My First Time - A Look Back

I posted this story years ago when I was younger, many accounts ago :p

I wrote it a few days after the encounter so it was quite vivid still.

Anyway, I stumbled upon it recently when I was cleaning out my computer. Thought I'd edit it a bit with newer insights and share it for you girlies :)

So i had my first encounter with a guy last night and it wasn't so bad!

Let me describe myself first, I'm a virgin, 5'5, korean/vietnamese, pretty average, pretty boring and pretty sheltered

So i met him on craigslist a few months ago. He was 19 and I'm 22 in college. After many back and forth emails with men of all sorts, he was the only one I felt more connected to, not because of his looks or anything, but his personality and how he made me feel. I felt he wasn't crazy and he made me feel safe.

(After years of experience, I've come to realize it's very hard to find people who are sane and you can connect with on the internet, who would have thought?)

We hit it off, we texted and talked via Skype a lot throughout the month, all throughout the day. I wanted to make sure he wasn't crazy crazy, this was my first time and I didn't want to die tbh.

So after a month or so of speaking and sexting, i finally had the courage to meet up with him. He didn't really push for it and I liked that. Although I still felt very nervous, I felt like it was a safe bet, so I went with it.

We decided that i'd come over to his house at 11PMish when his mom was asleep. It was around 7pm on that day when we decided to meet. I had a few hours to get ready. I did my usual routine and got ready, shower, shave, etc, being asian, I don't have hair, so there wasn't much work on shaving. I did my makeup, put on my blonde wig, painted my nails pink and wore my favourite pair of pink/white panties that had ruffles on the hem. I had a matching pink bra and garter as well. I also slipped on white stockings with a cute hem. I threw over a very very baggy sweater to go incognito :p

I lived in a student house at the time with housemates and had to sneak out.

I was so nervous throughout dressing up but i was looking at those sissy tumblr captions, so it helped me stick to the mission!

Back then, seattlejasmine was my idol, I'm not sure if she's still so active, but she really inspired me, thank you, queen.

Anyway, it was 1015-20ish by now and I was ready to go. My room is attached to the kitchen. I waited for the housemates to get out and the adrenaline was pumping as i quickly and quietly shuffled out.

I ran to my car and finally was on my way to his place. He lived 30ish minutes away from me, the whole ride there i was soo nervous... like, trembling, like, omg, like should I back out type nervous. I wasn't nervous about him being crazy, but nervous about what was happening, my first time with a man, my first experience ever with anyone. It was also exciting, I had butterflies in my stomach and was having such conflicting feelings.

I finally got there, the drive felt like an eternity. So i pull up to his street, turns out there is no parking on his side of the street...... it's one of those main roads with houses on the side. So i had to make a turn around and park on the other side.

The other side was packed with cars as well, with only room for people who knew how to parallel park.... Tbh I suck at parallel parking (I still do)

I ended driving to another side street. Didn't think this could get any worse.

The whole time i'm thinking of backing out because i didn't want to walk down the street wearing what i was wearing, in case someone saw me. I wasn't very confident on my looks then.

I parked and texted him that i was there. I was telling him i was so nervous and he was telling me to just step back and breathe, take it easy. What I found really assuring was that he said he didn't mind if I wanted to back out either, he would totally understand. It calmed me a bit.

Anyway,

He said he'd come out and walk me to his house

Oh, i should add, This is my first time ever dressing in public. Ever. So i get out of my car, scurry down the side street and on to the street his house Is on like a little mouse. Luckily there were no cars and people walking - only the terrifying blaring lights of some the surrounding houses still up at this hour.

I meet him on the his street, he says hi, slaps and gropes my bum underneath my sweater... what a gentleman. He's bigger and taller than I thought, which I didn't mind, I like size difference.

He takes my hand and we walk back to his place, like the car ride, this felt like infinity walking down that street. I am out of body right now, adrenaline pumping, just got my bum gropped, and this random man is holding my hand, guiding me like I'm a lost little girl. At this point. So many emotions are going on in my head and I don't even think I'm there.

We quietly get inside his house through the side door, it's all dark inside and he leads me to what seems like a living room in the basement, he also grabs my bum a few more times.

At this point, I'm just trying to acclimatize to where I am.

He let go of my hand and sat down on the couch, me, not knowing what to do, i decided to approach him and sit on his lap facing him. We look at each other for a while and i decided to peck him on the cheek because i don't know.. This was my first time kissing someone, especially a guy. I like the roughness of his face though.

He ends up guiding my face to his and we end up kissing. It's also my first time kissing and I love the feeling, feeling his roughness press against my lips. We ended up making out, It was amazing.

We broke the session only for him to take off his pants. He had boxer briefs on and I ended up sitting back on his lap, making out with him and grinding slowly on him. I could feel his rock hard cock straining against his boxer briefs and under my panties.

He took off my sweater and I was in my bra and panties sitting on his lap, still slowly grinding on him. I loved the feeling of his hands exploring my body as we continued where we left off.

It was the hottest experience of my life, it felt so right. I'm leaking precum in my panties as we make out. It was very out of body.

While making out for what seemed like an hour, I decide to be a naughty little girl and reach around and play with his crotch area. His cock is really hard at this point and i'm just rubbing it through his boxer briefs. I never touched another man's cock before and I was so excited to touch his.

I can feel the outline of his thick cock through them. I keep stroking it while we're making out and i decide to put my hand in his boxer briefs and take it out. It was at least 6 inches, thick, almost like sausage thick. His cut cock felt really smooth wrapped around my dainty little painted hands. It felt way different than touching my own little one. It was silky feeling and hard but also soft to the touch, It was such a new feeling for me as I stroked him up and down while making out with him.

I was trying my hardest not to cum as i was thinking about what was happening. I was his submissive and promiscuous little girl. Sitting on his lap, stroking his cock letting his hands explore my body.

After a while of stroking him, I felt more comfortable and i decided I would take it to the next step. I got up from his lap and slid down on my knees in front of him. I tried to be sexy and licked my lips while looking at him. He smiled and sort of laughed.

On my knees, I started playing with his cock with both hands. Stroking it slowly, playing with his balls. I started off very curiously, looking at what my hand was doing to him and his cock. He sat back and I kept playing. It was so interesting and fun. I was soaking in the idea that I was pleasuring another man and I loved every moment.

After a while, I got closer to his cock and started licking it like a little kitten trying new food. It felt so good to lick his cock all over. The silky, spongy, hard texture, it was so new to me and I loved it.

I ran my tongue on his shaft and slowly proceeded to the tip of his cock. It's such a strange but nice feeling licking a cock.. I was completely turned on at this point. he seemed to enjoy it and tilted his head back. I finally took the plunge and swallowed his cock the best i could. He took his hands and forced my head deeper and slower until i could feel his cock touch the back of my throat. I could taste his precum as well. I gagged like any normal person would and produced a stream of saliva as he took his cock out of my mouth.

I continued to give him a sloppy blowjob, so much saliva. I think i produced a lot of saliva because i was very intent on avoiding using my teeth. The blowjob i gave him lasted so long but i was in heaven going up and down on his thick cock. I felt like such a good girl pleasing my man.

My cock was throbbing now, trapped in my little panties. It was soo hard not to touch myself and make a mess inside my panties.

After a while, my jaw started to get tired so i started using my hands and just licking around. He then lightly tapped me and motioned me to sit back on his lap.I got up and sat back on his lap. he looked at me and asked me if i was willing to go a little further then a blowjob tonight. (When we talked before over skype, we had both agreed that it would be just a blow and go but I guess that wasn't the case)

I got caught up in the moment, i was super horny so i nodded yes. He kissed me and then slid his hand into the back of my panties. He played with my ass before he took out lube and started to finger me as I backed up on it.

He slowly wriggled his first finger in me. I'm used to a big dildo so this was fine and felt good to me. He then started to open me up, slowly entering his second finger..

He tried to play with my cock through my panties while he was fingering me but i stopped him knowing that if he kept touching me, I would cum.

Finally, he pulled my panties to the side exposing my ass and started to press his tip into me. I moved up a little closer to him and got up just a bit to spread my legs. Slowly, i lowered myself onto his cock. It wasn't working so he got more lube. We used a lot of lube. I was on his tip for a while and it finally went in after lots of adjustments.

Slowly, I went up and down so i could adjust to it. It was thick.. After a while of up and down motion, I finally got enough of it in me. I was holding on to him and leaning forward as it kept going in. It hurt a bit, my body was slowly getting used to his cock and he kept adding more lube. He started to thrust while whispering in my ear that i was being such a good girl for him, that turned me on even more and made me ignore the slight pain. I wanted to please him so bad so I tried my best to take him. I love the idea of being someone's good girl and pleasing them. I still love it.

After it went in and was adjusted, I slowly started riding him. he had his hands around my waist thrusting slowly and gently. He would kiss me every so often

I rode him and we started making out again. I started to reach around and play with the base of his cock and balls. His legs started to get tighter and i knew he was gonna cum. He took his hands and tried to take his cock out but i moved his hand away. I was this far in so i thought to myself that i might as well go the full way.

In hindsight, don't do this girlies, I was blinded by cock. Use a condom, I was young and dumb but it worked out.

He started to thrust faster and faster, his cock entering me was so smooth, it wasn't rough and I loved the feeling, like my body was made for his cock. I started to rub myself against him harder and lean into him more. I could feel his cock start pulsing in me. he started cumming inside me and I felt my insides warm up and my bottom become wet with the mix of lube and cum.

I kept rubbing against him until I came as well which was probably a few seconds later. He started to slow down the thrusting and then slowly came to a stop, we were both tired.

He pulled his cock out slowly and it slipped out really easily. We sat there, i was still sitting on his lap hugging him, leaned all the way, nestled into his neck. I had post cum clarity but I was so tired that it didn't matter. All that mattered was that I had just been fucked by this man and I really loved it. So many emotions in my head as his seed was in me, still leaking out of me into my ruined panties. We sat there in silence. I felt so warm inside and didn't want to move. He kissed me lightly on my cheek and i kissed him back. I sat on him for a while, It didn't want it to end.

We didn't exchange any other words, after a while, I got up, put back on my sweater and started to leave. He grabbed my ass again. He led me to the side door, we kissed again, I enjoyed the height difference, looking up to kiss my man on the lips. i walked to my car not caring who saw me. I felt so free and liberated. I was giddy like a school girl, a complete mess with cum soaked panties. it was around 1:30 when i got home. He texted me goodnight too.

We ended up seeing each other many more times throughout the years.