Buttman’s First Trans Date

She called me Buttman because she worked at the porn store and I was always there looking for Buttman magazines. Her name was Rose - a breathtakingly gorgeous, over 6-foot tall, pre-op trans woman with long, straight blonde hair, naturally pouty pink lips, broad shoulders, firm and shapely arms and legs and a hot, round ass. She told me she was a fan of the Buttman magazines as well. When she told me that, I told her we should hang out and watch some porn sometime and she was into it! So we made arrangements to meet up on that Friday night.

I was a little nervous. This would be my first date with a trans woman! Nervous? Excited? I didn't know what to wear or what to expect. It was like having a first date ever, all over again! I did consider wearing the skin-tight sheer half-top and the crotchless black leather booty shorts, but I thought that might be a bit much for a first date so I decided to just wear a t-shirt and jeans. Albeit a somewhat nice t-shirt with no logos, holes or hot sauce stains. One that fit nice and snuggly, to accentuate what muscles I did have.

I went over to her house, which was actually only a few blocks from mine. I even brought flowers. She opened the door and she was wearing a pink babydoll style halter top that showed a little midriff, blue cut-off jean shorts that showed a LOT of cheek and strappy, white stiletto high-heels which made her even taller and made her muscular legs look even longer...which excited me just a little more. The fact that she was so gentle and ladylike, but still taller and more muscular than me made me even more attracted to her.

She greeted me with a friendly, "Hey Buttman!" and a kiss on the cheek which gave me an instant boner. She invited me in, handed me a tall can of malt liquor

and I got straight to rolling blunts in her kitchen while we chatted it up for a while. We talked about movies, music and people but the conversation kept getting raunchy and going back to the topic of sex, with us laughing like dumb stoners.

She finally asked if I had ever been with a trans woman before. I said no, but I've been curious for a long time. She asked what I was hoping would happen that night. I had to control the urge to roll my eyes as, this was a question so many women had asked me on dates to intimidate me or throw me off my game. And then we would always end up having sex anyway.

"Honestly, I've been fantasizing about it a little." I said with a slight smirk.

"Ooh really?" She replied attentively. "Mmm, tell me your fantasy, Buttman!"

"Well," I smiled, trying to be sly. "I was just thinking we could watch some porn and play with each other's dicks and see where the night takes us."

We laughed.

"I like that," she said. "Such a romantic imagination you have!"

We continued to laugh over a couple shots of whiskey and then went to her bedroom. She turned on some porn while I lit the blunt. I stared at Rose's muscular ass in those jean shorts, cheeks halfway outside of them, with my mind going berserk imagining what her hole must taste like. On the TV, a pretty young trans woman was doing bukkake with a bunch of guys as Rose walked over to the bed and laid down next to me. I feel like she never stopped smiling the entire time.

We snuggled up next to each other as the movie played, our skin just barely touching. We passed the blunt back and forth. We talked a little. We made out a little. We giggled a lot. And of course, we glanced at the movie from time to time.

"Have you and your friends ever done that to a girl before?" She asked.

"What, bukkake? No, my friends don't get down. They all think I'm a pervert and I don't find any of them attractive enough to partake with them anyway."

"You ARE a pervert, BUTT-MAN!!!" she laughed out loud. "Need I remind you how we met?"

"Ok ok, I don't deny being a pervert, it's just that, amongst my actual friends, I am the only pervert. At least I seem to be."

"Right,"

"What about you?"

"What about me?"

"I mean...are you a pervert? Do you do bukkake???" Again we laughed.

"Oh my God!" she flipped her hair back as if to scoff at my audacity and then said, "I mean, a girl can dream, right?" And again, we laughed some more, lightly caressing each other's skin as we passed the blunt back and forth. She turned away from me briefly to put the blunt out in the ashtray, giving me another glimpse of that delicious ass of hers. She then turned towards me and said, "You should take off your pants, Mr. Buttman."

I don't know why, but I hesitated. This was exactly what I wanted to hear her say, so I was in disbelief.

"Get comfortable, relax! How am I supposed to play with your dick if you're still wearing jeans, you silly ass?"

Still laying in bed, I took off my pants and underwear. She stood up and took off her booty shorts. She looked at me as if seeking approval but my dick was out too and very obviously hard as fuck and smiling. She got back into bed and we scooted closer together, close enough to feel each other's skin and start stroking each other's cocks as we watch porn. We start making out again. She got a few good strokes in, from the bottom of my dick to the top, back down and back up, and then pulled her face away from mine to look down at my fully erect penis.

"Holy shit, Buttman, your cock is huge!"

"Yeah? You like it?"

"I love it. It's so beautiful!" She said, as she continued to run her hand up and down my big brown shaft.

"Yours is nice to, baby." I said, stroking her dick gently.

"Thanks," she said with a shy smile. "Guys don't usually compliment my dick. They usually avoid it."

"No baby, fuck them." I said with all sincerity. "Your dick is beautiful." I kissed her lips. "You are beautiful." We embraced and kissed for real this time. As blood surged through both our cocks, we grabbed onto each other's, jerking ferociously now.

"Do you think you can fit my big dick all in your mouth?" I asked with our noses and drooling lips still touching.

"Mmm, let's see..." she said as she licked her lips.

She opened her mouth and slowly but surely, fits the entire motherfucker down her warm, wet throat. She looked up and gave me the affirmative thumbs up and then proceeded to suck my cock - all the way down and back up, hard and fast creating a loud clicking sound with her throat, unable to stop the saliva from spilling out the sides of her mouth and down my balls, dripping into my asshole, which she started working with her middle finger.

"You like that, Buttman?" she asks with her mouth full of cock.

"Yeah, play with my hole, baby!"

She starts finger fucking my asshole as she sucks my cock harder and faster. I start playing with her ass. "Come on, sit on my face baby. I wanna taste your asshole!" I plead.

Without stopping, she climbs on top of my face. I suck her cock a little at first and then I plunge my tongue deep inside her sweet asshole and start fucking her with my tongue, just as hard and fast as she's sucking my cock. She loves it. She's squirming her sexy ass around, rubbing her asshole up and down my face as I jerk her cock and she sucks mine.

"It feels so good baby" she says, holding my head as she shoves her asshole in my face again and again. "Mmm, don't stop!"

I didn't want to stop. Ever. Her hole tasted like a very earthy cotton candy. It was divine. And her excitement as she pounded her ass into my face with her hand full of my hair made me so fucking horny!

"Now I wanna feel you deep in my ass, Buttman!"

She moved her pouting, eager hole down to my cock and inserted me inside of her. Slowly, she began to bounce her sexy, firm ass up and down on my cock while jerking herself off, moaning and groaning in ecstasy. Her straight blonde hair became slightly wavy as she started to break a sweat. She lifted her anus off my cock and spread one of her ass cheeks, so I could see her gaping hole winking at me.

"You like what you see, Buttman?"

"Yes baby, your hole looks so fucking delicious!"

"Mmm, you fucking pervert!" she giggled with sexual excitement. "Eat it, you fucking pervert!"

With her hole now loosened up by my cock, I could now shove my tongue even further up her asshole and fuck her deeper, getting an even louder and more intense reaction. She sat and bounced on my face again as I sucked and tongue fucked her sweet asshole and jerked her big, hard cock.

She moved her asshole back down to my cock and inserted me again. But I knew I wasn't going to last much longer. After another couple minutes or so, I blast cum into her ass, gripping her hips with all my might with all ten inches of my cock all the way up her asshole. We are both screaming blood murder by this point.

She moved her sexy, pouting asshole off my deflating cock and back to my waiting mouth and dumped a hot load of my own cum from her asshole into my mouth.

She begins to clean off my cock with her tongue, causing me to cum again almost instantly, this time in her face and possibly up her nose.

"Mmm, so hot baby," she said as she licked and kissed my cock. "So much cum!"

"I really fucking wanted you tonight, Rose."

She turned around and looked at me like that was the sweetest thing anyone had ever said to her. "Ohhh, babyyy!" She said as she kissed me. With her in my lap, we held each other and made out, passionately. The cum in her mouth flowed into mine, adding a creamy texture to go with the flavor of her asshole. She pulled back and smiled at me again.

"Can I fuck your ass now Buttman?"

Immediately, I was rock hard and ready to go again. "Yeah baby, fuck my ass!"

Enthusiastically, I turned around, put my head down and arched my back to present my eager asshole to her. She mounted me, taking her cock into one hand and my jiggling ass cheek into the other. She spit on her cock and rubbed it in as she inserted herself into me. I was so horny, I instantly turned into a little bitch, shaking my tushy back and forth, not only to excite her more, but also to express my excitement. I finally had the hot trans lady from the porn store up my ass and I was thrilled about it. She grabbed onto my neck with one hand and my chest with the other as I bounced and bounced and bounced until her cock was ready to explode!

"Fill my fucking asshole up with your hot cum!!!" I loudly begged, just the moment before she fulfilled my request. I let all the hot cum run out of my loose, used up hole into my hands and emptied it into my mouth and rubbed it all over my face. We made out again. Now our mouths both enjoyed the warmth and texture of both our cum, blending with the melody of flavors of both our assholes. Not to mention the aroma. It was absolute sensory overload.

"Oh my God" I said between sloppy cum kisses. "I want to fuck you over and over again."

"Me too baby" she said.

We let the bukkake movies continue to play as we intermittently fucked and slept for the rest of the night and following day. This had been the best first date ever!