Vanessa

Her name was Vanessa. She was very cute, about 5'4", slim, with big brown eyes and skin that was very clear and smooth. We had met online, of course. She had reached out to me for advice and friendship, as I was an experienced transwoman.

After talking online first and then over the phone, we met in person. It was at her place, since she wasn't all the way out yet. But when she opened the door, I couldn't tell that she was a man in any way.

Vanessa wasn't very tall at five feet, four inches tall when barefoot. She was a little shorter than I, both barefoot and now with me wearing five-inch heels and her in her four-inch pumps. Her eyes went to the floor as she opened the door and nearly hid behind it, saying in a very soft and surprisingly feminine voice, "Please come in."

"Thank you," I said with my brightest smile as I did. I heard the door close behind me, along with the deadbolt clicking into place, and I turned to face my hostess.

She had her hands clasped in front of her and her face downcast, as if embarrassed. I guess that I would feel the same way if our roles were reversed. I'd had the resources of a biotech company to help me with my unintended transition to womanhood, after all.

In my gentlest and softest voice, I called out to her. "It's very nice to meet you in person, Vanessa. You're even prettier in person." Kinda corny, I know, but I did mean it.

A furtive glance up to my face and then she returned her gaze to the floor. "Thank you...Jessica," she intoned in the same feminine, breathy voice.

"It's OK to look at me," I assured her.

"I...I know, I just--I'm really nervous, is all," was her reply.

I chuckled and told her that I could only imagine. And it was true. To the best of my knowledge, there wasn't anyone quite like me anywhere else in the world.

In a previous life, I'd been a man who enjoyed crossdressing and had dated a fun lady who worked for the aforementioned biotech company. Said company had developed revolutionary breast forms that she'd let me test out, but the nanites that the forms used had gone screwy, leaving me with not only breasts attached but with my body converted to a woman's but with my penis not just functional but with enhanced stamina, ejaculation output, and much shorter refractory period, while being thicker and longer. In retrospect, it was pretty great, but it had been a hard road to get there.

Since then, I'd had some adventures starting with my first love as a woman, Julie, but--well, you've already read that account, haven't you?

I snapped out of my reverie. "I'm dead serious, you're very pretty, Vanessa."

She looked up at me for longer this time. With a very sweet, genuine smile. "Thank you. I, um...it's nice to hear that."

"You look nice. Thank you for inviting me into your home."

"Thank you for coming over," she said, finally making more than two seconds of eye contact. "Um...would you like something to drink? I have iced tea, I can make coffee, I have some wine, probably a few beers in the back of the fridge..." she offered, stopping herself from rambling with visible effort.

"A glass of iced tea sounds wonderful after the heat of today," I said, trying my best to be gracious.

She smiled a demure smile and clicked her way into the kitchen in her simple black pumps. "Iced tea it is, then." I admired the view as she left the room. She was tall, slender, and genetically male so her hips were fairly narrow, but I could tell that beneath her flower-print sundress that she was smooth and toned. As she returned with two glasses of sweaty iced tea, I had noticed that she didn't have much in the way of a bust, but that wasn't a big deal to me. I had, after all, been in the same boat, and look how it worked out for me!

Focus, Jess. "Thank you," I told her as I took the proffered glass. I took a deep quaff and it was very tasty. "Mmm!" I exclaimed. "That's delicious. I'd love to know the recipe someday."

Vanessa blushed and looked down again. "Thanks. It's my Mom's recipe. I'd be happy to share it if you want."

"Definitely. That's great. So...should we get better acquainted?" I asked, trying to move this out of Awkward City.

"Oh. Of course! Please, sit!" she implored, gesturing to the couch and armchair that decorated her living room.

"Great furniture," I commented as I set my glass down, smoothed my skirt under my legs, and sat demurely, making sure that my stockinged legs stayed together. For now, I hoped. I chuckled internally at how, even after all these years since the nanites forced me into living as a woman, that the feel of my stockinged legs rubbing together still gave me a little shiver of pleasure.

"Thank you," she said with another blush, doing the same with what looked like a well-practiced motion similar to mine. I was impressed with how feminine this "girl" who identified as a sissy moved.

And that's no lie. When she had reached out to me on the site where we started talking, she had identified herself immediately as a sissy. Not female, not male, but a sissy. An effeminate guy who loves dressing in female clothing and having sex as a girl while retaining his male sexual equipment. I'd never been with someone who was a sissy, whether as a friend or more physically intimate, so...why the hell not? She'd been looking for advice and training on how to be more feminine and was looking to ultimately get into a relationship with a dominant female or transwoman like myself (although the dominant part was definitely flexible with me) and so I couldn't help but agree to at least meet her. She was so cute! A sexy little pout, pretty eyes, skin so clear and smooth I could hardly believe it, and for a non-nanite-modified genetic male, a fairly feminine shape. I just couldn't help myself helping this girl. That's how I thought of her, anyway.

"So...um..." she began, but faltered.

"Vanessa. Look at me," I said in a gentle but firm tone.

Her eyes looked up to mine after a second's hesitation. There was apprehension and some fear behind them.

"What did you want to accomplish by inviting me over?" I know it's a little bitchy, but I think she needed the push. Put it out there! Tell me what you want. Be femme, be demure, but you've got to communicate, little girl.

She bit her lip. Then the floodgates opened. "I know I'm not as girly as you but I was hoping you could give me some pointers or whatever and I just can't get over how beautiful you are, and I've seen some of the pictures and videos you've uploaded and I just can't get over how sexy you are and I love how honest you are about being into D/S and I'm so conflicted about what I am and how people will see me and I know what turns me on but I want other people to find it sexy and I know that deep down I'm a dude wearing girl clothes and everything everyone told me growing up is that it's wrong, and...I don't know what made me ask you to meet me IRL but...maybe you can just tell me that it's OK for me to be me and be like this, and--" That's when her tears morphed into sobs, and I got misty.

"Oh, honey!" I said, and moved as fast as I could to sit beside her and cradle her head against my chest. My full, cleavage-showing chest. Dammit. Maybe not the best move. But she needed someone to comfort her, so I hugged her tight, thinking that we could probably deal with any damage related to me literally shoving my tits in her face later. She needed a hug and a friend to give it to her.

She sobbed as I whispered as many soothing phrases as I could. "You're a very pretty girl, Vanessa," I began, meaning it.

"Do you," *sniffle* "really mean it?" she asked.

I gave her my most gentle and encouraging smile. "I really do, little girl. I've already enjoyed talking with and getting to know you. You're cute and girly and I'd like to help you in any way that I can, sweet girl."

She gave a smile that was so sweet it could rot teeth and looked me in the eye for a moment, then looked down. "Thank you. I'm really sorry. I--no, I already told you," she breathed, then took a huge breath. "Um...did you mean that part about helping me?"

"Of course I did."

"Even the any way part?" she asked, glancing up at me then back down as she bit her lower lip.

I cocked an eyebrow. "Why do you ask?" I inquired as a half-smile dawned on my face.

This time Vanessa blushed furiously but it was so cute. She didn't speak for almost a minute, and it was clear she was gathering her courage to say something. "I--can I show you me, first? I want you to tell me what I can do better. Then I have a request. Is that too much?"

I pecked her cheek and laughed a little. "Of course not. What you want to show me, ask me, or ask of me is completely up to you. I'm here to help, remember?"

She sniffled again and said, "Thank you, um, Jessica."

"You can call me Jess if you like."

"OK, Jess. Would you mind telling me what I can do to be better at girly?"

I sighed and smiled. "I haven't found anything you can improve on yet, but if you're bound and determined to have me find something, I'll humor you and look."

"Thank you," she said and unzipped the back of her dress. She took it off in a fairly seductive manner, enough so that I felt my womanhood stir in my extra-strength gaff, and then the dress pooled around her feet. "What can I do better?" she asked.

I stared. I couldn't find a thing. Besides her skeletal structure, which outside of me, nobody can help, she was the picture of femininity. Soft skin, painted toenails, and fingernails, she was hairless from the neck down. A girly purple bra and panty set, which outside of the impressive bulge deforming the panties, looked perfect on her, and a matching garter belt with nude stockings leading to high heels.

"I, um...I can't find anything, Vanessa. You're very girly with one...*ahem*...very large exception. I wouldn't change anything," I told her.

She blushed a little. "Yeah, I can't always hide that part. But are you sure?"

I stood up and got right in front of her face. "Yes, Vanessa. I am sure. Very sure. And I wouldn't want you to hide that glorious thing in your panties even if you could," I explained with another encouraging smile. "Besides, where the hell would you hide it?! That thing is massive!"

She grinned and looked down, biting her lip. If I didn't know better I'd say this girl was trying to get me in bed. "Um...thanks."

"Seriously. That--how do you refer to it?" I asked.

"In girl mode it's my big clit to me."

"Big. That's an understatement! Have you ever measured it?"

Another nervous giggle. "Once when I was younger."

"Well?"

"About nine and a half inches long and about eight inches around when I'm all the way hard," she answered, biting her lip again. My gaff was getting uncomfortable.

"Wow. You're bigger than I am, you sexy little girl."

"Thanks...it doesn't look weird with...the rest of me?"

"Not at all. You said you're a sissy, and sissies have clits, yours is just, um, really damn big. I've been with genetic women who have large clits, and they're sexy, too. From what I can see, you're at least as feminine as any genetic women I've met, though. Really, Vanessa, I've never met anyone as femme as you who wasn't born a girl."

She looked up at me with tear-rimmed eyes. "Do you...do you really mean that?"

I caressed her face, then leaned in and gave her a peck on the lips. "Yeah, I do. You're beautiful."

"Even though I don't have big boobs?"

I laughed. "That's not all that it takes to be feminine. I mean, look at me. Do I look feminine to you?"

"Well, of course!" she gushed. "You're fucking hot! Sorry."

I smiled. "Thank you and you don't need to apologize. I've been known to curse quite a bit, myself. So yeah, I do have some decent breasts but I'm not alone in this room in there being something else in my panties," I told her with a wink.

She bit her lip again and I surged again. "That's the other thing I wanted to ask for your help with," she said, clearly nervous.

"What is?"

"Um...what's in your panties."

"My cock?"

With a nervous giggle she answered, "Yeah."

"How can that help you?" I intended to cajole her into spelling it all out, to hear it said out loud. That would eventually help her feel a little more normal about her kinks, I judged.

"Well..." she trailed off for several seconds. Then she took a deep breath and declared, "I wanna suck it 'til you blow your load in my mouth," in one rushed sentence.

I wasn't all that surprised but I was still caught somewhat off guard. "Really?"

Again with the lip biting. She answered, "Really. I never have and I'd love to feel what it's like."

"Which part? Going down on me or me coming in your mouth?" I asked, raising my eyebrow again.

"Both. Neither. I've never done either one and I've been dreaming about doing it, or them, or whatever."

"Are you sure?" I asked.

She displayed zero percent of the nervousness or awkwardness I had seen since I'd crossed her threshold, as she looked me dead in the eye and declared with supreme confidence: "I don't think I've been any more sure about anything else in my life. Jess."

That did surprise me. Not what she said but how she said it. "I did say that I wanted to help you in any way, didn't I...?" I said in a mock reluctant tone.

"You did."

"If I agree to help you with this, you realize that it will have nothing to do with the fact that my favorite way to come is with someone's mouth wrapped around me, right?" I inquired with a wink.

It was too much and Vanessa giggled. "Oh, sure."

I couldn't maintain the façade anymore, either, and laughed. "I'd be happy to help a pretty girl like you with that, honey. Do you want the same thing, some pointers if there's something you can do better?"

"Would you do that for me?" she asked, looking up with nothing but apparently innocent hope.

"If you want that and I get a blowjob out of the deal, of course!" I laughed.

"Um...when can we start?"

"Where is going to be the most comfortable for you?" I asked. "I mean physically. I love the sight of a pretty girl on her knees in front of me with my cock in her mouth, but if you're not used to it the pressure on your knees can hurt after a while."

"I don't care. I don't want to wait and I'll put up with it. Can we do it right here, please?"

Her earnest expression did me in. Any intention of trying to protect her from her own lust was destroyed by my own. "If that's what you want, then of course," I said, sitting back down but not smoothing my skirt underneath me as I sat. Instead, I lifted it up, then hoisted my butt up so that I could take my thong/gaff off in one practiced movement over my thigh-high stockings and heels, flipping my skirt up onto my abdomen.

My significant girlcock flopped onto my tummy, most of the way hard already. Vanessa sank to her knees between mine, licking her lips as she eyed my womanhood. "It's beautiful," she whispered. "I didn't think I'd get an uncut one for my first time, but I was hoping."

I smiled down at her. "Thank you, sweetie. I'm glad you're not unhappy that I'm not cut. You can touch it if you want."

Her eyes devoured my cock as she reached out to touch it. I murmured approval when her soft, painted fingertips first made contact, then took a tentative stroke of my foreskin, quickly evolving to a basic handjob. "This is so cool..." she sighed.

"It is," I sighed. It felt really good. Not just guiding a cocksucking virgin but also her gentle touch. "You can go at your own pace, just explore me and enjoy yourself, sexy...I'll tell you if you're hurting me or if there's a better way for you to do something," I advised.

"Thank you for this," she breathed, making me twitch, just before she pulled my sheath back and planted her lips on the underside of my head, giving it the most sensuous kiss I have received anywhere on my entire body. She was not just getting ready to blow me; I think she really was trying to seduce my cock.

"You smell so gooooood..." she susurrated. We both fell silent as she began to worship my tool, sometimes kissing it, sometimes giving it little kitten licks, sometimes just rubbing the soft skin of her face over it. By the time her lips reached the opening of my foreskin, I was hard as marble, not just from the stimulation but also from how sensuous, seductive, and sexy she was in the way she did it.

I gasped when her lips finally enclosed the tip of my foreskin. She wasn't just making love to my cock with her mouth at this point. She seemed to be worshipping it. Little moans and grunts that indicated ecstasy came from her throat as her exquisitely soft lips and tongue touched my organ in such a sensual way that it took my breath away. "I love having your cock in my mouth," she breathed during a brief break before devouring me completely. I groaned and couldn't help but thrust my hips up into the warm wetness of her mouth, which made her groan in sympathy. This little girl was a natural born cocksucker.

"Oh, fuck, you're good at this," I moaned. Her oral ministrations were going to make me come a fountain, and it wasn't going to take long, either.

"So I'm doing a good job?" she asked with a "little miss innocent" face, then smiled and winked before stuffing my mouth full of her shaft.

"You're a fucking natural," I groaned. She was pulling my skin back just as her lips and tongue swirled over my hardness, the perfect synergy I needed to get off. Her soft breath exhaling through her nose tickling the hairless skin above the root of my cock just added to the sensations.

"This may be the best blowjob I've ever had, you sexy little sissy, and you're gonna make me cum in your mouth if you keep this up," I announced between moans, grunts, and groans. One of her hands was stroking me as she sucked while the other's fingertips danced over my tightening balls. My hands had pulled my blouse up and pulled the lacy cups of my bra aside so that I could pinch and tweak my nipples and caress my voluminous tits.

"Mmmmmmm..." she hummed around my erection.

"Oh, shit...so close, sexy...you sure you want me to come in your mouth?" I gasped.

"Mmmm-hmmmm!" she groaned around me.

"Oh, wow...Jesus...fuck--I'm gonna cum!" I cried as my balls tightened.

"Mmmmmmmmm!" she said around her mouth full of my girlcock as I surged, the first of a multitude of pulses shooting into her mouth.

"Oh, fuck! Fuck! Fuck!" I cried, feeling my enhanced dick shoot rope after rope of my jizz into her mouth. It was ecstasy.

I was trembling by the time I finished unloading my balls into her mouth and my breaths were ragged as I came down from the ecstasy.

"Holy shit..." I sighed, satiated all the way in a way I hadn't been in quite a while.

I watched her Adam's apple bob as she swallowed and sat back on her heels, a very satisfied look on her face. "You're delicious," she observed.

Once I could move again, I sat up and took her face in my hands. "That was the best blowjob I've ever had, sexy. Don't change a thing," I told her before kissing her with as much tenderness as I could. I could taste myself on her tongue.

"Thank you, that's very kind of you," she said softly, looking into my eyes. "And thank you for letting me do that. I've wanted to do that for as long as I can remember."

"The pleasure's all mine," I grinned. "Literally."

She giggled, a musical girly sound. "Don't be so sure about that," she argued and glanced down at the front of her panties. My eyes followed and landed on the front panel of her panties. The head of her clit was peeking out through the waistband and the shaft was as hard as any that I had ever seen. There was a large wet spot right near the head.

"Wow. You seem to have enjoyed yourself quite a bit, too." I could almost make out her pulse just by looking at her erection.

She bit her lip. "Yeah. That was really sexy knowing that I could make you feel that good with my mouth."