The Philosophy Teacher

"I don't know" replied Anna. "I just know I don't want to be apart from you anymore!"

"I'm feeling the same way but there are going to be complications. What will your parents think? What about our huge age difference? Are we going to live together? We really need to sort things out quickly before somebody gets hurt, namely your parents."

Anna looked at me in the same way she did when we used to argue about religion, all of those years ago in my garage. "Let me deal with my parents, they trust me. I don't give a shit about our age difference. And, the only possible person that will be hurt here is me if you make me leave you!"

We laid there looking at each other a little longer until Anna said, "Look, my parents are going to visit my sister Nadya next week. Why don't I stay here with you for the whole week and see if it works or not? When my parents return, I'll tell them I love you and want to be with you if we decide that's the way we want to go. Does that sound fair?"

I thought about it and said, "Okay, when do they leave?"

"The day after tomorrow"

"Do I need to make any changes around here, besides these sheets we just messed up?"

Anna laughed and said, "No, I want things to be the way they have always been, except I get to fuck you now! Oh, and you definitely still have to go commando!"

"You have to go commando too, then!"

"If you had been more observant you would have seen that I was commando!"

"Oh, right...you were, weren't you! I'm just an old fart!"

Anna laughed again, then said, "And no more of this old fart shit! You fuck like a twenty-year-old!"

I knew when I was beaten and told her OK. We laid in bed for several hours just holding each other until Anna decided she should go home. I laid in bed and tried to process what had happened that night. The only thing that I could come up with was that I had never been happier.

The next morning when I awoke I felt wonderful, maybe a little sore, but wonderful! I made coffee and sat back down and finished reading Anna's dissertation. It was, truly, an amazing piece of work. When I finished I just sat there marveling at what she had produced. This woman was a bonafide genius! At around 10 there was a knock on the door and I yelled for Anna to come in. She bounded into the room, threw her arms around my neck and kissed me deeply while crushing her breasts into me.

"Good morning!" Anna said. "Isn't it a wonderful day?"

"It is indeed. And, to make it even more wonderful I think you need to stop knocking on the door." I got up and went to my junk drawer and gave Anna a key to my house. "Not that you really need a key because I only lock up when I leave the place."

Anna beamed and then put the key into her pocket. "So, can we have another roll in the hay today?" Her smile was so big I thought her muscles in her face had to hurt.

"No!" I replied. "We have the whole of the next week starting tomorrow." I got up and poured myself another cup of coffee and then went to the fridge and grabbed a bottle of Coke and handed it to Anna. "We are going to sit out in the garage and you are going to tell me about your 6 years at Harvard. I want to hear about your academics, then your athletics and then all the rest of it, in that order!"

Anna looked at me with a pout so I left for the garage. She followed as I knew she would. I opened the garage door, got a couple of lawn chairs for us facing them out and then I sat down in one and Anna sat in the other. Once she got talking she forgot about her disappointment, it was like a dam had burst. She spoke of her first two years and how easy it was because she had read everything and discussed them with me. By the third year she was treading on some new things but really liked it. In her fourth year, she started grad school and loved it. It was like sitting out here with you when I was a kid reading and discussing and arguing...I was in heaven, though I wished you were there with me because you would have loved it too. Writing and defending my dissertation was actually a lot of fun. Dr. Brown, my lead professor (who reminded me of you a little bit, actually) was a great help. And then I was done!

I asked a few questions about a few points and about some of her professors but in the end, I was quite satisfied with her story. I asked her if she wanted another Coke but she said she would rather have water. I grabbed her a tall glass of ice water and one for myself and then asked her about her volleyball exploits.

She said playing volleyball was a great thing because it kept her grounded. The team was pretty weak but they all got along well and had fun. She said she remembered me telling her that it was too bad that she wasn't left handed so she could spike the ball, occasionally, instead of setting it which made trouble for the other team's defense. So, she taught herself how to hit left handed. It took quite a while but by her second year she was pretty good at it and she said I was right about how it opened up their other hitters. "I even crushed it a couple of times!" she said proudly.

It was getting to be lunchtime so I told her we should go in and have some lunch. As I fixed our meal Anna told me about her life in the dorms and all of the friends she had made. She talked about going to the big football game with Yale every year and all of the events she attended in Boston. She told me she had dated three guys while there. Two of them were quite nice and one was a total jackass. As we ate Anna continued her story until she was finished.

"Well, it sounds like you made the right choice going there." I said.

"Yes, it was great! I learned a lot, I had fun and I made a lot of good friends. You can't ask for anything more from college."

I grabbed our dirty dishes and started cleaning up. Anna asked if she could help, but I told her that there really wasn't much to do so she should just keep talking to me. When I had finished, I turned to ask her another question but was surprised to find her sitting there with her shirt unbuttoned and her breasts staring me in the face. "Jake, I'm kind of horny and I was wondering if we could make love again?" As she said this she got up off of her stool at the breakfast bar and walked around towards me. When she got around the end of the bar I could see she had dropped her shorts and kicked off her sandals. She walked up to me, pulled me into a hug and kissed me so passionately my resolve withered like a raisin on the vine.

We kissed for several minutes until Anna began pulling my shirt off and undoing my shorts. Before you could say 'howdy' I was as naked as she was and I was sporting another erection for the ages. I lifted her up and set her down on the kitchen counter where I buried my head between her legs and began licking and kissing Anna's vulva. She spread he legs wide with her heels on the edge of the counter. I aimed for Anna's clitoris and tried to bring her to an orgasm as quickly as I could. After several minutes of clitoral stimulation with my tongue Anna began crying out that she was going to cum! As she orgasmed, Anna shot another stream of ejaculate into my mouth, which I held there and then moved up to kiss her. I let her girl cum transfer from my mouth to hers as we kissed and her eyes widened noticeably while I did.

"Nobody has ever done that with me! I taste pretty good, if I do say so!"

I laughed as I straightened up and pulled Anna's bottom towards the edge of the counter and inserted, my now rock hard, cock into Anna's vagina. We both moaned with pleasure as I slowly sank myself into Anna's tunnel. She wrapped her legs around me and pulled me towards her like a bronc rider at the rodeo. Using her heels like spurs, Anna goaded me into thrusting into her faster and harder. She had developed a sheen of sweat on her breasts and belly as we fucked. Anna reached down between us to stroke her clit and began cumming within two minutes crying out as she did. I wasn't far behind her and shot my load deep into Anna's womb. When I was finished, I dropped my head between Anna's breasts and gasped for breath. As my breathing slowed I could hear her heartbeat with my ear against her sweaty skin. Anna held my head against her chest for quite some time before releasing me.

"Oh my god, and I use that term colloquially, Jake! That was fantastic! I've never climaxed twice like that in quick succession like I have with you! I've also left quite a puddle on your counter!"

We both laughed as I helped Anna down off the counter, lifting her over her puddle. When her feet hit the floor, she threw her arms around me and kissed me deeply. As we kissed I could feel myself get hard again. This girl was so damn sexy I could barely contain myself. We walked to my bedroom, laid down on the bed and embraced again. We ran our hands all over each other taking in, tactilely, every bit of the others body. After a while Anna pulled back, looked into my eyes and said, "Can I ask you something?"

"You can ask me anything...you always have." I replied with a grin.

"While in Boston I dated three different men, as I told you this morning. I had sex with all three of them because I wanted to be experienced for you. I thought about retaining my virginity but decided that was a little old fashioned and I wanted to enjoy sex with you from the start. I did, however, save something for you that I didn't want to surrender to a college boy. Something I wanted to share with you only. Will you have anal sex with me?"

I sat up and propped my head up on my arm and looked down at Anna with wide eyes, "You want me to have anal sex with you?"

"Yes, I do. One of the boys in Boston tried it, the one I called the jackass. He touched and licked me back there and, frankly, I thought it felt pretty good in retrospect. But I wasn't going to let him have coitus with me back there because it seemed so dirty. When I refused, he got all shirty with me and stormed off. I never saw him again, thankfully. But, he had planted the seed in my brain and I began exploring myself back there a little and liked the way it felt. I did some research online about how to proceed. Everything says to clean yourself thoroughly, use a lot of lube, go nice and slow and use lots of lube! I cleaned myself inside and out before I came here and I have a tube of KY in my shorts. This is the one thing I can give to you that nobody else has had. So, will you have anal sex with me?"

I was pretty flabbergasted by Anna's request. I had never considered anal sex in the past because I'd never heard of it before, except it was what gay men did. Vaginas and mouths seemed like plenty of orifices to get on with. Besides, it seemed to me that it would be pretty uncomfortable for the woman if my prostate exams were anything to go on (though as I thought about it, prostate exams didn't hurt, exactly, they were more awkward than anything).

"I've never had anal sex before and I really don't want to hurt you. Are you quite sure about this?"

"I am. This is something we can share together. I want you to take my virgin butt!"

Anna jumped out of bed and ran out of the room and came back moments later clutching her KY tube in her hand. She crawled back onto the bed and while on her knees looked at me pleadingly and said, "Please?"

"Okay, how do you want to do this"

"I think it would be best if I was on my hands and knees and you were behind me. I would like you to lick and kiss my anus because that really felt good when the jackass did it. Then, after a while you can put a finger in me and then two to loosen me up before using your penis."

"Wow, you've really thought this out!"

"I've saved this for you, so yeah, I've thought it out."

I got up on my knees while Anna crawled onto the middle of the bed on her hands and knees. I got behind her and began admiring her beautiful ass. It was perfect thanks to her years playing volleyball. I ran my hands over both globes and admiring the firmness of her muscles and the softness of her skin.

"That feels nice." Anna said as I continued rubbing her cheeks.

After a couple of minutes, I used my hands to spread her cheeks apart. I had never stopped to admire any woman's anus before and I'm sorry now that I hadn't. Anna's was a pink symmetric circle of radial lines emanating from the center. It was as hairless as her pussy and looked quite inviting. I leaned down and tentatively licked it causing Anna to shiver and to develop goosebumps on the globes of her ass.

"Oh my!" Anna groaned.

Taking her reaction as positive, I began licking her anus with more purpose and, occasionally, probing inside her with my tongue. Each time I stuck my tongue inside her Anna moaned loudly so I continued to probe her with my tongue. I could smell Anna's sex as she got worked up again so I decided to give her pussy a quick lick too. I couldn't believe how wet she was! This girl really liked anal stimulation! I decided it was time to delve into her with a finger so I grabbed the tube of KY and squirted some on my right index finger. "Anna, can you pull your cheeks apart for me?" She dropped her head to the bed, reached back and spread her ass cheeks wide for me exposing, both, her anus and pussy.

I reached down and smeared the KY on and around Anna's anus and then tentatively probed into her ass. Anna moaned deeply and said, "Oh yes! That's nice!" I slowly pushed my finger inside until it was all of the way in. After a couple of moments, I began pulling out and then pushing in again. I would, periodically, squeeze a little more KY onto my finger to keep it lubed up. I, also, pushed my middle finger into her sopping pussy sawing both of them together in and out of her holes.

"God, Jake that's wonderful!"

After a while Anna asked me to put a second finger in her ass so I added my, now slick, middle finger to my index finger and slowly pushed in. She groaned loudly again as I stretched her anus with the second finger. I stopped and asked if she was okay.

"That was a groan of pleasure, Jake! I'm loving this so far!"

After a while I put my ring and little fingers into Anna's pussy. Anna moaned and groaned continually as I sawed my hand in and out of her openings. Finally, she said she thought she was ready for my cock. I pulled my fingers out of her, slathered KY on my dick and on her slightly gaping anus. I aligned myself with Anna's opening and gently pushed forward. I could feel Anna push back against me trying to help penetrate her tight ass. After a few moments, the head of my cock slipped inside of her. Anna gave a slight yip and I stopped pushing immediately.

"Are you alright? Should I pull out?"

After taking a few deep breaths Anna said, "I'm fine, that first penetration stung a bit but the pain is waning quickly. You can push in a little more now. Just go slowly..."

I decided to take things in stages by slowly pushing in a little bit and then stopping. I couldn't believe how tight and hot her ass felt on my penis. I was very happy I had climaxed earlier because I now had some staying power. After ten minutes or so I had lodged my dick all of the way into Anna's ass.

I asked, "How are you doing? Are you okay?"

Anna leaned up and turned her head to kiss me. I ran my hands around her belly and up to her breasts, pinching her nipples while we kissed "I am wonderful! You feel humongous in my ass...humongously good! I think you can start fucking my ass now!"

When Anna leaned back down onto her hands I slowly pulled out about halfway and then slowly pushed back in. Anna gave off another contented groan so I pulled out a little further and slowly pushed back in. Then I pulled out all of the way so I could squirt some KY into Anna's anal cavity and squirt some on my erection before pushing inside of her again. I couldn't believe how good it felt to fuck Anna's asshole! The sensations were phenomenal as I pumped in and out of her slowly. I began fucking Anna a little faster now as my lust began rising. I had been fondling her breasts but now was holding her by the hips so that I could pull her back to me.

"OH JAKE! FUCK ME HARDER, JAKE! THIS IS WONDERFUL! FUCK MY ASS, JAKE! FUCK MY ASS!" Anna cried out.

I began pounding into Anna's ass. The sight of my cock sliding in and out of Anna's tight ass made me hornier and hornier. Anna reached underneath herself and began working her clit over as we continued our primal fornication. Before long Anna cried out that she was cumming! I could feel her asshole pulsing on me as I continued pummeling her anus. She was shaking and shivering and felt like she wanted to collapse but I held her up by her hips and continued pumping her because I was on the cusp of my own orgasm.

When it finally hit, I couldn't believe the intensity of it. My sperm exploded out of my cock into Anna's bowel shooting stream after stream deep inside of her. My eyes rolled back into my head as I grunted and groaned. I felt I was on the verge of blacking out so I fell over onto my side pulling Anna with me. We both laid there panting, my cock still buried in Anna's ass. My penis slowly shrank down and finally fell out of Anna followed by a stream of my sperm. I really didn't care because at that moment I had never felt better.

After a while Anna turned around to face me and gave me a sweet but passionate kiss. I pulled her into me and kissed her back. At this moment, I knew I was in for the long haul with her. We kissed and smiled at each other for several minutes until Anna said, "That was fantastic! It hurt a little but felt really good at the same time. I climaxed so hard I think I passed out for a moment! And then I could feel your climax and could feel your ejaculation inside me! I can't wait to do that again!"

I smiled and said, "Yeah, I have never cum that hard in my life. I never knew about anal or I would have tried that years ago! I hope I didn't hurt you, I got a bit carried away at the end there."

"Oh, no! You didn't hurt me at all! You were perfect!"

We laid there in each other's arms eventually falling asleep.

When we awoke, it was early evening. Anna decided she needed to leave to spend some time with her parents before they left on their trip. After she left I took a shower and went over, in my mind, everything that had happened in the past two days. I made myself some dinner and then read for a while before turning in for the night. I was startled awake by a warm body crawling into bed with me. Anna pulled herself against my back, hugging me from behind. I turned over to face her and could make out her smile in the darkness.

"Hello, lover! I thought you would like a good night kiss!"

I laughed and told her, "I'd love a good night kiss."

Anna leaned into me and gave me a very passionate kiss. As we kissed she pushed me onto my back and straddled me taking my now hard cock and sliding down on it with her pussy. Once I was buried into her vagina, Anna propped herself up on her arms and slowly fucked me. She looked into my eyes smiling as she lifted herself up and then sank back down. I could see, in my peripheral vision, her pendulous breasts swaying back and forth as she continued to slowly make love to me. I reached up with both hands and grabbed her nipples and began rolling them, hard, between my thumb and forefinger causing Anna to groan loudly.

We were both beginning to feel our climaxes rise as we slowly fucked. Anna bent down and kissed me deeply and I continued to pinch her nipples as we continued. Finally, Anna cried out that she was going to cum and then I felt the telltale squirt, her shiver and shaking body. I followed suit about twenty seconds later as I shot my seminal fluid into Anna's depths. She then collapsed on my chest and I held her there as we recovered from our orgasms.

After we had gained our breath back I whispered into Anna's ear, "That was the most wonderful goodnight kiss I have ever had!"