Hello all my crossdresser and sissy girls! It’s been a while since I made a real “how-to” post, so I thought I would give some advice on how to strap-on fuck crossdressers and sissies. Or rather, how to TAKE a strap-on and how to get yourself ready for it. The getting ready part can also apply to those that are going to get fucked for the first time by a real dick!

Now if you watch strap-on porn it looks easy. The crossdressers bends over, the girl, or guy, puts on the strap-on, slides it in slowly, then bangs the sissy hard. Easy! HAHAHAHAHA!!!! NOT! If you have never done it, that is NOT how it’s going to work! More likely you will feel pain like you’ve never felt before, you might rip your colon, and you just might have a nasty bowl movement. Not a fun time!

Now, I’m going to tell you what worked for me, others might have different ways and tricks. If you’ve never had anything up your ass, it does not feel natural at first. Your bodies first reaction is to close your anus muscles tightly and push it out. For the first few times practice on yourself, by yourself. Pick a time you can relax and know you’ll be alone. Now, start with something SMALL!

But before you even try a toy, there is something else you must do. In order to have a nice, clean time of strap-on crossdresser sex, you MUST be feeling good and not have much in your bowls. That means if you have been feeling sick to your stomach, seem to be having an “active” day and so on, don’t try any anal sex. If you are not in perfect form inside, you could have a nasty movement you can’t control.

No one wants that! So there will be some days you just will not be ready to try it. If you know your going to do it that night, eat solid foods that day that you know agree with you. Eat light, and try to empty your bowels just before you try it. If you feel “full” or just have that “not sure” feeling down there, DON’T DO IT! Also try not to drink a lot, as it can make you want to pee.

They have lots of toys you can find online or at your local sex toy store. Some are mini dildos you slip on your fingers like a point. You want to start with something about as big as your finger. Get one very small, a middle size one and a bigger one. Also get lube, LOTS of it! Anal sex is messy, no way around it. Lay a towel on your bed, strip naked and lay on your back. Put on the fingertip toy, or a small dildo you got.

Don’t get a toy too soft, or it will bend and not force it’s way in your ass. Ok, now put lube on the toy and in your crack. It helps if you shave down there. Spread those legs and touch your opening with the tip of the toy. Now, your body will try to close, to keep it out. So here’s what you do. Apply pressure on it, but not too hard. Relax, then push just like your doing a bowel movement. That makes your muscles open.

At the same time you do that push the toy harder, and it should pop in. Now, your muscles will try to close again, but it can’t because of the toy. It will feel very weird at first, maybe a bit painful. If you can’t take it, pull it out, relube and do it again. Try it as many times as you need. After a while your body gets use to it, and the muscle will relax. It may take 20 minutes or so, but it will relax.

Now, you may feel a huge bowel movement, like your body wants to empty itself. If your empty, nothing will happen. But if you are, well, you might have a mess. This will stop once you do it often and your body gets use to the feel of a toy shoved up there. There’s a lot to this huh! After your muscles have relaxed you can slide the toy in and out, feels good doesn’t it!

Once you have done that, you can try a bigger one, then a bigger one. How big should you go? It’s up to you. Some want to stay with a slim one, others want to see how big they can go. Most stick with a normal sized dildo or smaller. Once you have a bigger one in, try a long one and see how far you can get it before it gets uncomfortable. That way you can tell your partner to never go too far, or get a strap-on dildo only as long as you can take it.

If you go in too far, you hit something that can be very painful. Not sure what it is, but trust me, it’s not fun! Just slide a long toy in carefully until you feel it, it will not hurt until you try to push hard. So then you know how long to get a toy. That way your partner can slam it in hard and full without worrying about hurting you. So you’ve worked your way up to the thickness you want, you know how long you want it, good.

Now you can get your partner into the action! There are many ways you can have strap-on crossdresser sex. It’s the same as a guy fucking a girl up the ass. You can go on top and ride it, bend over and take it from behind, even be on your back and have your legs lifted high and wide! I think the best is having your high heels and stockings on, getting bent over the bed with your legs spread wide and knees locked straight.

You can be “forced” to have strap-on sissy sex, get it shoved in your mouth before getting your ass banged. If you trust your partner you can be tied up and get strap-on fucked, that is hot! Make sure your partner knows to use lots of lube. If it’s a long session, it may need to be re-lubed a time or two. The more you do it the easier and funner it gets, so do it often! Below is a strap-on I like, you can click it and check out all the strap-on toys they have.

So just take your time, do lots of solo practicing on yourself until your body is use to it. Strap-on crossdresser and sissy sex is great fun and the most feminine your ever going to feel. Well, unless you get fucked by a real dick, or a shemale! If you have any tips by all means let me know. Enjoy your crossdresser and sissie strap-on sex!

Strap-on harness and dildos for strap-on sissy and crossdresser sex