The night after Josie and I masturbated to Amy’s dirty masturbation video, I talked to Amy on the phone. Amy nervously said, “What did you think of the tape?”
I said, “What tape?”
Amy said, “Jack, I love the blackmail thing, but let’s just talk about this for real for a minute.”
I said, “Okay, I fucking loved that tape…so hot. I hope you don’t mind that I included Josie in the blackmail thing.”
Amy said, “I don’t mind…it turned me on that I knew she was going to watch it too.”
I said, “She and I masturbated next to each other while we watched it.”
Amy said, “that’s so fucking hot. Um…I have to be honest that I watched it a few times and I masturbated before I put it in the mail…giggle.”
I said, “Amy that was just ridiculously hot. You’re basically the hottest girl ever – not sure how I got you.”
Amy said, “Thanks…giggle…I guess you’re just lucky. Um, what did you think of me…giggle…fingering my ass? I can’t believe Josie asked me to do that. ”
I said, “Amy, I was stunned, but turned on, I mean I know you like it sometimes if I do that.”
Amy said, “I do. You know I do like anal sometimes…haven’t done it in a long time.”
I said, “I like it sometimes too. I enjoy pussy more, but anal is sort of naughty.”
Amy giggled and said, “Yes, to both of those. There was only one guy I did anal with. I like anal sometimes, but he just always wanted it. Started to piss me off, because he was a dick about it.”
I laughed and said, “I like anal, but it’s just sort of an occasional thing. I’ve never asked you for it, because well, we’ve been having lots of other fun.”
Amy hesitated and said, “yes we have. Uh…I’ve been kind of thinking about it though…I’ve been thinking about asking you to fuck my ass.”
I said, “Um, whenever you’re ready for it Amy. Also, I think I just came in my pants.”
Amy giggled and said, “Alright, well, when we get back to school, I’ll let you know when I am ready for it.”
I said, “Okay, and I promise I will never ask you for it.”
Amy said, “Deal, but I will ask you for it. Also, with the blackmail thing…I fucking love it Jack. And…I want you to feel free to push the limits there…but, if I don’t like something, I am going to say your real name, Jack. If I say ‘Jack’ in the middle of this blackmail stuff, you stop what you’re doing and we need to discuss something, alright?”
I said, “Okay…I think it’s fucking hot too and I would never want to do something you’re not into.”
Amy said, “I know you wouldn’t, but I want you to…to push it…no what I’m saying? Like if I am calling you Jason and I say ‘No’ or ‘stop’, you just keep going. If I call you Jack, you stop.”
I said, “Got it.”
Amy said, “Also, I don’t mind if Sarah, Mary, Josie, or Hyun know about this or even get involved in some way.”
We got back to school finally and it was great to see Amy all the time again. I stayed over at her apartment every night and we pretty much lived together. We did not do any blackmail stuff for awhile, but just enjoyed our regular sex. I wanted the blackmail stuff to come out of nowhere.
So, after a couple of weeks back at school, I figured it had been long enough that it would surprise Amy. One night, I was supposed to meet Amy at the library late at night to study. I went to the library and found a small study cubicle to set my things down. I wandered around the library looking for Amy. I finally found her in a row of shelves, looking at a book.
Amy was surprised to see me because I was early, and I moved quickly and purposefully toward her with an angry look on my face, so she would know I was playing as Jason, the guy blackmailing her. She gave me a worried look and said, “No, not you, how did you find me, Jason?”
I said, “Assume I always know your whereabouts, as I wrapped my arms around her and she put her arms up, but I just trapped them between us. I tried to kiss her and she moved her head and said, “Ewww, no don’t kiss me,” so I just licked her face. Amy said, “Nasty.”
Amy said, “What the fuck do you want? I made the stupid tape.”
I’m said, “Yes, well you didn’t exactly follow the instructions my gf gave you. You said some extra things…”
Amy said, “Fuck you! Making me fucking offer you my ass. You’re disgusting.”
Amy was dressed to be comfortable for a long night of studying. Her hair was put up in a messy bun and she was wearing baggy plaid pajama pants and tight little tshirt. She looked hot, even in these comfort clothes.
I ran a hand down into the back of her pajamas pants and into her underwear, slowly moving a finger down into her crack and pressing on her butthole. I said, “Yes, you did offer me this hole, didn’t you…,” I was slowly working the tip of my finger into her butt. She grunted, “Because you made me. Now get that finger out of there,” but I just pushed it further in.
I slid my other hand down into the front of her panties, touching her pussy at the same time. I pulled my finger out of her pussy and sniffed it, saying, “I can’t wait to enjoy my pussy some more.”
Amy said, “It’s not yours…”
I pushed my finger further into her ass and she made an uncomfortable face, wincing a little. I said, “Your whole body is mine…got it…if you don’t want that boyfriend hearing about all of this.”
Amy said in a strained voice, “Jason fuck stop…okay…,” as my finger was moving in and out of her ass, my other hand roughly grabbing her tits.
I shoved my finger all the way in and she grunted, then I said, “I have a cubicle on the fourth floor, come find me in 10 mins.”
I walked to a bathroom to wash my hands, then I went back out and ran into Amy.
Amy said, “Oh hi Jack, you’re here already,” and she gave me a hug and kiss.
I said, “Well, we agreed to meet now…”
Amy said, “Uh, go find my stuff on the third floor, I’ll come join you in a minute.”
I said, “Okay…where are you going?”
Amy nervously said, “I have to talk to someone quickly.”
I went to my cubicle on the fourth floor, it was in a quiet alcove and there were not many people, but there were some. Amy came along a little while later and nervously approached my cubicle. She said, “Jason,” in an annoyed voice and stood there with her arms crossed glaring at me.
I gave her a smug grin and said, “Good girl Amy, you’re right on time.”
Amy said, “Okay, well Jack is in this library dickhead, so let’s get this done fast. What the fuck do you want?”
Jason said, “Amy, get on your knees, right here, under the cubicle.”
Amy look around nervously and said, “Seriously?” I just kept pointing under the cubicle. She gave a heavy sigh and climbed under the cube, she barely fit and her head was ducked low. I unzipped my jeans and popped my dick out right in front of her face.
Amy said, “I’m not sucking your dick…”
I said, “You had no problem sucking it last time…I guess you want Jack to see those pics.”
Amy said, “Come on, I’ll give you a handjob…just…I’m not sucking it…that was a mistake that one time.”
I reached down and grabbed her by her hair, pulling her head toward my dick and used my other hand to smack my dick on her cheek. I said, “Amy, you sure seemed to enjoy it last time, now you are or I’m going to walk those pictures right up to your boyfriend. I bet he’d love that video, too. He’s right here in the library huh.”
Amy pushed away the hand on her hair and said, “Okay…fucking just let me get this over with asshole…and don’t cum in my mouth…seriously…” I let go of her hair and she put my dick in her mouth and started sucking it. She pulled her mouth off an said, “Is that enough?”
I said, “Look, you’re going to make me cum you little slut.”
Amy said, “But don’t you fucking cum in my mouth,” and she resumed sucking and said, “I can’t believe you’re making me do this.” She sucked me and I purposely made it last as long as I could. She paused, stroking my dick and giving me an annoyed look. Amy said, “dude, how long is it going to take?”
I said, “Well, that depends…are you going to give me a half assed blowjob or the real deal? Suck it like it’s your boyfriend’s dick. I know you enjoy sucking dick, so stop pretending you don’t.”
Amy groaned and then started really sucking it, the way she normally did. She looked up at me and swirled her tongue around the head, she licked up and down the shaft and then she sucked it, bobbing her head up and down quickly.
I felt like I was going to cum, but I didn’t tell her, I just pushed her head off my dick as I started spurting cum, so some got in her mouth and some hit her on the face and some got on her shirt. I grabbed her shirt and stroked the last bit on it, then wiped some cum off my dick and onto her cheek. Amy was looking at me in shock and said, “Jason…I’m supposed to go meet Jack now…shit.”
I said, “You said not to cum in your mouth and I tried not to,” then I handed her the photo of her nude on her bed and laughing. I said, “At least you got one more picture back.
Amy said, “Asshole,” as she shoved her way out from under the cube.
After Amy left me I moved down to the 3rd floor and found Amy’s stuff at a small table. Amy walked up a few minutes later and said, “Oh…hi Jack,” and she walked up and kissed me.
I said, “Your lips feel…I don’t know…they feel like after you suck my dick?”
Amy looked nervous, giggled and said, “I just had a lollipop.”
I said, “Dude, what’s that stain on your shirt?”
Amy turned red and said, “Oh, i had a glazed donut earlier, dropped it on my shirt.”
We sat across from each other at the small table and we were both really horny from the Jason thing earlier. Amy kept looking up at me with a sexy smile. Then I felt that she had slipped off her flip flop and was massaging my crotch with her foot. I gave her a look with raised eyebrows. Amy gave me a grin, passed me a note and then she walked away from the table.
I opened the note and it said, “Meet me in the South stairwell.” The library had a stairwell in each of the four cardinal directions, but students were lazy, so everyone took the elevator, even though there were only four floors. It was late, close to library closing time, so it was unlikely anyone would see us in the stairwell, but still risky.
I went into the stairwell and Amy grabbed me, hugging me and kissing me aggressively. I moved my hands down the back of her sweatpants and into her underwear, feeling her bare ass. Amy broke the kiss and whispered in my ear, “I’m so fucking horny,” and I could feel her breath on my ear. She said, “you made me suck your dick under that cubicle…and came all over me…it was soo…hot.”
I was reaching down the front of her pants now and fingering her, I said, “What are you talking about?”
Amy said, “Oh, right that wasn’t you I guess…whatever, Jack the blackmail thing…it makes me so horny…”
I said, “Okay, well I can tell you that Jason enjoyed your naughty little mouth.”
Amy was a unbuttoning and unzipping my jeans, she said, “well, I love having your dick in my mouth, but I need to be fucked.” My dick sprung out of my underwear and she pushed down her sweatpants and her panties. She turned around, presenting her bare ass to me, while holding the stair railing with both hands. I briefly squatted down to lick her pussy from behind, then stood up and rubbed my dick around her wet pussy. I moved a hand all over her ass and said, “You have the nicest ass ever Amy,” as I inserted my dick into her. Amy sort of moaned, “thanks,” as I slid my dick in her.
I grabbed her naked hips as I thrusted into her and she pushed herself back into my dick in time with my thrusts. Since she had only blown me less than an hour before, I was able to last a long time. Amy started whimpering and moaning, “Jack, fuck me hard,” and it echoed in the high ceilinged concrete staircase. I reached around the front of her and fiddled with her clit as I banged her from behind. I was starting to make noises too and I said, “Amy, I’m going to cum,” and she shoved me off her, turned around and squatted down. She sucked my dick hard, while touching herself and she made little moaning noises on my dick as the two of us came. After I came, she stood up, pulling up her underwear and pants and then we hugged and kissed in the stairwell, her mouth tasting a little like my cum. Amy broke the kiss, rubbing her hand on my crotch and said, “Let’s grab our things and go back to my place, I might want to suck that some more…”
Source: reddit.com/r/Erotica/comments/zmpkn2/blackmailing_my_gf_amy_part_2_mf_21_blackmail
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