The Making of Monica Ch. 06

The making of Monica. Part 6

Sucking my fist cock.

Linda and I remained good friends even after our sexual experiences. I think we had grown so close and so open with each other that after that night of the bar, coupled with alcohol and loneliness led us that first romantic night. And many others afterwards. All of which I will never forget. Especially considering I was dressed as a woman and on occasion was being fucked by a dildo she was controlling.

However, as fun as it was and as much as I was enjoying, the new sexual experiences. I knew as she did, that I needed to take the next step. I needed a man. I needed a real dick. And I needed to accept who I was and where I was going. So, about four months after our first sexual experiences with her, I finally agreed to a date with Giovanni. A guy known to all of us at the bar as Big Joe.

By that time, I would be hanging out frequently at one of the gay or lesbian bars near my neighborhood, dressed and living as Monica. I was friends with several women and another Crossdresser that hung at a few of these places; and with my new found friends and freedom, gave me the opportunity to spread my wings even more. Giovanni is/was the proverbial Dago. Sorry to any Italian readers, but there's no other way to describe him.

Giovanni is 6'0 tall, fairly thick build, with his thick black hair, slicked back with a heaping helping handful of hair gel holding it back. He usually wore a white long sleeve shirt, that was unbuttoned halfway down, revealing his hairy chest, his gold Italian horn or cross hanging from his neck. His shirt sleeves partially rolled up with the black hair of his arms exposed. He always wore black dress pants, coupled with his stylish pointed dress shoes and his gold pinky ring and Italian bracelet on his wrist. Giovanni always had a pocket full of cash and he drove a big black Cadillac car, which made him resemble the mobster I think he always wanted to be.

Giovanni had met me the first night I was out with Linda at the Lesbian bar. I was always curious on why a straight male would be hanging out at the lesbian bar, but as he later described it; "It was to protect the girls and not be in a bar full of testosterone fueled men." Giovanni was always hitting on me. I even went so far as to tell him I was a man, but he didn't seem to care. I don't really know if he was gay, or suspected he was gay or just needed to get laid by someone, cause lord knows, I never saw him with a woman.

Giovanni and I had several talks throughout the months. As I started to get to know him more, I knew he was a good guy with a big heart, but he wasn't someone I would have wanted to date. But after having him ask me out time after time, I finally agreed to dinner. I figured, for me, it would be an opportunity to go out somewhere dressed in a restaurant and be out on a date with a man I knew, instead of dating sites or a hope of meeting someone at a club.

Giovanni picked me up at the bar, because I didn't want him to know where I lived. He took me to a fine Italian restaurant (what a surprise. Right???) that he liked going to. We actually had a great dinner and a great conversation and he always addressed me as Monica and acted like a gentleman. In some ways I believe maybe I was falling for the big teddy bear, but I also felt that I wasn't sexually interested in him. My desires at that time still revolved around women, or crossdressers like me.

At the end of the night, he dropped me off back at the bar and didn't try to make a move or sleep with me. So, a week later when he asked me for a second dater. I agreed.

We went out for a second dinner date, followed by ice cream afterwards and we were just driving back towards the bar in his car, when he reached his hand out and laid it on top of my hand. It was soft and romantic and I felt that even though I wouldn't want to date him. I was interested enough to -- at least -- maybe suck his dick. And as much as "Monica" was ready to try men and experience dick, I wasn't going to take him home and fuck him.

I leaned over and whispered into his ear, "Do you know of a quiet dark place we could sit parked for a while?"

"Yes." He groaned out and started to change lanes to get us where we were going.

We drove for a bit longer until we came to a large parking lot, overlooking the ocean near a highway overpass bridge.

We sat and talked for a long time, while I was mustering up the courage to fool around. Giovanni leaned over and kissed me. I think it took me by surprise, but since I asked to go somewhere to be alone, I guess I should have expected it. I kissed him back and, in some ways, it was erotic, but was also weird, considering he was the first man I ever kissed. His strong, musky aftershave, lingered on his face as he swirled his tongue around my mouth. I almost started thinking, maybe this wasn't a good idea. But I also knew I was ready for a man, and even if this didn't go as planned, at least maybe I'd have my first gay experience.

As we kissed, I started trying to get into him/this more. His big pouty lips, covered over mine and his warm big arms, curled around me. I wanted cock. There was no doubt about it. I had made this change for a reason. I wanted to be a woman. I wanted to give head. I wanted to make my guy cum. So, even though this wasn't the best situation, I was going for it.

I slid my hand inside his shirt and swirled my hand over his nipples and through his soft chest hair. His hands cupped my breast forms and along the side of my face and neck. I wasn't overly turned on and I wasn't hard, mostly because I was nervous and still unsure of my feelings for him. But if I was going to have my first experience with someone male, I would rather have it be him, then some douchebag from a bar. I felt his hand slide up and along my left leg around my knee caressing my skin which was covered by my nylons. My toes were curing up in the high heels I had worn and my dress was a bit out of place, but still felt sexy covering my body.

I slid my hand up his inner thigh and for the first time in my life, my hand slid up to someone's crotch to feel a bulge in the pants and not the outline of a pussy. It was weird, but erotic as I literally felt his balls sitting tucked in his pants. His hand kept sliding further up my inner thigh and I was excited he was getting close to my cock as he was getting himself more turned on. But also getting me aroused as someone's hands were rubbing up and down my panty hose. I rubbed softly, but sensual enough over his dick to get him overly excited. Our kiss deepened and his breath thickened as I continued feeling him up, as his hand slid higher and higher under my dress. I broke from our kiss and looked him in the eye and reminded him again that I was a boy.

"I know." He spoke. "I like you Monica, I am not worried about what's below the belt."

"Okay!" I said as I leaned back in for more kissing.

My hand continued rubbing is crotch feeling the outline of his dick and as scared and apprehensive as I was. I wanted to suck dick. I started pulling at his belt trying to get it open. Giovanni had to pull his hand out from under my dress. He helped by sucking in his stomach and using both of his hands to get it open. I flicked both ends wide open, pulling at the button to get the pants unhooked. I fumbled with his zipper, finally getting it down and slid my hand down into his pants. I felt his short stubby cock trying to poke out of his underwear, as I continued caressing it. I felt a tingle inside of me I had never felt before and I felt like this is where I was supposed to be.

Giovanni opened up his pants flaps further and adjusted himself in his seat to give me better access. I pulled his boxers away from his waist and slid my hand down into them. It was my first touch of a male cock, partially hard and it was rather exhilarating. I stroked him softly, but firmly as we kissed more. But I wanted to suck it. I wanted it in my mouth and I hoped it would be everything I had been fantasizing about.

I adjusted my body and got up onto my knees on his passenger seat. Giovanni lifted his hips and slid his pants and underwear down slightly letting his cock free. I held it in my hand just staring at it, as I took a mental picture of the first cock I ever played with. It was stubby and shrouded in hair, which I wasn't fond of, considering I was clean shaven everywhere. But he was 100% Italian, so shaving it would have been a battle he never would have won.

I leaned my head down and before I could even fathom what was happening, I had his hard cock in my mouth. It was an enlightening, erotic moment being on my knees in a car, ass in the air, dressed as a woman and sucking my first cock. I felt this thick short cock sliding in and out of my mouth. His hard cock, which was not as firm as my dildos, was throbbing inside of my mouth. The feeling of his head, thick and plump, was riveting. I knew then. I absolutely knew. I wanted cock. OFTEN! Maybe not his, but I wanted cock. I was a changing into a woman. I was gay and I was going to be sucking all the dick I could get.

I bobbed up and down on Giovanni, listening to him moan and shift in his seat as my tongue swirled around his shaft as his cock slid in and out of my mouth. I was finally doing it. I was sucking dick it. I had finally found a hard dick! A real dick! Not a toy or vibrator. I was sucking cock and I was going to make this the best damn blow job he ever had.

My mouth watered and my body tingled. My head thrusting up and down taking every bit of his short cock as deep as I could into my mouth. His pubic hair, touching my nose and chin as I lifted and fell further and deeper into his lap. I wasn't hard, but I was surely turned on by sucking him off.

I don't know how much time had passed, because my head was spinning. In my mind I was screaming, "I am finally sucking cock!" I was happy, I was excited, I was turned-on and I wanted more. I wished Linda was here to see this. The girls at the bar, were here to see this. Anyone here to see this. The more time elapsed, and the more his cock slid in and out of my mouth, the more I was loving it. My mind raced, my thoughts going everywhere, but yet still grounded to the feeling of his cock sliding in and out from in-between my wet lipstick covered lips. But Giovanni's heavy breathing and hands being placed on the back of my head brought me back to reality.

"Monica, Oh god Monica." He moaned out, as he started pushing my head down harder jamming his cock deeper into my mouth.

Some people might think this is a bit unreasonable, but I was actually loving it. In my mind I was thinking take control baby, make me suck your cock. Force me!

I bobbed up and down on Giovanni for about another minute, working this blow job, getting into it, listening to his moans getting louder and louder; deeper and deeper. My cock actually starting to tingle and pulse, knowing what he was feeling. It was erotic to think my cock was buried deep in my panties, with a thin piece of the thong material running up my ass, my nylons holding it all in and my breast forms rocking back and forth in my bra. My wig slipping back and forth as I was sucking cock. And I knew I was turned-on by the blow job. But more importantly I was turned on by being dressed as a woman, giving the blow job!

Giovanni's hands started guiding the back of my head down further. Then up further. His moans and groans increasing, his plump little thick cock, fully erect. My mouth pleasing him, drawing him nearer to orgasm. I knew he was close; I knew he was going to cum. And I wanted to feel a cock explode in my mouth.

"I'm gonna cum Monica, I'm going to cum." He bellowed out!

My head sweating, my mouth and lips starting to get numb from sucking cock, my ass tingling, but my dick buried deep in my panties feeling different than it ever had before, waiting for him to cum in my mouth as I sucked him hard.

Within seconds Giovanni started whimpering loudly his hips started to lift up and down off his seat. Before I could even get ready, he was shooting his load deep into my mouth. The warm soft flow of his cum, salty and sticky filled my cheeks. I didn't want to swallow it, because I was scared too. But I wanted to make him keep squirting. I wanted to feel what it was like to have someone cum in your mouth. To taste it, to live it! I just kept it all in my mouth and kept sliding up and own on his completely hard and cumming cock.

"Holy Fuck Monica," he bellowed out, as he continued shooting his cum inside my mouth, as I never broke pace still bobbing up and down, longing for more.

I let his cum slide out from my lips and slide down his shaft onto his skin and hair, as he stopped squirting and started coming down from orgasm.

"Stop, Stop, Stop. He cried out as he grabbed my head stopping my motion.

I had got him off, but now the overbearing tingly sensations guys get after cumming was too much for him to bear. Although I must say, I wanted to keep sucking on him. I wanted to give a blow job and as apprehensive as I was about doing it. Now that I was doing it, I wanted more.

"You gotta give me a minute." He grunted. Followed by a long breath exhaling the word, "Whew!"

I lifted my head, sliding his dick out of my mouth, licking my lips and swallowing the last bit of saliva and cum that was in my mouth down. I was dripping wet with sweat and he was breathing heavy, his shirt wide open, little stubby dick sticking up and out of pants which were -- by then -- half way down.

"Did you like it?" I asked.

"Yes, I did." He replied.

"Good." I furthered.

It actually made me really happy to hear he liked it. I had just given my first blow job as Monica and even thought it wasn't necessarily who I thought my first experience would be with, it was a great first experience.

I sat back down in my seat and I wanted to whip my cock out, but I wasn't completely hard and truly wasn't horny. Plus, at that point I wasn't even so much concerned about getting head or fucking, my goal was to be fucked. So, there was no way after giving him a blow job, he was going to fuck me. I was just proud of myself for sucking his dick and tasting his cum. Giovanni and I sat out under that bridge in that parking lot for a while, until it was time to head home.

I held his hand all the way back to the bar, where he kissed me softly on the tip of my nose and said, "Thank you."

I got out of his car and walked towards the bar. But as he drove way, I turned and headed home. I wanted to celebrate with the girls and tell them all about sucking my first cock. I wanted to scream it to the world. But it was a moment I needed to have all to myself.

I laid in bed that night thinking about it. About him. I still had no desire to date him like a boyfriend situation, but I was surely glad he was the first guy I gave head to. I did suck him off a few weeks later after a night at the bar and all of us being overserved. But it was the last time I sucked his dick. I couldn't bear to sallow his cum down that night either and just spit it out. What I later learned about myself is that; if I am not really into a guy, or unsure about the dating situation, even if we are fooling around, I don't swallow his cum down. Some weird psycho thing, I guess. But, when I do like a guy or we are dating exclusively / I want to date him exclusively, I swallow every fucking drop down. Strange right?

My development for anal sex and oral sex developed even more after that night. The world hadn't changed much, just a small part of mine did. I knew I was destined for bigger and better things and I knew there would be a host of men wanting me ass, as I wanted their cocks. Through it all, I knew I could suck dick and get men off. After it all set in, I realized, I absolutely liked sucking dick and being a woman. Or at least an open and out crossdresser.

I bought one of those electric thrusting dildo machines -- like you see in porns - and had a fair share of fun with it, until I finally lost my anal virginity by a real dick some months later. But I must say that "toy", more like that "machine" gave me some incredible nights.

My true love came in the form of another crossdresser named Jessica. Who taught more about sex than anyone before and changed my world for the better.

I'll tell you all about her in the next chapter.