Hullo :o)
I've recently found a way to achieve multiple orgasms.
Yeah, I'm a guy.

This could take a while (I'm drinking, and feeling a bit chatty), so you might want to finish what you came here for and read this afterwards.
If you're even interested.

First off, it's not that muscle control thing where you just cum once, like normal, but you can let it out in "lumps". This is a series of distinctly seperate "endings" followed by a god almighty "finish" over the course of a few minutes. I've done this on 3 different occasions now, so it is a real thing, not just something hinky that happened once. And I can't really see any way of putting it to use with anyone else; it's pretty much a one man job, I'm afraid.

A quick bit of background, I suppose.
I needed a bit of cheering up, because nobody's going to be interested in a sad, boring, glum little fuck, are they. And I needed to feel a bit happier about myself, because if I don't like me then why the fuck would anyone else bother. Since there's nothing that makes me happier than "pretty" does, I thought I'd have a go at it myself and try being a sissy, for a little while at least.
And, yeah, it has worked. I'm feeling much happier and smilier now.
If I can just remember that I'm single now BEFORE I'm halfway home again, I might even get around to chatting up one of the boys or girls at the supermarket.

Anyhoo, on to the main event. I'd got myself dressed up all girly one morning, with my knob tucked away and panties pulled up really tight to keep it there and started watching some of those sissy hypno trainer thingees. My knob was kind of bent around in almost a full circle with the tip right back up against the base of my ballbag. It couldn't really get hard, just sit, squashed in there, twitching and leaking.

Those sissy hypno thingees are quite fascinating, and time sure does fly when you're having fun... ummm, yeah, ok, it was about 9 hours later. I'd worked myself up into quite a state and really, REALLY needed to finish. I was kneeling up on my seat, possibly leaning forwards to kiss or lick the screen at apropriate times (possibly; I can neither confirm nor deny that at this particular time), with a hand shoved down the front of my panties kind of just stroking and squishing myself with my fingertips in a girly sort of way when I came. It was a definite cum, not as good as you'd expect after 9 hours work, but a definite cum. I didn't really feel like I'd completely finished though. So I kept on going. I was still "up there", you know, still close, so about a minute or so later it happened again. And I kept going. Straight through a "WTF?" (I'm going to call it a half) and on to a real FINISH!

I was feeling rather happy at this point. (Well, you can imagine, can't you.) My legs had gone to sleep so I kind of fell off the chair onto the floor a little bit, giggling quietly to myself as I tried not to pass out, and dragged myself into the lounge for a smoke. I certainly felt completely finished (and soaked), but by the time I'd rolled myself a smoke I'd kind of realised that even without any makeup there was something I could put on my face to make me prettier. And would be a shame to have eaten all those pineapple chunks for nothing.
This one took a good 3 minutes (including crawling and smoke-rolling time).
So I'd call that 4.5 within about 6-8 minutes.

I staggered off for a quick look in the mirror (mmmm, so pretty) before collapsing in the shower. I may have been giggling and licking my fingers before I finally did pass out, I really couldn't venture to speak on the matter without a... oh, alright then, maybe a little bit.

Well, that was fun.

From subsequent experimentation I've found - it only takes about an hour or two to get worked up enough; I do need to be kneeling, or on my back with my legs in the same relative position; if I let myself get even the slightest bit hard it's only going to be a single finish (usually a pretty epic one, mind you); and it doesn't happen every single time no matter what I do (3/5 attempts so far).
I've never actually passed out again, but I do get damn close every time (that buzzy, tingly feeling and all those grey blotchy things popping up to say hullo are just part of the fun - you'll be fine).

You'll be fine? Ah, yeah. I'm kind of hoping that at least some of you will try this for yourselves and let us know how you got on (If only to break up the monotony of all the "faggot" and "tldr" replys I'm likely to get).
I'd fucking hate to be the only one who can do this, ya know. That would just suck arse.

My spun sissy fantasy all last night was, having a sexy 18 year old girl find out I'm wearing tiny little girl panties in a sex shop. Humiliated I beg her to keep quiet and let me run away in shame, but I'm led to the back to the porn booths/gloryholes and made to strip down to only the panties for her to not tell everyone inside. She grabbed my clothes as she snapped a picture with her phone camera, and told me to do whatever she said or I'll be left there in panties as she tells the whole store. She wants to film me saying my full name, address, and beg to be her sissy sex slave. Sissy porn is played while I masturbate till she gets back with " supplies " and I'm bound, blindfolded, with a choice of begging for chastity or being castrated. I'm crying like a real sissy bitch as she locks the smallest cage made on my now non existent penis, laughs, and breaks off the key in it. She tells me to decide either work the gloryhole for her to record and post online or be led out of the store by leash publicly and permanently her sissy slave.... Crying and humiliated I'm stopped at the front door of the store where I hear men and women laughing at me, she says out loud " you're not a man you're a sissy who will never touch that tiny little limp sissy clit again, I locked it in chastity and broke the key so you can only cum from having a sissygasm ever again. Then she slips something over my balls followed by pain, and explains the castration band stays on until I can cum like a true sissy. Proving that I am and always have been a sissy for dominant women and real alpha Males to use and abuse to fill their sexual wants and fantasies, or allow her to take the last of my masculinity permanently. Tears flow down my face as she records me bound, blindfolded, on a leash in front of a crowd of strangers at a sex store with the smallest chastity cage made and a castration band break my mind and any remaining delusions of being a man. I start to beg and plead with her to let me try and have a sissygasm right there with everyone watching and laughing as I swear to do anything she tells me to because I am her willing and obedient sissy slave for life if my mistress will allow me too try and save my worthless tiny sissy balls by having my first sissygasm right there for all to see. She agrees with conditions, my sissy clit is strictly off limits any touching or stimulation will cost me my balls no excuse, I must sit on and ride a dildo till I sissygasm or give up no vibrators allowed, and I have to suck every cock put in my face/swallow every drop of cum shot in my mouth/thank every man for his cum . I'm made to thank her for proving that I am not a man, and then she tells me the punishments for any failures plus I have to pick the handicap I want to endure while she she creates an online pay per view video blog to post all the humiliating videos she has got planned for my porn career. I can swallow one m2f transformation pill with every load of cum I swallow if I want estrogen lubrication on the 10 inch long 3 inch thick big black dildo, or swallow one pill everyother cum load but with numbing cream on the dildo make having a sissygasm take extremely long. I ask for more pills and estrogen lubrication and start to cry again when she says everytime I fail to swallow the pills or one drop of cum eagerly and with a smile another band will be added to my balls castrating me faster, failing to thank anyone sincerely results in an extra band, pill, and my home address. Every man I make cum before I can sissygasm adds a band I find out after I look into the camera and tell everyone that will ever watch my full name and that I wanted all this to happen and i willingly consented to this "forced feminization" video asking everyone to enjoy my "fantasy" come true of being actually made into a permanent sissy publicly in a forced feminization "simulation" movie with a forced fake smile acting excited about losing my failed life as a male. After the second band gets added everyone starts choking me unconscious with their cocks while telling me to rub my sissy clit and cum for everyone like the sissy I am, my castration is happening regardless and I should hurry up and have my first sissygasm and actually cum for the last time of my life. My first sissygasm has me shaking and moaning like a girl, then the blindfolded is removed as I cry and sob seeing my dead black balls knowing It's to late. I have to finish off the movie by thanking all the viewers, all the men who feed me their cum and feminization hormones, and my mistress for making my dreams come true turning me into a sissy that will never cum again. But my nightmare has just started... message me if you want to hear more.

I confess that i actually did kiss my dad's friends daughter while she was sleeping.
one day i was at her house and she was sleeping in her room. the adults were in the other room probably fucking or whatever, so i snuck into her room quietly. i made sure she was sleeping by poking her gently then i bent down and kissed her on the lips. not a sissy kiss either. i had my tongue in her mouth and everything. but then she woke up and i told her not to tell... she told and i denied it. also i was rubbin her pussy through her pants but she didn't know that.

I am 28 years old, live by myself with my dog, and havent dated in almost 2 years since my last boyfriend cheated on me. Since then I have become addicted to huge toys and random objects in my ass and pussy.

My little brother was living at home with my mom, but they were having a lot of issues, I knew this was in large part to my mom being a push over so I told her that I would let him stay with me and deal with him.

I think just being in a new environment and everything did the trick. That is until a few weeks ago. I started to notice that my panties would go missing, but then they would be in the dirty laundry, full of my little brother's cum.

At first I didnt say anything, I would just smell or lick his cum out of my panties and wash them. This went on for a couple weeks until he escalated to putting the panties he used back in my drawer. I noticed this one morning getting dressed and I slipped on a pair of boy shorts and felt they were wet and gooey right on my crotch.

I instantly started to rub my pussy and fell back onto my bed. I grabbed my hitatchi and was squirting into my panties within minutes. I called into work and walked into the kitchen in just my panties and bra. You could clearly see that my panties were soaked through.

Kyle walked into the kitchen and just stopped frozen, staring at me. I just looked over my shoulder at him and bit my lower lip. We stared at each other for what seemed like an eternity.

He finally left for school and I spent the entire day watching porn and using my toys. But I went into the guest bedroom Kyle was staying in with my laptop and a few of my favorite toys. I squirted all over his bed multiple times.

Once I was worn out I took off my bra and panties and left them on his bed. I got a shower and put on a new bra and panties that were very sexy, lacy, and low cut, and then I slipped on a pair of sexy heels.

I was cooking dinner when Kyle got home from school and he went straight into his room. I had finished dinner and went to go get him out of his room. Right before I knocked, I stopped and decided to just barge in on him to see what he was doing.

I opened the door really quick and saw my little brother with my panties wrapped around his cock. He didnt say anything, just kind of freaked out and tried to cover himself up. I just giggled and walked over to him, strutting my hips as I walked. I pushed him against the dresser, wrapped my hand around his throat and I could feel him shaking, and whispered in his ear "no more cumming without your big sissy's help, understand lil boy"

I backed my face away from his just enough so he could see my smirk and said "Good boy, now its time for dinner"

I let him go and strutted my stuff walking out of his room, knowing he was staring at my ass. After a very quiet dinner watching American Psycho...I made him go clean up the kitchen as I drank some wine and laid on the couch, spread across all the seats after I took off my heels.

I was so wet thinking about playing with my lil brother. He came back to watch the movie with me and sat at the other end of the couch. I put my feet in his lap and told him to massage them for me. I was kind of surprised at how well he rubbed my feet, but I still over did my moans a little bit to tease him. After about 30 minutes I started to rub my feet against his hard cock.

"Thank you for leaving me my gift that I found in my panties this morning"

He just got super red and didnt know what to say. I consoled him and told him that I loved it and what I had done all day. I told him that if he wanted to continue to get off under my roof, he wasnt allowed to do so without me.

He agreed and I told him to come with me and led him into my room. I laid on my bed and told him to get onto and massage my back. He started to get on the bed and I stopped him, told him to strip down for me. ALL the way.

He was such a good little boy, stripped down and his big cock sprung out. He sat over my ass and started giving me an amazing massage. I could feel his cock throbbing against my ass cheeks.

I asked him if he wanted to cum in the panties that I was wearing. He said yes of course, but didnt know what I had in mind.

I made him lay on his back and grabbed his cock. I pulled his cock inside my panties and started to grind my pussy against his cock, I was so wet I thought he was going to pop into my pussy.

I told him not to cum until I instructed him to do so and it was a waste of time. He covered my pussy within moments. I slapped him hard across the face and told him "Bad boy, now you have to be punised"

I pulled off my panties and sat on his face and made him lick my pussy clean. It was a strong mix of his cum and all the juices from my pussy. Once all his cum was gone he really started to suck on my clit and I squirted all over his face.
Then I took my panties and stuffed them into his mouth and told him to roll over on his stomach and close his eyes.

I got up and put my strapon on and grabbed a bottle of lube. I lubed up my strapon cock and his cute little ass. I was expecting him to resist but he just laid there. I slid my strapon into his ass and held him down. He just moaned and pushed his ass back against me.

"Ohh, you like having your ass fucked lil brother? You like having your big sissy fuck your ass?" and I thrusted into him even harder.

I started getting into a crazy fucking his ass and started to cum. I didnt squirt this time but it was still an amazing orgasm. I slid out of his ass and cuddled my lil brother as the big spoon and reached over and grabbed his soft cock.

"Did my good lil boy cum?" I asked

"Yes, I did twice"

"Twice?!? Wow, that is a good lil boy."

He asked me what this means now, between us. I told him as long as he keeps behaving, is a good lil boy for me, I will keep his cock and his ass happy. If he isnt, he can go and live with mom again.

Needless to say I wake up every morning getting my pussy eaten out. Then I return the favor and we get ready for the day.

His birthday is coming up and I told him he can do whatever he wants for an entire weekend with me. I told him in advance so he could start planning.

Cant wait to see whats in store for me...

"What " I asked her. I heard what she said but hoped I heard wrong,,actually prayed . She smiled and then back handed me ,reminding me that I was to refer to her as Mistress at all times,then confirmed what I thought she had said which was that I was to wear my pink satin lace bra and panties to church along with my pink lip stain . I told her I could wear my bra and panties and maybe not be noticed but there as no way that I would get away with my lips stained pink,,every one would notice ,,and it was church. She to;d me to ether go to My church dressed as she said or she would give me the address of another one for me to start going to . I asked what the catch was and decided that it would not be as bad going to the church she said even though I would have to go totally feminized because it was one of those churches that didnt care . She smiled and said they wouldnt say a word to me for being a male dressed like a female . She told me she would pick out my outfit and I had to go dressed like she said but after that it would be my decission how to dress and I said I would wear what she decided no matter what. I figured it was church and she would pick something like a woman would wear just sluttier than normally and was I wrong . I tried to reason with her and was told to shut up and get dressed in what I was given and not say a word about it or she would call Thomas and he would make me put the clothes on then drive me to my church and drag me in so everyone would see and tease me,,I quietly put on everything and got ready.I couldnt believe I was going to church dressed like a whore,,black PVC miniskirt that was a size too small , matching pink PVC panties and bra and thi hi stockings with high heeled shoes . I looked like I was whore on her way to work,,not a sissy on his way to church and was so nervous. Mistress made sure that I had to stop and get gas and that I would be late .All the close parking was taken so I had a long walk to the door but wasnt the only late person and wasnt hassled about my outfit at all . Once I was inside I was relieved to see that I wasnt the only male there dressed feminine , or the only one who looked like a hooker .