Date: Sun, 19 Feb 2023 13:08:46 +0000 From: teutonic1190 Subject: Dating Single Mothers 7 It's the mid-90s and, at the age of 30, I find myself single after a 9-year relationship. This series of stories shares my experiences of being back on the dating scene. The stories are a fictionalised account of activities, based on real relationships. If you enjoy reading these stories, do please donate to support this fabulous website which so fabulously plays host to our interests https://donate.nifty.org/ ---------------------------------------------------------------------------- Lisa was more of a distraction than a dating experience. This isn't as good a story as the dating ones but I thought I'd share nonetheless. Pre-mainstream internet, I came across Lisa on one of those telephone dating services. She lived in Leicester - I was in London -- had two kids: a girl of 4 and a son of six months, but was 19 years old and had a nice voice. Had to be worth a sniff, right? So one Friday evening, I left work, aimed the car up the M1, with the intention of ending a two-month pussy drought courtesy of a young lady in the final knockings of her teens. I arrived around 8.30pm, and her children were already in bed. Another typical single mum house: no carpets or wallpaper; hand-me-down furniture and broken toys. The wine and beer I'd brought with me were tucked into, but the idea of heading upstairs soon took hold as the ideal situation. Lisa was pretty enough -- nice dark hair past her shoulders and big blue eyes, my favourite combination. Stripping her off though, she had the kind of worn out body a woman twice her age in Medieval times would have had. Her once big, heavy tits, now hung long and empty, her areola still large and dark from having recently given birth, but the nipples thick and destroyed from prolonged chewing. She'd lost none of her baby belly, and it hung like a half empty sack of potatoes, riddled with stretch marks and blemishes. She'd had a go at shaving her cunt, but had clearly used a razor which had seen better days; her pudenda covered in the spots and tender rash typical of having been unceremoniously hacked. Fabulous, right? Who the fuck wants to shag a bony supermodel? Snogging and groping ensued and my hand disappeared between her chunky, cellulite-ridden thighs. Stroking at her sodden cunt lips, she suddenly interjected: "Sorry -- I'm on my period -- is that ok? I didn't want to put off seeing you for another week", she whispered, embarrassed. "No problem at all", I replied, surprised that I hadn't already detected the string of her tampon. With my response, she audibly relaxed and spread her legs open wide. I pushed my fingers against her cunt lips to open them and I didn't so much finger her... rather, my hand fell in! I've fisted many women, but I had never (and have never since) known a woman where my fist genuinely didn't touch the sides. Insider her, I didn't need to curl my fist into a ball -- it honestly felt like moving my hand inside a 10 litre bucket when I'm washing the car -- and in one corner of the cave I found the tampon lurking, not sure what possible good it had been doing. I grabbed the wet clump and pulled it out, pulling my tongue from her mouth and then pushing the red-soaked blob in to replace it. She sucked briefly before realising what I'd done and spat it out; being the gentleman that I am, I grabbed it and tossed it under the bed. There was no point trying to fuck her, so I got my first experience of double fisting a woman's cunt, interspersed with fucking her throat and her arse. The latter was, of course, filthy, but she didn't disappoint in ensuring that I was properly cleaned in her mouth between each penetration. ----------------------------------------------------------------------------------------------------------- It had been a long week at work which, together with the long drive up there, meant that I was out like a light once suitably spent. At some point during the night, my sleep was broken by a soft, little voice. "Mummy, mummy, I had a bad dream." "Is it ok if she comes in with us?", Lisa asked me. The bed was barely wide enough for two, but in my dopey state I said it was fine, and a little body slid in between us. I had to sleep on my side to stay in bed, and I was laying facing Lisa's daughter. My hand naturally relaxed just in front of me and I found my palm resting on a soft little thigh. I started to wake up and focused on the breathing of my two bedfellows. Convinced they were both asleep, I slowly stroked my hand up the little thigh, inside the cotton nightdress and found a small pair of cotton panties covering her middle. Gently I traced the outline of her little pussy, stroking gently up and down the front of her cotton-clad slit. The thrill of my bold action had my cock solid and I nuzzled up against the girl's face. I hadn't detected either of them being awake but suddenly another adult-sized hand landed on top of the hand I was stroking her with. I froze. "Don't go inside her", Lisa whispered. "OK", I whispered, thankful of her reaction. Her hand then released mine and she disappeared under the duvet to start sucking my cock while my caressing of her daughter's concealed slit continued. As her performance on my cock progressed, it was too much to bear just stroking the cotton. I withdrew my hand and put my middle finger in my mouth, coating it liberally in spit. I didn't want to leave a telltale sign of having penetrated her daughter's pussy, so I spread the girl's legs a little, hooked the crotch of her cheap, little knickers aside, just below her pussy, and introduced my middle finger to her virgin anus. I could feel my cum starting to rise, and Lisa was getting noisier and more active in her ministrations, so I went for a single push to impale the little girl's arse on my finger. She shifted about a bit, but didn't wake and within a few finger thrusts I was also filling her mother's mouth with cum. I pulled my finger out and held it to my nose as Lisa finished cleaning me up. ----------------------------------------------------------------------------------------------------------- "Shit, shit, shit..." I was woken with a start to find the bedroom filled with morning sun and Lisa running around getting dressed. "What's up?", I enquired. "I have to take Sian to the doctor for a check-up. I'd completely forgotten. My sister will be here in five minutes to look after baby Sam. I'll see you when I get back", and with that she was gone. I needed a shower that morning -- heaven knows what I'd come into contact with overnight -- and when I came downstairs I discovered a young ginger girl bottle-feeding a baby. "Hello", I said, surprised. I don't know why, but for some reason I'd assumed the sister would be of the older variety. "Hi, I'm Susan", she replied. "You must be Mike". Susan had none of her older sister's dusky (though hidden by multiple childbirth) good looks. Short, curly, ginger hair, glasses, no discernible tits or womanly figure. But a happy, smiley soul nonetheless. "You're from London, aren't you?" she asked, propping the baby against her shoulder for its post-bottle burp. "Yeah, that's right". "I think she's had to start looking further afield; she's had all the blokes round here", she laughed. "Bit of a slut, is she, your sister?" "Two kids by different dads by 19 is quite slutty, isn't it?" "Do you not much like your sister?", I grinned. "No, I love her to bits, just wish she'd choose someone decent rather than just shagging anyone." I laughed with her -- wondering what on earth I was doing there. Susan stood and took the baby upstairs to sleep off its warm milk. As she came back down, her loose, elastic-waisted jogging pants appealed to the devil in me. "So do you have a boyfriend?" "Every time Lisa shags someone new, I want a boyfriend even less. At the rate she's going, I'll be lesbian by the time I'm 16." "How old are you then?" "14", she replied. "You're very pretty", I lied, "lots of boys at school must fancy you." "Nah, they all want girls with big tits who put out for them." I got up from the armchair and set next to her on the sofa. "You really are pretty. You shouldn't be so tough on yourself." "I think Lisa will be back in a minute", she replied nervously. I grabbed her face with two hands and started kissing her freckled face, my tongue pushing into her mouth. "I don't really want a boyfriend", she panted as I pulled my face back. "Well you should at least know what it's like to have one", I reassured her. I squeezed at her chest through her t-shirt. Nothing. So slid one hand down and into the front of her joggers, while the other hand went round the back of her head to keep our mouths entwined. The hand inside her trousers pulled the knickers aside and started to stroke her plump teenage pussy, which had a light covering of soft hair. She fidgeted nervously but didn't push me away or tell me to stop. I withdrew my hand, grabbed the waistband of her trousers and panties together, and pulled them down to her shins. Letting go of her head, I then pulled them off completely so that she was naked from the waist down. "You won't hurt me, will you?" "Of course not. It's time you were a woman." "You won't make me pregnant, will you?" "Let's hope not", I laughed, and pushed her knees up to her chest to expose her teen cunt. In between the ginger freckles, her skin was pure porcelain and I spread her little cunt lips to reveal her pastel, baby-pink hole. With my left hand I held my swollen cock against her dry hole, while with my right hand I grabbed a handful of her ginger locks and pulled tight at the same time as ramming my meat home. I'm not sure which elicited the more pain, but the tears soon started flowing - which always makes me cum too quickly! -- and I noticed that my cock was streaked red as it punted in and out of her tight cunt; a world away from the bucket her sister had presented me with the night before. There was no way that I was going to pull out and I carried on thrusting right through my orgasm, ensuring that every last sperm was as deeply embedded as possible. Releasing her at both ends, I stood and wiped my blood-covered cock on the sofa's dishevelled throw. Susan looked up at me -- seemingly desperately searching for even a glimmer of affection. "I reckon you're a slut just like Lisa", I said as I fastened my trousers. And as I drove off, I passed Lisa and her little girl walking back to their home. ------------------------------------------------------------------------- Chapter 8, and it's back to dating. A single mother with pre-teen son and daughter, and an eventful trip to the seaside.