Some vacation fun with my best friend and his wife

It was a time I’d desperately been looking forward to: my first solo vacation in years. After more than a decade married, and years of raising kids together, my wife and I decided it would be our yearly Mother’s and Father’s Day presents to one another: a weekend each to just take a trip on our own or get away with friends, as an individual. 

My wife took a girls’ trip with some friends from college a few months prior, and now it was my turn. I’d originally tried to plan a weekend in Vegas but the friend I’d hoped to meet out there couldn’t get the time off, so instead I just decided to take a weekend away from the southern heat and go back to my home town in Michigan. My parents and most of the people I grew up with there were long-since moved away but a few good old friends remained in the area, and I figured it’d be a rare opportunity to reconnect after years apart. 

One of those friends was, in fact, my best friend from high school: a guy named Eric. He still lived in the area with his wife, Tina, who I also knew very well; I was the best man at their wedding. We hadn’t actually had a chance to meet up in a good 5 years or so, but we worked far in advance to coordinate this trip and ensure we’d get some overdue hang-out time.  

When I got into town and got settled in my hotel, Eric and I arranged to meet up for dinner and drinks at a bar-restaurant near his apartment. He told me Tina would be tagging along, slightly busting up our ‘guys’ night,’ but I really didn’t mind; I’d come to expect them as a package deal over the past decade. 

We met up at the restaurant in a nice reunion of hugs and smiles. Eric was virtually the same Eric as always: a large-framed midwesterner with short blonde hair, a short scruffy beard, and sporting the tee shirt of some heavy metal band. Normally pretty muscular, he’d gained some weight since I last saw him; still not back in his gym routine after the pandemic shut everything down for a year. Tina was about like I remembered her too: about my height with straight brown hair spilling down her back, and a decent figure under her jeans and tight black tee shirt. I’d probably best describe Tina as: a little trailer trashy and sometimes too outgoing and abrasive for her own good, but a very fun woman with a good heart and fairly pretty face. 

The three of us had a great dinner of catching up and sharing laughs from the stories of our years gone by. One thing that certainly hadn’t changed about these two: they still liked to put back the drinks. They both finished their first round before I’d drained half of my beer. As the calls for more rounds started coming, Eric told me not to worry about indulging too much as we were in walking distance to their apartment and I was more than welcome to stay the night there. I didn’t fight that offer at all as, really, kicking back and acting like a single dude again for a few days was the whole point of this trip. 

All in our mid-late 30s now though, none of us were making it to the last call at the bar, so after dinner and a few rounds, we made the walk back to Eric and Tina’s place to continue our reunion there. I was impressed by their apartment when we walked in - decent-sizeded living room off a fairly modern kitchen and a couple of bedrooms down the hallway; not a bad setup for a duo that had hopped from job to job for years. 

Tina brought in a handful of beers as we all took our seats in the living room and put Netflix on the tv - mounted on the main wall across from the couch. 

The three of us began draining can after can of beer, getting more tipsy with each empty that hit the recycling bin. Eventually our inhibitions were all severely lowered, our speech slurred, and none of us were making any effort to hold back on any crudeness; we were back to ourselves of 10-15 years prior and were just focused on having some drunken laughs together. 

At some point, Eric and I sat on the couch blathering on about nothing while Tina stood up at the open patio window, having a smoke and piping into the conversation now and then. As we chatted loudly in between drinks, I looked up to the tv and noticed that Selena Gomez had popped on the screen; a part of whatever show was playing in the background. My attention quickly shifted from the conversation to the singer/actress. She had long been a celebrity crush of mine who I couldn’t help but ogle at a bit whenever her image came across one of my screens. Let’s just say: I’d dedicated a few sessions of my ‘me time’ to Miss Gomez over the years. Clearly in my drunken state now, my attention had shifted a little too obviously to that old crush. 

“Yo Rick, you still with us buddy?” Eric asked smacking my leg lightly and bringing me back to reality. “See something you like on the screen or something?”

“Sorry,” I said with an embarrassed laugh. “What can I say: Selena’s friggin hot dude. Can’t help but stare a little.”

Eric agreed with a smile and raise of his beer can. Tina blew out a puff of smoke over at the patio window and chimed in.

“Uh-oh! Did Rick just pop a boner over there? Did we just find one of his jerk off subjects?” Tina said with a drunken smile - I told you she could be a bit crude…even more so when she’s drinking. 

“Fuck you…but yes, you did,” I said back jokingly. 

This got a big laugh from both Eric and Tina followed closely by a few comments about Selena’s finer features and masturbation in general. The three of us, and really the whole crew we grew up with had always been very open to talking about all things sexual or crude. We had little filter among us; a truth that landed each of us in the principal’s office once or twice growing up. 

Now, knowing these two’s affinity for sexual subjects and leaning into my own drunkness, I pushed the slightly ‘TMI’ conversation forward. 

“Honestly though, it’s not often I get to really use those jerk-off subjects anymore,” I said. “Between Lena and the kids running around - there’s not a lot of alone time in my house. You know how it is.”

Before Eric could respond, drunk Tina jumped at the topic from her spot at the window. 

“Are you kidding?” She said through slurred words. “This house has constant masturbation going on. I find this little fucker jerking it all over the place.”

Tine pointed at her husband when she said this. Eric laughed, clearly slightly embarrassed by his wife’s crudeness and, I assume, honesty about their home life, but he was never one to be frazzled or out-cruded by anyone. 

“Fuck yeah I do,” he said with a drunken smile. “We run a masturbation-positive house around here. It’s a goddamned jizz fest most days!”

I laughed at the banter between this odd couple. They certainly hadn’t changed since our younger days. 

After he took another swig of his beer though, drunk Eric tossed out another thought on the matter…one that did catch me a bit off guard. 

“Yeah man, if you need to jerk it, you go for it around here,” he said. 

My instant response was to just laugh again and raise my own beer in a pseudo-toast, but then I thought a bit more about what he said. Was he legit addressing me and not just making a broad statement about their standing house policy on the matter? Was Eric giving me permission to jerk off while I was at his home? That would certainly be new territory. 

While we’d always been open about the sexual topics, Eric and I had never had any ‘you show me your’s I’ll show you mine’ kind of exchanges as kids. Going to high school in the early 2000s, the era when ‘gay’ was still thrown around like an insult among young friends, those were lines that were rarely crossed as you’d never want to be mistaken as ‘not straight’ among the guys. Not that we were homophobic, our classmates who were LGBTQ were very accepted, but you certainly wouldn’t know it watching the media from that time. It was a ‘you had to be there’ kind of era that I doubt many of us look back on with beaming pride. Times had changed though. I know I’ve evolved since then and, if I were growing up in this more open time, I would likely be a much more experimental youth and more outgoing in my sexuality. 

Had Eric’s views also evolved to the point he was giving me that opening? Before I could even fully go down this line of thought or process the suggestion all the way, Tina’s eyes lit up as she flicked her cigarette over the balcony in excitement and quickly blew out her last drag so she could speak up. 

“Oh my god, you totally should, Rick!” said Tina excitedly. 

At this even Eric went a little wide eyed, although that may have just been for show considering he brought it up. 

“What, like jerk off? Like right here?” I said, trying to seem surprised by the suggestion but not put off. 

“Yeah! Fuck it, why not?” Tina responded. “You’re on vacation, you’re horny, and you can do it openly here for all we care. Not like we haven’t all seen your dick before anyway.”

I don’t think either of them had. Tina had made this claim while drunk in the past too, but I don’t recall ever exposing myself to either of them. At least I hadn’t until, potentially this night. 

If you’ve read any of my stories before, you know I’m definitely not opposed to situations like this. Between that and my drunk state, I was ready, internally, to drop my pants and go for it without another word. 

“I mean…” I said drunkenly, smirking at the suggestion of it all. “I could go for some of that right now.”

I looked over to Eric who, his wife being the instigator, seemed the only barrier to this becoming a reality. He just shrugged. 

“I really don’t care,” he said. “You can go for it if you want, dude.”

“See, this is an amazing plan,” said Tina excitedly taking a seat again on an easy chair next to the couch. “So, pop that thing out and enjoy yourself.”

She just stared at me and Eric just sat drinking his beer, trying to look disinterested. Even though I was pretty drunk at this point, I still couldn’t help but hesitate for a few moments. The worry rushed over me about doing this in front of such close friends and screwing up our friendship in the process. Would this be a mistake?

It felt like I sat there frozen for minutes on end, but in reality, it was probably 5 seconds at most. I was very drunk and this was really like that ideal scenario: being cool jerking it with true friends. I could feel my cock standing at rock hard attention in my jeans. I absolutely wanted to do this. 

“Eh fuck it,” I said with a shrug. 

I stood up and unbuckled my belt buckle and moved through the button and zipper on my jeans. I pulled them down to reveal my black boxer briefs that were clearly bulging with my boner in the front. I reached back up and yanked the underwear down below my knees in one solid motion. My uncircumcised 5.5 inch penis sprung out in a full, solid erection as I took my seat back on the couch: exposed with my pants around my ankles. 

“Damn dude!” said Eric, now looking much more obviously at my cock. “Selena really did get you going!”

“Like I say, not often I get to kick back anymore,” I said. “The prospect is pretty exciting.”

“I don’t think I’ve ever seen it hard,” said Tina, continuing her insistence that she had seen my dick before as she now leaning over toward me to get a better look at it. “You’ve got a hot cock.”

I said thanks, just glad the comments were positive. I quickly took my hard dick in my right hand and began jerking the skin up and down slowly; letting my purple head become exposed with each down-stroke and disappear back into my foreskin on the up. 

This situation was odd, to be sure, and I wasn’t quite sure how to conduct myself. I don’t believe there’s a manual to properly jerking off in front of your long-time best friends, and if there is I certainly haven’t gotten around to reading it. I continued with slowish paced strokes trying to seem…casual about it, I guess. Eric kept glancing over from the show on the screen to my cock, also seemingly trying to keep casual on the whole thing. Tina, the enigma she was though, made no secret her enjoyment of the situation. 

“Feel good?” She’d ask looking from my cock to my face. “You poor thing Rick. You should be able to do this whenever you want.”

Tina took another swig of her beer and then looked up at whatever show was playing on the tv; that none of us were really watching at this point. 

“Eric!” Tina commanded at her husband. “Put on some fucking porn or something to help your friend out. Be a good host!”

“Fuck yeah,” Eric said grabbing his phone and tethering the device to the tv. “You don’t have to twist my arm to do that.”

Eric immediately navigated to a porno site online and we all questioned what to watch. I told them I could get into almost anything at that point. Tina pushed for something extra kinky but Eric, being the one in command of the phone, went with a safer route and put on one of those videos of a ‘totally real, not at all staged’ dorm room party where everyone starts stripping and fucking. He’d get no complaint from me on that choice. 

I jerked my cock up and down at a medium pace as the group of college students began performing sex acts on the screen. Tina continued to split her attention between me and the screen while providing commentary on both sights, but she and I both found our gazes going over to Eric. He sat next to me on the couch with an erection of his own clearly tenting his pants. I couldn’t blame him for getting aroused at this point: the porno was hot on the screen and his best friend was literally jacking off right next to him. 

“Looks like you’re getting ‘inspired’ over there too,” I said to Eric. 

“Well, what do you expect,” he replied with a drunken laugh, motioning to everything going on around him. 

“Hey, no judgement, clearly,” I said back with a smile. “You’re welcome to enjoy yourself too if you want. I’m cool with it.”

Eric looked around the room and just shrugged. I was quickly about to learn that his views had too evolved since high school. He lifted his hips off the couch a bit to unbuckle his belt and undo his jean shorts (yeah, he’s a jorts guy for life). My friend’s arm made contact with mine, which was still jerking up and down on my hard dick, as he pulled his own shorts and boxers down in one swift motion. 

As Eric’s bare ass came back to rest on the couch cushion next to me, his naked, erect penis came into my view for the first time. It seems almost unfathomable that we’d never seen each other’s cash and prizes in our 20 plus years of friendship, but there were no secrets anymore. His cock wasn’t particularly large, about the same size as my own really, sporting a hairy blonde bush, and, unlike me, he was circumcised with a swollen purple head on the end of his boner. As I’ve said before I’m not turned on by the male body at all but I am by sexual energy, and could certainly appreciate my friend’s thick, hard rod in that moment. 

“Nice hog bro!” I said casually causing Eric to blush a bit with a smile. 

Eric grabbed his own boner in his right hand and began jerking it up and down; seemingly matching the pace I was moving over my own cock. So there we sat: 2 best friends since high school, sharing a small couch while we watched porn, provided commentary on the action, and jacked off next to each other for the first time. 

You’d probably expect me to feel surprised at the situation I was in, but I kind of didn’t. I’d certainly had my share of mutual masturbation moments over the years, and though none of those had been with Eric, I feel like this situation was always an inevitability waiting to happen. He and Tina were super open about sex stuff, even experimenting with swinging now and then, so had we seen each other more frequently over the years, I imagine we probably would have engaged in some sort of a three some  by this point. More so though, I firmly believe, after all of my experiences and research on the matter, that most people are just a ‘perfect situation’ away from being in a scenario like this one. I sincerely believe few people are ‘fully straight’ or ‘fully gay’ and rather fall in our own unique shades of gray. Sharing some self love with another person, I believe, is an experience most have tried or would at least give a go at if the opportunity was right. 

This was clearly the moment when Eric and my’s opportunity was right. We sat casually jerking off, but beginning to settle more into a steady pace as the moments ticked on. We even began letting out a few moans and deep breaths of pleasure as we became more comfortable in the situation. Meanwhile, Tina was excitedly watching us and trying to conduct this symphony of shared self pleasure, that she was clearly overjoyed to be witnessing. 

“Fuck yeah, this is awesome,” said Tina watching both of our hands go up and down rhythmically. “Eric, I know you usually do this naked. You should both take off your clothes. You don’t wanna make a mess on em, right?”

Eric gave his wife a bit of sarcastic resistance, but then we both agreed that she had a point about the mess; there was no doubt that this situation would end in one. We agreed, ‘why not?’ at this point. Both of us let go of our cocks to remove our pants and boxers the rest of the way off of our legs and shed our shirts; returning to our side-by-side spots on the couch completely naked. 

Now very comfortable, we settled back into our jerking; both of us spreading our legs to the point that my right leg was now making contact with Eric’s left leg. Eric spat in his hand and spread it over his cock head to help lubricate his strokes. I just continued to work my uncut skin up and down, but each stroke was now making a squelching sound of its own as clear precum had begun streaming from my tip, lubing up my head and leaving it a moist as it appeared from and returned into my tight foreskin. 

Tina commented on my precum, resulting in Eric looking between the two of us and then back to his wife. 

“What the fuck are you doing over there? Why are we the only ones naked?” Eric asked her. 

“You’d fucking like that wouldn’t you,” Tina said back to him. 

Suddenly, the mischievous look that had appeared over her face before returned as Tina’s lips turned into a deep smile. 

“Ok, how about this,” she said looking at both of us, “I’ll get naked and join in the fun…if…you guys give each other a hand.”

Eric responded with wide eyes and shock at his wife’s idea. I did too; feigning shock, really, as I’d secretly shared a hand with other dudes in the past. 

“What?” said Tina, still through mischievous smile. “If you two are gonna jizz watching me get off, you’ve gotta give me something exciting too.”

Eric looked over at me inquisitively. I was already getting the vibe that he was as ready to go along with this plan as I was. So, I decided to make it easy on everyone. 

“Bring it,” I said to Tina as I pulled my right hand off of my own cock, reached over, and grabbed Eric’s thick erection from his grip. 

I could feel his cock harden up even more in my grip as he sort-of sat up at the surprise of being grabbed. I wasn’t sure, initially, how he would respond to this, but he didn’t seem taken aback at all. Eric just reached over the top of my arm with his left arm and proceeded to grab my cock in his hand. My dick felt small in his large hand - Eric being a much bigger dude than me - as he put a tight grip around my erection and slowly slid the skin back; getting accustomed to my uncut member. Surprisingly, the feel of my best friend’s hand on me was even more arousing than expected, and far more of a turn on than it had been when any other guy had touched my penis before. 

Tina excitedly clapped as we began to slowly jerk one another. 

“Bluff called, bitch,” said Eric, jokingly to her. “Get your ass naked.”

Tina stuck her tongue out at him but quickly stood and started living up to her end of the bargain. She pulled off the tight black tee shirt to reveal a nude colored bra and dropped her jeans down to show a pair of gray cotton panties. It didn’t take long for her to unclasp the bra and let her decently large breasts pour out. Having a kid in a previous marriage, Tina’s breasts had certainly sagged over the years but still looked pretty good all things considered. She dropped the panties as well, letting a patch of brown pubic hair spring out. 

Tina stood before us naked and spread her arms out, spinning to show it all off. My buddy’s wife looked good with nothing on. 

“There ya go fuckers,” she said through slurred drunken words. “Now I wanna see those cocks blow!”

“Oh dude, you gotta fuckin’ see this,” Eric said to me as he slowly jerked my cock. “Tina - sit down and spread your cooch open; show Rick how fuckin’ wet it gets.”

Tina sat back down on her chair, without skipping a beat, and brought her legs up onto the chair with her - so her knees were up by her face and her thighs spread wide in front of us. Now, through the mound of brown pubes, Tina’s pink pussy became visible and her large lips parted willingly. She reached down with both hands and spread herself open. Her pink hole opened wide as she was very visible horny, so wide that I could easily see into her vagina from my spot on the couch. Her, also large, clit sat red and swollen at attention at the top. 

Eric was right: she was very very wet. 

“Damn Tina! You do get wet,” I said to her. 

Tina moved her right hand from holding her lips open and pressed two fingers into the wet opening - making a sloshing sound as she let out a moan and her body swallowed the digits up. She pulled them back out to reveal that they were now covered in her clear pussy goo. 

“I know right?” she said, holding up the fingers to me and spreading them apart to show the goo spider webbing between them. “Here…”

Tina got to her feet and started walking toward us as she dipped her fingers back into herself. When she got to us, she pulled the fingers out and told me to let go of Eric’s cock. She then spread the gooey fingers all over the head and shaft of her husband’s member - to his moans of approval - before dipping them back into herself, grabbing some more discharge, and spreading it in the palm of my hand. My dick pulsated in Eric’s hand as her warm juices made contact with my skin. I returned my hand to his cock and rubbed the goo all over his head before using it as lube to jerk up and down his shaft. 

Tina then repeated the process, but this time taking her freshly gooed fingers and spreading them over the head of my cock - as Eric pulled my foreskin down to give her an open target. As I moaned a little and closed my eyes in pleasure, Tina took an extra moment to enjoy rubbing her own fluids onto my hard dick. Her and Eric kissed as he reached down and stuck his own fingers inside of her, coating them with even more pussy juice before returning his hand to my cock and spreading it all over me. 

Tina went back to her chair and quickly spread her legs again; finding her large clit with her fingers and beginning to make fast circles around it. Eric was now quickly jerking his wife’s fluids up and down my dick; his hard grip squeezing my head with each stroke and causing me to squirm. My hand was also now flying up and down his cock with Tina’s juice leaving little friction between my skin and his. All of our eyes darted back and forth between one another’s bodies and exposed genitals. 

The whole situation was clearly more than Eric could handle. As Tina plunged her fingers in and out of herself, his dick began to really harden up in my hand and his breathing turned to gasps. I’d never seen my best friend in this state before, but his pleasure was intoxicating. 

“Oh fuck, I’m gonna blow,” gasped Eric. 

“Fuck yes guys!” Tina yelled out as her husband began to tense up and she diddled herself faster. “Cum in your friend’s hand babe!”

As she said that his hips really started to buck and his hand around my dick stopped jerking and just pulsated around my cock. I reached my left hand over and placed it around the shaft bottom of his gooey cock and speed up my jerking as fast as I could go with the other hand. Eric sort of grunted and shook as a big glob of semen erupted from the shiny tip of his cock and fired into the air landing across his shoulder blade with some splatting on the back of the couch. Rope after rope of cum came out as my hand milked his member - most landing on his stomach and chest but most of the last few weakening shots dribbled down from his cock head, over my jerking hand, and getting rubbed over his shaft as I gave him a few slow cool-down jerks. 

Eric’s breathing slowed back down as his body again relaxed on the couch and he came down from the orgasm. 

“Fuck, I haven’t had one that hard in a long time,” he said. 

Tina now had her knees pulled far back and was plunging her fingers into herself and then pulling them out and giving her clit some fast circles before plunging them back in. 

“Fuck! Now Rick’s,” she said gasping, clearly in view of her own climax. 

At that command, Eric reached his right hand over, spitting in his palm along the way, and grabbing my cock. He rubbed the spit over my exposed cock head causing me to twitch at the sensitive area being touched. He moved his left hand down to the base of my cock as I had on his. Then he started jerking my cock up and down, fast. His hand flew over my dick in a blur as all of the sensations rapidly started building in my loins. 

Tina crawled over to get a better look; perching her left knee on the armrest next to me on the couch. The smell and sounds of her soaked pussy being pleasured infected my senses as she now rubbed herself less than a foot from my face. As her other leg made contact with mine, all of the feelings became too much. 

I forced my hips forward against Eric’s grip as cum began exploding from my dick. The first shot arced up and landed on Tina’s thigh, the next few onto my own chest and stomach, and as more shots dribbled out they coated Eric’s hand just as his had mine. He gave me several deep, hard strokes to make sure every drop of cum released from my tip. 

As I came down from my climax, I quickly regained my head as I saw Eric lift his cum covered hand from its grip around my penis. He reached the cum covered hand over to his wife’s open crotch. She removed her own hand to let Eric’s in. He stuck two of his fingers directly into her waiting hole. I watched my white cum disappear with his fingers inside of her and could hear it squishing in her as he started fingering her with it. As her face started to crunch up in ecstasy, he plunged a third cummy finger into her and Tina lost control. She gasped and humped against Eric’s palm hard as she came around his fingers. Over and over she moaned, hitting high notes like I didn’t know she was capable of. 

Tina must have cum for a half minute straight before she finally started defending her muscles and coming down. As Eric pulled his wet fingers out of her, she sort of control-collapsed herself into the small crack between the couch arm and my body. She let her naked body drape over mine as Eric sat back down on my other side also making contact with me. We all just sat exhausted for a few minutes, paying no mind to each other’s various fluids all over us. 

The three of us probably could have fallen asleep like that, but eventually got up and cleaned up. After crashing on their couch that night, we woke up the next morning; a trio of three hung-over friends in our late 30’s. Eventually at some point in the morning, the previous night’s escapades were at least hinted at and we all seemed to come to a sober agreement that, ‘it was cool, no big deal.’ In fact we’d even have a bit of a second round the next night before I headed back home. Perhaps that will be a story for another day. 

Either way, I’d call my first solo vacation in years a relaxing success. I might even do it again next year…