A Day in the Convent

Like almost every summer since I graduated from elementary school, I was over at the convent of the elementary school which I had attended, doing some volunteer work around the convent. Even after I graduated college. I would try to help maintain the upkeep of the place, like painting walls, cleaning gutters, shampooing the carpets, replacing air filters, moving furniture around, whatever Sr. Mary Davis had in mind for me to do. I found it impossible to say "no" to her, as she had been the principal of my school and the reverend mother of the convent, and I was "groomed" from an early age to be obedient to her and try to do anything she says / asks to the best of my ability.

One time when I was considerably younger back in the 70's, she had me using a brush to clean the dust from the radiators in one of the classrooms. Apparently, I didn't do a good job, and she let me know about it. Since then, I knew I would always have to put my very best effort into anything she had me do. She was very appreciative of both my efforts and my output. In the beginning, I was just appreciative that either she didn't get mad at me or that I didn't disappoint her. Then later, I just became appreciative that she was appreciative.

So when I would return each summer to do some volunteer work from time to time, it was always a challenge to do the best job I could with what was asked of me. I continued to have this fear of disappointing her. It made me feel very timid whenever I was inside the convent, even now at 23.

Because their convent had extra bedrooms on the 2nd floor, various nuns would be sent there to stay / live, even though they didn't have a role at the school. Some would be "retired", "semi-retired" or whatever. I would see a few of them walking around outside the convent once in a while, and occasionally, I would see them in church if we attended the same mass on a given Sunday.

One of the nuns I would see there, Sr. Noreen, had intriguing breasts from what I could see. They seemed to be on the nice size side, and my mind often had me guessing the actual shape which may have been offset by the style of her bras. Sr. Noreen was an older woman, I would say at least mid 60's, probably older. She didn't wear a veil or a habit, as some of the other retired nuns did. Her hair was light gray, short, and cropped. It was short enough to see her long ears which seemed to complement her long nose and long narrow face.

I could never tell if her eyes were hazel, green, light blue, or even light brown. I never got close enough to look, nor did I ever look at her face to face for a very long period of time, as I was somewhat shy. All I could surmise was that her eye color was not distinctively blue or brown.

The shape of her face and lack of make up sometimes caused her to look somewhat like she had a man's face. Other than finding older women attractive in general, I didn't find her face attractive at all. But her breasts had me somewhat fixated. They were a nice size, but I couldn't imagine how they would actually lay without the support of a bra.

She had one of the rooms on the 2nd floor of the convent. Except for maybe once or twice when I may have gone up there for one thing or another, I was always usually either on the main floor or in the finished basement whenever I would be in the convent.

It was my 1st day back at the convent during this particular summer when I was 23. I had basically shown up in a shirt, shorts, and old sneakers. Sr. Mary Davis had given me a short "laundry list" of things she wanted me to take care of. I imagine this list had probably been building up during the course of the year, and now I was finally around to tackle it.

After I had been there for a while, Sr. Mary Davis apparently went out. I had thought she went shopping, but I couldn't be sure where she went or for how long she would be gone. Sr. Johanna and Sr. Maureen had taken time to be with family, as it was a summer break for them from the school year. It was very quiet in the convent. I assumed there were retired nuns around somewhere, and that they could emerge at any possible moment.

One of the last things on the list Sr. Mary Davis gave me involved tightening and adjusting a few things in the 2nd floor bathroom. After finishing up there, feeling I did the best that I could with everything, I headed back down the straight hallway to the staircase. One of the bedroom doors on the right was part way open. It either hadn't been open when I first went up there, or I didn't notice it. I went with my subconscious reflex tendency to glance in as I walked by.

I was astonished at what I saw. I kept walking.

"Jim!", Sr. Noreen called for me as she had seen me walk by. I had tried to just keep walking.

"Come here, dear", which caused me to instantly freeze. I started to tremble, as she was calling me back to what I just saw.

I came to the semi open doorway, and Sr. Noreen was just as I had just seen her when I had just walked by. She was looking right at me, as she was sitting up in her bed slightly, resting on her elbows, with her left hand hanging over a pillow which had her gold diocese ring on her ring finger. It was about a whole centimeter wide.

But other than white "granny panties", she was nude! I was horrified that I was looking at a nun's mostly nude body as she looked at me. Embarrassed, I tried to look away at the wall off to the side as I said, "Hi, Sister" to her in a quiet shaky voice.

"Come in. Close the door behind you."

The shade had been drawn on the one window in the room. The walls were a light shade of tan, and there was a small light lit on the table next to her bed.

"Jim? Look at me." I felt so uncomfortable, being asked to, no - "directed to", look her way as she lay there. And there were her exposed breasts. I finally got to see them. Indeed, they were a bit flabby, but not as bad as I might have imagined. Obviously, her bras had been evidently giving them good support and provided a good shape to them. But even though they lacked form on their own, I still found them appealing to look at. Her nipples and areolae were slightly on the tannish side. Not the pinkish red I had imagined, though her skin did have a bit of color to it. Other than a few subtle wrinkles on her face and fingers, her skin was otherwise smooth and not really wrinkly at all.

Her stomach was a little on the chubby side, but she really wasn't that overweight. It looked like a "healthy" chubby.

As I shifted my eyes from the wall to eye contact with her, I was once again in a situation to try to maintain eye contact without letting my eyes shift down, for I knew she was looking right at me, and she would easily know where my eyes were going. I couldn't be sure she wanted me to look at her body, even though she was aware she was nude, and not making any attempt to cover herself.

"Do you like them? I see you checking them out before and after masses sometimes."

I was busted. In fact, I had BEEN busted, evidently for a while now, without knowing it. As I've just now come to discover she knew, even more embarrassment came over me. All the while, I thought my glances had gone unnoticed. But this nun was now confronting me about having been checking out her body, and now she was showing it off to me. I felt really awkward. This came as a complete surprise. I felt a sense of shame, but it was shadowed / eclipsed with confusion, because she was deliberately letting me see her body. I couldn't have seen this coming, as it was not consistent with how I had characterized her character to be. I realized I really didn't know her. I had only thought what I thought about her, without knowing who she really was.

To me, she was a nun. Someone to be humble and shy in the presence of, and obedient to if necessary. If not because she was a nun, because she was an elder, likely 40 years or so my senior. Other than maybe her nice rack, I never made a connection between her and sex, especially because her face appeared somewhat manly to me. And she was, after all, a nun.

"Yyy...", I started, but was so hesitant as to saying a "yes" or a "yeah", as I was thinking I couldn't deliever it respectfully or sincerely enough. So finally I said, "They're nice, Sister." It was as respectful as I felt I could have put the compliment, having had no time at all to prepare myself for this encounter.

She sat up and beckoned for me with her arms to come over within arm's reach. I was feeling a bit weak in my knees, as if I could feel the timidness in my body to get close to the bed. But my sense of obedience overcame me, and I moved closer to where she could grab my waist. Once I had gotten close enough, she pulled me toward her, so that I was standing right at the edge of the side of the bed.

"Are they arousing you?", she asked as I felt part of her hand lightly touch my flaccid cock over my shorts. I remained looking at her face, watching it looking slightly down toward my crotch area. So I didn't see how she was touching me, but I could feel my cock developing an instant erection and bulging up the pouch in my jockstrap that I had on underneath my shorts.

Suddenly, I could feel her fingers curled against my waist, as she had grabbed a hold of the waistband of my shorts, lowering it and revealing my bulging jockstrap pouch. Though not the nun of my choice, but "a" nun had her face so close to my bulging pouch!

"Wow, you are big! It's nice to know I can still turn a man on." I could feel her fingers lightly running up and down my shaft over the pouch of my jockstrap, exciting my cock even more. I had long wished Sr. Mary Davis, or even the other nuns I was more familiar with, would have touched me in this way by now, as it had been a long time fantasy of mine. And now this was happening with a nun in the same convent, though not quite the nun of my choice. I was beside myself, wondering where this was leading. I was nervous at the prospect. How far was she going to want this to go. I was not prepared for this, as I never would have guessed Sr. Noreen had this in her. She had known for a while I had been stealthily checking out her body, and had kept it a secret that she knew.

She lay back a little, resuming resting on her elbow on a pillow. "Sit down on the bed", she softly commanded. She had brought my shorts to my knees. I wasn't sure if I should pull them up, take them off, or what. So I just sat down with my shorts around my knees.

"Go ahead. Feel them", she softly commanded, as I sat on the side of the bed with my back to her body. I thought it was bad enough that I had seen her mostly nude, but now she was going to have me touch her body too. This was surreal. I felt I had to be obedient, with a certain part of me wanting touch them anyway. But I felt so awkward and scared about doing so. My morals were confused and conflicted. Ultimately, the obedience factor took over.

I reached over, putting my hands at the sides of her breasts with a minimal grip. She started to move a little, and I wasn't sure what was happening. My reflex instinct made me withdraw my hands, but then she gripped my wrist, returning my hand to her breast. So I followed with the other. She moved my wrist a little, as if she wanted me to caress her breasts. So I started to slowly caress them. I was looking at them as I did so, and I noticed her nipples were starting to perk up a bit. Ironically now, I was too scared to look at her face, so I gave in to my visual fixation on her breasts. I was afraid to look in her eyes. While I have to admit I was enjoying fondling her breasts to a slight extent, it seemed spoiled as I was too nervous to enjoy it fully with this encounter that I could have never imagined would be happening.

Sr. Noreen reached up to grab my head and pull it down towards her left breast. I started by kissing it just beyond the areolae, and she gave it a slight "guiding" towards her nipple and I licked it, and eventually latched on and started sucking it softly.

After a few minutes, the other side of her body rose, and I could feel her hold on my body twist me until I was on my back, as her left nipple slipped out of my mouth in the process. She had situated herself to lay over me. My legs were still hanging over the side of the bed, and she reached down, hooking an arm around my thighs, as if to lift my legs up onto the bed. I kicked off my sneakers as my feet rose. I was lying fully on my back, with her laying over me. She dropped her right breast in my mouth for its turn, and I started softly sucking on it.

After a short while, she moved off me to lie alongside me to my right, tilting my head toward her. She pulled my head in to her right breast, and I started to suck the nipple again, as we lay side by side. I felt her reaching down and fondling me over my jockstrap pouch, as if to check to see if it was still hard. I still had the erection from the time she had lowered my shorts. Eventually I felt her yanking the waistband of my jockstrap down, and I lifted my body to allow it to slide down as far as she wanted it. It didn't really get past mid thigh. I started to get a bondage feeling, with my shorts at my knees binding them together, and now my jock holding my thighs together.

She grabbed my cock and held it briefly. I froze as she did, not knowing what she was intending. She let go and reached further down until she got to my balls. I could start to feel her playing with them, as if caressing them and exploring them with squeezes and rubs. I lay perfectly still with a feeling of helplessness, though I was enjoying every moment. But still I was scared, not knowing what was to come. Was she going to have me penetrate her. Was she going to stroke me to completion. She had stripped me to where she had access to my genitals, and seemingly went right for them.

Her hand moved back to my cock, and I could feel it slowly slide back and forth just a few times before it stopped. There was no lubricant. My body felt a slight sense of panic, that she was going to make me ejaculate on her bed and make a mess.

As she held my cock, she began to whisper to me. "One time when I was at the airport when the diocese sent me overseas on a misson, I was subjected to a strip search." I felt my cock become even harder at the mere mention, and I was a bit embarrassed, because I knew she could feel the further arousal as she held it. There was no hiding the fact that I was aroused at the thought of her being strip searched, because she had the evidence right in her hand. My facial expression was a look of shock and surprise, as I gazed at her, still not quite able to decipher the color of her eyes.

"Apparently, as I found out later, they had set the scanner to 'male', probably because I can look like one at times, and I guess my voice is a little on the deep side too. The way it was described to me, setting it to 'male' caused it to set off when it detected an anomalous mass in my upper chest. So I was taken aside into a private room by a male security agent, believing I was a male carrying contraband, and he had me remove my blouse and then my bra right in front of him. He apologized once he discovered I was, in fact, a woman who had informed him I was a nun. I forgave him, because I could understand how he could make a gender mistake like that with me. And we're all human after all."

She began lightly stroking my cock again, as if she told me that to further arouse me. I have to admit that it did, the idea of a nun having to expose herself to a man.

Nevertheless, I whispered back, "I'm sorry that had to happen to you."

"It's alright, dear.", as she continued slowly and softly stroking my cock a bit. I felt aroused by this nun calling me "dear", and I wondered if her strip search experience was actually a turn on for her, because she was mentioning it to me while she was holding my cock.

She stopped stroking again, but maintained her grip. "I became a nun after I was raped." Another surprise admission, but this time, it made my cock almost want to go limp right away. Yet her grip on it seemed to make it want to stay at least semi hard.

"As I was going into my apartment, two men came up from behind me and forced me inside. They held me down and took turns."

This kind of killed the mood for me, as I felt overcome with sadness that this had happened to her. I didn't know what to say, besides "I'm so sorry", which I did say almost in an instant.

She explained that she was subsequently encouraged to join a convent by her parents and a few close friends, so that God could watch over her more closely. She was only in her mid 20's at the time, and it made her unsure whether or not she could ever have a relationship with a man after that. So she kind of leaned toward becoming a nun, and her parents and a few close confidants encouraged her to do so.

It occurred to me that maybe this unfortunate experience led her to lose the desire to look womanly to a man, and maybe that's what caused her to start looking less feminine and more manly, with a seemingly unattractive countenance. And I could easily see her being mistaken for a man if she were wearing pants, making her ordeal at the airport understandable.

"Since I've been here these few years and with you coming over to the convent and being a quiet, well-manner boy, I started wondering what a man was like. Especially when I noticed you looking at my chest and acting like you weren't. I knew you were well mannered, but I also knew you were also just a mere mortal man. And I have to admit, it made me curious."

I wasn't too thrilled when referred to me as a "boy", but quickly got over it when she confessed that she saw the man in me. Which of course, got us to this point.

She started moving around, and I wondered if she was going to get up, and what I should do. So I just lay there motionless, as if on standby. She turned her body around and positioned herself to lie next to me, with her head near my cock. She grabbed the base of it with her hand.

"I've missed what a man taste like", just before I could feel her mouth coming in contact with my penis. If I heard right, she said "taste" instead of "tastes". I felt her tongue licking the top my penis, around the head and immediately below. It caused my erection to spring back up again. Once she mentioned the rape, I think that's when my erection died, or at least started to get soft. And now she was bringing it back to life.

Surprised at feeling her mouth on my penis, I gave an unexpected moan. It made her stop and ask, "Are you okay?" Through my breath I said "yeah", as the formal "Yes, Sister" was nowhere to be found in my mind by now.

She continued to explore my penis with her mouth, licking it a little, putting her mouth over what felt like the upper half of it, all while maintaining a grip near the base of it with her hand. It didn't really feel like she was sucking it. I lay there still, save for a few involuntary twitches or mini convulsions. Not knowing what else to do, I put my hand on her thigh,slowly sliding it up to her buttocks, over the granny panties. I caressed her buttocks over her panties, feeling it was something I "should" do, as she continued to explore my penis with her mouth, Her butt was a little on the flabby side, but not so incredibly out of shape. I didn't dare remove her panties.

I had considered my cock as a cock, but once she took it to her mouth, I felt like my cock had to become a penis at that point. As if it had to be considered a more respectable entity, rather than something crude and a mere joystick. After all, a nun, someone I considered as a highly respectable entity, was taking it to her mouth in an unprecedented experience for me. I felt confused as to what my role actually was in what was really taking place. This seemed to be a form of "acting out" on her part, stemming from a bad experience that happened long ago, yet left her with a developing curiosity in the years since.