It started with a throwaway comment after a few drinks during a night in with my flatmate. “All of your celebrity crushes are so old… I bet you’d never do anything with a guy that age.”
I was in a confrontational mood and wasn’t going to lose this debate, so I vehemently assured her that I would, no problem. “So you’d… I dunno… blow an old man?” she asked, laughing and taking another swig of her drink. “No way you would.”
I assured her again that I would, and that age isn’t that important. I almost spit out my drink at her response. “Prove it then”.
My first mistake was probably asking her how. My second mistake was not telling her to shut up and that she was drunk. The conversation only escalated from here, and by the end of the night a bet was in place – the winner is the person who gave a blowjob to the oldest guy they could find by the end of September. My flatmate had even written out the rules, and I was defiant and drunk enough to agree to them all:
1. The winner is whoever gives a blowjob to the proven oldest guy by September 30th
2. Photo evidence of the person’s ID and the act taking place is required
3. The blowjob has to be until the guy cums
4. The winner gets to choose any one (legal) forfeit task that the loser has to carry out
It was surprisingly coherent when we woke up the next morning and realized that we weren’t drunk enough to be at least somewhat serious about it, which in turn meant neither of us was going to back down. We were now two 18 year-olds on a mission, and our competitive spirits meant there was no chance of me – or her – saying let’s forget it and moving on.
My flatmate struck the first blow (sorry) by meeting a 43 year-old a couple of days after we made the bet – I’m not sure where she found him, but I went and created a Tinder account… and this afternoon, I blew a 48 year-old in the back of his car.
Unsurprisingly, I got plenty of matches on Tinder, but most of them didn’t believe me or were incredibly creepy and I felt uncomfortable even thinking about meeting, so it was a relief to find a seemingly normal guy who was concerned about my safety and making me feel comfortable. We talked and figured things out, and eventually a plan was set.
This afternoon, after a lazy morning I took a shower, changing into a lacy black bra and thong, and slipped into a black dress. My flatmate knew where I was headed – we’d agreed to that for safety above all else – and so wished me luck with an off-hand comment about feeling free to get cold feet if I wanted.
I’d agreed to meet him reasonably close to me, so it was about a 10 minute walk to the car park near a big park – there were a few other people around, and the car park had security cameras, which eased my worries. I also spotted the blue car I’d been told to look out for, and as I headed over towards it I saw the guy getting out of the car. He had a slight beer belly and a beard, and was wearing a t-shirt and shorts in the humid weather – he was reasonable looking and well-kept, at least.
After complimenting my looks, expressing surprise that I really was genuine and that I’d actually turned up, we talked out in the open a little – about the weather, what I study and other small talk, before the chat turned to whether I was still open to doing this and whether I wanted to go for a drive and find somewhere quiet. I told him I was ready, and so he invited me to hop in the passenger seat as he got in the car, and off we set.
As he’d traveled from a little further afield, I was in charge of suggesting locations, and so I gave directions to drive around and check out other locations around the outskirts of the park. The first couple of places were either busy or not suitably quiet to park up, but eventually we found a road that was out of the way, secluded and with nobody in sight. Agreeing this seemed like a good place, we sat in awkward silence until he suggested we slide the front seats forward and get into the back, which he duly did, moving the seats and climbing in the back before I followed.
After checking once again that I wanted to go ahead with this, he tentatively asked if I’d be willing to show him a little more of me to help excite him. We’d discussed this on Tinder and I’d agreed to it, and so I reached back and unzipped my black dress before sliding it off my shoulders and wriggling out of it, leaving it on the car seat. I was now sat in my lacy bra and thong, with his wide eyes admiring me and complimenting my body and looks.
Remembering I needed evidence at this point, I asked if he had ID – he fished out his wallet and took his driver’s license from it, and we spent a little while with him awkwardly finding ways to hold it that showed his date of birth but not other important information while I took a photo, and he enjoyed me shifting around and leaning over to get a good pic.
“I’m really ready for this now if you are” he told me. I confirmed I was, and so he raised his hips and pulled his short and boxers down together. He wasn’t completely hard but was partway there, circumcised and (according to him) about six inches. I shifted around on the back seat to kneel across it, brushed my hair back behind my ear, and lowered my head. And there it was… I had the dick of a stranger 30 years older than me in my mouth.
He groaned surprisingly loud as I started to suck and move my head, and it wasn’t long before he was completely hard in my mouth. Even my flatmate didn’t know, but this was only the second cock I’d ever sucked, and so I took some time trying to figure out what worked. Thankfully he was pretty vocal, groaning when I did something he liked, and I soon found ways to use my mouth and tongue that he seemed to be really enjoying.
He sat there enjoying the sensation for quite a while it seemed, before I felt a hand resting on my bare leg, then sliding up to my ass. “Is that okay?” he asked, and I nodded while continuing my work. He squeezed and stroked my ass for a bit, before I felt his fingers shifting to press against the fabric of my thong. He rubbed up and down tentatively, which caused me to sigh at the pleasant sensation. This only led to him rubbing more firmly up and down the fabric, making me whimper while I desperately tried to concentrate on what I was doing rather than getting turned on and wetter.
I don’t know if he’s noticed that, but I felt his fingers at the edge of my panties, and then sliding underneath until his fingers were now directly rubbing my pussy. “Ohhh you’re so wet” he exclaimed, and I felt him seeking out my clit and rubbing it as best he could from inside my underwear. He quickly got frustrated by this I guess, and I felt him remove his hand before awkwardly taking hold of the waistband of my underwear and tugging it down until they were around my thighs, exposing my pussy.
I was still trying to focus on my job at this point, but that ended once a finger slid up and down my pussy and then slid inside me I couldn’t help but lift my head up to moan. This only motivated him to carry on, and he started fingering me with one, and then two fingers. I hadn’t been touched by anyone else all year, and I hadn’t expected to get so turned on by this, but now I was moaning and pushing back against his fingers as I could hear and feel them pushing in and out of me. The blowjob had been forgotten for now, but he didn’t care, and moved to rubbing my clit fast. He was now urging me to cum as he flicked my bean as fast as he could, and within a minute or two he was asking if I was going to cum as I nodded, still leaning over him until I was moaning loud and shaking with an orgasm until I nearly collapsed onto him.
Recovering my breath, he asked if I was okay – still completely hard, he asked me to finish him off “however I liked”. I’m sure he was hoping for more given my current state (and part of me was tempted), but I instead breathlessly reminded him to take a photo or two of me for evidence, as my mouth returned to his dick.
He was more verbal now, taking a few photos while telling me how good it felt and how he was ready for his turn to cum before putting his phone down and simply enjoying the experience. I was completely focused on my mouth and tongue getting him off, and I got the impression he was getting there now I knew what worked for him.
It was a few minutes I think before he warned me he was close, and I bobbed my head faster and swirled my tongue until he groaned that he was cumming and I felt my mouth filling with my cum, which I managed to swallow as quickly as I could. Finally he was finished, and I looked up, again getting my breath back, and suddenly feeling self-conscious about being in a guy’s car in just a bra, with my thong around my knees. I pulled my knickers up, and we sat on the back seat for a while, cooling off and regaining composure, before I eventually put my dress back on. He sent the photos he’d taken to my phone and deleted them in front of me.
He offered me a lift back, but I actually wanted a longer walk to cool off, so told him I’d be okay to walk back and leave him to it. He thanked me, and told me he hoped to meet me again if I ever wanted. Half an hour later I returned home to my flatmate hovering and waiting. “Well?” she asked. I missed out the details of my own orgasm, but showed her the evidence, and I’m now in the lead in this insane bet…
Source: reddit.com/r/gonewildstories/comments/igk11u/a_bet_with_a_flatmate_led_to_me_sucking_off_an
Should have told her you cummed, it would have really proved your point
So damn sexy. Life is meant to be lived