Wait for Jessica in your room

You trudge up to your room exhausted and hear loud music coming from Nicole’s room. Clearly she expects Jessica’s visit just as much as you do. You strip down and change into sweatpants and t-shirt before watching reels on your phone to pass the time. Shortly after 10, when your parents are likely asleep you get a text from Jessica. “I’m coming over, help me in!” You and Jessica had lots of practice pulling her through your bedroom window over the years. You had offered many times to sneak into her room, but her house was smaller than yours. You had the advantage of your parents sleeping downstairs and Nicole always listening to loud music to cover your noises.

Jessica was dressed similarly to you, which wasn’t a surprise considering she knew she had to scale the veranda to get to your window sill. Not exactly something you want to do in a summer dress. After she was inside your room, she wrapped her arms around you and started kissing you, deeply and passionately. She always was a good kisser, it was part of the reason you had stayed together so long. Since it was so risky to have sex, doing other things became so much more important. She ground her petite 5’2” body against you and you could tell she knew you were getting hard. She was purposely pressing and shifting against your cock, bringing it to life. “Are you ready for your present?” Jessica moaned in your ear while she continued to wriggle against you. Fuck yes, you are. “Please…” you say to Jessica. “Good.” Jessica steps back to the middle of your bedroom. “Now close your eyes, and no peeking!” You like where this is going and dutifully shut your eyes while playfully covering them with your hands.

Barely a moment goes by with the slight russell of clothes before you hear Jessica’s voice. “Ok, open them…” You open your eyes to drink in the sight of your gorgeous girlfriend in the sexiest red lingerie you have ever seen. Red stockings held up by a garter belt frame a semi-sheer pair of red satin panties. A red lace bra with similar sheer material makes up the cups, hinting at the light pink colour of Jessica’s nipples. “You are fucking gorgeous” you manage to utter while you sit on the edge of your bed.

“I’m glad you like it” Jessica poses for you, showing off her toned teen body. “I’m going to treat my birthday boy tonight.” Then she drops to her knees and crawls towards you, her hands slide up your thighs and grab the waistband of your sweatpants. She tugs at them as you lift your hips off the bed so she can pull them all the way off. Your cock bounces as it escapes the elastic of your pants and Jessica giggles a little before looking up at you. She straights on her knees, taking a hair-tie from her wrist and making a quick ponytail.

She grabs your cock by the base and begins to suck and lick your balls. “I’m going to treat these especially well.” Jessica whispers between the sounds of licking and sucking. “I’m going to treat all of this….” Jessica takes a long, slow lick up the underside of your cock to the tip “so very well.” She finishes those words with her lips on the head of your cock before she takes you into her mouth. The heat from her mouth envelops your cock and you feel her tongue slide around the rim of your head. She only could ever take the head of your cock, but that was more than enough for you. You are already so close from the excitement at the strip club, and Jessica knows you well enough to notice.

“Don’t cum for me just yet. You haven’t had your full present yet.” Jessica leans back, reaches behind and undoes her bra clasp, letting her perky teen tits free from their lace prison. You had seen Jessica naked many times, but something about the lingerie made this especially erotic. Jessica rested between your knees, letting you calm down and come off the edge of coming while she looked up at you. “I can’t wait till you’ve had the procedure and I can finally feel this big cock in my cunt” Jessica gently grazes you with her fingers and your cock jumps. “But since we have to wait…there is one other way I can feel you inside me, besides my mouth.” She looks up at you slyly as realization spreads across your face.

Jessica lifts up a small bottle of lube she must have had in her pants pocket. She looks you in the eyes while she squirts out a liberal amount into her hands, using both hands to spread the oil up the length of your shaft. This was definitely new.

“Are you sure you're ready for this?” You ask, knowing she wouldn’t be offering if she wasn’t serious. Jessica reaches behind her and starts toying her asshole with the oil, spreading it and pushing it past her anus. She looks up at you, hunger in her eyes and her hot breath on your oiled up cock while she fingers her ass. “I want to feel your cum inside me, Ryan, and I can’t wait till you get the procedure…” Jessica stands up and turns around. Only now do you notice the red satin panties split at the back, leaving access to her ass. She backs up and grabs the base of your cock with one hand, lines it up to the tight oily hole of her ass.

She looks back at you and bites her lip before pressing down on you. At first, you don’t think you will be able to fit in, but she works you back and forth, whispering and moaning, “I want you inside me, I want you inside me” Until you grab her hips and pull her down onto you. You feel the tight ring of her ass open around the head of your cock and slide down your shaft as you enter her. She gasps and moans as she hovers half way down your cock, getting used to the sensation. Then with one deep breath, she lowers herself the rest of the way and moans again. “Fuck Ryan, you’re so big..”

Jessica slowly begins to rock and grind on you. The feeling is amazing and the tightness of her asshole ring grips the shaft of your cock as she moves. Jessica reaches down underneath the front of her panties and begins to massage her clit as you slowly fuck her ass. You watch as your shaft slowly pulls out and then pushes back into that tight little hole. Jessica’s breath gets faster and her moaning gets louder. You think to yourself, Nicole will definitely hear this. But you are too enthralled in the moment to care. You can tell Jessica is getting close to coming and the thought of her doing that while your cock fills her ass brings your right to the edge.

“Please cum in me, please cum in me” Jessica moans as the orgasm begins to take her. Your balls tighten and you grab her hips as you explode into her while she has a leg shaking orgasm in your lap. You reach up and grab her, leaning back and holding her on top of you while she trembles.

“Happy birthday” she murmurs as she rests against your chest.

Later, after you have both recovered, she puts her sweats back on and gingerly climbs back out the window. “Best birthday present ever” you whisper to her as you kiss her goodnight.

“I’m glad you liked it, I definitely did.” Jessica smirks before lowering herself down to the ground and heading back home. Jessica left the oil with you, “for next time” and you collapse on your bed.