0 comments/ 79841 views/ 2 favorites On the Lips Ch. 01 By: PrincessErin Heather stood in front of her bathroom mirror and smiled at herself. "Not bad," she thought. Her blonde hair was still thick and shiny and she was still able to put it in a ponytail without looking like she was trying too hard. She looked quite cute in her tennis outfit and as she leaned over to tie up her running shoes, she smiled as her soft round breasts pressed against her top. She grabbed her racket and house keys and made her way down the street toward the tennis courts. She had lived in Winterwood Village for over five years and loved it. It was a gated community and had all the amenities that were important to her. There was a tennis court with a cute tennis coach named Jason. The pool and fitness center was the best in the area and Mark, the lifeguard, was very cute in his black swim shorts. Heather waved to her neighbors as she entered the tennis courts. Jason was waiting for her and she couldn't help but stare at him. She knew from chatting with him that he had graduated from college last year and since the only thing he really loved to do was teach and play tennis, he was ecstatic to get this full time job. "Hi Jason." Heather walked up to him and kissed his cheek. He was almost twenty years younger then her, but he still reacted to her body. She glanced down and could see his member pressed against his tennis shorts. "You ready to get beat?" "Yeah right!" Heather and Jason began their set. Jason was amazing at tennis, but after coaching Heather once a week all spring, she was almost on equal footing with him. Now that it was summer, they played once a week. Both of them were sweating and after three sets he had won. They made their way to the sidelines to grab some water. "I told you I'd win." "Young guys are so cheeky." "You love it." Heather laughed and after making sure no one was watching, she kissed him softly. They had kept their affair secret for almost four months and so far it was working. "You going to be home later?" Jason whispered against her lips as he ran his hand up and down her inner thigh. "Unhuh." Heather was trying to concentrate, but every time he touched her she went crazy. The couple pulled away from each other and Heather made her way back home. She knew that Jason was staring at her cute butt as she walked away and she loved it. She walked up her front steps and admired her home. She had one of the only bungalows in the community, but she loved it. It was just her and she didn't need the large five bedroom mansions that most families lived in. She had never gotten used to the idea that money was status in Winterwood. She entered her home and made her way to the master bathroom to shower and change. She let the warm water cascade down her body and as she rubbed her body with vanilla body wash, she could feel her inner thighs were wet with her moisture. She resisted the urge to touch herself. Jason would be over soon and would help her with that urge. Heather was showered and changed into a short summer dress. She was sitting on the couch when she heard a light knock on the patio door. She got up and smiled as Jason stood in her backyard grinning. She unlocked her door and the moment Jason stepped in, he picked her up and carried her to the bedroom. She wrapped her legs around his hips and moaned as he grabbed her butt cheeks and squeezed. "What's the lesson today baby?" Heather nibbled his earlobe as her hands rubbed her shoulders. "Rough sex. Tiffany liked when I bit her neck last night. I want to do more." Heather slid off Jason and undressed quickly. He did the same and they lay on her queen size bed. "Pull me into your lap." Heather spoke harshly to Jason, needing to get him angry so the rough sex would be intense. He did as she demanded and they looked into each other's eyes. He rocked her back and forth, knowing his cock was rubbing her pussy. She moaned. "Push yourself inside me and hold my hips tight. Bite and then lick my neck." Jason was moaning loudly as this older woman gave her directions. He did as she asked and before long he was bouncing her on his cock while his teeth dug into her neck. She smelled like vanilla and it was driving him crazy. "Flip me over. Bend my knees and rub my clit while you fuck me." Heather was so close to cumming. She always got so turned on when she gave him directions. It gave her power and purpose. "Fuck you feel good baby." Heather nodded as she lay on her back. Jason was gripping her legs in the air with one hand while his thumb pushed on her clit. She exploded in an intense orgasm. "Don't stop. Remember last time." Jason nodded and continued to thrust. If he hadn't jerked off before coming over he wouldn't have lasted. Looking down at Heather trying to catch her breath pushed him over the top. He thrusted one last time and emptied himself inside her. "Was that good?" Jason looked at Heather for approval. He had learned so much from this older woman and was desperate for her approval. "Yes sweetie. You can bite harder. It will leave marks, but she'll love it. You can also spank her ass while she rides you." Heather glanced down and seeing his cock twitch she giggled. "You want to try that?" Jason nodded and Heather climbed back into his lap. He kneaded her butt and then tapped lightly. "No harder. With your cock inside me the pain and pleasure will drive me over the edge." Jason lifted his hand and spanked her hard. Heather gripped his chest with her long fingernails and breathed in hard. Jason spanked her again and again. He watched as Heather rode his cock roughly and when she came she twisted his nipples. "Oh fuck!" The intensity of her orgasm along with his nipples being twisted drove him over the edge. He unloaded his cum inside her again. After they recovered, he got up. "I have to go. Mom thinks I'm still at the tennis courts." Jason leaned over and tried to kiss her on the lips, she turned her head so he could kiss her cheek. They had a rule about kissing on the lips. "Next week, same time?" "Of course baby." On the Lips Ch. 02 Heather was lying by the pool in a cute one-piece swimsuit. She loved how hot September had been since it meant that she could continue to suntan and relax outside. She loved the Florida weather and wondered why it took her so long to move here. She rolled onto her stomach and looked up at Mark. Mark was the lifeguard at the pool in her gated community. Heather had lived in Winterwood for over five years and loved it. She looked back at her book and then looked up again and gasped. Walking towards her was Jason. Jason and she had been having an affair, but after their last get together, which was over a month ago, she hadn't seen him. She remembered how angry she was when she went for her normal Wednesday afternoon game of tennis with Jason. Instead of finding her cute young lover, there was this girl named Amanda in his place. "Can we talk?" Heather sat up and let Jason sit on the edge of the lounge chair. "My mom made me quit four weeks ago. She got me a job at my Dad's office. This was the first chance I had to come back and visit. I had to tell her I'm visiting Mark. I'm sorry." "That's fine. Well it's not, but not much I can do about it." "Wish we could have one last time." His voice was low and she was thankful that the pool was almost empty. "I know." And with that, Jason got up and walked out of the pool enclosure and was gone. She lay back in her chair and closed her eyes. She knew it was only an affair. She knew he had no feelings for her, but it still made her feel like crap. When Jason had first approached her about their arrangement, she was shocked. He was a virgin coming out of college and his girlfriend Tiffany assumed he was more experienced. Heather had spent four months teaching Jason everything about sex. Now it was over. "Miss. Miss." Heather felt someone shaking her gently and when she opened her eyes there was a shadow over her. Mark was standing above her waking her up. "I'm sorry to wake you, but the pool is closed." Heather blinked and realized she had fallen asleep. "I'm sorry Mark. I'll quickly get my things." Heather grabbed her things while Mark watched over her. Mark was just out of high school and had taken this job for the summer. She wasn't sure why he was still there, but figured it wasn't her place to ask why he wasn't in college. Mark and Heather walked to the gate that enclosed the pool. He was walking a little too close to her, but she didn't mind. He was quite tall and muscular, much different from Jason who was shorter and thin. Mark had a dark tan from being outside all summer and his blonde hair had turned almost white from the sun. Just before she stepped out of the enclosure, he leaned over and whispered in her ear. "I'd love an arrangement like you had with Jason. Older women turn me on and you are just simply sexy." With that he closed the gate and walked to the office to do some paperwork. Heather was left standing there stunned. Her mind was processing what he had said. She and Jason had never mentioned their arrangement to anyone, but she knew that many of the wives slept around with each other's husbands. The only difference was that she was with someone younger. The next day, she cancelled her tennis match and instead decided to go to the pool. She debated on what swimsuit to wear and decided that instead of the conservative black one-piece that she normally wore, she would wear the two-piece red suit. It wasn't really a bikini since both the bottom and the top covered a lot of her skin, but it did show off her belly and she was thankful she never had children. There were no stretch marks nor was her belly flabby, well not yet at least. She walked into the pool area and settled herself on a lounge chair. As the day progressed, the little kids went home for dinner and she was left alone with Mark. She decided that a month without sex was driving her crazy. She walked over to where Mark was standing and looked up at him. "Hi. What sort of arrangement do you think Jason and I had?' Mark grinned. "He told me that you taught him a lot about sex so he wouldn't look like an idiot in front of his fiancé." Heather's face fell. She didn't know that he had proposed to her, but it all made sense now. Tiffany was from a well off family and it wasn't proper for her future husband to work as a tennis coach. "That would be correct. Think you can handle someone much older then you?" "You're not that old. You're quite cute and you've been driving me crazy in that swimsuit all day. Let's cool off." Mark turned and dove into the deep end. He hardly made a splash and as he surfaced she couldn't help but grin. She entered the water slowly by the shallow end ladder and he swam towards her. Mark leaned over and tried to kiss her on the mouth. She turned her head and he latched on to her soft neck. His hands ran over her breasts and pinched her nipples. She couldn't help but moan and totally forgot that they could get caught. "God you're sexy." Mark nibbled her earlobe while sliding his hands into her bottoms to find her round butt. He squeezed her butt cheeks and ground himself against her pussy. All Heather could do was continue her moans. Her body was on fire and she totally forgot that she was supposed to teach him about sex. Mark spun around and lifted her onto the edge of the pool. "I've never licked a pussy before. Tell me what to do." "Lick slowly around the outside and then lick my clit. Go between slow and fast. You can finger me if you want." Mark's eyes glazed over when he pulled her suit to the side to reveal her pussy. She kept it trimmed and the soft blonde hair framed her wetness perfectly. He leaned in and did as she said. "Am I doing this alright Heather?" "Yes. Don't stop. I'll tell you when I cum." Heather arched her back and felt Mark's tongue continue his assault on her pussy. She pushed him harder against her pussy and cried out the words harder and faster to tell him what she needed. "Cumming." She could barely whisper that word as her body shook. It was so intense and she opened her eyes to look at Mark. Mark was smiling sheepishly at Heather. "Was that good?" "More than good. I need you inside me." Mark pushed down his shorts and gripped his cock. It was a little shorter then Jason's, but much thicker. She watched as he began to stroke himself. "No. Don't make yourself cum that way. Let my pussy do that." Mark nodded and in one thrust was inside her pussy. He thrusted back and forth and closed his eyes. She could tell this was either his first time or one of his first times since he was using the same rhythm he used to jerk off. He cried out and came inside her. "Wow that was amazing." "I'm glad you approve. Was that your first time?" Mark blushed. "Yeah. But I've made out with a bunch of girls. And Jason told me you like when your butt is squeezed." Heather smiled and exited the pool. Mark did the same and after she picked up her things she kissed him on the cheek. He tried to move his mouth to meet hers, but she resisted. "I don't kiss on the mouth. This is sex. Pure and simple. No feelings or emotions." And with that Heather walked back to her bungalow. On the Lips Ch. 03 "What the fuck are you talking about?" Heather was yelling at the top of her lungs as the people at the meeting stared at her. "I'm being evicted? I own the house." Heather was pacing the room as the members of the board of directors of her gated community informed her of their decision. "Mrs. Regan. It is evident that you have been having, shall we say, unacceptable relations with the staff. We cannot have that at Winterwood. You will get the full amount for your home and we have already arranged for a moving truck for the end of the week." Heather just glared at her neighbors. At forty-two, she was much younger then most of her neighbors. In her mind, she figured that these old people had pretty much dried up when it came to sex. It wasn't her fault that younger guys found her attractive. It wasn't her fault that she had gone from teaching the tennis coach how to have sex to fooling around with the lifeguard after hours at the pool. "Fine." Heather stormed out of the meeting room and walked straight to the pool. Mark was there and he tried to avoid her. "Mark. Just come over here." Mark walked over to Heather. "I'm sorry if this costs you your job. I'm moving out at the end of the week. It was great while it lasted." "I know." That was all Mark could say and then he watched the woman who had taken his virginity walk away from him forever. *** Heather had moved from her bungalow to a condo apartment. She had spent the last two months examining her life and realized that she was through with men. Her first boyfriend had been her first everything and when they got married after college she had been thrust into the life of a stay at home wife. When her husband had died, just after their fifteen-year wedding anniversary, she realized she had nothing. They had chosen never to have children. She had money, but that was really her husband's money not hers. She had just been asked to leave the prestigious gated community she had lived in for the last five years for what the board of directors considered "inappropriate relations with staff members." She decided that she would try to curb her sexual appetite. She had her fingers and the showerhead and was going to stay away from men, especially young men. Heather was at a charity auction. She had thrust herself into charity work and was currently working the coat check. She was wearing a silver gown with low heels. All around her rich couples were coming and going. She was shocked to find out that the ball would probably raise close to one hundred thousand dollars. That was an insane amount, but she just nodded and went along for the ride. Once everyone had arrived, she walked around the room making sure that no one else needed her help. She felt a tug on her elbow and when she turned, she was face to face with a young man. "Can I have this dance?" The man was about twenty years old and had cute glasses. His hair was dark as were his eyes. "I'm actually working the charity function. I don't think it's appropriate." "Hush. We're dancing." Heather was led onto the dance floor and tried to think sensibly. The man held her close and they swayed to the music. She wrapped her arms around his neck and everything felt perfect. She tried to calm down her breathing and felt her heart beating so fast. The song ended and the man walked away, not saying another word to her. She spent the rest of the evening trying to see this young man again. He was nowhere to be found and she hated her body for reacting the way it did. Heather was one of the last to leave and as she made her way to her car in the parking lot, she found him leaning against it. "I'm Drew." "Hi Drew. I'm Heather." Drew pulled her towards him and pressed her against the driver's side door. He then pressed his body against hers, his tongue circling against her neck. He took her car keys, unlocked her door, and opened it. Her eyes were closed and her body was reacting to his lips. She could feel her nipples harden and her panties were already damp. Before she knew it, he stopped kissing her and had guided her gently into the driver's seat. "Have a safe drive home." And with that, he walked towards his car, got in, and drove off. She sat stunned in her car for a few minutes and then made her way home. She lay in bed trying to forget Drew and how she just wanted to grab him and kiss him. She reached over and grabbed her vibrator. It was pink and had only been used a few times over the year she had owned it. She turned it on high and pressed it against her clit. She cried out as a wave of pleasure crashed over her. She cried out Drew's name and let the little rabbit buzz against her swollen clit. Each time she made herself cum she imagined Drew's cock inside her. The idea of a younger man was so appealing to her, partly because it made her forget how old she really was. "Fuck." Heather held the vibrator inside her and thrusted her hips. She was covered in sweat and her inner thighs were throbbing. She rolled onto her side and passed out cold. On the Lips Ch. 04 Heather spent the next few months in a perpetual state of fantasy. She had sworn off all men, but Drew just always happened to find her. Every single charity function she attended, he was there and they would dance, cuddle in private, but nothing more. He would always bring her close to orgasm, but then leave her stranded in the parking lot or hallway. She was falling for him hard and fast and she didn't even know his last name. Finally, she decided to take matters into her own hands. She was attending a BBQ at a local park to raise money for a children's hospital. She dressed in slacks and a button up top. She saw him and immediately walked over to him. "Answer some questions for me. Who are you and why the hell have you been seducing me?" Drew laughed. "Well Heather. I wanted you to make the first move. You are sexy and cute and intelligent. I know you're hung up about our ages. A little birdie told me what happened to you at Winterwood." Heather stared at Drew. She had made so many mistakes in the past, but couldn't bear to make another mistake again. "I can't." Before Heather had a chance to move he grabbed her and pushed her against the picnic table. His hands were all over her body and she instinctively lifted herself up to sit on the edge of the table. He wrapped her legs around his hips and ran his hands up and down her sides. "You are so gorgeous. Go on a date with me. Velvet Room. Seven o'clock on Friday." Heather rolled her eyes. She was too old to be going to dates, but she was so drawn to him that she couldn't say no. The next Friday, she waited outside the restaurant for Drew. He was right on time and they entered the restaurant. She noticed that people were staring at the two of them and she hated that she was almost old enough to be his mother. He was the perfect gentleman and they chatted about normal every day things. He drove her home and walked her up to her apartment. "You are gorgeous Heather." He leaned in and tried to kiss her. He latched onto her neck and sucked hard. "Do you want to come inside?" Drew nodded and she led him to her bedroom. They undressed each other slowly. He was going so slowly that it was driving her crazy. He nibbled down her chest and flicked his wet tongue against her breasts. She tried to reach for his cock, but he wouldn't let her. Finally, he slid inside her and she felt so good she almost cried. She came numerous times and each time he was hard again, thrusting inside her, concerned only with her pleasure. In the morning, Heather awoke feeling a warm body next to hers. She moved a bit and every muscle in her body was sore. She remembered the night before and smiled. It was so intense, both physically and emotionally. She looked over and Drew was awake. "Can I tell you something Drew?" Drew was lying on his side facing her, tracing circles against her bare stomach. "Anything sweetheart." "I was married for fifteen years. He died in a car accident. After him, I never kissed anyone on the lips. It was too personal." "That's fine. I just want to make you feel good. You are so beautiful." Heather blushed and he pulled her on top for another round of lovemaking. *** Heather was slowly getting used to having Drew around. He was so sweet and romantic. Her kitchen was always filled with flowers, but there was something missing. She couldn't kiss him on the lips. She had gotten better at not being so self conscious when they went out together and she found out why he was at so many of the same charity functions. Drew's mother had made it her life's work to run three different charities. Drew had graduated from college the year before and had become, as he liked to call it, his mom's slave. His official title was personal assistant, but either way he enjoyed running the business side of her organizations. It was a rainy Wednesday afternoon. Heather was relaxing on the couch while Drew was out doing some errands for his mother. His mother was actually quite nice, but had been a bit concerned when Drew had introduced Heather as his girlfriend. Things were going quite fast, but the sex was so amazing that it was worth it. "Hi sweetie." Drew entered her condo with her mailbox key along with her mail. He was always doing sweet things like getting her mail and she was coming to enjoy being pampered. He handed her the mail and she gasped as she held a letter in her hand. Opening it up, she swore under her breath. "What's wrong Heather?" Holding a gold embossed wedding invitation in one hand she blurted out. "Jason is getting married and he invited me." Heather walked into the church with Drew by her side. She was attending the wedding of her tennis coach and by her side was a man that she loved dearly. Of course, it wasn't that simple when she thought about it. Jason had been the tennis coach at the prestigious gated community she once lived in. They had been secret lovers for over four months and she had taught him a lot about sex. Of course the reason she was doing that was to impress his girlfriend Tiffany, whom he had proposed to only a few short months ago. Drew and Heather sat on the groom's side of the church and she looked over at Drew. Drew was twenty years her junior and they had been dating for just a few months. She had always been drawn to younger men and he was the third man in his twenties that she had dated since her husband had died. The wedding began and she tried not to giggle as no less then eight bridesmaids made their way down the aisle. They were wearing these bright pink dresses while holding pink roses. Actually everything was pink, the flowers, the dresses, and the shoes. The ceremony was long and boring and they wrote their own vows, which were sappy and romantic. Heather was thankful when it was over and they made their way over to the fancy hotel where the reception was being held. After dinner, there was the bouquet toss and cake cutting. Drew teased Heather about going up to catch the bouquet, but she refused. When the dancing began, Drew asked her to dance and she said yes. She had avoided Jason all day and was shocked when he was next to her on the dance floor. He smiled at her and she smiled back. From all they had been through, the communication between them was clear. Both had moved on and she had gone from only expecting to be used for sex to being truly in love with a younger man. Drew and Heather had gotten a hotel room for the night and both had just a little bit too much to drink. They stumbled to their room and, once inside, were all over each other. Drew kissed Heather's neck while pulling down her dress. Once her dress was around her hips, he pulled down her bra and grabbed her breasts. They were the perfect size and he sucked on one nipple then the other. The whole time he was walking her towards the bed and pushed her back against it. He watched as she wiggled out of her bra and panties. She slid her dress off of her completely and began to undo her shoes. "Shoes stay on. They're so fucking sexy." Heather grinned and watched as Drew undressed and climbed on top of her. He thrust his cock inside her and began to fuck her. She was on her back and he was holding her feet in the air. Drew kissed the inside of her feet as he thrust his hips harder and faster. "Cumming." Heather cried out as she came. Drew moaned and flipped her over onto her hands and knees. He thrust back inside her. He came quickly and as he pulled out, he saw how wet his cock was. "Kiss me." Heather had rolled onto her back and was looking up at Drew. "On the lips?" Heather nodded. Drew grinned from ear to ear as he leaned down and for the first time kissed her on the lips.