Just Another Pathetic Humiliated Loser
- 3 years ago
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To keep things confidential, I’ll just call myself Clarissa. This letter is the first erotic one I’ve ever written. I don’t know why I decided to write it. Having done so, I’ll probably write more, if something as interesting as the story I’m about to tell ever happens to me again. I’m sure that it will. I’m a girl who finds erotic adventures, if they don’t find me first. I should be honest and admit that I didn’t write this story to help anybody. There probably won’t be anything in this story that people find useful. If I’m wrong about that, I guess that’s good, but I really don’t care. Mainly, I wrote this story because I like the idea that some man or woman might be able to bring themselves to a nice orgasm by reading about a situation that I found myself in/put myself in. That’s the kind of joy that I hope to bring people.
It might help the reader to know what I look like. I’m a petite, 22-year-old Latina woman. My hair is dark brown, straight, and hangs just a few inches past the height of my shoulders. I have firm, but natural, B-size breasts; 26B to be exact. I seem to have a constant naughty expression on my face, thanks to the twinkle in my big, brown eyes and the perpetual smirk on my full, puffy red lips. I don’t want to seem full of myself, but it’s important to be honest. I can’t go out in public without causing jaws to drop either with lust or envy. I suppose part of these reactions have something to do with my insistence on wearing the hem of my skirts above mid-thigh and tops with necklines that plunge somewhere between the middle of my cleavage or lower. If the weather is warm, when I’m not wearing a skirt, I’m probably wearing tight bicycle shorts that end less than an inch below crotch-level. If the weather is cold, I tend to wear tight jeans or stretch pants that provide an excellent view of my little tight behind and my thin, yet finely toned, legs.
I grew up in Texas, but moved away from home to study English at Brown University. I just graduated a few months ago. I wanted to experience what it’s like to live in New York City, so eight weeks ago I decided to take a job as a bicycle courier, since there really aren’t that many jobs for English majors in Manhattan. I’ve really enjoyed it, so far. My work allows me to meet people all over the city and it’s great exercise. It pays pretty well, too. Since I’m very efficient at making my deliveries, it’s enough to pay for my little one bedroom apartment in the Village. I guess my only complaint has been that I really don’t know many people in the city and I’ve been a bit lonely.
At Brown, I got used to having lots of girlfriends and, well, having regular sex was nice and something I have missed very much. Since graduating high school, I haven’t been at all interested in tying myself down to one guy. I chose to find a group of hot guys at Brown who were ok with sharing casual sexual encounters with me, whenever it made sense for me to hook up with them, according to chance encounters with them at convenient times or to my own whims. The system worked out very well, even though many of the guys were involved more seriously with other girls. For the most part, I seemed to have a talent for picking guys who liked to get together for a fuck session, but would keep it on the down low. That way, I was able to have my fun without being Public Enemy #1 among the female students. Now, things are different and it has been frustrating. I’ve been working so much and it has been surprisingly difficult to meet people in this overcrowded city. It doesn’t help that I’m very picky about who I get involved with, even casually.
Just a few weeks ago, the tide turned a bit. I made a delivery to a 34-year-old anthropology professor at NYU and took the time to ask about his research on the Mayan civilization. I took some courses in human anthropology at Brown and found it all very fascinating. Intelligent men, when they talk passionately about their discoveries and search for knowledge, seem to send an electrical pulse directly to my clitoris. I couldn’t resist asking whether he’d like to go for coffee with me sometime. Usually, I hate to be the one to make the first move, but I made an exception in this case. He agreed to meet me on Sunday afternoon, which was my only day off, at a Dean & Deluca close to the university. We really had a good time. He was very funny and smart, so we decided to go out for dinner a few days later. On our third date, he kissed me goodnight before I went up to my apartment, but then we seemed to get stranded on first base.
On our fourth date, we held hands and he kissed me at the end of the night. Then, it was the same on the fifth and sixth dates. It wasn’t that I didn’t enjoy his company. It’s just that things didn’t seem to be progressing at all. I found it all very frustrating. I thought it was ridiculous that I hadn’t had sex for three weeks. At Brown, and back home in Austin, I had sex at least three times per week. I think it was making me a bit crazy. By the end of our seventh date, I decided to take charge of things more. When he walked me home to my building, I asked whether he would mind walking me to my door, since there had been some issues with break-ins at my building, recently. That part was a lie, but I thought that I could get him into my apartment and then into my pants if I could get him up to my door. When we arrived at my door, I thanked him for a fantastic evening and I pressed my body close to his and kissed him, practically shoving my tongue down his throat in the process. I thought it was a pretty obvious clue. I invited him in for coffee. To my horror, he told me he was very tired and needed to get on back home. It was only just after 8:00 PM!
Angry, insulted, and sexually frustrated, I left him to enter my apartment. I stormed into my bedroom, tossed my purse onto the bedside table, and threw myself onto my bed. I keep a long vibrator/dildo in my drawer that, I’m sad to say, I’ve had to use quite a lot over the past several weeks. I grabbed it, hiked my mini-skirt up to my waist, lifted my knees up, and spread them at a 45-degree angle. I twisted the switch on the dildo to make it vibrate and sucked and licked it until it was sufficiently lubricated. Then, I used my left hand to pull my panties to the side and, with my right hand, I guided it slowly into my pussy. It felt so good, but I couldn’t shake my resentment for having to resort to an electrical device to maintain my sanity. I just didn’t think it was reasonable to expect someone as hot as me to find it so difficult to get laid.
Leaving the dildo vibrating away inside me, I reached over to the table and retrieved the phone from my purse. When I moved in, I ran into a man from the upstairs apartment. He had given me his number and told me that I should call if I ever needed anything. He was reasonably attractive, but I hadn’t really seen him much, since then. We passed each other in the lobby a few times, but that was all. I know it seems a bit desperate, but I thought that it was worth a try. I called his number and said, “Hi, Drew, this is Clarissa. I don’t know if you remember who I am, but I live in the apartment just below you and…”
He interrupted me and said, “Of course, I remember. What can I do for you?”
I asked, “Are you at home right now? If so, are you alone? I mean, are you busy at all?”
“I’m just watching TV right now. Yes, I’m alone. What’s up?” he replied.
I said, “That’s great news. I know this might sound a bit strange, neighbor, but I have a big vibrator inside me and I’d really prefer that the thing inside me were attached to a man, y’know?”
After a few moments of silence, his response was, “Of course, I’ll be right down.”
I put the vibrator back in the drawer and heard a knock at my door just a few seconds later. Opening the door, I discovered him dressed in sweat pants and a t-shirt. Plus, his feet were bare. He said, “I’m sorry for how I’m dressed. I promise that I’m clean. I just didn’t expect to be going anywhere tonight.”
I smiled and reassured him: “No, it’s totally fine. I think you look very
good to me.” I wasn’t lying. He was a tall and good-looking guy, who just
happened to be very casually dressed. Also, my hope was that he wouldn’t be
wearing clothes for very long. I took him by the hand and pulled him inside.
Closing and locking the door, I guided him into my bedroom.
I was worried that he didn’t think I was serious, so I told him, looking intensely into his eyes, “Please stand here in the doorway. Once I’m in position, I’m all yours, baby.” With that, I crawled up onto my bed on my hands and knees and pulled my skirt up onto my back, giving him a clear view of the red, bikini-style panties that partly covered my ass. I turned my head around to look at him and wink as I pulled my panties to the side to reveal my ass crack and my pussy, which was still glistening and engorged from working it with the vibrator.
I will never forget the look of joy on his face as he realized he wasn’t dreaming and that he was experiencing the best surprise of his life. As I watched, he stripped completely naked with lightning speed and then made a gesture with his hands that I interpreted as: “Is this ok?” I nodded, sincerely, since he was in obvious great shape and his large and gradually increasing erection looked so delicious to my sex-starved mind. He stepped forward and wrapped his fingers around the material of my panties that would normally be covering the treasure between my legs, pulling them down to my knees. He positioned me at the edge of the bed, such that my feet and ankles were hanging off the end, and then I felt his cock sliding easily into my slippery opening.
I couldn’t help moaning, “Oh, my…”, as he thrust his around seven hard inches into me in one stroke and started fucking me so fast that I could hear his balls slapping against me with each stroke. Although I was well lubricated, his cock was thick, so I could feel my pussy stretching, especially as the large knob at the end partially popped out and then in again as he slammed the length of his shaft fully into me each time. He seemed to notice and gasped, “Oh, yes. You’re so tight.”
After several minutes, Drew slowed his thrusting a bit, obviously wanting to enjoy every second of his good fortune. Now, I felt him sliding in and out of me very gradually. It was wonderful, since it allowed me to feel every inch in both directions. Meanwhile, he used his hands to grab and smack my ass roughly, but not causing any serious pain. I thought I would cum at any moment, when I was suddenly distracted by a knock at the door. Instinctively, I knew who it was and I admit that I still harbored some resentment from the events that took place earlier in the evening. I told Drew, “Wait, stop. Just pull out for a few moments. I’ll be right back.”
I got up and let my panties fall the rest of he way to the floor. I also wiggled out of my skirt and took my bra off, which left me naked except for the little white tank top I was wearing that did a bad job at hiding my nipples from view. I closed Drew behind in my bedroom and walked to the door of my apartment. I put on a phony smile as I answered the knock, encountering (as I expected) my anthropology professor (his name was Nick, if you care) standing on the other side. I pressed a finger to my lips to discourage him from saying anything and then I gestured for him to follow me into the apartment. It was very gratifying to see how wide his eyes got when he saw me practically naked. I will forever enjoy imagining about what he must have been thinking was going to happen as he watched my naked ass as I led him to my bedroom door.
Once I reached the door, I turned and said, “Professor Nick, can you please take a seat there?” as I gestured to a cushioned chair that was in position facing my bedroom. Once he got settled, I opened the door, bringing Drew, with his wet and throbbing erection pointed toward the ceiling, into view. I got on my knees less than two feet from where the professor was sitting and beckoned for Drew to come over. He grinned as he approached and I wrapped my fingers around his cock to stroke him a few times, keeping my eyes directed at Dr. Missed Opportunity as I did so. After literally rubbing it in for a while, I directed my gaze to my neighbor’s throbbing dick and plunged it deep into my mouth. Out of the corner of my eye, I could see the professor’s face was beet red and that he was shaking from humiliation and probably a lot of regret. Between sucks and slurps of S.’s cock, I explained, glancing over at him, “Professor, you should have fucked me when you had the chance. It could have been you with my lips around your cock, but you just clearly don’t have the balls that my friend, Drew, has. Now, as a lesson that I hope you never forget, you are going to stay here until he shoots his load into me.”
With that, I motioned for Drew to sit on the couch across from where the professor was sitting. Facing the professor, I guided Drew’s cock into my pussy and rode him in that position. Listening to his moans, I knew he was very close to filling me up with his cum, but I thought it might be nice to give him some options before that happened. I asked, breathlessly, “Baby, do you want to cum in my pussy or maybe on me somewhere? What about in my ass? What do you think?”
S. replied, “mmmmmm,” so I knew I couldn’t count on him to make a decision just then.
I slowed my rhythm on Drew’s cock a bit and turned to the professor. I told him, “So, as though my friend isn’t having enough fun tonight, I’m going to make the decision for him. I think he might really love to squirt his load into my ass, don’t you? I mean look at me? Who wouldn’t, right?”
With that, I pushed up and off of Drew’s cock. As I removed him from my pussy, we made a wet, slurping noise. Since that night, the memory of that sound has helped me bring myself to orgasm so many times. I got down on my hands and knees on the floor, angling my body so the professor could get a good view of my rear entrance. I instructed Drew, “You’re cock is soaking wet, so don’t be shy sweetie. Slip your dick into my ass and don’t stop fucking it until you fill it up with your thick, hot dick juice.”
Drew didn’t hesitate long before positioning himself behind me and easing his cock into my ass. It felt so long and huge in there. The sensation was overwhelming and I helped to enhance it by reaching between my legs with one hand and playing with my clitoris. I think that wrapping my tight ass around his cock kept Drew on the verge of orgasm for dozens of strokes. As he fucked me, Drew spanked my ass and pulled at and pinched my pussy lips. The combination of stimulations was more than I could take and I came violently and very loudly. My body shook so hard from the orgasm that Drew had to stop thrusting into me and simply held the length of his cock deep inside as I tossed my body around. Somehow, he managed to stay on me as I thrashed around.
Just as I was catching my breath, I felt Drew’s balls and stomach pressed even harder against my ass. He shouted something incoherent and his cock jerked and unloaded gobs of hot semen into me. I rested my head against my arms, relishing in the hottest sex I’d had since moving to New York. Although the professor must have been very disappointed that it wasn’t his own cock exploding inside of me, I knew that he was unable to take his eyes off of us the whole time. Maybe he didn’t get to fuck me, but at least he could take the images of what it would have looked like with him.
With his cock still inside me, Drew rested his body on my back. He kissed my cheek and groped my tits as his cock slowly softened. I turned and kissed him passionately, thanking him so much for being there for me. Wrapping my arm around his neck, I said, “You are such a good neighbor. I hope we can do this again sometime.”
To the professor, I said, “You can go now.” At that point, the professor stood up awkwardly, since it was apparent that his penis was stiff from the scene he had just watched. He walked briskly to the door and out of the apartment.
My neighbor and me spent all of our free time over the next week or so having sex. It has slowed down a bit, since then. His girlfriend came back from a trip out West, so he hasn’t had as much time for me. Still, we do find each other free quite often and he only lives a flight of stairs away. It doesn’t matter. I’ve met more people since those early lonely days in New York, so I’ve got many more options for sex than I had in those dark days. I hardly need to use my vibrator at all any more.
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- 20.03.2023
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