This is the first part of an ongoing discovery of anal sex for me. Can't promise it will be hugely exciting and unfortunately I'm quite wordy so it will be long!!!

This is probably quite boring in comparison to some of the exploits I have read on here. So I'm 51 and up to now a had a very active but I guess "Vanilla" sex life. I hadn't had any sexual encounters for 4 years prior this due to health etc. I've never had anal sex - the nearest i came to it was when a then girlfriend tried to stick her finger up my ass during a blow job and i freaked out! I have tried a few toys and vibrators on myself and been a little MEH! Until I met a local girl on an internet dating site. From the onset she was very sexual and within a couple of days chatting she asked if I would be up for her pegging me. This is something I had toyed with in my head over the past few years, watched lots of videos, bought myself a few anal dildos but never really imagined i would ever explore any further. Over the next the few days we explored other fantasies and I finally admitted to one that I had never dared to admit even to myself. That I would to love to know what it would feel like to suck a cock and be fucked with a real cock. This sent her into raptures and we discussed at length how this could play out with her involved. During the conversation of fantasies I asked her if she would shave my bits - more of as dare. We had swapped pics and videos - something I had never done before so even that felt quite liberating. She sent me a video of he using her dildo and apologised for her "unkept" appearance. She went on to say she wouldn't shave her pussy until she was ready to sleep with me. In my 51 years i have never actually seen a woman masturbate - suffice to say i watched it a few times, I don't think I have wanked myself so much as I did in those initial 2 weeks!

We eventually agreed to meet a week later. We rented an Air BnB for the night somewhere in Cornwall. On the actual day it was all a little awkward as we had never met in person. I find it odd meeting someone I have seen pics and videos of before meeting them! I had bought some toys and lube off the internet in preparation but honestly had no idea how the afternoon and evening might progress. To be fair, I will call her Claire, wasn't really my type physically, but she had piqued my interest via messaging and although a larger girl had a very attractive figure, but on the drive to the cottage we chatted and seemed to get on and have some sort of connection. It is strange meeting somebody for the first time in person after you have been so intimate via texts!

We arrived at the cottage which was stunning and settled in. We cracked open the beers and wine and chit chatted. I decided I needed a shower and just in case i paid careful attention to my ass more in hope than anticipation. I was massively aroused purely because of how graphic and intimate we had been via text and how almost desperate she was to peg a guy. My fascination with being pegged was the idea of someone having control over me. Apparently it had been a fantasy of hers for years but every guy up to now was thoroughly repulsed at the idea. I thought id chance my luck and put by boxers on and wrapped myself in a towel and came out of the bathroom, grabbed a beer and sat back on the sofa next to Claire. She didn't seem fazed by this or turned off - I'm fairly skinny where as I would describe her as voluptuous. We carried on chatting, at which point I thought to heck with it and asked if she was actually going to shave me or was it BS. Her response was "grab the razor!!" At that point her phone rang which was her daughter, checking up on her. I scooted behind her on the sofa with my legs either side of her, it was obvious I was aroused as it was pushing against her back. I reached inside my towel and boxers and started stroking myself, i grabbed her free hand and placed it on my cock. She immediately started to wank me off, part of me thought Id come there and then as I hadn't been touched by anyone in nearly 4 years! She continued her phone call and i reached forward and under her shirt feeling her breasts through her bra. I managed to get my hand inside and tweaked her nipple making her gasp all the while she was still on the phone. Whilst I pinched and twisted her nipple i reached with my other hand and unbuttoned the top of her jeans and the the zip. I probed further and felt her panties . I pulled them aside, and discovered that despite what she said in our previous texts she had shaved completely. I found her lips and gently pushed a finger into her. She physically gasped, still on the phone and closed her legs tight trapping my hand, all the time still gently wanking my cock. I was in ecstasy, a woman rubbing my cock whilst i was actually touching pussy, I withdrew my hand and tasted my finger, she tasted define and so wet. She hung up her phone call and turned to face me and began wanking me faster, i unbuttoned her blouse and pulled one of her tits out. At that point she asked if I liked them? She had them done a few years ago, they were fantastic, pert and just the right size. I managed to lean forward and take a nipple in my mouth provoking another gasp whilst desperately trying to get my hand back in her jeans. With that she pulled the towel open and freed my cock from my pants and took my whole cock in her mouth. It felt utterly amazing and as he slid up and down flicking the end with her tongue I was in serious danger of blowing my load. And then suddenly she pulled back, straightened her clothes, i I thought I had blown it.

She then demanded i got the shaving gear out. I admit I was a little embarrassed, I was rock hard and it was obvious and in just a towel and she was fully dressed. I dutifully retrieved the razor, foam and a bowel of water. I was told to remove the towel and pants and lay back on the sofa. This was new territory for me, not in control, naked, aroused with a woman about to shave my bits. She lathered up by balls and then my ass. I was torn between hugely turned on and a little embarrassed. And with that she starting shaving me, grabbing my cock moving it this way and the other. It felt amazing, sexy, vulnerable. Weirdly we made idle chit chat while she brazenly was doing the most intimate thing i had ever experienced. The razor was shit and after a change of blade and having done about half of it I lost my bottle and said i needed a beer. I towelled myself off and thought what the hell and stayed naked. I was now hairless on my balls and groin!! So we went back to sitting on the sofa chatting, me completely stark naked. We kissed a lot, i fondled her tits i managed to get her jeans completely undone and started to finger her. God this girl got wet but as soon as she seemed to start enjoying it she pulled back. She demanded that she wanted to finish shaving me to win the bet and demanded i lay back down. it felt amazing her lathering up my ass and it was obvious i was enjoying it. At this point I mentioned I had bought some toys with me. She raised her eyebrows and asked if I was expecting something to happen which I just replied "ever hopeful". She asked to see what I had - a selection of beginners butt plugs and a double ended strap on. She picked each one up and studied intently and then asked who they were for to which i replied I hadn't thought that far forward. She demanded i lay back down as she hadn't finished my trim which i dutifully did. I could feel her finger probing round my ass as she finished shaving, once or twice I prayed she would slide a finger in but up to now no luck. She suddenly announced she was finished and began rinsing me off and towelling me dry. I was told to stay still and I suddenly felt something cold and wet on my ass and a gentle pressure as she tried to push something hard in. At that moment I didn't know if i was going to die of excitement or embarrassment but my cock gave me away, I could feel precum leaking out. And then suddenly it was in, no pain just an odd feeling and she started twirling it around inside me. It felt fucking amazing! How's that she asked? I wasn't sure how to answer, did i admit it felt great or admit i felt ashamed for enjoying it? With that I felt her pull it out and very quickly the same pressure at my ass and then in. This time it felt fuller. She was slowly pulling it in and out which felt define. I confess I was terrified I was going to come there and then and also about cleanliness - my biggest fear about anal play was shitting on something or someone. I can not explain how erotic it was to have met this woman who was giving me this pleasure and getting off on it. And then suddenly she pulled it out, a slight uncomfortable feeling as it came out but no biggie and so far no grimaces or explanations about cleanliness! I knew what was coming, the biggest of the three. Once again i felt the lube on my ass and then the pressure and then a little discomfort as it was pushed all the way in. I still cant explain the feeling, the intimacy of someone playing with my ass for the first time ever and apparently enjoying it. I felt full, almost like i needed the loo and incredibly vulnerable with my legs akimbo and erection in front of a virtual stranger! Once it was in she suddenly sat up and poured herself another glass of wine. I wasn't sure what to do but she announced she needed the loo. So i got up and sat back on the sofa. I t was an odd feeling feeling my bum full but every time I moved i felt these pleasurable twinges. Claire came back out and asked how it felt. I admitted it felt amazing and her reply was "it does, i love that feeling" and for the next 20 mins i squirmed around enjoying the pleasure and turned on that I was sat naked in front of a woman who was obviously enjoying the situation. It felt so liberating being with someone so open about sex and what she wanted. We talked more about fantasies, it was erotic having this conversation face to face rather than text and every so often she would place her hand in her blouse and rub a breast or between her legs and squeeze them tight. I was beginning to feel slightly uncomfortable at being so aroused for so long. I was desperate to cum but I don't have the confidence to wank myself in front of someone, Our conversation was getting more explicit and intimate as the alcohol flowed. We were talking about bi sex and how she would love to see me be fucked by a guy and suck his cock whilst she watched. We got so far as looking at escorts on a site. I'm sat there stark naked with a butt plug in looking at male escorts cocks deciding which one we would enjoy and discussing how it would play out. So fucking horny and part of me was screaming "what the fuck is happening, am I gay?". For the first time ever I'm admitting to myself, let alone a third party, that i want to suck a cock whilst someone watches and discussing what it feels like to have a bloke cum in your ass and as my cock gives me away that I'm incredibly turned on at the thought! At 51 I have never even watched porn with anyone, now I'm shopping for cock and she just wants to watch because she is horny at the thought of watching me get fucked. Not interested in watching me fuck a female Its hard to explain how hot that is to find someone who would indulge in that fantasy let alone be so up for it. I confess at that point I had no intention of ever pursuing it, it was vaguely exciting but having never touched another cock it was equally repulsive but i could she was getting flushed at the idea. Its also quite terrifying seeing the size of guy's cocks and thinking that must hurt!!! And the thought of swallowing cum is disgusting, i have at points tried mine and i take my hat of to the women have swallowed my load! At which point Claire, bless her, tells me I'm well endowed. To be fair I've four years of pent up frustration, a butt plug that is sending wave of pleasure every time i move and a woman sat next to me that would seem nothing is taboo!!!! I don't think my cock has ever been so hard or leaked so much. To this day this is one of the, admittedly many, memories of her that turn me on.

Without warning she asked if she could fuck my ass? i thought this was BS so I was like yeah right! She told me to lay down on the sofa. She grabbed the cock part of the strap on, knelt on the floor beside my groin. She pushed my legs as far apart as they would go and pulled the butt plug out. and placed it aside .At this point I admit I nearly bailed, I wasn't sure if I wanted this or the emotions afterwards. Without saying anything she squirted some lube on her hand and before i knew what was happening i felt her push a finger inside me, it actually hurt a little from her nail and then she began exploring and fucking me with her finger. OMG! This was everything I had ever dreamed off, all thoughts of shyness and embarrassment gone. I found myself pushing against her finger wanting it further in, then the same little pain and i can feel a second finger, i can actually feel my ass being stretched by her fingers. I'm pushing down to get her in as far as possible She fucked my ass, twirling her fingers, touching nerves i didn't know existed. I feel this feeling of pleasure growing in my groin that I have never felt before and I'm all in. And then suddenly it stops and she has pulled her fingers out. I open my eyes and can see her lubing up the strap on cock. She's not wearing it, its in her hands. It looks huge - at least 7 inches and twice the girth of the last butt plug. "Are you ready? I'm going to fuck you hard" Again that pressure on my bum but it wont go any further, i feel her remove it and apply more lube. This time more pressure and then it hurts but its in. Fuck me it feels huge. She slowly moves it in and out and I confess its uncomfortable Not sure I'm enjoying this - the feeling is akin to needing a shit! But slowly it becomes easier and i can feel it going deeper and deeper. The weird thing is I can hear her breathing hard, hear her muttering how fucking hot this is. She is actually getting off on fucking me. And the feeling is for me completely new. I've fucked myself with dildos it never felt like this, always a little unfulfilled and dirty I'm gasping asking her to fuck me harder, telling her how good it feels - I'm never vocal and then suddenly I feel her take my cock in her mouth. She doesn't move her head just takes my entire length and gently sucks whilst fucking my ass. I can feel something building, I feel like I'm cumming but the feeling just keeps building and building and she is now ramming this impossibly big, to me, dildo in my ass to the hilt and suddenly I feel this orgasm was over me, this explosion, it felt like Id pass out. I shoot my entire load in her mouth and she is till fucking my ass until I have to ask her to stop because I'm literally shaking. She has swallowed every drop of my cum and has that look in her eyes of being massively turned on. She sits up and just smiles at me and says that was fucking hot, I'm so wet. I'm a little embarrassed because i made such a racket, i just cum in this girls mouth who i only met for real a few hours back, I've just been fucked in the ass and loved it and she's still fully dressed! I got up and went to the bathroom, lets slightly bowed and still shaking and pulled the dildo out which was a little uncomfortable. Glad to report no cleanliness reports. Now, in the past when I cum I confess I just want to lay back and sleep. This time different. I read years ago that when blokes cum its not an orgasm and I was like Meh! Now I know. I had shaky legs and balls and an ass that to me that felt gaping and a woman still dressed....

So, the evening did continue and became one of my most memorable sexual encounters. If you want to hear the next part let me know and if I've bored you, sorry