Who Going to Pay for University? (Closed)

[Cum_Inside]

Anna focuses on cleaning her lover’s cock first before she turns to Shane. Her tongue traces down his body following the ropes of cum until every last drop has been swallowed, before Anna tugs Shane up by the hair and guides him to the bed, leaning his chest over the mattress with his ass positioned perfectly to accept her lover’s final present.

She slowly pops open the top of the lube bottle, knowing that in the silence of the apartment the sound is loud and intimidating. She holds the bottle up over his ass, letting some drizzle down into the crack there. She spreads that around with two fingers, coating them and the rim of his ass until she’d satisfied. She presses her index finger against his pucker, watching how it recoils away from her touch. She pushes steadily until it’s buried to her knuckles inside him, listening to his deep moan and enjoying his flinch away from the intrusion. “If you can’t even take my finger, you’ll never take his cock,” she murmurs. “Are you a virgin, baby?”

 

[garajd]

Hearing a nervous sound from Shane, "I think he is, baby girl. You sure you want to do this to him right now. Maybe you should just use your anal plug on him and let him work up to my cock?"

 

[Cum_Inside]

Anna pouts but nods, stretching him with one finger and then two, working him open just enough to take one of her smallest plugs. “I guess we could do that. But what makes us so sure Shane here will come back for more? He might run for the hills and I was so looking forward to it,” she whines petulantly.

 

[garajd]

"Trust me, baby girl, he will be coming back here. Won't you, Shane?"

Shane nods meekly, knowing that whatever happens before he leaves, he is already caught in our game of kinky sex. "Anna, love, let me play with Shane a bit while you get a pad of note paper from my desk. I'm sure Shane will be happy to give us his phone number and address so that we can reach him whenever we want him to come over and play."

As she runs to get the paper, I pull out the small plug and insert Anna's vibe into his ass and turn it up to full speed; that ought to loosen him up. Once Anna gets back and writes down his phone number, she calls it from her phone . . .it rings.

"OK, love, now you are going to get your wish. Grab the tube of lube and get my cock all lubed up."

 

[Cum_Inside]

Anna is more than happy to oblige. She might stroke his cock an extra few times more than necessary to ensure he’s adequately coated in lube, but it doesn’t appear that he minds. She waits, perched on her knees just as she knows he likes for further instruction. Anna is careful to not step out of line as she didn't quite punished for her misdemeanour of allowing Shane into her bed in the first place.

 

[garajd]

Releasing Shane from his cuffs; he does need to be able to balance himself when Brandon takes his virgin man pussy. Removing the vibe from Shane, handing it to Anna to take care of before she intends to use it again, "OK, baby girl, lube him once more and finger him as deep as you can."

Sitting back on his heels, Brandon watches as she does as directed; this time her finger is inserted quickly and deep. Shane seems to take it a little easier this time, but the true test is yet to come . . . the girth of Brandon's dick.

"Let me know when you think our little boy is ready."

 

[Cum_Inside]

Anna is careful to work him open slowly on two fingers, then three and finally four. She gauges his readiness by his moans of pleasure and when he starts to wiggle and thrust his ass back against her fingers. This task is hard for her, impatient though she is. With Anna’s preference for anal verging on the border of slightly painful, doing this much preparation is a foreign feeling.

She presses a soft kiss to Shane’s back as she murmurs what a good boy he’s being. Brandon watches from his place at the foot of the bed, nodding in approval at how unhurried Anna is making this despite how badly he knows she wants this to actually happen.

“Are you ready to take daddy’s cock, slut?” She questions, totally at odds with the soft, careful manner to which she’d prepped him. She wants him to come back, feel free to engage in any future play sessions, but she’s also not exactly vanilla and loves the thrill of being so humiliated. Sometimes that desire reflects on how she talks to her sex partners.

“Once he breaches your tight ass for the first time, he won’t stop; you’re daddy’s good little boy to do with as he pleases. You have to be sure this is what you want. The safeword is red,” she offers, waiting nervously, wondering if he’ll use it despite his obvious pleasure so far. Being prepped for anal is much different than actually following through - it’s a scary thought and Anna wouldn’t blame him if he backed out, even though she doesn’t want that at all.

 

[garajd]

"OK, Anna, my turn." Moving up behind Shane, out new toy, I look to Anna, "Guide me up there, baby girl."

Using Anna as an instrument in taking Shane's anal virginity places her in a role of being my slave at the same time, not allowing her to just sit back and watch her little boy-toy get fucked, but actually having to be a participant in his de-flowering!!

"That's it. Now just wait for me to pop his tight hole. Then you need to be caressing his balls and stroking his cock, helping him get as aroused as possible."

 

[Cum_Inside]

She firmly wraps her hand around Brandon’s cock, running the head back and forth over Shane’s clenching asshole, smearing even more live around. Anna holds his cock steady over the rim and Brandon pushes, applying the pressure he needs to open up that tight little sphincter enough to allow his cock inside. Shane grunts loudly as the head pops through, and Anna rocks back onto her heels to get a close-up as her love takes their newest partner’s anal cherry. She smiles widely, loving the show already.

Anna’s left hand is absentmindedly fondling and stroking at Shane’s cock where they’re pressed against the bed as she watches the scene before her.

 

[garajd]

As soon as he breaks thru, Brandon thrusts until he is soon balls deep in Shane; gripping his hips, giving Shane a little time to accept the abrupt intrusion. Looking over at Anna as she strokes Shane's erect cock, Brandon can see the moisture from her starting to coat her pussy lips.

Reaching down with a hand, he touches her thighs, enough of a hint for her to lie back and open her sex to his touch. His fingers easily penetrate and find her clit to tease and arouse.

 

[Cum_Inside]

She can’t help but throw her head back for a moment and absorb the skillful touch of his fingers on her clit. She forces herself to focus, watching how Shane trembles and moans in regards to the rod buried in his ass. Brandon’s cock is large and Anna has to admit how proud she is that Shane could take it all, even though he’s not half as good as Anna.

Oh well; another hole for her love to fuck when Anna can’t be available. It seems to take forever before Shane gives a tiny, almost imperceptible nod of his head. Brandon immediately pulls back only to drive his cock back inside and the sound Shane lets out is so fucking sexy that it causes Anna to clench her lip between her teeth as she feels her pussy get just that much wetter - halfway between a strangled moan and a scream.

 

[garajd]

Brandon never anticipated being in this situation . . . fucking the ass of a young twink half his age while finger-fucking his young lover . . . three orgasms ready to explode, and it looked like Anna would probably be the first to let go. Watching her lying on her bed, reaching in under Shane and stroking his cock as Brandon's acted as a piston driving in and out of his virgin man-cunt . . . definitely not what either Anna or Shane imagined when they came home from the club.

 

[Cum_Inside]

Anna came first, squealing as Brandon drives a finger inside and pinches her clit simultaneously. Shane’s still a little ways off from hisnorgasm, and Anna’s strokes are definitely lazier now as she sprawls back on the bed, her energy sapped. Now she just enjoys the performance the boys are putting on, knowing Brandon still has a little while before he’s ready to cum, too, since he just did not all that long ago.

 

[garajd]

Brandon can see that Anna is enjoying the show in front of her . . . probably not what she had ever considered as a possibility from Brandon. First, he shot a load all over Shane's face after the young twink sucked his cock, and now, the 'old guy's' cock is buried in his ass and Anna is lying there enjoying every thrust by Brandon.

He doesn't really care if Shane cums again or not; Shane is obviously really tight, given he was a virgin until a few minutes ago. Looking into Anna's eyes, "You ready, baby? Ready for me to fill your boy toy's ass with a load of hot cum?"

 

[Cum_Inside]

“Fill him for me daddy,” she bosses. “Let him know how wonderful it is.” Brandon doesn’t need any more permission (not that he needed it in the first place) before he’s pressed his hips into Shane’s full ass and his balls pull up, pumping the first of many ropes of warm jism deep into Shane’s bowels. He grunts every time he releases a new torrent, and Anna can’t wait to suck that all back out again.

It takes another minute before Brandon pulls out, his softening cock covered in dollops of sperm. Anna knows her job inside and out by now so she immediately drops onto her knees and slurps his dick into her mouth, cleaning him. After thatms done, she immediately turns to Shane to get a better view and maybe a taste from the source.

He’s breathing hard, dick still hard between them. She didn’t expect him to cum the first time he does anal - it does fucking hurt! It can take a while to get used to it and to glean any pleasure from it, so she understands. She reaches under him and strokes him off until he orgasms, spreading his cheeks with her free hand and looking in awe at the white cream leaking from a reddened pucker.

“Can I, daddy?” She asks. Brandon nods from his position still at the foot of the bed watching his sexually deviant baby girl as she leans down to suck her man’s cum from another dude’s rosebud. She moans at the musky taste, wasting no time swallowing it all down.

 

[garajd]

Nothing surprises Brandon anymore . . . Anna licking his dick clean are dumping his load in Shane's man cunt, bringing Shane to an orgasm, then kneeling and licking all of Brandon's cum out of Shane's freshly fucked ass . . . but he would have to admit that the ending of this scenario was not what he expected.

"I'm going to take a shower in my suite. Where are you and your toy going to clean up?"

 

[Cum_Inside]

“We’ll shower in my bathroom,” Anna responded, gently helping Shane up and herding him into the bathroom. He winced, limping for the first few steps before he drew himself up to his full height. They wash each other quietly, not speaking until they step out and dry themselves off.

“Are you okay?” Annaleigh stroked a hand down his spine in support . He gave her a small smile, nodding in reassurance. “I’ve had a lot worse. It was an... interesting morning, to say the least,” he laughed. “I certainly didn’t expect a pretty little thing like you to be fucking an old man - even if he is hot,” Shane teased.

Anna grinned back. “I hit the jackpot, actually. Sometimes I wonder why he picked a silly little girl like me when he could have anybody,” she admitted.

Leaving that subject alone, Shane began to gab about random things: his dog, what classes he’s taking, his extensive DVD collection and so on. They find they have plenty of things in common and they both agree that they’re definitely going to have to do this again very soon. He has her number from when she called his phone earlier, and the kiss for goodbye they shared as she walked him out is already full of fondness. Brandon is nowhere to be seen, but Anna isn’t too worried. He does like his long showers, after all.

Anna curled up on the couch with a bowl of cereal, half watching the television and half thinking about the strange turn of events. It wasn’t long before Brandon nudged her over a bit so he could slide in underneath her and she moved obligingly.

****

Life continues. Anna’s schooling became hectic due to the encroaching exam period and she doesn’t have very much time to spend with Brandon between tutorials, group study sessions and reviews. He’s been coming home later and later, always in a good mood, and it makes Anna wonder if maybe he has a girlfriend on the side. Of course he’s pleased that Anna has been putting forth so much effort into her class work and therefore he doesn’t complain about her lack of free time, but it’s odd for them not to be having regular sex. She knows the change in routine must be affecting Brandon as well even if he says nothing about it.

On the evening of her last exam, when Anna finally managed to drag herself into the penthouse she’s mentally exhausted. She dropped her backpack and shoes in a heap on the floor before venturing deeper into the condo. Brandon’s deep laugh is echoing in the wide space of the kitchen and she started in to greet him when she overheard, “I’ll be sure to do that, darling. I’ll take you to the Middle Spoon (a fabulous restaurant that only serves drinks and dessert - Anna’s favourite) tomorrow evening. It’s been too long since I’ve had a night out with a beautiful woman...”

She froze. It felt impossible for her to believe what she’d just heard, but Anna isn’t actually that surprised. He’s an attractive older man with his life together. He lives in a massive penthouse with a great job, has no wife or kids to chase after since he’s started to pay them to leave him alone. Only a spoiled brat of a university student with whom he has no real attachment to - she’d always been expecting the other shoe to drop, but hadn’t expected it to be so soon. Of course he’d meet someone better suited to his lifestyle. It had always been an insecurity of hers and she’d thought she hid it well, but as she turned and tiptoed down the hall and locked her bedroom door behind her, the anxiety of him leaving her takes over and her back slid down the door until she was sitting with her knees bent up to her chest.

Her “relationship” with Shane is just sex and they both know it. It’s why Brandon allows it to go on at all. If she was to develop actual feelings, Anna knows Brandon would put an immediate stop to it. Even though they’ve admitted to loving each other, it doesn’t change that Anna is a broke college slut being paid to fuck him. She has nothing to nothing to offer him; no income other than his own money, no education, no valuables - no nothing. This woman he’s talking to is no doubt leaps and bounds more impressive than her. A much better choice to have a relationship with.

Anna tries to swallow down the sick feeling in her stomach. Jealousy.

 

[garajd]

Obviously, her school work is of paramount importance to both of us; that is why this relationship was established. It does seem, of late, that she is spending more time away from the condo on more than just school. Brandon knows that she is fucking Shane on a pretty regular basis; for the two of them, it is all about the sex.

A couple of weeks ago, Brandon received a call from a former relationship (actually close to 5 years ago); she is going to be in town later this week on business and is open to dinner with him. Their relationship by now is entirely non-sexual; they parted on the best of terms and have remained in contact thru the years. As Brandon wraps up this phone call in the kitchen, he hears Anna enter the apartment and, as quiet as she tries to be, hears her bedroom close. He assumes that she has heard the end of the phone conversation . . . and is, understandably upset.

Giving her a few minutes, he walks down the hall and knocks on her door, "Anna, come to my office. We need to talk."

 

[Cum_Inside]

She listens obediently, but only several minutes after he has walked away and has left her in silence. Anna knew that he most likely realized she’d overheard him and thstbthis conversation would be one she probably would usually avoid at all costs, but she pushed herself to her feet regardless. She didn’t bother to knock, making herself comfortable in the chair she seemed to spend the most time in throughout the who penthouse.

“Yes, sir?” She asked coolly, hiding her negative emotions deep inside. She folded one knee across the other and waited for him to speak. Those green eyes of hers betrayed her, though. There was a deep sadness present in them as she waited for him to tell her their relationship was over - that he’d found another much better match.

 

[garajd]

"I am not going to pretend to know everything that is going thru your mind right now; I can make some guesses, and probably be pretty close. I know that when you came in this evening, you probably heard me on the phone in the kitchen; obviously, I didn't try to hide it from you, and in a few minutes, I will explain a few things to you."

"On the other hand, baby girl, you have continued to see Shane and use him as you personal fuck-toy, getting nothing from him but sex; it shows that your emotional needs are not being met by him. He is getting what he wants. Someone to fuck who will not make any demands from him other than his cock when you feel the need."

"So, tell me, what is going on with you?"

 

[Cum_Inside]

Anna frowned in perplexity. She’d only seen Shane a handful of times since their first encounter. Brandon talked like it was a regular occurrence. “No, he doesn’t meet my emotional needs. You do. But we’ve both been very busy lately. My exams are just finishing and you’ve been working long hours. The last time I had any sex was with you on this very desk last week,” she responded, reaching out to slide a hand across the smooth surface.

“I love you, Brandon. Shane is exactly what you said he is - a fucktoy when we can’t come together. I won’t see him anymore if that’s what you’re getting at.”

 

[garajd]

"So, you also want me to believe that the phone call you walked in on this evening has nothing to do with what you are feeling right now.?"

He is ready to tell her who he was talking to and what their connection is (a relationship that ended years ago, ended amicably, and they still have dinner when in the same town), but he needs her to tell him what is going thru her mind before he offers an explanation.

"Any decision about you continuing to see Shane is yours; I will not dictate who you can and cannot see . . . or fuck, for that matter."

 

[Cum_Inside]

Anna shook her head, refusal to describe her feelings at the tip of the tongue. Instead, she said, "so what? It's not like you're not allowed to see other people - you just said I could fuck Shane whenever I want. The same goes for you. I'm your sugar baby; this next year is the last year of my schooling, Brandon. Our agreement won't last forever. You're free to pursue whatever you want."

 

[garajd]

He could tell that Anna was holding something back; she was not being honest with what she was feeling. He knew it. And she knew it. But unless he could get her to say it, they were at an impasse.

"You just said that you love me. And there should be no doubt in your mind that I love you too, Anna. You are far more than my sugar baby; you are my baby girl, my lover. And this thing with Shane; I won't stop you. I would just prefer that anyone we involve in our relationship is someone that we both have fun with; honestly, I thought Shane was going to be one of those."

Looking at her across the desk. "Anna, as far as I am concerned, what we have is no longer an 'agreement'. We are two people in love who also enjoy exploring some fun that many people would consider 'outside the lines'. Is there anything else that you want to ask me?"

 

[Cum_Inside]

Anna was desperate to ask about his new lady-friend, but he wasn't talking about it so she didn't bring it up. She had to play it cool - he was a grown man allowed to have friends. Anna was his girlfriend, but she wasn't that girl that policed who her man spoke to eve though she was one jealous bitch.

"Shane will play with both of us - you just haven't expressed any interest so he's been staying away," she shrugged, rising from the chair. "You can't blame me for that. Can I go? I'm tired from my studying so much," she asked, rounding the desk to kiss him softly. "I'll meet you in bed."