But she's dating my son (closed for Submissive Luna)

The hotel room looked more like an apartment at first. Roy was there pouring a previously opened bottle of actual Tuscan Wine. "You have to try this. You can never get this imported properly." He offered her a glass and gave her a once over.

"Damn, you look great. I'd ravish you but the mission is too important." He gestured to the hotel, "And, I'm sorry this is one of the smaller and newer hotels. I couldn't convince the Foundation to spring for the good hotels for an unproven agent."
 
Serena smiled at Roy as she accepted the glass of wine from him. Taking a sip, she enjoyed the mix of flavors on her tongue before she swallowed.

"Thank you Roy. You look good yourself." She looked around the room, still in awe of the size. "This is a small one? It's wonderful Roy. I have never stayed in a hotel room so big before. So, tell me. What will I all be doing on this mission?" She asked as her eyes roamed over his body and she has to silence a moan that threatened to escape from her lips.
 
Roy took a breath, and looked Serena over as well. "You're going to be taking the place of a Prostitute. He set down the wine and continued, "It's your cover. We need you to take pictures of a tattoo."

He pulled out an envelope with some pictures of a stone wall. It looked like it could have been from a tomb or pyramid but there were runes or markings with various notches carved into the wall.

"This is a vault underground in Ireland. We have fabricated a key, but we need the combination. Currently it's under the control of a Bond Like Villain we only know as Scorpio. We managed to track Scorpio to a mansion, here in Italy. We also know a prostitute was hired for the evening's festivities. Sadly, she was paid in advance so we can't get the money, which is fine because we need her out of the way. She was vetted for any health issues or STDs and given 3,000 Euro with an invitation to this party."

Roy produced a black invitation with gold lettering in Italian. "According to this, she was going to be called Clara. And, all we know is that Scorpio has a tattoo that looks like a Celtic knot with a Dragon and a Hound. The knot is an algorythm so we'll need you to get a picture of it from exactly 8 and a half inches away. Too close or too far and we won't know the distance between the spaces of the knot which is the most important. So, hopefully you'll find the tattoo and tire the subject out long enough to grab a picture or two."

"This will, of course, make you an international spy. You sure you're up for it?"
 
Serena walked over and sat down on the couch as Roy explained her assignment. Her mind already whirring with possibilities and trying to figure out the best way to tire the man out.

"Do we know anything about Scorpio beyond the name he goes by and his tattoo? I do like to be prepared Roy. I'm assuming you have an outfit for me? How will I make sure Scorpio doesn't come looking for me?" The few questions she had just seemed to come flooding out. Her face reddened a bit before she stood and trailed her hand down Roy's face before lightly pressing her lips to his.

"Yes, I am up for it. I will find the tattoo, get the pictures and then come back to you." She stated before kissing him again. "When is the party?"
 
"Scorpio owns the mansion, so it shouldn't be too hard. Technically that's who paid..." He checked the invitation again, "Clara. Right. Clara." He looked at his watch, "Party is tonight. You're supposed to show up at 10. I'm sure you'll be greeted by someone important if not, Scorpio themselves. That should give you a few hours to get ready."

He moved as if he were going to give Serena the note, but pulled her to him instead. "I'll be here waiting for you. Be careful." He then kissed her, caring and tender. "I kind of wish we had time, but I can't send you off to be a high class escort who books clients back to back. To maintain your cover. Never blow your cover."
 
Serena moans softly into the kiss as she wraps her arms around him. "Yes...maintain my cover." She said softly before kissing him again. "I think Clara is going to wear a skin tight red dress that comes to mid thigh. I will be careful Roy. I promise. I have both you and Josh to come home to. Should I wear a wig or go with my normal hair?"

So many thoughts went through her head as she planned for her mission tonight. She was going to have to make sure to get into the mindset of Clara to make sure she pulled this off. Her gaze lifted to Roy's eyes as she thought about returning after the mission and just what he would do when she got back.

"Roy, I am confident that I can do this. I will make you proud." Serena said while looking at him.
 
Roy kissed her one last time then said, "I'm going to head to the bar. I'll wait for the party to start and head back up here. I'll leave a key with your name, not Clara, at the front desk. I don't want you having anything that can link you back to this place on you. Now, get ready. You're on your own from here out."

He left, heading down to leave Serena to get her persona on.

...

The agents had arranged for a car for her to drive, so no one would have to be in the loop. It was an expensive European model that said 'I'm made of money' and the GPS had the best rout already plugged in.

Scorpio lived in a huge mansion, there was a parking area in the front and lots of guests milling about. Most of them looked young, some didn't look like they were of legal drinking age in the states but that didn't stop the wine from flowing.

A large doorman took the invitation that "Clara" had offered and told her to follow him to a study. "Make yourself comfortable. The lady of the house will be with your shortly."

The woman who'd walk in later was older, tall and svelte. She had pale green eyes, thin lips and a nose that looked a little too long but simply added to her exotic face which was framed with copper hair with red highlights. She wore a gown that hugged her body and only exposed her arms and back, all the way down to her hips. The front covering all the way up to her neck was topped with lace and still managed to show off her pert nipples and fake, yet masterfully sculpted breasts.

"You are British? So I speak English. Yes?" She said with an accent that was hard to place.

Once the introductions were done she dove right into business while looking the woman she knew was Clara over, "Yes. Today my son is 18. I want him to have proper woman give him proper first time. You will make him a man first with your mouth then with your... body. All natural."

She took out an envelope, "You have been paid to travel here. This is extra should... anything, unexpected develop after tonight. Am I clear? I don't want to deal with anything after tonight. Do you understand?"

There was no way the son was Scorpio, so already this mission was sounding complicated.
 
Serena ran her hand through the black hair of the wig. It felt so real that she almost couldn't believe that it was a wig. The agency hadn't spared any expense when it came to the disguise. She supposed it wouldn't do them any good if she got found out. As the woman walked in, she watched her closely and listened.

"Yes Ma'am, I understand." She said in a rather good British accent as she accepted the envelope and put it in her small clutch purse. Her room mate in college had been British and she has been fascinated by the accent so the room mate helped her learn how to pronounce things in it. "Are there any other special requests you have for your son?" Serena asked as she sat and crossed her legs. The thigh length dress was perfect for the job and she felt sexy wearing it.

She was going to have to figure out who Scorpion was. She wished that Roy was there but she was on her own and determined to make him proud and get the pictures.
 
"My only request is that you teach him not to cum quickly. To control himself and savor the pleasure. As for your entrance, it will be just before midnight. Someone will come for you and take you back stage and let you know when to head to find him at the dance floor."

She gestured to a large portrait over the fireplace, "That's him. The older one. The picture is a few years old but he hasn't changed THAT much." The young man she was referring to looked thin with short styled hair and wore a tailored suit with a clean save and innocent eyes. One could imagine he did well in school and might even be a little shy.

"You have just under an hour. Feel free to... freshen up." She said this, the matron looked Serena over as if she might be trying to size up what was under the dress. "Yes. This will be perfect. Any last questions? I have to return to the guests."
 
"Freshen up Ma'am? You believe that I need to freshen up?" Serena, as Clara asked. "I do believe you would prefer me to stay well clothed until after my entrance. I will make your son's night. Trust me, it will be a night he won't soon forget but also one you will not have to worry about either. I will be fine until it is time for my entrance." She said confidently as she kept her eyes on the woman.

Serena was going to look around the room while she had a chance and maybe find out who Scorpio is before she ended up in bed with the kid. She really wanted to solve this puzzle and make Roy happy.
 
The woman looked Serena over and nodded. "No, you're fine. Just wanted you to have the option. Very well, wait here and someone will come for you when it's time to meet Lorenzo. Enjoy a drink or... whatever it is you like to do." She gave Serena an over the shoulder glance one last time as she walked out.

A large man in a suit closed the door and waited outside.

The room was larger than Roy's study. In fact it was impressive. I didn't have any art work like the previous rooms, the only things close was the portrait over the fire place, but it did have a desk, dry bar and various photos on the walls and desk or shelves. In them, mostly, were pictures of the woman Serena had just spoken with and an older man in various vacation spots.

There were a few of just the woman and the young boy, so this was clearly the office of the man of the house. The desk was locked, however, and the books on the shelves seemed real.
 
Serena walked around the room slowly as she let her eyes scan the room. So Lorenzo is the boy and he couldn't be Scorpio. Could his father? She wondered if she could get close to the man of the house easily tonight. She looked closer at some of the pictures to see if she could spot even part of the tattoo that Roy had told her about. She needed a confirmation on her mark somehow.

She scanned each picture closely before going over and scanning the titles of some of the books. He had quite the collection in here from some of the classics to some very scientific books.

For a moment, her mind wandered to Roy. She wondered what he was all doing during this mission. Her heart slipped a beat as she thought about both Roy and Josh before she shook her head to clear the thoughts. She needed to stay Clara for this and stay focused. Taking a deep breath, she let it out slowly and started to rescan the pictures.
 
There was a vacation photo that gave Serena pause. It was probably Hawaii or the Bahamas, but the man was topless wearing a hint of swim trunks and a necklace of shells, while his wife, the lady of the house, still wore a sexy one piece.

That was the common denominator. Even now she was wearing a dress that covered her up, while accented her curves. Rescanning the photos it seemed the woman never exposed her midriff and dared only to show off the top of her cleavage.

Serena couldn't expand any more on this as a knock, nice of the guard, announced the door was about to open. When it did the guard looked Serena/Clare over and then around the room once. "Let's go." he said in a clipped and thick accent.

He took her to the stage and moved away while she waited for the curtains to open. Just then the live band started a song that was probably least expected, and as the energy of the party shifted the curtains opened...
https://youtu.be/Wrbdc--KmEE

"Clare" was the focus of the spotlight but it was well overhead so as not to blind her. The party boy, Lorenzo, was being shoved into an empty area of the dance floor at the base of a dais while he nervously tried to shy away from what he must have viewed as the sex goddess here to bless him with his new manhood. Even with his bronzed skin tone it was clear he was blushing. The newly minted 18 year old was fully aware of what was to take place.
 
As the guard knocked, she turned and moved towards the door. Was Scorpio not a man at all but the lady of the house instead? She had never had to seduce a woman before. Guess she was going to make the son a man and then try to convince the lady of the house to let her have some fun with her.

She followed the guard, a bit nervous as to how her entrance was going to work. She soon found out as she was let on stage behind a curtain. As the music started and the curtain opened, "Clara" smiled and let her body move with the music. She danced a bit to the music as she made her way towards the shy boy.

As she reached him, "Clara" moved her arms around him and danced against him to the music. After a few awkward moments, Lorenzo started to dance with her. She turned and while they danced, she purred into his ear. "I am Clara. I am going to make this a night you are never going to forget. Want to dance a little more first or slip away?"

Serena pressed her body against his as they danced and she could feel his growing erection. Smiling to herself, she sucked on his earlobe before grazing her teeth over it as she released it. She felt him shudder and she slipped her hand between them to cup his growing member and give a gentle squeeze before winking at him. She realized that she had him too worked up to answer her question so as the song finished, she looped her arm in his and they walked over to his table. He took a much needed drink from a glass. She wasn't sure what was in it but he seemed to relax a bit.

Lorenzo reached over and took her hand before placing a kiss on the back of it. He then started to lead her away from the table and through the crowd towards the rest of the house.
 
As they walked away a few of the friend cheered, knowing what was going to be going on soon. Lorenzo put up much bravado at the start, but once they were away from the party "Clara" could feel his hands getting colder as he grew more and more nervous.

When the finally reached his bedroom, Lorenzo opened the door and stood aside so his date could enter first. The room was the size of her first apartment. It even had it's own wet bar and mini fridge. The entrance was a sitting area with leather furniture and a big screen TV with various game controllers on the coffee table.

The back was the bed, larger than a king with purple and black comforter that matched the purple, red and black pallet of the room. Even the movie posters, most of which were Marvel or Star Wars, kept mostly to the same color pattern. It was almost as if the were either selected for this room, or the room was decorated around the posters.

Lorenzo stepped in and closed the door, locking it. "So... You are... English?" He asked with a heavy accent that failed to make his nervousness. "They tell me you are to teach me sex. Yes?"
 
"Clara" looked around the room, making mental notes of any ways she could leave or places they could be spied on. "Yes, I am English." She replied as she walked around him, watching him. "I will teach you the ways of sex, Lorenzo and I think you will enjoy it. Relax a bit. It's not as fun if you are tense or nervous. Your mother made a request but I want to know, what do you want? What would you like to do to me or have me do to you?" She asked as she lightly trailed her finger along his jaw line, down his neck and to the top button of his shirt.

She worked the top few buttond so the top of his shirt opened and she grazed her nails on his chest gently. She wanted him to relax, not stay all tense. She could have more fun with him but her true mission was his mom. She would have to see how she could get close to her as well.

Slipping off her shoes, she set them by the door before leading Lorenzo over to the couch in the sitting area. As they sat, she wrapped her arms around his neck and placed soft kisses along his neck while she waited for him to answer her question. She wasn't going to let him get away with not answering this one.
 
Lorenzo was nervous, and stuttered shyly, "I... I watch the movies." He shuddered under her lips and his hands lightly touched her sides, too high to be sexual, too low to be platonic and too light so as to do anything that would make all this stop.

"I like... I want." He was breathing fast now, "I want you to suck it. Then I spray it on your face." He deflated a bit, almost as if he was embarrassed to admit that. Clearly it was something he'd seen in porn time and time again, and had built up a fantasy about it ever since.

While his mother did want her to user her mouth and then her body without condoms, she did specify that he was to learn to control his orgasm and learn to enjoy the pleasure. Yet the inexperienced 18 year old only knew how to masturbate until he made himself cum to porn clips.
 
"Clara" smiled at him as she unbuttoned his shirt the rest of the way and kissed down his chest. "I have another idea. How about I suck here..." she said as she trailed her fingers over the bulge in his pants. "And then I will sit on your lap and ride your cock." She watched him, her eyes gleaming.

She really did want to give him a night to remember. She slid down his body, laying kisses down his stomach until she got to his pants. She unbuttoned the pants and tugged on them and his boxer briefs. He lifted himself slightly as she pulled them down all the way. She knelt before him and smiled at him as his face turned red. Moving her face closer, she licked up the length of his manhood before wrapping her mouth around the head. She didn't want to give him too many sensations at once. Pulling back, she looked at him. "Your mother wants to make sure you don't finish too quickly. Can you hold back as much as possible and when it becomes too hard, tell me?" "Clara" asked sweetly.

She tried really hard to make sure she was being nice and acting like a prostitute. She didn't want to blow her cover at all.
 
As expected, the boy now turning man lay there nervously still. He let Clara work him over with her mouth making noises of approval and passion but simply laying still. It would be only a minute or less before he would gasp and notify his Sex Teacher that he was getting close so that she could stop.

"I do not understand." He said about the 2nd or 3rd time she stopped, "I thought I was supposed to... you know... do it." Clearly confused that he was not allowed to cum when he felt the growing need to.
 
"My dear Lorenzo, it is wonderful to cum but you don't want to finish too fast. You want to make sure you have pleasured your partner as well. It wouldn't do toy any good to reach your orgasm and leave your partner unsatisfied. This is part of what your mother wanted me to teach you." Clara said, her breath caressing the tip of his cock as she spoke. Clara thought for a moment before shifting up to his face again.

Leaning in, she nipped at his earlobe before whispering in his ear seductively. "Pleasure me Lorenzo. Show me what you have learned." As she spoke, she reached a hand back and unzipped her dress. Standing, she let it fall to the floor in a puddle around her feet. "Come Lorenzo...show me baby. Make me call your name in pleasure. Then I will show you how things really feel." She said with a wink as her bra dropped away as well so she was only standing there in a thong.
 
Lorenzo's eyes just fell to her breasts the moment they were exposed. He reached up and cupped the soft and succulent mounds kneeding them and watching as they responded to his touch. While he was entranced for just a few moments, it was an almost awkward trance he'd fallen into.

Finally, his hands moved to her hips and his eyes down to her waist. He sank to his knees, but only to get a better look as the woman before him. 'Clare' could tell he wasn't breathing, as if he didn't want to do anything to end this moment, and as he got to his knees he placed a series of kisses on her warm and inviting sex. Awkwardly and inexperienced he continued to kiss and lick at the out edges of her until he finally grew bold and seemed to remember something he'd seen in porn.

He pressed two fingers at the sides of her slit and began to flick his tongue at random across her warmth. He kept going, waiting for either instruction or a reaction.
 
"Clara" tried to be encouraging to Lorenzo as he awkwardly tried to please her. She watched as he stood mesmerized by her body and couldn't help a smile as he sunk to his knees.

As he became a bit bolder, without a word of encouragement needed, a soft mom escaped her lips. "Lorenzo, would you prefer we move to the bed?" She asked as she tipped her hips to grant him better access.

After a few more licks he got to his feet and then went over to the bed. "Clara" laid down and spread her leg. "Now Lorenzo, I want you to put your face between my legs and do what you were doing before but aim for this..." she places a finger on her clit. "And this." She slides her finger down to ro her hole to show him where to go. "If you do well enough, you may even get to taste my cum before I let you fuck me with your hard and impressive cock." Her smile was genuine as she watched him move to the bed with uncertainty.
 
Lorenzo watched, showing he was good at taking direction. His hand, however, seemed to unconsciously stroke his thick and iron hard shaft. He leaned in, moving his hands to rest near Clara's hips and did as he was told.

It took only a moment for him to figure out he needed at least one hand to help part her lips as he licked and kissed her clit, then moved down to do the same with her entrance. His technique was more mechanical at first, then he started to grow bolder and pressed his mouth to her sex and began to truly explore her with his tongue.

He began to eagerly lick deep, exploring the walls of her cunt with his tongue before pausing to actually suck and lick her nub for a few moments, but it was clear he liked plunging deep into her folds as he fucked Clara with his tongue like a starving man begging for a meal.

Whatever hesitation he had was now shattered as he started to even hum his satisfaction and desires against her almost as if he wasn't even aware he was doing so, just letting his primal urges take hold.
 
As Lorenzo became more eager and confident, she started to enjoy herself. He wasn't even close to the skill level of Roy or Josh but he wasn't bad once he got into it.

Moaning, she moved her hips a bit grinding into his face as pleasure started to build. "That's it baby...like that. Keep going. Mmmmm" 'Clara' moaned. She wondered that he would actually feel like buried inside of her. She has to admit that his cock was rather impressive. She was so glad that it wasn't small because that would have made this mission harder.

Putting her hands on the back of his head, she ran her fingers through this hair as she bucked slightly when he sucked on her engorged clit. Her orgasm was so close and she was surprised as how well he was doing. Her moans grew louder as his tongue plunged inside her again.

"Mmm Lorenzo.... I'm going to cum...don't stop...Looorrrenzoooo!" Her voice hitched as she cried out his name. Her orgasm ripping through her body as she coated his tongue with her juices.
 
Lorenzo grunted in surprise, but to his credit he continued to keep his mouth tight against 'Clara' and kept doing what he was doing, even as she cried out in ecstasy. While still new to all of this he stopped when she stopped moving, not knowing she was still in the after throws of her orgasm.

"Now?" He asked, moving up her body and placing the head of his throbbing cock against her soaked pussy. He paused, waiting for a response for only a second and thrust into her assuming her gasping and lack of objection to consent. He groaned and whimpered as he felt the sensation of sliding into a woman for the first time.

"Si, cosi mi...!" He muttered, pressing deep into her and gasping for breath. He groaned as he pulled back and thrust into 'Clara' again, then again more quickly. In seconds he was hammering his hips against her, his hard but experienced 18 year old cock driving him to seek more and more pleasure.
 
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