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Sweet Alice

By: Akito01



It is typical in these sorts of confessional stories to change names to protect the innocent, but in this case the concept of 'innocence' barely applies. That said, I will refer to my friend here as Sweet. If you're old enough to remember the singer Matthew Sweet, then hopefully it won't seem too odd to call him that. I think the gender ambiguity of that name is entirely fitting for this story.

Without going into too much detail, I'll simply say that we met by happenstance, and formed a quick and easy friendship despite his being some years younger than me. He was also from the UK, and true to the stereotype, took the activity of bar hopping as a serious hobby.

I should say, I'm not much of a drinker. I know it is an unmanly thing to say but it doesn't take more than a couple of beers to get my pleasantly buzzed. Sweet enjoyed chiding me on that point, and so always enjoyed that when we hung out together to provide plenty of drinks. I never turned down the invitation, and on this night, as was almost always the case, the beers were cold and in plentiful supply.

Picking my brain on whatever topic happened to come to mind, I think Sweet enjoyed watching the process of my getting progressively drunk, and the way I'd get more and more talkative in an increasingly ridiculous way. Also, as per usual, our conversation inevitably came to center on girls.

"Well, I think just about any girl who cosplays is sexy," I remember saying. "I mean, short or tall, thin or fat, they're all kinda amazing, just because they have that willingness to show themselves off like that. Some of those anime costumes really show off some serious skin."

"That makes you hard, doesn't it," Sweet prodded me, nodding in agreement. "I bet you think about having a girl dress up like that for you in the bedroom, yeah? Your own personal cosplay girl to play with?"

"Well, that's gotta happen, right? I mean, I can't believe those girls don't experiment with their boyfriends all dressed up like that. You gotta think; the guy is dressed like Link, the girl like Zelda, they get back from the convention to their hotel room... It would be pretty awesome."

"You know I like to dress up," Sweet reminded me.

"Oh, I know, but crossdressing isn't the same thing."

"Maybe not, but I haven't told you that I do have one particular outfit that is very definitely 'cosplay', if you're curious to see it."

"Really? Um, yeah, sure, bust it out and let's have a look at you. What kind of outfit is it?"

"You'll see," Sweet said, happily stalking off to his bedroom.

Alone for a short while, I finished off my beer and waited for Sweet to reemerge. I didn't even really stop to think that, while he had shared his secret fetish to me in the past, this would be the first time I'd actually see him cross-dressed. I guess because it was supposedly cosplay, it didn't occur to me to think of it as crossdressing, because a fair number of guys cosplay as girl characters as a kind of joke.

"I hope I'm not too late for a very important date, mmm?"

I looked up to see Sweet standing before me, transformed. His face was framed by a long sleek blonde wig, and he wore a simple blue sleeveless dress with white pinafore apron, knee high white socks with delicate ruffles on top, and shiny black shoes.

"Ah, Alice in Wonderland," I exclaimed, delighted and amazed.

"I'll have you know that I'm much happier in heels, but the costume demands flats," Sweet said, demurely lifting his skirt a little to show off for me.

"You look really amazing," I told him earnestly. "I mean, you have the body for it. The dress really makes you look feminine."

"Do I look pretty?"

"In that wig, yeah, you totally do. I mean, if you put on a bit of makeup, you could easily pass for a girl cosplaying as the Disney version of Alice."

"In that case, what if I put on some lipstick?"

I nodded eagerly.

Sweet momentarily ducked away to do exactly that.

"I never thought you'd be into cosplay," I called after him.

"Cosplay is just a word for dressing up, and believe me, I am a fan of dressing up."

"That's... really cool. A lot of people might think it's weird, but I totally think it's cool," I rambled in my drunken way, trying to find a way to compliment Sweet without seeming too weird about it myself. "But, why the Alice costume in particular?"

"Isn't Alice in Wonderland an allegory for puberty and becoming a woman?" Sweet explained, reentering the room. "Don't you think someone like me would naturally be drawn to the character for that reason? Transformation is a rather strong theme in that story, right?"

"Yeah, I guess so."

"Truth be told, this was a leftover from another very special encounter from some time ago. The reaction was so positive, I had to keep the whole thing, wig and all."

"Positive reaction?"

Sweet just smiled enigmatically, red painted lips and blonde hair making that gesture strangely seductive.

I wasn't lying about Sweet being well suited to that costume. In the gap between her knee length skirt and tall white socks, my eyes locked onto the bare skin of his legs.

"Wow, your legs... You must shave, right? They're so nice, I mean, really nice legs. Can I touch them?"

"You want to touch me up," Sweet asked, stepping up to my chair. "My dear, you can do anything you want to me, naughty boy."

I don't think I entirely understood the meaning behind Sweet's words in that moment, but I didn't hesitate to lay my hands on his warm thighs and gently caress the smooth skin of her legs up his skit. Lost in the warmth and haze of my drunken state, I didn't even think of how I was amorously fondling my friend; I only thought about how I was touching and feeling a really nice pair of legs.

"I'm getting very aroused," I nervously admitted, pulling back my hands from the hem of his skirt. "I'll drive myself nuts if I keep going like this. You look too good."

"Getting hard are you," Sweet teased, looking down at my crotch.

"Yeah," I helplessly admitted.

"I bet you'd like to do something about that," Sweet grinned.

"I... It's getting pretty tight in there."

"So, tell me," Sweet said, leaning over me, voice very low, very quiet. "What if I took care of it for you? What if I be your little cosplay doll for tonight, and I suck your cock as much as you want, all night long?"

What would my answer have been if I hadn't been lightheaded with drink and horny as hell with an erection straining against my trousers? What would I have said if Sweet hadn't been dressed like a cute blonde in a blue dress and white socks? If I remembered this wasn't a 'real' woman, but my friend that I talked about girls with? I can't answer any of those hypotheticals, because the fact was I was drunk, randy and smitten by Sweet's blonde hair and smooth lovely legs. So, I said, "Yes. Yes, please."

Kneeling at the foot of my chair, Sweet laid his hands on my thighs and trailed his fingers up to the rise of my crotch. Looking down at him, his blonde wig made it seem like it really was Alice undoing my trousers and easing them down, along with my plain white briefs, to fully expose the length of my erection to the air. I clutched nervously at the plush arms of the chair as Sweet held the base of my cock in one hand and began to taste and tease my glans with his tongue. A few moments later, those red tinted lips closed around my cockhead and Sweet took me fully into his mouth.

Perhaps what I'm about to say is either shocking, obvious, or both, but I have to state that there was no difference in the feeling of Sweet giving me head than with any girl I'd been with before. No, in point of fact, I think this was even better. The way Sweet pleasured my cock with a languorous pace and dedication was the best I'd ever experienced before. My breath came in broken gasps as my arousal began to peak, hips rising off the chair. I'm sure that being drunk made the process longer than it might normally have taken, but the end result was inevitable just the same. I could feel my pre-cum seeping onto Sweet's tongue, and with tired eyes I watched his blonde head hovering and bobbing over my lap.

"Oh, God," I rasped, my toes flexing and twisting in my socks, teeth clenching as I felt that breathless moment of no return overtake me. Sweet kept his soft red lips firmly planted around my shaft as the thick streams of my warm ejaculate flooding into his humid mouth.

I gradually regained my breath as Sweet swallowed down the last dregs of my messy orgasm. I wasn't thinking or feeling anything at all, except for how awesome this felt, and how glorious that blowjob was.

"You came so much," Sweet observed, genuinely impressed. "I think you've been keeping that pent up for a long time."

"I... It's been a while," I admitted, looking down to where my moist and softening penis was resting in Sweet's massaging hand. "I wish it didn't have to end."

"Who says it does," Sweet said, smiling. "The night is still young, after all."

"Yeah, keep doing it," I breathed, sinking back into the chair. "Just, please, don't tell anyone we did this, alright?"

"Of course I won't," Sweet reassured me, tugging off my pants.

I quickly peeled off my shirt; so that once my socks were taken off I was completely and comfortably naked. Sweet remained just as he was, the perfect image of Alice, keeling there on the carpet in that prim blue dress and white apron. I sifted my fingers through his faux blonde hair, letting it cascade over my lap as Sweet resumed tasting and sucking on my now fairly soft cock. Even in my post orgasmic state, it still felt pleasurable, even relaxing.

"Can I lie down," I asked, finding the chair less comfortable than when the evening started.

"Sure, come over to the couch."

Lying there, I let my hand trail up and down Sweet's back and through the hair of the wig as he bent over my body and took control of my genitals again. Playing with my balls in one hand, he noisily licked and kissed my cockhead, making wonderfully salacious theater of his attempt to revive my erection. Indeed, he would very shortly prove to be successful, and under his skillful care was once again hard and pulsing.

Holding onto the base of my cock very firmly, Sweet made it stand upright so he could very precisely lick and tease my glans with only the tip of his tongue. As the pearls of pre-cum began to emerge from my slit, he very deliberately smeared it in circles so that it merged with his own saliva, making my cockhead shiny and wet. I groaned, wordlessly begging him to take me deep into his mouth, but Sweet had plans of his own. His hand restricting my ability to thrust and move, he flicked his tongue rapidly across my sensitive glans, and then alternately licked up and down the underside of my length.

The feeling was intense, not like any oral sex I'd ever had. My prick ached for penetration, to thrust, to feel engulfed. If I had asked him, I'm certain he would have sucked me again, but I trusted what he was doing, and the sensation of his fast and calculated tongue bath was so unique I didn't want it to stop.

I tensed visibly, balls tight to my body, catching my breath. Only then did Sweet take me into his mouth, just in time to catch the first jets of my orgasm. Staring down at the top of his girlish head, I breathlessly emptied my supply of semen into the welcoming mouth of my friend. I said nothing, frozen in place until the last orgasmic spasms died down, and even then I could only let out the most profound gasp.

Sweet chuckled lightly, delighted by my loss of self-control and his own sexual mastery. Did he intend on seducing me from the very beginning? I can't say for sure, but those were the kinds of questions one asks well after the fact in cold reflection. There, on the couch and basking in my post orgasmic bliss, I could think of literally nothing.

At some point I had either fallen asleep or passed out, because my next memory is of waking up with a rampant erection, and the lips of Sweet riding it up and down. No longer drunk, but with the pressure of an impending hangover, I mentally scrambled to make sense of what was going on.

"Oh, I see you're awake," Sweet observed, a slight tone of disappointment in his voice. "I was curious to see if I could get you off in your sleep. Did I make you have any naughty dreams?"

"No, I don't think so, I don't remember," I stammered, looking down my sweat stained body to where Sweet leaned over me. I was reassured by the sight of the blonde wig on his head. Perhaps it doesn't make much sense, but seeing him still dressed as Alice, and Alice naturally being a girl, it put my mind at ease about being sucked off like that.

It also seemed like Sweet had applied more lipstick at some point, because my cock had a very distinct red smear all along its length, and as he bobbed his head up and down, his lips glided over my flesh with little resistance. My head swam with the conflicting sensations of pleasure and pain, but it is fair to say that pleasure ultimately won out, because I didn't do anything to stop Sweet from deliciously molesting me. I held the back of his blonde head and encouraged him to take me even deeper, to suck me even harder.

"Take it all," I ordered him, voice rough, genuinely excited by the sight of his feminine face pressing down to my lap. There was a strange sense of freedom I had in that moment, that he was really my private cosplay doll devoted entirely to my pleasure. I didn't have to worry about being polite or nice, I only needed to lay back and enjoy the feelings of him sucking me off.

When I came, it was with a slow lazy intensity, a suffice wash of warmth, my semen more oozing rather than jetting into Sweet's wonderful mouth. I moaned aloud, my head lolling back onto the couch. I enjoyed every moment of this orgasmic bliss. My hand slipped off the back of Sweet's head, and as his tongue scraped against my softening erection, I nodded off to selfish sleep.

. . .

As strange as it may seem, the next morning was not awkward or shameful. Certainly, I remembered everything that had happened. However, dressed in normal clothes, Sweet no longer looked like the blonde haired Alice who had sucked my cock all evening. Still, he was openly amused and delighted by his conquest of me, and teased me about it over coffee.

"You really need to get yourself a girlfriend," Sweet observed. "You had so much cum saved up, it made me wonder if you even masturbate to relieve yourself."

I blushed, remembering the intensity of my first orgasm last night.

"Well, it is hard to meet girls," I explained lamely. "Especially the right kind of girl, you know?"

"Hmm. Well, it seems to me, you might need another outlet for sexual relief until that right girl comes along."

"It's... I mean, sure, but, unless..."

In truth, I wasn't sure what I intended to say next, but Sweet didn't hesitate to fill in the gaps.

"If you ever want another night with Alice, I'm sure I could arrange it," he smiled. "Our little secret, yeah?"

"Yeah."

Sweet Alice Returns



After the night I previously described to you with Sweet, it naturally occurred to me to wonder if he had seduced other men in a similar manner. It may seem silly or naïve, but I honestly had no idea. With some sly delight, this is story Sweet told me.

Naturally, to preserve the identity of all involved, I will continue to refer to Sweet as exactly that. He was not dressed as Alice on the night in question, however. No, for this impromptu house party he was dressed in something more typical of his crossdressing style; a sexy blue dress and black heels that showed off his legs and slender figure. 

Now, I realize in telling this story second hand, some of the finer details are going to be lost. How large was the house? How many high school seniors were there? How drunk did everybody get? I cannot say for sure, but at the least the party was large enough to include many people Sweet had never met before.

One of these strangers was a lanky blonde guy who, beer in hand, approached Sweet with a polite and hopeful nod.

"You look really nice," he told her.

"Thanks very much," Sweet replied. "However, you should know I am crossdressing."

"Whoa, I'm not into that," he loudly proclaimed, perhaps afraid anyone might have noticed their brief exchange.

"You came clean right away," I asked Sweet in surprise as he told me the story. "You didn't want to string him along?"

"Honesty is always the best policy," Sweet assured me. "Not everyone is as open minded as you. Some guys can get very upset if they think they've been fooled, and when you add alcohol into the mix..."

I nodded, not needing anything more to be said on that point.

As it turned out, this wasn't the end of the story. It was much later into the evening, when the crowd had thinned and various couples found things to do with each other than dance and drink. Sweet was alone by now, having taken refuge in an empty bedroom to enjoy some peace and quiet, and stared to think about calling a cab to head back home.

This was when the blonde fellow from before wandered into the room. He seemed pretty relaxed, which put Sweet at ease as he came to sit on the bed beside him.

Sweet was curious about his apparent change of heart, but he was rather shy and found small talk difficult. This suited Sweet fine, since small talk was boring and he had other things he really wanted to know. 

"So, tell me, have you ever had a blowjob before," he asked, smiling.

The young man stammered for a moment, as if too affronted by the suggestion that he lacked sexual experience to offer a coherent answer. Then his expression softened, and he quietly admitted, "No."

"You know, I could give you one if you want," Sweet said, leaning towards him, the long hair of his wig brushing against the other's shoulder.

"What, no way," he exclaimed, shaking his head.

Still, he didn't get up to leave, and Sweet trusted his instincts not to give up. Besides, he was great fun to tease.

"I promise not to tell anyone," Sweet assured him. He licked his lips in a deliberately exaggerated way, hoping to either turn him on or make him laugh. Either way, he could see his expression relax, his posture less defensive. Was he considering the opportunity of receiving his very first blowjob? Was he imaging the feeling of those red lips surrounding his naked manhood? The growing bulge in his trousers seemed to answer those hanging questions.

"OK," he finally surrendered.

Sweet quickly leapt up to close the door, then knelt in front of him, watching as he nervously opened his pants and let free his erection from his briefs. A virgin cock; pristine and pale, but hard and eager. Sweet was tempted to ask if anyone had even touched his cock before, but he didn't want to make him feel even more nervous. Whatever the case may be, he was about to receive an education in the delights of oral sex.

Taking hold of the base of his cock, Sweet didn't give him the opportunity to second guess his decision and slipped the thick head between his lips. I felt myself getting hard myself as Sweet told the story, my cock responding of its own accord, recalling the sensation of those painted lips.

I think Sweet must have noticed, as he took delight in describing how the guy moaned out loud as he sucked him. Lipstick visibly smeared along the skin of his cock as he moved his head up and down over his lap.

"Don't slow down," he begged Sweet, his hands clutching the edge of the bed.

Sweet didn't need to be told. Within mere minutes, his entire body seemed to stiffen and tremble, his warm thick semen flooded into Sweet's mouth. The poor lad must have been aching for it for the longest time, judging by the amount of cum Sweet ended up swallowing down.

The guy clearly loved the experience, and whatever revulsion he may have had towards crossdressing was most certainly a thing of the past. Still, he begged for him not to tell anyone.

"Don't worry, your secret is safe with me," Sweet assured him as he got up to leave.

"Lucky fellow," I remarked. "Most of the house parties I ever went to never ended that way for me. I wonder how he felt after the fact, you know? Was his mind opened, or did he feel weird that one of his most formative sexual experiences was not with a 'real' woman?"

"It's fun to be someone's first," Alice mused, momentarily leaving the room. "Sometimes, they even come back for more."

"You really are one of a kind," I called back. "I think I've learned a lot from you. I used to think of the whole gay-straight, male-female thing was very clear and obvious. It isn't, though, is it?"

"I dunno. You tell me."

When Sweet returned to the room, he was wearing a sleek back haired wig, light makeup, and fresh red lipstick.

"It looked as if my story got you a bit excited," he said, nodding towards the rise in my pants.

There wasn't much I could say to dispute that.

As if recreating the scene he'd just described, Sweet knelt in front of my chair and waited for me to undo and pull down my trousers. I hesitated, but much like the young man at the party, I found it difficult to resist the erotic promise of those soft lips and talented tongue.

And, just like that unnamed virgin, I let out a loud appreciative moan as I felt Sweet's mouth close around me. It is difficult to write in words the exact feeling of his tongue on my glans, the erotic pressure of his sucking me, his head bobbing up and down. I gently laid a hand on that feminine black hair, pretending for the moment that Sweet was an easy party whore who I'd had the great fortune to meet, and watched the skin of my prick turn reddish in color from the still fresh lipstick. 

All too soon, I felt my balls go tight, my hips rise from the chair, and my teeth clench as the first burst of semen erupted out of me into his mouth. Without flinching, Sweet captured and consumed all of my ejaculating cum, barely a drop escaping his soft lips.

In the aftermath of my orgasm, Sweet looked up at me with clever eyes. 

"I have other stories I could tell you too," he said.

"Maybe another time," I told him weakly. "Or, you know, at least give me a half an hour or so..."