A Life Imagined

"That day when I hurt my knee you held my hand. It was the first time a guy had held my hand and I never forgot you."

What could I say? I didn't even remember that part but I didn't care because he was here. He was on my couch and I was in his arms. Before he could say another word, I leaned into him and we were kissing again.

"Just so you know, I've never done this with a guy but you, you are so damn pretty." I was looking into his eyes when he said that and I could feel myself melt and my little cock begin to drip.

Phillip began to get up from the couch but not before scooping me up in his arms. I instantly wrapped my arms around his neck and released my kiss. My mouth suckled his neck as he walked into my bedroom with me in his arms.

He had a men's cologne and a musky sweet smell. My God I can still remember that scent even now as I type these words.

This was the moment that I'd been waiting for and it felt so good. He put me down on the bed and I sat up on the edge. Phillip was in front of me and started fumbling with his belt and his pants. I was so eager that I'd lost myself in the act. I finally pulled his pants down to his knees and in front of me was his gorgeous cock.

The head of his cock looked big and the shaft of his cock was thick. His balls were full and they were nestled on a well-trimmed bush of blonde pubic hair. Taking it in my hand I couldn't get over how heavy it felt. Before I could overthink it, I slid his cock into my mouth. The muskiness of his crotch, the scent, it was too much. I moaned...

I had researched it to death, I'd seen gay porn, and read the articles and now I was putting my knowledge to the test. I suckled his cock allowing my tongue to slather the underside of his cockhead. I slurped the excessive saliva, swallowing it. I couldn't get the head past my gag reflexes but he didn't seem to mind.

After a few minutes, he had my head in his hands, and now he was moving his hips. He was fucking my mouth. I couldn't help but moan and slurp up the precum and saliva. His grip on my head begin to tighten and his breathing started to become erratic. He wasn't going to hold out much longer.

That first rope of his semen hit the back of my throat and laid flat on my tongue. I jumped the instant he did it. Then another and another, I swallowed. Another and another, I kept swallowing. Finally, he was starting to slow down. I was able to hold his last few shots of semen in my mouth. I wanted to savor it, to taste him.

Looking up at that handsome face I opened my mouth so he could see how full it was with his seed. Then I closed it and took a big swallow. He was done. He pulled up his pants and kissed my forehead. Told me how nice it had been to see me. He politely excused himself and I got up to walk him to the door. And that was that.

When I closed the door behind him, I leaned my back against the closed door and couldn't help but laugh. I'm sure Phillip enjoyed his blow job and probably felt like he'd gotten one over on me. The fact was I had allowed everything to happen. He wasn't some stranger and he was very handsome and very much worthy of my first blow job. Plus, for him to just get up and leave afterward without any real conversation made the whole thing perfect. Just perfect.

~~~~~~~~~~~~~~~

Enough of that.

Work was finally over and I finally made it home. I was exhausted but soon I'd be on the couch and going over some of my medical books for the upcoming fall semester. I wanted to be ready for the new semester and get a head start. Turned out that maybe my body wasn't into the idea of a head start. It didn't take long for a minor headache to set in and I knew I had to stop and get my mind right.

I jumped in the shower and let the water fall over my back as I leaned forward against the shower wall. The water was as hot as I could stand which to some may seem scalding. For me, it was the right temperature and I was quickly overcoming my brief tension.

Growing up I hated my body then as I got older my attitude started to change. I have my mother to thank for that. After that disaster of a prom night, we started to get a deeper connection. Then when I came out to her, she decided that I would be the daughter that she'd always wanted.

She wanted me to buy clothes that fit my body type. The only problem with that is that clothes that fit my body type are women's clothing. Young Miss to be more precise. It's something that I kept going back and forth with. I'm a gay man and not a trans woman. But she was right. Because of the circumstances of my pubescent years, I was left with a very feminine body.

So, it stands to reason that I look good in clothing designed for women. Still, I haven't worked up the courage to go out in public dressed in that style of clothing.

But in the safe comfort of my apartment it's different and tonight I wanted to feel pretty. I wrapped a towel around me after my hot shower and set off on picking out something comfortable to wear. I go and pull out a nice pair of pearl white satin short shorts. Hip huggers basically with loose leg openings. The waistband is nice and tight around my hips and the leg openings are baggy enough that they barely cover the curves of the bottom of my ass cheeks. A true definition of cheeky. A nice matching camisole top and I should look and feel great. After I dry off and finish with a nice scented lotion over my legs and bottom and allowing that to dry off, I slip my shorts on.

I blow dry my hair and then slip over the camisole top. Looking at myself in my full-length mirror I can finally exhale a sigh of relief. Yes, I do look and feel great. Checking myself out, I turn and see my ass cheeks peeking out of the bottom of my shorts. My camisole hanging on my perky nipples as they make themselves noticable. Nice, I think to myself.

Making my way to my vanity table, yes, I have a vanity table. My mother bought it for me and I couldn't tell her to take it back could I. Checking myself in the mirror I decide to go all the way. I've taught myself the fine art of makeup, not a lot, nothing flaming but just enough to satisfy my urge. When I finally finish, I find myself horny and starving.

That's when I do what I do best, fuck with the pizza guy. I order myself a pizza and make sure that I look really good. I love fucking with the pizza guys when I doll myself up like I've done tonight. The look on their faces when I open the door is priceless.

As I sit on the couch checking out my nails, I start to feel like I have such a sad life. I'm a gay man but I refuse to be sexually promiscuous. I could drop my moral compass and go to the peep show rooms and leave the door unlocked and just suck cock there.

I could go to the truck stops and maybe find some truck driver to fuck me in the shower rooms or his semi. Then again, I could be classy and just give my ass away on Tinder or any other social app. No, not me, I can't do that. And don't start with me sucking Phillip's cock! As I said, I knew him.

The loud banging knock startles me.

I jump with excitement when I hear it. I couldn't wait to see the look on the delivery guy's face when I open the door looking like I do tonight. Running into my room to check myself one last time. Turning to look over my shoulder at how great my ass looks in my satiny hip huggers, I was set.

When I opened the door, my heart almost jumped out of my throat. Standing next to the pizza guy was the chef. I froze, and there I stood, wearing clothing that barely covered me. Everything from the small amount of blush on my cheeks to the little touch of gloss on my lips, there I stood. I was freaking the fuck out! Without skipping a beat, the chef stepped up.

Reaching into his pocket he pulled out a money clip and slipped the delivery guy a $10 tip and grabbed the pizza from the gawking pizza guy.

"Have a good night kid, the show's over."

With those words, he stepped into my apartment and closed the door behind him. I was speechless. For a whole second all I could do was stutter. What do I call him I thought to myself, all I've ever called him is the chef or Chef? He must have seen the confusion in my head with the backlog of thoughts fighting to verbalize themselves so I could say something, anything! Fuck!!

"Jack, baby. Say, hello Jack...how's your evening, Jack?"

Placing the pizza down on the coffee table I was still regrouping mentally. I could tell that he'd just showered; his hair was still wet. He was wearing old biker boots and old worn jeans. A t-shirt with some old rock band's name across the chest along with a black leather jacket.

His jet-black hair and trimmed 5 o'clock shadow on his face. His gorgeous smile, all of him, I was taking in all of him. Still, how did he find out where my apart...

That's as far as that thought went. Grabbing my hand, he pulled me into his arms, and just like that he was kissing me. I was on my toes sliding my arms around his neck and he was bending down to meet me halfway. There I was in what I'd been fantasizing about for the past two years. Dressed how I liked to dress, flaunting it for the man that I wanted in my life.

I loved how, "Jack," kissed me. He was passionate, slow, and responsive to my reactions to his kisses. He slid his hand under the waistband of my shorts while his other hand had made its way under my camisole, finding my breast, my puffy nipple. He had me, and God help me. So many questions ran through my mind but for the life of me, I couldn't think of any one question to ask.

His hand was no longer just inside my waistband he was pushing my shorts down and groping my ass. When I finally felt the waistband slip past the curve of my ass cheeks I moaned. He stopped manhandling me long enough to pull his jacket off. I went for his t-shirt and pulled it up over his head, tossing it on top of the jacket on the couch.

I was in awe of what I was looking at. His chest was like a bodybuilder's. Well-developed pecs, his traps, his biceps, and abs, all of it, defined to perfection. Add to that, his chest is covered in thick black curls that just beckoned me. I found myself stepping into him and kissing his chest through those soft wonderful curls. Then he stopped me.

My shorts had fallen to my ankles at that point and he took a step back to look at me. I was terrified at that moment. Was he going to laugh at me? There was no compression shirt to make me look flat-chested. Were my breasts going to become the deal-breaker that sent him walking out the door? I felt like a total freak show, I was so scared.

"My god baby, you're gorgeous." He said as he lifted my blouse to suckle my breast. First one and then the other before allowing my top to drop back over my breast. He stepped back to look me over again.

"You're perfect," he said with a look that told me that my breasts were fine, no, they were perfect.

I was speechless. Then he started looking around my apartment. I stepped out of my shorts leaving them on the floor. I led him to my bedroom, turning on the lamp next to the bed. I sat him down and dropped to my knees to take off his boots. Placing them neatly next to my nightstand.

Standing him up I unbuckled his belt and his pants. Dropping them down, allowing him to step out of them. Folding his pants and placing them on the bench at the foot of my bed I pushed him back, sitting him down, moving between his legs. That was all that he needed. He took over from there and began kissing me again while palming my ample ass. While he entertained himself with my ass I pulled my camisole over my head and tossed it on the floor.

I could tell how much he loved my ass by the way he massaged it and kneaded my ass cheeks. Pulling them apart exposing my pink asshole to the cool airconditioned air. He picked me up in his arms and laid me on my back moving his knees between mine.

"Tell me you have lube baby girl."

I gave a pouting glance towards my nightstand without saying a word. He smiled and kissed me again before making his way over and pulling the lube from the top drawer. I lay there terrified of what I was about to do. How well did I know Jack? Other than work and sneaking around like a love-struck couple I didn't know him, not really.

Then I started to rationalize in my head that this wasn't some one-night stand hook-up. I mean, he's been chasing me for almost a year now. I told myself that I wasn't being stupid. I knew this man and he may not be what I end up with but I can allow this to happen.

With all these thoughts running through my mind I never took my eyes off of him. I watched him in awe as he squirted a generous amount of lube over his thick shaft. I had unknowingly begun to spread my legs for him and pull my knees back. I rolled my hips so that my virgin hole was angled up for him to access with ease.

It must have been a sight because the lust in Jack's eyes was beyond intense. I had positioned my left hand above my head flat on the mattress palm up and my right hand was palm down with the tip of my pinky in the corner of my mouth. I had begun to nibble on it while I watched him.

He positioned himself between my legs and I finally felt the tip of his rock-hard cockhead pushing against my hole. He didn't say a word, he just grunted. I yelped and exhaled at the same time. The head of his cock had broken my seal, he was inside me. I started to hyperventilate and Jack froze. He allowed that piercing moment to pass.

My eyes closed and my feet dangled in the air contorting while my toes curled uncontrollably. He pushed again, and again I yelped. He pushed again, and I squealed. Again, he pushed, and this time I moaned. He started sliding his cock back and forth in small gentle strokes. I lay there, mouth wide open, moaning with each sensation his wonderful cock was giving me.

He started going deeper and I instantly slid my arms under his arms and around his back. Pulling his body closer to mine. His knees kept nudging my legs further apart but more importantly not allowing my legs to close. I dug my fingers into his back and my toes into the side of his hips. This was all he needed, his balls were against the bottom of my ass, and he had finally pushed in all the way.

Pulling his cock all the way out to the tip of its head and slamming back into me all the way made me yell. But this only emboldened his lust, he did it again and again and again until he was in a hard steady rhythm. Jack was fucking me and I was hanging on. I could feel his cock rubbing over and over my prostrate, the feeling was too much.

I didn't want to cum so I thought about anything and everything else while this man fucked me. Don't cum Joseph, don't cum I kept thinking over and over as I gritted my teeth and dug into him harder while spreading my legs as wide as I could spread them. I was kissing his throat, his chest, his shoulder.

"Joey, pleasing a man isn't the same as pleasing a woman baby."

What the fuck?? I was hearing my mother's voice in my head as if she was there! Oh my god! Was that all that I could think of? Really?! Jack grabbed my legs and threw them over his shoulders. My attention went back to him, no more thinking of stupid shit. I was screaming now...

"Oh my god, Jack!! Oh, my fucking god!! J-Jack, J-Jack, J-Jack!! Oh babe, oh babe!"

I was screaming out and he was balls deep inside of me with his face buried into my neck grunting and growling. That was all that I could handle and I started spewing load after load onto our stomachs and chest. My body was quivering uncontrollably while he kept going. Jack kept fucking me for another half hour or so until he finally rolled me onto my stomach.

I didn't know how much more I could take until he shoved back inside of me. It took him another half hour or so and once again I was screaming. This time my screams were muffled by my mattress and instead of digging my fingers into his back, I was digging them into my bed. Jack let out a series of loud grunts, each one with a matching thick stream of his semen spewing deep inside of me.

As soon as I felt his cum, I came a second time...

I felt as if I would pass out after my second orgasm. When I came to my senses, I held on to him. His cock would twitch sending shivers through my body each time.

I don't know how long he lay on top of me but it was a feeling that I didn't want to end, and then, it did. He rolled off of me, my thoroughly fucked hole making a gentle gurgling sound as his cock pulled out of me. He spooned me and held me tight. Neither of us speaking, I clenched my hole shut because I wanted his cum inside of me forever.

Then I passed out. When I awoke, I was alone in my bed and Jack was getting dressed. Rolling over on my side I couldn't help to think, what the fuck? He's leaving?

"You're leaving?" I asked in soft protest.

"I am, baby doll," he replied as he flashed that gorgeous smile.

"Why? Stay with me," I partially begged.

"I can't, I got shit to do and I can't put it off." He replied.

He stood up and came over to me. He leaned down and I rose to meet him halfway. He kissed me.

"Joey baby I need you to be patient, ok?" I seductively blinked, nodded, and whispered, "Yes sir."

"Now get up and lock the door behind me. Where are your shorts, honey?" He asked as he looked around my bed.

"In the living room, on the floor where you dropped them," I answered seductively.

In a quick second, he'd gone and brought them back to me. Handing them to me along with my top and kissing me again.

"Get dressed baby, walk me to the door so you can lock it."

I did as I was told, slipping on my shorts, pulling them over my ass before standing up. I didn't bother with my top, leaving it on the bed.

I had to gather myself for a moment because I could feel his seed trying to drool out of me. That wasn't happening, I thought to myself. I gingerly made my way behind him as he pulled me along by the hand. We stopped at the door and kissed one last time. Then he was gone and I turned out the lights and got back in bed.

I lay there, in my bed finally allowing his cum to drip out of me. I could feel it becoming smeared against my ass and shorts. My ass, becoming a mess and I loved every minute of it. I don't know where this is going, this thing with Jack and I, who knows.

For now, it was finally starting to become the life I always imagined...