My parents passed away in a car accident when I was fourteen, and since no relatives were able to take me, I was placed in a Catholic orphanage in the late 1970s. The orphanage got most of what money my parents had, which wasn't a lot, with only a bit left over for my college education. Most people didn't want to adopt a teenager, and so although I had a few close calls, I wasn't adopted.
I grew up in Our Mother of Sorrows Convent and School outside of the city. The orphanage was actually phased out while I was there, and so by age eighteen I was their last orphan, occupying an almost empty wing of the charming old place, which was built in the Gothic style. I ate with the Sisters in their dining hall, and was still going to their Catholic high school.
My favorite teacher was Sister Margaret, who was the youngest of the nuns, although since she'd just turned thirty-five she wasn't all that young. She had dark hair, a pretty face, and a shapely figure--which was, of course, covered up by her habit.
A priest from a nearby monastery came to hear my confessions. I promised not to do the sin that I finally did for the first time at the age of 18, of touching myself for pleasure. But after resisting, sometimes for a week or two, I'd give in and confess again.
Sister Margaret taught history and literature, and I'd had her in one class each semester for the last three years of high school. We'd gotten to know each other pretty well, and she knew my sad story. Her story was also poignant, since she was also an orphan, having lost one parent as a young child to cancer, and another to a hit-and-run a few years later. She sometimes talked about how our orphan-bond gave us things in common. She enriched my life intellectually in so many ways, and also boosted my self-confidence. A few times after I turned 18 she'd said, when we were alone, that she thought I was handsome, and would be popular with the women in college--to which I blushed, and said I hoped so. I'd gotten into a good state university with a scholarship, in part because of Sister Margaret's recommendation letter, and would be starting in just a few months.
That senior year that I'd turned 18 I knew she could tell by how I gazed up at her from the front row of her class with admiration--and something more too--that I liked her a lot. Sometimes I stayed after class to talk with her, and we'd have good chats on all sorts of topics. When I was with her alone, I started getting erections around her. She was so lovely and empathetic, and so clearly liked me, that when I was around her I'd almost always get hard.
For weeks I hid it with books on my lap, or my book bag, but terrible sinner that I was, for the last few weeks of the school year I actually wanted her to notice that I was hard for her. Since I was mostly not masturbating, as the priest instructed me at confession, I would get erect around Sister Margaret quickly. What would they expect would happen? I knew it was visible when I stood up, because of the thin fabric of my school uniform slacks. My class with her was the last period of the day, and so I could stay after class as the school emptied out and talk with her.
I knew it was crazy and wrong to show her that I was hard for her, but I did it anyway. The first time I did it when I stayed after class--sometimes holding my book bag in front of me to hide it, and sometimes putting it down so that it was revealed--she seemed to be both shocked and pleased by what she thought she was seeing in my slacks. She blushed at first, but then recovered and kept glancing at it.
So I decided to do it again, but the second time not hiding it at all. I still had my book bag as we talked after class, just in case, but I just left it at my feet. She blushed again, and a few times she looked like she was about to say something about it, but ended up just smiling and seemingly encouraging me, as she glanced more obviously at my crotch, again mentioning that she thought I would be a success with the college girls. Each day when she first saw my hard-on for her through my slacks, she would blush and smile in a charming way, and then after a while look up at my face, clearly trying to concentrate on keeping eye contact.
When it was the last week of class I was even more bold one day. I didn't put on underwear, and so my hard cock was even more clearly outlined than unusual through my thin tan slacks. My cock head is somewhat large, and as I glanced down after the end of class, I could see that the outline of my mushroom-shaped head was clearly visible, at the top of the outline of my rounded six and a half inch cock.
"Sister Margaret," I said, after all the other students had left, as she was erasing the chalkboard in a charming back and forth motion, with her shapely ass toward me.
"Yes, Ben," she said, turning around and smiling.
As usual, she looked down at my crotch. But this time she didn't look away.
In fact, her eyes widened a little, and her nostrils flared, as she stared at the even more clearly outlined form of my erection in my slacks.
Smiling, I started talking, as she kept staring.
"Well, Sister Margaret, as you know, we're down to our last week of class. But I was wondering if you'd be willing to do an Independent Study with me over the summer in literature, maybe on all of your favorite novels that we haven't yet read in your other classes?"
Then I intentionally pulsed my cock once as I spoke, and her eyes widened a little more, as she kept looking at my bulge. She swallowed a bit loudly, and I could see she was breathing a bit more heavily than usual.
"Yes, Ben, I'll do an Independent Study with you," she said, and then she looked up at my face, "But since, as you just said, we're down to our last week in this class, and we're alone, I feel I finally need to say something to you. For the last few weeks when you've met with me alone after class, I've noticed that you often seem...aroused. What I mean is that you seem sexually aroused around me, Ben. Do you know that an outline of your...erect penis...is visible to me through your slacks?"
Now it was my turn to blush with shame, and my courage collapsed.
"I'm--I'm so sorry," I stammered.
Looking down I put my hands in front of my crotch. This was suddenly a disaster. I thought I'd seemingly misread that she'd been subtly encouraging me. I struggled to think of what to say, and I realized I had to tell the truth.
While still looking down with shame, I managed to get out, "Yes, Sister Margaret, I'm so sorry. It's...it's because I love you. Each week at Confession for the past few months, I've told the priest about my love for you, and even....my sinful thoughts about you. I've even confessed that when I talk with you after class that I get excited. Should I report myself to the principal, to Mother Superior, for punishment?"
Sister Margaret laughed nervously, and then said, "No, Ben, that's not necessary. Please don't do that! I'm confessing to a sin myself now, but actually part of me is flattered and, I'll confess, even though I really shouldn't, that I sometimes get...excited too, seeing how attracted to me you are. But I'm glad you're aware. I wouldn't want this to happen around other women--except for maybe when you're alone with your future wife, when you're in college or something."
"It only happens around you," I said, still looking down.
This was more or less true, because the other nuns were all quite a bit older.
"Really?" she said with a laugh, and then added, "Well, if it's just around me, and only when we're alone, then maybe it can be our secret. It's inappropriate, and it's a sin, but still, don't feel too bad. You obviously have strong feelings for me. You can even take your hands away, and show me again if you want. I've gotten kind of used to seeing you aroused around me. What kinds of sinful thoughts do you have about me anyway? I think it might be useful for you to talk about."
I slowly took my hands away, and then looked up at her smiling face, and shyly smiled back. My erection had softened over the previous couple of minutes, but as I realized she was seemingly encouraging me again, I could feel it start to grow again.
She smiled warmly at me and nodded, giving me encouragement, and then with pleasure I noticed that she was looking down at my crotch again, and continued to smile broadly as she observed my erection under my slacks growing again for her.
