Posing for Anna Ch. 03

The day after the night before... my head was still spinning from the events of the previous evening. Once more I gazed at the clock waiting for it to finally reach 4:15 so that I could go back to Anna's studio. She was obviously delighted when she saw me at her front door.

"Oh Martin! I'm so glad you came, I had feared that last night's shenanigans would've scared you off!" she said as she ushered me inside.

"Not a chance" I replied, "I've been clock-watching all afternoon because I just couldn't wait to get here!"

"You really did enjoy it didn't you" said Anna.

"That's putting it lightly! Last night I had the most powerful, most intense and most explosive orgasm I've ever experienced!" I said.

"The rest of the ladies have a tough task on their hands to surpass Melanie's skills then!" chuckled Anna.

"You could say that!" I replied.

We went out the back door, across the garden and into the studio once more. The fibreglass rock had gone, into the storeroom, and in its place was the couch with the red velvet drape.

"I had a bit of an idea this morning about how to make this series of paintings a little more intriguing, if you're up for it of course" said Anna as she closed the door behind us.

"Oh yeah, what's that then?" I asked.

"Well, in times gone by artists would often mix their paints with things like egg yolks and olive oil to give their paintings a distinctive sheen and I was wondering if you would be able to give me something to mix in with the paints I'll be using for this picture" Anna explained.

"What, do you want me to go down to the shop to get some olive oil?" I said not quite catching her meaning.

"No, I could've done that myself earlier!" chuckled Anna, "What I want is something only you can give me".

"Such as??" I asked.

"Your semen, silly!" she replied.

"My semen??"

"Yes, that way you can be in the picture in more than just a depiction of your body -- you can literally be a part of the painting!" Anna said enthusiastically. It certainly sounded like an attractive proposition.

"Ok then" I said, "no problem, you can have as much as you like -- or should I say, as much as I can make".

"Oh thank you, thank you!" Anna said as she hugged me.

"But there's just one thing though" I said.

"What's that?" asked Anna.

"If you want it you have to come and get it for yourself" I said with a wink.

"I was hoping you'd say that!" Anna said with a smirk, "Take your clothes off and let's get started!!"

And so, once again I undressed. As I took off my clothes, Anna went into the storeroom to find something for me to ejaculate into -- a small pot would have sufficed but she could not find anything suitable in the confines of the storeroom or the studio as a whole for that matter.

"Damn and blast!!" exclaimed Anna in exasperation after several minutes of fruitless searching.

"Oh well, I guess it'll have to wait until next time" I said as I stood in front of her completely naked.

"Unless of course..." Anna speculated.

"Unless what?" I asked.

"Just wait there, I'll be right back" said Anna and she disappeared across the garden and into the house.

Several minutes passed before she returned. When she came back to the studio she didn't seem to have anything in her hands which indicated that she still hadn't found a suitable receptacle for my semen.

"No joy?" I asked.

"I've found just the thing -- I always keep a couple in my handbag because... well, you never know when you'll need one" Anna said.

"One what?" I asked.

"One of these of course!" Anna answered and held out the object in her hand -- it was a condom.

"Whoa there!" I said, "I don't mind you giving me a handjob but I don't think I'm ready to have sex with you -- not yet anyway".

"Relax" said Anna, "I'm not ready for that either, I'll only be using it for collection purposes only".

"Well, that's ok then" I said, somewhat relieved. Truth be told, I had no problem in principle with having sex with her -- she may have been more than twenty years my senior and may not have been the most desirable looking specimen of womanhood under her loose fitting bohemian style clothing, but she was a woman nonetheless and it had been so long since I had last had sex that I would've done it with just about anyone. But I didn't want our relationship to progress to that stage until I was certain that there was a genuine chemistry between us. And besides, I rather enjoyed the CFNM nature of our relationship and I was happy to keep it that way -- at least for the time being.

Anna tore open the packet which contained the condom.

"Well then, I suppose we'd better get that thing nice and stiff!" Anna said, obviously referring to my penis. We sat down together on the edge of the posing stage, I spread my legs apart a little and Anna set to work. She softly stroked my penis and coaxed it into life, the gentle stimulation causing me to become engorged rapidly. As soon as she was satisfied that I was fully erect, Anna wasted no time in retracting my foreskin, a little too forcefully causing me to wince somewhat. She placed the condom over the tip of my exposed glans and then rolled the thin latex sheath over the rest of my penis, enveloping it in its entirety.

Now that I was ready, Anna set to work. She started to rapidly stroke my penis, it became clear to me at that moment that this handjob would not be for my pleasure. It was merely a means to an end, Anna wanted my semen to mix with her paints and the sooner she got it, the sooner she could start painting. I didn't mind so much that my pleasure was of the least concern to her, in fact to my surprise I discovered that I rather enjoyed being emasculated in this fashion -- to be less of a man and more as a source of a vital commodity.

Dwelling on that thought was enough to send me to the point of no return, Anna must've been tiring from the effort of masturbating me so quickly and vigorously as her stroking slowed down substantially. But she had just done enough and I felt the all too familiar tingle course through my veins as my body prepared itself for my imminent ejaculation. Mere seconds later I ejaculated into the condom filling it with as much semen as I could muster.

"Good boy, good boy!" said Anna, again addressing me as if I were an obedient dog. I didn't mind it at all, in fact I found it rather endearing.

Once the last of my climax had subsided, Anna carefully removed the condom from my gradually softening penis and inspected its precious contents.

"Mmmm... should be plenty for today's session" she said. She took a small plastic syringe from her work table and used it to suck up as much semen as possible from the condom, once she was satisfied that there was enough in the syringe she placed it back on her table and then discarded the condom in a small waste bin in the corner of the room. She then took some tissues and gently cleaned the last remnants of semen from my penis.

Now that she had what she wanted we wasted no time and once more I adopted my now familiar pose. As Anna set to work I had to smile as every few minutes she would squeeze a little more of my semen from the syringe into her paints as she worked. Strangely, the rest of the evening's session flew by and before I knew it we were finishing up. Once again I allowed Anna to observe me as I relieved my bladder and also let her watch me as I showered.

By the time I left for home I was more certain than ever that this was the most wonderful thing that had ever happened to me, I was experiencing a world of sexual bliss in a way that I never thought was possible and I was loving every second of it.

The next few sessions -- both with Anna by herself and with the ladies painting group -- followed pretty much the same routine. Anna would give me a purposeful handjob before the solo sessions and, following the 'Androlos' sessions, each member of the group took turns in 'rewarding' me for giving up my time free of charge.

Each of the ladies had their own style, Sue gave me an absolutely amazing orgasm by giving me a classic handjob followed by her pulling back my foreskin as far as it would go and then licking my exposed frenulum until I ejaculated right into her waiting mouth, swallowing every drop.

Meera preferred to just stroke me gently until I was fully erect and then using her index finger, liberally lubricated with her own saliva, to massage the very tip of my penis right at my meatus. It was a simple technique but it delivered a truly knee-trembling orgasm.

Janelle was probably the least satisfying, she just seemed either keen to get it over with or not all that concerned with giving me as much pleasure as she could. Either that or she simply wasn't as experienced in pleasuring a male as the other ladies were.

Rita on the other hand, was utterly amazing, she kept me on the edge of the point of no return for ages until she finally allowed me to cum after a full twenty minutes of on-the-edge stimulation.

Only Mavis and Jenny remained and to be honest I wasn't looking forward to Mavis's turn at all. The other ladies were fine but Mavis was almost old enough to be my grandmother and the thought of being the plaything of a little old lady wasn't very appealing -- it almost made me feel physically sick at the mere thought of it.

So when on the Monday evening Anna announced that it was Mavis's turn I almost felt like appealing to her to let Jenny have her turn instead. But unbeknownst to me Mavis was harbouring a secret.

"Mavis is a retired doctor" said Anna as Mavis approached me and cupped my testicles in her cold, wrinkly hand.

"To be precise" continued Anna, "Mavis is a retired urologist, and what she doesn't know about male genital anatomy isn't worth knowing so it's a pretty good job that Martin here is chained up for his safety because he is going to have one hell of a ride!"

She wasn't wrong, Mavis's hands worked their magic all over my private parts but as soon as I took my eyes off her she did something that I never saw coming from such an apparently sweet old lady. She licked her left index finger... and then shoved it right up into my anus. I let out a scream of pleasure and pain as her finger penetrated me ever deeper into my rectum. She began to stimulate my prostate gland, which had me fully erect in a matter of seconds.

The intensity of the sensation grew and grew and before long my penis was so erect it felt as though the skin on my shaft was so taut it could split apart at any moment because of the strain. Precum was oozing out of my penis in a long sticky dribble that almost reached the floor. My whole body was trembling and I knew I was approaching an almighty orgasm.

I had reached the point of no return, I felt my orgasm wash over my whole body causing every bone, muscle and sinew to shudder and shake out of pure ecstasy. I looked down expecting to see my semen shoot out of my penis like a bullet from a gun. Except that not a drop of semen escaped from my throbbing erection. I had just had my first 'dry' orgasm.

Once it had subsided, Mavis continued to gently massage my prostate, not once during all this did she touch my penis. She gave me three more 'dry' orgasms, each one as earth-shattering as the last, before she finally took hold of my penis and masturbated me until she finally allowed me to ejaculate. And when it finally happened I came so hard that my semen shot out a clear eight feet from my body. And I also ejaculated so much that it felt like I was pissing the stuff out.

"Unnnngggghhh!!!! Aaaaaahhhh!!!! UUURRRRRNNNNNGGGGHHH!!!!!!!!" I screamed and growled as I experienced the most earth-shattering, intense, powerful, mesmerising and ecstatic orgasm I had ever experienced in all my life! My wrists and ankles burned with intense pain as I strained against the manacles holding me against the artificial rock.

As soon as I had finished ejaculating, Mavis released her grip on my penis and extracted her finger from my rectum. I had experienced something that never in my wildest dreams did I ever think I would experience -- a multiple male orgasm. I was utterly drained and I felt I could no longer stand up and I collapsed forward, only the chains at my wrists and ankles prevented me from falling onto the floor.

With her work done, Mavis went into the shower area to wash her hands. Once she had finished she approached me as I still chained up, and said "I hope you enjoyed that young man, because I know that I certainly enjoyed giving it to you!" And she just chuckled slightly, kissed me on my sweaty forehead and rejoined the rest of the group as they put on their coats and took their leave with a cheery "See you next week!" addressed at both Anna and I.

As soon as Anna released me I could do no more than just sit on the edge of the stage and contemplate what had just happened.

"You see, you should never judge a book by its cover" Anna said as she handed me a much needed glass of water.

"That was..." I gasped, "that was... well, words fail me."

"Mavis says she used to love giving her male patients an orgasm when giving them rectal exams and over the years she got pretty adept at it" said Anna, "in fact, she used to love it so much that she used to give her male patients a rectal exam whether they needed it or not, she said the youngest man she ever gave one to had only just turned 18 a few days before".

"I wish I could've had her as my doctor!" I replied,

We just sat and talked for ages, I was still naked and desperate for the toilet. Once again Anna asked if she could watch, which by now I was only too happy to let her.

"You don't need to ask you know" I said as I stood before the toilet allowing the golden stream of my urine to flow from my penis into the waiting bowl as Anna watched it happen before her eyes, transfixed as always, "It's quite ok by me, really".

"I know" Anna replied, "it just seems... I don't know... somehow disrespectful to just assume that it's ok for me to watch you perform such a private bodily function without asking".

"Well from now on you don't need to ask" I said, "if I don't want to let you watch, I'll be the first to let you know ok?"

"Sounds fine to me" Anna smiled.

We sat and talked for a couple of hours and once again it was gone midnight before I finally got to put my clothes back on. I had discovered that I absolutely loved being Anna's nude plaything, I could tell by the look in her eyes that simply being in the presence of a naked male was such a pleasurable experience for her.

I wondered if she masturbated to the mental image of my naked body as soon as I left her house. I had had my first ever experience of a multiple orgasm that night, it was the most amazing thing I had ever experienced. I did however, become conscious about how much my arse was hurting however, but it was certainly a price worth paying and I couldn't wait to let Mavis have another go on me someday. But the next session -- the final session of the 'Androlos' painting would surpass everything that had happened so far.

Before that however, there was another three regular sessions to get through. Once again, as usual I was naked throughout -- Anna masturbated me to collect some of my semen to mix in with her paints and at the conclusion of the session I allowed her to watch me as I urinated and showered.

I was eager to discover what Jenny, the youngest member of the ladies art group was capable of and that week seemed to pass more slowly than ever before.

But eventually, the time came and as I was chained to the rock for the last time I was sure I would be in for an amazing experience. And I wasn't wrong in that assumption although it was far from what I expected it to be. As the final session came to its conclusion Anna announced to myself and to the group that tonight it was Jenny's turn to have her way with me, and it was to be as much for her benefit as it was for mine.

"Jenny has decided that she doesn't wish to play with Martin's 'little soldier' -- instead, she was wondering if it would be ok if you did her the honour of being her first" said Anna.

"Her first what?" I replied.

"I want you to be the one" Jenny said, "I want you to be the one I share my first time with".

"Wait a minute" I said, not quite believing my own ears, "do you mean... do you want me to have sex with you?"

"Yes, I want you to take my virginity and make me into a woman and I want all of us here to share in it" Jenny answered.

Anna unshackled me and handed me a condom, suddenly I became aware of a sense of pride and flattery coursing through my being. I was being asked to take a young woman's virginity in front of the rest of the group -- I felt truly honoured to have been asked to do it but I was still nervous nonetheless. Would I be up to the job and would I be able to put on a good enough show for the rest of the group?

I decided -- what the hell! And I signaled my agreement by tearing open the foil packet which contained the condom. Jenny however, had other ideas.

"I don't want to use a condom" she said, "I want my first time to feel special -- for both of us. I want to feel him fill me with his cum and I'm sure he would want to feel everything too and not have our special moment spoiled by having his manhood encased in latex".

"Well, only if it is ok with Martin -- don't forget Jenny, that he has a right to decide whether or not he can potentially father a child, I mean, I'm sure his sperm is pretty potent and if he got you pregnant it could be a pretty tricky situation for both of you" said Anna.

"It's ok Anna" said Jenny, "I'm on the pill -- have been for ages. So whaddya say Martin, will you do it to me without a condom?"

I only needed to think about it for a fraction of a second -- I tossed the condom on to the floor.

"I always hated these things!" I said and Jenny's eyes lit up.

"I can't believe this is happening" Jenny said excitedly, "I can't believe I'm really going to have sex!"

Jenny wasted no time in getting herself undressed. In a way, I didn't want her to be naked as it would ruin the CFNM experience for me but Jenny's naked body was such a beautiful sight that I knew that on this occasion, I would be more than happy not to be the sole performer. The next few minutes were a blur, all I know is that I was hard in seconds and I couldn't wait to take her innocence, but I knew that I had to take my time.

So we spent at least a quarter of an hour just exploring each others bodies, all with Anna and the other members of the group looking on. I fingered open her labia and I could clearly see her hymen -- she was most definitely a virgin. I let my tongue caress her clitoris causing her to squeal excitedly. By now my penis was dribbling precum everywhere, I wanted to just shove myself inside and pound myself into her vagina, but once again, I knew that I had to take things slowly. I had never taken a woman's virginity before but one thing I did know was that breaking the hymen could be painful for her and so I knew I had to be gentle with her. Jenny got up onto the stage, laid down on her back and spread her legs open, ready for me to deflower her.

So I offered the tip of my fully engorged penis to the lips of Jenny's vagina and gently prised them open, rubbing myself gently up and down along the length of the slit-like opening, I heard her take a sharp intake of breath -- readying herself for the pain to come.

I pushed forward a little, Jenny yelped slightly as a shock of pain flashed across her whole body -- I stopped dead in my tracks. After a minute or two I tried again -- again with the same result. At that moment I felt the best approach would be to take her by surprise, so for my third attempt I decided not to be quite so gentle. I thrust myself forward with much more force and as Jenny cried out in pain I could feel her hymen giving way, splitting apart, and then as soon as it tore open my penis shot up inside her vagina and all of a sudden I was within her -- balls-deep. Jenny was a virgin no more. The other ladies clapped and cheered as their friend lost her innocence before them.