Loving Tiresias

[1]

Chapter 1

Yes, going home with a guy I just met at a party thrown by a friend of a friend wasn’t a great idea. But, in my defense, one, I was drunk and, two, I was horny, and, three, I was young and stupid.

Is that four reasons?

Anyway, the sex was great, what I remember of it. I do remember taking off his pants and being thrilled he already had a hard-on. It’s not that I mind giving blowjobs. I sort of like giving them, but I’ve been with half-drunk guys before who couldn’t get it up no matter how long I sucked on their dicks.

More importantly, Michael’s cock was perfect. It was even beautiful. Not too big and not too small; I felt a little bit like Goldilocks. And believe me, guys bragging that they have a foot long in their pants don’t get laid nearly as much as they claim. Very few women want something that big in their pussy. On the other hand, something that is more akin to an unimpressive dry erase marker is a disappointment to everyone involved. I like average and I was thrilled when Michael had exactly that.

I remember sucking him a bit, not that he needed it, but because I wanted to. He did his fair share of the work as well. He went down on me like a champ. The last time I was with a virgin was with my high school boyfriend and I am never doing that again. Michael knew exactly what he was doing between a woman’s legs. I loved looking down at his shaggy blonde hair as he ate me out.

Yes, since you asked, he did make me cum that way. It wasn’t the greatest orgasm of my life, but it was fun.

And yes, we fucked. We weren’t so drunk that we forgot the condom either. We did the classic three: missionary, cowgirl, doggy. I don’t know how many times I came, but it was more than a handful. He came only the once, but that seemed to satisfy him.

Then we fell asleep.

That’s when it all went weird and strange and sideways and pear-shaped.

 

I’m all for experimentation in the bedroom. Toys. Games. Bondage. Spanking. Lingerie and fetish wear. Role playing. I’ve only done a handful of threesomes and they were always with two guys. Not that I was opposed to doing a MFF. Having sex with a woman one-on-one wasn’t on my bucket list, but I could see it happening in a group situation.

What I’m saying is that I’m open-minded and short of some extreme stuff, I wouldn’t automatically say no to anything.

But I distinctly remembered falling asleep next to Michael.

I woke up next to a woman.

I was a little girl about it. I didn’t exactly scream, but I yelped and jumped out of bed, dragging half the covers with me getting them into a tangled mess on the floor. This caused me to completely uncover her and prevent me from having anything to cover myself with.

Naturally, my actions woke her up.

“Who are you?” I demanded of the stranger.

Even though it was way too early in the morning and I was a little hung over and she didn’t look her best upon waking up, I could recognize she was pretty and, if I’m being honest, she had a better body than me, so of course I started hating her right away.

The strange blonde sat bolt upright, made a half-hearted attempt to cover herself, an action which was mirrored by me covering my boobs with my left arm and crotch with my right hand. I wasn’t sure why I was doing that.

“Oh shit!” she muttered, blinking and looking around. “I fell asleep.”

“Yeah!” I all but screamed at her. “You fell asleep in my bed! Where the fuck is Michael.”

I was proud of myself that I had remembered my previous night’s partner’s name.

“I’m Michael,” she said. “I mean, I’m Michelle. Just Michelle.”

I glanced down at her crotch. She had a blonde triangle of curly hair and, very distinctly, no dick. No cock. No frank and beans.

I knew I had sucked cock last night. I knew that I had been properly fucked by that same cock.

I was drunk, yes, but was it out of consideration that I would have gone home with a woman?

I wanted to say yes, that was impossible, but I knew it wasn’t. I could have, but I knew I hadn’t.

Did I somehow hook up with a cross dresser, a woman pretending to be a man, and take him...her...home? I didn’t see a strapon harness and cock anywhere on, in, or around the bed. Sure, she could have been wearing one, but I knew I had sucked and fucked a real cock, not some realistic dildo.

Had I?

Michael...or Michelle...or whoever—I was already getting confused on names and I had only been awake for a minute—moved to pull up the sheets just high enough to cover her crotch.

I wanted a better look. Not because I like looking at people’s naughty bits—though truth be told, I do, a little—but because I was starting to have all sorts of doubts.

As I started to lean forward for that close inspection, I caught myself. What the hell was I doing?

This whole thing was insane.

Okay, so I had picked up a woman who was maybe crossdressing as a man and had some lesbian sex which—as I remembered it—was pretty damn good.

What was the problem?

I straightened up and grabbed my robe from the hook where I kept it next to the door.

Feeling a little bolder now that I was covered up and my guest was still naked and exposed, I took a deep breath and said, “Okay, let’s start over. Sorry about my reaction. I was certain I had gone home last night with a guy.”

“You did,” said Michelle.

I blinked. “I’m sorry, what?”

“You did,” she repeated. “You went home with a man last night.”

“Uh...I’m not trying to be close-minded or anything, but I’m looking at your naked tits right now and those, along with everything else I’m seeing, tells me you’re a woman.”

She shifted uncomfortably in my bed and tried to casually cover her breasts with her arm. Her hair wasn’t nearly long enough to cover them, so that part of my memory was intact.

“You went home with a man last night. We had sex. And then during the night I changed from a man to a woman,” Michelle explained like she was giving me the basics of biology.

“That’s not how sex works,” I said, still more than a little confused. “That’s not how gender works. That’s not how humans work! How did you just…” and here I gestured without purpose, “just change into a woman?”

She shrugged and said, “I don’t know. It happens every time I have sex. I change from male to female or female to male.”

I just gawped at her.

“I’d better go,” she said, slipping out of the bed to gather the clothing I had strewn about the room last night when I had stripped Michael before we had sex. I watched her closely. I felt that was my right because it was my damn apartment and I was still confused as hell.

Casual Oxford button down shirt.

Jeans.

Black socks, ankle high.

Plain sneakers.

No bra.

Boxers.

She had boxers and no panties. And no bra.

She started dressing as I watched. Definitely no dick between her legs. I definitely remembered sucking a dick last night. No micro-dick either. It was full sized. Not exactly huge, but big enough to satisfy me.

The boxers were big enough to go over her hips but weren’t exactly a good fit. Besides, the boxers over panties look had expired two decades ago. I continued to watch her dress.

Jeans were an okay fit, but lots of guys wore baggy jeans while women preferred them to be a bit tighter. I know I did. My ass actually looks better in tight jeans than unclothed, I’ll be honest.

The shirt was the giveaway.

Her tits weren’t that big, but they were big enough Bs or Cs. The shirt was tailored to a slim body. She couldn’t get it buttoned up. Her boobs prevented it. Some women would go braless under such a shirt, but not looking like she did.

We both looked down at her compressed boobs trying to escape the shirt. It was a terrible look.

“Do you have a sweatshirt I could borrow?” she finally asked me.

“You want to borrow a sweatshirt from me?” I asked evenly. I understood why, but I was reluctant to give her what she wanted.

“Yeah. So I don’t have to walk home like this. So I don’t get catcalled by every fucking piece of shit I pass on the street. Help a girl out.”

“Aren’t you a guy?” I asked her, half curious, half trying to piss her off.

She didn’t answer my question. “I promise I’ll return it. Girl code.”

“You’re a man.”

“Right now I’m a woman. Here,” she said, digging in a pocket of her jeans and pulling out a man’s wallet. She removed the driver’s license and showed me the picture and the address. “See? I live in the city. I should probably call a Lyft or Uber. I should have worn a jacket last night, but it was so warm out.”

I grabbed the ID away from her. Michael Campbell. The picture was striking. It was the man I fucked last night. I recognized the brilliant blue eyes and shaggy blonde hair. I held the picture up where I could easily compare it next to Michelle’s face. It was the same face, only more feminine.

I glanced at the height. Five foot ten. I’m five eight. Michael wasn’t that much taller than me. Michelle was tall for a woman and I was certain she stood five ten.

“Do you have a twin or something?”I asked. “Are you transitioning?”

“No. I told you. Every time I have sex, I change gender. Yes it’s fucking weird. I meant to leave last night before this happened. It’s a fucking pain in the ass. Sorry to upset you. Can I please borrow a sweatshirt or something?”

In a morning full of surprises, I surprised myself in that moment.

I kissed Michelle.

She was shocked for a moment before she kissed me back.

I remembered the kiss. It lacked the stubble from Michael’s beard but her tongue and taste and feeling, it was all the same.

I had never kissed a girl before. It was more enjoyable than I would have guessed.

It was long and drawn out. I felt her tits mashed up underneath Michael’s shirt pressed up against my own hidden under my heavy robe. It was weird and exciting.

I had fallen asleep the night before promising myself I’d give Michael a wake up blowjob because he seemed like a nice guy and maybe we could make a relationship after our sleazy hookup.

Those plans had been derailed.

Michelle broke the kiss and pushed me back. I think she was just as surprised as I was, which only made sense. I wasn’t acting rationally.

“What the hell was that all about?”

“I wanted to see if...if you still kissed the same.” My explanation made no sense. That was fine.

“Okay, I need to go now,” she said, dropping the sweatshirt issue.

As she started to step away, I grabbed her arms, holding her in place. “Let’s have sex,” I propositioned her. I had done that before with a few men. It had always worked with men because...well, men are men and I’m a rather good fuck and fairly attractive, if I do say so myself.

“What? Why?”

“If we have sex, you’ll change back to a man, right? That’ll prove you’re not lying.”

Michelle laughed at me. “It doesn’t work that way. If I’m a woman, I have to have sex with a man to change to a man. If I’m a man, I have to have sex with a woman to change to a woman. See?”

“That makes no sense.”

“I didn’t create the rules,” she said bitterly. “Just let me go and we’ll forget this ever happened.”

I let go of her arms and stepped back, letting my robe fall open, displaying myself to her. “Let’s have sex. I’ve never had sex with a woman before.” I was still determined to get a close look between her legs. I wanted to prove she was either a liar or I wasn’t going crazy.

Michelle gently shook her head back and forth. “You know, I’ve never had sex in the morning.”

“Okay…”

“It’s because I run out of the bedroom the minute after I’m done having sex. It’s hard to explain all of this,” she said gesturing to her body.

“I can understand that.” I couldn’t understand it at all, but I was rolling with life. “I woke up horny.” I honestly couldn’t explain why I wanted to have sex with Michelle right then and there, but I wanted it.

I stepped closer to her. “If you switch back and forth between being a man and a woman...have you ever had sex with someone of the same gender?”

Michelle actually blushed. It was cute. “Uh...yes. I’m bisexual.”

“I guess that makes your little problem a little easier to deal with.”

“Yeah.”

I had been edging closer and she hadn’t bothered moving away.

At this point we were basically nipple to nipple. Except I was wearing an open robe and she was wearing an Oxford too small for her tits.

Michelle made the next move. Stepping forward, mashing her tits against mine, ducking her head to kiss me.

It was an intense kiss.

Okay, let’s be honest. I’ve drunkenly kissed a couple of women before, mostly to excite guys who were watching at a party or in a bar.

This was nothing like that. It was so intense I felt it right in my pussy.

I was getting wet. I had never gotten wet for a woman before.

From there it was easy to move things forward. I let my robe drop off my shoulders. Michelle put her hands around my waist and drew me in tight before cupping my ass. I struggled a little against her—she was bigger and stronger, but not significantly so—but I managed to open the two buttons she had fastened allowing her to drop the shirt.

We moved back to my bed. Her jeans and boxers came off.

I was on top, half crouching on her, when she slipped a hand between my legs to feel my wet pussy.

I moaned. I pushed my tongue deeper into her mouth to encourage her further. I couldn’t help myself; I started rocking my hips to get more friction from her fingers onto my clit.

“You sure you’ve never had sex with a woman before?” Michelle asked me, briefly breaking our kiss.

“Never.” I put my mouth back on hers and kept kissing. At this point I couldn’t help myself. I wanted to know my own limits. I moved off her mouth and down to her neck and kept moving down.

Eventually I had moved enough that Michelle’s fingers pulled free of my pussy. My lips found her breast and then her nipple. I sucked the sensitive little bit of flesh into my mouth.

Michelle moaned.

My hand found her other nipple and I gently squeezed.

She shivered.

Feeling bolder and more adventurous, I continued my downward descent.

By the time I got to her smooth, hairless belly she caught my jaw with her fingertips, stopping me and tilting my head up. “You don’t have to,” she said.

I grinned at her. “I want to.”

She didn’t stop me when I went lower, down between her legs.

I was positive the person I had fucked the previous night was a man. I remember having a dick in my mouth.

Michelle was definitely a woman. Mound. Clit. Slit. Lips. Hole.

I licked my first pussy wondered what exactly I was doing, but loving it anyway.

I had had lovers who hadn’t the first idea of what to do when confronted face-to-face with a pussy. I had other lovers who were artists when it came to cunnilingus.

I did to Michelle exactly what I liked having done to me.

Okay the smell and taste weren’t a thrill to me. At first. But then I quickly got used to it and even started to like it.

Sex is like that. You start off not knowing what you’re doing and for the weirder stuff, you aren’t sure if you’re going to like it, and then you wind up loving it.

I’m not bragging, but I was an immediate expert at eating pussy.

It took a couple of minutes, but I made Michelle cum. Judging from her moans and cries of passion and the way her body quivered, I was the best lover she had ever had.

Well, the best female lover she had when she was a woman.

After she recovered, Michelle panted heavily a few times. “You’ve done this before.”

I shook my head. “No. Never. You’re my first.”

First woman and first gender-changing partner as well. If she wasn’t lying about that.

“Well, you’re a natural.”

I crawled up her body and kissed her. It seemed like the right thing to do. “Thank you.”

Without warning she flipped me onto my back and once again her hand was between my legs. I resisted her manipulation of my pussy but I didn’t know why.

“Want me to go down on you?” she asked, kissing the side of my neck.

I shivered at the kiss.

“Um...sure.”

She pulled back a bit. “You don’t sound so enthusiastic.”

“When I woke up this morning…” I started to say and then realized that my morning had gone off the rails almost immediately.

“Yes?” she asked expectantly.

I shook my head. “Nothing went as planned this morning.”

“It’s turned out good so far,” she suggested.

“Yeah...but I was hoping to get fucked hard by a nice cock.”

We both looked down at her crotch. She had pretty pussy, but there was a definite lack of dick between her legs.

“I could help you with that...if we could find a man to fuck me. But then again, I wouldn’t turn back into a man again until tomorrow.”

“Ugh. This whole situation is giving me a headache.”

“Do you want me to make you cum?” she offered.

“Yeah...but I was hoping for some cock. Some hard cock.”

“Do you want me to use a vibrator or dildo on you?”

I had several in the bottom drawer of my dresser. Even for a single girl, I had way too many vibrators and dildos. But I could use those on myself anytime I wanted.

“No...I just really wanted cock.”

“I can make you cum with my mouth,” Michelle offered and moved lower on my body. “I promise you I’m really good at it.”

She moved down to my soft tits and took a nipple into her mouth. I shivered at the sensation. I had no reason to doubt her words. But I still wanted more.

“I’ve never been so eager to be fucked in my life,” I whined.

Michael grinned at me. “I think I know exactly what you need.”

She rolled off my body and instead of going for my dresser—though she didn’t know where I kept my toys—she instead re-positioned herself kneeling next to my body.

Before I could ask what was going on, she slipped her middle and ring fingers of her right hand into my pussy. It was nice enough and I was wet enough. I didn’t mind at all when she started jilling me off.

“Mmm,” I moaned.

Ducking her head she caught my other nipple in her mouth and lightly bit down.

I gasped. I liked the little shock.

But I liked what she was doing with her hands even more.

By now she was moving her fingers in and out of me pretty damn fast. Every time she penetrated me fully, the hand slapped against my swollen pussy. It felt good. Really good.

She had average sided hands and fingers. It would have been a godsend if she had fingers like sausages.

A few seconds later the slightly derogatory term squish mitten suddenly made sense to me. I was extremely wet. Every impact of her palm against my clit was an electric thrill. I could feel her fingers curl up inside of me and that was hitting the right spot that I never knew that I had.

In short, in less than two minutes Michelle had me writhing around on the bed begging for release.

I wasn’t ashamed of some of the filthy things that I said...I just hoped that she wouldn’t remember all of them.

When I came, I came hard.

The shakes came first, and then the sudden rush of euphoria and relief. I was floating on the natural high the orgasm gave me when I realized I hadn’t just cum.

I had squirted.

At first I thought that I had peed that bed. That was just crazy and I was in the right frame of mind to realize exactly what had happened.

“I’ve never done that before!” I blurted out to Michelle.

She licked her fingers with a triumphant grin. “Glad to hear it.”

It took me a moment to realize that she was tasting my pussy off her fingers.

It was unexpectedly hot.

“Have you ever squirted?” I asked her.

As soon as I asked the question, I realized how stupid it was.

How would she answer it?

What about all the orgasms she had as a man? Would that be considered squirting, shooting semen?

Michelle looked away from me briefly, but she wasn’t the shy or retiring type. “Not as a woman. But I’ve given plenty of them as a man and a woman. Mostly as a man.”

“Right,” I said uncomfortably. “This is all still pretty crazy. I mean, I went to bed with Michael and woke up with Michelle.”

“Welcome to my world.”

“I just don’t know what to think.”

My bed partner rolled over and out of the bed. She started dressing once again. I didn’t know what to do this time.

“Where are you going?” I asked.

“Home.”

“Do you have to?”

She laughed. “I certainly can’t spend the rest of my life in your apartment.”

Taking the initiative, I jumped out of bed and hopped over to the closet where I pulled out my favorite sweatshirt. I had stolen it from my ex-boyfriend right after college. We broke up right after college.

“Here.” I offered it to her. “This should cover you up fairly well. I don’t have anything else that’s bigger unless you want my winter jacket.”

She gratefully accepted it from me. “Thank you.”

I watched as she continued to get dressed. It was strange to see her pull on the boxers Michael had left on my bedroom floor. I wanted to offer her a pair of my panties, but that seemed like too intimate an act, even after what we had done the night before and this morning.

Michelle buttoned her shirt just enough to keep it closed. She was showing off a huge amount of cleavage. I was a bit jealous.

Then she pulled on the sweatshirt and zipped it up, hiding her boobs away.

I was disappointed, but it fit her well.

I’m sure Erik would be pissed I was loaning it to another lover.

Or maybe he’d get off on the idea of me fucking a woman.

“You look good,” I told her.

It was a lame compliment.

“Thank you.” She stepped into the sneakers she had worn to my place as Michael. Against all reason, they fit her perfectly.

What do large shoes mean on women?

I didn’t know the punchline to that joke.

“I want to see you again,” I blurted out as she looked around to make sure she hadn’t forgotten anything.

Michelle looked surprised at my sudden outburst. “I don’t think you mean that. I have a...complicated life.”

“I still want to see you again,” I said boldly.

“As a man or as a woman?” she threw back at me.

I tilted my head to the side. “Either.” Spinning around, I grabbed my phone off the dresser where I always kept it. “What’s your number?” I asked.

Michelle’s eyes narrowed at me but then she spoke the digits. I put them in my phone and sent her a text message.

“You’re serious?” she asked me.

“Why wouldn’t I be?”

She didn’t have an answer for me. A second later we both heard her phone vibrate inside her jean pocket.

“That’s me,” I said.

“Thanks. I’ll give you a call. Later.”

She walked out of my apartment door.

I wasn’t sure what the hell I thought or believed.

 

 

 

Chapter 2

 

I’ll admit it. I was infatuated. While most of my time with Michael was spent when I was inebriated and most of my time with Michelle was spent having sex, I still felt a connection.

This was something I knew I had to ignore. Michael was just a drunken hookup. Michelle was the first woman I had ever had sex with. Of course they were the same person and that only complicated things.

Like...how the fuck does he...she...change from male to female and back again? Or was I just being naive and I had actually gone back to my place with Michelle because I was drunk and horny and wanted to experiment?

But I saw his ID. I saw her put on his boxers and...everything else.

I was ready to put it all behind me as a drunken episode I’d tell my therapist someday, or maybe my doctor when dementia set in.

I was a good girl. I didn’t call. I didn’t text. I told myself not to think about Michael. Or Michelle.

I had already decided to move on.

That didn’t mean that Sunday night I didn’t put myself to sleep by masturbating and fantasizing about Michael and Michelle. I had them both in my bed at the same time and the fantasy was amazing, even to me, its creator.

So by Monday morning my life was back on track. I had told myself to forget Michael.

And then I got a call from Michael. That’s how I put him into my phone. Michael. No last name. No eggplant or peach emoji.

“Who the hell calls someone without texting first?” I asked myself. Everyone thinks that being a commercial artist is fun and easy. It’s not. I spent way too much time on my own in my studio working on commissioned pieces of art that didn’t interest me at all. That’s probably why I had way too many drunken hookups. And Tinder hookups. And other hookups.

Plus I probably had a personality flaw or two.

I looked at my phone and Michael’s name for far too long.

I didn’t know if I should answer it or not.

Since I was unable to make a decision, it eventually just went to voicemail.

I waited the minute or so for him to leave a voicemail.

I didn’t listen to it.

And then he texted me.

Maybe Michael was as socially awkward as I was.

Hey. I have your sweatshirt. Give me a call or text me. I’ll drop it off whenever you want.

I didn’t answer it right away. I didn’t want to sound desperate.

I wasn’t desperate. I could hook up with anyone I wanted, whenever I wanted.

Okay, maybe not anyone, but I was slutty enough and pretty enough.

I was proud that I waited all of five minutes before I replied.

I work at home. Drop it off whenever you get a chance.

I was cold.

I had to be.

No answer. I didn’t need the sweatshirt.

I just wanted him back in my bed.

Or her. I’d be happy to fuck Michelle again.

The rest of the day was fine. Lots of editing details on the digital files I had been working on. I forced myself to focus. I needed the payday that came when I submitted the files.

And yet I kept checking my phone every time it buzzed.

It was into the evening when I finally got what I wanted.

I’m five minutes away. Are you home?

I didn’t answer because I’m a coward at heart and I immediately rushed to the bathroom to dash on some makeup and do something with my hair.

I wanted to be presentable, but I wanted to see how willing he was to come to my place without a blatant invitation.

Five minutes after he texted, my bell rang. I didn’t run to answer it, but I wanted to.

My place was small. It wasn’t like I could delay forever.

I didn’t want him to show up and just leave.

After checking the peephole, I saw it was Michael. Unfortunately, I live in a building full of artists and students and other assorted dregs of humanity. My peephole showed no detail and the fish-eye lens seriously distorted everything.

I opened the door and smiled at him.

Michael was as gorgeous as I remembered. Five foot ten. Shaggy blonde hair. He also wore a nicely fitted suit that showed off his body. I remembered what that body looked like naked.

I wanted to see him naked again.

I wanted to feel his skin against mine again.

“Hey,” I said casually and leaned against the door frame, not letting him in.

“Hi,” he said with a winning smile that was either the result of superior genetics or thousands of dollars worth of orthodontics. He held up a bag that contained my sweatshirt. Erik’s sweatshirt. It wasn’t a crappy plastic grocery bag. It was a brand new shopping bag. Clean. Still with the original creases.

I saw the Rolex on his wrist.

I took a second look at his suit.

I wasn’t an expert, but it was fucking expensive.

Michael liked slumming.

I felt used.

I still wanted to fuck him.

“Your sweatshirt,” he said, shaking the bag at me.

I took it from him. “Thanks.”

He smiled at me.

I smiled back.

This was going terribly.

I should have asked him if he wanted to come inside. I should have asked if he wanted to go out for a drink. I should have said I wanted to fuck him.

Instead I said, “It belongs to my boyfriend.”

Fuck!

Michael’s eyes widened a little.

Fuck! Fuck! Fuck!

“I mean my ex-boyfriend.”

Shitty recovery.

“Oh.”

“Ex-ex-boyfriend.”

That wasn’t any better.

“I just wanted to show you that I wasn’t lying,” he said.

I blinked. “Lying?”

He gestured to his face. “This is the usual me. Well, sometimes. This is how you met me, right?”

“Right, right,” I chuckled. “You look good no matter what...um...form you’re in.”

“Thanks.”

“Want to come in for a fuck?” I asked.

His eyes went wide. Again. I was so fucked.

“I mean, do you want to come in for a drink?”

Michael smiled and let out a chuckle. “I thought you invited me in for a fuck.”

“Would that be so bad?” I asked, stepping aside and gesturing at my humble artist’s loft.

He walked in and I followed. I tossed aside the sweatshirt bag as I headed for my meager little collection of alcohol. Unfortunately in my tiny apartment, that meant I had to turn to the side and slide past Michael.

Unfortunately?

No. I meant perfectly.

We met eye to eye and my tits all but mashed up against his chest. We were too close. There was nothing else to do.

I kissed him.

He kissed me back. I parted my lips just enough and an instant later his tongue was in my mouth.

He pressed me up against the wall.

It was going better than I had anticipated.

I had to know. There was only one way to do that. I moved my hands down his body and went right for his crotch.

When he felt my groping, he pulled back a bit and looked down at my hand.

After he glanced back up at me I said, “Just checking.”

“I do have a cock.”

“I know. It’s hard.”

“Do you want to fuck?”

I liked Michael. He got right to the point.

“Yes.”

We started stripping off each other’s clothes as we moved toward the bedroom. His suit probably cost more than my monthly rent.

He didn’t seem to mind me dropping the jacket, tie, and pants to the floor.

I didn’t care about my ratty t-shirt, overalls and ancient hoodie.

By the time we got to the bed, I was down to my cami and pink cotton panties.

He was wearing boxers that looked and felt as expensive as every other item of clothing he was wearing.

Surely he had been slumming when he was at Jessa’s party.

I went down on my knees and pulled down his boxers to mid-thigh. His cock popped out and I took it in my mouth.

“Oh...fuck yes,” he moaned.

His pubic hair was the exact same shade as Michelle’s. Maybe there was a little more of it, but it was the same shade. I looked up at him with his cock in my mouth, taking as much of it as possible. I liked the light scattering of chest hair he sported.

I wondered where that hair went when he changed into Michelle.

That didn’t make any sense.

“Is something the matter?” he asked.

I couldn’t answer because my mouth was full of dick. Also, I didn’t know what he meant, but then I realized I had stopped sucking. I was just staring up at him, not sucking or licking or anything. I took his cock out of my mouth.

“Nothing’s the matter,” I said. “Just looking at you. You’re so handsome.”

He had the good manners to blush a little and look to the side. “Thanks. Do you want to keep going?”

“Oh hell yes,” I said and started sucking his cock again.

Not that it’s something I brag about, because it’s impolite to say the least, but I suck a mean cock. I’ve gotten lots of compliments. I could tell that Michael was close to cumming.

“Do you want to cum in my mouth?” I asked, taking a break while stroking his cock.

“Sure. Do you mind?”

I shook my head. “I love swallowing.” Okay, that was an exaggeration, but I loved the reaction from my partners when I did it. I blurted out the next question without thinking because if I thought about it, I would never say it. “If I do, will you change into a woman?”

The question hung between us.

We locked eyes.

“No.”

He said it in such a way that I felt like an idiot. I knew I had been hallucinating. Maybe someone had spiked my drink and imagining Michael as Michelle was just the aftereffect of LSD or whatever.

“Right. Sorry.”

“I can only change into a woman after traditional sex. You know. Penis in vagina.”

I paused again in my blowjob. “Really?”

The feeling of being an idiot washed over me.

“Why would I lie about that?”

“I...I don’t know.” I was still kneeling on the floor in front of him, looking up, his cock in my hand.

“Don’t worry, the change doesn’t happen until after I go to sleep.”

“Okay,” I agreed and for lack of something better to do, I started sucking on his cock again.

I wanted to fuck him. I wanted to feel his cock inside me, but at the same time, I didn’t want him suddenly changing into a woman. That apparently wouldn’t be a problem unless he spent the night again, but seeing that he showed up at my place in a suit he probably worked a traditional nine to five and most likely wouldn’t stay over.

Then again, I sort of wanted to fuck Michelle again.

An idea suddenly occurred to me. “How did you change back into a man?” I asked right as he was approaching nirvana.

Michael groaned in frustration. I didn’t blame him.

“I fucked a guy,” he grunted at me.

“Oh.”

When he was Michelle, he had admitted to me that he was bisexual, but did that apply to Michael as well?

“Is there someone you regularly...get with?”

I was getting jealous and I barely knew Michael. My emotions were taking hold of things I had no right to.

“Sort of,” he said. “Barring that, there’s always a bar and Tinder.”

“Right,” I agreed.

“I don’t want to be rude,” he said, “but are we going to talk or are we going to move things forward here?”

“Oh right. Sure.” I bent my head and returned to the blowjob. A million thoughts were flying around in my head, but I still focused on the fellatio.

The little noises and his body motions were the giveaway. In a minute he had crossed the point of no return and I was going to make him cum.

As a special treat to us both, I kept my lips wrapped around his cock head and when he came, he filled my mouth.

His cum was thick and rich and I could taste the saltiness on my tongue. I had to swallow hard a couple of times as he continued to ejaculate. While he didn’t exactly cum in buckets, it was damn close.

When he was done, Michael staggered back to my bed and sat down. I stayed on my knees a moment longer, swallowed loudly one more time, and then got up. I went to the kitchen for a glass of water, returning as I drank it.

“Holy shit do you know how to suck cock,” he complimented me.

“Thank you.”

“Do you want to keep going?” he asked.

I looked at his deflated cock. It was still handsome, if a little damp. “I don’t think you have it in you right now.”

“Give me a few minutes.”

“I can do that.”

“Great. I wouldn’t want to leave you...unsatisfied.”

I walked around the bed, finishing the water. I was still in my cami and panties. I liked the feeling of being dressed—sort of—while he was naked. It gave me a power rush. Putting the glass on the floor next to my bed, I laid down next to him, feeling his warm body against mine.

“I have one more question,” I said.

“Okay,” he said softly.

I hoped he wasn’t going to sleep.

“What about anal sex?”

Since I was already looking at him, when his eyes popped open I was pleasantly surprised. “What about it?”

“You said you only change when you have PIV sex. What if you have anal sex?” I looked at him innocently.

“I don’t know,” was his answer.

“What do you mean you don’t know.”

“Uh...I don’t know. I’ve never had anal sex.”

My eyes narrowed. “You have got to be kidding me. You’ve never done anal.”

I was sex shaming him, but it was accidental. Honest.

“Can’t say that I have,” he replied, trying to brush off my accidental humiliation of him. “I’m more into pussies and mouths.”

“What about dicks?”

“What about them?”

“When you’re a woman, do you like dicks?”

“Yes...and when I’m a man. I told you. I’m bi.”

“And you’ve never had anal?” I asked skeptically. “I mean, when you’re a woman, not once has a guy you’ve been with asked to fuck your ass?”

“No…?” He said it like a question.

“Has a guy ever tried to fuck your ass?”

“I mean, probably, but I always just insisted they put it where it belongs.”

“Okay, you totally have to fuck me in the ass!” I declared and jumped out of the bed to go to the bottom drawer of my dresser. I’m always prepared when it comes to sex.

Well, almost always prepared. At least 99.9% of the time.

I wasn’t prepared to go to sleep with Michael and wake up with Michelle.

I bounced back on the bed with a bottle of lube in one hand and a box of condoms in the other.

“Ready to fuck my ass?” I asked him, turning around and shaking it at him.

I’m not a great dancer. I sometimes forget to eat. Before I started making decent money as an artist I sometimes didn’t have enough to eat. As a consequence I have a small ass. I wondered what Michael was thinking when my small ass inside my pink cotton panties was shaken in front of his face in a manner that couldn’t have been all that attractive or interesting.

“You really want me to fuck you in the ass?”

“Yes!” I dropped to the bed, dropped the condoms and lube, and pulled up my cami, tossing it to the side. “I love anal sex!”

I raised his eyebrows and gave me a skeptical look. “Really?”

“Yeah. Why would I lie about that?”

Flopping back, I pulled off my panties and tossed them aside with a bit of flair. My little strip of black curls needed some attention. I was getting stubble on the sides, but I couldn’t worry about that right now. I needed to focus on getting my ass ready for Michael’s perfect cock.

“Uhh...most women aren’t into anal sex,” he said. His cock was semi-hard. I hoped the idea of plunging into my black depths got him excited.

“I’m the exception,” I said as I lifted up my legs to my chest and applied a heavy dose of lube to my back entrance. While I did like anal sex, preparation was key. He wasn’t going in dry. “I think more women would like anal if they were simply more open to it.” I paused. Michael hadn’t moved. “What’s the matter?”

“Are you sure about this?”

“Yes. Why are you questioning me?”

“It just seems odd...and a weird thing to do on a first date.”

Now I paused. “Is this a first date? Wouldn’t it be a second date?”

“Is it a date at all?” he asked me. “We hooked up at that party and now I came over to return your sweatshirt.”

“Erik’s sweatshirt,” I corrected him. “My ex-boyfriend.”

“Right.”

“Well, I’m having fun and getting to know you, so I consider that a date.”

“Okay…”

“Look, do you want to do this or not?” I asked him bluntly. “If you’re afraid or something else...maybe we should rethink this.”

His attitude changed immediately. “No! I’m into this! I just want to make sure that you want to do it.”

“It was my idea,” I reminded him. Seeing that his cock wasn’t hard enough yet, I leaned over and took it in my mouth, surrounding his flesh with warmth and wetness.

I don’t know the reason but he got real hard, real quick. Not wanting him to have second and third thoughts about what we were going to do, I grabbed the box of condoms, opened one up and rolled it on his cock.

When I backed away, he looked down at his dick with a surprised expression. “I didn’t even feel you put it on.”

“A trick I learned years ago.” I laid down on the bed and opened up my legs. “I really like anal, but I need to get warmed up first. Go down on me?”

I didn’t have to ask Michael twice. He moved over to me and got down between my legs.

While my memory isn’t perfect, his technique was much the same as Michelle’s. That is to say, he ate pussy with skill and enthusiasm.

I let myself relax. I wanted to cum because an orgasm before anal sex made getting buggered easier and more fun.

My hands went to my tits and I idly played with my nipples as Michael sucked on my clit and shoved two fingers into my pussy. I was excited because anal is so much fun with the right person.

I was convinced Michael was the right person.

It was just a mild orgasm, but it was enough.

“Oh...yeah,” I moaned.

He lifted his face from my pussy. “You like that?”

“I love it. Now shove your cock up my ass,” I told him.

He seemed confused. I put my hand on his cock and pulled him to me.

Naturally he hadn’t put any lube on yet. I grabbed the bottle from the bed and got him good and slippery.

I couldn’t remember doing it this way before, with a man kneeling between my legs as I applied lube, but it worked.

Michael was genuinely confused when I pulled my legs up to my chest and smiled at him. “Okay, go ahead. I’m nice and relaxed and ready.”

“Don’t...don’t you want to turn over.”

“Doggy style?”

“Yeah.”

I shook my head. “No. I like this position better.”

“On your back?”

I was getting tired of all his questions.

“Yes. On my back. Please fuck my ass now or get out of my apartment.”

He opened his mouth to answer me, but then he tilted his head to the side and nodded.

“Okay then.”

I kept my hands behind my knees, pulling my thighs against my body, as he fumbled with his cock, trying to find my back entrance. I allowed him to find his own way. It was his first time, after all. And I was using my best lube. My ass and his cock were extra slippery.

Even his fumbling around felt good.

And then he finally found the right location and angle and he pushed inside me.

“Oh...fuuuck,” I groaned as he opened me up.

Michael froze.

“Did I hurt you?”

I flopped my head back and forth. “No. Feels good. Just...go slow.”

He started to push further into me.

It was wrong.

“No! Wait. Just...just give me a second to take it in.”

One of my tricks was just to be patient and wait a minute to let my body get used to the welcome invasion. My sphincter eventually relaxed and Michael was a bit surprised that he started sinking further inside me.

“Oh...yeah. That’s good,” I muttered. “That’s great.”

“Holy shit,” was his entire commentary.

“Now, slowly go in and out. Don’t fuck me like a gasping fish. Gentle is the key.”

“Okay,” he nodded.

Since he was on his knees and my ass was in the air, it was easy to let go of one leg and slide it down to my pussy where I pushed a pair of fingers inside, getting them wet, before I started running them over my clit.

“What are you doing?” he asked me.

“Just fuck me,” I told him.

Already I was too distracted by his cock in my ass and my fingers playing a concerto on my clit to have enough brain power to carry on a conversation.

Apparently anal sex was enough of a novel experience for Michael that he didn’t want to keep talking. He slowly pumped his cock in and out of me.There’s an art to buggering a woman and he was a natural at it.

I was moaning and making the little noises that embarrassed me when I reflected on them after sex, but in the moment I was enjoying everything he was doing to me and how my body was responding.

I wasn’t worried about his pleasure. Michael already got to cum once and it took no special art to make a man cum a second or even a third time. A woman’s pussy is a complicated organ and I knew how to play mine like a virtuoso.

It had been a while since I had been buggered so it didn’t take me long at all to reach my first orgasm. It wasn’t an anal orgasm but one originating from my clit. I could tell the difference. I didn’t let Michael know that. I only screamed a little as I came.

“Holy shit did you just cum?”

“Uh-huh.”

“Did I do that?”

“Uh-huh.” He had helped, but he wasn’t the primary driver.

“I could feel you clamp down on my cock when you came.”

“Uh-huh. Keep fucking me. Make me cum again.”

With a nod, Michael went back to work on me.

I don’t think I ever had straight anal sex, if such a thing exists. I always had to play with my pussy when someone’s cock was up in my ass. More than once I had wondered what it would be like to just be fucked in the ass without putting my pussy into play, but tonight was not the night.

Emboldened by my earlier orgasm, Michael was chuffed at his anal sex skills. He fucked me well. I came again. It was easy for me to cum a second or third or more times once I had my first.

Michael suddenly stiffened. His entire body, not just his cock.

He was cumming.

I loved the expression on his face.

Men had cum in my ass before. I wasn’t a big fan of having semen inside my ass so I had started insisting on them using a condom when they buggered me or I needed a promise to pull out before they completed.

When he was done, Michael collapsed on the bed next to me. “Was it...was it good for you too?” he asked, half laughing.

I kissed him.

“It’s always good for me. I love having my ass fucked.”

 

 

Chapter 3

 

I want to thank you for a great night.

I looked at the text and smiled. Michael hadn’t spent the night. He claimed an early morning meeting at work. It was a nice lie. At least he took the effort to come up with something semi-plausible so he didn’t have to spend the night.

But I was thrilled when he texted me. It meant he wanted to see me again.

I wasn’t stupid.

You’re more than welcome. I had a great time too. Want to do it again?

I was being bold. I liked being bold.

And I was curious. I wanted to be sure he wasn’t a liar about shifting back and forth between man and woman.

It only took him a minute to reply.

Yes.

Perfect.

But I had to know. We had fucked the night before and according to him, he would change into a woman after sex.

Send me a dick pic, I texted to him.

The reply was more or less what I expected. You’re kidding.

Why would I kid about that?

His answer was exactly what I expected. I’ve never been asked for a dick pic from a woman before.

Interesting. Write the number 678 on your thigh. I don’t want you to send me a fake. But I think I’ll recognize your cock.

There wasn’t a response for a long time. I took that to mean he was doing what I asked. Maybe he was jerking off a little too, getting his cock big for a good visual.

I didn’t need that. I just wanted to make sure he was still a man.

When he sent the picture, I wasn’t sure if I was thrilled or disappointed.

It was his cock. I was well-familiar with Michael’s cock now. I had dreamed about it the night before. It was perfect.

It lay heavily against his thigh with the 678 written in what looked like black Sharpie. His pants were down to his knees and he was sitting behind a huge wooden desk.

That’s hot, I sent back to him. I thought you were supposed to turn into a woman after having sex with a woman.

I only change if I have PIV sex. You gave me a blowjob last night and we had anal.

I thought about that for a long time. In response I sent him a picture of my pussy.

It wasn’t a photo, it was a hand-drawn charcoal drawing I had done by sitting on the floor with my legs spread in front of a mirror.

I sent him a message as well. Maybe you need to fuck this pussy again.

Keeping my more pornographic art on my phone wasn’t necessarily a good idea, but I didn’t live my life by just following good ideas.

Did you draw that? He asked a minute later.