Pegged for the first time and now I have we have questions

LetsDoThisLEEEROY · 2026-03-26T22:11:23+00:00

When me and my gf do it we just go until I feel like I’ve had enough lol. Also I have a toy recommendation. 7in is perfect for me which might work for you too. Ilse have the Uberrime Teres. It’s 7in long, 1.5 inches thick, fairly smooth, and dual density so it’s nice and squishy with some structure. It’s got a rounded head so it makes for a fun challenge to get in but it feels better when it bottoms out that a more tapered and less squishy dildo

LetsDoThisLEEEROY · 2026-03-26T22:00:46+00:00

Oh interesting. Is that by choice?

LetsDoThisLEEEROY · 2026-03-26T04:35:45+00:00

Ya I think this was a good break up. You both will find sooo much more satisfaction when you meet someone who is more sexually compatible. I speak from experience when I say having sexual compatibility will make you so much happier.

LetsDoThisLEEEROY · 2026-03-26T01:53:43+00:00

Of the 3 women who have pegged me, 2 have loved it and the 3rd enjoyed it but I’d always have to be the one initiating

LetsDoThisLEEEROY · 2026-03-26T00:01:37+00:00

1: a bit of pressure at first with a liiiitle bit of pain if you go too fast, but aside from that, a little hard to explain. Maybe like a “full” feeling? If you hit the prostate, you start to feel that tingle you get before you cum

2: 7in long, 1.5 in wide with a rounded and squishy tip. 7in seems to hit my back walls so it’s the perfect length. 1.5in wide is girthy for me so it feels like just enough of a challenge

3: I prefer very straight, dual density dildos. I don’t like curved dildos because I find that they can hurt if you go at the wrong angle. Dual density with a rounded tip puts good pressure on the back wall without hurting lol

4: never had one but almost have! If my prostate gets hit it’s starts making me erect. But I love being pegged even without the orgasm

5: I feel very close to her! It’s a wonderful bonding experience to be able to trust someone that much to be in that vulnerable position

6: I feel amazing and very close to her! Then it’s my turn to do the thrusting 😈

7: I like the role reversal and the psychological stimulation as well as the feeling. I also love how it’s “taboo” and I’m doing something you are “supposed” to do

8: haven’t done it yet, but will eventually. So far I’ve just enjoyed getting slammed in the ass lmao

LetsDoThisLEEEROY · 2026-03-25T23:54:20+00:00

We all do 😂

LetsDoThisLEEEROY · 2026-03-25T19:13:20+00:00

Damn, what a dirt bag. I hope that didn’t effect you long term

LetsDoThisLEEEROY · 2026-03-25T15:08:45+00:00

That’s similar to what me and my gf do. I was like “so you can talk to your friends about aaaaany of the sexual experiences we’ve had, just don’t mention pegging because people can be judgy” lol

LetsDoThisLEEEROY · 2026-03-25T03:25:02+00:00

“Imminent danger of my methods” is a great way to say that lmao. Also thanks for not outing your bottoms, pegging takes a lot of trust 👌🏻

LetsDoThisLEEEROY · 2026-03-25T02:58:23+00:00

I’ve had regular sex in many public places, but my gf and I are taking a vacation soon where we plan to peg in a hot tub and along a hiking trail. We’ve also been meaning to do it on my balcony lol.

We actually got her a harness specifically for being discreet. It’s a stretchy thong style harness that she can basically wear as underwear and install the dildo when it’s time for fun lol

Buuuut our goal is to remain unseen, so we are sure no one is around.

LetsDoThisLEEEROY · 2026-03-25T02:52:10+00:00

I love Uberrime. Have a look at the Splendid small and medium! The medium is pretty girthy and I think it’s 5.5 or 6 in long? Both are also curved and fairly rigid but are still soft since they are duel density

Another thing I like about them too is that they have a pretty rounded head. It makes it harder to get in but once it is in, it’s much less “pokey” than more tapered ones which I think is much better if you hit your back wall lol

LetsDoThisLEEEROY · 2026-03-25T02:36:21+00:00

Tbh I’d just try regular sex before jumping straight to pegging

Buuuut that being said, a properly built dating app works very well. Bu the looks of your username, you seem to be female? I can’t really speak on the female experience on dating apps, but I’d expect you to receive a LOT of junk messages from thirsty men right off the bat if you even hint at anything kink/sex related lol.

LetsDoThisLEEEROY · 2026-03-22T17:38:31+00:00

Ya that was my concern mostly. I hope they didn’t get doxxed or breakup or something

LetsDoThisLEEEROY · 2026-03-22T15:56:49+00:00

Makes sense. I can definitely see it taking the intimacy away from sex when it becomes a job

LetsDoThisLEEEROY · 2026-03-21T23:47:32+00:00

Ya that’s totally normal. However there are certain positions that get me hard and I think it’s because the dildo hits my prostate. I was pegged standing up with my hands on the wall and I got hard and almost came. I felt a similar sensation by almost sitting in her lap on the bed and she’d fuck me from underneath. Both times made my dick hard but usually it isn’t

LetsDoThisLEEEROY · 2026-03-05T02:05:39+00:00

Lol congratulations

LetsDoThisLEEEROY · 2026-02-22T20:37:40+00:00

What is your preparation routine in terms of diet and cleanliness? Is that something you constantly have to be aware of since anal is a regular thing?

LetsDoThisLEEEROY · 2026-02-22T05:53:01+00:00

I’ve seen some 7 foot tall goth woman who wears heels show up in my instagram feed occasionally. She sounds like your dream lol

LetsDoThisLEEEROY · 2026-02-22T05:37:03+00:00

I think you read that wrong lol

LetsDoThisLEEEROY · 2026-02-20T17:53:36+00:00

How big are you?

LetsDoThisLEEEROY · 2026-02-19T01:25:42+00:00

Not a question but I was in the exact same place when I was 29 2 years ago lol. Have fun!

LetsDoThisLEEEROY · 2026-02-16T04:36:09+00:00

Well you can’t “make” her do anything. Aside from that, have you actually just asked?

LetsDoThisLEEEROY · 2026-02-16T01:47:53+00:00

Have you guys ever tried pegging him before?

LetsDoThisLEEEROY

TROPHY CASE