The advice for anyone starting anal play of any sort is
Start small and work your way up to bigger sizes slowly.
Use plenty of lubrication. Re-apply if you’re having a long session.
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Thats my take on thingsi never force him to donthings he feels uncomfortable with Hope you’re keeping well
About an hour ago. Girlfriend had just got ready for work. She works at a restaurant in town and wears a work uniform. I asked her to peg me which she moaned about as she thought she might be late in. I said she could just put the strap on over her uniform to save time. When I was ready I called her up to the bedroom. I was ready for her. I passed her the LH 6 inch length basics dark flesh colour dildo with ‘strap on me’ pants. She quickly put them on and I got on the bed on all fours. She eased it into me slowly then started to fuck me harder and harder. I was pushing back as well. I stopped and told her to fuck me hard. She did this for about 5mins and I could feel myself cumming. I was really loud at this point and I came really hard. Cum dripping from my soft cock. Loads of it. I had to compose myself for a few minutes as it had really taken it out of me. I cleaned up and she when off to work. We kissed and I told her she makes me really happy. What a woman. Xx
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An hour ago.
Flogged all over my upper body front and rear then knelt on the edge of the bed and pegged from behind.
Emotionally draining.
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About a week ago. First time in a while I was able to cum hands free. Mind blowing orgasm and wife just kept going. Get like I was in another dimension of time, LOL.
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Too long ago
I haven’t tried pegging yet but am super keen to try it
Been a few days about 3-4
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Been a couple of days now plus wife working a night shift tonight.I am absolutely gagging for it and can hardly concentrate at work today as i need it so bad.Tonight i will go to bed and dress in my most frilly feminine pink lingerie with white stockings.I will also place a framed picture either side of the bed.One will be Bailey Jay,the other Daisy Taylor and they will both be showing their lovely hard-ons.Wife can never resist an invitation such as this so once again i will be the recipient of 8 lovely inches inside me.This will also play into my wifes hands who will then become Mistress and punish by flogging or caning me on my return home from work on the evening.My crime,fancying T-girl cock over her wonderful Pussy.Bliss.How on earth can i get through the next 20+ hours 
It was supposed to be today but the eldest grandchild has a day off school so he’ll be with us all day.
Bugger!
Was meant to be the other night but OH decided she wanted to watch me fck myself while she masturbated for me was in the 69 position but where she could see my ass think she wanted it like that so she could lick my balls at the Same time and was really handy when I came she scooted down and took it in he ex mouth
My last anal was only last night - in the past week we have been quiet and last night my husband wanted a spanking - so I got my new paddle and got him wearing my knickers and gave him a nice spank - then I decided to give him a pegging - so within a minute he is bent over , knickers down and I’m riding him deep with my thinner dildo strap on - we were loving it - then he asked if I needed penetration before he ejeculated and we reversed and he was then deep inside my anus riding me good …
Great night 
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So long ago i cant remember
We included some pegging last weekend (like 10 days ago) including, finally, our first time putting the ever-so-slightly larger dildo to use. It’s about 3/4 inch longer than our starter dildo that came with the harness, I think, and wifey really enjoyed having the extra length for maneuverability. And I just liked it all around.
She took me from behind, bent over the bed, to get started. We transitioned to a face-to-face position - pillow under my hips and mostly holding my legs up over her shoulders and it felt very good that way. We found a position there that felt very good stimulating inside, and she was grinding on my penis (she had also worked a dildo inside her vagina held in place by her catsuit and was running the Womanizer on her clit). I came rather suddenly in this position from the combination of all things - I wouldn’t go so far as to say that I had a prostate orgasm at all as the grinding was a significant contributor, but I also was barely even semi-erect when I came so I’m still trying to piece it together. Either way it was a tremendous feeling.
We took a quick pause to slip her out of the harness and then she sat on my face for her orgasm - she actually kept the Womanizer on her clit, she just wanted me to drown between her lips while she held that power over me, which I was happy to oblige.
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Unfortunately for me wife doesn’t like the idea of it, shame as I’d like it.
2 days ago.
2 new dildos to try out but recently she has taken to caning or flogging my ass before she pegs it so I was caned then pegged twice. Once with each didlo.
My favourite was an 8" long x 6" girth dual density dildo. It felt great in my mouth and my ass.
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Gosh, been about 9 months now. Far too long really.