Condoms aren't as bad as guys make them out to be.
Talk to your partner about menstrual sex and decide on some ground rules.
Don't place too much pressure on yourself to make your partner orgasm.
"All they do is protect us from infections and from becoming fathers, but all we do in return is give condoms a hard time."
Sometimes condoms get a bad rap. All they do is protect us from infections and from becoming fathers, but all we do in return is give condoms a hard time. Where’s the love? Condoms themselves shouldn’t cause UTIs for men unless they’re carrying bacteria. UTIs are most commonly associated with bacteria in the urethra, kidneys and bladder, as well as weak immune systems. Keep in mind that a condom is more likely to be exposed to bacteria from contact with the hands, mouth and anus. But there is research that suggests women whose male partners use a condom and spermicide appear to have increased amounts of E. coli bacteria in the vagina, which can lead to a UTI. Also, some people have allergic reactions to the condom material (usually latex) or the spermicide/lube, which can resemble a UTI. As for the male libido, some people have a psychological reaction to using condoms that can affect their libido. Knowing that using a condom can decrease his sensitivity, sensation and possibly impact his erection can mess with the mind. But is that really the condom’s fault? What percentage of men are actually OK with having sex with women on their period of menstruation? The percentage of men who are OK with menstrual sex depends on age, culture and spirituality/religion. Unfortunately, more guys aren’t OK with menstrual sex than those who are fine with it. The important part to focus on is that your boyfriend was willing to try it. It sounds like taking some precautions beforehand can help the next experience be more memorable for the right reasons. Laying down a towel beforehand, wearing a condom, choosing a day with a lighter flow, and showering can all help ease menstrual sex anxiety. Some people establish menstrual sex rules like no fingering or cunnilingus. It’s all about changing your perception of menstrual sex so that it is positive, fun and not a big deal. Also, you’re right about the help that menstrual sex has with cramping. Intercourse and having orgasms has been associated with relief of menstrual cramps, because they help release the muscular tension that’s been built up in the back and pelvic region. I’d suggest you and your boyfriend be honest, share your thoughts and feelings, and talk about ways you can both set the stage for a pleasurable and enjoyable second menstrual sex adventure. Wouldn’t take it personally that your girlfriend hasn’t had an orgasm from intercourse -- it’s more common than you think. Most women reach orgasm in a variety of ways, and placing emphasis on one particular method often puts too much pressure on both partners. This is likely something she’s dealt with before you ever came into the picture, so it’s not just you. Most postmodern sexologists believe orgasm is the responsibility of the individual. The important part is that she is able to share an orgasm with you during foreplay and other activities. I wouldn’t put pressure on you or her to prove her wrong. That doesn’t mean you both can’t try new toys (a vibrating cock ring or vibrator) or activities to add to the pleasure you already experienced. A common technique that attempts to incorporate orgasm with penetration is called the bridge technique. In short, you stimulate her in the manner that helps her reach orgasm (oral, fingers, etc). Before she reaches orgasm, you insert your penis and “bridge” intercourse with orgasm. You can continue the stimulation that helped her get to the point of orgasm (likely clitoral stimulation) along with the penetration, or penetration only. As you get the hang of it, you can both experiment with elongating the time you bridge. One drawback as a male is that you would have to be ready, aroused and erect when she reaches the point of orgasm, which adds to male erectile performance pressure. Who knows, an intercourse orgasm may sneak up on you if you both can find ways to take the pressure off. Remember, orgasm shouldn’t be the goal of sex but should be a part of the sexual process. I think pleasure and enjoyment are more realistic goals. 
