Jenny's Struggle Continues

Blackmailing Jenny for Wendy and Brooke

It had been a few days since Jenny's run in with her neighbor and landlord Nick. That whole weekend was just strange and she tried to forget about it by immersing herself in the new college semester. Everything seemed normal with her roommates and her boyfriend, so again Jenny was just trying to forget about everything.

Of course, Nick couldn't let that happen. He had spent the past few days editing the video he took of Jenny almost naked and on her knees rimming his ass and jerking his cock until he came all over her. He now had all the dirt he could possibly want on Jenny, which meant she was under his complete control. The next step was getting that same leverage on her other two smoking hot roommates.

"Hi Jenny its Nick. Come by tonight - I have a maintenance situation I'd like to discuss with you" - Jenny cringed as she saw the message come across her phone.

"Great... I was hoping I was done with this creep. Hopefully this is a sincere maintenance issue" she thought.

Jenny arrived later that night to Nicks wearing her usual short shorts and a t-shirt that belonged to her boyfriend. She wore no make up - she was trying to be as unattractive as possible (a hard feat for someone as naturally beautiful as her).

She was greeted at the front door by Nick with a huge smile on his face "Ah Jenny! Glad you could make it. Come on upstairs so we can discuss the maintenance issue".

Jenny rolled her eyes and followed Nick back up to his office where she had been embarrassed just days before, and she saw that Nick had a friend over.

"Jenny this is my buddy Dan - Dan, this is Jenny. I owe Dan some money but he agreed to a blowjob by a college girl if I could swing it. Just so happens I have plenty of incriminating video on you Jenny, so if I were you I would just go along with it. You know I'll share all the video with the whole campus AND your boyfriend otherwise.."

Jenny knew he was right. She shot Nick and angry look and walked over to Dan and got down on her knees before starting to yank his pants down.

"Not so fast not so fast! I love how eager you are, but we need you to be comfortable first... strip down to your bra and panties" said Dan.

Jenny complied without protest and discarded her boyfriends shirt to reveal her neon pink sports bra. She then peeled her short shorts down her tanned thighs leaving her in just her bra and a pair of black boy shorts that hugged her tight ass.

"Damn..." muttered Dan, in awe of this beauty in front of him. Dan didn't really know Nick but they met a few weeks ago at a buddy's house to play poker, and Nick put up more than he could afford... when Nick made the offer of a college blowjob, he figured it'd be someone much less attractive than Jenny.

Dan had Jenny lay down on the couch with her head leaned back over the arm - he walked around behind her head and instructed Jenny to open her mouth. As she did, Dan started to plunge his 6 inch cock down her throat. Jenny noticed that while his dick was a little shorter than Nicks, it was just as thick and Dan's balls were HUGE.

Dan couldn't believe the site in front of him as he eased the rest of his cock down this hotties throat, causing his balls to come to rest on her eyes and nose. As Jenny started to drool around the cock in her throat, Dan began to reach down and play with her tits through her sports bra by tweaking her nipples. Jenny was not expecting this and let out a little yelp, which Dan and Nick took as a moan of encouragement.

"Wow, I knew she was a slut! Listen to her moan on your cock" Nick exclaimed while walking around to different angles snapping pictures to increase his stock of blackmail on Jenny, as his cameras throughout the room continued to video.

Dan began sawing his slobbery cock in and out of Jenny's hot mouth, causing her to gag and sputter around the sizeable tool. Dan had pulled her sports bra down under her tits at this point, causing them to be pushed up together under her chin.

"OK Jenny I'll tell you the other reason I called you over, say yes if you can concentrate while taking his cock" said Nick.

"Uh huhhh" *gag gag* Jenny managed to get out.

"Great! I love that you can multitask. I'll get straight to it - I want to have the same leverage I have over you, over your roommates too. You are all way too hot, living right next door to me - I have to take advantage of this opportunity! So, you know them better - how are we going to make this happen?"

Dan pulled his dick out and Jenny wiped the slobber from her chin "You really think I'm gonna help you fuck my friends after what you are doing to me? You must be crazy!"

Nick replied "Jenny.. I know you're blonde but you're not THAT dumb! Come on... do we have to do this every time? I am not kidding, I have PLENTY of pictures and video of you being a little slut and all the contacts of everyone who matters in your life and more... you have no choice"

Jenny realized he was right and that there is no point in fighting... she didn't know what to do... "OK... Wendy is a slut and everyone knows it so you'll have to find some other way to get to her.. her family is racist so if you can figure out a way to get some pictures of her with a black guy, that would work. Brooke is so obsessed with her boyfriend that her cheating with anyone would be plenty"

Dan reached down and pulled her sports bra completely off, came around, and sat on the couch next to her. While squeezing her tits, Dan instructed Jenny to take her panties off and start masturbating while she jacked his cock. Without thinking, Jenny peeled her tight panties down, sat back on the couch with her legs spread and started jacking Dan off while rubbing her clit.

Nick replied to her "Well Jenny it looks like you have a plan and place. Make one or the other happen by this weekend, and the other by next weekend. For each week you go past, I'll come up with a new punishment for you for motivation" he smiled.

"This week will be some form of public humiliation... we'll see if I need to think of anything past that".

Jenny was in a daze as she heard her instructions - she just continued pumping Dan's cock and rubbing her pussy, which was starting to become extremely wet due to her manipulation and Dans hands on her tits.

After a few more minutes of this, Nick had Jenny lay down on the couch. Dan stood over her head, alternating between fucking her pretty mouth and having her lick his ass - all while mauling her wonderful tits. Nick took up a position between her legs - but he didn't fuck her. He wanted to save that for another time.

Instead he had Jenny reach down between her legs and jack his cock, instructing her to occasionally rub it on her wet slit. With her other hand they had her alternate between rubbing her clit or jacking Dan's cock as well. Nick's room cameras were getting some very hot video of these two older men dominating a college hottie.

At one point when Nicks cock was hard and wet from rubbing on Jenny's tight pussy, he backed his hips up, took his cock in his hand, and pushed Jenny's legs back. Very delicately he eased the head of his penis into her tight anal opening.

Jenny immediately stiffened up and back her head up off of Dan's cock, trailing drool back to it, "What the hell!" She exclaimed.

"Oh relax, just poking my head in a few times for fun - I won't actually fuck your ass... today" he replied.

"OK last trick of the day Jenny and you're free to go!" Nick said. Jenny was actually excited to hear what it would be so she could get the hell out of her and take a scalding shower.

"I'm fan of putting a time limit on these things so you feel more inclined to participate. You've already got us both all worked up, so I will be generous and put 5 minutes on the clock. If we don't both cum in 5 minutes, 1 of your hot photos will get posted on the local college hotties site. 10 minutes, 5 photos - I will keep them all anonymous for now, don't worry. Just knowing your body is being seen by so many is hot!"

Jenny couldn't believe what she was hearing, but had a feeling he wasn't done..

"In addition to this, after 5 minutes I will stuff a dildo in your tight little pussy. After 10, one goes in your ass. If you somehow take more than 15 minutes to get us both off, we'll both fuck your ass and cum in your mouth. Sound fair? Good! Go!"

Jenny practically fell off the couch and started jerking both cocks furiously in front of her. Unfortunately from Nicks talk, both had gone flaccid. She worked them back up to rock hard in no time and started alternating her deep throat on each, working up a lather of slobber and precum dripping down onto their balls, her chin, and her tits.

As Nick filmed with his phone he announced "4 minutes in!"

"Shit!!" Jenny panicked.. she knew Nick was a sucker for rimming, so she focused on his ass. She pushed his legs back and dug her head in under his balls - still managing to jack his cock AND Dan's at the same time.

"Ugh.. five.. ahhh minutes!!" Nick yelled as he grabbed Jenny by the hair and slammed her face down on his shaft til her nose was buried in his pubic hair "aggghhhhhh!!" He yelled as he filled her throat with spurt after spurt of hot white cum that Jenny had no choice but to gulp down.

"Well done Jenny, but you still have one more cock to go" Nick said as he retrieved the 10 inch dildo to stuff into her tight pink pussy. Jenny looked back and saw the dildo was thinner but also curved with bumps and knots all over it.

"Reach back and spread that pussy babe" Nick instructed "by the way, clock is still ticking!"

Jenny reached back with both hands while bending forward more as well, and took Dan's cock all the way into her throat, gagging for what seemed like the 100th time today. Jenny could hear Nick snapping a picture of her devouring the cock in front of her while spreading her pussy as if inviting someone to fuck her.

Nick slowly inserted the dildo into her tight pussy, surprised at how tight she was "Wow! What a tight pussy, I knew it was a good idea to save it... just a little taste to help you get this all in there" Jenny could fee Nick push her ass cheeks apart and lick from the top of her asshole down around her pussy before he started fucking her snatch with his tongue. Nick finally was able to push the whole 10 inches of the curved dildo into her now dripping wet pussy.

"9 minutes in Jenny! Looks like someone wants it in the ass!" Yelled Nick.

Dan was struggling to hold off on cumming, doing everything he could to hold back.

"Nnnnn nnnnnnn!" Moaned Jenny around Dan's cock, responding to the time gone by. It was harder to concentrate on getting Dan off with Nick sliding the long curvy dildo in and out of her pussy - it felt like each little bump on the shaft hit the right spot inside of her!

"Aaaand ten minutes!" Nick exclaimed, with Dan flooding Jenny's mouth with cum only seconds later. Jenny swallowed what felt like a gallon of the thick hot cum, but she also had a lot dribbling down her chin and covering her luscious tits.

"OK now rules are rules Jenny.. Since you took more than 10 minutes, you need a dildo in your ass as well. Since we don't have anything to time you on, you'll keep them in until you cum, and no faking or I release pictures including your face!"

Jenny, defeated, just shook her head. She stayed on all fours and lowered her head down, pushing her ass up higher.

"No no no Jenny, you are going to do this yourself and we are going to watch and film. Get on your back on the couch, spread those legs wide, and put this dildo in your ass" Nick said as he handed her a smaller 6 inch black dildo that was thicker than the one in her dripping wet pussy.

Jenny didn't hesitate and took the dildo from him, trying to stick it in her virgin asshole - she had especially never thought about the idea of something being in her ass at the same time as her pussy!

She was struggling to insert it, so she slowly pulled the long knobby dildo out of her pussy to try to get some lubrication there. It felt like she was pulling it out for 5 minutes it was so long.

Nick made sure to get a great view of her slightly opened up pussy, slightly raw from the dildo fucking.

Jenny rubbed the head and sides of the black dildo between her pussy lips and began to insert it in her ass after it was coated in her pussy juice. She bit her lip as it inched in, sawing back and forth a few times to loosen up her own tight asshole. This alone got both men hard again, and they came closer to watch and jerk off.

With the anal dildo fully inserted, Jenny began pushing the 10 inch curved dildo back into her pussy. Once she got it buried all the way and tried to fuck herself with it, her anal dildo would start getting pushed out - she had to keep stopping to push it back in.

"Here, let me help you with that" Nick said, still jerking his cock towards her tits and face with his right hand but starting to fuck her ass with the dildo and his left hand.

Jenny never thought the sensation of two shafts alternating in and out of both of her holes would feel good at all, but the closer she got to orgasm, the harder she and Nick slammed the dildo's into her holes which caused her firm tits to shake and her breathing to increase towards orgasm.

Seeing this incredibly hot girl in front of him getting double shafted and almost cumming made Dan cum all over again, this time shooting ropes of her stomach and tits. The warm sensation felt good to Jenny, who was in a trance of almost cumming at this point.

"Oooohhhhhuuuuuuuhhhhh fuck my assssss!" She yelled, right on the edge of orgasm. Nick couldn't hold back any longer and shot his second load over her tits and face, with a decent amount hitting her open mouth and lips. He slammed the black dildo deep into Jenny's ass, finally pushing her over the edge and making her cum.

By the time Jenny came down from her high, Dan had shook hands with Nick confirming his debt was cleared. Nick had already taken Jenny's panties and instructed her to go home without them.

Still in a daze she put on her boyfriends shirt, which almost instantly became soaked with cum, showing her tits through the shirt. She pulled on her short shorts as well and stumbled back to her apartment next door to grab a shower.

When she got out of the shower she had a text waiting from Nick, with a picture attached. "Don't forget about our plan" - the picture was of the local college hotties website and feature her, although it showed no distinguishing features, from behind spreading her pussy, one dildo in her pussy, another of a dildo in her pussy and another in her ass, a few of her covered in cum with a black mark over her eyes so people wouldn't realize it's her... she hated to admit that it turned her on a bit, but was still very angry about her arrangement with Nick...

She couldn't dwell on it too long as she had a party to plan for Brooke.