How to deflower a Russian virgin with a little help

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As Einstein might have said once, “Confusion is good.” He might have said that. Or not.

Happy readings with my first DIY chapter, "It is always good to know how to deflower virgins.”

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OK, let’s look back for a second. As a pro diver, I was fucking cute vacation babes on a weekly basis; half of them were in some kind of relationship. But I was only making 1200 USD a month as a diving instructor, working six days a week and being a nitrogen wreck on Sundays. After roughly a year working at night for Anna in the mansion, being a well-paid male whore, I quit diving altogether. I just wanted to make sure it was a stable income, so I waited a little before storing my fins.

Of course I was not in the league of those Monaco whores, who charge at least 7000 USD for two days, but I got paid 1000 USD per night, plus extras. So, I was making five, six times my diving salary, doing what I liked best. The big advantage was that I could simply choose each time which babe I was going to fuck—no need for wining and dining! Of course I was nervous with my first married order, Daphne. Thank God my boss Anna had not booked any secret watchers (as far as she was telling the truth…).

After a while, I fucked myself up to a good standing among the regulars, and slowly, bit by bit, I was getting more bookings. The breakthrough was, of course, me fucking Irina's daughter Natalya against her will, for two days in a row, knocking her up, paid for by her own mother, with more than 40 voyeurs watching from the secret rooms built around the main stage. From that moment on, I was one of Anna's top three best-booked white male whores. But of course, such a booking is rare, and I was well aware of that.

Usually, Anna, my boss, would send me an email with three- or four-women’s pics to choose from. Normally, they were sophisticated; well-maintained, with a good, sexy body shape; and married to rich, ugly husbands who made their fortune by working hard and not having time for their trophy wives. Those sexy wives would have quickly become pregnant in the first year of marriage, securing their income that way. Once their offspring were independent enough, they would have nothing to do but keep in shape. Many of them would go to the gym with their teenage daughters, preparing them for a life without working by simply spreading their legs now and then.

It was Irina, the mother of Natalya, who confided in me, when we were having drinks together one evening on the mansion's terrace, that it was exactly how I thought it would be: find a rich guy and get knocked up.

“That's it," Irina simply said.

I hadn’t seen her for a longer period, perhaps even 12 or 14 months after she booked me to breed her daughter for her. A baby girl was born from those two days of fornicating that ovulating youngster, but I was to stay away, which was OK for me. Just lately, she started visiting the mansion again, and I would catch a glimpse of her almost every week, and she had become a regular, enjoying watching other people fuck. I had no bookings that night. Anna, my boss, did rent out to certain customers rooms without a whore so they could fornicate in all anonymity, but she preferred renting out her whores because the turnover was much better.

Irina was the one who walked up to me as I was enjoying on the mansion's terrace a mojito, looking out over the valley. It was a nice, warm summer evening, and all staff and guests were dressed accordingly. Flimsy, that is. I wore a white tank top and some old used-up shorts since it was my day off. Irina asked if she could join me. She had recognized me from afar, and the moment she stood next to me, I could see what a sexy babe she was, with her big 90D (40C) tits on her petite 157 cm (5 ft 2 in) frame. Her tits were bigger compared to her round, sexy ass, and I believe she was Russian or something like that, with her little Eastern accent, topped with killer green eyes and blonde hair.

She sat down on the lounge chair next to me. “So how are you doing?” Irina wanted to know, extending her arm, her soft hand massaging my cock through the thin fabric of my shorts.

“No fucking today?”

“No, no bookings, Irina. How about you? Care for a little lap dance on my growing cock?” She kept kneading it, my rod now trying to stand upright in my shorts, but it was stuck in one leg of my shorts, showing its thick outline towards one side, almost horizontally.

“Let me help you with that.” Irina opened my shorts, quickly grabbing my painfully hard cock and freeing it from its entrapment. She kept my shorts pulled down on my knees to have a good look at my fully erect rod. Her hand didn’t let it go, and after wrapping the other hand around it, she measured with both her small hands its length, holding her hands side by side. Three hands were needed to measure my entire cock length, the cockhead still visible.

“Can I suck it a little before I decide if I book you now?”

"Sure, Irina, have a taste.”

Irina leaned in over my fully erect phallus, and her pink Chanel lips kissed my purple helmet two, three times, taking her time before tasting me, before taking me in her married mouth, playing with me, making my cock twitch, and leaving a pink lipstick smear on my shaft. A glob of precum popped out of my cock slit, and Irina happily licked it away, enjoying the sweet-salty taste. “Do you have more of that big boy?” she whispered. “My little Russian mouth is soooo thirsty.”

A new waitress came to us and asked a bit shyly if she wanted to drink something. She was young, just 18, cute but overwhelmed by the sight of seeing a customer nibble in public on a big cock. A very big cock, she thought as an after-thought.

Irina let go with her mouth of my ready cock and looked up at me as one hand held my cock.

“What are you having?” She casually asked me, looking at my cocktail. "Mojito," I answered.

“Two mojitos please.” She kindly asked the young waitress. "What's your name, honey?”

“Annely.”

“Could you please tell Anna that I will have the terrace package, plus bareback, but I will pay the rest tomorrow? I only have 800 USD with me,” and she gave Annely the cash. “And don’t forget the drinks.”

“Sure. I will be right back, Ms.” And she quickly walked away to deliver the message to Anna.

Before she was out of sight, I could check her out. A young sexy babe, not realizing what a little good-looking slut she could be. But instead of that, she was wearing the most conservative mansion clothes we were given. The choice of clothes within the clothing package we all received was pretty good. From tight tank tops all the way to evening wear. And she chose the polo… Anyway, she must have been 18, because no workers were legally allowed under that age. Was she Russian too, just like Anna? I guess she was 5.1 ft (155 cm) with natural boobies, and probably they were 70 C (32 B). I could sense a sexy hour-glass figure, but she wasn’t showing it. The way she blushed as she saw a guest lick the side of my shaft was too cute to be true. Maybe she was a virgin? I just wondered for a second, perhaps Annely lied about her age?

Matching her young cuteness was the shoulder-long blonde hair and the green eyes. And the blushing. Irina had seen me looking at Annely and saw her blushing too, but she had other things on her mind, which were standing right in front of her red lips, and she lustfully resumed sucking my agitated mushroom, making sure she was only sucking on the big purple head, her tongue licking my most sensitive frenulum.

“I think your cock is ready for me.” She stated, while softly massaging my two swollen balls, approving of their warmth and fullness, her hand softly preparing them for spewing my cum inside her womb. Irina stood up and casually undressed next to me, carefully placing her clothes on her lounger. Some guests watched what she was doing, hoping for a free little sex show right here on the terrace. She was wearing no bra or panties, and her pussy mound was nicely shaven, with a small landing strip showing me the way towards her opening. Her breasts were beautifully pear-shaped, narrower and less full at the top, gradually sloping downward into a fuller, rounder bottom. They were not aged at all from all that titty sucking of her daughter.

After deciding if she wanted to ride my cock facing me or not, she carefully stepped over me, bracing herself on my shoulders. On purpose she held her face really close to mine, her lips almost touching mine. Her aroused pink nipples were ready to be sucked.

Irina lowered herself onto my cock with practiced grace, her tight married pussy gripping my shaft as she sank down inch by inch. Her green eyes locked onto mine, half-lidded with lust, her red lips parted in a soft gasp as she bottomed out, her ass resting against my thighs.

"Fuck, you're big," she breathed, adjusting to the stretch. She began to move, slow circles at first, grinding her clit against my pelvis. Her pear-shaped tits swayed hypnotically with each motion, the pink nipples hard and begging for attention.

I reached up to cup them, thumbs brushing over the sensitive peaks, making her moan and ride me harder. The terrace was open-air, and a few guests had paused their conversations to watch the show—Irina didn't care. In fact, she seemed to thrive on it, throwing her head back and arching her spine, her blonde hair cascading down her back as she bounced on my cock with increasing urgency.

"That's it, fuck me," I groaned, gripping her hips to guide her rhythm. "Show these people how a Russian slut takes cock."

She laughed breathlessly, a wicked sound, and leaned down to whisper in my ear. "I want that waitress. Annely. I want her to taste you while I ride you. I want to corrupt that little virgin."

Before I could respond, I saw Annely returning, her tray trembling slightly as she approached. She couldn't look away from where Irina's pussy was swallowing my thick shaft, the obscene wet sounds unmistakable in the warm evening air.

Irina slowed her movements but didn't stop, keeping me buried deep inside her as she turned to the young waitress. "Annely, honey, put the drinks down and come here."

Annely set the mojitos on a small side table, her hands shaking. "Ms., I should really—"

"Nonsense," Irina purred, her Eastern European accent thickening with arousal. "You've been staring at this magnificent cock since you first saw it. Don't you want to know what it tastes like?"

Annely's green eyes darted between us, her face flushed crimson. "I... I've never..."

"Exactly," Irina cooed, lifting herself off my cock with a wet sound that made Annely gasp. "That's why you should try it. Look how beautiful it is."

My cock stood upright, glistening with Irina's arousal, the purple head swollen and still leaking precum. Irina reached out and took Annely's small hand, guiding her closer until she was standing right beside the lounger.

"Just a taste," Irina encouraged softly, her other hand stroking my shaft slowly. "He's clean, he's safe, and he tastes divine. Don't you want to know what you've been missing?"

Annely bit her lower lip, her chest heaving beneath that conservative polo shirt. She was trembling, but there was curiosity in those green eyes—curiosity and a hunger she probably didn't fully understand yet.

Irina gently pushed on the back of Annely's head, not forcefully but insistently, guiding her down until her face was inches from my cock. "Lick it, baby. Just the tip."

The first contact was tentative—a quick dart of pink tongue against my slit, tasting the bead of precum there. Annely made a small, surprised sound at the taste, then licked again, slower this time, exploring the texture of my cockhead.

"Good girl," Irina praised, her hands now working on Annely's conservative outfit. "Now take it in your mouth. Suck on it like a lollipop."

Annely opened her mouth wider and took me in, her inexperience obvious but endearing—too much teeth at first, then too shallow, her tongue unsure where to go. But Irina was patient, coaching her, one hand on the back of Annely's head, the other unbuttoning that stupid polo shirt.

"Relax your jaw, honey. Yes, like that. Deeper now, let him feel your throat."

As Annely slowly began to find her rhythm, her natural enthusiasm taking over, and started to suck harder.

Right then, as Irina saw how aroused she was, she stopped her, whispering her to take off her polo. Annely let my cock and raised her young arms to help Irina with her goal.

Irina stripped away the polo, revealing the lacy white bra underneath—surprisingly delicate for such a conservative girl. Irina reached around and unhooked it, letting Annely's natural tits spill free. They were perfect, bigger than expected, high and firm, with pale pink nipples that hardened instantly in the evening air.

“You can suck him again.” Irina told the young waitress, letting her know she was in charge.

Annely was moaning around my cock now, the vibrations sending shivers up my spine. She'd found her confidence, bobbing her head with increasing enthusiasm, her blonde hair falling forward to tickle my thighs. She was lost in it, her eyes closed, completely unaware that Irina had stripped her down to just her panties—cute white cotton ones that looked virginal and obscene all at once. Her shorts hang around her ankles.

Irina caught my eye and nodded toward the empty lounger beside us. I understood.

Gently, I took Annely's shoulders and pulled her off my cock, her mouth making a wet popping sound as she released me. She looked up, dazed and confused, lips swollen and glistening. "Did I do something wrong?"

"Not at all, baby," I said softly, standing up and lifting her easily—she weighed nothing, that petite 155 cm frame light as a feather. "You did perfectly. Now it's time for the main course."

I laid her down on the adjacent lounger, her body pale and trembling against the dark cushion. Irina was there immediately, kneeling beside her, and removing both her shorts and panties. Stroking Annely's hair and whispering encouragement.

"Shh, relax, honey. He's going to make you feel so good. Better than anything you've ever done to yourself."

Annely's eyes went wide as I spread her legs, her hands instinctively moving to cover her pussy. "Wait, I'm... I've never..."

"I know," I said gently, positioning myself between her thighs. "I'll go slow. Tell me if it hurts too much."

Irina held Annely's hands, pinning them gently above her head, her other hand caressing the young girl's breasts. "Look at me, Annely. Don't look down. Look at me and breathe."

I guided my cock to her entrance, slick with her arousal and my precum. She was tight—impossibly tight—and I had to press firmly to even begin stretching her open. Annely whimpered, her face contorted with the unfamiliar pressure.

"Breathe out," Irina commanded. "Push out, let him in."

Annely exhaled shakily, and I pushed forward, feeling the resistance of her hymen. One sharp thrust and I was through, burying myself halfway inside her as she cried out—a sound of pain and something else, something that sounded suspiciously like pleasure.

"Shh, shh," Irina cooed, kissing Annely's forehead, her hands still holding the girl's wrists. "The worst is over. Now the good part begins."

I gave her a moment to adjust, feeling her virgin pussy fluttering around my shaft, so hot and tight it was almost painful for me too. Then I began to move, slow, shallow thrusts, letting her feel the friction without overwhelming her. As I pulled completely back, only leaving my swollen cockhead inside, I could see the red, bloody smears on my phallus.

"Oh god," Annely gasped, her hips moving experimentally to meet mine. "Oh god, oh god..."

"Feel that?" Irina whispered, her green eyes gleaming. "That's a real cock inside you. That's what you've been missing, you little slut. You were born for this."

The dirty talk seemed to unlock something in Annely. Her legs wrapped around my waist, pulling me deeper. "More," she panted. "Please, more."

I obliged, picking up the pace, driving into her with long, steady strokes. The pain was gone now, replaced by pure sensation. Annely's head thrashed from side to side, her blonde hair a mess, her tits bouncing with each impact.

"Touch her clit," I told Irina. "Make her cum on my cock."

Irina's hand snaked between our bodies, her fingers finding Annely's clit and rubbing it in tight circles. The effect was immediate—Annely's back arched off the lounger, a high, keening wail escaping her lips as her first-ever cock-induced orgasm ripped through her.

"Fuck, she's clamping down," I groaned, feeling her pussy milking my shaft in rhythmic spasms.

"Don't stop," Irina commanded. "Give her another. Train her right."

I kept fucking her through the aftershocks, not giving her a chance to come down. Annely was fazed out now, babbling and moaning, her nails digging into Irina's arms as she held her. The second orgasm hit even harder, making her scream loud enough that several guests actually applauded from across the terrace.

"One more," Irina urged, her own arousal evident in her flushed face and heaving chest. "One more before he fills you, Annely. One more like a good little whore."

The word "whore" seemed to trigger something in Annely—maybe the realization that she was being paid for, that this was her job now, that she'd crossed a line she could never uncross. She came a third time, her whole body convulsing, her pussy gripping me so tight I couldn't hold back anymore.

"I'm gonna cum," I warned, my thrusts becoming erratic, savage.

"Inside her," Irina ordered, her hands now gripping Annely's hips, holding her in place, preventing any escape. "Breed this little virgin. Fill her womb."

With a roar, I slammed deep one final time and erupted, pulse after pulse of hot cum flooding Annely's unprotected pussy. She felt it, her eyes flying open in shock at the sensation.

"Oh god, he's cumming inside me," she whimpered. "Oh god, it's so warm..."

"Take it all," Irina whispered, keeping her pinned, her eyes meeting mine over Annely's trembling body. "Every drop. That's a good girl."

I kept thrusting slowly, emptying myself completely, watching my cum begin to leak out around my shaft, mixing with the evidence of Annely's virginity on the lounger cushion beneath her.

When I finally pulled out, Irina immediately moved between Annely's legs, inspecting my handiwork with a satisfied smile.

Several guests stood up and gave us an applause, having truly enjoyed watching the fucking of a virgin.

"Beautiful," Irina murmured, dipping two fingers into the mess and bringing them to Annely's lips. "Taste it. Taste what you made him do."

Annely, dazed and compliant, opened her mouth and sucked Irina's fingers clean, her green eyes fuzzy with the aftermath of pleasure and the beginning of a new understanding of who she was—who she could be.

Irina leaned down and kissed her, deep and possessive, then looked up at me with a grin. "I think Anna's going to want to put her on the regular roster. After proper training, of course."

I collapsed into the lounger, reaching for my forgotten mojito, and raised it in a toast. "To proper training, then."

Annely just lay there, legs still spread, my cum slowly leaking from her freshly claimed pussy, looking like a young woman who had just discovered the answer to a question she hadn't known she was asking.

To be continued.