She wants to make me a sissy

My girlfriend told me she wanted to see my virgin ass fucked. She knows I like to wear panties so she gave me a couple of outfits to wear and gave me a few toys. She says I'm in training right now. She tells me to wear buttplugs and to fuck my ass with a dildo to prepare my ass to get fucked. I can wear a buttplug for hours now, but when I try to fuck myself with a dildo, it's still uncomfortable.
I think she is going to find a guy to fuck me next week. I'm not sure I'm ready for it. Has anyone else been through this? The whole idea turns me on but I gotta tell you I'm afraid I might not like it.
Also if any of you have some tips on what she should have me do for my training, she would love to hear it.

Just go woth her ideas if you are a true sissy you will love having a man inside your sissy pussy. One thing you need to do as a propper sissy is shave your whole body. My mistress has had me shaving for over 15 years and both she and I wouldnt have it any other way.... good luck and enjoy
I have finally decided to take control (total) and have sissy in panties daily lock sissy in her CB 6000s for good. No more feeling sorry after a few weeks and no more giving into her pleas for mercy! Welcome the NEW MISTRESS!

This all started a few weeks ago when she was too tired to go meet a bull she was talking to. So she told him I would come over and suck him off. I liked it! Since then she has sent me out to suck cock and I willingly obey her wishes. Now she wants to watch me getting fucked.

Here's another pic

I have to wear this all day today

lucky sissy lap

For a long time after I started to take it up the ass (in plastic from a strap-on) I found it very uncomfortable. I was turned on by the idea (and got off on that when I thought back on it later) but the physical sensation itself was uncomfortable and often even painful. Then one day my wife had me bent over the arm of her couch (a big round, foot wide arm) and was doing me and it was suddenly just wonderful.

I can't tell you exactly what it was - some combination of finding the right position to stimulate my prostate and my finally learning to relax my sphincter muscles properly I imagine - but it was a breakthrough and I've loved it since. I came that day as she fucked me without touching myself (although I think it owed as much to the friction of my little sissy dicklet against the coach as it did to the friction on my prostate.

Here is the best advice I can give you:

1. Practice relaxing your sphincter muscles completely. You will likely find this much easier if (A) your body is otherwise comfortable and (B) you are bent over (relaxing while getting pounded from the front and looking at him is hot, but it is harder - a more advanced position.)

2. Tip 1 above is why butt plugs have limited utility for sodomy training. Although a poorly aimed dick or dildo can hurt by banging the back of you rectum and missing the prostate, the bigger and more common pain for most people is the resistance of the sphincter (designed to make sure things go one way generally) to the intrusion. Because plugs have flared bases, the sphincter - the very part you need limber and elastic for you lover - doesn't get any stretching. (In fact, it closes tightly to try to prevent the plug from coming out.)

3. If your girlfriend is open to it, ask her for more practice with a strap-on before the big day. Go slow and use plenty of lube and practice relaxing. (If she can't/won't obliged with the strap-on, at least do what you can with a dildo yourself to practice relaxing those muscles.)

4. When it happens, make sure you are well lubed and ask him to ease in slowly, stopping frequently if necessary so that your anus can adjust. Don't be afraid to have him back-up some so you anus can pucker around him properly. Take care with you position and height. For most males it feels best if his dick is sloping a bit upward into you and not down. Again, don't be afraid to have him pull out completely and ease again slow. Once he is in, let it sit a bit and then have him go slowly in and out. If he slams in fast at first or starts jackhammering right off, it will hurt -especially for a virgin like you.

5. No matter how it feels, make sure and tell you girlfriend that you loved it. After all, we don't want her backing off you sissification, do we? If it was uncomfortable or painful, tell her that too and tell her that you hope she'll work with you and practice so that it the pain or discomfort doesn't happen the next time.

Good luck fellow sissy!
Pantalone, Wittol, oblate, abnegator, fellator, pathic, irrumatiophile,fop, epicene, cotquean, skivvy, thrall, and pilgarlic.