My Wife’s First Time With My Best Friend

Recently I was at home and I heard my wife’s phone ring. She was gone shopping with her friend so I picked it up and it was a message from a high school friend Dennis. He had been a boyfriend on the block. I touched the message and it said -
 
"It’s been fun flirting with you on the phone but you still have not sent a naked picture that you promised. I know you said you have DD's but I have not seen you since high school. I would love to see them. It cold out here in South Dakota and your hot body, even a picture, would be fantastic!! I love nasty chatting with you. A spicy one would be fun, after all I sent you one of my cock and you said, 'Mmmm, I love your cock, always did!!' Waiting for your pic honey chat soon."
 
I heard her car pull in and I put her phone down on dresser where she left it. She came in and asked if I had seen her phone. I told her I had been in garage but I thought I saw it on the dresser this a.m.
 
She hot-footed to the bedroom and got her phone and, relieved, she said, "Man, I thought I lost it!!" I said, "Glad you did not!!"
 
She has a smart phone and watch and knew she had gotten a message. 

Which one of the two are you more like?
 
Myself, I'm more of a Voyeur. Just something about watching gets me going!!!

Last year, my husband revealed that his biggest fantasy was me being a hot wife and fuck other men. He said it turned him on to see another man’s cock in all my holes.
 
A few months ago, he took me to an upscale hotel in Dallas, I finally gave him what he wanted.  He was the wildest Saturday in my life. 
 
First, he booked an in-room massage for me.  The masseur was a young, well-built black man.  As I laid on his massage table, he slipped out of his clothes.  I swear his cock hung nearly to his knees. At the end of the massage, he started rubbing my clit and fingering me.  He brought me off several times. He then moved closer to my head and started rubbing my tits, pinching my nipples, and fingering my cunt at the same time.  His semi-hard cock was within a foot of my mouth so I reached out and put in my mouth.  He instantly became hard as I sucked him.  He then grabbed my head and pushed his cock down my throat.  I soon felt and tasted his cum flowing down my throat. 
 
After he left, I texted my husband and told him to come up to the room.  I thanked him profusely and stepped into the shower while J laid out my clothes for the evening.  When I finished my shower, I saw my outfit J picked out.  It was a blue silk dress with chains with three chains across the back.  Obviously, no bra tonight.  He also didn’t pack any underwear as he wanted me to go “commando.” A new pair of stilettos accompanied the beautiful dress.  When I finished my makeup, I slipped on the dress.  The dress was very short, only 3 inches below my pussy.  The material was very clingy and you could clearly see my nipples and areolas. After I finished dressing, J told me an Uber was waiting for me outside to take me to a fancy cocktail bar about 4 blocks away.  He told me to sit at the bar and order a drink.  He would be along in an hour or so. 
 
I nervously climbed into the Uber.  As I slid into the back seat, the hotel door man got a good peak up my dress as it slid up my thighs.  Our sex life was beginning a new chapter. 
 
I walked into the bar and felt the eyes of every guy turn towards me. I sat at the bar and ordered a Manhattan. It didn't take long for the first guy to sit next to me.  Within 5 minutes, a handsome Hispanic man asked if he could sit next to me and buy me a drink.  I nervously agreed.  As we chatted, he scooted his chair closer to me and placed a hand on my thigh.  My bare thing!
 
He repeatedly eyed my body from top to bottom.  The dress that was hugging my body, and my swaying breasts.  I wore a gold necklace that hung just above my cleavage. He lifted my necklace up to look at it and brushed my breast as he did so. 
 
Shortly after another guy approached. He was also handsome & charming, but there was a bit of an edge to him. He bought me a drink, we chatted a bit, and this time I did feel excited.
 
His name was E and he owned his own business. He was very handsome so I really didn’t care about that information.  As we started our second drink together, husband arrived.  I now knew where this was going. 
 
The three of us had a nice dinner and did some dancing.  E- then asked if I wanted to get out of there. I knew what that meant, so I eagerly said yes.
 
The three of us to our hotel room.  J made us some drinks while E started to caress and kiss me.  The drapes to our room were open.  As admiring the beautiful Dallas skyline, E slipped my dress off which sank to the floor.  He asked me to keep my shoes on.  I watched our reflections as E kissed me all over.  He lifted me up and pressed me against the window. The glass was cold against my bare breasts but I didn’t care as E’s hot breath kept me warm.  Soon he pushed me onto the bed.
 
I pushed myself away from him, turned around, got on my knees and unzipped his pants, revealing a nice, uncut cock. I gave E the experience of his life, sucking him off in front of the window. I started slow and methodical, but after warming up starting sucking him at a feverish pace. He groaned, occasionally telling me how good it felt and how I was a good little cock sucker.  His hand grabbed my head, pulling me deeper into him. I took every inch of him in, then felt his cum shooting into the back of my throat as he gave a deep groan.  He held me there as I took all of his cum in, swallowing every drop. As his half hard cock left me mouth, I looked up at him, giving both him and J a mischievous grin.
 
He took forced me back onto the bed and started licking my cunt. I felt my first orgasm of the evening come over me as he licked my cunt, tongued my clit, and fingered my asshole. 
As I came down from my orgasm, I felt his hard cock slip into my soaking wet pussy. He asked if he needed a condom.  I said “No, I want your raw cock in me."
 
His cock started sliding in and out, in and out. The whole time he whispered in my ear, telling me how good my pussy made him feel... how tight it was... how wet it was. How naughty of a girl I was for taking in the cock of a man I just met.
 
He moved me over onto my hands and knees. He kept sliding in and out of me, dominating my pussy as he fucked me hard.  "Oh yeah, fuck me." I said to him. He started thrusting harder into me. I felt my second orgasm of the night building. "Don't stop, I'm going to cum."
 
My body gave out as my second orgasm overtook me. Holy shit did that feel good. Just as I began to come down from it, I felt him give a big thrust and cum deep inside my unprotected pussy.
 
He collapsed onto my back, his heavy body pressing me into the bed. "God you're so sexy," he growled into my ear.
 
We laid together in silence on the bed as J watched us basking in the afterglow of our fucking. I then felt J on the bed.  He was on his back with a nice erection.  I took him into my mouth then J said, "Ride me please."  I straddled J and started riding his cock. 
 
J then grabbed my waist and pinned me.  I then felt E working a lubed finger into my ass.  I slowed my pace and steadied my breath as I took his entire finger in my ass.  I bit my lip and waited for the next step.  I then felt E slip his cock into my ass.  I now had my husband in my cunt and my new lover in my ass.  The two men started fucking me in earnest.  "Fuuuuccckkkk..." I groaned as his cock entered me again. J and I did anal sex all the time, but this was a bigger cock than I was used to plus J was in my pussy making every hole tighter.  I simply hung on for the ride of my life. 
 
After letting my ass adjust to E’s cock, he started thrusting into me, very slow and methodically at first. He then started fucking me like his life depended on it.  It didn't take long until my most powerful orgasm yet overtook me. I let out a groan-scream as my ass pulsed around his cock.
 
E and J kept fucking me through my orgasm, gradually picking up the pace. Then the let out a groan and came inside ass and cunt. My holes were now filled with cum. 
 
It was the best Saturday of my life.  Counting the masseur, I took two loads in my mouth, two in my cunt, and one in my ass.  After E left, J and I cuddled and drifted off to sleep.  I had the sweetest of dreams.

Lately we have both been having a fantasy that I'm not sure how to make reality. I'm not even sure we want to.
 
Basically the fantasy is we both go out to the same vanilla club as singles. I do the single girl thing of flirting and dancing with hubby acting as back-up from across the room. At some point during the night I choose one guy and have sex with him in the parking lot. Hubby will be close to offer protection if something goes wrong but otherwise will not be known to my partner.
 
My question is 1) Do you think it is possible to pull this off safely? 2) Since we have always insisted on same room swinging would this damage our relationship? 3) Has anyone else had this same fantasy or actually gone through with it?

The following is a work of fiction, the product of my own pervy imagination. Enjoy.
 
"I'm just saying," Dan said quietly, "conference sex is a thing."
 
"Geez, honey," Jenn rolled her eyes. "It's a work conference, not one of your pervy fantasies."
 
The airport crowds flowed around the young couple, people drifting in and out of shops and food stands or making their way to the security lines that stood between them and their flights.
 
"Why can't it be both?" Dan grinned.
 
"Perv," Jenn growled, but the twinkle in her eye betrayed her amusement.
 
"All I'm saying is..." Dan started.
 
"... that if some guy tries to pick me up at the hotel bar, you're ok with me *fucking* him," Jenn whispered hotly.
 
"Well..." Dan flushed.
 
"You're a perv," Jenn replied with an amused grin. "Have fun with the house to yourself. Try not to spend the whole time I'm gone jerking off to porn."
 
"No promises," Dan grinned back.
 
<<<>>>
 
Lounging on the couch, Dan let the late night TV wash over him. He smiled when his phone rang.
 
"Hi, honey. How's the conference?" he said as he answered it.
 
"Boring seminars, pushy vendors, the usual," Jenn replied.
 
"Having fun?" Dan chuckled.
 
"Oh yeah," Jenn's sarcasm practically dripped through the phone. "I just love it. What are you up to?"
 
"Oh, you know... wild party, drinking, smoking pot, a bunch of naked coeds in the hot-tub begging to suck me off." Dan stretched out on the couch.
 
"You're bored and watching late-night TV, aren't you?" Jenn laughed.
 
"How did you know?" Dan asked.
 
"We don't have a hot-tub," Jenn pointed out.
 
"Fair point," Dan conceded. "What are you up to?"
 
"Well..." Jenn hesitated teasingly.
 
"What are you doing?" Dan perked up.
 
"I thought I'd go down to the hotel bar," Jenn replied.
 
"Looking for a guy?" Dan teased.
 
"Perv," Jenn laughed. "I'm meeting some friends for drinks... but..."
 
"But what?" Dan sat up slowly.
 
"Remember that little black dress you liked?" Jenn replied.
 
"Yes?"
 
There was a long pause, and Dan's phone chimed to announce an incoming picture. Glancing down he saw Jenn, standing in what was clearly a hotel hallway, reflected in a mirror. Her dark hair hung loose around her pretty face and brushed her shoulders, bare except for the spaghetti straps of the little black dress. It clung to her curves, emphasizing her fair skin, the swell of her breasts, her tight belly. The hemline lay just low enough to avoid being totally slutty but high enough to suggest wicked thoughts. Dan's breath caught in his throat. His sudden hard-on was almost painful.
 
"Wow," he breathed.
 
"I thought you'd get a kick out of that," Jenn's voice teased through the phone.
 
"Are you wearing panties?" Dan wondered aloud.
 
"Yes," Jenn laughed, adding, "perv."
 
"Take 'em off," Dan said.
 
"No," Jenn gasped, plainly shocked.
 
"Take your panties off," Dan insisted.
 
"No," Jenn replied breathlessly. "You know how short this dress is."
 
"Off. Right now."
 
"Right... Dan, I'm in a hallway. I can't." Jenn laughed shakily.
 
Dan said nothing, waiting. There was silence on the other end of the line. After a long pause, his phone chimed again.
 
Jenn stood, reflected against the mirrored doors of a hotel elevator, a tangle of thin, black fabric gripped in one hand. Her dress was hiked up just high enough to offer a teasing peek at her neatly trimmed pussy.
 
"Beautiful," Dan breathed.
 
"I'll call you later." Jenn's voice was husky. "Perv."
 
<<<>>>
 
"Damn time zones," Dan muttered to himself.
 
It was either terribly late or hideously early. He'd fallen asleep on the couch to the drone of the television, alternately watching old movies on Netflix and entertaining himself with fantasies of what Jenn, panty-less in her slinky black dress, might be getting up to.
 
The last thing she'd said was that she would call later.
 
Rubbing bleary eyes, Dan glanced at his phone.
 
There were several messages from Jenn.
 
The first was another picture that made him instantly, painfully, hard again. The picture, shot up below the hem of her little black dress, showed Jen's naked pussy, wet and puffy, between her two long fair legs. She must have been sitting on a barstool, her legs parted, holding her phone down by her knees.
 
JENN: Like what U C perv?
 
JENN: U up? Haha
 
JENN: Guy got me a drink.
 
JENN: OMG I think he saw me take that pic!
 
The last message was another picture, this one of Jenn sitting on a barstool, smiling, a drink in one hand while her other hand pulled her top down just far enough to flash a bare, hard nipple at the camera. Her legs were again spread, flashing her pussy too.
 
It took a moment for the significance of the picture to register in Dan's mind. She had a drink in one hand and was flashing a tit with the other. Someone else was holding the camera. Someone who had seen her take that upskirt pic. Someone who had bought her a drink. Someone who had snapped a pic of Jenn flashing her tit and pussy in a hotel bar.
 
The last picture had been received more than an hour ago.
 
Dan felt a strange twist in his stomach, nerves and maybe jealousy. At the same time, his dick was achingly hard.
 
His hands shook as he started to type out: Who took that? His finger hovered over the send button, then slowly he deleted the message, typed a new one and sent it.
 
DAN: Hot pic.
 
He stared at his phone, waiting. After an eternity, a minute passed. Then another.
 
DAN: U naughty tease
 
Another endless minute passed.
 
DAN: Fell asleep. U have fun flashing the bar?
 
After another minute, Dan realized that, despite the time zone difference, it must be late there too. Jenn was probably back in her room by now, probably even asleep herself. There were lots of good, simple reasons why she didn't reply right away. She might not even see his messages until morning.
 
He managed to force himself to wait almost a full four minutes before firing off another text.
 
DAN: U still up?
 
More minutes passed and suddenly his phone chimed.
 
JENN: CEnt tAlk call pater
 
DAN: U drunk lol?
 
DAN: Jenn?
 
DAN: U ok?
 
DAN: JENN?!?
 
JENN: C a 'll later
 
JENN: nifht
 
Dan stared at the strange texts, confused and worried. He went so far as to almost hit Jenn's number on speed dial before changing his mind. Drunk... or whatever she was... Jenn obviously would call him 'later.' Pushing her wouldn't help anything. He forced himself to put his phone down and go to bed. He needed to get some sleep. Right after he dealt with his raging boner.
 
<<<>>>
 
It was only thanks to work of his own that Dan managed to spend the next morning doing something other than agonizing about Jenn. Without the distraction, the simple fact of the several hour time difference probably would have driven him nuts. Instead, he actually managed to put his worries out of his mind and so didn't jump instantly every time his phone chimed.
 
Still, when she did finally call it didn't take him long to pick up.
 
"Hi, honey," Dan said brightly.
 
"Hey." Jenn's voice sounded oddly subdued.
 
"So, what do you have going on today?" He asked.
 
"Just more seminars," Jenn replied. She was nervous, Dan realized. He felt that odd twist in his gut again.
 
"So..." Dan hesitated.
 
"Yeah, I..." Jenn stammered.
 
"You got a little crazy last night?" Dan forced a smile into his voice.
 
"Yeah," Jenn replied carefully.
 
"Too much to drink," Dan said, offering his explanation as fact.
 
"No," Jenn snapped.
 
"Really, 'cause those texts looked pretty drunk," Dan insisted.
 
"I wasn't drunk," Jenn countered angrily.
 
"Oh, come on," Dan said. "You could hardly type."
 
"Yeah, well it's hard to type when you're getting fucked!" Jenn shouted into her phone.
 
Silence feel between them. Dan could hear distant chatter through the phone and wondered suddenly where Jenn was exactly. Probably walking through the hotel to her first seminar, he realized. Strangely, he found that part of his mind was wondering what the seminar was about.
 
"I'm sorry..." Jen stammered after a long silence.
 
"You're joking," Dan declared.
 
"I'm..." Jenn started again.
 
Dan hung up. His breath was coming in ragged gasps. His hands were shaking. He would have thought he was furious, but for one undeniable fact. His dick was so hard it was about to rip through his pants. He wasn't angry, he realized. He wasn't even jealous. All he felt was raw, violent, desperate lust.
 
His phone rang again.
 
He answered, "Getting fucked?"
 
"You'd said..." Jenn stammered.
 
"What were you doing?"
 
"Those fantasies you kept telling me about..." Jenn sounded close to tears.
 
"Shhh," Dan said soothingly. "Just tell me... when you texted me last night. That last time. Tell me why couldn't you type right."
 
"I told you..." Jenn muttered.
 
"No, tell me exactly what you were doing at that moment."
 
"Getting fucked," Jenn replied.
 
"Tell me," Dan insisted.
 
"What do you want to hear?" Jenn replied. "Do you want me to tell you I was on my belly. That the phone was in front of me, and I was trying to type while... while he was...."
 
"Was what?" Dan prompted.
 
"Was inside me. Was fucking me." Jenn said, her voice growing husky. "Was pounding from behind, so hard. So hard I couldn't type properly."
 
"He knew," Dan said. "About me."
 
"He knew." Jenn confirmed.
 
"You were..." Dan took a deep breath. "Fucking. When I texted, you were fucking another guy."
 
"Yes," Jenn said soft. "I was. I was fucking another guy."
 
"Who?" Dan asked, feeling surprisingly calm about the question.
 
"His name's Tim," Jenn replied slowly. "He's here at the conference."
 
"You met him in the bar," Dan said. "He's the one who took that picture."
 
"You saw... oh, right, the picture in the bar," Jenn said. "Yes, he took that. He saw me taking the pic I sent you. The upskirt pic in the bar. I didn't know he had at first. He came over and bought me a drink. He was nice. Flirty but not pushy. Then he said he'd seen me taking it. He asked who I was taking it for."
 
"You told him about me?" Dan felt a little shocked.
 
"Yeah, I did," Jenn admitted. "He asked about the picture, about why I'd taken it... and I told him about...
 
"You always go on about your pervy fantasies," Jenn continued. "About wanting me to... to fuck another guy. We talked about it at the airport. I took my panties off, right at the elevators. I didn't tell you: the doors to that elevator opened right after I took them off, a second after I sent you the picture in front of them. Two guys got off. They saw me. I know they did. They saw me standing there with my panties in my hand, my dress hiked up. They saw my pussy. They didn't say anything, but I know they saw. How could they not have?
 
"It turned me on. Riding down in that elevator, with no panties on. Knowing those guys had seen. It turned me on so much. So, when I got to bar, when Tim finally told me he'd seen me taking a picture of my pussy, right there at the bar... I was so turned on. I told him. I told him my man had told me to take my panties off. That you wanted me to flash guys at the bar. So, he offered to take another pic for me and I flashed my boob at him... and like, half the bar. I bet so many guys saw.
 
"I was so turned on... and Tim was nice... so, I told him. I told him your fantasy... about me fucking another guy."
 
"... and he decided to be that guy," Dan concluded.
 
"No," Jenn snapped. "I decided. You kept talking about your fantasy, and it became my fantasy. Tim was nice and he was flirty but even after I told... after I told him about the fantasy, he didn't push. He hinted a lot, but he didn't assume or insist. So, I decided. I invited back to my room."
 
"... and fucked him," Dan said.
 
"Yes," Jenn answered confidently, "I did. I fucked him. I stripped for him and I sucked his cock. He has a really nice cock, Dan... almost as nice as yours. He played with my tits and he ate my pussy and then... then he entered me and it felt so good. Oh god, Dan, it felt nasty and wicked and so very good. He fucked me and fucked me."
 
"He was fucking you when I texted," Dan repeated.
 
"He heard my phone. He stopped, to check it," Jenn replied. "When he saw it was you... he just flipped me over, face down, and pushed back inside me. He told me I should answer. It really turned him on. He just went wild. I think he wanted me to call you, but I texted instead."
 
There was another silence.
 
"It's really hard to type," Jenn added lamely. "When someone is fucking you that hard."
 
Dan laughed. Suddenly, unexpected, he just started laughing. He couldn't help it. He just laughed and laughed. Slowly, Jenn started laughing too, until finally the two of them were just laughing uncontrollably over the phone. All the tension between them bled away. Almost all. The knot in Dan's stomach, at least, was gone. His raging hard-on, he thought, was in danger of doing him serious injury.
 
"Are you... ok?" Jenn said as the laughter finally faded.
 
"Are you wearing panties?" Dan asked.
 
"What?!" Jenn replied, shocked. "Yes!"
 
"Well, take them off," Dan demanded. "Right now, take 'em off. Sluts like you don't wear panties."
"Dan!" Jenn exclaimed, shocked by his use of the word 'slut.'
 
"What, I'm a perv for wanting this," Dan said firmly. "You're a slut for doing it. In fact, I think no more underwear for you for the rest of the conference. No bra, no panties. Nothing."
 
There was a long pause, then Jenn replied, "Ok."
 
"So," Dan said. "Take 'em off."
 
"Dan," Jenn hissed, "I can't... not right this second. I'm in the hotel lobby."
 
"So, everyone in the lobby heard you yell about getting fucked," Dan replied.
 
"God." Jenn's embarrassment was plain. "I know, but I'm not taking off my panties for them."
 
She paused, "Wait a second."
 
Dan could almost hear her moving across the lobby.
 
"Where are you?" Jenn asked.
 
"At home, in my office," Dan replied. "Where are you going?"
 
"Ladies' room, dummy," Jenn replied.
 
"Men's," Dan said firmly.
 
"I can't," Jenn whispered, shocked.
 
"Do it," Dan insisted.
 
"Shit, shit, shit," Jenn hissed into her phone. "Ok, perv, I'm in the Men's but I'm going into a stall... and it's empty so no one has seen me."
 
"Yet, slut," Dan chuckled.
 
Dan heard her muttering and shifting for a moment.
 
"OK," Jenn said when she was done. "They're off."
 
"Panties and bra?" Dan asked firmly.
 
"Yes, you perv," Jenn replied hotly. "but you're out of luck because this skirt is a professional length."
 
"I bet your blouse looks nice too," Dan grinned.
 
"Shit," Jenn snapped.
 
"How wet are you?" Dan asked.
 
"Perv," Jenn shot back.
 
"Tell me," he insisted.
 
"Oh god, I'm soaked, OK," Jenn replied. "I'm completely horny and you're probably lucky there's no one else in here."
 
She paused a moment before asking, "How hard are you?"
 
"I'm so hard, honey," Dan replied. "I can't believe how hard all this has made me."
 
"I can," Jenn actually giggled, then groaned.
 
"Are you touching yourself?" Dan asked, a little shocked.
 
"That's what you want, isn't it?" Jenn purred into the phone. "I'm here, in the Men's restroom, with my skirt hiked up around my thighs, touching my dripping pussy. It feels good, Dan. It feel nasty and dirty and so good."
 
"Just like last night," Dan prompted, reaching into his own pants.
 
"Oh yes," Jenn moaned. "When he touched me, I just shivered. I knew it was what we'd talked about, but doing it... I felt like such a bad girl and that just made it better. Oh, Dan, when he put his cock in me, it was so... ahh... so good."
 
"You dirty slut," Dan groaned.
 
"Tell me you're stroking it," Jenn growled. "Tell me you're holding that beautiful hard cock."
 
"I am," Dan replied.
 
"Say it," Jenn demanded.
 
"I'm stroking my hard... uhh... hard... cock," Dan groaned.
 
"You're thinking about him fucking me, aren't you," Jenn panted. "About him inside me. His big cock... ahhh... so big... in my pussy. My wet little pussy, all stretched out around his... uhhh... big cock... as he fucked... fucked... oh god... fucked me."
 
"Oh shit," Dan moaned. "Oh honey..."
 
"That's it, Dan," Jenn panted, "cum for me. Cum... ahhh... cum with me."
 
"Shit!" Dan roared, his body spasming.
 
"Oh God!" Jenn shrieked into her phone.
 
For a time, the both sat panting through the phone at each other.
 
"I can't believe," Jenn gasped out, "that I just rubbed one out in a Men's hotel restroom."
 
"Slut," Dan teased. "Call me after your seminars are done."
 
"Perv," Jenn replied.