Logan - Making Rent

In my third year at NYU in 2004, my friend Jason found a great deal on a rent-stabilized apartment in Greenwich Village. It wasn’t a great apartment; from the looks of it, I’d say it was last renovated in the early 70s. But the Village is a prime location, and while going to college, it was unbeatable. It meant our place was within walking distance to all the best bars, which meant sex, sex, and more sex. We lived it up, too. 

For two years, neither of us had a steady girlfriend, and neither of us was ever sexually frustrated either. We’re both good-looking guys, and we stay in shape. We hit the gym a few times per week, and Jason hooked me up with a few modeling gigs that he couldn’t take because he was already booked. I didn’t go to school for any kind of art, but it was still fun and easy money.

When 2006 rolled around, we had been out of college for the better part of eight months, and I had yet to find a job where I could use my business degree. Jason was working more and more as a paid actor, in the city and out on the West Coast. He would toss me a modeling gig for extra cash when they popped up, and that was helpful because I have student loans to pay. 

Unfortunately, or fortunately, in the spring, Jason got cast in a recurring role on a show that shoots in North Carolina. He warned me it meant he’d have to give up his room in our apartment, and since our lease was coming up in May, he recommended I start hunting for a new roommate or think about moving. I didn’t want to move, and because it was such a great location, I figured it would be easy to find a new roommate.

I went on Craigslist and posted an ad. Jason has a nice digital camera, so he helped me take a bunch of photos, including a good one of me as the potential roommate.

I must have gotten hundreds of responses over the next few weeks. Most of them turned out to be scams. A bunch of them wanted to know more about me, including my sexuality, which surprised me. I know the Village is a gay friendly neighborhood, but I didn’t realize there was an assumption that a good-looking guy living in the neighborhood was assumed to be gay. I asked Jason if that was a common rumor, and he said it was and laughed that it hadn’t been something I heard.

I interviewed a few guys, let them tour the apartment, but none of them wanted it once they saw how small the bedrooms are for the price. I tried to point out that the price is below average because it’s rent-stabilized, but they were all willing to live in Brooklyn or Queens for the same price and more square footage.

When Jason moved out at the end of the month, he was generous enough to pay for that month anyway, since I still hadn’t found a new roommate.

Over the next few weeks, I tried again to get a roommate through online channels, while working extra shifts in the hopes of covering the entirety of next month's rent if I didn’t find anyone. Again, I got a bunch of nonsense emails, a few legitimate hits, a surprising amount of pictures of naked men, but only a few came to look at the apartment. None wanted to move in, though.

“Logan, what’s with you today? You’ve been kind of a dick to your tables all day, and you’re banging around in the kitchen more than usual.” José asked as I filled up two glasses behind the bar with soda.

I shook my head, sighed, “Ugh…I’m just stressed.”

“You ok?” He asked, cutting up lemons for cocktails.

I tossed cherries in one of the Cokes. “I need a new roommate, and I need them by next week,” I told him in a huff.

“No shit, you still haven’t filled Jason’s spot?” He asked, sliding a bunch of sliced lemons into a jar.

“I can’t believe how hard his room is to fill,” I told him, getting a glass and filling it with ice.

“Well, it’s kind of a shithole,” he joked.

“No, it’s not, and it’s prime location,” I fired back.

“Sure…but, I’ve been there, man, it’s like a frat pad, I’m shocked you keep living there,” He said.

“It’s a great deal, and it’s rent-stabilized,” I said.

He made a face of surprise, “Well, that is nice, but even still, the building is old as hell, and when you walk in, it looks like you’re going to murder or rape me, probably both,” he chuckled.

That made me laugh, “yeah, I noticed that in some of the pictures, so I repainted Jason’s room white, and got shades for the lamps, but it’s not that bad. Plus, the food in this neighborhood is unbeatable, and you’re right down the block from some of the best bars in the city.”

“Did you upload those pictures in your ad?” He asked.

“No, I don’t have a digital camera,” I told him.

He chuckled, “Bro, you’re going to have to work the corner if you keep using those photos.”

I smiled, “Thanks, man. That’s helpful.”

“Hey, bro, I got a camera you can use. I’ll bring it to work tomorrow, just don’t break it,” he grabbed a bin of clean glasses and started putting them away.

“That…is helpful, thanks, man.” I took my tray of drinks over to my table, feeling just a little lighter knowing I can get better photos up. It was still weighing on me that I had a week to find someone.

I took José’s camera home the next night, took a bunch of pictures, and posted yet another ad online with the updated photos, including one of me as the roommate.

The next morning, I responded to only the emails that seemed like they weren’t a complete waste of time, even the ones asking if I was gay. After my morning shower, I was walking around naked because it was a freedom I didn’t have when Jason was still living here. Then I went online to field a few more emails.

One was a response to me telling a guy that I’m straight.

JoshBig27: That’s a shame, you’re hot.

Me: Thanks, man, but I’m looking for a roommate and don’t mind if you’re gay.

I had a similar back-and-forth with a dozen other emails. Then I got dressed and rushed to work. Of course, I forgot to bring José back his camera, and he gave me shit for it, especially since our shifts don’t overlap for the next three days.

When I got home, I set up some appointments for guys to swing by and look at the apartment, one of them, to my surprise, was JoshBig27.

All of the tours ended the same, with them telling me, “I’ll think about it.” Josh seemed to be checking me out more than the apartment, which was flattering, but I felt the need to remind him that I was just looking for a roommate. “And, even though I’m not gay, this is a pretty gay friendly neighborhood, so that’s a perk,” I told him.

He wet his lips and looked up and down my body. I was wearing a sleeveless workout shirt and gym shorts because I planned to hit the gym after this showing. “Oh, I know it’s a gay friendly neighborhood, but how would you feel if I brought guys home for…you know, sex?”

This was a first, and I felt myself blush at the idea of gay sex happening in my apartment. “Umm…I guess, it wouldn’t bother me as long as it doesn’t bother you that I bring home women almost every weekend,” I chuckled.

“Do I get to watch?” He asked, seemingly as a joke, but the look in his eyes made me question if it was.

I blushed again, “I…ummm….”

“Joking, of course,” He cut me off.

I pushed forward, “So what do you think?”

“Hmm…it’s a bit dated, but the price is doable. When do you need to know by?” He asked.

“Preferably today or tomorrow. Rent is due on Tuesday next week, and I don’t want to cover it on my own,” I shrugged, feeling a little exposed by that statement.

“Ah, ok, well…I’ll have to let you know. I have two other places to look at today, but I like you and the location is great,” he crossed his arms.

“No problem, you have my number. Text me either way,” I told him, and then walked him out.

I hit the gym and then went to the store and picked up some food on a budget. Then sat down to watch a DVD when I got a text from Josh. 

Josh: I didn’t want to leave you hanging, but I found a place on the LES that I’m going to take.

This hit me hard. I thought he was going to take the place.

Me: Damn, ok, thanks for letting me know.

I decided to trade my tea in for a whiskey and Coke. Jason left all of his booze, so the place may not have any food, but plenty of liquor to wash away the stress. About twenty minutes later, I hopped on my laptop, responding to more emails and looking at my bank account, which was $500 short of making rent.

One email was a response to me telling a guy that I’m straight.

Carl91NYC: That’s a shame, with a body like that, you should rent that room by the hour instead of monthly.

I read the comment and almost spit out my drink. I was about to delete it because it was stupid funny, but then I took another sip of my drink and read it again. And again. With the liquid courage running through my body and the looming deadline of rent being due, I started typing out a response of pure curiosity.

Me: That’s flattering, how much could I get by the hour?

I hit send, thinking it was harmless. I’m not homophobic, and back in high school, I jerked off with a few of my friends, even tried swapping blow jobs once. It was fun, and it felt good. I definitely blew my load in my buddy's mouth, but I was never attracted to guys, so that fooling around stopped when I started having sex with girls.

A few minutes later, after sending a response, looking into the apartment, and seeing if it was still available, I refreshed the browser, and I had a new email from Carl.

Carl91NYC: Depends on what you’re willing to do. I can think of a lot I’d do to you, but only if you’re willing. [He attached a picture of his body, another of his dick]

He looked about ten years older than me. I’d say mid to late thirties. He’s in decent shape, but probably doesn’t go to the gym or isn’t getting enough cardio to be cut. His dick was hard in the picture; mine is seven inches circumcised, his looks about the same size, maybe a little smaller. The picture didn’t do anything for me, but I did give it a long, hard look, wondering if I could suck a stranger's dick for money. I decided to respond and put all the cards on the table.

Me: Well, I’m straight but need to make rent. I need to make $500.

I hit 'send' and then started hitting 'refresh' so many times that I was worried my internet had broken. Then a response came through.

Carl91NYC: $500 is steep, even for a sexy straight boy like yourself. I could do $200, but it would need to be worth my while.

My heart was pounding out of my chest reading his offer. What does “worth my while” even mean? Would I need to fuck him? I don’t know if I could do that. If I were horny enough, maybe, but if you told me to fuck a guy in the ass right now, I don’t think I could even get hard.

Me: I’ll be honest, I don’t think I could get hard for another guy, at least not hard enough to get paid to fuck him. I could give a blow job, though, that doesn’t require me to be hard, right? What would you pay for that?

I put my laptop down, then went to take a piss. I took a shot of whiskey and hit refresh. He already responded. I hesitated, as if clicking on it somehow was agreeing to suck his dick. It was the only new email, though, so I clicked.

Carl91NYC: In my experience, straight guys don’t give blowjobs worth paying for. To be clear, I was saying I can do $200 to do you, not the other way around.

WHAT!? He wants me to bend over and take it from him? Absolutely not. No chance. Out of the question. I’m not gay, and that’s the gayest of gay things anyone can do. I shoved my laptop away and refilled my whiskey and Coke. Pacing the apartment, which wasn’t easy because the living room is small and the love seat and chair take up 90% of the space. Fuck, this place is a shithole, isn’t it? I looked around at the walls that aren’t straight, the one window that looks into an alleyway, the hardwood floors that haven’t been polished since before I was born, but I do love this place.

I sat back at my laptop and opened his email again.

Me: I hadn’t realized you wanted to fuck me. Honestly, there’s no way I could do that for $200. Like I said, I’m straight, and if I were to let that happen, it would be a one-time thing, and I wouldn’t do it for less than $1,000.

I hit send, laughing to myself. Out of pure curiosity, I went on the Men Seeking Men section to see what guys charged for sexual favors. I went down a rabbit hole of guys willing to give it up for free, dozens of them claiming to be straight but wanting to take it up the ass, which made me laugh. There were a few guys who did look like models who didn’t outright say they were looking to get paid for sex, but it was implied, and there were a series of numbers that ranged from $100 to $400, depending on how good-looking they were and what they were looking to do. It got me thinking I could get $50 for a blowjob, and if I did that ten times, I could make rent. Do I want to suck ten dicks to make rent one time, though?

Carl91NYC: $1,000 is steep. I could go $300, since you’re “straight,” but you have to take it in the ass.

That was all it said. My heart was pounding. Could I take it in the ass? If this guy is willing to pay $300, how much could I make if I post an ad, auctioning off my ass as a virgin straight boy ass?

I took another shot and went to the M4M section and created an ad:

Straight guy trying to supplement rent. Never been with a guy, but in a bind, just need to cover rent. Let me know if you're interested, and we’ll go from there.

I pulled out José’s camera and took a few pictures, similar to the ones I saw other guys had posted, and uploaded them. None of them had my face, though, that was a risk I wasn’t willing to take.

Another whiskey and Coke later, it was a little after 9:00 pm, and I was feeling pretty drunk, so I decided to hit refresh on my email. I was shocked at how many responses I had. Way more than were interested in the apartment.

I was still on the fence about actually going through with any of this, but I did start firing off responses. A lot of them were asking similar questions, so my answers got almost to a copy/paste variation of the same information.

“6 foot, 165 pounds, 7 inches, circumcised.”

“Need to make $500.”

“Condoms only.”

“I don’t know what that means.”

“Yes, I’m actually straight.”

“Swallowing would definitely cost you extra.”

“I don’t do drugs.”

“I’ve never tried that.”

“I’d let you do that to me, but I’m not putting my tongue there, sorry.”

I was actually having fun with some of the emails. While I’m not into guys, it was an ego boost to see how many guys were interested in me sexually, and some of the filthy things they said they wanted to do to me. I did have to Google some of the things they asked me. I had never heard of rimming, or poppers, or frotting, in all of my sexual experiences with women. Though rimming an asshole and eating a girl out are only different by about an inch, I still had to Google it to be sure it was what I thought it was.

Some guys didn’t respond after that first inquiry, but others wanted more pictures, more info, and I gave it to them. Most of them were not interested in paying my asking price, but a couple were, though their demands were more than I was interested in for the most part.

WaltDickney69 sent me a few pictures of himself. He’s going grey, says he’s 35, but looks older. Nice smile, good body, very corporate, says his dick is six inches…not that I care, but good to know.

WaltDickney69: Straight here, looking for a clean guy to fuck. Married, so I can’t risk catching anything. Are you really a virgin?

Me: I’m an anal virgin. I’ve had sex with a lot of women, and I’m not actually into guys, not even bisexual, but I’m willing to rent my untouched ass for the right price, one night only.

WaltDickney69: Send me a picture of your ass.

He was the first person to ask for a picture of my ass; everyone else wanted to see my dick. I stood up, shoved my shorts and boxers down, and tried my best to take a picture of my ass, taking a few to make sure I got one. Then plugged it into my laptop and found one that was in focus and sent it to Walt.

WaltDickney69: Mmm, very nice. You must work out or play sports. Look, I don’t want to waste your time or mine. Tell me your number, and let's see if we can’t set this up for tonight.

Damn. This got very real, really fast.

Me: $500

WaltDickney69: I can do $500, but you get nothing if you don’t make me cum. I prefer to cum in your ass, but I can cum in your mouth, and you’d have to swallow. If you’re down, send me your address in the next email.

Holy shit. This guy is going to pay the full $500, and all I have to do is let him fuck me?! How bad can it be? If those gay guys can handle it, so can I. At the worst, it’ll last what…fifteen minutes?

I sent him my address and took another shot. I was already feeling drunk, but there was no way I could do this sober.

WaltDickney69: I’ll be there in 30 minutes. Make sure you’re cleaned out.

Cleaned out? What the fuck does that mean? I opened Google, “gay sex + cleaned out”. The results were mortifying. I suddenly felt in over my head, but I ran downstairs, down the street to the local sex shop, and drunkenly asked, “Do you have an enema?”

The guy behind the counter, a hefty, unshowered fellow, chuckled, “First time?”

I leaned on the counter, “Is it obvious?”

He walked down the aisle and came back with a little black box. “This will do the job,” he said.

I picked up the box and looked at it as if I knew what I was looking at. Then nodded in approval. “Are there instructions?”

He smiled, “Yeah, don’t worry, it’s not complicated. Do you want anything else?”

I shrugged, “What else do I need?”

He took a deep breath, “Condoms, lube, poppers, butt plugs, some guys like to start with vibrators or dildos…”

I raised my hand to stop him from continuing. “I have condoms, but lube would probably be good, and I only found out about poppers tonight. Are they safe?”

He made a face and wobbled his head from side to side, “safer than coke, definitely helps if you’re going to bottom,” he said.

That’s all I needed to hear, “Ok, hook me up. Is it like a pack of three or… how does it work?”

He chuckled, sliding open a glass door under the counter, “Tell you what, these are on me, they are middle of the road strength, perfect for beginners at…everything.”

“Thanks, man, you’re alright,” I said, hoping it sounded like the compliment I was going for but too drunk to word with eloquence.

He smiled, “Cash or credit?”

“Cash,” I said, pulling out my wallet and handing him cash. There was no way that was going on my credit card statement to haunt me in the future.

I rushed back to my apartment. I only have about ten minutes to “clean out” and get ready for Walter…Walt… shit, is that even his real name?

As soon as I was done, I slipped on a pair of clean boxers, unsure if I should be naked or what when he arrives. I put my condoms with the new lube and the little brown bottle on the dresser I use as a nightstand. I felt a little less drunk, so I took two quick shots, polishing off the whiskey. It was now ten minutes after he said he’d arrive, and I was starting to worry he had changed his mind. When the door buzzer went off, I almost jumped out of my skin. I buzzed him in and waited the longest ninety seconds of my life as I waited for him to come up the creaky stairs to my door. I watched through the peephole the entire time. If he looked like a murderer, I wouldn’t let him in.

He looked exactly like his photos, except in a casual polo shirt and khaki pants. I unlocked the door, and he looked me up and down. I never felt like such a piece of meat in my life. I was so focused on him and the “what ifs” about him that I hadn’t thought that I might be a disappointment. What do I know about what guys who like to fuck guys are into? What if I’m too masculine for him?

He smiled, “Logan?” My name in his deep voice ran a chill up my shirtless spine.

I suddenly felt so nervous that I’m literally shaking. “Yeah,” I said, my voice cracking, and I cleared my throat quickly, trying to drop my voice an octave, “Yeah.” I let him in. Closing the door, I quietly latched the bolt. I have never felt so unsure of what I’m doing in my life. Am I supposed to make the first move? What is the first move? Fuck.

He seemed to pick up on my insecurity and took control. “Where’s the bedroom?” He asked.

I pointed and then realized I should lead the way. I don’t know if it was the booze or my nerves making me lightheaded, but I almost tripped over the throw rug, and when he chuckled, I suddenly felt a little less nervous.

We walked in, and he took his shoes off and then reached for me, pulling me by the waist into him. I had to fight my instincts to push him away. I’ve joked about stuff like this with guy friends, but it always ends in one of us pushing the other off. With Walter, I need to try to be into it, at the very least, not shove him off. It was tough when he slipped his hands into my boxers and cupped my ass cheeks, letting out a moan that sounded like a growl, then started kissing my neck. His scruff was like sandpaper on my skin, not entirely unpleasant, but definitely surprising. He smelled good, like he was freshly showered, thank God. I wasn’t sure what I was supposed to do, so I let him keep going.

He kissed my neck and then went to the other side, trying to kiss me on the lips in between, but even drunk, I had the wherewithal to turn my face and not let him. He took that in stride, without skipping a beat, and continued kissing my neck, then down my pecs, and started nibbling on my nipple. This got a reaction from me. I’ve never had someone suck on my nipples before and…wow, what a rush. I even heard myself let out a little whimper, a sound I’ve heard women make when I suck on their tits…now I get it. He sucked a little harder, and it became painful. “Ahh, shit,” I pulled back.

He grinned, dropping down, both of his knees popped as he put himself at eye level with my crotch. He slowly and dramatically pulled my boxers by the hem so he could reveal my dick like it was a new car in the showroom. I was shocked to see it bounce and start to spring to life. He seemed pleasantly surprised and nuzzled against it; his scruff was much more apparent against the sensitive skin of my penis, but I tried not to be a pussy about it. This is for him, I reminded myself. I closed my eyes and reached down to run my fingers through his hair as I would any of the women who have been in this position.

He was really eager, though, licking my ball sack then my crotch, really getting in there in a way women never have, and it was turning me on. My dick had gone from six to midnight pretty quickly, considering how much whiskey I’ve had, I’m surprised I was able to get it up at all. “Mmm, that feels good,” I mumbled as his tongue started running up the underside of my shaft. His hands were the largest I’ve ever had wrapped around my cock, and he knew exactly how to stroke a dick while sucking on the tip. It was almost like he was going to suck my cum from my balls and use my shaft as a straw. I’ve never had so much suction on my tip, and the way he worked his tongue over the head had me weak in the knees. “Oh shit, that’s so good,” I mumbled, widening my stance so I don’t fall over and so he has easier access.

He let his hand sink further down my shaft, twisting as his mouth followed his fist down toward the root. The grip of his fist and his mouth was overwhelming, and I was quickly finding myself in a position I hadn’t expected to be in. “Uh…” I cleared my throat, “I’m getting close,” I warned in an almost whisper.

He pulled off immediately, giving me a few more slow strokes as he examined my dick, then stood back up. The tent in his pants was obvious now. My heart started racing again, the nerves flowing through my body as I watched him yank at his belt, then the button, pulling down the zipper, his white briefs bulging out the open fly as he pushed the pants down. Then he pulled at the collar of his shirt, lifting his arms, and the shirt came right off.

I took the situation in. I’ve been in similar situations in the locker room at the gym, when guys get too close and I’m changing after a shower. That felt natural; this was intimate and exciting. He wasn’t changing into his gym clothes; he was getting naked and expecting me to be the one to put out. I watched as he stepped out of his pants, and the shirt dropped to the floor, then took in the sight of his almost naked body. I have to give him credit for being in decent shape, but I wasn’t sure how to proceed from here. He again sensed my hesitation and reached out to pull gently at the back of my head. I knew exactly what this maneuver was and went down to my knees to do to him what needed to be done. 

Inches from his brief-covered crotch, I could smell soap and a manliness mixture that wasn’t altogether a turnoff. My nerves had my hands shaking as I reached for the waistband of his underwear. I took a deep breath and decided to get it over with. I hooked my fingers into the waistband and pulled them down to his thighs in one quick yank. His cock flew out, almost hitting me in the face, and I even let out a “whoa,” which made him chuckle. He didn’t give me a chance to look it over, not that I really wanted to; I wanted to do the deed and be done. He pulled my head in, and I felt his warm cock against my cheek as my nose went into his pubes.

The last time I did this was in high school, and it was a very different scent with a very different expectation of the outcome. A much smaller cock, too. Walt’s dick was definitely all of six inches, but he was thicker than I was, and he had a lot more visible veins than I did. He grabbed his cock and aimed it right at my mouth. I let it touch my lips first, then I let the spongy soft skin pop into my mouth, slide over my tongue, and hit the back of my throat, where I instantly gagged and pulled off. I gave him a few jerks, not to be outdone by his skill level, I wet the sides of his dick with my tongue and tried again to get him in my mouth. Gagging again, and again, but after a few minutes and with his guidance, I was able to push past the gag reflex and get him in my throat for brief moments before pulling off instinctively.

As I bobbed and jerked up and down on his dick, feeling his warm cock in and out of my throat, I started to think, this isn’t so bad. I can definitely do this. Maybe if I give it all my effort, I can get him off like this and won’t have to take it up the ass? I doubled my efforts, trying my best to do to him the things I like being done to me, even cradling his balls. He seemed to be enjoying it, flexing his cock in my mouth. I could taste what had to be his precum on my tongue; it was sweeter than I remember it being the last time I tried this. When I thought he was close, and I was bracing myself for him to squirt into my mouth, he yanked his dick out and smeared his slimy tip on my lips and groaned as he held himself back from blowing.

He gripped my hair in his fist and stared down at my wet lips, “Get on the bed,” he ordered, letting go of my hair.

I stumbled to my feet, almost hopping up like a frog, and then sitting right down on the bed, falling back, I let the room spin for a second as I felt the drunken decision start to weigh on me. I shook my head clear and tried to stay in the moment. This is it, he’s going to fuck me, and then this will be over, I told myself.

“In the middle,” he said as he stepped out of his briefs around his ankles and crawled onto the bed from the foot.

I shimmied to the center of the bed and then decided to lie on my front, which I assume is the easiest way for him to do it, and this way I don’t have to look him in the eye as he fucks me. I felt his knees spreading my legs, and my stomach suddenly felt butterflies, and my ass muscles were clenching like I was doing squats at the gym. His hands ran up my thighs and gripped my ass cheeks, spreading them and letting air onto my hole. The way he massaged my ass felt really good; maybe this will feel better than I thought. I folded my arms under my pillow and buried my face in it as he continued to examine my ass. Massaging it, spreading it to look at the hole, then rubbing his thumb pad directly on my pucker. That feels surprisingly good, and I let out a subtle “Mmm,” as I breathe out.

He shifted his weight, and I unexpectedly felt his breath on my hole. Then he drooled on my ass, and I felt myself cringe. A man just spat on my hole. I buried my face deeper into the pillow in disgust with myself. Maybe if I suffocate myself I’ll pass out and won’t feel a thing, I thought to myself as his finger started swirling the saliva on my pucker, which…now that he’s giving it purpose, I realize feels… kind of good. He tried to push the tip of his finger into my hole, and my ass instinctively clamped shut, and I groaned, making him chuckle.

“Oh, you’re tight, a true virgin pucker,” he said to himself out loud.

“Oh shit,” I moaned into the pillow as I felt his tongue suddenly licking my hole. A feeling I’ve never experienced before, but…”Oh man, that feels…so good,” I mumbled and squirmed under the pressure of his tongue lapping at my hole.

He spread my ass with his hands so he could get better access to my crack. I tried to hold still, but this is a pleasure zone I didn’t know I had, and Walt is licking it like it’s the last meal he’ll ever eat. “Oh my God, fuck, mmmm,” I moaned into the pillow, grinding my now hard dick into the blanket, spreading my legs to give him easier access. When his finger snuck back into the mix, the tip pushed in, but it didn’t push him out or clamp down like before. It’s an incredibly weird feeling to have something pushing in, but it’s not bad. Walt wiggled his finger a little as his mouth dropped down and attacked my grundle and then my balls, sucking one into his mouth so hard it made me groan loudly into the pillow, and he let it slip back out. I realized his finger had slipped deeper into my pucker while he did that and I was both in awe of his mysterious ways but also, “Mmm, fuck,” I groaned in pleasure as he pushed on something that made me feel like I was either going to piss or cum and I couldn’t tell which as I grind my cock harder into the mattress.

He kept alternating between his finger and his tongue until he suddenly slipped a second finger in, and that made me groan. His rigid finger felt so foreign in my tight pucker, even though they were barely past the first knuckle; it felt like a bit too much, and I started to get worried about how his dick was going to feel. Then he pulled his fingers out, and it was his tongue again, and I moaned like a little bitch with pleasure and spread my legs wider for him. When he was able to sink two fingers into my hole without me trying to pull off, I realized whatever he was pressing on inside my ass was another pleasure point that I didn’t know I had and wish I had explored while masturbating for the last twelve years. “Mmm, fuck that feels good,” I mumbled into the pillow.

He slowly pulled his fingers out, “I think you’re ready,” he said, and I felt him reach for the lube. “Roll onto your back, I want to see your face as I pop your cherry,” he said.

I nervously and drunkenly flopped onto my back, my dick instantly going soft at the sound of a man telling me he wanted to penetrate me with his dick. I watched as he lubed his dick and then put some on my ass. “Ooh…cold,” I mumbled. He didn’t say anything, he just smiled and pushed two lubed fingers into my pucker. “Ahh, nghhh,” I groaned and clenched, but the lube allowed him to keep pushing in until he couldn’t get physically any deeper. With the lube, it didn’t feel as weird or bad, I guess.

“You ready?” He asked, slowly pulling his fingers out and adding a little more lube to my pucker.

I didn’t have much choice but to be ready, so I nodded and whispered a hoarse, “yeah.”

He shifted closer to me, hooking his hands under my knees and pushing them up, “hold them up,” he said, and I grabbed my knees. I watched as he started rubbing the tip of his dick on my hole.

“Umm, aren’t you going to put on a condom?” I asked, confused.

“I will, but I gotta open you up first. Trust me, you don’t want me to try and open you up with the condom already on,” he said with confidence as he continued to wiggle the tip into my pucker.

“Ok,” I wasn’t sure how any of this worked, so I had to trust that he was the expert here.

“Take a deep breath and push out when you feel me start to push in,” he said, looking into my eyes. I nodded, from between my knees. I felt him adding more pressure, and I tried to push out, but the pressure from his cock head on my hole had my ring clamping shut. He pushed a little harder, and the tip popped in, and the most fierce pain shot into my guts.

I dropped my legs, and he popped out of my ass. “Oh fuck, that hurts, fuck, ahhh,” I groaned, rubbing my hole to soothe the pain. “Shit…ungh,” the pain continued to sting even though his dick was out. I felt like my hole instantly bruised or something. “Fuck, is it supposed to hurt like that?” I hissed.

“It’s ok, it always stings the first time, once I get my dick in it always feels better,” he said in a calm, masculine voice that was somewhat reassuring, even though I’m not sure if it feels better for him or me in that scenario.

“Fuck man, I don’t know,” I mumbled as the pain started to subside.

“Just let me get my dick in, then I’ll wait for you to get used to it before I fuck you,” he said.

I would’ve told him to fuck off, but I need the money, so I let him back between my legs. He pushed my legs back up, and I hooked my arms under my knees, bracing myself for that sting to return. I watched as he added more lube to his dick and then lined back up. “Deep breath,” he said, and started adding pressure. This time, when the head popped in, it stung but didn’t feel like I was just punched in the asshole by Mike Tyson. The discomfort was intense, and I groaned, but I let him push deeper before I needed him to stop.

“Ahhh…fuck, wait…ungh, wait,” I groaned, dropping my legs so my heels landed on his pecs. He leaned against my feet and pushed his dick another inch slowly into me. “Ungh…shit, ahhh, fuck, man, that’s too much, ahhh,” I groaned, pushing my legs against his chest but he pushed forward and continued to add weight, pushing my legs back toward my chest, my heels slipping off his pecks and my legs went right over his shoulders as he sank more cock into my no longer virgin hole. “Unghhhhh…mmmphhh, fu—--ck,” I groaned, feeling my hole stretching around his cock and the head deep inside me, where no one has ever touched me.

“Just breathe,” he said.

Easy for him to say, he’s not experiencing his asshole being stretched open by another man's cock right now. I groaned again, telling myself, It won’t last long, just a few minutes for him to get off, and then I get paid. That had a bit of a calming effect, and I took a deep breath for him to see I was listening. While being stretched and filled with a cock was a bizarre feeling, it was somewhat humbling. Being a bit of a hound the last few years and going from girl to girl, I’ve basically been using them for my own pleasure and not really putting in the effort to make sure they were enjoying it. When I opened my eyes and saw the look of pure joy on his face as he circled his hips and wiggled his dick inside me, I could tell how much he was enjoying the feeling of taking my anal virginity, and that made me feel less like a prostitute and more like a saint.

I stopped pushing back on him and let him get a stroke in. As soon as he reentered, he went just a little deeper than before, and I hissed, “Ahh…fuck.”

“That’s it, give me that straight boy ass,” he mumbled to himself, pulling out a couple of inches and then shoving right back in.

“Fu-huck,” I groaned.

“Let it out, relax, and it will feel better,” he promised.

I don’t know how to relax with a dick in my ass, but I am feeling less pain, at least just from being penetrated. When he gets deeper inside, it still stings like a mother fucker, but it’s not as awful as it was when he first popped the head in. “I’m ok,” I told him, grabbing my knees and holding tight so he could fuck me and get it over with.

“Mmmm, you’re so tight,” he moaned on the next slow stroke into me.

“Umm, you should put on a condom now,” I reminded him.

“Aww, you don’t want to feel my cock entering you?” He asked, pulling halfway out and pushing in balls deep.

“Ungh…fu….ngh, you need to wrap up, man, I don’t want you to cum in me,” I said through clenched teeth.

“I don’t have to cum in you,” he said, sliding in deep. “If you don’t want me to.”

“Mmmph, ughhh, fuck, dude, you said you’d use a condom,” I reminded him, trying not to upset him.

He chuckled, slowly pulling out, “You’re right.”

His dick popped out of my hole for the first time since he got in, and I let out a sigh of relief. I don’t know how gay guys can do this for fun. I reached down and felt my hole to make sure I wasn’t broken or bleeding. He reached for a condom and started rolling it down his shaft. He added more lube and was right back to pointing it at my hole.

He pulled my legs up, and I grabbed them for him as he adjusted his cock on my pucker and started pushing in. “Ahhh…shiiit,” I grunted. Feeling him push in burned like hell. “Ngh, fuck,” I hissed and clenched.

“Just relax, you’ll open back up,” he insisted, leaning over my legs again, pushing my knees to my chest as he got most of his inches inside me.

“Mmmph, fuck,” I groaned through clenched teeth. Reminding myself, it won’t last long, it won’t last long, it won’t last…”Ungh, fuck,” …long.

He started pumping into me, slow at first, but then faster and harder. He kept looking into my eyes, I’m not sure what he was hoping to see, but it wasn’t going to be pleasure if that's what he was hoping for. I was just happy to be feeling less pain as he continued. Not great, but not terrible either.

After a few minutes of rabbit fucking me, he pulled out and huffed.

“Did you cum?” I asked, breathless and hopeful.

He chuckled, “No,” and flopped down on the bed next to me. “I want you to ride me.” He stroked his cock.

He wants me to…what? Ride him, cowgirl? I felt my stomach lurch at the idea. How humiliating. That’s how girls like to ride my dick when they are cock-loving sluts. I’m not a cock loving slut. I’m a straight guy, doing this for rent money. I huffed and flung my leg over his waist, landing right on the mattress on the other side of him. I sat on his cock, letting him aim it at my hole, and slowly slid down. “Ungh…hmmm,” I groaned, having control over the entry speed, it wasn’t as bad.

He grabbed my ass and started rocking his hips up. Only able to move an inch up and down into my hole from this angle, it wasn’t bad. I put my hands on his chest and started rocking my hips on top of him like girls do when on top of me. Ok, that…that actually feels kinda good, I’m not mad at that. It’s still weird having a cock in my ass, but something about it does admittedly feel good. He thrust up as I pushed down, and his dick hit a little deeper inside me. “Ungh…fuck,” I groaned. He did it again, and again. “Mmmm,” I heard myself moan, sounding too much like a girl. I felt self-conscious, but continued riding Walter’s dick. He reached between my legs and started playing with my dick. “Mmmm, fuck,” I moaned, the feeling of getting my prostate stimulated and my dick stimulated was a combination I’ve never experienced before. “That feels good,” I whispered.

“Yeah, ride my dick,” he mumbled, not missing a beat.

It started feeling really good. I was able to slide down his dick with no pain now, and if I adjusted my ass just right as I slid down his cock, I pegged my prostate just right and, “Fuck that feels good,” I moaned, throwing my head back. He started stroking my dick faster, and I rocked harder on his dick. “That feels so good,” I moaned. Leaning back, he rocked his cock up into me, and it hit something inside me that triggered the start of my orgasm. “Oh fuck, oh fuck,” I rocked my hips. “I’m cumming,” I moaned in a high-pitched voice I didn’t know I had. “Oh….fuck,” I moaned and felt my ass clamp on his thrusting dick, my balls instantly trembled, and cum shot out of my dick over his shoulder, hitting my pillow. Streams of cum coated his chest as I rocked and rocked on his dick, my entire body trembling as an orgasm exploded through my entire body in a way I’ve never experienced before. “Mmmm….fu-ugh, mmmm,” I huffed and slowed my hips as the last of my cum dribbled out onto his stomach.

“Feel good?” he asked.

I huffed, “So good,” and smiled at him.

“My turn,” he said, rolling me onto my back without pulling his cock out. He started hammering into my hole.

“Ungh, fuck,” I groaned. The feeling of his cock pistoning into my hole quickly went from amazing to that feeling of friction and discomfort. “Ahhh, shit,” I groaned. He pumped faster into me. “Shit, man, are you close? Ahh.”

“Getting there,” He breathed, then he tried to kiss me, and I turned my cheek. The thought of kissing a guy is not even on the table. That’s too intimate.

“Fuck, I can’t, ungh, it’s too much,” I groaned, pushing him off of me.

He huffed, clearly annoyed, my cum dripping down his torso. “Well, Logan, I’m not paying you to get off. I’m paying you to get me off, and I want to fuck you,” he said, stroking his dick.

I felt my gut sink. He was right. Just because I shot my load doesn’t mean this is over. He is paying me to fuck me. “I know, I know, sorry, I just, it hurts like hell. It burns for some reason.”

He chuckled, “That’s the friction from the condom, it only gets worse as it goes on.”

“Well, shit, use more lube,” I forced a smile.

He shook his head, “It’s lubed up, so is your hole, you’re just that tight.” He inched forward and started pushing the tip into my hole.

“Ahhh….fuck, man, I don’t think I can do it,” I groaned, and he pulled back.

“Well…I’m not paying you if you don’t,” He insisted. We stared at each other from between my legs for a second. “I can take the condom off, you’re probably safe since it’s your first time,” he offered.

“It is my first time,” I said, feeling challenged.

“Do you want me to fuck you bare? I’ll cum quick, and it’ll feel better for you,” he said, tapping his condom covered cock on my hole.

“I…ugh…” I thought about the money I need. “Yeah, ok, but don’t cum in me.”

He ripped the condom off and spit on his dick, “I’ll cum where I want,” he said, pushing the tip of his raw cock into my hole, “Is that a problem?”

“Ungh…I guess not,” I said, unsure of how this is supposed to work and still trying to keep him happy so I can get paid.

“Good,” he pushed balls deep inside me.

“Ungh…mmmm, fuck,” I hissed.

He reached over to the nightstand, grabbed the little brown bottle, and used his teeth to rip the plastic seal off the cap. Then he shook it, twisted the cap off, and held it up to his nose. He inhaled dramatically, held his breath, and then breathed it out and did it again on the other side of his nose. He handed me the bottle. I have never tried these before, but I watched him do it, and didn’t hesitate. I did exactly as he did, but the scent surprised me, and something hit me hard, so I didn’t inhale quite as deeply. I instantly felt a dizzy, quick high. Yes, this is exactly what I need. I tried it again, this time expecting the toxic scent I inhaled deep.

“Hold it,” he said.

I held it and looked into his eyes, which had relaxed now that he knew I was going to let him fuck me until he’s ready to cum, and his face was a little red from the poppers as he rubbed my legs. I couldn’t hold it too long and blew the air out. I felt an instant rush, my heart started beating faster and harder, my head was spinning, I felt my entire body relaxing, and my head sank into the pillow. He started pumping his raw cock into me. It felt so slick, so smooth inside me, that burning sensation was gone, and his thrusting felt less painful, but not nearly as good as it was right before I shot my load.

“You’re so tight, I’m already getting close,” he told me after getting in a few regular thrusts.

I felt the poppers wearing off already and decided to go for another hit. This time, I tried to mimic his and did it on both sides. The rush was so intense and so quick that I thought I might pass out. He was really picking up the pace now, and I swear, even with the poppers helping me relax, his dick felt like it was getting bigger and bigger inside me, but that’s probably the poppers somehow.

“Mmmm, yeah,” he moaned, leaning over me, pushing my ankles up by my head as he hunched his hips up into my ass. “I’m about to cum,” he whispered, then leaned in to kiss me, and the poppers had dulled my reflexes, and he kissed me. It wasn’t terrible. I let him keep kissing me as he continued pumping his dick into me. “Mmmmph…mmmmph….mmmmmmmph, mrrrpmhhhh,” he moaned into my mouth and pumped his dick into me. I felt his cock twitching as he held himself deep in my ass, “Mmmmm….mmmmm….mmmmm,” he moaned into my mouth as he continued kissing me. His next thrust felt amazing, no friction at all, then there was one more that was even better, a feeling so good for a second I thought, if it feels like this all the time, I get why gay guys like this, but then he pulled out and broke the kiss. Sitting up on his feet, he huffed out of breath. “Fuck, Logan,” he shook his head and grinned. “Such a hot piece of ass,” he chuckled. Then leaned back, falling over onto his elbows.

I felt confused, “Are you going to cum?”

He chuckled, “I already did.”

My heart sank, “Did…did you cum inside me?”

He grinned, “Yeah, didn’t you feel it?”

I thought about it, and that subtle twitching of his cock, the warmth, the lube…Oh gross, that feeling of extra lube and no friction was his cum! I scrunched up my face, feeling gross and dirty.

He got up off the bed, “Where’s the bathroom?”

I pointed, “on the other side of the living room.”

He walked out, and I sat there taking it all in. I felt my asshole; it was coated with cum. I hopped off the bed and went into the kitchen to wet a paper towel and wipe my hole clean. He came out of the bathroom, looking refreshed. He smiled at me and went into my bedroom to get dressed in seconds. I hadn’t even finished wiping the cum off me before he came back out fully clothed.

“This is for you,” he handed me a stack of cash. “If you need more rent money next month, we can work something out,” he winked, and then let himself out.

I felt so dirty, I took a long, hot shower and then crawled into bed. I felt something sticky on my leg, reached down, and realized it was the used condom. I nearly gagged as I dropped it on the floor next to my bed. I tried not to think about what I had just done and rolled to my side, feeling something wet on my face, and instantly remembered I had the best orgasm of my life, shooting cum out of my dick while riding another man's cock, and that first wad of cum hit my pillow…and now it’s on my face. I got up, flicked on the light, and started ripping sheets and blankets off the bed. I was still too drunk to really let it settle in, so I grabbed a top sheet and flipped my pillow over and slept in the bed without sheets. After tossing and turning, trying not to think about Walters cum in my guts, I eventually passed out, satisfied that I would make rent this month.