Maing Me a Sissy

Thank you Oldbroad76 for editing.

At 27 years old and married, I thought all of the excitement in my life was behind me, and it was. For three years I was happily married and having missionary sex once a month. I worked long hours, as did my wife. We had a house and talked about kids.

For my entire life I had been following the normal blueprint that was life, but that all changed when out of the blue she left me.

Diane, my wife, one day couldn't take anymore, and in one blow, she admitted to having an affair with her boss, Jeffrey. She left me that night, and I haven't seen her since. Just her wardrobe full of clothes were left behind to remind me of her.

My name is Anthony, I am 5 foot 9, slim but toned as I go to the gym at least 3 times a week. I also have short, brunette hair, and although I hated to admit it, I have feminine features with my plump lips, bright blue eyes, long eye lashes, and naturally tanned skin.

For months after Diane left me I either went to work, the gym, or stayed at home alone. It all became one boring blur.

I didn't see it changing, and I didn't do anything to change it, but then I met Wayne.

--

Ten!

I grunted and dropped the weights after my chest press. I had just finished my final set and sat up. My face was red, and I was panting.

"Nice work." A deep voice said, and I jumped.

As I turned around, my eyes opened wide to see a giant, muscular black man standing behind me. And when I say black, I mean night sky black.

His body was hard to miss as he was only wearing a vest that barely covered him. He was well over six foot tall with arms like tree trunks. I thought that he must have had nearly zero body fat as he was pure muscle.

"Erm, thanks." I replied back, finding myself nervous next to this beast.

"I'm new to this gym," He said, his deep voice almost angelic like, "And I prefer to work out with someone rather than on my own."

"Oh, fair enough." I replied, still finding myself feeling awkward with him so near to me.

My chest was still heaving and I was sweating as I reached for my water bottle, but he grabbed it first and handed it to me.

"I'm Wayne." He said, his eyes staring into my soul.

"Erm, Anthony." I replied back.

"Nice to meet you." He said.

Before I knew it, Wayne's big, black hand gripped onto mine. I didn't consider myself small, but his hand engulfed mine.

"You too," I said to him. "I'm actually just finishing up."

"Shame," Wayne replied, "maybe next time."

He walked off after that, and I let out another heavy breath. Other than at work, that was probably the most contact I'd had with another human being since Diane left me.

Realising this, I made a decision.

I stood up from the bench press and walked over to Wayne who had set himself up on a cable machine. I couldn't believe the weight he was going to be lifting. It was nearly twice what I could lift.

"Hey," I said, and Wayne turned around and smiled, showing off his shiny white teeth. "I'll be here tomorrow at 7pm if you want to train together then?"

"Perfect," He told me, "see you then."

As he stared at me, I felt something... tingling. Which lasted even after I had left the gym. I couldn't explain it, but my body reacted in a strange new way just from speaking with Wayne.

Even with that, I was excited. Maybe this was me finally taking the first step in moving on with my life after Diane.

--

The next night after I finished work, I rushed to the gym. I wanted to make a good impression with Wayne, hoping to make a new friend.

When I arrived, he was already there and putting weights onto the leg press machine.

"Anthony," He bellowed out, which caught the attention of nearly everyone there, "just in time."

"Hey," I replied as I walked over, "legs today?"

"Yeah, if you're cool with that?" Wayne asked.

I nodded as I stared at him. I couldn't put my finger on his age. His ebony skin was silky smooth, but he gave off the impression of a wise, older man. I wouldn't have been surprised if he was anywhere from 30 to 50 years old.

"I'll go first," He said as he sat on the machine. "Then we can change the weights to whatever you need."

"Yeah, not a chance in hell I could do that weight." I joked back.

"Well, I have about twenty years practice on you," He joked back.

I watched as his thick legs tensed while he pushed the weights up. He was honestly a machine. He was pressing so much weight that I gulped at the sight of it.

As he pressed the machine, my eyes went all over his big, black body. Every inch bulged, and he was truly a god of a man.

"Okay, your turn," He said and stood up, barely breaking a sweat. "What do you think you can do?"

"Maybe half?" I said and struggled to take his weights off.

"No need to push yourself too hard if you want to go lower." He told me.

I agreed and took even more off before struggling to do my set.

During our work out we didn't talk a lot, and most of it was about workouts and a gym pattern that we could get into together. He seemed like a nice, warm guy.

Then when we finished and my legs felt like jelly, we made our way towards the door.

"Want to go for a quick drink?" Wayne asked me.

It's nearly 9pm,

I thought, knowing that my bed was waiting for me, and then work in the morning,

come on, try and have some sort of a life.

"Yeah, sounds good to me," I told him. "It might give my legs time to work properly again before I drive."

"Perfect, there's a place just around the corner, right?" He asked me.

"Yeah, I'll show you." I told him.

When the cold night air hit my sweaty body, I felt refreshed. The wind blew against my wet body which instantly cooled me down as I walked side by side with this beast of a man.

"So, you lived here long?" Wayne asked as we walked.

"I moved here about four years ago," I told him, "to move in with my wife."

"Oh, I didn't see a ring." Wayne said to me.

I looked at my bare hand awkwardly as we walked.

"We, erm, we separated a few months ago." I admitted.

Don't be depressing, you could actually make a friend here!

"But it's all good," I told him, "neither of us were happy."

"Women, hey?" Wayne joked back.

"What about you?" I asked, "got a wife waiting for you at home?"

"Me? No," Wayne said, "I find relationships too much of a hassle."

I chuckled when he said that, thinking back to many nights of Diane being in a mood with me over the smallest of comments.

"I get that," I replied. "So, no kids, I guess?"

"No chance," He told me. "And at my age, I doubt I'll have any."

"How old are you?" I asked, not thinking that it could come off as rude.

"43." Wayne told me as we reached the bar, and he opened the door for me.

We headed inside, and I got us a seat while Wayne went to the bar. He came back with two diet sodas and sat back down.

"Were you with your wife for long?" He asked me.

"She's the only girlfriend I've had," I admitted. "We'd been together since we were 18."

"Wow," Wayne said in honest shock. "I couldn't imagine being with one person that long! And you never, you know, got action elsewhere?"

"I didn't." I said, putting emphasis on the word "I" without meaning to.

"Oh, I see," He replied and placed a big, black hand onto my shoulder. "I'm sorry to hear about that."

Fuck sake, don't let him think you're some kind of loser.

"It's fine," I told him, "honestly."

His fingers dug into my shoulder like steel into butter.

"Well, I'll help you forget about her." He spoke in a deep, undertone.

That tingling feeling returned to my body when he said that,

what is this feeling?

What's worse is that while his big, strong fingers grabbed my shoulder, my cock started to twitch.

I sipped on my drink, and Wayne's hand left my body as he sipped on his drink.

"I take it if you were together since you were so young, and you didn't cheat, that she's the only woman you've been with?" He asked me.

This took me by surprise, and I nearly choked on my drink.

"Sorry," Wayne laughed, "I can be pretty blunt."

"It's fine," I coughed again and wiped my mouth, "but yeah, only one."

"What a waste," he joked back, "at least your mates should help you get some action, right?"

I looked at him, again wondering how to word it without seeming pathetic.

"Well," I said, "I kind of went all in with my wife... when I moved down here, I didn't stay in touch with my mates."

Wayne grabbed my shoulder again, and I'm sure he didn't mean to, but it made me feel tiny.

"Well now you have me." He said.

Once again, my cock twitched.

We chatted about general stuff that night, although most of it was Wayne asking about me and not revealing much about himself.

--

When I got home it was pretty late, but I couldn't shake this tingling feeling, or the fact that my cock was rock hard.

As I got into bed, I knew I was going to have a wank, something I hadn't done for weeks. But when I stroked my four inch cock and closed my eyes, Wayne popped into my head.

What the fuck?

But even as I tried to distract myself, I couldn't stop thinking about him and eventually gave up on fighting it. I was quickly wanking as I pictured Wayne's big, black body, and then I remembered his hand on my shoulder and wondered what he would feel like to touch.

Then I wondered what his cock would look like. If it was anything like his body, then it would be huge and dark black!

"Oooh fuck!" I moaned as I covered my chest and stomach in cum as soon as I pictured his cock.

That was the first ever time I pictured another man while wanking, but it was undeniably the best orgasm of my life.

--

The next night I was at the gym again with Wayne, but this time he became more touchy. He helped lift me off machines and used his big hands to guide me with my lifts. At first I tensed up, but after an hour I welcomed his touch.

His ebony skin felt so soft when it was against me, and when he helped me to my feet I felt tiny in comparison to him.

Once again, I came to the thought of Wayne that night.

--

A few weeks later, I had become very comfortable with Wayne and his touching. It took another step though when we were working our chest, and I laid down on the chest press.

I looked up at the bar above me when I was shadowed by Wayne. His tree trunk legs stood wide apart with only a pair of baggy shorts hiding what was beneath, the thing I had been fantasising so much about recently.

Wayne squatted down to help me with the bar, but when I realised I could see the outline of his cock, I couldn't focus on anything else.

Oh my god! It looks massive!

"Ooh fuck!" I grunted as I dropped the bar, but luckily Wayne grabbed onto it and easily put it back onto the support.

"You okay there?" Wayne laughed out.

My face was flustered, and the outline of his cock disappeared.

"Erm, yeah, sorry, I got distracted." I told him without thinking.

Wayne let out a heavy chuckle as I put my hands back onto the bar.

"Okay, try and focus this time." He told me, but as he spoke, I could see his cock moving around underneath his shorts.

My mouth began to water as I stared at the bulge, wondering what it looked like.

This time as Wayne lowered the weight, I focused and managed to do my set.

That night when I got to bed, I was lost in my thoughts.

So what, I was staring at his crotch? I'm single, and it's 2024, nothing wrong with being curious anymore. I mean, Wayne probably isn't even into that... but if he was... there wouldn't be anything wrong with exploring? I've spent all of my life with one girl, maybe I should try something different.

--

The next time I saw Wayne, I was nervous for completely new reasons. I had admitted to myself that I was attracted to another man, and not just any man, but a massive black man.

"Hey!" Wayne shouted as I walked over to him.

My cheeks felt flush, and my mouth dried up.

"Hey." I whispered back.

This immediately brought a new reaction for Wayne, a sort of victorious smile.

"Ready for legs?" He asked me.

"Yeah, sure." I replied.

As normal he went first, but I spent the entire time happily admiring his body. His short, shorts rode up his thick, ebony thighs. My eyes went all over his muscular body. His short black hair started to glisten with sweat as he worked out.

I realised that my cock was starting to grow as I stared at him, and I needed to keep it under control.

By the end of the workout, I was a horny mess. I knew that as soon as I got home, I would be wanking again over this beautiful man.

"You've never invited me to your place." Wayne suddenly said as we reached the gym entrance.

"What?" I asked.

"We've been coming here for ages now, and you've never invited me over," Wayne repeated. "They don't like black guys in your neighbourhood or something?"

"No!" I immediately replied back, not wanting to give off any sort of racist implication. "I'm sorry, I didn't think you'd want to come over. Do you want to?"

"Of course," Wayne said and wrapped a thick arm around me. "We're good mates now, and it's about time I see your house."

Is he interested the same way I am?

I thought. I wondered if this might be my first ever gay experience. I couldn't deny that the idea excited me.

We got into our separate cars, and Wayne followed me back to mine. When we pulled up it was pitch black outside, and I led him to my living room.

"Nice place," Wayne said as he looked around. "You must earn alright money to afford this on your own?"

"Yeah, I do alright." I told him. "Do you want a drink?"

"Thanks." Wayne replied and sat down on my sofa.

As I got us both a glass of water, I returned to the living room, and when I handed the drink to Wayne, I went and sat down on a single armchair.

My cock was stirring in my shorts, and my head was running wild with thoughts of having my first gay encounter.

"So," Wayne said as he placed his glass down, "seems you've been distracted around me lately?"

My heart sped up, and I felt shivers all over.

"I guess you could say that." I replied, wanting him to know that I was feeling it.

He leaned his elbows onto his knees and looked at me with seriousness in his eyes, like I was his prey.

"Have you ever done this before?" He asked.

I gulped as my throat dried.

"Done... what?" I nervously asked.

"You don't need to be coy anymore," Wayne replied, "we both know I didn't come here just for a drink."

There it is.

I put my glass down and looked at him nervously. Suddenly I felt really, really small.

"Oh, erm, no I haven't," I admitted. "Have you?"

"Yep," He replied which made my heart beat fast again, "but no one as masculine as you, but we can work on that."

What does that mean?

I didn't know what to do. Was I supposed to sit next to him? Kiss him maybe? Luckily, the more experienced Wayne took charge.

"Why don't you get onto your knees and come here." He suggested, but in a dominant, tone.

Oh my god, this is happening.

"N-now?" I stuttered as my fingers played in my lap.

"I'll tell you this now," Wayne spoke as he leaned back against the sofa and spread his legs further apart. "I don't like to repeat myself."

His dominant manner took me by surprise, but after that initial reaction, I was grateful that he could take charge and lead the way.

"Okay." I whispered.

I took a deep breath and looked at him one last time as I stood up.

"I said on your knees." He said slowly but confidently.

Oh god, what am I doing?

I thought, but I couldn't deny the effect it was taking on my hard cock.

As I sunk down to my knees, a hint of a smile could be seen on Wayne's dark face.

"Now, crawl to me." He instructed.

I felt stupid being on my knees in my own house, stupid and horny! Which helped guide my body to slowly crawl to Wayne until I was between his legs.

I can't believe I'm actually about to do this with a man.

From between his legs, I looked at his crotch and then his eyes.

"Take it out." He instructed, keeping his strong arms on the back of the sofa.

My own hands were physically shaking as I reached for his shorts. My fingers fumbled about with his waistband until I got a proper hold of them. I could see the outline of a cock in his shorts which filled me with excitement and nerves.

Then Wayne lifted his ass from the sofa, and I began to pull his shorts down. As they got lower, I first was greeted with his thick, black pubic hair.

I pulled further and saw the base of his shaft... he was so thick!

His cock was pointing down, and I kept pulling and pulling until... he sprung free.

"Oh my god." I gasped at the size.

After his cock, his shorts easily fell down to his ankles, and Wayne kicked them away. Looking at him now, his semi hard, thick, massive black cock was resting on his thigh. Even semi hard it looked the size of my forearm.

My own cock was rock hard at the sight of it.

"What do you think?" Wayne asked.

I couldn't take my eyes away from his dark meat as my mouth watered.

"You're so... big." I whispered.

"Look at me." Wayne ordered which made my body jolt up.

I dragged my eyes away from his cock and looked at the big black man in front of me.

"I need to make a few things clear before we start," Wayne told me clearly, and I nodded. "I'm dominant. And when I say that, I mean very dominant."

That was already obvious, and again I was happy to let him take charge. I had never been a dominant person myself anyway, so I nodded in agreement.

"Good, second thing," Wayne continued, "I'm not a faggot. When you take my cock, you are no longer a man. You're a slut for me to use. You have a mouth and a pussy, and yes, I intend on using both. Your dick is no longer a dick, it's a clit. If you're lucky enough, I will let you rub it and let you cum, but never before I cum. Got it?"

My mind raced. It all sounded so ridiculous. To start with him saying he wasn't a faggot but implying I was when this was my first ever time doing anything with a man. And then to say I had a pussy.... I couldn't imagine fitting him in my ass that had never been touched before.

Considering me as a woman... it sort of made sense in my head, and it made my cock go wild.

So, I looked at him and swallowed.

"I understand." I whispered.

"Good girl," Wayne said, and my body shivered with excitement. "Touch my cock but don't put it in your mouth yet."

My hands moved in slow motion as I reached to touch my first ever cock.

When my fingers grazed against his shaft, I couldn't believe the warmth irradiating off him. The fingers on my right hand wrapped around his shaft and moved around. He wasn't fully hard, but he was getting there.

I held his cock up, inspecting it all over as I held him in my hand.

The longer I held him, the harder he got. My own cock that wasn't being touched started to find amazing pleasure in just touching him.

He just kept growing and growing to the point where my fingers stopped touching around his shaft.

"One hand might be enough for your little cock," Wayne growled at me, "but around a real man's dick, you use two."

I nodded and wrapped the fingers on my left hand around his shaft. Even with both hands there was still plenty of his big cock untouched.

"Okay, start stroking me." Wayne ordered.

I'm wanking another man,

I kept thinking as my hands slowly moved up and down.

Wayne's big, black cock was now completely hard, and his purple head bulged, just waiting to be pleased. This shaft was thick, but his skin was so smooth. As my hands moved up, I saw his big, hairy, black balls lift with it and then back down again.