Theoretical Bisexual with Tranny Bobby Joe

I had always considered myself 'theoretically bisexual', but had never had a sexual experience with another man before I decided to come to the bar I was in now. The thought had been growing in my mind lately, and i had found myself thinking more and more about what it would be like. A man sucking my cock. Me sucking a cock. Fucking a man. Being Fucked. I had always thought it would be best to find someone else like me, who wanted to experiment, someone, some man i could fuck without them 'really' being homosexual. I had come to the conclusion, however, that that was hypocritical bullshit. That's what I wanted, what I wanted to do and what I wanted done to me. So rather than pussyfoot around, I had decided to act on my newfound resolve. I was going to go get laid.

I sat in the bar for a while before I talked to anyone. It was a real culture shock, and I began to doubt my rash course of action.I couldn't really see any of these men that I wanted to have sex with. What had sounded so good in theory just wasn't turning the trick in practice. I don't think I fit in really well, and maybe I seemed uncomfortable. So, I started drinking doubles.

Pretty soon I had renewed my resolve, and I noticed a woman staring at me. A real babe actually. Blonde, skinny, big tits, tight black dress. I locked eyes with her. Then I remembered where I was. Logically, I knew that this had to be a guy, but , 'wow'. I stared at my drink for a minute, thinking 'hey, maybe this is what I need'.

"Hi honey." She had walked over to the bar while I wasn't paying attention.

I was super suave. "uh uu hi" I stammered as I stared at her ( him, dammit. )

HE sat down beside me, rubbing his fishnet-covered legs against mine. "I drink paralyzers", he said.

Eventually, I clued in, bought drinks, and talked to him. His/her name was Bobby Joe. He had a 'fuck' look in his eyes as we talked. My cock was rock hard in my pants, and all I could think about was how those lips, covered in bright red lipstick, would feel on my cock. After the bartender turned away from bringing the second round of drinks, he reached over and squeezed my hard on through the crotch of my pants and licked his lips.

"Why don't we go back to my house" He said. I agreed readily and we went out to my car.

We discussed music on the drive to her house, with a lot of inuendo thrown in. References to 'pounding rhythym' , etc. Then, to my surprise, he reached over and started to undo my belt.

"What are you doing ? " I asked, as politely as possible. I was, admittedly, a little blasted, and this was distracting my driving just a tad.

" I'm going to undo your pants and suck you while you drive. I just can't wait that long.." he said. By now, my hard cock was exposed, and he leaned over, sucked on the tip of my cock for a second, and then swallowed my cock whole.

He began the best blowjob I had ever had. His hot warm mouth covered my cock and he roughly fucked me with his mouth, bobbing up and down while he greedily swallowed me. He moaned quietly and made lip smacking sounds as he devoured my cock. In and out of the ring of his lips my cock slid. Soon, it was too much, and I had to pull the car so I didn't crash. I spurted jet after jet of come into his mouth, which he greedily swallowed. After I was spent, he released my cock from his lips and kissed me. It was the first time I had ever kissed a man, and it was incredibly erotic. I tasted my come on his lips as he explored my mouth with his tongue.

"Can you get it up again, lover ? You have to, cause when we get to my house, I want you to fuck me. I want your cock in me, I want you to shoot in my pussy. Can you do that ? Can you make more boycum for me ?" This was the dialogue on the rest of the ride. While he talked dirty to me, his hands fondled my flaccid penis, which he had never bothered to put back in my pants. As we drove into the parking lot of his building, my cock was fully erect. Just before we got out of the car, he gave my cock a quick kiss.

"You're a virgin aren't you ? " he asked as we rode the elevator. I knew he wasn't asking if I had ever fucked a woman.

"yes." I answered.

He snuggled up against me and kissed me. "That's sweet. I love breaking cherries. then he did something completely unexpected. Out of his purse he pulled a tube of K-Y, and handed it to me. Then he bent over and flipped up his skirt, revealing no panties, and garter belts holding up the fish nets.

"Grease my ass. Stick your fingers in me" he said. I was shocked. I mean, right here in the elevator. But, I quickly squirted some K-Y on my finger, and applied some to his exposed, puckered asshole. It was neat and hairless, and I was incredibly aroused as I slipped my middle finger up his ass, making him groan. I was so tempted to pull out my cock and fuck him there, in the elevator. I wanted to fill his hole with my cock, to come inside him, to feel his stockings against my legs as I drove my cock into him.

I fucked two digits in and out of his ass while we rode up two floors, then, just as the doors opened, he pulled forward and stood up. There was no one there.

After he opened the door, we went straight to the bedroom. He lay back on the bed and spread his legs wide, dress pulled up around waist. His cock stood out, an erect six inches oozing precum. Just like he was a woman, I pressed my cock against his whole and slowly fucked my cock into his slick ass.

He groaned and stiffened when I penetrated him. His ass was like the best cunt I had ever been in. It was tight and hot and hugged my cock. Slowly, I increased speed, fucking him with greater urgency. My belly rubbed against his cock and I could feel his sticky precum on me.

"Yes. Fuck my ass. HARD. mmmm. Come in me. Shoot your cock off in my ass" he groaned as I fucked him. And I did. I came , shooting hot come up this guys ass. It was my first fuck with a man, and my orgasm was twice as powerful as it was when he sucked my come. I kept coming and fucking and coming and fucking and slamming into his ass, filling him with my organ and my seed. I was still coming when my cock slipped out of him and sprayed his groan and belly with streams of come. At last, I collapsed on him, trapping his erect cock between us.

After a minute or so, he rolled me over on my back.He got up, took of his dress, and removed the falsies he had been wearing, but kept the translucent teddy he wore beneath. He was hairless all over, and his skin shone with fuck sweat. I waited in anticipation, and not for long. He straddled my chest, planting his knees on the bed just under my armpits.

"Now I'm going to sit on your face. Open your mouth so I can fuck it ! " He instructed. I was overcome with sex. I opened my mouth eagerly, and got my first taste of cock. He fucked my mouth just like it was a cunt, sliding the first four inches or so of his cock slowly in and out of my lips. I moved my head along with his hardon, and after adjusting, was able to get a whole lot of it in my mouth. I sucked, and licked, and did everything I could to make him come. I tried to give the blowjob I always wanted. I was overcome with the eroticism of this man, dressed as he was, fucking my mouth, me sucking him, gripping his fishnet clad legs as he drove his cock into me. I wanted to taste his come, feel him come as he spewed come into my mouth, to swallow his pleasure.

That was not to be. He withdrew his cock and looked at me. "Do you want to finish like this, or do you want to roll over ? ". It was a hard decision. I wanted his come in my mouth, was caught up in the blow job, and was nervous about being fucked. But that was what I really wanted. I wanted the whole deal. Tense, I rolled over onto my hands and knees.

I didn't feel the cock against my anus like I expected. Instead, I got a shock when I felt Billy Jo's tongue on my ass. He licked all around it, then began to fuck his tongue in and out of my ass, slurping as he rimmed me. My cock began to harden again as i felt these wonderful new sensations on my ass.

Then I felt his lips leave my hole, and felt the cool slickness og K-Y on my ass. Slowly, he pushed a finger into my tight, virgin ass. I groaned into the pillow as he began to fuck me with his hand, massaging my prostrate with his finger.

"Do it, " I moaned, "Fuck my ass. Take my cherry. I want it."

He got behind me, and I felt the tip of his cock against my ass. His cock wasn't very big, maybe six inches long and as thick as mine, so I wasn't terrified or anything. It was very uncomfortable as he slowly penetrated me, but I bore down and tried to make my ass loose for him. When he was fully in, he stopped for a moment and leaned over, and asked me if I was okay. It didn't really hurt anymore, and I wanted to be fucked. I wanted him to come in my ass, to come like I had come. I wanted the good part of being fucked in the ass, and wasn't afraid of a little initial discomfort.

"Yes. Fuck me. Fuck my ass. Come in me."

He began to slowly work his cock in and out of me. I was stretched, but I felt deliciously penetrated. I was being fucked. I was kneeling there, passive, while this beautiful creature slid his cock in and out of me. He talked dirty in my ear, but I wasn't paying much attention. THe cock in my ass was my world, and I could think of nothing but the sensation as it slid in and out, fucking me, taking me like a woman, driving his cock into my hole. It was out of this world, an unbelievable new sensation.

His fucking became more frantic. He clutched my hips and began to fuck me hard, too hard in his passion. I whimpered in pleasure/plain beneath him as he roughly thrust into me and came in ass, spewing hot come in my ass. I could feel each jet as he exploded into my ass, still fucking my hole lubricated with his semen.

He rested on top of me for a moment, and then reached around to grip my hard cock. "Let's go take a shower", Billy Joe said, leading me by my hard cock to the bathroom.

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written by anonymous