Caroline

I apologise for the longer introduction but I feel it's necessary to let you know what you are in for!

This is a VERY long story. It is at 1,000,000 words now and is unfinished. Further writing will probably bring another 100,000. It is a fantasy, my fantasy, so I create the world within which it is set. Pretty much the same as ours but nicer! It is written in the first person, primarily because I like to write like that. That does present, however, a problem as the writer cannot delve into the thoughts of other characters. I overcome this by changing the narrator across the three major characters. The largest contributor is Caroline who is (in my mind) writing this while looking back on the early days of her life with Mike, the other major narrator. Occasionally Jo, the other main female character, with take over. This does lead to some repetition of events from a different perspective.

This was the first story I ever wrote and was written some 25 years ago before I ever posted anything on Literotica so you can understand that I wrote it for myself. It was posted some years ago but I removed it so it's being reposted. My wife describes it a Mills and Boon with sex -- lots of sex between several different people.

Be advised that, although most variations of sexual activity are described and enjoyed by almost everyone the primary focus is on anal sex. This is gentle and enjoyed with loving tenderness. There is virtually no sexual violence, indeed very little violence of any kind.

I will post the story in sections over several months (around 50 posts). I welcome comment and criticism although I would prefer the latter be constructive and not just vitriolic. Finally, apologies to US readers but this is written in British English so an ass is and arse!

Vitorio

~~~

Chapter 1.1

~~~

In which the story begins as Mike remembers his first time with Caroline:

I withdrew my still hard penis from her tight honeypot as she shuddered in another orgasm and lowered herself face down onto the bed. Before me was a sight to make a eunuch flinch. Here was this lovely young girl with the most beautiful bum laying naked face down on the bed. I looked again at the sweep of her body, down at the lovely indentation of her spine and small of her back, to the dark channel between the cheeks of her bottom. I loved the way her hips flared below her waist which, while not small, was perfectly in proportion to the beautiful cheeks below. I gazed on the indescribable rise of these cheeks and the curves they suggested. This was bliss indeed.

I reached forward and began to stroke her from shoulder to buttocks in gentle caressing movements, running my fingers lightly over the flesh, feeling the curves and contours of her divine body. I leant forward so that my cock was touching her bottom and whispered to her, "Now?"

She replied, "Yes, now, do it Please be gentle".

"As gentle as a soft breeze", I replied.

This would be her first time, she had never been taken in her bottom before. When we talked about this earlier she had expressed surprise that it could be done. She had read about it in books but thought it all a fiction. I told her that it was my favourite form of sex and I would enjoy it very much with her. She had asked why and I told her how wonderful her bottom was. I described the way her hips flared emphasised the curved shape of her body when looked at from the front or back. How it gave her a wonderful 'coca cola bottle' shape. At the same time, the way her bottom 'thrust out' behind, was so exceptionally enticing. There was a roundness to those cheeks and a beautiful shape to their return to her legs.

We were talking about this just after I had spent 15 minutes licking her fresh young sex and bringing her to her second orgasm. (Not the first time she had 'cum by tongue' as it were, but the first by a man!). I said how surprised I was that none of her previous boyfriends had paid much attention to what was undoubtedly a wonderful asset. She had replied by saying that most of them hadn't paid much attention to anything other than getting their dick inside her and/or shooting their load. She'd only orgasmed on a couple of occasions and that was more by accident than design.

I'd gone on to tell her that many women found anal sex to be very enjoyable and some even preferred it to vaginal sex. She'd asked whether it would hurt and I replied that the first few times might hurt a little but if the experience was nice, tender and loving she may grow to enjoy it. I had assured her that this was what I had in mind if she agreed to try. I also said that I thought it important that a woman should have several orgasms so as to be relaxed for the experience - so she could look forward to a few more.

At this point she suggested, sexily, that she might like to get better acquainted with my penis which hadn't featured since I'd taken her earlier. (I hadn't cum - when you get to my age you have to marshal your resources! -- my offering was hopefully destined for elsewhere!). She took hold of my, now slightly soft, weapon and moved her head downwards to my groin. As soon as she took hold I realised that, though she may not be experienced in straight or anal sex, she knew how to handle a cock.

She slowly began to work one hand up and down my tool and to fondle my balls with the other. I quickly became fully hard again as she bent her head to take me into her mouth, the head in first, then sucked strongly causing me some distress -- I was almost taken by surprise and shot my load (something I didn't want to do yet). Thankfully I was able to hold back! After the initial suck she began to lick like a lollipop from the base to the head, all the while playing with my balls in a most beguiling manner. Then back for another suck. Her mouth was a moist paradise filled with warm saliva as she sucked on my cock and stroked it with her hands.

I wondered just how experienced she was at giving head so I said, "Caroline, can you 'deep throat'?"

She looked up and, taking my cock from her mouth, replied, smiling, "How deep do you want it?"

"As deep as you enjoy", I said smiling back.

She began then to take all of me into her mouth. As she swallowed it, I could feel the back of her throat with the end of my penis and her nose tickling my pubic hairs.

"Jesus, Caroline", I said, "that is fucking fantastic. But not too much or you'll get a mouthful of male essence!".

She pulled her head back off my cock and looking at me coquettishly said, "I wouldn't mind," she said, "I think I'd like the taste of your spunk!" This from the lovely Caroline!!

She went back to sucking and deep throating my cock. Laying on my back I could look down and see this lovely blonde head bobbing up and down on my cock -- I didn't think that I could stand much more of this and, much as I would have liked to fill her mouth, I wasn't ready to 'waste' it here (at least not this time - but more later).

I put my hand on her head to bring her to a halt and she looked up, almost sadly, and stopped her most enjoyable sucking. She snuggled up until we were level and we kissed and touched for a while. As I kissed her my hands slid down to her lovely rounded bottom and I jokingly suggested that it was time I got to know it a bit better. She languidly turned face down on the bed, turned her face to me and smiled, "Go on then", she said.

As I sat up I gazed on the beautiful sight before me. The soft curve of her back indented by the undulations of her spine blending in with the upward rise of her buttocks and that valley of pleasure between. I leant forward and softly kissed her neck, her shoulders and the top of her spine. Then I ran my hands down the length of her back and over her bottom, feeling the smooth softness of her skin and causing her to utter a long drawn out "Ooohhh". I put my tongue at the top of her spine and began to run it down the whole length, gently tickling her and tasting the slight sheen of sweat that had appeared after her last orgasm. It was heavenly. As I reached the base of her spine I darted my tongue into the top of the crevice between her buttocks but I didn't want to go deep just yet. I wanted to try to bring Caroline to orgasm just by stimulating her anus and her tits. If I could do that, and she enjoyed it, it would prepare her well for her later anal initiation with eight and a half inches of my cock.

Still licking her body at the base of the spine and the top of her buttocks, my hands caressed her bottom cheeks and stroked the area at the top of the back of her legs, that very sensitive area near the perineum (I was saving this area for a little later!). Now I began to lick and kiss the cheeks of her bottom, determined to cover every square inch of this lovely terrain and, after I had done so, moved to that area between her legs. As I approached with my tongue she must have felt my breath brush across this most private area because she let out another long "Ooohhh" and opened her legs a little more. I reached up and parted her cheeks and looked at her tight crinkled rosebud. How small it was, how tight it would be. I almost came at the thought of my cock gripped by it. The ring itself was perfectly proportioned with a lovely golden sheen formed by the very light hair that ran over her buttocks. Her anus was not hairy (rather like her sex) and, to an old arse worshipper like me, looked so desirable. Again I experienced this animalistic desire to debase her, to take her dark virginity with my rock hard dick. To get as far inside her as I could and make her beg for mercy as I sodomised her before I filled her tight body with hot juice. But I allowed it to wash over me and disappear.

I began to lick the crack of her bottom at the top, gently flicking my tongue between the cheeks and then, using my whole tongue, giving a full lick, coating the valley with saliva. When I reached her tight little ring with my tongue she whimpered in pleasure and started to move her hand to her mound.

"Don't Caroline," I said, "Just 'feel' your bottom and boobs. You're going to cum that way". She muttered a little protest but moved her hand away.

I continued down past her anus and onto her perineum, that intensely sensitive part of both men and women, but I didn't go as far as her sex. I wanted the focus to remain on her bottom. Licking backward and forward between her vagina and her anus caused a continued shuddering in Caroline. She was mewing softly in pleasure as I continued to lick and kiss her.

I was getting quite excited myself at this stage, sucking and licking a beautiful girl's bottom and anus is a great turn-on for me, especially when I hope to take them later. (Having said this however, I enjoy doing it even if I don't get to do so). I moved directly to her tight little rosebud with my tongue, first coating it with plenty of saliva (not good enough for a penis but OK for tongue or finger). At first I concentrated on the area around the ring itself by holding her cheeks apart to gain perfect access. I wanted to stimulate her tits at the same time so I had to use my face to keep the cheeks apart. As I thrust my tongue directly into her anus I reached up with one hand and started to play with her tits. I noticed that her nipples were as hard as stones and, as I started to play with them, she moaned again in pleasure.

My tongue was now firmly planted in her back entrance which had loosened somewhat and opened a small amount. I rolled my tongue and began to push it in and out at the same time as playing with her nipples. After a few minutes of this most pleasant exercise I removed my tongue from her rosebud and, now that it was quite loose and covered in saliva, inserted my middle finger. As she was open I decided to take a risk and push it in quite a way quickly to see what effect it had. Hey, did she go wild! I couldn't believe the way she reacted -- she loved it. As I reached the second joint she thrust her bottom back at me and got my finger all the way in.

"Is that good?", I said.

"Oh, yes, fantastic", she replied, "I didn't think that it would feel this good, but I didn't think that you were going to put it in yet."

I laughed, "You haven't got my JT yet, only my finger. That comes later!"

"It feels so big and I feel so full. Will I be able to do it".

"I'm sure that you can, just enjoy the finger for the moment and let yourself go".

So saying I started moving my finger in and out to fuck her tight little arse. At the same time I continued to play with her nipple, pinching and squeezing. I was able to move my face nearer to her anus as my finger went in and out and was gently stimulating her ring with my tongue as it did so. I could see the tight rubber ring of her anus clutching at my finger as it invaded her. I was in seventh heaven at this time -- there's only one better thing to do than this! I had to be very controlled or I would have deposited my load on the bed and lost out on my aim of breaching this gorgeous bottom later (I'm afraid I'm a 'one shot' merchant now). She seemed to be enjoying my ministrations, so I thought I'd see if she could take two fingers. Her rose was definitely looser now after the fingering and very wet with my saliva so two fingers went in with a little stretching and, it seemed, without any discomfort.

Despite my increasing desire to 'rape' this beautiful virgin derriere, I didn't want to be too rough with her at this point, not to turn her off the idea of having sex this way for the first time, so I went very gently forward with these two fingers. I did, however, want to bring her to orgasm if I could. She was obviously enjoying the feeling of something in her back door because she started to move onto my fingers when they were withdrawn and I thought I detected an approaching orgasm as she again reached down to touch her sex. I didn't want her to do this so I thought that some talk may bring her on, as it were, so I said, "Caroline, do you like my fingers in there?"

She responded, breathlessly, "Oh yes, it's a lovely feeling. Strange but lovely."

"What about my tongue, did you like that?"

"Yes".

"What do you want now?"

She surprised my absolutely by replying, "I want you to lick me there, stick your tongue up inside and make me come. Please lick my arse. Stick your tongue in my bottom. Please!!"

How could anyone refuse such a lovely request, it looked like I was on track! I moved round, leaving her nipple, so that I was laying full length between her open legs and I could focus all my attention on tonguing this delectable dark retreat. I alternated between using my whole tongue to lick from the back of her sex across her perineum, across her anus, and up the valley between her cheeks; and pushing my tongue into her back passage. At the same time I massaged the cheeks of her bottom. It didn't take long for her to explode into orgasm as my rolled tongue was thrust into her tight little nether hole like a tiny penis. She thrust her beautiful rear back at me and shuddered before collapsing flat on her face. Her breathing was shallow and she seemed almost asleep afterwards as I crawled up level with her.

"Well?", I said.

"Oh god," she said, "That was like nothing I've ever felt before. I can't believe I said those things, used those words, but it was like somebody else taking over my body. I couldn't think of anything else except my bottom and what you were doing to it."

"Want to go for the whole thing?"

"Oh yes, I'd love to get that feeling again in my arse but you are quite big. Oh, there, I've started to talk like that again. It seems that, when I think of having you there, my head gets all 'dirty'."

I laughed, "I don't mind 'dirty', the 'dirtier' you talk the better for me. Do you like to hear that kind of thing?"

"I don't really know. I've never talked like that before and none of the boys I've been with have talked very much once they started".

"Well," I said, "Just say what you feel, and don't worry about size -- you'll manage. Take my word for it!"

She replied, coyly "Oh, I really do want to try it for real with your cock but will you make love to me properly again before you do it?" and looked at me with eyes so innocent I almost buggered her there and then!.

However, as I had in mind to take her again (I wanted her to orgasm again before I entered her virgin bottom) I responded, "Anything you want Caroline. What position is your favourite?"

"I haven't tried many 'positions'. I've been with quite a few boys but its always been pretty much the same, me underneath, them on top," she giggled, "fumbling around. With you its been different, you've thought of me and my pleasure. It's been a bit like some of the women's books that I read, you know, the romantic stuff."

"Perhaps its just because I'm older," I said, "and possibly a little wiser. I think sex is about giving pleasure as well as taking. I've had almost as much pleasure out of watching you enjoy yourself as I would have having an orgasm myself. I want you to enjoy yourself as much as you can. Have you got a fantasy position -- come on you must have read some things in these modern girls magazines!"

"Oh they're all very silly, they just talk about sucking but I do read Cosmopolitan and a lot of the women write in about being 'on top' -- can I try that?"

"Sweetheart, we can try anything you like. Tell you what, we'll start that way and then see what happens!".

So saying I began to kiss her lovely mouth and fondle her breasts to rouse her once again. My hand then went down to her vagina and started to stroke backwards and forwards along its length. She got wet almost immediately (I decided that this was one hot little lady!) as I focused on the little bud of her clitoris with my thumb.

"Oh yes," she moaned, "please do it now, I want you in me".

I rolled onto my back with my, now very hard, prick standing to attention, "Climb on board", I laughed, "its all yours!" I don't think that she was seeing anything funny, she was really hot and, without saying anything, she straddled my hips, took hold of my erection and guided it into her waiting honey-pot. She didn't bear down immediately but, from the look on her face, was obviously just savouring the feeling of my cock at the entrance of her vagina.

"Oh, that feels so different," she said. She looked me directly in the eye and smiled seductively as she bore down on me. The expression on her face was heavenly and I nearly spilt my load at the look of absolute pleasure she displayed. She continued to bear down on and take me all into her tight, hot tunnel of love. I'm not enormous but am fairly well endowed and she seemed to be enjoying every inch of it as she threw her head back and began to bounce up and down on my very erect penis. What a sight! She was beautiful, this young woman letting herself go with abandon, her small firm tits moving with her up and down motions, her face lost in pleasure.

I reached up and began to touch her boobs. I wanted very much at that point to put my arms around her and feel her body close to mine so I whispered, "Caroline" to bring her back a little way. She looked at me with wide eyes as I reached out to her and then she fell forward into my arms. We covered each others faces with kisses as she continued to pleasure herself on my cock.

"Don't cum yet," I whispered in her ear, "make it last, enjoy".

"It feels so good like this. I wish it could last forever".

"Turn round," I said, "I want to see that lovely bottom of yours as you work my cock."

Without getting off me she turned around and faced my feet. What a sight. As she leant forward I could see her tight little ring just behind my penis going in and out of her. It would open just a little bit as she rose up and tighten as she bore down. How I wished I had two cocks so I could fill both holes together. I reached forward and began to massage the cheeks of her bottom, pulling them gently apart to see more of her delicious rosebud as it clenched and unclenched. The view before my eyes almost brought me to orgasm but, again, I managed to hold on for the later anal initiation.