1. Sister Mary Catherine Finds Fulfillment in a Gangbang
by tunefulbob
Copyright© 2025 by tunefulbob
Erotica Sex Story: A beautiful young nun leaves her convent to find sexual fulfillment. This story contains a good bit of anal sex. So if you dislike or disapprove of anal sex, please do not read this story! Many of the illustrations are AI assisted.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Consensual Heterosexual Fiction Gang Bang Polygamy/Polyamory Anal Sex Double Penetration Oral Sex Big Breasts Size Illustrated .
I visited a local vineyard a couple of months ago, drawn by the reputation of a Bordeaux-style blend that it produced. The vineyard was owned and cultivated by an order of nuns, which had originally started out to produce altar wine. Over time the vineyard had expanded and had recently begun selling its wine commercially.
Little did I know that the visit would lead to one of the most extraordinary sexual experiences of my life.
I know a little bit about wine, which led to a conversation with the viticulturist, an elderly nun by the name of Sister Beatrice. The wine produced by the vineyard was a blend of Cabernet Sauvignon, Cabernet Franc, and Malbec grapes. When I asked if I could take a look at the vitis vinifera vines, she directed me to the nearest section of the vineyard where those grapes were grown. They were beautiful vines, quite healthy and expertly maintained. As I was examining the vines, I saw a young woman who had a pair of clippers and was trimming small bits of the vines here and there. She was wearing a loose-fitting top with long sleeves, a white skirt that was shorter than I would have expected, and a habit that covered most of her hair and flowed about halfway down her back.
When she saw me, she said, “Hello, I’m Sister Mary Catherine. It’s ... unusual to have visitors here among the vines. Can I help you with something?”
I was a little taken aback to see someone so young and beautiful in a convent. I think I may have stammered a bit when I replied, “Uh ... hi, I’m Rich. Sister Beatrice said it was okay for me to take a look at some of your vitis vinifera vines.”
Sister Mary Catherine smiled at my reference to the old nun, “It was most unusual for Sister Beatrice to agree to your request. She must have been terrifically impressed that you knew the botanical name of the grape vines!”
“She was most cordial, I must say. We talked a bit about her duties as chief viticulturist here. You know, I’d be most interested in seeing some of your newly planted, young vines. Are any of them nearby?”
“Yes, just down this row. I’ll show you the way.”
We walked single file as there wasn’t quite enough room between the rows to walk abreast. I couldn’t help but notice the sway of her shapely hips, which filled out her skirt quite beautifully.
I have a couple of abilities that are unusual. One is an enhanced level of empathy, a sort of sixth sense about people’s feelings, especially their wants and needs. Another is that there is something about my voice that appeals to people and influences them. It gives me a power of suggestion that is sort of like hypnotism, though not as strong. When I tell someone what I want or would like, they seem to want to accommodate me. So it hadn’t surprised me at all that Sister Beatrice readily agreed to my request to wander unsupervised in her vineyard.
One of several things I sensed about Sister Mary Catherine was a profound loneliness. Another was a powerful level of sexual need. In fact, the sensation that she was emanating was an intense desire to show me her naked body. And there was something else, an image of her lifting her leg to show me that she was wearing nothing else under her skirt. Rather impulsively, I blurted out, “Is it your usual practice to wear no panties under your skirt?”
She stopped and turned to me so suddenly that I had to bring myself up short to avoid running into her. Our faces were about eight inches apart, so I stepped back quickly. She was blushing, from her cheeks down to her neck. Her eyes flashed at me fiercely. But there was an internal struggle about what she should say to me. She finally settled on, “You should be careful not to say such rude things to me!”
“But ... but it’s true, isn’t it? You aren’t wearing any panties, are you?”
She flushed an even darker shade of red but said nothing. Her eyes were riveted on mine as if she were fascinated by some unusual sight. I smiled at her and said, “Wow, you are especially beautiful when you are annoyed and embarrassed!”
Sister Mary Catherine turned away without a word and continued walking in the direction we had been heading. “Our newly planted cabernet sauvignon vines are just ahead, on both sides.” She spoke while she was walking, with her eyes focused ahead in the direction she was walking.
“Tell me, Sister Mary Catherine, how does it happen that a woman so young and beautiful decided to become a nun?’
She stopped dead in her tracks. I could feel that she wanted to accommodate me by answering – but she didn’t know what to say.
She turned toward me, uncertainty radiating out from her as clearly as if she expressed it to me in words. I decided to make things easier by suggesting something else I would like her to do. “Would you come over here and kiss me?”
She walked toward me slowly and lifted her face to me, though with her hands clasped in front of her breasts as if to prevent me from pressing my chest against her them.
I kissed her oh so softly on her lips and folded my arms around her. She placed the side of her head against my chest and said, “Oh my goodness! What am I doing? What could have possessed me to let you kiss me?”
“I don’t really know the answer to that,” I told her honestly. “But I have to say that it was one of the loveliest kisses I’ve ever experienced. Will you let me kiss you again, this time more passionately?”
She accommodated me and moved closer. With our arms around each other in a gentle embrace, we kissed with our mouths open and pressed together firmly.
We continued to hold each other when our lips separated. I looked her squarely in her eyes and said, “My interest is in exploring your latent and repressed sexuality. Would you like to partner with me on that journey?”
She blushed deeply under her habit and said, quietly and hesitantly. “Oh! I ... I don’t think that would be appropriate. I...” She looked away but kept her arms around me.
“Your true nature is quite apparent to me. Are you afraid of your wild impulses? Is that why you joined a convent?”
She shook her head vehemently and replied, her voice trembling, “No, no! You don’t understand me at all! I came here to devote myself fully to God after ... after I became confused about some things when I was a teenager. I had an unnatural desire for things that were wrong and needed to be somewhere safe so I couldn’t do those wrong things. There’s nothing more to it than that.” She stepped away from me, her eyes darting around anxiously. “I think I should resume my work.” But she remained facing me, her eyes now cast downward.
“I don’t mean to embarrass you, darling. But what you thought were wrong things are everyday human things. I can tell that you have powerful impulses to do those natural things, and you have an exhibitionist streak as well which is nothing more than a realistic appreciation for your beautiful body. It wouldn’t surprise me if, in addition to wearing no panties, you also shave your pussy. Will you let me see your pussy? I think you want to show it to me.”
She gasped sharply, but more from surprise than from outrage, her face again turning crimson. When she spoke, it was in a voice that was barely above a whisper. “I don’t understand why you would say such things to me. Can’t you see that it upsets me and confuses me?” She still stood before me, though she had raised her eyes appealingly.
“What confuses you is probably the same thing that bothered you years ago, the things that made you want to retreat from the world. You were struggling with perfectly natural urges and desires that you thought were wrong and feared would overwhelm you.” I paused for a moment, as she seemed to want to say something. But she stayed silent, keeping her eyes locked on mine. So I continued, “You chose the wrong path, darling. Your nature demands that you go in the direction that your urges suggested. Coming here did not resolve your conflicting feelings – it could not resolve them because you chose a path that was totally at odds with your nature. I’m going to help you learn some things about yourself that will show you the right path for you.”
“What if you’re right? What will I do? I have a home here, and work that I find fulfilling. What you are saying is my path would require that I leave here.”
“You are still very young, my dear. There are many kinds of work you can do – including working in some other vineyard, which is something you do with great skill. So come back into my arms and let us kiss some more. You will know when you do that what I am telling you is true. Now, tell me what I should call you.”
“My given name at birth was Catherine. They let me keep it as part of my new name when I took my vows.”
“Your name suits you, Catherine – it’s very lovely. Now sit here beside me.”
She was unable to resist me – she didn’t want to resist me. We sat down together on a nearby bench and embraced. And we kissed, again gently at first, then passionately. Soon she was moaning, as desire rose in her.
“I want to kiss and caress you all over, my darling. Will you help me get your clothes off?”
She hesitated, then whispered “What if someone sees us?” There was something about the way she spoke that told me that part of her wanted someone to come along and see her beautiful, naked body.
But I tried to reassure about the fear she had expressed. “Well, it’s a quiet time in the vineyard right now. Is there anyone else working out here today?”
“No, I don’t think anyone even knows I’m here. I just wanted to do a little bit of pruning before the fruit begins to develop.”
“So no one will see us then. And if someone does, it will probably facilitate your leaving this place.” She looked around anxiously, clearly excited but nervous about complying. “I ... I don’t know what’s come over me. This isn’t like me at all. But ... I want to please you. If it will make you happy, I suppose I could ... let you see my breasts.” She hesitated only a moment longer before she took off her habit and began to remove her top. When she was done, she gazed at me, waiting for whatever I had to say to her next.
“Ohmygod, darling, your body is so beautiful! Your breasts are as stunning as your eyes, and that is saying a lot! Now lift your knee high enough to show me that I was right about your beautiful, bald pussy.”
Again there was that momentary hesitation. But it was clear that she truly wanted to comply with my suggestion. And, rather slowly, she did.
“You take my breath away, you are so beautiful, so sexy!”
I caressed and kissed her beautiful breasts and sucked on her perfect nipples. She gasped and held my head gently, pressing me to her breasts as the sensations of having her breasts treated so tenderly penetrated her consciousness. “Oh! That feels incredible ... I’ve never been touched and kissed like this before.”
I knelt down on the ground in front of her and began kissing her legs, just inside of her knees. She lifted her legs and spread them wide, invitingly, and said, in a trembling voice. “You are right about what I want, what I’ve always wanted. Take me, Rich. I can’t say no to you. Whatever you want, please take it.”
She loosened her skirt and left it lying on the bench underneath her ass, then gazed down at herself as if wondering how it had happened that she was naked.
I kissed the insides of her thighs, closer and closer to her pussy, then licked her inner and outer labia. I grasped her calves and placed them on my shoulders, leaving her legs spread wide, then resumed pushing the tip of my tongue inside of her pussy. She shivered a bit and sighed softly. When I pressed my tongue against her clit, she moaned. Her legs were quivering now. I knew it wouldn’t take long to bring her to orgasm. I pushed a finger into her pussy, marveling at how tight she was, and began fingering her g spot. As I expected, she was soon stiffening her legs, arching her back, and moaning and crying out softly “Oh ... oh! I think I’m going to cum! Oh yes ... yes ... I’m cumming, Rich! It feels so wonderful, so amazing!” Her whole body shuddered for several seconds, and then she began to relax. She lowered her legs and lifted my face, looking into it with wonderment and the dawning of affection and saying, “Oh Rich, thank you for that. That was the most wonderful thing that ever happened to me! You were so gentle and so loving, yet the feelings you gave me were so exciting! I loved everything about how you made me cum. It was perfect!”
She looked at my pants then and saw the bulge of my cock. “Will you fuck me now, Rich? I want you inside of me.”
“Yes, I will fuck you soon, Catherine. But first I want you to suck my cock. Have you ever done that?”
She looked up at me and shook her head, then said, “Will you teach me what to do?”
“Of course, darling. First, kneel down, loosen my pants and take out my cock.”
She knelt in front of me and gazed up at me, looking happy at the prospect of having my cock in her mouth.
Her hands trembled as she undid my belt, fumbled with the catch, and unzipped the zipper. It was obvious that all of this was new and very exciting to her. When she pulled down my underpants and my cock sprang out, her eyes widened in surprise. “Oh my goodness ... are all cocks so big? I’m not sure I can fit it into my mouth.”
“You will do fine, darling, though mine is bigger than most. First, caress the part under the tip with your tongue.”
She tentatively pressed her tongue under the tip of my cock, then pulled away to ask, “Like that? Am I doing it right?”
“Yes, that’s good, sweetheart. Now take the tip of my cock into your mouth -- and don’t touch it with your teeth.”
“Okay. Tell me if I do it wrong.” She took the tip gently between her lips and looked up at me for approval.
“That’s perfect. Now practice taking my cock into your mouth as far as you can, so the tip bumps against the back of your throat. You’ll have to concentrate hard so you don’t gag. But having the tip of my cock squeezed by your throat will be deeply pleasurable for me.”
“Aaah, that’s fantastic, my sweet Catherine! I can feel your throat squeezing the tip of my cock beautifully!” She either had a rare talent for this or perhaps was able to do it without gagging because of my suggestion.
“Now pump your mouth up and down on my cock, pressing your tongue against the bottom of the shaft continuously.” Once again she was amazingly good at it.
After a couple of minutes, I could feel my balls tighten and the urge to cum rise in my loins. “I’m going to cum soon, sweetheart. Keep my cock in your mouth but back off a little bit so you can swallow my cum more easily.”
Shortly afterwards, my cock began pulsing and spurting. Though the quantity was amazing to me, Catherine seemed to have no trouble swallowing it. She kept about three inches of my cock in her mouth until all the hardest spurts were done, then began pumping again, though not as deep, sucking on my cock and pressing her tongue against the tip as if she wanted to make sure there wasn’t a drop of cum left in it. That must have been pure instinct, as I had said not a word to her about that part of the process.
“Ohmygod, darling, that was as good a blow job as I’ve ever gotten from any woman. In fact, there are very few who have come close to pleasing me so much, even after years of practice.”
I gripped her elbows and lifted her. She clasped her arms around my waist and pressed the side of her face against my chest. “Oh Rich, I loved it when you spurted your cum into my mouth. I feel like I belong here, in this moment, doing everything I can to please you.”
She looked up at me and kissed me. We lingered for a while, pressing our bodies together. She looked into my eyes and said, “Now will you fuck me? That’s what I really want.”
I smiled at her. “You know, I think we should take this to my bed for the next part. Get dressed, go inside and gather up your things, and meet me in the parking lot. You can send a letter to resign, or whatever you have to do.”
She looked grave and uncertain. “I have to ask to be released from my vows. There is a process that can take months.”
“That’s ridiculous. They can’t hold you here against your will. Let’s leave and then you can ask to be released. It’ll be pretty obvious that you mean it if you’re gone.”
“They will want to ask me questions about what made me decide to want to leave the convent and to be released from commitments I solemnly swore to fulfill.”
“It’s all wrong for you, my darling. You didn’t know how impossible those commitments were when you made them. Just come away with me and let the process play out as it will. Let them know that you made a huge mistake and there is no way you will ever come back.”
“I think the Mother Superior knew all along this was wrong for me. She questioned me closely before I made my final vows. I believe ... I hope she will advocate for my release.”
She thought for a moment, then said, “Alright, I’ll do it. Give me fifteen minutes. I don’t have much that belongs to me. Even my clothes aren’t really mine.” Then she laughed, and said, “I suppose the underwear is mine – but I never wear the underpants.”
“Get your own things and take whatever else you need, whether it’s yours or not. I’ll pay them for it – you can send the payment with the resignation letter. Maybe a large donation will help them come to the right decision about these vows of yours.”
She laughed again, got a resolute look on her face, and said, “Okay! I’m going to do this. I really don’t want to be here a moment longer. I will see you in fifteen minutes.”
She put her clothes back on and hurried away after a last hug and a lingering kiss. And it was only ten minutes later when she ran to my car in the parking lot, carrying a small bundle of things wrapped up in a towel.
My home was a forty-minute drive. She said very little but was glad to hold my hand when I offered it to her. I told her about my house and the bedroom of her own she could have if she wanted it. I also told her I would take her clothes shopping the next day.
When we got to my house, I opened a bottle of cabernet and poured glasses for both of us. She left her little bundle in the living room as I showed her around and gave her a couple of light robes she could wear if she wanted. “Though my preference is that you wear nothing at all around the house. I can tell you prefer to be seen – and why shouldn’t you be? You are so very beautiful – seeing you unclothed will always be a source of joy to me.”
She smiled at me and began to undress, leaving her clothes in a heap on the floor. Then she took my hand, led me to my bed, climbed onto it and sat there, looking a little nervous but also looking like she knew that was exactly where she wanted to be.
‘NOW will you fuck me?” she asked, with a serious look on her face.
And I did, most gladly, but only after I had satisfied my appreciation of her beauty by kissing her and caressing her all over, her mouth, her neck, her shoulders and upper arms, her breasts and nipples, her tummy, the entire lengths of both legs, from her insteps to the insides of her thighs, and finally, her pussy and her clit.
By that time, she was panting with desire. She had kept grabbing and holding my cock – but there were times when it was out of reach.
First, I fucked her missionary style, starting with rubbing the tip of my cock up and down her inner labia. She spread her legs wide and tried to pull me into her. She was impatient for the feeling of having the entire length of her pussy stretched and filled. As I slowly inserted the tip into her, she said, “Oh god, I want you so much!! Fuck me, Rich!! Don’t make me wait any longer.” She was a virgin, and very tight, though her hymen was not intact. So when I thrust hard into her, the only resistance was from the constriction of her vaginal walls. “Oooooh,” she moaned as she felt me deep inside of her, with the base of my cock pressed against her clit. “THIS is what I’ve always wanted. I LOVE having you deep inside of me!” She was sighing and panting. I paused for only a moment, with my cock fully enclosed by her pussy, then began pounding and thrusting into her, slowly at first, then faster and harder.
It wasn’t long before her body tensed up, her legs wrapped around my hips and held me to her, and she began to cry out with pleasure and with joy.
Then I fucked her standing up.
And then I fucked her doggy style
And then I fucked her reverse cowgirl style.
And a couple of other ways as well. In every position, she came at least once.
As for me, the huge orgasm I’d had when she sucked my cock had helped me to refrain from ejaculating. Now, after building up to it for perhaps an hour of non-stop lovemaking, I was ready to ejaculate again. And I wanted to do it in her ass.
She was in reverse cowgirl position for the second time when I snapped open a tube of KY and lubed her asshole. She was startled. “What are you doing?”
“I’m going to fuck you in your asshole next, my darling.”
“What? I never heard of that. Won’t it hurt? Your cock is too big to fit it in there!”
But I could tell that she was intrigued. I pushed my thumb into her lubricated asshole, which led her to sigh with pleasure, and then to moan.
“Oh, that feels nice! Maybe I will like being fucked in the ass.”
“You will definitely like it, darling. You might cum harder that way than anything you’ve experienced so far. There are a lot of women who have their best orgasms with anal sex.”
I told her to rise up so I could pull my cock out of her pussy, then took my thumb out of her ass and quickly substituted the tip of my cock.
“Okay, darling, now ease down onto my cock. You can go as fast or as slow as you like.”
She slowly pushed down until most of the tip was past her anal sphincter. Then she paused. She was panting hard – my empathy told me that most of that was from pleasure, though there was a little bit off pain mixed in. I could tell that she was quite excited – and determined to have my cock deep in her asshole.
“How are you doing, my love? How does it feel?”
“It hurts a little bit, Rich, but I trust you that you will fit. I want to engulf your big cock with my ass! I want to see how it feels to have you deep inside of that hole!”
She pushed her asshole past the tip and began slowly sliding down. She was now moaning in the way that was familiar to me as the sound of her deep sexual pleasure. Then she suddenly took in the last few inches and stayed there with her beautiful ass resting on my belly. “Oooooooh, Rich, this feels WONDERFUL! I’m definitely going to cum sooooooon!”
With that she began pumping her ass up and down on my cock, and that was when my own level of sexual excitement began rising toward a climax. It was indeed soon when she started to cum. “Ohmygod, Rich, I’m CUUUUUMMMMIIIIIIIINNNNNG!”
As she was cumming, she slowed her pumping action on my cock. And when her orgasm began to tail off, she pushed herself all the way down on the hard rod that was thrust up inside of her and held that position. And then she started squirming around, grinding her ass against my tummy and her asshole around my cock. That was when I went over the top as well and started spurting into her – and my moans joined with hers. “AAAAHHH!! I’m cumming too, sweetheart!” My orgasm continued for a long time – at least a dozen strong, satisfying spurts before they began to taper off. She continued cumming for a while after I stopped. And I could feel occasional strong aftershocks for a minute or more after it first seemed like she had stopped.
“How did it feel to have your asshole stretched and my cock deep inside of you, my darling?”
“Oh my goodness! I really didn’t think I would like it. At first it seemed so strange ... But then it felt ... stimulating, exciting, even exhilarating! I felt so full and stretched out!!! And then when I came it was AMAZING!!!”
I kissed her and held her close. She snuggled up against me and soon was sound asleep. Not much later, I fell asleep too. That quickly became the norm for us – we finished every day with an intense lovefest, and then we snuggled and went to sleep. Of course we had sex in the mornings too, and oftentimes during the day as well. She had a room of her own. But it turned out that she never slept there.
I could sense, though, that there were a couple of itches that she had yet to scratch. One was her craving for others to see her engaged in sexual activity. The other was a desire to have sex with other men. She didn’t want to stop having sex with me – she just wanted other men too.
I had no objection to either of her desires. In fact, I felt a compulsion to help her explore these impulses to their fullest. So I tried to prompt her to talk about having sex in public and having sex with other men.
“Have you ever thought about having sex in public, darling? When we were making love in the vineyard, you expressed concern about being seen – but it seemed to me that your eyes glowed when you thought about that. Was I right? Did it excite you to think about somebody coming along and seeing us?”
She shook her head, with more vigor, I thought, than the circumstances warranted. “Oh ... no! That would be embarrassing! I would never be able to hold my head up again if we were ever observed making love in public.” I had a strong sensation that she was saying what she thought she should say rather than what she really felt. So I pressed the point a bit.
“You have such a lovely body, Catherine. I think you know you do. Doesn’t it bother you that I’m the only one who sees just how beautiful your body is, how fantastic your breasts are, what a lovely, curvy ass you have – and how extraordinarily perfect your pussy is?”
“Doesn’t that make it more special, Rich, that you are the only man who gets to see me. Besides, my body isn’t all that great. It has a lot of flaws.”
But as she spoke, she wasn’t looking at me. Her eyes were turned to a blank spot on the wall but were glazed and unfocused, and what she saw in her mind was being naked and being admired.
I knew what I had to do. It would be a kind of seduction.
The next morning, while we were drinking coffee on the deck and enjoying the view of the lake that edges up to my back yard, I said to her, “I’d like to take you to a matinee symphony orchestra performance and then to dinner at this sports bar I know that has great food and a very fine wine list – plus it has a wonderful ambience. Will you go with me?”
She was surprised but delighted by the invitation. “Why, Rich, what a lovely idea! I love classical music! What’s on the program?”
“Beethoven’s Ninth – one of my favorites.”
“Oh! I know that piece, though I’ve never attended a live performance. And the restaurant sounds like it will be great.”
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