda's face when Julie showed up with her Aunt Kerri! Linda asked us to meet at her place early on the Saturday of the pageant. I got Joey up extra early that morning since I'd need the time to get us both ready. I hadn't told Joey what to expect other than that I had a big surprise for him that I was sure he'd enjoy. Joey was thrilled when I showed him the outfit I wanted him to wear; it was a pink denim jumper with a white top, pink knee socks, and white girl's sneakers trimmed in pink. I handed him a pair of pink nylon panties with "Saturday" embroidered in a circle of lace and a sleeveless white Tee shirt with a tiny pink rose on it. "This is so great dad!" he grinned. "I never thought you'd buy girl's clothes for me." "I never thought I would either." I smiled and showed him the blue and white floral patterned dress I planned to wear. "How about calling me mom, okay? I helped him adjust the straps on his new jumper before I placed a long brown wig on him and carefully glued it down. I carefully donned a wig cap before gluing down the wavy auburn wig I bought for myself. As I changed into the panties, bra, and slip I planned to wear I was overcome with wonderful memories. They were all so vivid that I nearly started to cry. I fought back tears as I did the clasp on my bra and adjusted the length of my slip. "You look so pretty mommy," Joey told me as I applied foundation. "Can I wear makeup too? "You're still too young for real makeup Julie." I smiled as I used his girl name. "If you want, we can pick up a toy makeup kit for you to practice with until you're old enough." "Really?" he asked excitedly as he stared into a mirror. "You'd really let me practice wearing makeup?" "Of course, you have to learn so that when you're old enough, you know how to use real makeup." "You're the best," he shouted as he rushed over to hug me. "Can we do this a lot?" "Absolutely, we'll have lots of fun. We can go shopping for pretty clothes, and I'll teach you all sorts of fun things like how to jump rope, and take care of baby dolls, and lots of things girls need to know." I took out a bottle of nail polish and did my nails. "Would you like to wear nail polish too?" I asked Julie. "Am I old enough?" he asked. "Certainly, a girl needs something to make her feel pretty," I told him as I filed and polished his nails. It was pretty warm so I decided to forgo stockings and slid my new dress over my head and stepped into a pair of light blue, high-heeled sandals, sprayed on a little cologne, and then set off for Linda's with my pretty little niece. Linda seemed confused when she opened the door for us. "Hi, may I help you?" she asked, looking from Julie to me. "Do I know you?" "I hope so," I smiled and held my hand out in a feminine manner. "I'm Kerri and this is my daughter Julie." The names seemed familiar but she was still having a hard time placing us. Suddenly it all came together. "Oh my god, you're beautiful!" she exclaimed. "You two are simply gorgeous. Come in, Renee will be ready in a little bit. Julie, would you like to watch Renee get ready while I talk to your dad?" "My dad isn't here," Julie answered as she ran to see Renee. "My mom came with me instead." I followed Linda into the living room, scooped my skirt, sat down, crossed my knees, and placed my purse in my lap. "It's not polite to stare," I reminded Linda as she stared, open mouthed at me. "I'm sorry; I'm having a hard time getting over how pretty you look!" "That's so nice of you," I smiled. "I bought this outfit just to surprise you." "You certainly succeeded in that," she laughed. "Are you wearing lingerie too?" "Of course, what did you expect, a tee shirt and boxers?" "You really went all out?" "Matching satin panties, bra, and slip, they make me feel all girly inside," I grinned. "I just love that feeling!" Linda gave me a squeeze and a kiss. "Don't get too girly," she warned. "I still want your brother around!" Those words got me all choked up; could she know that I was working up the courage to ask her to marry me? Every time we were together the feelings got stronger and more of the doubts of marrying her faded. I felt certain that she was the one to replace Joan in my heart but I wanted to make certain that Joey would accept her. We had a great time at the pageant; Renee looked very pretty and after a talent competition where she sang and twirled a baton, managed to win second place. Afterwards, I treated everyone to dinner and a movie. "Your mannerisms and everything are perfect Kerri," Linda said as we dined. "You could pass anywhere." "Thanks, I've had a lot of experience. It's like riding a bike; I guess you never really forget how to do it." Linda gave me more compliments on my appearance that night than I could count. Each time though, I worried that perhaps she was looking more for a girlfriend than a husband. Julie, Renee, Linda, and I began spending a lot of time together; we shopped for outfits, went to dinner together, and made several trips to nearby amusement parks. We even planned a vacation at the beach; girls only, just like when I was younger. Everything was going along so well; Joan's mother and sister eventually met and accepted Julie and Kerri and to my relief, Linda wanted to spend just as much time with Bernie as she did with Kerri. I had known Linda for six months when I decided to pop the question to her. Julie thought the world of her and couldn't contain her excitement over having Linda as her new mom. I invited Linda over for dinner one evening after arranging for Christine to watch the girls. We were sitting there, listening to soft music when I showed her the ring. "I love you Linda," I told her. "I never thought I could love another woman after Joan died but I was wrong. You mean the world to me and Joey and I can't imagine anyone else I'd want to spend the rest of my life with. Please marry me?" To my surprise and dismay, Linda began sobbing hysterically. "Oh hell, I hoped it would never come to this," she cried. "I never meant for this to happen but I lost it when you got so upset over Joey's dressing up." "That's ancient history," I told her as I held her and tried to comfort her. "It had nothing to do with you anyhow. I'd been dressing as Kerri for so long, but I wanted to give it up for Joan. Unfortunately, Kerri was such a major part of me that I was finding it impossible to give her up. I told you that I had experience dressing as a woman but I've never told you how much. "Everything started out so innocently; I was going to go to the local Halloween party and trick or treating as a girl. Lots of boys had done it before but they probably didn't have as thorough a mom as I did. "I mentioned it before; whatever mom did, she did with unmatched zeal and turning me into a little girl for Halloween was not going to be the exception. "She borrowed a dress, shoes, and socks from a neighbor, and then went shopping for the appropriate underwear that I'd need. I didn't see the point in it but mom insisted that little girls did not wear boys briefs and tee shirts under their pretty dresses. She went shopping and came home with several slips, two packages of silky panties, a couple of pairs of knee socks, and a pair of girl's shoes and even a little girl's wig. "It looked like I was getting a sister from all of the clothes she'd bought. "Mom explained that since I was going to be a girl for the Halloween party and trick or treating, she wanted me to get used to wearing girl's clothes. From now until Halloween, I should dress and act like a girl so that I'd fool everyone when I went to the party. "Mom promised that no one would laugh or call me names and that was that. I wasn't about to question her opinion; I was a little kid, she was my mom, and mom always made things work. That evening I became Kerri, a sweet, nine year old girl. "Every afternoon I came home, took off my school clothes, and became Kerri. It didn't take long for me to decide that I liked being Kerri; the panties and slip felt so nice and smooth; dresses were comfortable even if I did have to be careful how I sat. I still felt funny though so mom asked dad to help by dressing like a lady. "It helped to see dad wearing dresses; he was my idol and if he didn't mind wearing a dress, then I wouldn't mind either! "Mom got dad a couple of dresses from the same thrift shop mine came from and bought him pretty underwear, stockings, and heels to wear. After she got dad all dressed, she surprised him with a pretty wig she'd bought and then put makeup on him. "'You're a pretty lady, dad,' I remember telling him. 'Just like mom.' "'Thank you Kerri.' He actually blushed at my compliment. "'Talk a little bit softer honey,' Mom told him. 'Good, now just a little bit higher pitched.' "'You even sound like a lady dad!' I couldn't believe it, mom had changed dad into a lady. "Dad grinned as started saying silly things about where it rains in Spain. "'Good job,' Mom clapped. 'Maybe we should change your name to Eliza Doolittle?' "Mom said that was a lady's name in an old movie. "'No, that's too old fashioned. Let's go with Susan or Suzie for short.' "Dad laughed and pulled me to his side. 'Hi, my name's Suzie and this young lady is my daughter Kerri.' "He showed me how to curtsy which made mom laugh. "Every night after work, Dad would disappear into his bedroom and my Aunt Suzie would come out. She'd help mom with dinner and anything else that needed done. Later, mom, Aunt Suzie and I would put on one of our pretty nightgowns and watch TV until it was time for bed. The next morning dad would go to work just like he always did. "One evening, Mom was teasing Dad about how pretty he looked. 'I'll bet you say that to all the girls.' Dad put his hand on his hip and fluttered his eyelashes. "'No, I'm serious,' mom insisted. 'Both of you are pretty enough to fool anyone!' "I don't know what got into me but fooling people sounded like a fun game. 'Do you really think so mom? Do you think we could really make people think we're girls?' "'Why don't we find out?' she suggested. 'We could go that super mall on the weekend, unless you girls are afraid?' "'We're not afraid, are we Aunt Suzie?' "Dad looked at mom and shook his head. 'No, we're not a couple of scared little girls, we'll do it!' "I jumped up and down, clapping and hugging dad. 'This is so neat dad! We'll show mom that we're pretty girls, won't we?' "Dad practiced putting on makeup and walking like a lady for the next couple of days; he even made short trips to the store to get used to being a lady in public. By the weekend, dad was as comfortable going out in a dress as any lady. "Dad put on a bra, slip, and pantyhose, and then stepped into a cute light brown corduroy skirt, white turtleneck top, and a pair of high- heeled boots. He put on his makeup, fixed his wig, and turned into a pretty lady. "'Your turn.' He smiled and helped me put on my first pair of pantyhose. 'You have to be careful with these Kerri; they can get runs in them and won't look pretty anymore.' "How could you not love wearing pantyhose? The feel of the nylon against my legs was like being given a triple scoop cone of my favorite ice cream. "'These feel so nice Dad,' I grinned as I rubbed my legs. 'I wish I could wear them all the time!' "'Don't call me Dad when we're out Kerri, remember to call me Aunt Suzie,' Dad corrected me as he adjusted my slip. 'But you're right, stockings do feel very nice!' "Aunt Suzie told me that we were going to go to the mall where no one would know us. We could shop and try things on if we wanted, just like real girls. "'Can I get some more pantyhose?' I asked hopefully. "'Why would you want to?' Dad asked without being critical. 'Once Halloween's over, you won't need them.' "'Please Aunt Suzie, they feel so nice. If you buy them for me, I promise to wear them.' Mom had heard me ask Dad to buy me pantyhose. 'You'd really wear them after Halloween?' "'Sure, I promise. I could get all dressed up and go shopping with you and my favorite aunt.' "'Well Suzie, I think we've got ourselves a daughter.' "'Please, please, I'll be a good girl, I promise!' "'Boys don't wear dresses and stockings,' Aunt Suzie insisted. 'Other boys might laugh and call you names.' "'But I'll be a girl!' I insisted. 'Girls can wear dresses and stuff and no one calls them names.' "'Why don't we try it for today?' Mom suggested to dad. 'If no one looks at you two funny and you enjoy it; we could do it again.' "'You're serious aren't you?' Dad asked. 'You wouldn't mind having Suzie and Kerri around after Halloween?' "'Aren't you girls having fun?' She had this nutty looking smile. "'I am!' I answered quickly. 'C'mon Aunt Suzie, please tell mom it's okay.' "'Let's see how things go today before we decide, okay?' Dad asked as he helped me button a white blouse and zip up a green jumper. 'If everything goes okay, there could be two more girls in this family.' "Mom put my wig on me and brushed it so that I looked just like the girls at school and we all drove to the mall. "Everything went so well, it was as if the whole day had been scripted. Mom, dad, I mean Aunt Suzie, and I spent the whole day shopping and no one ever seemed to notice a grown man and a little boy wearing dresses. "Aunt Suzie and I had a great time shopping and trying on lots of pretty clothes and since no one noticed us, mom bought each of us a dress and a nightgown. Aunt Suzie got some sexy looking underwear and I got several pairs of pantyhose called 'Little L'eggs'. "By the time Halloween came, I was comfortable wearing girl's clothes; Aunt Suzie and I did lots of things like grocery shopping together and she even bought me a toy makeup kit which I spent hours playing with. Sometimes, when mom, Aunt Suzie, and I were going to have a girl's day together, I'd bring my makeup into their room and pretend I was putting on makeup just like them. "The Halloween party was a lot of fun; my friends couldn't believe that I was really a boy and I won first prize - a gift certificate for a party at McDonald's, my favorite place to eat. "The next day was Halloween and mom had another surprise for me - I was going to go Trick or Treating as Shirley Temple! I wore ruffled panties that showed under a frilly dress that ended well above my knees. Under the dress, I wore what mom called a petticoat, which was a fancy slip that made my dress stick out. I couldn't wear stockings but instead I wore thin socks that covered my ankles and were decorated with lace trim at the top. A curly wig and patent leather shoes completed my change into an adorable looking little girl. 2Everyone thought I was so cute and gave me lots of candy, which helped make up for the teasing from some other kids. "By then, Dad and I were both hooked; Mom didn't mind so Aunt Suzie and Keri became part of the family. "We went shopping, to movies, and even took vacations as three women. Getting my first bra and being allowed to wear makeup were major events in my life, just as they are for a real girl. "When I met Joan, I told her about my dressing and she promised to try to understand. I told her not to worry, that I'd give it all up for her. I threw away my clothes, my makeup, everything; I wanted to be all man for her. "It was pure hell after a little while; I'd see her in a pretty outfit and wish that it was me wearing it. When we made love, I wanted to wear the slinky little negligee. If I was home alone, I'd find my self staring into her closet or fondling her lingerie. "When Joey first started playing with Bobby and wearing girl's clothes, I freaked out. I had always considered it harmless fun until I tried to stop and realized I couldn't! I felt trapped, that my cross-dressing was going to ruin my marriage. When Joan died, I carried those guilt feelings with me. I felt that I had failed her. "I didn't want Joey to have to go through what I did, so I freaked out. "I realize now that I had put myself through hell needlessly; Joan had promised to be understanding but I insisted that it wasn't necessary. "Someday, I'll explain all of this to him and if Joey continues to dress throughout his life it will be his decision. I hope he'll find a woman as understanding as Joan was or as you are." I finished my story and looked at Linda who was shaking her head. "You don't understand," she insisted. "That never happened, you never did those things, and they're all a figment of your imagination. They're all a figment that I put there when you threatened to report me." Linda explained that when I threatened to report her for abusing Bobby, she panicked. Bobby was all she had left and she couldn't bear the thought of having him taken away from her. She told Christine about her problem and Christine suggested implanting Post-Hypnotic suggestions in my brain that would make me forget about reporting Linda and remember a non-existent life as a cross-dresser. "Remember that day when you came over and I offered to get you a beer? The music I put on planted those ideas in your head. I'm amazed at how well they worked; you've created a very detailed life that never happened." She pulled away from me. "I was wrong to do that to you Bernie; I can't expect you to love me after what I did to you." "You mean that crappy CD you turned on?" I broke up laughing. "It was so bad; I turned it off and fell asleep waiting for you." I walked over to a bookcase and pulled down photo albums placed too high for Joey to reach. "These are proof that what I told you was real." I handed her the albums and chuckled as she looked at page after page of my life as Kerri; from that first Halloween to the vacations with mom and Aunt Suzie. We're planning a fall wedding; Christine will be Linda's Maid of Honor, our lovely daughters will be the prettiest Flower Girls ever seen and Aunt Suzie and mom are busy shopping for just the right dresses. I'll wear a tux for the wedding but after a brief honeymoon the family will be taking a girls only vacation for two weeks at Lake Erie. I'm sure we'll have some great pictures to start another album with!

Same as Pageant Playmates Videos

4 years ago
  • 0
  • 15
  • 0

Crossfaded part 2 Playmates

A few months have passed since the first time Meredith and I had sex and ever since then, we never really spoke of it. At one point, I was afraid it had made things awkward between us but it merely turned into a playful joke whenever a sexual topic is brought up between our group of friends. Of course, our friends don't know why we always laugh when we make eye contact so they just think we're immature idiots. On a Friday night, I asked for the weekend off at the club and as usual, I...

1 year ago
  • 0
  • 10
  • 0

A New Pair of Playmates

I live in a fairly conservative region of my State. As such, one might think sexual encounters are few and far between. Perhaps I am fortunate - lucky - or observant and focused. I believe it's more the latter than the former.I spend a fair amount of social media time on sexual chat sites. Over the past month, I met a guy - married - who has been discussing varietal sex with me. He has been discussing 3-way sex with his wife, and revealed that to me. I encouraged open, frank discussions - to...

2 years ago
  • 0
  • 10
  • 0

A New Pair of Playmates

I live in a fairly conservative region of my State. As such, one might think sexual encounters are few and far between. Perhaps I am fortunate - lucky - or observant and focused. I believe it's more the latter than the former.I spend a fair amount of social media time on sexual chat sites. Over the past month, I met a guy - married - who has been discussing varietal sex with me. He has been discussing 3-way sex with his wife, and revealed that to me. I encouraged open, frank discussions - to...

2 years ago
  • 0
  • 10
  • 0

Purchasing Panties and Finding Playmates

I've found a very easy (and fun) way to obtain the used panties of strange women. All of the thrift store chains around town carry used women's underwear.I'll put on some synthetic fabric sweat shorts with no underwear and go shopping. A lil caffeine pill is probably bad for my k**neys and heart, but it sure gets me in the perv mood.The first thing I do when I enter the store is look to see what cashiers are working, and I begin to scope out the youngest and cutest one they have available....

3 years ago
  • 0
  • 14
  • 0

My Life Part 22 New Playmates

Katie leaned over and kissed me. "I know after last week you said you weren't sure about Mounika. But, maybe you should give her another chance." "I don't know, love. I don't want to experience that again." Katie handed me the prepaid, and I read a cryptic text from Mounika. "Apologies again for the misunderstanding. The room has been cleaned, the old tenant moved out and went back to get her mom some help. New tenants are here, you would like them." Reagan came out, all...

4 years ago
  • 0
  • 9
  • 0

Playmates

When I was in college I was a top star on the women tennis team. I never turn pro since I broke my foot while trying to ride my boyfriend's motorcycle. I nevertheless still loved the game and play when I can. Once out of school however my playing time was limited because of work, but Tom (a sale's rep in the office next door) and I would play three times a week. We found a small private club near our offices. We both liked it since there were few weekday players there. Most of the time we...

2 years ago
  • 0
  • 17
  • 0

Crystal ClearChapter 4 Separation New Careers and New Playmates

"Ellen will be your very special assistant. She'll be your script girl, check your makeup, help you go over your lines, and keep you on schedule." Crystal smiled at me to be sure I thought I'd be taken care of, "And, of course, she'll keep you warm in bed, and she's promised to remind you that I love you even though I'm six thousand miles away." She laughed at her innuendo abd then whispered, "And I've left instructions that she's supposed to fuck you senseless at least once a...

1 year ago
  • 0
  • 8
  • 0

Intruders make the best playmates

It was a dark night ,black clouds covered the moon . You head up to bed after a long day at work. You live alone in a large house ,it is a good neighbourhood but there have been a few break ins as of late. Once you are ready for bed you crash down hard onto the sheets and fall into a restless and disturbed slumber. A faint sound of footsteps wakes you , was it footsteps down stairs you can not be certain . You lay there still and quiet thoughts of the news reports about the break ins filling...

Fetish
2 years ago
  • 0
  • 23
  • 0

The Adventures of Madames new Playmate

Playmate was contacted early that morning by Madame X. Eager to please, she dropped everything she was doing and set out for Madame's house. The drive to her new Domme's place took about 30 minutes, giving her time to wonder if Madame was finally going to use her body or was this to be another getting to know you chats. It was a good thing that the afternoon was sunny and warm. Madame had instructed her to wear a light weight sun dress. Her full, C cup breasts were contained by the snug halter...

BDSM
3 years ago
  • 0
  • 19
  • 0

The Playmate

Hello Little Miss This is the second of my "Little Miss" stories. Poor old Nathan. Love, and stay safe KT Pel xxx The Playmate "But what on earth is it?" Nathan was positioned cross legged on the living rug, just as I had instructed. It was Christmas morning, though there was little spirit of the season in the air. "It's a doll," I replied coldly, as I warmed my hands on the mug of hot chocolate Nathan had made for me. "Yes, I can see that Tabitha. It's the same...

4 years ago
  • 0
  • 22
  • 0

Playmate

Playmate by shalimar I took a break from my household chores on that early May afternoon and watched Miriam, my five-year-old and her friend, Sarah, learn a clapping song from two of the older girls in the neighborhood. The older girls are very patient with my baby and her friend as they learn the actions, rhythm and words of the song, "Playmate." As I watched them it brought back memories of my own childhood, sitting and watching the girls in the neighborhood do that and other...

3 years ago
  • 0
  • 23
  • 0

Finding Pet A Playmate

It has been a month since Master gave me His collar, claiming me as His. It has been a wonderful month filled with pleasure and love. I couldn’t have wished for anything more. That was until Master asked me to move in with Him. I was speechless. Ecstatic would be an understatement. Of course I accepted and was moved in within a week. We quickly got into a routine. I am to be in position in front of the door when Master gets home from work. The position I’m supposed to be in is me naked on my...

1 year ago
  • 0
  • 11
  • 0

The Adventures of Madames new Playmate

Playmate was contacted early that morning by Madame X. Eager to please, she dropped everything she was doing and set out for Madame’s house. The drive to her new Domme’s place took about 30 minutes, giving her time to wonder if Madame was finally going to use her body or was this to be another getting to know you chats. It was a good thing that the afternoon was sunny and warm. Madame had instructed her to wear a light weight sun dress. Her full, C cup breasts were contained by the snug...

3 years ago
  • 0
  • 11
  • 0

Pussy Playmate

It was a cold and rainy night in April and she was tucked as far back into the deep doorway of the older, brick office building as she could get, trying to get out of the wind and rain. It was Friday night and the building was closed for the weekend. Despite people's desire to enjoy themselves on Friday night and forget the toils of the week, it was a bad night to look for customers. In reality, business hadn't been "good" in some time. Between the wet, miserable thirty five degree weather, and...

Group Sex
3 years ago
  • 0
  • 21
  • 0

A Drabble Playmate

A few weeks ago, there was exchange which appeared on the Hyperboard which resulted in someone making the suggestion that a rather well known story reviewer try her hand at writing a drabble. Having never attempted one myself, my interest was piqued. The next day I had five. What follows is one of them. Playmate A Drabble by Deane Christopher Standing on the porch, Suzie, the precious five year old who had just moved into the neighborhood, hopefully intoned, "Mrs. Johnson,...

3 years ago
  • 0
  • 18
  • 0

teachers playmate

Ms.Smith:Katrina can you stay after class for a while Katrina:Sure Ms Smith:Have you been studing for your finals? Katrina:Yes,but i still need a little help Ms Smith:Well, would you like me to help u as a tutor? Katrina:yes that would be great Ms Smith:Ok well,come to my house after school today around 6pm Katrina:ok,see you later ~Later 6 p.m.~ The doorbell rings Ms.Smith:JUST A MINUTE(opens the door)Hello Katrina Katrina:Hi Ms Smith:Well come on in Katrina:you have i nice...

2 years ago
  • 0
  • 16
  • 0

Piss and Spunk Playmate

Mildred was sixty two and had never shaved her pubic hair and was proud of the fact. So was her recently deceased husband, who loved her to show as much of it off in public as possible. Over the years they became outrageously kinky trying most things at least once. But the two things that really made her randy were showing off her very hairy fat cunt and squirting piss. When younger she used to wear the skimpiest bikinis and panties. Now being fatter she had her swimsuits specially made with...

2 years ago
  • 0
  • 13
  • 0

Daddy Finds A Playmate

“I love San Diego,” Daddy said to himself as he pulled his rental into the Manchester Grand Hyatt Hotel.  It was Wednesday afternoon and he would be attending a convention at the nearby Convention Center.  It was for suppliers to the medical industry and his company was heavy into supplying medical instruments and operation hardware.After parking the car in the check-in loop, he made his way to the concierge station. Walking up to the counter, he could not help but notice the nice ass that was...

Seduction
3 years ago
  • 0
  • 16
  • 0

Saras Surrender Part 10 Pleasure Pain and a Playmate

I knew what Sara would be feeling in her tits and clit – they would be getting hot, tingling, and perhaps even stinging from the ground-up ginger root paste I had painted on them. I reached into my pocket and pulled out the control to the egg vibrator I had placed in her cunt and pushed the first button, starting it on its lowest setting: a gentle, persistent hum.Sara jumped, startled, then stopped hiking, and awkwardly turned back to look at me. I smiled at her, then caught up and stopped next...

BDSM
4 years ago
  • 0
  • 9
  • 0

Vol 2 Mom definitely heard my mature playmate

I told Sue I would be right back. I grabbed a pair of shorts and went out into the hall. I didn't see any light coming from Mom's room. I started down the stairs quietly, and when I got to the first floor, I started to look around. I picked up the clothes that were strewn about the den. When I got close to the patio doors, I saw Mom sitting out by the pool. She had lit some candles and was reading in one of the deck loungers. I took all the clothes back up to the room with me. Sue knew that...

2 years ago
  • 0
  • 10
  • 0

Summertime BluesChapter 2

Early Saturday morning Molly and Jacob were dressed in grungy sweats and ready to move into their new apartment. Molly could still detect the faint aroma of Zoe's personal scent as she moved around the dining room packing the last few items in boxes. It kept a smile on her face and her thoughts away from Camden. Jacob had just headed out with a large box when their father, Justin, appeared looking uncomfortable. "You're getting an early start," he observed. "Hey Dad," Molly said as...

2 years ago
  • 0
  • 17
  • 0

Seductive Swap Story 8211 Part I

This is real story of a two friends where we exchanged our wife with each other for bit lengthier live in relationship. Usually in swinging/exchanging wife with others, generally people will exchange partner for just a fucking session in just a week end visit or night visit to one of the couple’s home. In our case, to make our life spicy and have more thrill and adventure, we have decided to do this for bit longer period of time, where my wife will be with my friend for 2 months and where as...

3 years ago
  • 0
  • 11
  • 0

First Group Sex Encounter Of Radhika

Hi my name is Radhika Thakkar. This is my first story in ISS. I read stories on ISS. So finally i decided to write my story also. This was my first group experience. It occured with me in the conference room. Firstly my figure is 32 28 30. It was a regular day. I went to the office. On that day we didnt had much work to be done in the office. So we all were just sitting and enjoying in the office. That was a very unusal day because we generally had much work to do rather on that day we were...

2 years ago
  • 0
  • 15
  • 0

Jennifers Tale Part V

Previously: Uncle Jamie was astounded when he stumbled upon Jennifer’s elaborate masturbation scenario. Now: Jennifer is astounded by his pre-conceived response. But the story will make much more sense if you read parts I – IV first. Conclusion. I wasn’t sure if Uncle Jamie had intentionally left me with my finger still inside me, but I wasted no time before starting to experiment with the sensation. I was just beginning to believe that this could be very pleasant when I heard him returning...

4 years ago
  • 0
  • 13
  • 0

Submissive Cuckold At My Gym

I am 30 something man. Been reading stories on ISS for a while. So I thought after making a little effort I should also share a experience that happened with me. Lets get started then. I live in Bangalore and work for a large IT company. Our office has a gym facility on campus. Now I am not a heavy muscular person. I go to gym to stay fit and in shape. I have been going to gym in my college days as well. But after I started working it was not possible to go to gym regularly. When I joined this...

1 year ago
  • 0
  • 11
  • 0

The FavorChapter 39 The Cheerleader

Rachel came into my room late one afternoon and handed me a jewel box. "What is this?" I asked. "It's a present for you," she said as she walked out. "It's long, but try and watch it tonight if you can, and watch it alone." I shrugged, but finished what I was doing so that I could watch it. I sat down and popped it in my DVD player. There were no menus; the video just started. A gorgeous blonde appeared on the screen, and I recognized her. It was Brittany Douglas from my school....

3 years ago
  • 0
  • 12
  • 0

Wild College GirlsChapter 2 The Horse Ranch

The following day we all gradually awoke to a blissful morning, the smell of sex still in the air, probably emanating from their hot stuffed pussies. I had awoken a few times during the night to some squirming and moaning. Both girls were having erotic dreams throughout the night, stimulated by the huge intruders. Excited like two small girls on Christmas, both girls wanted me to take the temperature of their beer cans like I said. I complied and retrieved an electronic thermometer and a...

1 year ago
  • 0
  • 7
  • 0

MyFriendsHotMom Ashton Blake 23149

Ashton Blake is sick and tired of her son’s friend Peter picking on him. All he ever does is dig on him because he doesn’t go to the gym, calling him weak all the time. Well, Ashton’s had it! When Peter comes over blasting on her son before he even gets in the house, she tells him she wants to see how tough he is, and challenges him to an arm-wrestling match! Peter laughs and laughs and laughs…until Ashton takes him over the top! Completely emasculated, Peter feels like he can’t please a...

xmoviesforyou
1 year ago
  • 0
  • 9
  • 0

You Can Ring My Bell

Rachel Kent stood at the glass counter just to the right of the restaurant’s vestibule. Without conscious effort, the twenty-two year old redhead smiled warmly at the lunchtime customers as they came in, welcoming them to D’Martini’s. It was a greeting she had perfected long ago, which was good, because putting on a happy face was the furthest thing from her mind right now. Instead, her thoughts dwelled on the question of how had she had gotten herself into the mess she was in. No, that wasn’t...

2 years ago
  • 0
  • 18
  • 0

Survival

A Ford F-150 pick-up truck drove down a lonely stretch of road flanked by nothing but trees. I was relaxing in the back seat looking out the window, thinking about how my parents decided that we would be spending time at the family cabin. The drive to the cabin from my house is two days drive, far away enough that you don't have to worry about people disturbing your time with your family. Closest people are at least a ten minutes walk away where theres another cabin and midway point of the town...

3 years ago
  • 0
  • 10
  • 0

Kese Main Bani Cal Girl Part 8211 2

Helo frnds me sumanpreet kaur ek bar fr hajir hu apni agge ki story leke apne meri pehli story kese main bani cal grl ko bhut pyar diya apke bhut sare mail aye aur me ek bar fr bta du ki ye meri real story hai ab me age ki story par ati hu .   Usdin jab me hostel phuchi to mera bhut bura hal tha me chal b nahi pa rahi thi me bhut muskil se apne room me phuchi room me ja k mene nahaya aur fr so gayi sham ko musakan ka castmr k liye fon aya par mera bura hal tha to mene mna kar diya agle din fr...

1 year ago
  • 0
  • 10
  • 0

The Student Teacher BluesChapter 6

Bob was weeding a bed of Hydrangeas, which wasn't going well because he kept thinking of Cecelia and wasn't paying attention to what were weeds and what were Hydrangeas. It disgusted him a bit that he couldn't control himself. She was just a woman, after all, like any other woman, right? And, while he hadn't exactly sworn off women, like she seemed to have sworn off men... That distracted him. It was almost criminal that she had sworn off men. That no man got to bask in her beauty ......

1 year ago
  • 0
  • 7
  • 0

All mine part 1

“Eric.!? Eric.!? Eric? Where are you?” I could hear my stepdaughter, Sabrina, calling for me as she walked down the hall. I was laying in bed recovering from my hangover. One of my buddies from work had invited me out for drinks last night. I figured what the hell. Might as well. My wife had to work the next day and I would be at home alone all day to recover. We ended up going to a bar that I would frequently go to before. Becky was work. Becky is this hot beautiful bartender. She is very...

1 year ago
  • 0
  • 12
  • 0

The Ladies Dinner

The first thing Sarah noticed was how thin Jennifer was; her wide red belt tightly buckled around her waist. Her eyes then made their way up from her belt to her firm breasts, and then to her face. It was the face that stopped her cold. Chiseled, the sort of features that only result from hours in the gym. Finally she reached her eyes. They were deep and brown and would be easy to get lost in. She stared into them for several seconds oblivious to any idea that her gaze was being returned. Then...

Lesbian
3 years ago
  • 0
  • 6
  • 0

Strange RelationshipsChapter 16 Status Reports and the Climaxes of the Astronomy Club Meeting

Nate and Nora met Draper and Tenisha at the movie. The flick was a futuristic action-adventure yarn that pointed up the differences between male and female perception of such things; the guys were into it, their enthusiasm barely dampened by the pretense that it wasn't important for the girls' benefit, while the girls endured the spectacular gratuitous violence to make the boys happy, both vowing to subject their significant other to a more romantic feature in the near future. At a slow...

1 year ago
  • 0
  • 18
  • 0

The dancers

The screaming, yelling, and clapping of two hundred crazed women, combined with the relentless beat of a hard rock CD, never failed to get Rolando whipped into a frenzy before he hit the stage! Dressed in leather chaps, a g-string, cowboy boots and a ten gallon hat, he looked anything like an all American cowboy, but with a body that appeared to be chiseled from granite, Rolando was one of twenty dancers in the all male revue at the Hotsy Totsy Club. Seven nights a week the place was jumping to...

Voyeur
3 years ago
  • 0
  • 12
  • 0

April

Rob stood at the door, fidgeting and waiting for April to answer his knock. He could hear her approach, so he straightened his stance and put a pleasant smile on his face, hoping she wouldn't notice how nervous he was. After all, he was simply there to have dinner as a friend, right?Rob and April met each other two years earlier when they were in training for a tech support job at a major insurance company. Rob immediately felt a connection with April, and they struck up a friendship. All...

2 years ago
  • 0
  • 14
  • 0

My good friends wife

I was going to Japan that night but it is what happened during the day that I will never forget. She was my best friend's wife. Slim, 5'7" tall, small breasts with really long nipples, great arse which you would die for , long legs and long black hair which when lose covered her bums. She used to tease me and I her... I have always noticed that my cock and her nipples gave both of us away . Mine would form a tent in my track suit and her nipples would project even if she was wearing a bra......

Voyeur
3 years ago
  • 0
  • 35
  • 0

Vacation

Rose and Owen Harper saved up all year for their big family vacation. This year, they'd be taking their four children - 20-year-old Dean, 18-year-old Finn, and 15-year-old twins Lucy and Lily - to Florida. They were thrilled at the idea of taking the kids to the central Florida theme parks, spending time at the beach, and, most importantly, having some romantic time alone together while they were there. It was Rose's suggestion to hire a babysitter to come along for the trip. It made sense;...

2 years ago
  • 0
  • 10
  • 0

Construction

CONSTRUCTION Walking around this old two story house looking at all the repairs it needs is very depressing I know that half the work I can do myself but I can not do it all. I need to find a Handy man a respectable one . Looking in the phone book was no help too many of them I decided to drive around and look for places under construction I might be able to get one of the workers to come and give me a bid on the heavy work. I saw a sign that said Paul Longhorn Construction and slowed down they...

3 years ago
  • 0
  • 10
  • 0

One Last Job With VengeanceChapter 19

Getting a seven and a half tonner will not be a problem but this had to be the exact same model. A Mercedes Benz Atego would be another matter. These trucks are the workhorse of delivery firms. Once a firm gets one, they don't usually get rid of it until they have run it into the ground or it's so battered up it's not good for the firms' image. Not only that, it had to be white and in a good condition. There would be no chance of fooling anyone if the crew rolled up in a truck that...

4 years ago
  • 0
  • 5
  • 0

The school fair

It's the annual school fair. Every year the school sets up a variety of different attractions to raise money and have some fun. Normally you wouldn't come but for some reason, this year attendance is mandatory. You're in the school courtyard, where the main attractions are supposed to be, but so far it seems that not everything has been set up. There's what looks like a wrestling ring being put together in the center of the ground and various side attractions. One booth that seems to have built...

Fetish
2 years ago
  • 0
  • 13
  • 0

Twins

TWINS by Roy Del Frink A worried-looking John Spalding walked down the snow-coated streets of the big city one mid-December evening. He just couldn't stop thinking about his twin sister Joan. They did everything together while growing up. They even looked somewhat alike: long, flowing brown hair with blue eyes, both tall, and both skinny as a rail. John was now an accountant, while Joan was a top-notch real-estate agent. But John became unhappy when puberty brought the...

3 years ago
  • 0
  • 11
  • 0

Being Troy Jennifer

Being Troy / Jennifer - "Jennifer- come on," Mack was pulling at his arm, urging him at a whisper to move, "you have to get up- we need to get out of here." "What happened?" Troy asked trying to raise his hands, but he felt all wrong, exhausted and weird all at the same time. "I don't know; I just woke up. There is something in the house, we have to get out of here," he was pulling at him again. Troy rolled onto his side, feeling very strange and off balance and sore like he had...

1 year ago
  • 0
  • 9
  • 0

Craig HillChapter 59

The next few weeks passed uneventfully. Victoria got her fears under control but there was no change in either of their emotions. Their love pervaded their beings and percolated into the lives of everyone else who was close to them. Mark rang the Saddle Club. "Jim?" "Yes." "Mark Bowers." "Hello, Mark. I was going to talk to you. You've just about used up your guest quota." "I'm sure I have and I'll pay whatever I have to." "Nothing yet but you've only got one more guest...

2 years ago
  • 0
  • 9
  • 0

Loosening Up Book 10 Road Trip EastChapter 27 Louisiana Arkansas Missouri

Dave’s departure from the sorority house at LSU in Baton Rouge was delayed another day for multiple reasons – weather, but really the desire he felt to love the four new women in his life. The weather turned idea eventually. Traffic was light. The motorcycle was loaded and ready to roll. But four co-eds pleaded for goodbye lovemaking with him: Phoenix, Devon, Bonnie, and Mallory. Dave spent quality time with each of the young women, naked and embedded deep inside them as they also romanced...

3 years ago
  • 0
  • 15
  • 0

Corporate Takeover Part 3

The last few days since my trip to Boston were difficult. I thought of her often, actually maybe I should scratch that as I thought of her all the time. She was in my head. Kind of like waking up with a tune in your head and you continue to keep replaying it over and over throughout the day. Although I would say that this was much more pleasant. It was Monday morning and I was beat, what a way to start the workweek. I hadn’t slept well for days.  I would often lie awake at...

Straight Sex
3 years ago
  • 0
  • 11
  • 0

Crossdressed in public

hi ppl i m rohit….i m 16 yrs old and i live in delhi…i love to crossdress when i m all alone. i hv been doing this sicne i was 13 yrs old.i used to wear my mom’s clothes n gaze myself at mirror. though i was not a gay but i wanted to try gay sex once by turning to a women. it was in d month of june when my parents had to go to noida for some work and i was left all alone at home for a week. one evening i thought i should try crossdressing and go out to enjoy in public n tease some ppl.i...

Gay Male
2 years ago
  • 0
  • 12
  • 0

The Sexy Basketball Girl

The Sexy Basketball Girl I was pleased to see that a girl my age moved in across the street. Sixteen is a difficult age to be, you’re not really a kid anymore and you’re not quite an adult either. My hormones were raging and I jerked off a lot. I saw her bouncing a basketball on her sidewalk and went right over. I invited her to use my basketball hoop on our garage. I told her that I play in the paved driveway all the time. She introduced herself as Sam and said that it was short...

1 year ago
  • 0
  • 17
  • 0

IIT Preparation Kota Mein Amisha Ki Chudai

Hii, this is Daksh Kashyap, graduated from IIT Bombay. Please read my last story jisme maine bataya ki kaise maine mere papa ki friend ki beti Prachi ki chut aur gand mari. Ye kahani bhi Kota mein mere IIT preparation ki hi hai. Jab main Kota gaya tha to mera admission Allen ke 7th batch mein hua tha. Usi batch mein ek ladki thi-Amisha, jo bahut hi sunder thi. Waise to suit-salwar dress tha Allen ka, par usme bhi woh khatarnak bomb lagti thi. Uski height 5’6″ tha aur zero figure size. Meri...

3 years ago
  • 0
  • 8
  • 0

A weekend alone

My first story….completely true…and a pivotal moment in my life. The first part covers how I started enjoying kissing other boys. The second part tells how I lost my bi cherry to another guy and became actively and happily bi sexual. Part one As I boy growing up in a small English village in the 1960’s, sex wasn’t a subject that got talked about in an educational or overt way. The very conservative nature of our society at the time meant that any useful education was gained either from...

2 years ago
  • 0
  • 6
  • 0

Drive For ExcellenceChapter 7

We loaded our gear after a breakfast on Sunday morning. Will and I loaded up our weights first while Andy carried our bags out to Will's car. Ed brought his things over while we were trying to load everything. The car was full last year when it was only Will, Ed and me. This year we had to squeeze Andy and his stuff in too. We filled the trunk with the heavy stuff. Ed and Andy climbed in the back seats. Will and I gave them two duffle bags to hold on their laps. The last duffle bag went in...

3 years ago
  • 0
  • 14
  • 0

Cat and Mouse A Cresswell Industries Story Pts 3 and 4

III: Baiting the Hook The skies were dark blue when Rita's Porsche pulled up in front of Timmy's house. He was terribly worried that his mom was going to be out in front of the door waiting for him with an angry look on her face, but there was no one there. The lights inside the house, however, were still on. Rita was nice enough to undo the hairstyle she had given him, restoring his fuller hair to its original appearance, and she allowed him to wash off the makeup she had...

1 year ago
  • 0
  • 19
  • 0

Chachi8217s Milk Makes Me Fuck Her 8211 Part II

Please read the first part Chachi’s Milk makes me Fuck her and then come to this one and after returning from the vacation my father called me and my whole family abroad. We stayed there for 4 years and I finished my 12th over there before coming back to India for graduation in these four years. I had become much more mature and grown up by body and mind. I never really had a girlfriend except from a girl with who I just had some phone sex apart from that I had never been physically intimate...

Incest
2 years ago
  • 0
  • 9
  • 0

Gangbang Adventure

When I met my partner we had only been together a month when he asked me how many cocks I had fucked?Two and he was the second.Why?I asked cautiously.Well,he said it gets him off knowing that other guys have fucked me and if I was in the right situation would I be willing to give it a try.I said maybe but the guys would have to have hot bodies,good looking and hung like him.He smiled and we fucked like rabbits all night talking about it.I guessit was on the cards from that day on because 6...

1 year ago
  • 0
  • 6
  • 0

Ghost of Statum ShoresChapter 2

It was eight o'clock p.m. in the town of, Abbeville. In the middle of town, stands a huge white building with twirled pillars, and woodcraft that is pleasant to the eye. The bar was just a few short walks from the town's courthouse. Jean Leon was the owner of the establishment. He arrived in Abbeville just a few short months ago setting up his bar to make money, and found Abbeville very rewarding. He hired a few ladies that lived nearby, most were single. Work was hard for woman to find in...

4 years ago
  • 0
  • 16
  • 0

My favorite Babysitter

The babysitter used to cover what we called our split, the time my wife would go to work until the time I got home from work. It usually was no more than a couple of hours. I never really got a chance to spend time with the babysitter because as soon as I showed up she needed to head out the door to go to her college class. She was 18 years old and the neighbor’s daughter, it was a really convenient situation for all of us. She was definitely a site to see, about 5’6 with a slender build and...

2 years ago
  • 0
  • 6
  • 0

Sweet Peach

The graduation party was in full swing as I watched her dancing with her friends. Already eighteen and now finished high school she had a whole life of adventure waiting. Watching her and her friends was becoming titillating, almost erotic, their young bodies flashing legs and cleavage. Tight little asses in mini skirts, curve-hugging low-cut dresses, high heels, and stockings -all showcasing nubile young bodies as they moved to the music. My cock found it very interesting.When the music slowed...

Incest

Porn Trends