Bailey s BrotherChapter 11 Bailey Caught Red Handed
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Massage Chronicles - Milked And Pleasured By Bailey Part One free porn video
I first spotted the ads for Kate’s place a few weeks earlier. A quick survey of local reviews for her yielded quite mixed but generally negative results. There was something in one of the reviews that led me to believe that the reviewer was wrong. I couldn’t pin it down so I PM’d the reviewer. He told me that she was cute and young, but very rude to him and that his massage was rushed and disjointed.
This was a time when I was still new to erotic massage, and also quite shy. Still, I knew from experience that it was also very much about how you treat people. Especially when it came to erotic massage. It is a superbly intimate experience, where the connection with each other is extremely important.
The location was somewhat out of the way, but I called up Kate and made an appointment with Bailey.
I was taken aback by how young Bailey was when I walked in the door. Bailey was at the oldest in her very early twenties, which was probably close to or younger than my daughter. What I am doing here? I know for some guys, that is a turn on, but honestly, I was feeling apprehensive.
Bailey was about five-foot-seven with medium length natural looking eyelashes and cutting blue-green eyes. Shoulder length straight blonde hair framed her perfect completion, supple lips, and smallish nose. It looked like her hair was done that day, in an expensive salon. She had large breasts, at least a D cup, but a slim figure, and still the narrow hips and figure of a younger lady. She was put together like a fashion model. Striking was an understatement. Mouthwatering.
“Hey Zach, come in. Just put your shoes there.”
When I stood up, I was immediately up close with Bailey's great looks and mouthwatering breasts. I looked away quickly so as not to appear to be some kind of pervert.
Still, Bailey was a nice host. “Would you like a shower?”
"Yes I should, I am just coming from work"
Why wouldn’t everyone have a shower before the massage?
I relaxed with Bailey’s kind, caring demeanor, closed the door to the washroom and hopped into the shower.
Just as I turned on the tap and began to wet myself, I realized that there was no towel. That’s kind of awkward. I looked around the spartan bathroom to see nothing.
All of a sudden Bailey pushed the door open. “Here’s a towel.”
There I was, naked in a glass shower, sporting a semi-erect excited cock. Embarrassing.
“Um, thanks!” She wasn’t fazed at all my nudity and actually paused for a moment to size me up, before leaving. She didn’t really close the door, either.
I could see the silhouette of the bedding being adjusted on the massage table, through the water splashing on my face and semi-ajar door.
Was she watching me shower? Damn. I started getting uncomfortably erect.
“Just get on the table when you are ready, Zach,” Bailey peeked in and smiled kindly as I finished my shower.
I guess she’s seen me in all my glory. I rubbed and patted myself dry.
When I walked out of the bathroom to the massage table I noticed that there was no draping.
Hmm? What do I use, did she forget?
I grabbed the not very large damp towel from the shower and used it to cover my butt, wriggling my face into the head hole on the massage table.
Almost as soon as I was face down, a quiet knock on the door, Bailey’s soft but confident voice, “Ready, Zach?”
“Umm hmmm,” I mumbled through the hole in the table.
As I answered, Bailey snapped the wet towel from my body, leaving me 100% nude. The air cooled my slightly dampened body.
She isn't shy, that's for sure. There was kind of an air of confidence, like that of an older woman. I found it both attractive and a little uncomfortable, as my penis decided that it liked Bailey!
“What type of massage do you like, Zach?”
Sensual, I wanted to say. Afraid to say what I really wanted I stated a half-truth instead. “I work out a lot so usually get a deeper massage.”
“Okay sure, just let me know, if it’s too much, okay?”
“Yeah, no problem I will.” My voice sounded like I was chewing on a tissue, speaking through the hole in the massage table.
Bailey was quiet and efficient. She oiled me up and began. Her massage pressure was really unexpectedly good.
She worked all the muscles of my body professionally, without any sensual touching at all.
From my youth, I was still quiet and shy, a trait that lingered sometimes when I was uncomfortable. It was nice in a way that Bailey was not too chatty. Closing my eyes, and relaxing my breathing, I started to really get into her massage.
It was great and relaxing but after a while, I yearned for something more erotic.
“How’s the pressure?” she asked in a genuine way.
“Great, you are very good,” I complimented her, but it was true. At lease tickle me somewhere!
The back massage continued for quite a while. I was too shy to ask for something more; still, my muscles were putty in her hands.
“Do you want to turn over?” she asked, without a hint of anything more.
“Yeah, sure,” I guess you are going to see how much my cock likes this now!
I rolled onto my back, and Bailey tucked a pillow under my head.
She was really very hard to read. Was she going to do anything erotic at all?
She oiled up my chest and pectoral muscles; from over my head, she pressed down. As she did, the fabric from her top and bra pressed into my forehead.
Fuck, she’s got really big firm tits!
She leaned into me. Her chest was right over my face. Her strokes were going over my abs, but not going close enough to my groin for my liking. I pressed my tummy up into her strokes then relaxed. Go lower please, hun!
I don’t know if it was instinctive or wishful thinking, but as she pressed down, I tightened my abs again. Whether she planned it or it was a response to my animated body movements, her hands massaged delightfully lower.
Fuck yes!
There was expertise in her touch. She massaged firmly symmetrically over my abs, then parted her hands massaging down either side of my cock and balls then joining them together as her hands finished between my thighs.
Oh, fuck me! Mmmmm!
I moaned but Bailey’s blouse covered large breasts were pressing over my face. I’m sure I sounded a little funny with that muffled moan.
She spilled more oil on my groin while moving to the side of the massage table. I was about to enter heaven!
Her hands kneaded into my testicles with a purpose. It was not a light sensual touch, rather it was as if she was massaging my balls to produce as much sperm as they could. Any more pressure and it might have been painful, but it wasn’t. She worked my balls like she was kneading the baking dough into some sort of layered pastry. My cock thickened heavily, rapidly. I loved having my balls massaged, and Bailey was doing it perfectly.
How does a girl this young know how to do this? Fuck, she's milking my balls!
She grabbed one testicle in each hand and squeezed gently.
My cock was twitching, with every squeeze and tug on my balls.
"Mmmm," I gasped quietly. Fuck yes, use my balls, get them ready!
I knew that the hour of my massage time was concluding soon, I worried for a moment.
Oblivious of my worry, Bailey wrapped her two oil soaked hands around my shaft and stroked up all the way up my oil coated cockshaft, then down again.
I pushed into her downstroke. That's it, sweetie, milk it, milk my cock!
It was really slow; her grip was extremely firm, just like with my balls.
Firmly slowly up then down. Stopping just at the ridge in my cock.
Controlling, she's fucking controlling my cock!
I looked up to see it glistening and huge in her small hands. Bailey’s face was pretty but very serious. She seemed to be concentrating.
The pressure with which she stroked me was exacting. It was way too slow to make me cum, but it was wonderful, like edging.
YES!
Somehow intuitively though she was changing the pressure of her grip. It's like she knew what would make me cum, and what wouldn't.
My cock began to sensitize and I humped into her hands. Faster, faster, honey.
But Bailey kept on stroking slowly. Slowly but it was feeling better each stroke.
“Ohh!” I sighed, "That’s so nice!"
I looked up again to see my cock in Bailey's hands, It's like her slow strokes were willing my cock to such a gigantic oil coated monster. Damn, she’s gonna make me cum like this!
The tingly wonderful feeling of my climax was building in each slow stroke. "Mmmmm." The burn and my climax closed on the point of no return. It was coming but she was controlling it.
“Ugh shit!” I moaned as her slow strokes willed the cum to rise in my cock. So fucking slow. Bailey, you're killing me!
Previous massage girls would stroke faster and faster. Bailey didn’t change her methodical pace. Her grip was so firm on my rock-hard cock, there was no way I could stop myself from cumming.
Oh fuck god, yes!
I closed my eyes and fucked my cock into this young lady’s hands and felt the thick wads of cum land on my chest and stomach. Ropes of cum flung everywhere.
"Ohhh yes, mmmmmm!"
Bailey’s strokes urged every drop of cum out of me and slowed adjusting perfectly to the increased sensitivity in my cock.
Slower, then slower still she stroked. Lighter, more carefully, yet she was still urging more cum out of me. Her other hand pressed my balls. Her palm ground back and forth rolling my testicles against my thighs.
How the fuck did she learn this?
Bailey stared straight at my cock as a long slow drool of sperm pushed out of my gaping cum hole.
She's draining me of cum!
She cradled my shaft very caringly for a moment before going to the bathroom to warm up a washcloth. After washing the cum off my chest with the hot moist towel, I thought that I would be finished, and have to leave.
Instead, Bailey moved to the foot of the table and massaged each of my legs, feet and finished by lightly massaging my cock and kneading my balls one more time.
So, perfect.
"Do you want to have a shower again, Zach?"
"Yes, I for sure should clean up."
After showering I somehow felt apprehensive again. Bailey was so good but unseemly young to have both the expertise and for me to be massaged by her. Nervousness crept in as we said a pleasant goodbye.
"You should come back again. Soon, if you can," she asked in a sensuous, inviting way.
"That was amazing," I complimented her. Soon?
Turns out she was heading back to school to do her bachelor's, in Ontario.
I was way too nervous and shy at the time, fumbling for words or the right thing to say. We gave each other a friendly hug.
“Come back again, Zach, you’re sweet,” she whispered in my ear. Something about the way she said it, gave me a feeling that she was a girl that liked being in control.
Say something, you idiot. I couldn’t find any smart-alecky or charming things to say, so I just smiled stupidly as I left.
I did take Bailey up on the offer to come back, and it was one of my most memorable massages ever.
*
I didn’t forget about Bailey at all. She was the center of many sexy dreams and masturbation fantasies. Time went by too quickly, though. Work got busy and I did not make any appointments with Bailey. It finally looked like I could take off from work on a few days, and I called up Kate.
She didn't answer my phone call. Instead, Kate texted back: Sorry Zach, Bailey’s gone.
Damn. Okay, thanks anyway. I guessed that she had gone back out of province to school again. Can you get her to text me or can you text me when she's back?
About two weeks later out of the blue, I received a text from Kate - Bailey’s back!”
Cool, can I make an appointment? I was ecstatic and suddenly hard at least for a moment.
Yeah, can I give her your number to text you?
Absolutely
Later that day I got a text from Bailey. Hey Zach, do you want to come in for a massage?
Yes, I do, for sure, I thought you had gone back to school. I was smiling from the inside out as I waited for the reply.
Yeah, I am getting ready for school, but am back in town this week. Can you come on Friday at 5?
Friday, shit that’s a long time. Four days. I really wanted to see her right away. I was mulling over in my head a plan to get off work that day early so that I could see Bailey, as I formulated a response. I had to agree if I wanted to see her, didn't I?
Yeah, okay for sure.
Be ready for me, k?
Ready yeah sure. I didn’t understand what she meant but I agreed.
I mean it
What the hell? I was puzzled now by her text. This was a bit over the top. Was she being funny? Controlling? Or was it darker, a fatal attraction kind of thing?
Ready?
No messing around.
I paused before it clicked. She doesn’t want me jacking off or fucking. Holy crap. My cock hardened enough to nearly tear my work jeans.
Yeah, I can do that. My balls pulled up and cock throbbed as I texted her back.
No jo, right?
I didn't answer. I didn't know what to text back.
No effin neither, k?
Can you handle?
Shit shit shit, where did this girl learn this stuff? The blood rushed to my groin. I could barely think enough to finally text a response.
Yeah, I can. Jezzus! I craved her hands all over my body that instant.
I want u full k?
She wants me full? Full of cum!
understand?
Shit fuck shit, I ached in hardness; how could I possibly wait until Friday? My cock begged for release that instant. She wants me full of cum? Jeeezzz!
Yes, I understand. I liked it, it didn't really matter whether she had ulterior motives.
Great, see you on Friday!
It took me hours to calm down from Bailey's texts and subsequent sex-filled craze. I thought about Bailey on the commute home and most of the evening. I had even more dreams about her that night.
Tuesday
The next morning I rolled around and out of bed, half-awake with a hard-on like a teenager. After showering early, and having breakfast, I was thrilled with the sexual energy surging through me. I set the lubricant out and thought about stroking. Just before I did, I checked my email, then phone for messages.
There was one from Bailey. For some reason, I thought she was canceling our appointment but I clicked on it.
See you Friday
For some reason, I thought this was a belated echo of a message. It did look like the message was sent late last night. I responded anyway.
Yep will see you Friday I just sat there staring at the phone, wondering if she'd respond. Just as I set the phone down there was a 'ping.'
Did you remember?
Yes. I almost broke my promise, thinking of the lube on the bathroom counter.
U full?
YES!
Smiley face. - I look forward to seeing you Friday.
The workday went on with me trying to avoid thinking about Bailey, except every time my cock got hard, I couldn’t avoid but think of her. I checked my phone regularly all day, and into the night. I wanted to see a text from Bailey but there was none.
Wednesday
I woke up extra early that morning and wrestled with a constant erection in the shower. It was easily an hour earlier than my normal workday start. I checked my messages.
Hey, Zach u awake.
How did she even know I got up this early? I wanted to open a window and see if she was out there watching me. I couldn't risk getting caught by my wife or other family members with this kind of text exchange. It was crazy. I was turned on by this. By Bailey. I wasn't going to let this go.
Yes awake
U thinking about me
Yes
U hard?
Yes. I was painfully hard, damn.
U mess around?
No
U full?
YES, I was absolutely ready to explode. How was I supposed to wait until Friday?
Good -smiley face, see you Friday
Like a good horny boy, my cock soldiered to attention and would not go down through the whole morning. Even the commute to work I was erect the whole way. In some respects, it felt nice, in others a little frustrating.
It took about twenty minutes at work before the distractions helped calmed my cock down enough to be not bothersome.
Late in the day, just before the commute home, I fielded a call from a long-distance number.
This wasn’t unusual. Often I’d get calls from marketing departments or recruiters who were out of town. Nine times out of ten, they were nuisance or marketing calls. This one I answered.
It was a woman’s voice. "I hope that you don’t mind me teasing you?"
"Bailey?" I responded tentatively.
"Yeah."
"No, I don’t mind." I paused. "Do you do this for all of your customers?" Truthfully, I was ecstatic that she was calling me. My erection was practically tearing my jeans apart.
"I’m glad you don’t mind. Am I interrupting you?" There was a slight playfulness to her voice, for sure.
"No, not at all. My work day is pretty much over. Just finished paperwork and getting ready to start my drive home." I was putting myself somewhat at ease by the tone of her voice, and even though I was rabidly hard, it didn't sound like a woman who was crazy.
"Oh, that’s good. I am just having fun with you." Her voice pitched up at the end of the sentence.
Maybe she was having fun with this too. It was something that I'd never experienced before.
"It’s totally cool and kind of exciting."
"In what way is it exciting, Zach?" Bailey's tone of voice made this a distinctly leading question.
"Well, for one thing, I am constantly hard, and by the time I see you I am going to have blue balls!" I couldn't believe for a moment that I admitted that so candidly to her.
There was an awkward pause before she spoke. "I like that you are hard. Are you alone?"
"Yeah, I am, just me, everyone has left the construction site. Why?" I was anticipating something bad from Bailey and was not disappointed.
"Take your cock out for me." Her voice was quiet but serious.
"Jezzus um yeah, okay." I looked around to make sure I had shuttered the site office windows.
"I like you, Zach, you're a cool guy. Now stroke your cock for me. Not fast, just slow." Her voice was nearly a whisper, but a sexy whisper.
I did as she instructed.
"Shit yeah, it feels good, damn."
"Touch it lightly, don’t cum, okay?" Something about the slowness with which she was speaking and the tonality of her voice made me imagine her touching herself.
"Fuck, I want to." I really wanted her to tell me to cum right then and there.
"Mmm, I like that you want to cum for me, Zach. Just slow and light, don’t cum." Her voice was so soft and sexy.
"Fuck me, Bailey this is crazy, geez!" I nearly exploded just imagining her touching her pussy while she spoke to me. I wanted to ask her but didn't.
"Do you like it, Zach, do you like me teasing you?" Still the soft sexy voice.
"Yes, shit, it’s crazy." No one, no one had ever done anything like this to me at all. This is amazing. Was she going to start having phone sex with me? I imagined fucking her twenty-something cute body and watching her huge firm tits bouncing as I did.
"Are your balls full?" Her voice became louder and clearer.
"Fuck, they sure feel like it. Why are you doing this? I mean, no one has ever done anything like this before," I half begged for an answer, trying to ascertain her motives, while still enjoying her game.
"But you like it, right?" Again Bailey's voice pitched up and teased.
"Yeah mmm." I leaned back in my office chair admiring the giant hard-on, that was under Bailey's control.
"When you are touching your cock, Zach, what are you thinking about?" her soft sexy voice returned.
"You!" I admitted I hoped that was what she wanted to hear.
"Good. What are you thinking about me?" Her voice was softer and slower again.
"What I would do to you," I admitted. Yes, married or not, I would fucking fill you with cum, Bailey!
"Oh wow, I like that. While you are lightly touching your cock, tell me what you would do to me, Zach." Bailey's voice was steamy.
Do I admit it? Fuck, she must want me to say it! "Oh shit. Like I would fuck you, or like that, you’d be sucking my cock."
"That’s flattering, Zach, so do you think about me stroking your cock and playing with your balls also?" Something about her voice led me to believe this was what she liked. The control, and tease of stroking a man's cock.
"Yes, I do." I desperately wanted it.
"That’s awesome. I’m going to text you tomorrow morning and if you’re lucky maybe I’ll call you tomorrow at the end of the workday if that’s okay?" The sexy voice turned into a playful, more dismissive one.
"Yes, okay, yes, uh huh." I was a victim of this game. Staring down at my cock. If I knew where you are phoning from, Bailey, I'd come over there right now and fuck you!
"Byee, Zach." Without waiting for an answer she was gone.
The phone went silent while I traced my erect cock with one finger. Damn!
Thursday
After a night of pretty sexy dreams, I awoke the next morning to an even angrier erection. I instinctively checked my phone and was extremely disappointed to see no text message from Bailey.
I showered quickly and with the towel around my waist went back to my phone. This time there was a message from Bailey
Did u miss me?
Yes. I did miss her and want her so much.
U hard
Yes
Are you naked?
Yes. I dropped my damp towel to the floor.
Touch it and tell me what you are thinking about
You
What are you thinking about me?
I didn't answer her text
Be Honest!
Fucking you. I really did want to fuck her so badly.
Oh, Zach, you're probably a married man. Would you really fuck a girl my age?
I didn't answer that text. How did she know that I am married? I would really fuck her. I would but wasn't ready to admit it.
Does it feel nice when you touch yourself and think about me?
I shouldn’t and yes it feels crazy good.
I think it was at that time, I very much surrendered much of myself to Bailey, She was controlling the situation. Add to that, I liked it.
Good, are you full?
Fuck yes
Call you later
The text messages from Bailey stopped.
Fuck me, left hanging again.
The constant state of my erection was worsening, and I had extreme difficulty getting Bailey off my mind all day long.
Finally, the day ended, I wrapped up the project office and was about to shut off my laptop, when my cell phone buzzed.
The long distance number displayed on my phone. That call came in; it was her. Somehow she had figured out the optimum time at the end of my workday when I wasn’t busy and called me.
"Hi, Zach." There was that voice again; this time, Bailey sounded a little more anxious.
"Hey, Bailey." I awaited her next words.
"Is anyone around? Can you take your cock out for me?"
Anticipating Bailey’s call I had already closed my office blinds. I latched the door and sat behind my desk unbuttoning my jeans and letting them fall to the floor. My cock was super sensitive and fully erect already as I cradled it.
"Okay, I am undressed." I sensed that she enjoyed this as much as I did.
"Good, Zach, while I talk to you, I want you to stroke it, but don’t cum, never cum, okay? Not until Friday, when I see you, okay?" Bailey's voice softened.
"Yes, okay, Bailey, I’m stroking it and I’ll try." It was impossible not to be hard, and the urge to climax was equally impossible to ignore!
"Good, Zach, when you said that you wanted to fuck me, would it turn you on if I told you my pussy was shaved smooth?" Her voice was so soft and sexy.
"Yes." God yes, I would fuck her. I so wanted Bailey
"I just shaved, it’s really smooth, Zach." Her voice pitched up, like she was touching herself, or leading me somewhere.
I just breathed, trying to not furiously stroke my cock to climax.
"Would it turn you on if you thought that I was touching it while you stroke your cock?" She was either admitting that she was masturbating or actually masturbating.
It didn't matter.
"Yes." I must have panted out the words imagining those big firm tits and shaved pussy before me.
"You are kind of like that dirty old man, touching your cock, while you think about my shaved pussy. Do you like twenty-year-old girls, Zach?" She wanted to hear an answer.
"Just you." I guess I am dirty. I'd fuck her every day. Dine on her smooth pussy. Lavish her breasts.
"I like older men, Zach." Her voice was kind and meaningful.
I couldn't respond to that. What did she want me to say? I didn't want to say the wrong thing. A really big drop of precum was at the tip of my cock as I stared at it.
"I have to go, Zach, but I’ll call you tomorrow in the afternoon." It sounded like she was the one that didn't want to go this time!
There was a breathy sound. "Don’t cum, okay?"
"Yes." I stopped touching my steel-like throbbing erection. I honestly thought I could cum without even touching my cock while talking to Bailey!
"Remember our appointment K?
"Bye, Zach."
I didn't answer. I didn't really want her to end the call.
"I like you a lot, Zach!"
At that moment I realized how infatuated I was becoming with Bailey. I liked the control and the sexy texts and phone calls. I also realized that I needed to be careful. Could I really start to have emotional feelings for Bailey?
Needless to say, Bailey was on my mind constantly.
Friday
The next morning I found myself checking my phone constantly for messages. There were none from Bailey. I almost felt like this was a semi-cruel joke, and sometime today, the punch line would come. There was a pang in my stomach. If I really was developing feelings for her, this had to be a sign of that. This was the day. Five o'clock, I'd know. After all this, would it live up to expectations? Would it be something more?
That early afternoon while work was still happening, Bailey’s number popped up as an incoming call.
I rushed to answer it, "Bailey?" There was probably anxiety in my voice.
"Hey Zach, are you alone?" she asked.
"No, I am at the job site." I wished at that moment I could leave work and go see her.
"That’s okay, are you still hard for me?" Her voice was slow and kind.
My penis raged against my work jeans, and I moved about uncomfortably to try and hide my state of arousal. I had a wave of emotions but did not want to answer in case someone heard me.
"I’m looking forward to seeing you in today, Zach." The sexy twang crept into her response.
"Yeah, me too." I kept my answers slow and discreet, while my cock yearned for her. I yearned for her.
"Are you full? Are your balls full?" She was really teasing me now and knew it.
I walked around the corner of a building away from the other workers.
"Yeah, very." I looked down to make sure the bulge in my work jeans was not substantially visible.
"That’s good. I really want to help you after work, but I better let you go." She sounded different. Like she was anticipating something as well. "I can't wait to see you!"
"Okay, yeah, me too." I was deliberately discreet in case someone walked around the corner at an inopportune time.
"Bye, Zach."
"Bye, Bailey." I felt the need to say something else but didn't
I made every effort to close up the job site early and get on the road home, and the short bypass to Kate’s place where Bailey worked.
My mind wandered to her questions. What do I want to do to her, would I fuck a twenty-year-old girl? Was this just a fun game? Was there something more? Would I compromise my marriage?
Would I, would she want to? What if I’m nervous?
I reached into my mixed pill bottle and twirled the blue pill in my fingers. I was not going to let an opportunity slip if I got one.
Grace
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