Date: Thu, 9 Jul 2020 00:53:42 -0400
From: Jude St. Jude <judestjude2357@gmail.com>
Subject: Inadequate Men - Chapter 18 - Pajama Party

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