Two days later Jake and Eileen went out to eat again before heading to his apartment. He got them their usual drinks and they sat on the sofa, kissing between sips.

“The new Playroom is ready, so tonight we can try it for the first time. I wanted to ask if your period started, and if you've thought about how you want to please me?” he asked.

“Yes, it started yesterday. I've thought about what you said, that I should use any part of me except my pussy to have sex with you during my period, and I've decided I'll start with my hands.”

“That's a good choice. When we go to the Playroom, we can take your hand job skills for a test ride. But first, each time we go to the Playroom, I'll let you go a few minutes before me to get ready. You'll strip, place your clothes on the table by the wall, then stand naked in the middle of the room and wait for me.”

“Okay,” she said, mostly happy that he was okay with her idea of giving him a hand job.

“And remember the rules. No talking except "Yes, Master”, unless I give you permission to speak, and always do as I tell you,” he explained.

“Right. That's what I'll do,” she answered, happy to get started.

After finishing their drinks, he told her to go to the second bedroom which would now be their Playroom. On entering, Eileen saw a bed and a sort of massage table, though it looked a bit different than usual massage tables, with a padded step and cutout areas. There was also a table by the wall with some new items on it. She saw the usual lashes plus a new blindfold, but also a small paddle and some strap-like thing with a handle and fuzzy strands. Eileen was curious to explore the room further, but then remembered she was to strip and wait for him, so she undressed and put her clothes on the table.

When Jake entered a few minutes later, he found Eileen standing naked in the middle of the room, as instructed. He walked over and stood behind her, then placed his hands on her hips and ran them up and down her sides, over then under her arms, and eventually to her breasts. He caressed them gently, then cupped them, squeezed them a little, and ran his fingers over her nipples. She loved the feel as her nipples hardened in his hands. Her arousal began with a few minutes of pleasuring her breasts, which included a few pinches that hurt her nipples, followed by soothing caresses, which left her in the mood for whatever else he had planned. Then Jake stopped.

“I'll show you around our new Playroom,” he said as he walked her over to the massage table.

“We'll call this “The Table”. When I say go to The Table, you'll move to this end of it and kneel on these knee rests, then bend at the waist to lie on the table. Your head will fit into the round opening so your nose and mouth are free, and your breasts will fall into these side cutout areas. Let's try it so I can adjust the table to fit you.

“Yes, Master,” Eileen replied as she knelt on the padded knee rests, which she at first thought was a step, and bent at the hips to lay face down on the table.

Jake adjusted the length so her face fit the opening and her breasts fit, suspended, where there were side cutouts. The setup felt comfortable to Eileen.

“Okay, it fits you well. Let's head over to that step now,” Jake said.

“Yes, Master,” Eileen dutifully replied as she got off the Table and followed Jake.

He walked her over to a long and low step a few inches tall sitting on the floor near a corner, and she noticed there were lashes at its ends, and a hook hanging over it on the ceiling.

“This is The Step. When I say go to The Step, you'll get on this step and place your hands in front of you so I can put soft lashes on your wrists, and then I'll hang the lashes over that hook above. Your arms will be suspended above your head. Shall we try it to fit the height correctly?”

“Yes, Master.”

Jake then went to the table, picked up a pair of lashes connected by a strap, and brought them back to where Eileen stood on The Step, waiting. She put her hands in front of her and he put the lashes on her wrists, then lifted her hands and arms using the strap, and slipped the strap over the hook on the ceiling. Her arms were now suspended over her head. Jake checked her feet.

“Spread your legs,” he ordered.

“Yes, Master,” she replied as she spread her feet apart.

“Further.”

She spread them further, causing the strap to become almost taught since spreading lowered her height a bit. He loosened the strap just a bit, relieving any stress on her arms, then lashed her ankles to the ends of the step, and seemed pleased.

“It fits you perfectly,” he said. “When I play with you in this room, I will sometimes cause you some discomfort or pain for my pleasure, but I will always follow that with soothing. I hope you will always be happy to please me, and able to look past any pain and to the soothing,” he explained.

Then Jake unhooked Eileen, took the lashes off, and guided her to the bed.

“Please lie down on your back,” he told her.

“Yes, Master,” she replied as she lay on the bed.

“Here's a tube of KY Jelly and some tissue for you to use for my hand job, and I'll be lying alongside you and exploring you as you do me. Shall we begin?”

“Yes, Master,” she answered, a little uncertain of what was about to happen.

Then Jake took his clothes off and lay next to Eileen, but head to foot. With his penis already erect and just off her right hand, she realized what he had in mind. She squirted some jelly in her right hand and took it to his erect penis. Jake, having her pussy at his right hand, pushed her leg aside to open her up, and began to caress her slit up and down, causing her to squirm. He used his fingers to open her lips, caressing her wet pussy up and down, and swirling the nub of her clitoris as she began to rub his dick up and down. They were each enjoying the feelings that the other was giving them.

Eileen enhanced her grip by positioning her hand at the top of his penis, encircling its head, and tightening her fingers around it before sliding her hand down the length of his dick. He reacted by jerking his penis up to meet the focused pressure she was giving its head, and as she repeated the up and down movements, he was soon ready to climax.

In response, he sped up his swirls around and over her clit, causing her to wiggle and moan in excitement, to the point that she lost herself in the pleasure she was feeling and stopped pumping his dick. When that happened, Jake pinched one of her pussy lips very hard and she jerked in response to the unexpected pain. She quickly realized that she'd paused her part of this mutual satisfaction, and resumed her hand job.

Jake then comforted her by caressing the lip he'd pinched before he continued his diddling. Eileen noted his soothing caress, and his resumed clit play soon took her to the point of climax, ready to cum. They both continued to work each other and, sensing his pending release, she had a tissue ready to catch his spew when he came. She captured his spunk when he jerked repeatedly and shot his essence into the tissue she held over him. As soon as he had jerked the last of his ejaculate, she wiped his dick and put the tissue aside. Now it was her turn to tense and jerk, and she came from the pleasure his fingers had given her clit. They relaxed on the bed, both exhausted.

After a minute, he got up and helped her off the bed. They both cleaned up, got dressed, and left the Playroom for the sofa and another drink.

“So, how was your introduction to the Playroom?” he asked.

“It was wonderful!” she answered. “Did you like your hand job?” she asked.

“I loved it!” he answered. “You did very well!”

“Thanks. Sorry you had to pinch me to get me back to it... I got lost in the pleasure you were giving me. But thank you for the soothing that followed. Is that the kind of pain you mentioned I might have when you pleasure me?”

“That was just to get you to focus on what you were supposed to be doing. Other times I may give you some pain to make you more sensitive to the pleasure elsewhere, and a spank, tickle, or pinch can achieve that. It's to make you more appreciative of the good things I'll be doing. And it will please me that you'll endure the pain for me.”

“Okay. I guess I'll just have to experience it.”

They finished their drinks and Jake walked her home. After he left, Eileen wondered more about any pain she would feel in the Playroom. Would she be able to endure the pain to please him? Would the soothing he said he'd provide afterward be enough? Meanwhile, her period was still with her, so she had to decide how to satisfy Jake the next time they went to the Playroom. She'd never had anal sex but thought that might be the best thing to do next.

+ + +

Two evenings later, Jake took Eileen to a play, and they laughed through the entire performance of “Spam-a-Lot” at the local college. Neither had ever seen the old British “Monty Python” comedy on TV, but they got into their odd brand of humor and couldn't stop laughing. After walking back to Jake's place, they settled onto the sofa with wine and beer and talked.

“I'm so glad you liked the play,” Jake said.

“I can't remember when I've laughed so hard! Thank you for taking me, Jake,” she replied.

“Any time, Eileen. So, is your period still with you?”

“Yes. Almost done, by not quite.”

“And have you thought about what you'd like to do with me tonight?”

“Well, I'd like to try anal, if that's okay?”

“Sure. Have you done that before?”

“No, but I've seen it in a lot of porn, so I think it would be fun to try it.”

“Okay, then anal it is!”

They finished their drinks and he told her to go to the Playroom and get ready, so Eileen did. On entering, she took off her shoes, blouse, and skirt, followed by her bra and panties, and laid them on the small table. Naked, she moved to the center of the room and waited for him, wondering how the anal would feel and what else Jake might do with her.

Jake entered shortly after and smiled at her standing just where he had asked her to.

“Let's have you go to The Table,” he said.

“Yes, Master,” she replied and walked to the massage table, knelt on the knee pads, and laid face down on the table as he had instructed her. She settled her face into the round opening made for it, and her breasts fit, suspended, in the side cutouts.

Jake took his clothes off, got the KY Jelly and tissues, and went to her, placing the items in a bin at the table's side. Then he helped her move her knees to the side, spreading her legs and giving him easy access to her rear.

He reached down to her knees and began to slowly trace his fingers up her inner thighs, swirling as he went. Eileen loved the feel of it at first but soon found it to be quite ticklish, making her squirm. Jake teased her this way for a few minutes, causing her to become uncomfortable with the tickling, and waiting for him to stop. Soon he did stop, and then he rubbed her inner thighs firmly to remove the ticklish feel. Eileen thought it felt wonderful after the tickling he'd just done, and she wondered again if this was what he meant by always following any discomfort with comfort. If so, she liked it.

After he had massaged her, he slid his hand to her crotch and caressed her already wet pussy, tracing his fingers up her slit to her clitoris, avoiding the tampon string which was dangling there. She reacted with a moan for how delicious it felt. Soon Jake was rubbing her continuously, and her arousal was growing rapidly. She began to squirm with his diddling, moaning slightly every time his fingers ran over her clit. When he focused his attention there, swirling around and over her most tender spot, she was close to losing it, which is just what Jake was waiting for.

With Eileen all warmed up, Jake took the KY jelly and lubricated her anus, then gently pressed a finger into her anal opening. In and out, he caressed her tight hole, adding lube as needed while waiting for her to enjoy it enough to relax the muscles surrounding his finger. She felt very strange with his finger in her, having never had anything in there before. But it felt good in its own way, and she began to enjoy the feel of his finger moving inside her, and relaxed. It hurt a little when Jake added a second finger, forcing her anus to open more; she tried to squirm away but could not, held by the table under her hips. But soon two fingers felt pretty good too, and she relaxed further, beginning to moan a little with the newfound pleasure.

Jake sensed she was ready, so he removed his fingers, lubed his penis, and touched it to her, rubbing it around her opening before pressing its head gently into her. She moaned again as it stretched her, but the pain lasted only a moment, and as Jake began to press deeper into her, the odd feeling changed to a good feeling. He backed out a bit, but left his penis in her, then pressed deeper. It felt a lot like intercourse, yet different.

Jake continued to press deeply into her, then backed off partway before pushing deep again. She was hit with a new arousal after the near climax at her clitoris earlier, relaxed and enjoying it more than she expected to. She was happy that she chose to have him do anal. He was now pumping her hard, and only the table beneath her hips kept her in place. With a few extra hard jerks, Jake climaxed and shot his ejaculate into her, its warmth not as noticeable in her rear as it was in her vagina, but still a nice feeling.

When he was done, Jake pulled out and wiped his dick with one of the tissues, then wiped her anus off and placed the used tissues into a waste bin alongside the table. Then he left her and went to the bathroom to wash his hands. When he returned, he went to her pussy again, running his fingers up and down her slit, avoiding the tampon string while stopping to swirl her clit. She responded with more moans as her arousal was reignited. He continued to swirl and she squirmed as much as she could with her hips pressed against the table's edge. After the odd feel of his penis up her rear, this was a return to the wonderful feel of his fingers diddling her clit. It wasn't long before the orgasm in her was released, and she jerked repeatedly and came, all of her energy focused on her pussy. Her juices flowed, but the tampon held them in her and Jake's fingers did not get soaked. Eileen was spent and completely exhausted as she lay on the table in the afterglow.

Jake helped her up and they wiped with tissues again and got dressed, then left the Playroom.

Back on the sofa, he kissed her passionately. She melted in his arms, worn out from the sex and so happy, not only to have pleased him with the anal, but that she enjoyed it as well. They kissed for a few minutes before either spoke.

“Well, it seems you enjoyed yourself in there, you gorgeous woman!”

“I did, so much more than I expected. Thank you for being gentle with me.”

“But, of course. You pleased me greatly, Eileen, and I loved it. And I'll always make sure to follow any discomfort with comfort as I heighten your sensitivity for whatever sex we have. I said you'd love it, and you did, didn't you?”

“Oh Yes! You can do that with me any time!”

“Great! And I promise to give you new and wonderful sensations in The Playroom.”

“That sounds great!”

“Say, would you like to go to a movie Friday night?”

“I'd love to!”

“Okay. I'll stop by to pick you up at seven.”

They ended her visit and Jake walked Eileen home, kissed her again at her door, and left.

On the walk back to his place, Jake thought about the last few dates they'd had. He was really liking Eileen, and he was pleased with the progress he'd made in guiding her to be his Submissive, and how she accepted him as her Master.

Meanwhile, Eileen was happy about the good times she'd been having with Jake. He seemed to love her even though he never came out and said it. And she was enjoying sex with him, and liked the way he treated her during her period. She especially liked how he was pleased when she accepted some pain to please him, and how he comforted her afterward. She could see herself accepting more pain, as long as it wasn't too long or intense, since it pleased him, and she would be comforted and cared for afterward. She was happy being Jake's Sub and continued looking forward to each time they visited the Playroom.

<< To Be Continued >>