0 comments/ 11163 views/ 0 favorites For The First Time By: Serenata Cynda's palms were sweaty as she gripped the steering wheel. She had never done anything like this before. She spent the whole hour-plus car trip wondering if she was doing the right thing. As she pulled into his driveway, she realized there was no going back. Her body told her to walk to his front door; her mind was full of doubt. "What if he's a total creep?" she thought. But her body won. Something deep inside her, something sensual, told her to meet him. She needed to be loved in the way only a man can love a woman. And she had the feeling that he was that man. Cynda stepped out of her blue 1997 Chevy Lumina. It wasn't in perfect condition, but it worked. She was wearing a pair of jeans that flattered her round ass and ample hips. Her shirt was a dark blue, button-down with 3/4 length sleeves. She thought of it as her "sexy-casual" outfit. She took deep breaths as she walked up to his front door. "Okay, Cynda, you can do it," she whispered to herself as she rang the doorbell. Her stomach was full of butterflies. This was the first time she had ever met Alfred, or Fred for short. Fred answered the door. Cynda was pleasantly surprised. He stood 6'3" tall with gorgeous red hair and brown eyes. He was lean and muscular, a contrast from Cynda's curvaceous, womanly form. "You're even more handsome than I imagined you to be," Cynda smiled and broke the ice. "And you're more sexy than I imagined," Fred returned the smile. "Are you ready to go to dinner?" Cynda asked. They were going to go to dinner to see if the chemistry was right. If things went well, they planned to go to Cynda's apartment in the city for a night of really getting to know each other. Fred replied, "I'd love to go to dinner with you." She lead him to her car. He opened the driver's door for her. Cynda loved the gentlemanly notion. She started the car as he walked to the passenger side and got in. Fred gave directions to his favorite restaurant and before long, they were enjoying a great meal and even better conversation. Cynda felt the butterflies subside and her muscles relax. She wanted to take him home. By the time the bill came, the conversation had turned sexual. Cynda was getting very turned on and from the look on Fred's face and the tone of his voice, she figured that he was pretty turned on, too. Her panties were moist with anticipation. When the bill arrived, they split it 50-50. Going Dutch is always the best idea for the first date. They paid it quickly and headed for Cynda's car. They got in and before she started the car, she asked, "Do you wanna come home with me? I really want you to." Fred leaned across the seat and kissed her passionately. He licked her lips teasingly, but did not let her taste his tongue. "I take that as a yes," Cynda smiled as she started her car. The sexually charged conversation continued on the ride home. About 45 minutes into the trip, Cynda decided to try something. With her left hand on the steering wheel, she reached her right hand over to the noticeable bulge in Fred's pants. Through the cloth, she rubbed and massaged his cock. The conversation slowly died as Fred closed his eyes and leaned his head back. After about 10 minutes of rubbing, Cynda told him to unzip his pants and pull down his underwear. His impressive and very hard cock sprang free. She played with his balls, teasingly, for a little while. The she slowly slid his hand up his shaft and teased his head. She rubbed it with her thumb and forefinger until she felt a few drops of pre-cum seep from his dick. It was just enough lubrication. She slid her hand up and down his shaft. Soft moans escaped his lips. Her exit approached and she pulled off the highway. At a stoplight, Cynda leaned over and licked the head of his cock quickly. She could tell that he was about to cum, but they arrived at her apartment first. "We'll have to finish that later," Cynda coyly said as she turned off the car. Fred pulled his throbbing member into his pants and got out of the car. She unlocked the door to her tiny apartment and let him in. As soon as the door was closed and locked behind them, she dropped to her knees and unzipped his pants. His cock leapt from his silk boxers. In no time, Cynda sucked him off. He shot his large, sweet load into her mouth. She gulped to swallow it all. When he was finished, Cynda stood up slowly, keeping her face within inches of his body and her hands on his sides. Her face met his and their lips met. Fred could taste a hint of his salty sweetness on her lips and when he slipped his tongue in her mouth, the taste was even stronger. "Put your underwear back on, but keep your pants off," Cynda said as she walked to her stereo. She turned on Aerosmith's "Cryin'" and pulled a chair from her kitchen table. She pointed to the chair, "Sit there." Fred obeyed. "You can only touch me when I say you can. I'm going to put on a little show for you," Cynda smiled as she began gyrating her hips and unbuttoning her shirt. She sensually unbuttoned her blouse, slowly exposing her lacy bra. When it was completely undone, she tossed her shirt aside. She approached him and straddled his lap, grinding her pelvis into his as she touched him sensually. After a few minutes of that, she stood up again and removed her pants, socks and shoes. She was just wearing her bra and panties. Then she straddled his lap and pulled his shirt off, exposing his manly chest. Cynda kissed his ears, neck and shoulders. She could tell that he wanted to touch her, please her, but he couldn't. Cynda leaned back and unhooked her bra, letting her breasts fall out. Her nipples were hard and they ached to be sucked. "I want you to touch me now," Cynda whispered in his ear. "Touch my breasts. Rub them, kiss them, suck them–whatever you want." Fred rubbed her nipples between his thumb and forefinger while Cynda continued to grind her pelvis to his. She could feel the bulge growing in his silk boxers and her lacy panties were getting wetter and wetter. He moved his lips to her breasts. His hot, wet tongue felt so good on her aching breasts. Cynda moaned, for she was nearing orgasm. Her grinding became more furious and her breathing quicker. "I'm . . . cuming . . . I'm . . . cuming!" Cynda cried between breaths. While her body shook with orgasm, he continued to suck and lick her breasts. "Now it's time for the REAL fun," Cynda smiled as she grabbed his hand and lead him to her bedroom. She sprawled on her bed, still wearing her now-soaked panties. Fred kissed her on the lips, then kissed his way down to her pelvis. He removed her panties and began to lick her clit. "Not now, Fred. I want you inside me in the worst way. I want you to fuck me." Without missing a beat, he kissed back up to her lips. Their bodies were close together, hot and sweaty. Cynda loved missionary position because she loved to feel his body so close to hers. She tilted her pelvis up and he slowly entered her, easing into her silky pussy. Waves of pleasure rippled through her body with every inch of meat he thrust into her. Once he was fully into her, he held himself there for a minute. Cynda moaned loudly; she liked to be kind of noisy in bed. He slowly pulled out and started a slow, grinding rhythm. Cynda moaned and sighed with pleasure. "Mmm . . . Fred . . . faster . . . harder." He immediately picked up the speed. She felt his balls slapping against her ass. Their breathing grew faster and Cynda's moans grew louder. "I'm . . . fucking . . . cuming!" she screamed. Her pussy walls tightened and milked Fred's member until he came, filling her cunt with his seed. Breathless, they laid side-by-side on her bed, cuddling and whispering until they fell asleep in each other's arms. For the First Time A special thanks to LaliaLewd for the editing prowess. Please leave your thoughts and any tips you might have. Enjoy. * Dan stood staring at his reflection in the bathroom mirror trying to calm his nerves. Trying to stay in control, stay cool and relax. After all the make out sessions, heavy petting and the odd but incredibly satisfying blow jobs, Kassy said tonight was the big night. They were at Jeff's place, in his basement and the party was just getting started, everyone was getting changed out of there formal wear and pouring themselves a drink. Jeff's mom was more easy going then most everyone elses' parents and had offered up the basement for their own after prom party instead of going to the bigger, cop monitored, party that was held on the soccer field beside the school. Better you act crazy here where I can keep an eye on you was what she always said. Dan stripped off his dress pants and shirt and stood in his boxers as he rummaged through his back pack for his favourite jeans and t-shirt. With a quick knock, Kassy opened the door and slipped inside, she was already out of her prom dress and into more comfortable clothing. "Your still not changed?" she inquired as she put her arms around him and moved in close. "What have you been doing in here all by yourself, the excitement too much for yea?" She giggled and pressed her body into his, kissing him deeply. Kassy stood 5'8", with shoulder length brown hair and incredibly dark brown eyes. She had a nice tan form sun bathing the day before and her soft full lips felt like heaven. She was wearing a little pair of baby blue bed shorts that barely covered her ass and a care bear tank top that fit tightly across her C cup breasts and then hung loose exposing her belly. Kassy was just a little over weight but was too confident to let that stop her from showing off her body. As she pulled away they both looked down to see a bulge starting to form in the front of Dan's boxers, she gave him a sly smile and started to message his cock through his boxers. Dan closed his eyes and gave into the pleasure. He was hard as a rock within seconds. Kassy pushed him back against the wall and pulled his boxers over his raging hard-on, letting them fall to the floor. She kept messaging him and leaned in close, "how about a little release to ease the tension." Dan gulped and nodded his head and she worked his cock and kissed his neck and chest. Dan was lost to the world, lost in the scent of her perfume, the warmth of her mouth as she left wet kisses everywhere and her soft hands as they pushed him towards climax. He tried to fight, tried to last longer and enjoy the attention but Kassy cupped his balls with her free hand and picked up the pace of her strokes, pushing him over the edge. Moaning loudly, Dan came all over her hand and belly as she aimed his cock towards her. "Wow," she said "that's so much cum! You sure you'll have anything left for later?" She giggled and started cleaning herself with some tissue as Dan slowly came back to reality. Dropping the tissue in the waste basket, Kassy turned and kissed him on the cheek giving his cock one last rub and said, "don't be to long, everyone else is already mixing a drink." With that, she smiled and slipped out the door and back to the party. Dan took one more minute for himself before pulling his boxers up and putting his jeans on. All the tension that was there before was completely gone now and Dan was looking forward to the rest of the evening. He packed his tux up and slid a superman t-shirt over his head. Digging in his back pack again he pulled out his eight-pack and downed half a beer with a satisfied sigh. They had to get Kassy's older sister to get them alcohol as Dan had only turned eighteen three weeks earlier and while Kassy and the others at the party where graduating from high school, Dan still had another year to go. Turning the light out as he left, Dan stepped out of the bathroom and into the rec-room with the others. There was ten people, all close friends, with the exception of Dan who had only met them when he first met Kassy. The others had grown up together in town and went to the same schools there whole lives, Dan had moved to town with his mother only two years prior and had some trouble fitting in. He stood 5'10" with black hair and brown eyes, his slim build and glasses made him an easy target for the jocks. Dave, Jeff, and Will had slowly warmed up to him over the last year, only giving him a chance because he was with Kassy and the girls in the group liked him, cause he treated Kassy well. Or so they said. Dan put his beer in the fridge and gave Kassy a kiss as he wrapped his arms around her midsection. The two stood there laughing with friends and drinking as the night drifted on. Dan and Kassy found themselves a chair and relaxed with Kassy sitting on his lap as the others paired off on there own. The conversation continued here and there with each pair taking little break's to make out or fondle each other. Dan had his hand up Kassy's shirt pinching her nipples and messaging her tits as she slowly ground her ass on his lap getting them both worked up. When Kassy was turned on she got really wet and tonight was no different, a little bit of her shorts where damp with pussy juice and the smell that drifted up was intoxicating. She buried her face in his neck and started kissing and biting him as Dan surveyed the room. Will and Tammy where completely occupied with each other in the opposite arm chair and Jeff and Miranda where getting up and heading toward his room. Him and Dan exchanged nods as he walked by not trying to cover his hard on at all. Lisa and Katie where making out and moaning softly on the couch, they had their hands down each others' pajama pants. Cindy was kissing her way down Dave's chest when she noticed him paying way more attention to Lisa and Katie then to what she was doing. At which point she jumped off him and went to the bathroom without a word. Dave spent the next twenty minutes saying how sorry he was before she let him in and closed the door. Kassy moved so her back was to Dan and started bucking her ass on his crotch more and slid Dan's hand down the front of her shorts. To Dan's surprise her thick mound was gone; all he could feel was just a small strip. "You like that baby," she cooed, "I shaved it down for you; I wanted you to be able to see yourself fucking me for the first time without anything in the way." Dan didn't say anything, but showed is approval by sliding a finger deep into her wetness. She was soaked, her shorts were noticeably wet and what was left of her pubes where damp to the touch. He slid his finger in and out slowly a couple times then buried it to the knuckle and Kassy moaned with pleasure. He repeated the same motion over and over working his finger as deep as he could get it until she was ready to climax. Dan pulled his hand away and let Kassy lick her juices off, this was something that Dan loved to see and his cock was getting so hard it was becoming painful inside his jeans. He started to dry hump her as he buried his hand in her pussy again, this time two fingers and then three. He could barely fit the third finger inside her tight young pussy and she was moaning and begging for him to push them deeper. "Oh fuck baby that's it, finger me hard baby," she groaned, "ooohh yea! Fuck that feels good." She was grinding her pussy on his hand and his jeans where starting to get wet as Kassy soaked through her own shorts. Dan could hear sex all around him; Tammy was making loud slopping noises as she sucked Wills cock and played with herself. Lisa had Katie on her hands and knees on the couch as she finger-fucked her and licked her pussy from behind. Katie and Kassy locked eyes for a moment just before Katie came and collapsed. "It's so fucking hot when those two go at it." Kassy said as she pulled her shirt up so she could play with her nipples easier. Dan slid his fingers out of her and started working her clit, in quick circles. She reacted by grabbing both her nipples and pulling on them hard as she arched her back. Dan knew that meant she was ready to come so he put two fingers back inside her and fingered her as fast as he could. Kassy moaned and shuddered as wave after wave of bliss washed over her body. She fell back panting against Dan as he put each finger inside her slowly before putting all four in her mouth to clean them off. After she licked his hand clean, Kassy spun herself around so they where face to face again. She kissed him long and hard for several minutes before she stood and told him to fallow her. They went past the bathroom where they could hear Cindy begging to be fucked harder. They found Jeff's older sister's room, she was away at college for the last couple years and this room was barely ever used. Kassy closed the door behind them and the two grabbed each other again, kissing and groping. Kassy slid herself down onto her knees and started undoing Dan's jeans. When she popped the button and undid his fly his cock burst out fully erect and rock hard. Dan let out a sigh of relief now that the pressure was gone. Kassy pulled his boxers down and immediately went to town licking his shaft and sucking on his balls. Dan almost came before she even got his cock in her mouth and had to ask her to slow down a little. "Don't worry baby," she said between mouthfuls of cock, "it's your first time; you can come as much as you want." With that she went back to working his balls and rubbing his cock with one hand as she played with herself with the other. She stopped for a moment to pull her shirt off and discard her soaked shorts, giving Dan a moment to compose himself and finish undressing. She pushed him back onto the bed and straddled his knees, making a show of pushing her fingers deep inside herself. She moaned and bucked her hips as he watched, even this was becoming too much and Dan thought he might cum without her even touching him. But she didn't give him time, she garbed his cock with her wet fingers, smearing herself all over him and then swallowed his cock so deep she choked a little. That last action was too much and he came hard and without warning. He shot a big wad in her mouth before she could move away and then spurt the rest all over himself, Kassy and the bed. "oh god, oh shit, sorry baby. I didn't mean to get it in your mouth." He said, still trying to find the world in all this ecstasy. Kassy licked her lips and swallowed his cum. "Don't worry about it this time, oh what a mess; I'll clean you up before we continue." She leaned down and licked the cum off his belly and cock, spending extra time licking the tip. "I hope you're still ready for more." She whispered as she moved her pussy over his cock. Slowly and without taking her eyes off him she lowered herself down onto his still hard cock. Just the head first, Kassy held his gaze as she rolled her hips around and moaned softly. Dan had been waiting for this for his whole life and Kassy's pussy didn't disappoint. He thought that he might not be up to it after cumming moments before but once his cock slipped inside her every nerve in his body came to life again. Without warning she dropped down on him, buried him inside her juicy womanhood. Dan could feel pussy juice running down his thighs as she bucked back and forth. With a deep groan she started to bounce up and down on him with reckless abandon, her fingers found her clit and she rubbed it frantically as she built towards orgasm. Dan didn't even move, he just laid their drinking it all in. The sounds of Kassy moaning over his cock, the squeak of the bed, the wet slapping noise her ass made when she landed on his thighs. Her body glistened with sweat and sex, her tits bounced in rhythm and she pulled on each nipple with her free hand as her other hand worked her clit bringing her closer and closer. For Kassy the world was a million miles away, she had wanted Dan's first time to be special but once she got his cock inside her, she was only concerned with getting off. His dick was the perfect fit; it filled her up and was just long enough that she could feel the head reach the very depths of her cunt. She was fucking him with everything she had and she could feel a powerful orgasm building, screaming to be released. All of a sudden she felt Dan stiffen and suck in a huge lung full of air as he blasted his load inside her. She could feel his cum spraying all over her insides and that was more than enough to push her over the edge with him. Kassy's mind spun as her body was rocked with wave after wave of pleasure. She could feel every inch of her being come alive as she bounced on Dan's cock as hard as she could. The two of them convulsed and gasped for air as they tried to come back down to earth. She collapsed forward onto his chest and Dan put his arms around her, drawing her close as he slowly got soft insider her. Neither one of them spoke, they just laid there drenched in sweat, cum and pussy juice. The scent of sex filled the room and Kassy could feel his cum slowly dripping out of her but none of that mattered. She slowly slid to the side and rested her head on his chest. Dan was still breathing heavily when he noticed Kassy had already fallen asleep, completely drained form all her effort. He didn't try to wake her or even draw any covers up around them. He just held her naked body close to his and drifted off to sleep with her. For the First Time Taking a deep breath, I could feel my hand making its way to the door knob as my heart began to race. In my mind, I still couldn't decide whether to do it or not but everything seemed to be going in a certain direction. The door creaked slightly as it opened and I started to notice the outline of my landlord behind it. She was a really nice lady in her late fifties who could never have imagined what I was about to show her. As the door opened wider I was sure she started to notice me too. My dark purple blouse and black legging were far from outrageous but, taking into account that she has only known me as Chris, it must have been a bit of a shock. When the door was fully open, I closed my eyes. A small gasp greeted my reaction and I felt a lump in my throat. I could not utter a single word but finally, after gathering all the courage I had left, I managed to say something. I am so sorry Mrs. Lange, I'll understand if you no longer wish me to stay here and I will leave as soon as possible but I just had to do this. I could feel the tears rolling down my cheeks as she gently pushed me aside and closed the door behind her. My eyes still didn't dare to look at her directly and I didn't know what to do with myself. Then, to my surprise, I felt her hand on my shoulder. You don't have to leave Christopher, but tell me, how should I call you. Christine, I said. My voice quavered, barely making any sound. When I looked at her face, I could see that she was trying to understand something she was not yet ready for. Maybe my move was too sudden, but I could not continue like this any longer. I've been living in this apartment for almost two years and to Mrs. Lange I was just Chris, the well mannered guy who lived on the second floor who would just keep to himself without bothering anyone. I began to stutter when she guided me to the sofa and invited me to sit down. With a caring smile, she told me I didn't need to say anything, at least not right away. I took another deep breath and offered her something to drink. Yes, dear, she said. I think a drink is in order. I smiled and went to the kitchen, making sure my every move was as ladylike as possible. I didn't want to make a mockery of the whole affair. Once in the kitchen, I told myself to calm down and, seeing my reflection in the glass cabinet I had there, gave me a bit more confidence. I went back to my small living room with two glasses of whiskey and apologized in case I'd gone over the top with the drinks. Oh, don't worry about it. It's just what I needed. And, by the look of it, you need it too, she said. I sipped my drink, still looking at my lap, when she said, you look lovely. That color really suits you. It was the first time anyone had ever seen me as Christine and I didn't know how to react. We began to talk and I realized how my voice sounded forced and high pitched so I tried to relax a bit in order to sound more natural. At first she asked me about how I was doing at work and if I liked living here. We'd had this conversation a million times and I reckon she did it to make me feel more comfortable with what was going on. At some point the elephant in the room was too much to bear and she asked me point blank, why? I told her I didn't know. From a very young age, I knew there was something different about me. I was never an outcast at school or anything, but I knew I was just different. I told her how I started to dress up as soon as I moved out of my parents house, the internet being a blessing to us all, and how it would make me feel at peace with myself to be like this. How it was not just a thing that would turn me on but a thing I needed to do to be me. She was silent for a moment but then reassured me that it was OK for me to stay. I'd never given her any trouble and though we were not close, we always kept an amicable relationship. Thank you for understanding Mrs. Lange, I said. I promise I won't do anything like this again. I don't know what got into me. Oh, please, don't trouble yourself. I'm sure we'll have plenty of time to talk about this in the future but I think I must go now. Though she appeared calm, I could see she was still shaken by what had happened. It is not everyday that one of you tenants, who is a male, welcomes you as a young woman. I walked her to the door. And by the way Christine, you're quite lucky I live downstairs. Those heels do make a very distinctive sound when you walk around with them. I was speechless as she left but then realized I'd forgotten something. Oh, Mrs. Lange, I heard myself say in a girly voice. You forgot to collect the rent.