Reunion & Retirement Celebrations

It was September, 15 years after our 8th grade graduation that our school had planned our reunion. Coinciding with that, our 8th grade teacher was retiring after 46 years as a nun. She had a rather large frame and somehow managed to maintain her red hair. She was beginning to have health problems and decided what was best for her was to leave the convent & be in the care of her family.  And so with that, the 2 events were planned for the month of September, & one of my classmates, Maureen, had planned to attend both of them. Though it would be much simpler to register online, the "encouraged" method of registration for attending either or both events was to show up in person at the convent and sign up. This was a sort of a ploy for the nuns to be able to get their alumni to stop by and spend time with them prior to the reunion dinner. So Maureen had decided one Saturday in late August to drop by the convent and sign up to attend the events. Unbeknownst to her for the past 5 years, I had been doing my "Jock Maid Service" in the convent most Saturdays. Over the course of that time, the nuns had gotten frisky with me on occasion, and so sometimes we'd have a little fun. When we were kids, we always entered the convent through an open door in the garage leading to the finished basement. Down there were finished off rooms, 2 used as classrooms, and a nice size lounging room. Because we had classes there and the nuns knew us well, we were always welcome to just walk in that way. And so we became accustomed to doing so. On this one Saturday where Maureen dropped by to sign up for the reunion & retirement dinner, she figured she would just walk through the open garage into the basement like old times. What she would see and discover would shock her.  Maureen was a mild mannered Irish American girl who was on the quiet side, girl-next-door-type. She was attractive in her own way, shoulder length brown hair which she'd occasionally throw a little reddish color into. She had mahogany framed prescription glasses & had grown to about 5 feet 3 inches. Her breasts had developed nicely, as I had noticed already happening when I occasionally saw her during mass while I was in my high school years.  Being on the quiet side, she wasn't one to enter a place with a loud bang. So when she had walked in, her sneakers barely made a noise on the carpeted floor. And so she wasn't noticed as she approached the lounging room. What she first saw made her quickly step aside the entrance way to the room. With a curiosity, she peered around the corner of the entrance way, careful not to be seen, so she could see what was taking place. Inside the room where a lally column stood was me, wearing just my swim supporter jockstrap, with my hands cuffed behind my back around it. Facing me stood the nun who had been our principal. Her once firm beautiful breasts had become a little saggy, now shaped more like bullets perhaps due to her bra. Her hair had gone from salt & peppery back in the day to now a solid light gray. She had gained a few pounds, making her arms look strong. She was wearing her tight white habit, revealing the curves.  As Maureen peered around to see what was happening, Sister was saying things while giggling, like "What have we here. Huh?" As she was groping the pouch of my jock & pinching my straps to snap at my exposed buttocks. I was moaning at her touch as her hand was exploring the contents of my pouch. My cock was pointed upward with a raging hard on, feeling like it was about to push itself out from above the waistband. She was giving good gentle squeezes to my cock and my balls, as I was so turned on & horny. Maureen was in shock that Sister was doing this. She had no idea that I did cleaning work around the convent in my jockstrap. So she thought what she was witnessing might be against my will, as if I became trapped when I came to sign up for the reunion. Meanwhile, Sister & I thought we were having a private moment. Then the shock grew even further, as she saw Sister wrap her fingers around the waistband of my jockstrap, and proceed to lower it, exposing me as my hard cock just sprung straight out. Maureen kept watching as Sister continued giggling, saying teasing things like "My, what have we HERE?" She began fondling, tickling and squeezing my balls, as she began to slowly masturbate me. Maureen became frightened at the notion that I was actually being raped. But at the same time, she was excited to watch, while suddenly feeling a strange feeling coming over her. Only she didn't know what it was or what it meant. As I would soon ejaculate high into the air, Maureen ran out of the basement. She became so afraid to be there, and be caught there as to what she just witnessed. But still, this was our principal nun doing this to me. She didn't know what to do. She was confused, though in the back of her mind, she knew she couldn't report it. Maureen waited until after the Sunday mass was over to return to the convent. This time when she came through the garage and into the basement through the open door, she once again found Sister in the lounging room, this time alone. "Oh hi, Sister. I came to sign up for the reunion & the retirement dinners."  "Maureen! My, how you've developed!" Sister exclaimed, as she approached Maureen & felt her nicely developed breasts over her blouse. Maureen stood there stunned, having no idea Sister was going to reach out and feel he breasts like that. She did so by putting her hands around the outer sides & sliding them underneath, giving a brief jiggle as she felt the shape & weight of them. It caused Maureen's nipples erect & protrude towards visible little bumps under the blouse.  As the retirement celebration for our 8th grade nun teacher came upon us, all the other nuns from the convent were there, as were her family & close friends. During the course of the event, one of the close family friends who was the host had approached Maureen & invited her to a surprise private retirement party that was just for certain family members & close lady friends only. To be held in secret from the other nuns, because of the anticipated nature.... Little did Maureen know that in honor of celebrating Sister's retirement as a nun (& teacher), they would be hiring male entertainment. And that male entertainment would be me..... I also did male stripper parties on the side for women, whether it be bachelorette parties or whatever. So I was called upon for this occasion. The way I typically worked it was I would dance to 70's music while in a jockstrap, and I would allow guests to do whatever they wanted to me, including strip me of my jockstrap, do anything sexual to me or with me, tie me up, or what have you. At the request of the friend putting this on, I had agreed to be handcuffed and allow Sister to have her way with me however she chose. I knew she could/would do anything from spanking or swatting me to potentially fondling me & maybe even masturbating me. When it was time for the "talent" (me) to arrive, the 15-20 women, including Maureen, were already gathered. Most in age were mid 40's to maybe mid to late 60's (making Maureen significantly younger @ about 30). The music collection I brought to dance to was coincidentally the late 70's music that was out around the time we were in 7th and 8th grade.  When Maureen saw me, her eyes nearly popped out of her head. Here I was, once again in a jockstrap, but this time on display in front of several women. To see me like this, and recalling how I was vulnerably handcuffed last time stirred an anxiety inside her. There was something now sexually alluring about me to her. Perhaps perceived innocence of my exposed body. She was beginning to have thoughts about me that she thought she should reveal in confession. But for now she sat there, watching as I performed. I danced and shook my hips to the dance songs of our time as 8th graders. It was a strange element, with what was happening now, these 15 years later. I moved around the room, taking turns dancing in front of everyone there. As I approached some, they would stand up from their seat & dance with me and begin to teasingly touch me a little. Maureen froze as I approached her, and for a moment, I went into a little bit of a shock that she was there. This party was mostly for older women that I didn't go to school with. They were close in age to Sister who was retiring. I could sense Maureen's discomfort, as my own, and I would pass by her, just long enough to be polite & move on.  As i danced around Sister at some point during each song, she gradually got increasingly more comfortable touching me. They had Sister sitting on a sofa as then guest of honor, with most of the other guests on folding chairs around the sofa. As Sister had gotten more aggressive, her groping of me caused me to have to adjust my jockstrap a few times, as I was developing a full blown erection. Somewhere after about 20 minutes or so of "entertaining", the friend putting the party on noticed Sister had gotten comfortable touching me & I had gotten hard as a result of it. So she decided it was time.  To bring out the handcuffs. Maureen looked on, as I stood before Sister, shaking my pelvis to one 70's dance song. Suddenly, I could feel a hand grab my wrist and draw my arm behind my back. After feeling and hearing a cuff snap around my wrist, the host had grabbed my other wrist, drawing my other arm back. Hearing the 2nd cuff click in place had an even more stimulating effect on Maureen than when she heard the first one click on me. Because the 2nd one clicking meant that I was now fully under the control of all of them.  A slight feeling of a shortness of breath overtook Maureen as she continued to watch on. A hand swept at my calves, sending me off balance to fall toward the sofa. I felt some manhandling manipulation to my body as I went down, so by the time I felt myself totally horizontal my strap framed butt cheeks lay in Sister's lap, as I lay across the sofa. She gripped the pouch of my jock & shook it fiercely, making me achieve what felt like a larger erection than I ever had. She proceeded to lower my jock, causing my hard cock to spring out in midair & oscillate back & forth. She played with my exposed balls as she slowly teasingly stroked my cock. She was now no longer a nun, and therefore felt she was free to enjoy a man's body. And I was enjoying her enjoying it, as eventually my cock exploded straight up in the air like a volcano. Maureen couldn't help but look on as all this was happening. It was really captivating her, seeing me as Sister's captive. Seeing my cock explode again made her uncomfortable. So she told the host she wasn't feeling well & made a quiet sudden departure. She just couldn't be around people and try to deal with these feelings that had come over her. She knew at some point she had to go to confession. Just so turns out the same day I also went to confession. Just a bit earlier..... The frequent convent cleaning I did allowed the principal nun to keep tabs on me, making sure I dutifully went to mass each week, and to confession each month. It was Monsignor's turn to hear confessions this time around, & he's also the one who likes to watch out his rectory window to see if he can catch me in my jockstrap cleaning the convent kitchen, dining & bedroom windows. He has had me also clean parts of the rectory in a jock when all the other priests were away, & has kept it secret from them. As Maureen entered the confession stall & knelt down, she could hear something through the partition to the priest's chamber. Monsignor whispered, "My, you're so stiff & long. Look at you", followed by a stifled moan. My moan. I had been summoned to the priest's chamber as Monsignor's growing tension for wanting to play with my cock & balls got the best of him, and he wanted to jack me off right then & there.  By this time, I had understood the effect I was having on people by being on display in a jockstrap. And that people are only human, and that includes clergy. And so I allowed my body to be used, by otherwise abstinent clergy. If it meant being "Masturbated by the Monsignor", so be it. I have to admit I like hand jobs, and so I allow their use of my body to go on. This had become a bit too much for Maureen. After listening to me moaning as I was ejaculating, Maureen scurried out from the confessional box. She knew she wasn't ready to confess her feelings, but rather follow them along and explore them. The reunion dinner was coming up, & she knew that was the time she must make her move.  She began to think that if it had been okay for THEM to masturbate me, then perhaps masturbating someone was okay, and that her feelings of being turned on by watching it are okay too. They were treating me like a boy toy, after all. And they were the ones physically acting it out, not her. I was ready to avoid her out of the embarrassment that she had been put on the spot, witnessing what she had at the retirement party. Unbeknownst to me, she was there for those other times as well. So when it came time for the reunion dinner, my plan was to avoid her beyond maybe a polite "hello". But she approached me. We made small talk, & I could feel like we were getting comfortable with each other. I had explained my side stripper gig, since she now was a ..."party' to it. It seemed awkward for her to discuss, but she seemed very interested in listening to me talk about it. I felt a bit awkward discussing it, but felt like being sexually open with her might actually be a good thing. Until I began to sense it was arousing her, the whole thing. I could feel a developing closeness, with a bit of a sexual tension to it. We were attracted to each other, and she was at that party where things got sexual. So there was a bit of a sexual tension between us. She felt like she could, and wanted to, masturbate me, having that effect on me that she could see the nuns having. And I was attracted to her body, starting to have a desire to explore it with my hands.  Towards the end of the dinner, I invited her back to my place, as I really didn't want the night to end, at least not without having a chance. She seemed very relieved I had made the offer, and I could sense a dichotomy of the possibility of something happening, while also her reservations at being a conservative Catholic. In other words, I could sense she was horny for me, but I didn't think she was going to be willing to have pre-marital intercourse. Sure enough when we made it back to my place, there came a point where I began to slowly caress her as we chatted. Eventually, she began to reciprocate, and before I knew it, we were lying side by side on my bed, exploring each other's bodies with our hands. I struggled as I tried to unbutton her blouse with one hand. Getting no resistance to stop, I forged ahead until I had her white bra exposed and accessible to feel. I groped her nice breasts over her bra, whispering "they're beautiful" to her as I enjoyed their feel. She began unbuttoning my shirt as well. The feel of her undressing me, and how her body felt as I ran my hands over it cause me to get a really hard erection, which was rubbing into her thigh, as we lay side by side. After she had unbuttoned the last button, i stopped and removed my shirt completely. She did the same, and eventually as we lay back down, I reached around and unclasped her bra. I rolled my hands underneath the back of it and up to the shoulders, sliding her bra straps down her arms as her breasts slowly began to come exposed as I continued sliding the straps down her arms, causing the bra to slowly drop away, exposing her beautiful pale breasts with nice red areola and nipples.  I slid my head down to suck on her nipples while my hand continued to explore her all over. I found the zipper to her skirt, and slowly unzipped as I continued to suck. She was reaching for the belt on my pants, and I turned my body to lie more on my back so she could have access to undo my belt & pants, while still trying to keep her nipple/breast in my mouth. After she unfastened my belt, I could feel her undo the button, and as she moved her hand in to my crotch area, my zipper unzipped itself.  I felt she was soon to lower my jockstrap, as I was moving my hand around the periphery of her panties inside her open skirt. Her skirt fell away as I continued to maneuver my hand. I wasn't going inside her panties until she went inside my jockstrap.  Suddenly I could feel her hand on my jock. She was exploring the pouch softly, and running her hand around to feel my ass, and the straps that were framing them. I began to move my hand into her panties to feel for her clit, as I continued to suck on her breasts, taking turns with each one. I felt her hand as it slid under my jock. She had grabbed my cock and began stroking it intermittently, as she occasionally ran her hand down and felt my balls. She was very gentle with them, and for a moment, I stopped in my tracks from moving my hand around to experience what she was doing to me.  I began to breathe heavily. I was horny for her. Her hand felt so good. I felt as though seeing Sister manipulate me at the party drive her to this point where she now wanted her turn, and it made me so hot.  As she resumed stroking me, I began to work aggressively with her hand on my clit, trying to stir up a sensation. And I could feel she was turned on, and I wanted to up the intensity to give her an orgasm more than anything else in the whole world. So I began to get aggressive with my hand. I knew I minimally had to get her wet, and then, if she wanted my cock in her pussy, I would let her take the lead in that.  Thinking back, I was wondering had I been more aggressive to just mount her at some point, if she'd let me, be bothered by it, or what. But I was fine with what was happening. Boy was I fine. She had to stop stoking me as me masturbating her became too powerful for her and she was losing control of herself. She hung on tightly to my cock was I worked my hand away on her. It would occasionally move, but she wasn't really masturbating me, as she was overcome with how what i was doing to her was making her feel. And then it happened. She had an orgasm, and suddenly everything was very, very wet. When she couldn't take it anymore, she grabbed my wrist, and guided it away. Then she rolled herself over on top of me. I wondered if she would give me oral, but i also wondered if she even knew how. She guided me back onto my backside, took a tight hold on my cock, and started stroking it fiercely. I grabbed her wrist to slow her down, as I whispered "Ease up" in which I was referring to both the speed AND the grip. She had such a tight hold of me. I was so hoping she would go down on me, but I realized all along this would not progress beyond mutual masturbation. Which I was certainly okay with. She was able to position herself over me to use one hand playing with my balls, as she had witnessed the Sisters do. And also with stroking my cock as they had done in similar fashion. She had learned well from observing.  For me this felt different. She was non clergy. Since I was in elementary school, I always felt nuns & priests had all the power over me they wanted. Masturbating me once I became an adult was no different.  But this was Maureen. A former classmate. A peer. Exerting her power over my cock. Her dominance. Form someone I never felt was a dominant. And I ever just got her off without resistance. At that time, I seemed in charge. But now she had my cock, and my balls, in her hands. She had been moved to be at this point, by nuns no less. And that added to my excitement and arousal. I had positioned my hand to cup & fondle her breast as she was masturbating me. Between the feel of her breasts and what was going through my mind psychologically, my cock shot a seriously load, the first spurt of ejaculate hitting her hair. It was a shock for her to actually see it emanating forth. It gave her the ultimate satisfaction as there had been something driving her to jack me off & get me to cum & experience pleasure. There was a pleasure in it for her that she was coming to realize in the exploration of the feelings of what she had witnessed with the Sisters. That she could have this Affect AND Effect on me. Both exhausted from an interlude of mutual masturbation, we fell asleep in each other's arms. The next morning, I had gotten up & started making breakfast for both of us. Bacon, eggs various styles, hash browns, and I had some pumpkin cream cheese for a few bagels that were leftover. I prepared the dishes and then made the preparations to bring it back to bed, so we could enjoy it there. And who knows? Maybe pick up where we left off.....  As we dined our breakfast in bed, I revealed that I did that "Jock Maid Service" gig at the convent on most Saturdays. Maureen now came to understand what the incident she had seen was all about. But she was still too afraid to tell me what she witnessed that day. It would just be too embarrassing, not only to reveal that she had seen it, but that by now she had kept it secret for so long. The following Saturday, Maureen snuck into the convent basement, to see if she might catch us in the act again. By now, she was driven by all she saw AND by all she experienced with me. And sure enough she stumbled upon a familiar scene. The principal nun once again had me tied up to the lally column, and was teasing me, about to lower my jockstrap. And as she did, she heard a gasp. As i stood, tied to the lally column, I watched as Sister stepped out of the room, discovered & led Maureen into the room by the arm. "You like to watch us, hmmm?" Sister asked, as now Maureen was caught. Watching us. She had no other reason to be there now, as the festivities were over. But of course she WAS there, as she knew what I was up to in the convent on Saturdays by what I had told her when we had breakfast in bed. "Touch his jock", Sister ordered as Maureen just stood there stunned. "Go on!" Sister barked as she grabbed Maureen's wrist & brought it to the center of my pouch, where my bulge was hard with excitement. Maureen was afraid. She was caught in a situation where she was snooping, perhaps considered "trespassing", and how did Sister feel about all of it? She liked Maureen. Hell, she even took the liberty of squeezing her no developed breasts for Heaven's sake. Maureen reluctantly touched me, but I felt fully confident Maureen knew HOW to touch me, based on our interlude together. She just felt embarrassed doing it in front of Sister. And by Sister barking out orders, it seemed to be like a punishment for voyeurism, snooping, trespassing, whatever was causing Sister to seem forceful with Maureen. "Pull it down" Sister seductively said, referring to my jock, as Maureen had been fondling my jock for her for a few minutes by now. Maureen felt really super embarrassed, stripping and exposing me in front of Sister. It is just such an awkward thing to do, even though she knew full well that Sister had seen and touched my nude body already. To have to do it herself?....  With reluctance, Maureen curled her fingers around the waistband of my jockstrap & in a reluctantly slow motion, lowered it. My hard cock sprang out as the jock material came down over it.  I was all set to be masturbated by either or both of them. Sister instructed Maureen to do the honors. "Stroke him!"

Maureen complied, as we were trained to obey all of the nuns, especially the principal, when we were in that school. The principal had so much power. And to me with her breasts, she also had so much "sexual" power. Sister was enjoying watching Maureen masturbate me. Maureen felt awkward, being watched by Sister. But as she continued to stroke, she thought about how Sister liked to stroke me too, and in a bizarre way, became more comfortable to the situation as she continued to stroke.  Finally I shot my load, thinking in my mind how these beautifully breasted women are enjoying me get so sexually out of control as to ejaculate in crazy flying spurts.  And after I came, Sister and Maureen turned to each other. And smiled.