Lost My Virginity to a Bear Trucker

This is a true account of my first gay experience. I'm 32 years old, 6'3", with an average build. I don't have the chiseled chest nor the beer belly. I exercise a few times a week and take care of my body. People tend to find me attractive as I've been hit on by both women and men in the past.

Now, I never thought of myself as gay or bi, but I have been curious for several years now. So much so, that I tend to find myself watching gay porn more than straight porn nowadays. I even went so far as to purchase a butt plug and dildo online to try out and see if it is something I would like to experience. After a few weeks of playing and I'm embarrassed to say, online research; I was finally able to not only wear the butt plug for several hours, but also take the 8" dildo balls deep! I rode that rubber cock for less than 2 minutes before I was cumming all over myself! I have since made riding my dildo and watching gay porn a weekly thing. Not to mention wearing my butt plug out on shopping trips and sometimes at work.

Now everyone has a type, and I was quite surprised to find that I am most attracted to older mature men. Not just older men, but large men; fat bear type men. The large bellies and barrel chests just turn me on to no end, not to mention the large cocks!

I work at a retail warehouse and I'm around truckers and 18 wheeler almost daily. On occasion I have to go out on the "yard", and do trailer seal checks. It is a boring job checking 200 plus trailers to make sure they are sealed, but I have several hours to myself and I get to chat with over the road truck drivers now and then.

So it was a Thursday afternoon and I was out on the yard when I noticed a lone over the road driver with his cab parked in the wrong area. I walked to the cab and knocked on the door but got no response. The curtains were drawn closed and it is not unusual for drivers to take naps and get a little rest while they wait for their trailers to be unloaded. I waited a few more minutes then knocked on the sleeper compartment door and waited. I notice the cab start to shift and realized I had just woken this man up. The curtain drew back and the door opened up and there in front of me was a gorgeous bear of a man. He wore only boxers and I could clearly see this large erection through the thin fabric. He was a good 6 foot tall, and easily 280 lbs. And I couldn't take my eyes off of him. This is the man of my dreams, my fantasy in flesh!! He asked if his truck was finished and I couldn't seem to form words to answer him. All I could do was stare at his body and cock. I finally came to my senses and respond to him and told him he was just parked in the wrong area.

He told me his name was "Barry", and he just wanted some privacy away from the other drivers. I told him I understood that it could be hard to sleep out here with all of the noise and the drivers adding even more to it. Barry said he just wanted some privacy so he could get off! My jaw about hit the floor when he said that. I could see Barry's large cock throbbing and spitting hot cum in my minds eye and I immediately got hard. I guess Barry noticed as well, for next thing I know he is inviting me into his cab. I was so drunk on lust that without a word I took his hand and climbed in.

Barry led me to the sleeper cab (which is surprisingly a lot bigger than I thought) and told me to get comfortable. The cab is basically a mattress with a small tv/dvd entertainment stand. I was taken back a bit to see two guys sucking each other off on the small screen. All self control I had melted at that moment as I wrapped my arms around this large man and kissed him long and deep. It's funny, I thought kissing another man would be rough, and unpleasurable; but here I was with my tongue darting into his mouth and kissing him. I could feel Barry's hands rubbing over my chest, working my shirt off. I stopped kissing him and started undressing as fast as I could. Within seconds I am completely naked! Barry pulls his boxers off and I get to see his beautiful cock in all of its glory. I'm in heaven!!

Barry starts rubbing his hands all over my naked body and I can feel myself getting lightheaded. I stop him and explain that I want this to happen, I want it to happen real bad; but I have never done this before and I'm a little scared. He reassures me that he will be very gentle and take things slow so that we both enjoy what was to come. I shook my head yes and Barry gently pushed me on my back and ran his hands over my chest. His large hands caressed and squeezed my nipples, causing me to moan. He then took my right nipple in his mouth, and with his left hand gently squeezed my cock. I swear I almost shot my load right then and there! Barry continued to suck and play with my nipples while at the same time he stroked my cock. I couldn't believe how wonderful this felt! Barry slowly kissed his way down my chest and stomach until he was at my cock. Barry looked up at me and with a grin took my cock into his mouth.

Once again, I'm in heaven! Barry sucked my 6" cock all the way down his throat and back again, working his tongue on the tip and underside of the shaft. He had one hand on my cock and the other was working its way to my ass when I realized I still had my butt plug in! Barry reached my hole and felt the plug. He stopped sucking my cock and looked down, I was completely embarrassed. What was this hunk of a man going to think, would he still want to be with this freak that wears butt plugs to work? Oh the scenarios that were running through my head. Suddenly I felt a tug on my ass, I opened my eyes to see Barry pulling at the plug with a huge smile on his face. He must have seen the confusion on my face because he explained to me the his cock is 10 inches and with me wearing the plug all day my ass should be more inviting to his cock. Relief and excitement overcome me at that point as I realize I was holding my breath the whole time.

Barry goes back to sucking on my cock, but at the same time he starts to pull my plug out then in again; out then in again. Oh Wow!! It only takes a few minutes before I shoot my load. Barry opens his mouth and shows me that he didn't swallow my cum and moves up and kisses me. I get to taste my first load of cum as Barry transfers my load from his mouth to mine; I swallow every bit of it. Barry sits back and asks me how I liked it, I'm so spent I can't form words; I just move towards his cock and start sucking on it with everything I've got. Barry lets out a chuckle and tells me that I'll get better with practice but a 10 inch cock is not a good starter cock for my first time. I just wrap my lips around the head of his dick and swirl my tongue around the slit and underside of his shaft for a little bit until he is fully hard.

Barry pulls away from me and grabs a bottle of lube off the shelf next to the tv. He tells me to lay back as he folds a pillow in half and puts it under my ass. He pulls the plug out of my ass and lubes up his fingers and starts inserting them in my ass. First one finger, then two. On the third finger I tense up and Barry tells me to relax. He tells me to bare down on his fingers like I'm taking a crap and they will go in easier. I completely trust this man I just met and do as instructed. In they went, no objections; no pain. Barry works my hole with his fingers for a few minutes the pulls them out. I know this feeling of emptiness from playing with my dildo, but plastic feels nothing like actual flesh. I wanted more, I needed more; I wanted Barry's large cock.

Barry asked me if I was ready and I acknowledged that yes I was ready! He lined his cock up and slowly pushed the head against my waiting hole. I did as Barry said and bared down, and with a pop the head of his cock was in my ass! I would be lying if I said it didn't hurt, because it did. Barry being true to his word just left his cock the way it was. Slowly I started getting used to this large intruder inside me, and I longed for more. I nodded to Barry that I was ready and he slowly started working that marvelous cock in and out of my tight virgin hole! Man the sensations I was feeling from Barry's cock was truly out of this world. I started to moan so loudly I was afraid we would be heard back in the warehouse. I didn't even recognize the voice, even though it was coming from me. I was wanting more, and I wanted it harder, and faster!

Barry pushed my legs up on his shoulders and started spearing his cock in me. He would pull out all the way to the tip of his dick then slam back into me. By the third stroke my cock was shooting cum all over my belly; I hadn't even touched it! Like a hungry cum whore I licked up every last drop. Barry continued fucking my hole for a few more minutes before he pulled out and told me to climb on top of him. His large cock felt so much bigger with me sitting on it than ever before, and the sensations were multiplied. I was in control this time, I could determine how deep and how hard I wanted it. But most of all I could control how much Barry's cock milked my prostate.

Barry moaned and said I ride cock better than any woman he had ever fucked! I could not believe it, my first gay anal encounter and I'm already riding cock better than a girl! Barry allowed me to ride him a bit longer before he expressed that he wanted to cum. I dismounted his cock (once again feeling empty) and he positioned me on my hands and knees doggie style. Barry got behind me, lifted his belly up and rested it on my ass. I found that so hot, I was definitely attracted to fat/bear type men. Barry lined up his cock and rammed it in my stretched hole. God, it felt so good to be full again! Barry plunged in and out of me repeatedly, picking up speed with every thrust. I could feel his balls slapping against mine, but best of all I could feel his cock as it slid across my prostate.

My god the feeling! I never wanted this man to stop fucking my ass. I wanted to spend the rest of my days impaled on his cock. I could hear his moaning and breath quickening; and knew he was close to blowing his load. I started thrusting back at him and within seconds Barry was shouting he was about to cum. I could feel him trying to pull out, but I wanted to take his cum. I wanted to feel him shoot inside me! I thrusted back on Barry and shouted for him to cum in me, to make me his bitch; that must have done it because I felt Barry's cock tense up and start to spasm deep inside of me.

I could feel every jet of cum as it splashed deep inside my ass. Barry collapsed on my back spent. I could feel his cock going limp inside me, and felt a little sad that it was over. Barry finally pulled out of me and pulled me into a tight embrace. He spun me around and kissed me long and deep, like I was a long lost lover. We held each other for a good while longer before we finally broke the embrace and started to redress ourselves.

We were both startled by his CB radio coming to life letting him know his trailer was empty and ready for pick up. We exchanged numbers and agreed to meet up again as soon as possible. I left Barry's cab, and went back to work. Needless to say, I didn't get much done that day.

It has been 4 months since my first encounter with Barry, I have since quit my job and ride with Barry full time. We spend a lot of time in the back of his cab and I can't think of anywhere else I would rather be. I in my bear's embrace with his large cock up my ass is like heaven on earth, and I just can't get enough!