We were young, just out of high school. I wouldn’t say I was particularly good friends with Dylan, in that I never called him my best friend or, for that matter, even a close friend. He could be awkward, socially, and never quite fit in with my main group of friends. But we lived near to each other, saw each other frequently, and did plenty of activities together over the years growing up. To give a visual, at the time, I was about 160 or so pounds, dark brown hair and green eyes, tall and slim. He was thinner and shorter than me, blondish-brown hair and blue eyes. I played soccer and ran cross country. We had, at first, played soccer together, but he’d stopped playing sometime around sophomore or junior year.
It started innocently, at least from my perspective, or as innocent as two 18-year-old guys can be. It was a warm summer night, and I was at his house, lounging with him on chairs in his backyard. His parents were out of town, and we had somehow procured a 12-pack of cheap beer to split. We’d already had about 3 each. Graduation was a couple of weeks behind us, and the celebration parties had quieted down. We were talking, I think, about girls and sex–who was hot, who was not, who had done what with who, and the like. It was a conversation I’d had repeatedly since I turned 14 with all my guy friends and thought nothing of it. I wasn’t a virgin, at the time, but I could still count on one hand the times I had had sex. Then the conversation took a turn I wasn’t expecting.
“Maybe a weird question, but, how often do you, you know, jack off?”
It was a weird question (I remember thinking, not really a question I could see any of my other friends asking), but one I didn’t mind answering.
“Honestly, probably once a day. I mean, I don’t know if that’s a lot or anything, but I’ll have days go by where I don’t, but I’d say, on average, like once a day.”
“Yeah, same here.” He gave out an embarrassed laugh. “Do you look at porn?”
“Not really. I mean, I have before, but not frequently,” I said. (This, I think, was around the same time online porn and the like was founded or at least before I even knew what it was; porn was not freely and easily accessible like it is today.)
He just nodded, as if in agreement, but honestly I don’t know what he was thinking. We both took a few more sips of our beers. You could hear the cicadas singing and sun had almost completely set. For a moment, it seemed like any ordinary summer night. But I’d felt a charge run through my body once he had changed the topic from the sex others were having to me, in particular. It both turned me on and felt freeing, in a sense of divulging a part of me that I had never talked to anyone about before (or in any way other than typical locker room talk)–yes, I did masturbate, and yes, I did it once a day. I wanted, in other words, to keep the conversation going, and I was curious about him, too. And maybe sensing my eagerness or willingness, Dylan delivered.
“I mean, yeah, it’s hard to find good stuff, you know. A lot of the girls are just not hot, or you have to pay to watch. But I’ve found some good stuff that I like.”
“Yeah, like what?”
“Nothing like crazy, but you know, girls that look more like the girls we go to school with, and they’re with normal looking guys, not what you typically see. I’ve got a pretty good collection at this point.”
“Must be nice to have your own computer.”
“Want to see?”
“I mean, sure, yeah, what else have we got to do?”
I took another sip of beer and followed him into his house. I was remember thinking that I was aroused, but that was also par for the course of being an 18-year-old. We went into his room and he turned on his computer. While the computer booted up, he grabbed a chair from another room so we both had chairs. We sat down and he started opening some folders and typing in passwords or something, I wasn’t really paying attention, but after some time, he had pulled up a folder that had images and videos.
“You ready?” He asked.
He starting opening some images. They were about what you would imagine–hot, naked, college-aged women, striking various poses and of varying degrees of nudity. Some were just breasts bared, others were fully naked, still others were fully exposing themselves for the camera.
“Damn, these are great,” I said.
He kept flipping through more images, some tasteful, some more hardcore, and then he opened up a video and started playing it. It was, sad to say, typical jack-hammering type porn, but arousing nonetheless for the very fact that I was watching it with someone else.
“I don’t know about you,” Dylan started saying, “But I’m getting pretty horny.”
I think I just nodded or muttered a quick agreement. But he wasn’t wrong: I was horny, and I was hard, and I was sitting close enough to Dylan that our forearms were touching. The jack-hammering video had ended and he had started another–a lesbian scene.
“Do you think, I mean, you don’t have to, but, it doesn’t bother me if you want to jack off,” he said to me.
“Right, yeah, I mean, same. If you want to, go for it.” I could see the bulge of his cock under his shorts.
“Yeah, ok.”
I felt a burst of boldness and quickly pushed down my shorts so I was just sitting in my boxer briefs. He watched me, and then he did the same. I turned my attention back to the computer screen–one girl was making her way down the body of the other, kissing her breasts, then stomach, her hand moving down the other’s thigh and then up to the center of her legs. I put my hand in my boxer briefs, and, involuntarily, let out a small moan as my hand finally touched my hard cock. I started to move up and down my shaft slowly, feeling overwhelmed by the graphic sex scene unfolding on the computer screen and the fact that I was sitting right next to another guy who was also touching himself. I looked down, and saw that he was looking at my hand in my underwear. We were both going slow, restrained by our underwear, and still unsure how far we would be willing to go.
“Do you, I mean, should we take off our underwear, too? It’s a little hard to really jack off with them on,” he said.
“Right, yeah, I’ll take mine off if you take yours off.”
He nodded and we both stood up, looking at each other shyly, and then quickly pushed down our briefs over our hard cocks–we paused for a second, and then took off our shirts too–and then sat back down. I had seen him naked before, but never before hard. It felt different. More raw, maybe, or arousing in a way that felt forbidden, then the times I had been naked with the opposite sex. My heart was pounding. Our packages were similar. Both cut and both probably around 6.5″ to 7″, though I seemed thicker than him. We were both trying not to look at the other, but I could sense he was watching me out of the corner of his eye, the porn almost forgotten.
“This is much better,” he said, starting to stroke himself more regularly. I did the same and saw that the video had ended. The next video was of a guy and a girl, more sensual than the first and more similar to my own experiences. I remember comparing my dick and Dylan’s dick to the guy in the video and thinking that we stacked up well.
We both started getting into it, focusing on the video and stroking ourselves. Occasionally our elbows would touch as we shifted in our seats–it might have been on purpose or it might have been an accident, but not knowing, I think, was even more arousing. I would watch, briefly, to see how he jacked off–it was slightly different than me (I focused more on the head, and he seemed to focus more on his entire shaft)–and I could see the pre-cum starting to form on his tip.
“How long does it usually take you,” I asked. I let out a small moan after the question had left my mouth.
“Depends, but I think I’m getting close.”
“Yeah, me too.”
“Do you want to come?”
I just nodded and kept going, as the guy and the girl in the porn switched from missionary to doggy style, stroking myself faster and feeling close. Dylan did the same. By this point, while it all still felt surreal, his naked body next to mine, almost touching, most of the nerves had melted away and it seemed we both had a singular focus on coming.
I noticed that he had stopped watching the video and now was mostly focused on watching me touch myself. I did the same. We could hear the moans from the video, but it was so much more visceral to watch him and his cock and his hands and listen to the way we both tried to keep from overly moaning. With my free hand, I moved to cup my balls as I got close to finishing, speeding up; he did the same, both of us abandoning any remaining pretenses–we were going to come in front of each other and we were going to watch each other do it.
He came first, his eyes locked on my cock. His cum shot out of his cock, up to his chest and then down his stomach, as his body trembled, his breath shaky. I watched him and looked him in the eyes, and then felt the contractions all down my body as I too came all over my stomach and let out a deep moan. We both looked at each other, unsure exactly what the other was thinking, but realizing we had crossed some line.
“Here, I’ll get something to clean up with.” He left–and I remember thinking, holy shit, did that just happen? He came back with two wash rags, still naked and still hard. He, unlike me, had no hair on his body, I somehow only registered for the first time. Even his pubes were minimal. I felt slightly embarrassed as I cleaned up the mess. He stopped the video, and we both pulled up our underwear and our shirts. I was still incredibly turned on, but I didn’t know what to do or say at that point. It was all foreign territory. I think I muttered something about needing to head home; he nodded and walked me to the door. And then I walked home, still in shock.
***
“So, that’s all that happened? I thought you said there was more.” My wife was naked next to me in our bed, running her hands up my thighs and occasionally touching my cock as I told her a story I thought I would never tell anyone.
“Well, yes, but it had to start somewhere.”
I kept going with my story.
***
We didn’t talk about what happened that night for several days. But maybe after a week, I got a text from Dylan in the middle of a hot afternoon.
DYLAN: Hey man, my parents are gone again. Want to come over?
There was no doubt to his meaning. Saying his parents were gone “again” showed what was on his mind. I don’t remember what I was doing at the time–probably watching TV or playing a video game–but I was now both half-hard and nervous. Was I, were we, going to do it again? What did that mean? I had thought it over since it happened, but I had decided to pretend that it was nothing more than harmless fun. We were tipsy, horny, hormonal teenagers: this stuff just happens, right? I didn’t consider myself gay. Eighty percent of my day was probably spent thinking about hooking up with girls. It’s hard to really put myself back into the state of my mind at the time, but there was no denying the physiological reaction: my body wanted to go to his house, even if I felt some hesitation over the implications of what it meant for me and my identity.
And so I did go to his house, and so it continued as it did last time. Turning on porn, the (at this point, surely feigned) hesitancy about whether we would get naked as we sat next to each other, the same not so subtle glances at each other’s bodies and cocks, and the same awkward ending after we had both finished. It became something of a ritual; his parents would leave for work or go out of town, he would text me, and I would come over. His mom came back sooner than expected one time, but we were quick enough, I think, that there’s no way she could tell what we were doing.
Then things took another turn. By then, it was the middle of summer. Probably more than a month and half since our first time. I can’t remember exactly what we were doing, but my best recollection is that a large group, maybe a dozen or so of us–guys, girls, all recent graduates from the high school–had gathered in a local park one night. We had some beers and other alcohol; there might have been a joint being passed around, too. When we didn’t have a house we could all party at, the park was the next best option: it was not close to any major roads and generally stayed empty during the night, so the cops rarely stopped by, but it was big, with plenty of secluded areas, with wandering trails snaking between the trees and undergrowth.
At the park, we drank and laughed and talked, nothing unusual, at least to begin. I was there mostly because a girl I had been talking to, Hannah, wanted to go so I followed along. What cheerleaders were to football players, that was what Hannah was to alternative or indie kids. She was blonde and quite pretty, with sparkling eyes, and large breasts, but she preferred thrift shops, reading poetry, going to the concerts of obscure bands, and the occasional cigarette. She was a free spirit and we were a bit of an odd couple, but I was enough of a nerd to keep up with her, and I’d had a crush on her for a long time, and, if I’m being honest, I was dying to see her naked.
Hannah and I had started talking a little before graduation, but nothing much happened between us until a few weeks ago when I took her to go to a concert of a local band. We both had started opening up more to each other, finding we had more interests in common than we thought, and it seemed like we were clicking. I wasn’t sure it was ever going to be anything other than a fling. When we left the concert to head home, we took a detour and parked the car at the same park we were at tonight. I grabbed a blanket from the car and we started walking into the park.
It was past midnight and quiet save for the distant sound of cars. We walked to a meadow area and spread the blanket and laid down next to each other as we looked up at the stars.
She turned over on her side to face me. “That was nice, thanks for taking me, though my ears are going to be ringing for the next 24 hours.”
“They put on a good show, though, right? The singer is really good.”
“Agree. Also cute.”
“I didn’t take you here to tell me how cute you think other guys are.”
“Oh, really, and why did you take me here?”
That was an opening if I’ve ever seen one. I also turned on my side so I faced her laying down the blanket. I reached out and pulled her closer to me. Our faces now almost touching, we locked eyes and she gave an almost imperceptible smile. I placed my lips softly on hers and pulled her to close the remaining distance between our bodies; she met my kiss and more–her arm went around my shoulders and the back of my neck, pulling my mouth down into hers. I felt her tongue on my lips, and we started making out. I remember her breath was stale, but still had a hint of mint or strawberry that was intoxicating. I wanted more. I started moving my hand down her back. Her shirt had ridden up an inch or so, and I felt the skin of her lower back. When my hand touch her bare skin, she let out a small moan and moved to lay on her back, her hand pulling me to lay on top of her. There was no hiding my hardness at that point; it was now pressing up directly against her. As we moved our clothed bodies on top of each other, I started to move my hand up to her tits; she was wearing a black blouse with buttons and I’d been staring at the hint of her cleavage most of the night. My hand reached the bottom of her right breast. At the same time I cupped her breast, I pushed my hardness into her, and she let out a little moan and then pushed me off.
“Get on your back,” she said. I did as instructed.
While I lay supine, she sat back on her knees. She looked me in the eyes, bending forward slightly at the hip, and unbuttoned a few more buttons on her blouse–enough that I could see her black bra, which I saw now was a balconette that barely concealed her boobs. I’m not great at sizes, but they were easily a D cup.She put her hand on my cock and then moved to my belt.
“It seems you like?”
I don’t think I said anything; too afraid I would jinx the moment, I simply nodded in submission to whatever she had planned. She moved to unbuckle my belt and unbutton my jeans; I moved up my hips to help her pull them off. She pulled them down to my knees and then leaned over me, her hand reaching back to touch me on top of my boxers.
“Are you hard for me,” she asked. She was rubbing my cock through my boxers.
“Yes.”
She kissed me and then moved down my chest and abs, biting and kissing. I thought I was going to lose it. She reached the top of my boxers and used both her hands to move them down. Her hand grasped my cock. I’d had a blow job before, don’t get me wrong–but no one had ever looked so pleased to run her tongue along my shaft and then take my head in her mouth. She alternated sucking and stroking, meeting my eyes each time her mouth left my cock and giving me an impish smile. She started going faster and faster, and kept up a steady stream of “I want to make you come” and “I can taste your pre-cum.” She was preternaturally comfortable in who she was and what she liked and didn’t like; it should have come as no surprise that assuredness extended to her sexuality.
Her hand reached down to graze my balls and I involuntarily twitched and let out a deep moan, “fuck, Hannah, that’s feels so good–don’t stop.”
She didn’t. She took me as far into her mouth and she could several times and then she moved back to focusing on the head and stroking me at the same time. I felt the contractions of my orgasm starting–“I’m gonna come,” I barely let out in time–before she doubled down and took my entire cock in her mouth. She took a moment after she swallowed, and then helped pull up my boxers before she moved to lay down next to me again.
“We didn’t have anything to clean up with.”
She said it so nonchalantly, that I didn’t realize at first she was talking about swallowing my cum.
“That was incredible,” I said, “I want to repay the favor.”
She smiled, “Oh, you will. But not tonight.”
“Are you sure?” I would’ve done anything she asked at that point.
She nodded.
“Should I take you home?”
We folded up the blanket and made our way back to my car, hand in hand. Over the next couple weeks, we fooled around more. I finally ate her out one night when she came over and my parents had gone to bed (she eventually explained she was on her period and that was why she didn’t want me to go down on her at the park). Her taste was intoxicating, and I still remember the way her whole body shook when my tongue finally made contact with her clit after what must have been two or three hours of edging–while my parents were still awake, we would sneak off to a side room and furiously make out and touch each other, her hand grabbing my cock through my shorts and my hand finding her absolutely soaking wet. But we still hadn’t had sex.
And that was how it was the night we were all at the park, two or three weeks after our date to the concert. Around the time we were halfway through our alcohol supply, one of the guys ventured that we should play a game. Some of the girls, I remember, brushed him off. But, as we really didn’t have anything much better to do, eventually there was a debate–spin the bottle? truth or dare? seven minutes in heaven? never have I ever?–about what we should do. The crowd was probably 8 girls to 7 or 6 guys, so the odds were in our favor in any game. No one, it seemed, had ever played truth or dare so we agreed we should play.
I don’t remember much of it. Most of it was inane, I’m sure–who do you think is the hottest teacher, are you a virgin, prank call someone, etc. No one there was bold (or drunk) enough to take it to another level. But a few memorable things happened.Hannah, at one point, chose dare. I think everyone was waiting for it to happen, but one of the other guys finally got up the nerve: “I dare you to make out with Courtney.” Courtney was sitting next to Hannah; she was a petite brunette. She wasn’t my type, but she was cute and always struck me as innocent and certainly less confident in her sexuality than Hannah. Hannah just nodded like it was no big deal and then looked at Courtney. I saw Hannah look at Courtney; Courtney gave a small nod. Hannah stood up and, playing to the crowd, theatrically straddled Courtney. One of the guys let out a whistle. Hannah cupped Courtney’s cheeks in her hand and brought her lips to Courtney’s and suddenly they were making out. It was entrancing watching their soft bodies move and hair fall around their faces. It probably lasted all of 20 seconds, but by the end of it I was rock hard, as I’m sure all the other guys were as well. Hannah got up, took a quick look at me, and then gave a smile to the rest of the group.
When she sat back down, she looked at everyone and found the guy, Ethan, who had asked the dare. She looked at him and said truth or dare. I don’t know how he didn’t see this coming, but he didn’t, and he chose dare.”Ok, fair’s fair, Ethan. I dare you to make out with a guy. I’ll even be nice and let you decide who the lucky man in this group is.”
Everyone laughed.
“No way, I’m not into that,” David said.
“C’mon, it’s only fair,” Hannah responded.I remember venturing a glance at Dylan, who was watching with the same amused smile as everyone else. David and Hannah went back and forth, with others interjecting, until finally it got to the point it wasn’t fun anymore and Hannah threw in the towel.
“Fine. If you won’t do it, your dare then is to strip naked in front of all of us and then run to the other side of the field and back.”
David had already humiliated himself enough by not playing by the rules in the first instance, so he just sullenly nodded and then began stripping. Everyone started laughing and clapping until eventually he stood before all of us naked. If he was hard before, he definitely wasn’t now and he seemed on the smaller side to begin with. He started running across the field–a flash of white in the green grass–and we all watched and laughed.
That was when we heard a call pull into the parking lot 100 yards or so from where we were. David had just reached the other side of the field and was heading back, and we saw a flashlight making its way toward our group.”Don’t move!” We heard a voice shout.
There were two of them, it seemed. Definitely the cops. We all panicked, and started scrambling in different directions away from where the voices originated. Someone, I remember, had the foresight to grab David’s clothes to bring to him. There was no coordination; I was one of the last to start running, as I had taken a few extra seconds to shake out and roll up the blanket I had brought. Hannah, on the other hand, had almost immediately started sprinting away with some of the other girls. I made my way toward another grove of trees on the far side of the field. I was fast enough that I wasn’t worried about the cops catching up with us so once I was covered by the trees and on the path, I started walking. I didn’t see anyone else at first, but then there was Dylan.
“That was a close one,” he said.”
Yeah, we got lucky. Didn’t seem like they wanted to chase us,” I said, “anyone else with you?” He shook his head, and said everyone had split off on different paths.
Looking back, I saw the flashlights were pointed down at the ground and not toward the various places we had run. I sent Hannah a quick text to see if she was okay. Dylan and I kept walking together through the woods. I had driven with Hannah, but Hannah’s car was in the same parking lot that the cop car currently was. Hannah texted back to say she was with Courtney, who had driven but had parked at another lot and was going to ride back with her. She said they could try and find somewhere to pick me up, if I didn’t have a ride. I asked Dylan if his car was there, and he nodded, so I told Hannah I’d found a ride and would text her once I got home.
“So where’s your car,” I asked Dylan, realizing I probably should have asked that before I declined Hannah’s ride.
“It’s back at that lot.”
“Oh, how long do you think they’ll be there?”
“I don’t know, but I doubt they’ll stay for long. Probably can just follow this trail for awhile and then make our way back. There’s no way they can find us at this point.”
“They can run the tags of the cars in those lots.”
“I thought about that, but I don’t know, there were lots of random cars there.”T
here was a lull in the conversation as we kept walking.
“That was pretty hot, watching Hannah and Courtney,” Dylan said, suddenly.
“Tell me about it. Honestly, doesn’t surprise me that Hannah would be into it, but I was surprised by Courtney.”
“Same. Poor David, such an idiot he didn’t see that coming.”
“I know, I don’t blame him though.”
“So you wouldn’t have done the dare,” Dylan asked.
“I don’t know. That’s a lot of people to do it in front of, you know.”
“If no one was there, would you have done it?”
“I don’t know. Would you?”
“Yeah, I think so.”
On the surface, the conversation was innocuous, but the undertone was what we’d been up to the last couple months, jerking off with each other. Not touching, but not necessarily looking away either. I could tell where he was leading the conversation, and I wanted him to take it there, even if I wasn’t brave enough to do it myself. The adrenaline from the surprise by the cops and running was subsiding, and thinking about Hannah and Courtney kissing, and me and Dylan, started to turn me on.
“Have you before,” I asked, meaning, had he kissed another guy.
“No, I haven’t, assume you haven’t either?”
“No. Never really thought about it until tonight, I guess.”
There was another pause as we kept walking.
“Do you want to try?” Dylan finally asked.
“With you?”
“Who else,” he laughed.
I looked around; no one else was anywhere near.
“Let’s go back in this way,” I said, pointing to a clearing off the side of the trail. He followed me and we looked at each other. I suddenly was fully aware of his presence and his body close to mine. He was an inch or so shorter than me. My heart was pounding. He pulled up closer to me and put his hand behind my head to bring me down to his lips. My lips grazed his, and then we were kissing, making out. It felt different, not bad, but different than kissing Hannah or a girl. I could feel a bit of stubble, and it was rougher; more raw, in a way. He pulled me closer to him and suddenly I felt his cock pressing against mine. I moaned into his mouth and kissed him more forcefully, biting his lip. For a moment I just stopped thinking and let it happen, enjoying the pleasure and the feel of his cock against me.
Eventually we pulled apart and looked at each other.
“Do you want to?”
I nodded.
We walked further into the trees, off the path. I put down the blanket I had brought and we sat down on it next to each other. He pulled me into another kiss. I moved my hands into my shorts and grabbed my cock and started stroking it. I could sense he had done the same. I was lost in my own thoughts when I felt his hand on my shorts, on top of my cock. He pulled back from kissing me, and asked if he could touch me. I nodded, and moved closer to him to get the angle right. His hand touched my abs and then pushed against the waist of my shorts–my body trembled at the foreign touch, another man’s hand–and then he grabbed my cock and I almost came. He started giving me a hand job and asked, if it was okay, and I said yes, and kissed him more. I was getting close and he was expertly touching my cock.
I needed a distraction.”Can I touch you, too?” I asked.
“Yes.”
I moved my hand into his shorts as he did to me. It was a tight fit with my hand, and I felt his body also reacting to the sudden touch. Then I had his hard cock in my hand. It felt different from touching my own, he was smaller but not significantly so. But I felt powerful as I started to move my hand up and down his shaft, enjoying the feel and the sounds it was causing him to make.
“These shorts are making it hard to get the right angle,” he said.
“Yeah, let’s take them off.”
We pulled our shorts down to our knees, and moved back to sit next to each other. Our hands crossed again as we sought out the other’s cock while we moved our heads closer together, occasionally to kiss. I was already close to coming, electrified by the sheer nature of what we were doing–half naked in a park, touching each other and making out.
I was lost in what he was doing to me and didn’t realize it at first, but all of the sudden he was bending over and moving to take my cock into his mouth. He couldn’t take me very deep, and his technique was nowhere near as developed as Hannah’s, I thought, but it was incredible to look down and see Dylan giving me a blow job. I had stopped touching him when he moved to take me in his mouth, and now I ran my hand through his hair and moaned, telling him to keep going and that I was getting close. He nodded and kept it up, moving his free hand to my balls and gently playing with them. He moved a finger down to my perineum and lightly played with my asshole, something no one had ever done before. I remember bucking at the touch but it felt incredible. I realized I was making a lot of noise, and quieted myself, aware that others could still be nearby. I whispered to him that I was close to coming. He kept his hand on my balls, but stopped blowing me and moved to kiss me. I returned the kiss, tasting a bit of myself on his lips. He told me to touch myself and that he wanted to watch me come. I did what he told me, while he brought his finger up to his mouth, licked it, and then moved it back to my ass, drawing little circles around my asshole and teasing me. Then he pushed it into me and I came almost instantaneously.
“That was sexy,” he said.
“Yeah, it was,” I said.
Now that I’d come, I felt slightly awkward and more aware of our surroundings.
“Do you want me to help you out?”
“Can you do the same to me?”
He was rock hard and started touching himself. I grabbed his balls, feeling them in my hand and teasing him. Then, like he did, I wetted my finger and began exploring his ass. He moaned, and I kept running my hand from his balls to his ass, licking my finger again to ensure it was wet enough and then I pushed it inside of him. It felt tight, and hot, and I was absolutely shocked that somehow, I had ended up in this situation, but here I was. I started to finger his asshole as he jacked himself off faster and faster.
“I’m getting close — keep going,” he breathed.
I don’t know what took hold of me, but all of a sudden I had an urge to please him. Keeping my finger teasing and fingering him, I moved my mouth to his balls and gently took one, and then the other, into my mouth. He erupted. It was more come than I’d ever seen from him, and it kept coming.
We both laid back on the blanket, exhausted from our efforts and shocked, too, at how quickly everything had unfolded. I moved to pull up my shorts and he did the same.
“I guess the coast is probably clear now,” he said.
***
My wife looked at me, some mixture of shock and arousal. “I can’t believe that all happened.”
“Sometimes I can’t either.”
We were in our early thirties now and married for a couple years. During the pandemic, we spent more time together than we had in a long time and it sparked a renewal of our sex life. At some point, we started talking about fantasies and experiences. My wife was bisexual, something I’d always known, and she had dated women before we met. I had never told anyone about my experiences with Dylan that summer, and thought I never would. But then my wife asked the question one night.
“You know, we talk about me a lot, and what it’s like to be bisexual, but nothing really about you,” she said.
I just nodded. And then I simply said it, before I had a chance to reconsider.
“Well, I’ve had experiences, too, with a guy that is. I just have never considered myself anything other than straight.”
Her eyes glowed.
“Really?”
“Yeah, it was awhile ago. And never really thought I’d tell anyone.”
“Wow. I’m shocked, I mean not in a bad way, and not that I mind at all, to be clear. The opposite really. I think that’s obvious. And I love you no matter what.”
And that was it. She was respectful and gave me space. But it slowly started making its way into our dirty talk and fantasies. We had talked many times about involving another woman in a threesome. But never another man. And, one night, not so innocently, as we were having sex, she asked if I would be interested in having another man join us.
I thought back to Dylan and thought back to our experiences and looked at my wife, staring at me with a naughty smile.
“I would,” I said, as I pushed myself deep inside of her.
She moaned. “Oh, that feels good–keep going. When you told me,” she said between breaths, “I haven’t been able to stop thinking about it.”
“Oh, yeah? What do you think about?” I moved my mouth to her ear and lightly bit her neck as my other hand moved down to rub her clit as I kept fucking her.
“I think about you and a guy, together; what it would look like to watch you two touch each other.”
“And you want to join in?”
“God, yes,” she moaned and we kept fucking until we both came.
Afterwards, exhausted, we laid back and cuddled.
“So, will you tell me what happened between you and this mysterious guy so long ago?”
Kendall moaned, releasing a string of expletives as I thrust my cock back and forth into her wet pussy. I spanked her right cheek and then grabbed her hips, admiring the way the water from the shower cascaded over our bodies. Kendall, my thirty-year-old wife of three years, had long thought shower sex overrated. But our plush hotel shower not only had two showerheads, it featured a built-in marble bench that, upon first seeing it this morning, I immediately imagined Kendall bent over, her hands flat on the bench, wet, naked and waiting for me. So, after a couple hours relaxing by the pool, consuming one margarita after another, and admiring the way Kendall’s gorgeous ass filled accented her small, cheeky bikini bottoms, I was desperately horny enough to temporarily forget her past preferences. When we hopped in the shower to wash the stink of the pool off our bodies, I pulled her to me, desperate, bending slightly to match her height so I could run my cock between her legs and let her feel how I hard I was.
It turned out I wasn’t alone. She matched my fervor, pulling my head down toward her mouth and pressing her tongue against my lips. With one hand on the back my neck, and the other on my ass, she pulled my body to hers. I reciprocated in kind, letting her ass fill my hands and caressing my hand down her arching back. The water fell down our bodies, following the slopes of her breasts before meeting my skin and chest as we made out with unabashed urgency.
She moved back against the wall of the shower and pushed my head down. I ran my hands down the sides of her body as I kneeled, gently taking first one hard nipple and then the next into my mouth and sucking. I continued kissing down her stomach and then to her pussy and thighs. Amidst the lingering odor of chlorine, I could smell her arousal.
For our vacation, she had gotten a Brazilian wax but left a little strip of hair just above her clit. I kissed around her thighs, occasionally biting her in the way I knew she loved, and running my hands up and down her legs, cupping her ass at the end. I pushed her up slightly with my hands and used the temporary elevation to reach back to the bottom of her folds and let my full tongue run slowly up her pussy, stopping just before touching her clit. A few more times I repeated that action, before taking her folds into my mouth and sucking, using my tongue to reach inside her tight hole to taste her. Starting at her perineum, I ran my tongue up her folds and making my way to her clit, circling and gently sucking on her clit the way I knew she loved. She ran her hand through my hair and moaned.
“Harder.”
I pulled back for a moment and stuck my finger in my mouth, wetting it, before I went back to her clit. At the same time my nose touched her pussy and before I began sucking on her clit, I pushed a finger deep inside her hole–now leaking with her arousal–bending the knuckle slightly to rub against her G-spot. I began fingering her, in rhythm with the short, lapping licks I was delivering to her clit.
“I need your cock now.”
She pushed me back and then, fulfilling my premonition from the morning, she bent over the bench, waiting for me to fill her from behind. I took a moment to admire the view. Her large breasts, dripping water, her nipples hard. The delectable arch in her toned back leading to the source of my torture for most the afternoon: her wide hips and perfect butt, now blissfully free of her bikini bottoms. I drew my eyes back to her face; our eyes connected. She lifted one of her hands to push a stray strand of wet, blonde hair from her eyes.
“Fuck me,” she said.
I wet my fingers again, and ran my fingers up her slit, making sure it was still wet enough for me to push inside her, and then briefly teased her asshole with my thumb. As I pushed slowly inside of her, letting her pussy get used to my size, I watched as she re-balanced on a single hand so the other could rub her clit as I fucked her. Once her wetness had fully coated my cock, we kept up a feverish pace, both of us focused solely on coming. The tight, enclosed space of the shower filled with our moans.
“Spank me. Hard.”
“You like that,” I groaned, as the sound of my hand spanking her ass filled the marble shower.
“Again, fuck. Harder,” she gasped, “You feel so fucking good inside me.”
Her right cheek was starting to look rosy, so I next spanked her left cheek, feeling, as my palm met her ass, her pussy contract around my cock. I moaned, my balls tightening in kind.
“I’m getting close,” I said.
“Me too, don’t stop. Come in me.”
I kept up the pace, constricting my muscles to time my climax with hers. I could tell, by the way her hand was rubbing harder and faster on her clit and her uncontrolled moaning, that she was close to coming. I couldn’t hold myself off much longer.
“I’m going to come in you,” I moaned.
“Yes! Fuck me, Dan. Fill me. Fill my pussy. I’m going to come with you, fuck, fuck–” She trailed off in pleasure.
I groaned, filling her up with my come and feeling her contract around me, pulling me deeper insider of her. Her breaths deep and ragged, her skin flushed. I slowly pulled myself out of her, a white deposit of cum where my cock once was. She turned around and collapsed onto the bench, and I followed suit. Our cheeks were red, our breath heavy, the water still falling all around us and steaming up the bathroom.
“Holy fuck, that was good,” she said, “I might need to reconsider how I feel about having sex in a shower.”
“Or we need a bench for our shower at home.”
She ran her hand up my thigh and brought me in for a kiss.
“We better finish cleaning up, they’ll be back soon.”
The “they” Kendall was referring to was Emily and Ryan, who were traveling with us on our mid-summer Caribbean vacation and who we shared our expansive two-bedroom suite with. Despite the ample room in the suite–including dining, kitchen, and living areas–the resort had, in a questionable design decision, positioned the two bedrooms so that the beds shared a wall. When we checked in that morning and surveyed our rooms for the week, Emily had joked about hoping the walls were adequately soundproofed. Knowing Kendall, I thought, we would need more than just soundproofing to keep Emily and Ryan from hearing us.
I checked my phone as I dried off. We’d been in the shower for some twenty-five minutes. When we left the pool, Emily and Ryan said they wanted to stay longer, but I figured they’d be heading back to our rooms soon. I pulled on my boxer-briefs and then laid back on the bed, as I watched Kendall, wearing nothing now but a tiny little tan thong, pull out her hair dryer.
***
It had been a few weeks since I had revealed to Kendall my experiences with Dylan from over a decade ago. Dylan was the first, and only time, I’d ever had a sexual relationship with a man. Relationship might be too strong; we effectively were just fuck buddies that heady summer, using each other to occasionally scratch our needs. It was an experience that I had half-forgotten, half-suppressed, having decided long ago that it was something I would never tell anyone else about. Whereas female bisexuality is often fetishized by mainstream culture, male bisexuality is rarely presented favorably, and I felt straight enough that I chalked it up to experimentation. We both had gone to separate colleges following that exploratory summer and fell out of touch. In college, I exclusively dated women and, in fact, as far as I remember, never even thought about another guy sexually.
Confessions, though, I’ve found, have a way of unearthing more than expected. Particularly when I had a wife as deviously curious as Kendall.
She, of course, needed details.
What about Hannah, Kendall had asked. Did you keep seeing her? Did she ever find out? How many times did you and Dylan hook up? Was that the only time or were there more? Did you guys ever have sex? Did you ever hook up with anyone else? The questions often came when we’d been out on dates, enjoying good food and good wine, and the conversation, naturally, drifted to sex.
I did my best to answer her questions, feeling freed in a way to talk about experiences I realized I’d never fully processed. I explained that I kept seeing Hannah–and yes, preempting the question I saw forming on Kendall’s lips, we did eventually start having sex–but we kept it casual and fun, a summer fling we both realized would end with the end of summer. I didn’t ask about anyone else she was seeing (though I was pretty sure she wasn’t seeing anyone), and she didn’t ask me. I told Kendall that having sex with Hannah was exciting and sexy–nothing, of course, compared to her, I was quick to add–and she was adventurous and unashamed of her desires, which, of course, prompted a smirk and glance from Kendall that conveyed a knowing dominance. Always competitive, Kendall would take stories about former lovers as an open invitation to reassert her place at the top of my sexual totem pole, as it were.
But, despite that, there was something about messing around with Dylan that scratched a different itch, I told Kendall. It was taboo (at least in our unprogressive town), secret, different and, because of that shared bond, intimate in a way that sex with Hannah wasn’t. Nothing in our outward behavior changed; Dylan and I remained friends, but not close, and would see each other occasionally at parties but never went out of our way to talk to each other in public. Instead, we would sneak over to each other’s houses when our parents weren’t home. The pretext of watching porn together long forgotten, we would move straight to making out, feeling each other’s hardness through our clothes. We’d move to a bedroom and starting masturbating next to each other, occasionally helping the other out with our hands or our mouths.
I told Kendall that we’d never actually progressed to having anal sex, though, I admitted with some sheepishness, we tried. He’d admitted he was a virgin, and he’d asked if I wanted to try with him. We had fingered each other, so it seemed a natural progression. We didn’t have actual lube, so we made do with whatever we could find around his house, which, looking back, was an elementary mistake. Despite our efforts, he was simply too tight, or I was too big, or both, and it hurt him too much as I tried to push inside him.
By then, it was almost August and we started preparing to head off to college. We saw each other a few more times, but then went our own ways. And that was that.
***
Kendall was still working on her hair, and I realized I had gotten hard again, lost in thought. She looked at me in the mirror and then made a pointed glance at my now visible hard on in my boxer briefs.
“Ready again for me so soon?”
I was about to say something when we heard the door unlocking and the voices of Emily and Ryan entering the suite.
“Hey guys! We’re back,” Emily shouted down the hallway. “We’re going to rinse off.”
“Ok, sounds good, we just finished showering and I’m getting ready,” Kendall said. She’d quickly thrown on her robe and was talking through a crack in our door. “We still good for dinner in an hour?”
Emily said yes, and then I heard the door to their room close and the shower start.
Kendall closed the door and walked over to me, letting the robe pile at her feet and the mischievous grin I loved so much spreading across her face.
“I need to do my makeup soon, but think I can make you come with my mouth in the next ten minutes?”
***
After Kendall had expertly made me come for the second time that day, I threw on a linen shirt and some matching shorts and went out into the living area of our suite and grabbed a beer from our fridge. Ryan joined me soon, freshly showered and similarly dressed in light linen clothes. I noticed he’d gotten a slight sunburn from the extra time at the pool.
Him and Emily were similar in appearance to Kendall and me. Both Ryan and I were dark haired, and Emily and Kendall were blondes (though Emily’s was more natural colored). I worked out frequently and had generally maintained the lean frame I’d had from years of playing soccer and running. Ryan, it had turned out, also was a runner and we’d occasionally jog together on weekend mornings or, more lately, play a match of tennis at the courts near our houses. All of us were in our early thirties and we’d met last year when Kendall and I moved into our first house together. They were our neighbors, and, we soon discovered, a delight to live near. Like us, they were childless and were determined to have as many good times as possible before that changed–hence the Caribbean vacation, which we spontaneously agreed to a month ago as we drank and barbequed in their backyard.
Ryan and I sat around in the living area chatting while our wives finished getting ready and dressed for dinner. Kendall was the first to emerge. My mouth fell as I took in her dress.
“Hi boys, what are we up to out here?”
She twirled for us. She was dressed in a white romper, contrasting perfectly with her tanned skin, her blonde hair pulled back in a tight bun. The romper was backless, and the straps, attached to a lacy, low-cut top, only barely supported her large breasts. The cotton bottoms, with a subtle flower pattern, were no less modest: they barely reached a quarter of the way down her defined thighs–accented by heeled sandals–and appeared almost transparent. Whether she was wearing a bra and underwear or not, I would have to find out later (I thought not). I stole a glance at Ryan and saw that Ryan was having a similar reaction to Kendall’s revealing outfit.
“Waiting for you, of course,” I said, “You look gorgeous.”
“Why, thank you. You two clean up nicely as well. Emily should be out soon, too, but, in the meantime, how about a little pre-dinner champagne?” She walked over to fridge, pulling out a bottle of champagne we’d had room service bring in earlier as well as four champagne flutes from the cabinets. As she popped the cork, Emily emerged.
Emily was wearing a paisley print dress, almost sheer, that was as short as Kendall’s romper. Her hair, like Kendall’s, was done up in a bun, highlighting her neck and collar bones. The V-neck on the dress plunged downward, revealing her ample and tanned breasts, and, when she similarly twirled for us, we saw that her dress also was backless. Kendall let out a wolf whistle.
“Damn, girl, you look hot!” Kendall said, as she finished pouring the champagne into the flutes. “Cheers!”
We all held up our flutes and clinked the glasses together before taking a long swill of champagne.
“Well, boys,” Kendall began, wrapping her arm around Emily’s waist, pulling Emily into her, and giving her a small kiss on the cheek, “Are you ready to take your hot dates out on the town?”
***
Dinner was a fun affair. We were giddy with the newness of being on vacation and enamored with the location we had chosen–a treehouse-styled resort nestled in the jungles of a Caribbean island, with its own secluded beach down a sandy path. Conversation flowed easily all through dinner. The restaurant was outdoors on the edge of our resort, surrounded by tiki torches, and sat nearly on top of the beach. Gentle waves lapped at the sand. We had an isolated table over near the edge of the roped-off area. All too easily, it seemed, we’d finished three bottles of wine as the last course was taken away. But I, at least, was at the exact right level of drunk and, judging by Kendall’s animation and excitement, knew she was, too.
“That was one of the best meals I’ve had in some time,” Emily said. “Great fish.”
“Should we grab another bottle of wine? Or we can go grab drinks by the pool bar?” I asked.
“Unless they need this table, I’d say we stay here. This is perfect,” Kendall said.
When our waiter returned, he confirmed no parties were waiting for the table and they’d be happy for us to linger. We ordered another bottle of white wine and, after he filled our glasses, Ryan lifted his glass and proposed a toast.
“To Kendall and Dan. You two are great friends, and we are so happy we got to meet you this last year. I think I speak for both of us when I say, this vacation is exactly what we needed. Cheers!”
“Cheers!”
“Cheers!”
“I will say, I do feel like we got extremely lucky. We’ve never–some, maybe, eight or so different apartments later–had such good luck on our neighbors,” I said.
“Or had ones as sexy,” Kendall muttered, just audible enough for everyone to hear.
“Hey now, if you’re not careful, I’ll think you’re trying to pick me up,” Emily responded, with a knowing wink at Kendall.
“And what’s wrong with that?”
“Nothing. Just make sure you’re well-rested,” Emily said without skipping a beat.
We all laughed and took another sip of the wine.
“No, but joking aside,” I continued, the alcohol having the typical effect of making me more loquacious and open. “A lot of our friends now have kids and are harder to see and connect with. It’s already hard to meet new people at this age, and it’s nice, well–actually, it’s great–to meet another married couple that are like us and easy to be with and get along with. Really, now that I think of it, I don’t remember having one disagreement on what we would do this week or where’d we stay or how much things would cost. Effortless, in other words.”
“Totally agree, this will be a fantastic week and it all came together so easily,” Ryan chipped in. “But, to change topics a bit, while you mention it, I’m curious where you two are on the kids question?”
“You know, if it happens, I think it happens and we’ll be happy, I’m sure. But I don’t think either of us actively want kids at this moment. I guess, we like our freedom to do what we want when we want a bit too much to think about giving some of that flexibility away so quickly,” Kendall said.
“I feel the same way. My sister has a little three-year-old girl, a total delight and we love her. But I have to say, every time we finish visiting with them, I am always exhausted. And I look at Ryan and say, not ready for that full time,” Emily said with a laugh. “My sister’s boobs did get huge when she was pregnant. That side benefit, I wouldn’t mind.”
“I think you’re doing just fine as you are,” my wife responded, with an appreciative–almost lusty–glance at Emily’s cleavage.
“I am more than satisfied, don’t worry,” Ryan said.
Emily blushed slightly, and then said, “Plus, you know, having kids around seems like such a downer on your sex life. I’m in the prime of my life, I’m not ready to slow down, you know. I’m already cranky and irritable when I don’t get my eight hours of sleep. Add a baby onto that and, well, who knows what might happen. Well, actually, I know what won’t happen.”
I’d been quiet throughout this exchange, feeling the effects of the alcohol and the lingering arousal seeing my wife–and Emily, too–in their revealing summer dresses, but saw an opening to move the conversation toward more interesting topics.
“So, you two have been married about the same amount of time as us. I always like to compare notes. How do you keep it fresh?”
My wife laughed. “Always Dan with the serious questions.”
“Nah, I think it’s a fair question,” Ryan said. “Obviously we’re very happy with each other; it’s clear you two are as well. But I think it’s natural to have ups-and-downs, you know. The first year of marriage is incredible, I think, and then you start slipping into routines and roles, sometimes unconsciously and forget to check in with each other. So, for us, I think, being proactive about the relationship and having honest communication with each other have always been the priority. And it seems to all flow from that.”
Kendall and I were nodding along.
“We’ve seen too many of our friends get trapped into complacency about their marriages and their lives and go on auto-pilot and forget that a relationship takes work,” Emily said, picking up the thread from Ryan. “So, we both agreed that we’d always be open with each other and tell the other the things we were thinking or feeling. Even if we were scared it would hurt the other. Because I think we both agreed, we’re in this for the long-haul. We’re no doubt going to hurt each other at some point in our lives, that’s inevitable. But it’s way better, I think, to be hurt by words, which can be explored and talked about and considered, than by actions, which are permanent.