Helen Norsworth stood angrily in the corner of the room and watched as the concierge entered. The woman was wearing her signature look of heels, a slim dress hugging the curves of her toned body, and a masquerade mask. Only her blue eyes and blond hair countered the all-black outfit. Helen sniffed in disdain. She was more than just a client here and she expected better than this.
“What seems to be the problem Ms. -”
Helen cut her off before she could finish her question.”What do you think is the problem?” she asked aggressively.
The concierge took another step into the room, now able to see the member booked for the scene. He stood at the corner of the bar, already down to his underwear, his dark six pack glistening under the dimmed lights. He offered nothing but a confused shrug to the concierge. She went to check her smartwatch for details of the evening’s plans but before she could, Helen snapped her fingers to get the attention of the room back on her.
“Don’t do that. Don’t check your stupid notes,” she insisted.
The concierge took a moment to respond, seemingly choosing her words carefully. “I apologize, Ms. Norsworth, I am not sure what the issue is; however, we here at the Fantasy Hotel will do whatever is needed to improve your experience.”
Ms. Norsworth sighed. “Why am I here?” She had given strict instructions for this evening and yet somehow it was not close to completing her fantasy.
The concierge confidently responded as if she was reading off her intake notes. “You booked the master suite; it is your favorite room at the hotel and best suited for your fantasy. You said you were worried that as you age, you are less desirable and thus you have the fantasy to be the ‘MILF next door’. You want to take the virginity of a man in his early to mid twenties, which leaves him the right age range to be friends with your son. The taboo nature of seducing your son’s friend adds to the feeling of being desired that you came to us to fill.”
Helen nodded, but the concierge was missing the point. “That’s right, but what the hell is this?” She motioned to the shirtless man who was now pouring himself a scotch at the bar.
“That is Dylan. He is an experienced player here; one of our best at getting into character, and he happily picked up your contract for today. He has incredibly positive reviews and matched well with you in our profile database.”
Helen raised her voice. “Look at him,” she demanded, pointing to Dylan once more. “Does he look like a virgin that wants to be seduced by this?” she motioned to herself this time, her self-consciousness making her even more irate. Now nearing her 50th trip around the sun, her large breasts were not as perky as they used to be, she had some extra weight that she couldn’t get rid of no matter what she tried, and stretch marks taunted her when she looked in the mirror. All these things and more left her yearning for her younger years when anyone at a bar would be grateful to go home with her. Now, she was left using the Fantasy Hotel to feel desired.
“I… I suppose not,” the concierge responded in an uncertain tone. “We can reschedule your booking on the house and I will personally ensure we find you a partner that meets your desired appearance, although I do warn that the acting level may need to be sacrificed,” she added.
“I do not want someone acting,” Helen declared icily. What was this incompetent concierge not understanding here?.
“You… you want a real virgin?” the concierge asked with an awkward half grin as if someone was playing an uncomfortable joke on her.
“Yes,” she replied, her vehemence making the ‘s’ on yes sound snakelike.
“That’s preposterous,” the concierge scoffed. “The logistics of getting a virgin to join the hotel with informed consent is just -“.
This had gone far enough. “Anna,” she barked, using the concierge’s first name since nothing else was getting through her thick head. If the resulting flinch was anything to go by, it worked. “If memory serves correctly, we elected you because you follow our rules and get the job done. Is that no longer the case?”
The concierge gulped. “Of course, that is what I am here for,” she explained, taking a step back. “If you can reschedule for a future date, I will do everything I can to make sure you enjoy your stay,” she added.
“Take all the time you need, darling,” Helen said with a venomous smile. “But if you mess this up again, I will move for you to lose your job.”
“Of course, madam,” the concierge replied in a voice pleading for mercy. “I will make sure your next visit has the best candidate for your fantasy,” she resolved.
“Candidates,” Helen clarified with force.
“I’m sorry?” the concierge asked, worried.
“I want multiple candidates. Set them up all in a row for short meetings; I will select the best one to continue with. You’ve clearly lost your touch.”
“Very well, madam,” the concierge agreed before leaving the room, immediately to begin the search.
Only a few days later, while Helen was enjoying a drink alone at home, she got the phone call she was eagerly waiting for. It was from the concierge alerting her that the meetings had been set up. They confirmed the time for the following Friday.
Time moved slowly for Helen as she waited for the big day. When it finally arrived, she made sure to get to the hotel room early. This time, she wore a sundress, black with some floral patterns, and a white button up shirt over top. She swapped heels for a more casual flat. On the way into the hotel, the concierge greeted her with a smile, but she reciprocated with only a glare. She sat at the bar in her room, nervously swinging her leg back and forth with anticipation until finally, the first candidate arrived.
A man entered the room, visibly uneasy. He was a bit on the short side and had made some interesting wardrobe choices for the evening. He was wearing sneakers, cargo shorts, an unfamiliar brand t-shirt, and a flat-brim, snapback hat. He was a bit out of shape, and even with the hat on, she could tell his hair was an absolute mess. As he turned towards the bar, he caught sight of her and he froze like a deer in headlights.
Helen couldn’t help but grin as she saw the timid man before her. She stood from her bar stool and approached him. “What is your name, darling?”
The man remained frozen for a moment before shyly responding, “My… my name is Jimmy, ma’am.” His voice cracked with nervousness.
“I like that,” she responded with a smile. “You must be my white whale?”
“I, um, I’m not sure what you mean,” Jimmy responded, his fiddling with his fingers betraying his nerves.
“I mean you must be a virgin… one who is interested in an older woman?”
“Ye… yes ma’am,” he responded, his face now beet red with embarrassment.
“Honey,” she said kindly, “please don’t call me ‘ma’am’; it makes me feel old. Now come sit at the bar.” She motioned to the chair beside her.
Jimmy nodded and nervously made his way towards the bar. He sat one chair over so an empty seat remained between them. “What can I call you then?” he asked shyly.
For a split second, she felt badly about how uncomfortable Jimmy clearly was. However, these feelings quickly turned empowering as she sensed her control of the situation. With a swipe of her arm, she knocked the chair between them over. Jimmy’s eyes lit up with fear as the chair clanked against the hardwood floor. She smiled. “My name is Ms. Norsworth, but you can call me Helen.” She crossed one leg over the other making sure to gently rub her foot against Jimmy’s leg as she turned to fully face him.
Jimmy nodded, clearly unable to speak.
“Can I get you a drink?” She motioned to the wide selection of expensive booze available behind the bar.
Jimmy shook his head no. “I uh I don’t drink. Alcohol that is ma’am I… I mean Helen,” he added a moment later.
“What about water, darling?” she asked.
**
“Uh sure,” he responded, face beet red as he cursed himself internally for his awkwardness.
Helen swung herself around on the bar chair, getting up and walking towards the open end of the bar. She peeked over her shoulder as she walked and saw Jimmy blatantly checking her out from behind. She grinned as his eyes caught hers before he quickly looked down at his feet, trying to play it off. Helen filled two glasses of water and returned to her seat at the bar.
Immediately, Jimmy took a big gulp of water, attempting to manage his nerves.
Helen smiled again. She took a small sip of water and asked, “So what brings you here, Jimmy?”
Jimmy shrugged, unable to formulate an answer.
Helen did not fixate on the question and instead asked another. “What do you do for fun?”
Jimmy was quiet again, but finally he worked up to courage to speak about himself. He began telling Helen about his hobbies, specifically the role-playing computer game he spent countless hours on. After a moment, he paused as embarrassment rushed over him when it clicked in his mind he was babbling about a video game in front of a beautiful woman.
Helen seemingly recognized his discomfort and interjected. “I love hearing about things that make people passionate.”
Jimmy continued telling her about his game, filled with comfort from her kindness.
After a few more moments of chatting back and forth, Helen proposed a question. “Would you be interested in extending our visit?”
Jimmy had no hesitation and responded with a resounding “yes!”
A smile washed over Helen’s face. “Wonderful darling,” she declared. A split second later she bit her lip seductively and added, “Maybe we can fulfill the purpose of this meetup?”
Jimmy blushed, the vague sexual nature of the question washing away the comfort he had built up. “I… um… that would be good,” he managed to stutter out.
Helen giggled playfully. “It will be a good time,” she promised. Helen peered at the time before adding, “I need to clear my schedule, can you wait here for me?”
Jimmy looked around, a bit puzzled. “Sure I’ll, uh, be here,” he offered with a shrug.
Helen stood before Jimmy. “I’ll even give you something to keep your mind busy,” she said with a smile. Jimmy tried to protest, insisting it was not necessary but he was quickly silenced by Helen’s actions.
Helen twirled in a circle in front of Jimmy. She then slowly slid her hands up her thighs and under her dress. With a little wiggle, she shimmied to a low crouch before stepping out to the side a bit. When she stood up straight again she offered her hand out to Jimmy. He instinctively put his hand out. Gently, Helen placed her freshly removed panties in his hand. Jimmy stood in awe, staring down at the black, lace panties. He tried to speak but couldn’t. The thrill of holding the panties of this beautiful woman before him rushed throughout his body; he could still feel the warmth of her body on the fabric as he ran it through his fingers.
“Enjoy,” Helen declared as she gently brushed her hand against Jimmy’s forearm while she stepped past him, briefly peeking down to see Jimmy’s cock starting to push against his pants. “I’ll be back as soon as I can,” she added with a smile before exiting into the hallway.
Jimmy watched the large door close behind Helen. His mind was rushing a million miles an hour; he couldn’t fully comprehend what was happening. On one hand, it seemed inevitable that he was about to lose his virginity, something he had given up on years ago, believing it was never possible. Even with that, this was not some quick lay just to try and get rid of his v-card, a ridiculous societal expectation. It was instead, a beautiful, kind, woman who seemed truly attracted to him. On the other hand, he was holding panties he’d watched this beautiful woman remove and he knew with certainty that they had moments ago been rubbing against her pussy… the slim piece of fabric on the back had been undoubtedly wedged between her butt cheeks. His body yearned for release; he could feel his dick pushing hard against his zipper with a pleasurable ache. Without the ability to stop himself, he shoved the panties against his face, burying his nose deep in them inhaling with a deep sniff. He could smell Helen’s sexual essence fresh on the fabric.
***
Helen was greeted by the concierge as she approached the desk.
“Is everything okay, Ms. Norsworth?” she asked with an anxious tone.
Helen waited a moment to respond, feeling empowered knowing that the concierge was worried that the meeting had gone poorly. She glared at the concierge a moment before deciding to let her off the hook. “Everything is splendid. I will be extending my visit with this first candidate. Cancel the rest of the meetings that were set up.”
The concierge took a deep breath and her eyes softened in relief. “Very well, Ms. Norsworth,” she responded with a smile. “Enjoy your time with us.”
Helen could not help but tap her foot as she waited impatiently for the large, creaky door to her room to open, her virgin prize waiting for her. She did not know what Jimmy would have done alone in the room with her panties but her pussy ached thinking of the possibilities. Excitedly, she entered the room but her imagination could not prepare her for what she would see.
She walked in the room, her heart racing with excitement. To her surprise Jimmy was still sitting on the bar stool. He clearly had gotten up and sat back down as the panties she left with him were now neatly folded by where she was sitting. Helen tried her best to hide her disappointment. She sat down at the bar and asked, “Is everything okay?”
Jimmy smiled. “Of course. Are you okay?”
“I’m wonderful, darling,” Helen responded with a smile. “I am just a bit surprised,” she added, motioning to the neatly folded panties.
“Oh, yeah, uh, I wasn’t sure what you wanted me to do with those,” Jimmy explained.
“I wanted you to do whatever your desires told you to, dear,” Helen explained suggestively.
“Well I -” Jimmy went to explain what he did with them, cutting himself off, clearly embarrassed by his actions.
Helen bit her lip as she knew she had Jimmy right where she wanted him. “I already know you enjoyed them,” Helen declared, using her eyes to guide Jimmy’s to see what she was seeing. He looked down to his crotch at the wet spot that had formed through his shorts from his leaky cock. “So why don’t you tell me how?” she added.
Jimmy gulped. “Well I… I smelt them and kinda rubbed them on my face,” he explained.
Helen’s hips thrust ever so slightly as her body ached with eroticism. She unbuttoned the top two buttons off her shirt, exposing mostly skin and the smallest sliver of cleavage. “And then what did you do?” Helen asked inquisitively, desperate for details.
***
Jimmy was unable to hold himself back, blatantly staring at her exposed skin. Even without much breast really showing, his eyes could not look away. He did not answer Helen, or even acknowledge the question. It was as if the words never made it to his brain.
Gently, with one finger under his chin, Helen lifted Jimmy’s head so his eyes were forced to meet hers. “What did you do next?” she asked more assertively this time.
“That’s it,” Jimmy explained, causing Helen’s eyebrows to lift with surprise. “Then I folded them and left them on the bar for you,” he added as even with his lack of social skills he could tell she wanted more information.
“Didn’t you want to do more?” Helen asked sternly. “Didn’t you want to touch your cock?” she added, still staring deep into Jimmy’s eyes.
Jimmy could not help but squirm in his chair as the beautiful woman explicitly questioned his private business. “I… I did want to, but well, it’d feel wrong or disrespectful, maybe?”
“What would feel wrong about it?” Helen asked earnestly.
“You weren’t in the room,” Jimmy explained, still squirming under pressure.
She lowered her hand off Jimmy’s chin, his head naturally bobbing down to her chest again before once more locking in with her eyes.
“That is unbelievably sweet of you,” Helen said with a warm smile. Her smile quickly turned wicked as she posed a new question. “What would you have done if I was in the room?”
Jimmy’s face turned a bright red, his eyes darting back and forth from Helen’s chest to her eyes, and finally to the panties that still sat folded on the bar.
Before Jimmy could find any words Helen interjected again. “Would you have rubbed my panties against your hard cock?”
“Ahh,” Jimmy stuttered trying to find words. “Yeah?” he added, unsure as the situation still felt unreal to him.
“Why don’t you do that now?” Helen suggested pushing the panties across the bar top to Jimmy.
He stared at the panties, heart racing, and a nervous sweat building up on his forehead. “Okay, if that is what you want,” he offered.
Helen watched him for a moment as Jimmy stared intensely at the panties. She took his hand gently, the human touch enough to break his focus. “We only need to do this if you feel ready and want to. We can go as slow as you need or not at all if you don’t want to,” she explained kindly.
Jimmy’s eyes focused with fear as he felt like a once in a lifetime opportunity was slipping away. “I’m ready,” he declared assertively. “I’m just nervous and… well I don’t want to disappoint you,” he added shyly.
Helen licked her lips, “I am certain you won’t disappoint me,” she replied. “If you’re really ready then why don’t we get naked?”
Jimmy nodded, heart thudding with excitement and nerves. He stood up but his nerves locked him up again from proceeding.
“I’ll go first.” Helen smiled, undoing the buttons of her shirt before tossing it across the room.
Jimmy watched the shirt fall to the ground before returning his eyes to Helen. She was even more beautiful than he could’ve imagined as she now stood before him in a sundress. He was unable to speak but gave an ear to ear smile reassuring Helen it was okay to proceed.
Next, she slid the sundress straps off her shoulders. She smiled passionately at Jimmy before letting the dress drop, catching it near her waist. With her breasts now only slightly hidden by her bra, Jimmy’s mouth dropped open. Whereas Helen may have seen her breasts as used and not as perky as they once were, Jimmy saw a beautiful woman presenting herself to him, the sexy aura undeniable. To him, she was not an aging woman past her prime; she was a drop-dead gorgeous dream come true, and there was nothing Jimmy would change about her.
Helen lustfully watched Jimmy stare her up and down, turning around so her back was now facing Jimmy. His breathing became audibly rapid as she slid the dress down further, slowly revealing her ass to Jimmy. He couldn’t hold back a lustful moan as her butt wiggled in front of him.
She looked over her shoulder and giggled. “So far so good?”
Jimmy took a moment to field the question. “Fff… fucking amazing,” he managed to stammer out, clearly struggling to find the brain power to speak with all his focus rushing to a different location.
“Good,” Helen declared as she used one hand to unhook her bra, the other holding up the dress still covering her front, lower half. With a swift movement, Helen dropped her bra and spun around, presenting her breasts to Jimmy.
The rush of lust that raced through Jimmy’s body stunned him. He both instinctively stepped back, taking it all in, while also reaching forward with his hands. Having finally seen breasts before him, it was only instinct that the next step was to touch them. He caught himself and retracted his hand. “I’m sorry,” he muttered, surprised by his own actions.
“It’s okay dear, you can touch them,” Helen assured him. She took a step towards Jimmy so her tits were well within reach. Jimmy squirmed with excitement as he reached forward with both hands. Placing one on each breast, a warmth came over him. It was as if a long lost dream had finally been completed. The warmth, the softness, the little resistance to his squeeze. It all stunned Jimmy, and despite him imagining this moment countless times in fantasies, nothing could prepare him for how it felt to touch Helen’s breasts.
With Jimmy distracted by her tits, Helen took the opportunity to drop her dress the rest of the way before kicking it across the floor. She took a step away from him and he held onto her breasts like a lifeline before finally letting go. He could now see in front of him the fully naked Helen, her freshly shaven pussy just a mere stretch away from him.
“What do you think? Helen questioned, her voice betraying her with a hint of insecurity.
Jimmy simply groaned in response, unable to find words to describe Helen’s beauty or the lust he felt towards her. She tilted her head inquisitively, as if trying to encourage an answer from him. “I… you’re… well,” he stammered before taking a deep breath to compose himself. “You are the most beautiful woman I have ever seen,” he declared.
Helen’s smile reflected her relief. “Your turn,” she said suggestively, referencing the still clothed Jimmy.
He looked down at himself and kicked off his shoes, excited for the next step. Unfortunately, he froze again.
***
Helen smiled, his nervousness turning her on like nothing before. She kicked off her shoes, matching his action and leaving her completely naked. “Why don’t I help you out?” she offered.
Jimmy gave a reassuring nod.. She stepped behind him, knocking his hat off as she passed, then then lifted Jimmy’s shirt over his head and tossed it onto the growing pile of clothes. She embraced Jimmy from behind, giving him a gentle hug. Her body rubbed against his and she danced her hands across his chest. She felt him shiver as her bare breasts pressed against his back. Jimmy let out an animalistic moan as Helen kissed his back before pulling his shorts down. She rubbed her hands on the inside of Jimmy’s thighs, and without protest, she knew it was safe to continue. She gently pulled his underwear down and helped him step out of them. She admired his cute little butt. “Turn around when you are ready, darling.”
Jimmy turned slowly as if feeling self-conscious and his face fell when she gasped. Helen instinctively covered her mouth with her hands in a failed attempt to hide the noise. “You’re so sexy,” she declared as she looked up and down Jimmy’s naked body. It was just what she had always wanted, a real man. A bit out of shape, a bit awkward, but a real man, far from the ridiculous standards portrayed by the media, who really wanted her!
Jimmy’s expression appeared dubious but she knew he would understand when she showed him exactly how desirable she found him. Helen licked her lips as she stared thoroughly at his cock. It had gone a little soft with nerves, almost as if it was hiding from her, nervously nestled in Jimmy’s unkempt, curly pubes. Somehow, seeing that he did not groom himself with expectations of the evening turned her on even more. And the icing on top was his large balls, soaked with precum from his cock leaking. Helen knew she had to have them.
This time, Jimmy broke the silence as he nervously asked, “What do you think?”
Helen took his hand and guided him towards the bed. “You’re perfect. Where do you want to start?”
Jimmy followed Helen’s lead like a pet on a leash. As they reached the bed, Helen sat down on the edge of it and Jimmy stood before her.
Finally he spoke, nervously asking, “Can I touch you?”
“Of course, darling.” Helen happily obliged as she laid down on the bed, encouraging Jimmy to join her on it. She giggled as Jimmy awkwardly climbed onto the bed. Encouragingly, she added, “Touch wherever you want.”
Jimmy stared at Helen from above, his expression showing the awe he was feeling. Gently, Jimmy grasped Helen’s breasts. He squeezed them slightly as he swatted them back and forth like a kitten with a ball of yarn. Helen moaned at the feeling of his touch and her hips instinctively raised into the air as she desperately tried to thrust against any friction she could find.
“Why don’t you try with your mouth?” she suggested sternly through a moan.
Jimmy did not hesitate to follow the order. He leaned down, pressing his face against the soft, warm breast. His tongue escaped his mouth, instinctively licking.
“Good boy,” Helen moaned, thrusting more aggressively. “Suck on my nipple,” she added through deepening breaths.
Jimmy followed her instruction immediately. He sucked aggressively on Helen’s nipples rotating between left and right. His body fell against hers as he buried his face in her tits. Helen moaned louder as his weight fell against hers, his stiff cock pressing against her thigh.
“Good boy,” she added, again rewarding Jimmy for his obedience. “I love the feeling of your stiff cock,” she added.
“Th… thank you,” Jimmy responded nervously.
“I’m so fucking horny,” Helen declared with a sense of urgency. “Do you want to make me cum?”
***
“Yes please,” Jimmy blurted out as he froze, waiting for further instruction.
“I want you to put two fingers inside my pussy.” Jimmy obliged without hesitation, his two fingers sliding inside her wet cunt with ease. He was in awe of the moist warmth her pussy offered.
“Nnnow slide them in and out,” Helen added, her hips violently thrusting.
Jimmy followed along, sliding his fingers in and out. After a few repetitions, he started to get a rhythm going. His pace picked up as Helen, through deepening moans, instructed so.
“Don’t stop, don’t stop,” Helen repeated the first time begging for more but the second sternly commanding action. Jimmy watched as his fingers caused Helen’s body to convulse. Her legs shook before tightly squeezing together. Jimmy’s hand was pinned inside Helen and he did his best to keep the fingering motion going but the tight, squeezing legs left his hand unable to move. He smiled brighter than ever as Helen blurted out, “I’m gonna CUM.”
The leg lock loosened but with Jimmy frozen in awe, his hand rested inside Helen’s cunt. His own body was shaking with a mix of shock, pride, and lust. He watched Helen try to catch her breath.
“You did so good, baby,” she declared, staring lovingly at Jimmy.
Finally removing his hand from the warmth of Helen’s pussy, Jimmy collapsed beside Helen on the bed. He stared curiously at his soaking wet fingers.
“Why don’t you taste them?” Helen suggested.
Jimmy looked at Helen and then back to his fingers before excitedly shooting his fingers into his mouth. He sucked on them, his cock twitching, as he tasted the wonderful essence of a woman’s juices.
“How does it taste?” Helen asked inquisitively.
“R-really good,” Jimmy managed to stutter out.
Helen pulled his hand towards her. “Maybe I should try some,” she said seductively before she licked the full length of Jimmy’s fingers. Next, she briefly bobbed her head up and down, making sure to get every possible taste of herself off the fingers.
Jimmy moaned as he watched Helen’s actions, his whole body twisting with lust.
“You’re cute when you’re squirmy,” Helen said with a giggle. “Should it be your turn to cum?” she asked suggestively as she looked down at Jimmy’s stiff cock and the pool of precum on her thigh.
Jimmy pondered the question and he was sure he looked like a deer in headlights again.
“Well?” Helen asked.
“I’d like that,” Jimmy agreed shyly.
“Unless you don’t want to?” she teased.
“I do, but…” he stammered.
“But what?” she questioned powerfully.
Jimmy gulped as he tried to find the courage for his question. “Can I eat you out?” he managed to request quietly.
Helen moaned. “I think that can be arranged,” she teased.
Jimmy went to sit up and move towards the cunt he so desperately wanted to lick. To his surprise, Helen swung her arm out against his chest and forced him back to laying down.
“But first, I think it’s your turn to cum.”
Jimmy started to protest, but she cut him off.
“I’ll make you cum, then you can eat me, then you can fuck me.”
Jimmy was only able to nod along in agreement.
***
Helen propped herself up on the bed and slid herself down towards his lower half. As she moved she could not help but admire the soaking wet spot her orgasm had made on the bed sheet. She then paused and admired the tool she was about to work on. Even without being stimulated yet, Jimmy’s privates were soaked with precum. His curly pubes were weighed down by his juices. His cock, even fully erect, was not overly large. In fact, it may even be classified as below average; she certainly would only need to use one hand stroking it. It arched up with a slight curve and was covered in veins that were clearly begging for release. His breathing had increased with her just looking at it, the anticipation clearly a huge turn-on.
Helen grabbed a firm hold of Jimmy’s balls and he startled and squirmed in the bed. Helen giggled flirtatiously as she fondled the balls in her hand, feeling the moisture mixed with precum and nervous sweat. More importantly though, she could feel the power she wielded gripping the inexperienced man by his sack. He was at her control and they both knew it.
Jimmy squirmed as Helen worked her hand up from his sack to the base of his cock. She leaned forward, bringing her face towards his member and sliding her hand up towards the head. Jimmy squirmed. Just before her lips could caress the tip, Jimmy let out a loud groan as a stunning orgasm surprised them both.
A thick rope of cum glazed Helen’s face reaching from her pursed lips, over one eye and reaching the tip of her hairline. Before the next rope could launch, Helen instinctively took the cock deep into her mouth. Jimmy’s moans got louder as the soft warmth of Helen’s mouth embraced his tool. His sounds reached a higher pitch as his large load expelled into Helen’s throat. He squirmed on the bed as his orgasm finished, and Helen took pity on him, knowing he was going to be quickly oversensitive..
Helen watched his face go from content to mortified in an instant. “I am so sorry. That… that doesn’t usually happen.”
Helen smiled as she licked her lips, collecting all the cum she could reach with her tongue before swallowing it down to join the rest of the load she already happily consumed. “Darling, it’s okay, it happens,” she responded softly. “We’ve done quite a bit of foreplay and it’s your first time, this is normal,” she added, surprising herself with how sexy it felt to be comforting a worried man.
Helen shuffled herself to be sitting next to the still clearly worried Jimmy. “I promise it is okay,” she offered as she rubbed his back. His worried breathing began to slow as Helen’s embrace warmed his nerves.
“I really didn’t mean to,” he shyly emphasized.
“I know, baby,” Helen responded warmly. “It was still lots of fun and super hot,” she added, trying to build his confidence.
Jimmy shrugged showing his disbelief.
“It just shows how much I turn you on,” Helen added convincingly.
After a moment of silence where Helen continued to rub his back, building his comfort Helen asked, “Do you want to stop for now?”
“I want to keep going!”
Helen felt a craving for seeing more of his excitement. “Okay darling. I’m gonna need you to help me clean up a bit then,” she instructed.
***
Jimmy’s face became a bright red with embarrassment as he realized his cum was still glazing the top half of her face, even leaving her with one eye closed. Before he could offer an apology Helen softly took his hand.
“Can you wipe it off?” she proposed softly.
Jimmy never liked touching his cum. He often felt a disgust towards himself after cumming, usually regarding whatever video he ended up finishing to, but in this situation he knew he had no choice. As gently as he could, he scraped his cum off her face. His sticky load now sat uncomfortably on his fingers. With a sense of urgency he looked around for somewhere to wipe his hand off.
“I’ll take care of that honey,” Helen offered as if reading his mind. She took his hand and shoved his fingers deep in her mouth without hesitation. She slobbered on his fingers even licking down to his wrist ensuring she got every last drop of his cum to enter her stomach. “All better?” she asked teasingly.
“Y..yeah,” Jimmy managed to stammer out in awe of her actions, lust rushing through his body stronger than ever.
Helen smiled as she saw his eyes light up. “Do you still want to eat me?” she asked bluntly.
Jimmy nodded, unable to find words. Helen guided him to the floor where he sat on his knees. She positioned herself on the bed with her legs hanging off on either side of Jimmy. She spread her legs presenting right in front of his face her soaking wet cunt. Jimmy hesitated ever so slightly but a smile of encouragement from Helen was enough to continue as he buried his face between her legs.
His inexperience showed as he simply stuck his tongue inside her pussy. He was filled with joy as her juices settled on his taste buds, the wonderful taste of her essence fulfilling his every wish.
Her hips thrust her womanhood against his face. “M-move it around,” she instructed.
Jimmy moved his tongue around clumsily, hoping that even the off beat movements were enough to arouse her. She desperately thrust, trying to increase the friction to her pleasure spot. Jimmy’s mind had gone blank as his face was getting soaked with her juices, he was experiencing bliss.
“I want to ride your face,” she declared loudly.
Jimmy was shocked back to consciousness by her speaking. He would never object to such an idea but was unsure how to proceed. Helen sat up on the edge of the bed and took his hand, encouraging him to come close. She passionately kissed him, surely tasting herself inside his mouth.
“Lie on your back in the bed,” she demanded before taking an animalistic lick of his cheek to collect more of her own juices.
Jimmy simply nodded as he moved himself into a lying position in the bed. Helen climbed on top of him, positioning one leg on each side. He could feel the warmth of her pussy on his chest as she briefly paused for just enough time to teasingly suggest, “have fun darling,” before lowering her pussy onto his mouth.
Jimmy stared up in a loving fashion as he felt her pussy grind against his face, her taste and smell overwhelming his senses. All he could see was her tits shaking back and forth with her nipples pointing down towards him.
Helen did not hesitate as she quickly moved to an aggressive grinding motion thrusting her hips quickly and pushing her pussy deeply against his face. Her orgasm built quickly as,with only a few more quick thrusts, she leaped over the edge. Her legs trembled before her thighs pinched tightly against Jimmy’s ears, squeezing his head nearly to the point of pain. His mouth was filled with her juices more than it ever had been before. Without hesitation he swallowed as the juices flowed into his mouth.
Finally, her legs stopped quaking and she took one more deep thrust against his face, pushing his head deep into the mattress and taking everything she needed. She then lifted herself off his head, falling beside him on the bed with her breath still racing. Jimmy stared up at the ceiling, his own breath racing as he was able to breathe fully again. As he sat himself up, he saw his dick fully erect again. The arousal of tasting Helen had thrown him back to a desperate to cum stage quicker than ever. He then looked at Helen who was still slowing her breath as she wiped sweat off her forehead. “Thank you,” he offered to her.
Helen giggled., “You’re welcome, darling” she responded before adding, “You’re the one that should be thanked.”
She shifted onto her side and ran a finger teasingly down his chest. “You’re the one that just made me cum again” she explained. “You even swallowed my juices like a good boy” she added as her finger reached his erect cock, nudging it gently. “So thank you,” she added, smiling at Jimmy.
“You’re welcome,” he managed to respond, in awe of Helen’s continued sex drive.
“Tell me how you want to fuck me.” she commanded, looking him straight in the eyes.
The question stunned Jimmy; he did not know how to answer but felt confident that Helen would help him. “I don’t know.”
“That’s okay darling,” Helen consoled. “Why don’t we start with missionary?” she proposed before adding, “We can always switch it up.”
Helen laid on her back encouraging Jimmy to climb on top. He followed without questioning. His cock twitched with anticipation as he hovered above Helen. He thrust forward and his soaked cock ground against her inner thigh as he struggled to position himself properly. Before he had a chance to feel embarrassment, Helen comforted him.
“It’s okay darling, it’s something to get used to.”
She reached down and gently gripped his cock and it twitched at the sense of her touch. She pulled it towards her hole, forcing Jimmy to follow like a pet on a leash. She aimed it towards her entrance before reaching behind Jimmy, and with a firm grip of his butt she pulled him towards her causing him to enter her.
A high pitched moan escaped Jimmy’s mouth as he felt his cock embraced by her warm insides. He could feel it twitching inside her.
“Hump darling,” Helen instructed, whispering into his ear.
***
Jimmy began humping furiously like his life depended on it. Louder and louder moans escaped his mouth. Helen felt her body rock back and forth, his dick was just enough to tease her pleasure spot. The clumsy humping was hard for her to feel a sexual rhythm but it was undeniably sexy how desperately he tried to fuck her. The feelings of control and being desired raced through her body.
Just a second later, Jimmy managed to stutter out, “Should I pull out?” through rapid breathing.
Helen smiled. “Its okay baby, you can cum in me,”
As soon as she uttered the words, he visibly exploded and collapsed on top of her. Helen forcefully squished his head into her breasts as she felt his cock twitch inside her releasing a small, warm load. “Good boy,” she said softly as she rubbed the back of his head still buried in her tits. Jimmy was still thrusting his hips as much as he could without his body being lifted as he desperately tried to push out every drop of cum.
When his body could move no more he briefly rested against Helen with his head still embraced by her breasts. Finally, he found the strength to roll over and lay beside her. “Was it good for you?” he questioned shyly.
“It was amazing darling, you did so good!” she exclaimed.
“Did you cum?” he asked nervously.
Helen paused for a moment to find the right words. She then softly explained, “I’m not gonna lie to you sweetie. I did not cum from the sex but it was still super hot and you already made me cum twice. There is nothing I would change about this evening with you. You were perfect.”
Jimmy nodded along to her explanation. She was grateful he seemed to understand and didn’t appear ashamed..
“Thank you,” he muttered sleepily.
Helen let a fulfilled sigh escape her body. She needed no words between them as the perfect moment was enough. She pulled him in towards her. Their breathing synced up as they both rested in the bed, his head using her soft breasts as a pillow. Helen could not help but feel joy as Jimmy fell asleep on her chest. She stared up at the ceiling as he snored with her fantasy fulfilled.
She supposed the concierge could keep her job after all.