Slowly and gently so she enjoys it as much as possible.

Since Christie is already lying naked on her back, and the last orgasm she just had has sapped her of what little strength she had when you laid her down, you decide that it would be best if you let her remain in that position.

You remove your clothes until you are as naked as she, placing them in the chair by her desk. By the time you are finished Christie has regained enough strength to be able to lift her head to look at you. You can see her looking at your totally erect cock with a little trepidation. You can almost see her muscles tightening. You are going to have to be careful if you don’t want to verify all the stories she’s heard about how painful her first time will be.

“Christie” you say walking back to the foot of the bed “I need you to do something for me”

“Yes Mr. Doe?” she asks.

You lean over and look in her eyes “I need you to trust me.” you say in a calming voice “and I need you to relax.”

“I do trust you, Mr. Doe. I do. But I can’t relax. I mean this is going to hurt. It’s supposed to hurt. You’re going to tear my hymen and I’m going to bleed and...” she’s beginning to work herself up.

“Stop” you say trying to be both firm and soothing. She stops talking and looks up at you. You can see she’s still afraid. “Listen.” you continue “It doesn’t have to hurt, although it might … a little, depending on a lot of things. How wet you are … although obviously that’s not a problem…” she giggles which is a good sign. “… how tight you are, but more than anything how tense you are. The reason girls feel pain and bleed the first time is that they think it will hurt, that it’s supposed to, so they tense up, making their pussy tighter and the man they are with thinks he is supposed to keep going and tear their hymens or just doesn’t care enough about them to stop when he knows he is hurting them. Thinking it should hurt is a self fulfilling prophecy which is why I’m trying to make you relax, because even though I sort of bribed you into letting me be your first I want you to enjoy it as much as possible.”

She keeps looking up at you and you can several emotions cross her face, shock, anger and then trust. “O.k. Mr. Doe” she says, “I’ll try to relax. I want my first time to be good too and I think I’ve chosen the right person to share it with… even if he did sort of bribe me.” She smiles impishly.

“Thank you?” You say “Anyway. I want you to close your eyes and concentrate on relaxing all you muscles, especially those in your pussy.”

She does as instructed, closing here eyes and gently breathing in and out. As she does you make sure she remains just aroused enough to keep her pussy wet. Slowly her body relaxes and a soft smile appears on her face.

“O.k.” you say taking the head of your rigid shaft and touching the opening to her warm, tight, womanhood. “I’m placing myself at your entrance. Do you feel me?”

“Yes Mr. Doe.” she whispers.

“Now tell me when you are ready. I’ll move inside slowly. You tell me if it starts to hurt and I’ll stop.”

“O.k. Mr. Doe. I’m ready.” she sighs.

You begin to enter her and her forehead immediately tenses again.

You stop. “Christie?”

“I’m sorry, Mr. Doe, it’s just so big and I’m still a little scared.”

“Maybe we should stop.” you say.

“NO!” she says opening her eyes and looking at you pleadingly. “Please! I’ll be good. I’ll relax. Please. I want this. I want it to be you.”

“O.k.” you say “Let’s try again. When you are ready.”

A few seconds later. “O.k. Mr. Doe. Keep going.”

You do, still going slowly. She is VERY tight but also, thankfully, VERY wet. You watch her face and judge when she needs a rest, stopping until she looks more relaxed before continuing, until you decide you have gone far enough for your first thrust.

“How does that feel?” you ask.

“Mmm … ah … It feels … It feels … awesome.” she says her face beaming “You’re really big … I can feel my pussy straining around you but … but it doesn’t actually hurt… it feels like … like … I don’t know but it feels wonderful. Mr. Doe. You feel wonderful. Keep going … I want to feel you … feel you fucking my tight little twat.”

“Open your eyes” you say and she does. You reach out and take your hands in hers and then look into her eyes as you slowly pull back and then push into her again, this time a little further but again making sure she isn’t being actually hurt. You keep doing this until she is able to take you entirely inside her and reward her with another orgasm, better than the other two. You really enjoy the look on her face as it happens and feeling the spasms of her cunt around the entirety of your shaft.

After that, once you are sure that she is used to the feeling of you moving inside her, you gradually quicken the pace, watching her eyes widen at the sensations you are creating inside her. However you eventually are unable to hold back your own orgasm. You are about to pull out when it occurs to you that you can use The Pen to make sure Christie doesn’t get pregnant. You therefore let yourself go, pouring you seed deep inside her, and giving her another powerful orgasm to match your own.

You lie atop her, bathing in the afterglow and the feel of her young, post coital body. “I’m so happy” she says “I thought sex would be painful and gross, but it’s beautiful. I love it and I love you for showing me how nice it is… don’t worry I’m not going to try to break your marriage up … still I would love if you could teach me some more …”