This is my story and is also posted elsewhere.
*****
She knelt down next to his feet. He was sitting on the couch in his hotel room. It felt natural to take this position even though she only started chatting with him days earlier. She thought back to having first seen his profile, he checked the boxes of her "must haves." He was in his 40s, professional, and he noted that he was a writer. This intrigued her. She loved to read!
She asked if it was okay if she stroked his leg as they chatted. She thought about their first messages. He sent her a link to his profile and a list of his stories. She read one... And then another. He was dominant, forceful. His male characters had an edge. They knew what they wanted and they went after it. She just had to meet him.
He asked her about what she wanted that evening. He asked if it was okay that he touch her. She nodded enthusiastically. They discussed kinks, scenes, and limits. It was the most formal negotiation she had experienced prior to any play session. It helped her to feel at ease. She remembered his messages when she suggested meeting up. He discussed his potential plans for her while making sure she understood that her consent was crucial. He wanted her to feel comfortable. They talked about meeting in public first. They discussed the importance of making sure there was a connection and that neither felt unsafe.
In his room, they set up the toys that she brought. A butt plug, a stainless steel dildo, a wand, and a clit sucker. He picked up the butt plug, feeling the weight of it. He had a grin on his face knowing it would be a fun night. She was eager to get started. Typically the drive into the city would take under an hour, but traffic was an absolute nightmare. By the time they were getting to dinner, it was nearly 8. They each ordered a light dish, chatted about their life, kink, and their love of science.
Earlier in the day, over the app, they had a discussion around limits and expectations. They were in sync. It made meeting in person much easier. Once dinner had finished, he asked if she wanted to join him in his room. She asked if that was what he wanted. They were both excited but perhaps somewhat nervous about whether their connection would translate into a physical relationship.
"Take off your shirt," he ordered. His voice made her skin tingle. She loved his confidence. This is absolutely what she needed in her life.
"Yes, Sir," she replied. They were words she would say many times that night. She removed her shirt and put it on the floor beside the bed. He had her turn around facing away from him. He loved her black bra holding her amazing, large tits. He started to touch her shoulders, light touches, like a massage. Then he ran his nails over her back. Shivers ran down her spine. She desired him so badly, and finally feeling his touch made her senses come alive.
"May I remove your bra?" he asked. She was excited. She wanted to feel this man's hands on her body. She nodded and softly spoke in an affirmative. Hell, at that moment, he could practically do anything. He easily removed the bra and tossed it on top of her shirt. His lips touched her neck as he palmed her tits. His large hands felt amazing on her body. He knew exactly how to touch her. He had her remove her pants next, leaving her in only a pretty pair of black panties. He adored that she was wearing a matching set. She had come prepared for sex tonight.
He told her to face him and kneel. She was topless and he was still fully dressed in a collared shirt and jeans. He started to unbutton the top buttons of his shirt. She wanted to take off undo the rest of them. When his shirt was off, she kissed the skin just above his jeans, her hands touched his hairy chest. Her face nuzzled his already hard cock through his pants.
"Undo my belt," he commanded. She eagerly removed it, hoping he would let her remove his jeans next. Once again, they were on the same page. He told her to unbutton, unzip, and pull down his jeans. She did so, exposing his boxers and his hard cock. She wanted it so badly. She had told him how good she was at sucking cock. But first, she would need to earn it.
He had her kneel on the couch. The couch was directly next to the window. They were on the fifth floor. That was probably high enough that no one would see their kinky activities, he reasoned. He checked with his sub before opening the shades. She consented. He had her lean forward so that she was pressed against the back of the couch. He grabbed her tits like he owned them, placing her large breasts over the side of the couch.
"Look outside at the people walking by as I spank your ass!" He said as the first smack from his open hand landed on her ass. Soft moans came from her lips as he continued to smack her. The spanks became more intense. He varied the location, slightly, mainly focusing on her inner ass cheeks. But whether he hit once on the right before switching back to the left, or multiple times, she never knew. He also varied the pace.
"How are you feeling, slut?" He asked.
"Good," She replied. She liked that he checked in. She had expressed how much she needed to be spanked. She was starting to feel a calm coming over her. This was especially the case when he quickly spanked her hard over and over again in rapid succession. Those were the most intense moments, and also the time when she began to approach subspace. He was reaching about a 4 or 5 on her pain scale. He probably could have greatly increased that had he used his belt, but they hadn't negotiated that ahead of time.
He walked over to the toy collection and grabbed the metal butt plug. With only the tiniest amount of lube, he was able to insert the plug inside of her asshole. She clearly had previous experience with anal. She moaned as it went in, loving the fullness. As he spanked her, he pressed on the plug. The pressure of the plug in her ass felt amazing.