Day 27 Orgasm 31(Pegging Gang Bang) (Unrelated to actual participants)

He sat in the middle of his girlfriend and 3 other women on the king size hotel bed, and hoped he hadn't bitten off more than he could chew. They were all wearing strap-ons, every one of them. They had already figured out the order of who would fuck him when. Partly it had to do with the size of their toys. He'd given them his upper size limit and left the rest of the details to them.

He'd had this fantasy for so long! A pegging gang bang. Women fucking his ass for hours, one after the other. When one got tired, another would take her place. And it was finally happening!

They'd spent the last hour getting naked, sharing a bottle of champagne, donning their strap-ons and teasing him with kisses and hands on him everywhere. His girlfriend and one other woman had smaller toys in their strap-ons, and the other two women had larger toys.

His girlfriend had the privilege of fucking him first, and wanted him tied down. She liked it when he couldn't move while she fucked him. They each took a wrist or ankle and secured him face down with the under-the-bed restraint system. These women had thought of everything! His legs were spread far apart, and the vulnerability of feeling so wide open was thrilling. They put pillows under his hips, raising his ass up to be used and abused.

When his girlfriend marked the beginning of his fantasy by sliding her toy to the hilt into his ass, he was beside himself with excitement. He was the kind of guy that could keep having orgasm after orgasm while being pegged. His record was 8. He'd never actually tested how long he could keep that up and how many orgasms he could have. His girlfriend always tired out, but with 4 women, who knew how long he could keep going!

The first orgasm usually took him about 15 minutes. His girlfriend grew tired and tapped out to be replaced by her partner on the small cock team. He could feel it building slowly, but the second woman stopped just shy of letting him come. She'd played with him before and knew his signs. She didn't want him to come yet, preferring to tease him for a bit. But she did want to be the one who gave him his first orgasm of the night. Laying on top of him, motionless, she thrust into him once in a while, keeping his ass happy and wanting more.

Finally she sped up and hit a short and fast rhythm that sent him moaning and thrashing against his restraints, spilling come all over the bed. Everyone cheered and one of the other women put a hash mark on the piece of paper by the bedside. Oh yes, they were keeping track for him.

His girlfriend wanted his ass again, inspired by watching him come, and wanting to see if she could give him a repeat. She loved being at the end of the cock that sent him over the edge and made him moan and thrash. She loved watching him strain against the restraints when he came, and wanted to feel him do that underneath her.

About 7 minutes later he told her he was going to come again. She started fucking him hard and fast with what was left of her energy. He did a lot more than moaned when he came that time. He roared with pleasure and over-stimulation when she refused to stop, reminding him with her sweet but insistent voice in his ear that this is what he wanted, right? To be used over and over again for their pleasure. She had her own orgasm from the excitement of that moment, and again tapped out. Another hash mark for his orgasm was placed on the paper.

Team big cock came into play, and they were ready. They flipped him over, his ass up on the pillows and let his limbs free. One of them kissed him and played with his nipples relentlessly while her partner slowly pushed into his ass. He took her bigger toy, no problem. After 2 orgasms it was a piece of cake, and a very delicious one at that.

He held his legs up for her, and she fucked him slowly, pulling her cock all the way out and then guiding it back into his ass. She made him feel the thrill of the head clearing his sphincter each time. Then she sank it into him as far as she could, pushing into him further when it was already in to the hilt. Over and over again, the same pattern. It was driving him insane with the measured pace. Not quite enough to come, but totally up to her; not his decision.

Finally she roughly pulled him over and up onto his knees and began fucking him faster, pulling him into her with his hips. Oh this would get him there. He came again, announcing it for the woman keeping track with the paper. He made so much noise when he came each time and they commented on that, all saying how they loved it. The other big cock woman took over and pushed him down on the bed, onto his side. She spooned him and fucked him from behind, holding him against her firmly. This woman was athletic. She was like an unstoppable machine and fucked him through another 3 orgasms in quick succession.

Her partner took over again after that and put him on his stomach again. He was warmed up now. It was easier to make him orgasm, so she took great delight in perfecting the technique of making him come over and over. Short and quick strokes at just the right angle. He held his hand up every time he had another, because at this point he could barely speak. Team small cock cheered with every successive orgasm and put down another hash mark. It all became a blur to him after that. There were times when he thought that he couldn't stand any more pleasure, only to prove himself wrong as he peaked again and thrilled to the sensation.

Finally he called a stop to the fun because his ass was getting too sore. He was trembling and shaking...and smiling. He wasn't in full control of his body and he didn't care. He was exhausted.

"I'm done, ladies." That was the agreed upon phrase that would end the gang bang.

His girlfriend stayed with him, cuddling him while the others packed up. They brought warm washcloths and cleaned him up. Then they all helped him get into the other king bed that was still clean. He snuggled between the covers and fell asleep almost instantly.

The women all high-fived each other quietly and moved to the other end of the large suite, where they shared another bottle of champagne. They drank to a successful gang bang, and to making fantasies come true. They talked about how hot the experience was, how much they had enjoyed it, and how a couple of them would love to receive the same treatment someday.

His girlfriend climbed in bed with him after the other women left.  She had clearly been inspired to make this man's dreams come true. One down, after tonight.

He woke the next morning early, with a very empty stomach. He'd slept through dinnertime and now it was 5am. His girlfriend snored softly next to him. The beginnings of dawn had begun to light up the sky.

He closed his eyes again and took stock of his body. He clenched his ass and felt the soreness. Nothing serious, it would be gone in a day. His stomach muscles were sore from all the spasms, and he still felt tired.

Suddenly his eyes flew open and he reached over to the bedside table, grabbing up the piece of paper. His eyes focused and he began counting the hash marks, the groups of 5.

Good Lord.


He laughed softly, had a moment of feeling incredibly grateful for his life, closed his eyes and went back to sleep.

19 Responses

  1. Fantastic story and well sought fantasy! Not much detail on the size, but I found myself hoping for some struggle to take the largest one or maybe one larger than he anticipated (with consent, of course).

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