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I'm a total top and have been almost my whole life, however when I was just starting out exploring gay sex, I thought we both HAD to bottom and top equally, or somewhat equally. I had fucked my best friend several times at this point and he always seemed to love having my thick cock pounding a load into his hole.  He had repeatedly eaten my hole and fingered me, and it mostly felt good so one summer day I was so horny it was nearly painful and I decided to invite my best friend over for a fuck.

I was masturbating in the bathroom to kill time and started fingering my asshole.  It felt good, like I said I was incredibly horny.  I grabbed a dildo shaped object and put oil on it and slowly pushed it against my hole.  The object had a round end that was the thickest part of it, and it tapered down to the thickness of a finger.  The thickest end wasn't really very thick, about the size of a half-dollar coin.  It hurt like hell getting it past the second anal ring, but since the object tapered so much it was mostly smooth sailing after I got the thickest end past my inner ring.

I slowly worked the thickest end in and out of my hole, trying to get it relaxed and used to penetration.  About then my buddy showed up and we got onto my bed and began sucking each other's cock.  He was leaking precum more than usual, so I guess we were both more than the usual amount of horny.  He got between my legs and started sucking my cock and fingering my hole.  I rolled over onto my stomach and he got the hint and crawled on top of my body, forcing my legs open so they were spread wide.  He spat and lubed his cock head, ready to penetrate my ass.

Now I should say, that the biggest thing I'd had up my hole was the object I had just recently been fucking myself with and his cock is still, as of today, the biggest I've ever seen in real life.  It's over nine inches, uncut and incredibly thick.  I felt him place his wet cock head on my slightly oiled hole and start to insert his monster cock into my virgin hole.  Initially I cried out, although UI knew the first time would hurt.  Looking back all I can say is how dumb and uneducated we were.  We should've been using oils, or lube or anything besides just our spit to have our virgin holes fucked the first time and many times after. 

Anyhow, it felt like a telephone pole was being pushed into my ass and up into my stomach.  He lay completely on top of me working his gigantic cock in and out of my battered hole.  I was crying but he couldn't see it. All I could do was lay there and take his cock hoping he'd cum as soon as fucking possible.  It didn't take long, but it felt like an eternity before he finally filled my hole with his cum. 

I immediately went to the restroom and expelled an enormous amount of cum and some blood, but surprisingly I wasn't bleeding as much as I felt like I should be.  I rubbed my tender hole with my fingers and stuck two fingers inside my cummy hole while I jerked off, shooting cum all over my chest, stomach, wall, and floor. 

My first time getting fucked was a painful experience, but we didn't know the proper way of losing or taking a virgin hole.

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Painful and bloody is a great way to start. How else will fags learn that they exist to suffer for male pleasure?

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      SESSION 1: Establish ground rules with your sissy and especially about making her obey you and submit to your will. Get to know you sissy and what makes her tick. Make sure she agrees to trimming her body hair and dressing up sissy gurly clothes for the next meet which should be either at your place or a hotel room.   


       
      2) Establishing follow up sessions. This is where sissies may try to get away so it is very important to start as you mean to go on with her. Your second meet with the sissy must get them into their gurly outfit and vulnerable to you. You must be charming and reassuring and to the sissy at first in order to get more and more of your own way of them. My greatest advice here is to ask the sissy if you can record and take pictures of her in gurly dressed mode for your personal collection. In the moment, they will tend to say yes and do it. A simple picture of her in her outfit of a skirt and panties (or better still as sessions progress, on her knees sucking your dick) could well be the key to her entire enslavement. Your power and control over the sissy can be fully established from then on. From then on you only need suggestively say you like the picture and want to send it to her friends if she is reluctant to meet. Record her every time after that to ensure you have plenty of face pics of her being a sexy sissy.  During the first meeting, make her cum, be verbal, make them tell you what a bitch they are. Make her promise they will be your sex toy. Make them give you their word they will suck your dick in the next session. This is important, you don’t want to put your sissy off by demanding too much in the first session. So each session must build on the last doing more of what you did with her last time and a couple of new things you didn’t do last time;

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      3) Chastity is another way of grooming for gaining control and domination over your sissy. This is better for long term and for training them to be submissive sissy cum sluts. Sometimes sissies have that moment of wake-up and sometimes regret which is especially likely when they finally cum. They will do anything before that moment, but can feel like they went to far once cum. So you must take advantage of that to groom them into doing anything you want. It is important to keep your sissy turned on by keeping their clitty erect but do not let them cum whilst you are still training them. Not allowing them to cum will keep them submissive, turned on, and obedient. Sissies are more likely to do anything you want while they are turned on but less so after they have cum. So you can do whatever you want for however long you want. Make the sissy learn to enjoy their orgasm denial so they feel trapped and needy to be nice to you. If they are resistant to this initially, you can keep pushing it, and just put it on them if you can convince them to be tied up to stop them satisfy themselves without your permission. Start gaining their trust about tying them by tying their hands up for short periods getting longer each time. Forgiveness over permission. Use a chastity device that cannot be removed without a key, which you keep.

      SESSION 3; Sissy to be in bra, panties and skirt. Make removing her tights and top a ceremony. Make her clitty hard and make her let you put your dick in her mouth with some sucking. Make sure you tie her hands up for at least 10 minutes. Finish by masturbating and cuming on her face then let her cum on her skirt and make sure you tell her that its her reward for sucking you. Homework for sissy; To practice cleaning herself with enemas if she is not already good at doing it. Make sure you give her plenty of how to guides on enemas to read and tell her that she will be tested next sessions. Any resistance to completing her homework can be broken by reminding her of your photo album. At this stage, your sissy can also start growing her hair long or she can get an expensive wig.


       
      4) Training you sissy is very important and the longer you take to do it the better you will transform her into a total obedient slut. Before starting this session make sure she has a proper enema and starts to acknowledge her gurl pussy with your command; “Clean your gurl pussy”. At this point you should not let your sissy cum more than once a week as keeping her horny will keep her wanting more from you.  It is important for her to associate her own pleasure with after she has satisfied you. In order to do this you will need to make more use of controlling your sissy’s orgasm and her chastity device.  Suggest tying her up both arms and legs this time and get her to agree by saying she will be allowed cum as a reward. Once she is tied up, put on the chastity device so she has no say about it coming off or staying on. Prolonging how long it will be before she cums will make it more intense for her and then there will be much less chance of her regretting anything you make her do for you. When she lets you fully tie her up she has no say with what happens and this will dis-empower her and allow you to properly start her sissy training. You can now start to anally train your sissy to cum without stimulation from her gurly clitty and to eventually cum without being hard. This will be easy now that you have her completely tied up. Teasing around their gurl pussy with your fingers will help. The goal is to have them only cum from anal stimulation. If you have to, make them wait another week if they can't cum without touching their clitty.

      SESSIONS 4-10; Get your sissy used to wearing pink knee high socks, skimpy pink panties, hand cuffs, ankle cuffs, neck collar and leash. This time make sure you cum in your sissy’s mouth and make sure she swallows you cum. If not punish her by spanking her bum.  Stroke her clitty from behind like a bitch so their cock is pulled behind their legs while you finger their pussy. At this stage 2-3 fingers are enough. Make sure she cums with your fingers deep in her pussy. You must now tell you sissy she is only allowed to cum if something is inside her pussy. Homework; Your sissy must keep practicing her enema skills at least twice a week and this time she has to use a medium butt plug in her pussy. She must keep her butt plug inside her pussy overnight for 8-10 hours whilst she is asleep. After each session make sure her butt plugs are getting large in preparation for sessions 11.  


       
      5) As time goes by with this regime you will want to introduce more changes to your sissy’s life. These changes will cross the "point of no return" and will keep her as a sissy longer than anything else. They may resist to these ideas, but you can keep pushing it on them and on some level they want it more than anything in the world. Ultimately, it is their choice and you are just bringing their inner sissy from within them.  Shaving smooth will make a huge difference in how girly the sissy looks and just keeping her body hair trimmed is no longer good enough. You must encourage the sissy to get laser hair removal all over her body. The final stage will be her facial hair as symbolic act of surrendering her old male identity. Another suggestion would be for your sissy to have her ears and nipples pierced and make her wear a necklace with a “sissy slut” tag that she is not allowed to remove. Making her wear makeup outside is another humiliating way to feminize your sissy in public, such as a trans or gay club. The final step is the one white sissy’s think about the most. They feel it is their destiny and that is a final step to submitting and giving up their ego for humiliation. This includes bareback sex and hormone treatment for your sissy. Make sure your sissy knows that you are never going to use condoms and that she has no choice about this. There are two types, anti-androgen and estrogen. Estrogen will have the most effects, such as face breasts and a submissive tendency. Anti androgen will make them more petite, less muscle, and make their gurly clitty smaller. Tell them they need to look pretty and pleasurable for you and that they are better off this way. Affirm it is who they are on the inside. It is best if you administer the hormones to your sissy yourself at then end of each session. Tell them they can only cum, if they have their hormones. There is research to suggest that hormone pills can be dissolved in a little water and then injected into the anus, the deeper the better. Large syringes can be used for this purpose. Once inside her pussy, her body will quickly absorb the hormones.  Only when your sissy has accepted her injection should you let her cum.

      SESSIONS 11-15; Completely strip your sissy in this session and make sure she is completely tied up. Use her mouth and have her suck your dick until you feel near to cumming. Then get between her legs and start introducing your sissy to the feel of having your dick rubbing her pussy. Rub your pre-cum over your sissy’s pussy and push just the tip of your dick inside her pussy. In every session onwards push more of your dick insider her for longer. Reward her for each bareback session by letter her cum. Make her hungry for more of your dick. Homework, in addition to her other ongoing assignments above your sissy should now be only allowed to cum if she a) has a large butt plug in her pussy and has taken a hormone pill.  


       
      6) Enslaving the sissy is the goal. Establish Dominance and always push your sissy to being ever more submissive. This will be easier the longer they take their hormones.  Treat them like a sex toy. Your sissy’s pussy needs more than just female hormones to soak up. A sissy pussy also needs cum insider her to soak into her body. A sissy must take bare dick with no protection from the injection. Nothing must block your cum from going deep inside her pussy. Receiving creampies from her Mistress is a sissies ultimate surrender to you. Make sure she knows that this is going to happen to her and that she will be impregnated with your cum and become your breeding whore. This will forever make her your sex slave, submissive and obedient cum slut. As an extra you can save your cum between sessions by freezing it. You can then use your cum during sessions to dissolve some hormone pills. This mixture can then be injected into you sissy’s pussy after you have cum inside her. Make sure before she is allowed home that she then keeps her hips elevated off the bed for a couple of hours so that every drop soaks deep insider her.   

      SESSION 16 onwards; Your sissy should be tied up and she should expect you to cum in her pussy whenever you want from this point onwards. The first time you cum inside you sissy make sure she begs you not to pull out. Make sure she knows you are getting close to cumming. Make her beg and beg for your cum before you finally give it to her. Her first insemination should be with her on her back, arms tied up, legs tied above her head, hips raised up on pillows and with you pounding her pussy. After cumming in her pussy inject her with any cum and hormones and leave her in that position for at least a couple of hours.   

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