Weekend Update: Friday's Double Feature

Friday. Friday. Gotta get down on Friday.

I couldn't resist. Orientation with the new job that morning. I'm excited about the position and I start on Monday. More on the guy that I told you about in my last post. He deserves a name...I'll go with Caleb. Caleb and I have been talking on a regular basis for the past 4-5 days. Honestly, he has been reason why I even log on to Grindr. So we're chatting and I ask if he'd want to meet up. Not for anything sexual, but just somewhere to talk to him more. I've seen his face and at this point, he'd not seen me at all. He says yes and we figure out a place to meet. After all that talk, he asks if I could send a picture of me just so he'd recognize me once we met at the restaurant. I felt really comfortable with him, and was more than happy to send him a pic. We talk for a little more, then he had to log off so he can visit with his family in town. I log off as well, then took a nap, just so more time could pass until that evening... I woke up really horny and decided to log back on to Grindr to see if I could have a little fun before dinner. Now in hindsight, that probably makes me seem like a whore, but I don't care. Just a horny young guy living my life as I want to.

As soon as I log on, I spotted a picture of a guy flexing his bicep. Started chatting him up and we agree to meet at his hotel (conveniently three miles away from where I was meeting Caleb for dinner.) He was an older guy, but very handsome and sexy for his age. As I was driving to the hotel, I started to wonder about what the hell I was doing. There were multiple times during the drive over I had second thoughts.

"Is this guy gonna hurt me? Do I tell Caleb about this? This is going to be an interesting evening, can't wait to blog about this!"

Alright, so I wasn't all nervous. But enough to where I brought a knife with me just in case this guy tried something crazy. Hey, I gotta be safe in more ways than one.. right? He texts me the room number as I pull in the parking lot. I make my way in and head to the elevator. Get to the fourth floor, knock on the door. He took a little bit to answer, and for some reason I thought,

"I wonder if this is a undercover sting operation? Oh wait, there was no money involved, I'm good."

He opens and he's just as I described. I take my jacket off on the couch, make our way to the bed and just talk for a bit. Talked about the upcoming big game on Saturday, the NBA season, what he does (attorney), what I will be doing, etc. Then we get a little touchy-feely. Touching leads to kissing, leading back to touching. Touching to clothes coming off. He was a great kisser, something that seems to be a little hard to find. At least for me it is. At this point we're down to underwear. He kisses and licks all the way south and I'm hard as a rock at this point. He begins blowing me. He was a little rough at first until I had to coach him a little. While he's blowing me, he rubs on my nipples and chest. Great level of detail he had with his hands. Then we get into a 69. Now I'm not blowing my own horn, but I give great head. So during the course of me blowing him, he stops me at least three times. I love giving pleasure and since I was receiving at the same time, it was great. Seeing him respond to me blowing made him that much more excited, thus making me more excited too.

He then asks if I wanted to fuck him. I had never fucked a guy, so I declined. He knew I hadn't before hand, so he was cool with me not wanting to. We rolled around kissing and touching and jacking each other off for a good amount of time. We finally get to a place where we were both ready to cum. We both get into a good rhythm and I come first. Probably one of the best orgasms I've had in a while. I'm ready for him to cum, so I continue to jack him when he stops me to grab a towel for me. He wipes me up and gives me a final suck. Felt amazing. I continue to jack him until he came. Good explosion for him as well. He wipes himself and he asks if I wanted to take a shower before I "met my friends for dinner." I had plenty of time, so we take a shower together and continued to talk. He washes me all over and I do the same.

We had great conversation afterward and he tells me he comes back in town every couple of weeks if I wanted to do this again. I told him to let me know whenever he's back and we'll go from there. I was a little vague in my answer just because I  didn't want to get his hopes up (or mine for that matter) for us hooking up again. We say our goodbyes and I exit the room. As I leave the room, I see a man and woman (obviously a couple) head my way. I automatically felt like I was making the walk of shame down the hallway as I give a nod to the guy. He smiled and gave the same nod. I'm sure he knew what went down, but I didn't care. As I made my way to the lobby, the receptionist gave an extra happy "Have a good night." Of course I wanted to tell her I already did and on to the next part of the good night, but I refrained. I was sure everyone knew what I just did in that hotel room, which is kind of funny to think about. I get to my car and let out a huge laugh.  Don't know why. I just felt like laughing.

I make my way down the road to dinner. I was about 15 minutes early, so I just sat in my car and waited.  The restaurant was surprisingly empty by the looks of how many cars were in the parking lot. I parked in a position where I could see the door as well as anyone entering the parking lot. Time passes. More time passes. About 20 minutes later, I decided to call Caleb to see if he'd gotten lost. Ring. Ring. Ring. Ring. Ring....

Caleb: "Hey, you here?"
Me: "Yeah, in the parking lot. You're here too?"
Caleb: "Just walked inside."
Me: "Oh, I must have missed you..."

At this point, I'm getting out of the car and he walks outside. Immediately smile at each other and walk inside. Make our way to our seats. I could tell he was a little bit nervous and to be honest, so was I. He was exactly the way he was in his picture. Cute. Not in a "sort of cute, but I'll say cute anyway because I have to be nice when you sent me a pic" but a "better than the picture cute." And his shyness was very cute as well. We make small talk with little awkward moments in between. Don't get me wrong, the moments weren't that awkward. Just small pauses in conversation. I like those moments. Just to see what the recover move or topic is going to be. After a couple drinks in, Caleb becomes more comfortable and we once again, talk about anything and everything. After those drinks and the water I ordered, I had to go to the restroom. And as a guy that knows a little touch goes a long way, I touch his shoulder as I pass him. I get back and we continue conversation.

It was just a solid good first meeting. I don't know what else to say besides that. We pay, get up and head out the door. I ask him what he's doing after this and he said he's going home to crash since he was up all day. (Which I'd already known from talking to him earlier.) I was fine with that, I was ready to go home too. He tells me he had a great time and hoped that he hadn't scared me away. I told him that I don't scare easily and told him that we'd have to do this again soon. He agreed, gave a big hug and we parted ways.

Pretty sure I was on cloud 9 the entire way home. I get in the drive way and I get this text:

"It was great meeting you tonight. I had a really good time. :-)"

I reply: "Hey, just stepped in the door. The feeling is mutual. I had an awesome time. I'm making it my mission to get you to like some type of vegetable! :-)"

He doesn't like vegetables at all. I absolutely love them. I'll get him to love them too.. ha.

Needless to say, we've been texting since then. No plans to meet back up at the moment, but I'm sure it'll happen soon.

I think that's a good enough post for now. Be sure to comment or email me if you want.

- Under Wraps
underwraps87@gmail.com