One Night Stand

I had never gone out on a date before today. It always seemed to be an event that would elude me, seeing as I never really took the time to try and ask someone out. However, things are different when a friend sets you up.
“I got to say, I never thought that I’d have as much fun as I did with you, Thomas.”
His name is Conley Kavanah, a teacher like me and also a mentsch.  He’s a tad short, reaching up to my ears, and also a bit on the bulky side with his round face and browline glasses making him look younger than what he actually is.
Apparently, he was one of two suitors Anthony had found for me to go on a ‘practice date,’ using people that owed him favors.  While I applaud my friend for doing things that merit such compensation, it makes me wonder just how low of an expectation they had of me.
“Oh, we’re almost there!”
Conley pointed to a cream-colored house. It was a humble and comfortable little place, which seemed to fit with the image I had of Conley.
When we got to his porch, I figured that this would be the best time to end the night.
“So, umm…thanks for going out with me today,” I said. Despite not really feeling much during the date, I still couldn’t help but blush saying that, “Sorry if I made you cancel any plans you had for today.”
“Don’t worry about it.” He gave me a gentle pat on the back, “I had a lot of fun. To be honest, I didn’t expect much from one of Anthony’s friends. I thought you’d be some deadbeat loser who got desperate enough to beg someone for help.”
Gee, thanks. I really needed that. Did you really have to add that deadbeat part, though?
“Though, umm…I guess this taught me not to judge someone based on their acquaintances. So…sorry if I offended you.”
“Eh, no trouble at all. I’ve been dealing with misconceptions for a long time now.”
God, this got awkward fast. I think it’d be best if I end this quick.
“Alrighty, I think I’m going to get going now. Thanks again for the fun night, Conley.”
As I was getting to walk away, he suddenly called out.
“W-Wait.”
I turned to him. In the evening light, I could make out a faint blush on his puzzled face. He looked as if he was wondering what to do next.
“I-I was wondering…d-do you want to come inside for a drink?”
I sighed. Well, not like I had anything better to do.
“Sure.”
---
Inside his home, I felt a lot more relaxed when compared to earlier. The living room alone gave me the homey sort of feel that I missed for a while now.
“Go ahead and have a seat. I’ll be back in a moment.”
I give him a nod before sitting down on his couch.  It’s not as firm as the one me and Anthony have back at the loft, but it sure is comfier. God, I could probably take a good nap on this thing. But I think that would be a bit rude.
…not like I owe him my kindness much, especially after that ‘desperate deadbeat loser’ comment.
“I’m back.”
I looked up and saw Conley walking towards me with two glasses in his hand.
“You sure took your time.”
“Well, all I had was grapefruit soda and a bit of vodka. I hope you won’t mind.”
“Don’t worry about it.”
After taking the offered glass from him, I took a sip of the drink. The mix of carbonation and alcohol burned my throat a bit, but it still tasted good.
After he joined me on the couch, we talked for a good while. I can barely recall what much of it was, but I assume most of it had to do with work. However, just as I was about to excuse myself and leave, he asks me a question that seems to bring my mind back from its haze.
“You’ve ever done it with a guy, Thomas?”
“Huh? Mind repeating that?”
His face was bright red as he asked me again,
“I said, have you ever done ‘it’ with a guy?”
And now I was red in the face.
“Well, umm…I’ve whacked off with another guy before but that’s about it.”
For the first time in the entire evening, I became a bit too aware of my date. I could feel his soft, hazel colored eyes glancing up and down my body. His lips quivering as he tries to ask another question.
“W-Would it trouble you if we…”
His voice trailed off. But his wish was obvious.
“You want to try it?” I asked him. Conley gave me a nod. I’m sure that was all he could muster, since he looked ready to die of embarrassment.
“I want to try it since I’m not too sure if I really like guys, or if I’m just going through a phase.”
God, that sounds like something someone ten years younger than us would say. But then again, some people don’t find themselves until they’re older, so who am I to judge?
“Um, well…if you want to. I mean, it’s not like I have anything else to do, but if you really want to do it...I guess we can.”
“You sure?”
Oh god, he’s giving me a puppy-dog look that just tugs at me. There’s no way in hell I can say no to him like that.
“Yes, I’m positive.”
He let out a sigh of relief. What are you so relieved for? Did you really expect someone to reject you with that look of yours?
“Alright then, can we go to my bedroom, then?”
---
He had me lay down on his bed before lying out at my side. His hand was on my chest, circling his palm a few times against it. This sort of image reminds me of an ad for a brothel, but I think I should hold my tongue.
“So, umm…what should we do?” He asked in a cute voice. God, I don’t know if he’s playing innocent or asking me a legitimate question. I guess I should humor him.
 “We have to get hard first if we want to do anything.”
“O-Oh, yeah. I forgot that.”
Let’s hope you don’t forget to breathe too while we’re at it.
He let the hand on my chest go down, stopping just below my belt. His face turned a dark red as he gave me a gentle squeeze. I sucked in a breath sharply.
“Ah, d-did I—“
“Don’t worry, it’s just that I haven’t been touched like that in a while.” I gave him a smile before putting my hand over his, “Just keep going. I’ll tell you if you do something wrong.”
Conley gave me a nod before continuing his teasing. His palm massaged my bulge gently, just putting enough force behind it to make me feel it. Before long, a tent formed in my pants.
“Wow, you’re bigger than I imagined.” He said as he rubbed a finger along the tip.
A part of me wanted to ask what he expected, but I decided to take that little ego boost without question.
“You want to see it?” I asked.
“Can I?”
I don’t know, can you? I think a better question would have been ‘May I?’
“Take it out if you want to.” I told him as I put both my hands behind my head.
Like a child carefully unwrapping his present, Conley undid my belt and pants before slowly undoing my zipper and pulling down my briefs. I let out a low groan as my cock was whipped out. Damn, I never felt so relieved to take off my clothes.
“Woah.”
He looked a bit too surprised by it. What, never seen a dick in your life?
“Something wrong?” I asked him,
“Well, umm…it’s just…”
He ran a finger along the length of my cock, stopping just above my scar. Ah, that’s why.
“Never seen a circumcised one before?”
Conley shook his head, “All the ones I’ve seen have the skin around them. Isn’t it a bit sensitive like that? I mean, mine’s very sensitive when I pull it back.”
“I don’t know. It’s never bothered me.”
He continued to stare at my dick like some urologist making a diagnosis. After a few moments, he spoke again.
“Mind if I change position?”
I shook my head. He’s the one who wanted to do this, so I think it’s fair for him to push things along.
“Alright then.”
He got up over me, and turned around, his rear to me and his face to my cock. Damn, I just barely noticed how tight his pants are. They clung tightly to his tuche and bulge, leaving very little to the imaginati—
“Oh fuck!”
I slammed my head back against the pillow as I felt Conley start sucking on the head.  He was clearly unsure of himself, since every time he tried to go past the tip, he would stop. I guess he wants to avoid rubbing his teeth along me. Points for caring, I guess.
“Go lower,” I told him.  As if my voice was all the encouragement he needed, he went straight for the hilt. However, it seemed to be too much for him. He quickly came back up, having nearly choked on me.
“S-Sorry Thomas,” He said in his softest voice. Great, now I feel bad for telling him to go lower.
“Just take it slow, Conley.” I gave his tuche a gentle slap as encouragement, making that bulge between his legs twitch, “Take as much as you can handle.”
“O-Ok.”
He went back down, this time using a hand as a buffer for him. While much of what he did was with his lips, the small rolls of the tongue he did along the head kept me from trying to correct him. It seemed he was getting it, little by little.
I guess he needs a reward for his work, huh?
“Mmf—!”
I felt him suck a little harder when I took hold of that bulge of his. Through the thin fabric, I could feel his cock just begging to be let out.  And I decided to give it the release it demanded.
When I pulled the zipper down, his cock slipped out, already stiff.  Just like its owner, it too was short and chubby. Damn, I can barely close my hand around it.
“You’re a dirty boy, Conley.” I muttered as I started to stroke him. I gave it a quick milking motion, just tugging enough to make him feel it. I could go deeper or faster, but I felt that he wasn’t going to last long if I did that. I mean, just from this alone his tool was dripping with precum.
“T-Thomas…”
Conley pulled away from my cock, making me shiver a bit from the sudden cold.
“What is it?”
“I was wondering…do you want to try putting it in?”
I gave his ass a good smack, making him whimper. What do you think?
“I-I’ll take that as a yes.”
He undid his suspenders and pulled down on his pants, finally giving me a perfect view of his ass. Unlike others his size, Conley’s rear was nice and round.  God, I just want to stick my cock in there and—
“C-Can you get the lube from the drawer next to you?”
He snapped me out of my daze.  Damn, I am really letting my dick do a lot of the thinking right now.
I looked over to the side and saw the bottle in question.
“What do you want me to do?”
“Pour some of it on your fingers and slip them inside me.  I-I trust that you’d go slowly, but I’d rather be prepped than risk hurting something.”
I gave a small grunt of acknowledgment before popping open the bottle and slicking my middle and index finger with the liquid then pouring some onto his waiting hole.
“Wait, before I start: did you clean out back here?”
I couldn’t see his face, but I’m sure he was blushing brightly.
“I-I did.  That’s why I took a while when I went to get the drinks. S-So you don’t have to worry about any accidents.”
“Hehe, so you had all of this planned, huh?”
I rubbed the fingers along his entrance, his body trembling in anticipation
“Mhm.”
 “You’re a dirty boy, Conley.”
He let out a small gasp as my fingers pushed in with little resistance. It seems that he is no stranger to putting something up here.
“Do you finger yourself?” I asked him as I moved the slick digits within him.
“I-I do. I…I started back when I was getting my degree. It just felt so good, and—Aaah!”
He bucked his hips towards me as my finger made contact with his prostate. It was a bit deeper than I expected, but the reaction is still the same.
“You like rubbing against this, huh?” I continued to apply some pressure to the organ,  making him let out a louder moan.
“S-Stop that! I-I’m gonna cum if you keep doing that!” He yelled. With a wry smile, I pulled out my fingers and gave his ass a squeeze.
“I think you’re ready for the real thing.”
Once he got off of me, the two of us quickly stripped ourselves before climbing back onto the bed. This time he was the one beneath me, with my body between his legs.
“Are you sure you want to go all the way?” I asked him as I lubed my cock up, “Once I start, we go until we finish.”
“I’m sure.” He wrapped his legs around my waist and brought me closer to him, the head of my cock now rubbing against his hole.
“Take a deep breath,” I told him as I grabbed his supple thighs and pressed inward.
“Aaah~!”
He grabs hold of me and pulls me closer, unwittingly making me shove myself in all the way. Conley clings to me rightly, my face nuzzled into his chest. I could hear him trying to stifle the pained sounds he was making. I should help him take his mind off the pain for a bit.
“Mmmh…”
I took one of his nipples into my mouth and began to suckle on it. While I wasn’t too sure of this and didn’t even know if it works on guys, I figured it was the best I could do in this position. To my surprise, it seemed t work a bit.
His cock twitched between us as my tongue tease the nib. By the time I pulled away, he seemed to have calmed down.
“Better?” I asked him. He simply nodded, his mind still foggy from my lip service. Just to be sure, I gave him a quick thrust. Although he still let out a grunt, it was clear he was no longer in pain.
Taking hold of his thighs once again, I began to buck my hips gently into him. He looked at me with those big hazel eyes, pure lust hidden beneath that innocent façade.
“T-Thomas. C-Can you…d-do something for me?”
“W-What is it?”
“C-Can you…talk dirty?”
I looked at him with surprise. Damn, I pictured him as the kind who wanted sweet nothings in his ear.
“Y-You sure about that?”
“Y-Yes. ” An all too devilish smile spread on his lips, “I want you to talk to me like a dirty whore.”
I swallowed hard. Shit, I’m not that kind of guy who just talks smack to someone in front of me. But I guess I can—
*Ba-dump*
Suddenly, I felt something strange.
“Mmmgh—!”
I began to thrust harder in Conley as that strange feeling within me bubbled up.
“You really like my fat cock up your ass don’t you, you little bitch?”
God, where the hell did that come from?!
“Y-Yes, I love it, I fucking love it!” Well, glad to see one of us isn’t freaking out.
My hands moved from Conley’s thighs to his arms, pinning them down as I angled myself and began to thrust deeper into him.
“You want to be made into my little pig-slut, huh? You’d be more than happy to let me fuck you in every way I want, huh?!”
By now, skin was slapping against skin. God, whatever took over me was merciless in more ways than one. However, it seemed that Conley didn’t care, because the look on his face was that of someone in pure ecstasy.
I could feel my orgasm building up quickly. If we keep this up, I was bound to lose it.
However, it seems the ‘thing’ knew this, since it quickly stopped sat back, my cock in full view of our bottom.
“If you want my cum so badly, come and bounce on this. I want your little bitch ass to work for it.”
By now, I shouldn’t be surprised that he would listen to me, but what did surprise me was how fast he did it. With little warning, he got back on me, keeping the pace that we had.
God, in this position I could see my cock going in and out of him as he rode me and stroked that fat cock of his.
“Yeah, that’s right, milk that dick.” The thing within me said. I couldn’t deny that ‘milking’ part since with each thrust I could feel him tightening when hip met hip, and loosening when we would separate. Fuck I wasn’t going to last like this.
“T-Thomas, c-can I kiss you?”
*Ba-dump*
When he said that, I felt my body come back to me fully. He suddenly let out a moan
“P-Please, c-can I Thomas? I-I’m almost there…”
I didn’t second guess myself as I grabbed his head and slammed our lips together and began to match his thrusts. He let out a whine as I felt something warm hit my body. He tried to pull away right after, but I kept him against me as I gave a few more good thrusts before cumming deep inside him. I myself let out a few short moans as I let him ride out my orgasm.
Once I was fully spent, I pulled out from him and let him drop next to me.
We laid there for who knows how long, our pants being the only thing heard. Finally, after what felt lie an eternity, Conley spoke up.
“That was intense.”
“No shit.” Was I could muster. I looked down at his ass to admire my handiwork. Cum dripped out from his still-gaping hole, and there were a few bruises on his hips, which I’m sure he is going to feel tomorrow.
“S-So, umm…how was I?”
“Well, you were my first. So I really can’t compare.”
“But, I mean…did it feel good?”
I patted his head,
“Hell yeah it felt good.” Normally I’m a bit more eloquent about this, but my brain is still a tad too slow right now to dig through my vocabulary.
“I-I’m glad.” He looked down at the mattress with a sad look on his face.
“Something wrong?”
“Well, it’s just…this felt amazing, but…only in the physical sense.”
In the end you really are the type that likes being made love to, huh.
“Hey, it’s no problem. Sometimes the first isn’t the right one for us.”
He smiled at me. God, he looks so adorable when he does that.
“Oh, umm…should I do something about your chest?”
“Huh?” I touched my chest and felt something sticky. Oh yeah, I forgot he came all over me.
“Here, let me take care of that, Thomas.”
“H-hey, wait. Don’t use your tongue!”
---
Once we got cleaned up, the two of us dressed and said our goodbyes. It was a fun evening, but in the end it was only a simple fling for the two of us. No hard feelings, seeing as neither of us had the experience or expectations to have ended up the way we did (Well, at least on my end).
As I headed home, there was a slight skip to my step. Guess sex does wonders for the mood.
---
Looking back at that night, I realized that the moment I spent with Conley was perhaps the last ‘normal’ moment I would ever have.