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It’s a Hard Life (part 3)

"It became a different kind of package holiday when I found myself involved in an unexpected age-gap tryst"

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Here’s a fond memory from a holiday a few years back. I was in my twenties, newly single and had come on a Spanish resort holiday with a couple of mates. I had been looking forward to relaxing, so when my friends headed into town on the first night I decided to stay back at the hotel and just read my book on the terrace. As I lay on the sun lounger thinking about dinner, I heard an upper-class English man’s voice nearby: “What are you reading?”. I glanced over to my right and saw a man, perhaps in his sixties, lying nearby. I wasn’t really up for chatting, but he seemed friendly enough. We talked about the book a little and then got to discussing what we thought of the resort and the local area. It turned out he and his wife had been a couple of times before and knew the surroundings quite well. I Introduced myself. ‘Roger’ he said, walking towards me with outstretched hand. Something about his slightly military air made me unsure whether he was telling me his name or just confirming that he had heard mine. He told me he and his wife were going to have dinner shortly, and did I want to join them? It seemed rude to decline, and I thought perhaps they could tell me a little about the local attractions. I went back to my apartment to get changed and a little later I walked down to meet them in the open-air dining area. The two of them had already arrived when I got there. Roger’s wife wore a brightly coloured tunic dress and had light silver-grey hair worn up in a knot. From a distance she struck me as slender and elegant, attractive even. I got to their table and sat opposite them. Roger’s wife seemed to be about the same age as him – the creases at the corners of her eyes and some wrinkles around her mouth told me she was a confirmed sunbather, but her forehead and cheeks were smooth and her lips full. Diane, as she was introduced to me, was retired but had been a hospital nurse. She had a calm and sensible but friendly air about her, and I warmed to her quickly. During dinner they asked me about my life and seemed genuinely interested in my replies. They told me about their life travelling the world – Singapore, India, France (the countries I remember). After dessert, Roger told me he had to go back to their room. I moved to leave as well but Diane insisted I stay to help her finish the wine. As it turned out, this involved ordering another bottle - which we took care of fairly efficiently. As the restaurant emptied and the conversation slowed, Diane reached out to me across the table and for a moment I thought she wanted me to take her hand. She slid her arm back and revealed what I thought was an after-dinner mint on the table. Diane fixed me with her gaze and whispered: “I like you, young man”. I looked down again and realised she’d passed me a condom. I remember thinking that as figurative gestures go, this was pretty unmistakeable. I slipped it into my pocket. She rose carefully to her feet and took hold of my arm. We walked hand-in-hand through the dimly-lit arcading and up the tiled steps to their apartment. As we entered, I saw that Roger was sitting in a chair by the desk, reading a book. He did not look up. Diane turned to face me, and I silently raised an eyebrow. She smirked back, twitched her nose, and nodded. It occurred to me I was probably about to fuck a stranger in front of her husband and I wondered if perhaps this was the kind of thing that happened a lot with well-travelled people. I tried to look as casual and un-surprised as possible. Diane stood facing me and reached up to pull a clip out of her hair. She tousled it with her fingertips which allowed corkscrews of glossy ash-blonde to unravel and fall past her shoulders. She took a step towards me and kissed me on the cheek, then the other cheek – and then on the lips. Stepping back again she playfully tapped me on the nose with her index finger. She reached down with crossed arms and grabbed her dress by the hem, pulling it up and over her head to reveal a pink two-piece bikini, worn on a firm, tanned body. She tossed the dress to the floor and put her hands behind her back to unclip her bikini bra, rolling her shoulders forward to let the bra fall away. She had small but shapely breasts, lightly freckled cleavage and with tan lines marking the division between public and private skin. Sliding her bikini bottoms down past her smooth hips and thighs she revealed a small, neatly trimmed patch of white pubic hair. At this point I noticed that her height had been accentuated by cork wedge sandals, which she kept on (naughty girl). She walked over to the bed and laid back, stretching and flexing each of her long legs in turn, and then cast me a plaintive glance. I’d been so absorbed by this show I had forgotten that I was supposed to be part of it too, and quickly slipped off my trainers, shirt and boxers, being careful not to snag my stiffening cock on the waistband. As I climbed onto the bed, I reflexively glanced around to see what Roger was doing. His book was now laid face-down on the desk next to him, and he seemed to be pulling on one of the buttons on his fly. Diane reached out and gently laid her fingertips on my jawline, as if to turn my head and guide my focus back to her. She held my gaze and put her hands behind her head, also spreading her legs to fully reveal her trim fanny. I knelt between her legs and leaned over to kiss each breast in turn. Then I sat back and reached out with both hands and splayed fingertips, ever-so-softly skimming them down her body, from her shoulders, over her now-hardened and erect nipples, across the faint creases of her tummy and converging on her crotch. She gave a sharp intake of breath and shivered a little, drawing up her legs either side of me. I reached to either side and did the same from her feet, tracing over her knees, past her thighs and delicately, slowly, brushing my fingertips against her warm labia. She let out a soft sigh, which became a gentle moan as my fingertips traced around her inner thighs. I spent several minutes tickling, stroking and massaging until she was panting eagerly. With a flat hand I began to softly rub her fanny in circular motions, first one way and then the other, until she began gently to buck her hips and moan deeply. She looked down eagerly at my stiff dick, and I saw that her face and chest were flushed red. I reached down to the floor to retrieve the condom she had passed me earlier and rolled it over my swollen cock. Diane suddenly sat up and pulled her bedside drawer open, producing a bottle of lube. She pumped some onto her hands and beckoned me forward. I held myself over her in a press-up position and she reached down to massage the clear gloopy liquid over my stiff member. With eyes narrowed and lips pursed, she tilted her head to one side while slowly and tenderly lavishing the lubricant on my dick. Her soft, slender hands massaged their way up and down, occasionally cupping and stroking my tight ball sack. The feeling caused me instinctively to make small thrusting motions, and I was impatient to get inside her. I took some lube from the bottle and stroked it into her vagina and around her swollen clitoris, occasionally pressing a thumb or finger inside her. I was momentarily distracted by the rapid rhythmic squeaking of the chair behind me, but I did not look round. Instead, I looked Diane directly in the eyes, took a firm hold of her wrists and forced my hard cock inside her, which made her grunt and moan with a new urgency. The tight, slick feel of her vagina around my rigid pulsating cock was pure ecstasy as I set about pumping hard and fast. I seemed to lose myself in a frenzy of thrusting, the sight of her small breasts jiggling up and down serving to spur me on to fuck her harder and faster. She threw her head back into the pillow as she writhed with pleasure, helplessly taking the pounding I was giving her. As I felt my balls begin to boil over, the rattling and squeaking from the chair behind reached a crescendo, and suddenly I was aware of Roger’s dick appearing from the right. Diane turned her head towards him and opened her mouth wide, just in time to catch several thick strings of cum on her tongue as Roger wanked his climax away. The sight of my new retiree friend Diane messily swallowing cum while helplessly moaning for my cock was more than I could bear: the tightness that gripped my balls released itself in spasms of ecstatic pumping, and I filled the rubber completely. The room seemed to spin and Diane wrapped her legs tightly around me, as if to squeeze out every last drop. I held her close and felt her heart thump as her moans subsided to gentle sighs. By the time the pleasure had subsided, Roger was in the bathroom. I slid myself out of his still-panting, cum-spattered wife and pulled on my boxers and shirt. “Mmmm!” she hummed softly as I stroked her hair one last time. As I stood to leave, she opened one eye and murmured “Perhaps no condom next time?”. I smiled, nodded gently, and left. Exhausted, I walked back along the open-air passageways to my apartment, past the restaurant which was now closed and quiet, save for the hissing of the cicadas in the darkness.
Written by Racingpoint

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