Who Going to Pay for University? (Closed)

[Cum_Inside]

She nods as her fingers ghost lightly over her clit just as he told her to do. Massaging and pinching at it with two fingers, she impatiently waits as he preps her slowly with one finger, working it deeper and deeper inside her. When whole finger is buried inside with no discomfort, she can feel the press of a second against her rim.

The second finger burns a bit but she finds that although it feels much tighter it's not really a painful stretch just yet. The pad of her index finger rubbing over and circling her clit certainly helps. She knows the importance of proper preparation, but she's starting to become antsy and is thrusting her hips back on his fingers to help work herself open.

 

[garajd]

The thrusting of her hips gives Brandon a clear indication that Anna is wanting this to continue . . . and that she is mentally and physically preparing herself for his swollen cock to take her anal virginity. Once his second finger has penetrated her opening, he knows she is ready . . . and he is definitely not going to hold back now.

Withdrawing his fingers slowly, feeling, and hearing, that familiar 'pop' when her tight pucker releases his fingers, he hops off the bed, opens a drawer on his night stand and grabs a tube of lubricant. Showing it to her as explanation of his sudden moves, he opens the tube . . . a generous dollop on his fingers to coat his cock, and another dollop to coat and smear on her tight pucker . . .

"OK, baby girl, here we go . . . take a deep breath and relax as much as possible."

Brandon, presses the head of his cock to her opening, and with one quick thrust, pops the head into her ass . . . then stops to give Anna a chance to adjust to this latest invasion.

 

[Cum_Inside]

Beyond the nervous butterflies, the first thing that pops into her head as his cock bursts through the ring of muscle protecting her sensitive insides is that, fuck, it hurts. The lube helps for sure, but the much bigger girth and length of his cock burns so much more than two fingers ever could. Her eyes are clenched tightly shut upon entry, but with some rapid breathing and the fact that he stops to let her adjust after the initial push, she's more curious than anything as she tries to look back to where his cock will soon be disappearing into her ass.

Slowing down her breathing and again, bearing down, Anna feels his cock sink just a fraction more inside as the tight suction of her ass pulls him in. She doesn't find that she minds the pain, actually, since she loves rough sex so much. There's something so intimate about the knowledge that the burn of the stretch is her accepting him into a place she's never let alone else before; she's giving him this gift and he's going to split her open on his dick and make himself at home more intimately than anyone has ever had the right.

 

[garajd]

Pressing forward slowly, but still pressing forward, he claims her ass as his; her gasping at the intrusion tells him all he needs to know . . . she has given this to him and is willingly committed her body, all of it, to him.

As he prepares to take the last inch, "Anna, look at the mirror on the wall." As her head turns toward the mirror, Brandon makes his final thrust and is cock is now totally buried in her.

 

[Cum_Inside]

His hips are pressed tightly to her ass and when she looks in the mirror all she can see his eyes watching her face as he withdraws slowly before giving her a mighty thrust and feeds his entire cock into her bowels once more. He must see the flinch there from the sting, but she's still rocking her hips back against him as he fucks her, so hopefully he understands that even if it hurts she still wants it.

Although it takes several thrusts, she starts to really enjoy the feeling of every inch of his cock sliding against her tightest insides and not just the sinful thought itself of exactly where she's let this man put his cock. "Fuck me hard, baby. I can take it," she tells him. As he impales her ass on his dick, she watches herself writhe on it in the mirror. His hands are gripping so tightly she knows there will be bruises tomorrow but she can't bring herself to care.

 

[garajd]

Hearing Anna moaning and encouraging him to "Fuck me hard!" is all it takes for Brandon to thrust deep inside her, upping the tempo . . . he can see her fingers are still busy grabbing at her clit . . . this is going to be explosive for both of them. It's been a long time since anyone let him take her ass, but never anyone with this much enthusiasm!

A few more deep thrusts, some grinding against her ass when he is deep, and the sensitive feel of his balls on her skin . . . "So close, baby . . . so fucking close . . . gonna fill your ass with my hot cummmmmm!"

 

[Cum_Inside]

His exclamation is all it takes for the fire to ignite and her fingers halt on her clit as she cums, moaning loudly as he continues to plow into her. She can only imagine that her ass squeezes down onto him like a vice as she orgasms, because the muscles of her pelvic floor clench tighter than ever and she has the biggest orgasm she can remember in the recent past, crying out and whimpering as she trembles against his body. Her hips are locked, unmoving as he uses her for his pleasure. His cock seems to pulse and expand in her ass as his balls tense and draw up, ready to fill her with his hot cum.

 

[garajd]

Every orgasm is an experience . . . every guy will tell you that! However, there are some that remain etched in your mind forever . . . and this was going to be one of those.

Sure, Brandon had fucked women in the ass before, but no one every gave herself so completely and openly to him like Anna.

"Fuckkk!!! was all that came from him. Still gripping her hips, probably leaving fingerprints, he arches his back once more and begins the first of several violent spasms of cum deep in her bowels . . . the sensation heightened by the grip that her body has on his engorged cock.

 

[Cum_Inside]

It's the first time Brandon has ever shot his cum inside Anna without any kind of barrier, and it feels like it lasts forever as he spurts. It's also the first time anyone has ever shot inside her bowels and it increases the intensity that much more. His sperm feels like fire insider her, coating every inch of her insides. She knows that she's going to want to do this much more frequently now that she has a taste for it - she also knows that she can't wait until he blows a load in her wet cunt, either, now that she can feel exactly what she's in for.

It sends her into another mini orgasm, quaking against him as she leaks even more juice, running down her slit and dripping down his balls.
"Yesssss, that's it," she moans.

 

[garajd]

As Anna lets go with another orgasm of her own, her tight muscles continue to grip his cock tight in her inner core . . . and even tho his cock is returning to normal, her inner ass muscles refuse to let go until she shivers thru another orgasm.

Once she finally shivers to a close, he leans over and kisses her on the back between her shoulders, "Holy fuck, baby girl, we are making a fucking mess on my bed." Reaching around to cup his tits in his hands, nipples still hard from the night, "But I don't hear anyone complaining."

 

[Cum_Inside]

She laughs. "We can always go to my bed," she says, as they bask in the afterglow of some of the best sex she's ever had. They stay like that for a few minutes as they catch their breath with him gently squeezing and playing with her tits. His cock is soft in her ass now, but when he starts to pull out the gaping emptiness he leaves behind makes her more uncomfortable than the pain of the initial penetration. His cum drips out from the rim and joins the puddle of their combined juices underneath her.

"That was so good," she enthuses with a wide smile. "When can we do it again?"

 

[garajd]

"Damn, little girl, now you are trying to find out just how fast this old man can recover!" Brandon responds with a laugh and a tight squeeze of her tits.

Rolling over toward the side of the bed away from the evidence of fucking good time . . . or a good time fucking . . . "We can do that whenever we want . . . but you do know the condition . . . keeping up with school. That's the last time I will mention your missing class today."

Getting up from the bed, "Let's strip these sheets before it all soaks thru to the mattress . . . and I do think a shower is in order."

 

[Cum_Inside]

She rolls out on the other side and grasps the corner of the sheets and tugging them off before gathering them up in her arms. She strolls down the hall to the laundry room, her ass jiggling as she steps. Even from his spot still at the side of the bed he can spot a big glob of white sperm dribbling down the inside of her thighs.

She returns to find that he's started the shower and has laid out a couple towels for them. He's standing under the stream of the water rinsing the sweat off his body when she climbs in behind and presses her chest up against his back, stroking tiny hands down his chest and even lower still to grasp his cock in her fingers. He probably had no idea how truly insatiable she is when he first agreed to take her on as a sugar baby, and now that she has some kind of idea of the pleasure he can give her she's going to make it worth his while. She strokes him back to full hardness before dropping to her knees and slowly working him to another orgasm with her mouth.

Once he's deposited a smaller but still yummy load of cum in her mouth, she stands to kiss him with a light press of lips. Quickly but thoroughly washing their bodies, it isn't long before they're dried off, have applied a fresh new set of sheets to his bed and are dozing off into a deep sleep with their naked skin pressed tightly together.

 

[garajd]

Gotta admit that when they are finally back in bed, it doesn't take Brandon long to fall asleep. totally spent after the night with Anna. It's been such a long time since he felt this calmness in his life.

Yes, he was Sugar Daddy, but at the same time, he was helping someone who genuinely seemed interested in making a better life for herself . . . would this last only until she finished school . . . or would it turn into something permanent. Too early to tell, but so far, it seemed as if there was some real connection . . . and affection . . . between the two of them.

No dreaming or weird thoughts tonight . . . just a solid night of sleep with a naked young body pressing tight against him . . . from someone who, for the first time in quite a while, had some stability in her life, and he was providing it.

 

[Cum_Inside]

Anna slept better than she had in days tucked up in his arms. Over the weekend they both puttered around the penthouse, him in his office and her doing various things after she finished any assignments that were due. It was about middle of the afternoon on Saturday when she dug out her pathophysiology textbook to do some studying for her midterm on Tuesday, and she spent the rest of the day curled up there on the couch reading and making notes.

It was much easier to study when she didn't have to worry about working three jobs - she could be as leisurely as she liked without worrying that she didn't have time to focus on a certain bit of text because there were more important topics and then missing easy points on the test. She noted that as the time they spent together progressed, Brandon was being quite a bit more affectionate with her, dropping a kiss on the top of her hair as he'd walk by to get a drink from the fridge or always texting her good morning if she was still asleep when he left for work.

The weeks passed quickly for them as they got to know each other, spending sweet moments curled up in bed or on the couch talking, going out to dinner or to movies, and of course those raw times he would press a hand down on her spine and strip her panties off before pressing his cock inside despite where they were in the penthouse. Anna was sure there was no room they hadn't fucked in yet, fond memories all over the apartment. Anna spent more time at home naked than she did dressed, to the point where she didn't hesitate to wander the hallways or laze around the house naked if she so chose, but instead did prefer mostly stuck to a simple tshirt and panties. Brandon certainly didn't seem to mind.

It had become normal now for him to always find her curled up in his bed when he was ready to wind down for the night and she had found her own little niche in the bed against his side. Slowly, some of her personal belongings and clothing started to make its way into his room; the first time he opened his underwear drawer to find a handful of lacy panties tucked into the corner neatly he swallowed a fond laugh, but that was only the beginning.

It was one of those days almost at the end of the winter semester for her third year that she was propped up against the arm of the couch surfing through the channels on the TV wearing Brandon's favourite pair of panties (royal blue and lacy - they contrasted so well with the pale complexion of her skin) and just a white camisole, that the pounding on the door startled her. She was home alone, and although the penthouse was well protected, Anna always felt better keeping the door locked in the daytime when Brandon wasn't home - he was supposed to be home an hour ago but had texted that something had come up at the office and he would be late but that he'd bring home dinner.

She could hear a woman's voice screeching on the other side but couldn't make out her words. Carefully padding to the door, she hit the button for the video feed. The woman banging her fist against the steel of the door was pretty, she noted. Long blonde hair, bright blue eyes. She had a decent sized chest and from here her legs looked pretty long, but the scowl on her face detracted from all that. She was swearing and cursing, demanding, "you asshole, how dare you change the locks! Open the fucking door and let me in! How dare you lock me out of my own house!"

 

[garajd]

Brandon was running late; an important client had called at the last minute with a serious problem. After a few minutes on the phone, and then 30 minutes with one of his best tech's, the issue was resolved, the client was happy, and Brandon and his tech could go home. Because of the seriousness of the problem, and the value of the client to the firm, Brandon gave the tech $100 to treat his family to dinner.


Early on, Brandon had learned that Anna was a sucker for pizza from a particular place, along with a specific wine. So, he took the few extra minutes on his way home to pick up the pizza and wine for dinner tonight. As long as he had beer in the fridge, that made any pizza acceptable.

As he entered the building, the security guard approached him, "You daughter stopped by today and before I could intercept her, she was in the elevator and on the way to your apartment. I guess she will find out when she gets there that we changed all the locks and entry cards six months ago."

Brandon took a deep breath and entered the elevator, not looking forward to the confrontation that was going to face him . . . and Anna. Sure enough, exiting the elevator, she was there, ranting and raving in the hallway between the four apartments on his floor.

 

[Cum_Inside]

Anna's first presumption that this was someone he'd a prior... arrangement with, but that thought was easily dashed as she watched the elevator doors open and Brandon step out. His mouth was curled in distaste as he called, "Alie!" with a sharp reprimanding tone. The woman's hand froze just before it made contact with the door as she whirled to face him, still spitting curses angrily.

Anna's heart dropped. Alie. It wasn't a sugar-baby at all (that might have been easier to deal with); she was his daughter. They'd spoken of his family before just enough that she might recognize the names if they came up in conversation. He always passed quickly over the subject and it was clear he wasn't too pleased with them, so she never brought it up. She hadn't yet had to deal with any of his family but she had been well aware at some point it was very likely the two parts of his life might collide.

Anna just always imagined it would happen peacefully - that they would meet somewhere mundane like a coffee shop, or that it wouldn't happen at all. She had never imagined explaining why a woman even younger than Alie, less than half her father's age was half-naked in his penthouse! She scrambled down the hall on barefeet in her rush to grab some pants and a better shirt.

When she returned, she could still hear raised voices outside the door. It was obvious now she wasn't going to leave without getting what she had come for in the first place.

 

[garajd]

Facing his daughter in the hallway, "Get the hell out of her, Alie. You have no reason to be here without calling first. You know the rules that I established for you and your brother. You get your monthly allowance on the first of each month . . and you leave me alone. Until you get past some of the hatred that your mother planted in you, you are not welcome in my home. My home . . . not yours."

Standing there, face to face, "If you prefer, I will call security to physically remove you from the building and then get a restraining order. Your choice, Alie, but I am not opening that door until you get on the elevator and leave. I will let security know you are coming down and they will escort you from the building."

After a couple of minutes . . . nothing spoken . . . she leaves and enters the elevator. Brandon calls down to the Security desk to confirm that she has indeed left the building. Once he gets that confirmation, he enters the apartment, looking for Anna.

 

[Cum_Inside]

The pure anger in his voice is something Anna hasn't heard before; it scares her slightly. Because she stands just inside the door chewing on her thumbnail, he almost crashes into her as the door opens. She's pondering quite heavily now - she hadn't known that Brandon also pays his children a monthly allowance. The idea that she gets the same treatment as his children sickens her for some reason... that to him, he can just throw money at people to get them to do what he wants.

Not only that, but Anna is younger than them, is not related and most likely gets relatively close to the same amount per month that they do, what with her allowance and all the extra things he buys for her, just in response to her putting her mouth on his cock. She's not stupid, always understanding the agreement between them, but now that she has some more insight into his family relations, she wonders how on earth he could treat them so coldly. What had happened to cause this rift? Would he ever throw her out into the cold and pay her to stay away like it appeared he had done to his own children? Maybe he was only keeping her around because she was still useful to him. How much longer until that faded and he found someone else to spoil and fool into thinking they meant anything to him?

With her heart in her stomach, Anna realizes what that sick feeling is - she cares for him. Anna has developed feelings for him these past few months and she wants things to be different - she doesn't want his money; doesn't want to be his sugar baby. She just wants to be someone he chooses to come home to because he cares and not because he's paying her for sex.

Biting back tears and that nauseous feeling that has settled in her tummy, Anna says, "I'm not hungry," before disappearing into her room and shutting the door with a definitive click.

 

[garajd]

Giving her a few minutes while he carries the pizza and wine to the kitchen, Brandon walks down the hall to Anna's bedroom. Knocking on her door, he steps inside and sees her stretched out on the bed,

"Anna, please listen to me for just a moment, then I will leave you alone. I'm sorry you had to see and hear that. Obviously, I should have told you more about the relationship, or lack of a relationship, between me and my kids. I care about you very much and I didn't want to fuck that up be bringing my kids into our relationship. Please forgive me for hiding that from you. I will be in my office if, and when, you are ready to talk to me."

 

[Cum_Inside]

She scoffs but says nothing more than, “I think I’d just rather stay right here,” her thoughts are troubling and he’s not helping - his declaration that he cares for her may have put a smile on her face at one point, but all it does is sour her stomach at the moment. Of course he cares - he cares for the sweet young body he’s fucking, not Anna herself.

She knows maybe she’s being a little over dramatic over this, but she can’t help how she feels. She doesn’t know when these feelings crept up, doesn’t know when she started to fall in love with him, but she knows she needs to tamp those feelings down and get over them before they grow into a monster that she can’t do anything but let devour her. If she doesn’t stop them, she’ll only be hurt when he decides he’s had enough of her and throws her out.

“Goodnight, Brandon,” she says instead, closing her eyes and making it clear she’s done with the conversation.

 

[garajd]

Brandon closed the door behind him and retreated to the den, grabbing a beer on the way. He lost himself in the basketball tournament games before going to his own bedroom and trying to sleep. Between his fight with Alie and now Anna shutting him out . . . it was going to be a rough night.

Up early the next morning, as usual, he was in his office looking over some mail and the newspaper; he realized that his relationship with Anna was not good right now, but until she was ready to talk, there wasn't much he could do.

 

[Cum_Inside]

Anna laid awake listening to him move around the penthouse for a while before she ventured into her ensuite and got freshened up. She decided that she was going to go out shopping and take her mind off everything. When she reached for her phone, she noticed that there was a notification from Tinder - she couldn't even remember the last time she'd checked it, so wrapped up in Brandon and getting settled in and the (admittedly) phenomenal sex.

She hesitated. Maybe going on a few dates would be exactly what she needed to get her mind and heart off a man who was never going to love her. Thumbing through and responding to the messages that looked the best, Anna dressed quickly and styled her hair in loose curls before practically dashing out of the house before Brandon could get a word in.

Over the next several days, leading up to a week, all of their conversations happened by text message. Anna made sure to not be home when he was, and she could tell his frustration was reaching boiling point.

Tonight, Anna panicked when she heard the main door click closed. Brandon wasn't supposed to be home for another hour! She was hoping to be dressed and gone on her date (with Michael, a friendly 29 year old architect who loved dogs and craft beer - they'd been talking pretty much since that first day and while he was into her and quite funny, Anna wasn't sure that she was interested in much more than a free meal) before he returned.

She froze in front of the mirror where she was lightly applying a dab of lipgloss to complete her date-night look as she heard his footsteps venturing further down the hallway towards her. She had on a tight pair of dark wash blue jeans and a wine coloured shirt that dipped low over her cleavage to provide a tasteful peak, and her favourite pair of black stilettos. Her hair was twisted and gathered back from her face, makeup subtle but defining her eyes and the natural pout of her lips.

 

[garajd]

Since his blowup with Alie in the hall, which Anna had seen and heard, Brandon had made several attempts to talk with Anna, but apparently had her mind made up that his feelings about her were only to get her attention for sex. She had managed to avoid him and had responded to his texts in one or two word replies. Time to deal with this, once and for all.

Leaving the office early on an afternoon that he knew was an early class day for her, he walked into the apartment and dropped his briefcase in his office. Walking down the hall to his master suite, which required him to pass her room, he looked in just as she exited the bathroom, obviously dressed to go out. The look on her face was a dead giveaway . . .

Walking into her bedroom, which basically was against their agreement unless invited in, he firmly took her arms in his two hands, backed her up and sat her down in a chair in the corner. He had no intentions other than finally addressing the gulf between them in other manner than by words. Yes, she liked their sex a little rough sometimes, but Brandon did not treat her or any woman in his life with physical violence . . . one line he never had and never would cross.

"Anna, we are going to talk about us and get this resolved. After that you can make your decision about staying with me, or leaving."

 

[Cum_Inside]

She looked up at him as she pushed her to sit but didn't fight against him. She knew they had to resolve this at some time or other, so she figured that they might as well get it over with. She just hoped they resolved it quickly enough that she could make it to the restaurant in time.

"Fine, Brandon. But I've got a date waiting for me, so please make it fast," she replied trimly.