Fetish Focus: His First Cock

Greetings degenerates and other lovers of kinky erotica!

This is a very different story for me.

It's only the second time I've written a story from a man's point of view, and even though I'm more comfortable with it than I was the last time I tried it, it has still been a learning experience. I want to thank my husband and the other men who proofread through this.

I also want to explore crossdressing if I do any follow-ups to this story, so I'm submitting it in the crossdressing category primarily for the reason, even though this chapter is as much about male-on-male bisexuality as it is the crossdressing.

If a threesome with two men and woman, where the men are sexually involved with one another isn't something you're comfortable reading, bail out now. Same of course for men wearing women's clothes.

If this story isn't your cup of tea, please check my submission list, since I have nearly eighty stories published here under a variety of categories. Something may grab your interest.

Like the rest of my stories, this takes place in a happy alternate reality where STDs don't exist, and people have no need to worry about birth control.

Large parts of this story were inspired by suggestions from a fan of mine right here in the Literotica chat rooms.

I hope you all enjoy this.

IsabellaEmily

~~

"Are you ready Jeremy?" Emily asked me.

I used to call her Aunt Emily, but she's not really my aunt. She was my mother's college roommate and has been a friend of my family for as long as I can remember. But standing outside her bedroom door like this it seemed more appropriate to think of her as just Emily.

"I am," I said. "I'm a little nervous, I guess. But I want to do this."

"Good," she said. "I've been looking forward to this all day. So has Colin."

"Colin?" I asked. "Is he...?"

"Colin is a crossdresser," Emily told me. "Not full time. Just for sexual play. When he goes out, he sometimes calls himself Carrie, but mostly he's just Colin, a bisexual who likes both men and women, and enjoys sexually exploring while dressed as a woman."

"Is he dressed now?" I asked. "As a woman?"

"Oh yes," she grinned. "He and I agreed that it would be fun to help you live out your handjob fantasy, and we wanted to do it right. Like you his sexual needs have more variables than he could find in strictly heterosexual relationships, so he has a soft spot for helping others have first time experiences."

"Sounds good to me," I said, grinning despite my nervousness.

"Just like last night," Emily said. "Enjoy the experience for what it is Jeremy."

She put one hand on the doorknob and wrapped her other hand around mine.

~

A few years ago, Emily moved down here, and when she found out I was attending college in the same town she got my number from my mom and invited me over for dinner.

She had been an honorary aunt in my life for a long time, and we'd always gotten along, so I happily accepted her invitation for a homecooked meal.

When I got to her house last night, I discovered that she was just as nice as I'd remembered, and as we ate and caught up, I found myself feeling more and more comfortable in her presence. She was easy to talk to and a great listener and seemed genuinely interested in me.

She asked me all about my classes and social life, and I found myself telling her things that I hadn't planned on sharing with anyone.

Ever.

Before I knew it, we were several hours past dinner, sitting in her front room by the fireplace, sipping wine with our feet propped up talking about my sex life.

After hearing the details about how I lost my virginity to my older sister's best friend when I was eighteen, she asked me what else I was attracted to.

When I tried to sidestep the answer, she looked at me with a knowing wink and asked if I had ever acted on my attraction to other men.

Maybe it was the wine, or my comfort level with her, or the fact that I'd never had anyone to really confide in about this stuff, but soon I was admitting things to her that I'd sometimes contemplated keeping a secret until my death.

I admitted that even though I'd always thought of myself as straight, a few years ago I'd started wearing women's panties, and I'd become so enamored of the way that my hard cock looked and felt in a pair of lacy or silky panties that I started thinking about other cocks.

I'd never taken the step of trying anything sexual with another man, largely because I wasn't romantically attracted to men, but I spent lots of time fantasizing about touching and stroking and tickling and pleasuring other cocks.

"Do you want to have sex with other men, or just play with their cocks?" she'd asked me, her eyes bright with curiosity.

"I'm definitely not ready to have sex with another man," I admitted in the flickering firelight. "But I can't get away from the fantasy of stroking cock. Especially if it's poking out of pair of panties or out from under a skirt."

"Just stroking?" she asked with a smile. "And the panties and the skirt are a part of it?"

"Well stroking for starters," I said. "Eventually I want to try more. And since I love the way my own cock feels when it's hard inside a pair of panties, that's definitely something I want to experience if I ever get brave enough to play with one."

"What do you mean if you ever get brave enough?" she asked, refilling my wine glass. "If you have a partner who wants you to experience this with them, what is there to be afraid of?"

"I'm honestly not sure," I said. "I guess I just don't know where to find that partner."

"Why are you waiting to look?" she asked. "Do you think this is a fantasy you'll outgrow?"

"No," I said. "I won't outgrow it. I used to think I might, but I accept that my attraction to crossdressers and transexual women, and even some men, is a part of who I am."

"Our desires may grow and evolve, but our core attractions are often innate," she said with a soft and knowing smile.

"But I have no idea how to find an experience with a cock," I said. "I don't want a relationship with another guy, and I don't want some guy to think I'm using him just for my own sexual fantasies."

"Some guys would really get off on that," she said, a twinkle in her eye.

"True," I admitted. "But I have no idea how to find them."

"Let me ask you two important questions," she said. "One, would you be willing to take that step if I found the guy for you? And two, are you wearing panties right now?"

"Well, yes," I said softly.

"Yes?" she asked. "To which question?"

"Both," I said with a grin.

"Good," she said. "Because I know a guy, a sort of friend with benefits, and he'd be very willing to sit back passively and allow you play with his cock until your heart was content."

"Really?" I asked, my heart thudding.

"Oh my yes," she grinned. "He loves to have his cock pleasured. However he is an exhibitionist. He wouldn't want something one on one with you. He'd want me there to watch. Do you think you could enjoy playing with his cock with me there watching you do it?"

I took a sip of my wine and considered it. Before that moment it had never really occurred to me that it could be thrilling to experiment in front of someone, but suddenly it was something I very much wanted to do.

Hell, it was something that I needed to do now that I'd thought about it.

"Yes," I said. "I would do that. I'd love doing that."

"Oh good," she smiled. "He gets off on being watched, and I'm one of the people he likes to get off in front of. Do you think you could come back tomorrow night?"

"Seriously?" I asked, hope flooding through me.

"Of course," she grinned. "I'd love to help you stroke your first cock. Provided you do something for me tonight."

"Okay," I said, wondering what price I'd have to pay for her to arrange for me to touch another man.

"Take your pants off," she said with a grin. "I want to see your panties."

"Are you sure?" I asked.

"Completely," she said. "Show me. Right here."

I stood up and moved in front of her, unbuckling my belt, and undoing the front of my pants and dragging the zipper down. She sat quietly, watching me in the light of the fireplace.

I pushed my pants down and stepped out of them, leaving a pair of lacy pink panties on.

"Oh wow," she said quietly, leaning forward. "You've shaved your legs."

"Yes," I admitted. "I like the way it feels."

"Those panties look delicious," she said. "And so does what's inside them."

I felt my cock twitch, and took a deep breath, hoping that it wouldn't offend her if I became fully erect.

She reached out and put her hands on my thighs, dragging them up along my skin and I felt my cock throb to full hardness, stretching against the panties as my body responded to her hot touch.

"My oh my oh my," she murmured. "You sure fill out those panties Jeremy."

"I get hard so easily when I'm wearing them," I said.

Of course, any good-looking middle-aged woman touching my thighs would have made me hard, regardless of what I was wearing. But in that moment the panties definitely added to the heat of the experience.

"How often do you make yourself cum Jeremy?" she whispered, dragging her nails along my skin.

"Every day," I said with a shudder.

She reached between my legs and pulled her nails along the fabric of the panties, barely making contact with my balls through the lace, and I felt my legs go weak.

"Don't cum tomorrow," she told me. "No matter how horny you are you should wait until tomorrow night. If you're going to take the step to touch a cock, I want your arousal to be as strong as possible while you do it."

"Okay," I said, certain that the erection I had right now would still be rock hard by this time tomorrow.

"Let me help you wait until tomorrow," she whispered.

She leaned forward and kissed my cock through the panties, and it lurched uncontrollably as she put her hands on my hips.

"Quickly," she said. "Quick for your dear old friend Emily."

She pulled my panties down and they stretched uncomfortably over my throbbing cock, and then my cock was free and bouncing up, and she pulled me forward and caught my cock with her mouth.

"Oh jeezus," I moaned, feeling the wet heat of her tongue circling my sensitive tip.

She sucked me hard and then pulled her mouth away.

"You've had a blowjob before haven't you Jeremy?" she asked.

"Yes...yes," I panted.

"Good," she smiled. "I'd hate to rush through this if it was your first one."

She took my cock in her fingers and pointed it at her mouth again, and wrapped her lips around it.

She started to bob her head back and forth, taking my cock all the way into her mouth while she started to rub my balls.

I was so aroused by our conversation and by thoughts of this sexy woman helping me find a cock to play with that I was in no position to savor what she was doing. Which was just as well because she was pretty determined to make me cum as quick as she could.

"I think I'm gonna...I'm gonna," I grunted in warning.

"Mmmmm," she moaned with a mouthful of cock.

She pulled at my balls even faster and sucked harder, and suddenly I was throbbing feverishly in her mouth as I felt my cum swell up and spurt out of my cockhead.

She moaned again and my legs turned to rubber, as I grabbed her shoulders and felt her tongue lick at my spasming cock, as my semen spurted into her mouth.

At last I was done cumming, and she squeezed and licked at my cock a few more times, before pulling my panties back up and tucking my cock into them.

"That should hold you over until tomorrow," she said with a grin. "Shall we say about five?"

~

"Just like last night," Emily said. "Enjoy the experience for what it is Jeremy."

She pushed open the door and I followed her into her bedroom.

There were soft lights in each of the four corners of the room, so that even though it was comfortably dim, there was enough light to see everything.

In the center of the room was a king-size bed, covered with dark sheets. In the exact center of the bed was Colin. I guess he was an average sized man, but dressed as he was, he looked absolutely perfect.

He was wearing a tiny button up white shirt, tied together across his belly, and I had a sudden fleeting thought about why it was that I've always preferred looking at women with small breasts.

Colin was wearing a red plaid skirt that nearly reached his knees as he lay with his smooth legs crossed. He had beautiful blonde hair and I wondered briefly if it was his own or if he was wearing a wig.

In the soft light he also had on what appeared to be blue eye shadow, and I seriously wondered how it was possible that a man could look so feminine and pretty.

"Colin, this is my friend Jeremy," said Emily. "He wants very much to experience his first steps into this world with someone patient and kind and horny, so naturally I thought of you."

"Hello Jeremy," said Colin, in a throaty voice that so perfectly matched his body that I wondered if I was dreaming. "It's nice to meet you."

"It's nice to meet you too Colin," I said. "I'm a little nervous, so I hope that if I act weird you won't be offended."

"You won't offend me," smiled Colin. "I have been looking forward to spending time with you since Emily phoned me last night. Do you have any questions about me or my lifestyle or anything else? And for heaven's sake please make yourself comfortable."

"Yes," said Emily, "let's get comfortable. Undress and join us on the bed Jeremy."

Emily pulled her sweater over her head and then reached behind herself and unzipped her skirt, stepping out of it as she undid her bra. She sat on the bed and moved up next to Colin.

I quickly undressed, my eyes darting back and forth between the two beautiful and feminine bodies on the bed in front of me. The fact that one was a middle-aged friend of my mother and a real woman, while the other was a sexy man dressed as a woman only added to my arousal.

I was trying not to appear as nervous as I really was. As I stepped out of my pants I hesitated and looked at Emily.

"Those are sexy Jeremy," said Colin.

I was wearing a pair of red silk panties, and they felt exquisitely soft against my cock.

"Yes," agreed Emily. "Why don't you leave them on?"

"I'll fit right in," I said with a smile, indicating Emily's red panties.

"Come on and join us," said Colin. "Would you like to talk for a while?"

"If you'd like to," I said, crawling up onto the bed.

"Maybe later," said Emily. "Jeremy has been wanting this for a long time, and I see no reason to prolong the poor boy's wait. We can talk later."

"Right down to the pleasure," Colin grinned. "As I understand it you want to take your time and just sort of explore? With your hands, is that right?"

"Very much," I said softly, staring at Colin's soft thighs.

"Then I'm all yours," Colin said, lowering his head to the pillow, and uncrossing his legs. "Explore away. Nothing is off limits."

I glanced at Emily who nodded encouragingly.

"Go ahead honey," she whispered. "Touch him wherever you want."

I put my hand against Colin's thigh and moved my fingers up and down, loving the feeling of the soft skin. I worked my way down to his knee, and then back up, moving from one thigh to the other, each time working my hands closer to his skirt.

"If you keep that up, I'm going to start to get hard," whispered Colin.

"I want to make you hard," I said, with a sudden boldness. "With my hands."

"Then do it," said Colin softly. "Touch my horny cock and make me hard."

I pushed his skirt up and saw a pair of plain white cotton panties, and the telling bulge under them was the most erotic thing I had ever seen. I put my hand on his inner thigh and pushed my fingers into his panties, encountering his soft testicles and penis.

I lifted the panties with one hand, pulling his warm penis out with the other. Even soft it was a bit bigger than mine was when I'm fully erect.

"Wow," I whispered.

"That feels so good," said Colin.

I held it carefully in both hands, loving the way it felt hot and heavy and solid in my fingers, even though it wasn't yet hard.

I gave it a soft squeeze and Colin moaned, and I felt it pulse in my fingers. I wrapped one hand around it and held it firmly, using my other fingers to tickle along the cockhead, delighting to feel a slippery wet bubble of precum ooze out of the tip.

I used my fingertip to rub the clear fluid all over the cockhead, feeling the cock get heavier and heavier in my hand.

Without thinking I started to move my hand back and forth, holding the skin of the shaft tight as I tugged up and down over the thickening meat that was gently throbbing in my hand.

I stroked him slowly, loving the feeling of his erection getting longer and heavier in my fingers as I slid my hands along the hot skin.

Bigger and bigger he got, until he was fully erect and throbbing. I had only myself for a frame of reference, but he was definitely much longer and thicker than my very average not-quite six-inch cock.

I let go of his cock and started to massage his balls, watching the big cock bounce gently as it throbbed.

"So big," I whispered. "So beautiful."

"Isn't he though?" whispered Emily, watching me touch him from just inches away. "I knew he'd be a good choice for your first handjob, since there's more than a handful to hold onto."

"Just over seven inches," volunteered Colin. "I'm glad you like it."

"I'm jealous," I grinned. "But I love how it feels."

I wrapped my hand around it again and started to pull up and down, staring at the lovely sight of this stiff cock poking out of the leg of his panties.

"I love the way you're making it feel," whispered Colin. "Your touch is heavenly."

"I've had lots of practice on my own," I laughed.

"Here," said Emily leaning over with a bottle of lube. "Keep it slippery."

"That's cold," Colin laughed as I poured some onto him.

"I'll warm you up," I said, wrapping both hands around his prick.

I gripped my hands around him and started to stroke, my left hand squeezing the base of his rock-hard cock and my right hand sliding along his slippery length like I'd been jerking cock for years.

I moved my hand in a twisting motion each time it passed over his head, and he stared at what I was doing and shuddered.

"Fuck that's good," he groaned. "I won't be able to take much more."

"I'm sorry," I said, loosening my grip and slowing down.

"It's not your fault," he said. "I've been edging myself for several days, so there's almost six days' worth of cum backed up in me."

"What should I do?" I asked. "Should I slow down?"

"Keep going fast, and hold my balls," he groaned softly. "I'll tell you when to slow down right before I cum."

I took his balls in my hand and held them tight, while I worked my hand over his cock even faster.

"Oh fuck," Colin moaned, grabbing Emily's hand. "He's good."

"I think you're going to make him cum," Emily smiled.

"I want him to," I said.

For years now I'd dreamt of this moment, planning to get whatever cock I was granted a chance to play with nice and hard and to work up to the spurting ejaculation slowly. But here I was, so anxious to see Colin cum that I'd forgotten my fantasies of a long and slow edging session.

"It's close," Colin moaned. "Keep going!"

"Cum for me," I whispered, not sure he could even hear me as he stared at the ceiling with his eyes shut.

"When I say so start going really slow," Colin said. "Just hold me tight and go up and down slow without touching the head."

I gripped his cock like he said and stroked slowly.

"Like this?" I asked.

"Yeah," he grunted, "but not yet."

I jerked him as fast as I could then, holding his balls and staring at his beautiful body.

"You're so goddamn hard," I whispered.