Princess Heart Pt. 01

Spring - 2011

I was a month and a half away from 20 and Daniel was 54. In the six months that I had been dating him, our relationship grew from a shy encounter to him becoming my official first boyfriend. I had never even kissed a guy prior to meeting him through Craigslist and he was everything I had ever dreamed about, despite the age difference. It worked out for Danny too. He had once been married to a woman ten years before we met and for whatever reason, it didn't work out. I never asked him about it but he told me that he always wanted to be with a young Asian man and that my inexperience with guys was perfectly compatible, as I was only his third gay lover.

Throughout my entire life I had insecurities about fitting in with my peers. I never played sports and on the rare occasion that I'd watch a professional match, I would develop crushes on the players. That attraction was always accompanied with a sort of sadness knowing that athletic, handsome men would never want to be with a boy like me. I never dated in high school and instead focused on my grades and test scores. Emotionally, I felt like an outlier as well. Instead of flirting with girls, experimenting with alcohol or getting into fights, I secretly cried watching Pixar movies and fantasized about being a princess, waiting for a handsome prince to come take my breath away. I remember wishing that I could develop breasts like girls and when junior prom came around, I thought how nice it would be to be able to pick out a dress for a magical night with a handsome date. However, those ideas would just remain fantasies and high school came and went without any memorable experiences or relationships.

I met Danny through Craigslist in my second year of college. I had moved away from home, into a dorm 75 miles away and getting away from my parents and peers gave me enough courage to explore my sexuality. Danny was the first person I had been intimate with and he found a way to unlock my pent up femininity. His gentle touches with his backside of his hand, his kisses on my neck and the way he'd hold my hand made me feel so feminine and accepted for the first time in my life. He also made me feel really horny. Never in my wildest dreams did I imagine doing the things I'd do with him over the course of our two and a half year relationship.

One of those things was cross dressing. It started as a playful gesture. Danny suggested to me that I would look really cute in panties and offered to buy me some. The first pair of women's panties he got me was white boy shorts with little hearts on them. By the spring, he had a full drawer full of women's wear for me to dress up in, ranging from cute, innocent white panties with butterflies on them to scarlet red lace thongs. I even started wearing a bra for him because it made me feel more feminine and I often lounged around in his apartment wearing cropped junior's t-shirts or spaghetti strap tank tops and only panties below the waist. Personally, I preferred cotton underwear over nylon lace because it was more comfortable, especially when it came to bras. Later in our relationship, we would establish secret color codes for the color of panties I would wear. Pink would mean that I was ready for anal sex. White panties meant I wanted to swallow his cum. Almost always paired with my choice of panties was a feminine fragrance, which at that time was either Juicy Courure or Tiffany Sheer.

By spring break, we were officially a couple and we even talked about life after college. Throughout it all, he was very respectful of my inexperience and although we had sex almost right away, he rarely asked for it. At least not at first. Usually it would be me who signaled the desire to get fucked in my passive-aggressive way of wearing pink panties. As seductive as that may sound, it was probably less than once a week, as it was a tedious task to get completely cleaned out for sex. Much more frequent was cuddling on a weeknight, wearing my hello kitty pajamas and making out or giving him a blowjob. I must've sucked his cock 4 nights a week that initial Spring semester. On one occasion, I had my head on his lap like usual as I kissed the tip of his penis and I scooted myself up to the pillow so I could talk to my Danny face-to-face. With my thighs wrapped around his hips, one on each side, I proceeded to kiss his neck and whisper in his ear.

"Can you please cum in my mouth tonight? I think I'm ready to swallow you baby," I said to him. I felt like such a naughty little slut saying things like that and my small cock would grow to a mini erection inside of my little panties.

Danny stared into my eyes, his serious and lustful gaze attempted to confirm what I had just said. I nodded, still making eye contact with him, letting him know that I was ready to swallow my first man. He had come in my mouth before but almost instinctively, I ran to the bathroom to spit it out in the toilet. He was understanding but I felt bad about it since he'd been swallowing my cum since our first encoutner back in December.

Maybe the reason I had withheld swallowing for so long was the fact that I felt a little intimdated about the amount of cum I would have to swallow. What if I couldn't take it all down? At almost 260 lbs Danny was over twice my weight and even his gentle hugs made his hairy arms feel like boa constrictors. His cum load matched his size and I would usually require a towel to clean his love juices off of my body after sex. After I told him I was ready to swallow his load, we kissed as I mentally prepared for how I would suck his 7" cock to orgasm. I could tell Dan was excited by the idea too, as I could feel his plump erection pressed against my soft warm hole through my thin white thong. Dan eased his grasp and that was my signal to begin this next chapter in our relationship. I kissed his neck and worked my way down to his hairy pot belly. I spent a little time kissing his hips down to his all natural pubic hairs, making sure not to miss his sensitive spot, just below his pelvic bone where his hairs began to grow thicker. I reached for his penis with my hand, feeling a little relief that it was still hard. I playfully let his cock brush against my checks and lips as I teased him with kisses all around the shaft. I closed my eyes, similar to the way people naturally close their eyes when they kiss and slowly took Danny's full erection into my wet mouth. Neither of us said a word the rest of the time as a comforting silence filled the room, occasionally accented by the sounds of my wet mouth sucking on his penis. The sound of Dan's heavy breathing matched the rhythm of the squishy sounds I was making with my mouth. I looked up to see Dan's loving gaze fixated on my efforts. I could never take his entire penis in my mouth but I used my hands to stroke it up and down as I sucked on the upper half of his beautiful cock. He calmly ejaculated in my mouth and I instantly recognized what was happening. I didn't feel much of a "squirt" as I was expecting but instead I noticed more of an emergence of salty fluids building up in my mouth. I paused to swallow his first deposit and continued to bob my head up and down. Much of the effort from my point of view was making sure I didn't bite or scrape my teeth on my boyfriend as he thrust his cock as far as I could take him. I took a momentary breath like a swimmer emerging out of water to inhale some much needed oxygen and put his penis back into my mouth. The second gulp felt larger than the first and I repeated the motion a few more times thinking to myself, "that isn't such a big deal."

Weirdly enough, I still didn't quite consider myself gay in those early months, even after losing my virginity to a man. Not even after being penetrated wearing pink panties. I would say the day I felt like I knew I was gay was when I came out to my family much later. Surely, I enjoyed every moment of being with Danny and any sensible person would consider having sex with a man as a gay act. I just didn't connect the dots and digest it as "gay" at the time. I didn't deny it either but the labeling didn't matter to me. He was simply my first lover and my first intimate experience with another human being. I can't say I had any desire or fantasy to swallow loads of cum from random men, no matter how attractive they'd be. I guess you could say that I was "Dan-sexual." He was different. Swallowing his semen was a way for me to feel connected to my lover; to understand him better and to give him the gift of pleasure in return for loving me. There wasn't a thing in the world I wouldn't do for him and that was no exaggeration. I cherished having Danny's cum inside of my tummy and wished he could be inside of me forever.

Perhaps not associating as gay or straight was simply a reflection of my inexperience at age 19. I never really thought about how my romantic life would play out in my life. If you'd have asked me where I wanted to live or what job I wanted in the future, I could've given you detailed answers. However if you asked me about the person I wanted to share my life with, I'll admit I had no idea at that time. Dan was instrumental in helping me define that goal.

I confessed to Dan early on that I was inexperienced and he was very open about having me try different things. He was never pushy about anything and even when we had sex for the first time on our second date, he made me feel so sheltered. I loved the way he would kiss me with full tongue just as he would apply a gentle but firm pressure on my anus with his cock. It had a magical way of making me feel relaxed, to invite him to dilate my virgin pussy, as if my anus was giving him a loving hug. The overwhelming sensation led to an embarrassing episode of me bursting in tears as I moaned in pleasure, releasing all the complications of being so confused sexually but never being able to tell a soul about it. I spread my legs apart as if to tell Danny I had nothing to hide anymore. I wanted him, no, the entire world, to see that I was having sexual intercourse with an older man. Dan seemed to understand and knew how to leverage my tears into a climax I'd never felt before in my life. His French kisses intensified as his pumping sped up and he eventually came inside of his condom. A month later, we would decide together that we would stop using condoms during sex, another sexual milestone for me. Such was my sex life with Dan. Everything was new, unfamiliar, empowering and amazing.

Life outside of Dan's apartment near campus was far from exciting. I was a full time student taking all my required courses in order to apply to the Engineering program at one of the top Universities in the country. To be honest, I found it pretty easy and most of the time, I'd just finish my assignments by mid-week and spend my weekends at my boyfriend's place. Dan worked as a window installer which meant I didn't see him during the week as much as I wanted to. We texted each other almost every day and he would often give me "assignments" such as plucking out all of my pubic hairs and sending him a photo of my smooth little cock. It was around this time that he started calling me his "Princess" and "Cutie Pie." First by text and shortly after that, in person. One evening, we were talking about our turn-ons as we were having sex and he slowed down his thrusts to allow me to talk in between my moans.

"Cutie Pie, tell me what turns you on?", he asked me.

I had to think about it for a second. His hard cock came to a standstill inside of my body, waiting for my answer. Weird thing to ask me during sex, I thought. Perhaps it was because my little penis always shrunk to about an inch when being penetrated anally. I began to get self conscious.

"I really like it when you kiss me babe," I answered.

He gently palmed the back of my head and drew me toward him. We closed our eyes simultaneously as we kissed and his thrusting resumed. Our tongues danced around in my mouth, muting my moans and creating a whole new wet, sexual audio composition. For a second, I had completely forgotten that I was being fucked in the ass by a seven inch cock because his kiss felt so much more intense.

I took a breather and looked at my handsome Danny in the eyes.

"What turns you on babe?", I reciprocated his question. Creative me.

Danny pulled me toward his chest again and massaged my bare back with both his hands. His cock remained lodged inside of my body as he whispered into my ear.

"I want you to officially be my Princess and seal it with a kiss."

"Yeah?", I didn't know exactly what to say or what he meant. He continued to fuck me as I moaned my signature Japanese porn girl whimpers.

"I want you to wear a special dress for me and we can have a ceremony to make you my official Princess."

"I'll do anything for you Danny," I told him.

"After you get dressed and say your vows, I want to make it official with a cum kiss."

I looked down at my tiny cock and realized I had been oozing precum onto Dan's tummy this entire time.

"Now babe?"

"No, next weekend. I want to get you the perfect dress and cute little princess panties."

I let my tongue and anus do the rest of the talking as I kissed my Danny and gyrated my hips to allow my warm soft hole to swallow his cock up and down. Dan reached for my penis, growing it to a four inch erection in his hands and stroked it with his masculine hands.

He reached for my hips and lifted me up, momentarily disconnecting our bodies. I immediately yearned for his cock back inside of me, where it belonged. He got up from underneath and rotated me around to bend me over the side of his couch so that my butt was in the air and my face was resting on the arm rest.

"I love you cutie pie," he spoke directly to my anus as if it were my lips. I could feel his breath on my opening as he dug his tongue deep inside of my most sensitive area. I always felt a little self conscious when my man gave me oral sex like I was a girl, but I guess I had nothing to worry about since he kept going, making all kinds of squishy noises with his mouth.

"I love you so much babe, I want to be your one and only princess", I said with my face buried into his pillow. I began to cry again. Being stimulated around my boy pussy always made me feel emotional. It still does today.

Just as I responded, he penetrated me again from behind and pumped in and out at a steady and methodical pace. I felt so loose, relaxed and overwhelmed at the same time. Suddenly I felt like I had to pee and had no control of my body. My high pitched moans were rhythmically in sync with Danny's pumping. My entire body felt flushed with warmth and love. I lost all strength in my upper body and collapsed on his pillow as my man continued to fuck my ass. Tears erupted from my eyes with every moan and I glanced down at my little cock to see that it was squirting some kind of spermy liquids as well. Maybe it had been this whole time. I was having a p-gasm. Danny let me know he was about to cum as well but I was too spent to say anything.

"I'm cumming my Princess," he sounded emotional too.

He let out a loud grunt and I knew he was depositing his seed deep inside of me as my body remained limp. I had zero control of my anus. No way to tighten or loosen my muscles around my hole. Just a wet, lubricated opening to my heart for Danny to use as he pleased. Danny pumped every last drop of cum he had into me and pulled out to the sound of wet air suctioning out of my body. I didn't care. I was exhausted and full of love. I couldn't wait to become his official Princess and make him my official Prince Charming.