He Did What He Did To My Rear

I know this category is for lovers of anal, but there are some people who really don't love it, and this story is told from that point of view. As a complete departure from anything I have ever written on this site this tale of woe is told first person, from the female point of view, and is one woman's story of her sexual history and of losing her anal virginity. Please enjoy, and if anyone ever performs the rewritten lyrics live, or even records them please let me know how it goes, and also I would love to see or hear a recording of it if you can post it somewhere. BB1212

I had an old song by Tony Christie that my Mother used to love running through my head, but the words had somehow changed to better suit my dire situation. Yes dire. OK, I'm Sally Travis, I'm twenty eight years old, I manage a boutique fashion store, I live in a large city and so far I am unmarried. I... well I... I might just let the song tell this part of the story, OK?

Sunrise, this is the last day that I'll ever be,
Waking a virgin (at least one of three),
And I face this new day with much fear.
'Cos I foolishly promised my rear.

I started out in my journey to womanhood like a lot of girls. Through high school I was sweet and innocent. For a long time I didn't like boys, but then I kissed David Grange at a party when I was sixteen, and I thought I was in love. I thought he was in love too, but two weeks later he got sick of me refusing to let him go any further and he dumped me to try his luck elsewhere. I was devastated. It took me ages to build up the confidence to try again, but eventually I did. I managed to avoid doing anything more than kissing until I was eighteen, and even after that I took things slowly, but eventually I graduated from heavy petting, to giving, er, hand relief, then oral sex and finally I went all the way. Well I thought that was finally, but there was one more possibility that I never even considered at that stage. But now it was going to happen. Take it away Tony.

When I drove into town with the sun going down,
I went straight to a bar, my reluctance to drown.
With regret I had come, but I wanted to run,
From a nervous concern for my rear,
My last pristine part, yes my rear.

I sat on a bar stool and stared into my second Martini. I was wondering how I had let him talk me into this, and as I wondered my mind wandered back to Gerald Moore. He was my first first. Yes, I know that sounds weird, but he was the guy who took my oral virginity. Gerald was fun with a capital 'F'. He was on the football team, and while he wasn't one of the stars he always did well. We would go out on Saturday nights after the game and we'd end up at the local lover's lane snuggling together in the back seat of his car. He was kind and understanding with me, giving me time to get used to things. The first time we went there we just kissed, but the next time he gently rubbed my breasts through my clothes. This scared me at first, and I tensed right up, but after a while I relaxed and started to enjoy it. The sensations were nice, but the best thing was having his undivided attention. I was naive enough to think he was only considering me and my pleasure. A couple of weeks later he worked his hand under my bra, and the sensations got a lot better. Pretty soon it had got to the point where I was letting him suck my breasts and nipples, but only if there was nobody else around.

Eventually he convinced me to touch his thing. OK, I mean his penis, I'm sorry people, but I still don't like dirty talk. This is my story after all, and I can call it whatever I want. Anyway, it was reasonably early on a Saturday evening and he sort of begged me to at least touch it. I was terrified as he unzipped his pants and he took this massive thing out. Nervously I did touch it, and it was warm and sort of soft. Gerald told me what to do and I eventually worked up the confidence to stroke him until his thing squirted this sticky, gooey stuff onto his shirt. He drove me home without a shirt on, and I'm so glad my parents didn't see that. They would have had a fit. A couple of weeks later Gerald scored a goal, which is very rare for a defender, and he somehow convinced me that I should use my mouth on his thing as a reward. It was pretty awful. He smelled and tasted musky, and neither of us really knew what I should be doing. My jaw was aching when eventually, without warning, he squirted his foul tasting stuff into my mouth. I squealed, pulled away and retching I spat it out. Despite this he was happy while all I was doing was desperately searching for a drink so I could get rid of the taste. I got over my revulsion, and I did this for Gerald a lot more times. Eventually I grew to enjoy the power I had over his body as I sucked him and I also learned to swallow his stuff, just because it was a lot less messy. I also made sure I had a drink handy to get rid of the taste. OK, back to Tony.

Take a powerful brew, just to see this thing through,
Get a condom or two, and a lot of good lube.
Yes I recklessly promised my rear,
And I can't back out now I do fear.

With my third and final Martini I thought about Andy Deed, who was my second first. Gerald and I had gone to different colleges and we drifted apart. I had found a new group of friends, and they had all done it. I was the last and soon I realised that this was not an advantage. They would whisper and giggle about various boys and what they were like in bed. The girls weren't exactly what you'd call easy, I mean they were selective and they made the guys work for the reward, but they weren't too chaste either and they all seemed to enjoy sex. A lot. As a girl growing up I was given a strong message that sex was bad. Almost all girls were given that message, and that makes it hard to finally cross that bridge and try it. I didn't sleep with Andy because I was in love, I didn't do it because he sweet talked me either, although he had tried that on a couple of occasions previously, I did it because I was sick of being left behind.

It was at one of those student parties and I had drunk quite a few wines. I wasn't silly enough to just tell him that I wanted sex. By that time I had learned that boys, well at least the popular boys like Andy, want to be in control. It has to be their idea, but there is nothing wrong with steering their thoughts in the right direction. That night I had deliberately dressed sexy and I danced with Andy, making sure to make a lot of both eye and body contact. Eventually he got the idea.

"Wow, you're sort of different, are you horny tonight Sally?" he asked.

"Aren't you?" I replied, giving him my best sultry look.

Just a few minutes later we had found a private room, locked the door, and I was lying on my back on somebody's bed with my dress pushed up around my waist and my legs in the air as his condom covered thing pushed through my barrier.

I cried out in pain, but I was also relieved, at last I was fully a woman. Here's the song again.

I tensed, even as he was just lifting the sheet,
He acted like I was getting the treat,
But my sphincter was clenched tight with fear,
As I felt him approaching my rear.

I had expected pain when Andy had sex with me, and I got it, but I had also been told that this would get better, if not during this first time at least later. It was true. Andy had sex with me for only about five minutes before he finished and it wasn't even a little bit pleasurable for me, it was something I had to endure. He finally lifted his weight off me and pulled his thing out of me. Then he saw the blood on the condom. Surprised he asked me if I had been a virgin. He looked pleased when I said yes, and he left quickly, I think so he could tell his friends. I didn't care, because I had just gotten rid of what by then had become a major handicap. I had felt the pain of my first sex and I thought that was all the bad stuff over. But even then I never considered that other option. The option that all those years later I was now about to allow. I'll let Tony tell you this bit, I don't even want to think about it.

Well the cold lube applied, then his thing he did guide,
Well my nerve ends they cried, as he pushed it inside.
He was thick he was keen, and he sure made me scream,
He was more than too much for my rear,
My tortured, deflowered poor rear.

I had sex with four different boys while I was at college, but I never had a true one night stand. After that party Andy and I did go out for a while, but he soon decided I was too possessive because I didn't want to share him with the other girls who seemed to get more interested because he was attached. I did get to enjoy sex more too, but I certainly never felt the sort of pleasure that Meg Ryan faked in that famous scene from 'When Harry met Sally'. I did hook up with a guy called Harry at one stage for almost six months, and I promise it wasn't even a little bit because he was Harry and I am Sally. Anyway after I left college and went to work I dated a bit, and with practice and some trial and error I learned a lot more about sex. But years later I was single again and that awful biological clock was ticking. My wild friends had all settled down and they were all either in long term relationships or married. Two of them had already had a child and Amber Smith-Watson had just announced her pregnancy on Facebook. I know I'm not ugly, but it really hurts the confidence to be the only spinster in your social circle.

Rob was a guy I had dated a few times previously before he had moved to a different city. I had been rather disappointed when he left because he was handsome, he seemed to be honest, and we got on really well together. There was a good spark between us and his great well-paying job and the expensive car didn't hurt either. The only problem with Rob was that for some reason he really wanted me to try anal, and that was something I wouldn't even consider. Anyway, almost a year after he had left Rob turned up at my shop unannounced, shortly before closing time one Friday. It was really busy so we made arrangements to meet at a pub later that evening. As we sat together over a drink he told me his news. He had been given a promotion and this meant he had been transferred back to town and he had just got back on the previous weekend. Rob told me he was re-establishing friendships. He bought me a couple of drinks, he took me dancing, he took me home and he took me to bed. This wasn't a first for us, but it was the first time that we actually slept together and woke up in the same bed. When we woke up we made love again. I'll dwell on that nice happy thought while Tony continues the song.

Stretch my tight puckered hole, with your insistent pole,
Such a persuasive man with a back door resolve.
Yes somehow he conquered my fear,
And he finally plundered my rear.

Rob and I soon became an item. I had missed him and he certainly seemed to have missed me. We went to parties together and I even moved some important girly things into his bathroom because I was staying at his place every weekend. We talked seriously about moving in together. To tell the truth I quickly realised that finally I was in love. My friends were all more than a little bit jealous too, Rob had the looks, the style, the personality, well he pretty much had it all. I was thinking of marriage, and I decided that if he asked me I would accept. But then what he did ask me for was anal sex, and I told him I would think about it. This surprised me. I had always just said no, but to be fair I had never been this infatuated before. Rob was loving and attentive, that is for sure. He regularly gave me flowers, and on my birthday he gave me a beautiful diamond necklace. It was about two months later, in the week before his birthday, and as we were having dinner at a lovely French restaurant, that I finally gave in and with some trepidation I promised him a very special birthday treat. I never really considered the consequences beyond the act itself. Go on Tony, tell them.

Sun rise, this is the first day that I'll ever be,
Walking so tender, I sit carefully.
But it brings to my eye a large tear,
'cos he did what he did to my rear.

I have never in my life felt anything quite that painful, and not only did it hurt dreadfully at the time, but it also ached all through the next day. Walking was painful, sitting down hurt and don't even think about talking to me about going to the toilet. That day I almost swore off solid foods for good. Rob, of course, was well satisfied, and he treated me tenderly all day. Even so, I can't see me ever agreeing to endure that agony again.

But Rob is handsome, charismatic and quite well off. I wonder...

Take a condom or two, and tube full of lube
Stretch my tight puckered hole, with your insistent pole.....