Playing with Dolly - Ch. 03

Chapter 3. Return Flight

Author's note: In the first part of this chapter, Gemma narrates her experiences to us, and to Dolly. Trying to make it all dialogue, with quotation marks, would be hard and messy, especially as she's also quoting things previously said between Greg and herself. Therefore I've rendered what Gemma says as narrative, with Dolly's interjections in italics and parentheses; kinda the reverse of what I did for Dolly's reminiscences.

*****

Yes, Dolly's glass was empty, despite the recent generous refill. I topped it up again, and she swigged thirstily. As for her other request, I didn't know what to say. I turned off the recording and put the microphone and phone away. She then produced another glass from her bag.

("It's about time you joined me in a drink. Or do you stick to Prosecco?")

I accepted the rather generous measure of scotch she passed me. I didn't usually drink spirits, but having listened to her story, I was very churned up inside. I was sitting next to a woman who was quite literally living on borrowed time, talking about adventures she'd had nearly seventy years earlier. I'd heard tales of love, loss and premature death, and some stories which would have been banned as pornographic if anyone had tried to video them. Just conjuring up some of the images in my head was creating emotions and physical responses that would have seemed completely inappropriate in this context with anyone except Dolly. Her tales were having a strange effect on me. I doubted whether I could use more than half of what she'd told me, but I most definitely didn't want to stop listening. And she'd intrigued me with hints at her broader life story, which was outside the scope of my thesis, but about which I was eager to hear.

("Now come on girl, give an old lady a thrill. Tell me what young people get up to nowadays. Spill the beans. Does your boyfriend have a big cock? Does he fuck you until you scream? Do you like it up the arse? Can you take him in your throat? Have you had girlfriends? Have you ever had a threesome or an orgy? I'm not going to tell anyone, and no one would believe a senile old bat like me if I did. But I'd really like to know. Will you indulge me?")

I took a big gulp of my whisky. I could feel it burning in my mouth and my throat. And so I began.

I met Greg at university. He was eight years older than me. He'd been with a firm of accountants and management consultants for three years and they'd picked him out for the 'fast track' and put him on a part-time MBA course. We'd met, I guess as you do, at the bar. I was working behind it to earn a bit of extra money, and he came in and ordered a Mojito. I'd never made one before, so he coached me through the process. He tasted it and pronounced it good, and then he had me make another for myself, which he paid for. We chatted for a while, and he asked for my phone number. Then he said he had to go to discuss something with his tutor. I was disappointed when he walked away, even though he smiled back at me and winked.

The next day, he phoned me around lunchtime and asked if I was working that evening. When I said no, he invited me to dinner. I was rather mesmerised by his confidence, his looks and the fact that he had money. He picked me up in a brand-new Golf GTi, which he said was his company car. He took me to a swanky Italian place, and we had a lovely meal. I did almost all the talking; he was good at listening, and I found myself telling him a lot about me, but not learning much about him in return.

Afterwards, we went back to his place 'for coffee'. Unlike the rather squalid student accommodation I was used to, his was a smart apartment in a modern block, about five minutes' drive from the campus. He had some great views over the city, with a private balcony, no less. Instead of coffee, he mixed Mojitos. They were better than the ones I'd made for him, and we stood on the balcony, admiring the lit-up city beneath our feet.

"Did you enjoy this evening?" he asked.

"Very much. A lot better than serving behind the bar in the student union." I smiled.

And then he leaned in and kissed me. I suppose I was half expecting him to do so because I responded without even thinking. He was fit, handsome, sophisticated and a lot better off than I was, so why not?

And I suppose 'why not?' was what I thought when, a little later, we went back inside and he held me, and then started to unzip my dress. He undressed me slowly, with lots of kisses and caresses, and I helped him out of his clothes. He was supremely fit, lean and with firm muscles. I enjoyed running my hands over his smooth skin and feeling the textures and the hard flesh underneath. And talking of hard flesh, when he helped me remove his boxers, he was hard and quite big. He was also hairless - the first, in fact the only guy I've ever known who removed his pubic hair. It made him look more attractive, more powerful.

I liked the look of him naked. I loved that he took his time, with lots of foreplay. I'm quite skin-sensitive, so I really enjoyed the way he ran his fingers and his tongue over some of my less-obvious erogenous zones. I like being licked and stroked on my neck, in the crook of my elbow, behind my knees, the backs of my arms, on my breasts, not just my nipples, and particularly the insides of my thighs. Greg seemed to understand this intuitively, and I just melted.

It never occurred to me to ask him to stop, or for me to call a cab and go home. I wasn't the kind of girl who would fuck on the first date, but with Greg, I felt that I didn't want him to stop and, perversely, that he wouldn't, even if I begged him. By that, I don't mean he would've raped me, or that he was in any way coercive. Everything he did to me, I wanted him to do to me, and I didn't have to verbalise it. But there was this air of authority about him, so that I felt I couldn't refuse him anything, even if I'd wanted to - and I most certainly didn't.

Soon he had his mouth on my nipples and his fingers between my legs. His finger-work was very good, stroking, probing, exploring and teasing, never quite touching my clitoris. And then he slid down the bed and parted my thighs and POW! - his mouth was on my clit and I was about ten seconds away from orgasm. And nine seconds later he stopped and moved his tongue back. He licked my bum-hole, and I almost came then, but then he worked his way forward until he was a centimetre away from my clit, and then drew a circle around it with his tongue.

I was almost howling in frustration. He'd got me so close to orgasm, but he kept teasing me closer and then backing off. I was trying to force my clit into his mouth. He slid a finger up inside me and found my G-spot instantly. Most guys I'd had sex with until then would've needed a satnav to locate it, but not Greg. And then he was doing it again, this time stroking my g-spot while just gently teasing my pussy lips, bringing me close again and then backing off a fraction of a second before I could get there.

When he finally lifted his head, he said "Do you prefer to come first or while you're being fucked?"

I didn't use the f-word much myself. I was twenty years old and I'd had sex with just three guys, all of them pretty unspectacular and rather useless in bed. Greg's assumption that he was going to fuck me, and wasn't at all afraid to say so, sent a little shiver through me. Of course, he was going to fuck me. Of course, that cock was going inside me. I mean, what else was I expecting? It was just that, when he said it out loud, it felt strangely forbidden, a little scary - because I seemed to have no say in the matter - and, perhaps as a result, surprisingly erotic. Other guys had said things like "How do you want it?" Greg was different in so many ways.

I was desperate for release, but sex always feels better for me if I haven't come first. I was in a sort of trance, and all I could say was "Please be gentle. Take it slow. You're - you're so big."

And he is. I guess Greg is the biggest guy I've had. Now I'm used to him, I wouldn't want anyone smaller, but back then, a shy girl who hadn't lost her virginity until she was nearly twenty, I was a bit nervous about having something so big inside me.

("How big is he?" Dolly asked me. "Have you measured his cock?")

"He's around twenty, maybe twenty-two centimetres long, and quite thick. The longest I'd had before was maybe seventeen."

("What's that in real money, dear? I can't do this metric stuff.")

"I guess around eight inches. Maybe eight and a half."

("Ooh, a nice size. My biggest was over ten inches. Quite a whopper. Intimidating, but oh it felt so good!")

Ten inches! Wow! Well, Greg's quite big enough for me. He certainly was that first time. I didn't notice when he'd put the rubber on, but I felt it slide in my slit and my momentary fear that he'd try to go in bareback disappeared. And he'd got me so wet that he slid in more easily than I'd thought he would. There was a bit of resistance - I mean, I hadn't had much sex with anyone up until then - and I was aware of him stretching me. I screwed my eyes up tight and tried not to be frightened that he'd hurt me.

But he just stopped and said, "Gemma, open your eyes and look at me."

Of course, I obeyed. His face is handsome and he had this reassuring smile.

"I'm not going to hurt you, but you're very tight, so I'm going to slide in slowly and stretch you until you're comfortably full. It shouldn't hurt, but let me know if I'm going too fast for you. We're both going to enjoy this a lot. Just look at me and trust me. I know what I'm doing."

And oh my God he did! Oh, Dolly, you talked about Frank and your first few times, and I guess with Greg it was almost like losing my virginity all over again, but a lot better than the first time. He did take it slowly, and yes, I had to stretch quite a lot to accommodate him, but the sensations were good and it was exciting, having such a good-looking and considerate guy between my legs. Most of my other boyfriends had wanted a quick fuck, and although they all tried to make me come in various ways, they didn't always succeed. I could somehow sense that Greg was doing this for my pleasure, trying different moves to find out what I enjoyed.

It turned out that I enjoyed most of what he did. He angled his cock to rub against my G-spot and, given his size, I got a lot of pleasure from that. Then he changed position so that the top surface of his cock pressed on my clit on each stroke, and around then I felt the renewed stirrings of an orgasm. All the while, he was watching my face, occasionally bending to kiss me, or arching his back a little more so he could suck my nipples. He was good. Very good.

And then he did something no other boy had been able to do. He went in deep, all the way. At first, I wasn't sure. There was some contact with my cervix which was on the border of pleasure and pain. But then he somehow changed the angle again, pushed past the cervix and amazingly hit the very end of my vagina, right up against my womb. The sensations then were like nothing else I'd ever felt.

("I know what you mean. I used to love it when a man did that to me. It's not just the physical sensations. There's this sense of being impaled, of being so totally and completely fucked, and the whole world starts to revolve around the rhythm of that regular pulse, each thrust hitting right on that almost-inaccessible pleasure spot. There's nothing like it." Dolly's expression was wistful.)

Yes, now you put it like that, I know exactly what you mean. I don't think I'm particularly submissive, but in that moment, with a fit, powerful man between my legs, holding me down on the bed and thrusting something bigger than I'd ever felt before so deep in my vagina, deeper than I'd ever felt before, I felt possessed; helpless but happy about it. Almost deliriously happy about it. He wasn't taking anything from me; he was giving me something very precious, but somehow forcing me to accept that gift, and I was powerless to resist. Once or twice since then, we've played what I guess you'd call a 'rape fantasy'. Rape's a horrible thing, and I'm not turned on by it at all, but sometimes there's a thrill in feeling coerced into a sexual act where you're pretending you want to resist when you actually want everything that happens to you to happen. When Greg does that, and he thrusts in so deep, it's a bit like that first time.

Anyway, I was getting sensations like never before, and I was definitely on the brink of orgasm when Greg just shifted his weight a little, slipped a hand between us and got his thumb on my clit. I'm sure I would've got there without it, but he just fired off the most incredible sensations and I was jerking around and virtually screaming.

My legs were by now up and around his back so I could feel him as deep as possible inside me. And he whispered, "Do you like how I fuck you, Gemma?" And I was still coming, and all I could say was "Yes! Yes! Yes!"

"Help me get there," he said. "Tell me how you like it."

So I just murmured something like, "Oh yes, I love how your cock goes so deep. It feels fabulous, filling me right up. Fuck me, Greg. Fuck me, please. Fuck me."

It seemed that all Greg needed to get off was a bit of dirty talk from me.

("Oh yes. Men love that," Dolly interjected. I smiled at the almost sisterly rapport we'd developed.)

Now Greg was so big I could feel him pulsing inside me, and he just let out these long moans. And then he was kissing me, and I was hugging him with my arms and legs, and I must have been tripping on hormones because I felt fantastic.

("I used to love it when I was fucked by a man who really knew how to do it. I've had that feeling a good few times in my life, and frankly, you can keep all the drugs and the best champagne. There's no feeling like it, and I'm so glad you have a boyfriend who can do that for you." Dolly's wistful smile lit up her face.)

Afterwards, after he'd got us both some water - I couldn't face any more alcohol - and got rid of the condom, he said "You're beautiful, Gemma, and you're an amazing fuck. You're deliciously tight and I love the way you move and react when I'm moving my cock in your pussy."

I wasn't sure whether to be pleased or shocked. I'd been called beautiful before, mostly by guys who wanted to get inside my knickers - but no one had called me an amazing fuck. I felt that it somehow cheapened the rather transcendental experience that Greg had given me. But then I reflected that what we'd done was to fuck. He wasn't even my boyfriend then. I'd fucked on the first date, something that I'd never done before, and this could be just a one-night stand. Though if it was, it would still be the most memorable fuck of my entire life until then. So I just told him how gorgeous I thought he was, and how clever he was with that big and delightful cock.

We kept kissing and cuddling and stroking each other for a little while, and then he asked "Would you like to try again?" He was lying on his back and I could see that his slightly intimidating but surprisingly attractive cock was hardening, so I put my hand around it and began stroking it. It got harder and even more intimidating, and I couldn't close my hand around it. I knew what I should do - what any boy would want me to do, so I just bent forward and began licking and sucking the tip. There was a slightly salty taste, I guess of pre-cum, but not the rather acrid flavour I'd come to associate with semen. I'd tasted and swallowed enough of the stuff to know that it's not something I'd choose to consume, but I guess he must've cleaned up when he was out of the room disposing of the condom and getting us water.

He was too big for me to suck much of him, but he certainly seemed to be enjoying what I was doing. Then he said "Let me reciprocate. Sit on my face and then carry on with what you're doing."

We moved into a sixty-nine position, and I got more of his excellent tongue work; enough to encourage me to continue with the cock-sucking. He again slipped a finger inside me, and a little later, he probed my bum with another finger. I squealed and said, "No, please, I don't like that."

He just said "Wait a moment. Persevere. You may find you enjoy it more than you realise." And with that, he pushed his finger in, up to the second knuckle. I squealed again, but it was odd. The sensations as he slowly slid his finger in and out felt surprisingly erotic. Perhaps it was the newness and the naughtiness of what he was doing. When guys had tried that before, I'd always stopped them. I felt it was dirty and somehow revolting. With Greg, I was reluctant at first, but combined with the sensations coming from inside my pussy and from my vulva and clitoris, I found it weirdly erotic.

("Has he progressed to sticking his cock up your arse?" Dolly asked.)

No. He's too big.

(She smiled and said "There's no such thing as too big. With the right preparation, some patience and plenty of lube, an arse can accommodate any size of cock. Trust me. I did it a lot, with gents of all sizes. Most of the time, it felt very good." I just smiled and continued).

Anyway, he finally lifted me off his face, removed both his fingers from inside me, and I intuitively knew what we were to do next. As I climbed off him, he reached over to the bedside, retrieved and fitted a condom, and I straddled him and lined his cock up. There was a mirror over the bed, and I watched in amazement as I slowly lowered myself onto that big cock. This time, I knew it would fit and that it would feel good, so I guess I was less tense and he slid all the way in, straight away. And then I was riding him, controlling the angle and depth myself. I would lean back to get maximum g-spot contact, and then move forward so he could suck my nipples as I wiggled my pussy around to get clit contact with the top of his shaft. But the best bit of all was when I started bouncing on that cock, pushing it as deep inside me as it would go, and he got his thumb on my clit and another strong hand over my breast. It was wild and fabulous.

He kept saying things like "Fuck, Gemma, you're so gorgeous. Your pussy's so tight. Go on, fuck me, Gemma, ride my cock with that lovely, tight, wet pussy. Tell me how you like my cock. Tell me how it feels."

That's when I came, gasping things like "Oh God it's so big, so deep. God, your cock's filling me up so much!" It was all total crap, but at the time, we both enjoyed it. Greg started coming even before I'd stopped.

He drove me back to uni the next morning and promised to call. I'd had boyfriends before who'd said they'd call and never did, but I got two texts from him during the day, saying how much he'd enjoyed our night together and how he'd like to do it again. He called that evening, we had another date that ended in some more very hot sex. Three weeks later, I moved in with him. And we've been together for over four years.

("Is the sex still as good?" Dolly asked. I considered her question for a moment, remembering how Greg and I had fucked after my first session with Dolly.)

Yes. It's not always as wild and exciting, but it's still good. Now it's usually more loving and less frantic, except when one of us gets particularly randy for some reason and suggests or tries something new.

("But there's still nothing quite like the thrill of getting fucked for the first time by a skilful new lover. Especially one with a big cock, eh?")

Dolly, you're incorrigible. Yes, I guess you're right. But I've told you my story, or at least the most interesting bit; how it all started. So are you going to tell me more about yourself?