Thinking back on my first experience in sexual intercourse, to be plain, I wasn't very good. All of the wet dreams, numerous hard-ons, and "hands on" practice, doesn't really prepare you for that "first time". I kind of feel sorry for her now because I know I bruised her thighs and ass trying to poke my dick into her pussy and when I finally got there I came before I finished my first stroke. For her it probably wasn't very satisfying, but for me it was wonderful. She was patient and took me under her wing and tutored me in the art of lovemaking, slowing me down and showing me points of interest along the way.
I have in the years following, took it upon myself to carry on this training, to teach what had been taught to me. My first pupil was a preachers daughter, a 23 year old virgin with a body to die for! I swore to myself that I would take my time with this "student", to educate her as best I could. Well it took me about three months to get in her pants, I was ready to abandon this project and go with a already
trained partner. I was getting a little impatient because she would not even let me touch her tits for a month, we had kissed and kissed, moaned and groan, but every time I made a move she stopped me. I started telling her of the importance in being sexually trained and also that she wasn't getting any younger, you know like training a young pup compared to an old dog, she understood and finally agreed to give it a try.
The first thing was to show her how to gently stroke the penis, in which I gratefully offered mine as the study model, I showed her how to slowly stroke it up and down while keeping those sharp fingernails out of the way. This took a little longer than expected because she kept on holding it at the base. Now, if all the guys out there are like me, the pleasure nerves are in the "upper third" of the penis not in the base. After a while of stroking practice, she finally got the hang of it. A little while later I decided to try her on blow jobs. This one was a little harder for her to master, at first she had problems keeping her teeth out of the way, and after some ointment and a few band-aid's on my dick I told her that she might want to use a banana for further practice , just until she got more comfortable with something in her mouth.
While my penis was healing I thought it would be a good idea to explore her body and explain to her what a guy usually does to the female. I started with gentle stroke of the tongue around her nipples and gently sucking them while I teased her other nipple with my fingertip. All of this was well received by her, she was now breathing hard and moaning, so I decided to see if she was up to a little more exploring, I started kissing down her chest, moving farther down to her abdomen, the breathing was getting more advanced and the moans louder. I went a little further, unbuttoning her pants then slowly unzipping them, she arched her back to allow me to remove her pants, I pulled them slowly down, over her ass and there, lying directly in front of me was the most unkept lawn that I had ever seen in my life. Now, how do I approach this, do I just tell her that the 70's are over and you need to mow your yard or just calmly tell her that most sexually active women trim it up to promote a healthly lifestyle, I choose the latter and we spent the next few minutes manicuring it.
Finally, back in action, I leaned down over her pussy and used my tongue to tease her clit, she was moaning and arching her back, her hands had a handful of my hair, her fingernails tore at my ears, the pain was getting very intense but I hung in there. Her juices were flowing heavy as I took my tongue and gently entered her pussy tasting the fresh nectar, as her breathing got more and more intense, I went back to work on her clit, she then went into uncontrollable movements. I thought to myself, this would surely get her worked up so she would go all the way. I tried to stay with her to make her orgasm more intense, but wrong move, I lost contact with her pussy only to regain contact with her pelvic bone and the blow sent me off the bed into the floor. Dazed by the impact, I gathered my senses only to realize I had a busted lip," Oh my god!" she said breathlessly, "are you alright" I staggered to my feet "yea, I'm fine, did you enjoy that", still trying to catch her breath she told me that it was wonderful!
I proceeded to asked her if she was ready for the next step, she nodded yes. So went back through the steps she had previously learned, she took my cock in her hand and circled the head with her tongue, slowly stroking it up and down, so far so good and no teeth, for the moment I felt proud watching my student work hard and staying focused. My cock stood firm, throbbing, ready for the mission before him, going where no man had been before, this was the moment, the moment that every boy had dreamed about, the ceremonial deflowering of a virgin, this was almost like seeing Bigfoot in a way, it was something you heard about but none of my friends had actually done it.
I applied a thin layer of KY Jelly to the head of my cock and then slowly eased toward my intended target, 5-4-3-2-1.......We have insertion...I said we have insertion....Ugh, ugh, damn it, it would not go in, I kept pushing, harder and harder...nothing! I saw my cock, rock hard as it was, actually bow in the middle! what the hell is going on here? I put on some more KY and tried again...still nothing, this was tough! Finally I applied the remainder of the tube to my cock and her pussy, that should do it I thought, She was bracing for impact and I backed up to get a run at it, like on the movies where a cop gets a run and knocks down a door, only mine ended up like the comedy version where someone opens the door at the last moment and the cop crashes into the room! Her scream of pain in my ear and the pain coming from my nuts that had crashed into her ass was almost unbearable.
I looked down to see a intense expression of pain on her face "Are you alright" I asked, with a hurting voice, "Do you mind getting off of me" she replied painfully. So I got up and apologized to her "Geez, I'm sorry, I didn't think I used too much Ky since we were having so much trouble getting it in, I then noticed tears streaming down her face "I really didn't mean to hurt you!" I said, "Oh,no" she replied "it's not really that, I mean it does hurt a lot but I was crying because it was my first time", "Ah damn" I thought to myself what a time to get sentimental, my lip is busted and my nuts are killing me and this was becoming one of those Hallmark moments, so I give her a hug and let her finished crying, then she looks up and me and smiles "How about we clean up a little and finish this tomorrow, I really, really want you bad!" "Now that sounds good to me" I said "Do you think you could get me an ice pack?" "For your busted lip?" she replied "No" I said "I need it for my nuts!"
