Anna

He's leaving it up to me. Do I want this or do I want to stop? I know that I want this but how could he? Sid can have any woman in the world but he wants me? I desperately wish that I had more experience or that I was sexier. I watch as Sid waits for my decision. This is the second time he's wanted me. Sure the first time he was drunk but this time he's sober.

I reach behind for his hand and push it further up my back. Sid understands and slides his hand over my bra clasp as he sits up so that we're face to face. His clever fingers release by bra as his lips capture mine again. I wrap my hands around his neck and feast my fingers in his hair. It's dry now, thick and curly.

Both of his hands travel over the bare skin of my back, to my waist and then his thumbs each slip under my bra. I moan into his mouth when each thumb flicks a nipple. I lose control and my head falls back as he does it again. Sid's lips kiss and lick my neck from chin to shoulder as his thumbs flick again. I moan louder this time.

"You are so hot when you moan" Sid says in a deep, husky voice.

I guide his head back up so that I can taste his lips again. The heat rushing through me is nothing like I've ever felt before in my life. I've never had a man want me like Sid seems to or kiss me like he does or make me feel the way he does. Of course I've only slept with one other guy before so there isn't much to compare.

Sid pulls away from me and slides his hands up my sides taking both my shirt and bra with them. I put my arms straight up to help him and then I'm shirtless. I'm more than a little breathless and much more than a little turned on. Sid's eyes as he looks at my newly bare skin are overwhelming; but, then he reaches behind him and pulls his tee shirt off. I forget everything but Sid.

Sure, I've seen him shirtless before but never like this, never when I can just reach out and touch him while he's touching me. I'm desperate to touch him, everywhere, but I don't. I've never known what to do or how to do it. When I've been with Sid before, instinct took over and I didn't have time to think about anything. Now that we're here, alone, I'm unsure of myself.

"What's wrong?" Sid asks.

He cups my cheek and rubs his thumb over my bottom lip. I shake my head.

"Tell me Anna. We don't have to do anything else if you don't want to" he tells me. "Talk to me."

He looks so sweet and concerned that I blurt out "I don't know what to do."

Mortified, I pull my hands from his shoulders and cover my face. I want to pick up my things and run far and fast from this room, this house, everything.

Sid chuckles and I just groan my embarrassment.

"Oh, Anna. I'm sorry. I'm not laughing at you, honest" he tells me. "You said that you aren't a virgin. I mean you and I already, you know."

He's not letting me go so I lift my face and look at him. He's smiling but in a kind way.

"Yes we did and I had a boyfriend who I, you know, too. Anyway, I just don't have a lot of experience and it's, well, it's you." I stop and shake my head. "I think I'm just going to get my things and go."

Sid cups both of my cheeks and forces me to look him in the eyes again.

"You can definitely do that if it's what you want. Or we can get dressed and watch another movie. Or we can" he trails off. "It's up to you."

I'm stunned.

"You mean you still want to" I ask but don't complete my full thought.

Sid pulls me closer to him and kisses me softly. I'm close enough that I know that his kiss is the only thing that is soft. I can feel how much he wants me pressed up against me.

"It's up to you Anna" he says and kisses me again.

He leans his forehead against mine and waits. Again, he waits for my decision. We've already done this of course I push away everything that came after or else I would say no for sure.

"Yes" I tell him.

"Yes?" he asks.

"Yes."

"Oh thank God" he says and kisses me again, hard this time.

I dig my fingers into his shoulders, his gorgeous, hard, muscles. He pulls me even closer and his hips tilt up and I grind down against him. The friction gives me some relief but it also makes me want more. Sid kisses down my neck and I sit up higher on my knees to give him better access. His hands continue pushing me up so that my breasts are in line with his lips. I'm ready to beg for them but I don't have to because he leans closer to me. At first he kisses and licks the swells of each breast while his hands cup and push them up. He makes me wait, desperately, for his lips to find their final goal. I try to guide his head but he won't let me. I'm completely at his mercy.

"Sid, please" comes out of my mouth. I'm stunned. I never talk during sex; never.

He doesn't make me wait any longer for his lips to capture one of my nipples between them. He sucks, licks, kisses and sucks again. My nipple gets harder and harder and then he moves to the one and repeats. I'm lost in sensations that I've never felt before and overwhelmed by the heat coursing through my body. I'm vaguely aware that I keep grinding my hips against Sid's and his answer. I want more, much, much more.

Sid pulls away and shifts so that I'm sitting on the sofa and he's kneeling in front of me. He undoes the button of my jeans and then pulls so I lift my hips to help him. Now I'm sitting in front of him in nothing but my panties. I'm suddenly aware that my stomach is round instead of flat. My thighs must seem huge to him. He has probably never been with a woman like me before.

Whatever I'm thinking flies out of my head as Sid lifts one of my legs. He starts kissing my instep and then up my calf, thigh and hip before he moves to the other leg and repeats the same. My body is jello, absolutely jello and I can't do anything but watch as he expertly plays it. He kisses up my stomach and then pays special attention to one breast and then the other. His lips slowly travel up my chest, neck and capture my lips.

I feast my hands in his hair and his lips become more insistent. His tongue plays over mine, dueling, parrying, thrusting, over and over. I sit up straighter so that I can pull his body closer to me. His hard, naked chest against my own skin feels exquisite. Sid's hands slide down my back and slip inside my panties where his fingers explore the exposed skin. I'm suddenly desperate but my mind doesn't compute exactly for what. I just know that I need more.

The button of Sid's jeans presses against my skin and I realize that he's still wearing them. I pull away from Sid and he lifts his head. His eyes, oh my God, his eyes are almost black with their intensity. It takes my breath away for a few moments but then I remember my task.

With trembling fingers, I reach for the button on his jeans. My hands are shaking causing me to fumble a bit. I'm quickly reminded why I don't take control more often. While I fumble with the button, Sid leans down and kisses my neck softly and slowly. It both excites and calms my nerves. With the button undone, I turn my attention to the zipper and this goes much smoother. Sid helps me push them down and then he stands to take them off completely.

I look up at him unsure what to do next. Sid takes my hand and pulls me so that I'm standing too. He leans down and we kiss. It begins softly again, slowly, teasing. I feel his hard muscles when I slide my hands up his arms, to his shoulders and then around his neck. Sid's breathing changes and so does our kiss. It becomes more desperate and we're both breathing hard and heavy. His fingers find their way into my panties again and he pushes them down so that they fall at my feet. He pulls back slightly so that he can pull down his own boxer briefs and then he grabs his jeans. After fishing through his pocket, he pulls out a condom. Thank God I don't have to ask if he has any.

Sid sits on the sofa, pulls on the condom and then takes my hand so that I can straddle him. I have a flash back to our first time when he was fumbling with fast hands. This time is so different.

He doesn't immediately thrust; instead, we kiss again and again, heating up quickly. My hands travel over his shoulders, neck, into his hair, I can't keep them still. I want to touch him everywhere. I feel Sid's fingers tighten on my back when I tug has hair and angle his face more. The only thought that goes over and over through my head is 'more'. I need more.

I pull back, lift up slightly and place my hands on his shoulders. Sid uses his hand to guide inside of me as I push down against him. Oh God, I've never felt anything like this, never had sex this way before. It feels like I am completely filled with Sidney. I revel in the feeling of fullness and think that I moan. Sid holds me to him and neither of us moves. Slowly, his hips begin to move and cause me to rock back and forth. Wow, just wow. All other thoughts are gone and can't be formed. I start moving myself and alternate between the rocking and using his shoulders to rise up and down.

I think my head has fallen back because Sid is now kissing my neck. When he gets to my collar bone, he nips at me with his teeth and then laves it with his tongue. My body feels too hot. Sweat breaks out over every inch of my skin and there is this unfamiliar pressure building deep inside of me. This is so incredibly intense that it momentarily scares me and I stiffen up.

Sid moves his lips to my ear, kisses my neck underneath and then takes my lobe between his lips and sucks. At the same time, he stops thrusting and his hand moves between us. I don't know what he's doing but it all feels so good. Oh God, now I know as his fingers press and play with my clit.

"Come on baby" he says directly into my ear.

The pressure inside of me, his fingers on my clit and his breath in my ear must do what he wanted because I feel my body stiffen but in a different way than before. Sid starts thrusting again and I begin to shake as another heat wave rushes over my body. I'm vaguely away of Sid groaning loud into my ear as I collapse onto him.

It could be minutes or hours, I don't know, before I join consciousness again. First, I feel Sid's fingers stroke slowly up and down my spine. Then I notice that I'm a sweaty mess, my hair is everywhere and I can't seem to care.

"Are you still with me?" Sid whispers into my ear.

An involuntary shudder travels through my body at both his words and feeling his breath in my ear again.

"I'm still alive, right?" I ask.

His deep chuckle has the same effect as his breath did. Oh God.

"Yeah, you're still alive" he replies.

I snuggle into a more comfortable position so that my head is on his shoulder. The problem is that my head is more comfortable but my right leg is cramping, badly.

"I need to stand" I tell Sid. "My leg hurts."

Sid immediately stands and takes me with him. I slide down his body until I'm standing and can work out the kink in my leg.

"Better?" he asks.

"Yeah" I reply and look up at him.

Sid's hair is a mess from my fingers. His lips are even larger than usual and I feel a secret pleasure that it's from my lips. He's as sweaty as I am.

Sid leans down and stands handing me his shirt. I'm grateful and put it on. Being naked while we were, well, that's different than standing in front of him now. Sid puts on his boxer briefs.

We stand looking at each other in an awkward silence. What do I say or do now?

"Why don't we go upstairs?" Sid asks. "I'd love another shower."

He grins at me and I feel all of the awkwardness melt away. I'd love another shower too.

"Sounds good to me" I tell him.

We pick up our clothes and start walking out of the room. Sid reaches for my hand and pauses to kiss me. When he lifts his head, he's grinning again and then leads me up the stairs until we're at the bedroom floor. I'm confused when he turns to the left instead of to the right where the spare rooms are. I know that we're in his room immediately. First, it's huge and has a California king bed. The furniture and colours are all very masculine and there is a big screen TV on one wall.

He tosses his clothes on the ottoman at the end of the bed so I drop mine there too. Sid doesn't stop until we're in the bath room. Inside is the largest shower I've ever seen. It's as big as my first dorm room. There are multiple shower heads, two benches and looks like its sealed.

"I know" Sid says. "Most people spend the most money in their house on their kitchen. I spent it here. Come on."

Sidney

After our shower, and a little more play time, we lay in my bed exhausted. What is it about this girl? I trust her implicitly and that never happens. I'm always comfortable with her and I never worry about saying something stupid. She just fits, like she does right now, curled up beside me, in my arms; it's a little disconcerting. My iPhone is on the nightstand softly playing music. It's country which Anna seems to like since she's humming.

"You like country music?" I ask her.

"I'm from the south, remember?"

"You don't have an accent. I thought you grew up in Pennsylvania."

"My mother is from the south which means my sister and I are too. It doesn't matter where you were raised."

"How come you don't say y'all?" I ask her and am rewarded with a chuckle.

"When we visit my mother's family in the south, I definitely speak more southern and an accent develops."

"Ok, so I've always wondered. Why do some people in the south say 'y'all' and others say 'all y'all'? What's the difference?"

"Y'all is singular and all y'all is plural."

"Huh?"

She shifts and rests her chin on my chest so that she can look at me. I absently brush back a lock of her hair that's fallen over her forehead.

"If is saw you alone, I'd say 'how y'all doing?' If I saw you and a few others then I'd say 'how are all y'all doing?"

"That's weird" I tell her.

"That's the south."

She rests her check back onto my chest and absently begins to 'draw' circles on my stomach with her finger. I don't think she even realizes that she's doing it.

There's something that I've been curious about so I decide to take advantage of the moment.

"Anna, um, can I ask you something?"

"Of course" is her immediate response.

"Earlier, when we were having sex, you seemed embarrassed. I mean you even blushed."

"Maybe I was just hot" is her sassy retort but I sense something else. There's an undercurrent of something in her tone.

"I can definitely agree that you're hot" I tell her and kiss the top of her head. "But that's not what I meant. I hope that I didn't do something."

I guess I'm still worried about what she thinks of me. Fuck, I don't even remember the first time we had sex. It's a miracle that she's in my bed right now.

"Oh Sid, no" she says and looks up at me again. "It was wonderful this time, honestly."

She looks earnest and pleading for me to believe her; but, that doesn't explain the embarrassment.

"That's good. So what's up with the blushing?"

She puts her cheek back down on my chest but not before I see her cheeks pink up again.

"Sid, it's just that, oh crap, can we just change the subject?"

"No Anna. Now I'm really worried."

"Ok, fine. God, I'm so embarrassed. Look, Sid, I've um" she pauses again but this time I wait for her to continue. "I don't have a lot of experience."

Experience? With what? Oh, experience.

"Oh" I say. Great response, idiot. "You said that you weren't a virgin, right?"

"I wasn't a virgin but I've only been with one other guy Sid."

She tilts her face further into my chest clearly embarrassed with our conversation. It's starting to embarrass me that I've caused this but we're talking about it so might as well keep going.

"Oh" I say, again. Brilliant. "I never would have thought that" I tell her. Maybe I should just stop talking.

"You did notice because you asked why I was embarrassed."

This conversation is not going the way I anticipated at all. How do I get out of this now that I've started it?

"I meant that, um, by the way you" I stop. "Ok, can we just change the subject?"

Now she tilts her head up again.

"You brought it up!" she tells me.

"I just wanted to make sure that I didn't do anything wrong or something. I mean after our first time" I stop. I suddenly remember something that she just said a few moments ago. "You just said 'it was wonderful this time.' What did you mean? What happened last time?"

She tries to turn away from me but this has become serious and we need to talk about it. I sit up against the headboard and she wraps the sheet more securely around herself and sits cross legged next to me. I've already seen her. Why is she covering up?

"Sid, last time was fine" she tells me.

"That's not 'wonderful' like this time. What happened?"

She shrugs a shoulder. "Sid, it's not a big deal."

"Tell me."

She lets out a long breath and says "fine. Last time you were very drunk, more so than I think we both realized, so it didn't quite go like it did today."

"You mean I didn't get it up?!" I say before my brain can catch up with my mouth.

Now I'm the one who is embarrassed.

"No, I mean yes, you were able to, um, get it up."

"Ok, so what then?"

She looks up, shuts her eyes and then says "it just didn't last very long."

Oh. Shit. Shit. Shit. I really try to make sure I take care of the girl I'm with but it sounds like Anna had to take care of herself that night.

"I'm so sorry Anna. God, it doesn't feel like there are enough apologies in the world." Then another stray thought comes into focus. "Anna, you're not the kind of girl who would have a one night hook up with a strange guy at a party. How did that happen? Why?"

She looks down at her hands where she is currently twisting them in her lap.

"Lauren brought me to that party because I was upset. The guy I was dating turned out to be a complete ass and only dating me for my family's connections. He was another good-on-paper guy that my mother loved of course. I caught him with my father's chief of staff's daughter. Anyway, I was really upset and tired of my life and who I am. You were sweet and funny. You didn't care that I didn't look like the other girls at the party, tall, skinny, gorgeous. We went somewhere to talk and one thing just led to another."

"If all of that happened, how could you possibly let me near you now? I mean, I was drunk, we had shitty sex and then I didn't even remember. Why are you here?"

She looks stunned at my question and then is quiet for a long time. Finally she answers me.

"I guess that there's something about you that pulls me to you. I don't know how to explain it" she says softly.

I'm surprised because that's how I've felt since that time in the elevator. For the first couple of days, I don't think that I even remembered her name but after I got to know her, I was drawn to her over and over.

The look on her face is so raw and completely stripped of any artifice. We were having a wonderful day and I had to bring up all of the old shit. I guess it is better that we've talked about it so there's nothing between us anymore. Nothing expect that sheet she's clinging to her chest.

I take the sheet and slowly tug. At first Anna is surprised but then, slowly, she releases it so that it slides down and reveals her body. God, she's gorgeous.

When the sheet is completely gone, I toss it aside and lean over Anna pushing her back so that she's lying on the bed with my body covering hers.

"What are you doing?"

"It seems to me that I owe you an orgasm."

"Oh Sid" she says and rolls her eyes.

"Hey, I pay my debts and it seems I left you hanging that time before. I need to fix that, now."

She starts to speak but I cut her off with my lips. At first hers are hesitant but they respond more and more the longer we kiss. Her arms circle my back and I can feel her fingers digging into my skin. It's a major turn on.

If she's as inexperienced as she says then I wonder what kind of sex she's had with that one boyfriend. I instantly hate the guy because he's the only other man in the world who has seen Anna like this although, maybe not exactly like this.

I kiss down her neck, licking and nipping lightly as I go. Anna's fingers dig deeper into my back and I get hard in response. She moans and sighs. Those noises go directly to my dick and I feel like I might explode. I replay video of the last game in my head to keep from sliding inside and taking her. This is for her.

I slide down her body and Anna's hands slide to my shoulders now. I lave at one nipple with my tongue and alternate between sucking and licking. I play with the other, rolling it between my fingers and massaging her breast with my palm. I switch sides and continue my ministrations. I can feel Anna's hips begin to rotate against my stomach. I'm coming to learn that this is her body's way of telling me she's getting wet.

I look up at Anna and her head is thrown back and she's biting her lip. Her face is flushed and periodically she moves her head from left to right. Fuck she's so hot. While I'm still watching her, I slide my hand down her stomach and between her legs. Fuck she's so wet. At first I tease and only slide my finger over her labia back and forth. She tries to push against my hand for more but my body is still half covering hers so she's unable to move.

"Sidney!" she cries out.

I don't make her wait any further. Instead I slide one finger inside and feel just how hot and wet she is. I slip another finger inside and the use both to lightly stretch and circle each wall. Her hips start to rotate slightly. I could easily make her cum but I don't want to do that with my fingers. With her inexperience, I wonder if that guy ever went down on her. I'm betting not. He was probably some ivy league, southern dilatant that didn't give a shit about her needs.

I kiss down her stomach and push her thighs wide. When I reach her pubic bone, I watch her head raise and her eyes open wide with shock. Yep, I'm right. That asshole never did this with her.

Since I'm almost at the edge of the bed, I slide completely off and pull Anna with me so that she's lined up for me directly at the edge. With her legs wide, I can focus on my main goal. I pull open her labia and see how excited she is. She's definitely wet and her clit is engorged. Awesome.

Thinking that I should take it slowly, I leave soft kisses over the inside of one thigh and then the other. She sighs, almost mews, so I continue. First, I leave a kiss directly on her clit. Anna responds with an "ohhhh". Her fingers dig into sheets.

Next I take her clit between my lips. Her hips shift quickly and she moans at the contact. She is so sensitive right now after our shower and theatre fun. I push using the flat of my tongue and her hips tilt up while she moans again. I feel it directly in my dick again. Fuck.

I would love to drag this out more but I don't think that I have the self-control for it. I might just cum like a teenager. Shifting slightly lower, I slide my tongue inside of her and my nose makes contact with her clit.

"Ahhhhhhhh" she calls out and moans again.

I swirl my tongue for a few moments and then go back to her clit. Her hips begin to rotate and one of her hands comes down on the top of my head. She fists my hair and holds me there. So she prefers having her clit played with. I wonder if she even notices that she's holding my head there.

Slowly I increase the speed of my movements; kissing, sucking, flicking. I move faster and faster and the nails of her hand in my hair dig into my scalp. Her hips rotate and push against my face until I she finally stops, I feel her legs tighten and her juice runs over my chin. The hand in my hair falls back onto the bed.

When I look up, Anna's eyes are closed and she is still except for her heavy breathing. Before joining her on the bed, I use the sheet to wipe my face then I climb up beside her. She's lying still and hasn't even opened her eyes.

"Are you ok?" I ask her softly.

"Um" is all she says.

"Um?"

She licks her lips and slowly turns her head so that she's facing me. Anna opens her eyes and blinks a few times before focusing. Her lips curve up into a beautiful smile.

"Hi" I say.

"Hi" she tells me. "I feel like I should say thank you."

She blushes as she says this and it's so fucking cute.

"It was my pleasure" I tell her. "Is my debt repaid?"

Now she frowns and says "Sid, there was nothing to repay. Please don't feel guilty about that night. It was what it was and it's behind us ok? Can we just stop talking about it?"

She looks serious and upset.

"Ok Anna. Of course, we'll put it behind us."

I slide up the bed and pull her with me. She lies in my arms and I pull up the sheet and blanket over us. I want to ask her one more thing although I'm hesitant to do so. Screw it.

"Is that the first time a guy has gone down on you?" I ask.

I can actually feel her blushing against my chest.

"Anna?"

"Yes" she says.

"Yes it's the first time or are you saying yes to my saying your name?"

She's quiet for a moment then says "yes to both."

I feel like a cave man but I take immense pride and pleasure that I was the first one. It makes me wonder what other firsts she wants to experience. This definitely has possibilities.