Bottoming: What prompted you then, and now?

I can understand if you've been around the block and have done it many times over, but in those first few times that you went that route, I can only imagine how difficult and painful it must have been for you.

Do you think a lot of it had to do with the person that was manipulating you into doing it at the time. Was it the curiosity, or was it the alcohol, or the amazing rim job he gave you... In any case, it had to be something that prompted you to bottom, and continue to do so for this long. And because of that, do you feel any more feminine now than before you ever tried it? Is it one of those Dr. Jeckyl and Mr. Hyde scenarios where you're totally masculine in public and around others, but behind closed doors your estrogen levels gets the best of you when you feel a cock pumping your ass and/or dumping his load in you...

What's your story?

 

Still no responses huh?

 

I think it's your sig pic. Kinda creepy.

 

What's so creepy about it?

 

Personally i just like the idea of a big, older guy having his way with me. Being treated like a slut is a real turn on for me.

 

That's the way I am with it as well. I'm completely masculine outside of bed but I love to wear panties, get on my knees & get fucked like a little whore with an older man who likes to give direction. Older hard top daddies are my favorite. Especially if they are in shape & take good care of themselves.

I tried topping only time back when I was about 14 with my cousin but he was hairy as fuck & it didn't do anything for me. The only ass I'm gonna fuck is a females. Besides, when I first started fingering myself when I was a young teenager, I loved the feeling of doing something so naughty & it really baffled me that it actually felt so good & so I began moving on to bigger things and eventually a real man's cock. Although I rarely get fucked when I meet with someone, I usually only suck cock but I've been doing it ever since.

 

For me, it's simple. From the VERY beginning, I've ALWAYS had/HAVE the FANTASY of an older, bigger, stronger handsome "Daddy" type MAKING LOVE (NOT just fucking) to me as if I were his "WOMAN". This includes kissing, making out, cuddling (and "seeding" me regularly too). Although I'm a masculine (in appearance anyways) looking guy, I have ALWAYS had an UNDENIABLE "feminine" side too.
If I could find just ONE older, bigger, stronger and LOVING TOP "Daddy" type that that would NOT only like to MAKE LOVE to me... But ALSO someone that has a Dominant, controlling and somewhat "selfish" side (at least in the bedroom) who would get a thrill and TRULY EMBRACE "molding" me into his completely submissive SISSY BOTTOM boy, that would DEFINITELY be a DREAM CUM TRUE for me.
I've NEVER wanted or felt the need to top another guy, and I NEVER will. I'm a TOTAL BOTTOM with men, it's who I AM.

 

First time I bottomed I was drinking. Most of the time after I was sober. I enjoy topping also

 

For me it started in my youth and some occasional jerking off together. One of my friends was interested in more than jerking off. It evolved from blowjobs to anal curiosity, the consensus was that the smaller endowed would be”the girl” so to speak. Well, that was me and after several failed attempts we finally succeeded. I do think that it has an affect on someone in their youth. I am masculine on a daily basis but very submissive behind closed doors. I’m still small endowed and enjoy all things submissive from(in those days) watching girlfriends fuck other guys to watching my wife with other guys. I haven’t bottomed in years but still have the great desire to be a sub bitch for a man.

 

With my first wife the subject of anal didn't get started until we were married about 7 years and I gently fingered her bung while she was riding me and had an unbelievable orgasm...she was very vocal as I sank my entire middle finger inside her and feel my throbbing member. After several experiences like that I suggested she take my cock which she was very open to experience. With plenty of lube and repositioning several times I managed to slide in as she gasped and moaned quite loud...I pulled out, she says...NO, go back in...I do and she begins to ram her butt against me to get more of me inside until my 8" was bottoming out inside her...she started shouting "fuck me"..."fuck me" baby!...She got a hell of a pounding and had two orgasms. She was a anal whore after that night. If introduced properly many women find out they enjoy it. If the first time is a bad one they most likely will never try again.

 

My current wife is the only woman I've had anal with that enjoyed it and would orgasm just from an ass fucking.

 

As for me, I've always enjoyed anal stimulation. Started solo with a finger or two while masturbating. My wife soon discovered that I liked it, and would rim, finger, butt plug, dildos, and finally pegging with a decent sized strap on. Now I wonder what the real thing would feel like, and being filled with cum. I can dream, can't I?

 

You can always dream...I myself started enjoying anal with my present wife (1st wife would never stimulate my anus) with fingers, then vibrators, then dildo's to all out strap on fucking that is always fantastic. Now with her encouragement our boyfriend fucks me with his 9 1/2" and the feeling is over the top as she'll suck me during and then he blows his huge load deep inside me...OMG! I love being fucked in the ass.

 

The first time I bottom was with a friend. I had been curious for a long time about being with a guy as i grew up in religious home. It started with kisses and cuddling till finally I was swallowing his load several times a week to at least once a day. Finally after three months of this he said he wanted to eat my ass, It was disconcerting at first but it became enjoyable esp when he started fingering my ass too. The following week I caved and I told him that I wanted Daddy to take my virginity. He gladly did that night it took sometime but soon I took his 7in cock in my ass as hard as he could give it. I haven't found anyone bigger than that to try and its been almost two years since anyone has been inside my ass.

 

I gave my virgin ass up earlier this year at 55 to a real cock after a few years of the wife pegging me with larger and larger dongs. I was a little worried about our boyfriends 9 1/2" cock fucking me but once he eased his way inside I relaxed and was able to enjoy him balls deep and I seem to want him all the time since. I like my wife's strap on but his throbbing cock is far better.

 

Nice

 

I started almost by accident in the sense that I engaged in a few random three somes including two males one female, usually after drinking. I never thought much about it but then I started masturbating with anal toys and then I hooked up with a few guys before actually being bottomed for the first time. I had used a lot of toys so I felt ready. After that the enjoyment continued to evolve and I had some tranny hooker experiences where I asked to be there little bitches. After they made me suck their cocks I would beg to be fucked and even had one of them go ass to mouth because slutty bitches deserve that. That's what I found myself asking for when I was paying. I'm in a committed relationship with a girl and we just started pegging, which has been fun. But basically, what I learned over time is that my turn on as a bottom is being that person's toy. I want to be completely owned as their sissy bitch in panties before having my head pushed down and my ass pounded.

 

I've been using dildoes and plugs since I was a young teen. Even household objects if they were safe. So I'm used to having my asshole stretched and probed. The first time a guy fucked me was not uncomfortable at all. In fact it felt so good I actually had a hands free cum! You really can't feel much when he comes, so I usually prefer that he pull out and let me swallow his load! Sounds like fun, huh?

 

Well, I have had a lot of hot times sucking cock but I was not planning on giving up my ass. I meet up with a new guy and we got along great, even making out on the couch before we headed to the bedroom. His cock is beautiful, maybe 6.5". I loved sucking it, then he went down on me, sucking my cock, kissing my balls then lifting my legs and rimming me for a long time. Keeping my legs in the air he scooted up a bit and started rubbing his cock near my hole. It felt so good that I reached for the lube I had in my night stand and handed it to him. He was the first to take my ass.

 

One of my friend a few years older had suck me many times and also asked to fuck me. Finally I gave him and he fuck me until he shot his load into my ass. I came like I never had before and it felt so good having his dick in my ass. He continue to fuck me ever couple of week at his house or business. I always play hard to get but he always end up fucking me. I love the fucking he gave me until he couldn't hard anymore.