For general advice on pegging, take a look at the article “Pegging–A How-To Guide” . Going to be the pegger rather than the peggee?  Try the “A Woman’s Guide to Pegging“.

Looking for Part One on how to prepare in advance?  Look here.

So you’ve prepared in advance and now you’re ready to go—what do you need to think about on the day?

1. The more relaxed and aroused you are, the better it will be for everyone.  You may want to start out with normal foreplay and sex, so that both of you are in the right mind frame.  Make putting the harness on part of the event, so it doesn’t feel like the action has to stop midway through.
2. Be aware—and make sure your partner is aware—that it is completely normal if you lose your erection once you’re penetrated.  Your partner may worry that this means you’re no longer aroused or want to stop; communicating with her throughout will help everyone feel better.
3. When your partner is ready to penetrate you for the first time, focus on relaxing.  It can help to try to actively release the sphincter muscles (push, rather than squeeze). This is when you really need to be comfortable talking to your partner—if it hurts or is uncomfortable, remaining silent will only cause you to tense up, making it even worse. Tell her if you need her to slow down, pause, or stop. 
4. Before your partner has even begun, she should have made sure that you and the dong are both lubed; but as things go on, you may find that you aren’t lubricated enough any more—it is helpful if you keep the lube handy so that you can either reapply as needed or remind your partner.  Remember that she won’t have any way to know if you’re too dry based on feel; you’ll need to speak up or take things into your own hands.
5. Don’t expect to get it perfect the first time.  There is a lot going on during a pegging session and it isn’t going to come naturally.  If there is anything that wasn’t quite what you wanted, remember it afterwards and have a discussion with your partner on the finer details.  This is one activity that may take more work initially, but if you stick with it, it can be wholly satisfying for both partners.

As with all things sexual, having a sense of humour and being comfortable with your body will go a long way towards making this an incredibly enjoyable experience for all parties.  If things go wrong, it will just give you something to laugh about later—in the moment, shake it off, regroup, and try again. 

And when it goes very well, enjoy the experience full; and then start figuring out what you’re going to be doing for your wonderful partner to thank her for the wonderful time you had.  This might be just the time to find out what fantasy she’s been wanting to try out with you—she deserves her own bit of kink after all her hard work, doesn’t she? 

Got a question you need answered?  You can write to me at mcbirdie@sexshop365.co.uk. 

Related

• A Man’s Guide to Pegging–Part One
• A Woman’s Guide to Pegging
• Dear Birdie: Is there a trick to cock rings?
• Dear Birdie: What do the different types of toys do?
• Dear Birdie: “Why do men act so horribly when they don’t get their way?”