I had been exchanging messages with Debbie for a few weeks. We both wanted to meet in a safe place and follow where that led. After a few unproductive hours on the site one Saturday afternoon she came online and hinted at being free that night. A lonely weekend stretched ahead of me so I wasted no time in taking the hint. It would mean a long drive but my only other options were loneliness and Vodka while waiting to go back to work. I suspected she was online for a meeting that evening and was playing a little coy. Eventually we made arrangements to meet at a pub in her home town and we logged off. I killed some more time before dinner and making my way South.
Fears of another no-show were dispelled as I recognised her sitting on a low wall adjacent to the pub car park. Since accepting my need to re-learn the dating game I had given a lot of thought on how to handle first meetings. Characteristic of my bookish nature, I had bought a few titles on dating and NLP. I had started to develop the conversation structure which would transform those first few cringingly bad meetings into smooth, enjoyable and successful encounters. That she was for real gave me a chance to apply what I had learned.
Her profile picture showed only her petite back but we swapped face pictures before logging off so we could recognise each other – or change our minds. Unlike the many who used either old pictures or ones very carefully taken, Debbie’s were genuine. The area was quite run down and her clothes matched that. Jeans, trainers, T-shirt and nylon jacket had all seen better days. That sat at odds with her educated, plummy, southern accent.
Over a couple of cokes, I learned she had two children both still living at home. Her grown up daughter was full time carer for her severely handicapped teenage son. Debbie herself had serious kidney problems requiring several dialysis sessions per week. Between running the home, dialysis, and the college course she enthused about a picture emerged of an extremely demanding life. The site afforded her some ‘me time’. She was open about having been on the site intermittently for a few years. My early encounters had shown me just how much I had to learn about playing the game. Debbie was quite open about her experiences. Reading between the lines she played around when her health allowed in between prolonged spells of illness.
I gently prompted her to talk about what would put her off and what would attract her to meeting and playing with a guy. Thereafter I tried to do this with every partner. It was the most effective way of learning how to play the game and avoid being blown off without ever knowing why. Cock shots and gratuitous language were instantly ignored. Those were closely followed by one word or one-line introductions. Messages making no reference to the recipient that had been copied, pasted and sent en-masse didn’t fare much better. Introductions that referenced the profile and combined gentle humour with intelligence from those meeting the recipient’s requirements were a rare and welcome breath of fresh air.
Talking of her previous married life in the Home Counties, she painted a very pleasant picture of a nuclear family living in safe luxury. Despite the contrast with her present circumstances, she gave no hint of anger or self-pity. She was simply a nice person doing the best she could against a difficult set of circumstances. We chatted about nothing in particular until late into the evening. Nearly three hours passed unnoticed. I was genuinely enjoying connecting with her positive outlook and felt comfortable sharing some of the real me. In those early days I had yet to create the alter ego that later partners came to know. The increasing rowdiness from the men around the pool table made it progressively difficult for us to continue our gentle conversation. Using this as a pretext to move on she agreed and said to meet outside after powdering her nose.
Without the loose nylon jacket, I could see just how slim she really was. Her faded jeans showed equally slim legs and cute little butt. She wore no make-up. Her straight hair was plain light brown and cut short with a functional side parting. Despite this plainness, she had a natural beauty. Her spirit shone bright through green eyes as she described coming to terms with her son’s degenerative condition and her then husband baling out for an easier life with a younger model. As she described her own diagnosis, I wanted to take her in my arms and promise that everything was going to be alright. But she didn’t need me or any other guy. She had all the strength she needed to cope on her own. I was drawn to her spirit as much as her naturally beautiful androgynous body; and, of course, the prospect of my first real shag in two years.
Outside the pub, groups of men hung around; some swigging their pints, others obviously not old enough to be there legally. There was no sign of trouble but it was easy to imagine something kicking off on the slightest pretext. We drifted to the car. I was surprised it was already past eleven. Three hours had slipped by without me really noticing. Our rapport was very natural. Asking where we should head to, she replied it’s not far, just turn left at the roundabout. A couple of turns took us deep in to an old council estate. The exterior modifications and multitude of door styles advertised the houses had long since been sold to private owners. While it was free, I rested my left hand on her thigh without any resistance. Her instruction to pull in to a driveway confirmed it was game on.
With the engine and seat belts off she leaned over and gently kissed me directly on my lips. I had wanted to get my hands on her tiny body since we first sat down in the pub so did not hesitate to take her in my arms. Returning the kiss, my hands explored her thighs and body. She seemed content making out in the car like a pair of teenagers. Enjoying the anticipation, I lost myself in the moment until a volley of wolf-whistles from the passing youths gave an ideal chance to move things on. I suggested she either invite me in or send me home with a bulge in my jeans. She acknowledged my humour with a smile, suggesting I bring my bulge with me.
I sat on her bed in silence while she made some coffee. From the other end of the house muffled voices confirmed her children were in the living room. Without making reference to them she put the coffee down, pushed me backwards and lay on top. I was surprised at how quickly she took control. She clearly knew what she wanted and with a willing accomplice was going to get it. She broke away from our kisses to slide down my body. Again, taking me by surprise she began rubbing her crotch into my left thigh. I smiled encouragement and ran my hands through her hair, enjoying the juxtaposition of that petite nymph taking complete control. Sill grinding against my thigh, she tugged at my top. I sat up slightly to let her pull it over my head. With my top thrown aside, hers immediately followed and she pushed my shoulders back on the bed.
I couldn’t help but notice the scars on her body. One curved around from her spine to just below her tummy button. The other traced vertically from under her ribs to just above her pubic bone. For a few moments our hands explored each other’s bodies. Her bra slipped away to join the pile on the floor. Her tits were tiny, little more than firm nipples. They were easily the smallest and firmest I had ever played with. They felt fantastic in my hands. Their novelty spurred me on to undo my jeans. My cock was more than ready for her. As if following my cue, she pulled away from my thigh, stood on the bed and dispensed with her jeans to reveal white cotton panties. She tugged at my jeans. They were too tight to be going anywhere easily. Together we wrestled them off and she resumed using my thigh for her pleasure. Through the cotton panties, she ground against me in a steady rhythm. Her eyes were closed. She was enjoying a private pleasure as if she was humping one of the many stuffed toys scattered throughout the room.
I was more than happy to be used that way. My hands were enjoying the novelty of my first A-cups, and her wonderfully firm arse. With as little padding as her tits, it was solid against my grasping fingers as I pulled her harder into my willing thigh. I could feel the delicate panties becoming damper against my skin. The stiffness of my cock left no doubt about its readiness just as soon as those panties joined the pile of abandoned clothes.
She breathed heavily, as if close to cumming in her now soaked panties. She dropped a hand to the cotton. With her middle finger she rubbed round and round at the top of the dampness. Within a few brief moments, her face, neck and tits flushed red. I was expecting her to cum at any moment but she pulled back to reach for a bedside cabinet. Condoms and lube were thrown on the bed. A further rummage produced a neon-blue rabbit that would surely stretch such a petite figure. And then she retrieved a device I had not seen before. It looked like an electric toothbrush. But the end was a flat piece of plastic. A quick press of the button brought it to life and as quickly stopped it. I later learned it was a magic wand. She left them on the cabinet to get completely naked.
At last the panties were off. She was shaved smooth. Her tiny lips were glistening and wide open for her swollen clit to poke out from its hood. She passed a condom without making eye contact. I slipped it on, my cock twitching at the touch. She squeezed plenty of lube directly on to her lips. Rather clinically, she checked the condom was on properly. I leaned up, held her and tried to lay her on the bed but she resisted. Not wanting to blow it, I let her push me on my back once more. She was intent on going on top. That didn’t at all surprise me, given how she had taken control. However, I didn’t quite expect her to straddle me and turn round in one movement to hover over my cock in the reverse cowgirl position. Holding my cock upright, she slid its tip between her lips before lifting herself completely off. That gave a perfect view of her firm butt cheeks and swollen, glistening lips.
Lowering herself, she took a little more of my length, raised, then lowered some more. She took my whole length in her own time. Gently pushing it deeper was met with her raising her hips to resist. She clearly wanted to be completely in control so I relaxed and lay still. She settled into a very slow rhythm, taking my full length and gliding up the shaft and back down again. Her right hand rubbed at her clit as it had done earlier. She ignored both comments I made as she maintained the ultraslow rhythm. It felt like we were disconnected despite being joined in the most intimate way. She was in her own world, using my cock for her obvious pleasure. My entire focus was on my cock. I felt her tight around me, sliding over my tip so slowly it would take an age to let go. I just lay back and closed my eyes to enjoy my first real shag in two years.
Slowly, slowly, slowly she kept the rhythm, her breathing the only clue she was reaching her goal. Heavy breaths gave way to an occasional moan. Each moan coincided with another squeeze down the full length of my shaft. I so wanted to push harder and quicken the pace but she would have resisted. I just had to go with it. And so, it continued, her grip on me ever so slowly tightening with each moan. Up and down, up and down, she was lost in her own world. And so, it continued. Anticipation transitioned to frustration. Resist. Relax. Flow with it.
The inevitable started. Her core went into spasms against my frustrated cock. Her head shot back to release a deep guttural grunt. She was totally still apart from the hand still working her clit. Spasms squeezed and released my cock. If she kept that going it would have pushed me over the edge as well. Grunts gave way to gentle moans as she went limp and the spasms subsided. Her head fell forward as her breathing eased. Leaning further forward she slid off my cock on to all fours without even looking round.
Following the cue, I was up on my knees and guided my cock back inside. Slowly, I slid it all the way. As I eased back and forward, she remained totally still. My pace increased and she passively took it as I wanted. My previous frustration passed. I quickened my pace again to reach the plateau which would soon give way to the cliff edge.
It did so quickly. My load released causing a momentary paralysis. As the spasms hit, I grabbed her hips and bucked my jerking cock deep inside as fast and as hard as I could. After such a long, teasing, build-up the spasms seemed to go on forever. I felt three distinct spurts being jettisoned as I used her tiny body to take every bit of pleasure I could. I was floating on the waves washing over me. Fuck – that was worth waiting for. Every tension, every frustration, every niggle and every worry floated away as I held my still hard cock inside her. With a firm grip on her slim hips we remained completely still. My thumping heart gave way to hyper-relaxation. I just wanted time to stand still. My first real shag in two years. My cock subsided and slid from her. I released her hips from my grip. Without any reference to what had just happened, she picked up the untouched coffees and said she would get fresh ones as I cleaned myself up.
Source: reddit.com/r/gonewildstories/comments/lf9m1z/mf_first_shag_in_ages