I [F] Lost a Bet and Ended up Cum Covered and Photographed

I was in my last year of high school and had broken up with my boyfriend months earlier.

It was the first time in my young life that I was sexually active, but had nobody to help me scratch the itch. I had no idea what I was doing when it came to masturbating back then so as the weeks went by sexual frustration continued to build.

I myself am 5’4, 110lbs. I have raven-black hair past my shoulders, 36DD breasts, although they were not quite that big when the story took place.

None of the boys at school were interesting to me so I tried one of those online dating websites, where I was quickly swamped with all sorts of men. The attention was a nice ego boost, but I lost interest in the site fast. Out of the 100+ messages I received I think I only responded to 3 and only one of them really went anywhere. This guy, Jay, was 29 and recently divorced. He had 2 kids with his ex and said he wasn’t interested in a relationship, but would love to get to know me. It sounded like exactly what I wanted, a no strings attached hookup.

We planned a casual evening at his apartment, still under the pretense that we were meeting to ‘get to know each other’. By this point we had flirted heavily. Lots of innuendo, and teasing, but nothing explicit had happened. Regardless, maybe do to his age, I expected things to get hot and heavy quickly once I got there.

Unfortunately, when I got there he was hanging out with a group of people who were all having a card game in the kitchen. He introduced me to his 2 room mates, 2 significantly less attractive guys, and their girlfriends. They were all much older. This wasn’t the scene I was expecting.

Jay didn’t disappoint in the looks department though. He was taller than expected (about 6′) and looked to have a great body.

Jay helped get me comfortable. He mixed me a drink and let me look at his hand while he taught me to play poker. Eventually I picked up the rules and they agreed to let me into the game. I was having fun and even looked like I might win for a while, but I got crushed when it was down to me and one of Jay’s room mates.

After the game, the others left me and Jay alone in the apartment. He suggested we play some more poker, which I was very much into. He kept beating me without breaking a sweat which made me more and more determined to beat him. I could tell he was getting bored with the game though when he started to suggest we go watch a movie or something. I begged him for one more game, to which he responded ‘what’s in it for me?’

The way he said it peaked my interest and got me thinking again about why I came here in the first place. I asked him what he wanted. He said he would write something on a piece of paper and if I lost I would have to read it and do whatever it said. Clearly he had thought this out. I agreed hesitantly, not knowing what I was getting in to.

This time the game was different, more serious. He was folding a lot more hands and had stopped cracking jokes. Whenever he was winning he would start with some trash talk. I pried the whole game for hints about what was he wrote down but he wouldn’t budge. At one point the game was particularly close to being over and he said, “You can just get on your knees now.” Unfortunately for him I caught a lucky card and that actually put me in the lead. He wouldn’t shut-up about how lucky I was and I kept rubbing it in his face that he was going to lose to me. He in fact did go on to lose. I was proud of my win and insisted on retiring a champion, despite him begging for a rematch.

I peaked at the paper a while later just to confirm. He had actually written that I would have to strip down to my bra and underwear to give him a blowjob. Reading it, and imagining it, got me so turned on that I had almost wished that I had lost.

After I refused to play another game we agreed to watch a movie, but ended up watching Game of Thrones instead. This was back during season two and the ninth episode had recently aired. It was the battle of blackwater, a really intense episode that I ended up getting really into. He had seen it already, but said he wouldn’t mind watching again.

We cuddled up under a blanket to watch. He put his arm around me and I melted into him. It was probably just five minutes into the episode when he started moving his hand up and down my leg under the blanket. It really got me going and I repositioned myself so that my arm was resting on his crotch. Sort of subtly, but in retrospect not really. He kept moving his hand up and down my leg, getting increasingly bold with how much ass he would touch, or how close to my pussy he would get. It was driving me crazy. I could feel that he was hard underneath his jeans. Occasionally I could feel his cock throb and it was everything I could do not to just pull it out and start stroking. I preferred to be patient and let him make the first move though. It went on like this for such a long time and I started to get impatient enough that I moved my hand down to feel his cock better. I started stroking it a little over his jeans, trying to embolden him.

Surprisingly he said, “Who do you think is going to win the battle?”

And we got into a conversation about the episode, all the while he kept touching me. He was fully cupping my ass now as we talked.

He said, “If you guess wrong about who wins the battle you have to do what I wrote on the paper.”

I had to protest that this game of his wasn’t fair since I had nothing to gain. He suggested that I could write two things for him to do and he would get to write something else in addition to what he wanted me to do. Honestly, I just wanted to fuck at this point, but if this was how he wanted to do it I was okay with that.

Of course I guessed wrong (the lannisters won) and as soon as the credits began to roll I got down on my knees, ready to finally kick this off. He handed me the first piece of paper, which I already knew the contents of. So, I took off my shirt and pants, then pulled out his amazing (7″?) cock, the biggest I had ever seen. I worshipped that cock, the first I had touched, or tasted, in months. I started slowly with him, licking the tip and shaft, kissing it, rolling my tongue around him. I did this until he started to moan a little and thrust his hips. At which point I swallowed as much as I could and started to jerk him off while letting him thrust into my mouth. After a couple of minutes of this he told me to get up on the couch. He bent me over doggy-style, peeled my panties down to my knees and commented on how sopping wet they were. He started fucking me, not easing into it at all. He was giving me everything he had right away. Like I mentioned, I had never taken a cock this large before. He was stretching me and hitting my cervix. It hurt! But it felt amazing at the same time. I couldn’t stay quiet at all. Every time he trusted into me I cried out.

He reached his hands around my neck and started choking me while he fucked me. This was too much and I felt an orgasm start building almost immediately. I started to moan, “Fuck, I’m going to cum on your cock” and he started pumping even harder and faster until I collapsed from an incredible orgasm.

Before I could even catch my breath he unclipped my bra, flipped me onto my back and came all over my face, calling me a ‘good girl’ in the process. It was amazing to finally get off like I needed and I loved how rough he treated me. I had never experienced anything like it.

My eyes were shut tight with a pool of cum collected in the corner of one eye. I asked him for a tissue and he said he would go get it. I just laid back thinking about the amazing sex I had just had. A few minutes later he finally came back and handed me the tissue.

We cuddled together for a while and got to talking more about the show and how much fun we’d had that night.

Then I remembered, “What was the second thing you wrote?”

He showed me the paper that read, “Let me photograph you with my cum on your face”

I nervously laughed, saying I guess it was too late for that now, but he replied that he already got the photo and he showed it to me on his phone. I thought about making him delete it, but I like the idea of him having a souvenir to remember the night by. Besides, he didn’t know anyone I knew to share it with, and being covered in his cum was a huge turn on for me.

I stuck around for a while and we fucked again before I left, this time a little more gently.

That was my first time seeing Jay. A casual hookup that turned into a year-long casual relationship.

Source: reddit.com/r/gonewildstories/comments/k2xvu6/i_f_lost_a_bet_and_ended_up_cum_covered_and