What are you doing or thinking about doing you never imagined.

[69plus1]

I think I am a typical guy who has explored his sexuality at some point in life.
Up until my 40's I was a confirmed hetrosexual. Loved women especially eating pussy.
But at some point, about the time Penthouse Letters and Forum came out publishing an occasional story with some bi action for the men.
I really liked those stories to the point that I looked for only them and was disappointed when there weren't enough. This was way before the internet made finding these things easy to fine. I knew there were mags in the adult stores that were bi and gay orientated but the thought of anyone finding out my dirty secret prevented me from exploring that route.
So much later with the explosion of the internet I was able to explore these things in private. I found literotica and wrote stories as an outlet but soon that wasn't enough so I really started fantasizing ways to explore without getting found out.
Finally many years later I had my first experience with another man and loved it immediately. We spent a hot afternoon enjoying oral sex. All I had thought about was oral, giving and receiving. Nothing more.
At some point my partner rimmed me and I exploded with one of my most memorable orgasms.
A few, very few women had done this wonderful thing for me and i really enjoyed it, but never asked for it for fear of being refused.
But as I left that mans bed room on my way home I relived that feeling of having a tongue in my ass. I couldn't get that feeling out of my head to the point of thinking that maybe I would let him fuck my ass. I came very close to reconnecting with him to try to relive that wonderful ass licking and more.
Sadly I relocated and never connected with him again.
To speed this up, over the next few years my "I love sucking cock but I would never....." list changed.
My won't list changed from: would I let just anyone fuck me......or rim another guy......or god forbid kiss another guy!
Now after a few oral experiences I am ready to do it all.
My last cavet is I "don't fuck on the first date!" And kiss another guy?
Well when I find the right guy to take me anally I want his tongue to fuck my mouth like his cock fucks me ass.
So, finally, I guess my question is: What are you doing or at least fantasizing about doing that you never imagined you would do?

 

[nassauguy_2001]

I am constantly fantasizing about having a guy I know and trust fuck me bareback. I have always had guys use a condom, but I want to feel him unload deep in my ass sans the rubber. Maybe I will find the guy I trust enough to do this.

 

[55alive]

Being in my mid-50's, and married for 26 yrs, my thoughts seem to wonder, especially sexually. If it's a fantasy, then I would love to hook up with a Tranny. Having the best of both worlds, and then having her take my virgin ass.

 

[Jenna2641]

I'm thinking of trying chastity for 30 days. Not with a cage. Just self restrainent. Not sure I'll last.

 

[SteveBrad1]

I never imagined being with a guy. When I was 18 one day, I was in the shower at my indoor pool that I frequent. I never really noticed guys, but then noticed this guy's butt.

It was nice and tan and really sexy. I can't even remember his face now. I don't remember seeing his front.

I remember masturbating several months to him. Nothing really specific. But just picturing that cute butt. I always went out with girls, but this never bothered me. I thought it was just so hot.

I guess the image faded and I went out with girls again. Sort of forgot about it.

It was months later when I noticed guys again. I started at a restaurant with a lot of gay staff. They noticed me a lot. One guy asked me if I swim. He commented I have a swimmer's body.

I never got that attention from girls. Unless it was a girl you went out with. Girls look in public, but they're discreet. I still go out with girls. But I really really really have this streak of exhibitionism. Not even so much internet. Altho that's ok, more in person.

I started coming to work in tight jeans. Changing in the locker. Wearing thongs so they could see my butt.

Now, I was with one guy. But no longer. I really want to try another dick, but am not in a hurry. I've even dated a couple of girls this year.


What I'm *thinking* about is eventually doing two guys. Just being on all fours. With two muscular hotties. One in my ass and one in my mouth. I love both and can't *imagine* how it would be at the same time. That will take some time, but I'll get there. But oh gawd, right now! I am getting hard just thinking about two big muscular guys fucking me at both ends!

 

[69plus1]

Good luck

Jenna dear, good luck with that! I without went three days and it was the longest year of my life.

 

[Hornyguy888]

69ing with a cd

 

[sub2femdom]

69ing with a cd

I don't know that I ever considered doing something I said "never" to- but what turns me on certainly has evolved over the years... The hard no's for me are scat play and pain games, and I don't see that ever changing.

 

[Jenna2641]

Jenna dear, good luck with that! I without went three days and it was the longest year of my life.

Ya, thanks to a friend exchanging erotica via e-mail, yesterday was a rather trying day, but I have been doing better today. Despite the teasing, other distractions have kept me balanced.

 

[Jenna2641]

Day 4 complete & halfway through Day 5.

 

[Iwantsomeplease]

........

 

[SissySalina]

Day 4 complete & halfway through Day 5.

Hope you make it.
If the will is strong the mind will follow.
Completing the task is reward in itself.

 

[jakelc]

Introducing my wife to my boyfriend and suggesting (slowly) we try to make things work as a threeway. I’m not stupid enough to go marching blindly in and announce I want him to move in but an introduction and then a hint here or there. I always thought my sexuality and cross dressing would be hidden from her forever and now both are wide out in the open.

 

[Jenna2641]

Hope you make it.
If the will is strong the mind will follow.
Completing the task is reward in itself.

I think I can. I gave up smoking after 3 years by first setting 30 day, then 60 day, then 90 goals. The 3rd year stuck. And I do pretty good at month long exercise challenges.

5 days complete. Working on day 6.

 

[PleasePeesMe]

I'm fantasising

more and more about sucking a shemale cock. A big one.

 

[Jenna2641]

I think I can. I gave up smoking after 3 years by first setting 30 day, then 60 day, then 90 goals. The 3rd year stuck. And I do pretty good at month long exercise challenges.

5 days complete. Working on day 6.

Made it to day 13. It was a crazy on Day 11. I was listening to a cock sucking induction hypnosis mp3 & it got really intense. With a few more setting, I think I could have cum hands free. Very enjoyable. But still holding steady.

 

[sunshine9]

Made it to day 13. It was a crazy on Day 11. I was listening to a cock sucking induction hypnosis mp3 & it got really intense. With a few more setting, I think I could have cum hands free. Very enjoyable. But still holding steady.

Somebody pee on me. Please.

 

[UnderMyKilt]

So, finally, I guess my question is: What are you doing or at least fantasizing about doing that you never imagined you would do?

I have been fantasizing about, then thinking about, then researching, then planning and NOW I'm making reservations for a long four night weekend at a suite in a gay resort in Palm Springs. I have a day of business nearby and the rest is my time.

I could have "imagined" that, but I never would have imagined that it would be with my wife's blessing and at her suggestion! During a recent trip to Palm Springs as a couple, we happened by such an enlightened establishment and she "caught" me checking out some twinks outside (after I uttered "Mmm, mmm, mmm" under my breath).

She said, half jokingly, "Why don't you stay there when you come down for...."

"Really?" I said. "You'd be OK with that?"

"Sure!" she laughed. "You need it and it would keep you off my ass for a weekend."

After getting home, and after more conversations, the "joke" became reality.

Well...I take the "never imagined" back to a certain extent since we've never had any secrets. She always known of my gay/bi past (and I hers), my penchant for all things anal, my eye for the fellas, and my way less than vanilla sexual "needs". She's been more than a willing participant in incorporating those things into our sex life but she's older than me and...age...arthritis, pulmonary fibrosis, fibromyalgia and the physical toll of over 40 years as an RN have slowed her down and made many of our prior sexual acrobatics impossible for her. What we do together is still satisfying, but she knows I'm insatiable and it's implied that I might look for boys, but not girls, away from home.

This will be my fifth solo out-of-town trip in the last calendar year, for one reason or another, with the implied intent that I might attempt to hook up on each one. I hooked up on two of those trips, one sweet and intimate, one quick and dirty. This will, obviously, be the first with the explicit intent of having a long weekend of ass-fuckery and I fully anticipate the experience to meet and exceed my anticipation.

Still...who knew my complicated sexual life, would now seem to be so seemingly simple, when I'm a SEXagenarian. How appropriate.

 

[UnderMyKilt]

Made it to day 13. It was a crazy on Day 11. I was listening to a cock sucking induction hypnosis mp3 & it got really intense. With a few more setting, I think I could have cum hands free. Very enjoyable. But still holding steady.

Awfully quiet? 17 days? Yay or nay?

I don't think I could pull this off. I don't sleep right unless I've had an evening cum...LOL. I'd have to really have to put in some extra roadwork in lieu of sex and I'd probably lose 20 lbs in the process. (From the calorie burn and...because we often tend to do a little cannabis before sex which usually means...THE MUNCHIES.)

 

[charterguy05]

I think I am a typical guy who has explored his sexuality at some point in life.
Up until my 40's I was a confirmed hetrosexual. Loved women especially eating pussy.
But at some point, about the time Penthouse Letters and Forum came out publishing an occasional story with some bi action for the men.
I really liked those stories to the point that I looked for only them and was disappointed when there weren't enough. This was way before the internet made finding these things easy to fine. I knew there were mags in the adult stores that were bi and gay orientated but the thought of anyone finding out my dirty secret prevented me from exploring that route.
So much later with the explosion of the internet I was able to explore these things in private. I found literotica and wrote stories as an outlet but soon that wasn't enough so I really started fantasizing ways to explore without getting found out.
Finally many years later I had my first experience with another man and loved it immediately. We spent a hot afternoon enjoying oral sex. All I had thought about was oral, giving and receiving. Nothing more.
At some point my partner rimmed me and I exploded with one of my most memorable orgasms.
A few, very few women had done this wonderful thing for me and i really enjoyed it, but never asked for it for fear of being refused.
But as I left that mans bed room on my way home I relived that feeling of having a tongue in my ass. I couldn't get that feeling out of my head to the point of thinking that maybe I would let him fuck my ass. I came very close to reconnecting with him to try to relive that wonderful ass licking and more.
Sadly I relocated and never connected with him again.
To speed this up, over the next few years my "I love sucking cock but I would never....." list changed.
My won't list changed from: would I let just anyone fuck me......or rim another guy......or god forbid kiss another guy!
Now after a few oral experiences I am ready to do it all.
My last cavet is I "don't fuck on the first date!" And kiss another guy?
Well when I find the right guy to take me anally I want his tongue to fuck my mouth like his cock fucks me ass.
So, finally, I guess my question is: What are you doing or at least fantasizing about doing that you never imagined you would do?

Penthouse letters I agree changed things for me I too started reading the bi stories then tried on my sisters panties and went from there. I have not had much in my ass but want to explore more with a real person than a dildo but either way I never thought I would be thinking or yearning to feel a cock in my ass like I do

 

[richgo50]

I have been fantasizing about, then thinking about, then researching, then planning and NOW I'm making reservations for a long four night weekend at a suite in a gay resort in Palm Springs. I have a day of business nearby and the rest is my time.

I could have "imagined" that, but I never would have imagined that it would be with my wife's blessing and at her suggestion! During a recent trip to Palm Springs as a couple, we happened by such an enlightened establishment and she "caught" me checking out some twinks outside (after I uttered "Mmm, mmm, mmm" under my breath).

She said, half jokingly, "Why don't you stay there when you come down for...."

"Really?" I said. "You'd be OK with that?"

"Sure!" she laughed. "You need it and it would keep you off my ass for a weekend."

After getting home, and after more conversations, the "joke" became reality.

Well...I take the "never imagined" back to a certain extent since we've never had any secrets. She always known of my gay/bi past (and I hers), my penchant for all things anal, my eye for the fellas, and my way less than vanilla sexual "needs". She's been more than a willing participant in incorporating those things into our sex life but she's older than me and...age...arthritis, pulmonary fibrosis, fibromyalgia and the physical toll of over 40 years as an RN have slowed her down and made many of our prior sexual acrobatics impossible for her. What we do together is still satisfying, but she knows I'm insatiable and it's implied that I might look for boys, but not girls, away from home.

This will be my fifth solo out-of-town trip in the last calendar year, for one reason or another, with the implied intent that I might attempt to hook up on each one. I hooked up on two of those trips, one sweet and intimate, one quick and dirty. This will, obviously, be the first with the explicit intent of having a long weekend of ass-fuckery and I fully anticipate the experience to meet and exceed my anticipation.

Still...who knew my complicated sexual life, would now seem to be so seemingly simple, when I'm a SEXagenarian. How appropriate.[/QUOTE

Please let us know how your trip to Palm Spings goes. I would love to go and be able to dress up and be used and suck and lick. I am not passable and trying to lose 25 lbs. I am also 68 so time is running out. The wife might let me go. Again let us know how your trip goes. If you could let us know what resort and what month.
Don't mean to be intrusive but your post really hit the mark for me. This has become my fantasy

 

[Jenna2641]

Awfully quiet? 17 days? Yay or nay?

I don't think I could pull this off. I don't sleep right unless I've had an evening cum...LOL. I'd have to really have to put in some extra roadwork in lieu of sex and I'd probably lose 20 lbs in the process. (From the calorie burn and...because we often tend to do a little cannabis before sex which usually means...THE MUNCHIES.)

I made it to day 18 & day 19 is almost done. Tortured myself yesterday lots of erotic chat. I was leaking pre-cum like a faucet & one particular chat had me squeezing my thighs together in a way that almost drove me over the edge. But I resisted the urge to take mattees in hand & backed off. Whew!

 

[dango_dog]

I never thought I would talk to complete strangers about sucking cocks or anal. Reading a story about it is one thing talking to a live person is a whole other thing.

 

[Chi_Guy_68]

What I would never have imagined

Prior to about 10-12 years ago, I would never have imagined that I would fantasize or get turned on by the thought of sucking a dick. But I'm very turned on about that and often fantasize about doing it.

Then for the longest time I was only interested in oral with a man, but in the last year or so, I've gotten really curious about getting fucked. I'm more and more open to just having sexual experiences with another man - something I never would have imagined.

 

[Chi_Guy_68]

Prior to about 10-12 years ago, I would never have imagined that I would fantasize or get turned on by the thought of sucking a dick. But I'm very turned on about that and often fantasize about doing it.

Then for the longest time I was only interested in oral with a man, but in the last year or so, I've gotten really curious about getting fucked. I'm more and more open to just having sexual experiences with another man - something I never would have imagined.

Also for years I was just turned on by hard cocks (wanting to suck them and fondle them with my hands). But now I'm noticing being attracted to men (especially noticing the bodies of guys in good shape).

I'm still very attracted to women, but I see things I like on men beyond just a nice cock.