Guys Trip, Lace Causes a Stir Ch. 05

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I almost didn't believe it so I flexed to be sure, squeezing my cheeks and sphincter, both of them meeting with resistance. It was smaller and somewhat soft, but more than enough to know something was there. I was so glad that I asked Steve to stay there because it was an amazing position to wake up in. The feeling of fullness was amazing.

I couldn't believe that he managed to stay in, but I wasn't going to question it. Content with where I was, I reached back to put my hand on his hip, squeezed my cheeks one more time, then relaxed, "mmm."

Steve responded, "Mmhm" while turning his hand to cup my left pec. I was completely awake by this point but I was content to just lay there and soak in the experience for a bit. I pulled the sheet back up, then put my hand over his and settled back in.

I just lay there for a bit, lost in thought, amazed at how far we had come. Just a few days ago I had been terrified about how he might react when he discovered that I liked to wear panties and thongs, thongs being my clear preference. And now, here we were cuddling after making out, having amazing sex, and then sleeping together.

It wasn't long before I was brought back to the present. Steve had cautiously started to move behind me. His movements were so soft and slow as he gently slid forward and back. I could feel a little air between us right before he made a long, slow stroke back in.

As he was pushing forward I couldn't help myself and I quietly moaned, "mmmmm".

When he was completely pressed up against my backside again he paused. As soon as he stopped I felt his lips on my neck. I moaned again, "mmmm". He kept kissing and licking my neck, my shoulder, my ear but he also resumed slowly probing with his steadily growing and hardening rod.

He kept at it, long and slow, and I grew along with him. My cock was jutting out in front of me when I spoke, just above a whisper, "Keep going, just like that." I don't think he had any plans to stop but I had to make it last just the way it was.

Between kisses he replied, "As you wish."

With the gentle pumping, as opposed to the hungrier sex from earlier, my mind was a little more free so I could actually talk, "I love the feeling of you pumping inside me. This slow build is different, really nice...fantastic actually."

Steve's lips left my neck just long enough for a quick response, "Mmhm. It really is."

"Did you actually sleep at all?"

"Definitely. You wore me out."

"Yea, I'm sure it was all my fault." I rolled my eyes even though he couldn't see. "So I gotta ask then. How did you manage to stay in me while we slept?"

Steve laughed a little, "I wish. I was definitely still in you when we fell asleep but then I slipped out at some point. When I woke up I was a little disappointed to find that I was semi-hard but only tucked between your legs instead of inside you. Since I was out, I lubed up some more and tried to see if I could slip back in without waking you up. I was hoping you hadn't closed up too much since I wasn't fully hard anymore."

He finished up with, "As you can tell, I was obviously successful", and punctuated that by pushing all the way in, then flexing.

"Mmm. Yes you were." I reached back to pull him against me as I pushed my ass back against him and then part asked and part ordered, "Please keep going, but slow, just like you have been."

"With pleasure."

His hand went back to caressing my chest and he resumed and his lips went back to my neck.

I moaned softly, "Mmmm, this is...wow. I love this fullness, the feeling of you slipping in and out. I can feel all of your contours, every inch as you move."

"I can't get enough of being in you. You're so tight, and feeling your body pressed against mine gives me chills."

Thoughts of how this all started back in that little motel room in the middle of nowhere, "God, what a crazy trip."

"Yea, no kidding. Who would've thought. I know I never expected anything like this!"

I twisted a little to look back as much as I could while we talked. "I don't know about you, but I've definitely learned a thing or two about myself since this all started, real eye opening things."

Steve nodded before responding, "Somewhat for me as well. I've always been open to many different experiences in the bedroom, but there were still limits."

"Limits. That's an interesting way to put it. You have some experience but it's been a lot bigger leap for me, but certain things were more surprising than others, possibly the same things that surprised you."

Steve's movements hadn't stopped all together but had become less continuous. His slow thrusts would go and then you could tell when he was thinking or focusing on his words because they would pause. "How so?"

I was still enjoying the slow penetration, which was obvious if you could see how rock-hard I was, but I needed to move. "Don't take this the wrong way. This feels amazing, and anyone would be lucky to wake up this way, but I'm really interested in this conversation as well and I want us to be able to see each other."

After that I pulled forward a little so I could change positions. I was definitely disappointed when I finally got far enough for him to slip out. The gaping feeling was actually nice for a moment but the emptiness had me longing for him to fill me again. I pushed that thought back and rolled over in place until we were face to face, our hard cocks barely touching down below.

"There we go." I could see a little of the same lust that I was feeling in Steve's face. "You okay?"

"Absolutely, just missing that warm, tightness a little. But also happy to hear what's next."

"Alright, now where was I?"

It was a rhetorical question but Steve responded anyway, "You were about to say how you were surprised, what was more surprising, and maybe a little bit about what you have been learning about yourself."

"Wow, you aren't going to let me off the hook at all! Okay, here goes."

He smiled at that, "Nope!"

I paused one more time before diving in. "So, you saw on the very first day that I like wearing women's underwear." He raised his eyebrows but didn't say anything. "Okay, ONLY wear women's underwear. I suppose it wasn't a huge leap to think that I might be curious about some stuff, so things getting exciting in the motel room was probably not a huge step in the grand scheme of things."

Taking a little calming breath, I pushed on, "Then there was the little gift bag in this hotel. It was really fun slipping into those items, but it was a bit of a shocker to see where things went once I did! Playing around a little was one thing, but things went to a whole other level. I'm not sure if I was more surprised with where things went that night-the dressing up, the role-playing for lack of a better term, the complete giving in to the 'persona'- or realizing after that I really wanted to do it again!"

"At that point I was still attributing some of it to how the lingerie and then the costume put me in character. I can't believe I let the euphoria convince me that our little bet was a good idea. I wasn't going to back out though so I had to carry on, and boy was I glad I did. Once again, big leap forward in my mind. Not because of the actions, but because I realized how much I enjoyed them.:

Steve jumped in with a quick comment, "I was able to see, and then hear about, most of this but it's interesting to hear you talk about it. When you lay it all out l can see each step, and how big some of them must have been."

While he was talking I stole a couple of deep breaths, "Then you can see where I'm going next. You haven't said much but since I've been there for most of what you've done since we've been here I'm wondering if we might be on the same page."

"You don't have to answer yet. As you can see, everything up until that point had been exciting, maybe a little kinky, and filled with countless orgasms, really good orgasms, and could easily have been attributed to getting caught up in the moment. The biggest leap of all came when I realized that there was something that I wanted to do, something that really made me think."

I took another breath before talking about what we both knew was coming, "When I saw you sleeping there, obviously naked, I have to admit I got horny but that wasn't much of a revelation at that point. The thing that hit me most was after the nap when we were getting back into bed. Seeing you sitting there, casually naked, got me a little hot, but what really hit home was that I really wanted to kiss you at that moment.

"What the fuck was that all about?! Everything up until then had been purely physical, purely sexual, and I was thinking about kissing you. At that point I was still thinking it might just be experimentation, making sure I tried everything. But I couldn't have been more wrong. While we were kissing I got my biggest, hardest erection of the weekend, and from the state you were in when we stopped it seemed like you enjoyed it a little as well."

Right then he smiled and I felt the head of his manhood twitch against mine, "I guess you could say that."

"So, you can see all of the things that surprised me, some clearly more than others. I guess the overly simplistic way to explain what I learned about myself is that, not only do I really like sex with a man, I'm actually attracted on another level. haven't just been experimenting sexually, although there has been a lot of great experimenting...I've come to realize that I'm actually bisexual."

Nervously I looked at him, "So there you have it. For better or worse, it's all out there now."

Fortunately he didn't make me wait before responding, "Wow. That was a lot to get out. I have to admit my revelations mostly came long before this weekend. I've known for quite awhile that a man can do things to you in bed, make you feel certain things, better than most women. I've also known how much I enjoy a man's body, his ass and his cock. You already figured out most of that though."

I nodded and smiled, "Yes, and I have really enjoyed the process."

He returned my smile with a devious one of his own. "Unlike you though, I have kissed a couple of men before. You know, as you said, 'making sure I tried everything', but neither time really did anything for me. It wasn't that I was turned off or anything. It just didn't do anything for me so I haven't done it again."

"Gave it a couple tries and then you figured it wasn't for you. Makes sense."

"Sure, until you kissed me that is. That was a real eye opener for sure. You saw how hard I got from that kiss, and we weren't doing anything sexual at the time! So it seems that you and I have both come to a similar realization at about the same time."

"And what a realization it is! So, since this is new to both of us don't you think we should try it out again as often as possible this weekend just to be sure it wasn't just a heat of the moment kind of thing?"

He tried to be nonchalant about it but I could sense the excitement when he answered, "Well, I guess if you think it would help."

"We don't have to, but...", then I leaned in and gently pressed my lips to his.

He didn't hesitate to kiss back this time and we shared a long, soft kiss, our lips pressed softly together and our tongues lightly probing. My hand was on the back of his head, not to hold it in place so much as to let him know that it was right where I wanted it.

Steve was equally clear in showing what he wanted. His hand found my back and he just held it there. We were both lost in the moment, not pulling back but neither of us pressing to go any further in that moment.

Finally, I loosened my hold and we broke the kiss, "That seemed like a decent first test don't you think?"

"Yes, I think", but he didn't elaborate any further.

"I mean, we probably need a larger sampling to know for sure...more times and different situations would probably help." I was trying to match how casual he was trying to come off.

He agreed, "Yea, you're probably right."

"Okay, it's settled then. More verification to follow." After that, I started to move, "Don't move. I'll be right back." Before he got a chance to stop me I slipped out of the bed and darted off to the bathroom.

True to my word, I returned quickly. In my hand was a warm, wet rag from the bathroom. He had a questioning look on his face. "There's one more thing I'd like to do before we get up to go meet the other guys."

I climbed onto the edge of the bed and reached to take him into my hand. Then I gently, but thoroughly wiped his shaft clean, followed by his balls, making sure to stroke him slowly during the process.

He swelled slightly in my hand as I continued to lightly rub, now without the rag. He was still pretty calm, "Oh? What did you have in mind?"

I inched over the rest of the way until I was laying on my side facing him, only this time I was pointed the other way with my legs pointed toward the corner of the bed just past the outside of my pillow, "Let's start with this" and I took his penis into my mouth. Having just been cleaned, there wasn't much taste, but I really liked the feel of his soft member in my mouth. I was able to fairly easily take most of it into my mouth but I pulled back quickly so I could focus on sucking on the head, licking all around the coronal ridge.

I was looking forward to feeling it thicken and slowly push its way across my tongue, and I was pretty confident it wouldn't take too long.

"Mmm, I like that." The bed shook slightly as Steve shifted around. "But I want some too", and then he took my wakening member fully into his mouth as well.

I let him fall from my mouth just long enough to respond, "This right here is what I had in mind", and then I gently circled him with my hand and guided him back into my mouth, noticing immediately that he had already gotten thicker and longer.

I sucked on his glans and caressed his balls with one hand while the other rested against his bod, gently holding the base of his shaft. I wasn't in a hurry, and I could tell Steve felt the same as he continued to mirror my movements. We were both focused on the delicious treat before us and took our time.

We were both growing, lengthening and thickening with the passing moments. The feeling of him swelling, filling my mouth and trying to probe deeper, was intoxicating. I went from sucking just on the head to slowly moving up and down, sliding my tongue up and down his shaft. He continued to harden and I finally got that first, delicious taste of his thick precum. As soon as I tasted the excitement pushed some of my own out onto Steve's willing tongue.

It wasn't too long before we were both at our full length. For me, the combination of Steve's skill and the excitement of having him in my mouth had me going strong. I kept my pace slow but started taking him deeper into my mouth every few strokes, continuing on as he reached, and then entered my throat. I moved my right hand from his shaft to grasp his cheek and pull him toward me.

The angle my head was at, tipped up to reach for my prize, made it easier to take him in and I bobbed slowly up and then all of the way back down until at last my nose pressed against his balls, just above where my other hand lay. He had already shown that he knew what he was doing but this time he let me take the lead.

Every time I did something new, he wasn't far behind. When I bobbed slowly, he bobbed just as slowly. When I sucked harder on his spongy head, he sucked hard on mine. When I repeatedly lowered to the base of his cock, he lowered just as smoothly and easily.

Eventually I lost track of what exactly Steve was doing. I just felt pleasure growing as it coursed from my balls up through my shaft. All of my concentration was on worshipping his manhood as it repeatedly slid across my tongue and deep into my throat. It felt so thick and hard in my mouth and I couldn't imagine anywhere that I would have rather been or anything that I would have rather been doing in that moment.

Again and again I took him to the root and pressed my nose to his balls. As I continued I could feel them getting tighter, drawing up to his body. Each time I reached his balls I pressed my nose into them and swallowed, wordlessly urging him on.

God he tasted good, felt so good in my mouth, and oh god did I feel good right then as well. I was so hard and my balls were sucked up tight. There was no way I was going to last much longer and I was desperate to feel him throb in my mouth.

No sooner had that thought crossed my mind when I felt his ass clench in my hand as he thrusted against me, the head of his cock finishing deep in my throat when my he bottomed out against my chin. He held there and then pulled back, only to repeat the move again...and again...and again.

I moaned around his cock, thrilled when he started throbbing in my mouth. I flexed each time he thrusted, each time he throbbed. His throat was tight, squeezing me, milking me even as I worked to empty his balls one last time. We throbbed and pulsed, almost in unison.

Finally, he moaned around me shaft, harder than he had been and then I felt why as his warm seed entered my throat. It was a smaller load than I had felt earlier but the contractions and pulses were just as strong. His orgasm still had him bottoming out in my throat over and over, pumping into me again and again.

My climax started a little after his and was more erratic. I felt myself pulse and thrust then pause, and then the cycle would repeat. The pauses were sometimes short and other times longer, but the strength of each was just as strong as the last...until they began to fade and then finally stopped.

When we both were spent I suckled gently on his glans as he softened and shrank between my lips until finally I let him fall from my mouth, empty from the afternoon's activities. "That was exactly what I had in mind."

"Damn. You come up with some of the best ideas."

"You know," and with a smirk, "I really do."

"Well, I have one more much less exciting idea." It was one of my tamest. "Shower before we meet up with Ben and Ryan?"

Steve nodded and started to move, "That sounds like a great plan. Shower for two coming up."

I got up and followed him out, "Oh, one more, no two more things."

"What's that?" he asked.

"One, I want to surprise the guys with something again, just not sure what yet. And two, I know we've made progress and all, and we're both open to playing together just like we are, but..." and I trailed off a little, unsure of how to continue.

As always, Steve knew just what to say, "Just spit it out. When has beating around the bush ever helped?"

"Very true", I conceded, and then just blurted out what was on my mind, "I still want to dress up, maybe role-play a little, and get taken like a woman."

He winked at me, "Yes ma'am", and my cock twitched in response.

Steve turned to start the shower and I slowly followed. I thought about finding some clothes while it heated up, but then I decided that I was in no hurry to get dressed so why bother.

My mind was already working, trying to figure out the best way to surprise Ben and Ryan, and thinking about what naughty outfit I was going to wear next.

To be continued...

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AnonymousAnonymousabout 1 year ago

Amazingly engaging! I very much would love to be in Jimmy's place! I am bi and wear panties every day (nightgowns or other nighties every night)--though only a very few have ever seen that side of me. To have a single friend, much less 3, that were totally accepting and playful....fantasy life for sure!

AnonymousAnonymousabout 2 years ago

Did you ever get to suck Ryan that was about 10 inches long

trybimantrybimanover 3 years agoAuthor
Thank you

Thanks @thomb69! If only we could all get to have our fantasy experiences

thomb69thomb69over 3 years ago
Awesome series!

Couldn't stop reading once I'd started. You've perfectly captured some of my greatest fantasies as well as a few of my own experiences. How I'd love to find my own "steve."

trybimantrybimanover 3 years agoAuthor
Thank you!

@AHNuts00 - thank you so much for the very positive feedback. It means a lot! This one took me a long time to write. I tend to write in spurts and there were more than a few breaks along the way. I've really enjoyed writing this series. I've truly learned a lot about myself along the way. I'm glad you like the series!

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