8 comments/ 159429 views/ 27 favorites Virgin Sitter By: sensualsweety5 Leeann was a beautiful brunette. She stood about 5'5" with baby blue eyes and cute freckles. She had beautiful curves from her big breasts all the way down to her plump ass and thighs. She had just turned 18 and took on a job babysitting for a single father. The single father, Michael was a very handsome man for his age. He was in his mid-fifties and balding slightly. He had light brown hair and green eyes. He was about 5'11" and average build. Leeann had a beautiful smile that attracted Michael from the git-go. He thought she was incredibly sexy. He had to contain his desires on a daily basis as he knew any sexual contact with her would probably result in the loss of a good babysitter. One late night Michael came home as Leeann was sitting on the couch. She had on a tight tshirt and tight sweat pants. She stood up immediately to greet him. "Hey! How was work?" she asked. "Ha, long and tiring as usual. How'd things go tonight?" he said. "Oh everything went well, as usual!" she replied. After a short time Michael could feel his cock beginning to get hard. He casually sat down to hide it. He knew it was wrong but he began to think of a way that he could get Leeann alone some time. He instantly created a plan. "Are you free this Wednesday? I have to cover someone's hours at work and I don't have anyone to watch Johnathan." said Michael. "Uhm, sure. What time would you need me here?" Leeann asked. "Noon." he replied. Leeann agreed and went on her way home. Over the next few nights Michael was alone with his thoughts and planning out exactly what would happen. The truth was that Johnathan was going to be sent to his mother's for a few days and Michael would be alone. But not for long. Wednesday came around and Michael awoke and got himself ready by showering, shaving and putting on some cologne. He shaved his cock and balls and made sure that everything was in order. He was praying that he'd be blessed with invading Leeann's tight cunt. Before he knew it, it was noon. Michael heard a quiet knock on the door and he rushed to answer it. "Hello!" he said with a big smile. "Hey Mike! What's up? How's Johnny doing?" Leeann asked. "Uh, well...turns out, Johnathan left for his Mom's this morning. I completely forgot that it was her day to have him!" he blushed. "Oh. Well that's okay." Leeann said awkwardly as she put her hand on the door. Michael knew he was about to lose his chance. He put his hand on her shoulder, "Hey, if you wanted, I'm not doing anything. Would you want to stay for a little bit and watch this new movie that I just bought." he asked, hoping that she'd say yes. Reluctantly, Leeann agreed to stay. "Sure, what movie?" she asked. "I can't remember the title." he said as he strolled into the living room. She took a seat on the couch in her gym shorts and cute t-shirt. He could feel his bulge rub against his boxers inside his jeans that suddenly felt so tight. He grabbed a beer out of the fridge and motioned toward her to see if she'd like one. She shook her head no and giggled. He entered the living room and sat on the couch next to her. He was so nervous and wasn't sure how he'd make a move. Her phone vibrated. She had a text. As she closed her phone Michael noticed a photo of Leeann and a boy as her background. "Is that your boyfriend?" Michael asked curiously. "Oh, no. Haha, that's my cousin." she laughed. "Oh, I'm surprised." he said. "Why's that?" she began to get nervous. "Well, you're a pretty girl, I'm just surprised that you're not with anyone." he said kindly. "Oh, nope. There's never been anyone worth my time." she said confidently. He suddenly asked himself if she were a virgin. He almost had to know. "So..you've never even had sex?" he asked. He knew he was crossing the line. "...no..." she laughed uncomfortably. "Sorry. I shouldn't have asked." he replied. "It's okay. No big deal." she smiled. "There's nothing wrong with being a virgin or anything, it just sucks being the only one of my friends that is." she said. "Oh. That's unfortunate." he said as he locked eyes with her. He placed his hand on her knee. "There's nothing wrong with being a virgin. And guys your age don't know anything about women and how to treat them anyway!" he said, his bulge growing by the moment. She noticed his member bulging at the zipper of his jeans. She giggled. "I take it that you know how to treat a woman then?" she asked. She suddenly felt a little bit anxious and kindof wondered what it'd be like to have a sexual relationship with an older man. Michael couldn't contain himself any longer. He began to move his hand up Leeann's thigh. "In fact, I do know how to treat a woman." he said as he smiled and leaned in to kiss her neck. Leeann smiled. "I don't know if this is a good idea." she suddenly pulled away. "Oh..I'm sorry. I...I wasn't trying to make you feel uncomfortable...I..I just..I think you're beautiful...And I can't help it. I just wanted to..." he stuttered. Leeann cut him off "you just wanted to what? fuck me?" she asked. "Oh..oh no. I wouldn't say that...I've just wanted to explore you. And have you explore me. Make love I guess.." he was so nervous. Leeann cracked a half-smile and leaned back toward him. Michael smiled back and began to kiss her neck again as he slowly moved his hand up her thigh. Leeann could feel her nipples getting hard and a strange sensation going from her stomach all the way down to her tight virgin cunt. Michael began to lift Leeann's shirt with his other hand and slowly, he exposed her 32D breasts. He pinched one of her nipples as she let out a quiet moan. Michael smiled devilishly. "Are you enjoying this?" he asked. "Mhm." she quietly moaned. Michael's hand was now directly over Leeann's mound. He began to move his hand up and down along her slit. He could feel her warmth and slight wetness through her shorts. She groaned in pleasure. He was rock hard now. His pants were suffocating his member. Michael stood up and unbuttoned his pants. Leeann's eyes grew wide. "Don't worry." Michael said reassuringly, "I'm not going to make you do anything you don't want to, I'm just giving it some air." he smiled. Suddenly Leeann felt more comfortable and took off her shirt and bra the rest of the way. Michael grinned as he leaned down to suck on Leeann's nipples as he stood in his boxers, his member protruding. She groaned and moaned as he went back and forth between breasts while using his thumb to massage her throbbing clit through her shorts. she was moaning and groaning and grinding her cunt into his hand. Michael knew she was really liking everything. He knelt down as he slowly began to remove her shorts. To his surprise, she wasn't wearing panties! Michael gasped and smiled at Leeann. He pulled her shorts down farther to reveal a shaved cunt. "Oh wow!" he said, "you shave!?" "Yes." she giggled. Michael was so surprised. He could feel his cock throbbing. He wanted so badly for Leeann to voluntarily take his cock into her hot, wet mouth. But instead, he decided to take her juicy cunt into his mouth. He moved in slowly, inhaling her sweet scent. He was groaning in anticipation. He slowly inserted one finger into her tight hole. She groaned loudly and ground her hips into him. He grinned as he slowly moved his finger in and out of her virgin cunt. He picked up speed and twisted his finger around before suddenly adding another. She groaned again, this time wincing a little bit. "Everything okay?" he asked. "Mmm, yeah." she panted. He knew she wanted more, and he knew he needed to taste her sweet juices. He moved in closer and slowly extended his tongue and slowly slid it across her clit. Leeann let out a loud moan. Michael couldn't resist. He began flicking his tongue up and down against her clit. She writhed and bucked like mad as he held her legs over his shoulders and buried his face into her cunt. She was moaning and screaming begging him to stop as he relentlessly ate her pussy until she came. He licked up all of her juices and stared up at her. After licking her cunt clean, he slowly kissed from her cunt up to her breasts, to her lips. He passionately kissed her as his cock was bulging into Leeann's warm and tired cunt. He didn't want to ask for favors, but he wanted so badly for her to suck his cock. He rolled off of her and sat, lets spread on the couch. He began to rub his cock through his boxers groaning slightly. Leeann's curiosity led her over to him. She sat there naked and stared at his member. She casually looked up at Michael and he assured her with a silent nod. She began to slowly remove his boxers to expose his 7 inch cock. "Wow." she gasped "that's huge" Michael just snickered as he guided her hand around his throbbing cock. The touch of her skin against him made him groan. He began guiding her hand up and down his member. Soon, he let go and let her do the rubbing. Her hands were silky smooth and her grip was perfect. She changed speed and could occasionally run her thumb over the tip of his cock. She watched pre-cum seeping out of the tip and suddenly, she yearned for a taste. "Can I?" she asked as she looked from Michael's eyes to his cock. "Of course." Michael replied, not trying to sound too anxious. Leeann moved onto the floor and knelt between Michael's legs. With one hand holding onto his cock, she slowly kissed the tip. The sensation sent shivers down Michael's spine. He moaned in pleasure. Leeann stuck out her tongue and began to lick slowly from the base to the tip, and slowly flicking her tongue on his tip much like he did to her clit. He knew he wouldn't be able to hold his load much longer. Leeann opened her mouth and slowly took his cock. Inch by inch Leeann consumed his big cock. She couldn't take it all. But that was fine. She sucked and licked like a pro. Michael couldn't believe how talented she was with her mouth and hands. "Are you sure you've never done this before?" Michael panted. "Nope. I swear." Leeann giggled as she went back to his cock. It didn't take long before Michael knew he was going to blow. "I'm going to cum any second now." Michael groaned. "Should I take it in my mouth?" Leeann asked curiously. "If you want, yes.." Michael grunted. Leeann curiously placed her mouth around Michael's cock again and began to suck and bob her head up and down along his shaft. Within moments he unleashed his load into her hot, wet mouth. Leeann winced a little at the taste but swallowed his entire load. Michael was baffled at how amazing she was at giving a blowjob. For her first one especially. After Michael had finished and put back on his clothing. Leeann got herself ready and was curious as to what was going to happen now that she and Michael had done something sexual together. "So...what happens now?" Leeann asked. "If you're not busy, you can come over tomorrow." Michael replied with a big grin. Leeann smiled and nodded and gave Michael a kiss on the cheek. "Same time tomorrow?" she asked. "Same time tomorrow!" he said. Virgin Sitter Ch. 02 The night after everything had happened between Michael and Leeann, Michael found himself lying awake anticipating the events that would take place the next day. He knew that he had gone to far with Leeann, but he had waited so long and he couldn't contain himself any longer. He had to remind himself that she's still a virgin. He knew he'd have to go easy on her when the occasion would arise. Leeann was just as excited and anxious as Michael. She too lied awake and went over the day's events in her mind. Replaying every intimate detail. Getting wet at the thought. She was both excited and nervous for the next day, hoping that Michael wouldn't pressure her to do anything drastic. At about quarter to twelve Michael heard a quiet knock at the door. He knew exactly who it was: Leeann. She was earlier than normal and he immediately knew she was probably just as excited as he was. He opened the door coolly, trying not to come off too anxious or over excited. "Hey!" she said casually, smiling. "You're earlier than normal." Michael said with a silly grin. Leeann wrapped her arms around Michael with a big hug. He immediately reciprocated. They stood there in the door holding each other for a few moments before he closed the door. He didn't want any of the neighbors getting the wrong idea. Even though their thoughts would probably be accurate. Leeann made her way to the living room and took a seat on the couch where she and Michael shared their first sexual encounter. Michael entered the room silently with a friendly smile. Standing, he leaned forward to give Leeann a kiss. Surprisingly, Leeann brought her hands up to grab Michael's face and pull him in to her. He smiled as he gave in. She began passionately kissing him. Their tongues entwined in each other. Breathing heavily. Michael knew that Leeann wanted him just as bad as he wanted her. He slid his hand down her body feeling all of her beautiful curves. He worked his hand from her breasts down to her pussy. He slowly slid his fingers along the length of her slit. Feeling her smiling in mid-kiss. He could feel her warmth and wetness begin to grow. She could feel a slight bulge in his pants. Even Michael himself was astounded at the restraint he showed not to get himself too hard too quickly. Michael slowly pulled away from Leeann. Breathing heavily he asked "upstairs?" Leeann gave a smile. Michael knew her answer and continued to get up off of the couch. He extended his hand to Leeann and she quickly took hold of it. Michael lead Leeann upstairs into his bedroom. It was dimly lit with sunlight from outside. Michael lead Leeann over to his king-size bed and sat her down. She pulled herself back a little bit to lay on his pillows. Michael stood there in amazement. He couldn't believe what was happening. He had this beautiful, young, tight virgin in his bed. He was astounded. He could feel his bulge begin to rub on his pants. He began to unbutton his jeans as Leeann watched silently. He slowly removed his pants to reveal plain gray boxers with a lump outlining his cock. He took off his shirt and climbed onto the bed. He laid down beside Leeann and gave her a kiss on the cheek. Leeann rolled over and climbed on top of Michael, her cunt right against his bulge. He groaned a little bit and smiled at her. She began to pull up her shirt. Michael could feel his excitement building. She took off of tank top to reveal her perfect 32D breasts in a cute little black lace bra. She stared down at Michael and giggled. He began to unbutton her jeans. After undoing her jeans he slowly began to pull them down to hint that he wanted them off. Leeann rolled off of him and he positioned himself to remove her pants completely. As he slid them down he revealed she had no panties on. "That explains why you feel so wet!" he smiled. "Easy access!" Leeann joked. Michael got up to his knees and pulled Leeann up to the same position. Facing each other Michael leaned in and kissed Leeann. The two began kissing wildly like before. Leaning back and forth like a tree blowing over in a storm. Michael wrapped his arms around Leeann and unsnapped her bra. He took it off and threw it across the room. He looked at Leeann in the eyes and pushed her down onto the bed. He knelt down and began to suck on Leeann's beautiful pink nipples. She was groaning as he would play with her nipples, pinching one while sucking the other. Going back and forth between them as her anticipation built along with his. He moved from her nipples down to her naval. Kissing and licking. She had her fingers wrapped in his short hair almost begging him to go down further. And he did. He began kissing her mound and her hips writhed up into him. He smiled and moved down slightly more. Using his fingers to part her perfect pussy lips he placed his face between her thighs and began violently sucking and licking her wet cunt. He tongue fucked her hole and did circles around her clit with his tongue. His cock was throbbing in anticipation. Leeann seemed as if she may come at any moment. Michael took this opportunity to stop and get his dick covered in her saliva before penetrating her. He didn't want her to cum just yet. He slowly worked his way back up Leeann's body until he was up to her ear. He gently nibbled her earlobe. "I don't want you to feel pressured..." he whispered. "I don't..don't worry.." she whispered back. She gazed in his eyes and gave him a reassuring smile before pushing him off of her. He rolled over onto his back on the bed. Leeann straddled his legs while removing his boxers to reveal his 7 inch cock to her once again. She moved herself forward and began to suck on his balls. He let out a soft moan. She was so talented. She worked her way from his balls up his shaft to the head of his cock. Licking and sucking. Looking up to Michael's eyes seductively. She was being a lot more intimate this time around. After a few minutes of cock sucking Leeann climbed her way up Michael's body. His cock resting between her pussy lips he almost thought he'd explode. "Are we going to have sex?" Leeann asked. Completely shocked that she would actually ask Michael nodded. "If you want.." he said. Leeann smiled and nodded. "But I want you to go slow. Be gentle." she said innocently. Michael gave her a reassuring smile. "Here, lay on your back" he said kindly. Leeann positioned herself on her back as Michael pulled a condom from his bedside table. He placed the condom on his cock and rolled over on top of Leeann. He kissed her softly on the lips before positioning himself to penetrate her. He almost couldn't control himself. He slowly slid the tip of his cock up and down her slit, going over her clit and hearing her moan. He placed the head against her hole and placed his hand around his cock as he slowly pushed. He could see Leeann wince a little bit. He knew it probably hurt her. "Are you okay?" he asked. "..mm..yeah..." she said with slight discomfort in her voice. Michael pushed a little harder and was in. Leeann let out a slight sigh of relief. Michael was astounded that there was no blood as he thought that she would bleed, being a virgin. "You're not bleeding." he sounded confused. "I don't know why not.." Leeann said. Michael wasn't at all worried that Leeann may not be a virgin, he knew she was. She was so tight. He began thrusting slowly as he bent his head down to kiss Leeann. He slowly fucked her as she groaned and moaned. Letting out little whimpers when he would pick up the speed a tiny bit. After a few minutes of fucking her tiny cunt he pulled himself out and put himself back in a couple of times to get her used to his cock. She liked it a lot and would moan super loud when he would go back in. Michael knew he was going to cum soon. "Can I go faster or is this speed enough?" he asked patiently. "Not too fast." she said. Michael re-inserted himself into her and began to pick up speed with his thrusts. When she would begin to moan loudly he would slow it back down with harder pounds. He was going to cum any moment. He began to thrust a little faster and began to rub Leeann's clit with his thumb. She was almost screaming in pleasure. He could feel her cunt beginning to contract in orgasm. A few more fast thrusts and he too, came. He let out a few more pounds as he released his load and groaned. Panting, Michael pulled himself out of Leeann's sopping wet cunt. He rolled over onto his back and removed the condom slowly. Leeann laid there silently, catching her breath. "This is going to become a regular thing." Michael said. Leeann rolled over onto Michael and kissed him on the lips. "I know." she said.