Chapter 2

“Markie, you still have a lot to learn. So trust me. There’s more lessons here. For your own good. You promised you would obey.” He looked from my lips to his cock. “So do it. It’ll be easier than you think.”

It was a living thing, that moved on its own sometimes. But more importantly it was another man’s cock and then he dropped it in my hand. Wondering just how big the hot flesh would get, I started stroking it with considerable hesitation. Would it be five inches bigger than mine? Maybe four, or three? I was sure his would be at least two inches longer.

“Markie, you’re a beautiful woman and it’s ok for a woman, like Maddie, to do it, you know.” It seemed wrong to think of Maddie that way. But other women…

Stroking that slowly engorging member I started pondering the whole chicken and egg thing. Did having a big cock make him more dominant? Or somehow did him being more manly affect his testosterone so that he grew a bigger cock?

I shook myself free from my reverie, “Yes, sir?” I really enjoyed the coy grin he gave back to me.

“You’re too strong for these delaying tactics. Just get on with it. Why, I bet you’ll be better than Maddie at it.”

But it was still mostly soft, and not yet hard? There was a drop on the end so I wiped it off, drying my hand on my dress. Hearing him say the word ‘bet’ I leaped at it, “Like double or nothing?”

“No, you need to suck it. It’s not an idle exercise. It’s a lesson. But I’ll tell you what, if you’re better at it than Maddie, when you come back tomorrow you will have earned a massage.” He placed his hands on my shoulders as he said it, “I can feel some pretty tight muscles here.”

“Uh, ok a massage. If I win I’ll…”

I would have finished that thought but he pulled on my shoulders bringing my head down. I felt panicked so I dodged his cock but only ended up with my lips pressed to Chet’s nine and one quarter inch ball sack.

They weren’t sweaty. Though they DID seem so much larger from this close. And while my whole evasion tactic had been to avoid his cock it fell down anyway, draped over my nose.

“Let your tongue out, girl. Just poke the tip through your pretty lips like every other pretty woman.”

I held my lips tightly pursed. But then forced just the tip of my tongue out. It touched his sack and nothing happened. I wasn’t suddenly a flaming queer. I didn’t instantly turn into a cocksucker.

“Nicely done, beautiful. It’ll be easy to lick them now. You’ll feel so accomplished if you do a good job.”

Was this the point of the lesson – to feel accomplished? I opened my lips wide so I could bathe those big plums with my wet tongue. I imagined how good it felt for him, which wasn’t hard the way he squirmed in pleasure. I literally felt his calves flexing while his feet were so antsy down below me. I wanted it for myself someday. But for the time being I would have to live vicariously.

I tried out long swipes, circular licks, getting into the crevices, and made sure to give each testicle some individual attention. He loved it all. So when he said, “It’ll make me real happy if you lick up from the base to my mushroom head.” I wanted to make him happy.

By now that seemed like no big deal, but then I imagined the leaky head deep inside my mouth and yet again my fears arose.

“Markie! Just lick up from the base. You want to be a real man, don’t you? To get what a man gets from Maddie?”

Maddie wanted me to have more muscles. More confidence. To be more decisive. Chet wasn’t offering any of that… except that I already felt more confident. And he was urging me right now to be decisive – maybe? And when he put one of my hands on his testicles, asking me to caress them, I did it without thinking.

Oh fuck it! I’m strong enough to suck a cock. Even what was sure to be a big one like Chet’s. I wiped the wetness off the tip again. Then steeling myself, I stuck my tongue way out, rubbing it on his shaft just above his now spitslick balls. Forcing myself, I threw everything into the lewd activity, rising up on my knees in order to trace a wet path all the way to the top.

And then it hit me like a ton of bricks. The ache that had previously been in my elongated nutsack returned with a vengeance. No longer just discomfort it was now out and out pain. Did the bottle suddenly get ten pounds heavier?

I tried to pull back, to look. But Chet had his hands firmly wrapped up in the wig on my head, and he held me in place. “Hurts huh? I guess my foot is kinda on the weight.” The grin on his face was devious. “Push through it. You gotta fight for what you want. THIS is how you become a real man. No pain, no gain. Learn to face adversity, girl.”

I was so confused. Man, girl. Mark, Markie. Was I a pussy fucker or a cock sucker? I didn’t know.

“It’s for your own good. It’s a small thing for such a big gain.” Saying that he rolled the bottle gently with his foot, “When you’re used to it, and you expect it, it feels good, right? It’s a good pain that’s gonna make your orgasm so much better.”

I hadn’t imagined that I was going to cum as part of this. This was to help me. He wasn’t selfish. And upon reflection, the pain did kinda feel good?

Chet pulled on my head as he pushed on the bottle. It wasn’t too much – the string tied around my testis gave me a slow stretch. I looked at his cockhead. It didn’t look too bad. And then it was partly between my lips. There was some wetness there and, honestly, it didn’t taste like honey or even good. But he still made me do it.

A moment later and that bulb was pushing into me. I felt the ridge pass my lips. I didn’t know it was going to be so fat, that I was going to have to open so wide.

Then the downward tug on my nuts stopped, “Is that better? Now jerk yourself.” It WAS better. I moved my other hand to my cock. Only now I couldn’t support myself. The only reason my head didn’t fall forward, impaling me, was his hands holding me back.

Chet pulled my head up and down on what was still a dangerous semi-hard spear. Next he wormed the whole thing into my mouth so the squishy sponge filled me up, seemingly squeezing into every available space.

He pulled me all the way down until my lips were buried in his short pubes. Then not completely unexpectedly, he pulled on the bottle again. A low roar escaped my throat as Chet commented, “I bet they’re pretty fatigued after all the pulling, then resting, only to be yanked down again.” Then he tugged harder in staccato bursts. His evil laugh held the same staccato quality. And only now did his cruel cock grow stiff as a board.

“Don’t stop jerking, pretty girl. You’re turning me on sooo much. Your hair, your dress, your mouth, your pain, and your lust, all rolled into one.”

When his dick finally grew hard it no longer fit in my mouth, instead it pushed my head upward, making the stretch in my balls even more taut. Jerking was difficult in my state but I didn’t want to stop. I couldn’t stop sucking his cock either.

Grunting from the discomfort, as well as the excitement of sucking a more manly cock, I couldn’t tell the difference between one lusty vocalization versus another. My head was forced on his pole faster and faster in an ever increasing frenetic pace which I matched down below.

Suddenly Chet pushed me off and took over wanking his own cock. With relief in my nuts, I could pull on my own cock more freely. Together we beat our meats until he extended one leg out straight, really challenging the ligaments in my scrotum. I screamed and I erupted jets and jets of cum, which flew everywhere. Hearing my orgasmic exclamations, Chet came in pearly spurts too.

And in that moment I noticed two things: his hard dick was actually no bigger than mine despite my previous conviction, and that his cum load was no bigger either.

I had no time to compare our masculinity or the implications ’cause just then Maddie called. Panting from my exertions I answered the phone with the last vestiges of cockskin flavor still permeating my mouth.

“Are you there yet? Is my big hulking ex teaching my little husband something about being a man and weight lifting?” I would hardly describe Chet as ‘hulking’ and I chuckled inwardly when she mentioned weight lifting.

Chet held up a finger and mouthed some words to me, “Put her on hold.”

“Hold on a second.” And I pushed the hold button.

“Perfect. You did that exactly right. Let her wait. When you take her off hold tell her we’re busy and ask her if there’s something important. In fact, I want you to work in how totally available you are to help, IF it’s something important.”

I did what Chet said and oddly she became apologetic.

She asked when I was gonna be home. Chet could hear everything, “Don’t name a time. Say you’ll be home as soon as we’re done.”

Just before we hung up Maddie told me she loved me and then there was Chet putting words in my mouth: “Me too. Say me too. But don’t use the word love.”

“Tonight when you’re at home withhold all compliments. If she asks be truthful, but then add a pull-back. Instead of you pursuing her, pushing compliments out of your mouth, she needs to pursue you, trying to pull them out of you. Make her work for it.”

I said, “I don’t get it.” Which made him sigh, exasperated.

“Let’s say that asked you if she looks good in her new shoes, what would you say?”

“I guess I’d normally be truthful. I’d just say she looks hot and I like how the heels shape her calves and lift up her gorgeous butt. Is that so wrong?”

“Normally no. But tonight it would be. If she asks about some shoes, tell her the color is fantastic. Or that the heels are sexy. But focus on the shoe. If she pushes you, asking about her ass, then you say something like, ‘It’s very nice in those shoes, but the blue ones work better’ got it?”

Chet pulled me up onto the couch next to him. He told me to pick out a movie while he dug around in one of Maddie’s purses that I’d forgotten about. A minute later he handed me an old tube of lipstick that I knew exactly what to do with.

We watched an entire movie with his arm possessively wrapped around my shoulder except when I got up to pay the pizza delivery guy who looked a devil in a red dress up and down in a way I’d never experienced before. During our evening together Chet actually treated me like a real person.

Later, dressed in my normal clothes and feeling more confident, I stepped out the door with a new spring in my step. Chet clapped me on the back, “Mark, I’m glad you came over. See you tomorrow, cocksucker!”

The initial acknowledgement of my true identity turned into a punch to the stomach. I fumed at the audacity. I would never go back.

But at home I did the things I could remember and my relationship with Maddie was better than ever. Not just better for me but objectively better.

Until the next morning when she seemed to inexplicably just wake up a nutcase. I HAD to go back.

At Chet’s apartment he greeted me warmly, adding, “I laid out her sexiest lingerie for you. Two pieces actually. Go put one on.”

Yesterday I had worn the dress after losing a bet. Today I only wondered which two items he had laid out.

One was a very dramatic green push up bra ensemble with matching corset and hose. I fingered the lacy fabric which to me felt rough rather than smooth like it should. Though it must’ve looked super hot on my wife.

The other was a satiny padded bra, which would have helped Maddie look fuller on top. It came with a matching white thong and white stockings. The hosiery was so soft between my trembling fingers. I liked the elegant simplicity and I just knew that one would look best with her black wig. So I put it on.

Entering the bedroom, Chet whistled. Are you in the mood for another educational blowjob, or would you like that massage you earned?

I wasn’t feeling it like I had yesterday. And my shoulders… “A massage would be great.”

He guided me onto the bed then straddled my calves rubbing the stress out of me quite efficiently. When his hands passed the tops of the stockings, the sensation of bare skin on bare skin felt calming and exciting. He rubbed up to my tense shoulders then back down to my ankles only to repeat it. “Is that good, darlin’?”

Squeezing my thighs, his calloused fingers grazed my gems, awakening something in me. He pushed the thong aside and wrapping his hand around the baubles he manipulated them a little roughly, reminding me of the treatment they suffered only the day before. “I won’t hurt you, baby. Go with it.”

Prodding, twisting, and gently pulling, this different massage caused me to lift up, providing full access to this formerly abused part of me that needed these soothing strokes today. “I like how you present. Such a good girl.”

As both hands started coddling and spoiling my sack it came as a complete surprise when a slick thumb intruded easily into my relaxed chute. I just knew he was wrong when he said, “You’re still tense. Tight equals tense.” He wiggled his thumb around, “There! That should be better.” I thought to object, but before any words came out he had already withdrawn the offending digit.

Chet moved up, really getting at the tight knots I had between my shoulder blades. I relaxed again under his helpful ministrations.

And before I knew it the head of his cock was inside my sphincter. “What are you doing?!” I squirmed as if I could wriggle it out of me.