Curiosity Got the Better of Me

This happened with I was in my early twenties, after university I had moved far away from home for a good work opportunity. My girlfriend of a few years decided to move with me, but after a few hard months we broke up. The distance from her family was too much for her, and our sex life had taken a big hit. She still enjoyed sex, but only when I was initiated. Eventually I tired of always being the aggressor in our sex life. I wanted to spice things up, have her be more dominate and to explore my submissive side, but she had no interest in that. We fought about that and many other things before we called it quits.

A few months after she went home, I was lonely, bored, and horny. It's a lot harder to meet people outside of university and my co-workers were all older with families. My social life consisted of video chats with friends and family and working out. On weekends I liked to get high before playing video games and watching porn. The porn I watched since the breakup started with some basic female domination and eventually drifted into more things like transsexuals, crossdressing, and sissy porn. I had found some panties and a pair of yoga pants that my ex had left behind and started wearing them during my porn sessions. I got a little obsessed with getting dominated by a strong, confident woman, and with exploring my submissive and feminine side.

At some point the porn wasn't really cutting it and I was really missing a human touch. After much deliberation I wrote a post on Craigslist that said, 'I'm a recently single, open-minded, fit guy in my 20's whose looking for a woman to dominate me, and to help me explore my submissive side.' To help, I included a picture of me in yoga pants bending over, showing my fit, round ass, and my athletic and mostly hairless body. I knew it was a long shot to get a girl on Craigslist, but desperate times call got desperate measures.

After I posted, I decided to smoke a joint and take a shower to calm my nerves. When I got back to my computer, I was pleasantly surprised to see I had a bunch of replies, unfortunately none were women. All the replies were men and most were some variation of 'Hey, nice ass, wanna suck my cock?' with a poorly taken dick pic, which I ignored.

One of the replies, however, was a well written reply that said, 'Hey bud, I know your that you're looking for a dominant chick but those are hard to find. Lucky for you though, I know exactly what you are looking for. I've met several straight guys like you, and they always leave satisfied. I guarantee you'll have a great time, and you will discover something about yourself that you didn't know. Talk to you soon, Tony.' He also included a couple of well taken partly clothed full body pics. I could see he was a very fit and handsome man. He had well-defined chest and abs, covered with a bit of dark hair, and the sweatpants he was wearing hinted at something large beneath.

Maybe it was the weed or the loneliness or something else, but his post intrigued me. His casual confidence came through in his well written message and hot pictures. However, in my head I was straight, so I wasn't really going to consider it, right? I re-read his reply and looked at his pics again and each time I got a little and felt something stir inside me. I decided to take a walk to try and clear my head, thinking that when I got back, I'd realize how crazy this is. I got back and decided that despite the temptation, I was straight, and I wasn't looking to change that. But since he wrote a nice reply and that he seems like a good guy, I'd reply and let him down easy, or so I thought.

I replied, 'Hey Tony, thanks for the reply. I appreciate that you took the time to write a well written response and hot pictures, instead of crude reply and a dick pic. Your confident reply caught me by surprise and has me intrigued. However, I'm straight and I don't want to waste your time when I'm sure you have no problem finding a gay guy to have fun with. Anyway, I'm still hoping to find a woman to dominate me. Have a great night, Andy'.

To my surprise he replied again, 'Hey Andy, you're definitely not wasting my time, I know what I want. And, as attractive as you are, you won't have much luck finding women on this site. You can either jerk off alone again tonight or hang out with me. Besides, there's nothing wrong with 2 hot guys chilling out with a beer and a joint. No pressure to do anything you don't want to do, but you'll want too 😉. Here's my address, the buzzer code is 221. See your sexy ass soon! Tony... And not that you need more enticement but here's another pic that I know you'll enjoy <3'.

I was stunned by his confidence! He not only assumed that I'd come over, but also that I'd give in to him. I didn't open the picture right away as I tried to resist him, and I was thinking of how to turn him down. I kept looking at the email, trying to decide what to say, before my curiosity got the best of me and I finally opened the picture.

And when I did, I was mesmerized! He sent a full body nude that showed his dark hairy, ripped chest and abs off and his thick hard cock. And beneath his cock was a guy on his knees, who looked a little like me, with long, shaggy blonde hair and a smooth hairless body. His mouth was open, worshipping Tony's cock.

I must've been staring for a good 5 minutes before I realized that I was rock hard, playing with myself, imagining what it would be like if it was me. This time I didn't even fight it, I got dressed and nervously headed out to my first ever meetup with a guy.

About 15 minutes later I was standing in front of the buzzer. After a minute's hesitation, I took a deep breath and punched in the code. Two long rings later a gruff masculine voice chuckled, buzzed me in and said, 'come up'. I slowly walked up to the second floor and found his door. This was it; I was about to meet a guy up who's goal for the night was to fuck me for the first time in my life. My heart was pounding through my chest, so I paused for a moment to gather my nerves and knocked.

He opened the door wearing nothing but a pair of sweatpants, which did nothing to hide his large bulge. He was at least 6'3", around 220 pounds, and very muscular. I wasn't small at 6'0" and 180 pounds but he looked like he could pin me down with 1 arm. With a ripped and hairy chest and a thick beard, he looked like a man's man and made me feel small by comparison. He looked a bit intimidating, but he greeted me like an old friend with a big smile, while he told me to come in and make myself comfortable. As I slipped past him, I noticed him checking my ass out. I could feel myself get a little turned on at the attention.

He grabbed us some beers and sat down next to me to light a joint. We drank, smoked, and chatted for awhile, while I got comfortable. I couldn't help but check out his body, and he noticed this and kept 'adjusting' himself, attracting more glances from me. As the weed and booze hit, I started to relax and we were quickly laughing and having a good time.

Naturally, the conversation drifted to relationships and sex, and he asked me what brought me here. I told him about my last relationship and how I wanted to explore my submissive side with her, but she wasn't interested in that. I also told him about the porn I'd been watching and the fantasies I've had, and that I'd been hoping to find someone to take charge for once. I continued that I had never though that I'd meet up with a guy, but there was just something about the way he responded that unlocked something deep in me that I didn't know was there. I was embarrassed that I opened up so much, but he was a good listener.

He comforted me and said that I wasn't alone and that he's met up with a lot of guys like me looking for a strong woman to dominate them. However, he told me that what they really want is to submit to a dominate man like him, and that everyone of them has ended up worshipping his big cock and loving it. He then looked me in the eye and said with a smile, 'You might think you're different, but we both know what you came here for.' The way he looked at me when he said that made me blush, as I knew that if I stayed any longer, I would be worshipping his big cock. That was a scary thought for me, but it also really turned me on. I tried to calm my nerves by taking a big toke of the joint and gulping down the last of my beer. It helped for the moment and as I past the joint back, while he put something on TV. I was quite stoned and horny now, and I noticed that he put porn on TV. In it there was a fit blonde sissy wearing black garters and stockings. He looked a bit like me, and he was on his knees enthusiastically blowing a ripped hairy man with a large cock. It looked so hot, as the sissy took that cock as deep as he could.

I must've zoned out while watching, because I didn't notice at first that Tony has rested his hand on my thigh as he passed the joint back. I didn't stop him, so he slowly slid it up my thigh, gently massaging me, my cock was now rock hard. I let out a little moan when his hand brushed against my cock for the first time. He took this as encouragement and gently stroked my hard cock. His big hand on my cock felt so good, as I leaned back and let him explore. His hands ventured up my stomach to my chest, as he paused briefly to gently pinch my nipples. He then leaned in and pulled my face to his and kissed me.

My first kiss with a man was so different from what I was used to and what I was expecting. He kissed with passion and confidence as he pulled me into him and slide his tongue into my mouth. After a moment of shock, I relaxed and kissed him back. My natural instincts were to try and take control of the kiss, but in this moment, I couldn't. He was in complete control. He was dominant without being overpowering, rough without being harsh, it was intoxicating. He slid his hand down to my ass and pulled me on top of him so that I was straddling him as we continued to make out.

We made out with like that for what seemed like ages. I could feel his hard cock grinding against my ass as his hands explored my body. We paused for a second as he pulled my shirt over my head and tossed it aside. For a moment I thought of all the girls I had done that to, and how weird and hot it was to be on the other side of it for once. The thought quickly disappeared as he slid his hands up my chest to my face and pulled me in for another kiss, which I eagerly returned.

He broke the kiss and got me to stand in front of him. He looked at me like a wolf eyeing his next meal. I was powerless to resist now, but I didn't want too either. Whatever objections I had were long gone by now, a distant memory, overpowered by desire and lost.

He reached over slid my pants down, revealing my hard cock and smooth ass. He took a moment to look me over, and he gave me an approving smile as he squeezed my ass and told me to kneel in front of him, which I obeyed without even thinking.

He stood in front of me and chuckled softly and said, 'I told you that you were the same, sissy.' I flushed with embarrassment and opened my mouth to respond, but I knew it was true, so I closed my mouth and looked down, burning with embarrassment and desire.

He smiled down at me and said, 'Don't worry sissy, your secret is safe with me. Now take my cock out.'

I eagerly slide his pants down and his fully erect cock sprang out inches from my face. Without hesitation I reached up and took his cock in my hands. It was huge! I wrapped both of my hands around it and I automatically started to stoke his big cock, enjoy the feeling of his hard throbbing cock in my hands. I looked up at him and he smiled down at me and said, "That's it sissy, do what feels natural to you."

I blushed and took the head of his cock into my mouth. The taste of his pre-cum and the feeling of his hard cock was overpowering as I gave in to the moment and willingly took him deeper into my mouth.

He moaned in approval and a little surprise at how fast I gave in, 'My what an eager cock sucker you are, I'm going to have fun breaking you in, slut', he teased. His dirty talk and name calling was causing a weird mix of emotions in me, but the strongest one was a desire to please him.

He started to gently slide his cock deeper into my mouth and I took as much as I could. It was intoxicating to hear him moan as I blew him. It was my first time with a cock in my mouth, so my technique needed work, but I made up for that with enthusiasm. I was surprised to realize that I enjoyed sucking his cock. Feeling him throb in my mouth was intoxicating. I slid my hand down and realized not only was I rock hard, but I was also leaking pre-cum!

He was clearly enjoying my efforts as he picked up his pace, taking control and began to face fuck me. I gripped onto his muscular ass to hang on as he fed me his meat. I knew he was going to cum soon, but it still caught me off guard. His cock throbbed in my mouth, and I could feel the first spurt hit the back of my throat. Two more large blasts of cum in my mouth was more than I could handle. Thankfully, he pulled out to cover my cheek and forehead with the last two spurts of cum. I collapsed back, swallowing the rest of his load and trying to catch my breath.

'Now you look like a proper little cumslut', he laughed as he surveyed his work. 'But I'm not done breaking you yet, sissy', Tony said to me as he took my cock in his hand and lead me to the bedroom.

When we got there, he ordered me onto the bed on my back. He pushed my legs up so my ankles were by my ears. I was completely at his mercy with my ass totally exposed to him. He looked at me with a sly smile and told me, 'We have to get your ass ready for what's next.' I shuddered with anticipation.

He bent down still holding me and began to eat my ass like it was a buffet. I never felt anything else like it, his tongue was probing me in places I've never felt. It was amazing, and I must've been moaning pretty loudly since he stopped to take a breath and said, 'You like that slut?' 'Mmm yes sir' I moaned, and he replied, 'Good, we're just getting started.'

He ate my ass for awhile, and whenever he felt like I was going to cum, need stop for a moment, squeeze my balls, and tell me I'm not allowed to cum yet.

Suddenly he stopped and I felt him squirt a generous amount of lube on my ass and I knew that my anal virginity was about to be lost. I felt his cock slid up and down my ass as he gently teased my asshole with it, making me squirm with anticipation. He was clearly enjoying teasing me, as he pressed his hard cock against my asshole just enough for me to feel it but not enough to enter me. At this point I was dying to feel him inside me. I pushed back on his cock, trying to get it in me, but he wouldn't let me have it.

'If you want my cock, you're going to have to beg for it sissy,' he teased.

'Please fuck me,' I replied.

Smack! He slapped my ass hard and said, 'You will address me as Sir or Master! Understand sissy?'

My face burned with embarrassment, but I managed to stammer out, 'Yes master, I understand.'

'Good', he said, 'Now try again. And put some effort into it.'

'Please, Sir, I need your huge cock in my ass. Please fuck me and make me your personal cumslut!' I begged.

'Much better, sissy, tonight you will be my personal cumslut', he said as he slowly pushed his cock into my virgin ass. I gasped in shock when his large cockhead pushed in, he smiled softly at me and said, 'Just relax babe and you'll moaning like a whore in no time.' I tried to relax and breath as much as possible as he slowly slid in my ass inch by inch. It was a weird combination of pain and pleasure that took over me as he stretched my tight virgin ass. He slowly pulling it out a bit before pushing it in further, in a gentle fucking motion. The pain slowly subsided and soon I found I was pushing back against him, pushing him deeper into me. The pleasure was mind blowing, I had never felt anything like it!

Eventually, I felt his thighs pressed against my ass and he looked at me and said, 'Look at you, an hour ago you were straight and now you have my cum on your face and 9 inches of hard cock in you. You're a natural sissy!' I opened my mouth to reply, but only a moan came out. As he laughed, he started to fuck me harder.

As he kept picking up the pace, all I could do was lay back and enjoy the ride. As I started to relax a bit, it started to feel better. Before I knew it, I was pushing back against his thrusts. He noticed and picked up the pace, not letting me take control. He spanked my ass with his free hand as he fucked my brains out. He was in total control and was using me as his personal slut. And wow, it was amazing! I was moaning like a whore, as he pounded me. My cock was so incredibly hard, and my toes were curling in a mixed of pain and pleasure. It felt so good and in the position I was in, my cock was aimed right at my face. It was only a matter of time before I blew my load onto my own face.

He noticed and asked, ' Do your want to cum sissy?'

'Yes sir', I managed to reply between moans.

'Beg for it'

'Please sir, please let me cum!', I gasped.

'Now!' he moaned.

Just hearing those words sent me into a huge orgasm, I could feel my ass twitch and squeeze his cock as I blew my load all over my face and into my open mouth.

My orgasm sent him over the edge, and he with one last thrust he buried his cock deep in my ass as he unleashed his hot load into me. I could feel his cock throbbing and his cum spurting deep in my ass. It was so fucking hot.

He slowly pulled out of me, and I felt some his cum leak out of my ass, it was such a weird but hot feeling. We were both collapsed on the bed together, spent from the encounter. He cuddled me from behind as we laid there enjoying the after glow.

Eventually, we got up to clean up and I got dressed to go home. Tony gave me his phone number as he walked me to the door and said with a cheeky smile, 'For when your craving cock again, I'm betting by next weekend.' I blushed and mumbled an unconvincing, 'We'll see'.

He chuckled and said, 'See you next weekend sissy,' as he gave me a kiss and a quick smack on my ass on my way out the door.

I walked home in a daze. I was still pretty stoned, could taste him in my mouth and his feel cum in my ass. I felt like such a slut, and even more confused about myself. I got home and went straight to bed, exhausted.