A Favour for a Friend

"So, you see, I need some help with it, and I trust you. Say something?" Natalie asked, dropping the eye contact she'd managed, blushingly, to maintain to look into her mug.

I paused, thinking. Natalie's request was, needless to say, unexpected and a little unconventional: and I wasn't sure how I was going to respond.

Natalie and I had met almost exactly a decade earlier, when we started at the same university. A group of mutual friends had seen us spend a lot of time over the next four years together, and we were pretty close. It'd never come to anything more—not for any defined reason, just that we were good friends, and that was fine. I'd had a few girlfriends over the years, though I'd never been aware of Natalie being in any substantive relationship. I read between a few lines and thought there might have been a couple of dates, but none of them seemed to lead anywhere. In this regard, Natalie had always been rather reserved, and had never shared much about this side of her life, despite all the time we'd spent together.

We'd not lived in the same city for a half-dozen years, now, as I'd moved away to take a job—Natalie had stayed put, working for the university's economics department, and doing well at it. She currently lived in a flat near the city-centre, a perk of the post, in some ways. I came down to visit several times a year, and Natalie would, once in a while, come my way. We'd drink coffee, discuss our work, occasionally visit somewhere, cook together, and stay up late with a bottle of wine. In many ways, not dissimilar to when we were students. But at its heart, the problem Natalie wanted my help with stemmed from before I met her. A hereditary condition left Natalie with minimal strength and manoeuvrability in her legs: although she could stand and walk, it was painful, and outside her flat she always used a powered chair. In ten years, I think I'd known her visibly struggle only a handful of times, her stoicism and measured approach to circumstances impressing me. Natalie got along, day to day, quite well, with a handful of friends she'd occasionally call on to help with something specific. In its way, that's what this was, I suppose: something she needed a hand with.

After spending most of the day in the city, we'd retreated from the cold autumn day to the warmth of Natalie's flat, and were enjoying a mid-afternoon coffee. We had vague plans for dinner, but hadn't really discussed what we were doing that evening, or before I set off home after lunch tomorrow.

"You know, Matt, I often ask whether you're seeing anyone, but you've not asked after my love life for years. Don't you care any more?" Natalie joked.

I had to laugh at her mournful tone. "Just got bored of always getting the same reply, and getting the brush-off," I retorted.

"And, in truth, I've always been grateful you didn't pry," she admitted, "though it seemed as though you were curious."

"Well, I was: pretty, smart girl like you, I thought you'd probably get asked out—I assumed you weren't interested. Not entirely my business if you weren't..."

"Too kind," she smiled at the buried compliment, "but you know it's not really that straightforward."

"I know? Well, no, I've always found it nerve-wracking approaching a girl, but—not to blow my own trumpet," I caveated, wryly, "sometimes they approached me. So, why were you turning men away?"

"You've always taken me as I am, and I appreciate that. You've never been odd about my legs, or what they mean, but not everyone's as relaxed about that sort of thing. I'm not sure, really, I'm the dateable sort. Yes, sure, there's the occasional interest, but I don't know: I worry about how it would all work, you know?"

Carefully, not wanting to undermine the abnormal candour, I asked, "Kind of. You didn't want to just take it as it came, and see?"

"I'm not sure it's that simple. We've spent ages together, and you know what I can do, and what I find hard—you know how to help me with awkward furniture, and you've carried me about when it's been needed. I don't trust too many people to do that: you know that. With someone I don't know well, there's all the normal 'getting to know one another' nonsense that everyone faces, but...I just worry, I guess, that it'd be too much, and I'd stress about everything too much to enjoy their company. And now, you see, it's even harder."

She took a ruminative sip of coffee. Waiting, I didn't interrupt, or prompt.

"I avoided romance when I was a teenager. Well, I guess there was the occasional, uh, moment with boys from school at a party, but nothing more than a teenage kiss. Then, when we were at uni, there was enough to deal with without the complications relationships would bring me. Well, that's what I thought then."

Natalie swallowed, looked away, then looked back at me, blushing slightly.

"Sorry to be blunt, but after this long I know you'll cope. The problem is, I feel a bit old now to get on the dating scene for the first time."

I smiled at her, trying to cover for her discomfort. "Bit old? Steady on, we're only 28. And I thought there were a few dates you played down in recent years?"

Managing to rustle up an answering smile, Natalie clarified her embarrassment, "Yes, alright, there were a few—though I thought I'd kept them discreet!—but...well. Matt, I've not slept with anyone. There you go, that's what worries me. How's that going to work? No-one I might start a relationship will be in the same position, like they might, just, have been when I was nineteen or twenty. And I won't know what I'm doing. Well, I'd know what I was doing, I'm not a complete ingénue," she stumbled on, gesturing at her legs, "and I understand the mechanics, but how would these work?"

She sighed.

"Why are you telling me this?" I asked, gently. "I've never wanted to poke my nose in, and you seemed—well—I suppose 'resigned', now I think about it, to being single. Have you thought of playing a long game, and trying to build on a longer-standing friendship."

I realised what I was saying, and laughed at myself.

"I'm not trying to sell myself here, you understand; if you were going to hit on me, I think you'd have done it long before now."

Alarmingly, Natalie blushed deeper, rather than laughing.

"That's just it, Matt. I'm not trying to hit on you: but I do want to ask your help. I'm not asking for a relationship, as it were, just...some practical help. I've worked myself up, now, to worrying that my inexperience is going to stand in the way of seeing someone. Instead of just worrying about, you know, the first physical intimacy with them, I'll be worrying about it being my first time. And I don't want that kind of pressure in a relationship where, actually, intimacy is kind of key. It's my own fault, in a way: I should have got all that out of the way sooner, when we were all messing around at university, and most relationships didn't last too long. It matters more, now, and I've not figured out how I can deal with sex already, and I really don't want to take the burden of my virginity to a relationship. So, you see, I need some help with it, and I trust you. Would you say something?" Natalie asked, dropping the eye contact she'd managed to maintain, to look into her mug.

I paused, trying to gauge my move.

"Natalie, what do you mean?" I asked quietly, "How do you want me to help? Advice on what to expect?"

Finally, she grinned at me. "Damn it, you've always been too nice. No, advice I can get, in this wondrous age of IT. I need someone I trust, and who knows me, and where I hope it won't jeopardise the relationship, to—well, to use my metaphor, relieve me of my burden. I know I'm not the prettiest girl you've dated, no, don't argue, I'm not: but...would you like to spend the night with me, please?"

"Not knowing how to reply is becoming a pattern in this conversation, Natalie. I...don't know what to say. Don't you think it would get weird? Besides, what are we going to do? I agree, and we just strip off and screw on the sofa? I mean, I'm...flattered, I suppose is the word. It's a brave thing to ask, and a big...responsibility? You realise it'll probably be...well, awkward, like you said?"

"That sounds like you're agreeing, I'd say," she grinned, bashfully, then returned to her more customary repartee, "and I don't think you argued my deprecation of my looks enough, mister."

"That's beside the point," I objected, not wanting to laugh this off, "I don't want things to be odd afterwards, and it's not going to be—wouldn't be, I mean—entirely 'normal'. You've never shown any interest, before, in me like that. And any attraction I felt, I've put aside years ago, because you didn't seem interested. What I mean is, how do you think we go from just friends two hours ago, to sleeping together later?"

Seriously, now, Natalie countered me. "Happens all the time, doesn't it? Think about it: long term couples aren't actually groping one another in public all the time. Are we any less close than many lovers? We've spent enough time together. We've drunk too much together, made fools of ourselves, argued over all sorts of nonsense, and still been friends afterwards. This is just one more thing we do together—and if it's not so great, then just think of all the awful movies we've watched: they might have been crap, but we laughed it off and carried on."

"This from the woman saying that she's worried about the first time in a relationship? What's different?"

"I don't know, entirely. I guess it's that we know we can be platonic friends, and so it doesn't matter if the sex is awful—or if I find out it's not something I can make work. If I start seeing someone, that feels like it would be a deal-breaker, for a lot of men. And, maybe, me. I don't know. What I do know is that I've been thinking about this for months. I weighed up whether you'd be offended by even the suggestion, as well as the consequences. But I'm tired of not knowing what I'm missing, for one thing, and I don't want to be alone, either. Solving the latter, for me, now, means knowing I can make this bit of a relationship work. And at this point, I need it to be someone who likes me, knows me, isn't going to be weird about my legs, or how I look, and can help me. Please, Matt?"

"Can I think about it?" I asked, stalling.

"Of course: I'll make another coffee," she smiled at me. While she put the drinks together in the adjacent kitchen, I tried to think it through. She came back, and we sat in slightly tense silence for a few minutes.

I broke it: "I'm not saying yes, yet. But how would you want to do this? Have you thought?"

"A bit," she admitted. "Do you mean the, um, transition, or literally 'it'?"

"Well, both, I guess. I will modestly admit to some experience with the latter," I smiled, "but none with the former, unless you want to go on a date, which sits rather at odds with what you've said."

"Could we just have dinner as planned, share a drink, and assume I'll be receptive to your advances? I know you wouldn't expect to make any, normally, but I'm sure you could!"

"Yeah, that could work, I suppose. Oh, alright. One condition, though, and one question: if it gets uncomfortable, or odd, we call it a night, and like you say, laugh it off as a bad idea. Yes?

"Agreed. The question?" Natalie asked.

"A practical one: I didn't bring any condoms, as you might realise. Did your planning extend that far?"

"One better," she grinned, triumphantly, "I'm, shall we say, taking something. Though, to be frank, I'm probably infertile," she admitted, the smile fading slightly, "but that's another thing entirely."

"Oh...I'm sorry, Natalie, I didn't know."

"That's ok, it's not really ever come up, has it? Anyway, it makes this slightly more straightforward, I suppose. Now, what are you cooking me as part of your seduction?" she grinned.

Returning to more familiar ground, we planned our meal, and, as evening fell, started to cook. Our regular, habitual interaction resumed, though there was a slight, but palpable tension, now, between us. I found myself, on more than one occasion, looking at Natalie in a different way. A very stereotypical, male, appraising way: not something I'd done to her for a while. For all that, it was a pleasingly anticipatory appraisal; Natalie might have belittled her looks, but she was attractive. Small and slender, with long black hair, she was always well dressed, and when she chose to deploy it properly, had a knock-out smile. Despite my reservations, long-buried desire started to manifest itself. With, admittedly, some nerves. What Natalie wanted worried me, in truth, more than just anxiety about a new lover.

Our meal over, we returned to the scene of our earlier debate, and I refilled our glasses. Whereas, often, Natalie would sit across from me, in her own chair, this time she came to sit by me. By unvoiced agreement, we ignored the topic that hung, heavily now, between us, covering instead a litany of subjects less...pressing. I noticed Natalie was more often mentioning or reminiscing about our joint past—unconsciously, or not, reiterating our bonds of familiarity and friendship. I hope it helped her: I have to say it calmed and agonized me in about equal measure.

The wine helped, though, and after a couple of hours we were, I think, relaxed. Or as relaxed as we were going to be. Natalie leant across to refill my glass: her face a foot away from mine, I saw a chance, and kissed her cheek.

"Careful, I'll spill the wine," she smiled, concentrating, "I'm not sure you've got your timing right."

She finished pouring, and turned to look at me.

"Took you long enough," she admonished, before leaning over, and kissing me back. My stomach jolted, as I found myself somewhere I hadn't ever expected, my old friend's lips locked on mine. Quickly finding my feet, and rested a hand on her upper arm, and enjoyed the contact. Inexperienced Natalie might be, but she did know how to kiss.

Moments stretched.

Natalie broke away, beaming, her hair slightly dishevelled where my hand had crept into it.

"That," she said, "was better than I expected. Oh; sorry, that's now how I meant that."

"No offence taken; I have to agree," I grinned. Gently, I pushed her back on the sofa, and, my face above hers, kissed her again. With a free hand, I stroked down her arm, and held her flank. I'd picked Natalie up countless times, to help her negotiate steps, stairs, or transient difficulties. I'd never, though, touched her like this. Wondering whether it would feel strange, my hand slowly, cautiously, tentatively stroked further, onto her hip.

Natalie kissed me back, unabated, one hand creeping into my hair, her other reaching instinctively to my waist. I wanted to balance two things: going slowly enough that Natalie was comfortable, and felt in control, but not taking too long about it, in case we lost the moment.

Fearful that reality could interpose, my hand stole, softly, across Natalie's stomach, and edged to her chest. The small, smooth mound of a breast was there for the taking. Lightly, my fingers danced across the surface, and a first small gasp broke from Natalie. I froze.

"Sorry, you're ok," she reassured me, "It's good, I'm just...not used to it. Keep going," she grinned, pulling me towards her.

I did, stroking with more confidence across the fabric of her blouse. Beneath it, I could just make out the shape of a nipple hardening. Sinking my face into her neck, I freed the buttons of the shirt, and slipped a hand onto the warm, bare skin of her stomach. As I caressed, Natalie arched her back gently, pressing back against me. My hand found the lower bound of her bra, and slid onto the swell of her breast, nudging the now-prominent tip before I ran a delicate finger along the scallop edge of the fabric. Boldly, I crooked a finger-tip under the bra, and ran it along, catching Natalie's sensitive nipple as I passed.

Nat gave a little sigh, and gripped my waist. Eagerly, now, I abandoned her breast, and reached behind her, unsnagging the clasp of her bra. With a supporting hand on her spine, she came upright, and between us we discarded her top and bra. Her small, high breasts exposed to my view for the first time, I sank my face to them, enraptured. I cupped one, resting my thumb on the firm dark nipple, while I nuzzled the other, tugging it gently between my lips.

Natalie's hands, free to wander, quested across me. One ran down my back, across my arse, and onto my thigh. Slowly, tentatively, it edged over my hip, and towards my crotch. Hand and mouth full of her tits, I was already hard, and her reaching fingers inevitably found my shaft. Her hand froze, momentarily, and then, curious, explored its length. Her hand discovered the head, then her fingers gauging shape and size, stroked down to its base, and the softer tissue of my balls.

"My lack of practice is going to show here, Matt," Natalie murmured in my ear, "I want to get into your trousers, but I'm not sure how."

I took my mouth from her beautiful tit, and grinned at her, "I really never thought I'd hear you say that, you know. Undo the belt, and the catch; I'll probably get the idea, and we'll wiggle them down. Try?"

Nat laughed, "All right, I suppose I'm meant to be learning."

She followed my advice, and, with my willing aid, my loosened trousers fell to around my knees. Fearless, Natalie hooked her fingers into the waistband of my shorts.

"Here goes," she whispered, teasingly, as she kissed me deeply on the lips.

I chuckled around the kiss, one hand behind her neck as I leant on my elbow, the other teasing her nipple once more. Her hand ran up my inner thigh, and came to rest, cupping my sack. Gently, she held one ball between her fingers, exploring the soft shape within the compliant skin, before cupping them both in a small hand. I tried to stay still and quiet as she investigated, but a small sigh escaped my lips as her hand came up my shaft, and grazed over the sensitive frenulum. Natalie giggled, as she stroked back over the spot, enjoying my response. Wrapping her hand round me, she gave my shaft a squeeze, and tentatively moved her hand up and down.

Natalie looked down and watched my cock. She seemed fascinated by the foreskin covering and uncovering the head.

"That's surprisingly mesmerizing," she commented, watching intently.

"You obviously have an idea of the mechanics; I didn't assume you would," I commented.

"Yes," she smiled, glancing up at me, "This might be my first contact in ages, but I get the anatomy, and the basic mechanics. I've played with one of these before, years ago, but not so...openly, I suppose. You know, more of a hand-down-pants thing. This is much more fun."

"Well, personally, I think you're overdressed," I declared. As she toyed with me, I unbuttoned her trousers. "Do you want to take them off, or do you want a hand?"

"I'll do it," Nat said, releasing me to wriggle her legs out, and dump the trousers with her blouse. I quickly unbuttoned my shirt, and discarded my clothes, too. Drinking in the sight of her slender legs, my eyes ran up, over her small black briefs, across her flat stomach and breasts. Her face, though, looked a little uncertain, and I smiled encouragingly at her.

"Matt...", she began, "I'm worried you'll think I look strange. Would you come back here and kiss me, and stroke me instead of watching me take these off, please?"

It sounded fine to me, and I lay back down alongside her, and kissed her, full and deep, while I stroked her head with one hand, and held her waist. Keeping my attention occupied, Natalie quietly rid herself of her underwear, and lay naked and vulnerable next to me. Softly, slowly, sensuously, my hand smoothed a path down, and came to rest on a bare buttock. I paused, waiting, but Natalie didn't tense or flinch, and I took this reassurance as an invitation.