Saving Sissy

Yes, I had this schizophrenic feeling - on the one hand I knew he was a male, but on the other hand - he simultaneously presented himself like a pretty young woman, so I was constantly a bit confused, even giddy. The beer didn't help!

We all were drinking excessively and soon Anika became a bit detached from us, eyes glazed over, speech slow, mumbling something. Gabriel and I, on the other hand, were giggling like tipsy girls, discussing some creepy teachers at our college, sharing memories about failures and successes in college life.

I almost felt like I had known him for a long time, loved his light and pleasant energy; the talk was effortlessly flowing, as we seemed to understand each other with ease.

We soon relocated to a swing bench that could gently sway from one side to another, but as a consequence, we were now sitting much closer than before.

Meanwhile, Anika disappeared inside the house, going there with a bit of a wobbly walk, and didn't come out, so he and I were left alone talking about more and more private and intimate topics.

I shared with him that I was now single and had not had much luck with girls in recent years.

He, despite being so drunk, still had trouble explaining to me why he married Anika at all. But finally, after the fifth beer, he gave up and mumbled:

"Yeah... I just wanted to freely crossdress and wanted someone who would let me do it inside the house... I wasn't ready to find a man, my mother was alive then, I couldn't break her heart like that. So, I met Anika, and she gave me what I needed...more or less."

Even through the drunken haze in my mind, one thing caught my attention.

"But... you were interested in men at some point?" I asked, raising my eyebrows.

His face became more red, although it also could be a side effect of the beer.

"Kind of..."

"Kind of? Care to elaborate?"

He looked a bit embarrassed. "You know. Guys like me, small femboys and crossdressers are at the bottom of the ladder in the gay community. We are often held in contempt, used and brutalized. Rarely praised or cherished. And seldomly respected like daddies and manly tops. I once installed Grindr but uninstalled it the same day. I didn't feel safe. I wanted more than to just be a hole lusted for by some random guy who would use my body like a disposable tool. I wanted to be with one person for the rest of my life, who would love me and accept me as I am. It may sound stupid and naive to you, but I've been a romantic for as long as I can remember."

I hesitated. "It's not stupid Gabriel. I totally understand what you mean by that. I, myself, always craved to have a special connection and close relationship with somebody. That's why I never hooked up, I had a long-term relationship with all of my ex-girlfriends as I also wanted... more. The trust and devotion."

He blushed and lowered his head.

After a short pause, I added, "Have you ever tried it... with a man?"

Gabriel shook his head. "No. I wasn't that bold, or... rather desperate. I was living with my parents, before I met Anika. I was petrified to be... treated badly. I'm not exactly a tall and strong man. But what about you? Are you only interested in girls?" He redirected the topic to me, obviously having enough of confessions about his sexual life.

Biting my lips, I murmured: "I'm rather straight, but to be honest, I'm also open-minded and if the guy was pretty and cute, why not? I could experiment a bit."

I was surprised with my own words. The beer was strong, indeed.

He almost hid his red face behind the can, sipping the beer for quite some time, not commenting on my words. Honestly, I also had no idea how to even understand my own statement. It was really weird what I just said. Especially in front of... this pretty, cute guy.

I cleared my throat. "So, how do you... do it with her? Forgive me, I'm so inappropriately curious, but you are so much smaller than she is. I just can't wrap my head around that. Sorry."

His jaws clenched a bit. He was very embarrassed - even being that drunk! I was sure that if he were sober, I wouldn't get anything from him.

"I fuck her with a strap-on," he blurted out, his face even more fiery red.

I froze; in my alcohol-infused state it seemed pretty absurd, so I chuckled stupidly, and he suddenly looked even more ashamed.

"Is that so? Do you need it? So, how much are you packin?" My lips quirked.

He snorted and chuckled. "God, you are really nosy... and blunt!"

"C'mon... don't be shy. I won't judge. I'm not that big myself, only 7.5 inches." I winked.

He gigged. "Only? You are a funny guy. You call 7.5 'only'?"

I huffed. "But it's not 'porn size', for sure!"

"Well, how about that - I'm 3.5 inches. Less than half of yours..."

I raised my eyebrows, but even drunk I would never have shamed another man's cock. He avoided my gaze, looking somewhere in the dark garden.

"She calls it an overgrown clit," he added in a hushed voice.

"That's cruel, man! What a bitch. But if you fuck her with strap-on... you don't, you know... cum?" I had trouble arranging my thoughts into coherent questions. I was thoroughly buzzed.

He shrugged and averted his gaze. "She fucks me too. With another strap-on."

I must say, I was pretty shocked. His wife was pegging him?! How weird was that?

The silence crept up to the garden, I had no words. It was beyond me.

"Well, looks like you have an arrangement that... fits both of you?" I smiled dumbly to cheer him up, as he looked a bit constipated.

I also gave him another beer. I had to be honest - this discussion - it was too much! Even for heavy drinking, this was only my second meeting with this guy. I never ever had such a discussion before in my entire life. But, well, my curiosity and the alcohol were doing their job very efficiently.

"So... how did you get interested in crossdressing?" I changed the topic a bit, to better the mood.

He sighed, taking a sip from his sixth beer. I noticed he had some trouble aligning his lips with the hole in the can.

"It was my friends from high school. Girls, of course. They always said I'm small and cute and should actually be a girl. I was one of the smallest kids in high school. So, sometimes when I was invited to their homes they put makeup on me, and dressed me up, almost like a doll."

"And why did you let them?"

"Why not? We were good friends... and they made me look cute. After high school I kinda missed that. So during college I secretly dressed up in my room. I was also trying to date girls, but... you know. When we were finally in bed they were... unimpressed with me."

I chose not to comment on that.

"So how did you finally get to meet Anika?"

"On a public internet forum. She wrote a post that she would love to meet a crossdresser, and she happened to be from my town... so. We met and that's how it started."

"Was it love at first sight?" I sneered.

He winced. "Sadly, not that much. Initially, we just complemented each other's needs. She had trouble finding a boyfriend and was happy to meet me. I felt wanted. I told myself she was perfect for me because I knew... I truly wanted an unusual girlfriend. So, we kind of matched. But for me, it was more of a rational decision than an emotional one. It seemed to make sense. At least it did... then."

I drank the last two gulps from my seventh beer and leaned toward him a bit.

"I sort of understand that you have this... crossdressing kink. You could easily pass for a woman in this outfit. I must admit, I'm having serious troubles tonight - remembering that you are actually male. I constantly repeat in my head: He has a dick!" I burst into drunken laughter. "But once in a while I forget that, and I just have this strong feeling that I'm sitting next to a pretty girl!"

He wiggled his eyebrows a bit. "Well, I take it as a compliment..."

I winked slyly. "Sure it is. You are very cute. If you were dressed like that when I carried that fridge, I would have begged for that kiss, and not care about you being male..."

He responded with a typical drunk giggle, and leaned a bit toward me. Our heads were now very close, our shoulders touching. I felt a very pleasant shiver. The taboo... the forbidden. A male in a dress. Weird? Or... interesting?

"I was actually considering giving you that kiss, hahaha..." he replied rather briskly, and even winked.

I opened my mouth. "Seriously? You looked like I just killed your mother, so shocked and scared."

He bit his lip. "I just... you know. I was a bit overwhelmed. But the thought crossed my mind, definitely."

I didn't know why, but I started to feel my dick. It was bothering me pretty much the whole time we spoke, but kinda low-key. Now it was stiff and ready.

But why?

I never was interested in males. Yep, I liked small, cute women, but did he match the description? He surely could be confused with a cute young lady...

I ogled him. One strap fell from his slim shoulder. His collarbones were beautiful, pristine white, and smooth. He had a flat chest, but I was never into big tits, anyway. What else? Small hands, shaven forearms, slim waist...

Yep, he didn't have a pussy, but still, he had another hole that I also liked to use in the past, while in relationships with my exes. I could go with that, to be honest. His dick was small enough not to remind me too overtly about his manliness. So...

Wow. I suddenly went so deep into that? How did THAT happen?

I was actually considering having sex with a MALE?

Fuck. This beer was really strong.

I licked my lips. "Why exactly? I was just joking, you surely knew that..."

Gabriel also finished his sixth beer with a couple of gulps. He had trouble putting it on the table, so I helped him. His slim fingers lingered for a moment on mine. I didn't mind, for some reason.

And then he asked, closing his eyes and leaning down to the back part of the bench, his shoulder was now pressing on mine even more.

"Were you only joking, Evan?"

I knew it was a serious question, even if I barely heard his whisper. Even alcohol couldn't take the edge off that.

Gabriel had parted lips and closed eyes. His head was laying limply.

"To be honest, not entirely. I noticed you had pink lipstick and mascara. It made me... curious."

He didn't open his eyes, remaining in the same position with his head tilted back.

"You're thinking about it now, aren't you?"

I was really drunk, but still, this took me by surprise. I had to think for a second about how to answer.

"You know, you really do look like a pretty woman, Gabriel, for me it's very hard to remember that you have a dick."

"Or an overgrown clit..." He giggled, but sort of in... slow motion. It was funny.

"That's what she called it, but I wouldn't say it like that, she meant it to be disrespectful."

"She likes to tease me that my dick could fuck her nose, not her pussy. It gets lost down there...She can't feel anything".

"Maybe it's her problem... Maybe she should start to flex her Kegel muscles."

He chuckled again. "Oh. You are so sweet. But it's really small, Evan".

"You are small, it would be weird if you had a big dick. Disproportionate?"

Gabriel sighed. "You are trying to console me, obviously, it's kind of you, but it is what it is..."

He still didn't open his eyes; he was talking slowly, almost like falling asleep. Alcohol hit him hard. I had the impression that perhaps he was enjoying this dizzy state. He just... let it all go.

"Well it's hard to judge, I haven't seen it."

"The thought alone disgusts you, right? Seeing another man's dick?"

I raised my brows, he was becoming weirder the more drunk he got. Weirdly intense!

"No, why would it To be honest, after all this talk I'm curious how it looks."

He chortled a bit. "Well, I don't show my dick without a kiss first." Just after saying that, he started to giggle stupidly, obviously more drunk than I was; he also began to slide down, his arm now pressing on my arm with full weight. His head was so close to my shoulder that it only would take one inch, and he would place his cheek on my shoulder.

"I've never kissed a guy, Gabriel," I muttered, a bit uneasy.

"I'm hardly a guy. I'm something in between..."

Something in between? Hmmm...

Even being so confused, I could feel my arousal more and more. Because of the alcohol, I had trouble focusing on rational arguments - for example - was it wrong to be talking about kissing with a married man? It was probably a bad idea. Yet, ignoring this quiet voice in the back of my head, I immersed myself in the sweet feeling of relaxation and bliss that was surrounding me now.

I sort of stopped caring, nothing bothered me anymore, I was just chilling.

"I've never kissed a guy either," he mumbled, and his head finally was close enough that his cheek grazed my shoulder.

He tilted his head in a way that it would be easier now for me to kiss him.

I glanced at his pink, parted lips - they looked so soft. Inviting... Tempting.

"Do you want me to kiss you?"

In a normal situation I would never have asked that, it was too crazy. But I was far too tipsy to worry about the consequences.

"Only if you want it also..." he responded, whispering. "And I have a debt, don't I?"

He still didn't open his eyes, was this some kind of half-dream state for him? Unreal?

His way to get detached from reality?

I stared at his waiting lips. They looked nice, plump and pretty feminine. Maybe I could just try it?

What the hell, so what if he was a guy, he was also pretty, it made it easier for me, for sure.

I slowly lowered myself, feeling like I was diving into some different realm.

There is a first time for everything, right?

And...

... I closed my mouth over his pouty lips.

We began this experiment.

Gabriel from the beginning opened himself for me eagerly, no resistance whatsoever! I never kissed anyone giving me his mouth so submissively. I conquered and dominated his tongue, explored pretty much every corner of his pliant mouth, I could push my tongue almost to his throat and he was just... taking it. I overpowered his warm, wet tongue, rubbed over it, I almost invaded him with the fierceness of my kiss.

Fuck, it was an exquisite feeling.

I was drunk in this kiss, in him, fully immersed in this moment.

His tiny hand wandered over my chest and neck, ran through my hair. I moaned inside his mouth, and reciprocated with a similar gesture, but... in a downward direction. I grazed over his chin, slim neck and flat chest(I could feel tiny, hard nipples on my way down) and abdomen, then... in a wave of curiosity, I grazed over his groin.

Yep, I felt it.

Something small, yet hard, under my fingers. He moaned as I touched it carefully, gently stroked. It wasn't a clit, for sure.

I broke the kiss, but he didn't open his eyes. I looked at his lips. They were a bit swollen now, red and wet and so fucking inviting that I just had to kiss him again. I couldn't deny myself this feast.

So, I was kissing him more and more intensely, my dick became so crazy hard that it was pressing on my stiff zipper and I felt even a bit of pain. I grabbed Gabriel's arms, pulling him closer to me, sweetly pliant, not protesting at all even when I pretty much yanked him to my chest and put my hand on the back of his head, on his nape, kissing him in a passionate, wild way.

He wrapped his slim arms around my neck and just let me kiss him for as long as I wanted, and I wanted to do it for a long time... I finally also started to kiss his jawline, and his delicate neck. He smelled so nice, with a subtle jasmine scent.

I felt such a powerful desire for him that I sort of lost the rest of my rationally thinking mind.

That's why I unzipped my pants and... pulled his petite hand over my dick.

Gabriel gasped and opened his eyes.

They were glassy, unfocused, yet I knew he was in some small shock, touching my hard, hot shaft.

"Jerk me off, Gabriel!" I ordered, focusing my eyes on his face with crazy passion. Thank goodness there was such a high wooden fence, so neighbors couldn't see us.

He... obeyed!

His tiny hand started to move up and down along my shaft, and I could just focus on kissing his lips and neck continuously. Even with the alcohol intoxication, I could feel my orgasm quickly gathering in my balls - I was aroused like never before - and after maybe two minutes of his work, I spurted over my stomach, groaning loudly, and feeling delightful jolts of pleasure spreading from my dick.

Yep, I needed that.

Definitely.

I opened my eyes and looked down, catching his blurry gaze. Fuck, he was so drunk, he was like in a trance state... Yet, his lips were still super tempting. So swollen and plump now, I needed to suck on them, bite them, devour them, and when finally I backed out he... grabbed my hand and... mimicked my gesture from before.

"Jerk me off, Evan, please..." It was, however, pleading, not ordering.

I was in such a good mood, that a bit more of gender bending was still a possibility for me. I felt relaxed and almost... happy?

With some hesitation, I pulled his frilly dress up. He was wearing women's panties, pink in color. They were now strained with his dick... I freed it from his underwear and stared at it for a moment.

This cute, small cocklet was pink and hard, sticking out boldly, and his pubes were smoothly shaven. It was actually a pretty nice dick, only small. But nothing wrong with it. He had a shapely head that was glistening with pre-cum, and a smooth shaft. His balls were also small, shaven and pulled tight. I stared at this in amazement. It was really esthetically pleasing to ogle.

"That's a pretty dick, Gabriel! Yes, small, but very pretty. Cute, like all of you," I said with a soft smile, glancing at him. He was observing my face with rather unfocused eyes. He seemed to be only half conscious. Like a person swimming in a haze.

"Thanks... you are so sweet, Evan" he murmured.

I was wondering how I could jerk it off with my big hands. He had tiny hands that could handle his tiny dick. But what about me? Being sober I would manage it, probably with three fingers, but in such bedazzlement, I wasn't so sure. So, I darted a gaze at him. He was still observing me - waiting.

Okay. What could I do? Only one, very crazy thing.

VERY CRAZY.

Do it with my mouth.

Wow. YES. Madness.

But alcohol was my best friend in this situation. Gave me courage and the willpower to take such a bold initiative.

So, I slid on my knees beneath the bench and lowered myself over his small dick.

I took it all into my mouth in one move. He made a quiet whining sound, and gasped loudly, obviously in shock I would do such an insane thing. His both hands landed on my arms.

The taste was rather neutral, maybe a little salty around the slit. I could also smell the scent of shower gel on his skin. I squeezed my mouth around it and pressed my tongue to increase the friction. And I started to work on it, quite relentlessly. He was short enough, so I had no problem with gagging - I did my best with this advantage, sucking him off in earnest, tightening my mouth and tongue around him. I simply remembered what I liked, and I reenacted it on his dick.

The alcoholic haze also helped in dulling the other stimuli; the rhythmic movements, up and down, lead me into this kind of almost hypnotic, trance-like state, where I was just sucking him off, without realizing of how much time it could take, or how I felt about giving blowjob to another male. In a way - the beer haze shielded me from self-consciousness and worrying too much.

I have no idea how long it took me, three minutes or ten... time suddenly became an abstract idea for me.

I could feel the slight squeeze of his hands on my shoulders, where they were all the time, lying calmly, as I worked on him. Now his fingers suddenly clutched my shirt.