Courtesan Cop Ch. 06


Mandy remembered the summer when she had her first boy all to herself - not that they had had intercourse, that would have been out of the question - but he was the first boy whose pants she took down and whose penis she played with. He was actually her cousin Andrew, and he was only a year younger than her…

She had enticed Andrew into the boathouse on the promise of ice cream later if he’d just hang out with her for a while and be a good boy. Truthfully they both knew what was going to happen - she knew her plans, and she could tell from the look on his face that he hoped she would make advances. She liked how he’d developed into a good looking young man and was determined to have her way with him.
She decided that he was quite attractive, with his growing muscles, his cute round bottom - so ripe for spanking - and she just couldn’t keep her eyes off of the grown-up and filled-out shape of her cousin’s pouch.
And she had wanted to get her hands on him for quite a while.
So she had led him to the boathouse, and there she had kissed him.
She held him in her embrace, kissing him and even using her tongue. She had gently begun to massage his nipples and then had pinched them as they kissed, causing the boy to whimper into her mouth, and she felt his body going softer and more submissive in her arms.
She laid him down on a blanket she had earlier set out, and he didn’t resist but instead laid softly with his hands at his sides and let her cradle his head in her arm as she continued to play with his nipples and kiss him.
She knew the boy - like all boys - was something of a slut at heart, yearning for a female to touch him and do things to him. She knew he wouldn’t resist at all as she let her hand roam slowly downward from his nipple to his taut belly, and coming finally to rest softly upon his genital pouch. She just laid her hand there, letting him feel it, making him want it, and his response to her kisses became more passionate.
She could feel his penis stirring to erection under her palm, but she played her cards with the coolness of having calculated this plan all afternoon, so she just let her hand lay upon his boy-parts and listened to him moan in submission to her advances.
Ever so slowly, she cupped him, giving gentle reassuring squeezes, letting him know it was alright to let her touch him. She knew boys were easily aroused, having seen virtually every male she knew with an erection at least once, but she also knew it was best to take it slowly so that the boy could always tell himself that he had been seduced and helpless to resist.
She smiled as she felt his hips begin to wiggle involuntarily and his penis began to throb fully, getting stiffer by the minute. She felt the fabric of his swimming suit stretch as it was designed to, giving space for the boy’s penis to expand and lengthen in her hand.
She held him tighter and began to kiss him with more passion as she let her hand slowly slide up to the low-rise waist band of his swimming pants. Slowly, ever so slowly, her finger tips slipped under the waist band, and she followed the taut flesh of his abdomen downward, feeling the fresh stubble of his shaved pubic region tickle her hand as it moved down.
This was the moment of truth. It was one thing for a girl to cop a feel of a boy’s pouch - it happened all the time and was something a boy had to accept.
It was another for a boy to let a girl cup his pouch and hold still to let her really feel him up.
But it was the real breakthrough when her hand went down his pants to touch and feel his naked genitals.
It was well known that once a girl got her hand down a boy’s pants, and touched his naked flesh, it was a relatively easy next step to get the boy’s pants down or even off. If a boy laid still for a girl to slip her hand into his pants, he had already made the decision to allow her to milk him.
“Eureka,” she had thought as her finger tips touched her cousin’s swollen glans and her palm rested upon the stiffness of his shaft. She let her hand slowly and gently explore his hot flesh - such a mixture of soft and firm things. Firm but delicate testes in a soft scrotum, stiff erect flesh covered in the velvet soft and sensitive pink skin of his penis.
It was important to move slowly and let the boy’s arousal build so that he was beyond resistance, so she took her time kissing him and feeling him up. She showed him that she was gentle and nurturing, not harsh. She waited until his throbbing penis was fully stiff and pushing up against his pouch.
With her hand still gently fondling his naked genitals, she pulled her lips from his long enough to whisper, “Close your eyes and let me your suit down, Andrew.”
As she had expected, the boy hesitated only a moment before he closed his eyes, and then lifted his bottom to allow her to take his suit down. She gripped the waist band of his little trunks and wiggled the garment down his thighs. As she watched him surrender himself, she smiled in satisfaction, knowing that she would make him spurt.
It would be the first time she had ever taken a boy’s semen, so she wanted to do it well - just as she had read in a hundred trashy romance novels and magazine articles.
She began to kiss him again when he had relaxed back into her arm with his hands submissively at his sides once more. Slowly, she let her fingers wrap around his shaft, really feeling the iron-in-velvet of an erect penis for the first time, and it was very much as described in books and in gossip with other girls.
She began to stroke slowly up and down, as all girls knew to do from whispered and giggling conversations growing up. She was pleased that Andrew was responding with gasps and moans in their kiss and with cute wiggling of his slender hips.
She knew the kind of words that would make a boy melt in submission, and she whispered to him as she rubbed his penis, slowly increasing the pressure of her grip and quickening her strokes.
“Good boy, Andrew,” she cooed, “Just let me touch your pretty penis a little while. That’s a good boy, just relax and let me touch you. Yes, breathe deeply and surrender yourself to me…that’s right, good boy. It’s ok, Andrew, I’m just going to touch you for a while, you can be a good boy for me and let me play with your penis.”
She kissed him some more, and then tried some of the naughty phrases she’d read in the trashy novels. “Now lie still, pretty one, and keep quiet, we don’t want anyone to hear you moaning too loud, do we? What if your sister saw you letting me touch you with your pants down? She’d think you were a naughty boy… so be still now for me like a good boy. It will be our secret that you’re a naughty boy and you let me take your pants down and touch your penis.”
He whimpered submissively, and she continued. “I’m going to make you spurt your semen for me, Andrew. And you know it’s naughty for a boy to let a girl make him spurt, but I know you’re going to be my naughty boy and spurt for me. I know a boy tries to be good, but you really want to spurt for me. You can’t help but be naughty, and it’s okay. I understand…”
She smiled as his hips wiggled and he moaned in surrender to her. She said, “And what happens to naughty boys let a girl pull down their pants, Andrew? What do we have to do with naughty boys who spurt?”
“Spanking…” he whispered desperately.
“Yes,” she cooed, “Naughty boys who let girls play with their penises and make them spurt need to have a spanking. It’s only natural. But I won’t tell anyone you let me play with your penis as long as you are a good boy and lie still for me. I’ll give you the spankings you need, so we can keep this our secret. Isn’t that nice of me?”
He nodded that it was nice.
“ I know you need to spurt all your semen for me, but you must learn to be a good obedient boy and learn to ask permission to spurt for me, Andrew. So when you feel that you must spurt, you will ask me for my permission to ejaculate.”
He nodded emphatically.
“Good boy,” she whispered as she noted the typical boy-reaction to hearing all her words about being naughty and deserving a spanking for letting his pants down. It was so predictable, and amazingly easy to make a boy desperate to ejaculate.
Soon his breathing was labored and Mandy slowed her hand. “Not yet, I want to play with you some more,” she said, and delighted to hear his desperate whimpers. It made her so happy that she had brought him to the edge of ejaculation, making him completely in her power. It was so fun!
Then she thought of the things that would follow his spurting - later, he’d have to lie across her lap in submission as she swatted his cute bottom. She had spanked her brothers many times, whenever they were disobedient, and especially when she caught them masturbating - which was very strictly forbidden.
But that wasn’t the same as spanking a boy whom she herself had made to ejaculate. That would be amazing!
She said to him, “After I make you spurt for me, you’ll have to submit to a spanking, Andrew. You’ll be a good boy and take your spanking, won’t you?”
He moaned and opened his eyes. “Mandy…” he gasped as she sped up her hand motion.
“Yes, Andrew?” she whispered, speeding up her strokes even more, since she had read how fun it was to talk to a boy and make it almost impossible for him to answer because of her stimulating his penis.
“Ooohhh…” he groaned, “I… think… Aaaahhhh…. Oooohhhh…”
“I didn’t understand you,” she giggled, “are you trying to say something?”
“Aaahhh… please…. Oooohhh….”
“Please what, dear?”
“Spurt…. Ahhhh… for you…… oooohhh… please….”
She was delighted. “Yes, you may spurt for me NOW,” she said, “I expect you to spurt hard for me now, Andrew, I want to see all your semen spurt out of your penis now!”
According to all the magazine articles, it was important not to merely allow a boy to ejaculate, but to actually command him to spurt - to make his ejaculation an act of submissive obedience. Of course he would spurt anyway, but to frame his ejaculation as an act of obedience will increase his submissive feelings toward the girl who was controlling his penis.
The magazines said that this helped to make a boy become generally more obedient to a girl - and obedience is such a nice trait in a boy…
Mandy’s eyes went wide as she watched his first spurt. He was a fountain, as young men always were. She felt his whole body stiffen for a moment, and then release as his first spurt of semen came out of his penis and onto his belly. Mandy thought it was the most precious thing she had ever seen, and determined at that moment to see him ejaculate it again. Many times.
Mandy quickened her pace, watching in amazement as the boy spurted over and over, and feeling so proud that she had seduced him and made him spurt. She felt so powerful and in-control as the boy’s whole body shook and responded so fully to just a simple movement of her hand.
By controlling his little penis, she controlled the boy - just like the novels, magazines, and her girlfriends’ words had promised. It was too good to be true!
The look of complete submission on his face was priceless, and she exulted in her feelings of dominance over the boy as his semen began to slow into small spurts, simply running down her hand. She was in total control of his body, and the pink throbbing head of his penis continued to reward her with little spurts as she pulled and squeezed and stroked it.
She felt his body relax against her, she heard his little whimpers of completion, and she continued to gently milk little droplets from his penis as the magazine articles had recommended.
‘Never leave a drop left in him’ the articles said, ‘it’s important to show the boy that you require that he surrender every last drop of his semen, and that you will take it from him. This way, he will know it is not his choice in the matter, but that you are in complete dominance over his penis and his semen. Continue to gently milk his penis until it is soft again in your hand before releasing him.’
Mandy was thankful that the articles could provide such a good guide to milking a boy, and by following the instructions, she felt she had done a very good job! She had taken a boy’s semen! She felt like a real grown woman! It was a marvel to actually cause a male to ejaculate, and she knew she would remember her first time in great detail forever.
When he was finally soft, she laid his penis gently on his belly, and followed the pattern she had read. She cradled his head against her young bosom, caressed his face, and cooed encouragement and praise.
“That was a very nice ejaculation, Andrew. I am very pleased with the amount of semen you spurted for me. You were a very good boy for me and you did very well. Now just relax and rest a while.”
She kissed him on the forehead and she liked how he’d smiled with embarrassment and pride mixed together.
She continued, as the articles recommended. “Your penis looks very cute, all soft and covered with semen, Andrew. You just rest and I’ll clean you up.”
She got some tissues from her purse and cleaned her hand and then his belly and genitals. Then she reluctantly pulled his suit up and positioned him nicely in his pouch. She thought, ‘that’ll keep you from having an erection, at least for a while,’ she giggled, ‘but not too long, I hope.’
Later that afternoon, Mandy’s older sister Julia pulled her aside on the patio of the lake house. “What were you doing with Andrew in the boat house after lunch?” Mandy was fearful until she saw her sister’s knowing grin. “Were you making him naughty, Mandy?” she asked.
“I don’t know what you mean.”
“Of course you do. I saw the little stain on his pouch, sis, and he seemed quite relaxed.” Julia pulled Mandy close and whispered, “Tell me every detail.”
Mandy told her sister everything that happened and everything she’d done.
Julia was impressed. “My little sister is finally growing up,” she smiled, “so what are your plans now?”
“I want to do it again,” said Mandy, looking down and blushing a little.
Julia smiled, “Of course you do. Who wouldn’t.” She looked at her little sister and said with a wicked look in her eye, “Want some advice?”
“Sure,” said Mandy.
“I recommend that you do him 3 times a day, and spank him once a day for allowing it. That’s a pretty good ratio, I think. And you should tie him up at least a few times and do some T&D, that’ll really be fun.”
“What’s T&D?” asked Mandy.
Julia said, “Teasing and Denial, silly girl. Take him right up to where he’s asking permission, then you squeeze his penis at the base to stop him from ejaculating. Spend about a minute or two just fondling his testicles to let him half way cool down, and then start over. You can do this as many times as you like as long as he doesn’t actually start to spurt - but when he does, finish him. You tie him up and do this, and he’ll fall in love with you forever.”
“Wow, that seems almost cruel…”
“No, they love it. It’s like a spanking - they complain when you do it, but it makes them happy none the less. He’s a cute boy and if you don’t take full advantage of his 18th birthday, I will.”
Mandy frowned, “I want to take advantage, I assure you. I’ve already started, obviously.”
“Yes, well, good. Be sure not to waste any,” said Julia as she walked away.
Over the course of the following week by the lake, Mandy had taken her young cousin to the boathouse several times a day to masturbate him. When everyone else was on the lake, she took the opportunity to tie him hand and foot, and do a little T&D on the boy. When she finally let him ejaculate on those occasions, he really gushed for her.
She grew to love the T&D, she liked how the boy would writhe and moan and beg - very similar to what he did when she spanked him.
All day long, she treated him like her own boy, enjoying his body whenever she wanted, feeling and groping his pouch at any time others wouldn’t see her do it, in addition to playing with his naked penis for hours in the boat house.
She was very pleased to see how docile her cousin Andrew had become - he was very submissive to her after that first encounter and allowed her complete control of his genitals to fondle and play with as she desired.
In addition to milking him several times a day, she had taken him across her knee each evening, simply to remind him that he was a naughty boy for letting her take his pants down and do what she wanted with his penis. He submitted to the spankings without complaint and took them well.
The magazines consistently recommended that milkings and spankings should go together to bring a boy into deep submission, and it certainly seemed to work very well for her with Andrew.
The last night at the lake, before they were all to go home, she made him ejaculate the final time while she held the head of his penis in her mouth. It was her first taste of semen, and from that moment she knew why women raved about it.
It was a thrill to feel a boy ejaculate into her mouth - it was so intimate to feel the spurts of his warm rich boy-juice fill her mouth as he moaned and writhed beneath her - and not only did she find the taste of semen rather more pleasant than she had expected, but she felt as though it gave her a healthy ‘lift’ of attitude. No wonder she had overheard older women whisper of the importance of ‘not wasting any’. She regretted all the semen she had earlier cleaned up with tissues over the course of that week…
It was a wonderful time of discovery for her, and she had learned-by-doing about what to say to a boy during penis-milking to open up his submissive soul to her, how to employ over-the knees spanking to reinforce his submission, and to enjoy the healthful benefits of having ‘a little snack’ of semen.
Although Mandy had many other boys since then, Andrew would always hold a special place in her heart as her ‘first’.
Now her Andrew was all grown up and was now concubine to a nice woman who owned a shop… but in a way, he would always remain ‘hers’ since he was her first boy-toy, and she was his first mistress…

Mandy finished reminiscing about her cousin, and thought again about the Courtesan seated in the car next to her. Tonight would be another ‘first’ for the handsome young police detective. His first sheathing. And she hoped it would be special for him.
She stopped the car in the parking lot of Caledonia House, and a sharply dressed woman of about 50 met them at the door.
“You must be Mandy, and this must be our Jeffrey,” she said warmly.
“Yes, we are,” said Mandy.
“I am Mistress Karena, and one of my duties is to prepare the young Courtesans of our house for their first engagement. I am very honored to have this duty this evening, as I have followed the career of our young detective for quite some time.”
She smiled warmly at Jeffrey, “Don’t worry dear, I’m going to take very good care of you.” Then she looked at Mandy and said, “Please follow me.”
They walked through a long hallway and then down a flight of stairs, emerging into a spa area with a pool. They stopped at a reception desk and Mistress Karena retrieved a small bag, from the girl at the counter, and then led them to a private room medical exam room.
Jeffrey undressed down to his tiny pouch-thong and a nurse came into the room, taking his temperature, blood pressure, and weighing him. Then Karena handed the nurse the bag, which the nurse opened and retrieved two pills and two syringes.
Jeffrey obediently swallowed the pills and leaned over the table to receive the two injections on his hip.
All this time, Mandy greatly enjoyed looking at the young man’s body, and she imagined what it would be like to milk him as she had done with her cousin Andrew so long ago. He was quite a prize and she envied the woman who would take his virginity that evening.
Mandy’s curiosity got the best of her and she finally asked, “What are the pills and injections for?”

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