Confessions of a Player

[XPlayer]

Dear SBF brothers,

I have been a visitor to this forum for years now, and have always enjoyed the stories, fantasies and experiences shared by all of you. While I’ve always wanted to share my own past experiences, I’ve always postponed it, partly out of laziness. Now that I am approaching a new chapter in my life, I think it’s time I confess my “sins” for your enjoyment.

I have been racking my brain for the wonderful (and not-so-wonderful) memories of my exploits, and will share some statistics of my adventures once my recollections are as complete as I can make it. For now, I shall just be sharing my stories.

I’ve decided to share the stories now as I am now engaged to an incredibly beautiful woman who is quite simply the hottest babe I have ever been with. Her personality, our chemistry and all the other factors that normally bond two people for life are there, and so we have decided to share our lives together. So before I give up my life as a player (for the most part that is; my stories will explain further), I shall do my “confessions” for your enjoyment.

The stories that you are about to read are all about 85-90% true. The remaining 10-15% have been disguised for reasons of privacy, especially names, locations, some details (I may have forgotten some of the tiny details), timing of events, etc. The essential core of the stories are however, completely true. I will only post stories that I feel are rather exceptional in their impact on me (basically the ones I worth remembering), or those that are more interesting. The plain vanilla stories I won’t bother spending time typing them out.

In my years since puberty, I have had the pleasure (and the occasional horror) at having slept with over 250 women, in relationships ranging from the casual to the serious, one-night-stands, escorts, massage/spa ladies, GROs, etc. I know there were more than 250 but probably fewer than 300, though I have lost count of the number of ladies I’ve been with who required financial compensation for their time and company.

If you don’t like my stories, please feel free to ignore this thread. Otherwise, please enjoy.

XPlayer

[gilagila100]

huh ?? where's the stories ??

[Criminalz]

This is the story.

[jw51]

xplayer
Please start your stories with vivid descriptions.
I'm sure they are fascinating.

[XPlayer]

Sorry for the delay. Internet connection at home went down before I could post my stories. Now posting from a wifi connection in a cafe from my laptop. Don't have my stories on this laptop. Have already typed up a few chapters so by tomorrow I should have posted the first 2 chapters at least!

[XPlayer]

Part 1
The High School Years

1.1 The First Time

I lost my virginity at the age of 15, to my friend Millie, a pretty 15 year-old Chinese girl.

It all started one fine day during the school holidays. I was a studious 15-year old, model student you might say. Good grades, never got in trouble, well-behaved sort of kid. To ensure my grades stayed good, and possibly improve, my parents had arranged for a private tutor for some of the subjects I was learning. My tutor was a retired teacher with a great command of English, mathematics and the sciences. I wasn’t his only student, there were about 10 others in a small “class”. The class was split about 50-50 into boys and girls.

Among the girls, there was one, Millie, who caught my eye. She was a pretty Chinese girl about 2 months older than me, with dark brown shoulder length hair and light hazel eyes. We got along very well in class and exchanged notes frequently outside of class. We flirted a little bit quite often as we walked home after class, but we didn’t pursue it further. I think it was partly because both of us were at that innocent stage where we were both still shy in the presence of the opposite sex.

Well, during that particular school holiday period, we hung out a lot together, supposedly studying, but actually watching movies, listening to music and window shopping at the malls. It was on that fateful day, a Tuesday, I think it was, when she came over to my house around 9am. My parents were at work, and there would be no one but us at home for the entire day.

Millie giggled when she sat down in front of the big-screen TV. You see, I had managed to borrow from a close friend of mine, a collection of porn videos that belonged to his elder brother (who had gone overseas to study). Millie was curious and wanted to see the videos. I had seen porn before by that time, but as with most 15 year-olds, there was no such thing as too much porn.

We started watching a few videos. I don’t remember what most of them were (guess they weren’t particularly memorable), except for the original Debbie Does Dallas, and a couple of European videos (think they were German or Italian). They were the usual porn stuff, nothing extreme.

Anyway, to cut a long story short, Millie got kinda excited while watching (so was I actually, I had always watched porn alone up to that point in time, and had a raging hard-on with Millie lying down on the cushions on the carpet next to me). She started getting restless and asked me to turn the aircond on as she felt warm. We started to flirt some more, with lots of teasing about each other’s lack of sexual experience (we were both virgins at that time). The teasing got more heated and we started to tickle each other.

The tickling got more hectic, until I finally demanded that she stop or else I would kiss her. “Go ahead if you dare, coward!” was her reply as she giggle and tickled me again. So I kissed her, well it was more like a smushing of lips, and I just barely avoided whacking her nose with my nose.

Millie was stunned when our lips met. Then, when I kissed her again, Millie kissed me back. In imitation of the porn stars on the TV screen, our mouths opened and we frenched with lots of tongue action. With hindsight, our kissing skills were horrible. Our slobbering kisses were completely devoid of skill and romance. But for a pair of 15 year-olds French kissing for the first time, it was extremely exhilarating.

I was so excited at that stage, with my cock so hard, that Millie felt my hard-on press against her crotch through my pants and her shorts (I was on top of her at that point). “Tim, I think I can feel your thing,” she half-giggled breathlessly in between our frantic kissing.

Embarrassed, I rolled off her and onto my back on the floor, a little red-faced. “Oh, I’m sorry,” I muttered. Millie immediately sat up, and with a mischievous look in her eyes, asked, “Can I see it?” Shocked, at the sudden turn of events, I started to say no, when Millie’s hand brushed over my crotch. I stammered, “Ummm.. ok, I guess,” and then quickly added, “but only if I get to see yours, so it’s fair.”

[XPlayer]

Millie chuckled, and agreed. As I started to unbuckle my belt, Millie swiftly took off her t-shirt in one smooth move, exposing her breasts cupped in a lacy beige bra. I was feeling hotter now. I quickly took off my pants expecting, Millie to stop at revealing her underwear. But no, she had taken off her bra! Her bra was off, exposing her pert (around A/B cup in size) breasts and very erect nipples.

I just stared at that amazing sight of two wonderful breasts, the first pair of breasts I had ever seen live! Millie noticed I was staring at her breasts, and said, “Hey, not fair, you’re supposed to take them off too!” as she reached over and pulled down my underwear, exposing my hardened cock which was standing straight up.

I had barely said, “Hey!” when Millie said, “Oh, it’s standing straight up! You must be really excited! Hehehe!”

“You have such nice breasts,” I muttered weakly. Millie thanked me and then asked, “Can I touch it?”

“Uh-huh,” I nodded. She gingerly reached over and gently grasped my shaft in her hand. “It’s so hard, and it’s warm too!” She exclaimed, and started to caress my cock with her hand. “That feels very nice, Millie,” I breathed excitedly, as her cool hand rubbed my cock. It was more exciting that watching the porn movies, that’s for sure.

“Oh my,” I murmured again, as Millie’s hand rubbed up and down my cock. Her eyes were intent on my cock. My eyes were alternating between looking at her breasts and at her hand on my cock. At that moment, she glanced up to the TV screen, where an actress was giving this guy a blowjob. Millie turned to me and asked, “Want me to put it in my mouth like on the TV?” she asked. I just nodded, silently yelling in my excitement.

Millie lowered her head and swiftly put my cock in her mouth. As blowjobs go, Millie’s first blowjob on me was terrible. Her teeth scraped on my cock, she didn’t know how to deep throat, and could only take my cock in halfway. But at that time, it was my very first blowjob. And that was after having watched porn for the past hour. Barely 2 minutes had passed Millie started giving me a blowjob, and trying to imitate the porn actress on the TV screen. Suddenly I felt a wonderful wave of pleasure coming, and I knew what was going to happen. “Millie,” I started, “I think I’m going to – aaahhhh!” I bellowed, as I came. I shot huge loads of sperm down Millie’s throat.

Millie gasped and then gagged in surprise as my cum shot out. She pulled herself from my cock and sat up as my cock shot cum into the air and splattered her breasts. She hurriedly ran to the bathroom where I heard her wash and rinse her mouth.

A few minutes later, she came back to the living room, still topless. I had just finished wiping my sperm off my body with a wet towel and was looking at the damp patches on the carpet where some of my sperm had landed. I hoped that my wet towel had done the trick and no one would notice later.

Millie looked at me, and said in a rush, “Wow, I didn’t expect you to shoot like that so quickly, and so much! Is it safe to swallow it? I think I swallowed some by accident. It was a little salty.”

“Sorry Millie, I was too excited and it just came out,” I replied. Looking at the TV, I added, “I think it’s ok to swallow, they do it all the time in the movie.”

Millie looked at the TV, and agreed, “Yeah they do swallow it on TV, so I guess it’s ok.”
Then she looked back at me, and said, “That was a lot of fun, let’s do more!”

It was almost noon at the time, and the house phone rang, interrupting us before we could do anything. It was my mom, reminding me how to heat up lunch. So Millie and I decided to have a quick lunch. Lunch breezed by, as we were both impatient to get it over with.

We ate half a meal, washed it down with gulps of water, and in no time at all, we ran up to my room, jumped on the bed (it was more comfortable than the carpet) and quickly took off all our clothes until we were completely naked. Then copying what we had seen in porn videos, we frenched. I went down on her and licked her pussy, which had just a slight tinge of hair (apparently Millie shaved her pussy, following her elder sister’s example). Millie thoroughly enjoyed that, but as I was a complete novice, she didn’t orgasm. Another blowjob followed, but this time I stopped her after a couple of minutes, as I didn’t want to come so quickly.

“You want me to stop?” she asked, confused.

[soundworks]

sibei ho! Pls post more.

[12av3n]

Steamy story.I like!!!

[hugland]

Camping here

[paul^bibi^baby]

very good start ! can't wait for more ! up up up !

[best123]

camping here......and my humble 3 points to you!

[Neighbour]

Please keep i cumming

[XPlayer]

“Yes, I want to uh… ah.. put it inside your pussy,” I said nervously, not sure if she would take offense.

“I’ve never done it before, Tim,” she replied, looking nervous all of a sudden.

“I’ve never done it before either,” I said, before adding, “Come on, we’ve come so far, lets do it.”

“Umm, ok I guess,” Millie answered, “but you have to pull out, I don’t want to get pregnant, ok?”

“Ok, I’ll pull out,” I replied.

“You pull out, OK?” She insisted, sternly.

“I will, don’t worry.”

And so we began our attempt at sex for the first time in our lives. Our inexperience and nervousness made it far more difficult. For one, I had difficulty aiming for her pussy entrance. For another, Millie’s pussy was clamped shut, due to her extreme nervousness. It took copious amounts of lubrication (saliva), and about 15 minutes of trying before my cock suddenly slipped in a little.

“Oh!” Millie exclaimed. In my excitement at this sudden progress, I pushed myself in hard.

“Ahhh!!!!” she screamed as my cock apparently tore through her hymen and buried itself to the hilt into her pussy.

“I’m sorry, are you ok?” I asked worriedly. I had not expected the painful reaction.

Millie sobbed softly, “It hurts”.

“Oh god, I’m sorry,” I apologized, and started to pull out.

“No, no. no, let’s continue,” she insisted. “we’ve come this far, I don’t want to stop now”

And so I slowly pumped my cock in and out of Millie’s pussy. Her pain lessened and she started to feel pleasure too. We were actually doing it, we were having sex!

It felt so good that I could only last about 2 minutes after that. I held on for as long as I could, before pulling out and shooting gobs of sperm onto Millie’s breasts and stomach.

We lay on my bed for a couple hours after that, talking, kissing and cuddling. We cleaned up and Millie went home. She cried herself to sleep, she told me later. It was a sad and yet exciting time for her.

I apologized for what had happened, but that made her laugh. She said she wanted it too, so there was nothing to apologize for. Besides she said, now that I had taken her virginity, I had to continue to do it to her. She said it so seriously, I actually believed she was serious before she broke out in giggles.

After that fateful day, we continued to meet up whenever we could for sex. We watched more porn and practiced what we saw on each other. Eventually we got better and better at sex, and after about 3 months, I managed to give Millie an orgasm by going down on her.

We were terrified that she might get pregnant accidentally, but we were also too scared to buy condoms at the store. So I usually pulled out and came on various parts of her anatomy depending on what position we were in. Eventually I started coming in her mouth and she would swallow my entire load. We liked this the best though, as I loved the feel of coming with her mouth wrapped around my cock, and she loved the feeling of a spasming cock, plus she grew to like to taste of my cum.

Our relationship continued on an exclusive basis for the next year, at the end of which I began to have encounters with other girls, without Millie’s knowledge. Nevertheless, Millie and I continued to have sex on a regular basis for another 18 months after that (12 months till we finished our O-Levels, and 6 months after that). We never had a typical boyfriend-girlfriend relationship, as we acted more like friends, except when we were alone. And I guess we were never in love with each other. Our relationship eventually petered out when we both left for universities abroad. I went to the US, and she went to Australia.

We did meet up again for a renewal of our sexual relationship a year later during the summer, when we were both back for the summer holidays (winter holidays for her). For 8 great weeks, we had sex almost daily (usually during the day when both our parents were at work). And this time, she let me come inside her pussy, as she had gone on the pill before coming back from Australia.

Unfortunately, that was the last time we had sex, as we never saw each other again. We did try to keep in touch but distance, and more likely, other relationships got in the way. Nevertheless we did part on good terms and we do have those great memories.

[AD69]

Pitching my tent here liao. Looking forward to the next story.