#705: Prostate Massage
Just when Josh thinks life can’t get any better, Rachel introduces him to butt play. They’re getting closer as they tread the line between regular hook up and relationship. But that doesn’t mean the sexual fire between them is waning. In fact, Rachel gives Josh his first prostate massage and opens up the door to even more
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Transcript
As Josh left Rachel’s house he couldn’t help smiling to himself. They had had an incredible brunch and finished it off with some amazing sex...the perfect Sunday really. He felt lucky to have met Rachel as she was his equal in all manner of ways. She was intelligent, career focused, good looking, kind, and a very sexual person. Most of the time her sex drive rivalled his, which of course, wasn’t a problem. He was getting the feels, and hoped she was too.
Josh and Rachel hadn’t had “the” conversation yet, to decide whether they were exclusive and he had a rule that he assumed, unless both parties decided to only see each other, that the other person was shagging other people. Josh didn’t think Rachel actually was, but he hadn’t yet asked her so it was still a possibility.
Although not keen to admit it, Josh hadn’t had sex with anyone else in a while. After he started seeing Rachel regularly he slowly stopped messaging the other women he would usually hook up with. He didn’t need them, he had her. Luckily they lived pretty close to one another which made unplanned sexy nights much easier.
At first, he made a point not to stay over at Rachel’s. He liked to distance himself from the women he slept with, not trusting himself, or them, to get too close. But he got sloppy with his rules and ended up staying one evening after a wild night out, passing out right after sex. He had woken up in the morning to Rachel handing him a big glass of water, paracetamol, and a cup of coffee. That was probably when he first realised that Rachel was a keeper.
Josh thought about how he might react if he found out Rachel was still sleeping with other people. He said “people” because he knew she considered herself bi-sexual, something Josh didn’t have a problem with. In fact, it excited him to think about Rachel with other women. Basic, he knew, but still, he loved that she was open to all types of people sexually and that she had explored so much. It was a big turn on. Perhaps one day he’d be able to experience that side of her.
God just thinking about it had Josh fantasising and he’d only just left her place. He had come home quite early to prep for his Monday personal training clients. But all he could think about was Rachel, her warm smile, round breasts, beautiful moist…. Okay Josh, he told himself, fucking stop thinking with your other head and concentrate. He sat down and planned his clients workouts for the day, hopped in the shower and headed to the gym, naughty thoughts of Rachel still bouncing around in his head.
As the days passed Josh started getting ancy, he hadn’t heard from Rachel all week. He assumed she was just busy with work, she was always working so tirelessly. But he also wanted to make sure that everything was okay with them so he sent her a quick message asking how her week was going. Josh had learned that there was no point in not reaching out to someone if he was unsure of the vibe between them, it was always better to clear everything up and communicate.
Rachel got back to him almost instantly and Josh let out a sign of relief. He was right, she had been busy with work but she also said she had been researching a little surprise for him. He cocked his eyebrow at this, she had just planned him an amazing brunch, he surely didn't deserve more?
Rachel told him it was nothing too big, but just something she had also been intrigued by herself. He had no idea what she was talking about and she wouldn’t even give him the smallest of hints. Damn, could she get any better? They decided to meet up that weekend, at Rachel’s place again.
By the time Saturday rolled around, Josh couldn’t wait to be off the gym floor and at Rachel’s apartment. As he said good-bye to his last client of the day he practically ran home. He jumped in the shower, trimmed himself up, and put on a spray of cologne before dashing out the door in his t-shirt and jeans. Rachel said it was a casual evening and they’d be staying at her place.
Josh brought a nice bottle of Bordeaux with him, knowing Rachel loved her deep velvety reds. Besides, it was the least he could do. When he arrived at the door he found it hard to hold himself back from kissing her right away. She was so beautiful in her loose black jeans and crop top, blond hair flowing to one side.
They cracked open the bottle of wine and sat on the couch sipping on two glasses, both smiling and chatting. After the first glass was done Rachel asked if Josh was relaxed. A bit of an odd question he thought but he told her he was.
Rachel ushered Josh upstairs and told him to get naked and lay down on her satin bed sheets. Josh complied, unsure of what was to come. She slowly undressed in front of him, showing off her delicate maroon lingerie. Nothing crazy fancy, but elegant and sexy. She told him to flip over onto his stomach and he looked over to see her squeezing massage oil onto her hands. Boy, thought Josh, he was a lucky guy.
Josh could feel himself getting hard into the bed. Rachel always turned him on so much. She placed her hands on his back and slowly rubbed the massage oil into his shoulders, up his neck, and slowly worked her way down his body to his buttocks. She pressed her hands into his muscular behind and started to knead her hands deep into him. Josh groaned with pleasure. Who knew a PG massage would feel so good, and be so arousing?
Then Josh felt Rachel tap the inside of his thighs, asking him to spread his legs. He did as she asked and then felt her soft hand cupping and stroking his balls- it felt great. Just like last Sunday, she handled his balls so well that his cock kept growing.
As she moved her hand away from his balls, Josh felt a warm sensation around his ass hole. Rachel had started putting some lube around his opening and gently lay her body over his and whispered in his ear if this was an okay surprise. Josh knew she was asking whether she could give him a prostate massage. Josh hadn’t explored too much of this kinda thing but he trusted Rachel and gave a gentle nod.
Rachel then moved her fingers between his checks, relaxing the area, and then she made her way over his anus, dripping massage oil onto it, making sure it was well lubed. She then gently probed the opening with her finger, inserting it ever so lightly inside. Again, she asked Josh how he was doing. He replied saying that it felt good and that she should keep going.
Rachel seemed happy with this answer and continued to push her finger inside of him. Josh was surprised by how turned on he was, it was a new and exciting feeling. Rachel reached down to cup his balls again whilst she continued to move her finger in and out of him. The two feelings were almost too much for Josh to bear, he let out a deep, animalistic groan and said Rachel’s name.
Rachel cooed at Josh to turn over so that he was laying on his back. He happily did as he was told, as it allowed his now rock hard cock to be free. Rachel gasped upon seeing it so stiff and upright and she took the opportunity to tease his head with her mouth, swirling around his tip, still inserting her fingers into his asshole. Josh couldn’t believe how fucking good it felt for Rachel to be inside of him like this.
She continued with the blowjob, slopping up and down his cock, sucking and sucking, and teasing his head. Rachel could feel Josh was ready to explode, but she wanted to make sure she was in control of it. She slowed down her bobbing head and steadily licked up his shaft and then, right as she put his cock down her throat again her finger full inside of Josh she pressed upward, right on his prostate gland. What Josh felt next was the most intense orgasm of his life. He yelled out in pleasure, unable to contain himself any longer. His cum sprayed out of his cock into her mouth, filling it so much that it dripped down the side, Rachel being unable to keep it all in.
But being the good girl she was, she licked him clean before settling into him on the bed. Josh told her how insanely amazing everything had felt and that it was one of the best surprises he had ever had. Rachel smiled up and kissed Josh, pulling him into her and they rolled around on the bed, preparing to play again.