I met Chris online when I was about 25 years old, he was 29 and hadn't had much of a dating history. I had broken up with my ex about 9 months before, and I since the break up was so hearing breaking it took me a long time to start dating again. It had been 9 months since I had slept with someone.
I started up a profile online, mostly driven by the fact that I hadn't had sex in so long. But with the intent of actually meeting someone to date. It was only a couple of days of being online when met Chris. In hindsight I wondered what even drew me to him since his pictures were of him with his shirt off, he had a six pack and didn't look like serious dating material.
None the less, we matched... As I had already with plenty of other people so it wasn't all that exciting. However, he caught my attention as someone who was really keen to chat and meet up. At first I agreed and then cancelled the catch up since I felt like things were moving too fast for me and I hadn't thought this whole online dating thing through (which was fairly new at the time, but very popular).
He took the cancellation easily which in some sort of reverse psychology, tempted me to reschedule it rather than just cancel it. So I did, I apologised that i was 'busy' and set up a new time for the day after. Chris was easy going and flexible and happily accepted the new time, never forcing me to make a new time in the first place which I liked.
I met him the next day for a drink, he seemed OK I wasn't taking anything too serious or expecting it to go anywhere. But he seemed like someone normal who I'd be interested in speaking to again. I thought he was attractive, he had a full head of hair, tall, tan skin and he was European. Of course, I also knew that he was extremely fit under his jacket and jeans which helped.
By the end of drinks I was ready to go my separate way and play it cool. Until he turned to me and asked me if I wanted to go for a drive. I don't know why I agreed, but I did and even though it was already 10pm at night and I really didn't know him at all. For all I knew, his name might not have even really been Chris. But I got in his car not even knowing exactly where it was he wanted to go.
He said he wasn't sure where to go but very soon after that, came up with the 'idea' that we should go to the park near by. I agreed, there really wasn't anywhere else to go and I liked the fact that the park wasn't too far away from my car.
As we got there he pulled up into a dark spot, kind of creepy so I was either going to get murdered or hit on. He turned off the engine and we chatted a bit more before he leaned over to kiss me. I can't remember what he said before he did that or if the kiss was completely random. I was somewhat happy that I wasn't getting murdered. So I kissed him back, he was a good kisser and so it increased more and more sexually by the second.
It didn't take me much for me to drop my hand to his lap and pretend to innocently brush my hand close to his package on his thigh, since I was so sexually deprived. But my innocent brush was met with my hand brushing the shaft of his cock, which I had never felt a cock so far away from the centre of a man's pants before. I did not expect to be brushing his shaft this far on his thigh. I was surprised, but it immediately made my juices flow. I felt myself twitch and build up wetness in between my legs.
I was intrigued and instead of moving my hand away, I let out a moan and grabbed his shaft from outside his pants and squeezed it. I couldn't believe how thick it was either, it almost didn't seem believable that was I was touching a cock. I pulled away from kissing him to check if I was in fact touching a cock or not, my jaw dropped and I asked him is disbelief "is that you?"
Chris laughed and asked me "What do you mean?"
I responded shyly "I mean, what am I touching?"
He responded "... My cock".
He looked worried that I didn't mean to touch him or something since my questions was so strange.
I place my hand back onto him and leaned back in to him and said "wow" with nothing more to add.
He realised that when I placed my hand back into him it was permission to keep going. He said that he was uncomfortable and asked if I wanted to move into the back of the car. There was no one around so I did, I was undeniably wet and I wanted to rub slit over his pants immediately.
We got into the back and I sat on top of him, facing him and lowered my slit to his massive cock, sliding up and down through our pants. I was wearing a black pair of pants that were stretchable so it was thin enough to feel his length push against my clit. He panted heavily and I felt him twitching his cock at me more. I lifted up my top to expose my titts in my bra to him. He grabbed each one with both hands and squeezed while he panted in pleasure before pulling down my bra to free them.
He commented on them and said "You've got perfect titts" and continued to squeeze them and lick my nipples.
As he did he reached into my pants with both hands and squeezed and pulled apart my ass cheeks while lowering me towards his cock more. He was rock hard and I was soaking wet. I moved off him to take my pants off and exposed my black lace thong. He unbuttoned his pants ready to free himself but only readjusted himself within his pants before leaving them unbuttoned.
He leaned towards me and pulled my panties to the side, slide one finger down my slit and told me "You have a perfect pussy" before squeezing his package with his freehand and diving his tongue into my hole. He lapped up all my juices commenting on its sweet taste and how wet I was.
He tried to slide two fingers into me but I was so tight that he had to switch to just one. He put his finger in me and I could feel the whole thing, I hadn't realise how tight I had got over the 9 months.
He was shocked at how tight I was and looked up concerned and told me "you're REALLY tight"
I agreed without giving away how long I hadn't had sex for and instead I reached for his cock to free it. As I reached in and pulled him out I realised that he was actually bigger than I could feel through his pants. As a result, I unintentionally reacted and said out load "OMG that's huge! It's not going to fit!".
Chris smiled, I guess he was proud of himself but since he was pretty relaxed he said "It's up to you if you want to try, you don't have to"
The fact that he didn't push me made me want to take him in even more. We kissed and he rubbed my entrance trying to get all my juices on his hand and make sure I was ready. I lowered my slit onto him and rubbed him more to get get my wetness all over him ready to try him.
After a couple of minutes, since my hole kept getting wetter I said "I want to try"
He heard me and put his finger back in me, getting it all wet and switching to his second finger to coat it. Once they were both wet he put them both in me, he struggled but he rammed his fingers in after a couple of forceful pushes. He roughly pushed and pulled inside my hole to stretch me out ready to put his cock in. His fingers against my walls felt amazing, it was as though I was already getting fucked. He must have known he needed to get me bigger to even try. My hole kept excreting juices out as he fingered my little hole.
He took his hand out and rubbed my juices all over his cock. Then he pulled out a packet of lube from his centre console and rubbed more on my pussy entrance and on his cock. He said to me "I've never used this before so hopefully it's good".