Chapter 1: Kelsey Learns From Tiffany (Kelsey’s first sexual experience)
Chapter 1: Kelsey Learns From Tiffany (Kelsey’s first sexual experience)
Tiffany woke up from her nap, stretching out across her bed, feeling the soft comforter slide around over her naked body. She preferred to sleep naked as often as she could. She enjoyed the sheets caressing her bare skin.
She slowly crawled out of bed and headed for the bathroom, recalling her intensely erotic dream about her best friend. Fantasizing about the soft touch of Monica’s hands on her bare skin, feeling her warm flesh under her fingertips. She felt chills run down her spine and regained her senses.
Once there, she noticed something wet sliding down the inside of her thighs. Upon inspection, Tiffany realized that her entire crotch was glistening with moisture and it was running down her inner thighs. Her pussy began to tingle, causing more wetness to seep down her legs. Tiffany began thinking about what she should do to fix the situation.
She walked out of the bathroom and back into the large dorm room, heading over to her bed to retrieve a box she had stashed underneath.
She crouched down to grab the box and when her legs spread, cool air from flowed over her nether lips, bringing her nipples to stiffness. Pulling the box from under the bed, she opened it up and reviewed her choices. Passing over both her pink dildo and vibrator, Tiff grabbed the glass dildo which her best friend Monica bought for her. It had ridges that wrapped all the way around it in a spiral pattern. She also grabbed her purple pocket rocket.
Tiffany sat on the edge of her bed, spread her legs, turned on her small vibrator and pressed it against her clit. She inhaled sharply as the contact caused a fierce shockwave of intense pleasure to hit her clit and shoot outward, coursing throughout her entire body.
Pulling the vibe away from the top of her slit, Tiffany laid backward down on the bed, spread her legs apart, pressed the tip of the dildo against her wet lips and pushed it all the way into her tight pussy. Holding it inside, she took a deep breath and pressed the vibe against her clit again. This caused her to arch her hips upward a bit, and after a second she settled her butt back down onto the bed. Tiffany started pumping the dildo in and out of her, starting slowly but steadily increasing the pace. She could hear the noises of her own body, the wet sounds of her arousal. As she moved the dildo in faster and faster, the sounds got louder and more wet. She pressed the vibe against her little clitty harder and felt her first orgasm approaching. She pushed the dildo up into her pussy as far as it would go and held it there. Arching her back and hips off the bed slightly, her entire body tensed up and jerked as she came. Tiffany let out and low, quiet moan as she orgasmed. She continued to hold the vibrator and dildo in place, pushing for a second consecutive orgasm. It worked. Her body tensed up a second time. This time her stomach, legs and hips jerked upwards, causing her feet to slip and her butt fell back onto the bed. Even though it was a short drop, the impact forced her hips to bounce upwards, which in turn pushed the vibe hard onto her clit, and another orgasm leapt over her. It wasn’t nearly as strong as the first two, but it felt good, and surprised her.
Tiffany laid there, breathing heavily, holding the dildo deep in her pussy. She turned off the vibrator and set it on the bed next to her. She closed her eyes and started thinking about what she wanted Monica to do to her, starting to slide the dildo in and out of her and a slow and steady pace, building up the intensity. She wanted to take her time, enjoy her fantasies of her best friend and have fun with the glass phallus slipping in and out of herself. Tiffany took her left hand and alternated pinching and pulling on her light pink nipples. The longer she played, the more she enjoyed stimulating her puffy nipples. She didn’t have large breasts, they were a good handful, and big enough, at least in her mind.
Tiffany decided to turn herself over. She dropped down to her elbows, reached her right hand underneath her, between her legs and continued pumping herself with the dildo. She started panting and grunting softly, moving the dildo in faster and harder. The wet sounds coming from her were a little loud. At that moment she couldn’t hear anything other than the sounds coming from the dildo moving in and out of her soaking pussy. Her focus was completely on her ministrations, because of this Tiffany was unable to hear the door open, her roommate Kelsey returned from her afternoon class. Tiffany’s eyes were closed tightly, pumping her dildo into her pussy furiously, grunting and groaning, working her way to another, more intense orgasm, completely oblivious to being walked in on.
Kelsey’s eyes went straight to the glass dildo sliding in and out of her friend’s sopping wet pussy. She gasped and her face turned bright red from embarrassment. Kelsey was a very good and innocent girl. She had never let anyone touch her intimately and she had never even masturbated. She had never seen a girl masturbating before and the sight in front of her surprised her and piqued her curiosity. When she dropped her backpack and Tiffany didn’t notice, she decided she could watch quietly and see what all the fuss about masturbating was really about.
Kelsey stood silently as he friend kept working the dildo in and out of herself. She was intrigued by the sounds she heard coming from her friend’s obviously wet crotch. She didn’t know a girl could get that wet and was amazed. Then, she felt something she’d never felt before. Kelsey was breathing in short, gasping breaths as her face flushed, replacing the embarrassment with arousal. Her nipples began to harden, sending a tingling sensation through her body and straight to her crotch. This new feeling was a good one, and she had no idea what to make of it, she didn’t know what was going on in her own body. She also couldn’t take her eyes off of Tiffany. Kelsey took her hand and grabbed her denim clad crotch and squeezed, not knowing how she was supposed to react to these new feelings. All she knew was that it felt good and she didn’t want it to go away.
Tiffany pushed the dildo into her pussy one last time, as hard and deep as she could. Her body tensed up and jerked forward. A loud grunt like moan escaped her lips as she had her strongest orgasm of the day. As she climaxed, her pussy contracted around the dildo, forcing out her girl cum around the glass and onto her hand.
Kelsey noticed this and was amazed at what she saw. She didn’t know what was happening to her friend.
As Kelsey watched Tiffany, her jaw dropped. She was in awe of her friend. Her mind raced, wondering what had just happened to Tiffany, if she could make herself feel that good, what it would feel like to have that dildo inside herself. Her mind was full of curious thoughts, but her face was blank.
Tiffany, still reeling from the effects of her orgasms, pulled the dildo out of her now drenched pussy and realized she had forgotten a towel, seeing the decent sized wet spot she left on her sheets. She rolled over and laid down on her bed, setting the dildo on her stomach. At that moment she looked up and saw Kelsey staring directly at her, as if she was in some sort of trance.
Startled by Kelsey’s presence, Tiffany’s heart jumped a bit in surprise. She looked at her friend and realized she was just staring, and then noticed her hand over the crotch of her jeans and began to wonder just how long Kelsey had been standing there watching what she had just been doing.
“Hey Kels, are you all right?” Tiffany asked.
“Oh my God, Tiffany, I’m so sorry. I didn’t know... I mean... I...” She couldn’t comprehend what had just happened and why she felt the way she did. She was utterly confused and the embarrassment had come back to her in full force. Kelsey quickly bolted to the bathroom, slammed the door and locked it behind her.
Tiffany jumped off her bed, grabbed a pair of soffes off the floor, pulled them on and ran over to the bathroom. Knocking on the door she asked, “Kels, hun, are you okay? What’s wrong?”
“I don’t know, but I didn’t mean to stare. I shouldn’t have been watching you do that to yourself. I’m so ashamed of myself,” Kelsey replied through her tears.
Tiffany heard Kelsey crying. “It’s okay, I promise. You’ve seen me naked before, and what I was doing is natural. I do it all the time, and most girls do.”
“But that’s supposed to be private, and I’ve never done that before. I should have said something when I walked in.”
“Kels, please come out and we can talk about it. Also, don’t cry, I’m not mad, so just please come out.”
Kelsey decided she couldn’t hide forever. She wiped the tears from her cheeks, unlocked the door and slowly opened it. Tiffany lunged at her, not giving her a chance to retreat and wrapped her arms around her friend. Kelsey returned the favor and wrapped her arms around Tiff, not caring that her roommate was still only half dressed. She just held onto her, embarrassed and ashamed, full of emotions and feelings she couldn’t get a handle on.
“Kelsey, it’s okay, I’m not embarrassed. Please don’t feel bad because of me,” Tiffany whispered.
She let go and stepped back, reaching her hand up to clear what was left of the tears from Kelsey’s cheeks. Kelsey felt comforted by the contact. Tiffany grabbed Kelsey’s hand and walked her out into the room.
Kelsey sat down in the desk chair while Tiffany went into her closet, grabbed a wife beater and pulled it over her head, covering up her remaining nakedness.
Tiffany sat on the bed, facing Kelsey. She looked her in the eyes and asked, “Is there anything you want to ask me about what I was doing?”
“How long have you, y’know, been doing that?” Kelsey asked.
“I honestly don’t remember, but at least since I was about ten.”.
“What was that thing you had inside of you?”
Tiffany turned around and grabbed the glass dildo from her bed. She grabbed a towel from the floor and wiped it off, offering it to Kelsey. “It’s a dildo. Monica bought it for me.”
Kelsey reluctantly grabbed hold of the object and examined it. She could smell a pungent odor which was both semi-sweet and musky at the same time. She suddenly realized it was the smell of Tiffany’s secretions and turned bright red from further embarrassment. Nonetheless, Kelsey was intrigued by the scent she was picking up from the glass toy. Her arousal perked up, battling her continuing embarrassment.
Tiffany noticed Kelsey’s face turn a deep red. “Kels, are you all right? You seem a little flustered.”
Caught off guard, Kelsey looked down away from Tiffany and couldn’t think of what to say.
Tiffany tried to comfort her friend. “Hey, you can tell me what it is, we’ve known each other since we were kids.”
“I can smell your pus... your puss... your wetness on this.” Kelsey stuttered.
“Why would that embarrass you?” Tiffany wondered.
“Because I’ve never smelled anything like this before, and I don’t even know what I smell like.”
Tiffany stood up and started for her closet to get fully dressed. She wanted to try and make Kesley as comfortable as possible. But she had only taken two steps when Kelsey blurted, “Wait!” Tiff turned around and looked at her friend, staring up at her, still holding the dildo in her right hand.
“Can you show me how to...” Kelsey stopped, afraid to ask.
“...how to masturbate?” Tiffany finished.
“If you don’t mind. It just looked like it felt so good, and I’ve never even touched myself before.” Kelsey whispered to Tiffany.
“Sure, if you’re okay with it. It’s no fun if you’re nervous and embarrassed. You have to relax hun,” Tiff explained.
Tiffany walked back over to Kelsey, grabbed the dildo from her hand, went into the bathroom and washed it off with warm water in the sink. “Hey Kels, you should get undressed. Don’t be shy. We’ve got the same stuff.” After she finished, she gathered some items she was going to surprise Kelsey with. She had her razor and shaving gel, for sensitive skin, sitting on the counter. She was looking around for a bucket to fill with warm water.
Meanwhile, Kelsey turned red again, thinking about being naked in front of her friend. She had seen a few of her teammates naked while in the locker rooms back in high school, but she was always too afraid to change in front of them. She always ran off to one of the stalls and changed there, out of the view of everyone else. She bent down, untied her shoes and pulled them off, one at a time, and then her socks. She then stood up and slipped her hands under the bottom of her t-shirt. She took a deep breath to calm her inner fear and jerked her shirt up and over her head, dropping it on Tiff’s bed in front of her. Standing in her tight blue jeans and white bra, she had to muster all of her courage. She grabbed the button of her jeans, hands shaking, and undid it. Kelsey started taking deep breaths, calming her nerves, grasping the zipper and pulling it down. She closed her eyes, grabbed the waistband of her jeans and started slowly sliding them over her round butt and down her strong thighs. Dropping them on the floor and stepping out of them, she now stood in her simple white underwire bra and cotton bikini panties.
Kelsey placed her hand over the crotch of her panties and noticed there was a little wet spot at the bottom. She realized that must have happened when she was feeling all tingly and warm from watching Tiffany play with herself. She took her hand and lightly started rubbing her slit through her panties. She closed her eyes, let out a soft sigh and kept rubbing. She was amazed at how good it felt, and wondered why she’d never tried this before. Her breathing grew heavier and her chest began to flush. Kelsey stopped, realizing she still had her underwear on and that she had to get completely naked. She reached behind her and unclasped her bra, leaning forward and letting it fall off her shoulders and down onto the bed. Her breasts sprang free, and her nipples beginning to stiffen as the cool air passed across them. Her nipples weren’t as puffy as Tiffany’s. They were a bit darker, but still pink. They were longer and a little wider than Tiff’s. The areola was wider in diameter as well, at about two inches across. Kelsey suddenly raised her hands and cupped her soft breasts, squeezing them softly, then reaching up and pinching them. This caused Kelsey to gasp, as her nipples were rather sensitive. She couldn’t believe how good it felt to play with just her nipples. She couldn’t stop pinching and pulling on them. She felt that tingling sensation running through her body, pulsing every nerve throughout, and intensifying right at her crotch. She felt her pussy start to throb and could feel a wetness on her thighs. She stopped playing with her nipples, reached down between her legs and found the source of the wet feeling on her legs. Kelsey assumed it was the same wetness she saw seeping from Tiffany’s pussy when she was pumping the dildo in herself. She brought her finger to her nose and smelled it. It had a similar scent to what she smelled on Tiffany’s dildo. The smell on her hand was a little stronger, but less musky and more sour. She realized what she was doing and didn’t want Tiffany to see her thinking about tasting her own moisture. She wiped it off on her cotton panties, and without thinking, slipped her fingers under the waistband and yanked them down over her hips and all the way off and down her legs. She kicked them aside and stood completely naked.
Tiffany walked out of the bathroom carrying her razor, a can of shaving gel and two white towels. She dropped it all on the bed in front of Kelsey and headed back to the bathroom. This time she came out with only a cleaning bucket three quarters of the way full of warm water, which she set on the floor next to the bed. She grabbed Kelsey’s clothes and tossed them in the hamper. She moved the razor and can of gel over, took the towel and laid it out on the end edge of the bed.
“Sit on the towel, with your legs over the edge of the bed and spread them apart,” Tiffany ordered.
“Why, what are you doing?”
“I’m going to shave that messy patch of hair between your legs. It feels so much better without any hair to get in the way.”
Tiffany went back to the bathroom, this time grabbing the battery powered hair trimmer. She had noticed how much hair Kelsey had between her legs and figured it would be easier if she trimmed all of it down first, then shaved off the short stubble with the straight razor.
Tiffany returned with the trimmer and knelt between Kelsey’s thighs. “Hold very still. I don’t want to nick you.” She turned it on and started at Kelsey’s mound, running the trimmer over all of the hair above her slit first. She then moved down over the lips, carefully cutting away all the hair around there. “Okay Kels, now lay back down and spread your legs further apart.” Kelsey did what Tiffany told her and Tiff went back to work. She grabbed each of her lips and pulled outward, moving the clippers over the soft folds, careful not to get too close. Now Tiff pushed Kelsey’s legs as far apart as she could and trimmed the hair down by her butt and around the bottom of her butt cheeks.
Now it was time to apply the shaving gel. She the razor and can of gel. She popped the cap of the can off and squeezed a generous amount of gel onto her hand. She started lathering the gel into a foam with both of her hands, warming it up in the process. Tiff then started applying the now semi-warm foam to Kelsey’s crotch. She started the same as before, up on her mound, then she slowly moved down over her lips and finally down over the bottom area of her butt.
Kelsey felt the warm foam hit her mound and inhaled sharply. As Tiffany worked it down and over her lips, she felt that tingling sensation again, this time radiating outward from her crotch and through her entire body. Her nipples once again stiffened, but this time they became incredibly hard, much harder than either time before. It was as if they were cold, but her body was very hot right now. Her chest became flushed again. Her face getting red again, but instead of it being caused by embarrassment, it was caused by arousal. She reached up and cupped her breasts, kneading them, going on primal instinct alone. She started pulling and twisting her nipples. Her breathing became heavy again and Tiffany noticed.
Tiffany concentrated on the job at hand, but Kelsey’s sudden brazenness shocked her a little bit. She never expected her to start playing with her breasts, at least not while she was shaving her. Tiff took the razor and began shaving Kelsey’s mound, carefully dragging the blade over her soft skin. Rinsing the blade off in the bucket of water after shaving each section. She took her thumb and forefinger and pulled on Kelsey’s lip, stretching it tautly. Kelsey gasped sharply when she did this. Gently bringing the razor against the sensitive flesh, Tiffany pulled it from the crease where her crotch met her thigh and over her labia in toward the center of her slit. She continued this until one side was completely devoid of hair. Tiff then repeated the same process on the other side. She then carefully ran the razor over the area below Kelsey’s pussy and between her butt cheeks. There wasn’t a lot of hair to get rid of there.
Kelsey had her eyes closed at this point and was just overwhelmed with feelings and sensations she’d never experienced before now. Her chest was completely flushed red, all the way from her neck down midway over her breasts. Her nipples were the hardest they’d ever been in her life, even more so than when she was out in the cold without a bra, or after she’d taken a dip in a cold lake. She could feel her pussy throbbing and getting very wet at this point. She was consumed with lust and fire.
Tiffany ran her hands over the freshly shaved flesh and noticed a somewhat sticky moisture on her fingers after bringing them down over Kelsey’s lips. She then looked close and realized that Kelsey’s pussy was a deep pink color, swollen and was getting rather wet.
“Do you still have your cherry?” Tiffany asked.
Kelsey snapped out of her lust-filled daze, “My what?”
“Your cherry. You know, your hymen?” Tiff repeated.
“Oh. No, I think it broke while I was playing volleyball or something,” answered Kelsey.
Tiffany looked down and examined her friend’s clean shaven pussy and couldn’t help but notice that it looked like a fresh virgin pussy. The inner lips weren’t clearly visible, her clit was tucked in between the outer lips, which were, despite her arousal, tightly tucked together. Tiff could tell Kelsey was very tight and decided that no more than one finger would work to start with. She took her right hand, placed her index finger on the center of the bottom of Kelsey’s tight little lips and started pushing in. Kelsey took a deep breath, waiting for it. Pushing harder, Tiffany worked her finger in between the well-lubricated lips and into Kelsey’s tight, virgin pussy. It was tighter than Tiffany had expected and she was rather surprised that her one finger fit in quite snugly.
Kelsey couldn’t believe how good a finger felt inside of her. Her whole body was tingling and felt so alive. Her head was spinning with pleasure. She felt incredibly hot, like she was on fire, but it felt good, very good. She started breathing faster and instinctively raised her hips off the bed, forcing her pussy onto Tiffany’s finger completely.
“Do you want me to keep going Kels?” Tiff asked.
“Oh God yes, don’t stop now, it feels SO good!”
Tiffany carefully added her middle finger and pushed it in to join the other one. Kelsey was immensely wet at this point and Tiff could feel the walls of her pussy contracting in excitement around her fingers. She just held them in her, allowing her virgin pussy to get used to the greater insertion.
Kelsey released her breasts and dropped her hands to her sides. She grabbed the sheets and held on tightly, arching her hips higher into the air, lifting her butt off the bed.
Tiffany began pumping her fingers into Kelsey’s tight pussy. Starting slowly, then increasing the speed as she went along. Curling her fingers upwards, she turned them so on every stroke, they grazed Kelsey’s g-spot. As she moved faster and faster, Tiffany was getting her fingers very wet, wetter than she’d ever gotten them while fingering herself.
Kelsey suddenly felt a stronger tingling, directly inside her pussy. She didn’t know what it was, but it made her feel like she had electricity shooting throughout her body and exploding in her pussy every time Tiffany’s fingers went in and out of her slit. She didn’t know how much more she could take. She was beginning to get dizzy and very light headed. Her body was tingling much stronger than ever before. She kept pushing her hips up and back down, matching the movements of Tiffany’s fingers moving inside of her.
Tiffany then noticed Kelsey’s clit just barely peeking out from the top of her slit and realized she hadn’t really touched her there yet. She took her left hand, wet her index and middle fingers in her mouth and pressed down directly on Kelsey’s erect clit. Kelsey yelped at the contact but kept moving her hips in tune with Tiffany’s thrusts. Tiff pressed down even harder and started moving her fingers in circles, faster and faster.
Kelsey felt her entire body stiffen and felt like she was going to explode from her crotch outward. She clenched the sheets as hard as she could, arched up high and let out a loud moan. Then her legs started shaking and buckled, dropping her back onto the bed. She felt even more light headed than before, like her head was spinning in circles a hundred miles an hour. Her entire body was tingling intensely now and she felt and incredibly strong electric shock run through her entire body, she felt amazingly alive, and at that moment, she screamed, “OH GOD, OOOOOH, OOOOOH, OOOOOH!” She let out one last squeal as the first orgasm of her life pulsed through her innocent body, collapsing onto the bed. Kelsey couldn’t move as her entire body was throbbing and tingling.
Tiffany looked at her friend. Kelsey’s entire upper torso was a bright red. She had a sheen of sweat covering her entire body. Her eyes looked glazed over and she was panting heavily. She pulled her fingers out of Kelsey’s pussy, which was less tight, but more wet now. She climbed on the bed and straddled Kelsey’s abdomen, leaning down she pressed her two soaked fingers against her friend’s lips and pushed.
Kelsey opened her mouth and let Tiffany slide her fingers, coated in her cum, into her mouth and over her tongue. She was so out of it that she didn’t care, and in fact, she thought it tasted good. It was something she’d never tasted before and she licked Tiff’s fingers clean. When Tiffany removed her fingers, Kelsey closed her eyes, relaxed and fell asleep from exhaustion.
Tiffany hopped off the bed and headed for the showers. She grabbed her big towel and headed for the door, letting Kelsey sleep in peace and what she assumed must be pure bliss. “I’ll have to teach her how to do that herself later,” she thought to herself as she took one last look at her once very shy, innocent friend, laying naked on her bed with a shaved pussy, sleeping after having her very first climax. She noticed that her own pussy was very wet and she had wetness sliding down her thighs almost to her knees. Her nipples were painfully erect and she was starting to get flushed. She decided she would have to take care of herself again in the shower while Kelsey slept. She checked to make sure she had her room key with her, then closed and locked the door behind her, wondering what she was going to do about Kelsey after she woke up.