Date: Thu, 09 Mar 2023 14:45:12 +0000 From: teutonic1190 Subject: Dating Single Mothers 11 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/ ----------------------------------------------------------------------- This story returns to my relationship with Olivia, 33, and her children Robert, 12 and Holly, 10, who I introduced in Chapters 8 and 9. We had been away together for a weekend at the beach, to get to know each other better. Olivia and I had arranged to see each other again on the Friday evening following our weekend away. Whilst she was more than horny enough to keep me busy for a couple of days, I was a little disappointed to hear that Robert and Holly would be staying at their father's house that coming weekend. Having been given such a strong green light to play with her kids, I thought that Olivia deserved a treat, so booked us a table at a fancy new restaurant for the Friday evening. Arriving at her place, she looked stunning as she answered the door, catching her in the middle of putting her earrings on. She was wearing tight black leather trousers which hugged her arse and thighs wonderfully, a black silk blouse with a deep plunge onto her generous cleavage and high-heeled pointed boots. `I haven't put any lipstick on yet,' she said, `so that you can give me a snog before we leave.' I pulled her close and pushed my tongue deep into her broad, wet mouth, my cock pressing into her soft, sexy belly. `That reminds me: I need a wee before we go too,' and she stepped into the downstairs loo, leaving the door open. I'd driven for an hour to get to her house, so thought I'd join her and stepped into the small room and stood right in front of her, unfastening my trousers and pulling my cock out. `What are you doing?' she squealed, but there was no time for explanations as my golden jet hit her mouth and chin. I then lowered my aim slightly and flooded the opening in her blouse, sending a cascade down over her tits and belly, drenching her blouse. `You utter shit!' she yelled. `I'm ready to go out!' `Almost. You don't have any lipstick on yet. Go and grab another blouse and let's go,' I added, with a wink. Strangely, given she was soaked in piss from chin to waist, she took some toilet paper to wipe the last drops of piss from her cunt, then shuffled off upstairs with her trousers round her thighs. While Olivia was changing, her landline phone in the downstairs hallway rang. Instinctively, I grabbed it. `Hello.' `Oh... errr... sorry. Is Olivia there?' asked a clearly anxious and agitated female voice. `Sure, who is it? `It's Rachel.' I called up to Olivia and she dashed down to take the call, saying very little until the call ended with an `of course you can, of course it's alright. Just come.' Olivia gave me a slightly grimaced look. `We're not going out, are we?' I enquired. `I'm so sorry. She's had a massive bust-up with her boyfriend and he started smashing things up, so she's grabbed her kids and driven off. I can't leave them in the car overnight.' `It's fine,' I replied, planting a kiss on her forehead. `You'd better get out of those clothes and into something comfier.' ------------------------------------------------------------------------------------------------------------ Twenty minutes later, the doorbell rang and Olivia opened it to three shivering shapes. Unlike Olivia's bold and curvy size 16-18 form (UK sizes!), Rachel was a size 8 stick insect, her thin legs emphasised by her skin-tight yoga pants. Alongside her were a boy and girl around 8 or 9 years old. Not identical, but possibly twins? `Take them straight up to bed in Holly and Robert's rooms,' Olivia directed. While Rachel was upstairs, I quizzed Olivia. `Are the kids twins?' `Yeah, I think they're nine next month. Both really nice; very quiet, like their mum.' `Is Rachel a bit sub then?' `Pretty sure she is. She always goes for very alpha types, but seems to end up with the nutters,' she laughed We had three large glasses of wine waiting ready for when Rachel came downstairs. She took two big gulps before physically slumping in relief. `I just hate it when he starts breaking things. It scares the kids so much and just makes me so anxious.' Olivia moved to sit next to Rachel and put her arm round her. `You're safe now.' `Were you planning on a cosy evening in?' Olivia enquired, poking at Olivia's comfy lounge pants. `No, you literally just caught us. Two minutes later and we'd have been gone. I got changed while you were heading over.' `Oh, I'm so sorry. I've completely ruined your evening.' `It's fine. Isn't it, Mike?' Olivia replied, seeking my added reassurance. `Of course, it is. Though you'd be prepared for a suitable punishment, wouldn't you, Rachel?' I ventured. Both ladies lifted their head and looked at me. `Erm... what kind of punishment?' Rachel enquired cautiously. I stood up from the armchair, walked to the dining area and returned with a dining chair which I placed in the middle of the room. I sat down and patted my lap. `Over you go.' `What?' Rachel gasped. Olivia was wide-eyed, but silent. `I'd booked a table at the best restaurant in town for Olivia. It's only fair that you properly demonstrate how thankful you are to have such a good friend?' I patted my lap again. She seemed instinctively to know what was going to happen. Taking another gulp of her wine, she stood slowly. Olivia gripped her hand momentarily and whispered `It'll be ok.' Rachel stood alongside me, reticent to assume the required position. I grabbed her nearest arm and yanked her down onto my lap, ignoring her crying out as I twisted her arm to lock her down against me. The Lycra, taut on her bottom shone under the room's spotlights. Her arse cheeks were barely any larger than a teenage boy's and I was careful not to hurt my hand on her bony form as I delivered the first three slaps. Rachel was panting already, attempting to regain her composure. My grip on her arm felt good and tight -- suitably uncomfortable for Rachel - so I called on Olivia's involvement. `Come and pull Rachel's pants down.' Olivia's face lit up. This was clearly turning out to be an exciting evening for her after all and she wasted no time in dropping to her knees behind her friend, and yanking the waistband of both yoga pants and g-string down to Rachel's knees. She took a good look at her friend's exposed cunt and arse and then looked back up at me, nodding excitedly. I delivered ten hard slaps to Rachel's arse -- five on each cheek -- and by the last she was beginning to sob. `Olivia, run your nails over the welts.' Rachel screamed as Olivia's sharp nails traced their blade-like edges across the inflamed areas where she'd been spanked. `Why are you crying, Mummy?' All three of us looked towards the open living room door, where a shocked and tired little girl stood, bare-footed and wearing a long pink nightdress. Rachel wriggled to try and get free to attend to her daughter, but I held firm. Olivia stood and went over to the girl. `It's ok, Maddy, don't be scared,' Olivia said, taking her hand. `Mummy was a bit naughty, so she's just having her bottom spanked, but it's nothing to worry about. You deserve it, don't you, Rachel?' she asked, directing herself back towards her friend. `Yes, I do deserve it, sweetie. Mike and Olivia are helping me by making sure I'm sorry.' `Do you want to watch Mummy being punished?' Olivia asked Maddy, who nodded and climbed onto Olivia's seated lap for a ringside seat. I recommenced the blows, spreading them between Rachel's arse cheeks and the backs of her thighs, until the tears were free-flowing. `Oh God, thank you.' Rachel had finally relented; succumbed to the pain and allowed her anxiety to dissipate. I released the grip on her arm and she rolled off my lap onto the floor, revealing her entirely bald cunt. She smiled up at her daughter. `Mummy feels so much better now.' `Have you been naughty at all?' Olivia asked Maddy, who paused to think and then nodded. `I scratched Ewan's arm and threw one of his toy cars in the bin.' `Do you think you should hop up onto Mike's lap too?' She nodded and came straight over. No strong-arm tactics required; she lay straight across my lap. My cock throbbed before I'd even touched her. I undid my belt and trouser fly and pulled my cock out, pointing skywards, and then pulled her tight against me. Both women looked on wide-eyed. I lifted the long nightie up to Maddy's waist, revealing her full-size cotton knickers. `Take her knickers off,' I ordered, looking at Rachel, who immediately pulled them down and completely off. `Show me your daughter.' She knew what I meant and parted Maddy's legs before pulling her bottom cheeks apart to show me her tight rear hole. `And the rest.' Rachel breathed in heavily and lowered her fingers to spread her daughter's tiny cunt lips, revealing the pink inner form. We exchanged smiles and I closed Maddy's legs. Maddy's arse cheeks benefitted from a plump and curvaceous layer of puppy fat, and I had to severely restrain myself from slapping those delightful mounds as hard as I wanted. It was important to guide this innocent into the delights of being spanked, rather than dissuade her from offering her bottom to men for life. About half a dozen or so spanks in, her pale skin clearly marked with my handprints, she started to appeal to her mother about her discomfort, so I released her. She stood up straight away and looked back at me, her eyes falling immediately upon my raging cock. Noticing her shock, Rachel, who was still kneeling alongside me, wrapped her petite hand around my shaft and very slowly started wanking me up and down. Olivia came and knelt on the other side and ran her hand under and around my balls. `You and mummy need to say thank you to Mike for letting you stay here tonight,' Olivia said to Maddy. `You need to make him feel nice. Do you want to help Mike feel nice?'. Maddy nodded. I stood from the formal chair and sat on the sofa, pulling off my trousers and underwear in the switch. `Kneel between Mike's legs,' Olivia instructed, the two ladies settling in on each side of me again. `Suck Mike's cock,' Olivia ordered Rachel, who impaled her face on my cock head. I let her bob up and down within her comfort zone and then suggested that she give Maddy instruction on how to do it. Maddy started with some tentative licks of my swollen glans before trying to fit the whole into her mouth, careful to keep her teeth away from it. I stroked her head as she sucked so carefully, gagging occasionally as she took it too deep. `Your mummy still needs a bit more punishment. Shall we do that first?' I asked Maddy, who retreated to sit on the dining chair and watch. I grabbed a fistful of Rachel's hair and punched her head back down onto my cock. She tried to push away, and Olivia grabbed her hands and restrained them behind her back. With our victim suppressed, I started to force Rachel's head up and down, the head of my cock never leaving her throat. The drool soon started flooding over my balls and in short order she emptied the hot, putrid contents of her stomach into my crotch. Alarm struck Maddy's face. Rachel was crying uncontrollably, until Olivia smacked her face. `Take your top off,' Olivia ordered, `and clean Mike up with it.' Rachel pulled her tight, lycra t-shirt off, revealing her tiny, braless tits and pair of chunky nipples. I stood out of the puddle of mess she'd deposited on me and she started wiping me clean, before turning to the sofa itself. Thankfully of the wipe-clean, leather variety. `I still need to cum,' I announced, and scooped my hands into Maddy's armpits, lifting her and then placing her in an armchair. Pushing her legs wide apart, I buried my face into her tiny, virginal cunt, tasting the combined delights of her pussy and arse. `Your mummy was very naughty, being sick on me, wasn't she?' I asked. Maddy agreed. `So it's up to you now to make me feel better, is that ok?' Agreement received, I pulled her arse to the edge of the chair, her cunt exposed for my taking. Rachel was out of the room but Olivia came close, stroking her hand between my arse cheeks, teasing my rear hole with her finger. `This is so hot -- go on, fuck her. Fuck her little cunt. Make her a little sub like her mum.' `Open her for me,' I said, delighting Olivia, who held open her young labia with one hand and then, having licked her middle finger, pushed it gently inside the juvenile cunt, fucking it slowly with shallow movements. Without asking, Olivia then took my cock in her mouth and drooled liberally over it, in readiness for its adventure. Removing her finger from the little entrance, she took my cock in her fingers and guided it toward its goal. Once the head was wedged in the opening, she returned to playing with my arse, pushing against it in attempt to encourage my invasion of Maddy's sex. I grabbed Maddy's tiny waist and pushed forward firmly, only retreating slightly as each level of resistance was encountered. It was clearly uncomfortable for Maddy but it was important that she learned her role, and I continued to force my way in until the hilt had been reached. Fully embedded, I paused to allow her to become accustomed to being filled. She had been calling for her mother and Rachel, now completely naked, had returned to the room. `Ready for me to fill your daughter up?' She took her daughter's hand and nodded to me. `I'm so proud of my little girl,' she said to Maddy, and I started the full assault. Within a few strokes I could see on each withdrawal that the shaft of my cock was coloured red and this prompted me to hammer this debutante even harder. Olivia's finger was now deep in my arse and the combined evening's activities meant it wasn't long until I pushed for the deepest possible insertion and pumped load after load of my seed inside the young thing. Once I'd recovered my breath, I looked at the bewildered girl and declared that her mother would clean her up. Though not sure she realised there was any cleaning up to be done. `With her mouth,' I advised, looking a Rachel, `and she can start by cleaning me.' I grabbed Maddy's ankles and lifted them high as I withdrew my cock, wanting to ensure that nothing leaked prematurely. Following my lead from earlier, Olivia grabbed Rachel by the hair and pulled her face down to my cock, forcing her to take the spunky and bloody shaft into her mouth. She pumped her back and forth, demanding that she render me spotless. Once complete, I released Maddy's ankles and opened her legs, Olivia retaining her grip on her friend's hair and pushed her to lick her daughter's ravaged cunt. Rachel tentatively opened Maddy's pussy lips and a large blob of pink-streaked cum appeared almost immediately. Rachel made to gag, but Olivia persisted with ensuring the mother see the job through. With tears streaming again, Rachel tongue-scooped her way through the contents of my balls, now embedded in her daughter. I couldn't resist fingering Rachel's arse as she completed her job, suddenly conscious that I hadn't availed myself of her cunt that evening. Plenty of time for that yet, I thought. -------------------------------------------------------------------------- In the next chapter, it's the day after the night before, and Olivia's children come home from their father's house a day early. Meaning that I've got two mums and four children to keep entertained!