Her First Hall Pass

Anyone remember Craigslist Casual encounters?   It was early 2000s when Craigslist Casual Encounters was the go-to cruising spot for swinging couples, cuckolds and the bi-curious.  It was also the go-to for many flakes, and it was rare occasion when CL paid off (less than 6 times). That still did not discourage me to check MW4M listings regularly, looking for that unicorn swinging couple.  
 
One particular couple from Florida posted blurry nude pics of them standing with arms around each other and wrote "We are a married white couple looking for an  erotic experience with a well-hung, fit, dominant male.  Diana is 38, Dave is 40, both bicurious and submissive.    We are real, discreet and very selective, we expect the same from you. In order to be considered, please send nude pics and propose a DETAILED scenario.   Finalists will be asked to interview on cam chat, where we will get to know you better."
 
I was on business travel staying in a hotel and took a few pics standing naked in front of the hotel mirror, shaved cock in various states of arousal. I attached them to a message that read.  "Nice to meet you, Tommy here.  I normally only provide nude pics when I receive them first, but will make an exception for you two since I like your attitude.  As you can see, I am a well equipped stud with an 8" baby-maker and gym built body." 
 
"The scenario I propose is for you both to be my personal sex slaves.  This will entail following instructions first through pic exchanges, then on camera, then in my hotel room if you both prove to be worthy.   With that, I want you to both immediately shave your pubic region into a landing strips, then sent me pics with a sign in your hand saying 'for Tommy'. Diana, I want you to pull your panties down to your knees and Dave I want you fully nude and to provide a frontal with Diana standing behind you pinching a nipple with one hand and holding a finger into his lips."
 
I clicked send and poured myself a whiskey, kicking myself a little for being so forceful with my demands.  But it was the "submissive" keyword that gave me hope this was what they wanted.
 
Within 30 minutes a reply came in with two pictures attached.  The first was Diana in a red bikini top and bottoms pulled down to her knees.  A cropped red bush extending from clit to just under her navel.  I could see her nipples were rock hard and knew she was excited as she was arching her back slightly.  Her face was slightly blurred out but I could tell she was very attractive, with blonde hair in pigtails.    
 
The second pic was of Dave standing with a cute semi, pubic hair buzzed and shaped just like Diana's.  He did have a hard swimmers body, and his cock was semi hard.   Diana was behind him hidden, but as I directed was pinching his nipple with her red fingernail polish with one hand and  the two fingers of the other hand stuck into his mouth as he sucked.     Wow, he did it!  I guess the ball is in my court now
 
I drafted up another email with a video cam chat link for them to join, reminding them they have 20 minutes to join otherwise I'd disappear forever.  I stripped nude and put on a white terrycloth robe that the hotel leaves for guests, leaving it slightly open so that I could have full access to my cock on display if they showed up.
 
Within 10 minutes I hear a video call coming in and accept. The video was not yet turned on which gave me a chance to give their first instructions. "Hello, Dave and Diana, you both look very sexy and I love that you were compliant.  I want to hear your voices first, so please introduce yourselves and tell you what want from this."
 
Dave introduced himself in a nervous voice, saying that both he and Diana are very excited to please me.  Diana then introduced herself and suggested they should be spanked for all of the dirty talk they had after seeing my pic.
 
"OK, it's video time.   Turn it on!"  The camera came into focus with them both kneeling on their bed wearing exactly what I told them.  
 
"Dave, pull Diana's tits out of her bikini top."
 
He moves behind her and lifts the bikini tip up, her milky tits and big nipples spilling out.  
 
"Now Dave, take off her bikini bottoms and stand her up so I can check her out better."
 
Dave takes off her silky and places them on the bed, grabbing the phone that they are filming with.  Diana stands up and turns to wiggle her ass in the camera while Dave films.  
 
"Dave, spank her ass hard."  
 
She gives a little aroused shriek as I hear a crisp slap on her ample buttocks.  He gives hear a few more swats until her shrieks turn into moans and her ass turns pink.
 
"Now Diana, turn and hold your tits in both hands, try to suck your own nipples."
 
Diana does as she is told, holding her breasts and licking each nipple one at a time.
 
"Very good, now Diana take the camera and film Dave."
 
I noticed Dave's nipples were as hard as Diana's and asked him why?  
 
"Um, well it's a little cold in here and I'm quite aroused," he stammered. 
 
"Well, I want you comfortable, so go ahead and  put on Diana's bikini and see if that helps."
 
I hear him and Diana both gasp and hesitate.
 
"Dave, you already shaved your pubes it looks like you have a pussy.  NOW get dressed!"
 
Dave still had the red bikini bottoms in his hands and fumbled for a minute to find the waistband and slip them on.  Diana reached behind and untied her bikini top, then helped Dave get it on.  Just before I asked Diana pulled the bottoms up hard, giving him a power wedgie that left him looking like he was wearing a thong.
 
"Wow, you look like a super hot sissy Dave.  Do you feel feminine?"
 
"Yes sir I do". 
 
"Well then lay on your back and masturbate as if you were Diana.  Do it just like Diana does."
 
Dave lays back and shoves his hand down the front if the panties simulating rubbing a clit and fingering a pussy.  His other hand twists and pinches his nipple.
 
"Diana, put two fingers in his mouth and tell him to suck my cock."
 
Diana smiles with a devilish grin and does exactly that. "Suck Tommy's cock honey while I watch."
 
Dave is breathing hard and drooling on her finger... mouth making satisfied sounds as he sucks.
 
"Okay, that's great. For the final video I want Diana to sit on your face Dave as she faces the camera and talks to me."
 
Dave lays back and Diana eagerly lowers her pussy on his face... Her tits are swinging back and forth and nipples rock hard as she moans and wiggles.
 
"That's right, eat that wet pussy good Dave.  Lick her tight ass too while you are down there."
 
Within five minutes Diana is moaning with orgasm, looking right at me, tits shaking.
 
"Wow, that was hot!  OK now both of you stand up and face the camera. I don't like to see anyone not get off, so Diana I want you to jerk your husband off keeping his cock in those panties. Make him cum in them and then both of you go to bed just like that.  NO fucking or other sex, tomorrow we meet in person."
 
Diana gets on her knees in front of him and engulfs his panty-clad cock in her mouth.  He moans and holds her head, bucking as she coaxes the cum out of his cock staining the panties.
 
"Excellent, you two pass.  Go to sleep and tomorrow we will plan the next phase."
 
They both look surprised and a little disappointed that it is over.  I kiss them both good bye and promise to contact them in the morning.
 
####
Let me know if you like this story and whether I should write part 2!
 
 
 
 
 
 
 

My fantasy has always been to watch my wife get fucked by another man. We have been with another woman before which is a whole story in itself that I’ll tell you about later.
 
One night several years ago my wife and I had gone to a club. Not your ordinary club, but a good club for swingers and singles. The night had started out rather slow and we were not finding any action that I had hoped. My wife knows what she wants and that is what we go with. And that night we found what she wanted and it was such a great experience she knew she wanted to do it again. She had gotten fucked by a black guy and she had enjoyed it. So, when we got the chance, she wanted to try it again.
 
Being at a swinger’s club isn’t really her thing, but fucking in front of people or listening to them fuck is a big turn-on for her. Since we don’t live close to any swingers’ clubs or anything of that nature, we don’t get many opportunities to do anything like this.
 
A couple of years ago we got a chance to go to another club. Yes, one of those clubs. We were looking for a little fun and hoping to find something as good as the last time we were out. We talked to many people as the night went on and my wife was trying to figure out what we were going to be doing to have fun that night. There was a hot blonde that was interested in us and kept on grabbing my cock which my wife was loving because this was getting her going. My wife and I decided that this was not what we had in mind for tonight, so we just kind of let that slide and we went on to pursue something else. She said she would know it when she saw it.
 
My wife had put a couple of drinks down and was feeling pretty good now. She was a little more daring and said she wanted to go change outfits like she did when we had been to a club previously. We had brought the very same sexy outfit that was see through, so she went and changed into it. When she came back out, there was not one guy's eyes on anyone but her. Even the women were looking on in awe. She is a beautiful woman that knows how to control a room.
 
One guy came up to me and told me he was jealous. He said he would do anything to get to fuck my wife, but she just didn’t feel right with him, I guess. As we were standing around, in came this well-built younger black guy and I think she almost came right there. The look on her face was almost mind blowing. She got this horny grin and told me she was ready to start our night. As he walked by her, she gave him this dirty smile and took her hand and rubbed down by her cunt. He stopped walking and came over to her and asked if he could help her with anything. She just smiled and said that I think you already know what you can do. They danced around a little bit, but I could tell she couldn’t take it anymore, so she quickly unzipped his pants and took out his cock and grabbed it and lead him into another room like a dog on a leash.
 
I stayed back a couple of minutes to give them some time to get to know each other. When I did finally get to the other room, they had already undressed and she was sucking his cock. It was larger than mine. Not much longer, but thicker. I could tell she liked it.
 
My wife had picked a room where people would be able to watch if they wanted to. I stayed back in the wings and was kind of hidden so she really didn’t know I was even there.  As I watched my wife in action, I could tell she was enjoying every second of this guy’s cock. She was sucking it like there was no tomorrow.
 
Now it was his turn to return the favor. He got his face down to her pussy and started licking like it was candy. She was turning red and I could tell she was already about to cum. She was squirming and shaking and he was getting her cunt all ready for his big shaft. But before he fucked her, he now spread her legs out and started fingering her pussy to the point that she started squirting fluids all over the sheet they were laying on. It was like the flood gates had opened up and all the juices were flowing.
 
She finally had all she could take because I’m sure she had cum multiple times already and I could tell she just wanted to have him inside her. I heard her say to give me your big, black cock. He asked her if she wanted him to put on a condom and she told him no, she wanted to feel him inside her cunt.
 
He took her and spread her legs wide and slowly inserted his bbc into her tight cunt. She told him to go slowly because she said it was so big that she needed to get used to it. After several minutes of the slow movement, she said she needed him to fuck her harder so he started to go full penetration into her dripping wet cunt. She was telling him how good his cock felt, and how she loved fucking him.
 
They switched positions multiple times with her sitting on top of his cock and riding him like she has never ridden before. My wife took his whole cock inside of her as deeply as she could, rubbing back and forth and cumming time and time again.
 
They finally switched back to missionary style and were fucking hard when I heard her say to him, she wanted him to cum in her pussy. She said she wanted to feel his cum drip out of her pussy all night long. When he heard her say that, he started to pick up the pace and finally started moaning and said he was about to cum. My wife was now cumming herself and as he shot his load inside of her, she started squirming and shaking with every pulse of his exploding cock. Her body was red from all of her orgasms, and I could tell she was getting worn out. They had gone for almost 40 minutes of nonstop action. Not to mention that all the other people that had gathered around to watch started going to other parts of the place as they had gotten a show that they would remember forever.
 
When he pulled his now soft cock out of my wife, I could see the cum dripping down her ass. She was getting what she wanted, I guess. She would be able to feel his cum dripping out of her the rest of the night. But I didn’t realize that she was not done yet. She wanted more. My wife took his cock and started sucking on it again. I guess he was young enough that almost instantly he got hard and she took his cock and guided it into her cunt and said she needed more of his cum. He fucked her for another 10 minutes until he exploded with more cum inside my wife’s pussy again. Again, as I watched the cum drip down her ass, she was getting what she wanted. She was going to feel this the rest of the night.
 
They both started cleaning up a little and I slowly came out of the crowd that had gathered. She saw me and gave me that dirty little smile she sometimes gets. My wife asked me if I had enjoyed her show. She said she needed to have a little more cum in her pussy tonight and she now wanted mine. Her new little friend just kind of sat back in the corner and decided to watch us.
 
I knew I wouldn’t last long because I had almost cum multiple times just watching her. With some of the crowd still watching I got undressed, and slid my wet with pre-cum cock into my wife’s cum-loaded pussy. I fucked her until she started cumming. Her cunt convulsed so hard that it squeezed my cock and made me start to cum. I came in her pussy, mixing my cum with my wife’s new fuck buddies cum. I pulled my cock out and watched it all slowly slide down her ass. She got up and went over to our young fuck buddy and she gave him a long passionate kiss and said thank you for such a great time. He gave her one last little finger fucking and handed her a card of his if we were ever in the area again.
 
He left after he got dressed and we got cleaned up and went out to the main room. I had multiple people including women and even the bartender say that my wife was one of the women they would like to fuck if they ever got a chance after seeing her in action. I guess I’m the lucky one here.
 
Later that night when we were driving to our resort, she slipped her hand down pants and put her fingers in her pussy. She brought them out and rubbed them on my face. She smiled and said we gotta do this again sometime as we pulled into the parking lot to call it a night.
 
And what a night it was.

True story that is still in my spank bank.
 
This was way back to 2013, when you could find horny couples on Craigslist and Backpage.
 
I was on business in St Louis, horny in my hotel room browsing through casual encounters to see what I could see.  Replied to a few cuckold couple posts, most were just horny dudes hunting for pics. Then I ran across an ad "St Louis couple looking for DP fun".  I replied that I was interested and had a hotel room downtown.  
 
Cindy replied back when I asked her what they had in mind. "Splitroast me, tongue on my clit when I'm getting fucked, double vaginal, double penetration. You can spank me, pull my hair,  pinch my nipples if you get me hot enough." She then sent a pic of the two of them - Dave took it while he was fucking her doggie while she was sucking a huge dildo looking at a mirror. I sent a nude pic of me and anxiously waited a reply. She replied they were ready for the next step and would be downtown in one hour.
 
We met in an Applebee's right next to the hotel to see if we mutually wanted to take it further. They walked in looking like a normal suburban couple. She was definitely a BBW girl and did most of the talking. We got to know each other over a drink and quickly came to the conclusion that none of us were psycho killers and I gave them a key while they went back to the car to retrieve lube and condoms
 
After 15 minutes I hear a knock then the door unlock.  They both walk in smiling and comment "nice hotel." Cindy takes off the jacket she was wearing to reveal a lace teddy and fuck me boots that she must have changed into. She walks up to me confidently and gives me a wet kiss with lots of tongue as Dave watches and then joins in. Cindy then turns to make out with Dave while reaching back and fondling my cock through my jeans. I whisper in her ear, "Get on your knees and suck your husband's cock." Before I know it, Dave whips out his cock which is bigger and thicker than I've ever seen in person.  I get on my knees next to her and hold her hair back so that I can watch her blow him up close, moving her thong aside and fingering her sopping wet pussy loudly. She kisses me and I taste cock for the first time, albeit indirectly.
 
We then move to one of the two queen beds and put Cindy on all fours. I pull down her panties to her knees and give her big ass a few playful smacks. She moans and spreads her legs a little wider, showing us her wet pussy and I shift my spanking to it. She shrieks and moans as I finger her pussy. Dave takes off her bra freeing her huge tits with big red nipples. I grab one and then another... tweaking her big nips to make her moan some more. Dave is sitting back stroking his big dick looking right at her. I don't think we ever made eye contact.
 
Dave then throws two condoms down on the bed which is my cue to fuck her. I quickly pull it on, grab her hips, groan, and plunge into her wet pussy. Dave pulls her hair gently but firmly so that her face is in the air and her tits start swaying. I watch as he slides his cock down her throat and hear her give him the sloppiest BJ ever. Full on licks, lip pops, sucks his balls and fingers his ass as I fuck her harder, trying not to cum.  Then I feel as if I'm going to cum and suggest we switch positions. Cindy deep throats me and Dave starts to fuck her pussy hard as all hell making her titties bounce in all directions. She looks up at me and says, "This is so fucking hot, I love it." I grab her hair with both hands and start to face fuck her good.
 
All of a sudden she starts trembling all over and moaning guttural. She spits out my cock and tells us she is going to cum. Cum was an understatement, she literally gushed girl cum all over my hotel bed. I've never seen such a gush, it sounded like somebody flushed a toilet.  
 
"Sorry about the bed, but I told you I was a gusher," she says.  I suggest we all move over to the other bed and pull her on top of me. She is so wet that my pubes are soaked immediately. Dave pushes her forward onto me not too gently and we kiss as he works his cock inside her asshole. She starts to buck wildly and again tells us how hot this is. Her pussy is so wet that my cock falls out with every thrust into her ass. I suggest we switch positions and push into her ass as Dave fucks her with that monster cock. I spank her with every thrust talking dirty to her which sends Dave off to cumming inside her. We collapse for a minute and Dave excuses himself to get a drink of water. We are all sweating profusely.
 
But I'm not done with Cindy yet, and lay on her missionary, spreading her legs wide and fucking her well used, stretched pussy like mad. I fall out a couple times and then decide to put my slippery hard cock into her ass, butt fucking her missionary. I think this was a first for her, since she calls Dave in to check it out. He watches and nods then leaves the bedroom to sit on the couch outside and listen.
 
I give it to her for another 30 minutes easily, fucking her ass and rubbing her clit. She cums again and again but my cock gets desensitized due to the rubber and I can''t cum. As she is getting wore out, she asks me what she can do to get me off? I tell her that I don't think I can cum from fucking or sucking, come sit on my face and I'll jerk myself off. She looks at me devilishly and climbs right on top, lowering her big cunt right on my face, holds my head with both hands, and slides back and forth, giving me an opportunity to lick her ass. After two minutes of this I feel my cum boiling in my nuts and explode a huge load on my stomach. She smiles, licks some up and then snowballs me! Another first.
 
I lay there not believing what happened as they get dressed and pack up. I email her after to check if Dave was OK with all of this and she says sure. I never hear from them again.

This all started around forty years ago when my wife Beth and I had dated for a few years then married. It wasn't long after we married that I introduced her to her first big realistic porn star dildo.  When she first saw it she laughed and said, "That'll never fit in my pussy, are you nuts?!" But she agreed to trying and found not only did it fit but she really enjoyed it. She was amazed by how much she enjoyed it.  So much so that she requested I use it on her quite a lot. She also discovered she enjoyed big cock porn, she was fascinated by it. Soon was I combining using a huge dildo on her at the same time she watched big cock porn, this led her to experience huge orgasms. She couldn't get enough. She was finally exploring her sexuality and expanding her outlook on sexual pleasure.
 
One night after some really hot sex I  questioned her if she ever fantasized about fucking other men, especially well-hung men. She responded that of course she did, stated that most women had this fantasy, and she believed it was quite common. So I pursued it further and asked her if she wanted to try another man's cock and how much did she really desire to do it? She said that it sounded exciting and fun but she would never do anything to endanger our marriage. I said,  "What if I told you that I wanted to watch you have sex with another man, one that had a really big cock. Would you then consider it?" She laughed and said she'd be game if it was something I was serious about and really wanted her to do. She said, "Come on, let's be real. It's exciting and fun to imagine it, but to really do it? Please! That's a major game changer."
 
So I said, "I'm very serious. I've watched the way you enjoy the dildos especially while watching big cock videos. It turns me on big time seeing how excited you get and how many times you climax from doing these two things at the same time. I want to watch you do it for real. No BS, just watching you getting slammed by a big cock would be a huge turn-on for me. So what do you really think now that you know that I'm serious and am giving you this opportunity?"
 
I could see her giving it some serious thought, she didn't get mad or upset at me or the idea, no resistance whatsoever to my request.  The more she considered the idea the more it appeared to me that she was very intrigued with the idea and it excited her.
 
She started asking all kinds of questions, like wouldn't I be jealous, or think the worst of her, or what if she really enjoyed it and wanted more or didn't feel comfortable screwing another man, then what? Were there any rules and what were the consequences? Was I absolutely sure that I really wanted her to do this, because once done there was no going back!
 
After she finished asking everything she had concerns about I answered all her questions and we talked about the rules/boundaries we would have in place to keep it fun and exciting without any reservations or guilt. This was to make sure she fully understood my concerns and alleviate all of hers as well. It seemed she came to a decision at which point she smiled and enthusiastically said yes, she'd do it! Did I have someone special in mind she wondered? She said she had to agree to my choices for her sexual escapades or it wasn't gonna happen.
 
 I then informed her I was thinking of Bruce. Beth squealed with glee, she admitted she has had fantasies about Bruce for some time now and I couldn't have picked a better choice for her first time. She would absolutely love to fuck Bruce. She said she was getting wet thinking about sex with him.
 
A few days later I met up with Bruce for an after work drink. As we enjoyed several drinks we talked a lot. Soon I steered the conversation towards my wife Beth. I asked  Bruce to be honest and tell me what he thought about Beth. He admitted he thought Beth was smokin' hot. She had a killer body and was just gorgeous, always was friendly, and liked flirting with him when they were together. I asked him if he' ever had the chance would he consider having sex with her? He looked a bit concerned by my question but answered yes, he wouldn't hesitate to take advantage of such an opportunity. So I told him that Beth really wanted to have sex with him, and that I was okay with them hooking up. I explained that was my kink watching her get fucked by other men, it really turned me on. Bruce considered it for several minutes then said okay sure, he'd love to fuck Beth. Just give him the details when we're ready to make it happen.
 
When I got home I told Beth about my conversation with Bruce and what he said. She looked startled and said she couldn't believe I did that. So I asked her if what I did was so wrong and did she still want to go through with it? She excitedly said Oh hell yes she did, and no I wasn't wrong! So we made plans and set a date for Beth's first cock. 
 
The night arrived finding Beth both excited and hot with anticipation. She was dressed to kill showing off her sexy body wearing no underwear. When Bruce knocked on the door I answered it and escorted him into our house. Beth entered the living room and gave Bruce a big hug pressing her chest and pelvis into him and then kissed him on the lips. Bruce kissed her back and he sat down pulling her on to his lap. Nether one of them wasted any time, tongues going everywhere, hands exploring and groping each other, clothes coming off. Soon they were both naked and Beth got a pleasant surprise, Bruce was very well hung. She giggled with delight.
 
Beth took Bruce's hand and led him to our bed. She pushed him down on the bed and went to work on Bruce's big cock giving him an enthusiastic blow job. After a while Bruce flipped Beth on her back and went to work on her pussy and clit. Beth orgasmed in minutes, fully enjoying Bruce's skilled tongue. I stood in the background watching the show.
 
Soon Bruce moved into position between Beth's legs. As he rubbed his cock against Beth's open pussy and clit she responded with loud moans and started pressing her pussy against Bruce's cock. As he slid his huge cock into Beth's pussy she had a big climax. As he went deeper he increased his speed and Beth climaxed again. She was enthralled with his big cock pumping her pussy, she was moving her hips and swearing, telling him his cock felt so good. She looked over at me and said she loved how good his big cock felt inside her. She told Bruce to stretch her pussy good, to fuck her hard. She was in sexual ecstasy, a place she'd never been before. Her facial expressions showed pure bliss and the sounds she was making were hot as hell. I never seen her so turned on, she must of had a dozen orgasms, many of which were huge.
 
They fucked each other hard for a good twenty minutes then Bruce erupted into Beth's pussy, filling her with his cum. This gave Beth another climax. Afterwards he laid on Beth for a minute then rolled off her. He'd destroyed her pussy, it gaped open with his cum dripping out of her. They kissed and he got up to dress while Beth laid there spent. She looked at me and smiled big time. She said, "Your turn!", so I took sloppy seconds and enjoyed it beyond belief. Bruce watched us have sex then commented that watching real sex was so much hotter than any porno ever could be. He understood my enjoyment of watching my wife fuck other men. He said he'd like to do it again and Beth was all for it. So they made plans to hook up again. Then Bruce left.
 
Beth and I talked about how well things went, and how she wasn't prepared for how much she enjoyed his big cock. It was mind boggling! She thanked me profusely for asking her to do this, the opportunity to experience such awesome sex. She says she'll never be the same again and is looking forward to more big cock sex. So our new lifestyle began.