Hi Mommy

By Cathe

Published on Dec 20, 2007

Transgender

Hi Mommy ... Chapter 6

I felt surprisingly comfortable walking with Brian's arm around my shoulders, although it was difficult to make small talk. We walked slowly, taking in the sights and sounds of the city late at night. The streets were fairly crowded for the late hour. Not entirely surprising in a city where music and dance clubs are active until very late.

"I know a nice little cafe down the block that's open all night", Brian said. "Is that okay with you, Monica?"

"Sure, Brian." I said.

"Are you feeling any better now?" he said softly. "I was concerned back there. There was just something about the look in your eyes that wasn't quite right. Guy troubles, maybe?"

Boy - if he only knew! I couldn't help but laugh.

"In a way ... yes. I ... I can't talk much about it right now, Brian. I have to ask you to cut me some slack about personal subjects. I hope you're not offended, but I'm going through a difficult time emotionally. I'd rather keep things to myself for a while until I can sort things out."

We had stopped walking briefly, and I was facing him looking up into his eyes. Brian was as tall, at an easy 6-3, as I was small. I didn't particularly feel "manly" next to him. I didn't feel particularly manly at all, in fact. How could I, the way I looked? All I knew was I was comfortable with myself - perhaps more than I'd ever been. And that scared me. 25 years of my life had been spent trying to conform to a standard I simply could not meet, as hard as I tried. I had disappointed my father as well as myself. I could not be what he wanted me to be, nor could I be what I wanted to be. I couldn't even decide exactly what I wanted to be, but it wasn't what I was.

Always very emotional - I had more feminine traits than masculine. I tended to touch people - and that wasn't something men did. I loved nurturing kids - another trait men weren't supposed to have, or show if they did. I loved to dance, I loved music and art. I loved to cook. At gatherings, I would usually wind up in the kitchen with the women, rather than hanging around a pool table or watching sports on the television.

"Just give me some time, okay Brian?"

He gathered me in his arms and kissed the top of my head.

"Sure, Monica. Gee .. Your hair smells so good. Did I tell you how lovely you look tonight, by the way? Linda is a good friend, but I have a weakness for brunettes - especially when they're as pretty as you."

I kind of liked being held like this - hearing nice words. I squeezed against Brian again and looked up into his eyes again. I closed my eyes and opened my lips slightly - inviting him to kiss me. I don't know why - it just felt right. I felt Brain's lips touch mine and opened my mouth wider to accept his tongue. I guess I involuntarily moaned, because I heard it. Either that or it was Brian. I also felt his erection against my stomach. He must be hung like a horse if what I felt was any indication.

As we broke the kiss I dropped my eyes to his erection and laughed. "Is all that for my benefit, buster? That's quite a compliment!"

"Geez, I'm sorry if you're offended, Monica. I just couldn't control myself. It certainly is a compliment, though."

I laughed and took his arm, "Come on - we better get to the cafe before something happens. Ummm... Brian?", I asked softly. "Just how big are you, anyway?"

"Well, with any kind of luck - you'll see first hand soon enough!" he laughed.

What surprised me is I was looking forward to finding out exactly that, and what's more - I was comfortable with how I felt. "You never know, Brian - you might just."

The cafe was really nice. Quiet and private, about half full at that time of the morning. It was 2:00am before we realized it because we were talking so much - clicking like we were old friends. I was falling more and more into the female role as the night went by and I became more and more at ease with my new persona.

"I hate to call it a night, Monica, but I have about an hours drive home. I wish I could spend the rest of the night talking to you. I'm really having a great time."

Time for a decision, I thought. "Brian", I whispered, "You know Linda lives only a few blocks from here. If I invited you to spend the night with me at Linda's place ... could I trust you to go no further than I'm ready to go? I have to be very careful right now. I need you to say you'll give me all the time I need."

He again wrapped his arms around me. "I was hoping you'd ask me that, hon. I will give you all the time you need - I promise."

With that, we walked arm in arm the 5 blocks to Linda's apartment. It was almost 2:30am on what would be the second most significant day of my life. This night would define what my life was to become.

I used my keys to enter Linda's apartment and showed Brian through the door.

"Wow!", Brian whispered. "I had an idea Linda was doing okay, but this is really something!"

I wasn't exactly sure if I could pull this off or not. I worried about everything from would my hairpiece fall off, to would an errant hand discover what was inside my panties. As long as Brian was good to his word, I thought it would be okay.

"We both need some sleep", I said softly. "You may share my bed on the condition that you honor your agreement. I am going to change out of this dress. I suggest you get undressed and get into bed. I will join you in a bit. If you were asleep when I get back, it would be a help."

And with that, I turned and walked to Linda's closet hoping to find something that would conceal my secret.

I heard the bed squeak as Brian got between the satin sheets. I secretly wished I could hear the bed make a lot of squeaks when I joined him, but knew that was not to be. I took off my dress (funny how I already thought of it as MY dress) and jewelry - hanging the dress by the door to be cleaned. I took off my bra and panties, which were still wet with my leakage, and also put them in the hamper to be washed. My stockings and garter belt followed. In Linda's well-marked drawers, I found another set of panties and bra. Hanging on a wall were a few dozen nightgowns, baby dolls, and other negligees. I selected a floor length yellow nightgown that matched my bra and panties, and slipped it on. Did everything women wear feel terrific?, I wondered. Especially so with a hairless body. I sat at the dressing table and considered what to do with my hair, or rather Linda's hair piece. I ran a brush through it briskly, figuring if anything would make it fall off that would. It stayed in place, so tight were the 3 combs that held it to my own hair. I was almost tempted to take it off and brush out my own hair, but thought Brian might be curious what happened. I decided to put a chiffon scarf I found in the drawer around it like a head band - holding it back behind my ears, off my face. I was worried sleeping on it would ruin it, but being natural hair I figured it would be easily repaired. How right I was. Taking a deep breath, I stood and walked towards the bed, hoping Brian wasn't awake waiting for me.

Approaching the bed in the dim light, I saw Brian was indeed awake and waiting for me to return. I heard the sharp intake of his breath when he saw me in the light.

"Wow. I mean .... wow", he whispered.

He held the covers up for me to slip into bed beside him, and I couldn't help but smile at the knowledge that he still found me so attractive. I sat on the edge of the bed and looked at him, trying to get a feel for how this would develop.

"Are you going to behave yourself and go to sleep, or do I have to sleep with Linda?" I asked softly. But I was smiling as I said it.

"You are absolutely KILLING me, Monica. You are truly a vision to my eyes. Okay, I promise to be good, dammit!"

I slid into the bed and propped myself on one elbow, smiling at Brian. I saw immediately that he was totally naked - he hadn't even left his shorts on.

"Did you forget to leave your shorts on, Brian, or do you normally sleep naked as a jaybird?" , I said, with a hint of amusement.

"Oh", he whispered. "No, I didn't have an ulterior motive, if that's what you're thinking. I really do sleep naked. Would you feel better if I put my shorts back on?"

I couldn't help but laugh at his discomfort. "No - it's okay - I won't peek at you. Maybe. At least not until you're asleep!"

Without thinking about it, I slid over Brian and kissed him. I know I was acting crazy, but I couldn't help myself. I lifted my face away after a brief kiss and he reached up with his hand and brushed my hair back off my face.

"I love your hair back like that, Monica - it's very pretty and sexy."

As I leaned in to kiss him again - more passionately this time - I had time to whisper "let's see if I can make your package wake up again."

During the long, tongue swapping kiss, I slid my hand down his chest, running my fingers through his chest hair, until I reached his pubic hair. A bit further and my fingers found his balls, and slid up over his cock. Good God, I thought, he's huge! I wrapped my fingers around it and involuntarily moaned into Brian's mouth. He reacted immediately, shoving his tongue further into my mouth where I greedily sucked on it as if I was sucking on his cock. I played with another mans cock for the first time and loved every second of it. I felt it get slippery with pre-cum. I then did what I never in a million years thought of doing before. I broke away from Brain's mouth and dove down, immediately taking as much of his cock in my mouth as I could - which was less than half it's substantial length. It was so big I could fit one hand around it and still have more than I could handle in my mouth. As Brian moaned and put his hand on the back of my head - running his fingers through it - I began bobbing my head up and down his cock, sucking furiously, trying to stuff all of it into my mouth.

I was both gagging and moaning as it reached deeper and deeper into my mouth and throat, as Brian literally cried for mercy.

"Mmmmm! ... oh God Brian!....mwah...mwahhh...." All you could hear besides Brain's moaning was the sound of my lips slurping and sucking. I decided I wanted to taste him. "Cum in my mouth, Brian. Please...." I moaned.

"Oh Monica .. Oh baby ...." he was moaning. Out of the corner of my eye I saw Linda standing partially hidden behind her closet door. She was smiling. Brian was trying to reach between my legs, but I stopped him and gurgled "Um-ummmm" around his cock. Like he promised, he backed off as I continued sucking his monster cock. I shifted around so I was between his legs and got on my knees bending over. I now had a better position to try and get his entire cock in my throat. I took both of his hands in mine and entwined our fingers. Looking into his eyes, I began pistoling my head up and down his cock - saliva running ut of my mouth and down his cock to soak the sheet. Squeezing his hands, I began taking long strokes, and miraculously managed to get his entire cock into my throat. My lips were resting in his soft sweet smelling pubic hair. Breathing through my nose, I was able to keep his full length in my throat so I could squeeze my throat muscles around it. All Brian could do was moan softly and gasp for his breath.

"Oh God, Monica ... I'm going to cum, baby!"

I released his hands and slipped his cock out of my mouth and locked eyes.

"Hold my head and fuck my face, Brian. Fuck my face and cum in my mouth, baby. I want to taste you. Oh God ... I don't know what I'm doing, but I want your cum!"

Without a word, Brian slipped his fingers through my hair on both sides, which locked my head in his hands. I lowered my lips over his cock and Brian began to slam his cock into my throat. My hair flew about my face and Brian's cock and balls. It must be a mess, I thought, as he pounded his cock into my throat. It would be worth whatever it cost to have I restyled, I thought - I want this cock to unload in my mouth, into my hungry stomach. All of it - every drop he had. I wanted it all. As many times as he could manage to cum.

I needed it, and knew my destiny had been decided. From a small taste of his pre-cum, I knew I wanted to taste all the cum I could get.

I pulled my head away from Brian's cock to catch my breath, saying "wait a second. Let me change position."

I quickly slid around on my back, taking 2 pillows and lying back over them so my head fell at an angle over them. I motioned for Brian to slide up from behind my head and guided his cock back into my mouth so he knew what I wanted. In this position, Brian could fuck my face like he was sliding into my pussy - had I had one.

"Come on, lover, fuck my face now and give me your cum." I whispered - my voice raspy from having his monster cock invade my vocal chords into my throat.

Needing no further instructions, he leaned forward so he could support himself on his hands, his cock firmly in my throat as I wrapped my arms around his ass, pulling him into my mouth. My once pretty hairdo splayed out over the pillow. Saliva dripped off his cock, falling into my hair and on my face. Linda was still watching from her spot by the closet where Brian could not see her. I could see one of her hands working feverishly between her legs, her mouth open like a fish out of water.

Brian was pounding into my throat as my hands each grabbed his asscheeks and pulled him into me. I imagined what it would feel like to have him pounding his cock into my ass pussy. Then it happened.

"OH GOD!" Brian nearly shouted. "I'm cumming, baby - I'm cumming in your mouth. Eat it all, baby! Swallow my cum into your tummy!"

The first shot felt like a fire hose going off in my throat. It shot straight down my throat into my tummy. I could feel the warmth as it slid down. The second shot was at least as big, and it too shot right into my tummy. Then it seemed like a floodgate opened and cum just poured into my throat. It felt like I was drinking hot coffee as it slid down my throat to join the rest already in my tummy. All Brian could do was to keep pumping into my mouth, crying "oh god, oh god, oh god ....." until he was done.

I must have swallowed a few ounces at least of cum. Easily 2 shot glasses full - I could feel it in my tummy.

Brian groaned and fell away from my mouth, which was still sucking, trying to get the last drop of his cum. He fell back on the bed on his back.

"Oh my God" he whispered. "That was the most unbelievable blowjob I've ever had in my life! What planet are you from, anyway!"

I managed to pull myself up from the awkward position I was in and tried to arrange my hair. It was wet with saliva and residual semen. I leaned on the pillow next to Brian and slipped his softening cock back into my mouth, sucking out the last little bit I could get. Then I leaned my face close to his and smiled.

Next: Chapter 7


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