The Jenna Arrangement Pt 20

FORWARD

Another chapter from Jenna's point of view, although this time I'm skipping the diary format.

ALL CHARACTERS ARE AT LEAST 18 YEARS OF AGE OR OLDER.

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Living with Tommy wasn't as difficult or strange as I thought it might be.

I'd declined his offer to stay with him before I left for the summer, but was glad now he'd made it, after what happened at my mother's.

Funny, I don't even call it "home" anymore. And that's kinda sad.

I've been trying to pitch in around here and earn my keep. It's not like he's a slob or anything, but I've tried to help out by cleaning up the place a bit for him while he's at work, and occasionally helping out in the kitchen.

I've also been working on my Only Fans page, trying to build up some customers. And a paycheck.

I feel more than a little guilty, with Tommy having to pay for everything. He says he doesn't mind, but still, I'm used to paying my own way.

I called Mr. Rivers a few days after moving in. He's an old friend of my dad's, and a lawyer. He's going to look into getting my trust fund out of my mother's grip and released to me early. That would be a HUGE help.

In the meantime, I've managed to get a few clients on OF, but it's slow going and I'm not seeing a real profit yet.

With only a small group of "fans," I've been trying to make it as personal for them as I can; replying to their messages, thanking them, chatting, flirting, and of course commenting on the dick pics I encouraged them to send.

A lot of my friends bemoaned the fact they would constantly get unsolicited dick pics from men on social media. I've had that happen more than once myself.

But Only Fans is different, of course, and I figured I'd just go ahead and encourage them since I'd probably get them anyway.

And although I wasn't charging yet for "dick ratings," (a pretty common practice on OF, guys paying you to look at their dicks and "rate" them,) most of the guys sending them to me also tipped me a few bucks.

While I used to have fun teasing guys into jerking off for me on Omegle, and seeing them hard and aroused for me would get me off, the longer I was with Tommy, the less interested I became in looking at random dicks.

Still, it's part of the game on Only Fans, and I did find it both amusing and flattering to see all the throbbing members in my inbox along with comments praising my looks and content.

So I'd write them back, sometimes even a short, personal video clip to thank them and praise their penis, even if I found it pretty average, which, really, most of them were.

Then, while going through my messages one afternoon while Tommy was at work, I found one from a man named Philip.

There was also a picture, but not of his dick, just his face. There was also a tip. His message, addressed to my OF alias, read as follows:

"Dear Robin,

Greetings from London. My name is Phillip. I first just wanted to say how lovely you are, and how happy I am to have found your Only Fans. Your pictures and video clips are stunning and arousing. I've been enjoying them very much, if you get my meaning.

You're not, perchance, of Irish descent, are you? I have some family in Ireland.

I know you've encouraged your fans to send dick pics, but I'm rather nervous to do so, being honest. I'm afraid you won't find it all that impressive.

You see, I was born with arthrogryposis. I won't bore you with all the long winded details, but essentially it affected my physical development growing up, making it very difficult for me to walk or even speak properly.

It also left me with a micro penis.

While therapy and surgeries have helped me greatly in the other areas, (I am now fully able to walk, albeit with a cane, and speak clearly,) there was no significant growth to my penis, even after hormone and testosterone shots.

My condition has of course made dating and finding a steady relationship rather difficult.

At thirty, I've resigned myself to probably remaining a virgin for life.

And so I turn to outlets such as this to help fulfill my fantasies.

I tell you all this, not for your sympathy or pity, but only so that you'll understand why I respectfully declined your request.

Lastly, I just wanted to say that I wish you well in your endeavors; I know it cannot be easy dealing with those who may judge or condemn you for choosing this particular form of employment. Just know that I respect what you do and appreciate the service you provide to someone such as myself. I am including a £20 tip to show my gratitude.

I do not expect you to reply on any regular basis of course. I'm sure you're a very busy young lady. But I am always open to a conversation should you ever wish to just chat. (And by chat, I do not mean sexting, I'm sure that's an additional charge LOL).

Regards,

Phillip."

I reread his message several times, then studied his picture. He was handsome enough, with short, black, tightly curled hair and a nicely maintained beard to match.

His smile looked shy, but he had a happy twinkle in his dark brown eyes.

I felt very moved, not just by the tip, but by his kind and polite words. Most of the messages I'd received so far from other customers pretty much consisted of, "Hey baby, you're so fucking hot, I'd fuck that tiny body so hard you'd love it," etc.

I started to write a reply, then paused. No, he deserved something a little more personal.

I was dressed in some basic denim shorts and a baggy tee shirt since I hadn't really been planning on taking any pics or videos. I quickly changed into a cute pink crop top that hung loose just below my boobs and a matching pair of panties.

I took a few minutes to collect my thoughts, then began recording the video.

"Hey, Phillp, I just wanted to thank you personally for your generosity and kind words. I'm so glad you enjoy my content, it really means a lot to me."

Instead of putting on a fake, seductress smile and voice, as I'd done in some of my other video replies, I was instead my genuine self.

"I understand and sympathize with your fears about sending me more revealing pics, but I wanted you to know that it truly doesn't matter to me. What matters is that you are turned on, enjoying yourself, aroused. Because that's my goal; to take away your stress and worries for a little while and just let you escape and release your tensions."

I paused for a moment, and then, on a whim, started pulling at my shirt, revealing little flashes of my under-boobs.

"It makes me happy to make you happy, Phillip," I continued, showing even more of my breasts while leaning back to also give him a better view of my panties. I'd made sure to pull them up a bit snug to outline my cleft.

I casually ran one hand over my mound as I looked directly into the camera. "It would also make me happy to see more of you, Phillip. You want to make me happy, right?" I purred, giving him a playful wink.

"I'll never make fun of you, Phillip," I said, more seriously now. "Your penis size doesn't matter to me. What matters is turning you on, helping you get off. That gets me off too, Phillip." I kept using his name to make it more personal, making sure he knew I was speaking directly to him.

"I'm not going to ask you to do something that would make you uncomfortable, "I finished, "but if you change your mind, I'd really love for you to show me, okay? Hope to see you again soon, and thank you so much."

I blew a kiss then hit stop. I rewatched my performance to make sure it came out okay, then sent it.

It was only about ten minutes before I got a response.

"Robin,

I'm blown away that you took the time to send such a personal and sexy reply.

I do indeed want to make you happy. So at your request I am sending you a picture. You may not be able to tell because of my size, but I'm fully aroused after watching your video. So know that while it's not much, it's all for you, my Mistress."

Below the message was the picture.

His penis was indeed small, but otherwise perfectly proportioned. He was uncut, which I'd seen before of course, and his foreskin was pulled back to reveal his tiny pink glans.

His pubes were neatly trimmed, and his balls were also proportional to his cock size.

All in all it looked very normal, except for the size. It was tough to tell from a picture, but if I had to guess, it was maybe two, two and a half inches.

I was a little confused by the "Mistress" thing. I'm certainly no Dominatrix, and hadn't so much as hinted at that kind of thing in any previous clips or comments.

I wondered if he was hinting that it was something he was into, something he desired from me.

I decided to gently feel him out on it in my reply:

"Thank you, Philip, for sending me that picture. Such a Good Boy. 😉

I think your cock is beautiful. I know about having body issues. I mean, just look at my tits. They're not exactly massive either. But I've grown to accept them, and be proud of my body. I hope you can, too.

So I'm your Mistress now? Does that mean you'll do everything I say? 😈"

His reply came quickly:

"Sorry, the Mistress thing just sort of slipped in there at the end. I do enjoy a bit of light domination, although for obvious reasons I'm not really into humiliation. Do you mind? You don't have to of course. But I would gladly submit to you, my Mistress.

Oh, and I think your breasts are perfect."

He was so sweet. I didn't know much about domination or being a Mistress, only a few things I'd seen in some random porn, most of which didn't appeal to me.

But it appeared he didn't want to be humiliated or insulted, which I was glad for because that just wasn't my style.

But I could be a "take charge* kind of girl for him, if that's what he wanted. I most certainly could have a little fun with it.

I wrote back immediately.

"I don't mind at all. As long as you're a Good Boy for me. Your Mistress would like to video chat with you. I want to watch you get off to me."

There was only a short delay before his answer.

"I'm sorry, my Mistress, but I don't have any extra funds to spend on that sort of thing right now. But if you let me know your rates, I can plan for another time."

He assumed I was going to charge him for it. I know most of the women on OF did. I hadn't really thought about what I'd charge for that kind of thing, or even if it would be something I'd offer on a regular basis.

But I was bored, more than a bit horny at this point, and Tommy wouldn't be home for a few hours. And Phillip was just so nice. I decided I wanted to give him a treat.

"This one is on me," I replied. "When I want money for something, I'll tell you. I'm sending you my Snapchat. Be a good pet and come find me there. Don't keep me waiting."

I attached the link and sent the message.

I received his request at Snapchat within a few minutes. Moments later, we were face to face on video chat.

"H,h,hello, Mistress," he stammered.

"Hello, my pet. You're late," I teased, giving him a sexy little pout.

"I'm s,s,sorry, Mistress." I wasn't sure if his stutter was due to his condition, or if he was simply extremely nervous. I could see his blush even through his olive skinned complexion, and his eyes refused to look at me directly.

"Phillip," I said calmly, "look at me."

Slowly his eyes moved up. It's almost impossible to make direct eye contact on a video chat of course, but I could tell he was now looking at me on his screen.

"Relax," I said. "Take a deep breath. Don't be afraid. I want you to enjoy yourself, okay?"

"Y,yes, Mistress," he nodded, the tension leaving his face. He gave me an adorable, still shy smile.

"Good Boy," I said softly. His smile widened at that.

"Now," I began, adding a playful, seductive tone to my voice, "are you still hard for me, my pet?"

"Yes, Mistress."

"Good Boy," I purred. "Have you been touching yourself for me?"

His blush deepened. "Y,yes Mistress."

I gave him my best sexy grin. "Very good. Show me."

His eyes widened and he gulped nervously, but his camera moved lower until I was looking at his penis. It was hard and twitching, and he was stroking it slowly, using only his thumb and forefinger, working his foreskin back and forth over the tip, already glistening with precum.

"Mmmm," I sighed, "such an adorable little treat. Now don't go too fast, pet, I don't want you popping off before I give you permission to."

He didn't reply, but let go of his cock. It pulsed and jumped as if frustrated at the loss of attention.

Being on our phones made it awkward, but I wanted to be able to see more of him than just his dick while we did this.

"Phillip," I asked, breaking character only a little, "is there some way you can place your phone down so I can see all of you? I wanna see your handsome face while you jerk off for me."

We both took a few moments to arrange our cameras so we could be hands free and still see each other. I made a mental note that I'd need some kind of stand if I was going to do this more often.

Once settled, I turned again to face him on the screen. I was lounging back on the bed; he was seated in an office chair, his pants down around his ankles.

"You still have your shirt on, pet," I said, getting back into my seductress voice. "Take it off. I want to see all of you."

He silently obeyed, slowly unbuttoning it and tossing it aside. His chest was hairless, and he had a bit of what is popularly called that "dad bod" gut, but overall he was in decent shape. His legs looked slightly crooked, and his feet twisted at a weird angle. I suppose this was from his condition.

"Can you move your chair just a little closer, pet? I wanna see your handsome face better."

He awkwardly rolled the chair forward until I told him to stop. I could now see his facial expressions better while still being able to see his cock.

"Good, that's perfect." I got on my hands and knees on the bed, leaning in so my face was close to the camera, but also offering him a tantalizing view down my loose hanging crop top.

"I want you to touch yourself for me, pet," I whispered, reaching up with one hand to cup my breast under my shirt. "Do it now."

"Yes, Mistress." His hand found his cock and again he began his two fingered stroke.

I tweaked my nipple, feeling it stiffen, sending a dull ache through my abdomen. "I'm getting hot for you, pet," I moaned. "Do you want to see them?"

He nodded furiously, then remembered to speak. "Oh yes, Mistress. Please?"

I sat up, then slowly lifted my shirt, offering just a flash of my boobs and hard nipples before pulling it back down. I continued to tease them under the shirt, running my hand back and forth between them, moaning softly as I did so.

His pace quickened and I could see him shaking with excitement.

"Now, now," I chided him playfully, "did I tell you to go faster?"

He stopped his movements. "Sorry, Mistress."

I opened my mouth to speak, then hesitated. I'd played with some guys on Omegle before, but really never had much interaction other than teasing them visually while they jerked off.

I'd also of course had several video sexting sessions with Tommy. But those were different. We both seemed to instinctively know what the other wanted.

This was different. I didn't know Phillip at all. All I really knew was he seemed to enjoy me taking charge. But I didn't truly know what he wanted, or what scenario would get him off the best.

I decided the best approach was to just ask. "Phillip, if I were there with you, right now, and willing to please you in any way you wanted, what would you want?"

He was silent, his face again a bright red.

"Don't be shy, pet. Tell your Mistress what you want."

"I... w,w,would love a... b,b,blowjob." His embarrassment was so cute.

"Of course, my pet," I smiled. Again I took a moment to consider how to proceed. Then an idea hit me.

"Do you have any lube, pet?"

"Yes, Mistress." He reached over somewhere offscreen and came back with the bottle.

"Good. Now lube yourself up nice and slippery. This is gonna get messy," I winked.

I again positioned myself so that I was leaning in towards the camera, my face close to the screen. I considered for a moment getting the realistic dildo Michelle had gotten me as a prop, but I didn't want to make him feel self conscious since it was much larger than his penis. Instead, I decided to try something else.

"Now, I want you to do exactly as I say, and follow my every movement. I'm going to suck your cock, pet. If I use my tongue, you use a finger. When I use my lips, I want you to stroke in exact time with my movements. No faster. Do you understand?"

He nodded excitedly. "Yes, Mistress."

I held my thumb to my lips and, staring directly at him, stuck out my tongue, licking and twirling it around the tip.

He followed my movements immediately, running a finger around the tip of his glans. When I flicked my tongue along my fingernail, he got the hint and rubbed his finger just under his head along that sensitive spot.

"Good boy," I encouraged, "now cup your balls with your other hand and play with them however you feel comfortable."

Phillip obeyed, his eyes rolling back as he groaned in pleasure from the extra stimulation.

Once I was sure he was again focused on me, I began to suck my thumb. Slowly, starting on just the tip, then suddenly taking it all in my mouth.

He gasped loudly as his hand followed suit, forming a fist over his petite cock and sliding it down along his slim shaft, engulfing it completely.

Knowing he didn't have the length to jerk it the way an average man would, I moved my mouth up and down only slightly along my thumb, drawing my cheeks in as I sucked it tightly.

Again he mimicked me, his hand rocking over his cock while squeezing it with his fist.

Keeping my thumb in my mouth, I smiled widely, allowing the saliva that had built up to drip down over my fist.

Popping it out with a wet smack, I again addressed him. "I'm going to really suck you now, pet. Follow along as best you can, in whatever way works best for you. Only make sure you tell me when you're about to cum."

Then I began my "blowjob" in earnest, deep throating my thumb (which is, to say, not very deep at all of course) up and down, moaning loudly and allowing myself to drool even more on each suck.

Phillip was shaking in his chair, now using his thumb and two fingers to stroke his heavily lubed cock, his other hand still gripping his balls even tighter.

Despite his obvious excited state, he managed to still pay attention to me, slowing when I slowed, speeding back up as I did.

His groans increased in steadiness and volume, and I knew it wouldn't be long now.

"I'm...close, Mistress, I'm going to..."

"STOP!" I commanded, pulling my thumb from my mouth. "Hands off!"

Phillip looked dismayed, but obeyed. His tiny member twitched wildly. Small as it was, I could tell it was incredibly swollen with arousal just waiting to burst free, kept back only by what must have been a supreme effort of willpower.

"Please, Mistress, please." His head bowed, and the desperation in his voice was almost heartbreaking.

"Phillip," I said sternly, "look at me. Look at me, my pet."

Slowly, he raised his head. His eyes pleaded with me silently.

I relaxed my face, giving him my warmest, caring smile. "Good Boy. Now...cum for me."

I plunged my thumb back into my mouth and sucked it as hard as I could.

Phillip grabbed his still pulsing member and seconds later his cum blasted from him in surprisingly long streams to fall to the floor below him as he howled in pleasure, his body rocking so wildly I was afraid he may tip over his chair.

I spoke softly, sweetly coaxing him through as his body continued to tremble, then slowly relax as his orgasm subsided. "That's my Good Boy, my sweet pet, my good, sweet boy..."