Jessie
Saturday night…
“Wha…?” Jason mumbled as he sat up.
Naked, Jessie had just then lifted the blanket covering the young man up and had knelt on the couch with one knee when he’d jolted awake, startling her.
“It’s me,” she said quietly.
“Jessie?” he stammered.
“Yep!” she confirmed happily and moved to straddle him. As she did so, she noticed that he was still wearing his boxers.
“What are you doing here?” He was still waking up, judging from the tone of his voice and slurred speech.
She giggled and put both hands flat on his shoulders, pushing him back down to the couch. Leaning down, she kissed him briefly then focused on working his underwear off with one hand. As she did so, she felt his heart beating rapidly against his chest, her other hand easily picking up the sensation as it rested on his chest.
“What… uh… what are we doing?” he stammered.
“Fucking!” she said simply. “My boyfriend told me that I could help you lose your cherry when he was fucking me earlier today. I’m thinking that now is as good a time as any since you’re leaving for home tomorrow.”
His heart started to beat even faster against her palm, and a nervous smile came to his face that she could see even in the dim light of the den.
“Oh honey,” she commented, “you’re so nervous!”
She leaned back down to kiss him again as her hand began to stroke his swiftly swelling cock. He still had his arms pulled away from her and didn’t seem to want to use them to do anything to her.
“Wait,” he mumbled.
She stopped kissing him and fixed him with a stern gaze as she looked down.
“Don’t you want to have sex and not be a virgin anymore?” she asked quietly.
“I just… don’t know what I’m doing,” he replied.
“That’s okay,” she assured him, affectionately stroking his chest with one hand and his cock with her other. “I’m not going to be grading your performance, silly! This is my way of letting you get some practice in.”
She slid back off of him then, her hands reaching for his as she moved onto her back on top of his crumpled-up blanket. He followed silently, but she could clearly see his hands shaking from nervousness.
“You’re not going to do anything wrong, Jason,” she said, trying to sound reassuring. “Try not to be so nervous, okay? Don’t think about how you’re supposed to do it correctly and just do what comes naturally to you.”
She pulled him from his kneeling position down to one with him laying on top of her. His cock was as hard as could be and nuzzled her cleft happily.
“Just take your time,” she said, and gave him an encouraging nod. “Always be gentle when you enter a girl the first time, especially if she’s a virgin. It can be painful if you rush things.”
He nodded at her, then moved to a kneeling position and looked down.
“Do… I uh… need to… lick…” he stammered
She smiled and shook her head. “I appreciate the thought, but I’m already wet and ready for you sweetie. You can feel it if you like.”
He nodded and she watched as he reached down between her legs and tentatively ran his fingers through her slit and briefly inside. His smile confirmed what she’d said and he pulled his hand free, wiping it on part of the blanket beside him.
She watched him reached down and take a hold of his dick, then lean over her and prop himself up with his other arm, still looking down between them.
“Look up at me,” she said, and smiled as his eyes fixed on hers. “Men and women are made to fit together,” she said. “You’ll be able to find where it goes.”
He chuckled quietly, finally showing some signs of calming down.
“In fact, lay down on me,” she ordered, gently pulling at his waist with both hands.
“I don’t want to squash you,” he said, concern clear in his expression as he briefly resisted.
She snickered quietly and pulled again. “Just don’t put all your weight on me.”
He nodded and lowered himself down on top of her, the weigh growing until she smiled and nodded at his questioning stare. He was still awkwardly holding his hips up though, as if he was worried about hurting one of them.
“Whenever you’re ready, sugar,” she said sweetly.
He took a deep breath and hesitated. She was about to whisper some more encouragement when she felt his hips lowering and felt his cock nuzzling her pussy again. He thrust slowly, his cock sliding up her slit and away from where it was supposed to be going. She wasn’t going to correct him though, knowing that it would do him good to find it for himself. He frowned and slid back again, and she smiled up at him as he closed his eyes.
After a few more tries, he finally pushed tentatively inside.
“OhmyfuckingGod!” he whispered and groaned as she watched him with amused fascination.
He pushed completely in, and she sighed happily as she felt the modest size of his cock inside her. She kept still though, letting him take his time to enjoy the sensations.
He moaned weakly as he began to slowly withdraw, then thrust. Exactly four slow thrusts later, she heard him groan weakly and felt his cock pumping its warm contents deep inside her. She smiled, caressing his arms and back as he grunted and thrust uncontrollably against her a few more times.
With a low moan he thrust a final time and held still, a smile coming to his face as he opened his eyes and looked down at her. She returned his grin and giggled briefly.
“Congratulations,” she told him.
“Wow…” he muttered, laughing briefly. “That was… wow.”
She continued to watch him quietly, happy that he’d enjoyed it so much. He continued to hold himself in the same position and she was enjoying the feeling of his erection still nestled inside. He closed his eyes again, his smile growing before he opened them again and looked back down.
“Sorry… that I came so quick,” he said.
“No apology necessary,” she assured him. “Your first time is supposed to be quick!”
He nodded, his smile returning. She felt him start to move to extract himself from her, but she stopped him by pulling at his waist with both hands once again.
“You know, you’re still inside me and still hard, this is technically still the first time. Dex told me that I could only take your cherry and rarely lets anyone else but him have my pussy. So…”
He looked down at her, the nervous, hesitant expression returning.
“So,” she continued, “if you want to keep going, you can. I just won’t be able to have sex with you again before talking with Dex if you stop now.”
He smiled widely and paused for a moment of silent contemplation then nodded.
“I… kinda want to feel… what its like when a girl… cums,” he said hesitantly.
She giggled and nodded. “Well, start pounding your cock into my pussy and you’ll find out, handsome!”
He blushed in the dim light, and she giggled at the endearing sight.
“Are there any other positions you’d like to try?” she asked, smiling sweetly at him.
He looked briefly confused then shrugged. “I don’t know many,” he said.
“Here,” she told him. “This is a good way to get me to orgasm. Lay back.”
Moving in time with him, she felt him briefly slide from her pussy as he moved onto his back again. She followed, sliding on top and pulling his shaft back inside before he realized what she was doing.
Slowly, she began to grind back and forth of him, her hips gyrating forward and back and dragging her pussy up and down his hardness. He didn’t seem to know what to do with his hands, so she reached down and pulled them up to her breasts. From that point, he happily played with her orbs, squeezing and kneading them and tenderly pinching her nipples.
After a few minutes, she was able to grind a nice, comfortable orgasm out as he watched and played. It seemed that the sight of her cumming was highly arousing for him and as she slowed, he took a deep breath.
“Close?” she asked, drawing a quick but vigorous nod. “You can keep fucking me like this if you like…” she said, but then groaned as she felt him thrust weakly against her, his cock pumping once again inside her. “Oh… fuck,” she whimpered, closing her eyes as the delightful sensations of his warm cum filling her swamped her senses. “That’s it, baby,” she whispered.
A few seconds later he ceased thrusting and fell still, breathing heavily.
Taking a few seconds to recover herself, she held her position and simply watched him.
“All good?” she asked quietly, smiling as he looked up at her and grinned.
“Thank you so much,” he said. “That was awesome! I can’t believe how good it all felt.”
She snickered at him, then gave him a final kiss before he began to get up.
“I’m gonna go clean myself up,” he said. “Thanks again Jessie.”
She smiled happily and waved at him in the dim light, then watched as he left the room. With a contented sigh, she stood and gathered her clothes back up, then went to try and find a place she could sleep.
Making her way upstairs, she opened the door to Jack’s room, thinking she could just crash there and not disturb Dex and Donna, but John was snoring loudly, sprawled out on the bed. From there, she peeked into Dex’s room, thinking that maybe she could slip in and maybe they wouldn’t notice. Her boyfriend’s bed wasn’t all that big to begin with, though, and already had two people in it.
As quietly as she could, she stepped back out and shut the door, then turned and looked down at Don’s room. The lamp was still on, and she could clearly see his bed was empty.
“He won’t mind,” she said with a shrug, and walked quickly toward it.
Tossing her clothes to the floor beside the bed, she slipped in and pulled the covers over. It proved to be too hot after a few minutes, though, and she kicked them off. The last amusing thought she had before she drifted off to sleep was what Don would do if he came home and saw her laying naked in his bed.