When was the last time you had anal sex?

She wanted it this morning so I obliged 😃

Yesterday. i have written about my FB before on this thread. He's a Bi Latino Muscle Guy on the DL... so i always wait for Him to contact me. He's been breeding me for 6 years now (anally. i'm gay total bottom). The last couple of years, He contacts me 3-4x a week. He says that He loves to "bitch" me. That may sound mean, but it's not at all. He does love it if i wear lingerie, and lately He's been doing this thing where He reaches under me (i'm always lying prone) and holds my chest like i have breasts. Drives me wild, the way He touches and holds me, moves me. He;s a mass of muscle, to by the time He is done, i feel... tenderized. It never gets old for either of us, pretty amazing.

@Asteria So pleased this lucky guy is helping you to heal 😃

Late this morning. There's a female escort I've seen off and on for the past ---she informed me today because she keeps a diary--13 years. We start with me giving her an enema. Usually, she prefers a soapsuds one with a bucket . Today we used a fleet because she was in the process of moving and couldn't find her enema goodies. We had anal sex after and she shoved 3 glycerin suppositories up my butt as a farewell gesture. Since this also answers another thread about the last object put into your rectum, do I get double posting credit ? LOL

One week ago....me on my stomach and him coming at me from behind. denise

It's been a while. With my high school gf, it was our preferred way. Contraceptives were unavailable to teens at that point, so it was either that or oral, and neither one of us enjoyed that as much. So...back then, the back door was almost only door. After marriage, never, until divorce, and my girlfriend loved it. She enjoyed the domination and she told me once, "it hurts soo good!!" I was definitely being gentle, but I'm decent size when erect, so there's that. Her sex drive perished at menopause, so sex of any kind is nonexistent, but she is a wonderful girl. Fortunately, I'm 80, so horniness is (mostly) controllable. I LOVE to perform anal sex, and if my partner is female, I also enjoy anal stimulation, but I just never really liked pegging. Ideally, I would enjoy anal sex as often as about every third time, if she still did. As it happens, anal feels very different if you're performing. A woman's vagina is...well, indescribably pleasurable. Her backside is not at all the same. It's like entering a vault with a round massager at the entry. The pleasure comes not from the welcoming internals, but from the ring around the rectum and a much softer, easier internal experience for the performer. My high school girlfriend told me that she could feel me in her vagina, through the rectal wall. I assume that's part of the pleasure, although rectal/prostate massage is a huge turn-on for me, as are enemas (if given by an attractive/attentive female, so much the better). Humans are weird. As a Dom, I'd much rather "do;" as a pleasure seeker, I like all female stimulation.

Last Sunday with my wife. I was, as always for 40+ years, the top. I ejaculated in her rectum and watched her expel. Viva monagamy!

Monday night, my wife took a nice load deep in her bottom

@TexasJack.

You are a very lucky guy to have a most loving wife and to be able to experience this. My wife would never let me get near her hiney hole in any way.

@Trojan @TexasJack Count your lucky stars guys!

My lovely young girlfriend likes me to take her anally whenever I feel like it, which is usually about every third time we have sex together.

As an old man I grew up with fucking a woman almost exclusively in her purpose made for dicks vagina. But because my girlfriend likes to make me happy (and herself of course) we have anal often so I can creampie that hole as well. I do prefer her cunt but her ‘back hole’ does add a bit of excitement and variety to our sex.

My current "matrimonially entangled roommate" and I have not had sex of any sort in a few years. My efforts to secure a FWB have not been fruitful either. The only time my dick gets wet is when I take a shower.

I forgot to add to this thread from my last trip. I spent thanksgiving out in Palm Springs California and I'll give the highlights:

Flew in Nov 24 and after settling in, I booked a massage to help me unwind from the flight. Great gay masseuse who half through and having me suck him, took me to the other room where he had a sling. I got into it and he fucked me covered and and long. After he was done we went back to the massage table and he finished the massage.

The next day I meet an old buddy who came to my Airbnb and after we relaxed in my hot tub naked, went to the bedroom and after sucking him and rimming each other, he flipped me over and fucked me slowly and deep. He is 8.5, cut and thick and 6'3" and loves short husky older men like me. He fucked me BB and came 2x in me. There was lots of kissing and nipple play and more.

The next day an online buddy had me came over and he gave me several warm soapy enemas and began working my hole with toys and fingers and then slowly opened my hole with his pumped cock. He is about 6.5 long but thick as coke can. He also fucked me BB and went balls deep and did slow short strokes and built up the pace, then came long and hard in me. I was flooded.

The next day I took a rest day from getting fucked.

Day 4 I met another online buddy and his husband for a 3 sum that was amazing and I was spit roasted by them and now we are very good close friends. Both of them came to my Airbnb and when they walked in looked at each other and said loudly, Yes, he (me) is perfect! I was speachless and top 1 said we can skip the hot tub and pool and go to the bedroom. Top 1 was 8" thick and had me start to suck him while top 2 was husky chubby like me but had a 7" Coke can cock and asked me when I got fucked last...I laughed and said yesterday and he said, well you are going to get fucked and filled like never before. My ass was so clean and ready for both of them. They went back and forth with me and after several hours of play, rest talking and more play...they left 4 loads in me, 3 in my ass, 1 that I swallowed, I was an very happy bottom GWM. I slept so well that night.

Had to cancel another play date for the next day as my ass was still buzzing from my 3 sum.

So Sunday the day before I leave my buddy from the 1st day there came back and said he wanted to fuck me in the hot tub. He had some amazing lube and used a lube shooter to get more in me. Now Palm Springs have some strict noise rules, even for the day and he knew it too, so as we are getting in the hot tub he spreads my cheeks and puts a lot of the thick lube on my hole and had me squeeze my cheeks. He is standing in the hot tub and has me lean on the side of it facing forward. His cock is rock hard and starts to go into my cheeks and I feel him find my hole and goes in slow and he is making contact with my back and is hugging me and we start kissing as he thrusts his hips into me. The hot water, being outside, kissing each other and him fucking me was unbelievable. He came so much we both needed to relax in the tub before going inside. We went inside and he fucked me again and took forever to cum. I thought we were done he wanted to make sure I'd come back soon and said if I give you 1 more load I want you back here in the spring. I said yes Sir, as you wish.

I left to come home the next day and I am going back out to Palm Springs in 2 weeks. Going to see my buddy again and my 2 tops couple again.

I can't believe how many times I got fucked and flooded but I'll post each day next time. Pics of the fun to follow. I love Palm Springs.

It’s been decades, but the pleasurable memories have never faded. For me, it’s more exciting than vaginal sex.

@BottomBear nice hot story!

This past Monday. I have been seeing this lady off and on for over 10 years for a paid encounter. Usually we start with me giving her an enema and then do anal. This time I was so "plugged up" with sperm we skipped the enema. Didn't notice any difference afterwards compared to when I give her an enema pre anal. She did want an enema after because she gets constipated frequently. I guess you can say this last time we kind of did things ass backwards!

TexasJack

Sunday afternoon with my wife. I was the “top,” and I came in her rectum.

I also like the feeling of cumming in my wifes ass. It's tight and she loves it too.

I'm out back in Palm springs and last night I met with a top FB at my place. I greeted him naked and made out for about 20 minutes and then led him to the bedroom. We got on the bed and after more kissing and me sucking him balls deep, he is a solid 8,5 and thick, he had me lay on my back and lifted my legs to his shoulders. I'm short and husky and not super flexible, but he was able to go slow and started to enter me and moved closer and got deeper. Our eyes locked and he and I were so into each other as he pumped into me deep and strong. I felt him cum deep and long into me. We are both negative and tested regularly as well as on PrEP and doxy. After a brief break and kissing he was rock hard again and had me get into doggy and fucked me again, for load 2. A longer break and bed talk and him working my nipples got him hard again. He was ready for number 3, my hole was leaking and felt happy but my hole wanted more. He fucked me again face to face like the first time and was so aroused by my wanting more of him, he let his 3rd load deep in my used hole. I thought he was done and we made out more as he played with my sore nipples, he was getting hard and started to jerk off as we made out deeply and I said that I wanted him to cum on me and my cock. He let his 4th load fly and I couldn't believe how much he shot on me. This was over 3.5 hours and today I'm going to a gay couple house I met on my trip a few months ago, see a few posts below. I'm a happy used bottom GWM and looking forward to rest of my trip. Stay posted for today's adventure.

I got a cum enema from my Daddy on Wednesday ☺️

Last weekend. I told hubby it’s off the menu for a while as I had some bleeding after

My hub and I play golf and it has turned into somewhere during the day we will make a little bet. One wins, then we double down, I win both then I get a meal from where I fancy. Yes I am cheap, then he spends some time on his knees.

He wins, I spend time on my knees, then he gets his request. Me to dress as he pleases, a X rated photo session, or allow him to park the car. I was greased up, bent over and he had his way with me. But I enjoyed it as much as he did.

It’s been a couple months since the last time I had anal. I was the bottom in a pegging session and I loved it so much! I’ve never done anal with another male, but I’m definitely open to the idea as a bottom.

Last night we started out just kissing and messing around in missionary, taking our time. We switched things up with some oral, just enjoying each other, then he flipped me over. After we got ready, he slid in and we kept going for a while. I ended up on my knees and we finished in doggy. I came a couple times before he did.

Last night with a younger gentleman friend 🌷 and we've a date for enemas and more anal sex which will include my pegging him as we both want this with each other. 🌷🌷🌷 He is very gentle and loves enemas and I very much love enemas from him.

But as gentle as my younger friend is and how respectful of me he is, this man can and does 🥵 own me 🥵 when he buries his cock 🍆 balls deep 💥💥💥💦 in my bum. 🥰💋

Last weekend. I told hubby it’s off the menu for a while as I had some bleeding after

- sorry to hear about your problems - take care of yourself and listen to your body !! - but in my opinion there will be many other practises, who will be allowed to get satisfaction !! - all the best wishes for you to get a quick recovery in those special part's of your body !!

On Friday of my Palm Springs mini vacation this week, I met with the gay couple from thanksgiving 4 months ago, actually it was husband 1, as husband 2 was out running errands but knew I was stopping by. We had some small talk and making out! And he and I got naked and he had me sit on the couch as I sucked him for about 10 minutes and then husband 2 walked in the front door and saw us with his cock buried in my mouth...we all laughed as it seemed like a bad gay porno with me being the pizza delivery guy. So husband 2 said please continue as he got naked and went into the pool. I continue to suck husband 1 for another few minutes and then said let's go to the pool too. As we go outside he said to grab the chair and he lubbed up my ass and began to slowly enter me as I was grabbing the chair bent over. Meanwhile husband 2 was in the pool filming us. Husband 1 has an amazing cock with a left turn to it, he built up a great rhythm and with husband 2 still filming us, he came in me and kept going for another minute. Sex is much better with friends. I took Saturday off as my gay couple friends are having a pool party and I'm going. So now I'm going to make some new fun friends. Updates to come back probably tomorrow as I'm going to tired to do anything later. And the video of us fucking is so hot.

Last Sunday. I went to visit my special friend. After some delicious foreplay, he moved me onto my stomach and laid on top of me with his magnificently erect cock between my legs. While in that position, he used his cock to externally massage my prostate area while occasionally allowing his cock to slide up my ass crack and brush past my needy hole. At times, the head of his cock came to rest on my hole while he applied the slightest pressure causing just the head to slowly penetrate my well lubricated opening. He would then pull out. This went on until I was literally begging to be impaled by his ample shaft! He then flipped me over onto my back, pinned my knees almost to my shoulders, and mounted me with an animal thrust. Holding himself deep for a moment, he then began to slowly slide out then thrust ahead. In time, his tempo began to increase and I could feel his balls slapping my ass cheeks. It wasn't long before an orgasmic wave washed over both of us and we crumbled into a sweaty, cum soaked embrace. It was a nice way to spend the afternoon.