Surrogate Sister

This is my first published story. It involves partner sharing, so if that's not your thing, I'd move along. All characters and the events portrayed herein are entirely fictitious. Thanks for reading!

We were having The Conversation again.

Jill and I had been trying for a baby for a couple of years and it had become clear that the natural way was not going to be fruitful; the doctors did their tests and had concluded that the problem was with Jill's plumbing, and not mine. IVF was the only option, they advised, and even then they offered only an outside chance- and at a huge cost. We couldn't really afford it but we did have some savings we'd scraped together over the last year or two and reluctantly we allocated that as a budget for the process, even though it seemed like a huge and expensive gamble.

Various people had suggested adoption or surrogacy as alternative options. I had favoured the former and Jill the latter, and then as we argued on the merits, I ultimately caused a massive fallout by suggesting that we give up the idea of kids at all. I was happy with the idea of being a dad, but neither was I driven by the need to be a parent, while for Jill it was almost an obsession and I had idly wondered if we should not simply embrace a happy life as a couple. Jill had icily commented that if that was what I truly wanted, well knowing her desire to be a mother, perhaps we shouldn't be together at all.

It took a while to build bridges after my blunder after she left me to for a week while she stayed with her sister Emily, who lived across town with her boyfriend, Carl. Jill returned home a few days later and we reconciled very passionately in bed, shortly after I had made my grovelling apologies. As we lay in the afterglow, I had resolved to diplomatically agree to Jill's ideas on the subject, whatever they might be.

I was more than surprised by the suggestion she shared with me. Her sister, she said, was willing, - if not eager- to help Jill to have a child- to the point of offering her own services as a surrogate mother.

"Wow- well that's one heck of a commitment, " I said. "Is she sure about this?"

Jill explained. "Tim, I'm going to let you into big family secret. Even Carl doesn't know- so this is in confidence, ok?" She continued, conspiratorially: "Emily got pregnant as a teenager. Got persuaded into an abortion; I've not talked to her much about it before now, she never wanted to- but she regrets it now. She doesn't want kids of her own now, she says she doesn't deserve to have them; but she says doing this, having a baby for us, would be like making amends for the one she got rid of."

I remembered my recent resolution to agree with Jill's proposals, but this felt awkward. Jill seemed to be positively into the idea, but I thought it had obvious problems.

"Well, " I began carefully. "I suppose it gets rid of all the problems we had about surrogacy, having a stranger involved and everything." Tentatively I couched my positive response with a potential hurdle. "How about Carl, surely he wouldn't agree?"

"Carl: well. That's where the cash we've got saved up comes in. He's heavily invested in his business, and our 10K will help him out of a tax hole, from what I understand. Emily doesn't want to take anything for doing it, but Carl was over the moon about the idea when I said we had that put aside for IVF."

That was typical Carl. While I liked Em a lot, Carl was, frankly, a bit of a dick. He was a poser whose sole employment (other than working out) was a number of somewhat uncertain business interests. He flashed cash in public, but I knew he'd drained Emily's share of her and Jill's inheritance and he'd tried to tap me and Jill for "investment capital" more than once. Carl's charm however always seemed to win over the girls who thought he was an attractive, well-groomed rogue and even Jill always found a way to defend him when I griped.

I sighed, seeing that raising objection to Carl's selfish interest in the transaction was not going to be sustainable. "Well, I guess that's we were saving it for. And IVF was a huge gamble anyway."

"So are you alright about it?" My wife seemed surprised at how easily she had won this argument. I swallowed my distaste for paying Carl for the privilege of Emily's biological hard work and made a show of reluctantly agreeing.

"I suppose I am. I mean it's a bit weird it being your sis, but at least its someone we know we can trust, and if you are okay with it then I guess I am." I paused. "What are the practicalities? I guess I wank off into a jar or something and then she... puts it in, somehow?"

She looked a little tripidatious at this turn of subject. "Well that's something we need to talk about too."

"okay...?"

"Well, after her abortion and everything, Emily says she doesn't want any of the process to be, ah, artificial in any way."

"Artificial?"

"Well the actual... insemination; it has to be entirely natural, or she's not prepared to do it"

"Insemination- oh! You mean? With my actual-"

"Its her one absolute condition."

" So, she and I have to, you know?" I felt my face redden.

"Yeah. She won't have anything -- even a syringe."

"Jill, Are you sure you are okay with that?"

Jill frowned. "I think so. I'm not completely enthralled by it but on balance, it makes sense. The solution feels so neat, the DNA is going to be so close a match to you and me, and she so wants to help and heal some of those wounds from what she went through. Anyways, we've kind of worked out a system for how it will work."

With that she told me, with her familiar organisational relish overtaking any prudishness, about how the mechanics of my inseminating her sister would work. She would be present at all times, as would Carl. Jill would get me off while Carl would provide Emily her own warm up. When I was ready to cum, I would simply put myself into Emily and ejaculate. "So its not like you are fucking her, you are just cumming in her," explained Julie, as if that made all the difference.

"And Carl is honestly okay with all this?" I said incredulously.

"Turns out Carl is quite broadminded, so long as he gets paid."

I have to admit that the idea of cumming inside my wife's sister was not without its attractions. Even though it would be slightly constraining with partners present, overseeing it all. As I said, I thought Em was pretty cool and I'd be lying to say I didn't fancy more than a bit.

Not that I would have the freedom to fantasize about the idea for long in advance. With usual military zeal, Jill had plotted Emily's ovulation and determined that the weekend a week or so hence would be the most propitious time for the union. I was on strict injunction against any 'activity' over the run up to the date, whether mutual or solitary.

Now for a guy who wakes up with a hard on every day, that's a trial. But I would need all of those gallons of sperm that were soon practically sloshing around in the tanks. It turned out Jill was not expecting just one performance from me but had the whole weekend planned out.

I felt like a stud stallion being prepared to be matched with a prize mare for mating.

***

The weekend finally arrived. The anticipation was quite palpable and I'd even had some very interesting dreams, especially after a week or more of abstinence and left at least one wet patch on my side of the bed.

It was Emily's idea to dress formally. Jill was a bit hesitant but agreed, bringing out her usual black cocktail dress ("my fuck me" dress she called it) which emphasized her slim figure and flattered her boobs. I was barely able to not simply ravage her in the taxi on the way over. I went for smart casual, jacket and open neck shirt with good jeans.

Emily met us at the entrance to the flat, kisses and embrace for Jill and a blush and a peck on the cheek for me. I could tell Em was nervous, as usually she and I flirted casually but when I tried an opening line with her it fell flat and she looked pointedly at her sister and ignored it.

Carl, tall and broad, looked like a bouncer, filling his suit. Over-familiarly, he swept up Jill and to my annoyance my wife did not recoil in disgust, but allowed him to bend her back for a kiss on the lips extravagantly and for a moment too long. Releasing my wife, he gave me a half-smile half-scowl and after a moment offered me a hand. "Not sure who has the best end of this deal, bro," he gave me a wink, as usual trying to dominate the handshake with his muscular grip.

The evening progressed awkwardly, and as a result we all imbibed relatively heavily. Jill and Em had wisely decided that a heavy meal would be a bad idea, and the light snacks which Emily dutifully kept bringing out were pleasant but unfulfilling and as a result the alcohol seemed to take affect quickly. Carl kept topping up his custom "Old Fashioneds" and although his bragging about their efficacy was irritating, they did take the edge off pleasantly.

Emily and I were both nervous and she couldn't seem to even meet my eyes across the room, which made things a little difficult; fortunately Jill and Carl kept things moving socially. Jill, although imbibing fairly heavily herself seemed to disapprove of either Emily or myself getting too squiffy and after a couple of refills and just when I was starting to get comfortable, she suggested that we start to move on to the serious business of the night.

Carl interrupted. "Business before pleasure, darling. Does your husband want to blow the dust off that chequebook before he samples my wares?"

I glared at Jill who just rolled her eyes. Emily just looked away, embarrassed.

Shrugging I reached inside my jacket and pulled out a folded piece of paper, which I'd already written and signed. I went to pass it to Emily but Carl intercepted it with glee.

"You are such a pimp, Carl," I said dryly, while he grinned and made a big deal about checking the detail, and then pronounced himself satisfied that we could progress.

Emily dropped the lights and had lit some scented candles, setting a more relaxed atmosphere. Self consciously, both couples sat opposite each other.

"So... how do we start?"

It turned out to be less awkward than I expected. At Jill's suggestion, we simply all just stripped. We had decided that both Jill and Carl would get naked too, this would make things more comfortable for Em and I as things progressed. Jill started things off, simply pulling her loose dress over her head and proceeding to unbuckle her bra. I saw Carl take a long glance at her she unashamedly dropped it to the floor; I couldn't really blame him as the slightly dimmed lights revealed her slim yet shapely body from her small but perky breasts down to a newly shaved mons as she stepped out of her knickers.

The rest of us were less elegant than her but after some awkwardness all of us stood naked, each next to our partner in front of the two couches. I stole my own glances at Emily's body- consciously comparing her to her sister, my wife. Emily, the younger of the two, was an inch or so shorter, a redder in hair and lighter in complexion to Jill, hair middling long where Jill's was dark and short; body slightly rounder, and fuller, compared to my wife's athletic toned figure; Emily's breasts fuller- fleshy and pink tipped, Jill's smaller and shapely, upturned brown areolae ripe and erect. My description makes them sound very different but they were still clearly sisters and shared a lot more in appearance and poise than they differed by.

Any slight anxiety I might have had about performance was unfounded as I felt my cock stirring in appreciation of these two beautiful naked women standing so close to me. I saw Emily glance down at it and then up to my face, blushing as she gave me a nervous smile. Carl stood unselfconsciously leering at both the girls, confident with his muscular physique and a large, as yet un-woken cock hanging down against his thigh.

We began matters by simply making out with our own partners, opposite each other on the sofas. Jill and I kissed; deeply and passionately, and I was unaware of anything else in the universe at that point. I massaged her breasts and her hand found my cock and gripped it hard, stroking it and finding it already lubricated with substantial pre-cum. "Excited about fucking my sister?" she whispered.

"No, just you," I whispered back.

"Right answer, " she grinned. "I love you."

"I love you back." I swore, earnestly as we paused, looking closely into each other's eyes. "We don't need to go through with this, Jill. We can just fuck each other now, rip up the cheque and use the money on IVF after all."

She shook her head firmly. "No, stick to the plan, you are going to put our baby inside Emily. Don't pretend you don't want to." Finally she broke off, whispering in my ear "Tell me when you are ready!" and with that she trailed her lips down my body before engulfing my engorged cock between her lips. I sighed, knowing that "ready" would not be far away.

As Jill industriously kneeled at my feet, working her mouth on my cock, I had the opportunity to glance over her across at the other couple on the couch opposite. They were as deeply involved as we. Emily had her legs spread apart allowing Carl to finger her enthusiastically. He was rapidly plunging two moist fingers deep in and out of her and I had a great view of how wet she was. In return, she was vigorously stroking her boyfriend's now very erect tool. Carl appeared to be particularly well endowed - he certainly had some girth and a couple of inches of length on me, and I've never had any complaints. I was going to have some big boots to fill soon.

Carl was staring with avid interest at my wife's backside, as she was on her knees kneeling servicing me directly in front of him, so close he could practically reach forward and touch her. His view was no doubt improved by the fact that although she had one hand around me as she efficiently sucked my cock, her other was active between her own legs so Carl had a ringside seat as she fingered herself.

This very pleasant scene played itself out for a little while -- I'd like to say that it was a decent period, but if I'm honest after two weeks without any outlet and the stimulation I was receiving, my sap had risen very promptly.

Jill was stroking me with a smooth rhythm while she ran her tongue around my cockhead before trailing her fingers around my tight ballsack which always tips me over the edge at the best of times. Suddenly I knew ejaculation was imminent and I tapped Jill's head. Her eyes widened and she pulled back her head. I clenched everything tight so as not to spill my load into the air as I stumbled to my feet; Jill guided me towards her sister.

Carl reluctantly moved aside and Emily opened her thighs, looking wide eyed up at me as I moved between her legs, her pussy enflamed and pink, lips glistening wet under a fuzz of pale red-brown. Carl and Jill faded into the background, I was barely aware of them as I focused my attention on Emily. A red glow spread across her chest, which rose and fell enchantingly, her full tits quivering, their areolae pink and swollen (very unlike her sister's, dark and compact); her eyes, big and brown, wide; lips smiling. "I'm ready for you, Tim."

My cock was glistening wet with my wife's saliva and my own fluids; it was angry red and swollen bigger than perhaps I had ever seen it (not as big as Carl's, though, came the thought, unwelcome). I seemed to be frozen but Jill was right next to me and she took the big hard rod in her hand and nuzzled the head of it up against her sister's cunt, nosing its head between her pink parted outer labia, sloppy with her anticipation.

It was no effort to push forward and to penetrate Emily. I did so slowly but firmly, a collective sigh released as my length came to rest fully inside her. I was very quickly fully sheathed inside her- to the hilt, I could just feel the presence of the wall of her cervix against the end of my manhood, my balls tight against her back side. The feeling of that moment, the heat of her, the sensation of her flesh enveloping me- almost indescribable.

We were locked together, our respective partners might as well have been a mile away- there was just Emily and I in that universe then. Her hands were on my hips, drawing me into her; mine on hers, pulling her up to me. Our eyes were locked and she mouthed silently...

"Come in me..."

...and I did.

How many orgasms does a man have in a lifetime? Ten thousand? More? How many do you remember? Actually remember?

This one is stored deep inside- to revisit any time I feel like it.

It seemed to take ages for the first pulse to actually crescendo -- it was like there was so much which needed to get out the pressure just built up until suddenly it released. I swear I almost felt a physical recoil, from that first jet of semen I unleashed inside Emily. She felt it too, her eyes rolled back into her head and she bit her lip and pulled me tighter into her as the second torrent unleashed more of my pent up reservoir of sperm, up against her cervical opening and flooding into her fertile womb.

The waves of pleasure were now hitting me and I could not help but groan aloud as we rode each pulse of ejaculation together. Emily had been trying to hold it together but she could no longer conceal from the others what we both already knew- that my cumming in her had triggered her own orgasm and now the low moan escaped from her, strangled into a squeaky uncontrolled exclamation. We rocked closely together- no thrusting you understand, just me docked tightly inside her, and my semen pumping from me to her in barely diminishing pulses.

And then eventually, it was over. I seemed to blink awake, suddenly aware of context and other entities around us. I was still deeply embedded inside Emily, and she lay back on the sofa, head lolling back and arms asunder, but her legs locked around my waist and not letting me even think about pulling out.

Our partners, naked and somehow ridiculous, both on my right hand side, Carl seated and Jill kneeling with one hand on my back and the other just touching her own pussy.

"Fucking hell" exclaimed Carl.

"That was fucking hot babe," exclaimed Jill. "Tim, I need you to get out of my sister and give me as good an orgasm as you gave her. That's an order mister!"

"No." Emily's voice was deadpan, her head still back against the cushion and eyes still closed tight. "He's not coming out yet. I want to keep all that semen inside me where it can do what we need it to. You know that Sis." Unknown to the others she gave me a hard squeeze with the inside walls of her vagina; I twitched my cock in response.

"Okay," began Jill. "You're right, but I just didn't realise how horny this would make me. I so need to be fucked right now."

"Fuckin' A!" exclaimed Carl, his eyes wide and angry as he rose, his member extremely erect and swinging as he stood up aggressively. "C'mon man, you had your fun fucking my girlfriend, get your arse off and let me have her now!"

"Carl. We talked about this," sighed Emily. "You know you can't fuck me tonight, it defeats the whole purpose of this weekend. Come here and I'll give you a handjob to remember-"

"Yeah right, Tim gets to fuck you all weekend and all I get is a fucking wank- I can do that myself."

Carl's agitation was palpable; he was a big guy and I was still adamantly locked inside his girlfriend, her legs tightly holding me inside although my cock was no longer its full hardness, partly in response to his increasingly aggressive and jealous tone; I was not very well set up to defend myself if things got ugly. I didn't regret for a second what we had done, but I realised we had completely underestimated what effect it would have on us all.