Getting Back on My Feet Ch. 04

Marc had put the list of all the gay sex acts I was supposed to complete by the end of the year up on the fridge. He affixed it using a heart-shaped magnet. Nice touch, I thought.

A few days passed without anything happening between me and Marc. Given our work schedules, we really didn't even see each other much for a few days after he had made The List. Every time I walked through the kitchen or opened the fridge, though, I noticed it. It was posted prominently there, as if accusing me: "Come on, there's so much more for you to explore. You know you want to." The truth was, I didn't know where to start. Sure, hooking up with Marc and exchanging blowjobs had been exciting and sexy, but some of the things he had committed me to were pretty intimidating for a straight guy. Fuck, was I even straight anymore? Was I just experimenting? Bicurious? Gay? I didn't even know.

Three days after Marc made the list, I was sitting at the kitchen table eating a bowl of cereal and scrolling through instagram on my phone. Marc came into the room wearing a suit and rolling a suitcase.

"Hey Nick - I'm heading to NYC for work this week, so you'll have the place to yourself until Saturday."

"That's cool, man. I hope that you have a good trip!" I said.

He paused as he straightened up some things on the kitchen counter.

"You know, Nick, maybe you should use this time while I'm gone to make some progress on your list." Marc said, nodding in the direction of The List on the fridge. "I bet you could check a few things off while I'm gone...maybe go ahead and set up a Grindr profile." He smirked as he said this.

My face reddened when he said this. I hadn't really expressed my anxieties to him about continuing to experiment with the gay desires he had awakened in me.

"I dunno Marc," I said, fiddling with my phone. "Maybe this is all too much, too fast. Don't get me wrong. I loved when we hooked up - that was hot and fun...but some of these things seem pretty advanced for me."

Marc sat down in the chair across from me and looked into my eyes. "Nick, I know all of this seems new and a little bit intimidating. But you were the one who told me that you thought you needed to broaden your sexual horizons. All of this is part of that. Before you let me suck your dick, you had never contemplated doing anything sexy with another man. Like I said, you may find there are things you don't like, but if my suspicions are correct, you'll find a lot more things that you DO like. You just need to take the first few steps."

I looked down at my phone, not wanting to make eye contact. Deep down I knew he was right. My curiosity about sex with men had been piqued and I knew that I needed to go further down the rabbit hole.

"You're right, Marc. It's just that this is new to me, and a little scary."

"I know it is. But that's also what makes it fun! Being a little scared, exploring new things. Giving up control...not quite knowing what's going to happen next. The thrill of the chase...or being chased. Now, I've got to head out. But I hope you have a great week."

Marc gathered up his things and rolled his suitcase to the door. He pulled out his phone to order an uber. I got up and put my cereal bowl in the sink. I wandered over to Marc.

"OK, bud. I'm off!" Marc. pulled me in for a bro-hug, slapping my back as he hugged me. As he leaned in, he whispered in my ear: "Don't do anything I wouldn't do!" and then he bit my earlobe and gave my cock a playful squeeze. With that, he was gone.

I wandered aimlessly around the apartment for a while. I turned on the TV and flipped through channels, but I couldn't find anything that interested me. I messed around on my phone, scrolling through instagram. I was just restless. With Marc gone, I felt like I was just rattling around the apartment.

Idle hands are the Devil's workshop, as they say, and my idleness and curiosity started to get the better of me. I wandered down the hall to Marc's room. I surveyed the scene. I hadn't really taken note of my surroundings the last time I had been in here. Marc's room was so neat. The bed was perfectly made, with a slate-gray duvet cover. There was a bookcase in the corner. There was a tasteful mid-century dresser with a leather tray on it containing some spare coins. A scented candle. I noticed again the tasteful black and white photographs of male torsos that adorned his wall that I had seen when I had first toured the apartment. It was very much the room of a modern, fashionable and moderately well-off gay man.

I browsed the titles on his bookshelf. An eclectic mix of stuff for sure. Some science books. A few historical biographies. Some fiction. Tucked near the end of the shelf, pushed back a bit was something interesting: "The Joy of Gay Sex - Fully Revised and Expanded Third Edition." I took it off the shelf and sat down on the bed while I paged through it. There were illustrations of guys in all sorts of different positions. Guys blowing each other, guys getting fucked in the ass, a guy blowing two dudes at once. Unconsciously, my hand moved to my rapidly-hardening dick as I flipped through more of the pages. I stopped myself. I didn't want to make a mess in my pants in Marc's room. I made a mental note to come back for the book later so I could enjoy it more.

I stood up and continued my snooping. I opened up his closet. Nothing especially interesting. Some dress shirts and two suits. I checked the drawers in his bureau. Pants, t-shirts, socks. All neatly folded. I opened another drawer. It was his underwear drawer. Now this was a bit more interesting. He had some tighty-whiteys, some boxer briefs, and three skimpy Y-backed thongs in different colors. I chuckled as I caressed the soft material. An image of Marc's muscular body wearing one of these thongs flashed through my head and I felt my cock jump a little bit.

I put everything back as neatly as I had found it, not wanting Marc to find anything amiss and feel that I'd violated his trust. I returned to the bed and snooped through the drawer in his nightstand. Half a dozen condoms and a medium sized bottle of lube. I imagined Marc bringing different guys back to his room, seducing them, removing their clothing and underwear, laying them back on his bed, his partner rolling a condom onto his cock, and Marc lubing himself up and gently entering his lover, who moans softly as Marc's girthy dick opens him up. I imagined how Marc might feel, his rock hard cock invading yet another tight hole - maybe a new one, maybe one that he has fucked many times, the pleasure centers in his brain lighting up as his dick pushes deeper into his partner. I imagine his muscles rippling as he finds his rhythm and begins pumping in and out, his lover moaning uncontrollably and writhing in ecstasy as Marc holds him down firmly and takes his pleasure.

My breathing was shallow as I imagined the scene. I closed the drawer to his nightstand and hastily exited his room. He hadn't been gone for a day and I was already snooping through his things. I decided I needed to take a walk to calm down. I was going crazy just being in this apartment by myself.

I put on my shoes and headed out. It was an unseasonably overcast and chilly day in Los Angeles. I walked for what seemed like hours, thoughts swirling in my head. Was I horny? Definitely. Ever since Marc and I had hooked up for the first time, I had been in a state of elevated sexual arousal. I needed something to distract me. When I got back to the apartment I decided to call Carole to see if she wanted to hang out or get a drink.

Carole arrived about twenty minutes later. A knock on the door signified her arrival.

"Hey Nick!" She said brightly as she came through the door. She took off her coat and tossed it onto the sofa.

"Hey Carole. Thanks for coming over. I feel like I've been a bit anti-social the past few days. I just need someone to hang out with. You want a beer or anything?"

"God, yes. I'd love a beer."

Before I could make a move to get one for her, Carole made a beeline for the fridge and I froze. I knew that the list wouldn't escape her keenly observant eyes. She opened the fridge and grabbed two cold beers from the door and then closed the fridge. She paused. I could see her as her mind processed what she was reading.

"Nick...What. The. Fuck. Is. This?"

She took the list from the fridge and sat down at the breakfast table, holding the list in both hands as she perused it.

"Well, I guess I should be proud of you for actually following through and sucking Marc's cock. I honestly didn't think you had the courage to go through with it. But it says right here - checked off on September 2nd. Well, well, well. You have to tell me everything, obviously. But there's a lot of other depraved stuff here. What the hell is going on with you, Nick? For someone who told me a week ago that he wasn't thinking of turning gay, this looks pretty fucking gay."

I sat on the couch and put my face in my hands.

"I know, Carole. I know. Things just got a little bit out of hand after Marc and I hooked up. That list is really just a joke." I laughed weakly.

"Bullshit, it's a joke. You want to know what I think? I think that when Marc first sucked you off, it awakened something in you, a hunger that you never knew you had. And now that you've sucked a dick, you want to know how much further down this rabbit hole you can go. You want to know more about the pleasures of being intimate with men. Well, today's your lucky day, because I am going to help you out. We're gonna check at least one thing off your Big Gay Bucket List. I'm gonna help you set up a Grindr profile!"

Carole grabbed by hand and pulled me off the couch, leading me towards my bedroom.

"OK Nick, give me your phone and strip off your clothes!"

"Carole, wait a minute...come on, let's just take it easy. There's no way I'm setting up a Grindr profile!"

"No way, Nick. You're not gonna bitch out of this now. The correct time would have been before Marc sucked your dick, and you returned the favor. Now, come on, take off your shirt!"

Carole tugged at my shirt and pulled it over my head.

"Great. Now your pants."

She undid my belt and tugged my pants down. I was standing there in just my boxers while Carole navigated to the app store and downloaded Grindr. I could not believe this was happening.

"You are gonna be a hot commodity, honey. Lots of horny gay guys won't be able to resist the opportunity to break in a newbie like you. Sure, you've sucked one cock, but these studs will turn you out for real."

I blushed when she said this, thinking of the possibility of being constantly hit on by aggressive Grindr guys.

"Let's see...username...How about 'NewBicuriousDude69' hahaha! Password...we'll go with 'Cumguzzler420'. Age...38, Height, five-foot-ten. Weight, what? 165 pounds? Body type, hmm, I guess we'll go with toned. Position...let's say 'Vers', but I'm betting you're more of a bottom, hahaha! Ethnicity, white. Relationship Status, single. Let's see here...Tribes...I'm gonna say "discreet" because no one knows you love dick, yet. Ok, now, you're looking for Chatting - definitely. Dates - absolutely. Friends - sure, but only with benefits! hahaha!"

I looked over her shoulder as she merrily checked off various boxes and options for my profile.

"OK, now we need a profile picture. Give me a nice smile!"

I tried to give a natural smile and not look awkward.

"Come on Nick, give me a little enthusiasm!"

I struck a few poses. I flexed. I tried to look coy and innocent, smiling and biting my lip in this impromptu photoshoot. When Carole was satisfied, she said "OK, I think we are good on pictures. I think some guys may even hit on you in spite of these," she said sarcastically.

"Alrighty...now the "About Me" section...Where to even begin? Hahaha!"

Carole was having too much fun with this.

"Oh my god Nick, I cannot wait to hear about all of your sexy adventures with this app. It's going to be insane! Ok ok ok...About me. How about this? "38 year old dude, recently divorced from a woman. Lately I've become more interested in exploring my gay side. I'm not very experienced, but I'm eager to learn! What I lack in experience, I promise to make up in enthusiasm! I'm Interested in meeting up with guys for conversation, fun, or whatever."

The "whatever" was doing a lot of work in that sentence. But it was done! I had an official Grindr profile. I'd definitely heard about it before, and how easy it was for guys to hook up, but now I guess I was going to find out for real.

"Nick - you have to tell me everything about what happens on Grindr! I'm sure you'll have dudes salivating over the chance to break you in."

As she said this, she wandered over to my dresser, where I realized the as-yet unopened anal training kit was sitting. I had meant to put that away, far away from where anyone could see it. I still hadn't gotten up the nerve to use it.

"Well, well, well! I see we still haven't worked up the courage to open up the backdoor," said Carole.

She picked up the kit and fixed me with a serious look.

"You know, Nick, when you start meeting guys from Grindr, they're going to have certain...expectations. They're gonna be looking for a guy who can take dick. Now, think of how embarrassed you're going to be when you bring some stud home, and things start getting serious. He's gonna be rock hard and ready to invade your cute little rosebud, but you won't have any idea of what you're doing. You need to be prepared for that."

"Carole...What are you talking about? Who's gonna be bringing dudes home? No one's going to be invading any rosebuds!"

"Oh, Nick!" Carole scoffed. "You have no idea what you're talking about. The minute some muscular stud even looks in your direction, you're gonna be on your back with your legs spread, begging him to fuck you. You owe it to the guys who are gonna be owning your pretty little ass to at least kinda know what you're doing. That's why I bought you that kit. Although, I admit, I thought it was gonna be Marc who got to tap you first. Now with a Grindr profile and a week to go before he gets back, you could be 10 dicks deep, at least!"

I rolled my eyes, but my stomach fluttered a little bit too at the thought of being a total slut for the men of Grindr.

"Alright, sweetie. I gotta run, but this has been tons of fun. I hope you have a fun afternoon chatting with some hot studs on that app! I literally cannot wait to hear all about it!"

And with that, Carole headed out. I was still standing in my room, somewhat perplexed at everything that had just taken place.

I picked up the anal trainer kit from the dresser and looked at it. There were three cone shaped plugs, small, medium and large. I wondered what it would feel like...I'd never had anything in my ass before. Fuck it, I decided I would try it.

I opened the kit and felt the plugs. The silicone was silky and smooth, and each one felt pleasingly heavy in my hands. I took them to the bathroom and washed them off. Then I dried them and set them on the counter. I wanted to be fresh and clean for this, so I disrobed and got in the shower.

I spent a lot of time in the shower, letting the hot water cascade over me. It was relaxing, and I let my mind start to wander. I imagined Marc opening the door to the bathroom, wearing a towel around his waist. I imagined him dropping his towel, revealing his half-hard cock and opening the shower door and stepping in. "Room for one more?" He says, as his hands find my hips and draw me close to him, leaning in to kiss me. I started to get hard and stroke myself a bit as I imagined this scene, making out with Marc in the steamy shower. I stopped myself because I didn't want to cum before the main event.

I got out of the shower and dried myself off. In the bedroom, I arranged the towel on top of the bed and then I sat down. I uncapped the little bottle of lube and set it on the nightstand. I picked up the smallest of the cone-shaped plugs. It had a pleasing weight in my hand, and the silicone finish felt nice. I picked up the lube and squirted a generous portion onto the plug, and spread it all over. Then I laid down and put my feet up. "Well, here goes nothing" I thought.

I placed the tip of the plug at my hole and gently pressed. Nothing. I pressed a little harder. Still nothing. It hurt a little bit. I picked up the lube and squirted a dollop on my hole. The cool lube ran down the back of my nutsack and onto my "little rosebud," in Carole's words. I tried my best to relax. I pressed the plug to my hole again, trying to think of something sexy.

I closed my eyes and imagined a scene where I was in Marc's dimly lit room, lying on my back in his bed. There he was kneeling above me, his hard cock sticking out from his body. His hairy chest and abs visible in the flickering light of the scented candle that he had lit a few moments before.

"Nick, just lay back and relax," Marc whispered in a low voice. As I touched the tip of the plug to my hole, I imagined Marc's hard cock pressing into me, firmly and insistently. I pressed harder, and then my hole gave way and the plug slid into me. I gasped as the firm silicone plug found its home. I felt full, but in a good way. I hadn't noticed before, but my cock was achingly hard. I closed my eyes again and resumed my fantasy:

"Fuck, Nick, you're so tight!" Marc said as his beautiful seven-inch cock slid into me. "Don't worry, I'll be super gentle." I let out an incoherent moan and I spread my legs a bit wider and imagined Marc's strong hands on my chest, as my hole adjusted to the girthy cock now nestled firmly in my ass. I gently played with the base of the plug, slowly gaining confidence as my body adjusted to the feeling. I slowly pulled it out, enjoying the delicious feeling of the wider part of the plug coming out and my hole returning to its normal size, but now I was left with an empty feeling.

Once again, I pushed the tip of the plug to my hole, and this time it opened up easily, seemingly eager for the plug to find its place. I returned to my fantasy. Marc slowly pulled his cock out, almost to the tip, before he plunged back in. I moaned again, imagining Marc's muscular torso rippling in the candlelight as he slowly started pumping my ass. I sighed as I enjoyed the feeling of being full. My left hand wandered to my hard cock, and I started gently stroking myself. I imagined Marc's strong arms around me as he picked up a rhythm - in and out, in and out. I started stroking faster, imagining his strong hands gripping my ass as he tried to go deeper, kissing my neck at the same time.

I started breathing heavily as I imagined Marc intently bearing down on me, filling me up. I could see him in my mind's eye, gritting his teeth and feeling the pleasure of my smooth, slick hole, but trying not to cum. I imagined him letting out a moan as his balls tightened up and he filled me up with a big, hot, creamy load. This image was too much for me, and I started cumming all over my abs and chest. It was one of the biggest loads I could remember. I was drenched.

I laid there for a minute, trying to catch my breath. I slowly eased the plug out of my hole, savoring the feeling of it stretching me out again as the wide part came out of me. I tossed the plug to the floor, just laying there and enjoying the afterglow. What an intense fantasy that had been. Could I really go through with this? Could I really take the next step and enjoy full on gay sex? I was still scared, but I knew that I had to keep going, and that eventually Marc would take my ass.