It was decided that Dean would be in the back. Sam held Chalice but didn't enter her; he wanted her to focus on each new sensation one at a time. Dean lubricated his well-groomed fingers. He penetrated her with one, than another, until he felt her brown eye was warmed up and relaxed. Sam rubbed her clit until she was soaking, and then entered her. Dean smeared ample amounts of lubricant onto his member and performed the insertion as slowly and gently as he possibly could. Chalice was afraid it would hurt, but it was merely an odd new sensation. Dean pumped her softly.
She heard Dean gasp, and could feel him shivering behind her. He had never had this kind of sex with her and the sensation was even more intense than what had experienced with their previous lovemaking. Suddenly, like a wave, she could feel what Dean was feeling. She gasped and shuttered. A second later Sam yelled "Oh my God!" gasping and shivering.
"You can feel what I'm feeling, can't you?" Dean asked through clenched teeth.
"Yes. Can you feel what I'm feeling?" Chalice asked.
"Yes," both brothers answered through clenched teeth, realizing the three of them were psychically linked.
"Cas did not tell us that that was going to happen," said Sam.
"No he did not," said Dean.
The three of them lay there for a few seconds, perfectly still.
"Now I know what it feels like to have your dick in my ass, I'm scarred for life," Sam complained to Dean.
"Oh, really, because I've always wanted to know what it feels like TO FUCK MYSELF!" Dean responded, snarky as always.
"Oh God, this is my fault, I wish I knew how to stop it," Chalice cried. "It's actually starting to feel kind of good now, please, just concentrate on how good you make me feel…"
Sam and Dean realized that they would have to get over the greatest fear of the heterosexual male, which was experiencing anal sex, to be able to experience an amazing opportunity: knowing what sex feels like to a woman. They figured every guy had wondered that...does it feel better to a woman than a man, or does it hurt? Is she faking? What about multiple orgasms?
Plus they were feeling it through her, so it wasn't like they were doing each other.
Dean began to pump her even more softly than he had before as he stroked her hip and thigh. Her skin was so soft. He could feel her pleasure from his hand caressing her, from the warmth of his body behind her, his own soft warm skin. Sam began to pump her gently until he could gage what pleased her. The sensation of both of them inside her at once made her feel complete. They could feel her muscles squeezing them both. They were beginning to get into it. Too into it, Sam worried.
"Dean, don't blow your load…" Sam warned. "…and you neither," he said looking at Chalice.
"But you're hitting my G…" she moaned.
"I know," he sighed, "But we all have to get there at the exact same time, and we have to do this for 15 minutes."
"15 minutes! Why 15 minutes?" Dean demanded.
"Cas told us that, remember? Otherwise the spell won't work…"
"Who the hell said 15 minutes?"
"God! The cosmos! I don't freaking know! Just…remember tantric!"
"What!"
"Just…hold it in!" Sam commanded.
Dean let out a small moan then buried his face into the back of Chalice's head.
"Let's just take this really slow, and keep it steady," Sam instructed the others. Once the boys had their pacing synchronized, Sam and Chalice began to kiss. Dean buried his face in her hair. Feeling every sensation Chalice felt was incredible, intense, like nothing else they had ever felt before or would ever feel again. They could feel her love for them, her passion…she made each of them feel weak and strong at the same time, mighty yet powerless and free.
Three minutes went by. Chalice began to cry out, "Ohhhhhhh..Oh Sam! Ooooo…Oh Dean!"
Sam sighed. "I thought our lives were weird before..."
"Stop, don't make me laugh!" Dean begged.
A few more minutes passed. The boys were trying to ignore the sensation of the phantom penis in their rears, but the sensation began to affect their prostates. They weren't expecting to feel intense pleasure from this new unfamiliar source. Women, lacking a prostate, were at a disadvantage at enjoying anal sex…but now Chalice could feel it too, in stereo. All three bodies broke out in sweat. The rapture of one became the rapture of the three and was magnified exponentially. This was almost more pleasure than the human mind could process…but they continued.