Inadequate Men
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Chapter 18 -- Pajama Party
When Kyle got back to the office, he was relieved to find that the receptionist was still out to lunch and the waiting room was empty. He knew that this was completely irrational, and that objectively there was no visible sign that he'd just jacked off on the phone with a hot young stranger. Even so, he felt conspicuous, as if there were an invisible sign hanging over his head proclaiming the event.
He slunk back to his desk and buried himself in work for most of the afternoon, intermittently interrupted by a couple of associates who needed his guidance to prepare for a strategy meeting planned for the following morning. When he next looked at the clock, it was 4:30, and he began to think about winding down for the day.
At that point, he checked his personal email, and found something from Kyle in his inbox. Kyle had messaged him that morning requesting a personal day, and Jared had authorized it with a shrug, making a mental note not to drink boilermakers with his assistant ever again. He imagined that Kyle had awakened with a massive headache and spent the day in bed miserably taking Advil and watching soap operas, for which he'd once confessed a perverse fondness.
Kyle's email to Jared was as follows:
Jared,
Thanks again for giving me the day off. I also wanted to thank you for last night. I know that I was pretty drunk, so please forgive me if I did or said anything I shouldn't have. Like, for example, that crack I made about you knowing that I don't have much money. It was a joke, and I need you to know that I really didn't mean anything by it. But the part about you being a cool boss. That was real. You are the coolest boss I've ever had, and also the cutest. I guess I should tell you that I've had a crush on you for the longest time. I finally have the courage to say it because you've got a boyfriend, and now so do I!
And here's the thing -- I probably wouldn't have one at all if it wasn't for you. The advice you gave me last night definitely changed me for the better. I have to admit I was pretty bruised when you told me what I selfish jerk I am (I don't think you used those exact words, but that's what I heard). But I needed to hear it. So, headed into next week's depos, you're definitely the man who knows how to wield a chainsaw enema, so go get 'em!
When I got home last night, drunk as I was, I gave Ben a call. I mean, I couldn't not call him, right? He was sweet as always, and because I'm me, I just flat out told him I'm sorry for being a selfish jerk. He said he didn't have any idea what I was talking about, but when I got on to the part about pressuring him to do more than he was ready for, he got quiet and just listened. And I knew that I was right, I had been a jerk, even though he took more than half the blame for being, as he called it, maybe old-fashioned, even prudish.
We talked a little more and then we both segued on to what could have been another phone session. And since I'd just promised only a few minutes before that I wouldn't put any pressure on him about sex, I was surprised to hear him say something like, "Too bad we're not together right now." So I said, of course, "Me too," and that led us into more talk about what he might like to do with me if we were together.
And that gave me an idea. It sounded dumb, actually, and I didn't want to have him feeling pressured again by me. But I suggested that if he wanted to, he could come over to my place, and I would promise on a stack of Bibles that we could just talk, and cuddle, and fall asleep together if he liked, but I wouldn't try to turn things into sex under any circumstances.
Ben said it sounded kind of good, but worried about the time -- it was already after 9, and Ben lives about half an hour away. I told him not to worry and that, worst case scenario, I have this really cool boss named Jared who doesn't get freaked out when I take a personal day once in a while. But before he agreed, he checked with me again to make sure I was really, really OK with just talking, cuddling, and then sleeping. And, thanks to what you told me, I assured him that I was.
When Ben walked in the door, I could see in his face that he was nervous. But I just let him in, and led him over to the couch, and then sat in a chair across from him, and we drank wine for a while. (I let him drink faster -- he had a lot of catching up to do!) I think he was surprised that I wasn't hanging all over him for a change, but just talking and listening to him talk about his day. In fact, we talked for so long in that way that eventually he invited me to sit next to him on the couch. (I think the wine was doing its job!)
He took my hand, and we just sat that way for a long time, silently just enjoying the feeling. It's weird, because I've had boyfriends since I was 15, and we've done all sorts of stuff, and it's always felt great -- well, mostly -- or maybe sometimes not. It's confusing. I've always thought of myself as a very sexual person, but when I think about the stuff I've done, maybe I haven't always wanted to. And that's the first time I've ever said that to anyone. But what's weird is that just holding hands with Ben on the couch last night, I was starting to feel something I can't put into words, but I knew I wanted more of it. It was so gentle. He has really nice hands, and I never noticed that until we just sat there for a while holding hands, without me thinking, OK, what's next, what's next?
"This is nice," he said.
"It sure is," I said back. And then I added, "Maybe I'm more old-fashioned than I thought I was."
"I'm glad," Ben said. I could tell he really meant it, and was glad to just be able to enjoy each other's company in a physical way without any expectation coming at him from me. And, to tell the truth, I felt the same.
I kissed him very lightly on the cheek, and it felt so good. Then a few moments later, Ben returned the gesture, and it felt even better. There was something about the slow pace that we were going that made every feeling so much more real. We did this a few times back and forth. I would anticipate kissing him, and then move to kiss him, and then the kiss itself would feel so good as my lips actually made contact with his face. And then, I would pull back and just enjoy the sensation of just having kissed Ben, and that would also feel good. And then, after a while, I could feel him move to kiss me, and the agony of waiting but also the joy of knowing that he wouldn't let me down made his kiss feel even better. I'm just going to hope that as you read this, Jared, you're on my side. I think you are, and that I can trust you as a real friend.
By this time, it was almost 11:30, and we both noticed the clock at the same time. I still wasn't sure that Ben was going to want to stay over, but I invited him and said, "I hope you know that I'll honor my word to you -- just cuddle and sleep."
He looked at me for a while as I just stroked his face, and thought, Damn, I could really fall in love with this man. And after a few seconds, he said, "I think we could give that a try."
Before that, Ben and I had never slept all night in the same bed. Always, whenever I would try to get him to stay over, he would always say that he needed to drive home. Even on weekends, it was the same story. So my heart just about skipped a beat when he agreed to spend the night. And I was determined not to let him regret it in any way.
OK, so here's a thing: One of the things that Ben and I had admitted to each other on the phone was that we both have kind of a pajama fetish going on. (BTW, Jared, if me admitting this kind of thing is more than you want to know, maybe you should stop reading now.) So we had talked about this already, and I knew he had packed one of his favorite pairs of pajamas for the night. I showed him into the bathroom with his overnight bag, and led him into the bathroom, so he could brush his teeth and get ready for bed. Meanwhile, I planned to do the same using the kitchen sink.
But a minute later, he opened the bathroom door and called to me. Ben already had his shirt off, and what I could see of his chest for the first time ever was amazing. He had this really nice light dusting of brown hair that looks so masculine, especially because, as you know, my chest is just about totally hairless.
I tried not to make it too obvious that I was looking and asked him what he wanted.
He said, "We're about the same pajama size, right?"
I answered, "I guess so. Why?"
Ben suggested, "How about if we wear each other's pajamas tonight?"
I ran to my room and pulled out a pair of pajamas that I thought he'd look really good in -- a red flannel pair that I've been wearing since high school which, if they could talk, would probably have me arrested. I handed them in to him through the open bathroom door, and he passed me his own blue plaid pajamas. I rushed back to my room to try them on and, OMG, they smelled like Ben. His own indescribable masculine scent was imprinted all over them.
I haven't lived with anyone since college, so for a long time I really haven't experienced this little ritual of getting ready for bed with another man. It felt good to turn off the overhead light in my room, light a couple of candles on the nightstand, turn down the bed, and wait for Ben to join me.
"Hi," he said, knocking on the door, shyly.
I was just about to tell him that he didn't have to knock, but no words would come when I saw him. Maybe I'm an idiot, because we've only known each other a few weeks, but I felt for just a second that we had been married for years, and I was completely contented.
At the same time, seeing Ben in my pajamas was giving me a very different kind of feeling. Like I said, they're pretty old and threadbare, and since Ben is a little bigger than I am, they were tight on him in all the right places. Even though he didn't have a hard-on, in the candlelight, I could still see a really nice, clear outline of his cut dick hanging down along his left leg.
"Wow, Kyle," he said, "You look good."
"You too, Ben," I said, brushing the hair along his forehead with my fingers. "I'm glad we're doing this."
"Me, too," he said, taking my hand. "Um, which side do you like to sleep on?"
"The right side," I told him, leading him to the left side of the bed. We both got under the covers, and immediately gravitated toward each other for warmth.
"Mmmmm," he said, "It feels good to cuddle."
But he was shaking a little, and I knew it wasn't just from the cold. I asked him, "Are you nervous?"
He admitted, "Yeah, I'm always nervous when I'm with a guy."
I asked him, "Does it help to know we're just cuddling tonight?"
"Mm-hmm," he answered, "It really does." Then he admitted nervously, "I guess I just don't feel very confident of my abilities in bed."
I knew it took him a lot of courage to say that, so I reassured him, "I'm really glad you told me that, Ben. And you know, I'd rather just be cuddling with you tonight than doing anything else with any other guy in the world right now. Just being with you right now like this is all I want."
"Well, thank you," he said. "It feels good to hear you say that." Then he added, "And you know, you look really cute in my PJs."
"Thanks," I said. "You too." Then I remembered something else that we'd talked about on the phone, and I reached over and started gently tickling him on the ribs.
"Oh-oh," Ben said, but I knew from our talks that this was really an invitation. He'd told me that when he was a kid, his older brother used to tickle him without mercy, and if he laughed, then his father would come into their bedroom and punish them both. He secretly loved the attention from his brother, who was in his teens while he was maybe 10 years old, so he would stifle his laughter as long as he could to keep the connection going. Did I mention that his brother was an all-state competitive swimmer? One time, he told me, his brother wouldn't even let him get out of bed to go to the bathroom. He kept begging, but his brother kept tickling him and holding him down and telling him he should be able to hold it. He hasn't yet told me how that story ended.
Anyway, I was clear from our talks on the phone that getting tickled was definitely something he was into. I moved in closer, and got into position, then dug into both sides of his bodies with my fingers, and felt Ben squirm under me.
"You better not laugh," I whispered to him, "Or Dad will hear us."
He strained not to react as I slowly dug my fingers into his sides provocatively, tickling him. Then, as he struggled to keep his composure, I reached up and touched his face, tipping his lips toward mine. I touched my lips to his for the first time that night, just gently holding my lips against his very lightly, almost torturing both of us by withholding greater contact. I could feel our connection as both my breathing and his increased together with just this slight physical connection. I could feel that we were both holding ourselves back from deeper contact, and with our lips just barely touching I felt so grateful that this beautiful man I cared for was sharing my bed with me. And I could feel that he felt the same.
I pulled back just a little from kissing him so that I could see his face more clearly. And at that moment, we made eye contact in a way I've never shared with another man in my life. I touched his face, and he reached his hand up to touch mine. And the caring in Ben's eyes at that moment was so pure that I wanted nothing more than to be with him in exactly this way for as long as he would let me. Of course, it was a sexual connection, but it had nothing to do with the sex that I was used to, and even if it had, I felt so grateful that Ben had asked me to keep things between us basically PG rated. For whatever reason I didn't understand, holding back from sex was somehow allowing something deeper and more intimate than I'd ever known with a man to open up between us.
"Ben," I said, "I'm so glad to be with you like this."
"Me too, Kyle," he said.
Then, without even thinking about it, I added, "Tonight, let's not worry about what's going on beneath the covers, OK? Instead, let's just focus on what's happening above the covers." To illustrate, I pulled the sheet and blankets up to keep both of us warm, and kissed Ben again more deeply.
We kissed for a long time, and I could feel that Ben really let himself get into it for the first time. We just kissed and kissed, and I felt so connected with him, and I could tell that he did, too.
Then, something happened that I didn't expect. Ben took my hand, and pulled away from me for a little bit, so that I asked, "Is everything OK?"
"Yes," he said, "Everything is completely OK. But, Kyle, I need to tell you something." I just waited, with no expectations, but looked into Ben's eyes and let him know that whatever it was, it was OK. Then he told me, "This really makes me nervous telling you this. Kyle, sometimes when I'm with a guy, I have trouble getting an erection."
He didn't say anything beyond that. But I could feel that his whole body was trembling. And without even thinking, the words that came out of my mouth were, "Me, too."
I don't think he could believe what I said, probably because I couldn't believe it either. The first thing he asked was, "Really?"
Still without thinking, I said, "Yeah." I still hadn't thought about it, but even so, I knew it to be true. I told him, "It happens to me all the time."
"Really?" he asked again.
I answered, "Yeah. I usually avoid the issue by just letting a guy fuck me."
He answered, "I've tried that a few times, but I don't like it much."
I didn't want to tell him then and there that I've been a bottom since I was 15, mostly because I didn't want to disappoint my partner. So whenever I couldn't get hard, or when I got soft, I'd just let them fuck me, and pretend to love it. And sometimes, it was OK. But often, I felt like I was betraying myself. I didn't particularly want to get into it, but I know that eventually, I will. For now, I'm just telling you, Jared, and hoping that you won't betray me, too.
Instead, I just said, "I'm really glad you told me."
Even so, Ben still looked pretty shaken and insecure, though. He said, "Kyle, listen, it's OK if you want me to go. If you need a guy with a big, hard dick, I understand, and I'll go." He looked almost on the verge of tears as he said this. "I just wish I could be that guy, but I know I can't."
"No, Ben," I said, "Listen to me. It's OK. The same thing happens to me."
"Really?" he said again, like he couldn't believe that anyone else could ever have the same problem.
"Yes." I told him. "So, let's talk about it, and maybe we can help each other through this." And I reassured him again, "I'm really glad you told me."
"Me, too," he said at last. And as we lay next to each other, I could feel that Ben was finally relaxing with me in a way he never had before.
And I felt the same, so I said, "It kind of feels like the pressure is off."
"I know!" he said. "I'm really glad I told you, Kyle. I just didn't want to pretend, because I really like you, and if you need another type of guy to make you happy, I want you to have that."
I couldn't help but kiss him deeply when he said that. Did I mention how massively handsome Ben is? I felt so close to him at that moment. And the pressure really was off for both of us. We kissed for a while like that, and then I pulled back and said, "Doesn't it feel good to be able to kiss without feeling like it has to be more?"
"Yes!" said Ben. "I always feel like if it starts getting too hot, then I'll need to make an excuse why I'm not ready to do more."
"I get it," I said, "For me, I end up bottoming when I really don't want to. But I just assumed you were a top, so..."
Ben said, "Yeah, everyone thinks so, because I'm masculine or whatever. But listen, Kyle, I am so not a top, OK. But I'm not a bottom either. I'm just me -- whatever that means."
I told him, "I think it means that I like you a LOT, Ben. And I really meant it when I said that tonight, let's just focus on what's going on above the covers rather than below them. What do you think?"
Ben said, "I think I've died and gone to heaven."
I told him, "I know the feeling." And from there, we just kissed and kissed without worrying about the stuff we normally worry about. It must have been past 1:00 by that point, so for a while we just drifted in and out of sleep. At some point, I blew the candle out so the place wouldn't burn down as we slept.
That's not the whole story by any means, but for now, I need to sign off, because I'm exhausted. But I promise I'll finish telling you the rest once I wake up.
Again, thanks for the day off. I promise I'll make it up to you!
Take care, Kyle
To be continued...
Thanks for reading! If any of this story speaks to you and you've thought about writing to me about it, please do: judestjude2357@gmail.com. I promise to do my best to answer, especially if you're feeling alone with no one to talk to about this stuff. Thanks again, TJ