"Frosh" (closed)

[WatchingCloud]

Helen's blowjob was, as before, wonderful. The attention, however, was short-lived, a tease to get him worked up. He didn't mind too much, knowing what they were really here for.

Helen rose and reached for her boy shorts. Chase had long envisioned this opportunity - undressing a woman, getting his first view of a woman's pussy from up close. He felt comfortable enough (just) to ask if he might have the honors.

Helen smiled, and as she moved up closer to him, she said, "Please do."

Chase scooted forward to the edge of the couch and she stepped up close. He kissed her tight tummy, teased her belly button, and savored the feel of her smooth skin against lips and cheeks. Hands ran up her legs until finding the waistband of her boy shorts and began pulling them down.

He planted a few kisses downward on each inch of exposed flesh as it became visible. As he reached her pubic bone, he pulled back just enough to see her pussy as it was revealed. Her skin was incredibly smooth and there was a slight glisten to her labia. He caught just a hint of her aroma.

"Kiss me," she whispered as if reading his mind.

Chase leaned in, nose pressed into her mound, and planted a kiss just above her slit. Heaven. He kissed again and again, each time just a bit lower. Growing bolder, he flicked his tongue out and across her, getting his first good taste - surprisingly...fruity? She must have applied something in preparation for tonight. Whatever it was, he loved it. This was what he'd waited so long for - the taste, the feel, and smell. Everything with which porn fell short.

"Would you like to taste me?"

Chase thought he just had, but realized she meant really taste her. This was an awkward angle. He looked up and nodded.

"Very much."

She switched positions with him, leaning back on the couch while he got to his knees between her legs. Here, Helen was spread wide and fully exposed to him. He took a moment to appreciate her unique shape, the folds and color, the little nub of her clit peeking out.

"I'm, uh, new to this, of course," he said. "If there's anything I'm doing right or could do better, please let me know."

It seemed an awkward thing to say, but she knew he was a virgin and eager to learn. He couldn't have been the first to ask this of her. Helen's expression suggested she didn't mind a bit.

Chase leaned in, kissed her inner thigh on both sides, then licked up the entirety of her slit with one long, firm stroke. His tongue sank through her folds, absorbing far more of her flavor than before. Yes, this was tasting a woman, and it was better than he could have imagined. He took his time, exploring her with his lips and tongue, slowly working his way back up toward where he'd seen that clit poking out.

 

[LoriDean12345]

He took his time, exploring her with his lips and tongue, slowly working his way back up toward where he'd seen that clit poking out.

"Not yet," Helen said softly as she realized Chase was about to go for her clit. She'd had one or both hands on his head, encouraging him in his movements about her womanhood and now took a handful of his hair to hold him back a few inches. "I want you to look at me for a moment. I want you to know me … to know a woman."

As she stood, she pushed Chase out from within her parted knees. Leading him, they made their way to the suite's bedroom, where Helen turned on the overheard light and all four table lamps; the room was flooded with illumination as she went to the bed. She pulled back the layers of bedding until all but the bottom sheet were gathered along the very end of the king sized bed. Then, gathering the pillows against the headboard in the middle, she laid back … and spread her knees once again.

"Come to me, Chase," Helen said with a soft tone and a suggestively curling finger. The fingers of the other hand trailed down to her pussy and parted her outer labia, revealing the pink of her glistening inner folds; her clitoris was fully on display. "Come look at me … see me. I want you to know me--"

She glanced at his cock, which had softened somewhat but now -- as she revealed herself again -- was rapidly beginning to harden once more. She finished her statement, "--like I know you."

 

[WatchingCloud]

"Come to me, Chase," Helen said with a soft tone and a suggestively curling finger. The fingers of the other hand trailed down to her pussy and parted her outer labia, revealing the pink of her glistening inner folds; her clitoris was fully on display. "Come look at me … see me. I want you to know me--"

Chase could scarcely believe Helen was doing this for him. Maybe she fancied herself as much a teacher as an outlet for her clients. She'd said she preferred virgins. He wasn't going to complain one bit.

He crawled between her legs and bent down, his head no more than a foot or so away from her pussy. He marveled not just at the sight - her unique folds, the glistening pink that vanished into her vagina, the precious nub of clitoris - but her easy comfort and confidence. That was what truly made her so attractive.

"--like I know you," she continued.

Chase, after taking his time exploring her visually, began to run his fingers along her outer labia, getting a sense for how the skin yielded and how she responded. He continued on with the inner labia, fingers now becoming slick with her moisture. He ran a single finger tip up and around, but never quite touching, her clit. Her breathing was becoming a bit deeper, so he figured even his casual exploration was affecting her.

He slid that one lone finger back down through her slit and then tentatively inserted it inside her, first one and then two knuckles disappearing. It was another mystery from which the screen had been pulled back. She was every bit as warm and slick as he'd imagined it would be, yet also tighter. His cock throbbed at the thought of being buried in there before too long. But he wasn't done here yet.

"Is this okay?" It was probably a rhetorical question, given how her body seemed to be responding.

 

[LoriDean12345]

Helen's job, of course, was in pleasuring her Johns, not in seeking her own pleasure while on the job. If she was out to achieve her own orgasm -- or orgasms, plural -- she knew a handful of men who would leave the doors of their homes unlocked for her to pay a visit.

But sometimes she got lucky and found a young man with whom she might be able to have the best of both worlds. Chase seemed to be just such a man as he inquired, "Is this okay?"

Helen's chest was already rising and falling at the pleasure his fingers were causing, and she was beginning to shift her lower body a bit as he began touching her ever so sensitive clitoris.

"It's very okay," she told Chase playfully. She let him touch and explore her nub, folds, and hole for a minute or so, during which her reactions became increasingly more obvious. Helen purred, "You're a natural, Chase. You're gonna … you're gonna make a lot of women … very happy in the future."

She reached a hand down to one of his and guided his finger tips on and around her clit, giving him instruction on not only how to touch a woman but on how to read her reaction to his touch.

"Don't hurry," she told him, her breathing getting more strained. "Let your lover … set the pace … when you are pleasuring her like this. Feel free to ask if she likes it, but … don't act creepy … don't sound creepy. Make sure she knows this is all about her."

Helen continued to direct Chase for another minute or so. She already knew that she could orgasm is they maintained this. But, the young man hadn't paid to drive Helen to climax; he'd paid to be driven to climax by her.

"Would you like to spend the night with me, Chase?" she asked. When he looked into her eyes, Helen explained, "We could take our time … make love … rather than just … you know … fuck. Would you like that?"

 

[WatchingCloud]

"You're a natural, Chase. You're gonna … you're gonna make a lot of women … very happy in the future."

Chase was humbled by the compliment and hoped it would be true. For the moment, however, he was only interested in making one woman very happy.

Helen subtly guided his fingers and he absorbed it all, like a masterclass on pleasing a woman. He continued on for several minutes, going slow just like she told him, and watched as the heaving of her breasts continued to grow.

Would you like to spend the night with me, Chase?" she asked. "We could take our time … make love … rather than just … you know … fuck. Would you like that?"

The offer floored him. He got the difference between the two, even if he'd experienced neither. Or was she just offering him the opportunity to upgrade his level of service into a more comprehensive girlfriend experience? He knew what he wanted, and it was definitely spending the night. If he had to pay, though, could he afford it? Would he kick himself later for not taking the opportunity?

And there was the other bit. She was so likable, so accessible, he was falling hard for her. That couldn't possibly end well. He just had to keep reminding himself that she was a professional, not a girlfriend. He could do that, right?

"I would," he said. "I would very much like that."

His fingers continued their slow, steady stimulation as he looked her in the eye, trying to grasp what she really meant.

 

[LoriDean12345]

Helen saw the excitement in Chase's eyes and smile. But a moment later, there was hesitation as well; he was thinking about the money … his money … money he simply couldn't afford while on financial aid.

"No additional visit to the book store tomorrow," she said with a smile, not wanting to actually use the words you don't have to pay more for this. "So...?"

"I would," he said. "I would very much like that."

"Good," Helen said simply. His fingers had ceased their manipulation of her while his brain mulled over the new situation. She reached down to Chase's fingers, telling him, "Do this. I really like it, and other women will, too."

The front wall of Helen's vaginal canal, right behind her clitoris, had always been super sensitive. It was probably the part of the reason she almost always came when fucked doggy style by a lover and more often than not by a regular client. She instructed Chase to come sit up next to her, then placed his hand such that he could curl his finger upwards inside her.

"It may make your hand and fingers hurt after a bit … repetitive and all that," she said once she had Chase going, "But I'll cum. You'll make me cum, Chase."

She asked him to lean down and kiss her a couple of time, but other than that, Helen had Chase concentrate on what he was doing down yonder. He was good at following direction, and soon enough he had Helen writhing at his touch and crying out in building pleasure. She clutched the arm he was supporting himself with one hand while the other grasped at the bedding, pulling it free from the mattress.

Then, arching her back to press her pussy into his fingers, she drew a deep breath … held it for the longest time … then let it rush out of her in a loud gasp of ecstasy. Her body exploded in trembled and goose flesh as she pleaded, "Don't stop! Don't stop!"

Her orgasm continued for well over half a minute, not the longest but certainly not the handful of seconds many others had. When she finally pulled Chase's hand from within her clenched thighs, Helen collapsed to the mattress and pulled the young man to her for a long series kisses broken only by her gasps of air.

 

[WatchingCloud]

Chase listened intently to Helen's every instruction, noting how she responded to his touch in certain areas and how the tension built with time and persistence. Watching the orgasm build under his attention was a marvel and seeing her climax, begging him not to stop, was the most satisfying thing he'd ever done. Sure, being on the other side was fun, but this was special.

After her climax, he held still until she guided his hand back out of her and pulled him in close. Their kisses were magic, feeling to him as full of emotion and promise as would be the case with a long term lover. This was what a relationship was supposed to be like. He knew it was silly to think of it like that, given the true nature of their relationship, but it also felt so perfectly right.

"That was fun," he said between kisses. "Is it as good when it's a mouth?"

 

[LoriDean12345]

They laid there just holding one another tightly for the longest time; hands caressed a bit, mouths kissed a bit, but that post-climax moment -- the afterglow -- was as close to a lover's cuddle as Helen partook and enjoyed these days. How long had it been since a man had driven her to orgasm and then just held her without the immediate need to pummel her pussy and find his own bliss.

"That was very nice, Chase," Helen whispered to him after her breathing had returned close to normal. I think, by the time we're done, you're going to be one helluva love machine."

She chuckled and kissed him as she pulled him closer.

"That was fun," he said between kisses. "Is it as good when it's a mouth?"

Helen laughed, telling him quickly, "It can be."

She rolled him flat to his back and took a position over his groin. She kissed him again, caressing his chest as she said, "It can be, but … I think it's time I did something for you … don't you?"

Helen slid down the young man's body, kissing his flesh as she went, until finally she took his cock into her warm, wet lips. She worked him a bit, hardening him fully, then told him, "I want you to cum before we make love. It will make you last even longer … and I want you last … even longer."

She giggled again, then returned to sucking his cock. Helen took a different approach this time, not deep throating him as she had before but taking less of him into her mouth and using her saliva-coated hands to stroke the lower half of his shaft. It seemed to work even better than swallowing his full length, and soon enough Chase was filling Helen's mouth with shot after shot of jizz.

Helen wanted to get just a little bit dirtier this time around, so she waited until Chase opened his eyes to look down at her … then used her tongue to push all that he'd ejaculated back out onto him. The thick, white stuff flooded over his big, bulbous head and down his shaft, and just as quickly as she'd expelled it all, Helen began licking it up with erotic swipes of her tongue and swallowing it in little gulps.

She giggled when she was nearly finished, then even blushed. She finished cleaning him up, then said with another giggle, "That was fun. I hoped you liked that."

As he responded, Helen moved back up over top of Chase's groin, took control of his cock, placed it at her hole … and slowly sat down upon him … groaning at the feel of him slipping inside her wetness. She hadn't had a cock inside her in over a week, so she was a bit tighter than normal; Chase's girth was a bit more than average as well, stretching her out with just a touch of pain at first.

Soon, Helen was sitting fully on the young man's body, purring as she asked him, "How does that feel, lover?"

 

[WatchingCloud]

"It can be, but … I think it's time I did something for you … don't you?"

Chase smiled. "Well, if you insist."

He watched as Helen kissed her way down his body until reaching his cock, which she had back to full hardness with only a little bit of attention. "I want you to cum before we make love. It will make you last even longer … and I want you last … even longer."

Chase definitely liked that idea. She began giving him an expert blow job, but after getting his entire shaft slick with saliva she transitioned into more of a hand job while her mouth worked the end of his cock. It was every bit as pleasurable as what she'd done earlier in the week and he relished watching her work him over. As his climax approached, he closed his eyes and focused entirely on how her hands and lips and tongue made him feel. He grunted, thrusting upward, and felt his release go entirely into her mouth this time.

He opened his eyes to watch her squeeze the last little bit out, then she disengaged, smiled, and let his cum dribble out of her mouth and back all over his cock. It was incredibly erotic, made even more so as she went about licking it all back up. Ordinarily, he'd have gone soft after a climax, but this was too arousing.

Finished, she looked almost sheepish. "That was fun. I hoped you liked that."

"Like you need to ask?"

He expected to wait a while before going at it again, but Helen took advantage of his continued state of arousal and straddled him. He watched as she positioned herself over his cock and began to slowly sink down on him. That first little bit was unbelievable, the smooth, slick, persistent pressure. As she settled further, it was like he could feel the scarlet V vanishing from his forehead. Virgin no longer, and he didn't regret for a second how it was happening. This was so much better than his hand.

Finally, she had him completely inside her, the fit perfect. "How does that feel, lover?"

"Perfect," he said. "I think I could really get used to this."

She smiled and suggested they find out what he liked. With her on top, they began with the basic cowgirl. Chase got the chance to get used to the feel and friction of having his cock in a real pussy all while watching her bouncing breasts and facial expressions. Definitely a good position. She then leaned further back, altering the angle a bit - nice, but a little awkward. She leaned back forward, kissed for a bit, then rolled over to let him try missionary for a while. He liked being able to kiss while thrusting, but he was still eager to try more.

Next, he knelt while raising her legs to his shoulders. Again, not bad, and it was fun watching Helen play with her tits and finger her clit from that position. After a bit of that, she suggested another change.

He pulled out long enough for her to roll over and get on her hands and knees. With her butt up and legs slightly parted, her glistening pussy was fully on display. His cock throbbed and he positioned it in the cleft, sliding it up and down several times before finally plunging in. The leverage from being more upright and holding her hips made this perhaps the easiest position. Very nice, though he missed being able to look her in the eye. She seemed to be enjoying this one, though, and he found a steady pace that brought his next orgasm imminently closer. His thrusts were as deep as he could go and he felt his balls slapping into her crotch. Once reaching this point, his hips took over and he kept going until that blessed moment of release. He held steady, cock as deep as possible, until the first couple pulses subsided. Then he gently thrust a couple more times but realized he was a bit too sensitive. He held in a place just a little longer before finally pulling out. His softening cock, like her pussy, was a glorious, glistening mess of their combined juices.

Helen laid down and gestured for him to join her. They kissed and cuddled and slowly brought each other back down. He was going to need this again - often and regularly.

 

[LoriDean12345]

The look on Chase's face as he slid inside her was very satisfying to Helen. She couldn't count how many V-cards she'd claimed in her three years of doing this work, but it likely numbered close to 100, and -- of course -- that didn't include the guys who weren't virgins but, because of previously disappointing encounters, might as well have been.

And yet every time was somehow magical to Helen. Truthfully, the joy of being a man's first lover was the reason she did what she did; she could make far more money doing business types in town for conferences or corporate meetings and such, or well-to-do married men who were simply looking for something above and beyond what their wives were willing to do to, for, and with them.

But that wouldn't have held any excitement, joy, or sense of accomplishment for her. Chase's expression was almost enough to do this for free. Almost.

As they began making their way through a handful of positions, an increasingly excited Helen explained to Chase that sometimes women faked their pleasure. Between breathes, she told him, "Sometimes … we feel we need … to stroke your ego … as much as your cock."

Helen leaned down to kiss him passionately as they changed positions yet again, continuing, "I won't do that to you. I won't fake my own satisfaction. I will teach you how to ensure it."

And teach him she did. Each time they took on a new position, they looked or spoke to one another as to whether it made one or both of them feel good. For one reason or another, each was lacking a bit for one or the other of them. Each of them got close to orgasm a couple of times, but Helen slowed or even stopped them; she wanted them to cum together, and she told Chase so.

When she knew Chase couldn't hold out any longer, Helen moved to hands and knees, a position that nearly always made her cum … if she wanted. It didn't take long before the pleasure welled up deep inside her; with one hand supporting her body above the bed and the other grasping at the headboard, Helen arched her back and looked over her shoulder at Chase, urging him with sincere compliments and direction.

She wanted to watch the teen's expression when he came for the first time inside a woman, but Helen couldn't hold out herself. She turned back, knowing ecstasy was imminent, and dropped to her elbows as she climaxed. Helen wasn't a screamer, which she'd always been thankful for as she feared it would only make her look as though she was faking when she wasn't.

But she wasn't quiet either; after some erratic breaths, she held one a moment, then gave out a satisfied gasp. As her entire body trembled in ecstasy, she continued to draw in deep breaths and let them out in gasps of joy … maybe four, five, ten … she was never in the right frame of mind to count, although one time she'd recorded herself like this because she was curious how she looked and that time it had been just three explosive burst of air from her lungs.

Somewhere amidst her own orgasm, Chase came as well. She'd sensed his orgasm and somehow recalled the feel of his cock leaping inside of her without being able to really put her finger on the exact moment. Helen's head spun with euphoria that she didn't often feel while on the job.

After a long moment, she let her body fall forward to the mattress. Chase came with her, laying next to her and pulling her into his arms. They cuddled for the longest time while their bodies calmed. She finally asked simply, "Did you enjoy it as much as you hoped, Chase?"

She didn't know how long they simply laid there, but after a while Helen whispered, I need to pee. She slipped out of the bed to do her business, then called out, "Chase, will you come join me?"

By the time he got to the bathroom, Helen was already stepping into a steaming shower. As he joined her, she told him, "I want to be clean and fresh … and … to go back to bed and just sleep beside you … have you hold me in your arms. Is that okay?"

 

[WatchingCloud]

Everything about having sex with Helen was better than her dared hope. The way she connected with him made it feel like so much more than a simple fuck. By the time they were reaching a peak, he was as invested in her pleasure as his own. Seeing, feeling, and hearing her orgasm was the real climax.

Holding each other afterward, quiet and intimate, was every bit as good in an entirely different way. Their breathing and pulses slowed, fingers gently caressing skin. He could do this all night.

"Did you enjoy it as much as you hoped, Chase?"

"Nah," he said, smiling. "My imagination wasn't good enough for that. You were...are...incredible."

The word was inadequate, but he was pretty sure the sincere gratitude and happiness was conveyed. They held each other a while longer until she finally excused herself to use the bathroom. He unabashedly watched her cross the room, mesmerized by the wiggle of her ass atop those endless legs. Before they'd had sex, Helen had this intimidating aura about her - not her fault, just his feeling of being out of his league with her. Now, he felt comfortable. He marveled at how quickly that had changed.

After the toilet flushed, she called out, "Chase, will you come join me?"

He didn't need to be asked twice. He hurried to the bathroom and found the shower on and steam already beginning to condense on the top of the mirror. Helen was stepping into the spray and it was pretty clear she expected him to join her.

The hot water deflecting off Helen felt wonderful, but Chase's attention was lost in watching the water run over and down her smooth skin. She looked back at him with a smile. "I want to be clean and fresh … and … to go back to bed and just sleep beside you … have you hold me in your arms. Is that okay?"

Okay? It was beyond okay. He briefly wondered at what his roommate might think when he didn't come back that night. He didn't care. It was refreshing to be the one spending the night with a girl for once.

'I like how you think," he said, joining her with a kiss.

Chase found the soap, lathered up his hands, and began washing Helen's body. He worked from the neck down, enjoying the exploration of every bit of her body, not just the previously forbidden ones. He did spend done extra time on her breasts, however, as well as between her legs. When he washed her back, she pressed into him and he savored the frictionless sliding of their bodies together. His cock had hardened again at the frequent incidental contact and now it slid between her legs. She teased it with a squeeze from the front before he continued on with washing her.

Helen returned the favor, washing him thoroughly. Her touch was intimate, yet not intended to get him off, even with a bit of lingering on his cock. Once clean, they held each other and kissed a bit more before getting out and drying. Before long, they were back in bed, sheets pulled up and holding one another.

Chase was surprised at how he could be in such close contact with a beautiful, naked woman and not have only sex on the mind. The release from earlier surely helped. It was fun just being there, making idle chitchat and getting to know her as a person, a fellow student with dreams and ambitions, rather than just a professional he'd hired for a service.

"Not sure if this is violating etiquette, but how did you come to be in this...line of work? I mean, obviously, I don't object. Just curious how you got started."