In the Summer after my 24th birthday, I went on holiday with a couple of mates. On the first night they headed out to look around the town while I stayed back at the resort to take it easy.
As I laid on the sun lounger, eyes closed, I heard an upper-class English man’s voice nearby: “Just arrived?”. I opened one eye and saw a man, perhaps in his sixties, lying on a lounger nearby. He and his wife had been a couple of times before and knew the place quite well. I introduced myself. ‘Roger’ he said, walking towards me with outstretched hand. Something about his military air made me unsure whether he was telling me his name or just confirming that he had heard mine. As he passed by me, folding his newspaper, he asked if I wanted to join him and his wife for dinner. It seemed like a good way to learn a bit about the place, so after a quick shower I walked down to meet them in the open-air dining area.
Roger’s wife wore a white halter-neck dress and had tied back silver-grey hair. She was a handsome woman, elegant and with large breasts that her dress struggled to conceal. Creases at the corners of her eyes and wrinkles around her mouth told me she was a confirmed sunbather, but her forehead and cheeks were smooth and her lips full. Diane was retired but had been a hospital nurse. She had a calm and gentle air about her, almost motherly, and she drove the conversation with a kindly inquisitiveness.
After dessert, Roger jumped to his feet and announced that he had to go back to their room. I moved to leave as well, but as he walked behind me he gently placed his hand on my shoulder as if to keep me seated. Diane also insisted I stay with her, to help her finish the wine. It turned out that this involved ordering another bottle, which we took care of efficiently. As the restaurant emptied and the warm fug of tipsiness enveloped us both, Diane reached into her handbag and placed what I thought was an after-dinner mint on the table. She fixed me with her gaze and tilted her head to one side. I looked down again and realised she’d passed me a condom. As gestures go, this was pretty clear, and despite the age difference and the obvious question of how to avoid Roger, I couldn’t pass on the chance to see those boobs up close.
I took the condom and she rose carefully to her feet. We walked through the dimly-lit arcading and up the tiled steps to their apartment. The apartment door opened directly into their bedroom. Roger was sitting in a chair by the desk, reading a book, but he didn’t look up. Diane turned to face me and saw my look of confusion. She smirked, 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 older, well-travelled people. I tried to look as casual and un-surprised as possible, albeit with a rather undignified boner.
Diane stood facing me and reached up to pull a clip out of her hair. She tousled it with her fingertips, and a cascade of glossy ash-blonde unravelled and fell to 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 behind her neck and untied her dress, letting the fabric fall to her waist. Her heavy, freckled boobs swung free, subtle tan lines marking the division between public and private skin.
Sliding her dress down over her smooth hips and thighs 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 down on her back, stretching and flexing each of her long legs in turn. She 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 now-rigid 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 was pulling at 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. Her nipples were firm and erect, and her breasts soft and rounded.
I reached out with both hands and splayed fingertips, ever-so-softly skimming them down her body, from her shoulders, over her nipples, across the faint creases of her tummy and tracing her labia. 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 around her clitoral hood. 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 lost myself in a frenzy of thrusting, the sight of her huge breasts wobbling 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 stopped. 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 spurts 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. We laid together as one, and by the time I opened my eyes again Roger was in the bathroom. I gently slid myself out of his still-panting, cum-spattered wife. “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 protection next time?”.
I smiled, nodded gently, and left. I walked back to my apartment, past the restaurant which was now closed and quiet, save for the hissing of the cicadas in the darkness.
