My worst punt was many years ago, and one of my first punting experiences. It was late on a Saturday night, I was bored and horny, so used Craigslist to find someone for a quick outcall (shows how old this was, who uses Craigslist these days?). Saw a profile of a white, MILF (I was young at the time and preferred older women because they seemed to instigate action rather than me, which at the time I preferred because I was still new to punting and I still felt like I couldn't/shouldn't ask a women to performs certain acts or do things to turn me on because I didn't want them to think I was some dirty fiend). Anyway, exchanged some messages, and she said she'd be over in an hour.
An hour and a half later, no show, so I texted to ask if she was still coming, she said she was running late but was on her way. 30 mins later, still a no show. Texted to say forget it and she replies to apologise and says she's on her way, and to make up for it she'll do anal at no extra charge. Like the horny sucker I was, I took the bait and agreed to wait as she said she be 20 mins. 30 mins later, a no show. Text to say this time, really forget it, and she replied to say she was just looking for a parking spot and to confirm my address and she'll be outside shortly. At this point, I've been thinking about fucking for hours, but it's so late there will never be anyone else available, so again the little man spoke and I said OK. 25 mins later, she arrives.
I open the door, and what is standing in front of me is not what I was expecting. The photos must have been at least 10 years old, she has the drug waif look and, going by her slurred speech, she was clearly on something as well but, before I could even make a decision about what to do, she just walks past me and in to the flat. Now, where I was living then was a house converted in to flats, with thin walls and floors, so I could always hear what the neighbours next door and upstairs were doing, and I assumed they could hear me. This influenced the next set of decisions that I regret to this day.
Rather than asking this old, slurring women, who to me was severely inebriated in some way, to leave I was so scared if I told her leave that she would kick off a massive stink and tell my neighbours and probably the whole street what I was up to, and my life would be forever shamed and over with. So, I decided to go ahead and continue the meet as quickly and as quietly as possible. She asked if she could have a cigarette, but I said I'd been waiting so long to see her we should go to the bedroom. She shrugged her shoulders and followed me to the bedroom. I asked her to get undressed. She was wearing this fake, red fur coat thing and a white t-shirt underneath. She took off her coat, and took off her t-shirt. She wasn't wearing a bra, basically because he tits were so old and droopy it wasn't worth it. They literally looked like they had the life sucked out of them. I knew then and there I was going to struggle to even get hard, she repulsed me in every way. But my head is saying 'Get this over and done with, and get her out, or she'll scream and tell the neighbours'.
She took off her black jeans and her legs were bone thin, with bruises and scars over them. She asked me why I wasn't getting undressed (at least that's what I interpreted from her slurring). I couldn't tell her the reason was because my mind was racing with thoughts of repulsion, exposure of me punting secret to neighbours, thoughts of having to wash all the bedding because she was so repulsive I was sure she was transferring some disease to the bed spread and, worst of all, that she will give me a disease. But I felt I couldn't back out now, it had gone too far, she was undressed, I was young and scared of what might happen if I tried to back out of it. I was trapped in to having sex with this women.
I kept my top on but took my jeans and pants off. I asked her to help get me hard. Her hand touched my cock and I literally shivered in disgust at the feeling. She tugged for a bit but nothing was happening, then she leaned in to use her mouth. I remember closing my eyes because I couldn't take seeing my manhood have to experience what it was about to experience. Having to be touched by the mouth of a skanky old women. What else had she put in her mouth? What diseases does she have? My dick is going to fall off. I remember the first touch of her lips on my dick, and literally trying to pull away from her mouth, but she grabbed my cock in her hand and wrapped her mouth around it. I couldn't move if I wanted to. Her mouth was so dry, it felt like sand.
After about 15-20 seconds of me trying to think sexual thoughts in my head to try and get myself hard and get this over with, I asked her if she had any condoms because I didn't have any. She thankfully let go of my dick and grabbed her bagged, reach in, pulled out a box, and handed it to me, then went back to tugging my dick with her hand. I thought she had handed me a box of condoms. Turns out she handed me a pack of cigarettes. She was so out of it she couldn't tell what the fucking she was handing me. I told her she'd handed me cigarettes and she refused to believe me. I said look, these are cigarettes, and handed them to her. She looked them over and over for about a minute before agreeing they were cigarettes. I knew then she must of been on some drug that meant her mind was just not in the realms of reality at that point. She told me to look for the condoms in her bag. I grabbed one but, still not anywhere near hard, had to give myself a quick tug to try and make the little man wake up. After about two minutes I got a semi, told her to like back and put the condom on.
I climbed on top and put in the old codger as best as I could, thrusted about 3 times, then faked me cumming. That's right, I faked an orgasm. Even she, in her inebriated, hallucinagenic state still asked 'Have you cum already?'. 'Yes I have', I replied, and said look at the cum in the condom, as I quickly peeled it off and hid it from her sight. 'I need to go the toilet and clean up' I said, as a ruse to get the completely non-cum filled condom out of her sight and away from being incriminated. After spending a good 5 minutes in my bathroom making fake sounds as if I was cleaning my self up, I then emerged and said, 'Thanks for coming, I guess it's time for you to go now'. She got the cue, and was quickly dressed. I gave her the money, and shuttled her out of the flat as quickly as I could, I remember her trying to get her arms through her red fur jack as my hands was on her back pressing her forwards towards and out of the front door. I can't tell you the relief I felt when I firmly shut that door and she was out of my place. I have never felt so disgusted with myself. I took and damn long, hard shower, and removed the sheets and duvet from my bed and put them straight in the washing. I went to sleep ashamed and disappointed in myself, and didn't punt again for over a year because she had managed to disturb me that much.
