Virgin Pegger here

[Do****]

I really want to peg my partner, let me preface with he was the one who suggested it and asked for it. However I’ve never done it before and he’s never had it done as he’s just discovering new parts of his sexuality. I’ve had sex with women using a strap on, but I feel like I need to be much more gentle with him with it being both of our first time. SO MY DILEMMA. We have discussed it and have discussed how we are comfortable enough with each other, yet neither of us know how to initiate trying it. We are both verse switches which probably contributes to making the right moment to ask a lil awkward. Someone help?

[Au****]

Make sure you tease him first and play with his ass first. It can be really ***ful when you just push it in but after a couple pumps it does feel good

[ge****]

Has he done anything anally before? Toys? Fingers? If not then might be best to start there - maybe not as part of a scene but as part of normal intimate play.
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If he has done anal activities before, then introduce it the same way you did those but again maybe as part of normal more intimate play.

[Sk****]

So, definitely go slow. Start with just the tip in and out. Slowly start going in further and further. Just be real attentive to his body cues too, they should let you know when you're making him feel good. After he fully relaxed and lets it all in...there is where all the fun begins. Good luck to yall

[ja****]

Well.. take the lead on this one! Tease him for days just to make his mind goes along with his body.. and when you decide that today is the day.. make sure that he knows that its happening so he gets ready for it (maybe a text message in the morning: be ready, tonight is your night) and start with loads of kisses and cuddles and rubs, fingers, little toys until he is relaxed and ready for it.. and slowly go for it..and let him be in charge just to know how he likes it then.. buckle up its a bumpy ride

[vi****]

Did you pick out the dildo already? Get smaller and thinner, go mild to wild...lube too, lots. And just put it on and say bitch, bend dover

[Th****]

If he hasn't done anything on his own already, encourage him to do that first. It will give him an idea of his width and depth limits, what he can do to get himself ready, etc. Take some time together to shop for a toy that feels right for both of you. Then just incorporate it into the foreplay. Give his hole and the area around it some attention, and bring it out like you would any other toy.

[Ma****]

Communication is key in this as in everything. Talk about it as you show you already have. Start slow. Tease. Use smaller items or fingers. A small vibe. You can also use plugs. You can buy a set from small to large. This will help him train to take it. Plus can be worn for different lengths of time to help as well. Lube, lube, lube.

Not sure if you yourself have done anal before but if so just think of how you approached it and extrapolate from that.

If not just experiment with foreplay. Dependant on what you both enjoy and are willing you can add rimming in a well. Try to start with a blow job and while proceeding add a finger.

There are multiple ways you just have to settle on what works for you two.

I agree with @jaykkolins trade him about it it for a few days. Maybe edge him and include orgasm denial to enhance things as well.

Just my 2 cents though. Mileage may vary.

[SBdomswitch1369]

If he’s relaxed and can back onto it while you just make gentle thrusts, lots of lube, little circles and once it’s in there, nice and slow until he’s ready for harder/faster…..definitely worth the effort! ☺️

[he****]

All the advice so far is great. Def anal plug to see even if he like it. When your new its really weird at first and he might not even like anal play so test that out first. Also, and i cannot stress this enough- diet, immodium, and enemas! I cant begin to tell all the bloopers i have had with my Mistress. Last thing that a biggest thing for me is timing and mood. Some days i love it and other days my bootyhole is a no-fly zone. Just as long as you are safe and using open and clear communication- have a blast and i wish the best for yall!!:)😈

[Do****]

Start with mental butt plugs and Vaseline. Try the small for a bit. Doesn’t sit inside as easily and less pleasurable. Then medium for up to a couple of hours. Lots of Vaseline. See how it feels and how the prostate responds. Get use to the size. Then try probing with a smaller anal probe. One with ridges maybe. Then work up to a small dildo. You can get a dildo and straps from Love Honey. The purple dildo is small and smooth. Great to start with. But with anything other than butt plugs use actual anal lube. Not Vaseline. That’s for things staying in one place for periods of time. Not for movement!

[Do****]

Should completely say metal and not mental!