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Click hereContent warning: this story is between a cis woman and a trans man. If thats not your thing please move on. The trans man's "parts" are described in terms that could be seen as "female"
This story is a work of fiction and not based on anyone. All characters are above the age of 18.
Part 1
Samantha was fed up with James. They had been dating for 4 months and he hadn't made a move yet. She would have done it herself, but James was trans and she wasn't too sure how to approach it. She had stayed late at his apartment one night hoping that he would, but when she fell asleep on the couch, she woke up in his bed without James. He was sleeping on the couch out of respect. She appreciated the thought but she was horny. One day Samantha and James were watching T.V. at his place when it just came out:
"Why haven't we had sex yet?" samantha blurted out.
James looked over at her sheepishly.
"Well..." he began slowly. "There are two reasons. First, you know that I'm trans and I figured that there would be a conversation that I just kind of wasn't ready for yet. And second..." James looked down embarrassed.
"What?" asked Samantha. "There is nothing that you could say right now that is worse than what I am thinking."
James looked up at her then looked down and blurted out "I am really into BDSM and love to be dominated during sex"
A smile crept over Samantha's face. She loved to dominate people during sex. Samantha was bi and knew how to dominate men and women. With men she liked to see the power that she held over them and the need in their eyes as she was pegging them. But she preferred to fuck people with pussys finding them more fun. When James told her that she was trans she was thrilled to be able to dominate a trans man.
Sam looked over at James. Then got up without a word, took off her shirt and bra, and straddled James. When James opened his mouth to ask her a question, she put her nipple in his mouth and ordered him to suck. James was thrilled and surprised and obeyed happily.
With his mouth occupied, she took the opportunity to explain. "I love to dominate people during sex. It turns me on to be in control of another person's pleasure and to use their body for my own pleasure. We will have some conversations about boundaries and everything, but right now I just want to have sex with you."
Then she popped her nipple out of his mouth, got off him, and led him to the bedroom.
She pulled him close and eagerly kissed him and sucked his tongue into her mouth. The kiss left them both breathless and hungry for more.
Sam asked if he was comfortable being naked and when he nodded she ordered him to strip and lie down on his back on the bed. He naturally put his hands above his head and she smiled when she saw - he was a natural submissive and she loved it. She told him not to move his hands unless she told him otherwise.
Then she straddled his face and ordered him to make her cum with just his mouth.
He started with long slow licks up and down her slit. Getting maddeningly close but never touching her clit. He then circled her clit with his tongue still refusing to touch it. Then he plunged his tongue into her pussy as far as it would go and tongue fucked her. He managed to reach her g spot and tease it with his tongue. Sam was in heaven. This was the best oral she had ever received and she could feel the orgasm building. Her moans let James know that he was doing good. Her moans got louder. Suddenly Sam's pussy was empty and James' lips were wrapped around her clit. He sucked her clit and used his tongue to tease the end of it all at the same time. This pushed Sam over the edge and she came all over his face, harder than she had ever cum before. James did not stop sucking and Sam's orgasm seemed to last forever. When she was able to think again Sam ordered him to stop and she slowly got off him and laid down on top of him.
"Can I hold you?" James asked.
"Yes,you can move your hands," Sam replied.
James wrapped his arms around her and held her tight, pleased that he had been able to please her.
"As soon as I recover, it is your turn"
A few minutes later Sam had regained her composure and had enough blood in her brain to push herself up.
She started kissing James and he eagerly kissed her back.
"Arms back above your head" Sam ordered.
James quickly complied, eager for what was ahead.
Sam straddled his hips and started feeling around his chest.
"Do you have any feeling in your nipples?" she asked. Sam Knew that James had top surgery a few years ago but he hasn't told her any specifics.
"Not really. Sometimes if you pinch them hard enough there is some pain but thats all"
"Do you have a pump anywhere?" Sam asked.
"In the bag under the bed"
Sam got off James and hopped off the bed. In a bag she found all of James' toys. A few dildos, a few butt plugs, a collar, a blindfold, handcuffs, rope, lube, a sounding kit, a riding crop, a spreader bar, and the pump. She was pleasantly surprised with his collection, grabbed the pump and smiled as she knew that they would be returning to the rest of the contents of the bag soon.
She placed the suction cup over his left nipple and gently applied suction.
"Do you feel anything?"
James shook his head no.
Slightly disappointed, Sam took off the suction and bit down hard on his nipple. James jumped and she knew that he felt that.
"Are any of these toys off-limits?"
"No"
"Good"
Sam grabbed the collar and fastened it around James' neck. Then she picked up the riding crop. She started with a few gentle swats on his chest and stomach. Then moved down to his thighs and eventually landed a few blows directly on his crotch.
Sam placed a few of the dildos within arms reach of where she would be on the bed and straddled James again. She ordered him to suck her nipples again and was amazed at how good it felt. James was a master at alternating between sucking, biting, swirling his tongue around and it all felt so good.
Sam then laid down next to James and lowered herself so that she could reach his crotch, even being significantly shorter than him.
Her hand started on his chest and slowly slid down over his stomach and finally her destination.
"Is this OK?" she asked.
Sam wouldn't usually check in like this, but this was her first time with a trans man and she wanted to get it right.
James nodded eagerly hoping that she would continue.
She felt him between her fingers and asked "what should I call this?"
"My dick" James breathlessly replied.
Sam rolled his dick between her flingers feeling it stiffen between them. James let out a low guttural groan. It had been so long since he had been with a person who cared about his sexual needs like this. James had a high sex drive since being on testosterone and since his last girlfriend broke up with him 2 years ago, he had been using Grindr for hookups, but all of them there only cared about using him, cumming and a quick clean up.
Sam continued to play with James' dick and soon he was raising his hips to meet her fingers and whining whenever she took her hand away.
Sam's finger slid a little lower and her fingertips were at his entrance.
"What should I call this?" She asked.
"My boy pussy or my hole" James answered.
Sam nodded and then raised an eyebrow as if asking 'can I?'
James eagerly nodded and Sam slipped a finger into his boy pussy. She curled up to his special spot and he moaned "More".
Sam slid another finger into his sopping wet hole and James let out another groan "more"
Sam smiled and added a third finger to his boy pussy and started slowly finger fucking him. Sam knew from the size of the dildos that James could take more than just her three fingers, but she wanted to start slow and drag this out.
When James asked for more again Sam shook her head no.
James groaned "please mistress" and then his eyes shot open realizing that he had called her mistress without asking if it was ok. The smile on Sam's face made him relax as he knew that she was thrilled that he had slipped into his role as a sub so easily.
Sam said "not yet boy" and continued her pace with three fingers buried in James' boy pussy.
When Sam felt that James was putty in her hands she slowly pulled her fingers out and grabbed a dildo that was slightly larger and slammed it into James' hole resulting in James letting out a small scream. Sam left the dildo in as her fingers went to his asshole.
"Is this hole off limits?" she asked.
"All yours mistress."
Sam smiled and slowly slid in a finger that was already wet with James' juices into his ass. James relaxed instinctively and Sam slid another finger in. Sam reached over to the toys with her other hand and grabbed the lube and a butt plug. She slowly pulled her fingers, lubed up the plug, and worked it into his asshole. James let out another moan and his dick twitched at the new invader. Sam smiled pleased at how her actions were affecting James. She told James to close his legs so the dildo would not move.
Sam slowly started kissing James. She kissed his lips and then down to his neck. She made her way up to his ear and started nibbling. Then she kissed and licked her way down to his chest. She gave him hickeys all over his chest that she knew would be hidden by his shirt. Then she licked her way down his stomach. She pushed his legs open and finally arrived at his dick.
Sam slowly licked his dick and then took it into her mouth and sucked. Gently at first, then harder and harder. James started writing on the bed and had to grab onto the headboard to obey Sam's initial order of keeping his hands above his head. Sam kept up the pressure that she had on sucking his dick and slowly began to fuck his hole. The difference in sensations was driving James crazy. He spread his legs as wide as they would go and struggled to stay still. Sam made a note that she would have to tie him up next time.
Sam fucked him harder and harder with the dildo while sucking his dick. James was getting close to cumming. Sam used her other hand to grab the butt plug in James' ass and stretch him. That was enough to put James over the edge. Sam was pleasantly surprised that he squirted out of his dick and she was able to swallow some of him. She kept fucking him to prolong the orgasm.
When he was finally on the other side, Sam slid the dildo and butt plug out of him and threw them to the side. Then she moved up and held James. She told him how much she cared about him and was glad that she could make him feel so good. James buried his head in her boobs and told her how happy he was that she accepted all of him for who he was. Sam kissed him deeply and told James that she was thrilled that he was so submissive and they would be returning to his bag of toys very soon...
please keep writing!! i agree with the other comment that you can definitely slow down. I care less about the characters lol, but my horny brain would love if the sex was a bit slower. this is literally my dream scenario though, and I hope you keep writing (as a trans guy myself)
I loved how caring you made Sam. Only complaint I have is that you made two interesting characters and I want to know them better but it's rushed. You are a good writer so trust people will want to read more. Thanks for the story.