That Time I Got Topped Ch. 01

I'd been waiting for this for a long time. Willow was sexy and smart and she always looked so effortlessly great; she even turned the girls' heads. Sure, I wasn't the tallest, the richest, the smartest or the most well-endowed guy at the university. In fact, I'm very much the opposite. I'm not much taller than the average girl and I have a girly face and body. But I had dreams of making Willow my girlfriend and then eventually, my wife.

Willow had silky brown hair which she draped over one shoulder. She often played with her wavy bangs while she was lost deep in thought. Her clear blue eyes were captivating. The way she stuck her tongue through her teeth when she thought no one was looking at her was enchanting. As you can guess, I'd been pathetically longing for her from a distance. Willow and I were distant friends, on the same course at university, but I'd wanted more since I first set eyes on her, yet too nervous to ever say anything.

That changed on the night of a house party we'd both been to. I had managed to get her attention. As the party wound down sometime after midnight, Willow and I found ourselves laughing and chatting on the settee. After a whole year being stuck in the friend zone, tonight Willow seemed to be into me as hard as it was to believe. But the way she leaned in when I spoke, the way she watched my lips, the way she found any excuse to touch me and let her hands linger on me. None of that compared to her just coming out and saying it:

"Do you want to fuck me?"

"Wh--Willow... N-N-No, of course not."

"Todd, I'm asking if you would like to have sex. There's no need to be shy."

"It's not a trick? I was worried because I've liked you for so long and I thought you didn't like me and..."

To shut me up, Willow kissed me, stood up, and held out her hand.

My concern that she wouldn't want to fuck me--beyond my girly appearance--was that I had very little experience with girls. That is to say, none whatsoever. I was a virgin, though I didn't want her to know that.

"Come on. Let's go back to my place. I spoke to Sasha earlier--that's my roommate--and she's hooking up with some guy, so my dorm room's free."

We walked the streets to her dorm, my hand in hers. Her skin was soft and warm, while I was getting all sweaty and worried how I'd do. I didn't expect to be any good my first time, but I knew she wasn't a virgin and I really wanted to make her feel special.

She took me into her dorm and let me get comfortable on her bed. I couldn't believe that this dream of mine was about to come true. But Willow hesitated to undress me, let me undress her or even just fool around with me. Her expression grew increasingly worried.

"Are you okay, Willow? You haven't changed your mind, have you?"

"No, it's not that. I don't want you to think I'm a slut inviting you back here so suddenly, but I am a slut."

"No, that's not true." I stupidly tried to cover for her. It just came off awkward considering I didn't even know what was really upsetting her.

"Todd, it's okay. What I wanted to say is that I have a secret, and it's going to be hard to tell you, so I think it's best if I just showed you instead. Let me change into something sexier."

She sauntered into the bathroom and I eagerly awaited her return. I checked my hair in her mirror and wiped away any traces of sweat. It took her a few minutes to return, dressed in something incredibly sexy. She wore black lace panties and a matching bra with a body stocking over the top, missing material around the crotch for her to pull her panties aside. She stood taller than me in black stiletto heels, and had tied her hair into a braided ponytail she rested over one shoulder.

I was stunned speechless, but I didn't notice at first what she was so worried about. If she was worried about her looks, there was no reason to be. But she really did look so nervous to be stood in front of me like that, bashfully avoiding eye contact and holding her shoulders in for a small, submissive pose.

"You look amazing." I tried to cheer her up.

"You haven't noticed." She replied, still without looking at me. Her hands ran down her body, and she pinched the material at her panties. She pulled it aside, and as she did, I noticed the lump inside.

I wondered how I might have missed it before then, but I think I didn't see it because I didn't want to. Where a tight, shaved pussy should have been, she had a penis, locked inside a small, pink plastic chastity cage.

"I'm a sissy." She told me. "Sasha would only let me live with her on the condition that she could feminise me and my Mum would only let me move to the university on the condition that I live with Sasha. We went to school together, you see, and Mum always thought Sasha was more mature than me."

"I'm surprised, obviously, but I still like you. I want to do this."

"You have no idea how much that means to me." Willow chirped. I had set her mind at ease. She approached me for a kiss.

"It doesn't matter to me that you're a boy. I still think that you're the sexiest girl I've ever met."

"You're so sweet, thanks Todd. I'm going to take the cage off now, Sasha only lets me take it off when I'm going to have sex. She doesn't even let me masturbate. You have no idea how horny I am right now."

"Wait. You don't just want to have sex with me so you can cum, do you? I was hoping you liked me."

"I do like you." She promised. I would have been perfectly reassured if she wasn't so busy grabbing the key to her cage from a small box under her roommate's bed. She was so busy she wouldn't even spare a second to look my way.

She joined me on her bed to take off her cage. Her hands trembled as she tried to fit the key into the integrated lock, so I took my time to stroke her thighs.

"If you really like me, prove it. Leave it on."

"Wh-What?!" She begged me.

"If you don't, how will I know that you really like me?"

"I... I suppose." She whimpered, I think she was on the verge of tears. She handed me the key, and shut her eyes. That was all I needed, that promise. I couldn't actually make her go without getting that uncomfortable-looking cage off, I felt like a major wanker just lying to her.

So I put the key into the integrated lock, and watched her face light up as she realised she was getting out after all. Willow wouldn't look this gift horse in the mouth and wasted no time sliding the plastic shell from around her cock and followed hastily with the base ring. Then, she gave her cock a couple of tugs and sighed in disappointment.

"I think it gets smaller every time I take the cage off."

"Well, it's the most feminine cock I've ever seen." I told her. I mean, I wasn't lying, but she knew I was talking shit. But she leaned into me anyway. And rested her head on my chest.

"Thanks. Have you ever had sex with a boy before?"

"Uh, yeah! Lots of times!"

"You're not a very good liar. That's okay, I'll walk you through it. Something I like to play is 'biggest dick tops'. Don't feel like you have to say yes, but would you be open to me topping you?"

"Wh-What?! No way!"

"Then how about we compare dick sizes but we'll agree on different 'prizes'. What do you want if you win?"

"Umm... Let me think..."

I wanted her to be my girlfriend, but I didn't know if I could really make that demand.

"You can ask anything." She teased, almost as if she could read my mind. She softly stroked her flaccid cock meekly, not trying to get erect and give her size away, while still being desperately horny.

"If I'm bigger, I want you to be my girlfriend."

"Okay. If I'm bigger, I want to dress you like a girl and go on a date."

"In public?!" I yelped.

"Well obviously. I thought... I bet you'll look super cute. I'll let Sasha pick out your clothes and do your makeup and no one will even be able to tell you're a boy. She did all that for me when I was starting out, and no one could tell. You couldn't."

She'd shrunk, that's what she said. I really didn't want to risk being smaller than her and having to dress like a sissy for a date, but I wanted her to be my super cute femboy girlfriend. My cock wasn't particularly big, in fact it was smaller than average at bang on five inches. I'd just have to hope that no matter how big hers had started off, it was smaller than that after shrinking.

"Okay, it's a deal."

Looking on the bright side, even if she was bigger and I had to crossdress on a date, it would be time spent together of the romantic sort; time I could use to try and get her to fall for me.

I unbuttoned my trousers and slid them off. And then I took off my boxers. Watching my dick, Willow hungrily licked her lips. She began stroking her soft dick in earnest. I just needed to look at her cute face and girly body to get hard. Soon enough, we both sat there with throbbing hard-ons--and though hers was way fatter than my cock--at a glance there was no obvious difference in length. She stood up and I stood up and she rubbed the tips of our dicks together.

"H-How many men have you had sex with?" I begged. A huge part of me was turned off by the idea of her having sex with other men, I was hoping that the number would be low but she had described herself as a slut. But I needed to know. How could a virgin compete with all the studs she might have fucked?

"I've had sex with nine different men. You'll be number ten." She answered. She didn't lift her eyes from our kissing cocks. She didn't see how much that answer pained me. But I absolutely had to ask my next, even worse question.

"H-How many of those men have you topped?"

My question got her attention, and she looked up at me, smiling deviously. Her cheeks flared with a cute blush.

"I topped four of them, but not because I was bigger than those four, I was only bigger than two of them."

"Have you had sex with anyone where it was really obvious which of you was bigger?"

"It was pretty obvious with all of them. But there was one guy who had ten inches, he felt incredible. Wait..." She mused. "Are you saying you don't know which of us is bigger? You can't tell?"

"You can?" I barked back.

"I guess I've just had more practise at this than you have."

She placed our cocks against each other so our balls pressed together and the undersides of our cocks rested against each other with our shafts pointed upwards like to people stood back to back to compare height. As she stacked our dicks up against each other, the tip of hers rose just a centimetre above mine. It was only average length, but definitely bigger.

"Don't feel bad about it." She warned me. "I still find you hot. I'm looking forward to this. But I win the bet. You need to dress like a girl and go on a date with me. And I'm really looking forward to that. I've never been with another sissy before."

She could tell how much that teasing humiliated and frustrated me. So I decided to punish her for it. I'd be as rough as I could.

"There's only one sissy here. And she's going to learn that real men fuck, while sissies get fucked."

"Is she now?" Willow teased. "Well then, I think this big, powerful man better claim the sissy as his own, don't you?"

With that, I put a hand on her shoulder and forced her down to the floor. She knew what to do, and put a hand around my cock. This was the furthest I'd ever gotten with a girl, the view was incredible. Willow squat on the ground while her other hand played with her own cock. She looked up to me with her cutest expression.

"I'm way too horny not to get fucked tonight. So tell me if you get close."

Despite being absolutely horrible at edging when I'd previously played edging games watching porn, I don't think I could refuse a blowjob--my first blowjob--from this cutie.

She ran her face up and down my cock sniffing audibly. She just pressed her nose up against it and breathed in until my scent clung to her. And while she did, her hand frantically stroked her own plump cock. She was obviously extremely aroused by all of this.

Having run out of patience, she began to suck on the tip of my dick.

"Willow... That feels... So amazing..."

She didn't reply. But she did suck harder to acknowledge my compliment. She warmly cupped my balls with one hand, and continued stroking herself with the other, while she licked the tip and pushed her tongue left and right, gliding it over my sensitive tip.

It was only after all that, when she finally pulled the foreskin over my crown, to expose more smegma than I expected. I felt hugely embarrassed. I had forgotten to clean it during my last shower, but it was still a lot.

But instead of looking turned off, Willow looked excited. More than was natural. I'd heard sissies were the most sexually deviant nymphomaniacs you'd ever meet, but this was more than I thought possible.

She continued sniffing, and lapping at the tip and cleaning my cock of all that nasty smegma. And the drunken face she pulled told me that this was paradise for her.

"Does it really taste that good?" I begged. She didn't answer, she just took my entire cock deep into her throat while her sweet eyes gazed up to mine. But I did get a response, marked by her tightening her throat.

Shaking, she managed to rip her hand from her own trembling cock, and stroke mine as she bobbed her head up and down on the tip. I stroked her hair while she blew my cock.

I kept groaning to tell her what a good job she was doing, and she in turn massaged my balls, stroked my shaft and licked and lapped at the tip with the force of a vacuum cleaner.

Willow slobbered all over my cock, saliva dribbled down her chin and hung from her reaching down to the floor, her hand glided over my cock drenched in her saliva, and continued on, tickling my balls. Eventually her saliva trail met her other hand massaging my scrotum.

Over time, Willow took more and more of my cock into her mouth until she was deepthroating it over and over again. She was an expert, not gagging once no matter how many times she disappeared my whole shaft down her throat. She could also hold it for as long as she wanted, and wouldn't brake eye contact.

I couldn't stop moaning, my legs were wobbling, and my balls were tensing up. I had nothing to compare it to, but I would wager that Willow was an absolute blowjob queen.

With no sexual experience, I hated that I only lasted a couple minutes, but I was on the edge after that incredible blowjob and it was time for her to stop if I was going to fuck her. I'd need a few moments to cool off as well.

"Willow, I'm going to cum." I told her. She was watching me, but she didn't stop. This femboy was a tease, she wanted me to get as close as I could before she'd stop. I groaned and my left eye shut itself, as my body started shaking. My balls tightened so much, and my hips began to jerk on their own.

"Fuck, Willow, stop. I'm really close."

Again, she didn't stop. I noticed just how into this she was. Her dick was still so hard. Her eyes seemed glazed over. I don't know if she could stop herself. The overpowering smell of my dick had hypnotised her.

So I braced myself and fired an enormous load of cum down her throat. She pushed my cock deep into her throat and swallowed every wave of cum I launched into her. She filled her belly with every last drop. And then she collapsed onto her rear, and pulled my cock from her mouth. She looked so incredibly satisfied watching my dick shrink down to its flaccid size. But as the sense returned to her, I watched her face grow confused.

"You came." She realised.

"I told you I was close."

"I know, I know. I'm not blaming you, Todd. I messed up. Come on, lay on my bed, I'll get you hard again."

"Willow, I can't get hard again so soon. Maybe we could have sex another time?"

"No! I need you now. I haven't had sex in ages and Sasha doesn't let me masturbate, I told you that."

Willow was obviously panicking, her voice had gone high-pitched and she spoke quickly. But there was little I could do to comfort her.

"I'm sorry, Willow, but I can't fuck you now. You could masturbate now before you put the cage back on."

"No, Sasha doesn't like it when I do that, either."

She sat down on a wooden dresser between her and Sasha's beds, beautiful in front of the starlight decorating the city skyline through the window behind her. I sat near her on the edge of Sasha's bed.

Willow's fat cock hadn't lost a millimetre of length, she really was so hot and bothered. I knew that she was the one who messed up, but I still felt so bad for cumming too quickly. Like before, Willow avoided my eyes. Defeated, she put a hand on her chastity cage she'd left on her bed.

"I'm going to go have a cold shower to kill my boner. And it's late, you should probably go home. But you'll call me tomorrow, right? To plan our date?"

"Yeah, I'll call you first thing... Willow, come on, there must be something you can do."

"I told you, I'm only allowed to have my cage off when I'm having sex. You can't get hard again and you made it clear you don't want me to top you."

"W-Well... Yeah. But I want to see you get off."

"But I... You said you can't..." Her eyes pierced past the veil of my uneasy expression, and she came to a realisation. "You'll let me top you?"

"Yeah."

"You don't have to let me if you don't really want to."

"Come on, Willow, you're not going to make me beg for your cock, are you?"

She blushed bright red.

"That would be so hot. I don't need you to beg, I just need to know that this is what you really want."

"Willow, it is what I want. I want you to fuck me with your beautiful, fat cock."

"Well, shit, how can I refuse that? Since you're an anal virgin, we'll need lots of lube."

For a moment, I thought she said 'since you're a virgin', and I worried what might have tipped her off. But realising what she actually said didn't make me feel any better. I was a virgin, and it struck me that this was how I was going to lose my virginity; getting fucked by a femboy who had a bigger dick than me.

For the lube, it was back to the box under Sasha's bed. Right underneath where I was sat. Willow got onto her knees, and seeing her there, between my legs, I wanted another blowjob. But my dick was still far too exhausted for that, and could barely twitch. She eyed it hungrily, and then glanced up to me, and kissed it, before winking and pulling the box out. She opened it up and pulled out the bottle of lube, and a vibrator. She first lubed up the vibrator, and turned around for me to enjoy watching her slide it into her hungry arsehole. She pressed a button on it, and moaned softly to the humming it made sending ecstasy through her very core.

She looked back over her shoulder, and wore a dirty smirk.

"Like what you see?"

"You're so sexy."

"Thank you. Now, I need you to turn around."

I did as she asked. I got onto all fours on Sasha's bed, facing my arse out towards Willow."

She crawled over and delivered a soft spank to my arse.

"You're sexy too. You'll make a cute girl on our date."

Next, Willow began licking my arsehole, her soft velvety tongue felt so large and fat against my tiny hole. And it made me worry what her cock would feel like. But though this didn't feel like what I expected--I expected it to feel like she hit some magical pleasure spot that made my cock burst--but massaging those muscles felt good in a different way.

With my hole softened for her, Willow took the lube and squirted it onto two fingers.

"It feels better warm but I really can't wait a moment longer."

She fingered my hole, not too deep, but working to loosen my muscles to allow her thick cock entry.

"Does it feel okay?" She asked. "It doesn't hurt, does it?"

"N-No." I answered.

"Just wait until I hit your P-spot. That's when the real magic happens."

I liked her checking in on me. She really was girlfriend material, save perhaps, by the fact that she had a bigger cock than me and was about to fuck me. With my hole thoroughly lubricated, she poured a healthy dose on her own cock, and slathered it all over until her cock was dripping with it.