Author's Note: This is not fiction. It is a true account. It is 100% factual.

In my previous tale "Real life restraint" I recounted the true story of my first bondage experience and of the lady who allowed me to tie her. (Search my name to find it). In the closing paragraph I mentioned another girl from later in my life who I shared my first anal sex experience with. I have had requests to explain who she was. So this is the story of Rachael and of my journey into anal sex. This will be a difficult story for me to tell as I have to admit a few things I am ashamed of.

This story contains female bondage, sadism and male anal self insertion. Don't read it if you don't like these things.


Time = February 1991
Place = another small town in the UK
Event = my first anal sex experiences

When I first met Rachael she was going out with a friend of mine. I wouldn't say he was a good friend. In fact I would say he was a bit of an idiot. But he was harmless and was part of the group of bedraggled and miscellaneous motorcyclists and beer drinkers who I considered to be "my" people. I was twenty three years old. Rachael, or Ray as everyone called her, was twenty.

Ray had a beautiful face. She was stunning. Her pale milky skin made her high cheek bones, luscious red lips and black wet eyes seem exaggerated in size like a cartoon character. She had long blonde hair which danced down her back. She could have been a model. Her face was so perfect she could have been a super model. That is... if she had been six feet tall and slender. Unfortunately for her catwalk career she was barely five feet tall and had a body shape that could be described as "dumpy". She wasn't fat. In fact she wasn't really that wide at all, but her short stature made her look wide of hips and ample of thigh. And she was not blessed in the breast department. In fact she was completely flat chested. She had impressive nipples when aroused, as I would discover later, but Ray never entertained the pretence of wearing a bra. She just didn't need one.

Ray came from a dysfunctional family. Many of our group did. She grew up on a remote farm with her little sister, a domineering mother and an emotionally distant aggressive father. But in spite of this she grew up to be one of the most loving, caring and forgiving people I have ever known. I never heard Ray say a bad word about anybody. Even her abusive father or her boyfriend who regularly cheated on her with a string of women who he didn't even try to hide from her. Ray was so sweet I couldn't bear to watch her boyfriend make a fool of her. But she knew about the other women and it wasn't my place to get involved. I was very pleased when she finally dumped him.

She started dating other guys in our group and quickly gained the reputation of always putting out on the first date. Lots of men wanted to take her for a night out, not because she was a beautiful person, but because they knew they could get a fuck with minimum effort. Once again I found I couldn't bear to see Ray with other men. She was just so nice. She deserved to be loved and cared for. And not taken advantage of by every man she met.

I don't know why Ray was so easy to get into bed. Maybe she was making up for the love and attention she missed out on during her childhood. Maybe she was living the life her ex-boyfriend had. And did it in front of him as revenge. Maybe she just liked sex a lot. I knew the latter was true as we had discussed sex once at a party when we were both drunk and her boyfriend was in another room chatting up a tall brainless girl. She hadn't gone into detail but had made sure I knew she liked to experience a man's cock. I would have liked her to experience mine, but didn't offer that point of view to her at the time.

One evening I met Ray in a pub. We were both alone so I bought her a drink and we talked. I told her how much I liked her and two hours later I was in her flat, in her bed, between her legs. She was a good fuck. Tight and wet. And quite noisy. She panted loudly all the way through. I liked that.

After sex I asked her if she wanted us to spend the next day together. I had to drive into the city to collect some car parts and also needed to visit a friend. I suggested it would be fun if we went together. She seemed more excited by this suggestion than she had been about sex. I didn't think about it until much later, but I suppose most men who had just cum inside her would have lied about their intention to call her in the morning and left. I stayed all night. And I wanted to be part of her life. We were officially boyfriend and girlfriend from that moment.

Even though we lived in different towns we met four or five times a week. And every time we met we had sex. Over the next few weeks I began to realise that Ray was submissive. She wasn't submissive in the way the last girl I had tied up had been. Tamsin had a strong personality and liked to be in control of her life. But she gave up that control during sex and consented to being tied up as part of that exchange of power. Her submission was a gift to me. A gift which was taken back when sex was over. I think most people who enjoy a submissive role in their sex lives are of this breed. But Ray was different. She was naturally submissive. Not just for sex but for everything. Anything I wanted her to do she would do it without question. If I asked her to make me a cup of tea, she made it. If I told her we would have to change our plans as I needed to go somewhere, she changed her plans to match mine. If I told her to wear different clothes, she did. If I told her to take her clothes off, she did. If I told her to kneel, open her mouth and close her eyes, she did. She had a dependant personality. She had chosen me as her controller and let me make all her decisions. Looking back now, I only wish I had realised what a responsibility her trust in me was.

With a natural submissive in my control, it was only natural I tied her up for sex. Most of our sexual encounters involved ropes, straps and other means of restricting Ray's movement while I pumped into her to our mutual orgasmic pleasure. I started reading bondage fiction in pornographic magazines looking for ideas of how I could tie her in different ways. She never made any suggestions to how she preferred to be tied, she seemed to enjoy everything. But she enjoyed non-bondage sex just as much. She just seemed happy to be making me happy. We were both happy. But this was not to last.

I have suffered from depression my whole life. It comes and goes. The worst time was over about two years between the ages of eighteen and twenty. I had a good spell for a few years but then it came back. Now I understand my condition and take medication to see me through the dark times. But when I was younger I didn't know what was going on. I knew I wasn't happy and hoped I would be happy again soon, but I didn't understand the other ways it affected me and how it destroyed my relationships with other people. Depression is like a thick fog which slowly settles on your mind. It clouds your judgement and stops you seeing others clearly. It makes you take wrong turns because you can't see the right way to go. Sometimes it happens so gradually you don't notice it coming. I didn't realise my mind was losing sight of Rachael in the fog.

Depression affects everyone differently. When I was "in the fog" I didn't appear moody and sad to others. But it changed my personality. I lost all my self-worth and became emotionally numb. I lost my ability to feel empathy. I cared less about others. It's a Jekyll and Hyde phenomenon. My evil side was released. Or in Rachael's case, my sadistic side. Ray and I had experimented with pain as part of sex. I had spanked her a few times and had roughly pulled her nipples during sex. Judging by the sudden wide eyed facial expressions and tight lipped muffled squealing noises, it was obvious that nipple stretching was very painful for Ray. However, it never stopped us completing sex. She never tried to stop me before I was finished.

Seeing Ray in pain became extremely exciting for me. As soon as her face began contorting in discomfort my cock became so swollen it hurt. I wanted her to be in more pain. I had always had a latent sadistic streak and for years had fantasised about torturing girls. But doing it for real was so much better than using my imagination while I wanked myself off. My sadistic side was about to take over.

One afternoon we were watching an old film on TV. It was about a pirate ship. A woman had been captured and was tied to a grate. She had her dress ripped off just enough to see her naked back but not her arse or breasts. It was a 1960s film after all. Then she was whipped.

"That is hot. I'd love to do that to you" I said.

The next scene showed blood running down the woman's back from the cuts the whip had left.

"Not with one of those you don't" she said shaking her head.

I saw my opening. "Could I do it with something else?"

"What have you got?"

I was wearing a two inch wide leather belt to hold up my jeans. I unclipped the end, pulled it out and held it up so it hung down for Ray to inspect.

I tied her bent over the big wooden kitchen table. She lay face down on the top, her legs hanging over the side. The table was high and her legs were short so her feet didn't quite reach the floor. I wrapped the buckle end of my belt around my hand and took my first swing. I planted the belt straight across her buttocks with a satisfying whack. Ray tensed every muscle she had so violently she almost jumped clear of the table. She sucked air through the wide open mouth of a silent scream. Everything seemed to pause for a moment then she relaxed and started breathing again. I swung again. Ray reacted the same way. I swung again and again. After about six I undid my trousers and let them drop to the floor to release my throbbing cock. I kept swinging the belt to strike across her arse. By the time I had struck her about twenty times she wasn't jumping with each blow any more. She just lay there. She sobbed and sniffed. She was crying like a little girl.

I had to enter her. I put my cock between her legs but she was dry. I had never experienced Ray's vagina when it wasn't wet. I pushed the tip of my cock slowly into her wriggling it from side to side to work my way through the dry folds of skin. When I breached her internal cavity I felt the dampness on the head of my cock. Then her juice started to flow. She flooded herself and my length slid effortlessly inside her. I fucked her like a wild animal. I thumped into her as hard as I could. I only lasted a couple of minutes before I shot my load. I stepped back messily falling out of her and collapsed on the floor. My balls ached. It was an enormously intense fuck. An unbelievable experience. I had been so consumed by sexual release I couldn't stand up. As I calmed down and my breathing returned to normal I noticed Rachael was still crying.

I had to go to work so I didn't stay that evening. I thought about what I had done all night. I couldn't believe I had done that. I hated myself for doing it. I didn't hate myself for beating Rachael. My sadistic self had a basic need to feed from the pain of others. But I was sexually sadistic. That means I was not a sadist in normal life, outside of a sexual context. To watch Ray experience pain for my sexual pleasure was normal. I felt no shame in that. If Ray didn't like it, that was unfortunate but I wasn't going to apologise for doing it. What caused a massive increase in my self-loathing were two questions I couldn't answer. One- why did I get so turned on by Rachael crying? And two- why did I fuck her when she was dry and not sexually receptive? The crying question was just too weird and I didn't even try to figure that one out. But the question of fucking Ray when she wasn't ready for it troubled me deeply. What had I become? To force myself on an unwilling girl was... I couldn't even think the word. It was too terrible. Was I a rapist? No. I can't be. I am a sadist. I am an evil, calculating, torturer. I am sexually sadistic and proud of it. But I am not a rapist. I would rather die.

The next day I went to Rays as soon as I could. She was wearing a big loose skirt. We called it her hippy skirt. I guessed she was still very tender around the buttocks and didn't want tight fitting clothing for a few days. Later she told me it felt like really bad sunburn. I hesitantly apologised for forcing my cock into her when she was dry.

She smiled and said "It's OK. You just didn't give me enough time to get ready for you. Once you got me started I enjoyed it".

I couldn't believe it. She was fine with the whole experience. I wasn't a rapist, I was just guilty of premature entrance. Ray had just proved herself once again to be an amazing and truly wonderful person.

But this episode showed a fundamental difference between us. When I was strapping her arse, the most exciting part was seeing her react to the pain. That was the peak sexual experience for me. The penetrative sex was just the icing on the cake and a means for me to release the building pressure in my balls. The biggest sexual excitement was watching her suffer. But Ray saw it differently. To her the beating was something she had to endure to please me. It was not sexual. To her the sexual experience only started when the beating stopped and we locked genitals. She didn't gain sexual pleasure from pain. She gained pleasure from knowing I was gaining sexual pleasure from her pain. Rachael was not masochistic, she was very submissive.

After this somewhat tumultuous first experience of proper sadism we tried again a few times over the following months. I strapped her across the arse and back the next time. And I used a vibrator on her while I did it to encourage some compatibility with her arousal and my entrance. Ray didn't want to do it very often, claiming she needed at least a month to recover fully. But after what I had learned the first time, I didn't mind that at all.

My depression was not improving. The fog was still there and my sadistic character was strong. It wasn't long before I had more plans involving pain. One afternoon we got back to Rays flat and as usual we wanted to have sex. I tied Ray face down on her bed. Stretching her arms and legs tightly out to the four corners. She knew that now she was tied she wouldn't have to be very involved in the encounter. It was her job to lie still and let me do the work. She was expecting a relaxing screw with a few orgasms and then a quiet night in.

But I looked between her legs and thought "I'm going to fuck you up your arse."

I had always been fascinated with anal sex. When I first started masturbating at the age of twelve I very quickly realised the anus was a powerful erogenous zone and potentially very useful for sex. Even before I got the chance to read any literature to inform me of how anal sex worked I knew the anus had to be involved in sexual pleasure. I started to insert at an early age. The feeling of putting things inside me was exciting. It felt very wrong and very right at the same time. Using an object to fuck myself in the arse while I masturbated made it a much more pleasurable experience. The change in sensation in my stretched sphincter during orgasm was intense. The first time I felt this it was overwhelming and I had to pull the object out quickly. But I tried it again and soon became addicted to the intensity of the feeling.

When I was thirteen years old I had a set of felt tipped pens which were about 8mm in diameter and curved to a point at the end like tiny vibrators. I pushed one inside myself. The next wanking session I put another alongside the first. Then the next time, a third. Once there were three, the fourth could be pushed in-between them so it slid against the other pens and not against me. I hadn't realised the benefit of lubrication yet. As I fitted more pens into my arse it got more uncomfortable. But I kept going. After a few sessions I could fit in enough pens for the combined diameter to be more than my erect cock. Now I knew that I could take a cock inside my arse. I was immensely proud of this achievement. Although I was heterosexual and had no desire to actually have a cock inside me, I really enjoyed understanding how a girl would feel when she was penetrated in her back passage.

As I grew through my teenage years I became more adventurous with my anal insertions. At fifteen years old I found a glass lemonade bottle which was about eight inches long. It had a tapered neck starting at the cap which was less than an inch wide increasing to its full width of three inches diameter. But the reason I kept this bottle was the four inch long tapered neck was straight and gradual. I tried sitting on top of the bottle and lowering my weight onto it to see how much I could force inside me. This was not very successful as once my anus opened to around one and three quarters inches wide it started to become extremely painful. Even with ample lubrication. I didn't mind my anal stretching being uncomfortable. In fact I liked it to be uncomfortable. It made me feel like I was working hard to achieve something. But I didn't want to do it while I felt like someone was cutting my arse crack wider with a red hot knife. So I needed a better plan.

I made a harness. I glued a metal loop onto the base of the bottle so I could thread a leather belt through it. This belt was fixed to another belt around my waist. The result was a crotch strap which held the tapered end of the bottle tightly up my arse. I had a friction lock buckle at the front of the harness so I could pull the strap tighter to put more force on the bottle. I spread lubricant over the bottle and inserted it inside me as far as it would go. Then I'd pull the crotch strap with all my strength to make it as tight as I could. The strap dug into me as it went down past my cock and balls, pushing them off to the side. The waist belt squeezed me like a corset. I got the straps so tight there was only one direction the bottle could move. Up me. I would walk around the house naked from the waist down apart from my leather and glass contraption strapped between my buttocks. I'd squat down to the floor and bend over to touch my toes in order to work the bottle into me. It would very slowly push my anus open and under the tension of the straps it would very slowly creep up inside me. When I felt the straps become a little looser than they had been earlier, I pulled them as tight as I could again to keep constant upward pressure on the bottle.

I wore the bottle harness whenever I was alone in the house. Which was around once or twice a week as I still lived with my parents. Every time I wore it I could manage a tiny bit wider and deeper than I had the previous time. I had been wearing it for almost four months when I went to the kitchen to get a drink and squatted down to pick up a can from the floor. When I stood up I felt the straps had become slightly loose so I tightened them. Previous times I had done this it would take hours before they needed to be tightened again. But this time they felt loose immediately. So I pulled them tight a second time. I squatted down to the floor again and was overwhelmed by the most amazing mind blowing sensation as the bottle suddenly slid inside me. My anus had finally given up its grip on the taper of the bottles neck and had stretched far enough to fit round its widest part allowing the tension in the straps to slide it all the way up inside me. The whole bottle had gone up my arse. Just the very end of the three inch wide base stuck out. I was stretched as wide as I had ever been. I stood up and pulled the strap tight again to stop the bottle coming out. I was ecstatic. I was so pleased with myself that to celebrate I wanked myself off right there in the kitchen. Then I put a pair of jeans on, something I could never do previously as until now too much of the bottle protruded out of my rear. Now the bottle was fully inside me I could wear clothes again. So I went for a walk outside.

I wore the three inch wide bottle fully inside me for the rest of the day and most of the evening. I took great pride in sitting down just to feel its length shove up inside. I wanked myself off dozens of times until there was no cum left in me and my cock was doing the ejaculatory equivalent of a dry heave. If I hadn't needed to evacuate my bowel I would have left it in me all night. I didn't have to physically evacuate myself, just pull the bottle out and the waste fell out of me. I was a little concerned when I realised my anus no longer closed unless I made the conscious effort to hold it shut. But the anus is an amazing organ. Within an hour or so it had recovered and was operating itself as normal. A couple of days later I was able to fart with confidence. I continued to use the bottle harness on occasions when I felt like I needed the ultimate butt-fuck. Maybe three or four times a year, up until I was twenty years old. It worked best if I let my anus recover for a few months so I was starting again from the beginning. If I had used the bottle every day it would have went inside me easily each time. But if I allowed recovery time it took some uncomfortable strain and effort to achieve the full three inches stretch again.

I know someone will ask, "What does it feel like to have a three inch wide bottle inserted in your anus?" It's quite difficult to describe. You'll really have to try it to find out. But if you do, you will feel completely filled up. (Well Duh!) In fact you will never have felt so full. It'll feel much bigger than it actually is, like it goes all the way up and into your stomach. Your flesh around your anus will be stretched as tight as a drum skin and will be quite sore and hot for a while. But you'll get used to that. You may feel nauseas at first, but that will pass. And until you get used to the sensation, you'll feel like you're going to shit yourself all the time. Trust me you won't. If you really need to shit you'll feel a solid tension up inside your abdomen almost level with the small of your back. You'll learn to recognise that. You'll feel an incredible sense of satisfaction when you achieve your goal and the feeling when the tiny incremental movements of the bottle suddenly changes to one big thrust inwards when you stretch far enough to swallow the whole bottle is a tremendous rush. It's worth all the effort for that one moment. Would I recommend you do it? Absolutely yes. If anal stretching interests you, do it. You'll experience a host of sensations and emotions you never realised you could.

I stopped anal stretching when I was twenty two years old. I had done everything I wanted to. I didn't want to go wider. And I wanted to let my arse recover properly. Now, 24 years later, my arse has recovered all its strength and no medical examination would be able to tell I could once store a wine bottle up my rectum. The anus is an amazing organ and it's a terrible shame that most people do not attain the intense sexual pleasure they could from theirs. I wouldn't expect others to go to the extremes I did, but more people should enjoy modest anal sex of some kind.

Having made the decision to have anal sex with Rachael I went in search of lubrication. I had never had anal sex before so was not equipped. I found an especially slippy hand cream that seemed ideal and took half the tub to smear all over my cock. I hoped it wasn't an expensive product and made the metal note to buy Ray a replacement tub. Due to my years of experimenting with my own anus I knew that it was very possible to have anal sex without any pain. If it's taken slowly and gently until the recipient becomes accustomed to penetration. But my sadistic mind was in control today so gentle was not on the schedule. I wanted Ray to feel maximum pain so I could enjoy it. So I lay on top of her, placed the slippery head of my cock on her anus and pushed it in. It took a lot more effort to gain entry than I expected. A lot more effort than I ever needed to enter my anus. The head of my cock entered Rachael slowly and as I continued to push inside the tight grip pulled my foreskin down off the head of my cock so hard it felt like it would be torn off and I would be accidentally circumcised. As I progressed I could feel her squeezing grip strangling my cock all the way to its base. I lay for a moment to relax and enjoy the extremely tight grip she had around my swollen cock.

Rachael however, was not relaxed. She was in a very agitated condition. She was breathing very heavily and making a noise which sound like half grunting, half crying. She was tied tightly and completely unable to move anything except her head. So she moved her head a lot. She looked to one side, then the other, then straight ahead. I assume she was looking for something that would help her. But there was nothing. She was in pain and I loved it. I lay motionless on top of her becoming more and more aroused and enjoying the horrible spectacle of her trapped in suffering. After a while she calmed down a little and settled into a routine of slow calculated deep breaths. So I started to fuck her. Slowly sliding myself in and out of the vice grip of her anus. Not to fast as I wanted the experience to last. But as I started to enjoy it even more I couldn't help but speed up my thrusts. She was grunting loudly on each inward stroke and inhaling noisily through clenched teeth on every outward movement. Her virgin anus was unbelievably tight. I could feel every vein and slight undulation of my shaft as it slid up and down inside her tensed muscle. I shot my cum into her back passage. Now I was the one grunting noisily. The feeling was intense. It took all of five seconds to clear all the load out of my barrel. That is at least five times longer than it usually takes me. It was the best orgasm I have ever had. Rays arse was the best fuck of my life. Ever.

I pulled out and went to the bathroom to clean myself up. That's the only downside to anal sex. It can be messy. Then I untied Ray who also went to the bathroom and stayed there for over half an hour. When she returned she sat on the couch to watch TV and never mentioned what I had done.

She only ever mentioned anal sex once. It was summer and we were lying in the grass in the hills. Both naked as I had just fucked her arse. We had done anal quite a few times by now. This time she was untied in the regular missionary position.

She said. "It's getting much easier to do that."

"Doesn't it hurt anymore?" I asked.

"Only a little bit now".

And that was the one and only time she mentioned it. Ray was a true submissive. We never had a safe word. We never needed one. If Ray had said "stop" I would have stopped. But she never did. She never complained no matter what I did to her.

My depression was still getting worse. I wasn't communicating with Rachael much at all. I was drinking heavily. Our lives became mostly drunken sex with occasional painful highlights when I tortured Ray for my own pleasure. One weekend Ray suggested I didn't visit as she had to visit family. We both knew she was lying and she had just had enough. The fog closed in around Ray and she was gone. Gone from my minds view and gone from my life. I never went back. I realised I didn't love her. I don't think I ever had.

Rachael was an amazing person. She deserved to be loved and cared for. I wanted to do that but I ended up abusing her even worse than every other man she had met. I could blame my mental illness. It was certainly a large part of my problem. But that's not the whole story. I was an idiot. A sadistic self absorbed cretin. I didn't deserve someone as special and beautiful as Ray. She would be much better off without me. I withdrew into myself and became an alcoholic.

I saw Rachael every once in a while. We would pass at the shops or in a pub. She would smile and ask how I was. Even after the way I treated her she was still friendly. Then I moved away and lost touch. Twenty two years later I got a message from her on Facebook. She was still living in the same town. She was married with two children and was quite overweight. She sounds very happy. She still looks fantastic. I hope her husband appreciates how lucky he is.

After a few false starts I married too. She is the exact opposite of Ray. Tall, brunette, big tits and very much in control of her own life. I love her dearly, but when we argue I can't help wonder how my life would have been if my wife had been short, flat chested and blonde.

(PS - If you suffer from depression. Please seek help. If not for you, for those who love you)