Betty's Date

"I'm nervous." I said to my roommate, Deb, as I walked into the living room.

Deb had been my roommate since I moved to Philly for a job. She and her friend Mike had a room for rent. Deb was attractive in so many ways, her breast and hips were full and curvy, and her hair and make up were always on point. That's less of a big deal when you know that she worked at a salon for a living. "You? Nervous? Betty, you are one of the most confident girls I know. You're nervous about a boy?"

"Come on, he's like twelve years older than me, and what if he's not okay with my dick?" I was transgender. I had started transitioning about a year before moving to Philadelphia. When Deb found out I was transgender, she became more interested in me, and the interview went in my favor. She offered me the room at the end of the interview.

Our apartment was a fifth floor apartment in center city. There was no elevator making moving in a bitch. The apartment was an odd shape, after walking in the door, you find yourself in a thin kitchen. A counter top and table were all they could cram in there. There was a hallway at the one end, along the wall was the bathroom followed by the three bedrooms, each had a little window and door. The window was a nice touch as it made the small rooms feel more homely. The hallway then opened up into the living room, which we had a TV, couch, chair, and Wii set up in. Deb was sitting on the couch.

"Sit down, let me look at your make up."

At one point in my life, I was a short guy with poor luck with women and lots of social anxiety, but now I'm just an average height woman, I wasn't stick thin, but I kept my weight at a healthy level. I had black hair styled with straight bangs resting above my eyes and the sides going down long and straight, just past my tits. I wore a rockabilly style dress, it was purple with black polka dots, and a low neckline that held my tits in a prominent position. I had breast augmentation six months ago, and though my scars were visible, my breast were gorgeous. I measured a 36DD, and they really brought my look together. Above them was a large chest piece tattoo that, under the dress, connected to an underboob piece, it was nautical in theme with the entire thing being in the shape of an anchor. I had a few more tattoos on my arms and legs.

Earlier that day, I was waiting to get my septum pierced, when a guy came in waiting for a tattoo. He was tall, lean, and heavily tattooed already. His hair was unkept and his face had a septum and snake bite piercing. I crushed on him instantly. He sat down next to me on an old couch and looked at the TV. Hellraiser was playing.

At one point, he looked over at me, "I was suspended once, by piercings in my back."

I looked over at him, "That's an interesting ice breaker, was it fun?"

"It was, but I only wanted to do it once. I'm Kevin, but friends call me McCleod."

I smiled at him, "Is that because you're the Highlander?"

"I wish, but it's just my last name. Kevin McCleod."

"Can I just call you Cloud?" I asked, "You know, like Final Fantasy?"

He chuckled, "If you want." He smiled, "You going to tell me your name?"

"Nope." I grinned at him. "It's Betty."

"Betty Paige or Betty Crocker?"

"A little of both when I cook. I have a habit of just being in these sexually seductive poses." I was flirting with him, I couldn't even control it, but we were cut short when Cloud's artist was ready for him.

"Before I go, what's your number and are you free tonight."

"Yeah, I'm free tonight." I reached into my pocket and handed him a business card of mine. "Numbers on the business card."

"Wow, I never asked a girl with a business card out before. Cool."

"First time for everything." I said to him as he followed his artist back.

He texted me after I got home asking to meet me for dinner, and sent me a picture of a tattoo on his calf. I agreed and told him to meet me outside my apartment, and sent him a picture of my septum piercing.

Now, I sat on the coffee table facing Deb. She looked me over, checking my eye shadow and contouring. "Damn, I have a taught you well."

I blushed. When I moved to Philly, I was just plastering my face with cover up and drawing on exaggerated eyeliner. "I didn't get a chance to tell him though. I'm nervous."

"Betty, you're gorgeous, he's not going to care."

My phone buzzed, he was downstairs. "Well, going to find out, I'll text you if I won't be home."

"I'll be expecting that text."

I smiled at her before disappearing down the hallway to the kitchen and out the door. On the street outside, Kevin was smoking a cigarette. "Wow, Betty, you look fantastic."

"Thanks," I blushed. He was wearing a punk band shirt, vest full of patches, buttons, and studs, and cargo shorts. "I see you dressed up." His hair remained messy, but had been dyed dark green since I saw him earlier. I knew he was twelve years older than me at 37, but he looked so fucking hot.

"Well, I wanted to be fancy for you." He remarked. "So, there's a pho place near here, I was thinking we go there, fill our bellies, and if you aren't sick of me, my friend's band is playing a show tonight."

"That sounds like fun, I haven't been to a show in forever." I said lighting a cigarette of my own.

As we walked down the street, he asked a few basic questions. I told him I moved down here a few years ago for a job, that I worked a boring office job, and talked about some of the bands we both liked.

After we ordered our dinners, there was a pause in the conversation and flirting, and I figured now was the time to come clean. "So Kevin." I started, my heart was racing, I was scared how this was going to go.

"So, Betty." He responded, leaning closer to me on his elbows.

"I like you a lot right now, but I got to be honest before like, this goes further."

He showed some concern, but saw I was nervous and responded to break any tension, "So this might go further?"

I blushed, "I maybe, kind of hope so, but seriously, I got to tell you something before this proceeds." I paused I was nervous.

"You can tell me, babe."

"I uhm... I wasn't always a girl, I'm transgender."

He looked at me, eyed me up and down a few times. I sat there anxiously waiting for a response. He sipped his water, looked at me again. My mind was racing, my foot was tapping with anticipation.

"So that means," he paused, my heart was racing, "anal is on the table?"

I laughed. I laughed because it was funny and it unraveled all my nerves. I felt a stream of relief at his response. It was adorable. "Maybe." I responded, biting my lower lip while looking at him. "I wanted to tell you before, but I didn't get a chance when you asked me out."

He chuckled, "Betty, I look at you, and I just see a hot chick. I don't care who or what you were before, but I'm totally digging who you are now."

I blushed. "Thanks. I think you're pretty hot too."

The rest of dinner was pretty easy, and I was just completely enamored by him. After dinner we walked the few blocks to the bar where his friend's band was setting up. We stood outside smoking and talking to people. I recognized a few friends from other shows and was talked to them.

"Betty, did I see you walk here with Kevin?" Jessica, a friend of mine asked. She was a tall, skinny punk in short shorts and tank top.

I smiled at her, but curious where she was going, "I did, I met him earlier today."

"That's pretty cool, I'm happy you two hit it off, Kevin's a good guy."

"You know him?" I asked. I was curious to know a bit more about him.

"Yeah, he and his ex wife started the band Poison Mushroom, but he found her sucking off the drummer one night before a gig. The band and his marriage broke up after that. Guy hasn't had any luck since. He's a sweet heart though."

"Fuck, that really sucks. I didn't know that."

"Yeah, his ex and the drummer moved to Portland after the divorce, and he's been single since."

Kevin walked over, greeted Jessica and they exchanged pleasantries, then he turned to me, "Hey, band's about to go on, come on." He grabbed my hand and lead me to the front of the crowd that formed around the stage.

Three girls stood on stage, each with neon hair, fishnets and black dresses. The front woman introduced the band, Queef Smog, and went into their first song, "Kitten." A few kids started to mosh, and more soon joined in. I stepped back as bodies started to crash into people, and I found myself just outside the pit.

Before I could protest, my hand was grabbed by Kevin and he wrapped his arm around my shoulder in the pit. Together we smashed into a few people, were bopped around like a pinball, and I think I elbowed a guy by accident. I was laughing and smiling as we crashed into people, people crashed into us. His arm held tight to me though, and I loved feeling it. He was lean, and his grip on me was strong. I could feel my cock starting to twitch from just his strong embrace. After three short songs, the band took a moment to plead for beer.

Kevin hugged me and I squeezed him back. I looked up at his scruffy face, and wanted nothing more than to start making out with him. He could sense the want in my eyes, and leaned in to kiss me. I tilted my head up and closed my eyes, ready to accept his kiss. Our lips locked and I melted. It had been a few months since I'd hooked up with anyone, and I was craving this.

Our kiss was interrupted as the next song started and the moshing resumed. I was knocked away from him, bounced around the pit until I felt him grab me and pull me close to him. I was squeezed into his chest tightly and we continued our rampage through the rest of the set.

Afterwards, we stepped outside for a cigarette. He handed me one of his cigarettes and lit it for me, then he kissed me again.

"That was a lot of fun," I said between puffs. "I like your friends band."

"Yeah, they're really good. She was the bassist by the way."

"Oh cool, cool. The bassist was what one would expect, she stood to the side and bounced in rhythm of the songs.

He smiled, "I really like you, Betty. Something about you just draws me in."

"I like you too, man. I'm having fun."

"I'm glad, so, would you be interested in going back to my place? I'm just a few blocks away."

I bit my lower lip, I knew what would happen if I went back there. I really would not be able to resist any temptation once we were alone. I didn't take long to respond, "Yeah, we can do that."

"You're comfortable with that?" He smiled.

"Yeah," I smiled back, "thank you for asking though." I kissed him then put out my cigarette, "Lead the way."

He grabbed my hand and we walked down the street holding hands.

Kevin warned me that his place was small, and he was not lying. It was a one room studio, with kitchenette, small bathroom and closet. The walls were littered with paintings and posters for different punk bands. There was a futon couch in the middle, positioned facing an old TV with a VCR and Nintendo hooked into it. A book shelf was packed full of books, VHS tapes, and Nintendo games. Another shelf had vinyls and CDS, on top of it an old stereo. On top of the coffee table was a glass bong and a few empty beer cans.

"Told you it was small." He said as he walked to the small fridge, "Want a beer?"

"Yeah." He handed me a can, "It's small, but it's comfortable." I sat down on the couch. He walked over to the stereo and hit play on the record player. The needle lifted up, the speakers crackled as the needle hit the record, and then David Bowie started to fill the room.

He came back over and sat down next to me. "So where were we?"

I smiled at him, "I don't know, you invited a girl back to your place, now what do you do?"

"Hmm, I think this is where we get on our knees and pray for salvation from the lord."

"Oh yes, after all, I'm a very Christian girl, I follow my strict Catholic morals to a T." I chuckled.

"You're adorable. So, I do want to come clean about something myself."

I sipped my beer, and looked to him curiously.

"I had a really hard divorce a few years ago, ex cheated on me, and we broke up the band, and she ran off with the drummer. I was disenfranchised with dating after that and really hadn't planned on meeting anyone. Then I strike up a conversation with you." He pointed at me.

"And I infected your heart with my adorable smile?" I responded.

"Yeah, pretty much. You're really cool, Betty. You're something different, and I don't mean because of your past. You stood out to me in the tattoo shop earlier."

"To be honest, I don't date too much because I'm never sure how people will respond to my anatomy."

He smiled, "It doesn't bother me none, you're hotter than most girls I know."

"Ha, you think I'm hot. Bet you want to kiss me." I was being bold.

"Oh my, I think you're a mind reader. Are you in my head."

"Oh yes, and soon you will be under my control!" I called before launching myself at him, knocking him onto the couch and straddling over him. I held his arms down and hovered over him. "Now what will I do with my new mind slave."

His eyes filled with want, "Oh my, I sure hope you don't torture me!"

"Ha! Then I will torture you. I leaned down and kissed him on the lips. I could feel his stubble scratch against my chin as we licked lips. I felt his tongue push against my lips, and I opened to welcome it in.

As our tongues intertwined, he freed his hands and I felt them slide down to my waist, then one slid down and gripped my butt. I moaned and looked into his eyes. "Naughty, naughty."

He smiled at me, "Should I have warned you that I'm naughty?"

"Well, you got to save some things as pleasant surprises." I hovered over him, looking into his eyes.

"I think, now here me out on this, before we progress further."

"Oh, we're progressing further?" I asked.

"Well, I'm hoping that I'll have you on your back with your legs in the air, at some point."

I smirked at him, "Quite the fantasy, but dreams do come true."

He grinned at me, "But before then, do you partake?" He motioned towards the glass bong.

I looked at the bong, looked at him, then to the bong, and back to him. "Oh my, this thing? I don't know what this is for, nor have I ever seen one of these in my life. I am an innocent girl."

"You are so innocent, I can tell." He said placing the packed bowl into the bong's shoot, "But don't worry, this just lets you be more innocent."

"I don't know about that, it looks dangerous." I said grabbing it from him. He handed me the lighter and I lit the bong, pulled the smoke into the chamber, pulled the bowl out and inhaled the smoke. I coughed as I exhaled.

I handed to him, still coughing. "For someone who's never done this before, you worked it like a pro.

"Oh my, you caught me. I've used one of these before." He passed it back to me.

We hit it a few times, then he stood up and flipped the record and sat back down, putting his arm around me. I rested into his arms and listened to the music for a few minutes.

I rested my hand on his chest, and started to gently caress it through the shirt, then moved my hand up to his cheek and rubbed it with my fingers until I felt his hand grab my wrist. I looked up at him and he kissed me. The kiss became more passionate. Mesmerized, I didn't react when he pushed me onto my back and straddled me, my legs instinctively wrapped around him, and we went back to kissing.

My hands were moving under his shirt, feeling his lean build made me grow even hornier. I started to pull up on his shirt until he got the hint and removed it. He had a giant chest piece, and two big ones on his side. His nipples were pierced too. I pulled him back down and our kissing became more intense. Hes pelvis started to thrust a little, and I could feel his cock was hard. I started to dig my nails into his back, scratching down as we kissed.

His hands slipped behind me, and started to unzip my dress. I just let him pull it down my shoulders until my large tits popped out. He squeezed one as he went to kiss, lick, and bite the nipple of the other. I held his head and moaned as he worked over my nipples, I started thrusting my own pelvis into him.

"I think I know what you want."

"World peace?"

He chuckled, "Not so much that, he kneeled up and undid his pants. He pulled his pants up and then stood up in front of me, his erect cock hovering in front of my head. He was right, I did want it.

I sat up so that my face was level with his cock, and it was not a let down. Seven inches long, with a healthy girth, a few veins and a beautiful purple head.

"Oh my, I hope I know what to do with this." I said coyly, I reached my hand out and wrapped my fingers around the base and began to stroke. I moved close, inhaling his musk before wrapping my lips around his head. I stroked the shaft while licking the head, and then launched into small bobbing up and down. I felt his cock fill my mouth and I loved it.

I stroked the lower half while taking the top half in and out in quick steady motions, as more of my saliva lubed up the shaft, I started to take it further down my throat. I felt his hand on the back of my head, holding my hair back as I worked his cock over.

He moaned with pleasure along with the occasional, "Oh fuck," "You're amazing," and "Holy fuck!"

I was taking him deeper and deeper now, then with one good thrust I felt my nose reach his groin. I held it in as long as I could, then backed off and caught my breathe.

"You're a pro at this." He moaned.

"Shut up!"

"I'll shut you up." He cooed, before pushing my head down onto his cock and shoved it down my throat. He held the back of my head as he face fucked me. His dick entering into my throat quickly. He pulled it out, then shoved it right back in. He released my head and I coughed and gagged.

"You okay?" He asked looking down at me.

I grabbed my beer, took a sip, and composed myself. "I'm good, that was intense."

"You're throat feels amazing." He then sat down and pulled me between his legs, "But keep going."

Kneeling between his legs, I began to work his cock over again. I was bobbing once again of my own free will, moving up and down his long shaft, filling me up.

"Yeah, just like that, suck my cock like a slut."

His words just turned me on more, "Like a good little slut?"

"Like a good slut. Tell me how bad you want me to fuck you."

I pulled his dick from my mouth and stroked it while looking up at him, "Oh baby, fuck me. Fuck me like the dirty slut that I am. Fill me with your big cock and make me scream.

His cock was twitching with excitement as my free hand reached into my purse and pulled out a tube of lube. I squeezed some onto his cock, rubbed it in, and listened to him moan. I then switched hands, taking my lubed soaked hand and rubbed my ass, lubing it up to take him inside of me.

I stood up between his legs, and took off my dress and panties. I stood in front of him in just torn stockings and boots.

"Mmmm, that's a good girl. Now come and let me fuck you."

I straddled on top of him and lined his cock with my ass. I felt it push against me and start to stretch my hole. I pushed down a little, waited for my ass to calm, and pushed it again until his head popped inside of me. I moaned feeling the electric pain mix with pleasure. I took more in, pausing every little bit to ease it in. I started to hump gently, taking a little more of his cock each time. Then he was all inside of me and my ass planted firmly in his groin. My own hard cock dangled on his stomach.

He admired my tattooed body in front of him, unflinching when he looked at my own cock. "Someone's enjoying this."

I started to bounce a little faster on his cock, feeling his hands grip my waist tightly. "Oh fuck, yes."

His cock was rubbing all the right spots as I bounced quicker and quicker on his big dick, it stretching my insides with each insertion. I was moaning uncontrollably, gripping the futon behind him as he started to thrust in rhythm with me. His hands moved down and gripped my ass cheeks, then I felt a hard slap.