Old Flame Anal

We'd known each other since junior school, went through high school together and college where we started dating, although at the time we kept it relatively quite, or I did as she was a bit of a nerd. Besides experimenting sexually with my best friend Lyndsey was with who I lost my virginity, back then though she was limited as to would she would do. No blow jobs or licking her out just straight up missionary sex.

We both started university together and that's when things got awkward between us. We split up and didn't really talk to each other afterwards. I always felt bad how I treated her after that, she deserved better.

Move forward twenty years and we've both got our own lives, both got married and not heard from one another until suddenly out of the blue I got message. We messaged each other for a while before arranging to meet up one lunchtime. I was working near her office so we grabbed a coffee and had a catch up, it felt like we'd never lost touch.

We met up again, this time for lunch after which I walked her back to the office through the churchyard where we sat and kissed before going our separate ways. We met a few times like that and had a fumble with one another until one time we arranged to meet at her house when she was working from home.

On that day I walked up to her house, rang the bell and waited. The door opened and I looked at her, she looked beautiful, as soon as the door closed we starting kissing and headed for the lounge. We sat down and started cuddling, her hands wandered and she took off my clothes until I was sat naked on the couch. Lyndsey leaned into my lap and I felt her lips around my cock as she slid them down my length and started to suck me off. 'Wow, she's changed over the years' I thought. It had been a long time but she would never let me put my cock anywhere near mouth when we dating. Lyndsey continued to suck me as I moaned getting closer and closer to orgasm but it never coming then she removed my cock from her mouth and said "you'd better get going as I've got work to do." I was somewhat taken aback by her bluntness but knew she was meant to be working so dressed and left. On the way home I received a text saying how much she'd enjoyed seeing me and that we should do it again.

We met up regularly after that, either for lunch near her office, or at her home when she was working there. Every time we met up at her house we ended up in the bedroom and had sex. Every time I drove there my cock was stiff by the time I got there in anticipation of what was to happen.

Lyndsey was rather hairy downstairs, I didn't mind for sexual intercourse or for fingering but I didn't really fancy a mouthful of hairy muff so I let it be known that I like a nice shaven pussy if she wanted to be licked out which I wanted to do to her.

On this particular occasion I rang the doorbell and the door opened. Lyndsey hid behind the door as I walked in and closed the door behind me. There to my surprise she stood wearing a sexy negligee and nothing else. She looked sexy as hell. I stood and looked at her, the negligee barely covering her as I moved in and kissed her passionately and grabbed a handful of her perfect, plump ass. My hand explored her body and moved round to the front where I was surprised again, this time to feel her freshly shaved. She felt so smooth, so sexy and extremely juicy as I touched her and rubbed her pussy.

Lyndsey led me upstairs, I always enjoyed walking up the stairs behind her and admiring her ass, it always looked so good in tight jeans but it was perfection now that it was right on show as I was led upstairs. Once in the bedroom Lyndsey lay down and I looked at her as I stripped off, my cock standing fully erect as I lay beside her. I pulled up her negligee and looked at her pussy which looked amazing, she'd done a fantastic job of shaving and I moved my hand between her legs and felt her wet pussy. The feel of how smooth and juicy she was sent shivers through me and felt so good as I continued to feel her on my fingers. As I rubbed her clit Lyndsey's moans got louder and louder, the look of sheer enjoyment on her face was turning me on and making me want to satisfy her even more as I made her orgasm again and again. With Lyndsey's pussy now feeling sodden I slid two then three fingers inside her and pushed them knuckle deep as I fingered her as deep as my fingers would go.

After a while Lyndsey said "lick me, I want you to taste me on your tongue." I pulled my fingers out and positioned my body between her legs with my face inches from her. Being this close her pussy looked magnificent, so naked, so smooth, so juicy. I touched her pussy with my hand, wiping away some of her juices before I moved my face closer, extended my tongue and started licking. She felt smooth on my tongue and tasted so good, I pulled her legs right apart and pushed my face deep between them forcing my tongue right inside her as I licked her out deep. Lyndsey was enjoying this "oh yes that's good, why has no one done this to me before?" she said as she pushed her pussy into my face and started to grind on my tongue. I got even more turned on by how much she was enjoying it and by the fact I was the first person to do this to her. As she grinded herself on my face the taste in my mouth got stronger and wetter as Lyndsey clamped her thighs together, my head still between them and my tongue still inside her pussy as she moaned loudly and climaxed in my mouth. This turned me on immensely, she was being so sexy, she had turned into a sex monster and I loved every second of it.

Once she'd finished her orgasm and unclamped my head from between her thighs she said "I want you inside me, fuck me!" I was so turned on I would've done anything, but this I was going to do anyway. "Get on your knees" I said as she rolled over and knelt on the bed her ass pointing up at me. Lyndsey had a perfect ass I'd always admired and on several occasions I'd said about anal sex but she was never interested. I wasn't going to force anal on her but I often fantasied of fucking her ass.

I moved up behind her with my cock in hand and slid it easily inside her warm, wet, welcoming pussy. I don't know what it was but something felt just so right every time I was inside her, it felt like I fit inside perfectly, weirdly it felt like I was meant to be in there, I grabbed hold of her hips and started to fuck. I needn't be slow or gentle given how juicy and horny she was so I fucked her deep and hard ramming my cock into her as my balls slapped her arse. I loved it doggy style, again Lyndsey hadn't done it this way before we met again, her sex life must have been quite boring only having it missionary and not being licked out. I enjoyed opening her mind to new things and being the first at doing so, we both loved what we did to each other and got immense pleasure from satisfying one another.

I slammed into her fucking her deep and hard, both of us were moaning loudly and I'd be surprised if her neighbours couldn't hear, especially as it was a terraced property. As much as I wanted to and as close as I was to doing so I didn't want to cum in her yet, not that hole anyway given the chance. I slowed my down and sucked my index finger making sure I covered it completely with saliva. With my cock deep inside her pussy I moved my hand towards Lyndsey's ass and gently started to push my saliva covered finger inside her tight hole. As my finger slid in past the nail, then halfway and then knuckle deep Lyndsey's body stiffened in surprise, "what are you doing?" she asked. "Ummm, I thought you might like it." I replied. "It actually feels OK" she said as I held my finger inside her ass and continued to fuck her pussy.

With my cock sliding in and out of her pussy I started to finger her ass. I pulled my finger back and forth and each time her ass felt looser and looser. Lyndsey was obviously enjoying this and my finger now slid in and out with ease so much so that I spat on her asshole and pushed a second finger inside. This finger was a squeeze, it felt tight going in and I felt her ass stretch around my fingers. Once I had both fingers deep inside I kept them there and moved them round, wriggling inside her ass to get her used to it and try to loosen her hole. With two fingers inside I felt pleased with what I'd accomplished, not only was she sexy and smooth just for me she was now willingly letting me finger her ass which I'd never previously been allowed anywhere near. With my fingers in her ass I could feel my cock sliding back and forth in and out of her pussy and it felt very horny. If it felt like that to me imagine what it would feel like being on the receiving end! Lyndsey was on the receiving end and from her moans I could tell she was enjoying it, so much so she even let me do what I'd been hoping for and wanted for a long time when she said "fuck my ass." Hearing her say that, the way she did with such filth in her voice I was lucky I didn't cum in her pussy right then.

I removed my fingers from Lyndsey's ass and slid my cock out of her pussy trying to cover my cock in as much of her juice as possible as I did so. Once I'd removed my cock I wiped my fingers across her pussy before I rubbed her juices around her puckered ass hole.

I looked down and nudged of my bell end against Lyndsey's asshole and eased the tip of my cock inside. I felt her ass stretch as I eased myself inside her until her ass had swallowed up my bell end and I was pushing the length of my cock inside. Lyndsey stayed stiff and quiet as I continued to push myself into her virgin ass until eventually I was balls deep. She felt so fresh and so tight around my cock, it felt incredible. I held my cock inside her and said "does that feel OK?" "Yes, just get on with it" she replied.

My cock was much bigger that the two fingers it had replaced and I slowly started to pull back and push forward trying to get Lyndsey used to the size of me in her and stretch her asshole at the same time. After a while my cock started to slide in and out easier and easier and Lyndsey started to moan with pleasure as opposed to what previously sounded like moans of uncertainty. As she became looser and my cock slid in and out easier I started to get harder and faster with every stroke until eventually to my surprise Lyndsey herself begged me to do it harder. "Fuck my arse, fuck it hard!" she said. This turned me on immensely, especially as she was so against anal and was now begging for it. I didn't want to be too hard though as it was her first time but I did grab hold of her hips and pull her back onto my cock as I pushed into her fucking her even deeper. Lyndsey let out a shrill and said "oh yes, like that!" so I continued to pull her back onto me with every thrust as I fucked her deep until I pulled her back and kept her there as I continued to thrust into her fucking her ass as deep as possible. Lyndsey's moans got louder and louder as she got closer to orgasm until she let out an almighty scream, pushed her ass back onto me and held herself there impaled with my cock as deep as possible inside her. As she screamed I felt her hole body shudder and her ass muscles contract around my cock almost wanking me off in her ass, I let out a loud moan and came deep inside her.

After that time Lyndsey has remained clean shaven downstairs and has various negligees and sexy underwear sets in which she usually answers the door. She now also nearly always wants me to fuck her ass.