3 comments/ 94174 views/ 18 favorites Catholic Schoolgirl By: cattitude1965 I stood in the bright light of the hotel bathroom and examined my reflection in the mirror. My outfit consisted of a very short plaid skirt, a tight white blouse, white ankle socks, saddle shoes, white thong panties and a white bra. I had my long brown hair in pigtails. 'Yeah, I think he'll like this.' I thought smiling. "What's taking so long in there?" he called from the main room. "Be right out." I replied. I pulled a lollypop out of my overnight bag, unwrapped it and tossed the wrapper in the wastebasket. I opened the bathroom door. "Close your eyes." I called. "They're closed." he answered. I stepped out of the bathroom and walked to the end of the bed where he lay waiting for me wearing only his boxers and a smile. His eyes were squeezed shut. "Okay," I said. "Open your eyes." He opened his eyes and immediately sat bolt upright on the bed, his mouth half open. No words came. I smiled at him innocently. "Hi. I'm Cat. What's your name?" I asked shyly, running the lollypop back and forth across my tongue. "Paul." He said, eyes focused on the lollypop. "I'm Paul." "Hi Paul." I said, dropping my eyes demurely, studying my shoes for a moment. "Hi." he said, obviously stunned. "Do you want to play with me, Paul?" I asked, staring at the growing bulge between his legs. He stared intently at my mouth as I opened it and stuck out my tongue, running circles around the lollypop. "Yeah, sure. I'll play with you." he said. I smiled at him innocently. "So. . .uh. . .what flavor is that sucker?" he asked. "The nuns say not to call it a sucker 'cause nice girls don't suck things." I said. "Are you a nice girl?" he asked. "Not always." I said, studying my shoes again. "So what flavor is your sucker?" he asked again. I smiled at him seductively. "CHERRY." I said. His mouth dropped open and the bulge between his thighs grew. I held the lollypop out to him. "Do you want some of my cherry, Paul?" I asked, returning to the virginal facade. "Oh yeah, bring it over here." he said. I walked around the side of the bed and smiled down at him, holding out the lollypop. He took it from my hand and laid it on the bedside table. I frowned. He swung his legs over the side of the bed and pulled me onto his lap. He was surprised to feel my bare ass against his thighs. He lifted my skirt in the back and rubbed the soft warm flesh. "You're wearing a thong?" he exclaimed. I lowered my head, as if ashamed. "yes. . ." I replied. "The nuns say they're bad, but I like them. Is that okay?" "It's very bad." he said. I pouted a little in response. "I LIKE bad." he said. "How else are you bad?" "Well, sometimes I. . .touch myself. . .down there." "Really?" he replied. "Will you show me?" "I don't know. . ." I replied, acting unsure. "Come on. You said you wanted to play with me." he said as he ran a hand slowly up my leg, under the hem of my skirt and began to massage my upper thigh. I moaned softly, closing my eyes. He moved his hand further up and began to rub my pussy lips through the soft cotton of my panties. He covered my mouth with his, kissing me deeply. The crotch of my panties was more than a little damp. "Lay down and show me." he commanded. I crawled across the bed on my hands and knees, giving him a good view of my bare ass, the thin strip of white material disappearing between my cheeks. I lie down on my back and spread my legs a little. "Show me - now." he said again. I pulled my skirt up around my waist and slipped my right hand down inside my panties. I rubbed my hot pussy lips in little circles, working my hips in the opposite direction. I closed my eyes and moaned softly, enjoying this role-playing to the utmost. It didn't take long to feel a climax building inside me. My pussy was drenched. I began to slide my middle finger back and forth over my hard clit. Paul began to unbutton my blouse. I opened my eyes a little, smiling at him dreamily. He was straddling my hips, the boxers lost, watching my face intently, obviously enjoying seeing me in the throes of my solitary passion. He pulled the blouse open and undid the front hook on my bra, spreading that open as well. I began to whimper and rub my pussy faster, as my orgasm got closer. Paul leaned over and covered my breasts with his hands, kneading the soft milky flesh. "Oh that feels so good. . ." I moaned. And then my orgasm enveloped me. I rubbed my clit franticly, eyes closed, mouth agape, a long deep moan escaping my lips. When my body began to relax again, I opened my eyes. Paul knelt between my thighs and removed my thong panties. He pushed my legs farther apart and began to run his tongue up and down my wet slit, licking up my juices. "No," I said. "We can't do this. It's bad." "Does it FEEL bad?" he asked. He wrapped his lips around my pussy and sucked my clit gently. "No. . ." I said. "No, it feels so GOOD. . ." I closed my eyes and focused on the sensations his hot tongue was creating. He crawled up the bed and brought his body down on mine. His hard cock pressed against my inner thigh. My pussy began to throb with need. "I want to fuck you." he said, bringing his lips to mine. He pushed his tongue into my mouth, kissing me with such passion. My stomach did a somersault. I returned the passion of his kiss for a moment, wanting him inside me so desperately. But then I broke the kiss abruptly. "No, I can't." I whispered. "I've never. . ." I was completely lost in my role as the virgin catholic schoolgirl. Now the fantasy was mine as well as his. The line between fantasy and reality seemed to blur. I was totally into it, totally turned on by it. I felt incredibly aroused and yet somewhat apprehensive, as if it really was my first time. "Never?" he said. I shook my head. "You're a virgin?" he asked, playing his part to a tee. And I felt his hard dick throbbing against my thigh harder. "Yes." I whispered, looking into his eyes. He worked his hand between our bodies and began to slowly massage my swollen clit. "Look how wet you are." he whispered. "You're ready for me." He pulled his hand out and grasped his dick, rubbing it back and forth across my steaming "virgin" hole. I moaned softly. "Do you want me?" he asked. "Yes. . ." I replied breathlessly. "Tell me. . ." he said. "I want you. . ." I whispered, unable to control the desperation in my voice. "Oh god, I want you. . ." "I'll be gentle. . ." he whispered. A chill coursed through my body and I shuddered as he pushed his rigid cock into me slowly. When he had about half his length inside me, he hesitated. "This will hrut a little bit, but just for a minute." he said. "just relax and it'll start to feel really good. I promise." For a split second, I remembered my REAL first time - the momentary pain as my first boyfriend's cock broke through my hymen and then the extreme pleasure that came after the pain subsided. I smiled at Paul bravely now and nodded my head. He kissed me, softly at first, then growing more and more passionate. He broke the kiss and ran his tongue up the side of my neck. "I'm gonna make this virgin pussy mine." he whispered in my ear. He thrust his tongue into my mouth. When I began to moan and suck his tongue with desire, lust, he pushed his cock the rest of the way in, burying it deep inside me. I cried out, my body seemed to remember the pain for just a second. He began to stroke my hot cunt. I pulled my legs up and he grabbed them, putting them over his shoulders one at a time. This position provided not only deep penetration but also plenty of friction on my swollen clit. I moaned, "Fuck me. . .oh god. . fuck me, Paul!" All virginal pretenses were gone. I was so completely turned on, so hot, I just wanted him to shove his hard dick inside me over and over. We fucked like animals - moaning, groaning, whimpering, panting. It was the hottest sex we had ever had. We climaxed together, grunting and grinding against each other desperately. I could feel his hot cum filling me as my pussy contracted over and over, milking his cock of all its juice. When it was over, he pulled out of me and rolled over onto his back. I knelt between his thighs. I pulled the ponytail holders out of my hair and ran my fingers through it. 'What a sight I must be!' I thought. My blouse was wrinkled and hanging open, bra open, plaid skirt bunched up at my waist, I was still wearing the ankle socks and saddle shoes. I bent down and took him into my mouth, licking and sucking our combined juices from his cock. What a fabulous, erotic flavor! He moaned. I sucked him until he was hard again. "Fuck me. . ." he pleaded. I straddled his hips and lowered myself onto his dick. I began to ride up and down, varying the pace and angle of my strokes. Everything felt so damn good! I rested my hands on the bed, just above his shoulders and rode him like a whore, fucking him with total abandon. He grabbed my ass and began raising his hips off the bed to meet my strokes. I came hard, crying out, my whole body shuddering uncontrollably. When my orgasm subsided, he rolled us over so that he was on top. He thrust his cock into me, over and over. "Fuck me. . .fuck me. . ." I moaned again and again. Another wave of pleasure washed over me, causing me to gasp and whimper, clinging to him tightly. He fucked me harder, faster. "Yes, baby, stick it to me hard. . .Mmmmmm. . .fuck me hard. . .cum inside me!" I cried. His orgasm seemed to explode inside me, hot cum splashing against the walls of my cunt like lava. I'll have to let him "take my virginity" again sometime! Maybe next time I'll bring a friend! Catholic Schoolgirl Red Helen ran the best brothel in that county of Nevada, and one reason for its preeminence was that she catered to any preference a horny man might have, as long as it was within the law. Such a man was Rick Rhodes, who lusted after teenaged Catholic school girls. A long time ago, he lost his cherry to one of them, an older girl who attended school with him. Still wearing most of her uniform, she had bared her ass for his cock and, ever since then, the sight of a middy blouse and a plaid skirt around chubby youthful buttocks would drive him wild with lust. He went to Helen and told her what he lusted for. "I have just the girl for you. Come with me," she said, after taking his money, including a premium for meeting his particular needs. Before taking him to meet the brothel employee, who was guaranteed to be just what he wanted, Helen called the young woman who specialized in that specific fetish to tell her to get ready to serve a new client. While leading Rick to the part of her establishment where special needs like his were met, she described the girl who would be his sex partner that day. "Mary's 18 years old, and a genuine Catholic high school girl. At least she was, until she graduated a few months ago and came here. Her uniforms are the real thing too, because they're what she wore her senior year." Helen stopped and opened a door. On an overstuffed sofa was the girl of Rick's fantasies, plump and fair-skinned and wearing long white stockings, a white blouse and a dark blue plaid skirt that was pulled up, showing off most of her shapely bare ass. She had long, straight brown hair and was looking toward the door and grinning at him, as if she knew what he wanted and wanted the same thing. Helen left and Rick closed the door and hurried to approach his living fantasy, with his cock almost tearing a hole in his pants. Mary knew what was expected of her. "Oh, gosh, Mister," she said while smiling lewdly at the approaching man with the bulge in his pants. "You sure got a big thingy. I hope you don't want to put it in me. I'm a good Catholic schoolgirl, and a virgin." Rick went along with what he could see was part of the role-playing. "Yes, Mary, I'm going to stick my big, hard cock into your tight little cunt." As he spoke, he unfastened his pants and opened the fly of his jockey shorts, giving her a better look at his protruding erection, which she saw was actually slightly less than average size. Even so, her act continued. "Oh, no, Mister. You can't put your big thingy in my tight little cunny. I'm saving myself for marriage, like a good Catholic girl should. It would be way too big to fit in there anyhow." "Well, Mary, I can see how you want to save yourself for marriage, but what about me? Guys get sick when they get all hard like I am and can't do anything about it. You don't want me to get sick, do you?" "Gosh, no, Mister." During their conversation, Mary had remained lying on her belly, slowly pulling up her plaid skirt until it was above her hips and she was showing off the rest of her succulent ass. "But I don't know what I can do to help you." It was obvious to Rick what she would do. He didn't know if her hymen was still intact or not, and didn't really care, because he was sure his cock would be thrusting in and out between those delightful naked white hemispheres in a few minutes. For one thing, Red Helen certainly wouldn't let him down and, more important, he saw a plastic bottle of what looked like Aqualube standing in front of the sofa along with a folded towel. He stepped forward and placed his hand on her lovely ass, gently spreading her cheeks with his fingers. "What about in here, Mary? You'll still be a virgin and I won't get sick." She pretended to think about that idea for a few seconds. "Well, I guess that would be alright. Just as long as I'm a virgin for my rich, handsome husband on our wedding night." She reached under her body and pulled her skirt up until all the fabric was above her waist and reached back to spread her cheeks. "You'll have to use some lube, though," she cautioned, coming briefly out of character. "And a condom," she added, as she handed him the plastic-wrapped packet she had taken from under one of the sofa pillows. Rick had no problem with either of those requirements. He scuffed off his shoes and sat next to her to pull off his socks and pants and shorts and open the packet. After rolling the condom into place, he stepped up to the sofa where the Aqualube had been left. Trembling in his eagerness, he unscrewed the cap, placed the neck of the bottle against the small hole the former schoolgirl was holding open for him and squeezed in a big dollop. She enjoyed working for Red Helen, and really liked the feel of a cock driving in and out of her ass, at least as much as she liked it in her pussy. Her name wasn't really Mary, but that seemed like a good name to use when she was being fucked by a man who had that particular fetish. Everything else Red Helen had told Rick about her was true, including the fact she was only 18 years old, the minimum age to ply her profession in that county, and that she had been a student in a Catholic high school until her graduation the previous spring. It was her idea to tell some men she was trying to preserve her virginity, but it was also in keeping with the role she was playing. Her cherry had been broken long ago, but she liked to tell her customers, especially those with small cocks, that she was still a virgin who was saving herself for marriage so they would be willing to settle for fucking her in the ass. If the customers were really hung, she preferred to take it in her pussy. Another reason for the success of Red Helen's establishment was that her girls really enjoyed sex with their clients, and usually climaxed several times a day while working there. Rick knew some of what he had been told was to feed his fetish, and didn't care at all if he was being fooled by Red Helen and Mary, or whatever her name was, and he didn't ask any more questions. The sexy young woman's attire was luring him on and her lush bottom was exactly what he wanted to fuck. After squirting a gush of the lubricant into the small pink hole she was holding open for him, he inserted his left middle finger up to the knuckle to spread the lube all around the inside. When her ass was ready, he prepared himself by coating his cock with more of the contents of the bottle and climbed onto the sofa between her legs, which she was spreading for him. With the thumb and fingers of one hand, Rick reached between the plump ass cheeks Mary's hands were holding apart and pried open the pink rosebud they were framing so beautifully. His other hand guided his cock, and he leaned forward until he felt the tip press against the hole he and the former schoolgirl were creating for him. After moving it up and down for a few seconds, he thrust forward and uttered a grunt of pleasure as he felt the head wedge its way into the tiny opening. A few seconds later, he pushed again and sighed happily as his shaft burrowed in more deeply. Mary echoed the sounds of joy being emitted by the man between her legs. For several reasons, she loved her job working for Red Helen. The most important was that she immensely enjoyed all varieties of sex with her customers, who almost always treated her better than any of her boyfriends ever had, especially when it came to fucking her ass. The current man, whose name she had been told was Rick, was no exception. Whether it was part of their role-playing or not, he was actually being solicitous of her. "Does that hurt, Mary," he asked her. "If it hurts, tell me and I'll stop." "No, Mister. It doesn't hurt at all. It feels really good." "I'm glad to hear that. If it doesn't hurt, I'll keep going, because it feels great to me too." It really did feel great to Rick. Mary's ass was tight, and his cock was buried in her deeply enough he no longer needed to guide it. After pausing to wipe off his hands on the towel that had been next to the lubricant, he caressed her white and succulent cheeks, placed his hands on her shoulders and pulled back on them while carefully driving his cock in farther. She moaned, but he was sure it was from pleasure, either simulated or real, and he continued to imbed his cock in her ass in small increments. He didn't stop until it was all the way inside, and he could feel his pubic hair brushing against the soft insides of her cheeks. Rick lay like that for almost a minute, reveling in what was happening to his cock, while the girl squirmed under him, making it even better. He kept his hands on Mary's shoulders for leverage, and pulled his cock most of the way out, paused and drove it back into her. She was still tight, but the Aqualube was spread evenly all over the inside of her ass, and his hard shaft burrowed its way back into her until his hair was tickling her cheeks again. She moaned, more loudly this time, and the movements of her body became more intense. After once more lying on top of her for a minute, Rick drew back and stroked into her, and he could feel Mary trying to fuck back to meet him. "Do you like that?" he asked. "Oooo, yeah, Mister. It feels really good. Don't stop. Rick had no thought of stopping. Over and over, he thrust his cock into her tight, oily hole, and felt her trying to respond. The Aqualube was working perfectly, and there was no friction, just the tightness of her ass, her plaid skirt and white middy blouse under him and her moans of joy. Good as the fucking was, it could be better, if Mary was willing to change position. "Do you want to get on your knees?" he asked. "Okay, Mister, if you want me to." Most of Rick's weight was on his knees and, while keeping his cock buried to the hilt in Mary's ass, he straightened up somewhat, pulling on her hips while she pushed against the arm of the sofa. When they were ready to resume their fun, she was kneeling and leaning against that same sofa arm and he was on his knees directly behind her. With his first stroke, he drew back and slowly drove his cock forward. Mary felt the hard cylinder surging into her ass, stretching her sphincter open and expanding the attached channel and fucked back to meet it. By the time her body and his met, the entire shaft was buried in her ass, and she could feel his short hairs against the sensitive insides of her cheeks. She moaned in bliss, and her happy noises were matched by those of Rick. He drew back and thrust forward again, and this time when their bodies met, their sounds of joy formed another duet. He stayed in that position for almost a minute, reveling in the way her sphincter and other muscles in her ass massaged his cock, before pulling it away and driving it back inside. They continued like that, with neither of them saying much except to express their excruciating pleasure. The position was much better for Mary, because she could be a more active participant, rather than lying quietly and getting fucked. It could be better, though, and she was the next to make a suggestion. "Why don't you stay there and let me do the moving and ream myself on your big, hard cock." She was forgetting to stay in character, but neither noticed or, if one of them did, it was not important enough to mention. "Okay." Rick was no longer thinking of their fucking as being him and a Catholic school girl, but as a young woman with a fabulously tight ass. Even so, the blue plaid skirt brushing against his bare belly and the middy blouse under his gaze and the long, white stockings rubbing against his legs were enough to keep feeding his fetish. He stayed in place while Mary reached over the arm of the sofa and tugged against it, pulling her ass most of the way from around the cock that felt so wonderful inside her. This time, she was the one who paused, but it was for no more than a few seconds, until she pushed against the arm and impaled herself on Rick's cock. He kept his hands on her round, soft hips and let her completely envelop every inch he had, until her soft ass cheeks were pressed snugly against his thighs. She repeated those same movements for a long time, swaying back and forth slowly so they could both derive even more pleasure from their coupling. Mary could feel her orgasm building and knew it would soon erupt to the surface, but the cock filling her ass felt too good for her to rush anything. From the way the man behind her was breathing and sighing, she knew he would soon be cumming too, but she wanted to be first to climax. "Mister, can you play with my man in the boat and make me cum?" she asked. Except that the other Catholic school girl had addressed him by name, those had been exactly her words, and hearing them made Rick's climax draw rapidly closer. He reached his right hand around her hip to find her pussy, which was dripping with the fragrant juices Mary had been secreting and he had been smelling. When he found her clit, he was elated to see it had become so swollen it was completely free of its protective hood, so he gently pinched the little cutie between two folds of her inner lips and started stroking in the same tempo as her movements to imbed his cock in her ass. "Like that," she sighed, and started moving faster. Rick quickly got more active, thrusting forward to match her pace as his cock was enveloped over and over by Mary's tight, succulent ass and stroking her adorable clit at the same tempo. Her movements were becoming more erratic, and his hand and arm on her hips served the double purpose of keeping her upright on the sofa and giving him leverage so he could plunge his cock in harder and faster. "Uh! Uh!" she started whimpering and her movements became more erratic, until Mary uttered a cry of joy and started cumming. Her responses to that delightful condition became even more pronounced, so Rick took complete control of the action, pushing Mary against the back of the sofa and hanging onto her with the arm he had around her hip. His fingers and thumb kept stroking her clit and he drove his cock in and out of her while her voluptuous body tossed and bucked in front of him. He was on the verge of cumming when the hot former schoolgirl cried out ecstatically as she climaxed, and rammed her ass back against him for an ultimate time. After her orgasm, Mary relaxed completely, sagging toward the arm of the sofa, but Rick kept her upright while continuing to ram his cock in and out of her ass. A few seconds later, his climax welled up inside his body and exploded, as he shot a big wad of cum into his condom. He kept fucking with hard, deep strokes until he had ejaculated two more loads of semen before he sagged against the delightfully plump ass of the woman who had just shared with him the best fucking he had done in many years. After a few minutes of total relaxation, Rick carefully pulled his cock from the tight hole where it had given and gotten so much pleasure. The transaction between him and Mary and Red Helen's brothel was over, but he hoped they could do the same thing in the near future. After properly disposing of his condom and putting his clothing back on, he made that suggestion to the young woman who was still displaying her bare pink and white ass to his admiring gaze. "I think I'd like that, Mister." She smiled and continued. "But, you'll have to talk to Helen about that. I just work here." Rick left the small room, but stopped before leaving the brothel to set up a series of appointments for the next several weekends. His sex life had been adequate before, but he expected it to be vastly better in the following months. Thank you for reading this story by me, Boxlicker101. Here is an URL to many more of my stories: http://www.literotica.com/stories/memberpage.php?uid=207952&page=submissions I hope you had as much fun as Rick and Mary had. I like writing stories on Literotica, but I like it a lot more when I know that people are reading and enjoying them, and I appreciate it when readers take the time to express their opinions by voting. Like most authors on Literotica, I practically live for feedback from readers, either public comments or email to me. Such feedback, whether praise or criticism, helps me to write more and better stories, and I respond to it whenever I can.