How I Lost My Anal Virginity Pt. 01

Hello there, I thought you might enjoy this little tale of how I lost my anal virginity.

It all happened a few years ago with a pal, Rob. We were living in a block of flats and he was another resident. We had a few interests in common, so got along well and always had something to talk about.

But there was another factor that kind of interested me about him -- he was a 'bachelor', as we called them then. I often wondered about his sexuality? Was he hetro, gay, asexual? We never said anything on the topic, but I did wonder...

Now, before I go on, I should say that it wasn't strictly true that I was going to lose my anal virginity, for I'd stuck quite a few things up my ass in the previous years. I don't know where it started. I just suddenly thought one day that I wondered what it would be like to have something shoved up my ass?

Now, you're going to think that this first bit of my story is a bit tame, but bear with me...I started, as you do, with my fingers, but really couldn't get much sensation. Then, my wife was away for a few days and I thought, I've got to try something else. I didn't really fancy bananas or cucumbers, too rough, I thought.

A candle! We had some nice table candles, a convenient nine inches long. I tried that, the sensation was good, but too smooth and not fat enough, I felt I needed stretched out more. Then, I had a bright idea! I got some sheets of kitchen towel, wrapped them round the candle and put a condom over the lot.

Up it went. Wow! That was good. I fucked myself quite regularly with that for some time before getting hold of some proper dongs.

It's a great sensation having something up your ass. It's quite different from any genital play. But when I was doing it, I was always thinking that it would be sooo good to have a real live, hot, throbbing cock up there.

Anyway, I digress, a bit...back to Rob. This happened another time my wife was away. He'd been in our flat for coffee, so knew my wife was going on a trip for a week. 'Why don't you come over for supper one night?'

I turned up on the appointed evening and we had a very nice plate of spaghetti bolognese, quite a good cook Rob. He cleared the plates away and said there was dessert. He went over to the kitchen area and fussed about with plates and things.

I was looking straight at his ass and thought to myself he was wearing unusually tight track-suit bottoms, as his bum was really prominent. You could clearly see his crack. I noticed that he put his hand in his pocket, but thought nothing of it. He turned round and walked back to the table with the plates in his hands.

Immediately I saw that he had a big hard-on!

There was no mistaking it, it was sticking up at like forty-five degrees in his stretchy trackies -- a kind of long hard ridge. Could only be one thing.

It just came out of me, 'Rob, you dirty bugger, you've got a huge hard-on!' By this time he was just a foot from me, still holding the plates.

'Want to see it?' he said, grinning and putting the plates down.

In a second, he reached down, undid the cord and just pushed the trackies down. As he pushed them down, his big cock just popped out! He wasn't wearing underwear either. A lovely sight as his prick bounced up and down. He got his hand round it and give it a few twitches.

'Want to feel it?' Well, I was embarrassed at first, then I thought about how often I had dreamed about getting hold of a guy's cock. I nodded and reached forward to hold it.

It was everything I'd thought it would be, a lovely warm, hard but soft, springy feel. Rob had a good sized cock, not that big, just over six inches but fat. I rubbed my hand up and down it and really enjoyed the warmth.

While I was doing this, I didn't realise it, but Rob had edged forward and his cock was now only three or four inches from my face. Well, you know what happened next, without really thinking I just leaned forward...and took it in my mouth! It was lovely, all I had ever expected.

God, I gave it a real good sucking. The way it filled my mouth was just beautiful. Rob had a good long foreskin so I worked my tongue round that, then his foreskin sort of popped back and I got his full bulb in my mouth.

I took the whole thing in as far as I could, but with no experience of this I gagged if I got more than about three inches in my mouth. I sucked away. And, by the way, got my hand on his balls and felt them. They were big. I could feel my own cock getting uncomfortably hard as it expanded.

'Want to do something else?' I heard from above me.

'If you keep sucking me like that for much longer I'll shoot my load.'

Well, I was getting up to speed by now and knew exactly what he meant by that. I was beginning to realise that Rob had been at this before... I let his cock slip out of my mouth, looked up and said 'Yes, but how will we do it?'

'Easy,' he said, 'right here on the table. Just lie on your back. Here, put your feet on these two chairs.'

That was fine, but first I had to get my trousers off. That, I have to tell you, was going to be embarrassing. Nothing for it, I undid my belt and flies, pushed down my trousers, to reveal the pair of bright, fuchsia pink, tiny, woman's lace thongs I was wearing!

Did I mentioned earlier that I had a bit of a women's knicker fetish? No, I didn't think I had. I'll go back to that later, if I remember, but for now I started wearing female knickers or panties a few years ago.

I particularly like lacy thongs...love the way the fabric rubbed up against my arse crack and cheeks as I walked. Still do. Anyway, with my wife away I was wearing them all week in any case, so thought it would give me just a little extra sexual thrill if I wore them to Rob's. Not expecting what happened to happen.

As I pushed them down, Rob's eyes popped out.

'Oh, so who's the dirty bugger now?' he exclaimed. 'I thought there was a bit more going on with you than it seemed.'

Well, I could hardly say that they were the only pair of knickers I could find, could I, so I just had to look a bit sheepish, 'They're very comfortable.' Pathetic.

As I pushed them down, my cock sprang out, the relief huge as it had been getting quite sore. It wasn't quite as long as Rob's or as hard. In truth these days I usually have to pop a Viagra to get it up really hard.

Rob got hold of it and gave it a good feel. Lovely, first time I'd ever had another guy hold my dick (well, since a very young age). Rob grinned at me, then moved in, got both our cocks and started rubbing them together. Wow, that was a sensation I'd never felt before. Found out what it was called later -- frotting.

Got even better when he reached his other hand down and got hold of my balls. I don't know what it is about having your balls fondled. To me it's just the most beautiful sensation, especially when they get squeezed and popped quite hard for a l..o..ng time. They say some guy's balls are too sensitive to have them handled, well they should go on a training course.

I digress... We kept that up for a few minutes, then Rob said, 'OK want to get on the table?' I nodded and leaning back. From somewhere he got a cushion and put it under my head.

'Hook your arms under your knees, get better access that way.' My ass was then totally exposed.

Then he magicked up a bottle of lube. I saw him get a load of that on his fingers, then I felt one finger fumbling around my arsehole.

But not for long! I felt it go in and soon he was thrusting it in and out. I could feel my sphincter muscle starting to relax, then another finger went in. The sensations were getting better. He got another finger in and worked my arse steadily.

I felt his fingers come out, then something warm and round rubbing up against my anus. He started to push slowly against me and I could feel myself open up. Then he gave a bit of a harder shove -- and his cock was in me! As always when something gets shoved up your arse, it was a bit sore at first, but when he got his bulbous end past my sphincter, bliss.

As I said, I'd been wanting this for a few years, and it was even better than expected. His hot fat prick shafted in and out, the sensation in my arse was terrific. I just lay back and luxuriated in it. The difference from a dildo, even a big vibrating one, was total.

And he just went on...and on...and on.

I don't think technically Rob was priapic, but God he could keep it up for what felt like forever. I don't know, he may have been studying Tantric sex? They say if you do that, you can keep it up for ages and ejaculate at will?

That's another subject for looking up on Wikipedia. You'd be amazed at the sex articles on Wikipedia -- talk about if it moves fuck it, then describe it in huge detail!

To be honest, I tend to come quite quickly myself and have to work quite hard to stop myself ejaculating, but Rob it turned out just loved shafting in and out. He said the sensation he got from his cock skin just sliding in and out was terrific. He could hold off as long as he liked. I saw the shafting as a means to an end, it was the ejaculation/spurting/orgasm that I liked most.

Who was that Greek God, Priapus? Wasn't he the one with the stupendous cock? Yes...and no, I was thinking of the one who couldn't stop shagging everything in sight. That was Pan, half man half goat. Sorry, I had to look up Wikipedia again to get all this stuff straight...

If it moved shag it seemed to be Pan's motto. There's a great picture of an old statue on Wikipedia of him shagging a goat. Funnily enough, the statue doesn't have a very big prick, but hey. Anyway, I'm not sure Rob shouldn't have been called 'Fukus Continuos' but I couldn't find a Greek God called that.

I digress, again, apologies. Finally, he shot his load (that's Rob, not a Greek God). He must have been up me for half an hour, at least that's what it felt like. Lovely. He pulled out his still erect prick, and unfortunately there was a bit of brown stuff on it. I was a bit embarrassed, 'Sorry about that.'

'Shit happens,' he said and went off to the loo. He came back a minute later, his cock clean. It had gone down a bit, but all six inches were still swinging about. He looked down at my cock and I could see what he was thinking -- it was medium hard, but it wasn't going to go up his arse like that.

'I usually take a Viagra to get it hard,' I said.

'Oh, no problem,' from Rob. He disappeared into another room and came back with boxes of Viagra, Cialis and - what's that other one -- Levitra.

'A 50 Viagra would be fine.'

'Are you sure, a Cialis will help to keep it up for a couple of days?'

'Ah, I'll be OK with the Viagra for now.'

I swallowed it with some wine, then we both looked at each other and started laughing. I had a polo shirt on, Rob a tee shirt, we were both naked from the waist down, pricks swinging about, but we both still had our socks on! Talk about looking ridiculous!

We pulled off our tops then sat down on one of Rob's settees to take our socks off.

We both kind of looked at each other, then reached over and started fondling each other's cocks again. That was very nice, then I got another urge, 'Can I suck it again?'

Rob grinned and nodded and in seconds I was down kneeling on the floor between his thighs sucking off his dick. Even though it had gone down, it was still quite firm and there was plenty to suck and get hold of. I didn't realise until then how much I'd like doing that.

'Suck my balls,' from above. I hadn't thought of that, but I soon had them in my mouth, sucking and squeezing. That gave Rob a real thrill.

By then the V was working and I could feel my prick was really hard. I looked up, 'Want to try it now?'

Rob nodded. He got up on the table like I had and spread his arse cheeks, holding his hands behind his knees.

I'd never done this before, so I was a bit hesitant, but I got the lube on my fingers and prick and did just like he did -- finger at a time. I got him nice and loose, the feel of my fingers in his arse was very pleasant.

Then I grasped my cock and started rubbing my bulb along his arse crack. I located his anus and started to push gently against the hole, like he did to me. I think Rob's arse must have been a bit looser than mine, as I wasn't pushing very hard when suddenly it was in him! My knob end easily got beyond his muscles. I fucked away.

Wow! It was lovely. Sorry, I've said 'lovely' again. It's funny, when rogering my own arsehole, I'd often thought how much I'd like to have a real hot cock up there. But I hadn't thought how much I might enjoy getting my cock up another guy's arse. Turned out it was an exquisite sensation, quite different from being up a cunt.

There was something about the way Rob's sphincter muscles gripped my cock that was just...lovely. It was so good I knew I wasn't going to last. I tried my hardest to hold back, but it wasn't long before I had to shoot.

I felt my hot spunk pulse up my prick and into Rob's arse. I spurted up him half a dozen times and kept riding him until my prick started to soften.

'Sorry, Rob, I just couldn't hold it in any more.'

'That's OK,' he said, 'first time?'

'Yeah'

'Good?'

'Great!'

'Want that dessert now? Banana and custard.'

'I think I could do with a drink.'

Rob fussed around, then we sat down in front of his telly and watched some of his porn collection. Funnily enough, nearly all of guys shagging each other.

I particularly liked the shots where the one guy sat on the other's lap and you could watch his cock bouncing up and down while the other cock was up his arse. We were sitting fondling each other's cocks and I could feel Rob starting to get hard again.

'Fancy doing that?' he said.

'Sure.'

We got into position and in no time Rob had his prick up me again from behind, easier access this time. My cock started to rise and soon we looked just like the guys in the porn movie we were watching. I liked looking down...watching my cock bob up and down.

What an evening. Not what I'd been expecting of the evening, but at last I'd got what I'd dreamed of for ages, a big cock rammed up my arse.

Well, in the end I stayed in Rob's flat for most of the next three days. What did we do? We fucked and fucked and fucked. Talk about getting it out of your system! There was no doubt Rob was the 'dom' and I was the 'sub', he must have fucked me twice as much as I did him.

We did it everywhere and every way round. His favourite was to take me from behind, doggy style, or in his case more like stallion style. He liked doing that everywhere, over the table, on the settee, on the bed, in the bathroom.

Strangely, I actually found what I liked most was sucking his cock (and balls). But let's be clear, shagging his arse as much and as often as I wanted was just wonderful and so liberating.

You know, I've got a theory, well I've actually got quite a lot of theories, that quite a lot of male gay activity is not about preferring guys per se (Latin) -- it's about getting as much shagging as possible.

Of course, there's plenty of women nympho's about -- sorry I'm showing my age -- but shagging women can be quite hard work. You've always got to be thinking about what they're wanting, if you know what I mean... With two guys, it's much easier -- they just want to fuck...

***

In the end Rob had to go on a trip and my wife was due back in a couple of days anyway. Lucky I didn't have to walk far to our flat. You know the book, 'Tender is the Night?' Well, this was the sequel 'Tender is the Arse.' I didn't think I would be able to sit down for a couple of days.

Anyway, I was pottering about our flat...well, waddling I think would be more accurate, as I was trying not to move my arse about too much. Anyway, I was getting everything shipshape and the small jobs done that I promised I would do while she was away.

I was whistling as I worked, happy as Larry (who was Larry?), until a terrible dilemma occurred to me...what if anything was I going to tell my wife?

Shit, I thought, now I've got a real conundrum that requires great thought and intellectual rigour.

The problem was I'd really enjoyed having my arse fucked and certainly wanted more of it with Rob. Just thinking about it put a tingle in my bum. But if I kept quiet about it, opportunities would be few. My wife didn't go away very often and other than that it would just be a few snatched hours.

On the other hand, if I told her the whole story, how would she react? She'd maybe just go along with it -- at the other extreme threaten to divorce me!

Now, I want to make it clear that my wife and I had quite a good sexual relationship, inasmuch as we shagged at least once a week, quite often two. Indeed, she often was the one suggesting it.

She'd suck my cock if I asked and from time to time let me go down on her and suck out her cunt. Her favourite position was riding me cowboy style. She'd close her eyes tight and her face had a look of absolute bliss as she orgasmed.

But I guess she was a bit in the 'missionary' camp. I wouldn't say she was a prude, but she was quite straight-laced about the whole sex thing. She wouldn't really engage in any conversation about it or do anything, err, a bit more adventurous.

One of my suggestions, a little erotic tattoo on the inside of her thigh near her cunt? No chance. How about us making a little porn movie, you sitting on me riding me, your tits bouncing up and down? Me holding the camera above my head, zooming in occasionally on your cunt? OK, I didn't even suggest that one!

I did from time to time slide my finger down and run it around her arsehole, but she always gently but firmly removed my hand. Enough said.

I certainly could have done with more sex from her, but I wouldn't say I was sex starved. I just wanted a bit more and to do other sex related things, like a bit of cross-dressing, watching (more) porn, wanking myself off (OK, I did that all the time anyway)...and experimenting with anal.

What to do? Then, I had a Great Thought. I'd give myself a really good arse shagging workout. If it was as good as being fucked by Rob, I'd keep quiet. If it wasn't... I set to work.

By now I had four or five choice dongs hidden away. I put on all my cross-dressing gear -- the fishnet stockings, suspender belt, thongs, bra, a nice little mini dress in jersey wool with a leopard skin pattern. H & M, very reasonably priced. Got myself worked up and stuffed myself with all the different dongs.

Well, it was good...very good...but just not as good as it was being shafted by Rob's real, live, hot, thick cock.

You know, there's something I've got to say here. I am absolutely not a homosexual in the proper sense of two men loving each other and sharing their life together. That's fine and good luck to them...but what I wanted was sex. You know, to be truthful, on porn films at that time seeing two men kissing turned me off a bit. I just wanted their cocks.

Anyway that decided me. I would just have to tell her and see where it got me. The next day, my wife got home in a taxi late afternoon. We sat down, had a cup of tea.

'Anything interesting happen while I was away?' she said.

'Well, yes,' I said, taking a deep breath. 'You know I went over to Rob's for supper one night?'

'Yes...'

'We ended up having sex together. He took me anally -- pushed his thingy up me.'

Seemed a corny way to put it that way, but I couldn't bring myself to say he fucked me in the arse!

Silence...then, 'Oh, that seems unusual. Who would have thought it of him? Was it consensual? Did you want it to happen?'

She was clearly processing the most outrageous thing I had ever said to her!

'I think I need a drink.' She went to the fridge, took out a bottle of wine, poured herself a very large glass, took a very large swig and sat down again. There was further total silence for a minute.