Progressive Blackmail – Chapter 2 [FF][22]

[Chapter 1 is here](https://www.reddit.com/r/eroticliterature/comments/kd7674/progressive_blackmail_chapter_1_ff22/)

I’d managed to avoid Bobbie for the past couple of weeks, but we briefly made eye contact when I came into our friend Gord’s place for his Saturday night house party. I wanted to turn around and leave, but I figured that was just asking for trouble down the road. “I don’t want to stay too long, let’s just have a quick drink then go back to your place and you can do anything you want to me” I whispered to Jack. His eyes opened wide in surprise and excitement as he nodded then headed over to the bar area to get us a couple of beers. Turning around, Bobbie was leaning over me, clearly having rushed across the room.

“Hey there sexy beast” she chimed, “I’ve had my eyes out for you but haven’t been seeing you around. I almost feel like you’ve been dodging me, which would sure hurt my feelings!”.

“Hi Bobbie,” I responded, trying my best to smile. “We just dropped in for a couple of minutes. How’s it going?”

“Oh good, you know. Got some pretty sexy topless pictures of a dumb slut I know. Thinking about submitting them to Playboy. They’ve got some sort of ‘Horny Amateurs’ thing that doesn’t pay but accepts pictures from chicks who like to show off”

“What?!?!” I hissed as I pulled her in tight to me. “You said no one would ever see them!”

“Actually”, she responded “I said I wouldn’t show them to anyone who knows you. Does anyone at Playboy know you? Hmm?”

My shoulders slumped as I realized I’d been tricked. “Please don’t submit them to Playboy!” I begged “They’ll get shown around town in no time!”.

“Swing by my place tomorrow around 11 am and we can talk about it. I’ll let you see the pictures and would love to hear which ones you like best.” She started to turn away, then looked me square in the eye and said “Don’t be late!”.

—

I showed up at 5 minutes to 11 am in a cute, yellow sundress with a hat. I tried my best to look wholesome and was bracing myself for another tough session with Bobbie.

“Good morning” I said with a warm smile when Bobbie opened the door. The smile she returned was less predatory than what I’d been seeing from her recently. <More flies with honey…> I thought as I hefted the basket I’d brought. “I’ve got some pastries and a couple of coffees!”

Walking into Bobbie’s kitchen, I saw a Playboy magazine on her kitchen counter. It was opened to the ad soliciting amateur pictures. My heart sank that it actually existed, I’d half-hoped it was a bluff.

“I’ve often thought that we aren’t as good friends as I’ve always wanted us to be.” I began, setting down the basket. “Maybe we should go out to the spa together, my treat, and try to get a little closer to one another!”

Bobbie returned my smile. “We can definitely have fun together, but we don’t need to go out to a spa for that! I’ve got my camera all set to go in the other room!”

Tears hadn’t worked last time, so I tried to navigate this more carefully this time. “We seemed to… misunderstand one another last time we tried that. I just want your assurances that you won’t let ANYONE see the pictures or the video. What do you want for that? I can pull together a bit more money, I’ve been putting in overtime and saving. I have my car I could sign over to you…”

“Naw, I don’t need your money or your rust bucket” Bobbie cut me off.

“Now Bobbie” I told her “You fooled me once, I’m not getting myself deeper with you on this. Why would I trust you again? I’m not going to make things worse for myself.”

“I get that” she replied “But you admit I’ve kept my word, right? I did what I promised, even if it wasn’t what you hoped for”.

I wondered if I was falling for the same thing a second time as I reluctantly nodded.

“So, how about this, after today, if you go along with what I want, I promise to never show anything I have on you to anyone. I’ll keep it all as private as I can! I won’t show it to people you know, people you don’t know, or anyone. It’ll just be for me! Then this whole thing goes away and we don’t even have to talk about it again unless you want to bring it up.”

“I won’t!” I told her, “But I don’t want to give you an endless session to keep piling things on me until I reach my breaking point. I’ll give you 5 minutes, then we’re done!”

“Heh, I can’t do 5 minutes. How about 3 hours?”

We dickered back and forth until we finally agreed on 30 minutes, here in her apartment, that we wouldn’t leave and no one else would join us.

—

Bobbie had me sit in a chair she had set up in the middle of the room. Unknown to me (at the time), she’d hidden the video camera and had it recording the chair. There was about to be a far more explicit video of me, and I had thought the pictures were bad enough!

Making the most of her time, she started barking orders and had me in the chair with my dress hiked up. I flushed red as she had me pull my panties to the side and she began clicking from every angle. I didn’t notice that she carefully kept the view from the video camera unblocked!

After having me rub myself for a minute or two, she made me stop and hold open my lips. It was worse than a trip to the gynecologist, with the sexual atmosphere and humiliation added to being fully exposed.

After she’d snapped a bunch of close up pictures, she stepped back and ordered me to get myself off as fast as I could. I started going to town rubbing myself, thinking about my boyfriend and forgetting where I was to try to get in the mood. In the years since this happened, I’ve wondered why I didn’t just fake it, but at the time I didn’t want Bobbie to get angry if she could tell and it honestly didn’t even occur to me. I’d never faked with my boyfriend as we’d explored one another.

Bobbie could tell I was getting close to an orgasm when she told me to get up and kneel in front of the chair. She knew she had some great shots of me masturbating myself and that the video would be spectacular. After I’d knelt in front of the chair, Bobbie sat down in it in front of me. I should have gotten suspicious about what was about to happen, but at the time I was naive and had no clue what she was doing.

She pulled off her panties and pajama bottoms and picked up a Playgirl magazine from a nearby table. I imagine these days she’s probably looking at gay men’s porn, but at the time Playgirl was the only thing available with nude men. I was expecting she’d hand me the camera and get me to take pictures of her, when she looked at me, told me to “Get to work” and pointed at her crotch before looking back at her magazine.

“Whoa!” I said, realizing what was about to happen. “I didn’t know you were a lesbian Bobbie?!?”

Her face contorted with rage as she looked back at me from her magazine. “I *AM NOT* a lesbian!” she growled at me “I haven’t gotten eaten out for a long time now. I’ve been single for a while and my last couple boyfriends were garbage. They never wanted to do it and would give up and fuck me too fast. You aren’t a girlfriend to me, you’re a vibrator that talks. Now shut up and get in there, you’re wasting my time.”

Worried that she’d call off our deal if I delayed too much or tried to talk to her more, I moved up and put my hands on her spread legs. With a final dirty look, she went back to her magazine. I began caressing her legs and nuzzling thighs, hoping she’d change her mind.

“If you don’t get in there and start licking, I’m going to consider you not having fulfilled your end of the bargain,” she warned, not looking away from her magazine. I could see that she was getting herself worked up and had begun to moisten. This was a situation I’d never imagined myself in!

Everyone is surprised their first time eating pussy. Most people are enthusiastic about the activity, try to make the most of it and want to give a good performance. Everything about the experience hit me harder as I was doing something I WAS NOT enthusiastic about. Whenever I thought I might be meeting up with my boyfriend I’d tried to keep myself as clean as possible. Bobbie clearly didn’t care and she was still sweaty and dirty from not having showered today. There were hints of ass and armpit in her smell, which was almost overwhelming as she started to get turned on. Suppressing a gag, I wished I could send her for a quick shower before doing this.

As my tongue touched her pussy, the reality of the experience sank in and her cunt dripped moisture onto my tongue after the first couple of licks. I felt her stiff clit on my tongue and had the unmistakable feeling of having a pussy pushed in my face. Guiding her pussy lips to my tongue Bobbie told me to work around it before going directly on her clit.

A gooey mixture was oozing out of Bobbie as she moved with me and gave orders what she wanted me to do. I’d just quietly accepted whatever my boyfriend did to me, but Bobbie was making sure she got exactly what she wanted.

“Hike up your dress and start playing with yourself again” she ordered. When I didn’t respond for a couple of seconds she looked down at my ass until I did what she wanted. I wasn’t sure if she expected me to go under my panties or above them, but I started masturbating through my underwear, like I usually do at home. Unknown to me, the video camera was filming this perfect. Between me eating her out and masturbating myself, we were putting on a hard core lesbian scene.

For the next four minutes, Bobbie and I worked in tandem to get her off. She was smart to get me to start rubbing myself, as I became more enthusiastic about eating her out as I got myself turned on again. I was lapping at her clit when she began to shake and moan.

I did my best to make it good for her as she came, then started to pull back and get up afterwards. She gave me a cold look and asked what I was doing. Looking at her watch, she said she had another 7 minutes and I should keep working on her. In defeat, I resumed what I’d been doing and both of us orgasmed again.

I was shocked that she could be so cold to me right after I’d gotten her off. I’d felt waves of devotion to my boyfriend immediately after coming. She was unnatural! Shortly after the 7 minute mark, she looked at her watch again and told me that she guessed that was satisfactory and that I should fuck off.

I felt worse than I’d ever felt before as I tried to clean myself up a little and headed home.

<Thankfully that’s finally over> I thought to myself, unaware that I was completely wrong.

*Thanks to /u/*[*MrTSaint*](https://www.reddit.com/user/MrTSaint/) */u/*[*JaxsonDufreisne*](https://www.reddit.com/user/JaxsonDufreisne/) */u/*[*lover_of_all00*](https://www.reddit.com/user/lover_of_all00/) */u/*[*nakedinthebif*](https://www.reddit.com/user/nakedinthebif/) *and /u/*[*tnt4kink*](https://www.reddit.com/user/tnt4kink/) *for their comments on Chapter 1!*

Source: reddit.com/r/eroticliterature/comments/kdq9kq/progressive_blackmail_chapter_2_ff22