We were sitting at the long table, awaiting the speaker to offer grace. A young woman, looking to be about 25 to 30 years old, came to our table and asked if all the seats were taken. We told her no, sit down. She smiled shyly, and sat down with her tray of food.

She was about 5’7″ tall, and weighed about 120 pounds, if I was estimating correctly. She was wearing drab clothing, and had not applied any make-up. She wore thick glasses, and continually flipped her mud-brown bangs from her plain and ordinary face. Appearance wise, on a scale of one to ten, I rated her a 3. After eating, she got up to get a drink, and I asked one of the other people at the table, who was a local (I was visiting town to conduct research) if she was a nun. He told me that she was a librarian–damn, she fit the stereotype to a T.

She returned to the table with a glass of tea, and again smiled shyly. Since she was sitting directly across from me, I asked her where she was from. She mentioned a town in Texas, and I asked her how she had ended up way out here on the east coast. Her job, she told me. We exchanged names, hers was Anne.

As we readied to leave, she dropped a napkin and bent over to pick it up. For the first time I noticed that she had a fine-looking ass–one that I would like to fuck.

The next day I went to the library and ran into her again. She was the only person working in the small town library, but she was a very good worker. Only two or three other patrons entered the library all day, so she spent most of the day helping me. I could not help but notice that she was so very shy, and naive.

When it came time to close up the library, I asked her to let me take her to dinner to repay her for all of her help. She told me it was not necessary, she was there to help. I insisted, and finally she agreed to go.

I told her I would pick her up at 6:30, that I needed to shower and change clothes. She said she had to do the same.

When I arrived at her apartment, she came to the door, and was dressed as plainly as before, and still was not wearing any makeup.

She told me where most people in the town went to eat, so we went there. As we placed our order, I ordered wine, and she hesitated, saying “I rarely consume alcohol.” I replied, “just take a few sips, you deserve a treat after the hard work you did today.”

By the time we finished dinner, she had had two glasses of wine and was becoming more talkative. I asked if her boyfriend was here, or in Texas. She told me she had never had a boyfriend, that she had grown up on a small farm outside Amarillo, TX and had gone to a small private woman’s college. We chatted more small talk, then went to my car.

Upon arrival at her apartment, I asked if I could come in. She told me it was not a good idea, she was afraid people would talk. I pleaded, telling her I really needed to use the bathroom, which was the truth. She glanced around as if she was looking to see if anyone was watching, the told me o.k.

We went in the apartment–books were everywhere, but other than that it was neat. I did notice, though, that it was spartan, with very few colorful items. Everything was functional.

After I used the bathroom, I came to the living room, where she was standing by the door, ready to show me the way out. I reached for her hand, and held it in both of mine, and thanked her for her help today and for being such a good dinner partner. She smiled again, then I pulled her to me and kissed her on the lips. Anne struggled some, then began to respond to my probing tongue.

We pulled apart, and she told me something that shocked the hell out of me–”that is the first time I have ever been kissed”. “Did you like it?” I asked. She blushed, smiled, and nodded yes.

I pulled her to me again, and this time she did not pull away. I began to flick my tongue into her mouth, and finally she got the hang of it. I pressed my now hard six-inch cock against her cunt mound, and she pushed away. I persisted, and finally she began to push back.

Picking her up, I placed her on the sofa and we continued to kiss like a pair of teenagers. I put a hand on her breast, but she removed it. We kissed some more, and I could sense that she was getting more aroused.. Once again I put my hand on her tit. This time, she did not move my hand.

For a while I rubbed her tits, then I placed a hand under her blouse. She stiffened up, but as I continued to kiss her, she relaxed. I removed her blouse, and her bra and glanced at her nice tits. Firm, with a hard nipple.

Then I bent down and began to kiss her tits. First one, then the other. Anne was breathing heavy and even let out a slight moan ever now and then . Now my hand was under her skirt. “Please stop, I have never done this. Please stop.” My hand reached under her panties, and her cunt was wet.

She still tried to get me to stop, but I kissed her belly, then down to the top of her skirt. Her virgin cunt mound was just a few inches from my tongue and lips. I unzipped her skirt and slid it off her. She was now sniffling, crying, and asking me to stop, but I could not stop. I could see cunt hairs, and it looked like she had never trimmed them. Moving my head to her cunt, I began to kiss her pussy through her panties. Anne was now responding and I removed her panties. Placing my hand on her hairy cunt, I pushed a finger to her soaking wet cut and began to massage her pussy lips and clit. As I looked at Anne, she was flushed, and primed.

She was breathing deeply as I massaged her clit with my fingers, spreading her tight little pussy as much as I could.

I slid to the floor, and pulled Anne on top of me, placing her cunt right over my mouth. She was holding her cunt away from my lips, then I began to blow hot air into her cunt. It was too much for her, she gasped and pushed her cunt into my face.

As my tongue and lips worked all over her cunt and clit, Anne began to move up and down, then she pressed hard on my face and she began to moan. I could tell she was close to an orgasm, then one final lick and she groaned loudly, and I could feel a flood of her pussy juices rush out of her cunt canal.

“Bill, that was awesome. I have read that oral cunnilingus is good, but I had no idea how good.”

I rolled her off me, and moved my head up to her lips and kissed her while I was sliding my pants and shorts down. She was so naive that I honestly think she had no idea that I was preparing to ram my cock into her virgin pussy.

I placed the head of my cock on her cunt. Once again she was crying no no no, but as my cock touched her vagina lips, she stopped. I rubbed my cock against her cunt and now she was once again responding feverishly.

Rolling on my back, I pulled Anne onto me again, keeping my cock at the mouth of her pussy.
I began to apply pressure, raising my butt up and pushing my cock into Anne’s cunt. I was in about two inches, then more, then my cock met the hymen. Anne was saying “it hurts, it hurts, please stop, but she did not move. I put a hand on her soaking pussy, got it wet, then grabbed her but. Soon my finger was at her asshole. I pushed it in just a little as I began to kiss her tits, then as I shoved my hips up, Anne pressed down and I felt my cock go where no cock had been before. At the same time, my well-lubricated finger was in her asshole as far as it could go. I was moving it in and out.

Anne let out a stifled scream as my cock broke through her hymen., but continued to pump up and down on my rod. We were both soaking wet with sweat, but the sound of our flesh slapping together and Anne’s soft moans and gasps made it seem like heaven. Her cunt was so tight that I knew I was going to come any second, and then my seed shot out of my cock deep into Anne’s belly. She continued to move, and as my finger moved in and out of ass, then she too orgasmed. But as my dick went limp she stopped, and whimpered, “Bill, I never…” “I know, ” I said and once again moved my head down to Anne’s pussy.

I could see blood and sperm oozing from her cunt, but without any hesitation, I began to lick her clean. In no time at all, Anne was again in the throes of a huge orgasm.

We lay side by side, with her crying and me telling her I was sorry. She told me it was o.k., she enjoyed it, but that she had planned to wait until she was married before she had sex.

For the next few hours we lay there on the floor, talking, laughing, and kissing. Finally, surprising even me, as I am not a young stud, my cock got hard again, and this time I mounted Anne missionary style.

As soon as I was in, Anne said, “oh God, what if I get pregnant?” I asked her when was her last period, and she replied it ended four days ago. I told her we were good to go, she was o.k. and we fucked with wild abandon. Once again we were soaking wet with perspiration. I kissed her and we tried to force our tongues down each other’s throat. I rammed my cock as deeply as I could into this plainly looking girl who had a great looking ass, and once again put a finger into her asshole. She got even more active, and I rolled over on my back, pulling her with me. Now she was riding me hard, and the sound of fuck juices and bellies slapping filled the room. This time Anne began to cum first, and then I emptied another load into her.

I stayed all night in her apartment. She got up the next morning, and I told her I was going home, that I was sorry to have taken advantage of her. She assured me it was o.k., that she was 28 years old and it was time for her to become a woman. We parted on good terms, with the promise that if we ran into each other again, we would have an encore.