Advice to Peg a young first-time sub

Dear Mistress Geena:

My boyfriend wants me to peg him, but I’m worried he might not be ready. He is only 19 years old and has never had anything inserted in him, let alone been fucked. I know he’ll enjoy it, but I don’t want his first time to be painful. Should I try with some toys first, or just give him what he keeps telling me he wants – fuck him hard with my strapon?

Signed,
Anxious Pegger

Dear Anxious Pegger,

Thank you for writing to me and entrusting me with such a delicate matter. I can understand your hesitation and concern about pegging your boyfriend, especially since he is young and inexperienced. However, I believe that if both of you are open, communicative, and willing to explore, pegging can be an incredibly pleasurable and intimate experience for the both of you.

Firstly, it is important to have a conversation with your boyfriend about pegging and his desires. Ask him why he wants to try it and what he expects from the experience. This will not only give you a better understanding of his desires but also allow you to express your concerns and boundaries. It’s crucial to establish clear communication and trust before engaging in any sexual act, especially one that involves penetration and power dynamics.

As for your concern about his age and lack of anal experience, I would suggest starting slow and using plenty of lubrication. You can begin by experimenting with anal play through fingering, rimming, or using small anal toys. This will help your boyfriend get used to the sensation and prepare him for a larger object like a strap-on. It’s essential to take things at his pace and stop if he feels any discomfort. Remember, pegging is about pleasure, not pain.

Another tip is to invest in a good-quality strap-on and harness. It should be comfortable for both you and your partner, and the dildo should be the right size and shape for his body. You can also try different positions to see what works best for both of you. For example, your boyfriend can lie on his back while you straddle him, or he can be on all fours while you penetrate him from behind. It’s all about finding the position that feels most comfortable and enjoyable for both of you.

Now, let’s talk about the power dynamic involved in pegging. For some couples, this is a significant turn-on, and for others, it can be intimidating. If you and your boyfriend are both new to this, I would recommend starting with equal power dynamics. This means that you both have equal control and can switch positions whenever you want. It’s essential to respect each other’s boundaries and communicate openly throughout the experience.

You can also incorporate elements of domination and submission into your pegging play if you and your boyfriend are interested. For example, you can have him wear a collar and leash while you take control and give him commands. But always remember to establish a safe word beforehand to ensure that the experience is consensual and enjoyable for both of you.

Furthermore, make sure that your boyfriend is relaxed and aroused before engaging in pegging. This will help his body to relax and make the experience more pleasurable. You can start by giving him a sensual massage or engaging in foreplay to get him in the mood. You can also try using breathing techniques and relaxation exercises to help him ease into the experience.

Lastly, I want to remind you that pegging, like any other sexual activity, requires practice and patience. It may not be perfect the first time, and that’s okay. As long as you both communicate and work together, you will find your groove and make it a pleasurable and fulfilling experience for both of you. In conclusion, I encourage you to have an open and honest conversation with your boyfriend about pegging and exploring this new and exciting experience together. Keep communication, trust, and consent at the forefront, and don’t forget to have fun! I wish you both all the best in your pegging journey.

Sincerely,
Mistress Geena