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“Happy Birthday, John,” Grace announced as she arrived at my home and handed me a neatly wrapped, beribboned package.

I had not expected a present such as this.

I had expected Grace to come empty-handed.

“I’ve given your birthday present a lot of thought, and I hope you like it,” she continued. “I know it’s something you’ve been wanting for a long time.”

I had to be gracious. I instinctively embraced Grace and hugged and kissed her.

“I’m sure I will,” I replied.

She must have detected some disappointment in my voice, so after our hug she continued by asking “Well, aren’t you going to open it?”

“Of course,” I replied. “And thank you for being so kind and so thoughtful.”

I then proceeded to unwrap the package. I was sure I was going to be disappointed.

Inside were two tubes of KY gel and a packet of condoms.

I was relieved. Grace WAS obviously going to surrender her anal virginity to me as a birthday gift, as I had a sneaking suspicion she would.

“Grace,” I responded. “Come to bed with me now and let’s enjoy some vaginal before we have some dinner and start to think about anything else,” I suggested.

I knew that Grace would accept that suggestion because, hidden somewhere inside her exceptionally attractive exterior, she has a seemingly-insatiable capacity for taking my erections — an ever-willing desire that it seems I had identified, and suddenly ‘switched on’ in her, some years ago.

“If we do, will you be up to popping my anal cherry later?” Grace then enquired.

“Have I ever not been up to meeting your needs several times a night?” I replied.

So, without further discussion about what was to happen later that evening, Grace and I moved to my bed.

Grace and I had sexually joined hundreds of times before. Or, to put it more crudely, I’d fucked her hundreds of times before. I’d enjoyed every encounter. I assume Grace had done so too.

This afternoon was to be no different.

But I was unusually eager to get into her pants. Perhaps because I’d not been in them for some weeks.

First to again have a really good feel of her cunny — to have my hand slowly feel her oh-so-taut box, feel her oh-so-smooth box, feel her totally hair-free box, feel her oh-so-seductively rounded, so absolutely feminine box…to let a finger slowly feel its way up her vaginal canyon to finally lift and stretch her clitoral hood…to then have several fingers gently feel her oh-so-receptive clitoral knob, to gradually increase the sexually excitement that Grace was feeling and (if it is possible!) to make her even more sexually eager…to have a finger or two dive down into her vagina to feel her g-spot and then to feel her little love tunnel progressively become wetter and wetter.

And then, to follow this, to with a really good rogering.

I desperately needed to screw Grace that day. It had been weeks since she and I had last been in bed together. And, as you know, she has always provided me with a naturally tight, really satisfying screw, so — whatever else might happen later that day — I was determined that her visit was going to start with both of us naked in bed together, as physically close as we could possibly be, simply enjoying ‘a damn good fuck’.

I knew that Grace would expect me to run my hands all over her body. To feel my tongue and lips make contact with her most female of erogenous zones. For me to feel her clit….to play with her tiniest of tits…to run my fingers along the length of her anal cleavage and then touch, just so gently touch, the entrance to her ‘no, don’t go there!’ ass hole. For my fingers to dive inside her vagina and find and stimulate her g-spot — hopefully bringing her to orgasm before I had given any thought to penile penetration.

…And for the palm of my hand and my fingers to simply cup her box, allowing me to again savour the tautness, the silky smoothness of that very special area of her body…an area that, quite simply, totally captivates and excites me.

I was only too aware that afternoon that, if I let my fingers travel just a little further around her crotch, they’d be on or be in the virgin hole that Grace would soon be allowing me to fill.

I knew that I would eventually feel Grace’s tiny hands reach for my balls and for my male member, eager to ensure I had a totally stiff erection.

If I was lucky (as I was that day!), she would take my erection into her mouth and pleasure it by sucking, sucking, and by then sexually teasing me by repeatedly running her tongue along that oh-so responsive ridge that runs up the underside of my penis.

And then — somehow knowing I was very close to involuntarily ejaculating — she would ask “what are you waiting for?” and move so that her cunt was obviously ready to be entered. To be fucked, fucked, fucked…to, ultimately, be rewarded with generously wet spurts of jism that would be deposited somewhere deep inside her receptive little body.

Sometimes she would be lying on her back to receive her penetration. Sometimes on czech sharking porno her haunches in doggy position. Sometimes with her back to me, waiting to be entered from the side. Occasionally with her legs dangling over the end of the bed, craving an unusually hard fuck. And, once in a while, she would even move out of the bed and stand up against a wall with one leg pointing skywards offering me a clear, unobstructed passage into her tight little love tunnel.

Over the years this little lady, with her tight little cunt, had worked out how to add regular variation to our love-making. Which both of us absolutely loved!

That afternoon she elected to be penetrated in the simple Missionary Position…her legs splayed and pointing heavenward. And she ended up wet…and satisfied…and I ended up (as usual) exhausted!

I had given her, she had accepted, a ‘damn good’ – an ‘unusually damn good’ — screw. So, for a short while, we both just needed to lie together, simply savouring what each other had offered.

Eventually we thought about dinner. But before we left the bed I cheekily asked Grace to spread her legs again so I could just look at and appreciate the enticing, thoroughly feminine landscape that was usually hidden away between her legs.

Grace, being Grace, was not going to refuse this simple request…and I was not going to take any advantage of her then-submissive situation by trying to finger her or even trying to kiss her.

So I just looked at — and thoroughly enjoyed looking at — all this beautiful lady now willingly presented to my gaze.

And ‘down there’ she was visibly very moist.


Grace followed my ‘viewing’ by indicating she wanted to have a serious talk about what was likely to happen next.

“You ARE going to pop my anal cherry tonight,” she announced. “I’ve absolutely decided that, but I want to talk to you in detail about it first,” she said as we headed to the shower to rinse ourselves off.

Showers with Grace (and also with Rebecca!) are always special. They are fun, they are intimate. We do things, playing with one another, in the shower that we didn’t do in bed. And, not infrequently, I have Grace pinned up against the shower wall, or bent over, or bent over backwards, receiving yet another damn good fuck.

And, invariably, whenever we had showered together of a morning at the time she was living with me, I’d be late to work.

If my receptionists had kept a diary of my late days, they’d now have a diary of the days that Grace had started her day cosseting my sperm!

There was to be no sex in the shower that afternoon…but it was fun and I sensed, somehow, it was unusually intimate.

Especially as Grace allowed me to run my fingers up and down her buttock cleavage for longer that I had ever done before and, with a dab or two of KY Gel on my fingertips, allowed me to run my finger around and over her ripe cherry-coloured anal opening.

It was taut.

“You’ll have to relax your bum hole,” I advised. “If you are ever going to get the head of my man through your anal sphincter I’ll need a wide-open hole down there, not something that’s closed up. So, give it a go.”

She relaxed it a bit, but as soon as I touched her down there again, she would tense up.

“Just relax, relax,” I further advised. “You must absolutely relax and enjoy what’s happening to you down there, because if you don’t you’ll be screaming in pain as I try to push my erection inside.”

I think she got the message, but I still felt that convincing her to relax to dilate her anal opening was going to be something of an ongoing challenge.

This was the first time I’d really had a close look at Grace’s little rear entrance.

It was cute. Really cute! Seemingly made to be fingered! Not to be unnaturally stretched and opened up — even by me!!

Especially by me, with my size L or OS cock!!

Having dried ourselves and — sort of — dressed, we moved to the lounge room. Grace detoured by the refrigerator and poured both of us a glass of wine, before snuggling up to me on the sofa.

“John,” she started “I love you. I really love you.”

“And I only wish you had been inside my head over the past few weeks because I’ve really wrestled over what is about to happen and what I’m about to say.”

I was a bit taken aback. This was Grace being very serious. I knew I just had to listen.

“John, I love you. If I really didn’t love you there is absolutely no way I’d be here now, allowing you…wanting you to give me anal.”

“And, John, I’ve decided over the past few weeks, while thinking about things, that I really want to move back in with you. Not on a temporary basis but permanently. Because you are the most gorgeous, most caring, most loving person I have ever met.”

“Thank you, darling” I replied. “I’d love to have you move back in, but you are asking us both to make a huge commitment, so perhaps we could talk about that in some detail tomorrow, or even the next day.”

“Let’s just czech streets porno focus right now on what’s about to happen. You’ve obviously been thinking deeply about that too, and I’d like to hear how you’re feeling about it.”

Grace had obviously done a lot of research. She started by saying that she had moved from viewing anal sex as an unnatural act to looking on it as something that was perfectly natural and something that, she understood, could be intensely satisfying to both parties…and something that, essentially, demonstrated a couple’s trust and love for one another. And the more that she had read about it, the more convinced she had become that anal was something she wanted to be able to enjoy and to share with me.

Grace also knew it involved risks. Significant risks. There was the possibility of contacting AIDS or HIV (although she thought the chances of contracting either from me was virtually zero) and there was a real chance of her tearing or puncturing something on the outside of her anus, or even internally — and that would then become really serious. She also knew that having repeated anal sex could weaken the muscles around her anal sphincter, which definitely would not be a good look for her! But, she realised, perhaps the greatest risk was that fecal germs could make her really sick — especially if they were carelessly transmitted from her ass hole into her vaginal area.

She knew the precautions she should take, and she suggested how we should proceed: she would toilet, she would have a very warm bath, she would be lubed up and I would then start by inserting one and then two fingers into her anal cavity to dilate it as much as possible. After scrubbing my hands, we would both work to ensure my penis was fully erect and I’d put on a condom. There would be more lubing of both her back entrance and my condomed erection before I would lie on my back, erection pointing upwards and she would position herself on top of this and slowly lower herself until my erection was fully inside her. I had to promise there would be no thrusting until I had fully penetrated her and she was comfortable having my erection inside. And I had to be extra careful to keep my fingers, which should ultimately be providing her with vaginal and clitoral stimulation, well clear of her rear entrance.

And, I should never expect anal to become an everyday part of our lovemaking. It was to be an occasional ‘special treat’ to reduce the likelihood of gradually weakening her anal muscles.

I thought she had a pretty good checklist of what should happen that evening. It sounded clinical — but the reality is that the process of giving or receiving a first fuck, be it anal or vaginal, is a somewhat necessarily clinical undertaking.

And I, rather than Grace, was more likely to enjoy this once-in-a-lifetime experience upon which she was about to embark.

I told Grace there was just one thing I would add to her timetable. Once she has finished her bath I would separate her buttocks as widely as possible and, with gaffer tape, try to ensure they were kept spread well apart. This would help to provide unimpeded access to her tiny target hole.

And I cautioned her to act slowly, and be prepared to do things differently if, at first, she experienced difficulties or unbearable pain.

After a few more hugs and kisses, Grace told me she would skip dinner and “get it over with.” She suggested that I grab something to eat while she was soaking in the bath.

So the countdown to Grace’s anal defloration had begun.

Grace is petite. She knows I prefer her to appear to pre-pubescent, virgin-like and have no pubic hair. So there is nothing but skin (and that barest glimpse of labia!) below her bikini line.

In the bath, therefore, Grace has all the appearance of an innocent baby. Tiny tits and THE smoothest, THE most appealing ‘come hither and give me a feel’ crotch.

And a perpetual smile that was certainly not going to deter me from doing just that!

“Roll over and let me see how ready your beautiful ass-hole is now,” I suggested to her, before plunging my hand into the warm water and giving her an unsolicited feel, even trying to insert a finger.

“Darling you must relax. You’ve got to allow that hole to open right up, to become totally receptive. And you know how wide that has to become, because you know exactly what it has to accommodate,” I continued.

“Hop out of the bath and let’s see if the lube will help,” I then suggested.

After towelling Grace off, I had her lie on the bed face-down. First to tape her up, then to begin lubricating her ass-hole, then to see how easily I could slide my fingers into her virgin hole. I guessed this would probably be the most traumatic part of the evening for her — but, nonetheless, possibly the most important if her defloration was to be reasonably comfortable for her.

I succeeded in getting two fingers inserted. But barely!

It was evident that what must now follow was going to be painful to her. And that’s czech super models porno not surprising, because Grace is small!

She had some time to adjust as she sucked and squeezed my cock to help bring it to full erection, and watched while I rolled the condom down the length of my shaft.

We then lubed one another. Liberally. Very liberally.

I ensured that the much of contents of one tube were squeezed into her still-virgin hole and were liberally distributed around the rim of her anal sphincter…and that she felt totally wet and slippery to the touch.

Oh, how much I (and my erection) now just wanted to get inside that still-virgin hole!

It was a quick dash to the bathroom to wash my hands before I returned to lie on the bed, face (and erection!) up. “Are you O.K. to go?” I enquired.

Grace said nothing. She just positioned herself astride of me, facing away from me so I could not easily observe her facial reactions to what was to follow. I helped guide my manhood to the entrance of her hole and then moved my hands to gently hold her waist.

She lowered herself a little. A little more…and then let out an obviously painful “HOLY SHIT!”

“Take your time,” I suggested. “And try to relax some more down there.”

She tried twice more. I had the feeling we were making some progress, but very slow progress.

Grace was obviously hurting.

“I’m going to suggest you now lower yourself forceably and rapidly to get the head of my erection through that gate — just like I had to do when I popped your vaginal cherry,” I suggested. “If you want me to help, I’ll try pulling you down,” I added.

Grace indicated she wanted to try it first by herself.

Many seconds elapsed before Grace did so. She was probably steeling herself for the pain she would receive, and she was probably trying to relax her anal muscles.

But she succeeded — if accompanied by a loud, obviously-painful ‘aaarrhhh.’

But at last the head of my engorged penis was inside. And I imagined I heard a muted ‘pop’!

I was not yet deep inside Grace…but I was inside.

With a bit of wriggling by both of us, the head of my shaft gradually worked its way in as far as it was likely to travel.

So success! Grace’s anal cherry had finally been popped.

“How are you feeling? O.K.?” I enquired.

“Sore, but I think I’m alright,” she replied, almost in exasperation.

I then suggested Grace allow me to totally withdraw from her anal canal and that we try penetration for a second time, after which she should allow me to engage in some thrusting that might ultimately lead to my ejaculating.

That happened — a lot more easily, a lot more pleasantly for us both.

I even got to insert a finger into Grace’s vagina and started fingering her there while she ‘rode’ me. Grace was, I think, relieved to discover that anal was likely to be a more intense, a more rewarding, experience than even the best vaginal had ever been for her.

My erection had become quite flaccid by the time we eventually uncoupled…and I was surprised that the ever-thoughtful Grace had even supplied a sanitary bag into which I could pop the now very-wet condom.

I instinctively wanted to grab Grace’s ass and run my finger down to her newly-penetrated hole. “No, not until after I’ve had a shower,” I was sternly informed.

Neither of us slept well that night. I kept re-living what had just happened, wondering how much pain I had inflicted on Grace. And I was eager to again re-enter her behind.

I was also thinking how should I respond to Grace’s wish to move in with me permanently. When should I change my status from ‘single’ to ‘in a relationship?’ Should I ask her to marry me — immediately, some time later? Should I buy her a ring when she moved in, or should I mark the event in some other way (apart from giving her a loving, ‘welcome’ anal fuck!)? Presumably, if she was moving in permanently, at some time she would want me to father her child, so should we be thinking about moving to a bigger house? How might she re-decorate ‘our’ house? Would ‘my’ guest house discipline rules now become ‘our’ house discipline rules?

(Which, as an aside, perhaps I should explain to you! Grace now well knows that when she is asked to be ‘very, very good’ she will shortly be sucking cock, or exposing her tiny titties and cunny to a really good sucking. And if she is ‘bad’ [or, occasionally, ‘not bad enough’!] she will find her pants and panties are being removed for her so-cute little bottom to be warmed and reddened by a few well-directed smacks. And on the rare occasion that Grace becomes enraged, she will be firmly instructed to ‘stop…strip…then place your hands on your head…and just stand there while you cool down and I am able to keep an eye on you.’ Which, of course, I will do — very, very closely! — until her feelings of anger become supplanted by a self-conscious feeling of naked immodesty.)

And how was I going to cope with now not being able to provide as much practical sexual assistance to that stream of appealing young schoolgirls (all, coincidentally, from just the one high school!) who regularly provide me with opportunities to educate them and to, simultaneously, meet some of their most basic, most natural female needs? That was going to be (almost!) the hardest question for me to answer.

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