An Old Flame scratches an Old Itch

This all happened last month. If you don’t care about the background, head down to the XXX line for when the sex actually starts.

A little background on the key players (with names and jobs changed a little to keep things anonymous).

I’m Dan; my best quality is broad shoulders. I’m in my late thirties, I was a slow starter in dating, and hugely regret not having more fun in my twenties. I have an average length, girthy cock, which I shave when I remember (and it was shaved for this).

Maggie is my ex; she’s a private healthcare worker, and we dated about 10 years or so. She’s 20 years older than me, didn’t look it at the time, and somehow hasn’t aged since (she looks younger than me). She’s a fairly short redhead, has absolutely *huge* boobs (38DD), and looks like a cross between Darla Crane and Demi Dean.

NSFW reference pics, if you‘re interested:

[https://www.google.com/imgres?imgurl=http%3A%2F%2Fi.imgur.com%2Fh82iCFD.jpg&imgrefurl=https%3A%2F%2Fwww.reddit.com%2Fr%2FAgedBeauty%2Fcomments%2Fahn3j6%2Fdarla_crane%2F&tbnid=958Vr3wZG0uEYM&vet=12ahUKEwjCjdX3-IvzAhVHaBoKHSfKBDgQMygLegUIARCVAQ..i&docid=ZkFTykrSuFTGDM&w=800&h=1200&q=darla%20crane%20imgur&ved=2ahUKEwjCjdX3-IvzAhVHaBoKHSfKBDgQMygLegUIARCVAQ](https://www.google.com/imgres?imgurl=http%3A%2F%2Fi.imgur.com%2Fh82iCFD.jpg&imgrefurl=https%3A%2F%2Fwww.reddit.com%2Fr%2FAgedBeauty%2Fcomments%2Fahn3j6%2Fdarla_crane%2F&tbnid=958Vr3wZG0uEYM&vet=12ahUKEwjCjdX3-IvzAhVHaBoKHSfKBDgQMygLegUIARCVAQ..i&docid=ZkFTykrSuFTGDM&w=800&h=1200&q=darla%20crane%20imgur&ved=2ahUKEwjCjdX3-IvzAhVHaBoKHSfKBDgQMygLegUIARCVAQ)

[https://www.google.com/imgres?imgurl=https%3A%2F%2Fpbs.twimg.com%2Fmedia%2FCvJvCG1WYAA1VZx.jpg&imgrefurl=https%3A%2F%2Ftwitter.com%2Fdemideanmilf&tbnid=_70qgxVjOKH5_M&vet=12ahUKEwj0-8q3-YvzAhUIBRoKHXaKB2sQMygJegUIARCNAQ..i&docid=sH6_Jzq4uSCNwM&w=400&h=522&q=demi%20dean%20xxx&ved=2ahUKEwj0-8q3-YvzAhUIBRoKHXaKB2sQMygJegUIARCNAQ](https://www.google.com/imgres?imgurl=https%3A%2F%2Fpbs.twimg.com%2Fmedia%2FCvJvCG1WYAA1VZx.jpg&imgrefurl=https%3A%2F%2Ftwitter.com%2Fdemideanmilf&tbnid=_70qgxVjOKH5_M&vet=12ahUKEwj0-8q3-YvzAhUIBRoKHXaKB2sQMygJegUIARCNAQ..i&docid=sH6_Jzq4uSCNwM&w=400&h=522&q=demi%20dean%20xxx&ved=2ahUKEwj0-8q3-YvzAhUIBRoKHXaKB2sQMygJegUIARCNAQ)

She’s the best kisser I’ve ever dated – firm, but a bit sloppy – but we didn’t actually have sex when we were dating; she had a bit of a hangup as she didn’t want to sleep with anyone unless it was a serious relationship, and the more time went on the more it became clear we weren’t going to work out. We dated for a few months, broke up, stayed friends, and went on to see other people, although she was single at the point that everything below happened. I had no intention of ever dating her again, but can’t deny I still think she’s very, very attractive.

Cathy is my next ex; she isn’t relevant to the story, other than background! We were in a serious, long-term relationship (engaged, house, and all) for about five years, but broke up a few months ago. She had a completely different body type than I’d usually go for; slim, small perky tits (C-cup, technically, but felt smaller). This isn’t r/relationships, so I’m not going to go into the breakup, other than to say (a) it was slow and sad, and (b) it means that we’re talking a few months without sex, and years since I’d fondled a set of nice, massive tits. Even though we *were* trying to save the relationship – I had an idea of exactly what I wanted to do, *if* the relationship failed.

The relationship failed.

Over the next week I moved my stuff out, and needed to make an appointment to see Maggie (genuinely!). I made it the last appointment of the night, and as the date of seeing her approached, I wondered if I should make a move or not; as I got into the car to drive over, I decided. Game on.

The appointment panned out as it always did; chatting between us as friends, while she works – and I told her that we’d broken up fairly early on into the appointment, so we had most of the hour knowing that I was now single.

She asked what it meant for me, and I said that I wanted to enjoy being single; I’d spent too much time looking for “the right person” and not enough just having fun. I also asked how her dating life was – I knew she’d been focussing on one of her hobbies in favour of dating, how was it working out? Just small, inane chat, but also establishing that both of us were single.

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Once she was done, I pulled on my shirt and looked at her; I figured that if there was going to be a moment, this was it. I lifted her chin slightly, and kissed her – nice and slow, open mouths, our tongues finding each other. After a few seconds – 5? 10? She pushed my chest slightly, and took a step back; she looked off to one side for a second, looked back at me, and nodded. “Okay. Okay, let’s do this.”

I stepped forward – maybe we both did – and we grabbed each other, kissing more firmly. I had my hand in her hair, and closed it into a fist, tugging ever so slightly; one of her hands was on the back of my neck, and I’m pretty sure I could feel her nails, just digging in slightly. I ran my other hand up and down her back, trying to look like I was being sensual, but in truth, trying to work out how her uniform came off; I couldn’t work it out so moved my hands down to squeeze her ass, instead.

After playing with it for a bit, I took a step back, and unbuttoned my shirt looking at her all the time; I thought she might start taking off her clothes, but instead, she bit her lip, and started pulling at my belt.

With her previous hangup, I wondered what we’d be doing – I thought she might be a bit prudish, and that we’d end up having acceptable sex in the missionary position (which would be fine, but not the stuff of my fantasies). Instead, she pulled my trousers down to my knees, took my balls in her right hand and took my cock in her mouth, pushing it right to the back of her throat. I steadied myself on the table behind me as she slid her head up and down, the blowjob every bit as sloppy as her kisses. She held onto my ass with her left hand, not gently, her nails digging into my right cheek.

I’ve honestly never had a blowjob like it in my life; I leaned back and enjoyed it for a while, and a bit of me wanted to stay like this until I came. But I’d fantasised about her for the best part of a decade, and I wanted to do *everything*. I took a hold of her hair, and gently pulled her upright.

“I want you to take your top off.”

I pulled my shoes off with my feet, then bent over and pushed my trousers off completely, and watched her undo her top, leaving her in black leggings and a black lacy bra – her tits looked amazing. I stepped forward, now totally naked, and kissed her again, grabbing a handful of each asscheek and my cock pressing up against her stomach.

I’m fairly strong, and she’s fairly short, so I squatted down slightly, slid my hands down from her ass to her thighs, and lifted her up – she gasped – and I turned around and sat her down on the table behind me. I leaned forward and kissed her, her tongue moving against mine again, then kissed her neck, down her chest, and down her stomach – I pulled her leggings down, exposing her black lacy panties. To get her tights off, I had to step back and lift her legs upright – I held her legs up even after I’d got her tights off, and kissed the back of her knees, then her thighs, and finally pushed my face into her asscheek and kissed her there too while I slid my finger under her panties and pulled them out the way.

I moved back towards her pussy – it was trimmed, but not shaved – and I locked eyes with her as I slid my tongue in, and as I licked upwards, and found her clit, I slid a finger inside her for good measure. I played with her for a while – licking and flicking with my tongue, and sliding my middle finger in and out slowly, all while she moaned and ran her hands across my head. She stopped looking at me and leaned up while I carried on, and I moved my left hand up so I could squeeze her tit, glad she was short enough that I could reach – her rack was amazing, and I didn’t want to miss out on a bit of it – then brought my arm back down and held onto her thigh for balance, still licking and flicking with my tongue but never changing the speed of my finger going in and out.

Maggie looked down at me, and said “I want you inside me”. I took a step back, and she herself slid off the table; I turned her around, and bent her over, pulling her panties down around her thighs. I quickly and quietly spat into my hand, and rubbed it over my cock – I swear, it has never looked so big – and guided it into her. I wiped my hand on my leg, then held onto her waist with both hands, and started fucking, slowly at first to gauge the angle, then faster and harder. We both started grunting, and any pretence of lovemaking was gone, I pumped as hard as I could and she pushed back into me. I reached up to her bra, and managed to unclasp it with one hand (with a bit of effort). She pushed herself up a bit with her hands, her bra open at the back but still being held on with the straps; I brushed the straps off her shoulders and down her arms, it didn’t come right off but it was enough to release her *magnificent* tits. I grabbed her waist with my left hand again and carried on pumping, then reached forward with my right hand and held her right tit while I fucked her.

I took a moment to appreciate that I was finally fucking this girl I’d never quite got over, massive tit in one hand and hearing her moans echo round her room, but realised I was closer to cumming than I’d like, so I pulled out – probably a bit too quickly, but I didn’t want to finish yet – and dropped to me knees, slipping my middle finger into her pussy and rubbing her clit, kissing and nibbling her ass, hoping to make her come as I didn’t think I’d last long enough if we started fucking again. Luckily, we found our rhythm, and she gasped and came, and I felt her splash onto my hand (holy shit, I’ve never had that happen before). She moaned and gasped a little more while she caught her breath, and I (successfully) tried not to punch the air.

I stood up straight, and she pushed herself upright, breathing heavily; I reached around and put one hand on her stomach, one hand over one of her tits, and whispered in her ear “Will the table take both our weight? I’m not done yet.” She nodded, but didn’t say anything; I hopped up, sitting on the edge, then helped her clamber up. It wasn’t very dignified, and she snorted with a laugh (goddamn, it’s a sexy laugh) and said “Oh, god”, as she went back to being slightly embarrassed by what we were doing. She looked me in the eyes, and started giving me a handjob, and the smile changed, as we got ready for round two, which I realised would not last long.

I whispered “I want inside you” – and Maggie whispered back “okay”. I swung my legs up and she changed her position to straddle me; she guided me inside her and sat her weight down on me, both of us muttering “Oh, God” at the same time. She leant forward with her right hand next to my head, and I realised I must have unleashed her inner cougar – she had no embarrassment at all as she fed me her massive left tit. I started sucking on it as she started to ride me, and I gave both her tits a final, slow fondle, then ran my hands down to her waist, and crossed my arms behind her back, puller her closer to me so those tits were squeezed into my face and I started to thrust upwards into her.

The angle was a little awkward, so she moved backwards down the table slightly so I was looking straight into her face; I pulled her back in close so our heads were next to each other, and thrust into her again, speeding up quickly.

Like the hard fucking before, we didn’t moan slowly or gently, we just grunted as we fucked as hard as we could, but this time her mouth was next to my ear and it being so much louder and those massive tits being squeezed into me pushed me over the edge, and with a massive “oh, Christ, Maggie” I came harder than I ever have before. She did let out a gasp/moan thing, but I don’t think she actually came that second time, I think she was surprised by me exploding below her.

She lay on top of me, with me deflating inside her; we were both physically twitching while we caught our breath.

“I have to move”, she whispered, and rolled off; I could see her dribbling onto her table as she moved.

“Jesus – that was amazing” I whispered to her.

“Yeah” – she whispered back.

We got dressed, and I helped her clean up a bit; we kept telling each other that we’d been amazing, and said we’d talk later. I don’t know if we’re going to see each other again, as a casual thing, or if it’s just been an itch scratched for us. It certainly was for me.

Source: reddit.com/r/gonewildstories/comments/prjcw4/an_old_flame_scratches_an_old_itch