I've had anal sex before with my ex who was average and so the anal sex was comfortable. Recently I started talking to an old fwb again who is above average. His thickness is a major turn on and I'm really excited to start having fwb with him again but he wants to try anal for the first time. I'm almost hesitate due to do it because it's hard to give him a bj due to it being so thick that I have to really widen my mouth and jaw. Due to his size, how can I prepare myself to do anal? Mind you I'm not used to using lube or anal play or fingering. I'm not one to give up so easily, I really want to try for him because he has told me that the women he has already slept with refuse to give him head and to do anal. Any advice or suggestions would help. UPDATE: On Saturday, I finally met up with him and I told him that I really wanted to try anal for him but he was more concerned with hurting me (very sweet, I know) so he wanted to wait to try anal. So I was able to give him head and deepthroat him first even with his thickness which then caused him to cum too soon after we started to have sex afterwards. He felt so bad, but I was happy to satisfy him with head because I really did want to try for him. Within a few minutes he was able to get hard again and continue having sex, and when he finished he said I was too tight for him. LATEST UPDATE: we did it! No lube necessary just used my natural pussy juices like expected and it was very enjoyable and so he too enjoyed it. Unfortunately a few hours later I ended bleeding which is normal. So at the moment I'm healing and am not going to tell him because I don't want him to feel bad.
Lots of foreplay. Relax with message. Train over several nights or weeks with stages of plugs. Good quality lube. Take your time. Make sure you talk over all of it openly and be honest at all stages especially the final penetration.
I agree with "Straight Up"...wear a butt plug all day and you should use some lube for the thicker cocks. If you want to please him and have him in there make sure it goes in with little discomfort. Once he's in and starts going deeper you'll both be comfortable and satisfied. Relaxation and lube is really key to taking a thick cock up your ass.
Make sure to use a ton of lube and I would recommend getting two dildos of varying sizes and practice working up to that size...
I totally agree with you. After four years of being pegged by my present wife and progressing bigger and bigger I'm very receptive to larger now. Our shared lover just recently bottomed out his thick 9.5" cock inside me as my wife wanted to see us fuck having only sucked each others cocks with her involved or just watching us. We were all amazed how easily he slid in with her help guiding as she was sucking me off. We both had very intense orgasms. Having only sucked cocks I wish I had explored anal sex with all the hook-up's I had in my previous marriage behind closed doors for 15 years. My present wife is a trooper and enjoys my bisexuality and is an active partner in threesomes with Tom for the past couple years.
I was that way when I tried anal the first time. I used a butt plug and dildo's. My husband used the dildos in me and just got better and better.
So you didn't use any lube at all when you had anal sex with your ex who was average size? Did you have anal sex with him on a regular basis? And were you able to orgasm from it or not?
I didn't use or need any lube, we didn't have anal often either. I've orgasmed a few times with just anal but I've orgasmed plenty of times when I would rub my clit during anal sex.
The best way that we feel is to take your time no matter if it is your first time or your 10th time , i am one that is not in hurting my woman , use lube some have to use lots and there are those that do not , and if you are hurting your woman at first when you enter her anus then be a man and take the damn thing out . you will have more results if you do not force her into something she is not comfortable with Believe me ,
