Choosing My Sister's Partners

I leave the accommodation grounds and head straight for the coffee shop, only 2 blocks away on a corner. My mind races, thinking the best way to approach these candidates, how best to assess them and decide whether to waste time approaching... I'm a very confident person, born out of necessity to build and keep a base of clientele for my freelancing endeavours. But this is not a subject you normally breach in public to strangers... But it isn't illegal to matchmake, so I can do no harm in trying.

And I am already at the coffee shop door. I go cavalier mode, no scoping out, straight into the cafe like a normal person would, and join the queue. Jenna and I have had coffee here before, which helps me fit in as just a returning customer. I am the epitome of nonchalance, lining up and ready to order coffee - a cappuccino. There's a couple of girls in front of me, and as I look around the room, I can see a few people. 1 old lady, a couple about my age, 1 younger man on his own swiping and typing on his smartphone. A possible match straight away, but I won't get ahead of myself. I must take the greatest care to select my sister's first sexual experience.

I've ordered my coffee and exhanged some small talk with the waitress who is also the barista. She's a nice woman. Neither of the girls in front of me sat next to the lone young man, so I decide to go over to his table and gauge the situation. Standard clothing, jeans and tshirt. Slight hint of aftershave, he's clean shaven, short black hair which does it's own thing and suits him. He's drinking what looks like a normal white coffee. Keeping it simple, I can respect that. I take the plunge.

"Hey, sorry man, can I get your help with something for a minute?" I approach as I get his attention, not talking to loudly, keeping it low but friendly. He does the usual skeptical reaction, which I am prepared for of course.

"Oh, what's that?" He asks slightly defensively.

"It's complicated, you just seem like the type of person who could help me out... Can I sit and explain myself? I'm sorry to interject on your nice afternoon." I know that most people like to have the opportunity to help others. He squints, smirks and nods his head, waving his hand at the chair opposite him.

"Thanks man, I'm not after money. You seem like a helpful guy and that's a good start." I compliment him as I sit down.

"I try, so what are you after sir?" He smirks and throws off the compliment. Modest as well huh.

"Me? Just my coffee. It's actually someone else I am helping out today." I grow his curiosity.

"Uh-huh." He makes skeptical noises and takes a relaxed swig of his coffee.

"Ok, I'll be straight with you man. I am bringing someone back to sleep with my sister today, so I'm currently looking for a good person..." At this point the waitress approaches with my coffee. We know each other from my previous visits where I am usually with my sister.

"Hi, your sister couldn't make it today huh?" The waitress beautifully proves to the man that I have a sister and his eyes go from cynical to wide and surprised.

"Hi, yeah, I've just been at her place, she is busy just at the minute but I thought I would pop in anyway. Love the coffee here. Thanks!" I chat familiarly to the waitress as she tables my cup, to assure the man I am not some random hustler. She smiles and turns to go to clean another used table. I stay silent and hold my fresh Cappuccino to my nose, inhaling the incredible smell and ignoring him for a few seconds. He probably needs a moment to think about what to say next.

He finally says something after about 5 seconds.

"Okay, what makes you think I am the right guy?" He quizzes my decision to approach him.

"Oh, I'm still figuring that out. I'm not going to bring her someone just because he said yes." I explain.

"I didn't say yes." He retorts. I like his wit and throw him a wry smile of appreciation. This guy is actually pretty switched on.

"Alright, tell me a story about yourself while I load up pictures of my sister to help you decide." I throw an almost combatively coy smiling glance at him as I place down my cup and whip out my phone. He takes a drink while he tries to think.

"There's not much to me man, I just live and work a regular life here. I'm single if that helps." He is seeing where this thing goes, which I commend.

"Yes that all helps me actually." I go to pass him the phone with the first picture of my sister. Purple bra and underwear, about half of her face showing, the youthful curves and soft skin are sure to take his decision out of the equation.

"No, you can show me the pics if you think I'm good enough." He puts his hand up to signal a stop. I am taken aback and further impressed.

"Wow. Nice moves dude. That's no ordinary level of respect." We both drink our coffee for a second. I suddenly overhear a commotion behind me.

"You want me to always pay half, can't you just offer to treat me sometimes? You just ruin this with your stubborn frugality and rules!"

"I've done that before, besides, yours is always more expensive..."

The couple a few tables away are having a significant meltdown and we both get earshot of the escalation. After my eyebrows have returned to their home just above my eyes, I turn and throw my candidate a concerned, annoyed squint. He blinks at the ceiling and cringes at the couple's behaviour as they continue to argue.

"Hey man, what's your name anyway?" I ask, trying to remain undistracted by the noise.

"Bruce."

"I'm Elpy... Jesus, wait there a minute man..." I turn as I leave my seat to approach the table that the arguing couple is at. Bruce calls after me;

"Not going anywhere, Elpy Jesus!" He catches me right off with that and I turn and laugh loudly, thoroughly impressed by his wit yet again. I reach the arguing couple.

"Hey guys, you sorting this out?" I both offer help and infer they need to mind their manners in the same sentence. The woman is first to respond. She is roly-poly, about mid 30s, long scruffy black hair in some tied up description, large breasts and legs, and most other things too. Hamish is a ginger fellow with a friendly spectacled face, a slight portly bump in his belly but otherwise fairly square and strong looking in his frame.

"None of your business, but anyway my ruinous boyfriend just can't let me enjoy even a simple thing. So embarrassing!" She whinges. Her boyfriend looks at me with defeated eyes.

"I heard you from 3 tables away, so it is my business. Sir, is she right about you?" I scold them both.

"I'm so sorry man, I shouldn't have stood up for myself in here, I knew it would cause a scene." I glance at the woman as he says this and observe her visibly about to blow her lid.

"Woah, hold on man. You stood up for yourself how?" I ask him, and the woman immediately interrupts to change the subject.

"You just can't help it, you always make me feel bad about money, you can't just treat a woman to something nice without a fuss, damnit Hamish, I can't stand it!" The woman is in full soap operatic mode.

"Hamish. What wrath you have incurred?" I infer him to defend himself.

"I... Our bill is just over fifteen quid. I put a ten down on the table as you can see, and now here we are." Hamish explains. I see that there is a 10 on the table, more than half of the bill, and no other money has been placed down in the tray.

"Oh I see, you have put down a tenner, a gesture to pay more than half of the bill I assume?" I confirm with Hamish here that this is pretty standard male fairness with a touch of protect and provide thrown in. Classic reputable male behaviour.

"Yeah..." Hamish confirms. The woman is trying to interrupt but I am holding my hand up to her while I listen to Hamish.

"Okay, miss? Where is your share?" I finally turn to the woman who is now looking rather the goat.

"Like I said, he just won't treat me special, like I am just some regular person, I pay half, you pay half, where is the romance, I'm not asking for that much, just to feel like I have a boyfriend who cares..." her cutting words are clearly watering Hamish's eyes up.

"Bloody hell woman. Romance is a two way street, He's offered to pay more than half, and you have thrown that in his face AND put nothing down yourself. What a massive projection. You, miss, are the one kicking up a fuss and being stingy with money here. What a disgrace." I napalm truth bomb her on her appalling behaviour. Hamish is nearly in tears yet seems shocked that me, a stranger, is standing up for him.

"How dare you..." The woman defaults to outrage as she has lost the case. "Hamish I don't think this can work..." She throws in a casual, infantile threat to leave this poor man on top of her abuse. I have heard enough and pull out my phone as I lean over to Hamish, putting my arm over his shoulder to comfort him.

"Tell you what Hamish, my sister is looking for a nice man at the moment. Look..." Hamish stares into my phone screen with awe at the youthful, pert breasted, delicious slim and curvy figure. The look on the woman's face is far too blazingly thunderous to peer directly into at this moment.

"Bullshit, nice try mister asshole!" She blusters, thinking I am bluffing and calls it. But she is a moron, because she should have been able to tell by the look on Hamish's face.

"You know what? Yeah, yeah I'll meet her. To hell with it." Hamish says as I flip the pictures to also show him the one of me and Jenna, as the proof. I present to the world, Hamish, the absolute pioneer who will not be manipulated by insane narcissists.

"Hamish, don't you dare joke around!" This woman is still deluding herself. Hamish sends her a dutch stare of death.

"Linda, I don't think this can work." He brutally reflects her empty threat, but this time it's a loaded weapon. I give Hamish my phone with a contact sheet ready and he begins typing his phone number in. I glance at Linda, who has clearly realised that she has just completely ruined everything and is sat silently humiliated with her hands over her mouth. While Hamish double checks his number, I draw my wallet and drop a twenty on top of Hamish's ten.

"I think you can leave anytime, Linda." She glowers at me hatefully, as I taunt her, then looks at the money on the table. She actually then takes Hamish's ten, gets up and goes to leave. I think about stopping her for theft, but it's not worth it when we already won. The waitress I know, but don't know her name, has seen this happening. I look at her and apologise.

"I am so sorry, uh, I just wanted to make things right and stop the disturbance." She is glowingly smiling at me, and approaches to within a step or two of us.

"Elpy, the way you handled that was... incredible... I saw the tip you had down... thank you so much... I mean, what I mean is, thank you for doing the right thing here. That woman was awful."

I square up to the waitress and look her up and down. I haven't appraised her properly before. She's definitely in her mid fifties, her skin aged but healthy looking, the occasional wrinkle, but she's slim, and actually as I look at her now, has an amazing bust and rather inviting legs and buttocks.

"Hey, you know my name but I don't know yours, miss?" I ask her.

"Tracey. I'm Tracey." She blinks at me and continues to stare at me and the situation. I pick up Hamish's bill tray with the twenty on it and move to her, nice and close, to hand it to her.

"Here, Tracey. Keep the change." I softly rumble my voice next to her, standing intimately close to her while she takes the tray from my hand.

"Thank you, Elpy." She whispers with her mature, slightly smoke damaged voice. Her breath catches my cheek and makes me semi erect. I give her an intense stare into her eyes for a second before smiling and turning back to Hamish.

"All done man?" I offer to take my phone back.

"I'm definitely in there, and you have no other Hamish, so that's it." He explains.

"I'll text you either later, or in a couple of days man. You have my word. Take it easy til then." I assure him he hasn't dumped his manipulative woman for no reason.

"Thanks for all that." Hamish sits there exhausted looking. We both nod a farewell and I head back to Bruce and my coffee.

"Well that was something altogether else..." Bruce has been sitting back watching the drama unfold.

"I think that man just dodged a bullet with that woman, I mean wow." I express disappointment that some people are like that. "Anyway, you were about to tell me a story, any story, so fire on, I have time to kill." I sit down again and go to drink more of my cappuccino. Amazing how the foam keeps the heat in the liquid.

"Listen man, I don't know if I like this whole thing. It doesn't feel right to me, I should meet your sister before just getting in there and..." He explains the weird nature of this quest of mine.

"That's the sort of thing a good guy would say though." I explain. "And you have to consider my sister's situation. She's socially pathologically unable to say yes to sex, even if she wants to say yes. She has tasked me with helping her break that barrier, so I will do that."

"Huh." Bruce mulls over the problem. I go on talking.

"It's funny, something that just occurred to me right now. Most men are good men. There is a stigma in our society around men and how risky they are, but, I've already deemed 2 of 2 men that I have assessed today as suitable to spend time with my sister. Even I went in to this with a cynical outlook, expecting to cross out at least half of the men I assessed. Isn't that something."

"That actually makes perfect sense if you think about the statistics." Says a fairly switched on Bruce. "Who was the other guy by the way?" He tries his luck.

"Potential guy." I somewhat lie to him. "Need to know only, sorry." I deny him the information.

"Fine. Normally under those circumstances I would tell you to shove off. But your sister's problem requires further consideration." Bruce is irked but decides to sympathise.

"You can see the pictures. I think you are a good and honest dude." I hand over my phone with the pictures ready to go. Bruce stalls as he understands the gravity of attraction that seeing my sister's body will have on his decision.

"I can take you there right after this to help her out." I keep it simple with him. He finally takes my phone and looks at my sister's body shots. His white face reddens steadily as the images affect him.

"Jesus." He realises he can't deny my sister's soft figure. I drink towards the end of my cappuccino, a victorious gulp of sorts.

"How's this going to work then?" He wants to know the details.

"I bring you to her place, you get past the small talk and enjoy yourselves. You have up to 24 hours with her, from when we get in the door, so you should take control of the situation with her as soon as possible, so that she gets as much experience as she can. Remember, she is not going to be able to make intimacy happen, it has to be you that starts it, and she cannot say no, and if she does, you ignore it because she has already told me she still wants it." I lay it out plain as day.

"That's insane... but... I can do that." He agrees.

"After that, it's up to her to contact you again, so if you have done a good job of helping her through her barrier, you might be in for another encounter." As I finish explaining, Bruce and I have finished our drinks and Tracey with her long wavy red hair approaches us. She collects our cups and makes sure to bend over across my shoulder, obviously deliberately caressing the back of my neck with her significant mature yet soft breasts hidden behind her now fairly open blouse. I lean back discretely into her torso to body sign that I accept her gentle show of affection with great enjoyment. Thank you Tracey, I now have a brutal erection and need to find release. As she stands back up to relieve my head from her boobs, I turn with a big smile and talk to her.

"Thank you so much Tracey, I'll be paying for us both, so can you bring me the bill?" I virtue signal and show off a bit to Tracey in front of Bruce.

"Sure thing Elpy, in fact why don't you come over with me and get it?" Tracey makes the definite unusual request that requires more effort from the customer. But I know why and I can't help myself. I play innocent and hope I am not imagining her very intense flirting.

"Oh, yeah! Lead the way Tracey!" I get up to follow her to the counter and nearly forget to organize Bruce.

"Oh, Bruce, if you want to do that thing now, just wait for me here or outside, if not, see you next time!" I talk like we know each other and were talking about doing something. Half of that it truth at least. I follow Tracey to the counter and she passes into the staff side. She tallies up the table bill.

"Pay by card? No problem." She starts scripting our interaction ahead of my decision. "Oh, sorry, it's not working again. It works better nearer the thing through here." She beckons me through the staff area into the back room where there is a kitchen, an office, a toilet and a larder area. I follow her into the empty office and she closes the door behind me, with a latching sound. I turn at the sound of the door securing behind us and for seconds, Tracey and I face each other.

She drops the card machine onto the desk and launches herself at me, her right hand flying down my jeans and her left hand reaching around my back, going for full lips passion. I accept her intense lust and feel her fingers closing around my solid 7 inch cock. I ravage her mouth with my tongue and my hands dive into her blouse, finding her erect nipples and large round breasts softly giving way to my fingers. She unzips my jeans and tugs downwards on them while I squeeze her big silky boobs spilling from her bra.

She gets my cock to burst out from my boxers aggressively, while I lift her boobs out of her bra and start lifting her dark blue knee length skirt with my hands. She has wonderful freckles on her chest and forehead, incredibly sexy fiery hair and breasts from the gods themselves.

"Oh fuck, Elpy, give me your tip already!" Tracey's play on words is stupendously arousing, the big veins on my cock surge as my fingers curl around her panties and drag them down her legs. The back of my hand strokes her sticky wet pussy and drag strings of her lube down like strands of slime attached to my hand. The hotness of this is heavenly.

"You're getting the whole thing Tracey..." Our lips kiss pressingly and my hands glide up to her buttocks and my arms begin lifting her pelvis towards mine.

I lower her down over my flagpole of a dick and feel her slimy hot pussy touch against my shaft. Her legs wrap around my waist and I walk her into the door behind us. Her back meets the door and my cock sludges between her engorged labia and sinks deeply into her ginger hair decorated pussy. We moan and flick our tongues together. She squeezes me with her legs and tries to consume as much of my cock into her pussy as she can. I stroke her tenderly aged round ass firmly and pump against her body, making wet sludgy noises as my cock moves erratically back and forth inside her.

"Hurry, I have... to get back!" Tracey panics, her customers are out there and she's potentially neglecting them. I hardly let her speak as I suck on her tongue. I respond by quickening my thrusts into her, feeling her mature pussy submit to my invading cock. It' hasn't been a minute and I'm gonna fill her with my cum. She is so selfless, not interested in reaching her orgasm. Is she just rewarding me for my actions before? Either way, it's rude to refuse a gift.

"I'm coming inside..." I gnaw at her neck passionately as she sinks herself on to my cock as hard as she can. Her breasts bounce wildly as she takes the hammering.

"Fill my pussy, ooh quickly!" Tracey incites me to breed her so I pin her against the door and drive my cock into her a few more times, kissing, licking and nibbling her shoulder, collarbone and breasts. Her nipples are firm and feel great on my tongue as my head clouds over and semen starts pumping out of my cock and filling her pussy. She must feel the warm white gunge coat her insides as she passionately squeezes me into her body, and I feel her vagina contracting over my dick as it paints her inside.