At first I thought this would be a two part story, but it's looking like it will be at least three. There's not a ton of sex in this part, but lots of delicious build up that will definitely deliver in the third part.
I'm a very new author and totally reliant on feedback from readers, so send me an email and tell me what you think! I'm at eli_6969@yahoo.com.
This story contains explicit sexual content between adults. Also, don't forget to donate to Nifty to keep the archive going!
Eli
End of Part 1:
I'm finally at the point where I'm done waiting. I ready to find out what it's really like to be with someone who has a penis and I've figured out just the right person for the job. His name is Dave and we're meeting for drinks tomorrow. _____________________
Part 2:
I've known Dave for a few years, now. In our first conversation he made a joke about airhead women. I said "that's not funny, don't make jokes like that." I was prepared for him being defensive or to attack me, as usually happened when I held people accountable. Instead, he said:
"I'm sorry. You're right. I'm glad you said something."
That kind of set the tone for how things were between the two of us, at first. He was the kind but clueless cis straight white guy, me the political, outspoken multi-ethnic queerdo. After a few years of hanging out, working together and laughing a lot, we had gotten to be genuine friends. There had been plenty of awkward and teachable moments, though. Very early on he was super curious about how and with whom I had sex, I explained that since he and I weren't fucking, it was none of his business. Even then I knew I was attracted to him, though.
Dave is about 6 feet tall and sturdily built with just a bit of a belly. His hair is gorgeous. On his head it's dark, thick, and shiny. On his body it peaks out above v-neck shirts and is plentiful on his arms and legs, too. He usually sports a thick beard. He's got a beautiful, warm smile, a good sense of humor and is easy going.
One night, about six months after we met, he texted asking if I wanted to get together for drinks. I was utterly perplexed at the request. We worked together, but he didn't say anything about needing to talk about a project. Of course I immediately texted C and explored fun fantasies of him wanting to get in my pants. I joined him a few days later and it turned out he just wanted to spend time together. He told me about his two daughters and his ex-wife, they were in the midst of a not-so-great divorce. I talked about my then-partner and family. We commiserated about expensive lawyers and worrying about his relationship with his girls.
Over the years I met and spent time with his girlfriend, Monica, too. She's a journalist, fiercely smart and independent. She appreciated the role I played with Dave, at first, helping him to understand how his perspective as a cis, straight, white guy was limited. He said he felt like he met me at just the right time in his life, so he was better able to a be good partner to Monica.
Now, two years later, I scanned the bar to be sure he hadn't arrived a head of me. When I didn't see him I grabbed a booth and ordered a bourbon on the rocks for me and a scotch, neat, for him. I was strangely calm even though I was about to proposition Dave for sex, a request that could lead to me finally getting to play with a real, live penis! The thought got my dicklet hard and my pussy wet. Dave walked up to the table, smiled warmly and slid into the booth.
"Hey, thanks for ordering for me."
"Sure thing" I smiled back. I held up my glass, ready to toast, and said "to deepening our friendship!" We clinked glasses. I couldn't help but smirk at my toast, I hadn't done it intentionally, not exactly.
He noticed my smirk, "what is it...?"
"Ah, nothing, nothing" I replied. I knew if we got talking about something else I might lose my nerve, so I jumped right in, "Dave, I need to talk to you about something."
"Ok, this sounds serious" he half-joked.
"Well, kind of, but really fun, too." He nodded, waiting for me to continue. "So, I've told you about the people I've dated and been with lately."
"Yeah, but there's no one right now, is there? Oh, is that it, you're seeing someone? Is it serious? Do Monica and I get to meet them?"
I laughed, "No, well, not really, but good job in not assuming the pronouns of the person I might be seeing!"
He smiled, "I'm learning."
Again, trying not to let myself get side-tracked, "So, you know I've mostly dated women, enbys and trans guys, right?"
"Yeah"
"Well, even though I've never dated, or been sexual with someone with a penis, I've been really attracted to them for a long time." Dave knew I was sex positive and didn't shy away from talking about sex with accurate terminology, but he was still clearly caught off guard and a bit hesitant. He wouldn't meet my eyes and was fidgeting with his glass. I took a sip of my bourbon, rolling it around on my tongue for a bit before swallowing.
"I've felt this way for a long time and I've finally decided to do something about it."
After a long pause, Dave blurted out "Ok, is this some sort of a test, or something?"
I raised my eyebrows in confusion, "A test?"
"Yeah, like, it's not cool to ask trans folks about sexual things, we're not supposed to overly sexualize them, I mean, you... So, are you like, trying to see if I remember that?"
I laughed, "Dave, we're friends, sometimes friends talk about sex, that's what this is. It was different when you and I barely knew each other and you asked about my sex life!"
He breathed out, "Yeah, yeah, of course it's different. Sorry. I'm just so Catholic, I'm still getting used to it being ok to talk about sex."
"Well, you've been doing pretty well having talks with your kids."
He smiled and blushed a little, "Those are not getting any easier as they get older, but I'm glad they come to me with questions." He paused, looked at me, then continued, "So, does this mean I can ask you questions?"
"Of course, ask away!" I was actually glad this had turned into a conversation instead of a one-sided thing where I just asked Dave if I could see and play with his dick.
"Ok, so you said you've mostly dated women and stuff." I nodded, "does this mean you've never seen a penis?"
"Well, I've seen them, yes, at strip clubs, and clothing optional pools and beaches, but I've never touched one, an adult one, at least."
"So you've never been penetrated?"
"Dave, a penis isn't the only thing that can penetrate a vagina, there are lots and lots of options, fingers, vibrators, dildos, tongues, I've been penetrated by all of those."
"Yes, of course, of course."
"I had one person who wanted to try toes, it wasn't my thing, but, she dug it. Oh, and I'll never forget the night of a thousand vegetables, the things you can do with a cucumber are remarkable, they're quite flexible actually, but that's a story for another time. So, no, I've never had a penis inside of my vagina. I've also never handled one or sucked on one or watched it get hard."
"So, you're looking for a guy then? Or, a person with a penis, I guess, so you can, like, explore that?"
"Yes. But, I don't really want to date someone. You know I'm happier being single."
"Oh, definitely, your last few attempts at relationships weren't pretty. So, just something casual, then?"
"Well, I'm fine with casual but this is different. A penis is new territory for me. I don't want to rush into anything. I mean, the first time I'm faced with a real-life-adult penis I may find that I only like fantasizing about them and have no interest in actually touching one. Or I may enjoy the touching but not want to suck one, or I may enjoy the sucking but not want to fuck one. In my experience causal things work best when everyone is clear about what they want and I just can't do that in this situation because I really don't know what will feel right."
Dave was nodding the whole time. "Yeah, I get that. I totally get that. It's a really personal thing. You need someone you can trust, who won't have any expectations about what's going to happen. If you do decide you want to have sex, I mean, the penis-in-vagina kind, you need someone who you know will take things slow."
"Yes, I mean in a perfect world stopping at any point would always be no problem, but that is not the world we live in. I'm not actually even a big fan of penetration, I only like small dildos inside of me, small vibrators, so I'm really not at all sure whether I'll like the feeling of a penis in me. I'm really curious, and I know the vagina is really flexible. I've had some really, really hot experiences being penetrated, but not very many of them."
We sat in silence for a moment, then Dave started again, "I mean, speaking from experience, not all guys...um, I mean, people with penises, well, no, I actually think I mean guys, not all guys are great at hygiene. If you're interested in playing with a penis, maybe putting it in your mouth, you'll want someone you can be sure is at least somewhat, um, well, you know" Dave stuttered.
"Not stinky?" I laughed.
"Yeah, basically."
"Ehh, lack of attention to that kind of thing crosses all genders. I've got strategies for making showers part of foreplay, but, point taken."
"So, well, this is kind of cool, Sam. You're in search of a friend with a penis!"
"Actually, I'm hoping you'll consider being that friend" my heart was in my throat and I could feel my face getting hot.
Dave laughed, "right, sure, ok, let's go back to my place and fuck around for a while."
"I'm not kidding Dave, I want this, I want you."
He just looked at me. I couldn't read his expression at all.
"I mean, of course, only if this is something that Monica is ok with. Well, if you want to, first, of course, you have to want it first, but if you did, we, I mean you, would need to be sure it worked in your relationship with Monica."
Shit, shit, shit, this is awful. He has absolutely no interest in being sexual with me. What was I thinking? He's got a smart, funny, gorgeous partner, why the hell would he want me? This random, chubby, nonbinary person who may be really terrible in bed and just wants to use him for his dick!?!
Then he smiled and chuckled. He pulled out his phone and sent a text then looked back up at me. "Sam, I'd love to do this with you, I'm so glad you trust me this way. But I have a question."
"What is it?"
"Can Monica be there too? I mean, just to watch, if you don't want her to be part of things she won't be. She thinks you're totally hot. We've fantasized about you joining in since we first started fucking and I know she'd love to watch, well she'd love to do more, but she'd at least love to watch."
This was new information and made my mind buzz. Monica, fierce, fiery, sassy Monica thought I was hot? She wanted me? Hmmmm, this might be nice actually. I found myself turned on at the thought of sex with her, which wasn't surprising, but also relieved at the thought of her being there with us. Someone with a body-type that would be familiar to me, that I had practice interacting with and making feel good.
"Yes, oh my god, Dave, I'd love it if Monica were part of things too. The three of us should probably talk this over together, though. I mean, after you two do."
"I just texted her and said there was a chance we could have a threesome with you, this was her response" he held up his phone and it read: FUCK YES.
Dave really wanted me to go with him to Monica's place that night. I insisted that the two of them needed to talk about it without me there, though, so we agreed to go our separate ways. After another drink we left the bar together and he leaned in for our typical hug goodbye. It lasted longer than usual though, I drank in the feel of him, his solidness, his height, the softness of his sweater and his scratchy beard as his face brushed past mine. He paused with his face just a few inches from mine, leaned in, and kissed me. His lips were so much softer than I expected, even though his beard was rough. At first it was simply the meeting of two pairs of lips, but I couldn't hold back and stuck my tongue out to explore his lips. He groaned and opened up his mouth, granting me access, and began massaging my tongue with his. Chemistry was definitely not going to be a problem.
I wanted so badly to feel his cock, to run my hand down his chest and stomach and over his crotch. I wanted to feel whether his dick was hard. I knew my dicklet was hard and I was very, very wet. I stopped myself, though. This was too much, too soon, especially since he hadn't really talked to Monica yet. Come to think of it, I really didn't even know if guys get hard that quickly or just from kissing...? I was distracted from that thought when I heard the noise from the club across the street get louder, the door must have opened. Dave and I separated and glanced across the street watching a group of club kids laughing and chatting. The door shut and the thumping music receded to the background again. When we turned back to each other we were both flushed and smiling, he was holding both my hands.
Dave started trying to talk, "Sam, that was..., I mean, it felt really good to..."
"Yeah, I know. I was...It was really good."
"And we get to do this again, and more, shit, I don't want to wait, are you sure you don't want to come back to Mon's with me?" Dave released one of my hands, ran his hand up my arm and started stroking the back of my neck. His warm, soft hand on my neck went straight to my groin.
A moan escaped my lips, "Mmmmmmm, oh I really, really want to, but I still don't think we should."
He said, "you're right, you're right, I should talk to Monica first," but kept stroking the back of my neck.
I reached up running my fingers up his chest, "there's nothing saying we can't make out some more before you go, though." I grabbed his collar and pulled him down for another kiss. His mouth latched on to mine aggressively, he wasn't holding back now. I relished feeling how much he wanted me. I pushed my tongue back into his mouth and groaned. He ran his hands up the back of my neck and started playing with my hair. I'm much shorter than him, but he was bending down, so I could run my hands over his cheeks, his heavily bearded cheeks. I've got to admit, it felt weird kissing someone with so much hair on his face. Some folks I've kissed have had some hair, but nothing like this. His was so thick, but it was still sort of soft.
As we made out my mind went to his dick, again. Was it hard? What would it feel like if I rubbed it through his clothes? If it was hard, was it visible? He was wearing jeans. With that thick material I didn't think it would be very noticeable if he even was hard. My hands moved down the sides of his body to his waist. I wasn't exactly trying to cop a feel, I guess my body just went there.
I could feel Dave's mouth crack a smile, and he pulled away, "You want to touch my cock, don't you?"
I breath out, hard, "Fuck yes, I want it so badly." I knew my face was already flushed, but I felt it getting hotter. My eyes traveled down his body and rested on his crotch. There was definitely a lump. I hadn't checked him out before, so I wasn't sure if it was bigger now. "Are you hard?"
"Are you kidding? Of course I'm hard, here," he grabbed my hand and put it on his dick. I immediately noticed the bulk of it, the thickness and presence. There was no mistaking things, there was definitely a penis between his legs, and I was touching it. At first I left my hand where he placed it, just sort of, resting on top of his dick. His dick, my hand is resting on a dick. Right now. This is actually happening. I first squeezed it very gently, to get a sense of the contours, the shape. I had zero sense of size, based on what I was feeling, but I knew it felt good. I wasn't just a curious observer, satisfying some long-held interest in penises, I was insanely turned on. As I explored his genitals through his jeans I imagined what it would be like to feel his actual skin and I felt my diclit actually lurch in my pants. Ah, there are balls too! How could I forget about the balls!?! I continued my exploration seeing if I could distinguish balls from dick.
As I felt and rubbed and pushed, Dave groaned "God damn, Sam, we have got to take this to someone's house."
That brought me back to reality and I reluctantly removed my hand. "No, we really need to wait. Go home, talk to Monica, figure out what you want and what she wants. I'm not going to be a home-wrecker."
He sighed and nodded, "you're right, you're right."
"I don't know about you, but I'm going to go home and masturbate repeatedly, I may even cum on my drive home, just from the vibrations of the car" I said, laughing.
"Wait, you can cum repeatedly, like in a row, without waiting?"
"Yeah, I cum much more easily since I've been on T, but I can still cum over and over again, it's pretty awesome." I grabbed his hand and we started walking down the street towards where my car was parked. "You're taking the train to Monica's, yes?"
"Yeah, my stop is down the block."
We walked the rest of the way in silence, hand in hand. When we got to the station Dave turned to me and kissed me again, hard and wet, then smiled and said "I'll let you know how the talk goes."
"You two should totally fuck, too, would hate to let that hard cock go to waste."