The last couple of days have rocked my world.
First, I met up with Jeff, just to test the waters and settle a little curiosity I had. Ended up sucking his dick, and honestly loved it. So much so, I had to go back for another round the following night.
Except, our second meeting, things got more intense. I went in knowing that I would end up with his cock in my mouth and throat again, and I had a desire to let him put it in my ass too. I convinced myself that I needed to lose my anal virginity to this man. And, after a nice 69 session on his couch, followed by an intense shower together, where not only did I swallow his cum for the first time, but he also ate my ass for the first time ever, we finally made our way into his bedroom, where he took my ass and fucked me with his 7" thick cock. It was absolutely amazing.
But then, he crushed me when he told me that he was leaving town for a few weeks. Immediately, I was bummed out. I wanted to plan our next session. I wanted him to fuck me again. I wanted his cock balls deep down my throat. But, he was leaving. And, for at least a few weeks. Upon telling me that he would be leaving, he told me that he wanted me to get on Craigslist and find someone else to fuck me while he was gone.
I posted an ad at his request, and ended up getting a response from a guy named David. He waa 26, 6'3" and a bigger guy at 290 lbs, but he seemed like a good guy and his cock, though shorter than Jeff's, was nice and thick. We chatted through email before exchanging numbers. I told him I would be in touch.
Jeff and I managed to squeeze in one more meeting, the night before he left, where he fucked me in the ass twice, once in his bedroom with a condom and lube, the second time was in the shower when we were cleaning up. The second time, he didn't use a condom, but he showed off his amazing pull out game and gave me plenty of notice. After he pulled out, he started stroking his cock to finish the job. I turned around and dropped to my knees, opening my mouth and holding out my tongue, giving him a target between my mouth and my face. He shot his second load and covered a bit of my face, also getting some cum in my mouth, which I promptly played with before showing it off to him and swallowing.
"Damn, am I gonna miss this while I'm gone!" Jeff says to me with a smile, offering a hand to me to help me up to my feet. With the shower still running, I guide him back to where his still erect cock was getting hit by the water, took a hand and stroked his dick under the water, basically rinsing him off, then motion for him to step forward again. As he does, I lean forward and take his cock back into my mouth, and bob back and forth on his cock, giving him a hint of an ass-to-mouth experience, as his eyes light up and a surprised look goes across his face.
"Wow bud..." Jeff managed to say through his moaning. I never lose eye contact with him, even after he grabs the back of my head and starts to facefuck me with his last remaining stamina. When he finally ran out of gas, he pulled his dick out, and I swallowed the remaining traces of his cum. Only then, was I ready to get out of the shower.
As we were getting around after the shower, I took a brief look at his ass while he was bent over. Jeff, with a towel in his hands, stood back up and looked over his shoulder to dry off, before noticing that I was staring at his ass. I realized I was caught, so I looked up at Jeff, only to be greeted with a smile.
"Maybe soon, you can top me. For now, I'm enjoying your mouth and ass!" Jeff said, walking over to reach around and squeeze my ass once more.
As I'm enjoying the last few moments before I leave his place for the next several weeks, I find myself with a selfish desire to keep him here, so he could fuck my brains out. But, i knew that he must have had this planned for awhile, and he just didn't know that when we met, we would become more than a one time hookup. I don't want to say I was falling for this guy, but he was much more than a drinking buddy at this point.
We finished getting around, and head down to his living room, sitting on the couch where we first had any kind of physical connection. As I'm putting my shoes on, Jeff casually puts an arm around the back of the couch, waiting for me to sit back into. I sit up and he immediately drops his arm to my shoulders and looks me straight in the eyes.
"So, I've got to ask..."Jeff started. "...did you make any progress on the Craigslist hunt for while I'm away?"
I take a semi-deep breath in before I answer. "Yes, as a matter of fact, I did. I've been chatting to another guy, a little closer to my age, but he's younger. He's pretty interested. Asked me to come over sometime soon. He doesn't live real far from here, but he's definitely looking to get some head and top. I don't think he wants to give oral or anything at this point."
"Sounds like he's either not real experienced, or he knows what he likes!" Jeff said. "Think you're going to meet up?"
"I'm not really sure man. I mean, he seems cool...he's got a pretty nice looking dick...but, I'm kinda hooked on you to be honest." I say, putting a hand on Jeff's thigh between his legs.
Jeff smiles, looking down at my hand, then looks back up into my eyes. "I like your skills...even having just started, you're pretty natural at all of this! I really think you're a good guy too." Jeff said, then adjusts his position on the couch to where he can turn to face me better. "But, I didn't know where we were going after that first night. I didn't realize that you'd be here for a third time tonight, or that I would have fucked you three times now. I knew I was leaving town for a few weeks, but didn't know what to expect with you. So, after last time, I thought you should know. But, I also don't want you to stop having fun and wait for me because I'm not going to be here for at least 3 or 4 weeks."
I smile at the fact that he's trying to look out for me in the end, but I'm also unsure about meeting up with another guy, trying to get a feel for him, while knowing just how much fun I'm having with Jeff and how much he's already helping me discover about this lifestyle.
"Jeff...let me just ask you something..." I start, getting Jeff's undivided attention. "Even if I meet up with this guy...or any other guys...while you're gone...I still want you to be my main...my main..." I continue, suddenly at a loss for words.
"You want to be friends with benefits?" Jeff asked, finishing my thought.
"Yes! Thats it!" I say excitedly. "Do you want to be friends with benefits? Do you want to be my MAIN friend with benefits?" I ask him.
Unable to hide his smile, Jeff replies with "Fuck yes!" as he wraps his arm around my shoulders once more. "But, I want something." Jeff continues.
Feeling insanely relieved that this was going to continue between us, I answered back "What's that? What can I do?"
Jeff adjusts once more, turning to face me and places a hand on each shoulder.
"I want you to get ahold of this guy, set it up, and let him fuck you while I'm gone..once, twice, everyday, I don't care! I want you to go have fun, maybe learn a few different tricks to try when I come back. Hell, get with a couple of guys if you want. But, you've got something going with this one guy...set it up." Jeff said to me, no hesitation in his words.
"Okay. I'll text him tonight to set it up." I said, now running through the thoughts and excitement of meeting up with another guy. I'm pretty happy about how this talk has gone!
"Great! I'm leaving tomorrow morning and I'll check into my hotel room tomorrow evening. Try to go get fucked then!" Jeff said. "And remember...try to take pictures and video! Send me something to remind me of what I'm missing!"
I smile and nod. "No promises, but I'll try my best!" I say to Jeff. He squeezes my thigh and starts to get up from the couch.
"You want a beer or anything? I'm going to have to get to bed soon." Jeff says as he starts to head into his kitchen.
"No, I better go home and let you get some rest. Be careful heading out tomorrow!" I say, standing up and making my way to his door.
Jeff follows me there and holds the door as I start to make my exit. "I mean it...have a good time while I'm gone. We'll make up for it when I get back! I'll give you a call when I get in."
"I might have my mouth full of cock at that point!" I say and Jeff laughs.
"Well, if you're not too busy, I'll talk to you tomorrow evening!" Jeff says as I step out his door.
"Okay. Enjoy your trip. See you soon!"
"Goodnight."
"Goodnight man."
As soon as I get in my car and start it up, I pull out my phone. I bring up David's number and start a new text.
"Hey David. How soon are you available to meet up?" I text him. I'm still on a bit of a high from Jeff's cock, and I truly wish that I could go back in for one more round, but as I sit in my car, letting the engine warm up for a few moments before I hit the road, I sit and watch as Jeff closes his door and shuts off the lights in his living room. He's going to bed after 2 amazing rounds of anal sex. He's got to get some rest before leaving in the morning. It was a great Friday night, and I wish I could repeat with him on Saturday night.
As I sigh to myself, hoping for Jeff's speedy return, my phone buzzes in the passenger seat. A new email, or a Facebook notification maybe. I pick it up to take a quick look before putting my car in gear and leaving my official friend with benefits behind to get some sleep. It's a text. And it's from David. I was taken back by how quickly he replied, but I figured that his schedule must have been similar to mine and Jeff's. I open the message and a smile immediately forms upon reading it.
"Tomorrow evening. I want that ass." he had sent.
In a happy state of being, but also in a bit of shock, I think to myself about how awesome this was. Just earlier in the week, I was meeting a total stranger, preparing myself to give him a blowjob...first guy I've ever sought out to do so. A few days later, I've had his dick in my ass a few times, and I've swallowed his cum a couple of times as well. Tonight, we commit to being friends with benefits, a road that I had no idea where it would go, but I was excited to travel. And now, I was setting up a time to go meet another man and let him have his way with me as well. I didn't expect things to turn out this way, but I was beyond excited to see how things were playing out. This was going to happen.
"Okay. It's a date." I send back to David and he replies damn near immediately after.
"Looking forward to it. We'll talk details tomorrow."
"Can't wait." is all I replied with, but that's all I need to say in the moment. I put my phone down, back out of Jeff's driveway and head home to go to sleep.
The next morning, I wake up to the sound of my phone buzzing on top of my dresser. I get out of bed and go check my phone, and I'm greeted by texts from Jeff, David, and my girlfriend Kayla. I open up Kayla's text first.
"Hey baby! Hope you got some rest after work. I've been missing you, but between being sick, our work schedules, and things like this bachelorette party this evening, life's been a little chaotic. Hopefully soon we can get some time to ourselves. I need that dick! Lol! Give me a call when you can. Love you!"
Kayla was an amazing woman. She had a great personality, an amazing body, and she was absolutely fantastic in bed. The way this woman could suck a dick was phenomenal, and after several years together with her giving me oral, I actually picked up a few tricks from her and I had put them to play with Jeff. Not that I could ever tell her, but I owe her a huge amount of gratitude for teaching me how to properly give oral.
