A Bet is a Bet

Posted in: First Time Anal

They made a bet. If he lost, she got the privilege or bending him over and screwing him with a nice thick strap on, lube optional. If she lost, then he got to ravage her virgin ass. She lost and he was delighted.

“Be naked and waiting.” He texted her as he was heading home, but got no reply.

His cock was ready and eager. The foreskin had receded to reveal a fat purple head. He was so ready to bury it in a tight hot hole.

He entered his apartment and found it dark and silent. He kicked off his shoes and went upstairs. As soon as he opened the door to his bedroom he felt a hand grab his crotch.

He entered the dark room and relished the hand on his crotch. Any attention was welcome.

“Let’s get you out of those pants, big boy.” A quiet voice purred. His pants were unbuttoned and at his ankles before he knew it. His shorts soon followed. His cock was so happy to be free. It stood erect at attention.

“My girlfriend promised me that I could put it up her ass.” He muttered.

“Well, let’s come over to the bed and see if we can’t find your dick a nice hole .”

He allowed himself to be lead to his bed and lay down on his back. Pre-cum leaked from his piss slit and lubricated his purple head.

“You’re so big.” His girlfriend purred. She fisted his cock and slid the head up and down her pussy to coat it in her juices. She wanted him.

She lined up his cock with her virgin asshole and  gyrated her ass over it. Her sphincter clenches when the head pressed against her asshole,but she tried to relax and lower herself down. The head gained a centimeter and stopped. She wanted his cock up her ass even if her asshole didn’t want a blunt object in it.

“Thrust.” She told him.

He pushed his hips upward and she pushed out with her asshole. The head pierced her asshole a half inch and strained it. The fit would be tight. Her asshole was already protesting.

She fisted his cock and realized it was as thick as a soda can. She forced herself down on the thick cudgel,the head eager pushing pass her reluctant sphincter muscles. The tight ring of muscle clinched and protested, begging their owner to reconsider and not allow such a thick rod to pass. Their owner ignored the burning sensation and forced her asshole to open and accept the bulbous head.

It popped in suddenly. Her asshole clamped down just past the the fat head on the thick shaft.

It felt inhuman and she couldn’t suppress a scream.

“God, it hurts!” She screams.

He took over then thrusting another inch of thick shaft up her asshole.

“Stop!Stop! I changed my mind!” She cried, not knowing whether she really wanted her lover’s thick cock up her ass or not.

He changed position so that she was pinned to the bed under him then he withdrew his cock.

“Put it back in.” He commanded having enjoyed watching her feed his cock to her reluctant asshole.”A bet is a bet.”

She reached back and lined up his meaty cudgel with her asshole again. Her asshole had barely been stretched by the first penetration. She eased herself back against his cock,until she felt the head pressing against her hole then reached back to spread her cheeks and forced her hole to go back on his head. The tip entered her. She knew he was on point then and shoved her hips back. The fat head popped into her asshole for a second time. She screamed again. It hurt just as much as the first time.

He wasn’t satisfied and pulled his head from her asshole a second time.

She yelped. The retreat hurt just as much as the penetration.

He dried his cock on the bed covers and her asshole as well. He wanted to see how dry anal sex felt.

“Let’s see if you can get it in this time. I want at least 20 minutes of DRY anal.”

She loved him so much,but it just wouldn’t fit without any lube.

He must have had the same thought, because he wormed two fingers in her asshole and stretched it. Her hole would have to stretch SO wide to take him.

“Let me in. Take my cock up your ass for a third time.” He pressed the bone dry head against her asshole, but there was no give.

She ground her hips against him, trying her best to push out and accept his dry cock up her asshole.

He thrusted his hips forward,pinning the 18 year old fresh meat under him. It WAS going in her asshole,whether the tight ring of muscle agreed or not.  He thrusted his cock when he felt the slightest bit of give and succeeded in forcing half the head past the clenching muscles.

The burning pain was too much. She had promised her man a good fuck,but it was agonizing.

He shifted and tried a different angle,pushing his cock.

It worked, the rest of the purple head slipped past the resisting muscles and settled in her hot asshole.

She screamed and writhed, begged and pleaded then finally went limp.

He savored the tight feeling before shedding all restraint and pounding her virgin asshole for all it was worth!

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Rating: 7.2/10 (14 votes cast)
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Rating: +3 (from 5 votes)
A Bet is a Bet, 7.2 out of 10 based on 14 ratings

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