Date: Fri, 22 Sep 2023 12:55:08 +0000 From: teutonic1190 Subject: Dating Single Mothers 13 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. I'm always very happy to hear from readers who enjoy the themes explored. 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/ ------------------------------------------------------------------------- Dating Carol was a slow-burner. We'd met through a `lonely hearts' ad in the local newspaper. Our first meeting was for coffee/brunch and we'd been out of for drinks on a couple of evenings after that. She was delightful company and although I fancied her, there didn't seem to be any motivation from either of us to progress into anything sexual. Each meeting just ended with a nice kiss and nothing more. A couple of weeks in, she invited me to her place for lunch on a Saturday and told me that her 12-year-old son would be there. An indication, I felt, that things were getting more serious. James (Jamie) was a cracking youngster: blond and blue-eyed, with a sporty if skinny frame and curious about everything. As an only child, he had been spoilt rotten and, without the presence of a father figure, was clearly very close to his mother. During our meal, he was clearly very keen to keep playing with his GameBoy and kept fiddling with it, to his mother's annoyance. Food eaten, he was clearly disinterested in the post-meal conversation, but the persistent noise of the game finally saw his mother grab the little machine off him and hold it high above her head as he tried to grab it back. The two of them were simultaneously angry and laughing at the situation, and as Jamie climbed up to stand in his seat to reach his mother's hand, she suddenly brought it down and tucked her hand behind her back, away from his grasp. At this point Jamie's tactics changed. Feigning reaching across his mother to retrieve his toy, he started pawing at her tits over her blouse and, seeing his mother wriggle rather than chastise him, `accidentally' slipped his hand inside her blouse and into her bra. `Jamie!' Carol squealed, `Get out of there', she finally chided, slapping her son's hand away. Jamie looked back at me, grinned, and then slid back into his seat to see what would happen next. Carol was blushing. I winked at her. `Open a couple of buttons of your blouse', I asserted. It already had quite a deep neckline, showing the top of her cleavage, so any further revelations would be significant. Jamie was wide-eyed at my instruction. Carol stared momentarily -shocked at my direction. `What?' she gasped. `Go on, open a couple of buttons,' I said a little more firmly. Demurely, she complied, her face dropped down to witness the revelation. Her breasts were deep and tanned; I wondered where the white line might be. `Lift your boobs out of your bra', I continued. Carol swallowed audibly and her eyes were filled with horror and she looked across the table. Jamie's face was completely `Christmas morning'. Carol didn't delay following my instruction, and scooped deep into her bra to lift one tit and then the other out of her bra and over the top of the front of her blouse. Her tits were amazing. This was the first time I'd seen them. Long, deep, heavy mounds, entirely tanned, and with large areolae supporting long, thick nipples -- each the size of half a little finger. Jamie's head was snapping back and forth between gazing at these stupendous appendages and looking back at me to see what might happen next. `Now why don't you have a proper feel of your mum's boob's', I suggested to him. `But gently this time; caress and stroke them, rather than grab them'. He didn't need any further invitation and Carol was statue-still as his young hand started stroking under, over and around his mother's tits. `Don't be afraid of the nipples; gently tease them between your thumb and forefinger', I advised. Carol's breathing changed as Jamie's attentions turned to the nipples. Her body relaxed, her head tipped back slightly and her mouth fell open a little to allow slow, deep breaths. `Take your mum's nipples in your mouth. Circle them with your tongue and tug on them with your lips'. Jamie was back up with his feet on his seat in order to reach over and he tackled his new job like a pro. I stood out of my seat too, and came round behind him for a better view. They were both deeply engrossed, and I reached around to the front of Jamie's jogging pants to find his erection pushing at the material. `It's ok -- keep sucking them', I said, as he reacted to my hand. Carol's eyes had opened again and she was looking at me. `Jamie's rock hard for you', I told her. `Absolutely solid'. I moved my hand up to the waistband of the boy's pants, and slid inside, to find his hairless and beautifully smooth, hard cock, which I stroked slowly. `Let's show your mum what you've got, Jamie', I said, and started to tug his bottoms down to his knees. His arse was hairless and porcelain white too, and I stroked my hand between his cheeks. With his cock released, I could start to pull more confidently at his slim shaft and tease his small, soft balls. `Uh oh', I heard him mutter, at which signal I put my hand under his chest to lift him off his suckling duties, and point his cock directly at his mother's beauties. I held his cock in perfect aim as he released his energetic young sperm and liberally coated both breasts. His rictus grin told the full story of his delight as Carol looked down at the messy coating across her front. I released Jamie and started scooping the cum up with my fingers, Carol's eyes widening in reaction to my lifting the blobs up to her mouth. `Go on, don't let your son's gift go to waste', I encouraged, pushing my fingers against her lips until she opened wide to accept the nutritious cream. Once the majority had, to Jamie's amazement, been scooped and swallowed, embarrassment took over and Carol quickly stuffed her tits back into her bra, as she regulated her breathing. `Why don't you go and play in the garden or in your room?' she suggested to Jamie, who scampered off without complaint. `Well, that's the first time I've eaten my son's cum for lunch', she said to me, once the lad was out of earshot. `Fun though, wasn't it?' I enquired. ---------------------------------------------------------------------------------------------------------- I had been quite keen to empty my balls straight after Jamie, but decided to see how the afternoon played out. I took it as a good sign that Carol suggested I stay for supper and the evening, though she made no mention at all of the lunchtime activities. An afternoon of more conventional `family activities' and a beautifully prepared supper, after which Jamie was sent off for a shower on a promise of being able to watch a little TV with us before bedtime. Aged on the cusp of childhood and adulthood as he was, he soon reappeared sporting Spiderman pyjamas and damp hair. Not noticing the clock, the early evening family entertainment shows progressed, after the 9pm watershed, into more grown-up viewing and a TV drama scene showing a man roughly sexually abusing his wife. I glanced across to Jamie and his pyjama bottoms were tented as he stared, captivated, at the unfolding scene on the television. The male actor was punching the woman in the side of the head, as she lay, face down, being fucked from behind. Carol caught me looking across at Jamie, and I nodded to her to see her son's hidden erection. I waited for what seemed like 100 years for her response to the scene we all found ourselves in, and was finally repaid with two raised eyebrows and a little smile. `This is hot, isn't it?', I asked no-one in particular, pointing at the TV. `She loves him being so rough with her.' `But she's crying,' Jamie enquired. `With happiness', I replied. `She loves being able to release her emotions'. `Wow', Jamie replied. `Strip!', I broke the silence, looking hard at Carol. `Everything off. Now.' Carol leapt into action, undressing as fast as she could, until she sat, slumped and naked on the sofa. I grabbed her knees and pushed them up and apart to expose her cunt -- a glorious, shaven, car crash of folds and lips, her glistening fluid already soaking her, from her clit down to her arsehole. My head dived in to taste the fresh meat, my tongue pushing deep into both her arse and cunt. As I came up for air, I told Jamie to take his PJs off and to put his cock in his mother's mouth. I had barely started back on my feasting between Carol's thighs, when I heard the telltale sounds of a male orgasm. All too much for his juvenile senses, Jamie had already blown his load into his mother's mouth and she was looking down at me, her mouth open, showing me the collected pool of her son's mess. I nodded at her and she swallowed. Carol had clearly previously been in a Dom/sub relationship, knowing exactly how to respond to orders and how to behave in order to please her man. I decided to see how far I could push her. `Sit next to your mum,' I said to Jamie and, as he complied, I pushed his legs into the same position I had placed his mother. Grabbing his soft cock with one hand to start stimulating another erection, my tongue went to his virgin arse. Dribbling and working my tongue against the pink star, I started to work a finger inside too, hearing no complaint from him or his mother. Once I'd managed to get a second finger in too, I told Carol to get on the floor in front of my erection. `Drench my cock', I ordered, and she duly took it deep into her throat, gagging and coating it in her thick, wet drool. Her throat was a glorious sleeve for my cock, a place I knew I'd have to return to soon, but for now there was another mission. Completely covered in her natural lube, I lifted the head of my swollen member up to young Jamie's arse. `Push it inside your son's arse', I told Carol. With two fingers of one hand stretching her son's rosebud open, she grabbed the shaft and pushed it forward firmly, breaching his young entrance. Jamie let out a sound deeper than his young voicebox could ever normally have managed, as I ploughed forward to bang the hilt of my member against his arse cheeks. Carol knew exactly how to play her part, and as I started pile-driving her son, she slipped a couple of drool-coated fingers into my arse. `Go on, fuck him', she encouraged, pumping her fingers against my prostate. `Show him what it feels like to be fucked by a real man'. The dual sensations, together with her foul mouth, quickly had me approach my own crescendo, and soon the head of my cock was at its maximum swollen state and shooting load after load of my sperm into her pre-teen son's arse. It took a few moments for my erection to subside enough to pull out and allow me to view the bloodied and spunk-filled hole. `Clean your son up,' I told Carol, and without further guidance, her tongue mated with his arse and she began scooping up the mess as gravity brought it out in pulses. I slumped back into an armchair. `I think I'm going to enjoy dating you, Carol', I said with a smile. `And I think we're both going to enjoy having you around,' she replied.