"On your back."

"For a little bit, but I'm telling you the truth when I say that that will give you hours of pleasure after the initial pain."

"Uh huh. How do you want me, Jeremy?" Courtney asked, looking back up at the big teen.

"I want you in a pretzel..." Jeremy said, then laughed at her suddenly confused expression, "I'm kidding. On your back I want to stare into your eyes as I make love to you."

Her mother smiled "Good choice. Take your bra off Courtney, then lay down on your bed."

Courtney got back up to her feet, and unclasped the front closing bra. Smiling at Jeremy she slowly drew the cups of away from her breasts, revealing them bit by bit.

Finally she shrugged out of the bra, letting it fall to the floor, and stood there bare breasted in front of Jeremy for the first time. "What do you think Jeremy? Are...are they like you dreamed about?" She asked him softly.

"They're better than all the dreams I've had of you." Jeremy answered, his tone one of awe.

Courtney smiled, though Jeremy wasn't sure if it was for the compliment or if it was for telling her he dreamed of her.

Courtney crawled onto the bed, catlike and rolled over with her head on her pillow. Her knees bent, legs slightly parted. Her mother laid down beside her, on her side.

Caitlin put an arm around her daughters shoulder and under her head. "Okay, Jeremy...take my beautiful daughter's panties off."

Jeremy nodded and reached out, his hands shaking a bit as he knew he was about to see something that no one has seen but Courtney. He took a quick calming breath as he gripped her panties and pulled them off of Courtney revealing her freshly shaved and glistening pussy to him.

Unable to resist he brought the panties up to his nose to get a whiff of the scent there, thoroughly enjoying it. "You smell great Courtney."

"Thank you." Courtney replied, her voice shaky from both her arousal along with a bit of nervousness.

Caitlin stroked her daughter's arm, "Take a breath baby and calm down. It'll only hurt for a couple of seconds. Jeremy, get her wet. Here I'll show you the best way to do it." Stunning both teens Caitlin reached down with her free arm and gently squeezed Courtney's pussy lips together. Caitlin's breath was hot on her daughter's cheek as she continued, "Now make believe you have to go to the bathroom and you need to hold it in. Only don't hold it. Squeeze and let go rapidly."

"Oh, you mean squeeze the Kegels? O...okay mommy. Today is definitely a day of firsts that's for sure." Courtney said her voice betraying some more nervousness.

"Again calm down baby. And just squeeze."

Courtney nodded and proceeded to work her nether muscles. With her lips together the flexing caused her clit to rub against the hood, sending waves of pleasure through her young body. "Oh my God, that...that feels great."

"Jeremy, a tip. That little bud is the clit. When you go down on her don't just go right to the clit." Caitlin now separated her daughters pussy lips and gently, oh so gently, ran her forefinger along the area just inside of her daughter's pussy, "This area right here is just as sensitive to pleasure. Use the flat of your tongue..."

"Thank you Mrs..."

"Call me mom. Period."

"Uh...this is kinda weird as it is...that would just really weird me out a bit more."

"Fine then, at least call me Caitlin. I don't need you making me feel old here."

"Okay, Caitlin. What I was going to say is Sharon pointed out a lot during our lesson a couple months back. Mind you always good to learn from experience." Jeremy said, then leaned and licked Courtney's pussy the taste of it sending a thrill through his body. That coupled with Courtney's shuddering moan damn near made him cream himself.

In seconds he was lapping away, a hand around each thigh separating them further so he could dig in as deep as he could.

Caitlin had withdrawn her hand and was using it to stroke her daughter's face, "Feels good doesn't it baby?"

"Yeah, it does. Feels so good. I never want him to stop, oh...oh so good." Courtney said, grinding her hips into Jeremy's face as he ate her out.

Caitlin nodded, "I know the feeling. Oh God do I know that feeling. It's especially great when there's love involved. A connection. There's nothing wrong with just sex, I just always enjoyed it better when there was something bore than just lust." Caitlin looked down to where Jeremy knelt lapping away at her daughter, "Jeremy gently stick your pinky in and then hold it up for me."

Jeremy nodded, figuring that she wanted to see how wet her daughter was. Jeremy unwrapped a hand and gently stuck his finger into Courtney's virgin pussy, only going into the first knuckle. Courtney gasped at the intrusion, but didn't pull away. He then raised his pinky up for her mother to see.

Caitlin made a face then got up off the bed. "Jeremy, keep licking her. I'm going to get some lube."

Jeremy nodded, "Not a problem, Caitlin. Not a problem at all." With that Jeremy dips his back down to Courtney's pussy, burying his tongue into her wet pussy, as Caitlin left the room.

Caitlin was back minutes later with a tube of lube. "Okay, I'm going to apply this here into you, baby girl, and then squirt it on your cock." Caitlin undid the top on the tube, and knelt down beside Jeremy. She spread her daughter's lips as she squirted the lube into her pussy. Gently she spread the lube around and into her daughter's pussy, Courtney gasping and cooing at the sensation. Though she wasn't rejecting her mother's touch, her mind was racing wondering why her mother would be doing this, and acting so nonchalantly about it as well. "Jeremy stand up." Caitlin said as she finished applying the lube to her daughter. Jeremy followed her orders, and Caitlin tugged his boxers down, causing his large cock to bounce free. Caitlin squirted more lube into her hand and then applied it to Jeremy's cock with a light touch.

Jeremy groaned at the sensation as Courtney lightly played with the lube in her pussy as she watched her mother give her new boyfriend (and life long friend) a hand job.

Satisfied with her work Caitlin stopped and got back on the bed taking up the same position as before, her arm cradling her daughter's head. "Okay, get on the bed Jeremy, and position yourself at her entrance."

Jeremy nodded, and did as he was told. With his head resting at the entrance to her virgin pussy.

"Ready baby? This is going to hurt for a second. Her take my hand, and squeeze when it hurts." Caitlin said and grabbed her daughter's hand. She then looked at Jeremy, "Okay, thrust in and stop."

Jeremy nodded, and looked at Courtney. Courtney stared at him for a second, then with a deep breath she nodded to him.

Jeremy pushed in hard, he felt some resistance that gave way with an almost audible pop.

"OH GOD! OH GOD...THAT HURT, OH THAT HURT..." Courtney shrieked as Jeremy buried himself into her and stopped. Tears rolled down her face, and she squeezed her mother's hand hard.

Jeremy stared into her pain filled eyes, feeling a little guilty, "I'm sorry."

Caitlin kissed her daughter's cheek, "It'll go away in a second. Here, let me help."

Courtney nodded and Caitlin reached down and gently rubbed the top of Courtney's smooth mound.

After a couple of seconds the pain started to subside and the feeling of Jeremy filling her up started to feel really good. That coupled with her mother's gentle fondling had Courtney's hips moving, begging Jeremy to start fucking her.

Caitlin looked up at Jeremy, "Okay, start slow."

Jeremy nodded again and withdrew his cock halfway before slowly thrusting in again. The feeling of her virginal flower squeezing he cock was almost overwhelming, and he wasn't sure how long he was going to last. Or where to cum.