Room 359 with Rob

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First time homosexual experience.
9.8k words
4.66
35.2k
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Part 1 of the 2 part series

Updated 06/09/2023
Created 03/08/2020
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DeeOldman
DeeOldman
10 Followers

I'm Dave. Actually, I'm Dawei, but like most second-gen Chinese Americans I find it's helpful to have an Anglo name. I'm from the Bay Area, working in high-tech targeted mostly at intelligence scenarios.

So tonight, like many nights, I'm at the bar of a chain hotel in a town in Maryland, just outside Washington DC. The town consists mainly of low-slung buildings housing secretive government agencies and the military-industrial companies who supply them, along with hotels like this, and an occasional strip mall.

It's winter, dark and cold. There are no restaurants within a reasonable walking distance or good enough to be worth a drive, especially if you intend to have a drink. So, I'm here at the small bar—it's bright, the barman is friendly, the food is surprisingly good, and the drink selection is fine. It's an L-shape, with a total of about 8 chairs, I'm in the left corner at the end of the smaller L section.

I'm having dinner and drinks with Rob whom I'd met earlier this week in the hotel's small gym. We chatted briefly as we exercised and hit it off, so it's nice to have some good company over dinner for a change. Rob is Scottish, a former Royal Navy sailor. He's somewhere in his early forties, a few years older than me. He seems faintly military, except for his hair, which he wears in a long red ponytail. His accent is soft, but he has turns of phrase which sometimes leave me going "Huh?" until he explains "in American" as he says with a grin. We talked earlier about our jobs, but all he gave out was that he was a British liaison to an (unnamed) government agency. When I asked him what that meant in practice, he chuckled and said, "I liaise - in the overall context of the Special Relationship." I thought it best to not push for more info.

On the long side of the bar, there's a group of about 10 mostly 30-ish-to-middle-aged guys, with a single younger woman. The men are all in the business casual that is the dress code around here, polo shirts, slacks or chinos, casual shoes. The young woman is more formally dressed, a tailored navy skirt with pleats in an A-line, just short enough to be sexy but OK for the client's office; a white blouse (not-quite-see-through, but you can clearly see the outline of her lacy white bra); and black patent shoes with almost-stiletto heels. She and one of the guys are flirting.

"She's a real ride," said Rob appreciatively, then seeing my slightly puzzled expression, he grinned, "That's British English for hot or slut or both, depending on the context."

The group's talk is mainly about their companies, the technologies they sell, and the agency staff members they sell to or support. There's a kind of innocent enthusiasm for their products, and a slight contempt for the clients. As time goes on, the conversation gets louder, looser, less coherent.

"Pipe it down a little, guys, please," Rob says at one stage when the talk got loud, and the swearing ratcheted up. Everyone immediately complies. It's clear that he commands respect -- it's not his behavior, nor his language, just a kind of aura of quiet authority.

The group gets smaller as people drift away. The young woman and the guy leave together and head to the elevators, he drapes his arm around her shoulder, and she hooks her arm around his waist. I'm feeling envious of him and the likely end to their evening, upstairs.

Now there's only me and Rob at the bar. "OK then," he says, and reaches for the tab.

"Are you calling it a night, Rob?"

"Aye, but I could be persuaded to another if the company was good."

I motion to the barman. "Eduardo, can you get me another Chardonnay, and whatever Rob's having."

"Navy rum with ginger beer, Eduardo, please," says Rob.

"That sounds good, Eduardo can you switch mine to the same," I say.

We chat about nothing in particular while we sip the drinks, finally Rob drains the last of his and says, "I'm off to my room now."

"Turning in?" I say.

"Well maybe some videos to relax, then an early night. I'm going back through Westworld, I missed a lot of detail first time through."

"I loved Westworld!" I say.

"Want to join me?" says Rob, "I've got an HDMI hookup to the room TV, beats squinting at a laptop."

"That would be nice," I say. "I've got to hit the toilet first."

"Well, come on over when you're ready, it will take me a minute or two to set up the cable. Room 359."

We walk to the elevator, and I realize I have a bit of a buzz on, probably mixing the wine and the rum causing that. No biggie.

Back in my room, I pee. Then for some reason I take a washcloth, add some warm water and liquid soap, and thoroughly clean my knob. I accidentally drip some water on my slacks, so I quickly put on another pair of light khakis and decide to change my underwear as well while I'm at it. Ready. I take my room key and head to Rob's room.

"Come in," he says, as I knock.

I look around, it's an "Executive" room, two queen beds, an armchair, a desk, and an office chair, plus a large-screen TV, a minibar, and a full-length mirror on the wall outside the bathroom.

"Perfect timing -- would you like a drink? The minibar is well stocked."

"I'm OK for now," I say. "maybe in a while."

"Fair enough."

"OK," he says. "Westworld lined up. You can take the chair if you like, I prefer to prop myself up with come pillows on the bed, your choice."

I lower myself into the chair, Rob goes to the desk, clicks the laptop touchpad a few times, then plumps up two pillows on the bed next to me, and climbs on.

The episode begins. In the wild west town, the humans indulge in gunplay, bar fights, and sex with the theme park's robots. Then we're behind the scenes for robot maintenance. There are dozens of males and females completely naked as the technicians do their work. The robots (androids? -- I'm never certain) look and act completely human until the techs deactivate them.

Rob says "Actors, you've got to hand it to them, the men bollock-naked and the women showing their fannies to the world. I wouldn't be brave enough".

"Yep, agreed," I chuckle. Looking at them, I feel a slight arousal and my penis gives a couple of small twitches.

"More than their fannies, too," I say.

"Och, two nations separated by a common language," Rob smiled. "Fanny in British English is cunt or maybe pussy in American."

"Oh, I never knew that!"

"That's why you should never talk about your fanny-pack in England."

We both laugh and turn our attention back to the TV.

When the episode ends, Rob gets up and goes to the desk. He reaches down and rearranges the front of his slacks.

"I've got a half a stiffie from that," he says with a grin. "Another episode, or something else?"

"Whatever you fancy."

I stand up and go over to the desk beside him.

"You've got a bit of a tilt in your kilt yourself!" Rob grins.

I think, with a hint of panic, "He's talking about my penis, in Scottish!", then my rational inner voice says, "It's just guy talk."

I blush (yes, Asian men blush) and pull at my tee-shirt to try to cover the now obvious tent in my lightweight slacks. It just makes it more obvious.

"It's perfectly natural, you don't have to be embarrassed, it could happen to a bishop," says Rob.

"I was reared strict Catholic," I explain lamely. "Chinese Catholics are VERY religious - anything to do with sex was out of bounds -- it sticks with you!"

"I understand, my whole town was Presbyterian, everything fun was a sin in our kirk," he laughed. "Anyway, another episode, or something else? I've got the lot -- Netflix, Prime, HBO, Smutconnect..."

"Smutconnect?" I asked.

"Yep, it's a British streaming site, videos for a bit of whatever you fancy sex-wise. Great for relaxing with if you feel like you need a wank."

"A wank?" I said (I'd never heard the term before).

"Two nations again," Rob smiled. "Jerk off, beat your meat, masturbate"

"I-I-I don't..." I stuttered, then trailed off and blushed harder (meanwhile the tent in my slacks gave a little lurch). A little desperately I tried to explain.

"Where I grew up, the priests just called it self-abuse, it was a mortal sin, just below murder, so us kids never even talked about doing it."

"Except in confession," I thought to myself, and images flashed through my brain -- inside the church on a Saturday afternoon, dust twirling in the shafts of light from the stained glass windows, a smell of wax candles, fidgeting nervously with my friends as we awaited our turn to enter the confessional. "Bless me father, for I have sinned, it's two weeks since my last confession." You had to tell all your sins honestly, even that, or condemn yourself to eternal damnation. From behind the screen that separated you, the priest would question you -- "How many times? Did you take pleasure in it? Were you alone? How did you perform the act?" Sometimes you'd hear his cassock steadily rustling, and he'd clear his throat before telling you "Three Our Fathers and three Hail Marys, now go, and sin no more." I've left that behind a long time ago, but those kinds of memories are hard to shake.

"Well, if you don't wank, you're a unicorn, everyone else does," he grinned. "When I was at sea, it was everyone's favorite pastime - you could do it alone or share a wank with your mates. Life at sea is so boring most of the time, you need something like that. We had so many nautical terms for it -- polishing my knob, tossing at sea, raising the mast, hoisting the flag, rounding the horn; plus lending a friend a hand, helping out a mate, sharing my ramrod; or if there was an officer involved, polishing the brass." He chuckled, "Even the ship was called a frigate!"

"Yikes! I never would have thought that," I said, slightly shocked. He was so matter-of fact about something which had always been a big taboo in my life - I was more than a little flustered.

Rob went on, "When I first went joined up, I was pretty much ashamed of my own secret wanks, I'd been taught it was one of many roads to hell, and us Presbyterians don't have your Confession to wipe the sins away. The idea of wanking in company left me appalled. So I avoided it for ages, even though it seemed everyone else on board was at it. So one evening I was having drinks with some mates and it became pretty clear where things were leading so my curiosity (and beer) got the better of my fear and I thought 'Fuck it' and joined in. I realized I thoroughly enjoyed it, and over time it became 'Why not' and eventually just an enjoyable pastime that I looked forward to."

"Wow! another world," I thought, as I realized that is exactly what Rob's outlook on sex was compared to mine.

"OK then, video!" I continued in a rush, still a bit nervous at the direction of our conversation. "Smutconnect I guess."

Rob brought up the site. The front page was stills of people engaged in all manner of sexual acts.

"Want to pick?" said Rob

I looked at the captions -- one of them caught my eye "MILF enjoys BBC".

"Oh, I didn't realize the BBC did this kind of stuff!" I said.

Rob laughed -- "You haven't spent much time with porn sites, have you? BBC -- Big Black Cock."

"Oh!" I said again, then partly to end the embarrassment, "Sounds cool, let's watch that."

"I just want to get comfortable first, you get set, you can keep the chair, or you might be more comfy on the bed with some pillows like me -- you can use those pillows, I'll get some more," Rob said as he walked over to the wardrobe, took off his shoes and socks, undid his belt, pulled down his slacks, and hung them neatly.

I walked around the bed, shucked off my shoes, plumped up the pillows Rob had been using, and lay down at an incline against the headboard where he had been. I couldn't help a furtive look at him as he walked to the other bed to pick up some pillows and brought them over to set up. He was wearing a navy tee-shirt with black microfiber boxer briefs. The briefs clung tight to his lean body, and I saw the outline of his dick held in a ridge against his stomach by the stretchy fabric, pointed upwards towards the waistband. "It leans to the right," I thought (mine leans left).

Rob turned to me. "If you ARE thinking of a wank at some stage," he said, "you might want to remove the trousers. You don't want to get them wrinkled or stained, plus you'll need the freedom of access." He grinned.

Internally I shrieked to myself, "He's serious about masturbating together!"

I hesitated just a moment, then made a big decision. I swung to the floor, turned my back to Rob, and peeled off my socks, and finally after a brief hesitation, removed my slacks. I gave my tee-shirt a pull down over my now full-on erection, then turned and climbed back onto the bed.

Rob glanced over. "Nice knickers!" he said.

"What?" I said for the nth time that night.

"In American—that's a nice little pair of panties you're wearing."

I blushed (again), this time my cheeks were burning. "They're not panties, they're men's low-rise no-seam briefs." I responded.

"Nice color too -- my mum would call it Virgin Blue," he grinned. "There's no Y, how do you get your willie out for a stand-up pee?"

"No need to thread it through layers of cloth, the waistband is low enough you just need to pull it down, then up again afterwards. Simple and effective!"

Rob looked at me with a skeptical look.

"I'll show you." I said.

I thought, "Whoa, you're going to let another man see your cock," then argued with myself, "I'm just showing him how the underwear works, I think he's well used to seeing cocks - I've started so I'll finish."

I reached down to the waistband with both hands and started to pull the briefs down, but I hadn't reckoned with my now raging hard-on. The tip of my cock got caught below the waistband, and as I continued to push lower, my cock first reared up and then got pulled towards my toes, until the elastic sprang off with a tiny twang and my erection popped free, bobbed a couple of times, and remained pointed towards the ceiling. I hooked the elastic behind my balls and turned towards Rob.

"Well, that's the general idea," I said. "Normally there would be less resistance."

Rob laughed "OK I believe you. Nice willie, by the way."

"Thanks," I said, trying not to blush again as I unhooked the elastic from behind my scrotum and pulled the briefs (ok, panties) up. I had to use my left hand to press my cock flat to my abdomen and bent towards the left in order to pull the waistband over it. I thought, with a little shudder, "I just did something that I would never have imagined before tonight, and I don't feel any regret."

Rob had turned his attention to the video and lay back with his arms loosely crossed on his chest. In the video a hot woman played with a big stud's cock every way I could think of, and more. Meanwhile her partner reciprocated, with her cunt and her ass and her tits as his playthings. The video wasn't long, maybe 10 minutes. It ended with a cumshot, a closeup of the woman's face as she held his cock to her open mouth and massaged his cock - her mouth filling with spurts of cum, streaks of cum landing on her face, chin, nose, and in her hair. As his ejaculation finished, she took his cock and licked it like an ice-cream cone to clean it off, finally she opened her mouth wide to show the cum coating her tongue and hanging in a little string between her top and bottom lips. I kept my arms rigidly crossed over my chest during the whole thing.

I stole another look at Rob. His erection had swollen some more and was pressing hard against the tight fabric of his boxer briefs. I glanced down at my own cock - my knob was attempting to burrow under the waistband to freedom. I reached down to push it down and to the left a little more.

"Phew, Hot stuff." I said

"Some more?" asked Rob.

"Definitely!" I said. "That was certainly arousing."

"Same category? Or something different?" asked Rob.

"Up to you, whatever you choose is fine with me," I replied.

Rob got up and walked to the laptop. From behind I noticed how his ass firmly filled his briefs without overdoing it. I thought to myself, "Fancy a bit of that? Homo!".

He turned and came back. Maybe I imagined it, but it seemed he took a good look at my panties and their swollen contents as he walked and got back onto the bed. My cock stiffened a little more at the thought. I thought "You fancied his ass, now you're fantasizing him fancying you, this has to stop!"

"I set it on random continuous, we can just let it run without having to keep selecting." He came back and resumed his place on the bed. We turned our attention to the screen.

Random or not, the first video up was from the Gay Male category. I thought "I wonder if he did that on purpose?"

Hunky guys met up and did obscene things to each other - cocks, balls, mouths, hands in every orifice and every imaginable grouping. After a couple of minutes, it became a bit repetitious.

I saw some movement from the corner of my eye, and I stole a glance over at Rob. He had moved his hand down to cup his balls in his curved fingers. He gave a few slow squeezes, then dragged his fingers up his cock to the knob, then dragged the backs of his nails back down to the base. He continued, repeating the motions, slowly, deliberately, with no sense of urgency. My internal voice shouted, "I can't believe this, he's actually jerking off in front of you!" and again I gave an involuntary shudder as my own cock leapt at the sight, and I felt an irresistible urge to caress myself. As I moved my hand to my cock, Rob turned and looked at me with a smile. "Is that a cucumber you've got in your knickers or are you just glad to see me?" We both laughed and turned our attention back to our erections. I thought "He's flirting with me!"

At first I emulated Rob's up-down actions, but shortly I found I got more sensation from gently rubbing the fabric on the underside of my glans, making little circles on my frenulum, and occasionally digging in a little with my nails in a gentle up-down scratching variation. My cock was throbbing at this stage, and my erection was bigger than any I could remember.

After a few minutes I turned my head to Rob, and he looked back and winked. We continued our separate activity and I felt a little moment of recognition that my views on "self-abuse" had changed, and fast -- what was unthinkable an hour ago was now just a shared activity between mates -- enjoyable, harmless, maybe even good for you.

Rob spoke first. "Would you like a hand with that?" he said, nodding to where my hand was gently caressing my glans.

I froze for a second or so, thinking "That's another step into the unthinkable."

Rob said softly "In for a penny, in for a pound."

I nodded. My breathing was a bit ragged, and I had to clear my throat to reply. I heard myself say, not "OK", but "I'd love it", and I thought "Where did that come from?" Rob was definitely affecting my entire attitude to man-on-man behaviors.

Rob turned on his side towards me. Time slowed down for me - it seemed like ages as I watched his hand reach over and slowly come to rest on my cock. It's a moment I will never forget, another man touching my erection for the first time, the picture burned into my memory. He grasped my cock with his fingers and thumb opposed on my shaft through the light microfiber of my panties and began a slow stroking, up to just under the corona, then back to the base of my shaft, then back gain. I shivered with pleasure at his touch.

Making another decision to follow wherever the rabbit-hole led, I turned on my side to mirror his position. I had to clear my throat again to hoarsely ask "Sauce for the gander?". He got my meaning and said "Please!" with a grin and a nod. I reached out, and for the first time in my life, I touched another man's erect cock. "Swooning" seems like an old-fashioned word, but it's a perfect description of how I felt as we commenced a mutual cock-massage. My body was in a heaven of pure pleasure. I followed Rob's lead on the motions, and we lay quietly working away on each other's cocks. I kept my gaze focused on our hands, I wasn't sure if I was avoiding his eyes out of embarrassment, or if I was just eager to watch what I'd never seen before.

DeeOldman
DeeOldman
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