In Praise of Anal Sex - A Memoir

For years anal sex has held a deep, exciting fascination for me.

My addiction to bottom fucking started in the late 1960s in England where I then lived. I was an 18-year-old boy scout at a camp with some older boys. Sitting around a campfire one evening a Ranger -- as older scouts were called - regaled us with tales of a recent holiday he had enjoyed with his girlfriend when they spent most of the week naked, fucking often and in inventive ways. Of all the things he described the one that excited most was his description of sliding his cock into her backside and how tight it felt. Most of my friends laughed at this, but the thought of it made me feel incredibly randy and left me with an erection growing in my shorts.

Now, I wasn't a virgin. My then girlfriend -- I'll call her 'B' -- were fucking regularly -- often in the room next to where her parents were, but that's another story. This was in the early days of the contraceptive pill, and it wasn't easy for teenage girls living at home to ask their family doctor for a prescription. So, we played Vatican Roulette or the 'withdrawal method' as it is called. I remember at least twice where the initial spurts of my cum came just before I pulled out of her slick pussy leaving at least some of my sperm inside her. How lucky we were that she didn't get pregnant. How different my life would have been if we'd got it wrong.

Despite being sexually active I didn't get round to trying to have anal sex until a few years later when I was at college. 'C' was a voluptuous student friend of mine who enjoyed sex. While I played with her ample bum quite a bit, sliding my cock between the cheeks of her lovely arse, I didn't have the confidence to try to penetrate her there. She was confused about what I was or wasn't doing -- and so was I.

That was pretty much the pattern for the next few years / girlfriends -- lots of anal play but no penetration. I suppose I lacked the confidence to ask if they wanted to go further. That was to change.

It was the same with my first wife 'K'. I had realised by then that there are some women with whom I was confident enough to enjoy anal play and some with whom it just didn't seem possible. 'K' was one of those. Although I did spend quite a bit of time masturbating myself between her cheeks before I fucked her pussy.

My fascination with bums never left me. I lusted after every beautiful female bottom I came across, but being a loyal husband, I didn't do anything about it.

After my divorce I hooked up with an old college girlfriend who like sex in the open air. One day we were walking in the Lake District when she pulled me into a secluded hollow in a field to fuck. We stripped off and began with foreplay, kissing, licking sucking and finger fucking. Then she surprised me by kneeling down and licking my anus. I was startled and turned on. Although it didn't occur to me to try to have anal with her, another seed of excitement had been sown.

Later the same year a house mate of mine another 'K' invited me into her bed one night and while we were fucking, she slipped her finger between my arse cheeks, stroked my anus then pushed the tip of a finger into me. I have to say that it did excite me and that I orgasmed pretty quicky as she was doing it. Another seed of confidence and excitement...

I now clearly understood that certain women enjoyed anal play.

Then came my second wife 'M'. She was quite a sexual person who had a strong libido, but not much self-confidence so she was somewhat scared of her own desires.

She had a beautiful, rounded and shapely little bottom that I enjoyed playing with. She welcomed me sliding my cock between her cheeks before I fucked her pussy. A few times this resulted in me being so turned on I came all over her back instead of in her cunt.

M also initiated some anal games, including 'find the chocolate'. This involved her being naked in a fully darkened bedroom. I then had to find her in the dark and once I had discovered her hiding place, I had to find the chocolate hidden somewhere on or in her body. Sometimes she held it just in the entrance of her anus, so I licked and sucked it from there. Double chocolate heaven!

One evening when the children were in bed, we were fucking in front of the fire in the living room. She was lying face down over a large bean bag and I was licking her pussy and anus. As I licked her, I used my tongue to relax and stretch her tight little hole and pump saliva into her. Then I tongue fucked her, to which she responded by pushing her arse upward in invitation.

I knelt behind her and again slid my cock along the crack of her arse. I repeatedly allowed the tip of my cock to just catch in her anus before sliding further along and back. And then... my cock caught more firmly than before... I hesitated and then pushed a little harder and at a slightly different angle... and oh Lordy!... there was a pop as I slipped the end of my cock an inch into her ... Wow! The tightness and the heat... the taboo... the tension... Should I continue? I did. I had about half my cock length inside her when things became a bit bizarre. She started to say 'I don't want to...' but her words were cut off as she was overwhelmed by the most explosive orgasm she had ever had (or in fact ever did have).

What was I to do? As she came, I slid the full length of my cock into her and started fucking fully. The sensation of her beautiful little cheeks nestling between my balls and my inner thighs was so different to 'normal' fucking and added hugely to the excitement. The delicious tightness of her sphincter around the base of my cock combined with the amazing soft warmth of her back passage caressing and squeezing my cock was exquisite. I didn't last long - probably less than a minute - until my own orgasm pumped her backside full of my semen.

I found that breaking the taboo of anal sex (it was illegal in the UK until 1967) was part of the excitement. I also found that the thought of depositing my load of semen and sperm deep into her arse, into the 'wrong' place, was incredibly sexy. That excitement of unloading deep inside someone's bum has never left me and for me remains one of the highlights of a good anal fucking.

Afterwards I think we were both a bit shocked. She was uncertain whether she wanted to do it again but true to her character she often changed her mind. Over the next few years, we had anal sex occasionally. It was never as good as the first time because although I never forced her and she did enjoy it at the time, she remained guiltily unsure if she really wanted to do it again. Human beings are complicated creatures.

I have since learned that finding somebody who really enjoys a loving anal fuck is absolute perfection. But it was a few years -- and a few more willing bums sampled - before I found the 'holey' grail.

After divorcing my second wife I had what I can only describe as a Damascene conversion, but instead of the road to Damascus; it was a road in the French Alps.

One very warm day I was waiting for a friend on the terrace of a roadside café when a young lad -- he must have been in his early 20's - stood beside the road a few metres away from me and put his thumb out to hitch a ride. Nothing unusual in that but he was only wearing loose-fitting white Y-front underpants which displayed his bum and his bulging balls and cock really well. I have no idea why he was only wearing underpants -- it was a hot day - but he might as well have been naked... and he had a God-given arse. Fit, firm, manly, flat sided and rounded... and it made my heart go bump and my cock harden. I think I might have groaned out loud. It didn't take long for a man to stop and give him a ride... or perhaps he gave the driver a ride.

Up until then I had not been attracted to men's bums. Everything changed that day; I realised that I was bi-sexual. Thinking about it I didn't feel that it was strange in any way to lust after men. In fact, I tried to initiate a discussion with the friend I was with, asking him if he had ever had experience with other boys at school or at college. Unfortunately, he didn't follow up on the conversation, so nothing came of it.

I watched porn occasionally and now found myself looking at the male bums flexing and thrusting as often as I watched the arses that were being fucked.

Back home using the Gaydar website I met up with a gay guy who like to be fucked. My first time with a guy was a very enjoyable afternoon of sucking and fucking. It felt very strange to be playing with someone else's cock rather than my own but very relaxing to fuck him because there was no doubt that he really liked to be sodomised. He had a full, comfortable, pillowy arse and spurted his cum over his bed linen as I fucked him. I never went back because the sod gave me crabs. I was much more careful who I fucked after that.

I had a few more sexual encounters with a few guys I met online, but no anal sex was involved until I met a chap from Birmingham. He liked to wear female underwear, and I found that a guy wearing sexy 'girly' lingerie was a big turn-on for me. After some coffee and a chat, we adjourned to his bedroom. He sucked my cock to make me hard and then turned round and knelt on his bed, presenting his knicker-clad bottom to me. I pulled his red silk panties down and stroked his anus with my fingers, applying some lubricant as I did so. When he was ready, I slipped the head of my cock into his sphincter and, as he relaxed, pushed all the way in. Inside he felt incredibly smooth, silky soft and hot with a very welcoming tightness - one of the most comfortable anal fucking experiences I've had. It felt so good to bottom out in his arse that I came far too quickly. A learning experience.

My next sexual encounter was with a woman 'T' who I met via an online chat forum. It just so happened that she lived in San Francisco. Only an 8-hour flight from London. We chatted online face to face via web cams. She was very happy to strip off for me and show me her beautiful breasts, pussy and bottom. She told me that she had a 'thing for Englishmen' and I was quite happy to masturbate online while she watched. We agreed that I would fly to America for a week's holiday in northern California. A week before the flight we were talking online and I told her I wanted to 'kiss her everywhere, including her bum'. Her reply was "I want you to fuck me there."

What a week. She met me at the airport. We drove straight to a hotel and fell into one of those huge beds they have in American hotels. We fucked like rabbits for hours. A day or two later, as we came to know each other better and trust each other more, it was time for her to give me her anal virginity. She was very tight and became quite frustrated that I was having difficulty penetrating her anus. I spent a long time licking her, gently fingering her and lubricating her. We tried different positions. In the end I asked her to lie on her side with one leg straight and the other with the knee pulled up towards her waist. This enabled her to relax her bum cheeks and sphincter and we both gasped in pleasure as my cock popped into her bottom.

Very gently I withdrew and popped it in again and again eliciting little gasps as I did so. It was like taking her virginity time after time. She became fully relaxed and by degrees I eventually felt my cock go in as far as it could. Her lovely bum cheeks caressed my lower stomach, and my balls nestled against her pussy. Perfect! She was so willing and so tight that we fucked slowly and very gently that first time. With the help of me playing with her clit she came just as she was accepting my gift of a large load of semen placed as far into her back passage as I could press my cock. Heaven!

After then I nearly always fucked her pussy first and then used the wetness of her cunt and my semen to fuck her beautiful bum. I loved loading her backside with my fluids. One morning as we went down to breakfast, she had to rush off to sort out my semen dribbling into her knickers, about which I felt both guilty and very happy at the same time.

One evening we fucked while we watched television. She was kneeling in front of me while I fucked her pussy and then her bum. Over her shoulders I could see an old episode of Star Trek playing on the TV. To this day whenever I see a re-run of old Star Trek shows my cock twitches in my pants and I can taste and sense T's gloriously sexy aroma and feel her willing pussy and arse enjoying being fucked.

The most memorable fuck I had with T was early one morning. We'd fallen asleep after an anal fuck with me lying behind her spooning with her. When I awoke some hours later, I realised that my foreskin was still caught and held by her sphincter. It turned me on straight away, so I moved my hips gently backward and forward masturbating my cock in her bum and making myself hard again. Then I slipped it slowly into her. She awoke with my cock buried deeply into her back passage, which was hot and still well lubricated by my semen from the night before. We made beautiful, erotic anal love like that until we were both exhausted and fell back to sleep.

After that week I never met her again, but we kept in touch for a while. We both agreed that the week had 'saved our lives' as we were both recovering from the breakups of serious relationships. I fell in love with her and still feel like that about her. I will never forget you T.

A few months later I met 'F' the most spectacularly sexy woman I have ever known. A much better writer than me coined the phrase that perfectly describes how she fucked: 'refined carnality'.

She had medium-sized perky breasts with prominent nipples that always seemed to be hard. A slim waist offset her most magnificent arse. Large, round, firm and very 'spankable'. And she did enjoy being spanked, tied up, dressed in harnesses and having her pussy lightly whipped with a soft strap.

She was of mixed European origin, so her skin was a beautiful light olive brown. She orgasmed at the slightest encouragement. I once knelt between her legs and blew lightly on her clit. It took her no time at all to climax and for her pussy to become dripping wet and ready for my cock. She enjoyed all sorts of sexy games and indulged my every sexual whim including some fun water sports.

I'm sure she wasn't an anal virgin, although to excite me she pretended she was. I had talked to her for three months online before we met face to face. After we had a meal in a restaurant we fell straight into her bed. I soon realised that she had no inhibitions. We fucked regularly through the night.

As soon as I turned her over and began playing with her bum, she told me I could fuck her there. I needed no further encouragement. After a little fun lubricating her and feeling her respond to my every touch, I slid my cock into her tight little ring and massaged her sphincter with my tip. I tried to hold off as long as possible, teasing her arsehole. Of course, I had to give in to the temptation of being totally engulphed by her bottom, so I slid fully into her until her large cheeks stopped me.

I pulled them apart and started to thrust even more deeply into her. She responded enthusiastically by pushing up and back as I fucked her with long, deep and slow strokes. Watching the ripples of flesh that were generated by my hips smacking into her ample bottom was a total turn on. It was obvious to her that I was about to come, and she began to come at the same time, thrusting and moaning as I filled her backside with the first of many, many ejaculations. She was the only woman I have fucked that always had an orgasm when I buggered her. Perfect!

Our relationship lasted for two years during which time we fucked as often as we could. She enjoyed being fucked from behind and I loved watching my cock entering and withdrawing from her pussy or her anus. There is something about the way an anus pouts as you pull back that is extremely erotic. She also enjoyed double penetration as I introduced a butt plug into her bum as I fucked her pussy. She became almost helpless with lust and ecstasy when we fucked like this. It was a joy to experience and to watch her body react.

Beside a motorway in southern England, where it passes across some heathland, there is a solitary tree. I can never drive past that tree without my cock twitching at the memory of F and me rolling naked, fucking as the sun warmed my bum. As was my preference, laying face to face I first fucked her pussy and then turned her over, pulled up her hips so she was in a kneeling position. Then I spread her legs and pushed her shoulders down, so her bottom stuck up in the air before me. A couple of thrusts into her cunt lubricated my cock, which I then eased into her backside. Ah! That wonderful pop as the head of my cock passed through her ring; the silky-smooth plunge into her back passage; the warm elastic resistance of her buttocks being compressed by my lower tummy; the feeling of my balls slapping her cunt. Holding her hips and thrusting hard into her bowels while she moaned and sighed prior to losing control of her body as her orgasm made her dance on the end of my cock. I will never forget that afternoon. I often wonder if my current wife wonders why I have a strange secret smile on my face as we drive past that tree!

As a footnote to my relationship with F, I should mention that she had a drop-dead gorgeous daughter -- no I didn't fuck her -- who was the inspiration for my story 'Pink Mini'.

My next anal lover was 'D'. She described herself online when I asked as 'marriedish' meaning that although she still lived with her husband they were breaking up. She was another anal virgin who, while she wasn't the greatest fan of being fucked like that was very happy for me to indulge my desire to lie full length on her back, telling her sexy stories while slowly easing my cock in and out of her waiting anus. She was also bi-curious and I encouraged her to meet up with a couple who wanted a threesome with her. She enjoyed the experience of having sex with a woman while the man was fucking her. I was willing to join them but somehow it never happened. A great regret.

After D my next anal conquest was with a lovely warm Welsh guy called 'J'. He was a married cross-dresser who wore women's panties and loved to be fucked. My first time with him was in a pub where I surreptitiously stroked his arse while nobody was looking -- I hoped. The next time was in his car where he sucked my cock. It was all a bit cramped and difficult so for the next encounter I booked a hotel room.

He was fully shaved but had missed a few bits, so I offered to shave him. He took off his white frilly panties and knelt on the bed while I lathered his arse, cock and balls before carefully making him as smooth, sexy and fuckable as I could. His arse was too tempting, so I teased him with my tongue, which he loved.

Next, I laid him on his back and lying between his legs I fucked him as if he was the woman he wanted to be. Very sexy it was too watching my cock disappear under his balls and into his anus while his little cock bounced around playfully. Then after some more play I stood behind him as he knelt on the edge of the bed and fucked him again. He was really turned on by having my cock stretching his 'man cunt' and I think a large part of his pleasure was seeing and feeling how much pleasure he was giving me. He was a lovely guy but changing circumstances meant I didn't hook up with him again. A real shame.

And last on the list, but not least -- another K. I was on an extended holiday in the US. She had recently separated from her husband of 35 years, so she flew out to join me. I would have been quite happy with a platonic relationship to help her recover from her trauma but luckily for me she had other ideas.

We became closer as the days went by. One evening we started talking about sex. She eventually told me that she had only ever had sex with her husband. It was obvious that she wanted to have sex and, being the gentleman I am, I didn't refuse her implicit request.

So, we started fucking. All very cautious and vanilla at first as she became used to the feel of a body other than her husband's close to hers and a different cock giving her pleasure between her thighs. She had beautifully soft pubic hair, which was a pleasure to bury my nose in while I licked her to climax -- something that really turned her on.

One day, for variety, I folded her legs back as far as was comfortable for her, exposing her anus. I tickled her tight little ring with my tongue. She responded with an 'ooh!' sound so I carried on playing with her 'chocolate starfish' as my niece calls it. Later, after we'd had conventional sex again, we lay talking.

"I've always wondered what it would be like," she said. We both knew what she meant.

"Would you like to try?" I asked, sliding my finger between her legs and caressing her arsehole.

She nodded and clung on to me, a little bit embarrassed to be sharing what she considered to be a bit risqué.

The thought of another virgin bum to fuck turned me on even more. Having had a rest, I was ready to fuck again. I turned her over and put a firm pillow under her hips. Then I straddled her legs and slid my cock into her cunt to make it wet again. I spent some time lubricating my cock and spreading the moisture between her bum cheeks. When the time was right, I moved so the tip of my cock was lodged in the entrance to her anus. I pushed a little, so the first centimetre of my cock eased her sphincter open.

"Now push out as if you were on the loo," I said.

She did as I asked and relaxed completely so my cock head popped inside her. Oh man! Do I love that feeling! The tip of my cock trapped in a willing virgin anus, knowing that before long, with encouragement and gentle pressure I will eventually be up to my balls in a tight, warm bottom with her firm little cheeks nestling between my thighs. Heaven.

I spent a long time easing my cock into her with small thrusts so she fully relaxed. Once she became used to my cock invading her arse I started thrusting more strongly into her, but not enough the scare or hurt her. She responded by starting to enjoy it more and more, eventually wiggling and pushing her bum upwards for me.

That first time I didn't fuck her too hard or too quickly. I wanted her to enjoy it and make it last as long as possible. To my delight she became more vocal as she became more excited. Her orgasm took us both by surprise.

Still controlling my thrusts, I fucked her deeply and really enjoyed filling her back passage with my semen. As I've said before the feeling when you ejaculate your load into that taboo space cannot be beaten.

I lay full length on her back -- supporting my weight of course - letting my cock shrink while I kissed her neck and told her how good felt.

She surprised me by asking "Will we always do it like that now?" It made me wonder about her relationship with her husband.

"Not if you don't want to," I replied.

It turned out that she did want to. It became a regular part of our fucking. I usually fucked her pussy first, then licked her to another climax and afterwards as she relaxed from her second orgasm, I would turn her over, put a pillow under her hips and give her sexy little arse the bum fucking it deserved.

So there you are. This is a true story -- as true as any story based on memories can be - of a lifetime of enjoyable anal sex with a variety or partners. I hope you enjoyed it. I hope you enjoy your own anal adventures.

What is the best way to encourage a lover to try anal sex?

Take your time. Be careful. Be loving. Be kind. Be respectful.

Do I have any anal dreams left? Yes, I do. I have never been anally fucked. I'm looking for a suitable guy to take my anal virginity. Wish me luck.

Darius Thornhill 2025

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