As I got home and sat down at my desk, I pulled up my phone and opened the Whisper app. It was my best bet at finding someone to have sex with this late at night (it was 1:45am). I sat and thought, wondering what to post… what did I want to convey? Obviously that I wanted sex. But I needed something more… I didn’t want sex with just anybody, after all! Hmm…
I’m back in discord with M. I tell her what I’m thinking, wondering if perhaps she can think of something… We both ponder the question. Then I tell her what I keep thinking again and again… I want to post “Make me cum” or “Can you make me cum?” but I know that won’t get past the moderators… What do I change it to? .. Aha! Bingo! “Are you enough for me?” Post.
Instantly, my inbox is flooded. But I scroll through the responses, looking for ones that are nearby. I only talk to them unless someone elsewhere says something that catches my eye. There’s a lot of people to sort through but I start to gravitate around a specific set of people. The one guy isn’t even in town. He wants to drive from the other city over (a 45 minute drive) but it’s 2:45am now. If I tell him yes, I have to tell the other guy no… What if this guy backs out or doesn’t show? Plus it would be so late before he gets here! Okay, I decide to make plans to meet up with him later. Back to the other guy. We converse more, I’m getting more and more excited. I’m going to get my chance at having some sex again tonight!
My hopes are torn when I learn the other guy does not have condoms and can’t get any tonight. Well damn. So much for that. Ugh. I’m out of options now… I might have to just masturbate… The thought isn’t pleasant. But wait!
A new message flashes across my inbox. He (T) wants to meet. Now. He’s nearby, older (that means experienced right?). He has a couple of hours. He offers to pay my cab fare. Okay, I’ll go I decide. So I order the taxi.
The driver who shows up is none other than the friendly man who drove me that Friday from the grocery store. He was a nice fellow. I enjoyed chatting with him on the ride home and he insisted me meet again some time. He seems elderly. He looks at least 40-50 years old. I view him as a harmless old man hitting on a pretty girl.
I was embarrassed climbing into the van, looking over at S (taxi driver). He smiles warmly and says, “Hi stranger!” in a friendly chipper voice. I smile back at him and laugh, “It has been a while.” He asks me where I’m going this late at night and I fabricate a small lie about visiting a friend to escape the heat… Partially true, but mostly a lie. I cringe internally. I hate lying. But, I’m not going to tell this man I’m going to have sex with a man I don’t know from a hole in the ground. It didn’t matter anyway, anybody knows if you’re visiting someone this late at night you’re more than likely fooling around.
As we pull up to the house, S tells me to call him if I need anything and to be careful. He gives me a knowing look. He must see this all the time with his job…
I was nervous. The area wasn’t the greatest part of town and he was one of those people that look kinda scary. One of those people you almost instantly feel like you should stay away from. But I followed him inside anyway. He directed me to his room and I waited there while he dealt with his dog.
His room was small and cluttered. There was stuff everywhere. It wasn’t exactly dirty, just disorganized. I smelled cigarettes and I ignored the cloying feeling at the back of my throat. I hated cigarette smoke. But it doesn’t bother me as much now. He comes back into the room and sits down on his bed, motioning for me to sit down as well.
I sit with him and he lights up a cigarette, then offers me a joint. I take it, feeling relieved. It would help but my mind at ease and make me relax. We chatted for a while as we smoked, talked about nothing significant. He was one of those types of people that didn’t need responses. I got the impression he could talk for hours. All he would need is an acknowledgement that I was listening every now and then. A lot of the time he talked so quietly or so fast that I couldn’t make out what he was saying.
We chatted and smoked for maybe about 15 minutes. Then he started grabbing at me. We both knew what I was there for. I smiled a little uncomfortably as he told me I couldn’t be shy and not to back out now. I shook off my misgivings and said I wasn’t backing out as he began undressing. I did the same.
He came over to me and rubbed my breast. Then he grabbed my hand and pulled it to his dick. I knew what he wanted, that was obvious. I wrapped my hand around his length and jerked my hand up and down. The angle was awkward and my hand kept catching. It wouldn’t move up and down smoothly.
T grabbed some lube and laid in the bed. I put some lube on my hand and continued to give him a handjob. He poured more lube onto his dick. It was of a just below average length and thin. My stomach churned a little, knowing likely he would not be enough for me. But I dismissed the feeling and continued on. He was hard now.
As I handled him, he reached over and started to play with me but absentmindedly. There was no real intent or sense of purpose behind what he was doing. His fingers weren’t anywhere near where they needed to be. He stroked me between my opening and my ass, his finger flicking across it every now and then. I knew he thought it was my opening. I stayed quiet. After a bit, he moved his arm back and found the right spot. He shook his fingers back and forth across my clit and I clenched, shivering a bit at the contact.
He reached for a condom and put it on, then asked me to straddle him. I did. The whole situation turned awkward because he couldn’t get himself inside of me.. I was wet enough, despite the lack of foreplay. He just couldn’t find the right spot. Finally he made me lay on my back and still he could not get himself into me, going soft.
He shoved his fingers into me while he played with himself, trying to get himself hard enough again. I didn’t mind, it did feel good. But I knew he was doing nothing for my benefit. Despite that, I internally begged for him to be inside of me. I wanted to be fucked so badly. Finally, he flipped my leg over his shoulder, positioned himself over me and pushed down as hard as he could into me. At last! His cock was in me.
I moaned and closed my eyes, turning my head away as he thrust into me. My head was pressed awkwardly against the headboard and I thought of my ex. He always made sure I was far enough down on the bed that that didn’t happen. And if he ever saw my head move close to the headboard, he would pause everything and make me move down. Not T. T didn’t care, I doubt he even noticed.
Barely before it began, it was over. T pulled out of me and came over me. At this point I wasn’t sure if he was just pausing or if we were done. I hoped and hoped that it was just a pause. But no. We, no, HE, was done. He got up and threw a towel at me to wipe myself up. I did so and gazed with eyes full of disappointment. He didn’t notice. Of course. And I left shortly after that.
Once again I was driven home by the same driver. He asked me if I would go for breakfast with him in an hour after he dropped me off… I agreed. I wouldn’t be able to sleep and some company with a nice man didn’t sound bad to me. Plus, less time in the heat.
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