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Request from Tumblr: Reader is a very innocent guy when it comes to sex, he's never had an orgasm or even had a boner. He tells Jenna there's a weird feeling in his tummy and she finds his erection. She pulls him in her lap to cradle him and gives him a handjob with lots of praise and sweet words to comfort him and he cums all over his tummy. She gives him aftercare and he feels sleepy after his first ever orgasm and she gently rocks him to sleep whilst being cradled in her arms.
Disclaimer: Everyone in this story is above the age of 18.
You and Jenna were watching a movie when you start to feel... funny. She was in your lap, squirming as a result of a jumpscare on screen, when you felt yourself harden.
"Jen, stop." you groaned. You had never felt this way before.
"Oh, is that for me?" she teased.
Jenna turned to you, her brown eyes darkened and a glint of mischief in her eyes. "Do you want me to take care of that for you, sweetie?"You nodded, apprehensive. Jenna left the room and returned with a bottle in her hands.
Jenna gently pushed you onto your back and paused the movie. Jenna straddled your lower legs and pulled your sweatpants and boxers down.
"Don't worry, I'll take care of you." Jenna smirked.
"Jenna," you moaned as Jenna boldly reached inside your boxers and cupped your cock and balls in her hands.
Her warm, soft hands caressing and stroking your shaft while tugging on your swollen balls felt like utter bliss, causing your head to roll back into the pillow behind you. Jenna giggled and, torturously slow, stroked your shaft up and down a few times.
Without a word, Jenna slathered your cock with a copious amount of lube and resumed stroking you. Both hands stroked up and down his shaft, Jenna cooing with every upward stroke.
"Such a nice, big hard cock. I knew you would have a nice cock. So big, so hard. I want to see you pop. I want you to cum so hard you shoot ropes all over the island top."
Jenna's grip tightened, her strokes sped up, one hand working his shaft like she was milking him, the other rubbing all over the head of your cock. This went on for three more minutes, and Y/N's hips bucked up into her hand.
"Oh? Are you going to come for me, baby? Hmm? Go on. Cum. Cum for me, Y/N."
One of the hands rubbing your cock head dropped down to tug on your heavy, swollen balls, and Jenna's other hand became a blur stroking the shaft. You felt this tension, like your balls drew up all the way to your chest in preparation for spewing your cum, and black spots blurred your vision as you came with a roar.
"Jenna!," you moaned.
Jenna could tease you every day if she delivered pleasure that you experienced at the moment, all your pent-up frustrations flowing out of him through his cock, as Jenna kept stroking and tugging his cock and balls.
Jenna giggled. "I can feel your balls pulsing, and your cock twitching in my hand. Let it all out, baby. I've got you. I'll take care of you."
You shuddered, chest heaving, glad Jenna had you lay on the bed as your legs felt like jello. Several thick, long ropes of cum covered your stomach, and when your eyes met Jenna, she met your gaze while licking her cum-stained fingers.
"Delicious. Even your cum tastes amazing." You tried to sit up, but you collapsed back down.
"It's okay. I'll help you." Jenna helped you to your feet and to the shower. Once you were clean, the two of you went back to bed.
Jenna lay on top of you. You tried to keep your eyes open, but your body seemed to want to drift off.
"Goodnight, sleepyhead." Jenna whispered. She pressed a kiss to your forehead as you drifted off to sleep in her arms.
