Fact
29 Aug 2016


When I recently passed a lady (of apparently doubtful character!) standing hitchhiking next to the road, I was reminded of a fantastic experience I enjoyed many years back…

It would have been early nineties, and I needed to attend a tender site meeting in Phalaborwa at 10h00 on a Monday morning. My options were to either get up at sparrow-fart on Monday and drive through and hope to get there on time, or else to drive up on the Sunday afternoon, sleep over Sunday night in Phalaborwa, and have a leisurely breakfast and know I would be on time… I naturally chose the latter option!

I was on the M2 near the Cleveland offramp (not a very nice part of town) when I saw ahead of me what looked like a long-haired young lad hitchhiking, but with a mountain of baggage at his feet. I had no intention of stopping, but I slowed a bit as I passed, and looked across at the chap. To my surprise, I saw it was an older woman standing there, very flat chested and boyish-looking, but evidently female, and not looking very happy. I pulled across into the emergency lane and stopped, and then had to back up a long distance to get back to her, taking care to stop before driving over her baggage.

She ran up to the passenger window. I asked where she was going, and she told me she was on her way to Durban to go and stay with her daughter. I explained that I was going to Phalaborwa, and would be turning north up the N3, while she needed to go south, and that it was so close by it would be too much effort loading up all her luggage for that short distance - she would be better off waiting for someone who was going in her direction.

She was virtually in tears. She explained how she had been standing there for way more than an hour already, there were very few cars on the road anyway, but that no-one stopped, probably on account of all the baggage she had with her. She said she was really desperate! She asked where Phalaborwa was, and I explained that it was 500kms away, and in the wrong direction. She asked what I was going to do there, and I explained that I would be sleeping overnight, attending the site visit, and then returning on the Monday afternoon. She pleaded with me to help her out, explaining she was destitute, had no other options, and wanted to get off the road before it got dark, but no-one seemed to care to want to help her. She asked if she could then maybe get a lift with me to Phalaborwa, and then try to get to Durban on the Monday when there might be more traffic around (I must just look like the decent soft-hearted sucker type!). And then she said the magic words – with tears in her big blue eyes she said “I’ll make it worth your while”…

What the heck…. I had the space in the bakkie for all her baggage, the company was paying for my accommodation anyway, and I would at least have “interesting” company for the long trip up and back. She didn’t look the type who was going to try and mug me, and there was now the prospect of it being “worth my while”… So I relented and agreed to take her.

I spent ages loading all her cases and bags and packets into the back of the bakkie, and we set off. Along the way she told me the story of her life – pregnant before marriage, an abusive husband with whom she had stayed because she didn’t see that she had any other options, but he had since left her for a younger prettier model with bigger tits! She had tried to make a go of it on her own, but had long since run out of money for rent and food, had been living off charity for a while, and had now decided to go to Durban to live with one of her kids and try to make a new life. A really sad story…

She was probably in her early - mid fifties, I was in my thirties. Her face was not unattractive, but no make-up, long black hair looking like she could definitely do with a hairstylist, very slim boyish figure with narrow hips, skinny possibly to the extent of anorexia, and no tits at all.

During the trip, whenever I had opportunity, I looked at where her bosom should have been. It was obvious that she wasn’t wearing a bra (she had absolutely no need of one), but it was also obvious that she had very long prominent nipples, about the size of thimbles, which poked against the white buttoned shirt she was wearing. Occasionally I got a glimpse through the shirt opening of one or other of those nipples. I think she was aware that I was looking there.

Although I felt sorry for her situation (and I genuinely am a nice softy!), I also felt a bit mercenary, was quite prepared to help her, but expected to get my pound of flesh in the end for my troubles.

Deep into the journey, otherside of Lydenburg, I decided to push boundaries a bit and asked her what she had meant when she said she would make it “worth my while.” Maybe she regretted having made the offer. She seemed to consider for a while, looked a bit uncomfortable, but then obviously made her decision and slowly unbuttoned her shirt, exposed her nipples, and said “I’ll let you play with these.” I immediately took the opportunity, while still driving, and reached across with my left hand and tweaked her closest nipple. It was not even hard, yet it was so big! As I rolled it between my thumb and fingers, it grew harder, and a little bigger! I let her know that I enjoyed nipples, especially nice big ones like hers. She said she just wished she had boobs to match, but that she had never been blessed that way… Although, to be honest, I would like to have had a bit more boob to play with, I told her that her nipples were just great, and I was enjoying touching the one I could reach. She said she liked having them touched, as they were very sensitive.

I figured, nothing ventured, nothing gained… As soon as there was a safe spot to pull over, I pulled off the road, so that I could use both hands. I helped lay her seat back a bit, and then started to suck on one nipple while playing with the other. She seemed to really enjoy what I was doing, moaning contentedly. I tried my luck pushing a hand between her legs, trying to get at her pussy, but she kept her legs tightly together, and I left off as she didn’t seem to be wanting to play along, and I didn’t feel comfortable pushing the issue. Instead, I laid my seat back a bit too, undid my belt and top button, opened my zip, and pulled out my cock which was already half erect, to see what she would do. She reached out a hand and started wanking me, and once I was fully erect she leant over and took my cock in her mouth and started sucking me. It did not take long before she got me to climax, I warned her I was getting close but she just kept on, and I came in her mouth. She opened the passenger door and spat my sperm out onto the ground outside, found a tissue in her bag, and wiped her mouth. She buttoned her shirt back up. Feeling quite adequately rewarded, I zipped up and we continued on to Phalaborwa.

We booked in to the motel, only taking some of her baggage in, leaving the rest locked in the bakkie canopy. As it was Sunday and I was afraid that restaurants might close early, we just had a quick wash and dashed out for supper. She ate very little, taking most of her meal home as a take-away.

Back at the motel, I had a quick shower while she sorted out some stuff in the bedroom, and when I finished she went through and had a bath. I lay on the bed, wondering what might still happen that evening, given her resistance to my earlier attempt to touch her pussy. I had come out of the bathroom wearing my towel, and when she went straight in to bath, I dropped my towel next to the bed, and lay there naked, but covered by the sheet (it was hot in Phalaborwa, but we had a fan in the room). Thinking about her, and what she might be doing in the bathroom, I started to get hard again, but hid my erection and the fact that I was gently wanking by making a “tent” by raising my left knee under the sheet.

She eventually came out of the bathroom wearing a pair of short but loose-fitting sleeping shorts and a T shirt, her nipples again clearly visible. She fiddled around for a bit, getting ready for bed, including bending over her suitcase with her back towards me. As she bent over, I saw long silky pubes protruding from her short shorts, and they were BLONDE! That came as a surprise, as she had black hair…! My erection hardened even further at this revelation!

Eventually she was finished with her fussing around, and came to lie on the bed, lying on top of the sheet, her head back against the pillows, her eyes closed, with what might have been tears in the corners of her eyes. She said “Thank you that I have a safe place to sleep tonight.” I replied – “My pleasure. And you’re making it worth my while!”… I reached over and put a hand in under her T shirt, and started tweaking a nipple again. She smiled. I let go of my cock and brought my other hand out from under the sheet, pushed her T shirt up, and started sucking on one nipple, while massaging the other. Then I let one hand wander down towards her pussy, to see how she would react.

This time there was no resistance! I rubbed her pussy through her shorts at first, then ran a finger in alongside the leg of her shorts, probing amongst the hairs and found her pussy opening, and ran my finger gently along her slit. She opened her legs a bit, aiding me in my explorations. I found some moisture, and pulled it up towards her clit, and started rubbing her clit lightly. She moaned quietly…..

She reached a hand in under the sheet, searching for my cock. I made sure she found it. We lay stroking each other gently for a while.

Suddenly she let go of me, withdrew her hand, raised her hips off the bed, and slid her sleeping shorts down. I helped her get them off. I was presented with a view of a prominent “beetle bonnet,” covered in soft silky blonde hairs, not very curly, and seeming much longer than any I had seen before. When I commented about them being blonde, she looked at me as if I was a bit of a twit, and explained that she was actually blonde all over, but had died the hair on her head. She pulled the sheet down, and ran her fingers through my ginger curly ones, then said – “I’m glad you are not particularly big. Please don’t hurt me, I’m very tight, and I haven’t done this for a long time”… Then she sat up and straddled me, facing me, and lowered her pussy towards my cock, her caesarean scar very evident.

I ran the head of my cock along her slit, seeking for some more moisture, separating her labia. She tried to push down onto me, but she was VERY tight. It took a while before she was able to take me in, going very slowly, taking just a few millimetres more each time she pushed down, then pulled back up. Slowly her pussy stretched and opened up, with her increasing wetness also helping to ease the passage. Then finally I was all the way in. She started to ride me slowly, all the way up, and then all the way back down again. It was sheer heaven. She was so tight, I have never in my life experienced anything quite like it…

It was a truly wonderful cowgirl ride. She kept her T shirt in place, possibly embarrassed about her lack of boobs, but I had a hand inside, toying with her nipples, and with the other hand I rubbed her clit as she slowly rode my cock. Because I had already cum earlier in the day, and had been stroking for a while while she was in the bath, I managed to hold out long enough for her to cum first before I exploded inside her.

We both slept well!

Next morning, I wanted more of the same before going for breakfast and then for the site visit (the actual reason for my being there!). This time, however, she wanted to lie on her back, but placed a pillow under her hips to get the angle that she wanted, and I fucked her gently in missionary position.

I left her lying on the bed, while I jumped in the shower, dressed and went for a quick breakfast, before leaving for the mine. She had a leisurely bath and breakfast and packed up all her stuff while I was away, and was waiting for me in the lounge with our luggage when I returned at lunchtime.

I packed our stuff in the bakkie, and we started off on the road back home. Along the way I was once again treated to more views and feels of those magnificent pointy nipples, and yet another delicious blowjob.

We eventually got back to Gauteng, and I dropped her off at a truck-stop near Heidelburg, waiting with her to ensure that she got a ride with a decent-looking trucker, to take her and all her baggage on her way overnight to Durban and her waiting daughter. I hope she got there safely. I also hope that the trucker too got rewarded in some way for his part in ensuring she got there…. I most certainly was!!!!


Comments