A Life Imagined Ch. 02

I had spent my entire life trying to prove my masculinity and all it took was one glorious summer of just being myself to come to terms with who I was and what I wanted to be.

I wanted to be free of all the labels either given to me or imagined in my mind. I wanted to be free of having to hide, hide how I felt, how I wanted to love, and how I wanted to enjoy life.

That summer with Jack turned into a bittersweet summer. Let me start with the sweet.

Jack became a regular visitor at my apartment after that first weekend. At first, it was Saturday nights only then he’d show up on a Wednesday. Then he’d spend the weekends and by the end of the first months, he’d moved in.

Sex with Jack was always a new adventure for me that month. No matter what he did to me it was all new and exhilaratingly wild for me. That first month he’d fuck me for hours. If he wasn’t fucking me, I was sucking his cock. It was all so new to me that at times Jack had to push me back.

“Calm down tiger, you’re draining me of my superpowers.”

Yes, I was draining him of his superpowers but what Jack didn’t know was that I was gaining superpowers of my own.

When I was around Jack, I didn’t have to hide my body or feel like a freak of nature. I’m sure that may seem funny or odd to you. Let me try to explain.

I am a man and yes, I have a penis. Medically speaking it’s called a micro-penis. I also have breasts. Not fat chubby dad boobs or fat boy boobs. I have very perky, size-A breasts or cup size, should I say.

Being a male and having breasts is known as gynecomastia. This occurs commonly in older men or obese boys/men. Or, in my case, something that happens at puberty. Most of the time this issue works itself out. In my case it never did.

From the onset of puberty, I never received the jolt of testosterone. Instead, my hormones were dominated by estrogen and little testosterone. Because of this, I’ve been a man trapped in a very feminine body. Hence growing up feeling like a freak, trying to prove my masculinity over the years.

Now not only was I finally living my sexuality, that of a gay college guy, but I was also finally enjoying having a body that was appreciated. One that I didn’t have to hide.

I’ll never forget…

I had collapsed on top of Jack this one night. It must have been two or three in the morning. I slowly slid my ass up while his semi-hard cock was still inside of me when I caught him staring at my breast.

“You have creamy white skin and it’s so smooth,” he said in a soft low tone.

“I’ve never seen you shave any part of your body. The peach fuzz on the small of your back and all over your ass is so perfect it makes me want to kiss it all night.”

His words made me moan and uncontrollably roll my hips back until I could feel my ass cheeks pressing down on his massive balls. I could feel his cock inside of me twitch.

“But your breasts, oh my god baby, your breasts.”

My hands grabbed a hold of his biceps, I arched my back and my head tilted back. My hips started to roll slowly, sliding his thick cock back and forth inside of me. He moved his big, wonderful hands over my ass, cupping it with those powerful hands.

I had started to fuck him but with his hands, he was controlling me. He knew that his words had triggered me, and I knew that my tight pussy, his word not mine, had triggered him.

“Your breasts look like a desert baby,” he started speaking again in that low sexy voice of his.

“Creamy white skin, like vanilla ice cream. Your areolas are nice and puffy, the size of an old half-dollar coin, and the color of cotton candy. Your nipples are as big and the same color as raspberries.”

That was all it took, I had already cum early in the evening but his voice, his words, and his hands dug into my ass. I couldn’t take it.

I felt that pain from deep inside, from my prostate, I was going to cum. And I did, all over my stomach and his. Some of my squirts hit his chest. I moaned out loud. I sounded like a young woman, squealing as I collapsed on top of him. My cum, trapped between us.

The next day I went shopping for bras and never wore a compression shirt again. I felt empowered and wasn’t going to hide whom I was becoming. Don’t misunderstand me. I have no desire to be a woman. I’m incredibly happy with my tiny penis and not having to worry about a menstrual cycle. Not having to worry about being told what I can and cannot do medically with my body.

I have the utmost respect for women. But I don’t want to be one, I just want to be me.

By the second month, Jack and I started going out in public together. Come to find out, Jack is bisexual. Not scared to say it or live it. His preference is feminine gay guys. Femes, traps, sissies. He hit the lotto with me.

Still, he was odd in that when we went out, we’d go out of town. We’d travel to nearby Portland where there is this cool club where we’d hang out. Behaving like a normal couple that couldn’t keep our hands off each other.

When I asked why we had to go so far to be together in public he started taking me to his billiards nights and bowling league nights. Those nights I understood why we’d go out of town. It was for me, not him. In the beginning, I was nervous and scared. Who would see me dressed like I was? What would my family say?

When I started flirting with Jack all those months ago, I had shoulder-length guy hair. I wore a compression shirt to hide my breasts. Dressed and acted every bit of a young man of twenty.

At this point in our relationship, I had gotten my hair cut in a metrosexual or gender-neutral cut, a boy bob. My old color was what is called dirty blonde. Now my hair is ash blonde with platinum blonde highlights. I had started dabbling with make-up. Nothing flaming or outlandishly gay.

Just typical makeup that any of my girlfriends would wear on a casual night out. I wasn’t wearing only regular guy clothes anymore. I started wearing blouses, tops, jeans, and shorts from the young miss departments of the local boutiques and box stores.

Again, nothing flaming. Unless you knew me, you’d never be able to tell that I’m a guy. I know my boundaries and luckily for me, they’re a bit on the conservative side. Privately? Privately I have a different style.

Privately, Jack was treated to seeing me in teddies, camisole, and matching shorts. I love wearing silk and lacey panties. My penis is so small that I wear panties all the time and you can’t even notice my little guy.

That second month with Jack I began to blossom, and I loved every minute of it. Almost as much as sucking cock, and I love to suck cock.

I was at a coffee shop, and I ran into an old friend. We’d gone to high school together. I sat down in my normal spot to catch up on my emails and this guy couldn’t stop staring at me. I was in a white top, yes ladies’ top, and running shorts. Nothing crazy unless you knew me from years ago and are just now seeing me with breasts.

His name is Dawson and he played on the basketball team. I’d taped his ankles up so many times his senior year he had to know who I was. I didn’t understand his hesitation to say something to me.

“Joey?”

He’d finally gotten the nerve to say something. And here he stood. All six foot eight of him. He’d accepted a scholarship from our local university and was a year ahead of me.

I looked up and gave him my sweetest smile allowing my tongue to barely pass over my bottom lip.

“Hi Dawson, how’ve you been?”

He stood there with his mouth open trying not to stumble over his next sentence.

“Oh wow, it is you. I hardly, um, I mean, I almost didn’t recognize you!” He finally said with a gleeful smile.

With that, I offered him a seat at my table and he gladly accepted. He kept telling me how he’d seen me before on campus but hadn’t said hello before. He’d always been in a rush he claimed.

Of course, I knew why he’d finally gotten a moment for me, and I had to bring it up.

“Let me guess, you’d never really noticed my cute, perfectly round, sweet…” I paused for effect.

“Eyes? You’d never noticed my eyes before?”

He laughed and so did I. The elephant in the room was gone and now we could talk. Like a couple of guys that used to go to high school together back in the day. Dawson is a good ball player, but he’ll never go pro. Instead, he wants to get into coaching or maybe become an agent.

It was a nice little conversation and he finally had to run but not before getting my phone number. Later that night Jack had let me know that he would be out of town for the night. That’s another thing, Jack would disappear for days at a time. But that’s a story for another time.

Dawson called me up and I ended up inviting him over to my place to hang out. And yes, I sucked his cock. Dawson was every bit as nervous as I was. I’d only sucked two other cocks in my life. Something about Dawson intrigued me. Here is this giant of a guy that’s as white as I am. Was his body parts proportionate to his size I wondered?

And the answer was a resounding, hell yes!

I could not get over this thing that I’d pulled out of his shorts. I grabbed it with one hand and pulled on it hard to get it out of its confinement. And when I did my breath must have left my body because I gasped out loud. Real loud.

“Yeah, I knew you’d like that, suck my cock!”

With that, he slid his massive hand behind my head and forcefully shoved my face down into his crotch. My mouth opened obediently like it was what it was supposed to do. Jack has a thick cock and that saved me because it’s about the same thickness as Dawsons.

The length however was an entirely different story. He’d barely gotten half of it into my mouth when that fat cock head hit the back of my throat causing me to gag.

“You’ll be all right Joey. Just relax your throat muscles. Swallow my cock and learn to breathe through your nose.”

I listened to him as he lifted my head allowing the gag reflex to pass and for me to catch my breath. Then we’d repeat the process. Over and over, the base of his cock, my hands, and his balls had all become soaked with my saliva. My eyes were watering so much from each attempt of trying not to gag yet still gagging, that I must have looked as if I’d been crying all night.

He was talking to me as if I was some cheap slut.

“C’mon cocksucker, relax that pretty throat of yours. C’mon baby doll, show me you can suck a real cock.”

I know, I know, I should’ve been offended but I wasn’t. I was taking it like a dare. Like he was showing me that he was better than me because I couldn’t do what he wanted me to do.

I know it’s twisted but again, I’m not a girl. The guy in me wanted to show this mother fucker that I could do it and guess what? I did it.

I don’t know how long it took me, but he was fucking my throat. He’d pull back to let me breathe then he’d slam my head down until I could feel his balls on my chin. I could feel him start to tense up and that’s when I flipped the script.

I lifted myself off his cock and shoved him back into the couch. My hand was on his throat and my other hand holding a fistful of his balls.

“I bet you want to cum, don’t you? I bet you want to dump your cum in my mouth, and down my throat, huh?”

I tightened my grip on his balls and throat. On the one hand, he was scared as fuck about what I would do next, on another hand he was wishing he could breathe.

“Shhh, relax,” I whispered in his ear. “Now, I’m going to suck your cock like I want to, and you’re going to sit back and relax. Right?”

I could see the fear in his eyes until I gave him a smile that only someone who wants your cum in their mouth can give you.

He smiled and nodded yes.

I went back down on that cock, that large and glorious cock, and started sucking it slowly. I alternated deep-throating it and suckling his cock head until he could hold out no longer.

I don’t know how long it had been since he’d gotten a blow job but the amount of cum that I swallowed when he did cum, I can only guess it was during high school.

Dawson came so much that I had to stop swallowing and just let him finish on my face. It was the nastiest, most erotic thing that I’d experienced before that night or ever.

After I’d cleaned up Dawson wanted to play. But that was not going to happen.

“No, you are not getting that thing in me, babe. Get that out of your head.”

He grumbled and mumbled but he left knowing that I wasn’t about his silly dominance games. That day started my adventures in sucking cock and maybe that’s what ended my time with Jack.

He never caught me but by the last month of summer, he’d turned his attention to someone new. Call it Karma or maybe it was Jack’s need for balance. Like I said in the beginning, Jack is bi, and I guess it was time for a girl, a real girl for a girlfriend.

I was hurt for a whole minute, but classes had started back up and I had a new life in front of me. I had finally found some semblance of happiness.

As I said, it started sweet but losing Jack was a bitter pill I had to swallow…