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.
