Jacking Off is Hard To Do Ch. 1

"Shit! I'm going to be late... I can't believe I left the directions at home!" I spat out at myself in frustration. I'd been driving around this area for about 30 minutes now. I should have been there by now - her instructions were VERY specific in her email. I could have driven home, got the directions, and been there by now, I thought to myself.

"You moron..." I said with a short sigh. Reality was that I got way to excited when I got THE email from her. I mean, you don't just proposition someone in a chat room, and expect her to say "sure, how about tomorrow night, is 8 ok for you?" Well, some might, but I don't.

* * * * * * * * * * * *

15 stressed filled minutes later:

"Cliff... isn't it?" said the young lady that answered the door.

"Yeah... Moner?" I responded a bit confused. We were going by our chat room names... but this did not look at all like the woman I jerked my meat off too last night - on camera no less!

"No" she giggled, "that's my aunt."

I instantly blushed - I didn't know what to say...

"I'm exxxtacy, by the way," she said as she extended her hand and gestured me into the house.

"..You... you were in the chat room too, weren't you?" I stammered out, as what she just told me began to sink in.

"Yeah." she replied, then re-gestured for me to enter.

With another giggle, she stated the obvious; "You were telling the truth last night, you've never done anything like this before, have you?"

I slowly shook my head no, and entered the house.

She quickly took my hand and led me up the stairs as she yelled out "He's here", pause, "at least physically!"

"As long as he can get it hard, that's all that matters" was the reply.

* * * * * * * * * * * *

The night before (Thursday), 1:42am:

[MightyMoner] One condition though...

[CliffClaven] What, I have to go into cardiac arrest before I get to touch you!

[MightyMoner] you're right, you ARE a smart ass! I'm being serious.

[MightyMoner] are you serious about this or not?

It was at this point during our first chat session that this truly seemed like something "might" happen - emphasis on might.

[CliffClaven] ok. I'm sorry. I'm just new to this, and to be quite honest

[CliffClaven] I don't know how to act - I mean you're HOT! And well, I just...

[CliffClaven] can't believe this is happening.

[MightyMoner] Honey, I won't lie to you - Your not the handsomest guy around, but when you

[MightyMoner] said what your interests were, and then where you were from...

* * * * * * * * * * * *

Earlier Thursday night, 1:04am:

When I entered the first chat room, I was asked to message the room operator, exxxtacy, my kinks and my hang-ups. The automated message said "be honest if you want to get the password for the room where the real fun is..."

I almost left, but then I decided to give it a shot. I messaged her "kinks: large nipples (breast size doesn't matter). Large lips and clits. Mutual masturbation. Oral. Hang-ups: men (I'm straight). Too much make up on a woman"

I waited in the first room for a while, watching the text go by from the hundred or so other users in there - mostly guys. Many bitching about wanting the password to the other room, or claiming there was no other room, etc... After about five minutes of toying around on the PC, I left the room.

I was about to shut down the chat program and go jack off to some porn I downloaded earlier when I got a private message from MightyMoner: "send me a pic, and I'll do the same. You must be holding something with a recent date on it - clothing optional."

"Hmmm" I thought. A bit demanding, but I'm game. I got yesterday's newspaper (too lazy to pick up today's from the end of the driveway when I got home). I folded it so the front page was visible, and I positioned it right below my chin. I snapped a couple shots with my trusty web cam, and then I sent them to Ms. MightyMoner. She then sent me a couple pics, both clothed - holding TODAY's paper.

[MightyMoner] Too lazy to get the paper? hehe

[CliffClaven] yeah...

[MightyMoner] Ok. I'm interested. are you?

[CliffClaven] Yeah!

[MightyMoner] Send me a pic of your cock - hard!

[CliffClaven] I will send you one of my hard nipples - since you say you like those ;o)

I pulled my cock and balls out through the opening in my boxers, and began to stroke - I love masturbating almost as much as much as I love sucking cunt. The routine was familiar, and I was nearly erect when her picture came across. "Wow!" I said as I stepped up the pace with my strok'n hand. The picture was quite large, and the quality was superb!

It was a shot of her breasts taken from one side of her body. I could see both tits, but one filled the frame more then the other. Her nipples were quite large! She had a ruler held up to the one closest - it measured just over three fourths of an inch long, and she wasn't pulling on it either! Not only that, It looked to be about a half inch in diameter!

I quickly took a couple shoots of my cock, one from the side with my hand around the base, leaving about two thirds of it exposed. Then one of the head, showing off the slit at the top with just a bit of moisture coming out.

I continued to stroke with one hand, keeping it hard as I sent the pictures, and looked at the one of her beautiful breasts.

[CliffClaven] amazing... can I suck on them?

[MightyMoner] yummm - is that pre-cum? You know what this girl likes!

[MightyMoner] Well, let's just say I wanna watch you jack off...

[CliffClaven] I wish I could be sucking those at the same time. :O)~

[CliffClaven] and yes, I'm ready, willing, and [let me check] yep... able!

[MightyMoner] Ok, I'm connected - waiting for you to join.

I established the connection, entered the password, and boom! There she was - Nipples like rocks through her white T-shirt. She looked to be about a 36B. I was amazed at the clarity and the high frame rate we were getting.

She waved. I waved back.

[MightyMoner] I'm really horny - let's both get undressed right away.

[CliffClaven] Ok - luv your nips ;o)

[MightyMoner] like your bulge!

We both undressed - which requires more talent then one might think since it involved three tasks, 1) getting an eyeful of the other. 2) Staying in the frame so the other can see you, and last, but certainly not least, 3) Getting undressed.

[CliffClaven] Damn you're hot.

[MightyMoner] Well, you didn't lie about your cock.

She shook her titties in the camera for me... god were they nice.

In turn, I put my cock head close to the lens and slowly stroked from the base up to the underside of my head, keeping pressure on my urethra the whole time. Once I got to the top, a small amount of liquid popped out of my tip. Just enough to form a drip, but not enough to escape...

[MightyMoner] Oh god... I can see your ready. Me too. Let's do it.. No more talk. Just j/o!

[CliffClaven] Close up of cock and cunt while we do it, ok?

[MightyMoner] go!

We both repositioned our cameras and got comfortable. I placed mine toward the edge of my desk, focused on my throbbing cock. This way I could get in one of my favorite positions to masturbate - reclining back in my leather office chair, legs spread, one over each arm of the chair. This would give her the best view, and me the most freedom.

She moved the camera to what looked like a coffee table, and sat in a big overstuffed chair. She too spread her legs and placed each over an arm - I gasped when she focused the camera right on her creamy slit. I couldn't believe my eyes - she was completely, 100% shaved!

"Oh fuck!" I thought and grabbed my cock with my left hand and started stroking.

I made sure to point my cock head toward the camera on each up-stroke. I grabbed my sack with my right hand, and started to gently squeeze and caress my nuts...

Not only was she shaven, but her lips were huge! They were shaped just the way I liked them: normal toward the top, meaty and long in the middle, then tapered off toward her opening. She immediately spread her lips with one hand, and to my ecstatic joy out popped her clit! It was big! I let out a moan and stroked with renewed vigor. My cock was HARD. The pre-cum was flowing pretty good at this point, it was actually starting to lube my strokes a bit.

She was rubbing her nubbin now, with two fingers. Pushing, and grinding it. Her hips began to move up and down in a rhythmic motion. I brought my right hand up to my mouth and licked it, quickly returning it to my balls. Then the left hand, this time I put a copious amount of saliva on it, returning it to my cock. I stroked down it slowly to get it well lubed.

I began to fuck my fist as if it were a tight pussy, HER pussy - lifting my ass off the chair a bit with each thrust. Her attention was still on her clit, her pace quickening as she stroked it BETWEEN two fingers! All of a sudden, those two fingers dived right into her hole! As they were engulfed by her pussy, the other hand quickly moved up and under it to give attention to her clit. With each thrust of her hand, her fingers seemed to penetrate further into her vagina, until all I could see were her outer two fingers and the knuckles of the middle two.

This was becoming too much for me. My hand left my sack, and began its familiar journey to my asshole. I pushed on the opening with the tip of my index finger - a lot of resistance. I Moaned. Then began to push, until I had it in to the first knuckle. I laid my head back, watching the screen, feeling the build up as I stroked the full length of my cock, over and over.

She pulled her hand from her cunt. Repositioned it underneath her thigh, and slowly inserted one finger into her asshole, and two others into her wet opening. She then began pulling and twisting on her clit with the other hand, placing it between her thumb and forefinger.

Balls tightened. Asshole tightened around my finger. All my attention was on the underside of my cockhead. A deep, long, low moan escaped my mouth. "ahhhhggg yes!" I said gasping as the first load of sperm and seamen traveled up my urethra and exploded out of the slit in the head of my cock - landing at the top of my screen. I quickly moved my body forward in an attempt to point my cock lower, in the process forcing my finger deeper in my ass - another long grunt as more cum burst out of me and on to the keyboard!

Seeing this sent her into her own orgasm. She furiously pulled, squeezed, and twisted her fully engorged clit. All the while fucking her ass and cunt with her fingers. The first spasm hit her and she froze. My balls tightened again, and for the third time in just a few seconds, I spewed a load of jizm. Her quim seemed to visibly tighten around her fingers. With a bit of effort she pulled her fingers out, she arched her back, raising her pelvis, making her ass completely rise off the chair! My god, what strong legs she must have, I thought to myself.

She hadn't stopped tugged and rubbing her clit. Another spasm, the muscles in her thighs tensing and becoming even more defined. Then she suddenly dropped into the chair like a wet noodle. Her fingers vigorously rubbing the center of her universe, attempting to coax another orgasm from its depths. She tensed, the muscles in her ass visibly tensing, her pussy rubbing became eradicate, her body convulsing... In one quick swoop her legs came off the arms of the chair and clenched tightly shut, her hand trapped between the two...

I smiled still holding my rapidly shrinking cock in my hand... the cum on the monitor heating up and quickly running down my screen.

* * * * * * * * * * * *

Friday 8:05pm

"So you watched?" I queried, a bit in disbelief, but mostly I was turned on by the tale.

"Yeah. [giggle] I got to clean up after the camera was turned off..." Chrissy responded.

"She enjoys licking auntie clean... As I recall you were quite wet yourself dear", Mona added.

"Wow..." was all I could say. Images quickly filled my head of the hot 30-something woman and her niece, who couldn't be older then 22, engaged in a 69... my already half erect member twitched at the naughty thought.

"You understand the ground rules?" Mona asked.

"Yes." I stated.

"Repeat them," she said in a curt and demanding tone.

"Ok. I cannot leave the chair at ANY time. I cannot make physical contact with either of you. I cannot ask, beg, or otherwise plead with either of you to make contact with me. If you choose too, it is of your own accord, and you are in complete control." I repeated as if I were reading a legal statement at the bottom of a credit card agreement.

"Mona... why can't we just fuck him," Chrissy said half jokingly.

They both smiled, and Mona walked over to Chrissy, wrapped one arm around her waist and then leaned in for a short but highly erotic French kiss. My eyes kept darting between the kissing, Mona's delectable nipples poking through her blouse, and Chrissy's fantastic body... I was fully erect by now, and very uncomfortable in my jeans.

Mona's hand moved to her niece's tiny ass, clad in a super tight spandex like material. I was pretty sure she wasn't wearing any panties... the material was pulled up in her crotch, clearly outlining her mound, and the cleft that housed her pussy. Mona's other hand went for a breast, she abruptly broke the kiss and twisted and pulled one of Chrissy's nipple!

"Ouch! What was that for?" Chrissy hissed.

Mona responded in a cheerful voice, "You know we can't fuck him until we know he is clean... that will take some time... Until then we can make use of him in other ways."

Sounds like they have played this game before I thought to myself. I wondered how many other lucky guys have been in my position.

They both left the room. I took off my clothes as I was instructed to. I put on the white silk underwear - they were quite small and tight, and my cock was already hard from watching those two play. Almost half of my cock ended up sticking up and out the top. A bit of pre-cum forming in anticipation of the upcoming events.

I entered the room, there were three of the over stuffed chairs in it. Chrissy and Mona were each seated in one.

"hehe, I told you those would be too small for him" chided Chrissy.

Both were completely nude. My eyes locked first on Mona's nipples, which she was idly playing with, and Chrissy's breasts, which were smooth, young and firm. She was about a 36C, but sadly, she didn't have her aunt's elongated nipples. She sat in the chair sideways, her back against one arm, and closed legs over the other. With her long hair hanging down - she was breathtaking. I couldn't see between either of there gorgeous legs, but I could make out a faint, but none the less intoxicating, scent that is exclusive to aroused women.

Chrissy gasped at the sight of my cock, and moved her skinny hand between her legs. From my position, I could just see her hand moving up and down, quite rapidly. She bit down on her lower lip and tightly shut her eyes. In no time she let out a "oh yeah.. gonna... gonna... Yeassssh." in a high-pitched voice. She removed her hand from her pussy, moved it to her mouth, sucked on one then the other finger, looked at me and smiled.

"Don't mind Chrissy, she can cum on command," Mona stated in a raspy voice. Not once removing her stare from my mostly exposed crotch, she continued to tug and twist her super long nipples. "Don't mind her?" I thought to myself, "I almost came with her!"

Now that Chrissy's short matinee was over, I took a deep breath and sat down in the remaining chair. I spread my legs, put one over each arm of the chair... the underwear was quite confining. In this position, the material was putting a lot of pressure on my already erect cock and balls. As I tried to reposition myself for maximum comfort, the silky material pulled up my ass, and was applying pressure on my anus. It was uncomfortable, and pleasing at the same time.

"hhmmm... yess.. I like what I see," Mona purred as she tugged and twisted on a nipple with one hand, and buried her other in her, still out of sight, crotch.

To Be Continued...

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Comments are always welcome and strongly encouraged. I am looking for constructive criticism, as well as Women to exchange stories, fantasies, or just to ask / answer questions you might not ask someone you know.