My First Daddy - Becoming a Sissy

I was 19 and was just out of high school. I had a tough time in school, I was always the quiet nice guy type. That in combination with my lack of masculinity (girly face, skinny hour glass shaped body and big bubble butt and thighs) made it almost impossible to get laid.

I had what I thought was a serious girlfriend for a while, a beautiful freckle face redhead girl with a big butt named Jennifer. She had planted seeds in my head about not being an "alpha" because I couldn't make her cum during sex. She said her ex always made her cum and that it should be easy.

She wanted me to use a dildo on her that was easily twice the size of my cock. This made me realize I had a small cock and it made me think a lot about her getting fucked by bigger better cocks. This confused my sexuality.

I found out in the end she was cheating on me with her ex the whole time. Also I eventually found out she was fucking a black guy who graduated a few years ahead of us and had a reputation for having a huge cock.

She broke up with me. I'd have stayed with her no matter who she fucked but she had no need for my little cock and scrawny body. She chose real men because they could fuck her better than me.

After that there was a lot of jerking off and porn rabbit holes. I went on a cuckold porn binge first, thinking about my ex getting fucked by big alpha cocks. Then watched white girls with a big butt like hers getting fucked by black guys.

I would see the occasional cuck video where the boyfriend sucks the guys dick or eats his cum from her pussy. That started to turn me on more and more. At some point the cuck porn led me into sissy porn, where instead of just letting guys fuck your girl you let guys fuck you.

These types of videos explained what it is to be a sissy, and described what a sissy type guy is like. The description fit me so perfectly it was undeniable. I knew in my heart I was actually not a man and that I was a sissy boy. I continued to act straight in appearance and demeanor in public but behind closed doors was becoming a bitch.

I still had a few pairs of Jennifer's thongs at my house that I kept in a shoe box under my bed. I'd take them out and sniff them sometimes because they were dirty when she left them here and you could still faintly smell her pussy.

Eventually I had started wearing them, and they fit my big girly ass perfectly. I'd jerk off looking in the mirror or at pictures of my ass in her thong. I loved how it felt to have the thong slide up into my big butt and how sexy and girly my ass looked in a thong.

I only had a little bit of body hair poking out and since I wasn't having any sex or dating anyone anyway, I decided I'd shave some down there. The more I shaved the more some became everything, and it went from a trim to a razor shave. I'd shave myself smooth everywhere. It felt good to be smooth and soft and it made the pictures I was taking so much better. I was really starting to feel like a sissy.

On top of that I had started collecting what I could discretely gather for leggings and skirts that showed off my ass. I was dressing up taking pictures of my body all the time. I was learning that it felt good to behave like a slutty girl. The taboo of being a sissy was the only thing that turned me on, and the only thing I could think about most of the time.

Eventually I started playing with my asshole and fingering it and rubbing it every time I jerked off, which was often. I would put my soapy fingers as deep as I could into my ass every time I took a shower. Then I bought a butt plug, after driving an hour away to a sex shop so that I wouldn't be recognized.

I still hadn't done anything with a guy but all I thought about was cock now. I was watching sissy porn that promotes the idea of being with a "daddy" type, and that became what I was most interested in. I felt like I'd always loved older guys, I remembered wanting to please the older men in my life and looking for their approval. The taboo of having sex with a much much older man turned me on beyond belief. You can definitely say I have daddy issues..

Anyway, I became fixated with older men and would wonder how big there cocks were every time I crossed paths with them. I was starting to lust after older guys, even flirting with them being overly touchy every time I was around teachers, coworkers and even family that fit the bill. I was seeming to get only positive reactions. Older guys like me too, I guess they could sense that I was becoming a sissy. I just wanted to show them my body and my ass, I knew they would love it..

At some point I mustered up the courage to post on a personals page that allowed you to post a picture and a brief description of what you're looking for. I put a picture of my ass in leggings pulled down just enough to reveal my thong. I said I was a curious 19 year old sissy boy with no experience, looking for a daddy type to explore with. Well, my inbox was flooded with messages. A lot of the responses were junk but a few were exactly what I was looking for.

It felt so good to be wanted and to have people pursuing me, especially big strong horny men. I loved being complimented on my ass. I loved the filthy things the guys were saying to me and being called names like sissy, faggot and bitch. I loved the random cock pictures men would send me.

My confidence as a sissy boy skyrocketed. I knew now that men really did find my body to be as sexy as I thought it was. I had gotten so many men throwing themselves at me that I was feeling hotter than ever. This was all so new and fun to me, I must have cum a thousand times reading the horny messages and staring at all the cock pictures.

I started conversations with lots of guys. Most were impatient and pushy, that was kind of attractive to me in a way but I was also very hesitant and scared so I didn't click with those guys as much.

One conversation that started to develop was with a 59 year old guy named Kevin. He was assertive but loving and admiring. He gave me so much praise and it seemed like he was really into my body. He showed me so many pictures of his big cock and videos of him fucking his wife and jerking his cock.

He had a huge cock, maybe 8 inches but thick, similar to the size of the dildo my ex had. He told me how much he loved my ass and how he wanted to treat me like his girly slut. I told him I'm new and that I couldn't take his huge cock in me even if I wanted to. He didn't argue but was still eager to set up a date to play. He said he really just wanted me to taste his cock and that once I had a taste I'd be hooked. He was eager to make plans with me but also seemed very patient.

I really did want to suck on his big cock though. I was thinking about it all the time and chatting with daddy all throughout the day, looking at his cock and fantasizing.

I was super hesitant to go through with a meeting as I was petrified of family and friends finding out I had such a gay side to me. He was very convincing and reassuring, telling me everything I needed to hear to feel comfortable. After a few weeks of chatting back and forth via email, then text messages, exchanging a lot of pictures but never face pics, we finally set up a date to play.

He picked me up in a Walmart parking lot, it was cold and I had a big jacket on. I recognized the make of his car but had never seen him, when I opened the door and saw his face I was relieved, he wasn't handsome but a very plain looking slightly overweight daddy type, he had a welcoming smile. I had worn my leggings and thong, hiding them under baggy sweat pants. His car was warm and I felt comfortable and safe with him.

We had made plans to go to a hotel, he told me he already checked in and that we can go through a side door where nobody will see us. As he talked to me and drove he kept looking over at me with a deviant smile, he was steering with one hand and with his other gently caressing my thigh, which even through the thick sweat pants and legging sent electricity through my whole body. That was my first romantic touch from a man and I loved it and instantly craved more.

I was too nervous to do anything back but my cock was rock hard in my sweatpants, daddy's touch was exactly what I needed. He slid his hand under the front of my jacket and down my belly into my sweat pants. He felt my hard little prick pressed against my panties, he looked over and told me I was a good boy, I smiled back and said thank you daddy.

It was a short drive and we pulled up to the hotel which was a Hampton Inn. We went in the side door as he described and I followed him to the room. Instead of taking the elevator we went up the stairwell, he reached out and took my hand, now I was holding daddy's hand being guided to a hotel room to suck his dick.

My heart was about to pound out of my chest I was so nervous but I just went with things like I was on autopilot. I was scared I'd see someone I know or even a stranger, and they would see that I'm holding this old guys hand and following him like I was his girl. This part of the experience was unexpected but sort of thrilling.1

When we walked in the room he took off his coat and shoes. I did the same. The room was warm and I felt cozy and comfortable. He talked to me, I can't remember specifically what he said but I remember being afraid to speak, until finally I answered him gently. I took quick notice of the surroundings and saw the condoms and lube by the bed. This frightened me a little because we'd already agreed his cock was too big for me, so I was concerned he might have his hopes up about fucking me, which I still didn't plan to do.

He had unbuttoned his shirt and taken it off, he had a dirty white t-shirt on underneath that he began to take off. We had made plans for me to wear his big shirt, so as he took it off and handed it to me that was my cue to take my own shirt and sweat pants off and wear my daddy's musty man scented shirt for a while.

I felt good in the big shirt and my leggings. It felt good to be dressed like a girl and have my daddy admiring my body and me in real time. I felt sexy and wanted, a feeling I could never have gotten as a normal boy. I loved being a sissy.

I joined him on the bed and curled up next to him, he was sat up on the bed against the headboard, watching me and waiting to get his hands on me. He was wearing just his boxer briefs at this point. His cock was already starting to swell up. He put his arm around me and I instinctively rested my hand over the bulge in his underwear. His cock grew against my hand.

I had told him I didn't want to kiss prior to meeting and he was very understanding. So as we cuddled on the bed and his cock started to get hard I was just kind of looking down with my head on his chest. It felt good having my smooth face against his hairy chest. I felt his cock getting harder and could see it rising under my hand. He was groping my ass with one hand and used his other to pull his underwear down and let his cock pop out, it sprang out and looked bigger and stronger in person than I ever could have imagined.

I felt drawn to it, so when he told me I should put his cock in my mouth, I gladly took his recommendation. It was what I had dreamed about for so long now. I was in love with my daddy and his cock.

I kissed his cock and balls like I'd seen girls do in the porn I'd watched, then I slowly took his thick tool into my mouth. I couldn't believe I was actually sucking a man's cock, finally. I could smell and taste the mustiness and I gagged each time I tried to put it into the back of my mouth. I loved hearing him tell me I was a good boy and telling me that I'm a slut and a faggot. There was no going back now, I had really become a sissy cocksucker.

His hand was still on my ass but now he was tugging at my leggings, I moved my body to assist him with sliding them off. As he exposed my big girly butt, I heard him let out a moan and felt his cock twitch in my mouth. I was in a position with his cock in my mouth but my ass squatting next to him allowing him full access. He was rubbing my ass now, and gently slapping it. I felt his fingers explore the crack of my ass and slide gently under my thong. Now he was gently rubbing my ass hole, tracing the outline of it with his big thick middle finger. I felt like such a slut, I let out the most girly moan, even with a mouth full of cock.

I was in heaven sucking on his big cock now, having my sissy ass played with and loved. At first I thought the precum I was tasting was gross but I actually started to like the taste of it and was actively rubbing my tongue over the slit of his cock, lapping up every bit of it I could get.

The more eager I behaved the more daddy would tell me what a good boy I was and how I was meant to be a sissy and a faggot and a boy slut. His words melted into me and I knew he was right. This felt so right, like it's where I was meant to be and what I was made to be doing.

Daddy had my thong pulled to the side and was rubbing my asshole good. He took his fingers away and I'm guessing he smelled them and taste them, when he put them back they were wet and he rubbed harder now, I could feel my asshole opening slightly and it felt amazing. Then I felt a finger penetrate my ass, it was my first time being penetrated by anyone other than myself. Again I just couldn't believe I was on top of this big stranger, sucking his cock and letting him finger my ass.

I distinctly remember the first time I had both holes filled at one, he had the tips of his two thick fingers in my ass and his thick cock in my mouth as far as it could go. I loved this feeling and would have stayed in this position all night, but daddy had other plans for me.

He pushed me off him gently. He turned me around on the couch and pushed my back down, I instinctively poked out my ass and arched my back like a girl. I felt daddy's face against my ass, he was taking a big sniff of my ass crack. Then he kissed both cheeks before gently spreading my hole with his thumbs. Then I felt his tongue run up my ass crack, the again he ran his tongue from the bottom of my balls across my taint and stopped on my hole this time. I was shaking with pleasure.

He proceeded to tongue fuck my asshole, first starting with a gentle French kiss and building up to him just sucking on my asshole like it was a girls pussy. Meanwhile he jerked my little dick, milking me like the slutty boy I'd become for him. I quickly came and leaked a load onto dads hand, I felt his hand go away and could feel and hear the movement of him jerking his own cock, using my boy load as lube.

The whole experience so far had felt surreal. This was everything I ever dreamed of and more. And I could tell by daddy's lustful excitement and rock hard cock that he was loving it too. It felt so good to be able to please a real man and to be the object of his affection. I know it sounds crazy but I felt like I was in love with him.

This was the most sexual I had ever felt. None of my experiences with girls came anywhere near this. I'd have dove anything for daddy, I just wanted to be fully his. I felt like I wanted to be his girlfriend.

Then I heard the words leave my mouth.. words I thought I'd never say.. "Fuck me daddy", I said. In a pleading tone, as if he needed convincing. He stopped sucking on my boy hole. He was a gentleman and asked if he should put on a condom. In my cock drunk lust I told him no, I told him to fuck me raw and to breed me. With that he lined the tip of his cock up and gently started to push.

This was all happening so fast, I went from being scared of getting fucked to asking my daddy to fuck me. Even asking him to breed me raw. My own goriness and daddy must had gotten the best of me. I was truly becoming a slut for my daddy.

The tip went right in easy but as he pushed further I felt and intense pressure that built up and culminated in a deep burning feeling as he tried to push past my inner ring. It was a terrible feeling and even though I loved everything happening I just needed the pain to stop. I pushed daddy back and said wait. His fat cock slipped back out of me. The pain was still fierce and lasted a few more minutes. During this brief rest daddy flipped me over onto my back. He was holding me and kissing my neck, telling me what a good boy I am.

He looked me in the eyes and asked if I was ready.. not if I wanted to stop or keep going or any other option.. just if I was ready. I shook my head yes, even though I was so scared of him hurting me again. That's all he needed to take hold of my legs and put them in the air, exposing my little cock and boy pussy. He kissed me on the mouth deeply, shoving his tongue into my mouth.

He let go of my legs as he reached for the bottle of lube on the night stand, I instinctively kept the position, holding my legs up exposing my asshole and limp boy cock. I felt like such a slut in this position, but in the best kind of way. This is exactly what I wanted and what I had asked for by showing off my girly body and seducing this horny old man.

I started to come to the realization that he knew he would be kissing me and fucking me tonight, and I knew it too. This thought turned me on beyond belief, I was thinking about the fact that I am gay, and that I had come here to suck an old guys cock and let him fuck me. I felt him pour a little lube into my ass and work it in with his fingers gently.. I wondered why he hadn't used it the first time.. did he want to hurt me with his cock on purpose?

Just as that thought crossed my mind I felt him slide his big manhood into me, I was scared it was going to hurt again like it had moments earlier but to my surprise it slid in slowly, then slow stroke by stroke going deeper and deeper. Now I could feel him pushing past the spot that had earlier been my breaking point... only now it felt kind of good. He held me tight and I hooked my legs onto him, it felt amazing being underneath my daddy, with his big cock inside of me.

As he lifted away from me some I looked down and could see my little cock flopping around as daddy started to grind into me deeper. I reached for my phone and took what I could for pics and vids for a few minutes, as we discussed prior that we both felt okay with that as long no ones face appeared in the pictures. His grinding was too much and I put the phone down. I wrapped myself around him and held him tight.

I was in heaven, this was the most orgasmic I've ever felt. I had an old strangers big raw cock filling me up, grinding as deep as he could into my big girly ass. I could feel every movement he made with his big thick manhood. He was making me his bitch and marking me as his slut for life. Again I wanted him to be my boyfriend in that moment, I loved my daddy so much.

He continued to wiggle his cock deeper and deeper into my body. I let go and he sat up, turning me onto my side and pulling his cock out until just the tip was still in, with force gave one firm pound forward, as if to test my ass, I let out a girly moan and said "fuck me daddy" within the moan, as if the words just came out as uncontrollably as the moan.

That's all he needed to hear. He started pounding on me like a jackhammer, insuring my ass would never be the same. I'd be lying if I said it was all pleasure, as there was a lot of soreness and pain, but it was balanced out by the euphoria of finally being the slut I had wanted to be for years. I was proud of myself for going through with this and letting my daddy fuck me. I was even proud that he was in me raw. This is exactly what I wanted and needed.

Daddy pounded on me for another 15 or 20 minutes off and on. He jerked my cock off both times it got hard and made me cum all over myself twice. Then the big moment came, I could feel him tensing up and squeezing me harder and harder. His cock was starting to stiffen and it felt like someone was shoving a stone into my ass, then he let out a groan, telling me to "take his nut like a good faggot", for my part, I begged him to breed me, I told him to mark me with his cum and make me his bitch forever.