Have her straddle you

You kick off your black riding boots before taking a seat, the last thing you want is to have to struggle to get them off once you get started. Sally uses the opportunity of you bent over at the waist to peel the damp t-shirt off your torso and together you pull down your khakis and boxers. There is a moment of silence as she realizes just how large you are, but you see that same stubborn look of determination that you've come to admire.

Sitting on the couch you pull Sally towards you until she is straddling your knees. In this position her pink-tipped breasts are almost exactly at your mouth and you pull her forward just enough to take one into your mouth and suck on the puffy nipples.

"Oh My Godddd!" The pleasure she feels is evident as she digs her fingers into your short curly hair and pulls you tightly against her, it feels like she's trying to ram her tit down your throat. "That feels unbelievable." Thankfully, after the initial outburst, her tone drops to a hushed whisper of delight and you wonder if she is as conscious as you are about attracting attention, or maybe you're just lucky. After two or three minutes of sucking on her small tits and gently chewing on the hard nubs of her nipples, you pull her knees onto the couch so she is perched above you with your cock poking at her abdomen.

"I'm going to put my head inside you now, Honey." You tell her as you lift her into position and push the bulb against her dripping labia until it just barely slides into her virgin passage. "You can take as much or as little of my cock as you like."

"What?" She asks in surprise. "Like this, I thought you'd push it into me from above?"

"I told you Sally, I'm not going to fuck you." You murmur just loud enough for her to hear as you rub the juncture of your flesh and hers with your thumb. The ball of your thumb brushes her clit, playing with the hard little bump as she wiggles down a little more until you feel the restriction stopping your progress. This is, beyond any shadow of doubt, the tightest pussy you've ever felt stretched around your meat.

"Oww." She gasps as she lowers herself experimentally.

"You can stop here, Sweetheart." You murmur soothingly as your free hand rubs up and down her slender back and you continue to tease her pulsing clit.

"No." With her grit, she'd make a fine soldier. "Just let me get used to this." She rocks downward a few more times pressing herself onto you, each time wincing as her hymen stretches against your cock. The tightness of her cunt and the feeling of pressing against her like this is starting to take a toll on your self control, and for the first time you realize that this innocent virgin is almost certainly not taking the pill.

The first thing you should have done when you told Senator Williams that you'd take the job for the year is bough the biggest box of condoms you could find, but in spite of all he said - That train of thought is suddenly wiped from your mind as with a soft cry of pain the slender redhead lets herself drop onto your cock. You are still only half-way in, but she clings to your neck panting heavily.

"Oh God, that hurts." She gasps, "Are all men this big?"

"Shhhh," you whisper as if deflowering virgins is something that you do on a regular basis, "it will get better, I promise."