Date Night

It was a little before 2AM when I turned the key and opened the front door.

Rebecca was sitting on the couch. She turned off the TV, and, smiling, turned to me.

"I thought you said you weren't going to wait up?" I said.

"I lied," she said. "As soon as you left, I knew I wouldn't be able to sleep. I've been distracting myself with bad TV. I'm guessing by the time that it went well?" she asked.

"Yes," I said, cautiously. "It did."

"Good," she said. "Come sit with me?"

"Of course. Let me get a glass of water." I went to the kitchen, poured myself a glass. "Do you want anything?"

"No, I'm fine."

I sat down next to her, our legs touching lightly. After more than a decade of marriage, I could usually tell when she was angry with me; I was relieved that she seemed a little tense, but not upset.

She paused, looked away, and then looked back.

"Will you tell me?" she asked.

"I thought you didn't want to know any details."

"I didn't think that I did. But I do. I went from feeling nervous, to jealous, to... kind of excited? I think I want to know. I do want to know. If you'll tell me."

"Anything you ask to hear, I'll tell you. Can I ask you, for details, later? Tomorrow?" She'd never been willing to share any of her stories with me, and I'd always wanted to know.

"OK, yes. You can ask, and I'll tell you. Tomorrow. But tonight, you tell me."

She leaned over and kissed me. I wondered if she could smell Kate on me.

She shifted so her body was pressing into me, her breast rubbing my shoulder. She kissed me again, and ran her hands over my back, and down to my waist.

She pushed me back slightly, undid my belt, and popped the top button of my jeans. Her fingers traced a path under the elastic of my underwear.

"If I pull your cock out now, what will it taste like?" she asked.

"Latex," I answered, "and Kate."

"Kate's what?" she asked, with a slightly wicked smile.

"Kate's cunt. It will taste like her cunt."

She undid the rest of the buttons, pushed my tights down, and took out my rapidly hardening cock. She backed up, leaned down, and took it into her mouth.

"What does it taste like?" I asked, when she stopped for a moment..

"A little like your fingers after you've had them in me." She paused. "... and I'm not tasting much latex..?"

"Not much, no. Do you want the story?"

"I do," she said. "Let's go to bed. You can tell me there."

When we got to the bedroom, we took off our clothes and got into bed. I admired Becca's body - so different than Kate's, but no less beautiful. Larger breasts, and a bit more weight overall. A few inches taller. Darker hair - running towards brown than Kate's blonde. But she was still very attractive, despite our ages being closer to 50 than 40.

Becca got the gel lube out of her nightstand, and one of her vibes, and lay down next to me. She turned towards me.

"OK, so, the whole story. Where did you go? Where did you start?"

"We met at Vault for a pre-dinner drink."

"Ooh, who was tending bar? Did they recognize you?"

"Robbie. Yes, I think he did. But of course he didn't say anything."

"What did you have?"

"I had a dry rye Manhattan; Kate had a martini. We sipped our drinks and chatted and flirted a bit, and then it was time to head off to dinner."

"Which was where?"

"Strand. We had reservations for 7:30. We got there just a few minutes after that."

"And what did you order?"

"A bit cliche. We started with a dozen oysters and sparkling wine. Then we shared an appetizer of raw tune, avocado, and some kind of lime-based dressing. It was really quite nice."

"Mains?"

"I had the duck, Kate the halibut. We switched to a nice white by the glass for the meal."

"Dessert?"

"About half-way through our mains, I told Kate how attracted I was to her, and she asked me to come back to her apartment, so we skipped dessert."

"Ah, so the good part of the story starts here," Becca said, smiling.

"Yes. We hadn't parked near each other, so I got her address, and drove to her apartment. When I got there, she was waiting at the door. We kissed, and went inside."

"What's her apartment like? I want to picture it."

"One bedroom place. You pass the kitchen on the way in. Living room / dining room combo. Living room looks out onto a small patio. I didn't really see that, though. Bedroom's off to the side.

"We went in, and sat on the couch. She leaned over and kissed me, and I held her. We made out for a while. I was running my hands across her back, brushing her ass, and up her sides, brushing her breasts. She was running her hands down me, and brushed my cock through my pants a few times. I was already hard..."

"I'll bet," she said, smiling.

"At some point, she suggested we move to the bedroom. We went in, undressed ourselves and each other, kissed again. She got condoms out of her nightstand, and lube. She unwrapped one, and put it over me, and added a bit of lube with her hand..."

"And..?"

"Well... to be honest, this next part is a little embarrassing? We started having sex, me on top, missionary... and I realized at some point that I wasn't as hard as I had been? And then I started getting worried..."

"Oh no!" Becca said, with just the hint of a joking tone.

"Oh yes. Well, Kate noticed that I looked worried, and that I was getting soft, and she asked if everything was OK, and I admitted that I was very nervous. She smiled and suggested we stop for a bit and just lie together and talk and kiss some more. I pulled out, rolled off her, and she took the condom off me. And then we talked..."

"What about?"

"Well, she started out asking me what you and I normally did for birth control, and I told her about my vasectomy. She asked if it had been a difficult decision, and I told her that it hadn't been, as neither of us had ever wanted kids. She told me that she was similar - had never wanted kids. Her ex had an already adult child from a previous marriage and hadn't wanted any more, so that had been fine.

"I asked her what she normally did for birth control, and she pointed at the condom box. She said that she had been on hormonal birth control - the pill for a while, and an implant at one point - when she was married, but when she left her husband, decided to go off the pill. Before she got here, she had a longish-term relationship with a boyfriend, and thought about going back on the pill, but decided to stick with condoms. I asked if she was worried about the high failure rate, but she said she wasn't - she was over 40, and not terribly likely to get pregnant anyway.

"We talked a little about why she came here, what her job was like; she asked me why I'd been nervous, and I told her that she was the first woman other than my wife that I'd had sex with since I got married, 15 years ago. She looked a little surprised, and asked if that was true, and I told her it was."

"Was it?" Becca asked.

"Of course," I said, a little offended. "I never cheated." I was struck by a sudden thought, "Did you ever cheat? Before our arrangement?"

Becca smiled and said "I said I'd tell you all my stories tomorrow. Let's add answering that question, OK? I want to hear what happened next."

"OK," I said. "So, we talked a little more, and we kissed some more, lying side by side. I licked her breasts at one point. Before too long, I was hard again, and she rolled me onto my back, straddled me, and told me to lie still."

"Wow," Becca said, "that sounds hot."

"It was. So, she's straddling me, and she starts toying with my cock, brushing her pubic hair over it, then pressing herself down on it, shifting slightly... She was playing with me, but also getting herself excited, using my cock to push up against her clit, or near it, anyway...

"This went on for what seemed like forever. Whenever I started moving, she'd shake her head 'no' and tell me to not be impatient. She wouldn't let me play with her breasts or ass - she kept moving my hands back to my sides, or just across her lower back. It was incredible, and also incredibly frustrating..."

Becca began to look more excited then, and moved to straddle me. But she stayed fully upright, balanced on her knees just in front of my cock. She got the lube bottle, put some in her hand, reached behind hers and rubbed it over my cock. I gasped slightly at the sensation.

"Yes..? What more?" she asked "Don't stop now."

"OK. So she played with me for what seemed like forever, moving up and down my cock, pressing and then letting off the pressure. And then... she shifted just slightly. She'd been rubbing her labia up and down my cock, but now she moved so my cock separated them slightly. And... I could feel how wet she was, and my cock was covered with her wet in moments..."

Becca rocked back and forth on top of me, still holding my cock. She released it, took the lube bottle and squeezed out another bead, bent forward, and worked it into her ass. "Yes, go on..."

"So at this point, I still expected her to stop any second, put a condom on me, and then fuck me with her on top. She was playing with my cock around her cunt, shifting a little this way, then that... moving slowly, then a little faster. Still, whenever I tried to move, she'd stop me, and tell me to be patient, and not to be in a hurry..."

Becca grabbed my cock and guided it towards her ass, putting the head directly on her asshole. She paused, smiled, and told me to continue.

"And then, she shifted just a little bit more, and my cock was in her. She pressed herself into my pelvis, still playing with herself, while moving slowly with me in her. I started moving very slowly and she nodded. 'Slow,' she told me, 'go slow.'

"As this continued, it suddenly occurred to me that she was going to let me cum in her. And that since she'd been using condoms for over a year, and had been with just one partner until recently, that I wasn't actually violating our rules. I was... incredibly turned on."

"I'll bet," Becca said, smiling wickedly. She pressed down, putting just the tip of my cock into her ass.

"Fuck, that feels amazing," I told her, because it did.

"Um hum, I'm sure it does. But keep telling me the story."

"She started moving a bit faster, and I matched her, and she nodded... After a very few more minutes, she bit her lip slightly, inhaled sharply, and I felt the muscles in her vagina pulsing around my cock. She slowed and almost stopped moving while she enjoyed her orgasm, and then smiled at me. She started moving again, a little more rapidly than before, and I started thrusting up into her. I could feel my own orgasm building, and when it started, I pulled her close, and felt my cock throbbing...

"She said something like ''Oh, I can feel that,' and smiled again. When I was finished, she just lay on top of me, kissing me gently, for what must have been several minutes. I was incredibly relaxed, and also incredibly excited...

"She got up by kneeling over me, and some of my cum dripped out of her onto my stomach. She wiped it up..."

"Did she taste it?" Becca asked.

"No, just wiped it up with her hand and then got off me." Becca gave a little fake frown. "We lay next to each other then, and talked some more. I told her how incredible that was, and she asked me if it was worth being patient. It was.

"After a while, I was moving my hand over her pubic hair, just brushing the top of it, and she gave a little sharp inhale. So I moved over her, and started just brushing against it very gently. She put her head back into the pillow, and moaned a little.

"I took it very slowly, teasing her a little, moving back to just brushing her pubic hair and then stroking a little closer to her labia, and then moving up and putting a little pressure near her clit, then moving back...

"Eventually, I moved down and started licking, first up one side of her labia, then up the other, my hand gently cupped over her clit. I licked her ass, and she gave another one of this sharp little intakes of breath.

"I asked her if she liked a little anal stimulation, and she said that she sometimes did, but to go slow. I put a single finger in - she was so wet from my cum and spit and her wetness it was really slick. I only put it in a few inches, and could feel how tight she was around it.

"It wasn't long before I was licking her cunt directly..."

"Wait, how did she react? You were going down on her right after cuming in her. Was she surprised?"

"If she was, she didn't show it. I'd actually forgotten just how much I'd cum in her - the long build up, and that first failure. At some point, I was surprised when I really did get a mouthful... it had gone liquidity the way it does, and mixed with her wet. It was pretty intense, but she was enjoying my mouth so much at that point I didn't dare even change pace. She got closer and closer, and suddenly I felt her ass tighten even more around my finger, and then felt pulsing waves of contractions around it. I kept going, and she made a little squealing sound.

"I slowed my pace and backed off, pulling my finger out of her ass gently. She gave another quick inhale, but then lay back down."

Becca reached back, and, holding my cock, pressed down a bit further, then rocked forward.

"Does this feel good?" Becca asked. "Are you glad to be home and in my ass?"

"Yes, very happy to be back," I replied, closing my eyes with the pleasure of it. "And always happy to be in your ass."

"Keep telling," she said.

"OK, so we lay there a bit, and Kate told me that she never cums twice a day, let alone in the same few hours, anymore. I expressed some surprise, and she told me a bit of a story about how she used to cum multiple times all the time, but hadn't since her thirties. She thanked me for helping her realize she could do it again. She said the fact that they were such different sensations, such different ways of reaching orgasm, clearly helped..."

Becca started moving a little more assertively. I reached up and squeezed her breasts. She reached over, grabbed her vibe, turned it on, and pressed it against her cunt. I reached out and held it there for her; she kept one hand on it gently, to point me in the right direction, and adjust the firmness.

"So we're lying there again, and I'm hard again, and she reaches over and strokes my cock. And I roll towards her, and ask her to roll over. She does, and I get behind her. She's still soaking, and when I pull her hips up towards me and put my cock into her cunt, it is slick and warm and tight and just amazing. I start thrusting, and she starts trusting back into me. She has, as I'm sure you can imagine, the cutest little ass, and her asshole is just a perfect little pucker. It was quite the view. I fucked her from behind, and between her vigorous thrusting and my own, I started to cum pretty quickly. I held her tight against me while I came in her again, then pulled out and lay down next to her. She lay half on top of me and brushed my hair with her hand. We kissed a bit more."

Becca was now moving more vigorously, pressing the vibe into her mons firmly; I could feel the vibrations in my cock.

"So that's pretty much the story," I said. "Kate asked if I wanted to spend the night, and I said that I probably shouldn't the first time I was doing this, and she said that was fine. We made plans to have coffee together after lunch on Wednesday..."

"Did you want to spend the night?" Becca asked.

"To be honest, yes, I did. But I also wanted to come home to you. I thought you'd be asleep though."

"This is better, isn't it?" she said, thrusting a little more quickly. "Fuck, I'm really close. How about you?"

"Yes," I said, "very. Don't know how much longer I'll last..."

She took my hand with the vibe in it and pressed it harder, directly into her clit.

"Are you going to cum in my ass?" she asked. "You came in her cunt twice already today, just hours ago... are you going to cum for me too?"

"Fuck yes," I said.

She started moving her mouth in the way that I knew meant she was starting to cum, and as I thrust a little more vigorously, I felt myself start to cum, too. She started making a gentle sighing sound, and I felt her ass contracting around my cock. She thrust all the way back down on me, tucked her chin down and closed her eyes, and rode out her orgasm, while I finished in her ass.

"Fuck that was hot," she said, opening her eyes again.

"Yes," I agreed.

She pulled herself up off my cock, smiled wickedly at me, and turned around, bending over me and sticking her ass out over me.

"How does it look?" she asked. "As cute as Kate's?"

My cum was dripping out of her; a drop fell onto my stomach, and cum ran down her leg.

"Dripping my cum like that, your ass is the hottest thing I can imagine now."

She laughed and got up, wiping herself with our sheets, and headed into the bathroom.

She called out "When are you planning on having sex with her again?"

"Well," I said, "you are going to be gone all Friday and Saturday, right? I thought I might spend Friday night and Saturday with her."

"OK," Becca said. "Just promise me you'll be careful, and stay in love with me, OK?" I could hear the bidet spraying.

"Always," I called out, over the sound.

"You didn't mention it, but did you keep your ring on? The whole time?"

"Yes... I didn't even consider it, really. She knows I'm married; she even knows you."

"Yes, and don't forget you met her through me - you owe me for that, I think." She smiled. "But you fucked her, fingered her ass, everything... Wearing your wedding ring?"

"Yes. I didn't really think about it. If I had, I probably would have thought it was hot... a bit kinky, even."

"Hmm..." she said. "I can see that, I guess." She finished up in the bathroom, wiping herself dry with a washcloth.

She came back to bed and snuggled in next to me.

"You'll really tell me anything I want tomorrow?" I asked.

"Yes," she responded. "But if it is OK, can I only tell one story at a time?"

"So like one story a day?"

"Yes..." she said. "It seems like it would be more fun for you, and easier..."

"How many stories do you have?" I asked. We'd officially had an "arrangement" for over 6 months; this was the first time I'd made use of it. She had insisted on not telling me when she was using it. I knew of a few times, when I figured out what she must be up to, but I knew there were others... And now I suspected there might be some stories from the dozen years before our arrangement, as well.

"Oh," she said, "a few. I'll give you the number tomorrow, OK?"

"OK, I said, turning out my light. "Sleep well."

"Sleep well."