Adventures In Babysitting free porn video

Adventures in Babysitting By: Malissa and Gang Tommy Moore, was a bit of a loner all his life, no close friends other than the girls he went to school with. But he never dated any of them. Now as a senior in High School he was on the honor roll list. His mother was a bit concerned though, he seemed to not have any life outside of school. Of course she had her hopes, as he would often go to Laura's house for the girls study group, three or four girls he went to school with who needed his help with math. And then there was the occasional group outing to watch movies with those same girls. Laura lived next door and was the only one in the neighborhood close to Tommy's own age. The rest had already gone off to college already or were just beginning grade school. Evelin Moore had watched from the sidelines hoping the two might become an item, it would give her the opportunity to take a young girl to the Mother and Daughter events held in town every year, since Laura's mother had abandoned her with her father and disappeared. Laura's father Martin Styles was one of the most sought after bachelors in town, and Evelin was always flaunting herself in skimpy outfits trying to compete for his attention. But he never seemed to date anyone either. Tonight, as Evelin retrieved the mail from the box she found the usual invitation sent out by mass mail to every household in town. The annual Mother Daughter Summer Picnic was coming up at the end of the month, just in time for the end of school. Entering the house she heard the voices from upstairs in Tommy's room. Laura was up there with Tommy, her heart skipped a beat as her ears strained to listen. "No not like that silly, look I'll show you." Laura's voice. "Let her do it for herself, it's the only way she's going to learn," Mindy parker's voice said. Evelin's heart dropped, they were only studying if Mindy and another girl were here also. Deciding to see if they wanted a snack she made her way up the stairs to his room. The door as usual was partially open, and she stepped inside. "Tommy, you kids want a snack to," her question stopping as she took in the scene in front of her. Three teenage girls lay in the middle of her sons' bedroom floor, one she'd never seen before in just pantys and bra, doing makeup with a shared mirror. "Oh shit," screeched the half-naked one, as she scrambled to dash to her sons' private bathroom. "Mrs Moore we can explain," Laura bit her lip in fear. "I certainly hope so, where's Tommy?" she was looking around the room not seeing him. She realized she'd not been in his room since he started high school, it seemed more girly than boyish. The two girls looked at each other before answering. "In the bathroom Mrs Moore." "What, why was that girl half naked in my sons' room?" Evelin started toward the bathroom. "Ma'am, please don't be mad at him," Mindy said. "Yeah he's afraid you won't understand with all the pushing you've been doing trying to get him to start dating," added Laura. "Oh my god, the three of you and my son are," just then the door opened a crack and Evelin's head turned toward it. "Sorry Tammy," Laura said. "Tammy?" Evelin's shocked look was misinterpreted. Now both teen girls stood between her and her son. "You might as well come on out Tammy, let your mother get to know you. If she gets mad you still have me and Mindy," Laura said supportively. "Mom, Momma I, I can explain," Tommy/Tammy said stepping fully out of the tiny bathroom, now wearing a pleated mini skirt around her waist. Now Evelin stood taking in this beautiful young girl cowering between her son's closest friends. This couldn't be her son, she was too pretty. Her eyes fell to the two small mounds of real flesh pushed up on display by the half cup pushup bra. The hair was the same as her son's, the eyes, even his soft voice was the same. "Momma, please say something. Yell at me, tell me how horrible I am, something," Tammy cried, the tears rolling slowly down her cheeks. "Tammy? Is, is this really you?" Evelin asked her son. "I mean the girls aren't forcing you to do this are they?" Tammy snuffed back her snot before it could run and wiped at her eyes further smearing the eye liner under her eyes. "I'm sorry Momma please try to understand. Please don't get mad at them, they're just helping me." "Helping you?" Evelin reached out her hand slowly feeling of the now quivering flesh supported by the lacey bra. "How long have they been helping you? This takes more than just a day to develop." She tried to keep her voice calm, her tone understanding. "Since seventh grade Ma'am," answered Laura. "Seventh grade? But why didn't you say anything Tom, Tammy?" she quickly corrected herself. "You, you wanted me to date girls. You kept pushing for it, and I didn't think you would understand." Tammy said, the tears still rolling slowly down her cheeks. The phone ringing interrupted them, and she answered it. "Hello?" "Evelin, is Laura there?" asked Martin Styles, his voice sounding a bit strange. Evelin handed the phone to her, "It's your Daddy." "Daddy," Laura said then after a few seconds replied, "Yes but I think it may be working out." She listened again before answering. "Ok Daddy I'll tell her, thanks." She hung up the phone. "My Daddy's coming over." Evelin sat down on her son's bed still staring at him/her. "I can't believe this has been going on all this time and you never said anything," she finally said reaching out to pull Tammy in front of her. She reached over pulling a Kleenex from the box beside the bed and began dabbing at the young girls eyes, wiping away the ruined makeup. "We have a lot to talk about," there was a knock at the front door. Standing up she kissed her Son, now daughter's cheek, "Fix your makeup and finish dressing. I'm going to talk to Martin." When she opened the door Evelin saw the worried look on her neighbors face as she let him in. "Evelin, is everything OK? I mean, she's not hurt or anything?" "Martin, you knew about Tammy? I mean, you didn't ever say anything?" she led him toward the Den and the liquor cabinet. When she started to pour herself a glass full of bourbon he stopped her. "Evelin, this is not the time to get drunk, I know your mind needs to relax a bit to process everything." He put the bourbon back and took out a bottle of wine from the tiny refrigerator compartment. "Just enough to help you relax," he promised. "How long have you known about Tommy, I mean Tammy?" "Four years," he answered honestly. I thought it was just a phase at first. You know him letting the girls dress him up. They even said it helped them relax and study better." "But, I mean how could I miss everything right in front of me? She has breasts, not fakes but real breasts Martin." "You need to talk with Mindy's mother. She can explain those better than I can," Martin told her. "Sarah Parker, she's my Gynecologist. What would she have to do with this?" "Momma," Tammy came into the den followed by her two closest friends. "Dr Parker has been helping me. I went to her because I was scared to talk to you, and Mr Styles keeps telling me I need to tell you about everything." Evelin pulled her into a tight hug. "I'm right here Sweetie. Please tell me what is going on. If you want to be Tammy that's fine, I'll do my best to understand, as long as you're happy." They were soon joined by Dr Parker who smiled at Tammy as she saw her standing there all dressed up. "Evelin, Martin, Girls, I hope everything is ok here." Sarah Parker stated. "Sarah, why didn't you tell me about this?" "Because of Dr/Patient confidentiality, surely you understand that." "Have you been giving him/her Hormones?" "No I haven't. She refuses to tell me where she's been getting them. So I've been doing my best to monitor and help her not be so reckless. She needs to be on an actual prescription if she's going to do this. But she didn't want you finding out through your insurance." Explained Sarah. "Is it dangerous, I mean without a prescription?" "It's very dangerous, there is no way to assure the purity or actual dosages she's getting. So far she's been lucky and everything seems to be what it claims." Turning to Tommy, Evelin said, "No more hiding young lady. And no more un-prescribed Hormones. I do not want to lose you, no matter if you're my Son or Daughter, is that clear?" "Yes Momma," Tammy lowered her eyes to the floor. "Are you mad at me?" "For taking Medications without a prescription, yes. For wanting to be my daughter, No. I just wish you had told me when I kept asking you what was wrong." "Momma you kept asking why I wasn't dating girls. Like I was supposed to be into going out chasing skirts." Tammy blushed. "Instead of wanting my skirt chased." "You never said anything, you never wore anything as pretty as this around me. And I know you always left here dressed up as a boy whenever you went out with the girls to the movies and stuff." Evelin began. "Momma, I've had all that 'Tommy stuff' for years," blushed Tammy. "I've been dreading the day you actually opened my closet or my dresser drawers." "Or got the letters from school before she got home," added Laura. "Why on earth would she dread that? She's an honor student?" Tammy dropped her eyes as she opened a drawer of the desk beside her mother. She took out a letter from the school. Dear Mrs Moore, While we can understand your support of your son Tommy wishing to become a girl, and have made every accommodation to include allowing him/her to attend classes dressed up in the clothes and use the name of his/her preference. We cannot in good standing issue a graduation certificate at the end of school without a letter of intent specifying the correct name to be placed on the diploma. If we do not have a letter prior to graduation, Tammy will not be allowed to graduate with her class. Instead she will have to attend that ceremony as Tommy. Please respond in all haste so we may clear this matter to the School Boards satisfaction. Sincerely, Robert Frost Superintendent "When did this come? What does he mean by allowing you to attend classes as Tammy?" Evelin was stunned. Now she looked in the desk drawer that had always been Tommy's for doing his homework. The drawer was filled with neatly filed folders containing school correspondences from the last four years in regards to Tommy/Tammy. Shaking her head she finally looked up. "This is way in the out of bounds area, hiding mail from school, from me. Were you really that afraid I wouldn't understand?" "Yes Momma," she answered meekly. "I know you can't have bought very much with what I give you for an allowance or at the beginning of the year for school clothes." Evelin was hoping she wasn't shoplifting clothing. "No Momma I Babysit to earn money to buy things. Usually Laura or Mindy go with me to the Mall." "Wait, back up there, You Babysit?" "Yes Ma'am, she's really good at it too. She has regular customers that just adore her way with kids," Laura said. "Ok so I'm ready to admit to being blind about all this. But you are going to get that letter young lady," the smile crept lovingly over her face. "And as punishment you are going to go to this with me," she held out the invitation to the Mother/Daughter Picnic. "I, Momma are you sure? I mean I don't have anything that fancy. I'll have to go shopping, and to the Salon to get my hair done." Tammy stopped suddenly staring at her Mother who was grinning. Evelin knew it was going to take some time to get used to having a teenage daughter. But she was determined to make up for the lost time. "Grab your Purse young Lady, we need to start looking for outfits if we're going to match." "Uhhh, Momma, I kind of have a job tonight. I already promised to sit for Mr Anderson." Tammy said. "It's another Fifty Bucks I can put towards my dress for the Picnic though." "Fifty Dollars? How long are you going to be sitting there?" Evelin was suspicious, that was twice what she remembered ever being charged. "It pays Ten Dollars an hour Momma, that's the going rate these days. And if I do a good job and have Billy in bed asleep by the time he gets home I usually get a nice tip." "Ok we'll go tomorrow, or are you tied up with something?" "No Momma, I don't have another job until Sunday afternoon. Then I have to watch Grace Fenton while her Parents go to a Wedding." "Oh," Evelin didn't know the Fenton's. She'd heard of them, just never met them. "Evelin," interrupted Martin. "I've checked on them, they really are a nice couple. Tom is a Sheriff's Deputy. And Diane works for the DA's office." "Oh, ok. Maybe we should invite them over sometime, how old is their daughter?" "Momma, Grace is only eight, but she really is sweet." Tammy added convincing her Mother that it was ok. "How about I take you to dinner tonight and we can talk more about Tammy," offered Martin. "Do any of them know about Tammy, I mean you know, her not being fully a girl?" "Mr Anderson knows Momma, he recognized me the first time. But he understands and says he's always thought I was more girl than boy," Tammy blushed. "Ok then, you go get ready for work, and I'll go get ready for dinner," directed Evelyn. "Sarah, Would you and Mindy care to join us?" offered Martin. "Nothing too fancy just Sizzlin Sirloin." "Of course, and that will let me have a nice talk with Evelyn about Tammy." Soon it was just Tammy and Evelyn in the house. "Momma, do you think this skirt goes with this top?" Tammy held up a three tiered ruffled flower print skirt, and sheer white cotton top with full lace sleeves. "Yes but if you wear that you'll have to change your bra. You don't want a dark colored bra under a light top, it'll show." "Like this one Momma?" she help up a white lace bra and panty set. "Those would definitely go good with that outfit. But aren't you afraid it won't hide things enough?" she asked her new daughter. With a giggle Tammy held out a nude colored Gaff. "I'll be wearing this under my pantys Momma. It's specially designed to hide such things." "It looks like a thong," Evelyn pointed out. "It is Momma, I got it online from a place that makes things just for girls like me." After slipping it on, her mother watching everything wanting to know as much as possible about her new daughter, Tammy modeled it for her turning this way and that. "See, it works really well." "Yes it does but isn't it just a bit uncomfortable?" "No Momma, not if I tuck things right." She knew her Mother had watched wide eyed as she tucked her unwanted parts into her crotch and snugged the gaff into place. She saw tears welling in her Momma's eyes. "Oh Baby, I wish I'd known about this sooner," she finally said. "Maybe I can get them to change the order?" "Momma what are you talking about?" "Your graduation present," she said. "I kind of ordered it for my son. But now I need it for my daughter but it won't be the right color." "Momma what did you get me? I'm sure whatever it is it will be perfect." Evelyn was not about to give away the surprise, even if she now doubted her wisdom in ordering it. As they headed for the door she asked, "Are you going to use the car tonight?" "Yes Momma," she giggled. "Are you sure? Have you ever driven a stick shift in heels, it can be kind of tricky." Warned Evelyn. "Momma, I always drive in heels. Well I mean once I leave the house anyway. I have a pair stashed under the seat," now she blushed and her Momma kissed her cheek. Martin picked Evelyn up for dinner as Tammy left to babysit for Mr Anderson. Getting out of the car in the driveway she hurried to the door because she was running a bit late. The door opened as she was about to knock. "Tammy, I'm so glad you're here. Billy has been asking if you were coming since five o'clock. I guess he really likes you, I can't think of another sitter he's liked more." "Oh finally the sitter's here," the young woman Tammy had never seen before announced. "Well I suppose we better run along before we miss our reservations." "Sorry, I'm not that late," she started to say. "You're getting paid to be here on time," the woman flipped her hair as she hurried past, out the door. "Sorry Tammy, I really thought she was nicer than this. Billy can't stand her." he apologized. "It's ok Mr Anderson, you deserve to get laid. At least you're not married to her, so you still have some control. You just have fun, I know all the numbers if I need anything." "Steven, come on we'll lose our reservations." After they left Tammy and Billy played a learning game on the computer then watched Shark Tale, and Finding Nemo. By the end of Nemo he was fast asleep, and she carried him to his room and put him to bed. She'd just returned to the living room when someone knocked on the door. She peeped through the peephole seeing Steven Anderson. "Sorry they took my keys at the bar," he explained. "My date didn't go well." "No need to explain sir, she was a total bitch. You deserve better, someone nicer who likes kids." She tried to sooth his injured ego. "Just let me check on Billy one more time." she led the way down the hall where they looked in on the sleeping boy. She bent over tucking the covers in again when she heard his groan and felt his hand caress her ass. "Damn, I'm sorry Tammy. I, I shouldn't have done that. It's just that you're so, so beautiful, and sexy." She noticed his hard cock standing out in his dress slacks. She'd never been around him when he was drunk before, and his inebriated state seemed to be lowering his inhibitions about his babysitter. "Well I better pay you so you can get home, I'm sure your Mom is worried about you." As they retreated back to the living room his hand came up to her bottom to guide her along. She felt shocked to realize it turned her on to have an older man coming on to her. As he searched his wallet for the money she kept looking at his twitching cock. She knew he was horny, and that she was the current object of his desire. He came out with a hundred dollar bill. "Sorry this is all I have. But then maybe the extra will make up for my bad manners. The way I've been acting toward you. I just can't help it, it's true you know. You are a cream dream, and I don't understand why you haven't got a boyfriend yet. Damn there I go again. You better run along before I grope you again." Her eyes kept being drawn to his throbbing cock. "Sorry," he said as he picked up a throw pillow to cover himself. She didn't know why she just stepped forward her hand reaching out to pull the pillow away. Biting her lip first she said, "Umm, since it's all hard because of me maybe I should ummm," she let her fingers caress its length. "Do something to help you sleep better." "Tammy, I'm not sure you should be doing that," he breathed in a sigh of desire. "I hope I can do this right, I've never done anything like this before," she sank to her knees in front of him. Her fingers busy working the zipper and his belt at the same time. Of course she'd seen it done in the tube videos online but this was different. This was real, her heart pounded racing with excitement. She was about so give her first ever blowjob. She stroked its length lovingly as she drew nearer to the head. Her lips pursed as she kissed it, a soft giggle escaping her as she inhaled the scent of new sweat, not a stinky scent but one that invited arousal. Just like eating an ice cream cone, she told herself the same thing Laura and Mandy had told her about their own experiences. Starting with soft full lip nibbles, just a hint of tongue, she slowly worked up her courage to slide her lips around the head letting them close behind the ridge of the crown. Her tongue swirling slowly around as her fingers squeezed moving up toward her mouth, pushing the clear precum fluids out onto her tongue. She let out a little slurp as she tried not to giggle. Closing her eyes she tried to imagine she was one of the girls in the videos, her head bobbing back and forth as she sucked, her tongue busy smearing her spit over the length of the shaft as his hand closed around the base of her ponytail. "Oh god girl don't stop, don't stop." He panted. "So fucking pretty with my cock in your mouth." His hips began gently rocking back and forth and she held still letting him fuck her mouth, his cock pushing deeper and deeper until she was gagging on it. Her saliva and mucus flowing threatening to drown her as she drooled over his cock. Her own cock twitching in her gaff trying to straighten out, break free as she lost herself in the act. Her desire to taste his cum spurring her on. "Unnnn, ooohhhhhhh fuuuckkkkkk," he groaned as his cock pushed in deeper, the sounds of her gagging spurring him on. "I'm, I'm gonna cummmmm, ooohhhhhhh fuckkkkkkkkk," he began blasting his hot cum into her throat. She pulled back catching the next gush in her mouth before it slipped free and blasted over her face. Jet after hot jet of cum blasted out splashing over her face as she pressed it to her cheeks rubbing it in. her own cock twitching squirting into her pantys, splashing against her quivering anus making her cum even harder. When they both calmed down he looked down at her cum covered face. "Oh god I'm sorry Tammy, I, I shouldn't have done that." he apologized. Wiping up some on her finger, still looking up into his eyes she stuck her finger in her mouth and slurped it clean with a giggle. "I'm not sorry Mr Anderson." She stood up, and he kissed her lips. "You are just so pretty, I always fantasize about you doing just that every time you babysit for me," he admitted. With a giggle she kissed him back before scooping more of his cum into her mouth with her fingers. She winked and said, "Just think of this as me earning that tip you just gave me." "Shit, no please don't cheapen yourself like that. You're too sweet to sell yourself to horny old men." She raised up and kissed him again. "And you're too sweet to have to go to bed and jack off thinking about your babysitter. So it's mutual satisfaction, ok?" "Ok, if you're sure, but please can we keep," he began. "Just between us. I promise." She picked up her purse off the couch. "Same time next week?" she asked. "I think I want to try that again, practice makes perfect you know." He handed her another twenty. "That's to hold Friday open for me. But what are you going to tell your mother? I mean about the hundred?" Giggling she said, "The truth, you didn't have anything else so you paid me in advance for next week." He patted her bottom as she stepped through the door, his hand pressing her cum soaked pantys to her bottom. He watched as always until she was safely in her car and starting down the street. God I can't believe I just banged my babysitter, he told himself. Or that she hinted she wants a rematch. He looked up at the picture of his deceased wife, "Forgive me Julie, but she's just so damn sexy." Letting her hair down from the ponytail she quickly brushed it out getting rid of the evidence that had splashed into it. All the way home she kept giggling to herself about how things had worked out. She stopped and bought a soda to wash out her mouth. No sense in greeting her mother with cum breath. As an afterthought she spritzed on a bit more perfume to hide any other evidence she might have overlooked. She'd used the stop at the convenience store to break the hundred dollar bill so now she wouldn't have to explain it to her mother. They talked a bit and her mother told her she wanted to get an early start in the morning, they had four years of missed shopping trips to make up for. Lying in bed she thought about Mr Anderson, and how she hadn't realized he felt that way about her. That prompted her to think about comments made by Mrs Fenton. She called her a 'Sweet Little Kitten' a lot. And commented about how nice it would be to have a sweet young thing to play with sometime. Could she mean like lesbian sex? Tammy fell asleep wondering what it would be like to be with another girl. Laura called waking her up the next morning. "Your Mom invited me to go shopping with you guys today. I haven't had anyone but you and Mandy to shop with in ages, I hope its ok." "Sure it is, I'm kind of nervous about shopping with my Momma for the first time. Oh, hey have you ever heard the term Kitten before? You know like an older woman referring to a younger one as a kitten?" "Oh my god, who called you a kitten? That's a term used by lesbian Cougars." Laura told her best friend. "It wasn't Mrs Reid was it?" Laura sounded a bit jealous now. "No, no it wasn't I just heard the term in a movie is all," she fibbed. "Oh, ok." "Wait a minute. Are you and," Tammy suddenly realized how her friend had blushed. "Don't tell anyone, please." "I won't but you have to tell me everything. Now get your ass over here and help me decide what to wear." Five minutes later Laura was there helping her pick out her outfit for the day. Tammy stood in pantys and bra looking through her closet as her friend lay on her stomach across her bed saying yes or no. Finally, she had what they both deemed the perfect outfit. A three tiered ruffled light blue mini that came to mid-thigh, a low cut tank style white top with the words 'Live, Love, Laugh', printed across the front, and black fishnet tights. She quickly stood in front of her dresser mirror and began her makeup. "What shoes are you going to wear?" asked Laura. "Oh," she giggled. "They're in my bathroom, I wore them last night." Laura scampered into the private bath to return with both the shoes and Tammy's pantys from the night before. "Ok girlfriend, who's cum is crusting your pantys? You were babysitting or did you step out afterwards?" Tammy grabbed the pantys from her friend. "Geez Laura, not so loud. But if you must know it's mine." Just then her mother tapped on the door before entering to show off her outfit. The black lace top with the short black A line skirt, the black stockings and the three inch black strappy heels really showed off her features. She did a slow turn and both girls smiled and said very nice, Laura added, "Sweet and Sexy". Which got her curious look from Evelyn, and a raised eyebrow from her best friend. As she stepped out of the room, she heard Laura say, "Your mom is definitely a MILF, I'd lick that pussy all night long." A little shiver ran through Evelyn's body at the thought of Laura doing just that. The fact that she'd not had a lesbian relationship since Tammy was born though did nothing but to fuel her thoughts. "What was that about Laura, are you wanting to do my Mom now?" asked Tammy. "Oh please, I've wanted to do your Mom since Ninth grade. I mean look at those melons and those sexy legs that," she stopped as a quiver ran through her. "Too bad she's hung up on my Dad." "Hey you promised to tell me about Mrs Reid, remember?" prompted Tammy. "Yeah well that's not as exciting as your totally hot Mom. You hear a lot about Moms and Daughters tag teaming some guy, but not about a Dad and Daughter tag teaming a MILF." "Hey I'd tag team your Dad with my Mom," Tammy said suddenly realizing the thoughts Laura was putting in her head were turning her on. "Oh please, you've never had sex. You wouldn't know what to do with a guy, especially one as hot as my Daddy." "Yeah but if me and Mom tag teamed him together she could teach me like the mothers and girls in those tube videos," said Tammy mentioning the ones they liked to watch together at Laura's house on her laptop. Tammy's favorites though were the babysitter videos. After a long pause she continued. "So tell me, tell me about you and old lady Reid." Prompted Tammy about the woman who lived four hoses down on the opposite side of the road. She was also the school's History teacher and Librarian. "Is that what happens when she makes you stay after school? Are you two doing it in the library or what?" "Not so loud, your Mom will hear. And I don't want to get Myra into trouble, she's really nice and taught me a lot about girls." "Ok how'd it all get started? Did she just like force you?" "No, nothing like that. It, it was right after Mikey tricked me into doing it. And I was kind of pissed at my Daddy because he was going out with Jennifer instead of your Mom. And she didn't want a kid around." Laura fell silent a minute, and Evelyn out in the hallway thought she was finished, then she began again. "I was crying in the library, and she sat down next to me. She just sort of rubbed my back and asked me what was wrong. I don't know why I told her, you know the whole don't trust anyone over thirty five thing." Tammy giggled, "I think its twenty five now." "She was really sympathetic and gave me a hug and said sex with boys at my age was always like that because they hadn't learned to satisfy a girl yet. But she could teach me how to do it for myself." "You mean right there in school?" "No silly, we never do anything in school. She just has me stay late so she has an excuse to be driving me home," Laura blushed. "God the things she can do with her tongue," Laura shivered. "I'd love to do that with your Mom. I bet she knows how to make a girl squeal. So tell me what happened that you creamed your pantys?" "Nothing I just got to fantasizing about being a girl all the time and how much my Momma accepts me," she lied, hoping Laura didn't catch on. "Well you know it really is special. You remember what happened to Misty when her parents found out she wanted to be a girl. They threw her out on the streets and she got beat up and raped and," Laura didn't finish the sentence, they both knew about the tragic happenings to the older girl who had come out to her parents. The police had found the body in an alley behind a bar. The perpetrators had been tried and convicted, all five of them, but still it was too late for her parents who had suddenly realized they had lost their only child because they were too ignorant to accept the truth. "You know if I had my choice for a first time experience I'd choose your Dad, he's hot. And besides I bet he'd be real gentle too." Tammy stepped back from her dresser and turned around, "Well what do you think?" "I think my Daddy would be a good first time experience for you." Blushing Tammy said, "No my makeup, how'd I do this time?" "Oh," giggled Laura. "You look really hot." "Girls, are you ready? I thought we'd go to breakfast on the way," Evelyn said stepping into the room, she noticed Laura staring at her and realized how much her nipples were poking out through her top. She lagged back following the two girls out to the car, her own imagination beginning to work as she watched Laura's cute bottom wiggling in the tight skirt. Tammy was almost too afraid when Evelyn parked in front of Denny's, but then she relaxed remembering she'd been there before with Laura and her Dad. "Good morning Evelyn," greeted the waitress. "Who do we have here? Oh Laura and Tammy, aren't you two usually with your Dad?" "Hi Vickie, Mrs Moore is Tammy's Mom," explained Laura. "Oh, I didn't know you had a daughter Mrs.,," she suddenly realized who Tammy was. "So you've stopped hiding from your mother, have you?" "Yes Ma'am," Tammy smiled happily. Breakfast with her mother out in public was very nice. And after they got to the Mall Evelyn split her time equally between the two girls, helping them both find properly fitting bras. "I had no idea that no one ever taught you about proper bra sizing," Evelyn told Laura. "How does that feel?" "Wow I never knew a bra could be this comfortable before. Except for the pullover sports bras we wear in gym class." She noticed how Evelyn's fingers seemed to caress her young breasts with extra care and tenderness. She did much the same with Tammy, but not quite as much touchy feely. As they shopped wandering from store to store Evelyn caught herself growing excited by thoughts of Laura in her bed. The young girl seemed to be going out of her way to ask for advice, especially about bras and pantys. They'd just left Teen Pizzazz, when they ran into Myra Reid. "Laura, I didn't expect to run into you today, Kitten. Are you and Tammy out shopping together?" "Yes Ma'am it's my first time shopping with my Momma, I mean as a girl." "Evelyn, oh I didn't notice you. So what do you think of your little girl? Isn't she just awesome?" "Yes she is Ms Reid. I hope she isn't any trouble at school." "No, she's probably the best student we have. And I'm so happy to see that you're being so open and accepting of her." "I feel a bit jealous though, you've gotten to know her for the last four years. I just started last night," Evelyn was sizing up Myra and she thought it was because of Tammy until Evelyn said, "Come along girls we have appointments at Rose's Salon. I want my daughter to look nice for school, you too kitten," she said one hand on Tammy's shoulder the other on Laura's shapely bottom. While Evelyn discussed what was needed with the sales girl at the salon, Laura said, "Your Momma totally felt up my butt right in front of Myra." She giggled. "I think you only imagined it because you have the hots for her," chided Tammy. "No don't say anything, just watch her," whispered Laura as she twisted one side the front clasp backwards on the bra she was trying on before stepping out to get Evelyn's opinion. "How does this one look?" she asked stepping out and leaving the door open so Tammy could watch. Her mother was practically drooling as she said, "Oh Sweetie that's so," "oh my, the clasp is twisted. Here let me help Kitten." Her fingers quickly opened the clasp then turned it around the right way. She let the backs of her fingers curl around the underwire support into the cups, as she guided it back scooping the young breasts into the soft cups. Then stepping behind her she pressed her own breasts into the girls back as she began adjusting the bra for her, her fingers lingering overly long over the fleshy mounds. Before she caught herself her hand had slipped downward her long nailed fingers caressing over the front of Laura's damp pantys. "See that matches purrrfectly." She whispered into her ear drawing out the 'purr'. Then not realizing the girls were watching her every move she sniffed her fingers. Tammy couldn't help but feel a bit jealous as her best friend continued to tease her mother every chance she got while they shopped. Evelyn enjoyed her time with both girls, this was her big chance to have a daughter and she went a little overboard spoiling her. But she was very aware of how much Laura was teasing her. She was sure that Laura was doing it on purpose, and hoped that she might get a chance to find out how much the girl knew about girl on girl sex. She was in Tammy's room helping her put her things away when the phone rang. Going to her room she answered it. "Hello?" "Ahh, Evelyn. It's Martin, sorry to bother you," he began. "Oh it's no bother," she said. "I wanted to ask you a favor, I have to go out of town in the morning to collect a Deposition for a client's trial. I was wondering if you would check in on Laura from time to time. I'm not sure how long I'll be gone, but I hope to be back Monday night." "When are you leaving?" "First thing in the morning, are you sure?" "Yes I'm sure. It will be fun we can make a day of it together, and she can spend the night here with Tammy." They talked a bit more and then she hung up and returned to help her daughter finish sorting out her new makeup. Evelyn had to admit hearing the girls talking earlier and having Laura flaunting herself all day had really reawakened her lesbian lust. A lust she'd put aside when Tom, Tammy was born. Thoughts of being restrained while another woman teased her into orgasm sent chills through her. and thoughts of sex with another couple, well she and her husband had done enough swinging early in life that she felt a bit of an urge there as well. After she was sure that her mother was in bed asleep Tammy turned on her laptop, plugging in her headphones she went online to her favorite Tube video site. She giggled quietly to herself as 'For Her Tube' came up with the couples and Babysitter category. She scrolled down the page then selected a video of a pretty ash blonde babysitter in pigtails with an older couple. The man had brown hair and was well muscled like Mr. Fenton, the woman had long blonde hair like Mrs Fenton. Tammy had acquired two realistic dildos. One about eight inches long and thick enough that it was nearly the same size as Mr Anderson. The other was about six inches and very thin. As she watch the video she began sucking on the larger one, the smaller had been coated with KY and she was rubbing it around over her pucker imagining it was a real cock about to fuck her. But no matter how turned on she got, she couldn't manage to get it past the head without hurting her, she added more KY using her fingers. She was gagging on the one in her mouth almost able to take it in her throat. But the one at her ass wasn't going in without hurting. Then before she tried again she began cumming as she began to imagine the one in her mouth was Mr Fenton and her fingers were Mrs Fenton's. As she lay there panting catching her breath she heard the low moans from her mother's room. She knew that her mother was using her own toys again, her fingers dug into her tight pucker, now slicked with her own cum as she strained to hear that familiar moan of ecstasy. But instead of moaning out 'Martin' she moaned out "Yes Laura, oh yes lick it good baby," before she came. Tammy was up early still frustrated by not managing to take even her smallest Dildo. Her mother seemed chipper though as they fixed breakfast. Then around ten Laura showed up for the day. Evelyn had been thinking about her since yesterday, and the little ring her husband had put in the hood of her clit ached for attention. Wondering how the girl would react to bondage she fingered the pair of stainless steel handcuffs that lay in her top dresser drawer. Absently she wondered what it might be like if the four of them got together, not incestuous though, she couldn't bring herself to think that way, not yet. The two had disappeared into Tammy's room as Tammy began getting ready to Babysit. "You seem in a determined mood today," commented Laura. "You have to help me tonight, please say you will." "Yes of course but with what?" "I, Laura I still can't get the little guy in me all the way." she admitted. "Yeah well you need help the first few times. It's different with a real cock because they can squish down as they slide in until you get loosened up and used to it being there." answered Laura from experience. "So you'll help me tonight?" "I will if I'm not busy," she grinned. "What would you be busy with?" "Well I might just be Muff Diving your Mom. We are going to be here all alone while you're out Babysitting." "Well you have a better chance with my Mom than I have with your Dad." She pulled on her skimpiest stretch lace pantys over her Gaff, then pulled the matching lace pullover bra on, knowing her nipples would stand out when she got turned on. Then she pulled on a sheer white blouse and a very short, pleated Blue plaid mini. She slipped on her sexy open toe three inch heels, and began brushing out her hair dividing it in two. Pulling her hair up into high loose pigtails she giggled. "How do I look?" "Like a schoolgirl hooker," Laura giggled. "You got a lollipop to suck on?" They giggled as Tammy pulled a tootsie pop out of her purse. Before heading down stairs. With her purse over her shoulder she called out, "Momma, I'm off to the Fenton's." "Ok Sweetie, call if you need anything." Her mother was looking her over as she headed to her car. At the Fenton's Tom answered the door in his suit. After gulping he said, "T, Tammy you're right on time. Diane, Tammy's h, here." he was a bit flushed and Tammy noticed his stiff cock. Grace was there in a second hugging her favorite babysitter. "Look what I brought." She said as she pulled out the latest computer learning game for preschoolers. The Fenton's always let her play educational games with Grace on their computer, they'd even set it up so she could use it after Grace went to sleep. "Oh don't you just look edible," commented Diane. "Do you have a date after we get back?" "No Ma'am, I just felt like looking sexy today," she answered with a nervous smile. "Well we shouldn't be more than a few hours. But I'm sure Grace will be ready for a nap by the time we get home." The couple left, and Tammy and Grace began on the game. Four hours later she had Grace all ready for a long nap. She got her tucked in and asleep then went to use the computer downstairs. +++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ As it was already quite warm out Laura had changed into her string bikini, knowing that it barely covered anything at all. It was one that her father didn't like her wearing as it, 'Put too much on display and invited young boys and men to imaging things they shouldn't' he'd said. Coming down the stairs from Tammy's room she stepped into the living room where Evelyn was watching her Sunday morning news program. "Mrs Moore, I'm going to take advantage of the opportunity to work on my tan," she said. Looking up Evelyn swallowed hard seeing how well developed Laura was, "Oh my I had no idea you had grown up so much. You're definitely going to break hearts with that figure," she said feeling a stirring as her pussy grew damp. "I hope so," giggled Laura nervously. "I want to get rid of these tan lines though." He reached up and back, pulling both top and bottom strings on the bikini top at the same time and the little bits of fabric dropped to the floor as she moved closer to Evelyn. "Oh, ummm, yes I see what you mean," Evelyn subconsciously licked her lips, her hand rising up to trace a tan line from the side of the girls neck down to her tender young breast. Without realizing it she began gently squeezing it as the nipple grew hard pressing against her palm. Laura leaned into the caress, her own hand nervously reaching for the older woman's larger breast. Evelyn reached up with her other hand as Laura stepped in the rest of the way to stand, her legs wide apart straddling her knees as Evelyn tilted her head upward. Silently she tilted her head upward even as the young girl leaned forward, her tender young nipple brushing her best friend's mother's lips. Laura's fingers were busy opening the buttons of Evelyn's blouse, when her hand slid gently down to cup the young girl's crotch, her long nails lightly scratching along the crease of the moist shaved pussy that lay beneath the fabric, even as her lips eagerly suckled her teenage breasts. When Laura had the blouse undone she slid it down over the woman's shoulders, pleased to discover there was no bra, as Evelyn moved first one arm then the other to let it fall to the sofa. Laura moved one knee then the other up to the edge of the sofa kneeling over her lap as she pressed her breasts into the hungry older woman's mouth. Her own hands eagerly kneading those larger breasts, lightly pinching and tweaking the huge stiffened nipples. She felt Evelyn's hands as they cupped her ass cheeks gently guiding her around toward the sofa. Kissing softly down her tummy, Evelyn pulled the strings at the girl's hips letting the last of the bikini fall away as her lips grazed sexily at the top of her slit. A guttural moan of desire escaped Laura's lips as she lay back into the sofa cushions. Evelyn's lips kissing softly down over the damp lips, before her tongue pressed in at the bottom and licked upward, opening the folds like a flower in bloom. The drool coating her tongue as she swirled it over the tender clit, little mews of pleasure escaping the young girl's lips as she continued to suck and tease her clit. She wanted to make the girl beg her to let her cum, as she continued, each time pulling back just before she could cum, Evelyn would switch techniques, unsure of how long she could hold out herself. Suddenly Laura locked her thighs around her face and flipped them both into the floor, ending up on top. She pressed her advantage now as she looked down into the older woman's eyes rocking her hips grinding her young pussy onto her tongue and until she began to cum, her body stiffening as she spasmed. Without warning Evelyn turned the tables on her as she rolled the girl onto her back, then straddled her hips pinning her down as she began removing her wrap around skirt. She'd been hoping for this opportunity all day, and hadn't put on any pantys. "So Little Kitty, how hungry are you? Are you ready for some cream?" she was rubbing herself over the girls tummy, slowly inching upward as she leaned forward pinning the girls hands above her head, as their lips met and Laura tasted herself on the older woman's lips. "So how experienced are you little Kitten?" she grinned. "Have you ever been Titty fucked by another girl?" Evelyn raised up her hips and slowly settled down again her pussy covering a stiffened nipple. She ground out a quick little orgasm before moving to the other breast. Laura squirming under her thrusting her little breast up into her, feeling the wetness as it coated them. As she lifted up Evelyn moved upward again, hungrily sucking at the excited clit standing out from under the older woman's hood, the glint off the little silver ring caught her eye as she realized the her best friend's mother had a clit piercing. Laura began lapping more eagerly now, her tongue catching the ring giving it little tugs. Her face coated in pussy juices, she begged to cum again. "Oh you're such a horny little Kitty aren't you? But if I let you cum again then you will be mine, you know that right?" "Y, yesss, oh yes please, please make me yours," she pleaded. Then started with a shock as she felt the cold steel clicking around her wrists. She found herself with her wrists cuffed around the sofa leg as Evelyn began kissing her way down her tummy. "Tell me little Kitty, have you ever been bound by a Cougar? Did nasty Myra ever restrain you?" Evelyn hadn't played bondage games since her husband had died. But now all of her old desires had been reawakened. Now she was the one in control and she loved the feeling of power over the girl. "N, no Ma, ma'am," she answered half afraid, yet excited at the same time. With a grin Evelyn blew softly over her moist clit. "If I teach you, will you let me pierce you? Make you my very own little play thing?" +++++++++++++++++++++++++++++++++++++++++++++++++++++++++ She was checking her Email and Facebook when she realized that she also had access to the Fenton's bookmarks. Curiously she opened it and scanned down the list coming to one that screamed open me. The title was, "Horny Couple seduces she-male babysitter." She never heard the door open, she was concentrating that hard on the video. Suddenly Mrs Fenton was behind, her hands gently rubbing over her breasts. "You like that site?" "I, I," she stuttered in surprise. "We decided to look, after your bookmark showed up in our own," explained Diane with a grin. "You're a naughty Kitten, but we like Naughty Kitten's, don't we Tom?" Suddenly Mr Fenton was there beside his wife, his fingers caressing her cheek. "Yes we do, especially pretty ones with something extra to play with." Mrs Fenton had been busy opening her husband's pants with one hand, now she pulled out his erect cock. Kneeling beside her as he moved around, she asked, "You wouldn't tell on us would you, if I shared this with you?" "W, will you teach me to, to take it inside me?" she blushed. "We will if you tell us how much experience you have." Promised Diane. "We wouldn't want to hurt you," added Tom. It was unreal, sharing his cock, both of them sucking it at the same time. Diane encouraging her as she choked and gagged on it trying to get it into her throat the way the older woman had. She could tell he was getting close to cumming, "Keep going, we'll share it. This will help him last longer the second time." As she had sucked on his cock, his wife had slowly stripped her of her clothes, then stripped off her own. She couldn't help caressing and squeezing those large breasts pressing against her own as they both sucked that beautiful hard cock. Then suddenly he was spewing his Jizz out into her mouth and over both their faces. She almost came as Diane began licking her face clean. Then holding her hand, the older woman led her to their bedroom. Laying down, she pulled her into a 69. Tom was there teaching her how to lick his wife's pussy even as his wife started giving her, her first ever blowjob. She was growing closer and closer as she licked and sucked at Diane's clit. Then Tom got up and moved to the other side of the bed. She felt his hot breath between her cheeks. His lips nibbling towards her tight pucker. Her clitty as it edged into Diane's throat. Suddenly his tongue swirled wetly over her virgin girlie pussy. She pressed her face into that warm sopping pussy in front of her as she felt his tongue jabbing in and out, round and round. Her clitty was in Diane's throat as she began to cum. And still Tom speared his tongue in deeper and deeper. Diane had wiggled out from under her and knelt in front cradling her to her breast as she sucked greedily at her nipples. Her husband driving his tongue deep into her ass, pushing more and more of his spit into her. With a giggle Diane said, "Now it's my turn to get you all ready for your first cock." She traded places with her husband and she began alternating between her tongue and fingers, while Tammy sucked on his stiff cock. She soon found herself rocking backward, grinding her hips around, as Tom pushed into her throat more easily now. Her tears ran down her cheeks running her mascara as she swallowed it deeper and deeper, her saliva flowing in torrents down her chin covering his cock and balls help him slide all the way in finally. She almost cried out when he suddenly pulled away and traded places with Diane. Gripping her pigtails, Diane pulled her face down into her drenched pussy as Tom began slowly pushing into her. She jumped a bit, biting her lip as he popped past the ring of muscle. But he held still until she squirmed a bit. Then he pushed in deeper, each time waiting to let her get accustomed to his size. Reaching around, he gripped her clitty gently stroking. "Whenever you're ready baby, just go slow and easy," he said. She moved a little at first then more and more rocking back and forth until she was fucking herself on his cock. She felt him as he began fucking into her, soon he was driving in harder and harder, until she came. He pulled out quickly and his wife flipped her over into another 69. Then he slammed his cock into his wife's pussy. Gripping her by the hips he slam fucked her as he blasted his cum deep inside. When he pulled out, it began dribbling out and the two of them lapped it up together, bringing Diane to yet another huge orgasm, her contractions pushing out more and more of it. Then she flipped around and couple licked her face clean. "Why didn't you cum in my ass?" she asked him thinking she had done something wrong. "Oh baby, I wanted too, believe me. But you aren't ready for that yet," he said. "Not unless you want your Mother to be asking lots of questions," added Diane. "But don't worry, we'll help you be ready next week when you come to babysit." Before she left Diane gave her some advice. "You'll want to take a long hot soak, it'll help ease the soreness that you haven't started to feel yet. And I'll send you an Email with instructions on how to prepare before you get here next Sunday." A little confused now she asked, "But isn't Grace going to her grandparents next Saturday?" "Yes but I don't think your Mother knows that, does she?" She actually giggled with excitement, shaking her head no. ++++++++++++++++++++++++++++++++++++++++++++++++++++++++ Evelyn had licked and sucked Laura's clit to three good orgasms before she let her out of the cuffs. "Now little Kitten, who do you prefer, Me or Myra Read?" "You, I want to be yours," Laura answered. "And will you wear my special ring to show it?" Unsure of what she meant Laura said, "Yes Ma'am." +++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ It was only Seven PM when Tammy got home, but she noticed her mother's car was gone. A sigh of relief she got out of her car feeling the soreness that Diane Fenton had warned her about. She giggled as she sank into the hot tub filled with her favorite bubble bath and lay back with a wash cloth over her eyes. +++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ May I help you Ma'am?" asked the young girl in the piercing and Tattoo shop. "Yes we'd like to get a couple of piercings done if it isn't too late," answered Evelyn. "Oh it's not late yet," chuckled the girl feeling as if she'd just met her newest Cougar Kitten pair of the week. "Good, my daughter needs her clit hood pierced. And I would like to get my tongue pierced like hers." When Evelyn mentioned the piercing Laura stuck out her tongue to show it off. An older girl stepped out to get them to sign the forms. Then said, "It's good to see someone claiming this little Kitty. It would be a shame to let Mrs Reid continue to string her along like the others. Maybe they'll find someone willing to take them under their wing." She did Evelyn's tongue first then she asked, "Would you like a pair of Labia rings put in? That would let you put a lock on her when she's away from you at school." Without asking Laura she mumbled, "Yesh pleash," then giggled at herself. "You'll get used to it soon enough. And it will heal faster if you soak it inside her." it came out as 'soak it in cider', and the older women laughed. +++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ The sound of the car pulling into the driveway startled Tammy awake. The water had cooled off and she did feel better, not as sore. She was smiling to herself as she slipped on a blue baby doll nitie and went down stairs. Seeing the way Laura blushed, she knew that her best friend had gotten her wish, and smiled sheepishly. "Oh my god, you got your cherry popped," giggled Laura. To which Evelyn looked around to her daughter, her face glowing with that first time sexual afterglow. But what could she say to her daughter, as the three stood there looking at each other knowing. Her mother hugged her tightly, "Did he make you cum? Did he treat you right?" she noticed her mother's almost mumbled speech, and Evelyn was glad that she was learning quickly how to talk with the piercing in her tongue. "Yes Momma, Did, did Laura rock your world?" "You aren't jealous are you?" "No Momma, you deserve to be happy." They kissed cheeks. "So?" asked Laura. "Yes," she giggled. "Yes what?" asked Evelyn. At her nervousness Evelyn took her by the hand and led her over to the sofa. Her fingers smoothing her daughter's hair. "Tammy, if your first experience was with an older couple then I am happy for you. They'll be gentle and show you more than some dumb ass Jock in the backseat of his car. Besides, I won't have to worry about you getting hurt or worse. And I think the Fenton's are going to be good for teaching you lots of things I can't." she guessed correctly "Momma, I," her mother pressed her finger to her lips. "Outside the three of us, I don't want to hear it mentioned. They could get into a lot of trouble if the wrong people found out." she didn't have to mention her and Laura's situation was the same. But people would be more forgiving of her than they would a Sherriff's Deputy and an Assistant District Attorney. With a giggle Laura said, "Look what your Momma got for Me." she lifted her skirt and pulled her pantys to the side to show off the three new piercings. Tammy's eyes went wide seeing not just the clit ring, but the ring in each lip of her best friends Labia. "Does, I mean do they hurt?" I asked. "Only a little bit, but they'll heal fast. Your Momma got her tongue pierced too," she giggled. Suddenly I wanted my tongue pierced as well just like Laura and my Momma. I'd known about my Momma's other piercing. Laura had pointed it out to me one day when she was wearing her bikini on the patio. And then I'd snuck in and got a look at it when she was changing one day. I was looking at Momma now, my eyes pleading, trying to figure how I was going to ask her. "You want your tongue Pierced like Laura's, don't you?" "Yes Momma," I admitted. "We'll go Monday after school. Besides I've decided that maybe Laura can handle a couple of other piercings to show my love as well. But it is up to you both if you want them." she lifted my chin in the palm of her hand. "And you little Princess are going to the doctor and get a real prescription as well as that letter for school." I'd forgotten about that, and it showed. She chuckled, "Oh Sweetie, why didn't you tell me sooner? Just think of all the fun we missed together." As I lay in bed listening to my Momma and my best friend I tried to figure out what she meant by other piercings. My hands strayed up to my breasts listening to the two of them and I realized she was talking about our nipples.