Rakhi stroked his cock a little to make sure he was hard, as he wrestled with the condom packet. Once again, he had no idea what to do.
“I watched a video on this, Jack,” Rakhi said, and instructed him on how to put it on. Even though it was a ‘large’ size, it was still tight on him, and didn’t feel that comfortable. Jack didn’t complain though, as he really just wanted to get on with it.
Rakhi lay down on the bed and he got on top of her. She spread her legs around him and guided him in. Jack felt a little numb because of the condom, and he wasn’t sure if he was in, but saw Rakhi’s face, and she was grimacing as Jack pressed against her. He kept the pressure on, but was too overwhelmed and confused to know exactly what was happening. Jack’s dick was being squished a little, as if it was feeling resistance, and that didn’t feel right.
They carried on like this for a bit, and he looked at her. “Is it going in OK?” He asked her.
“I don’t know,” Rakhi said, and he heard a little cry in her voice.
“Did it hurt?” Jack asked her, mortified. She nodded at him, and he held her tight, pulling his dick away from her.
They both sat up a little, and Jack didn’t know if they were still virgins. It certainly hadn’t been this amazing pleasure experience like when they’d been making out. Jack saw some blood on the bed and was shocked. “Oh god!” He said and looked at her with a shocked face.
“Oh, that’s normal,” she said, and told him not to worry.
“I’m sorry if I hurt you,” Jack told her.
“You didn’t. It’s fine. I mean, you’re big, and there’s never been anything up there before, so…” she said, then paused, and said, “Maybe kiss me there again, and get me ready, and we can try again.”
Jack felt a bit weird about it, with the blood, and the fact that he had no clue as to what to do, but went ahead. He kissed, nibbled and munched on her, and she responded a little, but there was no sign of the ‘big moment’ that he had hoped for.
“Let me know when you think you’re ready,” Jack said, and carried on like a trooper. Jack began to enjoy it. It was pretty wild. This beautiful young girl had her legs wrapped around him and he was kissing her most intimate spot. Wow! Even though it was actually pretty strange, Jack felt good and knew this was a big moment for him. She tapped him on the shoulder, and he went ahead and put on a second condom.
They tried again, and this time, it was clear that Jack was in, as he could feel her softness, but it was still snug. As Jack entered her, once again, his dick felt like it had hit a wall, and was squashed, although he wasn’t in all the way. It felt uncomfortable, but he was more concerned with her being in pain. Jack didn’t give her any hefty thrusts, but put some pressure on, but he still didn’t think they were doing it right.
Jack backed off and looked at Rakhi. “You OK?” He asked her. She took a deep breath.
“Yeah, I’m OK,” she replied. “Can we take a break?”
“Of course,” Jack said and cuddled up next to her. He hadn’t known what to expect from a first time but it certainly wasn’t this. He didn’t care about not ejaculating, but he didn’t think it would be traumatic. Rakhi got out of bed, put on her shirt and panties and left.
“I’ll be right back, Jack,” she said, and Jack wondered if he’d blown it with her. Jack felt terrible, like he’d done it wrong and she hated him. Maybe he wouldn’t get another chance with a girl again for a long time. Jack lay back on the bed and cursed to himself, then put on his briefs and went to see if she was OK.
Jack went into the living room and saw Rakhi and Jini on the couch, talking. He went to see Urgo. He wasn’t known for his shoulder to cry on, but Jack thought he’d give it a go. He was in his bedroom, drinking a can of beer.
“Hey,” Jack said, sitting on the floor.
“Sup duder,” he said.
“So…”
“So…?” Urgo replied.
“I just busted her cherry,” Jack said, and Urgo’s eyes went wide. He high-fived him, but he didn’t feel like celebrating.
“I don’t think it went so well,” Jack told him, looking for guidance. He just shrugged, and Jack didn’t know what to say. At that moment, Jini and Rakhi, came in and he felt sick with worry that he’d fucked it all up.
But Rakhi sat on his knee and put her arms around him, so he knew it would be ok, at least for now. Jack kissed her sweetly. She looked at Jini and smiled, then they went back to their room. They got under the covers and cuddled up.
“You were lovely, thank you for being nice to me,” Rakhi said, and he could tell she was feeling vulnerable.
“Is there anything I can do?”
“No. I think you’ve done enough for one day,” Rakhi replied and they both laughed softly. “Just hold me and go to sleep,” she added, and Jack knew it was her way of saying she was done for the night.
