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Chapter 6
by
Callum95
How should John have sex with Claire?
Loving and Sensual
//I was going to do dominating and rough but as it is John's first time in this section of Sexual Privilege to a woman who he has loved and crushed on, i want it to be loving now but rough and raunchy later on. Btw at the end of these chapters, i always post questions on how the next chapter can progress. Put which one you want in the comments or even suggest a different way to do it. It isn't guaranteed, however, that i will do it your way.
John's initial instinct on this was to go all out and dominate the friend who he had been picturing like this for years of his life. But he also wanted it to be special, to be a moment he could forever reminisce on between the two. He was definitely a virgin, having a pornstar sized cock and a good physique genetically as he did not exercise at all still didn't get him laid due to how utterly awkward and silence he came in the presence of women. Claire was also a virgin, as she had said to him multiple times, she was scared to try sex on fear of it hurting her and that it wouldn't live up to be the wonderous thing people say it is but John was a man she was in love with and the prospect of sex with him didn't hold that fear and apprehension. There would be time later on for rough sex and for moments where Claire would moan out his name as he sheathed all of his meaty cock inside her in one thrust but not today.
Even though John was looking at Claire with lust and shock in his eyes, there was also a steady amount of fear and nervousness building up. Thoughts like "what if she doesn't like it?" or "what if i cum too early?" rattled inside his brain. Claire's eyes held the same lust, fear and nervousness with her thoughts being "what if he doesn't like my boobs?" or "what if it hurts too much?". Two young adults about to make love for the first time isn't as fast as you would think. John makes his way slowly to the bed, each step seemingly taking longer than the last. When he reaches the end of the bed, he takes stock on how perky Claire's breasts are, how well the nightie shows them off. He blushes as he stares at them longer than he meant to, earning a blush from Claire as well.
He gets onto the bed and crawls towards Claire, knees getting weak and hands getting clammy as he stares into her beautiful blue eyes and gives the first kiss. Claire doesn't respond immediately as she had been waiting nervously for the moment their lips would meet and she didn't know what to do. The result was a nervous kiss that didn't last long at first but the next kiss, they both lean in and start to kiss. It is still awkward but over the course of 5 minutes, all that the new couple can do is explore and experience each other in a new light as they have their first intimate moment. Lips and lips, tongues brushing up against each other, each other's hands exploring the others upper body.
The kissing stops when one of John's hands accidentally brushes off Claire's breast. This earns a small gasp of surprise from Claire and a look of panic from John. But Claire recovers quickly as she is starting to really feel hot and bothered, she looks back into John's eyes as she leans back for a second to remove one strap from one shoulder, going slow to see how eager John is to see her breasts. She goes to do the other and stops, gaining an almost whine from John as he anticipates what's about to happen. She removes the other strap and pulls down her nightie until her breasts are free.
THUMP THUMP THUMP THUMP
John's heartbeat increases as he lays eyes on the most amazing breasts he has ever see and he has wanted a lot of porn. They were C-Cup breasts, not the biggest in the world but perfect for John. Just the perfect amount to grab or suck and they look perky all the time. He moves his hand down to the right breast, causing Claire to moan slightly at the first time of someone else touching her breast and how surprisingly good it feels. He squeezes it lightly, getting harder in his pants as he feels the smooth and soft skin in his hands and the shivers of pleasure coming from Claire who suddenly goes back to kissing him, a bit more eager this time spurred on by the pleasure of being groped. This continues for a few minutes as he feels both breasts, squeezing and flicking the nipple before he stops as he feels her hands exploring his crotch, causing his boner to go from semi hard and hard immediately. The bulge forms in his pants, alerting her quickly that he is eager for her to touch his cock.
So she pushes him down on the bed and removes her nightie, showing her smooth and smoking hot body and her tight but still wet pussy. John's boner starts to become painful as she does this slowly to again tease him. But soon enough, she is in-between his legs, looking at the bulge forming on his jeans. Slowly and shyly, she unzips his pants and puts her hand in his pants to fish out his hardening cock. Her hand finally comes into contact with his cock, shocking her immediately to his amazing 8-9 inches of cock but she thought it could just due to how squashed his dick must be. With a minute of struggling, she manages to finally bring out his cock through the zipper hole and now it was time for shock to run rampant on her face as she starts at the longest cock she had ever seen.
She had watched porn and always infrequently as she wanted to feel her first orgasm when she first had sex. But the cocks on the videos could not shine a light on the thick, meaty pole that shadowed her face. She did not know that along with getting the boy of her dreams, she would get a cock that she would most likely become so used to that other dicks just don't do it for her. With that, she starts to jerk at his cock slowly, watching it as it seemed like it may erupt at any minute. John was loving the attention on his cock, he had to hid a smile that confirmed that she didn't seem scared of his cock but just curious, the handjob already threatened to make a inexperienced young adult like him cum so he gripped the bedsheets and tried to hold off to enjoy the pleasure.
Claire continued to jerk off his cock, looking with lust as a piece of precum would dribble from his shaft and roll down his entire shaft, leaving a trail that seemed to make the cock more alluring. Slutty feelings that she had never experienced welled up in her, what if she became addicted to this cock? What would it be like to be fucked for hours by a cock like this?. But she held back, as she wanted this to be loving too. So she focused on the veins of his cock ,the feeling as it slightly throb in her hands after each pump of his cock she would do. After 10 minutes of a slow and teasing handjob, unknowingly from her, she prepares herself mentally for it as she wraps her lips around the very top of his cockhead in which John says "no stop! I have a better idea."
Claire reluctantly moves around from the large cock as John asks her for her hand, in which she nods and then slightly pulled so she would end up straddling him, his cock hovering so close to her clit before he asks her to turn around so that her dripping, now eager pussy is over John's head and his cock was inches away from her lips. Their first 69! John starts off first by placing his tongue on her clit, earning a moan from her louder than expected as he gets to work flicking it with his tongue slowly as to not overwhelm her. She follows by placing her mouth around his cockhead and sucking. Both of them aren't doing a good job but they don't realize it. John continues to explore her pussy, whilst focusing on not cumming. Feeling her pussy folds as he runs his tongue over them or Claire's shiver when he touches her clit with his tongue. Claire moans into his cock from her pleasure, causing **** pleasure to him who can feel the vibrations run through his shaft as he feels her warm, wet mouth suckling at his cock tip. However, due to inexperience, they both cum rather early.
Claire's whole body starts to shake almost uncontrollably as a wave of great pleasure overcomes her entire body, making her feel like nothing could ever go wrong as her pussy shoots out a sizable load of pussy juice all over John's surprised face. Claire twitches in pure mind boggling pleasure as she moans onto John's cock, causing him to cum as well. John's orgasm is the most powerful one he has ever had, nothing from masturbating comes close as he feels like his entire cock is radiating pleasure. Not only that, his cumload is bigger than he starts to unload his stocky cum all over the place. One massive spurt enters Claire's still pleasure stiffened mouth before she becomes aware of what is happening. She starts to suck again, making another couple of loads fill her mouth with thick cum which she swallows without question but she has to stop sucking to breathe meaning the rest cover her face and chest in white strands of cum.
The new couple are tired and content but John wants to make love in the traditional way too before they succumb to sleep. So with a good bit of effort, he manages to move Claire so she is laying next to him. John shakes Claire to make her wake up a bit as he asks her to lay next to him. She complies, happily wanting to snuggle next to him. He removes his top, pants and underwear whilst laying down, throwing them to the floor before whispering to Claire "I want to take your virginity, do you want me to?"
Claire is awake enough to be shocked at the bluntness of the question but they had already done some lewd stuff so she whispered a yes with a nod. He pulls her so they are both laying on their side looking at each other, as he lines up his cock with her (in a reverse spooning sex position) dripping cunt and sinks the tip of his cock into her folds. She immediately shouts in pleasure and pain as she feels the intrusion. She asks him to stop and go multiples times as he tries to thrust more in but at the moment, 4 inches is all she can muster. It is enough to break her hymen, however, and so it is sealed that John took Claire's virginity (there will be no blood as i think it would ruin the scene). So John accepts her limits and starts to slowly thrust the 4 inches in and out of her pussy. John feeling her inner pussy walls tighten around his shaft, lubricating it even more and Claire feeling the veins of his cock rub against her sensitive walls. This earns groans and moans of pleasure from both of them as they embrace each other fully, naked and in love. They are both sensitive from the previous orgasm so it only takes around 5 minutes before they both explode in orgasm again.
Claire shakes again as she cums in tandem with John. She feels panic for a second at the thought of John's cock pumping her full of cum but John manages to remove the shaft so he can come onto her body whilst she squirts on his shaft and lower body. Both moan and sigh happily at the first time having sex. They both knew it would be an common activity. John vowed to last longer and Claire vowed to be able to take all of his massive cock.
As they both drift off to sleep in each other's arms, John thinks to what tomorrow will hold for him. Will he go for a second round with Claire or will he try it with the more experienced MILF Abigail, Claire's mother?
What is John's plans for tomorrow?
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Sexual Privilege
Freeuse for One
These branching stories are going to have 3 very simple premises: 1) You exist in a world where your character AND ONLY your character gets to have sex with whatever group or groups of people you choose wherever and whenever he or she desires. 2) The circumstances under which he or she can have sex with that group can be specified generally or specifically. 3) The response of the people you have sex with and/or the general public can be chosen.
Updated on Jun 11, 2026
by Cross C
Created on Aug 31, 2017
by SanctifiedVillified
You can customize this story. Simply enter the following details about the main characters.
With every decision at the end of a chapter your game state can change. Here are your current variables.
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