The first time my future wife, Anne, had anal sex it was…uncomfortable.
She was with her friends, Jane and Emma, in Jane’s basement bedroom along with Jane’s boyfriend Ed. They were gossiping about a girl they knew who’d let her boyfriend fuck her ass. Jane was disgusted. She couldn’t understand how anyone could enjoy it.
Anne, who thought of herself as kinky but who hadn’t really experienced all that much, was indignant. She defended the poor maligned girl and the entire concept of anal sex. Unfortunately for Anne Emma liked to push boundaries. She kept challenging Anne, demanding to know how far Anne had gone, why Anne thought anal sex would be nice, whether Anne herself would do it. Anne kept making bolder and bolder statements, while Jane got more and more disgusted. Finally Emma asked a question that shocked them all.
“Would you let Ed fuck you up the ass? Right now?” Emma had a huge grin on her face. Jane gasped in shock. “Jane will, obviously, never let him, so it’s not cheating. If it would be so great, prove it.”
Anne was taken aback. She’d been vigorously defending anal sex as something that could be pleasurable. She’d been trying to put on a bold and confident front about her sexuality and she’d, in all honesty, she’d been trying to shame Jane. She was also extremely horny, both from the proceeding conversation and the shocking suggestion.
“Well, of course I would.” She tried to sound sure of herself. “But, clearly, Jane would never agree to that. She’s too disgusted by the idea.” Both girls looked at Jane. Ed tried to stay as quiet as possible. Jane looked deeply uncomfortable.
“Fine.” She blurted. “Go ahead. He’s never getting my ass. Might as well have yours.”
“Fine” Anne retorted. It absolutely wasn’t what Anne wanted, but she wasn’t about to back down. She abruptly bent over the end of the bed and pulled her pants down. Just a little. Just enough to expose her ass. It was a sudden movement and her friends were shocked. They weren’t expecting her to actually do it. They certainly weren’t expecting that they would watch.
“What are you doing?” Jane asked. She was obviously very uncomfortable with the turn of events.
“I want you to see how nice it can be.” Anne responded smugly. She was just as uncomfortable as Jane, but she didn’t want it show. She wanted her friends to believe that she was absolutely confident in her sexuality. She looked back at Ed. “What do you say Ed? Limited time offer.”
Ed looked at Jane. Jane hesitated until Emma nudged her.
“Fine.” It was a whisper.
Anne bent over more, pressing her chest in to the bed. She reached back and spread her cheeks. In a strange gesture of modesty she pulled a blanket over her back so that her friends could see almost nothing. Her ass was open, but only to Ed. She tensed as she heard Ed moving towards her. She had no idea what to expect.
When Ed thrust in to Anne’s ass it was like a rod of pure fire. He went in dry, hard and deep. He tore at her tender flesh and she screamed in agony. Her fist clenched the bed covers and a sob caught in her throat. It was nothing like Anne had expected
When he pulled out, it wasn’t a respite. it hurt as much as going in had and was followed by another long hard stab deep inside her. It was harder, faster and more painful than anything Anne had imagined. Anne looked up at her friends. Emma was fascinated by the brutal fucking. Jane had a twisted little smile. She was happy to see Anne suffer.
Ed was oblivious to Anne’s pain, or just didn’t care. He pulled out and rammed into her again. It hurt. It hurt a lot. But Anne wasn’t going to let Jane know that. She turned her grunt of pain into a moan of pleasure. Jane’s smile wavered.
When Ed pulled out Anne faked a whimper of desire. When he thrust into her again she let out a long groan, ending with a whispered. “Yes.”
Uncertainty crept across Jane’s face. Anne escalated her moaning. Fire felt like it was radiating from her ass, Ed’s cock felt like it was tearing her, but Anne gave no sign. Instead she started to beg.
“Please, Ed. Please.” Jane’s face was red with fury.
“Harder, Ed. Fill my ass.” Anne hated every thrust but taunting and tormenting her friend brought its own pleasure. She begged. She pleaded. She panted and shouted. She channeled her pain and humiliation into an erotic performance. Ed picked up speed, grabbing her waist. He started to whisper Anne’s name.
Emma leaned forward. Sitting at the head of the bed the girls couldn’t see much of what was happening. The blanket blocked even more.
Jane looked like she was about to stand, to call a halt. Anne prayed that she would. The pain was intense. She didn’t know how long she could last.
“Own my ass Ed. Make my ass yours.”
With that Ed exploded. He thrust forward hard and Anne screamed. He stayed deep inside her while he finished, then collapsed on her back, driving her to the bed.
“That was amazing.” He whispered. “You’re amazing. That was the greatest thing I’ve ever felt.”
Anne smiled as Jane suddenly go up and stomped out of the room. It has been an ordeal, but worth it
Source: reddit.com/r/eroticliterature/comments/w3b0xy/uncomfortable_first_anal_fmf