An adult stories – My Wife wants a Hall Pass by Lifestyle66,Lifestyle66 Author’s Note: This is another stand-alone story with more adventures of my favorite swinger couple. You can expect some fun with extra-marital sex.
The Prologue is one of my other stories, “A Different Proposition — 750 Words”. This is a brief scene which encapsulates my main couple’s relationship. So, for those of you who criticized that story and said their marriage would never last, read on.
*****
Prologue — Thirty Years Ago
I’m a clueless geek, but also a sex addict. And I like my girlfriend-with-benefits, Jan because she enjoys sex as much as I do.
After college, I finally got a good job offer from a computer firm, located in a city a ten-hour drive away, and I asked Jan out that same evening. I took her to a nice restaurant and ordered wine with dinner.
After her first sip of wine, Jan asked “So, what’s the occasion?”
“I got a job offer today, and I’m going to accept it.”
“Where’s the job?”
“It’s in the city, at least a ten-hour drive from here.”
“Are you giving me two-week’s notice?”
“I don’t want to. I like our time together.”
“You know what I told my last boyfriend, Ray, when he wanted his fuckbuddy to move with him.”
“You’re not a fuckbuddy to me. I like being with you.”
She said in a sweet, sing-song voice, “Are you saying you won’t be able to stop thinking of me? Or maybe you can’t stand the thought of being away from me?”
“I guess,” I said somewhat dejectedly.
“Okay. But you know,” she said in a determined tone “… I’m like Barbie. That bitch has it all… And I want it all!”
“What do you mean?”
“Oh, come on! You KNOW you’ve never said the L-word to me.”
“So?”
“This bitch wants it all,” she said sternly. Jan smiled as she cocked her head to the side and cupped her ear with her hand, sweetly drawing out the words saying: “I’m waiting…”
“Okay!… I love you!”
“Now was that so hard?” and she smirked in triumph. “I love you, too.”
“So, you’ll move with me?” I asked hopefully.
“Of course not!” she said sternly. “You’ve only made it through step one.”
She again cupped her ear with her hand. “Next?!… The bitch is waiting…”
“… Okay, bitch! Let’s get married.”
She looked back at me smiling and lovingly said, “But I’m ‘your’ bitch! It’s close enough. The answer is ‘yes!’ Now, here’s what you’re going to do…”
Jan went on a lengthy, rapid-fire monolog for the next few minutes, telling me everything I was to do, and what she would do over the next two months! She even told me which ring to buy, where to buy it, and how much to pay. She already had this planned and rehearsed in detail!
“And don’t let them con you into paying any more for the ring. You can be naive sometimes… My best friend, Marlene said she’ll set up my bachelorette party with the theme; ‘No Holes Barred’. You can get your friend Eric to do the same for you.”
“You planned this? You didn’t even know I got a job offer, or that I would propose!”
“I knew you were smart enough to get a good job. And I saw the signs you were hooked on me. I just waited and reeled you in.”
“And what’s this ‘No Holes Barred’? You’re going to fuck other guys before we get married? And take it in your ass, too?”
“Probably not, but you know how wild Marlene can be. So… maybe. … And Ray fucked me in the ass sometimes, so it’s not a virgin hole. But if you do fuck anyone at your bachelor party, use condoms. And don’t invite Brenda!”
“You never told me you took it in the ass.”
“You never asked!… And it’s not like we haven’t fucked others. So, do it or not. But it will be your last chance at freedom before you’re mine! After you say, ‘I do’, this is your pussy and that’s my cock. We’re going to spend our first week together fucking our brains out. Then we’ll fly to Florida for a week. I always wanted to go to Disney World.”
“Don’t I get any say in this?”
“You went away to college and picked your career and job. Now, it’s my turn! You’re going to work and make money. I’ll find another job to make even more money and plan our great fucking life together. Got it?!”
“Do I get blowjobs?”
“You had to spoil the moment! You know I don’t like to do that.”
“Well, you were going on and on about everything you want, including getting fucked in the ass!”
“Okay. You’ll get blowjobs, but not all the time. Tonight, you’re going to make love to me, slow and easy. And you’re going to use the L-word!”
“I can do that.”
Jan rolled her eyes and said, “I love you!”
“And I L-word you, too.”
Intro
The company vice president, Walt, was shaking the client’s hand as our group walked out of the conference room, leaving after the meeting. He always likes using this business club’s meeting rooms, trying to impress potential customers with the upscale surroundings of the penthouse view and its nice, members-only restaurant and bar. Walt invited the client to the club’s bar for a drink after the meeting and he asked me to join them in case they had any more technical questions. But I was planning to stop at the electronics store in the adjacent mall, before heading back to work.
The VP gives me a great deal of flexibility after our thirty years of working together. He finds the clients and leverages my tech expertise to impress them into signing the contracts. And he assigns me to fix the problems other technicians cause, to keep the clients happy. We’ve made a good team together over the years, … and we’ve both made a lot of money.
While the rest of our contract team went into the restaurant for lunch, I stood alone at the club’s elevator to go down to the adjacent mall’s shopping level. Checking my tie in the reflection of the mirrored doors, I straightened it, making the tie’s divot a little more prominent. Although I don’t always wear a jacket and tie to work, my wife insists that when I do, there is a proper way to wear it.
She always dresses to impress in her sexy styles. Her preferred work clothes are neat slacks or a short skirt, with a silk blouse unbuttoned just enough for her cleavage to attract attention. The push-up bra emphasizing her ample chest and four-inch FM heels gives her already tall athletic figure a sensual, but commanding presence among her male or female peers at work.
Seeing my own image in the reflection, I self-consciously straightened my back and pulled my shoulders back, correcting the posture of that tall, athletic guy with slightly greying hair.
My cellphone pinged, and I glanced at the screen to read a new text from my wife. ‘Locator app shows your phone in the club or a hotel room above the garage. Having fun without me there to watch?’ and she added a frown emoji.
When we play with others, it’s always when we’re together at swinger house parties, and we both enjoy watching each other. So, I know she’s teasing and trusts I’m not really with another woman in the hotel.
I replied ‘Client meeting in the club. Join me for a drink?’ I sometimes ask my wife to meet here after work for a drink, but she must be on a lunch break from her accounting job. I could always do my shopping some other time, so I invited her to join us at this business club’s restaurant. I knew Walt would like to have Jan join us there as ‘eye candy’ for our client, because he knows her and how much she always enjoys flirting and teasing. He’s known her for thirty years, and he appreciates the show, watching her command the men around her.
Her next text said ‘I saw your car. How about a quickie?’
I love my gorgeous wife. Her high sex drive keeps our life interesting. So, I replied: ‘I can be at my car in ten minutes.’
Her flirting response was ‘Find me, and she’ll be ready in the back seat of MY car. Clock’s ticking!’
She must have found a relatively safe, secluded parking spot to start this. My wife’s ‘Clock’s Ticking’ response is her game, like a geo-hunt where people use maps or a GPS to find a hidden cache. Only in this hunt, my goal is to locate her cellphone within the next ten to fifteen minutes via the locator app, as she sits in her car somewhere in the parking garage.
She’ll start a countdown timer on her phone for the ten minutes I told her it would take to reach my car. Then she’ll move into the back seat of her car to take off her pants and panties and lay across the backseat with her shapely legs spread. Her long auburn hair is probably brushed out, with one side pulled back over her right ear with a hair clip, for her usual office look. And she’ll keep her silk blouse on to save time, not needing to reveal her ample chest to further excite me. The game prize, if I find her in time, is her shaved pussy on display, ready and waiting. She’ll wait in that position for me to find her, hopefully before anyone else happens to pass near enough to her car within the next few minutes. It’s all part of the thrill for her. She once said, “If another handsome guy finds me first, you might get sloppy seconds.”
The cellphone app shows me where her phone is located on a map, but not the garage floor number. And when her timer goes off, she’ll start getting dressed again to leave her car. So, at most, I might have a few extra minutes to catch her still at her car. Then any consolation prize will depend on her mood and whether she’s in a rush to get back to work.
I always give her a short, but realistic time limit for these quickie meetups, so she can plan her lunch break. But today, she’s in a flirty, teasing mood with ‘Clock’s Ticking!’
The app showed me she’s parked within sight of the garage stairwell. So, I’ll take the elevator down from this penthouse club to the top floor of the four-level parking garage, and rush down the stairs between the garage levels until I spot her car. Now, if that damned elevator would just hurry, I’ll probably win today’s prize!
***
The Lifestyle
My wife, Jan and I were social outcasts in our small rural school, me because I’m a geek, and her due to her outspoken personality challenging the most popular kids in our class. We finally started dating during our senior year in high school when she directed me to take her to the Prom. And we continued together during our two years at Community College. We were both virgins when we started dating, and we remained exclusive with each other for those three years. After we both finished the two-year college, I went away for two more school years to earn a bachelor’s degree in computer science at a university, while Jan lived with her parents and found a local job as a waitress.
With me going off to the distant university, we decided it might be time to take a break in our relationship, rather than agonize over missing each other. It’s like the 1960s oldies song: “I Wonder What She’s Doing Tonight.” Rather than wonder if she’s out with another guy, we agreed we would both date others. I knew she would be out dating, and probably having sex with other guys. And she knew I would be shopping around for sex with other women. We didn’t want any angst or surprises between us. We just agreed to see how things worked out when we got back together.
During my time away, I hooked up with a few different girls around the university, including Brenda. She was a year younger than me, and I met her at a bar near the school. We had some good times together, fucking in the car, on a blanket in the park, in my off-campus room, as well as on the hood of my car in a parking garage. But when my best friend and apartment roommate, Eric found out who I was with, he told me I wasn’t the only one she was hooking up with during those months we were dating. He said he had her in a gangbang with three other guys afterhours at the bar where she worked. And yes, he was still my best friend after that, because it wasn’t his fault she was into gangbangs without telling me. After a shot of penicillin, I knew she wasn’t working out for me in the long term.
Jan later described some of her fun times, too. Hers included fucking a guy in a nightclub men’s room, and living with a guy, Ray for a few months who was five-years older and had his own apartment (until he moved away). And then there was the time she and her best friend, Marlene went on a week-long vacation and drinking binge. Jan told me that during their binge week, one morning she woke up in her hotel bed next to a guy she couldn’t remember meeting the night before. She couldn’t even remember his name. She was shocked later that morning, when she saw police setting up crime scene tape and an ambulance crew taking a girl’s body out of an alleyway. She said, “That could have been ME!”
Jan and I got back together after I finished my degree program. It was probably just luck neither of us needed ANOTHER shot of penicillin. We decided we’d both had enough of those wild experiences, and it was time to think about settling down. So, at her prompting, I proposed marriage later that summer when I got the job offer from Walt.
Decades later, with the kids grown and out of the house, we were both beginning to get bored, and we both felt the middle-aged longing of ;’Is this all there is?’, and our old wild streaks came to mind again. So, we began exploring a discreet swinger lifestyle with other couples. We knew if any of our friends or work colleagues found out about our new lifestyle, it might result in some negative, judgmental consequences. We thought it wouldn’t be fair if one of us was seen by a friend or neighbor when out with another play partner. Whether seen just having dinner and dancing or going into a hotel with someone other than the spouse, it might cause the other one a problem at work or at least ridicule from some of our common friends. So, we agreed we’d only play around with others when we’re together, since we’ll both then share the same risk.
We also mostly like watching each other when we’re with other couples at house parties. I did give Jan a ‘hall pass’ once for sex alone with a guy she was lusting for, to play in bed in a one-on-one situation. But that was in a different room in the same house. It wasn’t really cheating, since I could have fun with other women there or could have gone in to watch them.
Over the years, Jan stayed in touch with her former live-in boyfriend, Ray, via letters, e-mails, and texts after he left. He moved away for a job transfer, and Jan wasn’t ready at that time to leave our hometown to follow him. Although they broke up, they parted on good terms. Ray has since married and now has his own family. And I wasn’t jealous of Jan keeping in touch with her old “friend with former benefits.” He and his wife lived over two thousand miles away, and Jan hadn’t seen him in the thirty years we’d been married.
As part of our own sex together over the years, Jan and I would describe some of our sexual encounters with others. Jan told me Ray bought her a glass beaded anal rod for her to try anal sex, which she still occasionally uses. Okay, … he might have had that hole of hers before me, but I still wasn’t jealous. I wasn’t particularly interested in fucking my wife in the ass. And she said she wasn’t really into it very often, even with me. But she was comfortable telling me things like that and telling me every time she exchanged e-mails with Ray.
Old Flames
One evening after work, we were sitting at the dining room dinner table when my wife said, “I had a voice message on my phone today. It was from my old boyfriend, Ray. He said he’s here in town for business and staying at the hotel about five miles from here. He wanted to know if I’d be interested in getting together with him for dinner on Friday. But I can’t go.”
“Why can’t you go?” I asked, realizing with the way she phrased it, she hadn’t yet contacted him to say ‘No’, and she was fishing for my reaction. “We don’t have any plans on the calendar.
“Because you and I are married,” Jan said with a definite hint of concern. “Wouldn’t you have a problem with that?” she asked.
“I wouldn’t be jealous, if that’s what you mean,” I pointed out. “You can still go out to dinner with him.”
“He and I lived together,” Jan said as if I needed to be reminded. She paused as if letting me think about that, then added in exasperation, “He might want me to go to his hotel room after dinner.”
So, that was where she was going with this! She was trying to be subtle to see if I’d give her a hall pass to fuck her old boyfriend.
“That’s alright with me, too,” I said, knowing they’d had sex together long ago. Since my wife’s hysterectomy four years ago, she can’t get pregnant. So, in my mind, this would be just one more time, doing something they’d done before. “I’ve seen you with other guys at the swinger house parties.”
“But we’ve both agreed we’ll always be together at those parties,” Jan said.
“Okay, then,” I said as I realized what she meant. Then after a few seconds thinking about it, I spelled out her real concern, “So, if I say you can go out and fuck an old boyfriend, I could call up my old girlfriend, Brenda. She only lives about thirty miles from here. And the last time I talked to her, when I ran into her at the mall, she said she’d like to get together again sometime.”
“No way!” Jan insisted. “You’re not going out alone with her!”
“If you can go out with Ray and fuck him,” I calmly pointed out, “then I should be able to go out and fuck someone I know from the past, too. That’s only fair.”
“But you don’t have a problem with me fucking him,” Jan said sternly. “I DO have a problem with you fucking her. She’s single now.”
“Okay… ” I said, drawing out that one word. “You don’t trust me with her.”
“I don’t trust HER!” Jan said, raising her voice.
“You know I won’t accept any double standards between us,” I calmly went on. “So, if you want a hall pass with Ray, I deserve something, too. If you don’t want me seeing Brenda, I could always make a pass at a divorcee who never wants to get married again. … I know, Walt’s secretary, Carol! It would just be sex with her.”
“NO FUCKING WAY!” Jan almost shouted at me. “Her sister works at my accounting firm! How embarrassing would that be, if she spread the word my husband was fucking around on me?”
“Okay, then. Here’s another deal,” and I went on. “You can go to dinner with Ray. … But, if you have sex with him, text me before you start, then make a video of the two of you doing it and send it to me.”
“WHAT?” she asked surprised. “A video of us fucking?”
“Yeah,” I said. “Or at least a one-minute video of you sucking his cock.”
“I’m not a porn star!” Jan pointed out, as if that would make a difference. “And why do you want a video? Do you intend to use it to divorce me for infidelity?”
“Of course not,” I calmly assured her. “We’re swingers, so that would be stupid of me to accuse YOU of cheating, when you can easily find witnesses that I’ve fucked other women. And why would I divorce you? I’ve watched you suck and fuck other guys! The video isn’t even something new to you, since you allowed Sarah to record us in an MFM with her cellphone that time her husband was fucking you.”
“So, why the video?” she asked again.
“If you have sex with him, then why shouldn’t I see Brenda?” I asked. “Just because YOU say so? I deserve something in exchange, if you want to limit me, and that’s just what I want! If you insist that I can’t see Brenda, then set your cellphone camera to record video, prop it up on the nightstand aimed at the bed, and send it to me when you’re done. It will be like I’m there sharing with you like we do at house parties. And leave the lights on! Otherwise, I can call Brenda.”
“NO!” she insisted. “You’re not calling Brenda!”
“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.
“Not really,” I said. “As she describes it, ‘It’s situational.’ She doesn’t go out looking for other women to play. But if the circumstances are right, she’s not averse to it and she’ll play with a woman she likes.”
“… Are you?” Ray asked after another brief pause, and I knew that was what he was really looking for.
“No,” I said calmly. “I’m not interested in other guys in any way. I prefer just straight sex with women and their unique warm, wet openings.”
“But you had Jan using her mouth on you,” Ray noticed, “Would you know the difference if a guy did that to you? And she said you two sometimes do anal.”
“I’ve only fucked Jan in the ass when she wanted it,” I explained. “And when it comes to oral, that’s really something just between me and her. She’s rather demanding and self-centered most of the time. So, when she goes down on me, it’s like she’s giving me a present without having to say ‘This is all about you tonight’.”
“I remember her being self-centered,” Ray said.
“So, I appreciate it, when she does that,” I went on. “It’s her way of showing me that she’s thinking of me. … Now would you mind if I ask you a question?”
Ray took a deep breath, then sighed, offering “Yeah, I prefer guys. Jan wasn’t the first girl I was with. But I had a very close friend for several years, until his job transferred him away. Then I met Jan and I found we just didn’t have the same connection. It was different with her. She would get moody sometimes, and we just didn’t communicate as well as I did with him.”
“Does your wife know?” I asked.
“Yes,” Ray said. “She’s known since we first got together. She doesn’t mind. She just doesn’t have the same sex drive as Jan. So, Dedra encourages me to find some relief elsewhere without her. And she sometimes gets together discreetly with a boyfriend. According to Dedra, her boyfriend is ‘not marriage material.’ So, after the kids were born, ours became more of a marriage of convenience, meeting the expectations of our jobs, the kids’ school friends, and our neighbors and other friends as the normal couple. That’s why she insists on our ‘no pics or video’ rule. It could change the optics of our marriage. But I’ve never told Jan, even after all these years with our e-mails or texts.”
“That’s your choice to not mention it to her,” I admitted. “Although Jan will sometimes go one-on-one with another woman, she’s told me; she NEVER wants to see two guys going at it together.”
“Really?” Ray said surprised. “That’s rather hypocritical.”
“And she’ll admit that,” I assured him. “I think, in her mind, she likes to control men with her flirting. … We were at a swinger party once, when she saw a hot looking guy she wanted. Another woman was flirting with him, so Jan went to him and quickly went down on him, right in front of the other woman. Jan’s very competitive! She probably doesn’t want to compete against other men for her flirting target’s attention. So, if you tell her you’re Bi, she might start seeing you as competition.”
I pulled up in front of his hotel, and as Ray was getting out of the car, I said “Stay in touch. If you and Dedra come to town again, maybe we can all get together. You’re always welcome at our house. But remember, I don’t lean that way.”
“Too bad,” Ray said, then added “You’re rather handsome.”
I just chuckled and smiled before replying “In your dreams.” He smiled back and closed the car door.
Thanks
When I walked into the house through the front door, I took the two steps up from the foyer and walked up to Jan standing in the living room. I wrapped my arms around her, pulling her in close to kiss.
“Now that was a wild evening,” I said as I held her in my arms, “even by our standards. I didn’t know you liked it in the ass so much.”
“I don’t … usually,” Jan admitted. “But when I was younger and trying to impress him, I tried things like that for him. I did the same to trap you.”
“Trap me?” I asked as I released her from my hug. “How did you trap me?”
“Oh, come on!” Jan exclaimed and chuckled. “How many times did I suck you off in the car when we were dating? But I got you!”
“That’s right,” I observed. “You don’t do that anymore.”
“Well,” Jan hinted, “maybe since you’ve been very good to me tonight, I might do it again.”
“But anal, and in a DP?” I inquired.
“Every once in a while,” she explained “it can be interesting and different. And Ray was the first a long time ago to patiently show me how much I could enjoy it. So, with him here, … and you, … it just felt right. This was the first time I’ve ever done it with two guys, with one in my ass, not even when Ray and I were living together.”
“That’s one thing I love about you and this lifestyle,” I said. “It brings out things you’ve never really confided to me.”
“It’s not about keeping secrets or not confiding it to you,” she said. “It just never came up, because as I said, I don’t usually like it. But … once in a long while… in the right conditions… I think … Hmmm, maybe tonight?”
I chuckled, “We’ll just have to search for more special conditions to see what else you might like, … The cuffs and tethers again?”
Jan just laughed, “We’ll see.”
***
She looked down at my pants and noticed my stiffening shape through the material. “I see you’re getting ready again,” she said as she smiled seductively.
She turned and went to the ottoman to retrieve two cushions, as I dropped my pants to step out of them and I sat in my usual swivel chair. She dropped the cushions on the floor between my feet. As I sat there with my cock in hand, lightly stroking it to keep it interested, Jan knelt between my legs.
“Maybe you could take off your dress,” I suggested.
“I’m not doing all of the work,” she said with a chuckle. “You could help,” and she raised her arms up over her head.
I grabbed the waist of her dress and pulled it up over her head. Jan now knelt there between my legs, naked with those beautiful tits and legs in my view. I was firm now, but my member wasn’t yet fully hard.
Jan wrapped her right hand around the shaft. As she lowered her head toward it, she stopped, tilting her head to the side, looking at it with a curious expression.
“I like this nice smooth head,” she said as she touched the tip with her left hand. “How do you want me to start? Sucking the head? Licking the shaft? Or licking your balls?” Her left finger was sliding softly along as she touched to emphasize each part in her teasing way.
“You could start by sucking it.”
She finished lowering her head toward it as she used her hand to guide me into her mouth, and she stopped with just the head fully inside her lips. I felt her tongue teasing the underside of the head. Then slowly she continued lowering her head down, the length of the shaft disappearing between her lips until she had half of it in her mouth. Her fingers were still wrapped around the bottom half of the cock as her lips met her hand. She pulled her head back up until the tip was almost out of her mouth, then she suddenly and quickly drove her mouth down again taking it back in.
Her first few head bobbing motions were this quick down and slow withdrawal. Then her pace began evening out. She just bobbed her head down and up on me at a steady pace.
A few seconds later, she sat back to tilt her head while keeping my cock in her mouth so she could look up into my eyes. My eyes went wide as I smiled in appreciation. Then she looked back down to focus on her task at hand.
Jan kept her right hand wrapped around the base of the shaft, her lips meeting her hand with each downward drop of her head. She soon began stroking me, with her hand moving up and down the shaft between the base and her lips, she continued awkwardly bobbing her head. She then started stroking faster than her head bobs, before getting in sync. She started moving her hand in time with her head, keeping her hand in contact with her lips. That hand-mouth combination felt fantastic on me.
After a minute of this, she sat back on her heels lifting her head off my cock, just stroking it with her hand. She switched hands to continue stroking at the same steady pace with her left hand, before dropping her head back to suck it.
This continued for another minute or two, and I anticipated her boredom with this activity soon setting in. I expected her usual sudden suggestion that she should lie down for me to fuck her. But I smiled and said “Your non-stop sucking and stroking feels great. He’s getting closer to cumming.”
“That’s what I need,” Jan said, “feedback…so I’ll know what you like.”
“I like your sucking and stroking it just as you are,” I said. I put my hand lightly on the back of her head, to give her the suggestion I wanted this to continue. I could feel the cum rising up my rock hard member as it was preparing to explode.
Jan glanced around. “I don’t see any tissues. What am I going to spit it into?” she asked.
With her right hand, she picked up her discarded dress next to her and brought it under her chin. “I can use this … It’s washable.” But soon, she dropped the dress into her lap to shift hands again.
It took at least another minute or two as Jan continued to change positions. Using her right hand to stroke me, she was moving her mouth in unison with her hand as she bobbed her head. She shifted to her left-hand stroking as she looked at me, then more of the head bobbing on me, and I felt the pressure building in the head.
I stood up from the chair to stand in front of her with her right hand still stroking me. Placing my hands on the back of her head to lightly keep her from getting up, I helped by pumping my hips toward her mouth, shoving my cock into her gorgeous lips as I face-fucked my wife.
Jan sat back on her heels and tilted her head back. Still rapidly stroking me, she opened her mouth and kept the tip of my shaft at her tongue. Her eyes locked on mine as I smiled down at her. This was the erotic sight I wanted to see; my wife kneeling in front of me as she jerked me off into her open mouth.
“Oh, yeah! That’s it. Just like that!” I said.
Jan stroked the shaft just a little faster, keeping her mouth in front of it. She would try to look at my cock, then shift her gaze back to my eyes. As my breathing quickened, her eyes glistened with excitement, and I saw her other hand move down between her thighs to rub herself. She took me back into her mouth, closing her lips around it and began moaning, with her other hand moving faster below her.
Watching her in that position as she knew what was coming, pushed me over the edge. “That’s it!….I’m getting very close…Oh…Ohh…Aggghhh!”
She opened her mouth again so I could see it when I let loose the first of several shots. Her lips were open in a wide “O’ with her tongue under the head of my cock, and she tilted her head back a little further. I kept my hand on the top of her head as several waves pushed more of the cum out of me. Jan just kept her mouth there, holding the purple tip over her tongue and I could see the thick, white fluid slide across and down from her tongue, pooling behind her bottom teeth. Her head was tilted back enough to keep it from dripping out from her bottom lip.
When the waves subsided, I dropped my hands from her head. I wasn’t holding her there. She could have easily moved away at any time. But she took the hint I wanted her to stay there.
Jan pulled her head back, tilting up to look at me. With her mouth she swirled her tongue around to show me the thick white liquid still there. Closing her lips, she bent her head slightly forward and made an obvious show of gulping, before looking back up at me and opening her mouth to show me she swallowed.
“Not bad this time,” Jan said rather cheerfully. “Maybe it was due to not shooting directly into my throat, so I didn’t gag on it,” she said, as if analyzing the experience.
Then I offered her my hand to help her stand.
Bedtime
Jan is an unusual woman. She’s not possessive and demanding of hugs or cuddling after sex. Her attitude is always ‘Okay, we’re done.’ Then it’s ‘let’s move on to something else.’ So, there’s never any hugging or cuddling after we have sex, or after she gives me a blowjob like this. It’s just done, and time to move on.
“That was fantastic,” I said. “I love seeing you in that position.”
“I know how much you like me doing that,” Jan said. “So, are we even now for me getting together with Ray? No Brenda, right?”
“We’re okay,” I reassured her, and paused before adding. “… I know that you could have fucked Ray at his hotel, and still come home to take care of me, too. Women can have far more sex than any one guy can give them. But we’re in this marriage and the lifestyle together. We do things we both agree on together. If you don’t want that, then it’s like you say: ‘We all make choices.’ If you want to forget that and you ever go off on your own, then it’s just fair that I will, too. There won’t be any warnings or negotiating. After you do it, I can do the same thing whenever the time’s right for me, forgetting about us.”
“I know,” Jan said dejectedly, “no double standards.” After a pause, she softly added “… You were flexible and that was something special you did for me this evening. And I don’t know if any other husband would have been as thoughtful. I like what we have, together. Thanks for being the best husband. Now let’s just go to bed.”
“Okay,” I said.
As we walked toward the bedroom, the visions of my gorgeous wife kneeling there with my cock shooting into her open mouth and that image in the mirror as she was getting fucked in the ass in our DP started getting to me. But even if I could get fully hard again, fucking her would have to wait until morning. I didn’t want to spoil the mood.
Thinking back to my conversation earlier with Ray, if my wife ever asks me about it, I’ll tell her the truth. But I knew it would change her relationship with him. So, I’ll leave that for her longtime friend to reveal to her, when he feels the time is right.
When we were ready and getting into bed, Jan propped herself up on her right arm, her head off the pillow, saying, “I want your shoulder tonight until we go to sleep.”
“My shoulder’s always there for you,” I said, as I reached my left arm out for her.
She laid her head on me, moving in close to snuggle.
“I love you,” she replied softly, as she ran her left hand over my chest.
“And I L-word you, too,” I replied, pulling her in closer against me.
######
Author’s Postscript:
Ted and Jan dating and their adventures when he was away at the university are in the first three Lifestyle series chapters, starting in “Lifestyle Ch.01: A Geek Beginning”. This also shows their first date.
The details explaining Jan’s occasional desire for anal sex and what prompts her self-reliant attitude is best described in the story “Lifestyle Ch. 11 — Demons Past”.
This main couple’s introduction to the world of swingers is in “Lifestyle Ch. 05: Mentors”.
Jan first violating the same room rule, with Ted allowing her the hall pass during a house party is in Chapter 9, the second half of “Lifestyle Ch. 08/09: Clubs/Parties”.
And Jan’s situational Bi experiences with other women develops slowly through several chapters, beginning with chapter 9, and is also shown in standalone stories “Her Bucket List: Strip Club” and “The Real Gift: Her Fantasy”.