Teddy Bare Pt. 01

Once Natalie had announced she'd finished work for that day she offered me a cup of coffee, an offer I gladly accepted. I was once again desperately in need of a leak however, and so as she set about preparing the coffee I went into the bathroom to relieve myself. When I came back into the living area a few minutes later I was greeted by the sight of Natalie sitting on one of the settees twirling my underwear around her index finger.

"It's a shame you have to put these back on," she said as she tossed them over to me. "I've quite enjoyed having a nice, naked young man around my humble abode."

"Well, there's no rush - I don't have to put them back on right now, do I?" I answered her as I tossed them back onto the rest of my clothes. "I distinctly remember you offered to make us a coffee."

Natalie smiled and returned to the kitchen.

"Of course I did," she said with a smile as she resumed preparing the coffee.

I had surprised myself at how quickly I had come to seriously enjoy being naked around her - I felt no shame about my nakedness anymore, and in fact I even began to feel empowered by it. The other boys at school taunted me because they had something that I had been deprived of, but to Natalie it didn't matter at all that I'd been circumcised - she could see past what had been done to me. So I remained naked for a little longer as we sat and sipped our coffee together, and of course, it wasn't long before the subject of what had happened earlier in the studio came up.

"I er, I hope you didn't think I was abusing your trust, suggesting that I masturbate you like that," Natalie said to me.

"Not at all," I assured her. "In fact, it was the most amazing thing that's ever happened to me. I never saw it coming in a million years, but I'm glad it happened - I really am."

"Well, thank goodness for that," Natalie said. "The last thing I wanted was for you to think I was taking advantage of you."

"If I had thought that, I wouldn't have let you anywhere near me," I replied truthfully.

"So I guess that means you wouldn't be at all upset if I did that to you again, huh?" she ventured.

"Nope!" I responded without any hesitation. "As far as I'm concerned you can do that to me as much as you like! I trust you, Natalie - like you said, I wouldn't be so comfortable being naked around you if I didn't trust you."

Natalie smiled, and for a moment my heart swelled. But then her expression changed, and I knew that something had entered her mind that had soured the moment.

"I'm glad to hear that," she said to me with a weak smile. "But if you're going to trust me, I guess there's something you ought to know about me - it might change your opinion of me."

"I'm sure it's nothing bad," I answered. "But if you don't want to tell me I won't mind."

"But I feel I have to tell you," Natalie said and then took a very deep breath. "I don't suppose your mother ever told you why I left the teaching profession?"

"She said that we 'ingrates' had pushed you to the limits of your sanity," I replied.

"Well, that much is true, in a way," Natalie answered. "And that would be the 'official' reason for why I left teaching, but it wasn't you and your classmate's behaviour that was at fault - it was mine."

"Yours? How?" I prompted her, because for all those years I had felt that somehow myself and the rest of my classmates were at fault for her leaving the school as abruptly as she did.

Natalie took another deep sigh before continuing.

"I've never said any of this to anyone before - not even to Frank when I tendered my resignation," Natalie began.

Frank would be Dr. Frank Magnusson, the headteacher at my old school.

"Being a teacher, especially in an all boys school, was turning me into something I didn't like, something I'm now truly ashamed of," she went on. "I felt I was becoming a monster - a predator, and that if I didn't take drastic action I feared I might've done something truly appalling. You see, the real reason I got out of teaching was that I found myself becoming attracted to, well, underage boys."

To say I was shocked would be an understatement, but I remained calm and allowed her to continue.

"I knew I had to get away before I did something stupid," she went on. "I'd read newspaper stories about teachers who had taken advantage of their students and I knew that unless I did something drastic I would likely become another one of those salacious headlines. You know the sort of thing - teacher jailed for sex with underage student. I felt almost physically sick at myself - I simply had to get out of that environment."

She let that revelation hang there for a moment before drawing another deep breath and moving on.

"So I resigned," she went on. "And to begin with I found another job in another school in Ipswich. But it was co-ed, and it wasn't long before I found myself back at square one. I resigned for a second time, except that time I knew I would never teach again. So I had to totally reassess my life, and I found myself taking solace in painting as a way to try and express myself. A friend of a friend saw my work and asked me if I could paint a portrait of her husband for their wedding anniversary. I had nothing much else to do on the horizon, so I accepted.

"To cut a long story short, she was delighted with the outcome, as was her husband when he unwrapped her gift to him. One thing led to another, and by the end of that year I'd had five more commissions. I had gone from geography teacher to professional portrait painter in the space of just under a year, and I've been at it ever since.

"With the money my mother left me when she died, and the life insurance payout I received when my late husband was killed at work, I bought this old tub and set up my studio here. That was three years ago now, and I've never looked back."

"Wow, I don't really know what to say about that," I said to her.

"Knowing I had nearly succumbed to temptation shook me to my very core," Natalie went on. "But reading about the potential consequences of giving in to my urges was a definite wake-up call. I, er, I hope all this doesn't change your opinion of me - I'd hate to have to end things like this, but I'd totally understand it if you'd rather run a mile from the sick pervert who lusted after teenaged boys."

I thought carefully for a moment about my response. Then it was my turn to take a deep breath before continuing.

"Natalie, I'm glad that you feel that you can confide in me, and I'd like to say on record that it doesn't change my opinion of you," I said to her sincerely. "You recognised you had a problem that could potentially be very damaging, both to yourself and any boy who might've got caught up in it, but rather than let it consume you and let it drag you down into depravity, you took positive action to nip it in the bud - and I have to say I admire you for that."

"You do?"

"Absolutely," I affirmed. "It would have been far too easy to have just allowed that inner demon to drag you down, and for you to possibly have ended up in prison or something, but you stood up to it and said "no - I am not going to be that person." You realised that you were better than that, but that working in that environment in such close proximity to the objects of your desire was toxic for you, so you made totally the right decision to get out."

"I know, I know that now," Natalie responded tearfully. "I hated myself for a long time - I felt physically sick once I'd stepped back and realised what was happening to me, about what I could have done to an innocent young man. I thank whatever omnipresent sprint there is up there looking over us for dragging me away from the brink - I can honestly say I'm a different person now. I no longer look at teenaged boys with lustful eyes anymore."

She turned to look at me in my current nakedness and continued.

"I still look at the male body as one of the most beautiful things in all of creation - as far as I'm concerned there is nothing more pleasing to the eye than a naked man who is confident in his body and uses his inherent masculinity for positive ends - but the difference now is that it is fully grown and emotionally mature men I feel attracted to."

"I think I ought to raise a toast," I said as I picked up my mug of coffee.

"What to?" Natalie asked me.

"To redemption," I said. "Specifically, your redemption."

"Redemption," Natalie repeated, and clinked her mug against mine.

"Believe me, if what you told me changed my opinion of you, I would have run out of here in seconds!" I said as I set my coffee down.

"Even though you're still naked?" Natalie enquired with a chuckle.

"Even though I'm still naked," I confirmed. "And I would have done, had you not explained how you changed yourself for the better. And besides, I think you're much better as an artist than you ever were as a teacher - your lessons were always terminally boring!"

"Oh, get off! They were never that bad!" Natalie huffed in reply.

"Well, perhaps that was a little harsh, but then I never really enjoyed geography at all, no matter who was teaching us," I capitulated.

We sat and drank the rest of our coffee, but time was getting on. So it was with some reluctance that I finally put my clothes back on and made for home. My head was spinning with everything that had happened over the course of the past two and a half hours. I'd had my very first sexual experience and it had been incredible, and also there had been Natalie's confession about her close call with ephebophilia (that's sexual attraction to adolescents by the way - go look it up) that could have seen her in prison at worst, or at the very least fired from her job should it ever have come to light.

If that afternoon taught me anything, it was an important lesson in trust. I had shown, albeit subconsciously at first, that I trusted Natalie enough to be comfortable being naked in her presence and allowing her to touch my most sensitive and intimate parts, and she had shown trust in me in return by confiding in me about how she had come so perilously close to becoming a perverted monster. As I cycled home I tried my best to process it all - but I knew for certain that modelling for Natalie was one of the best things that had ever happened to me.

And things were going to get even more interesting as the work on her painting continued.

* * * * * *

The next few modelling sessions followed much the same pattern - I would strip off as soon as I arrived, and would remain naked right up until it was time for me to go home. She would also give me another handjob each time, except that from then on it was because we both enjoyed it - she enjoyed giving me pleasure, and I certainly enjoyed receiving it! She had moved on from preparatory sketches of charcoal on paper and on to putting oil onto canvas, and I had become more and more adept at holding and maintaining the pose.

Around midway through the third oil on canvas session, Natalie asked me something that led to our relationship taking another turn into the unknown.

"So, have you had any success in finding a girlfriend since we first met, Teddy?" she asked me as she worked.

"Sadly, no," I replied, trying to keep as still as possible.

"I'm afraid I simply have trouble believing that any girl wouldn't want you as her boyfriend," she responded as she dabbed some paint onto the canvas. "But like I said before, it's their loss."

"Sometimes I feel like I might die a virgin," I said, with genuine melancholy.

"Oh, don't say things like that!" Natalie chided me. "You'll meet a decent girl one day, you'll see."

"It certainly doesn't help that any confidence I had in talking to girls was basically taken from me by the other boys at school," I went on.

"Because you were circumcised?" Natalie surmised.

"They basically told all the girls about it," I responded dejectedly. "And they told me that no girl would be interested in me because my cock is basically inferior to theirs."

"Ugh! If I could get my hands on those horrid boys for doing that to you!" Natalie said with a slight growl of anger. "Being circumcised does not make you inferior in any way! A little different, maybe, but certainly not inferior."

"Yeah, well, since then I've never had any confidence when it comes to women," I said with a sigh.

I tried hard to fight back my tears, but it was a losing battle.

"Except with me," Natalie observed. "I mean, you have enough confidence to pose nude for me. And to let me touch you intimately."

"That's different," I said with another deep sigh.

"In what way?"

"I don't know - it just is, somehow," I replied. "Like, you're my ex-teacher - it sort of feels different somehow. Which I know makes no sense at all, since you're no longer my teacher."

"I hope you don't think I'm making light of things, but you need to get laid, badly!" Natalie chuckled.

"Yeah, well the likelihood of that happening is remote at the very least," I groused.

Everything went quiet after that and Natalie returned to her work. She mixed paint on her palette and applied it to the canvas and kept on dividing her attention between her painting and my naked body. After a while however, she abruptly dropped her palette and brush onto the work table.

"I'm sorry, I can't go on like this,"she said as she wiped her hands on a piece of cloth.

"What? Why?" I asked her, still diligently maintaining my pose.

"I've been fighting against this for the last few days, but it's clear that I'm going to have to do something about it," she said with a sigh of her own. "You're a beautiful young man, Teddy, and I've enjoyed painting you and getting to look at your naked body, not to mention giving you handjobs, but I can't resist myself anymore. Teddy, would you like to have sex with me?"

"Wh-what?" I gasped.

"I said, would you like to have sex with me?" Natalie reiterated.

"I - I don't want it out of pity," I responded, which was true - no matter how much I desired a woman to pay attention to me and for me to share myself with, I wanted her to do it because it was what she wanted too, and most definitely not out of sympathy or pity.

"I'm not doing this out of pity, Teddy," Natalie tried to assure me. "I want to do this because I think you are a handsome and wonderful young man."

"For real?" I asked her, seeking confirmation.

"For real," she asserted.

She mounted the platform and urged me to take her hand.

"I want you, Teddy, I have done ever since I first met you," she said to me. "Would you like to come into my bedroom?"

I stared at her hand for a moment, still maintaining my pose throughout. She was offering to take my virginity, and even though she was more than twice my age I couldn't help but admit that she was still a good looking woman.

I reached out to her and took her hand.

Natalie smiled broadly and helped me down off the stool.

"Are you sure about this?" I asked her as she led me out of the studio.

"As sure as I've ever been about anything," she replied as we traversed across the open plan area towards the door that led into her bedroom. "And I'll be honoured if you'll allow me to be your first."

I could barely speak around the lump in my throat and so I just responded with a meek acknowledgement of acceptance.

She took me into her bedroom and she turned to face me. Compared to the rest of the accommodation in the old Thames barge which was illuminated from above by large skylights, the former captain's cabin was much more dimly lit, with the only source of natural light being several small portholes. The sun reflected off the water of the river the barge was moored in caused a ceaselessly moving pattern of dappled light that danced on the low ceiling.

"I'd like to teach you everything you need to know about how to treat a woman," Natalie said as she stepped towards me. "As long as you'll let me."

I nodded in response, still not able to coax anything from my vocal cords.

"And I'll teach you exactly how a woman should treat a man, too," she added. "Lesson number one - sex is not a competition, it's as important for a woman to please her man as it is for a man to please his woman."

"Wh-where do we begin?" I croaked.

"Well, since you're already naked, perhaps I ought to join you," Natalie said. "Would you like to do the honours?"

"What? You w-want me to undress you?" I stammered.

"Lesson two - foreplay is very important, and undressing each other makes for perfect foreplay!"

I hesitated for a moment before Natalie gave me a prompting look.

"It's okay, Teddy, I don't bite!"

I swallowed hard and reached up to the collar of her blouse. One by one I unfastened each button, taking my time with each one and gradually revealing the creamy white bra she wore underneath. Once the last button was undone I gently pushed her blouse off her shoulders.

"There, that wasn't so hard, was it?" Natalie said as removed her arms from the sleeves. "Now all you have to do is help me take off the rest."

"Er, yes, of course," I responded.

I reached down to her waist and unfastened the buttons of her paint spattered old jeans that she wore in the studio, and fairly soon I was pushing them down off her wide feminine hips. Her panties (or knickers - I can never tell which is which since I'm definitely no expert on women's underwear) matched the style of her bra. It was at that point that my penis responded to what my eyes were seeing - Natalie may have been in her mid forties, but she clearly looked after herself.

"Er, how do I take off your bra?" I had to ask her.

Like I said, when it comes to women's underwear I'm certainly no expert!

"Just reach behind me and unhook the clasps," she instructed.

So I leaned forward and reached behind her and located the clasps. To my surprise they were fairly easy to unhook, and as soon as it was unfastened it was a though it just fell off her shoulders. Her bare breasts were revealed to me in all their glory. Once again defying her age, her breasts were full and perky, and were crowned by pert nipples encircled by large areolae. They weren't the largest breasts in the world, in fact you could say they were rather small compared to some of the top-heavy glamour models I'd see pictures of during my adolescent years, but they were nonetheless perfect in my eyes.

"Like what you see?" Natalie asked me with a grin.

"Very much so," I answered, my voice wavered as I tried to speak, making me sound like a pubescent teen rather than the fully grown young man I was.

"Well, you'd better help me out of my knickers then," she said with a slight wink. "I think you'll like what's in them even more!"

"Er, okay," I replied.

With trembling hands I placed my hands at the waistband of her knickers (well, that was what she called them, so I elected to do the same) and hooked my thumbs into the waistband. I drew them slowly down her hips, and revealed her most intimate feminine inner sanctum. she was clearly a woman who took great pride in her appearance - her pubic hair had been neatly trimmed into a narrow strip, just dense enough to give her the appearance of a fully grown woman yet not too dense as to obscure her outer labia.

"Holy shit!" I gasped as I took in the sight of Natalie in all her naked glory.

She looked more like a woman in her late twenties than mid forties, with soft smooth skin, just tanned enough to not make her look too pale. I guess you could say that her figure was slim, but not too slim, strong yet at the same time delicate. I liked what I saw. I liked it a lot!

"You, you're so beautiful!" I said, my compliment entirely genuine and sincere.

"Thank you," Natalie replied with a smile. "I guess that ought to be lesson number three - it never hurts to pay your partner a nice compliment!"