Third Time Getting Lucky

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"True. Come see, see which you'd prefer. Quite happy to be elbowed out in the night!"

It was interesting, seeing a guy's bedroom complete with a lifetime of possessions. I never really had, before. Oddly intimate, entering and noticing all the items on the walls, the shelves, and on a large desk.

Nothing particularly embarrassing, but I did spot a framed photo turned face down among various others. I assumed it had fallen and stood it up.

"Do'- do' -- DON'T do that!"

I dropped it and looked curiously at him. It was the first time I'd heard him speak sharply to anyone.

'S, s,s, SORRY. It's, it's it's it's the ex... Guh-uk, kuuh." He sounded like he was being strangled. I waited. Then the word he wanted exploded out. "Clare. Ex. Ex. Ex. Painful."

He shrugged, clearly more upset than he was trying to come across as.

"The ex? Just the one, then?"

Another shake of shoulders. "Pretty much. Thought we were doing really well, until dumped me a couple months ago. Met a guy at college... Could have told me before I spent five hours driving down to fucking S, S, S, S... outhampton..."

"Southampton's a hole," I agreed, trying to get into the spirit.

"Yeah. Should have dumped her when she first went there," he tried to joke. "Anyway, it's a nice photo frame, hoped to replace the photo soon..." He looked up at me, shyly.

"I gurn, terribly."

"Excellent. We'll match." He smiled.

In the end he came to say goodnight to me, got into the bed, and we both slept soundly as sardines until morning. I could get used to that. We did some gentle canoodling but nothing that would be too distressing to halt when interrupted. I was liking getting used to that, too.

The next day we packed picnics and squeezed into his sister's Beetle, which seemed an impractical vehicle for taking camping. The plan was to camp out in the Shropshire hills. After a bracing walk through stunning countryside, it was time to erect tents before seeking out a dinner in a pub -- always the best way to eat when living under canvas. We got Bill and Ruth's up fine, and started on the second. I couldn't figure out how the inner went on the frame.

Tom was dismissive of my incompetence of putting it together. "It should be fine. I put the old tent up to check it was all there, just like they tell you, but it was mouldy, so I got the other one out -- it's definitely got all the poles, inner and outer bits!"

Bill inspected it carefully.

"Young Thomas?" he intoned. "You have, indeed, an A-frame of poles. You have, indeed, an inner and outer canvas which match each other. However, they are for a dome tent..."

We tried to improvise and get the canvases to attach to the A-frame, given the weather wasn't expected to be windy.

It didn't work. It was going to have to be all four of us in the one two-man tent. Ruth was already way too sloshed from Bill's hip-flask to drive home.

"Ach, it'll be fine, said Bill. Ruth and I looked less convinced. I'd slept in the open before, but it wasn't warm enough yet.

We had an excellent meal, and hiked back in the dark, carefully. With Tom supporting me on one side and Bill on the other, I didn't fall over, but it would be a relief to get to bed.

It turned out that the tent might well be generous for two, and feasible for three, but I was the smallest there, and for four, there was not an inch of remaining floor space. We lay heads to tails in our sleeping bags, opening the flap to make it less stuffy. After a lot of banter, I grabbed Tom's feet to use as a pillow, to stop the chaps from kicking my face again, and got some bursts of sleep.

The next day, Sunday, we drove back early, for a slap-up Sunday lunch. I didn't take much persuasion to have a nap after -- though it turned out that wasn't what Tom had in mind while everyone else was out.

Getting me to stay awake took a more effort on his part.

He was good with his mouth, though. I don't mean speaking. Back on board with filthy fun, I offered my gratitude and rashly promised him whatever he'd like.

"You sure? You know what I'd like, but only if you could...?"

"I would, too, if we can get my stupid subconscious on board..."

"Only if you're sure."

"I'm sure I want to! I can't promise anything else."

It looked promising. He was hard; I was wet.

He got a tube of lubricant on the job -- applying half of that was a lot of fun from my point of view.

We put a pillow under my bum: "they recommend it in Company and 19," I said.

His rubber-clad cock felt cool against me, but not unpleasant.

"Go!"

He tried, attempting to push forward, folding my labia out of the way. Suddenly I felt that pressure. It hurt ever so slightly, but more importantly, it was reliving that nightmare yet again.

I rolled sideways, pushing him off as he scrambled off me. At least we were getting better at that bit.

"Karen? It's me, Tom. It's OK. Honest. You OK? Karen?"

I squeezed his fingers, let him hug me, enjoyed the warmth. I couldn't think of anything to say.

All too soon, it was time to shower before his parents returned.

I calmed down under the hot water. And managed to return the favour to him, not because I was carefully keeping score, but because I felt he really deserved a good time.

As long as I was completely in control of the positioning, I decided I quite enjoyed the odd bit of sucking cock. Watching the effect on the men they were attached to was fun. Three men, made happy, now, and all perfectly happy to lie where I wanted if it got them getting their rocks off!

At least I was successful at one bit of a sex life.

"Is it OK, come to you again next weekend?"

I was relieved he still wanted to. Though after the tent fiasco, he possibly felt the same way.

"Yes! I can even provide a bed for both nights..."

"Luxury!"

"Yeah. Can't promise a clean bathroom, mind you. We're trying to house-train Alec and Charlie, but not much joy so far. I swear they just pretend to be incompetent at cleaning!"

A couple months went by, with us seeing each other most weekends, and of course being able to chat via Say at work. A few evenings, I even stayed late and got the bus home so we could carry on talking, much more productively and privately than via home or phone-box, and of course it was free. Even before 6 pm! These were the days when we were still asked to make business phone calls after 1 pm, where possible. If someone called in the morning, you knew it was important!

Tom and I were having lots of fun in bed, but still no successful sex.

Then there was a long, long fortnight, of too much work for both of us, family events preventing us seeing each other on the middle weekend. That second week really dragged.

It was Saturday, finally!

Tom appeared at lunch time. The others were out, so we decided we might spend time in my room now, socialise later.

The cheeky bastard teased me loads. I wanted sexual pleasure, but he was stopping just as it got good. Git. I couldn't wait for later that evening, when I would have my revenge.

Ben and Delia returned, so together we ordered takeaway curry. Alec was visiting family, Charlie out elsewhere. Our conversation -- Ben and Delia with me -- took its usual flirtatious turn.

"You and Delia should get together and provide 'entertainment' for me and Tom," Ben suggested. I reminded him that Delia wasn't interested -- she shrugged apologetically as usual.

Tom twigged. "But you would be?"

A quiet question, but going to the root of my heart.

My face burned.

Ben had always taken my sexuality in his drunken stride, but I'd never been sure how much he'd believed it anyway.

"Yeah," I said, casually as I could.

There was a short pause that seemed endless to me.

Then Tom observed, calmly, "Well, who wouldn't be?" He made it sound like a compliment to Delia.

But then there his subsequent low query, "D'you actually like men, though?"

"Yes!" I was vehement.

"Oh. Just ch,ch,checking," Tom gestured in a frantic back-paddling motion.

"No, that's not the problem," I said obscurely, wanting to cry.

Tom put his arm round me and we felt connected again.

Delia eyed me curiously when she returned to the room with Ben, but said nothing.

Eventually, we went upstairs to bed. I wanted so much to prove that I really did want to be with him, not any woman or anyone else, but was still terrified if I thought about it too much.

Then I saw Tom lying flat on his back in the middle of the bed, arms out to his sides. Totally unclothed.

Beautiful.

"What are you doing?"

"You're in control. Do what you want." He shrugged, as best he could while supine.

I looked down at his naked body, a cross across the bed.

I liked it.

Now, what to do with my own personal Jesus?

I smiled. I stroked his torso up and down, and the same for his legs. I climbed up to kneel over his thighs and he eyed me lasciviously, licking his lips but remaining still. I brushed his sides, ran a finger down his neck, his chest, and enjoyed re-exploring his body from this new angle.

Eventually, I might pay some attention to his cock. But not yet.

I teased him with running my hand round under his balls, round the base of his cock, twisting some of the wiry hair around. He was liking it all. He folded his arms behind his head and looked at me, eyes twinkling as he challenged me.

"I'm not doing anything. Just lying here. Anything that happens, it's all you." He looked meaningfully at the bedside table, whereupon stood condoms and lube.

I thought about it.

We both knew that it was the tiniest thought of force that had me freaking me out. So this, no weight even from his side... just maybe...

I used my palm to check he was at full stiffness, kissed his tip, and went to get a rubber out of its wrapper.

"I'm not helping you," he commented. Cheeky git.

"You'll just have to wait for me then, won't you?" He watched my every move as I got the thing out, flipped it the right way round, slowly rolled it down him and stretched it into position, added a good squirt of lube on top, got some on his stomach making him wince at the cold gel, scraped it back on to my hand and started coating my vulva lips with it.

"Probably still won't work, you know," I said, to manage both his hopes and mine.

But we both thought it might.

I knelt down and straddled his thighs, and stotted upwards on my knees towards his head. His cock was right below me. Tom removed his hands from behind his head -- I suppose it did look a bit 'service me, wench' - and put one under each pillow.

All as unthreatening as he could possibly be.

He was my plaything now. A boy toy. Oh, fun...

Concentrating on thinking of him as a toy, a giant warm dildo, I sat down an inch, and another.

The tip of the rubber touched my cunt lips, and then I felt the substance of his cock. I pulled myself an inch more upright again, until I was above it.

I reached between my legs to part my labia, and put them to either side of this upstanding post. I bent my legs again so his cock slid just a tiny bit inside, maybe half an inch.

It was spreading me open much more than my fingers or his could. Like my vibrator, I remembered. 'It's just like playing with myself with any other toy,' I reminded myself.

I tentatively sank down another couple mill, and another half inch, and another. I was feeling opened, stretched all around, and it felt like it ought to hurt soon, but it wasn't yet.

It was beautifully intense, yet gentle. Tom was still transfixed, gazing at me like I was a goddess. For the moment, I felt I was. He was clearly praying that this moment would last.

I decided to sink down a little further, slipped a bit and took more of him inside than I'd intended. I cried out, then realised that, while I was feeling a bit full and pressed upon inside, all around the circumference of my vagina, it didn't actually hurt.

Bloody weird, mind you.

Half his cock must have been inside me by then. I met his gaze and nodded, all OK!

He relaxed into enjoying himself, and I tested tentatively raising myself up and down. Oh, man!

The feeling was exquisite, delicate pressure, made all the better by watching the blissful expression on Tom's face. I was making that happen! Me! And as I relaxed, and got used to these new feelings, I wanted more.

So I let myself flop down as far as I could; suddenly fearful at the end that my cervix would get bashed in and it would hurt, but the fear was unfounded. It didn't hurt at all.

I was just filled up. My cunt was full of cock.

The sensation was so good, it was life-changing.

The feeling of having his whole, sizeable cock inside me, filling and stretching me, firm and solid there, was incredible. Sitting comfortably, his groin under mine, was good, but the best bit was that every tiny movement either of us made -- and we both made lots of them -- made part of my pussy throb. It had me moaning, overcome with the intensity of the feeling and all the emotion.

Ah, the emotions! The relief of knowing I could have a sex life! And that I was loving it! The relief of knowing I could give a man this kind of pleasure, and the satisfaction of doing so -- I was definitely, at least somewhat, heterosexual -- those feelings were all good too, but I recall catching sight of the wall clock -- twenty past midnight, it was -- and feeling that I finally had a hobby.

I wanted to do this again, lots.

I leant down over his body, and contemplated stretching my legs out behind me, but dismissed it as too complicated. I couldn't quite reach his face for a kiss, but got a close-up view of his expression as he reached his peak of pleasure -- which felt very good from my end, too.

Yes, this was a huge breakthrough. One small thrust for a man, a giant leap for my mind.

I dismounted only when my calf started getting stiff, and fell down next to him. We lay side by side, hugging each other and grinning inanely.

It took about fifteen minutes before we tried again, same technique, then a couple hours before attempting missionary position.

Which took a few goes to sort out the right angle, but now I knew how cock was supposed to feel inside, it was fun figuring it out. The fear was gone; now I knew sex could be good, I just wanted to keep practising until it was great. And this was getting pretty damn good.

By the following afternoon, the twelve-pack of condoms was almost depleted. It had been a bloody good weekend, getting out of bed only for meals. And the sex was good, even if I hadn't had one of those impressive-sounding orgasms, just general waves of happiness.

We decided on one last round before we had to part. Tom was trying his hardest to make it as good for me as he could, and it occurred to me that maybe, faking an orgasm wouldn't be such a bad idea. So I tried a bit more moaning and gasping, breathing in deeply, just playing it up a bit.

Clearly the acting triggered my subconscious, as suddenly, my cunt took over, writhing wildly, throbbing like a motorbike inside me, and I was groaning and crying, nearly screaming, because I completely could not stop. It was a total loss of control of my body, like I'd feared, only not, because this time it was pure raw sexual power taking me over, not violence.

Letting go like that was astounding.

Quite apart from the emotional breakthrough, my cunt felt rich and deeply satisfied for the rest of the day. I suspected my housemates could figure out what had happened from my complete failure to hide the huge grin on my face, especially as Tom's expression was fairly similar. Thank goodness only Ben and Delia, wearers of similar faces on many a morning, were there to see.

I couldn't wait for the next weekend.

No matter what happened with Tom, he'd given me the gift of enjoying sex with men.

Apparently his sisters had suggested the plan to him, when they'd wheedled out of him that I seemed to be scared of sex.

As a result, he'd forgiven them for pretty much everything they'd done to annoy him when they'd been teenagers.

Well, just about. Older sisters can be incredibly annoying.

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8 Comments
AnonymousAnonymousover 1 year ago

That was so very beautiful. In every respect. Thank you.

Ravey19Ravey19almost 3 years ago

Good enough for 5 stars. A little long winded but I do love longer stories with plenty of detail. I particularly admire how you've brought Karen with her problems and medical conditions into the story and made her they key character.

Lovecraft_LoreLovecraft_Lorealmost 3 years ago

5 stars.

I normally hate rapey back stories but this one seemed to work.

AnonymousAnonymousalmost 3 years ago

Excellent! Love it....

AnonymousAnonymousalmost 3 years ago

Beautiful story. And this line "Yes, this was a huge breakthrough. One small thrust for a man, a giant leap for my mind." had me genuinely laugh out loud. That's rarer than getting one off on this site 😉. Thank you.

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