Holiday Loving Ch 01

Holiday Loving - Memoirs of a Woman of Pleasure Ch. 01

I lose my virginity and meet a loving couple

Author's notes:

1. This is a work of fiction. The activities and practices described in this story are not necessarily either condoned or recommended. If you choose to do anything described in real life with real people you do so at your own risk.

2. All characters are fictional and any likeness to any living person is purely coincidental. The story is purely imaginary and, to the author's knowledge, bears no relationship to any factual occurrence.

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I lay on the bed, flat on my back, panting hard. My mouth and throat were dry from over-breathing; my body felt relaxed and gloriously awake, my pussy tingled. I gazed into the two pairs of eyes looking down at me with love, both faces smiling as they watched my response, waiting for my reactions. I focused on Brian, his lithe tanned body leaning towards me as he squatted on the bed, his semi-hard cock glistening with our combined juices.

"Oh Brian, that was wonderful," I managed at last between gasps. "I never knew sex would be so fantastic."

Brian smiled and bent to give me yet another kiss on the lips, wordlessly. I changed my focus, gazing at the other pair of eyes, upside down above my face.

"Thank you too, Jenny, you punished my tits so wonderfully," I said to Brian's girlfriend as she smiled at me. She mouthed a kiss to me.

Slowly my breathing eased as I recalled the memory of how this situation had developed. Yesterday (was it really only yesterday?) I had my 18th birthday. I hate parties, probably the only teen in the world who does, so decided to just have a few friends around. There were about fifteen of us, sitting around, listening to music, having a few drinks and talking about our lives so far. Those who were over 18 talked about their 18th parties, others about how they intended to mark their milestone in the next couple of years.

By midnight everyone had gone except Brian and Jenny. They didn't go because it was their house in which the party was held. Over the next hour the topic of conversation turned to sex. Brian and Jenny had been an item for nearly a year and described the great sexy sessions they had together. Instead of the normal sexual relations, in which orgasm seemed to be the goal, they were into tantric sex, in which giving your partner pleasure over an extended period of time was the ultimate aim. Being young, fit and healthy they avoided some of the more extreme practices of orgasm denial for extended periods of time and both enjoyed multiple orgasms during each session. They also commented that they enjoyed sexual relationships with other people, both as a couple and separately. The upshot of this conversation was that Brian asked me if I was still a virgin, to which I replied truthfully that I was. He then asked if I'd like to remedy that situation and after a few moments thought I agreed. The rest, as they say, is history.

Brian, Jenny and I retired to the bedroom and Brian and Jenny stripped me. I was really nervous and embarrassed to begin with and even Brian reminding me that we'd seen each other naked many times because we were brother and sister was no reassurance. However, once I was on the bed and both Brian and Jenny began caressing me and arousing me, I lost all sense of embarrassment and responded in kind. Very soon my pussy was drooling, as was Brian's cock, and he lay me gently on the bed and slowly entered me. The feeling was amazing, far better than the tampons that had been in there before. As he began to move slowly and gently inside my love tunnel, the thought of pregnancy occurred to me. It was only a couple of days before my next period was due so I considered it to be a slight risk only, well worth while taking to feel the delicious skin-to-skin contact of his rampant cock inside me.

Jenny knelt behind my head, her drooling pussy only inches from me as she leant forward and cupped, then caressed my tits. Gradually she increased the stimulation and began squeezing and pulling on my nipples, which rapidly engorged and became ultra-sensitive. It took very little time before I was responding to these two centers of stimulation, writhing on the bed as the sensations became stronger, the waves of sexual ecstasy washing through my body, causing the soles of my feet to tingle, my head rolling from side to side as my two lovers took me to ever higher levels of pleasure.

My orgasm crept up on me unnoticed, probably due to lack of prior experience. I felt like I needed to pee, then a crashingly intense sensation washed over me, causing me to scream at the same time as I felt in a dim recess of my mind Brian's hot cum squirting into my pussy. I writhed uncontrollably beneath Brian's body and he lay on me, deeply engrossed in his own orgasm. Jenny bent forward and kissed my nipples, then she and Brian shared a kiss.

Gradually I came back to reality, panting, hoarse, dry-mouthed. Brian withdrew from me and crouched between my wide-spread legs, gazing at me lovingly. I shook my head, trying to clear it from the remnants of the endorphins from my orgasm.

"I need to cum," said Jenny to neither of us in particular, "Feel like an all-girl session?" she asked me.

"I-I don't know," I replied, "I've never had any sort of session until just now. I guess if you want to teach me I'm an apt student."

Jenny leapt off the bed and went to a dresser where she pulled something from a drawer. She approached me with what looked like a long thick sausage with one end rounded and looking vaguely like a man's cock, and the other with some straps attached.

"You seen one of these before?"

"No, never," I replied, "What's it for?"

I had a fairly good idea what it would be for but needed to check.

"It's a strap on dildo. Brian's cock's useless for a while as you've taken all his starch, so I want you to fuck me with this. So if you stand up I'll fit it to you."

I rolled off the bed and stood up, my legs still feeling weak, and Jenny quickly and expertly strapped the dildo around my hips. I noticed there was a pad that pressed firmly against my pubic bone just above my clit and felt really nice.

"Now, I want you to do me doggie style," Jenny instructed me as she positioned herself on all fours on the bed, head low and ass high in the air. "Just kneel behind me and wriggle forward until you can slip the end of the dildo into my cunt."

I did this and found it slid in easily as Jenny was very wet. I pressed forwards, pushing the rubber cock into her until I felt some resistance.

"That's far enough at present. Soon you'll be able to push it in further once my cunt relaxes. Now, fuck me with it."

I started slowly fucking her, pushing in, pulling out, feeling the way in while the dildo pressed against my clit, giving me a burst of pleasure each time I pushed in. I sped up, pushed a little harder, feeling Jenny respond. I held her hips for more leverage and watched as Brian knelt on the bed, a knee each side of her head as he reached around her and caressed her tits, as she had done for me. Jenny began humping backwards at me, clearly wanting more. I gave it to her, pressing harder, feeling my clit respond as the pressure came and went. I felt I was getting close to cumming and hoped Jenny was also. The whole scene was clearly having its effect on Brian whose cock now stood to attention once again.

A few moments later it was all over. Jenny came hard, I also came from the clit stimulation and we both collapsed sideways onto the bed, panting rapidly. I made a resolution to increase my fitness so I could enjoy longer and more intense sex sessions, thinking also that sex was probably one of the best exercises there was. Eventually Jenny moved away from me, the dildo falling from her hole, then she unstrapped it from me.

"I think Brian has another present for you," she whispered in my ear.

I looked at his grinning face and knew she was right.

"Make like a bitch in heat, bitch," he growled.

I took up Jenny's previous position and felt Brian move behind me and impale me on his rigid cock. There was nothing gentle or tantric about this sex - it was a straight out slam dunk fuck. I stayed with him as he fucked me hard, pressing the head of his cock against the end of my cunt repeatedly as he reached around me and squeezed and pulled my clit, causing a combination of pain and pleasure. I felt Jenny's hand between his legs, pulling his balls downwards and squeezing them to prolong his endurance.

In a relatively short time it was over and I felt Brian deposit his second load of incestuous cum deep within me as I went over the top and came hard, my second time ever on a cock. He stayed inside me for a short time, enjoying the sensation of his sister's cunt enveloping his cock.

"You don't know how long I've fantasized about this," he whispered in my ear, "For several years now I've dreamed of fucking your nubile young body, but now, it seems my dream's come true and the reality is far better than the dream."

I turned sideways and gave him a deep sexy kiss, then he withdrew and we all lay on the bed, pulled a blanket over ourselves, cuddled together and slept.

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The sun shone down on my almost naked body as I lay on a recliner on the beach, working on my tan and surreptitiously watching others from behind my shades. It was eight months since I lost my virginity. I'd tried for a replay of that night but was told in no uncertain terms that before either Brian or Jenny would consider it again, I needed to find a man of my own. How did I do that? Where did I go to find someone for a friend and lover?

The obvious answer was dating websites online, so I wrote my profile and received many replies. After sorting out the obvious sleaze balls, I agreed to meet several men in public cafés, but was disappointed. Almost all of them were in a relationship and wanted a bit on the side. At that time, that wasn't what I wanted. I wanted a man who was all mine, someone to come home to at night, someone who was there for me, not having to dash off and placate a suspicious wife or partner.

However, I was horny. That night with Brian and Jenny had awakened a part of me that I hadn't known existed and I liked that part. But it needed feeding. I began masturbating, daily at first, then gradually more frequently. I got contraceptive advice and had an implant inserted which I was told would lessen or eliminate periods. For me it eliminated them , meaning that I was always available. If anything, this made me feel hornier until I would use sex toys frequently, often spending the day with something inside me, impatiently waiting till evening when I could arouse myself manually to orgasm several times. Clearly I had become a nymphomaniac.

I had also worked hard on my fitness and health, joining a gym, running increasingly long distances, toning my body, sunbathing naked on my secluded patio and at the beach in my tiny bikini. I upgraded my wardrobe, tossing out all the non-sexy clothing and only buying and wearing clothing that showed off my body, emphasizing my tits, legs, ass and pussy. I had also had my pussy waxed, leaving only a small tuft of hair immediately above my clit.

But none of this solved my problem of being alone and finding a caring boyfriend who would be devoted to only me. Maybe I simply set my standard too high. Maybe I needed to redesign the paradigm. There were lots of very desirable men around. I saw a great many every day, many of whom I would gladly go to bed with, so perhaps that was what I needed to focus on. After all, there really was no need to have one steady boyfriend to the exclusion of all others, was there? I considered Brian and Jenny; they were a couple but they didn't only have sex and sleep with each other. They brought other people to their bed and visited other people's beds, both together and separately, so what was holding me back?

"Do you want to be alone by choice or are you waiting for someone?"

The gentle, manly voice awoke me from my self-pitying train of thought. I opened my eyes and focused on a tall well-built man of probably about 30, wearing brief swimming shorts which showed a nice bulge in front, who was standing looking down at me. I gestured to the vacant area of towel alongside me.

"Neither, unless you're the person I'm waiting for," I replied.

He sat on the towel.

"I'm Stan," he introduced himself.

"Hi, Stan, I'm Mandy," I replied.

We shook hands formally and incongruously.

"Great day," he began, "You from around here?"

"Yes, I live a few blocks from the beach. You?"

"Nah, not that lucky, I'm just visiting for a few days on my own then my wife's joining me for another week together."

I chewed this over in my mind for a few seconds, wondering what to do, what I wanted, how I should approach this situation. Was it an opportunity, the answer to an unspoken prayer? Or was it a minefield destined to lead to heartache and disappointment? What the hell, I thought, I'm despondent enough - a bit more won't even be noticed.

"So would your wife approve of you chatting up nearly naked girls on the beach while she's not here?"

He laughed, a gentle natural sound she decided.

"Well, I'm sure she wouldn't be overjoyed, but certainly she likes me to be happy. We have a reasonably open marriage and are very truthful to each other about ourselves."

"Oh, that sounds an interesting relationship," I replied, propping myself up on my elbows to get a better look at him.

"Yes, it is. How about you?"

"I'm single and not in a relationship, but I wish I was."

Why did I have to say that? I don't want to scare him away, but I really do have to let him know I'm available, but I seem to be throwing myself at him, blinded by my neediness. Oh well, what happens, happens.

"So how can a gorgeous chick like you be single? Are you gay or something?"

I remembered fucking Jenny with her dildo. It had been enjoyable, but certainly not as enjoyable as Brian fucking me. I might be bi, but certainly wasn't gay, yet, I added for myself. I laughed.

"No, I'm not gay. I guess I'm just inexperienced and really have little idea of how to pick up a guy. Maybe shy would be a better description."

"Yeah, it's hard these days with all the perverts online and never really knowing how a person will respond. There's so much lying that it must make it hard. I'm so grateful for Gloria, my wife, as being married in a reasonably open marriage allows us to have sexual experiences with other couples, which saves all the angst and heartbreak that you must feel."

How had this conversation gone from a 'Hi' to talk of sex so quickly, I wondered? Oh well, if it was Ok for him, it was Ok for me. Let's see how he reacts to my next statement.

"Yes, I certainly feel that but even more than that I feel really horny all the time and apart from masturbation, which doesn't seem to last, I have no way of relieving it."

Omg, did I really say that? What will he think? I watched his face, which showed a warm loving smile.

"Yes, that could certainly be a problem. I think I know a possible solution, however. Would you like to come to my cabana and we could discuss this in greater depth?"

Shit, now I'd done it. How to get out of this one and still remain on speaking terms? Then I realized that this was the very invitation I'd been seeking and it was only my old self that was now trying to reject what I had been offered. Geez people are complex, especially me. I smiled in what I hoped was a welcoming smile.

"That sounds like an excellent idea. I've also been cooking for long enough so some time out of the sun would be wonderful. Lead on."

Now it was his turn to be taken aback. Perhaps I was too forward; perhaps I was supposed to play hard to get and not surrender myself so quickly. These games were too complex, too new. However, he visibly recovered, stood and offered me his hand. As well as the hand I noticed that the bulge was now considerably larger. I mentally hugged myself; satisfaction may be close at hand.

We strolled hand in hand towards the buildings, chatting amiably about inconsequential things. We crossed the road and he led me to a small and quite secluded multi-level building. We entered and climbed the stairs to the top floor, where he used a card to open the door. The unit was compact and opened onto a private, partly shaded deck overlooking the beach, with solid balustrades and no possibility of being overlooked by other people. He offered me a seat and asked if I'd like a drink; I chose iced water and sat in the shade. He re-emerged with two frosted glasses of iced water and placed them on a table, then sat on the sofa beside me, letting his hand rest on my bare thigh. My instinctive reaction was to brush it off, but I restrained myself, instead placing my hand on his bare thigh.

We sat like that quietly for a few minutes, watching the waves which were just visible over the balustrade. Eventually I asked the question I really wanted answered.

"Do you do this often? I mean, pick up a girl on the beach and take her to your apartment?"

"Hmm, sometimes, but I wouldn't say often. My wife does occasionally too, usually a guy but sometimes a girl. She's bisexual, you know."

So am I, maybe, I thought.

We chatted about home life, our history and other inconsequential things as we sipped our water and I allowed his hand to move upwards towards my pussy while mine moved slowly towards his increasing bulge, itching to pull his shorts off and caress his obviously huge cock. I figured he was equally keen to remove my bikini and see what goodies it contained. Eventually I could stand it no longer.

"Hey, I wanna see your cock, you wanna see my pussy and tits, so what are we waiting for? Do you wanna strip me first or will I strip you?"

Again that flash of incredulity at my forwardness in not sticking to some unwritten rules passed over his face, but was gone in a second.

"I want to strip you," he replied, breathlessly, "Stand up, now."

Oh shit, he wants to strip me in public standing on his patio where everyone on the beach will be able to see my tits. So what, I thought carelessly, let them look. I'm proud of them. I stood, as ordered, and he also stood, moving behind me to undo my brief top. He pulled it away from my body then came around the front and looked at my tits for a long moment.

"May I touch them?" he asked at length.

Silently I nodded assent and he reached out and cupped both breasts, one in each hand, caressing them, gently squeezing each nipple between his thumb and forefinger. He then lowered his head and kissed, then nibbled each nipple in turn.

"Beautiful," he breathed.

He then knelt down and hooked his thumbs in the sides of my bikini bottoms and tugged the brief garment downwards, slowly revealing my shaved pussy, until he had them around my ankles.

"Step out," he commanded.

I lifted each foot in turn and he tossed the garment to the side. He pushed his hands between my knees and moved them apart, causing me to spread my legs for him, then he buried his face in my crotch, his tongue licking my dripping pussy lips, tasting my juices.

"You taste delicious," he said after he came up for air.

He stood and pulled my body against his, kissing me hard on my mouth, allowing me to taste my sweet nectar on his tongue.

"My turn," I said huskily as I knelt down in front of him.

I undid the tie holding his shorts then hooked my fingers in the elastic and pulled them down to his ankles, watching his cock spring outwards and upwards as it cleared the elastic waistband. He lifted each foot in turn and I removed his shorts, then reached up and caressed his cock and balls. His cock grew even harder and was drizzling precum from the opening. I licked the precum off and stood, pressing myself against him and kissed him deeply so he could taste himself. I then knelt again and took his cock in my mouth.