A Change of Relationship Ch. 01

Author Note: This story is original and fictitious, includes only consenting adults, and features elements of gay sex, crossdressing, feminization, and cuckolding. This is the first in what I have planned as a 5 chapter series. Please read, rate and comment! I'd love to hear what anyone thinks or ideas you have for future iterations!

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I swung the door open to the honeymoon suite, tossing my suitcase in and stepping through the door. My best friend followed me in. But not like, my wife is my best friend, no, just my best friend Ryan. Megan and I were to be married the previous day, but it hadn't come to be. The week before I'd found text messages, and then photos of her and her secret lover.

I'd seen pictures of them together. And "together." And not just in her pussy. Or just her mouth. But in her ass too. She'd never even let me put my penis there. And he was... Well he was really well endowed. He dwarfed my manhood. I will always remember the deep, ebony skin of his shaft buried in my fiance's pale body.

After the tearful argument, in which she didn't even promise to stop seeing him, she'd left the house. She sent me a picture an hour later of her panties around her ankles and her lovers legs between hers. She'd gone straight there to be fucked. She sent it out of spite, as if I had done her wrong somehow.

She sent me a text a while after, where she explained that I should have just accepted that she wanted to see him and didn't want to stop just because we were married. That I was a nice guy but I couldn't satisfy her needs because my penis size wasn't to her liking, and that she needed a man to have at least eight inches (Darren had nine) to please her. My five inches was well short.

Heartbroken and emasculated, I went to cancel our honeymoon stay but found the reservation was not refundable. So I decided to take the trip anyway. Since it was for two, I invited Ryan along. He'd been supportive after the fact as my would have been best man. I hadn't told him the details, nor anyone actually.

The bell hop helped us with the rest of the luggage. "Congratulations, you two." He said as he was leaving. I realized what he must think.

"Oh we're not-" I started

"Thank you very much, we're very happy!" Ryan blurted out. He chuckled as the boy left, smiling at his joke. " You know people will assume we're a gay couple all week. This is a couple's resort, you know."

"Jeez... Oh well right?" I reddened a bit but laughed it off. We got our stuff to get situated and I scoffed. "I hadn't even thought about the one bed thing." As we entered the room and saw the king size bed, complete with the hotel's rose petal heart laid out.

Ryan guffawed. "Like I said... couple's resort. At least it's a king right?" He said as he tossed his bags to the far corner by the balcony sliding door. "Some view! It's an awesome place. Good place to move on, right bud?" He gave me a slight shoulder jab.

"Yeah... I hope so anyway." We settled in and made our way to the hotel's bar and restaurant, had some dinner and drinks, and I tried to forget about the heartbreak and enjoy the time. Ryan was jovial, and supportive. We'd been best friends for years, since high school. I had been a pretty nerdy kid, slim and 150 lbs soaking wet. I could have been picked on a lot except for Ryan. Ryan was the opposite. Somewhat of a jock, but kind and cerebral. He was a big guy, he was 6'3" now, and somewhere around 230 lbs, and muscular at that. Nobody had picked on me with him around. I was glad he was here. I felt safe with him. Nurtured, even. We got a little bit drunk, reminisced about school and work, and eventually headed back to the room and passed out in the bed opposite one another.

I woke as sunlight filtered into the room. It was warm in the room, and I had just a sheet over me, and the briefs I wore to bed. I looked over and did a double take as I saw a sleeping Ryan propped in a halfway sitting position, the sheet near his waist. I could see he was completely naked. The sheet came up to cover up his genitals, but left his pubic stubble and the v shape of his pubis bare.

I couldn't believe he had slept nude in the same bed as me. We'd changed around each other before but never had been fully nude. I mentally slapped myself as I realized I was looking at his barely concealed private areas. It's natural for guys to look at guys right? Just for comparison or whatever? That's what a therapist had told me once when I explained the uncomfortable curiosity I had always felt in men's locker rooms. I realized I had a throbbing erection. Morning wood, what are you gonna do about it?

I rolled onto my side and feigned sleep. My side position would hide my bulge if Ryan woke up. I kept my eyes slitted open, looking at my naked friend. Nobody would know, it wouldn't hurt anyone that I was looking at him. I was just jealous of his athletic body, it didn't mean anything. As I was arguing with myself, I gasped internally. I saw a twitch of movement, then another from his sheet. He was getting an erection. His deep breathing seemed to confirm he was sound asleep. The sheets bulged slowly up. Then the tip of his glans just peeked above the hem. I watched, mesmerized. The sheets slid away at last.

His penis throbbed in his lap, and I stared. He was big, to match the rest of Ryan's body. Probably eight inches. Well more than my five inch manhood. He was uncircumcised, but the glans exposed itself fully when he was erect. He had prominent veins, with a central thick one running along the top. His head was a deep purple, the shaft matched Ryan's olive tinted skin.

It was perfectly straight. I remembered seeing my fiancé's lover's penis in the photos she had bombarded me with. I'd felt so much anger and hurt, but if I was totally and completely honest with myself, I had felt a tug of curiosity, of almost... admiration? Something about seeing another man completely exposed and fully aroused made it feel like I was in on some secret. In a sense I had been, but not in a good way, I thought.

I was pulled from my inner monologue by Ryan shifting on the bed. He'd rolled over in his sleep to his left side, meaning this erection was now lying on the mattress, almost at eye level with me. I was staring right down the barrel, so to speak. It was a view I never thought I'd see before, and it was so strange to see, like his manhood was staring straight into me. I had the strange urge to take my unswear off, to be nude together.

I was afraid the movement would wake Ryan though. Was our being mistaken for a gay couple all weekend somehow influencing me? The thought crossed my mind that anyone that saw us as a couple would make some assumptions based on appearances about who played which role. I wouldn't be looked at as being "on top," we'll say.

I heard Ryan breathe a little more sharply and screwed my eyes shut to avoid any chance of being found out. I felt him roll over, sigh, and then slight motion. Repetitive motion. Slow but rhythmic. Was Ryan... masturbating? In bed next to me? There was no way, right? I stayed stock still, breathing quietly and deeply to mimic sleep.

I dared to crack one eye minimally. The image was fuzzy, but I could make out Ryan's silhouette. I saw his arm, and his hand wrapped around his strong, thick- Jesus I couldn't believe I just had those thoughts pop up about my buddy's penis. But it was unmistakably his hand, slowly stroking his erection.

I wondered if he was fully awake, or doing this in his sleep/almost sleep. I did that sometimes, not fully awake but I would wake up with my boner in hand. I watched him stroke with fascination, secretly enjoying this glimpse into my friend's most private self. It made me feel oddly close to him. Intimate almost.

Ryan had always been so comfortable with any situation, seemingly unfazed by anything. He would go with the flow. He might even not care if I saw him jacking off, honestly. A sudden impulse came over me, and for one brief moment I seemingly lost every inhibition I had. I opened my eyes, smiled slyly, and softly said "Good morning to you too..." sleepily.

Ryan jumped, and pulled the sheet to cover his exposed manhood. "Uh... Morning... Sorry I was just uh..."

"I know what you were doing man, just relax, everyone does it right?" I said, sitting up to his level.

"Yea just, not in bed with their friend..." He chuckled nervously."I'm just really used to doing in every morning and I wake up like this and..."

" Well I mean... Don't let me stop you." I said, looking him in the eyes.

"You mean you would just be... Like okay watching me do that?" He looked at me incredulously.

"I mean... I'm the same, with the morning thing I mean... I could join you, maybe if we're both doing it, it wouldn't be weird?" I said softly. I pulled the sheet down on me to show my bulging briefs. He looked at my groin and then back up at me. He smiled slightly. I couldn't believe what I was doing, I felt like I wasn't in control of my own actions somehow.

"If you're game, then I'm game. I'm really comfortable with nudity, and we're best friends after all, why shouldn't we be comfortable like that?" He said, with a hint of mischief.

"Agreed..." I pulled down my underwear, and kicked them off. He pulled the sheet back down. For a moment, there was silence and stillness, as I think we both processed that we were two naked, fully erect men in bed together. I watched him look at my privates. I looked at his. I was much smaller than him in every way, but he still seemed intrigued. Almost on cue, we began to stroke our own shafts. "You... do you always sleep naked?" I asked, almost as if to make small talk during what we were now doing.

"Oh, yea... I always have really." He said. I watched him answer, his body slowly oscillating as he stroked.

"You like it? Sleeping naked, I mean."

"Oh yea, for me it's the only way. Sorry if it made you uncomfortable, I figured I'd be awake and dressed before anything... anything happened."

"Oh, no, like you said, we should be comfortable right...? I think maybe I'll try it too, sleeping nude."

"You should man! We'll do it together." He smiled.

"Okay, yea... I will." We smiled at each other.

"Do you want some lube?" Ryan asked quickly.

"Uh... yea, that sounds good. You have some?" I asked shakily.

"Yep, just let me grab it..." He said. He stood up from the bed and walked naked to his suitcase by the balcony door. I watched as he walked. He was powerfully built, every part of him. I'd seen his musculature and size before, of course, but I could see that his penis, testicles and butt all seemed built for power.

His penis was large, thick and strong looking, his testes hung low and heavy, and his butt was thoroughly toned and proportional. This was the longest I'd ever looked at a naked man before, and it felt like I was getting away with something. I realized that I was literally checking out my best friend. What was happening to me? I wondered to myself.

He snagged the small bottle from an external zipper compartment, and strode back into bed, his erection and his balls swinging slightly left and right with his stride. He slumped back into bed, and I noticed he slid closer to me than he had been before leaving. Our elbows nearly, but not quite, were touching. I watched as he took the bottle, cracked the tilt top open on the little "Swiss Navy" bottle, and drizzled the fluid onto his thick glans. I watched it cascade down, and his hand entered to coat his rod fully.

I watched unabashedly now, my arousal cancelling out any self consciousness about him catching me staring at him. Maybe it was possible I was a little bi curious? I wondered to myself. I'd never considered it. I surely couldn't reveal that to him, he would think I was like, into him then. It was just erotic being naked with any person, I told myself.

"Here you go" he said, snapping me to the present. He didn't hand me the bottle though, he leaned over, positioned the bottle about 3 inches above my penis, and squeezed it out, personally pouring lubricant onto my manhood. I hurriedly put my hand on my penis and spread the cool lube around. I saw the bottle close as he held it, noting it was marketed as anal sex lubricant. I wasn't sure what to think about that. I blurted out without thought.

"Anal lube huh?" I said with a slight, automatic, nervous chuckle.

"Hey what can I say? Sometimes a lady I pick up likes giving up her butt!" He laughed.

"Wow, can't say I have the same burden to bear." I said with an internal grimace.

"Well I mean you've been in a relationship for a while, didn't she..." He trailed off, realizing he may have overstepped.

"Nope... She never did. Not with me, anyway... I've never done it with any girl actually." I said.

"Well I mean, it's not like it's better than pussy, you're not missing out much really. It's more of a submission thing than anything, I think. Girls don't usually get that much from it physically, but -" He stopped himself from continuing, stroking his cock again now.

"That makes sense yeah..." I followed his lead and began to masturbate with our newly slick erections. "I have to say, I appreciate that you've been here for everything after everything that happened. It's made a big difference. And this, being super comfortable, everything... it's nice." I said to him.

"Don't even mention it, man. I'll always have your back. For emotional or lubricant support." He laughed. I laughed too.

"I gotta say, I'm jealous of you. Down there, ya know." I said, turning red. I just couldn't help but somehow talk about his cock. Like I had to work it into conversation.

"Oh, man, don't sell yourself short. You know what they say, size isn't everything. Honestly it can be a pain. Finding underwear that fits right, stuff like that." He said, trying to make me feel less self conscious, but the image of him struggling to fit his genitals into a bulging pair of underwear didn't accomplish that at all. I felt strangely vulnerable... maybe even feminine when I looked at his manhood.

"You don't have to try and make me feel better, I just have a smaller one and you have a great... Well ah, I mean a really big one." I said, fumbling over my words.

"Well, thank you, I'm glad you think it's nice!" He laughed. He looked at me quietly after. I looked back. He seemed to stare right into my soul for a moment. Then very quietly, he whispered to me. "You can touch it, if you want to."

I responded instantaneously, maybe too quickly. "What- uh... no I just meant... I... I'm not gay Ryan, I don't-"

"I know you're not gay, you don't have to defend yourself from me. But you just have seemed intrigued. I think it's normal, ya know? And how often do two guys get to be completely alone together like this? You think it's big, nice, whatever. I'm just saying, you can touch it, if you want to."

"I... have you done something like this before...?" I mumbled nervously. How did he know i wanted to touch it?

"I have a pretty active sex life, as you're aware. And I'll even tell you that yes, There have been a few guys in there. Doesn't make me gay, doesn't make me anything. Or them, no matter what they wanted me to do to them. At some point I think men should experiment, you know? They were the same as you, just curious, interested in the male body. Specifically, my dick, but yea."

I was a bit shocked. I'd had no idea Ryan had slept with men. I didn't, like, care, I just hadn't thought so... "I don't know, it just seems...-"

"Wrong? Gay? It's just us man, it's whatever we want it to be. Those are just words, and we're just friends. Best friends just being comfortable." He stopped stroking, and got to his knees on the bed. He pivoted, so that he was facing my direction, his long cock perpendicular to my body, even with my own. He was offering it.

I stared at it. He looked down at me, shrugging in a "What's the harm?" Gesture. I hesitated. "Here..." He said. Without warning, he swing his leg up and over my body, straddling me. My eyes went wide in surprise. His cock now swung to face me directly, only about 6 inches from my face.

This was the invitation. I could refuse, tell him to get off, and forget the whole thing. Or I could reach up and take him in my hand, and go to God knows where with him. I thought about my ex. A beautiful woman. But with so much pain. And I thought of Ryan. A man, somebody I didn't think I had this sort of reaction to. But so much comfort and soothing feeling.

Who cared if he was male? I reasoned. I was comfortable with him. Naked with him. And I... I had a want in me to... Please him? Satiate curiosity? I couldn't be sure. I sighed, looked up at him, reached out, and grasped his penis in my hand.

It was like I'd received an electric shock. The sensation ripped through me. The heat from his member, the absolute rock hardness, the thickness, smoothness, and the slippery skin. He moaned. I looked up at him to see him smiling. I'd accepted his invitation. Now he had me. I was holding another man's stiff cock in my hand.

"Not so bad right?" He said with a grin.

"No... No its... Like I said it's... You have a really nice dick. It's... Big. Really big."

"You should have seen this black guy that goes to the gym I go to sometimes. Now that's big. Like nine or ten inches maybe."

I made a mental note that it seemed he went to an interesting gym, if he was seeing men with erections...

I came back to reality to find his lubricated cock still in my hand. I could feel it pulse. Instinctively, I slowly began to pump. Ryan moaned. He seemed perfectly at ease allowing another man to stroke his cock. I felt the voice trying to tell me to stop this, that I wasn't gay, fading away. I pumped a little faster, and a little deeper. I realized I was deliberately trying to pleasure him now. I couldn't believe what was l happening, but Ryan seemed to have almost anticipated it. I paused.

"Did you... Did you think that this would happen?" I asked, looking in his eyes.

"Of course not, how could I guess? Though..."

"Though what?" I asked pointedly. My hand still wrapped around his hardened shaft.

"Well, I had a feeling. And sometimes when other straight boys have seen me... I mean my dick... Well it seems like it has an effect. Always seems to be the same. They want to see it. Then they want to touch it. Then pump it. Then..." He trailed off.

"The... Then what?" I asked, like asking for the next symptom of a disease.

"Don't worry about that. Let's just have fun." He said.

"Tell me. What happens with these guys?"

He sighed. "After they stroke it, then they want to suck it. And then... They ask me to fuck them with it. " He said with a"fine but you're the one that asked " tone.

The images of Ryan's cock in my mouth involuntarily popped into my head. Then the image of it... being thrust inside my ass. I should have been repulsed. But I could feel nothing but intrigued. Curious. Lustful for it. Had that been what these other guys Ryan had bedded felt too? "Oh wow... And you...-"

"And yes I did. Fuck them. Went all the way. But that doesn't mean anything, Evan. It doesn't mean that I expect you to do that for me. We can just relax, be naked, and have fun as guys together. We-"

"Would you?"

"Sorry?"

"If I asked you to. Would you fuck me?" I asked pointedly.

"Evan you're my best friend. I wouldn't want anything to come between that..."

"What if I begged you to?"

"Evan... I feel like you're asking for a different sort of relationship... You'd be getting a different side of me."

"How do you mean?" I idly massaged his erection. Imagining it inside both my openings. I felt... Obsessed. Completely out of control.

"I mean that when I take another man like that... When I take him in the ass... It's a dominant/submissive relationship. I'm the dominant male and he's the feminine, submissive one. It's how I prefer it. If you were to ask me to take you, that's the sort of relationship we would have. When we were in private. You'd submit to anything I wanted. You'd have to accept that."