Too Good To Be True Ch. 20

"So, those are the first three requirements." Courtney continued, "The last three are important. If you agree to join, you will be part of Tom's harem."

Ruth's eyes widened at the word 'harem'.

"You agree to have sex with Tom, and no other men so long as you are a member of the harem. Then you agree that if you have any sexual interaction, not just sex, but anything sexual, you will immediately leave the harem. You won't try and stick around in the harem because having moved on from Tom, you won't try to just come back to him. We can all still be friends, but you won't be part of the harem anymore. Finally, while you are a member of Tom's harem, all sexual activities must be consensual. You can't force Tom to do something he doesn't want to do, and he can't force you." Courtney finished her explanation.

"...Harem... that's kinda hot." Ruth murmured, then thought for a moment, "But what if I want him to make me do things....?"

"If you want him to make you do things, then it's consensual. You will have to set up safe words and let him know what kind of things he can do, or if he has any limits." Courtney shrugged.

"So... um.... I want to join. This is exactly what I wanted, and I guess it's better because you have this so much more set up than I thought it would be. I thought you were just a bunch of girls letting a guy fuck you. I figured he must have a big dick and be good with it or something." Ruth breathed.

"Oh, he has a great dick, and he definitely is good with it." Courtney laughed.

"So, um, what more do I have to do to join?" Ruth begged.

"Well, if you were watching you would have seen the girls nod when they decided they were okay with you, took a bit for you to win over Suki and Khloe, but being willing to strip when Tom told you to, seemed to be enough." Courtney told her. "If you want in, and are willing to live by the rules, you're in."

"Really?!" Ruth gasped, dropping her panties in excitement, then picking them up hurriedly.

"Yeah, if you don't want to, just don't go blabbing to anyone, but if you want in, you're in." Courtney assured.

"I want in. So, who is in charge? Like I can't tell if it is you, her, or Tom?" Ruth asked, confused, motioning to Sarah.

"Well, Tom and I are in charge, I guess. And I guess since if you have anyone who is over the other between me and Tom, I guess it is Tom. I am Tom's girlfriend, and when we graduate I'll be marrying him. I'm his main girl. Sarah is graduating in a few months with a Doctorate in Clinical Psychology. She is making sure that no one gets into the harem that doesn't need it. This is a group to help each other, not a place for easy fucks." Courtney replied. "Brittany is graduating as a Doctor of Medicine, at the same time, though she'll need to do her residency before she can really practice, and she is helping make sure we are all healthy."

Ruth looked at the two girls with a new respect.

"The rest of us are graduating in a year or two." Courtney replied, "Tom and I are Computer Science majors, with Tom having a business minor. Debbie is a Communications major. Abby is getting a degree in Economics. Suki is a Business major. We'll all be graduating next year. Khloe is in Law School. Tina is getting a Master's degree in Physical Therapy. They graduate the year after that."

"We all bring different things to the harem. Everyone has their space." Courtney explained, "But I am the lead girl in the harem, the queen of the harem, if you will, and Tom is my king."

"Gotcha, you are the Queen. Tom is your king." Ruth affirmed, "Um... I don't mean to be rude, but I have been wet for most of the day... Could I... have sex with Tom now?"

"Anyone have any objections?" Courtney teased as Ruth rubbed her thighs together to try to ward off her clinging desires.

"For goodness sake, let Tom fuck the poor girl already." Brittany laughed, and the rest of the harem chuckled with her.

I laughed and rose from my seat, and walked to the newest member of my harem.

"Are we going to have sex right here in front of everyone?" Ruth asked quietly, clearly unenthusiastic about the idea.

"No, not unless you want to." I informed her, taking her hand. "There are plenty of perfectly good beds in this place, but if you say it again louder I'm pretty sure you'll see Debbie get fucked out here tomorrow."

"She does it in front of people?" Ruth gasped.

"She's a bit of an exhibitionist, it turns her on to know people are watching." I informed Ruth and started to lead her from the room.

Courtney called from her seat, "Ask her if she'll do the photo?"

I nodded and led her from the room.

Dana saw me exiting with the girl, and Ruth's obvious expression, and winked at me before walking in to talk to Courtney.

I led her to the nearest open room, and led her inside. Once the door was closed, I turned to her.

"Now, I know most girls dream about their first time having sex. Is there anything in particular you want? If not, I can explain how I've done it with the other girls for their first times."

Ruth stood there, staring at the bed, her back to me.

"I'm finally gonna do it... I finally get to know what it's like." She breathed.

I walked up behind her and slipped my hands around her waist.

"Um... as sweet as that is....um... how do I say this... I don't want my first time to be... gentle..." Ruth told me, removing my hands. "I know everything has to be consensual, but I... um... I consent to you raping me for my first time."

"What?" I asked, certain I had just misheard.

"I'm sick of men who I can push around. I want a man to throw me around and do what he wants with me. I want you to force me. I want to resist you and you take me anyway." Ruth breathed.

"Oh, I don't think rape is what you want. Rape isn't sexy. It isn't hot. It isn't fun. What you want is dominated. I can dominate you. But we will have a safe word, and if I go to do anything to you that you expressly don't want. You can use the word." I told her.

"No, I'm pretty sure I want raped." She shuddered.

"What do you think rape looks like?" I asked.

"You'll tear off my clothes, hold me down and fuck me." She said, "You'll use my pussy as your cum dump. You'll tell me I'm a slut and a whore and I deserve to be used as such. And you'll fuck me until your balls are sore from pumping sperm in my pussy."

"What you just described is domination. Rape would be much simpler. Heck, why even rip your clothes. Yeah, I'd hold you down, flip your skirt up, use your pussy, not care if you got off, and leave. All a rapist cares about is getting off." I told her. "If you want to resist me as I dominate you, that's fine. But we will have a safe word, and that will make sure you are not hurt."

"We can have it, but I won't use it." Ruth murmured, "You can do anything to me."

"Okay, if I start doing something you aren't okay with, just say 'Peppermint'. You got that." I asked.

"Yes, I can say peppermint." Ruth said.

I had done a couple of fuck sessions like this with a few of the other girls, when they really wanted rough sex. I always tried to make sure it still felt good for them, but if they wanted it rough, I could do it.

I stepped up behind her, and reached around, grabbing her tits.

"What are you doing?" She gasped, trying to push my hands off her breasts, but her breath caught, and I knew she was fully into the roleplay, and she was really excited about it.

"Giving you what you deserve, slut!" I growled, grabbing her arms and pulling them over her head, forcing her onto her tiptoes.

"Aahh!" She gasped, "No, stop!"

I pulled her blouse up, around her elbows and wrists. I knew she had planned this, because most women didn't wear strapless bras for just anything, but it would be much easier to remove in this rape-play session. I pulled her arms behind her back, and using the blouse to keep her elbows from pulling apart, a quick knot on her wrists, and her arms were immobilized. I had figured out this with Courtney after she read about it online.

"No, please, stop!" She gasped, flushing and breathing hard, she tried to pull away, but I just looped an arm around her waist, keeping her from retreating.

"Fuck you, you whore, look how easy you are making it for me." I teased, pulling her strapless bra down, exposing her tits, before undoing the loose claps and tossing the bra aside. I picked her up and gently tossed her onto the bed.

"No, please, leave me alone!" She pushed me away with her feet. The flush in her face and her erect nipples gave away how much of a turn on this was. Her arms struggled behind her back, but being unable to really move her arms made it hard for her to break free of the simple knot holding her blouse on her wrists. Anyone who has tried to knot clothing knows it wasn't easy to do effective knots, but by knotting it tight enough that her elbows were locking her wrists in, it didn't matter.

I threw off my shirt, and Ruth gasped. I dropped my pants and boxers in one motion, showing her the 6 inch cock that was about to take her virginity.

"Fuuuuck." She gasped, her horniness almost making her drool, she fell out of her role play, and her desires were plain on her face for a second.

"Such a fucking slut, as soon as you see a dick worth shit all the fight goes out of you." I teased.

Brought back into the role-play, Ruth gasped. "No please, I'm a virgin! You'll tear me apart." She gasped as I approached the bed, she pressed her feet forward, pushing me back.

I easily lifted her legs, aiming them over my head, which prevented them from kicking me and as a perk revealed her bare pussy and ass.

"No panties? It's like you are begging me to fuck you virgin cunt." I continued, I could tell the talk was helping her be in the role-play.

"No, they just got ruined. I don't want this!" She gasped. The fact that they were laying on the floor, in fine condition, just reinforced that she was doing her best to make this role-play work.

I removed her shoes and socks from her flailing legs, and slapped her ass. "Nothing you do will matter, slut. I will take you and fuck you how I want."

"No, please!" She begged, and I couldn't tell if she wanted me to move faster or if she was just really loving the role-play.

I couldn't see a zipper on her skirt, so I just pulled and the elastic slipped down over her ass.

"NO!" She gasped. Now naked, she was blushing furiously, and flailing her legs, though one of my arms under her knees kept them where I wanted them.

My right arm was holding her legs, but I reached down and started massaging the sopping cunt of my new harem girl with my left hand..

"So wet, you say you don't want this, but your whore cunt wants it. It wants my giant cock to destroy it." I told her, then seeing how wet and lubed my finger was, I decided to push things. "And what's this?" I moved my finger down and pressed my finger into her asshole. It sank in a knuckle.

"Oh, Fuck! Leave my asshole alone!" She thrashed I could tell there was some legit fear, most girls were scared of their first anal fuck, so I wasn't surprised.

I pressed my finger further in, the lube from her pussy was plenty and I was soon a full finger up her ass.

"Whore, I'll fuck what I want, when I want, how I want, and you can't DO anything to stop me. What do you have to SAY about that?" I pressed, knowing I had to remind her about the safe word. If she legitly didn't want me to fuck her ass after her pussy, she could just say the word.

"No please, have mercy on my poor ass!" She begged.

I nodded, if she really didn't want it, she would have said it and I presented a golden opportunity. Her ass would be mine after her pussy.

I pushed my shoulders up to hold her legs, freeing up both of my hands to grope her exposed pussy and ass. She was now pinned, curled with her tied arms on the bed under her, so she could support herself, her feet just hanging by the headboard. Her ass and pussy were pointed skyward as my fingers violated her ass and explored her pussy. Courtney wasn't wrong, Ruth's hymen was tight and I could barely get my finger inside her pussy at all without it blocking my progress. She was dripping pussy juices so I lowered her ass a little bit to get the pussy juices dripping down her ass to help lube the finger in her asshole. I pumped her ass, lubing it with her own juices.

"Fuck, you're going to tear my ass!" She gasped, grunting as my finger probed her bowels.

"Oh, you think my finger is bad, just wait until it is my cock!" I told her.

She shuddered as my finger massaged her clit while my other hand finger fucked her ass. She was having her first orgasm from anal stimulation and clit stimulation. I kept up those and started using my thumb to play with her slit and tease her vaginal hole. The relentless stimulation made her cum again.

"FUCK!!! Why does this feel good!?" She gasped.

"Oh, I am just preparing you so you don't pass out when I rip open your pussy and ass. I like my women responsive." I told her, and when she started to shudder in her fourth orgasim I knew it was time. I extracted myself from her ass, and lined my cock up with her baby tunnel.

I pushed into her opening, her hymen stretching tight as my the head of my penis played 'just the tip' with her fuck hole.

Ruth started coming down, "Wait, don't-"

I pushed, popping her hymen like a gusher. I pushed in, slowly going deeper as Ruth gasped.

"FUCK!!!! That hurts!" She gasped, shuddering and cumming again on my cock. It couldn't be hurting her too much because she was pushing back into me.

I shifted to where my ass was pointed toward her legs, so her asshole was available to me again as I fucked her newly deflowered pussy. I knew from fuck sessions with Suki that this dick angle was good, and while Suki loved anal, I had only begun exploring Ruth's ass.

I reinserted my left index finger into her ass.

"FUCK! Why am I cumming again?" She moaned, her ass still pointed straight up, letting me use gravity to make my thrusts into her pussy harder and deeper.

The pussy juice was living her ass well, so I went ahead and stuck my middle finger in her ass with my index finger.

"Shit! Fuck! You're going to rip my ass apart." She gasped at the additional intruder, but her pussy told me she was turned on.

I continued to loosen her ass as I plowed her pussy. I knew this virgin cunt was too good for me to last long, but Tina and I had been working on maintaining my erection and delaying or skipping my refractory period, the time after I ejaculated when my erection faded, regardless of my arousal. I used a few of these tricks here. I was concentrating and stimulating my dick to keep the flow of blood as I dumped my sperm in Ruth's fresh pussy.

I dumped four or five squirts of cum in her pussy as she came again.

I'd discovered that less experienced girls got overwhelmed and that led to some INTENSE orgasms. Ruth had one of these as pumped her cunt full of sperm.

"FUCKING GOD!!!!" Ruth screamed, moaning as her body trembled.

I knew her higher brain functions were toast right now, so I stepped around and lined my still erect dick up with her back door. I placed my dick on her picked asshole and slick with sperm, her virginal blood and a lot of pussy juice, it slid in an inch.

Ruth gasped, "Oh, fuck! You fucker! Oh, my ass..."

"One way or another I'm fucking this ass." I told her, playing into the role-playing. "It'll be a hell of a lot nicer for you if you keep that asshole relaxed." And I pushed in another inch.

"Fuck! Let me get used to it." She gasped.

"No." I teased and pushed in another inch.

"God, my poor ass..." Ruth whimpered.

I feared I might be pushing the whole "rape-play domination" thing, so I started playing with her still extremely sensitive clit. She couldn't stop herself from orgasming and when she did, I pushed in until I bottomed out.

"FUUUuuuuUuuuCk!" She moaned, torn between the pleasure of her orgasm and the feeling of my cock splitting her ass open.

I gave her just a minute, I knew mercilessly driving my dick into her ass like that would be intense. Then after she had a minute, I started thrusting and fucking her ass.

"Ohhhh, my ass...."she gasped as my dick continued its invasion of her anal cavity. But I could tell she was building to another orgasm.

I may have been being a little more hardcore than any virgin deserved, but I think part of me almost wanted to make an example of her for future girls. Regardless of remaining erect, my refractory period would prevent me from cumming in her as for at least 10 minutes. If I fucked her ass for ten minutes straight, she wouldn't be sitting comfortably for a week. But she had straight up asked to be raped, and when I warned her, she had insisted. If I was going to 'rape' her, I was okay with her sitting gingerly for a week.

So, bound and contorted, I continued to plow her virgin ass as my sperm, her virginal blood and more juices from her still surprisingly aroused pussy dripped down her ass, continuing to lube her ass as I fucked it. After a few massive anal orgasms, Ruth's moans became more and more guttural, and I realized I'd fucked her to the point that her brain was mostly shut off. I grinned as I continued to plow her ass, until I felt the climax building and I began shooting my sperm into her thoroughly fucked ass. I must have dumped one of my biggest loads ever in her ass, not very often is there over ten minutes of buildup to a climax like that.

I enjoyed the pulsing sensation as her ass clenched and released around my cock, allowing my erection to fade until her ass pushed me out.

I lifted myself off the thoroughly fucked girl and allowed her legs to flop so she was lying on her back, her face still in the blank expression of being fucked brainless.

I untied her arms and tossed her blouse on the floor.

As her arms moved, her face twitched, thought bubbling to the surface.

"Ohhhhh...." she groaned. "You didn't hold back." And she began to stretch her stiff arms then shifting her hips and legs.

"Would you like to cuddle while feeling returns to all of your limbs?" I asked.

She nodded humbly then rolled into me. I wrapped my arms around her, feeling her breasts pressing into my chest.

"Sorry if your ass is sore. You never used the safe word." I defended myself lamely.

"I didn't bother remembering it." She admitted, "Otherwise I might have used it when you started on my ass... I thought my virgin vagina would hold your... ow.... attention longer." She murmured shifting her ass. "I should have paid attention, ow, I'm not sure I'll be able to sit normally for a few days."

"You... You were supposed to remember the safe word to use if I did anything you weren't okay with?!" I chastised her, "If you weren't okay with me having anal sex with you, that is an important detail! I am not here to rape my girls!"

"You didn't." She assured me, "I mean, I figured eventually you'd take my ass... just not the first time. And to be honest... I fucking loved being treated like a fucking whore and fucked however you wanted. Fucking God! That was the first time a man has been real with me instead of being a fucking pussy!" She moaned, "God, if more men were like you, I would have lost my cherry years ago... Damn, where have you been?" And she pulled me closer.

Not the reaction I expected when she just admitted she didn't want her ass touched and I not only fingered it, but fucked it for at least ten minutes! Checking the clock it was closer to fourteen before I'd dumped my sperm in her ass.

"Oh yeah, you remember how Courtney mentioned a photo when we were leaving the group?" I asked.

Ruth nodded, stretching her hip.

"It's kinda a tradition in the harem, when a new girl joins and loses her virginity, we take a celebratory photo of you post your first fuck." I told her.