A Night with Jeff

My second visit with Jeff took a different turn.

After meeting up with Jeff by way of his Craigslist post, I ended up giving oral to him. I didn't realize it at the time, but Jeff helped me discover my bisexual side and my oral fetish. I enjoyed the act of using my mouth to please this man. I discovered that I had a bit of a submissive side and enjoyed when he stood up in front of me and took control, fucking my mouth like he would fuck his ex-wife. I even enjoyed the act of him shooting his load over my face at the end. I wanted more. I knew I would be back. So did Jeff.

At the final few moments of our first night together, Jeff said "Maybe next time, we'll try anal?" and it caught me off guard. This man wasn't just out for a one time blowjob. He wanted more. This man, whom I just met a few moments before he had me on my knees with his dick in my mouth, wanted to take it to another level. He wanted to put it in my ass. He wanted to fuck me.

"Ummm...." was all I could bring myself to say at that moment, still processing everything that had just happened.

"No pressure Chris. I'm not going to force you into it. Hell, you don't even have to come back if you don't want to..." Jeff said, before I cut him off with "I'll be back! I just need to think it over." A smile spreading over his face, Jeff replied with "Okay. Let's plan it out soon."

As I started to head out the door to leave for home, I turn to face Jeff who is right behind me. He's all smiles tonight and I make sure to keep it that way. I reach down and grab his cock for one last squeeze and let him know that I had a great time and I promised to come back soon. As I turn to leave, he grabs my ass and then gives it a little smack. When I turn my face to look at him, he's still grinning and he says "Maybe next time..." then gives me a wink. If it wasn't so late and I wasn't needing to get to bed, I would have given him more head there. Instead, I told him good night and that I'd text him soon.

The following day, I woke up from a fantastic dream about the previous night, but in my dream, Jeff and I went even further and had anal sex. Everything was so vivid and seemed so real, I woke up with some pretty extreme morning wood. I went and took care of that first thing, then got around for the day. When I sat down to have some breakfast, I noticed I had a couple of texts. First one was from my girlfriend saying she had come down with some bug and wouldn't be able to swing by after work before I went in. I text her to make sure she was good with any medicine or anything and she said she was okay and not to stop out. That got my mind going, and immediately I thought of hitting Jeff up for round 2.

As I went to bring his name up to start texting, I remembered I had another text to check. Ironically, it was from Jeff. I opened it up and read it.

"Hey Chris. I just wanted to reach out and say I really enjoyed meeting you last night, and I really had a great time. I'm always down for another visit from you, but I don't want to seem pushy on it. Especially that last little part I mentioned. I'd love to, but I completely understand if you don't want to. Hope to see you again soon!"

I felt a little relieved in knowing that he wasn't going to push anything, but after last night's events and that dream I had, I couldn't help it. I had to go see him again. I wanted to suck him again, and I thought I wanted to go further.

"Hey Jeff. I enjoyed myself a lot last night too. You definitely opened my eyes to a new world, and I truly enjoyed having your dick in my mouth. I want to do it again. Maybe even let you put it elsewhere too..."

I hit send, not expecting to get a reply for several hours as he was at work. I continued to make breakfast, and about 30 seconds after I sent my message to Jeff, he replied.

"When do you want to meet?"

"Free this afternoon before I go to work?"

"No, as I'm working until 5 this evening. But, feel free to swing by after work again."

My heart started beating faster. I was beyond excited to go see him again, and I wanted to make sure he was just as excited to see me.

"I'll be there. Be ready to get that dick sucked again. Maybe you can fuck my face some more too. I was really into that!"

"Yes! I'd be happy to do that! It's a date!"

"Oh...and not saying it will happen, but if the mood is right...have condoms and lube ready."

After a few moments of a pause, Jeff replied with "Are you sure?"

"We'll see what happens...but be prepared."

"Okay. I'll stock up after work. See you tonight!"

As the day went on from that point, I was getting more and more worked up. All I could think of was the previous night, his dick in my mouth, using me for his pleasure. It was so incredibly hot, but it was a total surprise. I never in my life expected to go out of my way to have sexual experiences with another man, and here I was...setting up a second "date" as Jeff had called it, ready and willing to use my mouth again. I was thinking maybe this time, I'd actually taste his cum and see how I like it.

But then, the dream came back into my thoughts. I had been giving him head, then I let him come behind me and put it in my ass. Just thinking of how vivid the dream was made me rock hard again. I kept thinking about it and how he was gentle at first, then building up the pace and strength in his thrusting. I found myself playing with my dick as I had this vision, so I took it to my bedroom where I laid on my bed and had a towel beside me. I lost the jeans I was wearing and started to stroke myself.

As I continued to stroke my dick, waiting for my 2nd orgasm for the day to happen, I kept thinking about that dream. It seemed so real and so enjoyable. I couldn't stand it anymore. I had to test the waters. I grabbed a bottle of lube from my dresser and put some on the tip of my finger. I adjusted myself back onto the bed where I started to stroke again, but then I reached back and rubbed the lube on my asshole with my finger. As I lightly played with my own ass, instinct kicked in and I unexpectedly slid my lubed up finger into my ass and started to finger fuck my own asshole. It was absolutely amazing! I found a good rhythm between stroking my dick and fingering my ass, and in almost no time, I shot a huge load up onto my stomach and almost my chest. As I was cumming, I kept fingering my ass, but at a much more intense pace and rhythm. When all was said and done, and I came down from cloud 9, I had my mind made up...

Tonight, Jeff was going to fuck me.

Jeff and I continued to text off and on through his work day, trying to make the time pass more quickly for both of us. I had to go work from 3pm til 11pm and he was off at 5pm. I truly wanted to just call off of work and go to his place and play together for hours, but I knew that wouldn't work out. My time to go into work had come around and I told Jeff to keep my mind going while I was at work. So, he did.

He sent me about 5 or 6 different cock pics, then sent me a link to a video of him using a sex toy he had recently bought. It was basically a rubber ass for guys to use as a masturbation toy. The video started with just the toy laying on Jeff's bed. Then Jeff comes up behind it and spanks one of the asscheeks before massaging it. He then crouches down and starts to lick on the hole of the toy, spreading the cheeks with his hands. Finally, he stands up, sporting a nice hard on, lines his dick up, slides in, then he mounts the toy on the bed and fucks the toy. After a few minutes, he pulls out and shoots a load on the cheeks of the rubber ass. He knows what he wants, and I know what I want. I want it now!

A few hours go by at work, and the machine I'm running breaks down. My boss gets ahold of our maintenance guy, but he can't fix it, effectively shutting me down. I asked my boss if he had any other work for me, and he told me he didn't. He checked the time, and at around 7:30pm, asked me if I was good to leave for the night, even though the rest of the shift would be unpaid. I didn't even hesitate and said yes. My boss laughed and joked with me, saying "Answered that quick...must be getting laid after work." He had NO idea how right he was.

After leaving work, I text Jeff, making sure we were still on.

"Hey Stud. Yeah, we're on. I just got home from the store. Picked up a few beers just in case. And, some condoms and lube...also just in case!"

"Haha well good to be prepared!"

"Yeah, I'm just gonna hop in the shower before you get here...wanna be nice and fresh for you."

I smiled to myself after reading that, turning the corner to pull onto his road.

"Well, wait about 30 seconds and check outside." I send to him.

As he walks to his front door, I pull into his driveway. None of his neighbors are home as they're all out to dinner or out at their jobs, so I don't hesitate to make my way to his door.

"You're here early!" Jeff said, holding the door open for me. Before he even has a chance to fully shut the door, I'm reaching down and grabbing ahold of his cock, trying to bring it to life instantly. He finally gets the door shut and locked, and he turns his focus to me. "Not that I mind..." but before he can finish, I'm down on my knees, undoing his fly and fishing his cock out. I immediately start to suck on his member, getting the blood flowing, as he tries to realize what is happening.

"A little horny for cock, are you?" Jeff says, looking down at me as I work his cock with my mouth. He bites his bottom lip while I look up at him to make eye contact, as he's nearly balls deep in my mouth and throat.

I pull his dick out from my mouth and continue on with my hand, stroking his hard cock with my spit as a lube of sorts. "I lucked out and got off work early. Had to come try to get a couple of rounds in." I promptly put his dick back in my mouth and go back to trying to suck his soul out through his cock.

"We can make that happen. Luckily, I've got a few rounds in me. You worked me up last night!" Jeff replied, then grabs ahold of my head and starts to facefuck me with everything he had. It was so damn hot! I thought for sure that the way he was going, it wouldn't take long for him to cum.

After about a minute of standing in front of me and fucking my face, Jeff pulled out. I was expecting his cum, so I closed my eyes and stuck out my tongue. He took his dick and tapped my tongue with the head of his cock. "Just so you know..." he started. "...I tend to last a while sometimes."

"Good." I say, with a smile on my face. "Just so you know...I want to taste your cum tonight."

Jeff's face brightens up after hearing me say that. "We'll make it happen. Mind trying something?" he said. I stand up from the ground and he gestures over to his couch in the living room. As Jeff is fully nude at this point, I take the liberty to go close the blinds and draw the curtains shut. I then sit on the couch and wave him in. Jeff walks over.

"I want you to lay down here, with your head hanging off the side or the armrest. I do as requested, and look up to see Jeff's cock and balls inching closer to my face as Jeff straddles closer to my head. I know what's about to happen, and I'm beyond happy to let it. I open my mouth wide, and lick on the head of Jeff's dick. Jeff tilts his head down and smiles. "Good boy." he said, before mounting my face fully and fucking my mouth.

As I'm laying here, getting dick rammed in and out of my mouth, I start to feel even more horny. This man I just met yesterday, already came on my face last night, and might do it again in a moment. I feel my own dick strain against my jeans, rock hard. I suck my lips around Jeff's cock as much as I can, slobbering all over his cock as he's using my mouth as a fucktoy, my eyes rolling back in my head. "It doesn't get much better than this!" I think to myself. But then, it does.

Somehow, I was unaware to the fact that while he was pounding away on my mouth, Jeff was on top of me undoing my own jeans, getting my cock out. He had been playing with it for a minute as it kept getting harder and harder, then when it dawned on me what was happening, he put my cock in his mouth and started to give me head while he was fucking my mouth. I was VERY impressed with how well he was sucking my cock. I moaned with a mouth full of cock as he continued to suck me. We were in full 69 mode and I was ready to burst. I couldn't hold it much longer. I tapped his ass to get his attention and he pulled his mouth off long enough to say "Do it!" then he went back to sucking and facefucking. I had no choice. I blew my load straight into his mouth and he kept sucking. He swallowed every drop.

In the meantime, I took his cock as deep as I could, thinking he was going to return the favor down my throat. He stopped and got up.

"What's wrong?" I asked.

Jeff just smiled. "We gotta get cleaned up. Come on...it's shower time."

He offers me his hand, and holds it as he leads me upstairs to his bathroom, across the hallway from his bedroom. As he walks in the bathroom to start the shower, I stand in the hallway, peeking into his bedroom. He had left the light on, and I see his nightstand right beside his King sized bed. I noticed on top of his nightstand, he had a brand new box of condoms and bottle of lube sitting out. The man was prepared, just in case. I smiled at the thought, then I officially made my mind up. He was going to take my anal virginity. My ass was his.

After getting the shower started and warmed up, Jeff got into his hallway closet and got a couple of towels and washcloths. He noticed me peeking into his bedroom, and crept up behind me after setting the towels and washcloths in the bathroom. He closed in on me from behind, and I feel his cock, still rather hard from our time downstairs, pressing up against my bare ass as he grabs ahold of my shoulders to get my attention. I'm caught off guard, but I'm loving it.

"I told you, I'd stock up just in case." Jeff says into my ear as he's behind me, pressing his cock even harder into my ass, briefly running it between my ass cheeks. I can tell that it's what he truly wants, and tonight, I'm gonna give it to him.

Having just blown my load a few moments ago, my cock is already starting to come back to life, ready for round 2. I turn around to look Jeff in the eye, and our cocks rub together as I spin around. Mine starts to stiffen up again and his is already rock hard and ready to go.

"Good thing you did." I say to Jeff, him looking down at our cocks grinding up against each other before he takes both into his hand and rubs them together back and forth. He looks up at me, waiting to see what else I have to say. "Tonight, my ass is yours." I say, feeling Jeff's cock immediately twitch against mine. A huge smile spreads across his face, and I continue. "But first, I need to suck your dick in the shower." He grabs my hand again and leads me into the bathroom, stepping into the warm water of the shower.

As the steam of the water started to fill the air, things were once again heating up between Jeff and I. The moment the shower door was closed, my hand was wrapped around Jeff's cock as we stood face to face in the shower, stroking him back and forth, making his cock go fully erect again.

"Do you want to kiss or make out?" Jeff asked in between his moans.

I hadn't thought about that part of this yet, but in the moment, I wasn't ready to kiss another man. "You can kiss my neck and chest if you want." I replied, and almost immediately, Jeff's lips had found my neck, kissing it, using his tongue to gently lick some areas of my neck, really getting the mood going. I'm still stroking his cock, wanting so bad to have it in me soon.

As though he could read my thoughts, Jeff stops kissing my neck and steps back into the water a little. I look deep into his eyes, then slowly down to his cock, which somehow tonight seems even more erect. "I want to last a while in your ass." Jeff says, once again getting my eyes to focus on his. "Suck my first load out." he said with a smile on his face. Who am I to say no?

I drop down to my knees, the warm water now running down Jeff's body and into my face a little bit. I open my mouth and proceed to start giving some extra sloppy head to Jeff. I'm making myself work more spit up to help give him a great blowjob, as well as getting some help from the water from the shower head. Jeff stands there momentarily just letting me suck away, getting his cock further and further into my throat every stroke. After a bit, with his cock still in my mouth, Jeff asks "Can I please fuck your mouth?" I stop bobbing my head along his shaft and nod "yes". He grabs ahold of my head and starts to fuck away at my mouth. This is the point in my life where I discovered how much I love getting facefucked in the shower.

Jeff keeps pumping away and I feel his cock start to twitch again. "Where do you want my cum?" Jeff asked while speeding up his thrusts. I close my mouth tightly around his cock and reach between his legs, putting a hand on his ass as he is mouth fucking me. I'm tasting this load tonight. I have to.

Jeff gets the hint and starts moaning. "Get ready." he warns, but then a second later, he starts twitching inside my mouth, unleashing a flood of cum. His tastes sweet, but there was so much going into my mouth while having his dick there too. Without much of a choice in the moment, I decide to go for it. I swallow his load.

As he continues to cum, I take a page out of the playbook of girlfriend's from both past and present, and start sucking his cock back and forth as he's pumping his semen out in ribbons. As much as I've enjoyed it in the past, I figured he would too.

"Oh fuck! Keep going!" Jeff begged, as I continue to swallow his cock and cum. I'm in total shock as just yesterday, this whole scenario just seemed like a fantasy...today, it was a reality. When I felt his cock stop twitching in my mouth, I finally stopped the ambush on his dick with my mouth and looked up at him again. His face is flushed and he looks as though he just ran a marathon.

He offers a hand as I start to stand up, and I look him in the eye. As he continues to catch his breath, he offers a smile and a major twinkle in his eye. I opened my mouth wide and show him that none of his cum remained, and his smile grew even wider.

"Good man! How was it?" Jeff asked before turning his eyes to my cock and wrapping his arms around me to pull me in closer, cocks touching again, and both his hands found one of my ass cheeks to fondle. He proceeded to start kissing on my neck again before I could answer.

As I start to lose myself to the moment again, I start to moan as Jeff is hitting the sweet spots on my neck and caressing my ass. I want him SO BAD at this point. I would have let him fuck me there if he was ready.

"It wasn't bad...didn't plan to swallow, but it wasn't bad." I say. Upon hearing this, Jeff started kissing my neck with even more passion. "I probably won't make a habit of that, but I think I could on occasion."

Jeff stops kissing my neck, but continues to grind his cock into mine and keeps a firm hold on my ass, gripping the cheeks and slightly spreading them. Suddenly, I feel his fingers moving in between my cheeks, and I get a feeling that things are about to start moving to the next level. I'm excited and nervous all at once, my cock twitching from the thought of what's about to go down and Jeff can read me like a book. His eyes lock into mine again and he smiles.

"Well...let's see if we can start a new habit tonight." Jeff says, then without so much as a warning, I feel one of his fingers start rubbing around on my asshole. I tense up momentarily as Jeff continues to tease my hole. I lean my head towards Jeff and find myself kissing on his neck and shoulder. Jeff keeps his focus razor sharp and continues to rub my hole. "Are you ready?" Jeff whispers into my ear, briefly sticking his tongue out and running it along the side of my neck immediately after. I'm putty in his hands.