I knew within the first five minutes that Derek Small was a very special young man -- and I'm not talking about sexually.
First of all, it was apparent that he was what you'd call "a good boy" and had obviously been very well brought up. Mike hadn't told him anything about the reality of what went on between me and my boarders, or young men, as I preferred to think of them, but even so, he didn't have a trace of that macho swagger that most well-endowed males seem to possess. He just came across as a serious young man, looking to get out of a noisy, freshman-filled dorm, so that he could get on with his studies. I remember be really struck by that.
What did he look like? Well, to cut to the chase, he was a hotty. Tall, a bit lanky (I got the feeling he'd fill out a bit more as the years went on), he had nice brown eyes, a full mouth, well-tended brown hair and a ready smile, handsome overall in a rough and ready way. He was quite nervous as we talked that afternoon on the patio and basked on a late fall day that felt like a genuine gift. Winter was closing in fast. He told me he'd been brought up on a horse farm and there was a bit of that genuine "farm boy" feel to him. He said "ma'am" more than anyone I'd ever met.
Mike, on the other hand, I was relieved to be shot of him, to tell the truth. Talk about a polar opposite to his replacement. He'd arrived full of swagger. Again not knowing what went on, I got the impression
his
idea was that he was going to seduce me. Within a day of his moving in, he put some really laughable moves on me.
First, he came out of the bathroom completely naked, towel thrown carelessly over his shoulder, cock partially erect. Obviously, he'd waited to hear me coming up the stairs. When I turned the corner, there he was, completely unabashed.
"Oh, I thought you were downstairs," he said looking me in the eyes. His eyes then travelled down to his cock which was swelling even more, his obvious intent to get me to look at it as well. "I hope you're not offended."
I shrugged, trying hard not to laugh. "No. I've seen the odd penis before. Now if you'll excuse me..."
Walking by him in the hall, he turned and his now-erect cock brushed my hip. I should have given it a good hard slap to teach him some manners.
Once in my room, I allowed myself a good laugh. That little prank meant Mike was going to wait a good bit of time until he got into my pants. A little frustration would be an excellent way to bring his childish behavior to a screeching halt. When we finally played, it would be plainly clear to him that I was the seducer and he was the seducee.
I learned later that Mike's behavior wasn't completely his fault. He'd lost his cherry at a very early tender age to one of his older sister's friends. That had started him on a tear through his neighborhood as the local women found out about the randy young man with the big cock and excellent staying power. It's truly amazing how many housewives will risk their marriages to experience a bit of pleasure from a well-hung man. Mike learned pretty quickly that he had a gold mine between his legs, and all those early lovers facilitated his change in attitude. No wonder he had that swagger. In his mind, little old Doreen Jones-Gonzalez, the middle-aged widow woman was destined to be just another notch on his pistol.
Derek, on the other hand, had none of that. It struck me as rather sad that he viewed the size and girth of his magnificent cock as an impediment to his happiness. How refreshing! This time I would only have to teach him how to use it, not beat the swagger out of him before we could get down to the serious work of making him an excellent and sensitive lover.
That was the only way to describe Derek's manhood: magnificent. I didn't think I'd ever seen a cock that was more perfect. Okay, I'll admit I've always been a size queen. Ramon, to whom I'd surrendered my virginity at the advanced age of 22, had been rather well-hung: 8 inches and pretty fat. He really knew how to wield it, too.
Sexually, I count my blessings every time I make love that I had such an experienced and wonderful teacher. It was worth the pain of high school and early college, with its cruelty and desperation to someone painfully shy, not particularly good-looking and consequently unpopular. I covered my pain by hiding behind books and my intellect, the one place where I actually had some confidence.
How Ramon had managed to see through all of that to the real me is still a mystery. I remember so well that first kiss from him. Sitting side by side at a table in a seminar room, we were discussing a paper I'd just written. He'd simply stopped my chatter, taken off my glasses and kissed me. It was all rather chaste, but it was the first time I'd ever been kissed romantically.
Something in me ignited and before the end of the night (a long, long night), I was no longer a virgin, I'd experienced multiple orgasms and had a pretty good idea of what sex could
really
be like.
Derek, on the other hand, had been jumped by a horny housewife, used, then discarded. His story about his fumblings after that made my blood boil. I so wished that I could have been his first. Here was a young man who so richly deserved what Ramon had given me.
I wasted no time in beginning the process of introducing him to what sex could actually be like. I spent the first 10 days or so of his time with me finding out more about him, and letting him settle in nicely. One night, he opened up about how he was shy around girls, didn't have a steady (I already knew that from quizzing Mike) and was generally as inexperienced as I'd already guessed.
Sitting back on the sofa as we talked, I made sure he got a good eyeful (not that I hadn't done a bit of that already in order to prime the pump) as I stretched out on the sofa. I gratifyingly noticed once again the predatory gleam that all males seem to get when ogling a female they find attractive. There was also a bit of a stir in his pants, so I immediately decided that tonight was the night.
It all worked perfectly: him coming out of the bathroom after showering and an invite to spy on me by my bedroom door being left partially open. My newest student took the bait perfectly.
I must admit to being more than a little turned on as I took off my robe while he watched from the hall -- complete with a gratifying little gasp as it slipped from my shoulders -- and I made sure I primed the pump a little more by playing with me breasts and nipples, always a big turn on for me. I could tell from the moisture and the second audible gasp from the hall when I touched myself between the legs that we were both more than ready for a roll in the hay.
It took everything I had to keep from laughing when I called him into my room. Such a poor little puppy dog face! It was clear that he thought I was going to boot him out of the house. Little did he know.
I made sure I gave him a good look at my body as I sat in a rather unladylike pose on the chair I pulled up. I also wanted to make sure that he knew who was boss. The distance his bathrobe was sticking out in front almost had me drooling, though, and when I had him take it off, it took every bit of my will power not to just throw him down on the bed, mount him and fuck myself into oblivion.
Derek's cock was very long (10.75 inches I found out later when I measured it) and nearly as fat as my wrist. Two things past that made it a further stand out (sorry for the pun): its head was huge, almost the size of a tennis ball, and it turned up slightly at the end. I mean, if I had to design the perfect cock for someone of my tastes, this was it. He also had a huge set of balls, so I was going to get generous amounts of semen, something I also love.
Somehow I managed to take it slowly that night. I can't tell you what it felt like to touch such a magnificent cock and to know that I could do whatever I wanted with it. I would be lying if I said that it doesn't give me a sense of power to control these very masculine young men that I take under my wing, and the cock that I was sliding along that first night belonged to someone whom I instinctively knew would make an incredible lover.
Teachers go their whole careers, working with thousands of talented students, and maybe only once or twice if they're extremely lucky do they get a genius. Derek's demeanor and his equipment led me to believe that he could fall into that category sexually.
I hadn't planned on actually letting him penetrate me that first night. Most of that was for him. I wanted to bring him along slowly and carefully, but partly it was for me. I knew what an important part anticipation plays in experiencing really great sex.
In the end, though, I just couldn't resist and I took Derek with his back to my bedroom wall. His hands on my rear end burned as I impaled myself on him again and again, and when his cock swelled and got impossibly hard prior to his orgasm, I nearly swooned.
He left me a complete wreck, lying on my bed that night. I'd told him I wanted to shower with him, but let me tell you, it was hard to get moving. Once in the bathroom, though, my lethargy fell away. This time I did stick to my plan and gave him a hand job. It was good for him, and great for me, since I just love masturbating men. I also wanted to observe just what that massive organ looked like when the crisis arrived.
The dear boy had me so worked up later, that I had to bring myself off twice before I could unwind enough to fall asleep. My biggest dildo hardly satisfied me. Once again, I was sorely tempted and nearly went down the hall to Derek's room. But success in my little "course of study" was completely dependent on keeping control of the situation.
Little did I know how hard that would become over time.
-=-=-=-=-=-=-=-=-
We were coming along rather nicely when the Christmas break arrived and Derek would be gone for 2 weeks. Normally, that's a nice time for me to decompress from first term, visit with friends, eat more than I should and be able to wander around the house naked without having my young boarders think that I'm gagging for more sex.
Something was different that first year with Derek, though. I constantly had him on my mind. What was he doing? Was he thinking of me at all, or had he met some sweet young thing who had the intelligence to recognize just what a find he was? She'd seduce him, make him hers and I'd get a phone call saying he'd decided to switch schools. For the first time in my life, I lived in fear that one of my boarders would disappear.
I also was climbing the walls in sexual frustration. That final week of the fall term, we had fucked ourselves into oblivion and it surprised me how much I missed Derek's tender touches, his warmth and humor, and of course his magnificent cock.
I found myself masturbating 2 or 3 times a day. I watched some of the old videos of me that Ramon had shot with all combinations of men and women, then I'd think of Derek doing the same things. Out would come one of the dildos. I took myself on the bed with me knees drawn up, plunging those fake cocks in and out of myself almost savagely in my search for satiation from the itch that was consuming me.
One of them had a suction cup, so I stuck that on the tiled wall of my en suite bathroom. Even with a vibrating butt plug buzzing away and that latex monster ravaging my cunt, I still couldn't get what I was aching for.
On Christmas Day, two separate things happened, both rather unexpected. I was in the kitchen eating a solitary breakfast and feeling thoroughly sorry for myself. Later that day, I was to go to dinner at a colleague's house. It would be the usual convivial evening, we'd pop Christmas crackers, read the bad jokes they contained, wear our tissue paper crowns and indulge in way too much food and wine. After dinner there would be some sort of silly game, we'd listen to music and I'd wobble home very late. For some reason I dreaded the whole thing that year.
Then the phone rang.
