This is a complete work of fiction, any similarities to anyone is purely coincidental
Anna the Intern
Most people see me as loud mouthed and obnoxious, but generally harmless. I work in a “man’s Industry” if there is such a thing anymore. So for the most part I fit right in at work. There are some women that work with me, but for the most part they are nothing to write home about. We do get some interns there from time to time though, and once in a while I see opportunity to exploit the occasional young and innocent girl. This has always been just a fantasy though, until last week.
I was browsing through craigslist rants and raves, looking at the ridiculous fake posts of women doing the Friday flash, and I recognized a familiar face in a picture. It was one of our new interns, a naïve girl named Anna. She was interning from BYU for the summer, trying to make enough of a mark for the management to offer her a permanent position. I’m not sure if she was posting on a dare from one of the other engineers or if perhaps an angry boyfriend had posted the picture for her, but it was definitely her. I decided that if I was ever going to act out one of my twisted fantasies this was the time to give it a shot.
I clipped the picture from the posting and printed it out on high quality paper and put it aside. I then watched her for a week or so watching to see what she drove, and what time she left every day. Since I ride a motorcycle to work every day and everyone knows it by sight, I waited until my last night shift the following week. I went home, caught some sleep, then drove my little beater car back to work just in time to see her pulling away as I came down the street.
I wasn’t sure what I was going to do, how I would approach her, or what to even say. As it turns out I got extremely lucky. I followed her into the city, where she stopped to pick up some friends, before heading on to a couple nightclubs. I kept my distance, just the thrill of this little hunt keeping me sated for the time being. They pulled up to 440 Castro, which was located in the Castro district in San Francisco. My heart sank thinking that this girl was neither innocent nor naïve, and she was going to one of the cities premier gay bars. I pulled to the side and pulled out my camera which was already equipped with a 200mm lens so I was able to focus right in on their group as they exited their vehicle to make their way back to the club. What I saw lifted my spirits. She clearly did not want to be there, merely caving in to peer pressure from her wilder friends. I snapped a couple pictures of her from the back going into SF’s “premier” gay nightclub.
It was a boring 2 hour wait sitting in the car waiting to see them come out, but sure enough here they came everyone laughing and having a good time. It was easy to get another pic of her from the front this time, obviously in higher spirits laughing and having a good time. It seemed to me that she was probably elated at finally leaving, but the pictures would tell a different story. I took a couple more of them getting in the car to leave then I went home to put together what I thought was a fairly ingenious plan.
The next day I went out and bought a couple trac phones, a voice changer for one of them and a pair of google glasses I had already had my eyes on. Then the following Monday when I went back to work I put my little plan into action.
I hung back when everyone else went to lunch, then slipped into her office and laid the trac phone and an envelope on her desk. The envelope contained the nude picture I had pulled from the internet, the photos of her going into the gay nightclub with her friends, her parents contact info, and at last my other trac phone number with instructions for her to call me the next Friday night at exactly 7pm. All I had to do now was see how she behaved throughout the week, and if it looked bad I could just abandon my plan.
This poor girl looked extremely stressed the rest of the week. I actually expected her to quit and go running back to Utah. I thought twice about my plans for her at least once during that week, but she showed no signs that she had told anyone. There weren’t even any rumors floating around about her.
Friday came and I had a reservation at a seedy motel. The kind that doesn’t check your ID, even if you rent three rooms so the center one has maximum privacy. At exactly 7 my phone rang. “H-Hello” she kind of rasped into the phone, obviously terrified of the position her friends had put her in.
“Are you a lesbian?” I asked, my voice changer making me sound a bit Darth Vader-esque.
“Um, no. I am not” she replied.
“What would your family think if they saw the pictures I took of you?” I said sounding as villainous as I could. My legs were shaking like crazy with excitement and a little fear.
“Please, don’t do that!” she sobbed into the phone. “They wouldn’t understand what they were looking at, my father would disown me”
As she said this she began crying uncontrollably for what seemed like an eternity while I waited for her to compose herself. “Why are you doing this?” she asked as she regained a little control.
“Your friends” I lied “they think you are a bit of a prude, maybe they are right. They told me that if you wouldn’t go along with the party they set up for you to mail the pictures straight to your father. From what I hear maybe I should just do that since they’ve already paid me and everything.”
“No!” she stammered, obviously confused. “I’ll double whatever they paid you, please!”
“I’m not interested in your money.” I told her “but maybe we can work something else out if you can meet me here”
“Okay” she cried, “just tell me where to meet you”
I gave her the address to the motel, and told her the room number to go to and that the room would be open when she got there, just go in and sit down. The phone instantly went dead as she hung up.
Of the three rooms I bought for the night, I was in the center. The one on the south side was on the corner overlooking the parking lot and the rooms shared a door to walk between them, as so many of these little places do. I have always wondered why these rooms were like this, but I was extremely happy for the convenience tonight. That is the room I sent her to, it afforded me the ability to see if she brought anyone or was followed so I may have an opportunity to escape if this went badly.
I heard the door close to the other room, a second later my phone rang. “I…I am here, Just as you told me”, she truly sounded just as I had hoped. Her voice was laced with fear and anticipation of what she was going to be asked to do for her freedom from the situation that her “friends” had put her in.
“Change into the clothes on the bed, then call me back” I barked at her, then hung up the phone.
I found myself wishing I had the foresight to rig up a camera so I could watch this delicious spectacle that was just two feet from me. After a long 2-3 minutes she called me back. “I can’t wear this, there aren’t even any panties…” she was babbling something about god and the church and her family. “That’s fine” I told her “we can forget about this deal and go with the original, What was your dad’s name again, let’s see here, oh yeah it was..”
“NO, PLEASE, I’LL DO IT” she screamed, then whimpered “you bastard”
“In Two minutes if your little ass isn’t in that lingerie, that’s exactly what I am doing” I said “no more bullshit I’ve got better things to do tonight than deal with some sheepish prude” trying not to sound as excited as I really was.
I heard her scurrying to try and figure out the lingerie in the next room, obviously she’d never had even the simplest of sexy underwear. A short time later my phone rang again. “I..I am dressed as you told me” she whimpered into the phone.
“Good, there is a door adjoining these rooms, come through to me now” I commanded her.
As the doorknob began to turn I turned on my studio lighting I had set up in my room. My google glass and camcorder were both taping this for prosperity. Though she couldn’t see it because of the bright lights in her eyes.
Anna isn’t what most of the guys at work would fawn over. She is brunette and around 5’ tall maybe 100 lbs soaking wet. She has small breasts and slightest hint of hips, just enough to tell you she is female. She is the epitome of petite. If they could see her like this it would probably change their minds, I was glad that none of them would be relishing this like I would. I had her in matching lingerie all white with blue accents, garter, stockings, a see through baby doll nightie, that tied in the center between her almost nonexistent breasts. Other than the lack of panties it is what I envisioned a girl like her might wear for a new husband on her wedding night, (and probably never again) but not when someone like me is about to manipulate and defile her innocence.
I noticed that she didn’t shave her little pussy bare like most girls do these days, probable more out of naiveté than tradition or anything. She did however keep herself reasonable groomed, no monster bush or anything. She looked almost totally untouched, and where so many fathers in the world hope their little girls are and fail, it looked like this one succeeded.
“How old are you Anna?” I asked her.
“Twenty four” was her reply.
“Twenty four? And your body looks like this, so completely untouched? Are you lying to me Anna?” I wasn’t trying to intimidate her anymore than I already had, but I was in awe of her purity, even though I should have expected it. “How many men have you been with?”
“NO! I’m not lying!” she snapped at me, “I don’t lie, which is a concept that I am sure that people like you are unfamiliar with.” And then as if remembering the situation she was in her defiant attitude immediately disappeared, and she answered “I have only been with one man, my fiancé, Michael.” She started to tear up “Our families kind of pushed us together, and they expected us to wait until we were married, but we gave into our lust one night…I…I didn’t even enjoy it…”
“So only one man? And only one time?” I asked, stunned by the answer. “What didn’t you like about it Anna? Why didn’t you enjoy it?” I was pushing her, trying to get her to open up to a stranger who was about to do god knows what with her. I felt a twinge of guilt about my plans for her that night, but my rock hard erection pushed that emotion away easily.
“Yes” she whimpered, back to her sheepish self again. “Only once, and it was over very quickly, he ejaculated inside me and we both freaked out, if I got pregnant and our families found out they would all be ashamed of us and maybe disown us…” She looked down, genuinely ashamed of herself. She was a very intelligent confident woman at work but here in front of me she was trembling, uncomfortable with her body, ashamed of the desires she confessed to having in that fleeting moment. I remember thinking that it was a travesty what religious families like hers did to their kids.
“Do you know what I made you come here for, Anna?” I asked her.
“I’m not stupid” she replied. “I knew when I read your note and made the call that you were an evil foul man and that you wanted what my daddy told me all evil men want, and it was confirmed when I saw these sinful clothes you’ve made me wear.”
“I won’t argue morality with you here tonight Anna, maybe another night, but let me assure you, ALL men want what I want from you. There is no evil in lust, in the desire to pleasure and be pleasured by a woman. I can see why you think what I am doing to you is evil. I can even agree with you that it is evil. But I learned a long time ago that you can’t just live with fantasies your whole life, sometimes you need to act on them, and when the perfect opportunity arises, only a fool lets it slip through his fingers.” Then I told her “Anna, you are my fantasy, and what I am going to do to you, I have fantasized about since the first day I saw you.”
She looked up at me for just a moment, her eyes staring intently into mine as I said that. Then, just as quickly she looked back down at the floor, her cheeks flushed and full of color. “Please just don’t hurt me.” She wept a little as she pleaded. “I have done everything you have asked, I am not even sure I can live with myself after what I am going to allow you to do tonight. But my family has far less chance of seeing my sins if I go along with you, and I know I can’t live without my family.”
With that I approached her. I pulled the string from the sheer nightie that I had made her wear. As it fell to the floor I ran my hands down from her shoulders across her little breasts. She winced and almost pulled away from me as I brushed my fingers across her tiny nipples. I marveled at their size, smaller than my hands by a fair amount but still sexy as hell, she had dark pink areolas about the size of a nickel on each breast. Her skin was a pale milky white color, she had obviously not spent any time playing outdoors on the weekends, there were no visible tan lines. Her skin was flawless, soft and smooth untouched for the most part by any man. She shivered and tears formed in her eyes.
“Anna, I want to hear you say what we are going to do now”
“You are going to make me have intercourse with you. “ she replied.
“No, Anna, You are going to let me fuck you tonight.” I said. “That is what I want to hear you say. Tell me you are going to let me fuck you tonight.”
She looked up at me again, I have no idea whether she could actually see my face or recognize me with the lighting behind me. She was fighting to not be the little whore that I was going to make her. I could tell she was afraid of liking this. She hesitated for what seemed like several minutes, in reality I am sure it was only 10 seconds or so. “You are going to fuck me, and I am going to let you.” she whined.
“Okay, turn around, you are a small flexible girl so I want you to bend over and hold onto your ankles do not let them go for any reason.” I commanded her. She looked confused as she slowly turned and bent at the waist. As her slim fingers grasped her ankles she must have finally realized why I had her do that. She was no completely exposed to me. More exposed than she ever had been to any man. I ran my hands up both sides of her thighs and over the top over her ass, my thumbs gliding up her inner thighs over her little slit and puckered ass. I wanted to pull my raging hard on out and just cram in in here all at once, but I fought the urge and continued my exploration of her almost pure form. In truth I wanted this to last longer than the whores I had been with, what would be the chances for a repeat performance? Then there was the fact that she had asked me to please not hurt her, and being the kind hearted gentleman I am, I wanted to make her enjoy what I was doing to her. Even if she wouldn’t admit it.
I leaned over and put my face in her crack, running my tongue down over her little rosebud and down to her cunt. She flinched as I made contact and I felt her tense up as my tongue brushed past her ass. I pushed her lips apart with my tongue and at the bottom found her little clit, coaxing it out of its hiding spot. I felt her knees tremble and she let a little moan escape her throat as I began lapping at her clit, and I felt her begin to get wet. She tasted fresh and clean and as she got wetter, her moans became a little more pronounced, though it was obvious she was trying not to enjoy what I was doing. I hadn’t actually planned on going down on her. But when I saw how untouched she was and thought about how there was a good chance no one was ever going to do this to her again, I felt compelled to give her and experience that she could enjoy. I was still rubbing her from thighs to ass and back with my hands as I did this and I stopped and raised my head for just a moment.
“What are you doing? Why did you sto…aahhhh” she almost screamed as I ran my fingers inside here for the first time. She was soaking wet but so tight I am not sure if it was pleasure, pain, fright, or all three that drove her reaction. I pushed my middle finger into her tight cunny as far as I could and I could feel the entrance to her cervix. I rubbed the spot just above and all at once her cunt clamped down tight enough to hurt my finger and she screamed and started to fall over.
I caught her as she lost her balance and realized, she just had her first orgasm of her life.
“Oh, what was that?” she asked me. In that instant I felt like the biggest pervert on earth, like I was taking the virginity of a 14 year old girl instead of a 24 year old woman. This Young lady was truly as naïve as they come.
“It was an orgasm, Anna” I said to her, resisting the urge to use a term of endearment on her like sweetheart or lover, reminding myself that she was my prey, my victim if you will. The truth is I was very confused by the fact that she had truly enjoyed what I had done to her so far (at least in my mind) and by her sudden ease with what I was doing. Whether it was real or imagined, I still have no idea.
I carried her small body to the king size bed, laying her down on it to recover while I prepared for what was next. I turned off the studio lighting and turned the lights down low in the room. I no longer cared in that moment she saw my face, I was going to fuck her and would pay the price if there was to be one. I quickly shed my clothed and turned to her and she immediately got nervous again. I am guessing that she never got a close look at a cock before.
Now, my cock is average at best. Six inches, circumcised, with a well-defined, fat purple head and a thick shaft. Every lover I have had has told me I have a beautiful cock, but no one has ever said it was big. So when she started asking me questions I got a little chuckle out of it.
“Are they all that big? My fiance’s is smaller, is it going to hurt? Will that fit in me? Do you have to do this? Please have some mercy on me you’ve already humiliated me so much…” she begged me as tears began to stream down her face.
I didn’t answer any of her questions, instead I pulled her to me at the edge of the bed. I held her tight against me as she sobbed into my chest. I was literally in the toughest predicament of my life. I felt shame and guilt for what I had done and was going to do to this fragile confused woman. But at the same time I was overcome with lust that was driving me on. I felt just like the cartoon character with and angel and a devil on his shoulders. Everything about the situation had changed, she wasn’t the little prude I had taken her for, nor was she a cast iron bitch that needed to be taught a lesson. She was just a scared little girl in a woman’s body, well age wise anyways.
As I stood there at the edge of the bed holding her, trying to make a decision, I noticed something change. She had stopped sobbing. Her breathing was still ragged, but she seemed to shift from being scared and upset to...something else…then I felt heat on my cock and I realized that when I pulled her to me her legs were around my waist at the edge of the bed and my cock had been pressed against her now soaked pussy.
I looked down at her as she was looking down at my cock nestled between her legs, not in a position to actually go in without a little maneuvering, but still there nonetheless. Already this sexual encounter had topped the charts for anything she had experienced in her life.
“Anna, look…” I stammered. My guilt tortured me and fought with my sick pride.
She looked up at me, I could see recognition sweep across her face. “Go slowly, please Drew” she said to me, using my name.
I tossed the glasses to the side. Bending down to her face I gave her as gentle and loving a kiss as I could while entering her body. I pushed the head of my cock into her cunt causing her to gasp in pleasure and pain, she was so tight. I have been with my fair share of women. Done just about everything with a woman one could do and I have never felt anything like I felt entering this woman. Her cunt held me like a vise and seemed to squeeze and massage my cock as I began to move back and forth in rhythm with her as she ground her hips into mine.
She dug her nails into my back and smashed her mouth against mine our tongues entwining, overcome with lust. A primal desire was driving her that she had never felt before, she was reaching for another orgasm, the second of the night and of her life. Her hips bucked back and forth on my cock as I thrust in and out of her hot, wet pussy. I could feel the greatest orgasm of my life building in my balls, traveling up my shaft. In just a few minutes this situation had gone from me coercing this woman into sex, basically raping her, to something else entirely. It was mutual, we were fucking each other maybe even making love it was all blurring together. Because she was so incredibly tight I could feel every change inside her as her orgasm began to wash over her. Her legs locked around my waist began to shake violently, I could feel twitching and rippling inside of her and when her cervix began to spasm against the head of my cock it pushed me over the edge. I unleashed a torrent of cum into her sweet little box, and just as the confines of her tiny cunt made it possible to feel her every spasm and contraction of her orgasm, it also enabled her to feel mine as well. My cock pulsed and swelled with each spurt of semen I was releasing into her, and with each spurt her orgasm seemed to reach a new height, it felt for a moment like we might both die of pleasure.
We collapsed onto the bed together locked in the afterglow of what we had just done. We looked into each other’s eyes. I wasn’t sure where this was going to go, but I didn’t care.
She broke the silence first. “I should hate you for this but I can’t” she said, “Where do we go from here? Do we go anywhere or is this still a sick twisted game? Because it feels like something incredible just happened, for both of us, and I can’t ignore that.”
All of my guilt came back at once and I answered “Something did change, I don’t know what that was, I have never felt anything like it in my life” and I added “You should hate me, I should pay for what I have done to you, and if you want me to make it right I will confess everything to anyone you choose. However, you are right we just experienced something incredible and any price I have to pay will be worth it…”
“Maybe God did this to both of us…” she responded.
At first I wanted to brush the thought away. I certainly never have done anything worthy of any deities’ affection or any God’s love. But in the end what she said seemed right somehow. I chose to swallow my doubts in that moment and go with her heart. I figured maybe she had enough for both of us.
“Maybe” I replied “Does this mean that you’d forgive me for everything I have done to you?”
“No” she said, “but it’s a start.” With that she turned back towards me, kissing me and taking my renewed erection in her soft hand and gently stroking it. “and, we can get working on the rest right now."