My "Good Boy"

There she was again. Tall and curvy, cleary the woman spends an awful lot of time in the gym at the squat rack, I thought. Those legs. Wow. But I turned my head away from the impressive view before she realized that I was once again staring at her, jaw unhinged and tongue half-lolling from my mouth. I chucked; it wasn't quite that bad. But it wasn't far from the truth, either.

I made my way up to my apartment. I didn't know where she lived. I didn't know her name. I'd never even exchanged a brief eye contact-head nod moment. And I figured, a tall and curvy woman like that was probably well off of the market.

I was twenty-seven. Once divorced. I know, right? Well, I got married young, right out of college, at twenty-three, and the truth was that my ex-wife and I were far too young, immature and stubborn. So that dark period lasted about two years, and then there was an unsettled six months as we extracted ourselves from that doomed union. I had moved on, moving away for a much better job and was feeling pretty good about myself. The only problem was, I'd not met a woman.

It was not for lack of trying. I did the dating apps and sites and I swiped right and I sent emails and texts. I got replies, I got ghosted, I got bots that wanted money for sex. It was all frustrating at times and yet I did not stop looking.

Since it was a Friday night, I decided to go to my favorite place. One block down there was this little hole in the wall Irish bar. My mother was born in Ireland and though her accent has faded some being in the States for a while, I had a soft spot for all things Irish. Including their pubs, and this was a good one. Later that night, there'd be a singer and the pub would be pretty hopping but the clientele generally was couples first, single males second. A lone woman walking into the place would have been virtually attacked with attention.

I got a table, near the wall, and ordered my usual drink and food choice. The waitress was a pretty, young girl who took the orders efficiently and moved off to the next table. She was not big on chit-chat. I was sort of staring out into space not really looking at anything. I was aware that the doors opened and a couple strolled in, then three single men, and then to my surprise, the beauty from my building.

I did not turn my head nor did I move my eyes, but I was sure to study her in my peripheral vision. I saw her scan the bar once, then a second time, then she shrugged. When she walked directly towards my table, I had no choice but to look directly at her. She stopped in front of me.

"You live in my building," she stated flatly.

"Yes, I do. I've seen you."

"I've seen you," she replied, offering a ghost of a smile.

"Hey, grab a seat before you get accosted with drinks and attention," I offered.

Her smile was wan and she accepted gracefully, sliding into her seat opposite me. We got to talking a little bit. I learned her name was Trisha, that she had been in the building for two years, that she worked about two blocks from where I toiled and that it was her first time in this bar. She learned that my name was Kevin and that I was a semi-regular here, because of my Irish heritage.

The conversation actually flowed pretty smoothly. It felt like a first date, to be honest, and a good one. I felt a bit of a spark and I leaned in just like she leaned in. We sat there until close to nine, until the bar was crowded, noisy and tight and I saw a lot of eyes ogling her and she seemed to be growing uncomfortable in the mob. So we paid our bill and left, returning to the busy sidewalks filled with people all going to the clubs and bars or returning from supper or maybe just out for a walk.

We exchanged numbers; it was clear that I was not getting an invite to her place. But all budding relationships have to have a first step, and unless I was very much missing things, that first step was taken.

Three weeks later we enjoyed our first sexual touch, but it was a one-way street only. We met at the bar, as we had done the past three Fridays in a row, and this time she invited me to her place. She invited me into her place and it was soft and feminine and I saw immediately that it was a million percent homier than what I had done to my apartment, which was nothing. I resolved to at least get a painting on the wall, and maybe a floral arrangement somewhere.

She led me to the couch and we sat and watched TV. We had been holding hands and kept holding hands as we snuggled closer and then we kissed. It was as passionate of a kiss as I had enjoyed in a long time, and I was content at the moment merely to kiss. The darting of tongues and the sweetness in her mouth, combined with the faint aftertaste of the whiskey she'd consumed, was pleasing. The natural reaction occurred and my erection pressed hard against my shorts.

She shifted to turn sideways to me, draping one arm almost protectively around my shoulders, and planting the second on my crotch. "Can you handle it if we do it my way only?" she whispered.

My cock, pressed by her hand, spoke for me. "Yes."

The kissing grew hotter; her body sort of trapped my arm against hers and I was aware of my upper arm trapped between her two firm breasts. But I could not touch her back. This might have started bothering me until she unzipped my shorts and drew my penis out. Her stroking was the best touch I had ever had another woman give to me. She stroked it expertly, soft and slow, not gripping and jerking like it was a teat to be milked.

There was one thing that my ex-wife had liked best about me during sex. I was a moaner. She loved hearing my sudden noises, filled with sexual longing. It burst out when she gave the upper region of my shaft a sudden squeeze.

"Mmmm, a moaner," she said instantly, her fingers sliding up to tease the hole at the tip of my cock. "I love that," she told me and then pressed in for a deeper kiss again. She played with my cock expertly, eliciting several more moans from me. The pleasure built steadily.

"Do you want me to suck your cock?" she asked me, her lips right at my ear, her fingers curled around my hardness, using the steady dribble of my precum as a lubricant.

"Oh god yes," I replied.

"Will you moan for me?" she wanted to know.

"Yes, I will."

Then she said a curious thing. "Good boy," she grinned. I was pushed down onto her couch as she nestled in between my legs. She looked up at me as she held my cock, stroking it lightly. Her eyes burned into mine as she pressed my rigid flesh to her lips and held it there.

"Are you going to give me a big load of cum?" she wanted to know.

"Yes!" I assured her.

"Mmmmm, I love taking big loads of cum in my mouth and on my face," she told me.

The rapid-fire thought pinballed through my brain: ohmygod she's a cumslut she's a cumslut ohmygod. Her mouth opened and all such thoughts were instantly blotted out by the most skillful blowjob that I'd ever experienced. She was perfect, her tongue swirling around the head as she held just that part in her mouth, all warm and wet. Then the slippery pleasure of her mouth moving down the shaft, taking more of me into her mouth.

"OoohhhhHHHHHhhhh," I moaned in delight, wanting to squirm under her body.

She picked up on my moans and her intensity picked up. My cries and moans grew closer together, more insistent.

"Oh Trish, Trish, oh god, I'm gonnnnnnaaaaaaa...." I groaned as my balls gave one final churn and the almost-visual of falling over a cliff was complete. The orgasm hit, the first eruption of cum hitting the back of her mouth and she moaned then, a loud noise, greedy and wanting. She jerked me harder and faster, gripping a little more tightly at the base, and improving the orgasm. Spurt after spurt of milky-white cum erupted and filled her mouth, and she swallowed hard and fast and not a drop was left out.

Finally, the orgasm subsided and my cock began to go flaccid. She released it and released me, and sat up, her fingers lightly toying with the top of the flesh. She grinned at me, her tongue poking out and slipping a droplet of cum into her mouth. She swallowed and moved close. "Will you kiss me?" she asked me quietly.

I had a hesitation. But not a long one. "Yes," I whispered, almost amazed at my own reply. I had heard of such things before but had never done it. And then she used that little phrase again, a lopsided grin. "Good boy," she said and then kissed me hard.

There was a taste. Not a bad one, I guess, but the lingering taste of my seed in her tongue was definitely there. And as I kissed her, again reveling in her ability to kiss, I realized that I didn't much care. I kind of liked it.

We sat up and I asked her if she was sure that she didn't want me to touch her and make her feel good.

"I feel wonderful," she assured me, pressing a fingertip to her lips. "Although," she added almost as an aside.

"Yes?"

"So I gather you now know that I have a few kinks," she chuckled.

I matched the tone and nature of her chuckle. "Yes, I gathered."

"I have a few more and one's really important to me," she said next.

"Okay," I said, waiting for the other shoe to drop.

"I love hypnotizing people," she said simply.

"Oh," I said, surprised. "I've never...what got you into that?"

She smiled. "I was a psych major!" she giggled. Continuing in a more serious tone, she told me that she loves it as a tool to help people unlock potential in their brains. Or, she added, to unlock the latent aspects of their psyche so that they can more fully enjoy their life.

"So is this clinical?"

She shook her head no. "No, this will be simply for pleasure."

"You're not going to turn me gay or anything, are you?" I asked her.

She smiled, although perhaps less confident than before. "Hypnosis cannot turn you into something that you are not. But if you have latent gay tendencies, then hypnosis can help you unlock that so that you can discover for yourself the pleasures of it," she corrected me.

"So you can't make me do something completely against my will?"

"No, I cannot," she assured me.

"Then sure, what the hell," I said.

She nodded. "Tomorrow, two o'clock?" she suggested.

"Sure," I agreed. We wrapped up the night shortly thereafter, and I went home with a satisfied cock and a bit of a wondering mind. I suppose that my questions would be answered in due course.

The next day I knocked and she opened the door and ushered me inside. She had set up a chair for me to sit in and after exchanging a hug and a warm, soft kiss, she took my hand and led me to the chair. She pointed out that there was no sense in waiting.

I warned her that I doubted that I would be able to be hypnotized. She nodded and agreed that it was very possible, but suggested that we try anyway.

At some point I recall watching her and listening to her and feeling really good all around. When I stirred back to life, I saw that I had lost nearly ninety minutes of my life. We talked long and wide about what she discovered. She said that it was all good information for her to have and no, I wasn't a psycho or anything all that remarkable. I told her that I was relieved.

But she said that she had to get up at an ungodly hour to catch a flight at an ungodly time to fly to an ungodly city for a conference that work was making her attend. She promised to call me but basically kicked me out of her apartment. I did not feel too bad; in fact, I felt really kind of relaxed overall given the lengthy hypnosis session.

After a mostly productive Monday - surprise of all surprises - I did my usual weeknight routine, hitting the gym and then coming back to the apartment to shower away the sweat of the workout. Trish said that she would call me once she was back in her room and coming down from the day. I checked my finances and while they weren't great, they weren't awful. I flopped on the couch and in the absence of anything else to do, idly flipped through some online dating profiles. Nothing much engendered interest, so I flipped over to the default activity that men do when they are alone and bored.

I had not even gotten a minor swelling of my cock when the phone rang. It was Trish and I greeted her warmly. "Hi baby," she said and I could hear the smile on her face as she said that. We chatted for about twenty minutes, light stuff, mostly reporting aspects of our work day. We signed off and as we did, she told me that she hoped that I would be a good boy for her. I had a chuckle at that and blew her a kiss into the phone, and that was that.

I got up and went over to fetch my laptop. My phone was okay for browsing porn but not as good as the laptop. So I set that up and stripped out of my clothes, and began idly looking through the things that usually made me hard. I stroked lightly but in truth I knew that I wasn't much feeling it right now. The usual movements of a big-titted woman and a big-cocked man going through the motions of sex without any of the intensity did not hold much allure.

It was funny, but I thought of Trish then, and how she liked cum. I started clicking on more riskier videos, and finally I saw one that made me frown. For some reason I felt like I didn't just want to click on it and watch it, but I NEEDED to do so. It was a tall, rather muscular shemale with a big cock and no pubic hair stroking it to a big orgasm. I found myself transfixed suddenly, and my hand moved in conjunction with hers. Although I did not orgasm, I was now very hard and into the scene. The best part about the site I preferred was its suggestions based upon the video just watched; I clicked on another and watched, transfixed, as a big-cocked shemale slowly stroked her organ to its impressive girth, and then spewed cum on herself. I was even harder now.

I kept stroking slowly to video after video of hung shemales stroking to orgasm. I was getting closer and closer to orgasm myself, and almost on cue, there was a video where those same sexy shemales with big cocks had men slurping on their organs. One after the other, the shemales came onto the faces or into the mouths of the men. Some pulled out and coated their chests, a few came onto the man's hard cock, a few into his ass. But at the conclusion of that video, I moaned again and my own cock began to spurt.

The lengthy session made the first three eruptions of my orgasm more powerful than usual. For whatever reason, my vision shifted to watch the head of my cock as I came, and I could see the long ropes of semen rise up and hit me, on the face and lips, the neck and the chest. The droplets were hot and slippery and that creamy scent of a man's semen hit my nose hard. I managed several more pulses, but each one moved steadily down my chest and belly and then finally I was left with the slow dribble of that last big, thick droplet oozing out.

I licked my lips, tasting that thick droplet of my cum, and smiled. It was not awful, somewhat to my surprise, but neither was I suddenly addicted to its taste. And I felt so relaxed that I ended up falling to sleep right there, letting all that cum dry off of me. I slept through the night into the next morning, where with some dismay I cleaned up and started my day off otherwise normally.

The next evening, I again chatted with Trish. We were on the phone for about twenty minutes before she changed up the nature of the conversation. "Hey, can I ask you a pretty personal question?"

I laughed softly. "Yes, but I don't have to answer."

"Ha ha," she said. "Seriously, though, I was going to ask you if you masturbated last night."

"Oh," I said, surprised. "Why do you want to know that?" I asked.

"Just curious I guess. I mean, I did," she added.

"Well, since we're all in the interest of offering up TMI," I teased, "yes, I did."

"Oooh, was it good? Mine was slow and hot and I came hard," she reported to me.

Well, that was enough to stir my cock in my pants. "Mine was about the same," I reported. Then, feeling like I wasn't giving her enough details, I continued quickly. "I edged twice, I think. Then I had a big, uh, big cumshot," I said.

Again, I could hear her grin. "Oh, that's such a good boy!" she praised me and as before, I felt a surge of pleasure at hearing that phrase. My cock stirred in my pants as well, more than it had earlier.

Her voice suddenly dropped into a conspiratorial tone. "Can I tell you? I watched some shemale porn, god it makes me hot!"

I was surprised; I would not have expected that. "Funny thing, that's what I ended up cumming to," I told her.

"Mmmmm," she purred warmly. "Oh that's hot, baby, that's so hot," she whispered into my ear. "I'm going to go now. I'm going to play with myself until I cum, and I'm going to watch shemale porn again!" she told me.

"Oh my god," I groaned softly.

"Will you do the same thing, baby?" she asked all breathless.

"Yes," I told her.

"Oh, such a good boy!" she said with particular emphasis on the last two words. Not a minute later we hung up and I was naked and had the first of the videos cued up. I watched avidly transfixed as this time a very cute, soft-looking woman with a big shemale cock not only stroked herself, but she was able to self-suck and she came on her own face. I kept watching this particular woman as she fucked another shemale, then fucked a cute girl. Watching a feminine body with a big cock slip deliciously into a pussy brought me to the edge twice.

Finally, I got to a video again where lots of shemales were cumming all over everyone. There were self-cums, self-facials, facials on men and women and couples and other shemales. Everyone was getting cummed on, and everyone looked like they were having the time of their lives. After the three edges I forced on myself, my cumblast that night was as big and strong and powerful as the night before, and I might have even arched my hips up off of the couch a little and held my cock to aim it towards my face. I got a few drops on my face but overall, the volume and strength of the orgasm did not match the prior night's, though as I had done the prior night, I was so relaxed and pleased with the result that I struggled to rise from the couch. But this time I did, washing up before tottering off to bed.

The next night I asked her when she was coming home, and it was going to be the following day, Thursday, but not getting home until later in the evening. She did not waste much time in redirecting the conversation.

"So tell me about masturbating last night," she directed me.

"It was good, I watched this girl, she has nice, long hair, soft boobs and a big cock. I must have edged two or three times watching her," I reported.

She chuckled. "I wonder if we watched the same girl?" Trish asked. She said her name and I agreed that I had watched her.

"Tell me what you liked best about her?" Trish suggested.

I did, focusing on her pretty looks, her nice body and of course her big cock!

"Oh, you're such a good boy!" she moaned. "I wish I was there to show you exactly how aroused you're making me!" she said.

"I like hearing you say that," I said.

"Good boy?" she asked.

"Yes."

"Does it make your cock twitch, baby?"

"A little, yes," I admitted.

"Maybe I can guide your masturbation tonight," she suggested lightly. "Have you ever done that?"

"No," I said.

"Would it turn you on for me to verbally guide your masturbation?" she asked breathlessly.

"Yes," I smiled.

"Oh you good boy, you good fucking boy!" she moaned. "Take your cock out," she ordered immediately.

I shimmied out of my pants and by the time I kicked them to the side, my cock was semi-erect. "It's in my hand," I told her.

"Let me send you a video," she said next. "How can we do this?" she mused. "Maybe a dirty chat room or something?"

We put our little pleasures on hold while we found a chat room system capable of showing the same porn to us both. It didn't take long, and then in a soft, whispery voice, Trish said "I'm going to send you the video now, and you stroke slowly for me, baby," she guided. "I'm going to be touching myself the same way," she breathed.