My Wife wants a Hall Pass

"Then I want a video," I insisted. "Deal?"

"We'll see," Jan said somewhat reluctantly, then added quietly. "Pervert!"

"But I'm YOUR pervert," I said in a loving tone as I chuckled.

***

Ray's hotel was only five miles from our house, and it had a nice restaurant off the lobby. But Jan texted Ray, telling him to meet her at a different restaurant closer to our house and about three miles away from his hotel. She said that would send a clear signal that she wasn't going up in the elevator to his room afterwards. And she wanted the distance from his hotel, so she wouldn't be tempted to go to his room if she drank too much.

On Friday, I arrived home from work early, with Jan already there getting ready to meet her dinner date by six o'clock. She chose her favorite short, black, tight fitting cocktail dress which she wears when she's trying to turn me on during our date nights. And she was wearing a sexy black bra and pantie set with her tall, 'fuck me' heels.

"It looks like my flirting wife is trolling to get some action from him tonight," I noticed.

"Well, you said I could," Jan said, "as long as I get it on video. So, I'm out to convince him to set up the camera."

"Go for it!" I replied with a chuckle "He's married, so I doubt he'll agree to that."

"So, that's really why you wanted the video!" Jan said as it dawned on her.

"No double standards," I said with a laugh. "If you want to control me, I'll control you, too! Just remember the new rule: No video, no sex! Otherwise, I call Brenda or WE have a problem."

"I got it. And I'll remember," she said in resignation.

Jan came over to me, wrapping her arms around me in a loving hug. I leaned down and kissed her, then said in a soft voice "Go have fun. I DO love you. But try to be discreet."

"I love you, too," she said in her soft voice.

After she left, I turned on my phone tracking app to see where she went. It's not that I don't trust her. We use the locator app for our sex games. So, for this sex hook-up, it's appropriate for me to know where she's going. If she went to the hotel, and I didn't get a text and video soon after, I could call my former girlfriend to find out if she's busy, before it gets too late this evening.

Dinner and Texts

The app showed she went straight to the restaurant, and I saw she was still there over an hour later. I was wondering if she caught his attention and convinced him to allow video, or if she even remembered the agreement. I texted: 'How's it going? Will I get a video tonight?'

Two minutes later, she replied: 'Not tonight. He says too risky. Too bad.'

I sent: 'Have you tried all your tricks. Hand him your panties across the table. It always works to get what you want from me.'

It took another five minutes before she replied: 'He has them in his pocket. Still didn't buy a video.'

I knew my wife was horny, reminiscing with her old boyfriend, so I replied: 'Compromise. 3-some?'

That only took her a few seconds to send back: 'We'll be home in 30 minutes! CU there. Thanks!'

Going to our front bedroom, I placed our usual toys, lube, tissues, and blankets at the ready, where we've used them when having play pals here in the past. Then I opened a bottle of Jan's favorite wine.

As I was pouring her glass of wine, Jan's car pulled into the garage. They came in together through the door to the garage, and I handed my wife the glass of wine, holding out my right hand to Ray. "It's nice to finally meet you."

"Yes," Ray said as we shook hands, then we walked into the living room. "I've heard a lot about you over the years."

"Jan said that you're married," I pointed out, not trying to embarrass him or slow things down, but just wondering about their relationship. "Does your wife ever travel with you on trips like this?"

"When she can get the time off from her nursing job," Ray said. "But in case you're really wondering, we're both into playing with some couples near where we live. And she allows me to play separately, too. She's just adamant that there will be 'No pics of us with anyone else, ever, for either of us! Or else!' I don't want to have to lie to her. But I can understand your wanting quid pro quo with Jan and the video requirement."

"Yeah," I said. "Jan doesn't want me playing separately with an old girlfriend. So, I deserve some compensation."

"I just didn't want him going back to Brenda," Jan responded. "She's now single and on the prowl."

"Like you don't trust me," I said with a chuckle.

"I don't trust Brenda!" she said insistently.

"Jan always tried to control me, too," Ray said to me. "I told my wife I was getting together with Jan this evening. I didn't know if she'd play, but I had my hopes since I knew you two were swingers. I would have been satisfied just seeing her again over dinner, to at least enjoy her flirting."

Round 1

After a brief pause, Ray added "Dedra and I have always been open about sex and we play around. But I've never done a threesome like this. When we play with other couples, it's been one-on-one for us. I always wondered what it's like to DP a woman. So, how do we start?"

"I don't know about a DP. But you could start by undressing me," Jan suggested, as she stood from her chair.

Ray stood and reached to her waist, grasping the material, lifting her dress over her head. He let it drop free to the floor beside her. My wife stood there wearing just her bra as Ray leaned in to kiss her. She put her arms around his shoulders in a passionate embrace.

Stepping in behind her, I unfastened her bra and pressed my hardening member against her ass. Looking over her shoulder at Ray I said, "Maybe we should take her to a bed."

Jan stepped back and dropped her arms from his shoulders, allowing the bra to fall onto her dress. Then she took Ray's hand and led him to the front bedroom.

As Ray and I were stripping out of our clothes, Jan sat at the bottom edge of the king-sized bed. Ray walked around to stand beside her at the left edge of the bed and she laid back, turning her head toward him and she grasped his cock, directing it to her mouth.

I went to the nightstand on the other side of the bed to retrieve a rabbit vibrator and returned to kneel between her spread legs. I inserted the vibrator and started playing with her pussy to warm her up.

After a few minutes of playing like this, Jan pushed my hand and vibrator away and inched her way across the end of the bed to the center, giving Ray room to crawl onto the bed. As he knelt there to the left side of her head, I crawled onto the bed on her other side. She had her right hand on his cock and grasped mine with her left, turning her head from one to the other, taking turns sucking on us.

We were staring down at my wife when Jan turned back to take his cock again into her mouth. Then Ray caught me by surprise when he reached down alongside Jan's hand and wrapped his hand around my stiff shaft.

I'm not Bi, so I reached down to brush his hand away saying, "You don't need to do that. She'll handle it." Jan didn't react to any of that, just focused on her own tasks at hand.

After another minute, Ray moved off the end of the bed to stand between her legs, grasping her calves to pick her legs up and spread her open. She reached down to guide him in as he slid his stiff shaft into her. He began pumping into my wife, while Jan kept her head turned toward me, with my cock in her mouth. But out of the corner of my eye, I noticed Ray mostly kept his eyes on me, and I wondered if he might just be worried about my reactions to him fucking my wife.

After a minute in this position, I suggested Jan get on her knees, and we moved her into the center of the bed. I turned her ass toward me and entered my wife from behind, while Ray crawled to her head and fed her his cock again to suck.

Jan seemed open to suggestions from either Ray or me, and she readily moved to whatever either of us asked her to do. I think she wanted this evening to be special for both her decades-long friend and for me. She seemed to want us to get along, and she was probably still concerned that I might get jealous, or that Ray might react badly.

But I think we were all enjoying our time together, fucking my wife from both ends. As I heard his breathing and excitement grow, I heard Jan reacting with her own moans. When she gets feedback like that from her guys, it seems to increase her own pleasure. And I felt the buildup in my own cock, as the pressure seemed to rise up the shaft.

Ray kept looking at me and started shoving harder into her, putting his hands on the back of Jan's head. His thrusts became erratic as he neared his orgasm, and he held her, not giving her a chance to give her mouth a break. And she wasn't even trying to pull away from him!

I felt the pressure of my own load growing closer to the tip. When it finally seemed at the end, I thrust deep inside her and paused. Then with two more erratic thrusts, I let out a low groan, saying "OH, yeah! There it is," and my body tingled with the release of that first shot deep inside her.

Ray seemed just as excited, and as my cumshot went off into her, he shoved deep into her mouth, and I heard her gag at the same time, before he pulled back a little. It must have been a sudden spurt from him then which seemed to catch her in the back of the throat. Jan gagged and coughed again, letting his thick, white fluid drool out around her lips, dripping onto the bed. As my stiff shaft pulsed a few more times to finish in her, Ray was pumping the rest of his load into my wife's mouth at the same time.

I reached for the box of tissues nearby, pulling a few to catch my cock when I withdrew. And Jan grabbed a few to wipe at her mouth, then reached for her pussy to catch my load as it came out of her.

My wife coughed one more time, and said, "Wow! You two certainly seemed to bond over me, cumming at the same time!"

Ray and I both chuckled, and I said, "Well, you know how to bring people together."

We decided to take a break, heading back out to the living room. But the evening wasn't over.

Intermission

Jan refilled her glass of wine, and the three of us sat in the living room to talk.

Ray said he and his wife played around with a few people they encountered, finding couples at a bar about 40 miles from their house. And he asked how we set up our contacts in this lifestyle for our play dates. Jan mentioned the lifestyle web site we use, and I pulled up our web site profile on the big screen TV to show him.

"You two should try setting up a profile on this site," I said. "I'll text you the link and our profile name. Check with your wife to see if she'd be interested. Maybe we can get together in the future."

"That would be great," Ray said. He paused, then added with a melancholy tone "You know, you're a lucky guy to have landed Jan. I almost stole her away."

"But you didn't propose," Jan said, with a hint of sarcasm.

"You talked too much!" Ray said dismissively, as if explaining.

"All women talk too much," Jan replied. "You just couldn't handle me!'

Ray chuckled a little before adding "You weren't ready for me."

"What do you mean?" Jan asked with serious concern.

"I don't think you realized how much you mentioned Ted when we talked," Ray said, as if explaining how she behaved.

"Ted?" Jan asked, surprised.

"Yeah," Ray went on adding, as if just stating facts, "You often mentioned things the two of you did before you met me. ... I knew it was just you, being you, saying whatever was on your mind and not dissing me. It seemed you had something more on your mind than just the two of us. So, when I got that other job offer, I asked if you wanted to come along. But I knew you might be waiting for something else."

Jan awkwardly glanced between the two of us, and I just smiled in understanding, realizing what Ray meant. After a few seconds he broke the awkward silence, asking Jan; "Do you remember the toy I bought you?"

"Yeah. I still have it," Jan admitted, appreciating the change of subject. "But we don't use that very often."

"Very often?" Ray said in surprise. "I wish Dedra would try it even once."

"Well, bring her here sometime," Jan said coyly "and maybe I can turn her around."

Ray looked surprised. "You go there, too? Wow. I thought you were straight. You have changed from that reluctant ass I took thirty years ago."

Jan laughed, then said "You'd be surprised, newbie!"

I was starting to get hard again, so I said, "Speaking of ass, maybe it's time to try again."

We went back to the bedroom for seconds.

Round 2

When Jan laid back on the bed with her head on the pillows, I crawled onto the bottom of the bed and between her spread legs. She reached down to grasp my now hard shaft to guide it into her opening and I start pumping into her in the missionary position. Ray knelt at the head of the bed and offered her his stiffening shaft at her mouth.

Jan's lips soon had Ray hard again, but after a few minutes, he got off the bed and went toward the bathroom. I pulled out of Jan's pussy crawling up to lay beside her, and she rolled over on top of me. Reaching under her, she grasped my stiff shaft to guide it in as she slid down onto it. She leaned forward, holding her arms straight, poised over top of me and quietly said, "Thanks, for not spoiling this for me."

"You know I like doing things to make you happy," I said. "And you always seem to take care of me, too."

She started slowly rising up and down on me, massaging my fleshy shaft with her warm, wet hole, and I whispered to her, "Lean over. I want to feel your tits on my chest."

Jan lowered her upper body down onto me, lightly brushing her nipples on my chest as she began to bounce her hips up and down, sliding her wet opening over my cock.

I noticed Ray when he returned from the bathroom, with his hand on his fleshy shaft and stroking himself. He was staring at Jan's ass, her thighs spread open and her knees on either side of my hips, with her pussy impaled on me. When he glanced at my face, I quickly shifted my eyes toward her ass and back again, giving him a quick nod. He reached to the dresser, picking up a bottle of lube to squirt a liberal amount on his member, and crawled onto the bottom of the bed between my feet.

Crawling into position behind Jan as she was still riding me, Ray put his hand on top of her ass to stop her bucking. She turned her head slightly, trying to look over her shoulder at him before saying, "If that's what you have in mind, go slow. You're bigger than the glass rod. And I haven't loosened up with it."

Ray positioned the head of his well lubed cock at my wife's rosebud, and I was still firmly inside her as I felt his length start pressing into her other hole.

"Stop," Jan suddenly said, then calmly added. "It's hurting. Take it slower, and back out and in again, a little at a time."

Ray worked his cock into my wife's ass, in and out, taking it slow, as I saw her face grimace a little each time he pressed forward. I laid there patiently waiting, watching her eyes grow wide and sometimes shut as she endured his intrusion. I could feel his length along my cock through her, as he slid further in. Then with one final, long push, he passed her resistance and slid all the way in to stay there.

"You have it all," he said.

I looked into Jan's eyes, smiled, and asked, "Are you ready?"

She rose off me a little, picking her hips up until she was still barely poised with the head still inside. Then she said loud enough for Ray to hear, "Go ahead."

Ray and I started thrusting into her in this awkward position, with me bucking up into that pussy, while he pulled most of the way out and slid back into her ass. As we were fucking her, Jan and I both glanced to my right, looking at the large wall mirror to see the three of us. She was sandwiched between me and her former boyfriend, as he fucked my wife's ass.

Jan closed her eyes as she focused on this new feeling, being penetrated in both holes at the same time. Then I felt her starting to rock on her knees, getting into it and trying to buck onto both of us! I soon had to just keep my back arched up with my cock at the best angle, letting her do the work of slipping her pussy back and forth onto me.

When she opened her eyes, I could see them gleaming with excitement as she began rocking back and forth faster. Her breathing was coming out in gasps with "Oh. Oh. Oh! AHHHH!" sounds until she went over the top with her orgasm. She paused, and I felt her pussy spasm, squeezing me and her body started shaking.

Ray and I weren't as fast finishing in her this second time around, or at least I wasn't. I kept pumping up into her, and I felt Ray's cock through her thin membranes, pumping even faster.

He must have been enjoying this sight of Jan bent over, her ass cheeks spread, as he fucked that opening his own wife forbids. When Jan's spasms stopped, he finally growled as he made a few final slower thrusts, then stopped, buried deep inside. I felt her body move as he bucked his hips a few more times against her ass cheeks, shooting his second load deep in her bowels, before collapsing onto her back. His weight pushed her down onto me, and we laid there just a few seconds in an interconnected pile.

Jan was the first to react after giving him that few seconds.

"Oooffff. Dead weight! It's time to get off," she said as she tried twisting out from under him.

I didn't finish cumming in her this time as she pulled off from my still firm cock. But Jan and I would have all night together. And she's always accommodating for me when we're in bed alone later. I handed her the box of tissues to catch the cum dripping from her still open ass, and I pulled a few out to wipe her wetness from me. Then we all cleaned up a little, dressed, and returned to the living room.

It was getting rather late now, as Ray said, "I need to head back to my hotel soon. I still have to pack to catch my plane in the morning."

"Too bad," I said. "We have spare rooms, and you could spend the night."

"Maybe next time," Ray offered "if we plan ahead. I wouldn't mind spending the night in bed with her again."

"That's unlikely," Jan said. "Ted's the one I always want to end the night, with my head on his shoulder. That's what keeps us together."

"I understand," Ray said. "But I can dream. And it would still be nice to wake in the morning, finding your ass in the kitchen, ... maybe ready to go again."

"Maybe," she replied with a flirting tone. "But next time, convince your wife to come along. I want to see Dedra with Ted, too."

"I'll call an Uber to head back to my hotel," he said.

"No need for that," I said. "I can give you a ride, it's only fifteen minutes from here."

Guy Talk

"I think I've had enough to drink tonight," Jan said. "And I need a bathroom break, so I'll let the two of you go without me."

Jan walked Ray to the door giving him a final hug and kiss. "Mmmmm," she moaned, then broke the kiss, laying her head on his shoulder. "I'm glad we had this time together."

"Me, too," Ray replied. "I was thinking of the possibility all week and hoping for this with you."

"Now I'll be thinking of you like this every time you e-mail or text," Jan said. "Let us know when you get back home safely, and when you'll be back."

"I will," he said, "and I'll see if Dedra can come next time."

After one final kiss, Ray and I went out to my car for the drive. Once we were in the car and headed toward his hotel, he soon broke our awkward silence by hesitantly asking "Do you mind if I ask you something?"

"That's a loaded question," I replied. "Go ahead. What's on your mind?"

"... Is Jan really Bi?" he asked after a pause, and I realized he was easing into some other concern.