Work had been stressful, I had recently broken up with my girlfriend, and I had not long turned 40. I needed a break, from life, from everything. I decided that I needed a vacation. I had not done a solo vacation in a long time, but I had to this time. Two weeks seemed like a long time, but a break was absolutely required.
I scoured for good deals and offers and settled on an all-inclusive resort in the Spanish Costa del Sol. The brochure pictures showed a beautiful pool area, a great swim-up bar, opulent spa facilities, and nice-looking hotel suites. The cost was a bit steep, but I really didn’t care; I deserved it.
When it came to it, I did feel a bit self-conscious initially. A guy on vacation by himself, amongst the couples and families on the bus from the airport, I felt like I stood out, and it took a few days for me to feel 100% comfortable. A few people even stopped to talk to me around the pool or at the bar over the first day or so. Brits tend to do that, they see another Brit on holiday, and they need to make themselves known and complain about the food, the weather, the Spanish or whatever. But there were some nice people at the hotel, and I soon relaxed into it.
One couple I got to know early in my trip was a British couple in their mid-fifties, Ray and Janine. No disrespect to Ray, but admittedly, my attention was mainly drawn by Janine. She was very friendly, relaxed, and clearly comfortable in her own skin. She had a very….I suppose, lived-in body, large breasts stuffed into her bikini top, and stretch marks around her hips and stomach, but if anything, it added to her charm. Her finger and toenails were immaculate, and her dirty blonde hair was long. She was attractive for an older woman, and I was certainly happy to say good morning to her every day as I took my spot around the pool and made idle chat at the sunloungers as she topped up her tan or at the swim-up bar getting an afternoon cocktail. Ray was an amiable guy. I sat and had a beer with him once or twice a day at the pool bar, discussing football or pointing out some of the pretty women around the pool, although that was mainly him. I reminded him that he had a beautiful wife lying on a sunlounger at the other side of the pool. He just nodded in agreement, seeming interested that I had referred to Janine as beautiful.
I tried to read a book I had bought with me, but the chatter from the other holidaymakers around the poolside and the music that the hotel piped in just made it impossible. Plus, I had to agree with Ray, there was a lot of flesh on show, which distracted me a lot of the time, and I was grateful for the tinted lenses of my sunglasses, not giving my eyes away as I stared, probably too much at some of them. But Janine was the one who kept catching my eye. I lay on my front on my sunlounger, trying to make sure my back got the same tan as my chest already did. I heard the click of shoes on the poolside floor, and I knew it was her. The rhythm of the stride carried a confidence, and I tilted my head slightly up to see Janine’s well-groomed feet in her gold strappy sandals that had a small kitten heel as she strutted to the bar. My nose got a waft of her sun tan lotion that she was covered in. She saw me looking.
“Don’t get up, I’ll buy this round!” she said jokingly and ran her hand over my shoulder playfully as she walked past, as I lay, still face down.
“Oh, ok, no problem. Next one is on me then!” I called back, watching her hips in the orange sarong skirt she had wrapped around herself as she went by.
“Promise?” she said with a wink as she turned back to me.
Was she flirting with me? – I wondered to myself, but I brushed it off as nothing. She was just a friendly woman. She strutted back past me, placed a cold bottle of beer on the floor in front of me, and kept walking. I took a gulp of it, and then I dozed off, and by the time I woke up, they had gone, retreated back to their room, I guess, as it was approaching early evening and dinner was calling me as well.
The following day, at around lunchtime, I was sitting at the swim-up bar in the pool, and I saw Janine approaching, swimming slowly toward the bar. I had noted that she enjoyed a Pina Colada as a general rule, and asked the barman to prepare one. Janine reached the bar and ordered her Pina Colada, as I had guessed. “There is already one on the way. I never did get my round in yesterday,” I said with a smile.
“How thoughtful of you,” she said back, and gratefully accepted the glass from Carlos, the barman who had pretty much learned our drinks orders by heart anyway. “So, what brings you on holiday by yourself?” she enquired, moving to the underwater stool next to mine, a little closer.
“Well, life has been difficult recently. I just needed a break, and there was nobody to go on holiday with, so it was either go by myself or don’t go at all,” I explained as she nodded along, seeming to take pity on my situation. I flinched briefly as I felt her hand on my thigh, making my cock twitch ever so slightly.
“Well, you did the right thing by getting away,” Janine said. You need to unwind, and there are all sorts of ways you can do that when you are on vacation.” She finished her cocktail and swam away from me, leaving me with a hard cock, causing me to keep my seat for a bit longer and be thankful that the stools were below the waterline.
Later that afternoon, back at the pool bar, while I sipped my fourth beer of the afternoon, Ray came and sat down. “Wow, look at the pair on her!” he laughed as he gestured towards a young Spanish woman standing at the other side of the bar.
“Does Janine know you perv on all the women around the hotel?” I joked with him.
“Of course she does, and she is just as bad,” he replied
“What do you mean? She stares at the women as well?” I said in jest.
“Sometimes,” Ray said bluntly, making my head turn to face him. “She knows and appreciates an attractive woman when she sees one, and doesn’t mind me looking. She also gets to check out the fit guys as well. She has mentioned you more than once.”
“Has she? Hehe.” I tried to laugh it off. “How did she mention me?” I asked, semi-rhetorically.
“Well, she tried to see if you could be added to her list of free passes!” Ray chimed back with a laugh.
I was too shocked to even check if he was kidding or not. He gave me a slap on the back as he strolled back to his sunlounger and his wife, chuckling to himself.
That evening, I went to the hotel’s Cabaret Lounge after dinner and stood at the bar. There was a Jazz band playing, and they were actually pretty good. I stood sipping a bourbon, and I saw Ray and Janine at a table across the room. They waved me over, inviting me to join them. I walked over and was admiring Janine before I even got to the table. She looked great in a Black cocktail dress that reached her knees, but rode up slightly as she sat, Black sheer nylons and a very elegant pair of high heel shoes. She patted the seat next to her, gesturing for me to sit. We chatted and enjoyed the music, and shared a bottle of wine. Janine’s hand drifted to my thigh under the tablecloth on more than one occasion as we talked, her eyes meeting mine every time she did. She excused herself to go to the bathroom.
Ray leaned over to me. “You never said what your thoughts were about being one of her free passes.” He said bluntly to me.
I blinked at him, “I wasn’t sure if you were kidding or not. I assume you are?” I replied, not sure where this was going, but knowing where I would quite like it to go.
“We have an understanding. We are quite…adventurous, I suppose. Our neighbours at home have no idea what happens in our house a lot of the time, and they are probably better off not knowing.” He said, very matter-of-fact. He didn’t even wait for me to reply.
“She is interested, and I would be happy to…share her, if you were interested?” Ray enquired.
Oh my god, it is going where I hoped! – I looked at Ray as he glanced up to see Janine returning. “Well, I….I mean, she is very attractive, but…I guess, maybe.” I stammered just as Janine sat down, the smell of her perfume wafting into my nostrils, which I think she had put on in the bathroom, as I hadn’t noticed it earlier.
“Well, my darling, looks like he is happy to be your free pass!” Ray laughed as he looked at his wife and put his arm around her waist. “Shall we order room service to our suite for three?” he said, directing the question at me.
“Oh, yes, sure,” I said, trying to keep my cool. They stood up, and Ray went to the bar to order something for delivery. We headed to the elevators and rode up to their floor in a slightly awkward silence. We reached their suite and stepped inside, where I was offered a seat. They had booked a very top suite by the look of it, with a living room area with ample seating. Janine took a seat next to me, her hips and legs leaning against mine. The doorbell rang, and Ray greeted the waiter, returned with a bottle of Champagne and popped the cork, pouring us all a glass.
“To new friends!” he said cheerfully, to which Janine and I both raised our glasses, and I took a big swig of the bubbly to gather my thoughts.
I didn’t really have time to, as Janine turned to me, rested her hand on my crotch, feeling my semi-erect cock, took my glass from my hand, and placed it on the table next to her. She leaned into me and pressed her lips against mine, as her hand rubbed and explored my groin, kissing me deeply as she fidgeted to unzip my trousers. She fished around and freed my now throbbing cock, stroking it as it twitched. She stood up, not releasing the grip on my shaft and backed toward the bed. Dropping to her knees, she took my cock into her mouth and ran her tongue along the length of it expertly. I could tell she had likely had a lot of cocks in there over the years, and I let out a gasp of appreciation.
Ray had taken a seat in the armchair slightly in the corner of the room and was observing what was happening as he sipped his Champagne. Janine stood up to face me and reached to unzip the back of her dress, allowing it to fall to the floor, pooling at her feet, revealing the Black sheer nylons to be stockings, held in place by a garter belt, attached to some very expensive-looking underwear. As she stepped out of it, I couldn’t keep my eyes off her. She sat on the edge of the bed and lay back on her hands.
I knelt in front of her, and gently placed my hand on her slender ankle, and traced circles on the bone of it, and ran my hands up her long legs.
“Wow,” I said, as it’s all I could think of to say, as I leaned forward and ran my tongue along her thigh, reaching the skin at the top of the stocking, running my fingers on the silvery lines of her stretch marks on her hips. I reached under the elastic of her lace panties and slid them down. Her pussy was exquisite, and I instinctively reached out to run my fingers over it, making her moan at the touch.
I couldn’t resist, and I leaned in and plunged my tongue into her, forgetting that Ray was watching and my initial trepidation about it. Her pussy was clearly well-used over the years, but it was well-groomed and tasted sweet. I got lost in it for longer than I realised, and only came up for air when I felt Janine’s thighs tighten around my face as she convulsed in an orgasm that sent her head back onto the mattress as her arms gave way.
My cock was so hard by this point, and I stood up, grabbed hold of her hips and pushed her back onto the bed, away from the edge, and got between her legs, lining my cock up to her still twitching pussy and pushed myself inside her. She cried out and pulled me in close to her. I pounded into her with deep thrusts, and she pulled me in with each one, her breasts pressing against my chest as her fingers dug into my back.
Ray was watching with great interest, had stripped out of his clothes and was stroking his cock as he watched. Janine looked over at him. “Come over here, darling,” she invited. Ray strode over to the bed, close to his wife’s face, and fed his, admittedly, huge cock to his wife. Janine leaned over and bobbed her mouth on her husband’s cock as I carried on fucking her. She gagged on his cock as it touched the back of her throat. My thrusts got more urgent as I edged closer.
“Oh my god! Oh, I’m gonna cum! Oh Fuck!” I cried out as I blasted a stream of semen deep inside Janine, making her moan at the warmth of it, as she still had her mouth wrapped around Ray’s aching cock.
Ray let out a grunt as he finished in Janine’s mouth, which she swallowed down greedily, gulping the thick ropes of cum as if it was a treat to her. Ray slumped down on the bed next to Janine, and I lay on the other side of her. Janine lay there grinning like the cat that got the cream, which I guess wasn’t far from the truth, and we all breathed heavily, catching our breath. I was still amazed that the evening had turned out the way it had, thinking this was by far the best vacation I had had in some time!
Ray and I caressed Janine’s body as we lay next to her, and she reached down, stroking our softening cocks, rolling our balls in her hands, as our fingers flicked and squeezed her nipples and groped at her breasts. We poured ourselves another glass of champagne and sipped it. Ray and Janine revealed their long history of swinging and wife swapping. Turns out Janine’s list of free passes was quite long, and so was Ray’s. Janine was not against another woman joining them and sharing Ray, if Ray allowed guys to share her.
The conversation, and Janine’s soft fingers, had roused both Ray and me back to the point of being ready again, and Janine certainly did not want to call an end to the evening just yet. Ray sat slightly upright on the bed, and without a word, Janine climbed on top of him, reverse straddle and lowered herself onto him as he took hold of her hips. I watched with interest as she allowed him to enter her ass, and she took it beautifully, groaning as his massive cock disappeared inside her. Ray put his hands under her thighs and took her weight, her legs raised slightly in front of her. Her high-heeled shoes were still on, adding to the allure. She looked at me and said she wanted us both.
I got myself in position, between her legs, finding room to find my feet in between Ray’s legs and feet underneath her, and she grabbed my cock and guided me into her soaking wet pussy, which squelched as I pushed it in, with my previous load still swelling around in there.
“Oh fuck! Oh my god!” Janine groaned as the feeling of being filled in both holes brought her to orgasm almost immediately. The full feeling of the double penetration made her shake. It took some figuring out, but we eventually found a nice rhythm, matching each other’s moves as Janine rocked between Ray and me, as we both pushed our cocks into her steadily.
We were a sweaty, noisy mess, as Janine got owned on that hotel bed, culminating in Ray and me, almost simultaneously ejaculating inside his wife. I came hard, my second load into her messy cunt, and Ray shot pulses of it into her asshole. The duel cumming sent her into orgasm again, shuddering as she climaxed, and she put her arms around my shoulders, pulling me close as she rode it out.
We fell back onto the bed and lay there for several minutes. I was struggling for what to say, being clearly not as used to this as they were. I had had threesomes before, but never with another guy, but I had to admit, the thrill of sharing a man’s wife as he watched and eventually joined in was better than I was expecting. I was offered the use of the shower before getting dressed. I turned the water temperature up high to almost scalding, just to check if I would wake up. But I didn’t; I hadn’t dreamed it!
I got dressed, and we said goodnight, and they both thanked me for my company. I walked down the corridor to my hotel room, wondering how I would be able to look them in the eye at the pool the next morning. Something told me they would find it easier than I would!
