Caroline

She was obviously nearing another orgasm so I suggested changing positions before that happened. She reluctantly climbed off me and I positioned her on her side with the top leg drawn up to her chest. This exposed both her pussy and anus. God, it was difficult not to bugger her then and there but I put my penis in her sex and began to stroke her in earnest. She seemed to like this position, especially when I started to tease her exposed clitoris and it wasn't long before I sensed her approaching orgasm. I would have liked to take her from the rear 'doggy style' before she came again but I feared it would be too much for me to be able to hold out much longer. Moving over her I ran my finger around her ring piece at the same time as my other hand played with her clit. As soon as my finger touched her still lubricated nether hole she pushed back so my finger entered to the first knuckle. She came almost immediately with a cry of "Oh fuck, fuck, fuck" and her body almost vibrated as the pleasure coursed through her. Again I had to exercise complete control -- believe me not easy when you see a beautiful young woman completely lose herself in orgasm.

So here we are, at the point where she is giving me her anal virginity, the first man to go there. The first male member to split those beautiful cheeks. The first man to stick his JT into that tight little cavern of love. The first man to fill her bowels with his cream. They say that sex is mostly in the mind -- it certainly was in mine. I didn't think that this first initiation would last very long, I certainly wasn't going to!

I knew that it was important for the future that this went well so I reached for the tube of KY on the dresser.

"Kneel, Caroline", I said, "stick that lovely derriere in the air".

She pulled her knees underneath her and pushed her bottom up in the air. I gently parted her knees and pushed her head down so that she was totally presenting herself for her virginal trial. She was looking back at me with a soft smile on a face that looked a tiny bit apprehensive.

"Will it hurt?" she asked again.

"Yes, it will at first," I replied as I massaged the cheeks of her bottom. I wanted to be honest with her, "But if you enjoy it the discomfort should go away."

"I hope so", she said, "I want this to be good".

"I'm going to use some lubricant to make it easier," I said, "just try to relax".

As we were talking I squeezed some KY and began to massage my cock with it. When it was nice and covered I squeezed some more and started to massage it around Caroline's anus. Not right inside yet, just around the tight little ring. Then another squeeze, this time directly into her bottom hole, and a massage gently inside. She gasped as I applied the KY and I asked, "Are you OK?"

"Ooohhh, that feels good. It's cold!!", she laughed as she pushed back slightly on my massaging finger.

"I'll warm you up in a moment", I laughed back and pushed a little further in.

"Are you ready", I asked.

"Oh yes", she responded and thrust her bottom back a me. "Stick your cock in my arse, fuck me up the arse, pleeeease".

Obviously focusing on her bottom released a totally different, completely uninhibited Caroline. I placed my now fully erect cock at her tight little ring. It seemed impossible that this tiny opening could receive it but I was certainly going to try. I pushed forward gently on the puckered anus which failed to open up to my attempted entrance.

I said softly, "Relax, just open to me". She sighed and, suddenly, my cockhead surged past the obstruction and was buried in her rectum. Caroline gasped and I kept very still. I wanted her to get used to the feeling of my cockhead inside her and, if I did move too much, I would end up spilling my load. Caroline herself also kept very still. I could see the skin on the small of her back 'fluttering' as the feeling of being buggered registered on her.

The pressure on my cock was marvellous. Her anal ring was gripping my penis just below the head where it narrows; it was like a tight, but extremely pleasant, rubber band. I savoured this for a few moments then said to Caroline, "Are you OK? Does it hurt?"

"I'm OK and yes it does", she replied breathlessly, "but keep going."

I continued to push forward into her tightness and, after another two inches, stopped again for her to get used to the feeling. This brought a sob from her, it was obviously painful.

"Is it still hurting," I asked, concerned that she should enjoy this first experience of anal sex.

"Yes," she said, "but it's not so bad. Go on, I want to try to have it all, please. Don't mind if I hurt a bit."

I looked down and saw her beautiful bottom, set below her waist like an upturned heart, pushed up in the air and thrust back towards me. I saw that lovely valley between violated by my solidly erect penis driven four inches into her anus. The tight walls of her rectum were gripping my cock and I felt again this animal desire to drive into her completely, to rape her with no care for her feelings. To debase her, to cause her pain, to thrust forward so hard that I would bury myself inside her. It was difficult to resist but thankfully I was able to do so and remain (fairly) calm. It seems to me true that the male sex drive is very basic and sometimes difficult to control.

After a few moments of stillness Caroline seemed to relax a bit, the pain apparently subsiding so I pushed forward a little more to get about 5 inches into her. At this point her sob changed to a little sigh and she began to mew softly, rather like a cat purring. I figured she was enjoying it! "How is it now?" I asked hoping she was.

"Mmm, that's nice. It hurts just a little bit but it's a nice hurt. I don't want it to stop. Is there any more?" she asked coquettishly.

My response was to thrust all of 6 inches into her but I felt an obstruction at this point. She wasn't used to anal sex so she almost certainly hadn't prepared herself to be buggered. I thought it best not to try for any more penetration: what I had was driving me close to orgasm and I had to last a bit longer - I hadn't really fucked her here yet. So I stayed still for a while and massaged her bottom with my hands until she started to, very slowly, move herself on my swollen member. This was the sign I needed, she was OK with me inside her, she liked being sodomised!

I drew myself out until only the head was inside her and looked down again. Her tight little anal ring was gripping me as if it never wanted to let it go. I drove forward, releasing some of the tension that was pent up in my body and mind. I still didn't go too hard, I wanted her to enjoy this. I got 6 inches in and withdrew almost totally.

Caroline looked back over her shoulder and said breathlessly, "Come on, fuck my arse. Fill me up. Oh how I want your cock in my arse. Give me it all. Come on, fuck me, fuck my arse. Fill my arse with your spunk. Cum in my arse."

This was almost too much for me. Obviously, Caroline was very sensitive to anal stimulation. It seemed to bring out a completely different side to her. I started on her sweet nether entrance in earnest, backwards and forwards, stroking her as hard as I dared. She was moving onto me so hard that I was sure it must be hurting when I hit the obstruction but she seemed to be over the moon.

I knew it wouldn't be long now, if fact, I was amazed I had lasted this long. Sure enough I began to experience the gathering of feelings prior to orgasm. My whole being was centred on my penis thrusting in and out of Caroline's clenching little (virgin no longer) rosebud and my balls dangling tightly below. I sensed as well that Caroline was nearing orgasm too; her breathing was coming in gasps, her body seeming to writhe in the pleasure she was receiving from me inside her tight rear channel.

Then I came, like a crashing wave (it really was like that -- no kidding) hitting me, and I began to pump my essence into Caroline's bowels, deep inside her. As I pumped, Caroline let out a long,"Aaaaaaaaaaaagh" and I could both see the effect on her body and feel the clenching of her anal tract on my cock. It was as if her orgasm was trying to milk cum from my body. I'd seldom felt anything like this before, it wasn't often that anal or straight sex had ever given me this intense feeling of being milked, drained, used, if you like, by this woman to satisfy the desire of her virgin bottomhole for my offering.

I finished cumming after 5 or 6 jets and Caroline came down from her high soon afterward. I like to remain inside a woman after anal sex until I get soft and am 'expelled'. It's a great feeling. On this occasion, however, my orgasm had been so intense that I needed to withdraw for some rest so I pulled out of Caroline while still quite hard. I could see the puckered ring or her anus, which had expanded to take my penis, closing gently. There was a little dribble of cum as I removed myself and it almost seemed as this ring was reluctant to let any escape. Slowly her anus closed and I bent forward to place my tongue on her rosebud and gently lick the mucus and spunk. Caroline sighed again and lowered herself down onto the bed.

I moved back up level with her and, in that calm period immediately after orgasm, placed my arms round her and hugged her close to me.

"That was fantastic," I said truthfully, "did you enjoy it?"

"It was out of this world," she said, "I don't think that I have ever experienced anything close to that feeling. I was like being full up all over. I could feel everything your prick was doing and when you started to cum, I could feel it inside me."

"Would you do it again?"

"Oh yes please, Now?"

I laughed, "I'm sorry darling, but whilst the spirit is very willing, the flesh is weak. It will be a while before I'll be fit for anything. It's not every day that I get to stay hard for a couple of hours, bring a beautiful girl to orgasm five (?) times and then come in her delightful derriere."

"I actually came six times, twice with you in my bottom", she replied, giggling. "I suppose I'll have to wait until next week then".

"So we're going to do this again are we?"

"You bet," she said. And then, "I must go to the loo, back in a minute". I watched as this lovely young woman got off the bed and went into the bathroom, she was indeed a thing of beauty with a body (and particularly bottom) to die for.

"Mike," she said when she returned and lay down beside me, "can I ask you a question?"

"Of course darling, fire away".

"It's a bit embarrassing really but I wanted to ask whether you put it all inside me just now, only I didn't feel you up against me? Aren't I awful? It's just when I think of you in my bottom I don't really care about being 'proper'".

"Don't worry about that, no I didn't put it 'all in'".

"Why, were you frightened of hurting me?"

"I didn't think that I was hurting you," I laughed, "you seemed to be enjoying it at that time."

"Oh, I was. I was just curious. I sort of wanted all of you. I suppose I was being greedy."

"I can handle that," I said smiling. "The reason is sort of difficult to explain without being crude. If you think of it that your bottom is designed for pushing things out not for something to be put in."

"Yes," she interrupted, "but it was nice when you put it in."

"Shush you minx and let me finish," I chuckled. "Well, if there is something in your bottom waiting to come out then anything trying to get right in won't be able to."

"Oh," she said, looking pensive, "I see. Well what can I do about it?"

"Well I'm not an expert", I said, "....

"You certainly knew what you were doing in my bottom," she interrupted laughing, "it seemed pretty expert to me!"

"Hush woman, and listen, some women I have known prepare for sex by ensuring they are empty there. Some gay guys I know, and I mean as friends (I only like female bottoms), who do this a lot use an enema beforehand when they get ready for sex. They say it's the best way because it's clean and they are more sensitive and experience more sensuality when completely empty. Some of the woman I've been with have told me they used enemas. Those who were very sensitive in their bottoms said that they enjoyed it as a prelude to anal sex."

"Oh, I understand now," she said, blushing slightly. She was such a charming girl; a blush when talking about it now but totally sexual when getting down to the anal sex. "I'll ask Joanna about it. She's a nurse."

"Will you tell her about having anal sex for the first time"?"

"Oh yes, we talk about boys and everything. I'll be able to tell her that I've been with a man! not some silly boy. She'll be really interested and she'll be really jealous that I've found you."

"Thanks, you make me feel young again. I only wish that I could perform like a youngster."

"I like you as you are. Nobody has ever made me feel like you did today. I can't wait for next week!"

"Come on," I said, "let's have a shower together."

And we did.

We had a long lunch (it was after two by the time we had dried off). I realised that I had been hard for nearly two and a quarter hours and only come once, maybe there was life in the old dog yet. After lunch I took Caroline home and watched her swaying bottom as she walked up the path to her door. I wondered whether I would have another go at making love to that delicious bottom.

Note from Mike:

This and the next chapter were written some time later at Caroline's behest.