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Breaking in sweet Jennifer

Would you like to see it for real? I asked her

When Jennifer came to me it was like a new life beginning. Jennifer was delightfully sweet and innocent who, straight from a convent at nineteen, had never had a boyfriend. She wanted a room to set up her independence and to get settled in with her online university studies.

I was the owner of a hotel which had been converted into bed sitting rooms. I was delighted to give her a room for a minimal rent in return for some small chores around the house. At forty two, maybe I am old enough to be her father. With my wife having deserted me five years ago for another I was all bitter and twisted. But my sexual ardour was still very much in place, especially now with Jennifer around.

I was having all sorts of carnal fantasies. Wondering how she would be if I had her. But never imagining just how it would turn out, wondering if she would be interested in an older guy and would want that guy to teach her the fundamentals, for want of another word. She felt she had missed out and quickly wished to discover her true self in every way.

I have to say it was not a sordid affair and my Jennifer was a natural.

She wanted to learn the ways of the world, having been sheltered for so long in a convent. Her hormones were going absolutely berserk she told me during an early conversation. Now was the time to venture and discover her true self and achieve her aims in life. She chose me to be her 'tutor' in almost all aspects and I was about to experience the happiest days of my life in the most unexpected ways.

Although Jennifer was innocent enough regarding the ways of the world she had a natural instinct and ability to recognise without restriction or inhibition her sexual desires. She confessed quite openly that she had been masturbating since her late teenage years. She found joy and relief from that given the boring day to day business of study in a convent.

She came to me saying quite candidly she wanted to discover all. I felt I was just the right person to teach her. She said thought the world of me and maybe even more. She was that unsure what could be the real thing, or just a sexual liking that would pass. That she wanted that opportunity to discover, with me, for herself.

Who was I to deprive her of that? But I had to be sure she was fully aware of what she was asking and that it could develop into something more serious. She said she felt comfortable with me and trusted me implicitly. She wanted to have sex with me because seemed right and that she fancied me. She wanted at last to share her wildest dreams with a guy she adored.

The very first time we actually started to get together was sheer magic. I explained to her how guys, in particularly this guy, liked the lure of the feminine sex. Particularly the way she dresses, her grooming, and the rest of it.

She was driving me insane; sitting there before me in such a delightful short skirt with those very alluring black hold- up net stockings I asked her to wear for me. Now they are a real turn- on. She looked up at me from her armchair peering into my eyes. I explained how nice it would be to see a little further up her skirt, saying how it would be sublime if she just slightly parted her thighs making a tease for me.

"Like this, Peter?" she asked doing what I'd asked very coolly, lifting that delicious skirt up a little more and parting those gorgeous young thighs to a point where, in seeing the darkness between, my masculinity was already beginning to show head.

Jennifer sort of looked down at me; obviously seeing what was going on beneath my trousers and asking curiously if what she was doing caused that.

"Would you like to see for real?" I asked excitedly, the male in me becoming very ardent and frisky. Thinking about how it would be if she raised her skirt even higher to reveal her underwear.

Her look said everything, those delightful sparkling and deliciously inquisitive brown eyes and that simple nod that said she would.

"Then I shall begin" I said. By which time I had already reached a full erection which was trying ardently to get out of my trousers.

Jennifer looked intently as I slowly unzipped, finding it inside my briefs and ever so gently easing it out, watching her reaction as I did so. I was wanting for her to hopefully enjoy the moment just as much as was I. Jennifer looked intently as I dropped my trousers and my briefs to show her the full works, I was conscious of my balls hanging as they do. I don't know why but I have always imagined they had too much! So I quickly cradled them believing that would make them look better. It was sort of a guy thing but I had to give a good impression. There was a short pause, would Jennifer react or just remain as she was, wide eyed, mouth slightly apart? But looking extremely gorgeous and wanting.

"You like Jennifer?! I asked and her gorgeous smile said everything.

"I have never seen one like that before, Peter."

"How do you mean?" I ventured.

"Not fully erect" she glowed like she wanted to touch.

"You can touch if you like,” I said, "see what it feels like."

And she did, it was the very first time for her to touch a guy she told me. I felt a quiver in my loins as she touched more. I closed my eyes and thought what a lucky guy I was.

"Squeeze it" I said laughing, I wanted to keep it from getting too serious, for it to be a fun thing too.

And she did, very gently but meaningfully and it felt so nice. Those tiny hands doing things they’ve never done before, I ventured to stretch back the foreskin to expose the bulbous fullness, for her to examine. I saw her nostrils shallow. She sniffed me there and it was nice.

"Smell nice? I asked.

"Wonderful," she responded and all at once I yearned for her to take me into her mouth.

For the next few minutes we were to share the most sexually thrilling time I had ever encountered with a woman during foreplay.

"You can wank it if you like!" I offered and she complimented me saying how wonderful it looked, how warm and nice to touch. I showed her how to jerk it to give the best sensation.

I showed her how to manipulate it, to stretch it back and explore the glans with her finger tips, teasing the p-hole explaining that is where the male seed comes out. It stood high leaning against my stomach. She was absolutely keen to learn. Feeling her explore my cock in the most delightful way was something I will never ever forget.

"It is very big, Peter, bigger than I ever imagined."

"I hope you are not disappointed, Jennifer?"

She chuckled and assured me it was fine. I explained to her that is what goes inside a girl, and she queried would it be too big to fit?"

I laughed and told her not to worry. I assured that would soon be rectified with some gentle preparation. I said that she now needed to show me her sex. That gem between those black stockinged thighs, her skirt now raised to reveal blue panties that suited her so much, that delightful tight bum looking so wonderfully inviting. I had a sudden urge to do everything but held myself back. I didn’t want to spoil it all. I liked the girl and wanted to make the first time perfect for her. She was keen to show me. I undid her skirt for her and her blouse too, and then her neat little bra which I undid at the back to reveal delightful firm breasts with gorgeously defined pointed nipples.

She smelt like a girl, the natural scent I had missed for so long, a real attraction to the male libido to be sure. She wanted me as much as I wanted to fuck her. But I knew that would spoil it all because first I needed to prepare and groom her. So we could both enjoy, I said to her to just tell me if anything I did would repel her in any way and I would immediately stop.

I couldn't stop the temptation offered to me as she sweetly parted those gorgeous thighs, exposing the sheer whiteness between stocking tops and panties. But most of all there it was just waiting for my spoiling, sweet virginal and quite wet pussy.

I knelt between her, lifting her by grasping underneath her knees and pulling her to me nice and high and wide. I leant forward and pushed my face into her sweet femininity, pressing my tongue gently into the crevice through the silk panties. Licking, tasting and moving my mouth around and around. I gently manoeuvred her panties aside so I could feel and taste her rosebud. Turning my tongue around and hearing her first moans as I started also to gently work finger into her.

Pausing for a moment saw her arm reaching out, her hand striving to reach my throbbing cock. I altered my stance so she could enjoy me as I enjoyed her.

"Now you squeeze it like this" I said to her and showing her how - squeezing its length and massaging it.

She responded immediately and I was thrilled to see the flush on her cheeks again as she felt me firmly. And she didn't stop - she was enjoying so much. Now confidently rubbing and stroking me and below, discovering my balls, me telling her that is where the seed is kept for fertilising babies inside a girl.

"Inside here?" She asked touching herself, making a small hole with her fingers where mine had just ventured. It seemed well worked and although she was obviously a virgin it had been well masturbated I could tell - so for me it was a delight to touch and taste her femininity. The sweet velvet feel of a pussy which was already very moist with the touching, I moved into a kneeling position again, prompting her to open her thighs wide enough to let my head lodge between to do the business.

I sucked her gently, being sure she wanted that, but her body language had no problem with that. She pushing her sweet young virgin pussy into my face, smothering me as I continued to lick and taste her. Then the moans again and I knew I was on a promise. Her thighs stretching outwards even wider as I gave get a real good licking and sucking out. This pussy would be so good for me, I'd never had a virgin before, I would do it so gently, I was intent on her enjoying her first fuck with hopefully many more to come as I taught her more fundamentals.

Then I showed her how we could both enjoy each other orally by laying in a sixty nine position. She took to sucking cock like a natural, her sweet small mouth stretching so wide intent to take as much cock inside as she could. To see her cheeks stretching as she so enjoyed this new experience was magic. I felt myself pulsing every time she sucked and showed her how to cradle and gently squeeze my balls as she did so. It was delight! Heaven...

"I do believe you are ready for it," I declared hearing her sigh.

"Yes please, and soon."

So the fuck was nigh. I gently held my cock upright and teased her rosebud with my p-hole which she loved. Just the look on her face was so wonderfully provocative and appealing. All the time I gently pressed it around her sweet pussy lips, feeling the wetness build to take the fullness of my stiff cock. I started to insert it slowly and gently, her mouth opened, her eyes rolled back. I felt it slip tightly into her, a little difficult at first but gentle thrusting I made it through her hymen, she yelled a bit as I released her virginity and then she was a woman through and through. She said it was okay to carry on and not to stop.

I gave her the most wonderful first fuck of her life because I wanted it to last forever but to make sure she would want it again and again in so many ways.

Jennifer, my special girl forever...

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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