The Making of Monica Ch. 05

Heading to the bars.

Weeks had gone by after my first night out with Linda. She continued helping me with makeup, being my friend, talking to me and walking through my change. But she knew, as did I, that it was time to take further steps.

Linda talked me into going to one of the lesbian bars, she frequents dressed as Monica. I was leery, but figured it's a lesbian bar, so what's the worst that could happen? We agreed to go Saturday night that next weekend. I picked a long flowing blue dress with nude colored thigh highs, white two-inch heels, with a set of white pearls and matching earrings and my long brown wig. I met Linda at her place and she touched up my makeup and we headed out.

I was always nervous about coming and going from my building dressed, as someone might recognize me. But I was also nervous and still uneasy about a bar. But when we got to the bar, we hung with a few of her friends, most of whom accepted me without reservation. I sat with the girls all night having a few drinks and being part of a group. It was rather enlightening and erotic to be "a girl" sitting with the girls and just being part of the group without judgment in a safe place. And even being hit on by Giovanni. Yes, the straight guy in the lesbian bar. Whom I'll tell you about in later stories,

However, after the nervousness eased, I was so turned on being in a bar room full of lesbian(s) and/or their admirers that I was semi-hard the whole night. After watching so many lesbian porns believing that some of the women in here were going to go home and have sex, kept me envisioning them seducing each other and it being REAL. Not paid actresses, not some Hollywood set, some porn movie money shot! These women were for real and I was more willing to take my transformation forward to be like them.

We left that night and headed home. As we drove the wind blew through my wig, the warm, moist California air enlightening me. The feeling of women's clothes covering me, making me feel sexy, coupled with time out with a newly discovered trusted friend, made me want this permanently. I was out. I was alive. I was living my dream and even though I hadn't come out to anyone close to me. I was ready and I was becoming Monica. But as much as I knew it was time to move forward. That "forward" meant being out on general public, regular bars, at the malls, at concerts and restaurants; and that was still a scary thought.

Over the course of the next few weeks, I would take those baby steps alone. I would head out at night and go to places I knew I wouldn't run into to any friends or family fully dressed. I would shop, walk the mall, go to the grocery stores and I interacted with people at those locations. I'm guessing some may have known, others maybe not. But the point was; I was out. I was outside dressed and I was interacting with the general public. I was taking steps and I was beginning to get more comfortable.

I was ready for more. I asked Linda if we could go to one of the "Meat Market" bars in our area. I explained to her that I wanted to try and interact with both men and women and see if they would know, accept, or discover my secret. Linda agreed and we set aside another Saturday night the following weekend and went.

I dressed in a knee length black skirt, with black thigh highs on underneath. I had three-inch black heels on, with a light-colored sequenced shirt on top, breast forms in. My gold necklace around my neck and a small bracelet to match on my wrist. I was spritzed in my favorite perfume and I had a small handbag I was carrying. All topped with my long blonde wig. Linda was dressed in a short length white skirt, no pantyhose, matching high heels, a blue shirt and a long flowing white open front sweater over the whole ensemble.

We drove to the place and arrived like two queens walking into the festival. We stood proud and tall and even though my stomach was doing flips and I was shitting a brick, I held my confidence. The place was crowded and it was scary for me being out in a new location, which was busy and noisy, but I went for it. Linda and I grabbed two seats at the end of the bar and just waited to see what happened.

Throughout the course of the night, several men had approached us and tried to make conversation. Some I'd chat with, some I just waived off, but through it all, I had managed to hold my composure and had some interaction with them at a bar. I don't think anyone of them knew I was man, or a crossdresser and even if they had realized it, they never mentioned it. It was absolutely fabulous. I was enjoying this freedom. The sensation of being a woman and having people approach me and talk to me was unbelievable.

Of course, we all know these types of bars are famous for hook-ups and sexual experiences, which I wasn't concerned with because I knew I wasn't leaving here with anyone except Linda. But, just to know that men were approaching me and Linda as well, was rather solidifying. And to be honest there was a couple I chatted with briefly that night, that I may have thought about dating. And as I sat and chatted with them, watched others wandering around the room, I began to want men more. I wanted to be seduced. Wanted to be fucked and I wanted to suck dick for the first time. I was tired of dildos and toys; I wanted a real cock. I wanted to taste someone's cum. I wanted to give a blow job!

As the night drew later, Linda and I decided it was time to go. We wanted to celebrate this moment privately with a toast of Champagne back at my place. We headed out and made our way home. But that's when things took an interesting turn.

When we got back to my condo, we stood around in my kitchen and laughed and giggled re-living the night. Both of our high heels clicking on my tile floor as we walked back and forth, getting everything ready, I was so enamored by her. So enamored by being here -- at this moment -- being dressed, being out, developing my lifestyle more and being free. I popped the champagne bottle open as we yelled "Hooray," laughing at each other. Linda and I poured a glass and she finished that one rather quickly, as we talked deeply about our experiences and thoughts of our night.

Linda refilled her glass and was walking out into the front room when she said;

"I cannot believe the night we just had."

I was seconds behind her walking into the front room, each of us holding our glasses of champagne.

"I know!" I replied. "It was amazing."

"I cannot believe how many men thought you were a woman. I don't think anyone of them suspected a thing." She bellowed out.

"I agree." I replied. "I think most just saw me as Monica."

"Come here, let me look at you." She spoke as she set her glass down, her hands reaching out for mine.

I set down my glass on the table as Linda's arms extend out and downwards as mine came up to hers. We held hands and we stood there starring into each other's eyes as she just complimented me time and time again.

"You look amazing." She whispered out. "I cannot believe how far you've come. You should be proud of yourself."

"I couldn't have done it without you!" I replied.

"I am proud." I followed up. "And happy. I am finally happy."

Linda's head tilted slightly and she smiled almost welling up in tears, because she knew, like I was beginning to know, how much of a release it is to finally accept who you are and where you're heading. Linda pulled me in for a long hug, whispering in my ear, "I am happy for you."

But when we pulled back from that hug, we both stopped face to face staring into each other's eyes. The moment was silent, the only sound I heard was the beating of my heart, which I believed was thumping out of my chest. Linda pulled me in for another hug and held me tighter and longer. I could smell the sweet perfume she was wearing and it had been forever since I had held a woman.

When Linda pulled away this time, we didn't hesitate, we both leaned in for our first kiss. It was something I never expected, since I was transitioning "to a woman" and was fantasizing more about dick. But I couldn't control myself, or contain my desire for her.

Our lips met and we held them together closed, but softly pressing against one another's. Our lip sticks mingling as we stood embraced. Our lips parted and our first deep kiss began. Her soft, almost fearful tongue, slipped into my mouth as mine was reaching into hers. Our tongues swirled around as our mouths opened more and I pulled her closer into my body. Linda and I stood kissing deeply for several minutes, never breaking free.

Our hands rubbed up and down each other's bodies. For a brief moment, we broke from our kiss, looking deeply into each other's eyes, only to resume kissing again. I was about 6 inches taller than her in my heels, so I kicked them off to come closer to eye level with her. I felt Linda's hand caressing and cupping my ass over my skirt, feeling my bare ass underneath. I was so turned on. My hands rubbed and caressed her chest, feeling her older, yet sexy plump tits. Our kisses deepened and our lust grew stronger as we petted and caressed each other more.

Linda's hand worked around from my ass and up and down the front of my clothes. She started softly lifting my skirt at the sides of my legs as my cock got extremely hard in my thong.

"It has been forever since I've had dick, but I want this." She moaned out.

I helped lift my skirt up all the way past my waist line as her hand started rubbing and caressing my cock, which was poking out of my thong. Linda kissed her way down to my chest, kissing my fake breasts over my shirt as her hand was rubbing me, trying to stroke my cock. She slid my panties to the side, letting my cock and balls free as her hands grabbed and pulled on my shaft. She edged her way down and came face to face with my hard cock.

Linda looked up at me just before she slid my hard dick in her mouth. She slid my shaft in and out a few times, before withdrawing it and licking up and down the shaft, swirling her tongue around the tip, only to slide it deep back into her mouth. She bobbed her head back and forth for a while, bringing me closer and closer to cumming. I was grabbing and cupping my fake breasts and my ass was tingling. I was holding the end of my shaft along my skin, at the end of it, while Linda slurped back and forth. Her soft moans and whimpers coming from her mouth through the blow job.

There was no doubt. As much as I wanted to try men and experience cock. I needed to be in her. I needed her pussy and I needed to cum. What an exhilarating feeling it was standing there dressed in women's clothes, getting a blow job by a woman.

I helped Linda back to her feet where we came face to face again. I guided her back onto the couch where she laid flat with her ass partially hanging off the cushions. She started lifting her skirt as I got down onto my knees. She had no panties on and her wet pussy was awaiting my touch. I was actually surprised she was clean shaven, I expected someone her age to still have pubic hair.

I knelt in and lowered my head as started kissing and licking her clit to slit. She spread her legs as open as far as she could, rocking back and forth as I ate her out. My free hand stroking and pulling on my hard cock as I kept listening to her moaning out; "Monica! Yes, Monica!"

She came quickly all over my face, as I just kept going hearing her high-pitched squeals coming from her, as her hips rocked back and forth.

"Fuck me!" She cried out as my tongue was buried deep inside her pussy.

She edged further back onto the couch as she pulled off her shirt, pulling her bra cups down letting he big saggy tits out. I started kissing up her stomach along her ribs making my way to her tits. I kissed, sucked and licked both nipples listening to her moan as her arms wrapped around me.

"Put your dick in me!" She moaned out.

I started to climb further up on top of her, getting myself aligned. I slid my cock inside her soaking wet pussy, feeling myself fall into her loose, wide-open slit. I started pumping back and forth as our mouths met as we kissed deeply while my cock was nestled deep inside her.

Her tits rocking back and forth as my hands were grabbing, slurping and holding them as I pumped back and forth. My cock was rock hard throbbing and ready to explode. It had been so long since I have had sex with a woman and the feeling of being with her, while dressed was beyond erotic.

I felt my asshole tingling and I wanted a cock inside me as I was buried deep inside her. Linda rolled me off of her guiding me down onto the floor. She climbed off of the couch, ripping her shirt and bra off. She climbed over top of me, grabbed my hard cock and slid it up inside herself again. Linda rode me slowly and deeply at first. Her dripping wet pussy surrounding every inch of my hard cock. My wig slipped slightly and she tried to adjust it as her tits bounced up and down. Linda unbuttoned my shirt and was cupping and caressing my breast forms, as she bounced up and down. Linda rode me for about 5 minutes until I started moaning out, I was going to cum.

Linda answered my moans by moaning out, "Cum in my pussy! Cum in it!"

Hearing that, after all we've been through and how much I admired her, made me ready to explode.

"Linda, I'm cumming!" screeched from my mouth as I felt my orgasm release.

My body thrusted and quivered as I started shooting my load deep inside of her. Linda still bouncing up and down while my cock was pulsing, thrusting and cumming inside of her.

"I can feel you cumming!" She cried out as I was releasing every drop inside of her.

"Monica, Fuck Monica! You're cumming!" She bellowed out time and time again.

Linda rode me softly for a little more, until she pulled my cock from her pussy slowly sliding her body further up towards my face.

"Eat your cum out of me." She demanded as her pussy lips hit my mouth.

I licked, sucked and swirled my tongue deep inside her slit as I felt her wetness and my sticky cum oozing out of her and all over my face. I ate Linda out until she orgasmed again and pulled herself off of my face. Linda edged down, but lowered her face, licking and slurping along my lips, relieving my face of her juices.

Before the night was over Linda and I had sex again, this time in my bedroom, with a dildo and a lot of lube. It was the first time a woman rammed a dildo up into me and fucked me while jacking me off. I only wish I had a strap-on. She fucked my ass hard and deep, until I squirted my second load all over my stomach. But she surely opened up the door for my first male gay experience, because after that night, knowing I could have a cock in me and cum that I wasn't controlling made me ready for more. I was ready to be a woman. I was wanting to be with a man and I was -- without a doubt -- ready for cock!

Linda and I did sleep together a few more times before I finally gave my first blow; and eventually (different guy) had my first anal sex experience. But as much fun as we had, she was a lesbian and I wanted to be woman and with a man. It was a great set of experiences and a great set(s) of lessons, but in the end, we weren't meant for each other. We were destined for other things.

And this story isn't about sex with women, it's how I became a woman and how I turned to cock and men for my pleasures. So, with that said, let me tell you about the first blow job I ever gave. His name was Giovanni.

To be continued...