Third Time Lucky

Like a lot of stories on Literotica this one has elements that fit within other genres; erotic couplings being one. However, I think you will agree that overall, it is a Romance.

The storyline is from my own imagination so please don't tell me that the characters would or should have done this or that. The actions and reactions I've written fit with the way I wanted the tale to unfold.

Remember, if you really hate it that much you can simply stop reading...

Constructive comments on the actual writing are most welcome and if you spot a fault with the editing then it's all mine and I apologise in advance.

All the characters that engage in sexual activities are over the age of 18.

Enjoy.

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Third Time Lucky...

From somewhere in the distance the faint sounds of passing traffic filtered through to me as I lay my head back on the sun lounger. Mingling with the chatter of people in the pool it formed a distracting noise that threatened to lull me off to sleep.

The five-star hotel we were staying at was situated at the end of a short tree lined driveway, hidden away for privacy but was, unfortunately, still close enough to the road for it to be heard.

Sighing inwardly, I gazed unseeingly up at the virtually cloudless blue sky through my DKNY polarized sunglasses. Vincenzo was late, as usual, and it set me on edge knowing his tardiness was delaying the conversation I needed to have with him when he finally arrived. I had put the moment off for a while now, waiting for the right time but it had never seemed to come.

When he had told me he had several business meetings down on the Amalfi Coast and suggested that I accompany him, I knew that the moment had waited for had arrived. I would have to do it; I couldn't put it off any longer.

Apparently his wife was spending a few days in Paris, shopping, and rather than go alone he wanted to take me along with him. In reality it meant she was off with one of her young lovers and my boss was taking full advantage of her absence.

Not that that's as bad as it sounds.

While I did work for him at the company's head office in Rome, I have to confess that I was also his mistress and had been for the last eighteen months.

It was a situation that I was about to bring to an end.

Trying to relax, I lay back, letting the heat of the afternoon sun soak into my skimpily clad body. The tiny scraps of material and string that comprised my bikini did little to cover my slender figure.

Two small triangles of red concealed my areola and nipples while leaving most of my modest 34B breasts exposed to the sun's rays. Between my legs another fragment of the same material just about hid my freshly depilated sex from view.

My thoughts turned to what I was going to say to Vincenzo later and how he might react to it.

'Would he be angry or just philosophical about it?'

'If it annoyed him would he fire me?'

It was all something of a concern to me, being alone and so far from home.

"Scusi signorina."

Slowly turning my head, I looked over at the man who had sat down, uninvited, on the sunbed next to me, the darkened lenses hiding my blue eyes.

"Yes?"

Slightly annoyed at the disturbance I made sure the tone in my voice reflected the fact.

"Perhaps you will permit me to buy you a drink?"

Studying the stereotypical Italian male in front of me, I took a deep breath. It was a situation I had found myself in countless times during my stay in Italy and had so far always managed to extricate myself from without too much difficulty.

Bare chested with a gold chain around his neck he was wearing the briefest of swimwear and had a smirking expression that made me want to slap him, even though he was a complete stranger.

"No thank you."

"Aw come on baby.... don't be like that. Maybe we have dinner later as well."

"No. Thank. You." I repeated my refusal making sure to state each word slowly and clearly.

His expression didn't change as he ignored my rebuttal and continued to press me to have a drink with him.

Getting angrier by the second I beckoned him to lean closer to me so I could whisper in his ear.

"Fuck. Off!"

"Fuck you, you stuck up bitch."

My comment had had the desired effect and I smiled as he stood up, snapping angrily at me before he stalked away.

Ignoring the rest of the lascivious looks I had been getting from the men around the pool for most of the afternoon I closed my eyes and went back to waiting, letting my mind drift onto how my current situation had come about.

********************************************

To understand the full story, I should really go back to the beginning, the start of my time at university.

I, Chloe Wainwright, arrived at university a rather naïve and innocent nineteen-year-old from a small village in Devon. Immediately, I found myself totally overwhelmed by the scale of everything around me when I first set foot on campus.

It was all so very new to me and doing my best to fit in I threw myself into fresher week trying to make friends and find things I wanted to do.

That was when I met Connor McCarthy and my life changed overnight.

On the Wednesday morning I was wandering amongst the various student society stalls in the gymnasium, all vying to get my attention and join whatever activity they advocated, when I saw him.

Six feet tall with messy brown hair and rather penetrating blue-grey eyes he was standing alone, manning a table that advertised the university's sailing and water sports club.

I thought sailing was only a marginally better option than joining the college trainspotters society but he looked so cute that I just knew I had to talk to him, so I made my way over to his table.

"Hi, I'm new and I umm.... I wondered what water sports is all about?"

His grin when he answered made me go weak at the knees.

"I guess you've never sailed or anything?"

Sheepishly I shook my head and confirmed his appraisal of me.

It turned out he was only minding the stall for a few minutes while the society's chairman had gone for a coffee so we weren't speaking for long. However, by the time his friend returned Connor had confessed to being a sailor and occasional windsurfer but, more importantly for me, he had asked me if I would like to go for a coffee with him.

It was an offer I had happily accepted.

If I'm being totally honest I fell for him big-time within that first half-hour.

I hadn't really had many boyfriends and those I had had were generally the platonic kind, so the feelings he aroused in me were unfamiliar and more than a little exciting.

Our friendship started that very same day and I quickly found myself spending a lot of my free time with Connor. Always hoping it might develop into something more and finding myself continually exasperated by his lack of romantic interest in me.

After a month I knew I was in love with him, without a shadow of a doubt, but he always seemed a little reserved with me, even though I thought of us as best friends.

Everything I did to get his attention never seemed to work.

I even tried sailing and went windsurfing, both of which I found I liked, but Connor still kept his distance and never made a move on me. Short of physically throwing myself at him I didn't know what else I could do.

A few months went by in this way and, frustrated by his lack of romantic response, I eventually agreed to go on a date with Dean Blackwell.

Dean had a reputation around the university as being a bit of a player but, as I was trying to make Conner jealous, he seemed an appropriate choice. What I didn't realise was that he had only asked me out for one reason.

I had inadvertently told a couple of my female friends that I was still a virgin, something almost unheard of at university. Unbeknown to me this little titbit of information had become fairly common knowledge and it was Dean's stated intention to relieve me of my virtue, with or without my consent.

Our date wasn't anything special or expensive, we were both students after all, and he took me to a local pizza restaurant and then on to a bar for a drink afterwards.

Dean Blackwell didn't interest me in the slightest. I was well aware that he had a bit of a reputation for playing the field and I had no intention of seeing him again.

However, our evening surprised me and went relatively well, I even managed to keep up a sensible conversation with him for most of the time.

Everything was fine until he drove me back to my lodgings.

Politely thanking him for the pizza and the drinks I slid out of the car and started towards the front door of my building when he came after me.

"So, you gonna invite me in then Chloe?"

A little surprised by his actions I declined, "I don't think so Dean."

That was when he got more insistent and grabbed hold of my arm.

"Aww c'mon don't be like that. I did take you out after all."

"I said no Dean." Raising my voice, I told him a little more forcefully, trying to pull myself free of his grip.

"Listen to me." He snarled, roughly dragging me around the side of the building, "You're going to be a bit more appreciative. Do you understand?"

Shocked by his behaviour it took me a moment to gather my wits and I barely struggled as I allowed myself to be led away.

"What are you doing? Let go of me. You're hurting my arm."

Finally coming to my senses, I started to resist.

Dean laughed, "I'll let you go when I get what I want."

As he said it he reached for me and started to touch me through my clothes.

To say I was terrified would be an understatement, especially when he started to grope me, fondling my breasts and then attempting to put his hand up between my legs.

"Please.... don't. Please..."

Scared he was going to rape me I tried to push him away, sobbing and begging him to stop as I slapped futilely at his arms. He was much too strong for me though and I began to panic when he started to undo my jeans.

"You're gonna give me what I came for." He sneered at me.

"No, please. Stop. I don't want to."

I knew I was too weak to prevent him doing whatever he wanted, and I was convinced I was about to be raped.

That was when he was suddenly yanked away from me and thrown roughly onto the floor.

"Leave her alone you fucking arsehole!"

"What the fuck!" Dean snapped, lying on the ground.

"I should beat your fucking brains out." Connor stood over him, his fists clenched as he threatened him.

"What do you mean? She's the one that wanted it."

Getting up Dean brushed himself off and tried to suggest it was all me and that I had been the one leading him on. However, Connor wasn't listening to his lies.

"Like fuck she did. If you come anywhere near Chloe again I won't be responsible for my actions. Do you understand me shithead?"

"Sure, sure, you're welcome to her. Little miss prissy isn't fucking worth it anyway." Dean snorted, trying to retain some sort of dignity as he slunk away.

Waiting until he had disappeared from sight Connor turned back to me pulled me into an embrace, "Are you ok?"

I nodded, my tears soaking his shirt as I clung to him, "I... I am now."

Tipping my face up towards his I looked into his blue/grey eyes and felt myself melting, wondering why he didn't want me.

Then he kissed me for the first time.

For a moment I froze, my greatest wish was coming true and I simply stood there doing nothing.

Almost panicking I wrapped my arms around his neck, my heart rate soaring as it thudded urgently against my ribs, and fervently returned the kiss.

"I'm sorry Chloe, it should have been me taking you out." He whispered as our lips broke apart, "Not that piece of shit."

"But you... you don't like me like that. I mean you.... you've never said anything."

He kissed me again, "I know. I've been in love with you from the moment we met but I've never had the courage to tell you."

"You have!"

"Yeah, I'm sorry if I've ruined our friendship but I...."

Connor never got the chance to finish his sentence as I pulled his mouth down to mine and began kissing him desperately.

"I..."

I started and kissed him again.

"...love...."

I gave him another kiss.

"...you to."

I finished by planting a final long scorching kiss on his lips.

From that moment on we were together, my plan for the evening had worked, although not quite in the way I intended.

It was six weeks later and we had been a proper couple for all of that time. Although things were certainly becoming hotter between the pair of us I had managed to keep Connor outside of my panties, albeit a little reluctantly on my part.

He knew I was a virgin and hoped that at some point in the near future I would let him take my maidenhead. However, always the gentleman, he was content to wait until I was ready.

It had become our normal routine for us to spend the weekends together. So, it was no surprise for me to find Connor at my place when I got back in from my last lecture of the day on Friday.

Not particularly wanting to cook I had been thinking about ordering in on the way home but waited until I got in to see if he agreed.

"Hey babe. I thought we might have a take away tonight. What do you think?" I called out as soon as I closed the front door behind me.

"Great idea, what do you fancy?" He looked up from where he was lounging on the sofa reading a text book.

"I don't really mind. But not pizza, we had that last time." I said after a moment before adding, "And I don't want a curry."

"That doesn't leave a lot. How about Chinese?"

Dumping my backpack by the door I gave his suggestion some thought.

"Yeah that sounds good. Where were you going to order from?"

"How about that place on the corner? What's it called?"

"Peking Palace. I think I have a menu somewhere."

"It's ok I got it on my phone."

Dropping on to the couch I put the television on but ignored the quiz program it was showing as I made my selection from the menu Connor had called up on his screen.

The delivery arrived forty-five minutes later and, opening a bottle of wine, the two of us sat down to eat. Apart from responding to my boyfriend's usual questions about my day I let the meal pass quietly as we ate and reflected on my decision.

Once we had finished and cleared the remains of our dinner away, I cuddled up to him on the sofa to watch a film.

"Connor?" The rom-com I had picked had only been playing for a few minutes when I whispered huskily in his ear, nibbling at his neck as I did.

"What?" He tried to keep his attention on the screen as my lips did their best to distract him.

"I've been on the pill for a month now."

For a moment he failed to register exactly what I had just said as I sat, grinning at him, waiting for his response.

"You've what." He suddenly sat up and turned to look at me, his face a mixture of surprise and expectation.

His expression was so serious I couldn't help but giggle, "I.... I went on the pill a few weeks ago."

My meaning obviously hadn't fully registered with him and he struggled to say something sensible.

"So, err... does that mean..... you, you want to... umm.... I mean..."

Leaning in to kiss him tenderly I let my lips press against his, my tongue pushing between them and tease into his mouth. I could feel my body trembling expectantly when his hand slipped between us, cupping my modest breast through my top, his finger and thumb searching for my half-swollen nipple.

It was a few minutes later that, flushed and aroused, I sat back and fixed my gaze on him, my fingers twisting nervously together. I had made the decision to give myself to him completely and I was certain it was what I wanted.

Unable to tear my eyes away from his I whispered, "I think I'm ready. I'm in love with you Connor and I.... I want you to be my first and take my virginity."

Swallowing hard I could feel his dick growing to its full size and tenting out his jeans as it pressed against my side.

"I love you to Chloe you know that. But are you sure about this?"

I swallowed and nodded, biting my bottom lip nervously, "I'm sure. I want you to... to fuck me."

He kissed me, pulling me into his arms as mine slid around his neck.

It was gentle at first, our lips barely touching but slowly it became more intense, his tongue probing into my mouth to toy against mine while his hands resumed their exploration of my body through my clothes.

I could only groan expectantly when his hand moved up to cup my breasts again, caressing the now firm nipples that stood out through the thin material of my top.

"You... you will be gentle... won't you?" I pulled back for a moment to whisper to him, my eyes never leaving his, "You know I.... I've never...."

"I promise." He kissed me again, "We'll go as slowly as you want."

My response was frantic, my fingers twisting in his hair as I returned his kisses ardently, the dampness between my thighs growing with every second and soaking my knickers.

"Take me to bed Connor.... Please. I want you to... to love me." I pulled away and gasped breathlessly, desperate to finally have him make me a complete woman.

Rising up off the sofa he held out his hand to me, gently pulling me to my feet and leading me through to the bedroom. Following submissively a step behind I could feel my stomach tightening with anticipation while my heart beat out a rapid tempo against my ribs.

It was finally going to happen.

Once we stood by the bed I slipped into his arms again, kissing him passionately, as he started to undress me. Peeling my top off over my head he discarded it onto the floor before running his hands down my body to begin unfastening my jeans.

Briefly breaking apart so I could push them down my legs to pool around my feet, I blushed and avoided looking him in the eye when I stepped away to kick my jeans aside, leaving me standing in just my bra and panties.

With a grin Connor hurriedly started to strip off as well.

Helping him to unbutton his shirt I ended up ripping it open, sending buttons flying everywhere, before unzipping his pants and yanking them, along with his boxer shorts, down so he was left totally naked.

"Oh my God it's... so... big." I gasped softly, my eyes widening as I stared at his almost fully erect cock, my fingers automatically wrapping around his swollen manhood, "I'm not sure..... if... it... will... fit."

The only other pricks I had seen before were on the few porn videos I had watched and while my boyfriend wasn't as big as some of them he certainly wasn't the smallest either. With a solid length of 7 inches and a girth of around 5" he looked and felt huge in the flesh and I had serious concerns about him fitting inside me.

"Don't worry Chloe. It'll be ok, I promise." Drawing me back towards him his lips found mine again, "I'll go as slowly as you want."

Fumbling at my plain white cotton bra he struggled to undo it until eventually I stopped him and, with a sly grin, reached behind my back to unhook the strap and peel it away from my small breasts.

Shyly I avoided his gaze and hooking my fingers in my little white panties I slid them down my shapely thighs, giving a man a view of my naked body and shaven sex for the first time.

My small 34B cup breasts were firm, topped with dark areola and hard little nipples, and stood high and proud on my chest. My slender frame tapering slightly in to my trim waist and then flaring out again to my hips and pert rounded bottom.

"God you're beautiful." Connor gasped his eyes large as he saw me nude for the very first time.

"No, I'm not. I'm too skinny." I bit my lower lip shyly, attempting to cover myself with my hands at the same time I protested quietly at his comment.