My Awakening Ch. 01

After 40 years of denial and hiding in the closet, I finally told my best friend whom I had known through all those years that I may be bi or even gay as I had also been attracted to men for as long as he'd known me. I'm so glad I did as he not only was the first man I've ever had sex with, he's now my first and hopefully only boyfriend. In the two years we've been a together, he's taught me so much about myself, about my being a natural submissive, and about my desire for both genders. He was able to draw out my deep, hidden secret fantasies and has been working to make each fantasy come true.

Like today. I've often fantasized of being taken by a completely unassuming but good looking man that I had never met before. Kinda like if I were to meet this really handsome guy at a bar and somehow, his gaydar would go off as he would check me out from a few stools away. But here I was, now spoken for but spoken for by a really imaginative and supportive boyfriend.

I had no clue that Ron had been planning and making arrangements for me to finally get taken by that handsome stranger until breakfast. While we were eating, Ronnie asked me if I wanted to go to Home Depot. I was pretty eager as I nodded yes since we both always liked checking out the other guys and seeing if any of them were checking us out as well.

"You've been wanting to check out some window shades for a while now, anyway. Plus you've been fantasizing of some random, handsome stranger getting into you, too. I know of such a guy and I trust him. He and I used to play together back about ten or so years ago when he was in his early 20's. He's an all around decent guy, excellent kisser, amazing mouth though not as good as yours, and he loves mid fifties, chubby bears like you."

Here's my chance to get fucked by a total stranger with permission from my boyfriend. I could feel my cock stiffening at this opportunity. Ronnie looked over at my bulging shorts and just smiled. He then said, "Come here. Kiss me then go get yourself lubed and plugged. And use that new plug I bought you. The one for lovers. I also want you wearing the same booty shorts you're in right now. And I need you in bikini underwear to help restrain the plug in case it comes out. Make them black as my old friend loves men in black underwear."

As I kissed Ronnie thank you, I shuddered as he ran his hand across my now stiff cock. I wanted to release so bad but there's no way I'd do so unless my lover had emptied himself in me first. I especially wouldn't do so right now without Ronnie's express permission first. Nope. I'm going to have to wait until Ronnie's friend empties himself inside me. If I let him.

In just a few seconds, I had sprinted upstairs and dug out my largest training plug. I lubed it up and inserted it inside me until I felt the base go past my sphincter. I sat down on it ensuring that the base was pushed directly up against me. I found my cutest pair of CK black undies Ronnie bought me a while back and put those on. After putting my shorts back on, we left for Home Depot.

Normally, the ride over to the store took about 25 to 30 minutes depending on traffic and time of day. Though today was no different, the ride seemed to last forever. I was so excited but so nervous at the same time. On the way to the Home Depot, I kept gently riding my plug up and down, then trying to get the tip to tickle my prostate. I wanted to be well lubed and loosened up enough, just in case.

"His name is Rick," Ronnie said. "He saw you and I together at the mall a few months ago. I noticed him in the crowd and we just sorta nodded to one another. I also caught his smile and the thumbs up he flashed me. He kinda knew we were together and I could tell he appreciated what he was looking at walking by my side."

Ronnie continued, "I know you've had this fantasy for a while where you meet some random hot guy to fuck you. I know you've also wanted us to explore adding a third to the bedroom now and then. I want to make both of those desires happen but it has to be with someone I trust. I know Rick rather well and I know I can trust him. If this meeting works out and you two do have some sexual chemistry, then I'd like for Rick to be able to join us every now and then."

Ron then looked over at me and noticed me squirming on the plug. He said, "Good boy. Get loosened up for him. Make sure you're well lubricated. He's fairly well hung and I don't want him hurting you if he does penetrate you."

I looked down at my shorts and could see precum leaking through. I was that horny. I think if some decent looking guy were to just touch my cock right now, I'd cum in my shorts. It took every fiber of my being to keep from stroking myself. I wanted to save it, just in case.

Ronnie then started laying out the ground rules for this to take place. First off, there were no expectations of me doing anything I did not want to do. No meant no. If I didn't like Rick, I would not be required to go any farther than the initial meet. This was going to be all about me first.

"Above all," Ronnie said, "This is sex only. In the end, you're coming home with me and will always be in my arms. The only 'I love you's' will be traded between you and I. Rick's already promised that he has no intention of getting between us."

We drove into the parking lot in silence. After exiting Ronnie's truck, Ronnie walked alongside me saying, "I'm gonna go in with you to check out the shades. I'm not going to point out who Rick is nor am I going to walk you right up to him to introduce the two of you. Instead, he's going to find you. I don't know if he's going to come up behind you and just fondle your ass? Or maybe he'll be a little more subtle and accidentally bump into you? Or maybe he'll try to give you a warning that he's somewhere nearby by making your butt plug go off remotely."

When I heard that, I looked over at Ron. I knew I must have had a mortified look on my face. Ron smirked and said, "Yeah, I met with him a few days ago and paired that plug with his phone. Just in case."

Once we entered the store, my head was on a swivel. I was checking out virtually every man there who appeared to be decent looking and probably in his early to mid thirties. That was pretty much all the information I had to go on.

We got to the shades and Ron just started looking through the options available. I was too focused on trying to find who Rick may be to look alongside Ron. Ron found a set he liked and asked me what I thought. All I could do was stutter and mumble. I was so self conscious of the wet spot in the front of my shorts that the precum had made.

Ron told me to continue checking the shades for options I may like. He needed to go find a sales rep to answer a few questions. Then off he went.

I'm flustered by now. I could care less about shades that just a day or two prior, I was saying we needed new ones. No, I was more interested in Rick and seeing my fantasy come true.

Without warning, my butt plug went off. Bzzzzzzzzzz! Though it was supposed to be much quieter than similar plugs, it did still make a little noise. I looked around in horror, hoping no one would hear. I then noticed one younger man walking with a really hot looking man about his age. He was kind of half smiling while looking at my face, then looking down at my back side. I swear he knew I had a toy there because it looked like he was grinning and biting his lower lip. Then he made eye contact with me and my heart skipped a beat. Was this Rick? If so, why would he be there with another man? Ron never said anything about Rick being partnered or my having TWO strange guys just fuck me today.

I eased my back up against one of the displays, hoping the display would absorb the vibrating sound. It also gave me a chance to scout around for Rick. I made eye contact with that really cute guy again as they both walked by. Neither gave a hint that they were going to stop or anything. That younger guy broke eye contact and looked straight at my bulge. No way I could hide the precum that was leaking through the front of my booty shorts.

No words needed to be spoken. He definitely liked what he was looking at just judging by his smile. He made eye contact one more time, winked, then caught up with his partner.

I didn't see anyone else who seemed to be paying attention to me. Once I got over the initial shock of someone possibly hearing me, I began perusing the shades, hoping Rick would make his appearance known soon.

I didn't have to wait too long. I stepped around the corner and walked over to another display. I bent over to read what the tag was saying when I felt a hand brush across my ass.

I thought to myself, "Was this it? Could this be Rick or did someone accidentally brush their hand across my ass?"

I stood up straight and took a step back and stumbled into someone else behind me. I felt one hand squeeze shoulder and another hand squeezed my ass. My heart was pounding hard. I turned around and stammered, "Excuse me...m-m-my apologies."

"It's OK, Brent," a soft spoken voice said. "Hey, look up here. It's me, Rick".

I looked up to where that soft spoken voice was and noticed he had such beautiful blue eyes. He definitely was a decent looking man. I then gave him the ol' up, down, up glance to see what else could be working in his favor. He was well tanned and had the hands and body of a man who had been doing physical labor for the past fifteen years. He also had this cheerful smile that was disarming and just drew anyone in. In just those brief moments, I could see he had a very friendly, easy going demeanor about him. I also couldn't help but notice his bulge and how he had it neatly tucked leaning to the left.

Rick grinned when he saw me check out his cock. "Yeah, Ron was pretty sure you'd like me. Looks like he was right, huh?," he asked.

I nodded as I tried choking out a "yes". I couldn't believe that this tanned cutie would want anything to do with a chubby guy who's thirty years older than he is. And he's a dominant top at that! Most guys like him expect us older bears to be the top.

"I take it I'm right?", Rick asked?

"Oh, hell yes," I replied. "How long have you and Ron been planning this?"

"Only about a couple of weeks. I bumped into Ron at the new coffee shop over on Main Street maybe two weeks or so ago. We decided to have coffee for a few minutes to catch up. I told him I saw both of you at the mall a few months ago and complimented him on his taste in men."

I blushed at that and asked, "Is that when you two decided to surprise me with this meeting?".

"Not necessarily then, no. As we were talking and catching up, it became apparent just how much he cares for you. He told me of some of your fantasies which, by the way, are totally hot! He told me he loves helping you make your fantasies come true. He also told me he loves bringing out the kinky side in you and he wants to push that side of you to consider broadening your horizons. Then we talked about me and how I'm not currently with anyone. From there, we shook hands and left."

Rick continued, "A few days later, Ron IM'ed me on FB. As we messaged back and forth, he told me of his intent to make one, possibly two of your fantasies come true. The thing is that Ron wanted those fantasies to be with a guy he knew and could trust, but not someone you knew as well. Where I'm not with anyone right now and where Ron already knows I think you're cute as hell, he pretty much point blank asked me if I wanted to fuck you with his permission. No way in hell was I going to say no to that chance."

"What about ground rules and all that?" I asked. "What about your previous relationship with Ronnie?" I pressed on.

"First off, Ron and I were never in a relationship. It was more a mutually agreed upon FWB where it was purely sexual and nothing more. We played together for about a year before drifting our separate ways. Ron picked me because he knew I would never violate any boundaries or ground rules he set upon. He knew that I would never violate any of YOUR boundaries as well."

I noticed Rick looking down at my cock. With a mischievous grin, he pulled out his phone and upped the vibrations a notch. He saw my cock twitch in response. Rick looked me dead square in the eye and asked, "It looks like you want this fantasy to come true, don't you?"

I could only nod. The thoughts and ideas swimming through my head right now were overwhelming. Finally. I'm going to be fucked by some random hottie like the little cum slut I have been fantasizing of becoming.

"Come. Walk with me as I pay for these things. Then we can go to my truck and talk in private."

"What about Ron?" I asked. "Shouldn't we wait for him? Maybe he wants to talk with both of us as well?"

"Ron already knows what's up. He disappeared for a reason. He wants this to be completely up to you, whether to follow me and chat in private or not. When we get outside, you can either go back to Ron's truck and that'll be the end of this, or, you can follow me to my truck. It's your choice and there will be no hard feelings at all if you choose to go to Ron's truck."

I shook my head. "Let's go pay then we'll talk in your truck. I'll text Ron to let him know where I'll be."

As we approached the register, the two guys who had walked by earlier were also in line just ahead of us. The guy who had been eye fucking me earlier noticed Rick and I. "Hey, Rick!" he said. "Pick up anything good here?"

Rick looked over at the guys, smiled, then said, "Hey Randy, hey Ben. Yeah, I got lucky and picked out some really good stuff here." He tilted his head in my direction while smiling.

Both guys looked over at me and grinned. They caught Rick's meaning. I stood there a little flustered as these two other complete strangers had an idea what was going to be happening to me.

After Randy and Ben paid for their items, the guy who had been making eye contact with me so many times turned to Rick and said, "Have fun. Do everything I would do!"

Rick just laughed. He turned to me and said, "His name is Randy. The quieter one's name is Ben. I'll tell you more once we get outside. In private."

Rick paid for his stuff and handed a couple of items over to me to help carry out. Once outside, he pointed to where his truck was. It was a truck, all right. It was a semi. That's when he told me he had just finished dropping off a trailer at the old paper recycling plant over in the industrial park. He figured it made more sense to just meet me here in that since this was right on his way home.

We got to Rick's semi and he was actually rather sweet. I'd never climbed up into a semi before so he helped me from behind. Of course, he also gave my plug a gentle push, ensuring it had stayed inside me as I was climbing up.

When Rick got in on the driver's side of the cab, he looked over at me with a mischievous grin. He whipped out his phone and bumped my plug up another notch.

"Ohhhhh, you evil bitch!" I exclaimed as I ground down on the plug without even realizing it. By now, I knew what I wanted and where I wanted this to go.

Rick leaned over to put his phone in the cradle on the dash. Once it was secure, he reached over with his right hand and squeezed my cock. I ground down on the butt plug even harder in order to keep myself from cumming in my shorts right there.

"My mind was made up as soon as Ron finished his proposal. It feels like your mind is made up too, isn't it?"

I could only nod. If this man didn't fuck me soon, I was going to rip his pants off and try riding him right then and there. But I didn't need to go that far.

"Why don't you get back there in the sleeper, then?"

I got up, turned, and made my way back into the sleeper. Rick slapped my ass a couple of times then grabbed my hips and pulled me back toward him. He proceeded to kiss the small of my back, then worked his way down and started biting my ass through my shorts.

"Bastard!" I thought. Fucking Ron told him the fastest way to get my motor running! Now I'm totally defenseless! I don't think I'm going to last very long once Rick gets into me.

Rick released my hips and reached around to untie my booty shorts. He then said, "Ok. Get in there. I need you to get ready to make me cum."

As I was continuing my way back into the sleeper, I felt Rick deftly slide my shorts and underwear down to my ankles. Once I was clear of the front of the cab, Rick pulled both pieces of clothing away from me.

"Lay on your side and face me," Rick ordered.

I lay on my left side facing Rick as ordered, fully exposed, cock rock hard. Rick reached over and stroked my cock very gently. I arched my back toward him and moaned like the whore in heat that I was.

Feeling Rick pull his hand away from me, I heard him say, "Open your eyes and look."

Opening my eyes, I could see Rick's hand in front of my face. My precum was smeared all over his hand. "Clean it off!" he ordered.

As quickly as I could, I licked his hand clean. I've always liked the taste of my own cum so this was another delight for me.

Once Rick was satisfied with my cleaning job, he said, "On your back. Knees up, legs apart. You're about to get your first load of cum for the day!"

"First load of the day?" I thought. "Is he implying more?". Then I remembered what Ronnie has said. If this meeting works out, Rick will likely be joining us for a few threesomes.

"So, does this mean you'll be fucking me again later on today then?" I asked.

"Look at you! I haven't even entered you yet and you're asking for more! To answer your question, possibly. Ron told me that if you enjoyed getting fucked by me this afternoon, I'd be able to come by this evening after dinner for a second round. After Ron fucked you of course."

I couldn't take it much longer. I wrapped my arms around Rick's neck and started kissing him. He pulled the butt plug out of me with a dull plop.

Rick broke the embrace. He told me to remove my top while he proceeded to strip off his jeans and underwear. Once his beautiful cock was free, I proceeded to suck his cock. Just hearing this beautiful man's moaning told me I was having the desired effect. By this time, I didn't care if he cum in my mouth or if he cum in my ass. I just wanted to give him pleasure. I wanted him to come back later that evening, much like he and Ronnie had agreed to.

"Mmmmmm! Oh, daddy!" Rick moaned. "Ron said you were an amazing cock sucker and he wasn't kidding."

Rick abruptly pulled out of my mouth. Before I could ask what was wrong, Rick started kissing me. Hard. His tongue probing my mouth like a hungry animal. As he was kissing me, Rick gently pushed me all the way down onto my back. He crawled over between my legs, then lifted them up until my knees were resting on his shoulders. As he pulled away from our kiss, I could feel his cock head right at the entrance to my ass.

I reached down and got the head of his cock in position. "Now," I said. "Push gently."

Ever so slowly, Rick entered me. He had no problem at all since the butt plug already lubricated and loosened me up a lot.

"Ahhhhh ffffffuuuuuuuccccckkkkkk!" was all Rick managed to say until he was balls deep inside me. Once he had his cock buried to the hilt inside me, he stayed there for a bit.

"Everything OK?" I asked. Now it was my turn to be just a tad bit michievous.

"Ohhhhhh....not a thing, daddy. You're just as tight as Ron had said. I'm just savoring the moment because I'm not going to last very long inside you."

I smiled at that. The thought of a chub like me turning on a stud like him so that he wouldn't last very long turned me on just a bit more.

Rick slowly eased himself out of me until the head of his cock was right at my entrance. "Uunnhhhhhh!" was all he could manage as he plowed right back into me.

I grabbed onto my knees trying to draw them ever so close to me so Rick could get as much penetration as he could. It didn't matter. Rick pulled out then slammed back into me. I could feel his balls slapping against my ass with every thrust. I looked up to see the look on his face. He looked like a wild animal taking his prey. His focus was on his cum and there was nothing I wanted more.