Need help broadening myself.

[Chrishasso]

A few months ago, a girl I’ve been dating/fooling around with introduced me to a whole new world and ever since I’ve been wondering about it and hopefully this is somewhere I can find some help.

As someone in my mid twenties, I’ve always been more of a stereotypical guy who likes girls and has an intense sex drive. I’ve always been up to trying some of the kinkier things, and my sexual friend and I enjoy a little tying up from time to time. Like I said, a few months ago, she tied me up spread eagle and started her usual game of lick and tease until she reached my thighs and started to lick further and further towards my ass. I was really nervous and unsure, kind of pulling away, but I was pretty aroused and it felt wonderful. After not to long, her tongue was penetrating me and the way it wiggled and squirmed inside me, made me lose my mind...

After she had been teasing my ass and stroking my now extremely hard cock, I started to moan for more and she started pumping her fingers in and out of me. It was a feeling I had never even imagined and I was going wild. After seeing how much I was enjoying it, she pulled out her favorite toy, which is a long phallic vibrator and she started to slowly play with it around my asshole while her tongue played. I have to admit, after a while I was begging for more and my deviant fuck buddy began to work lube and the toy into me. After not to long she was working the vibrator in and out of me while she went back and forth from teasing me about how much I was enjoying it, to licking or kissing me in a myriad of ways. I eventually started to lose it, and while panting uncontrollably I came unlike anything I’ve ever felt.

Afterwards, I felt really self conscious and she teased me about it at work the next day. So I set that off limits... I said I’d enjoyed it, but it’s not for me... For the next while, trying to keep it a secret, I couldn’t stop making every masturbation session I had turn into me finding something to help me feel the same unreal experience via something in my ass. Not to mention I found this site and read story after story involving pegging or being bottomed.

I then started to try and figure out how to get my partner to do it to me again without hurting my pride... Because I’m still a little embarrassed about how much I really enjoy the experience. So... I started to try and get caught playing with my ass when my friend was going to come over. I did things like try and leave the little egg vibrator I got to use in my regular solo times, or lift my ass off the bed while she went down on me... But eventually I just made it so I couldn’t help but be caught and started using the vibrator on my ass while she slept next to me...

When she woke up to me doing it, she kind of just chuckled and started helping after admonishing me a bit for trying to hide or deny how good our first session was. It was horrifying, but so arousing... Since then, our sex has gotten even kinkier and she keeps talking about how bad she wishes she could teach me how good a real cock feels cumming inside you. Little by little, I’ve come to really want to know what it’s like.

I’ve come to enjoy sucking on her toys, being pegged, and cleaning up my own cum both inside her and off myself or whatever I end up making a mess on. In our fantasy talk, she’s gone so far as suggested bringing another cock into our regular sex games. I really love our friendship and damn, is the sex the best I’ve ever had, so I want to try and make it even better.

All of the above, said... I am incredibly aroused by a good looking (I really don’t want to offend anyone) transsexual woman with a nice cock... I can’t stop watching videos of guys being bottomed by a sexy woman with a cock... And I love when I can find the occasional video of a guy being drilled by another guy while he makes out with or stares into the eyes of his female partner... That being said, I fully understand I’m a masculine bisexual guy now, but I’m needing a little help to work through the thought before we finally make it real.

I’m kind of hoping this forum can help me through either some good role play and good advice to help me get more comfortable faster... I admit, the fact that I’m kind of safe from too much ridicule on here as the internet keeps me a little more anonymous, as I don’t know how I’d take coming out just yet, as I’m still working through it. But I have to say, Everything my partner and I have done has really made me more aroused than I ever have known, and the climaxes are beyond all explanation, I’m addicted. I can’t stop thinking about it, but it’s just to myself... I’m hoping I can get more confidence through interactions with all of you.

Hopefully I haven’t upset or disrespected anyone through this story, it’s not my intention... I’m just trying to grow in all of my new experiences.

DMs and posts here are both appreciated, thank you beforehand for sharing.

Chris

 

[blowit]

I for one cannot see anything in this post that could upset or disrespect anyone so please stop worrying.
What you will have done is make a lot of men, myself very much included, extremely jealous of your relationship. Go with it so far as you both feel comfortable would be my advice.
One minor point. If you're taking cock in the arse you are being 'topped' as opposed to bottomed.

You're a very lucky man.

 

[CandiCame]

You don't have to come out until you're ready and sexuality is complicated. I don't know enough from your post to know if you'r even into guys, really, or just really like anal. And there's no shame in either one! I just want to point out that liking anal doesn't make you bi, liking people of different genders does. If you do then that's cool. I'm also a bi guy who loves anal.

I'm actually not sure why you hid this from your gf when you liked it so much and she also seems to be into it.

You don't have to figure everything out right away. Sex is supposed to be fun- that's the point of sex. So try not to get too scared or freaked out. I know all this is new, but your g-spot is in your ass for a reason, it's totally natural to be into it. Just go slow, use more lube than you think you need, and figure out what works for you. You've got a supportive partner to help and it seems like everything is going to be fine. Honestly, you'll like it more once you stop being so nervous- if you're chill and relaxed it's even better.

I don't know if you're into it, but if you smoke a bowl first it'll settle your nerves. I think that you really just need to do something, beforehand, to settle your nerves. You're cool man. Anal's fun.

And if you find out that you do identify as bi, guys are fun too. The real ones don't vibrate but they do lots of other fun stuff.

 

[2wayroad]

Indeed you are lucky. She has opened a door for you that can not be shut. And you should be thankfull for it. I came to these realizations on my own. It would have been so much better with an intuitive guide like your friend.

Do not try to categorize yourself. Sexuality is a spectrum, not a series of boxes. You are not gay, bi, pan whatever just because you enjoy receiving anal sex.

That having been said. It’s going to be easier to have another man present with your female friend there. Trying to find, then objecify a trans woman will be difficult. You will already have a woman present. My advice is to try with a man. I’ve been the receptive partner with men for years and now find I prefer it over hetero sex.

You have been adventurous and open minded to this point. Your female friend recognized something in you and brought it out in you. Try it, if you don’t like it, that’s okay. It won’t make you gay. I don‘t know why so many think that one experiement forever changes their sexual identity. Many men have sex regularly with other men who lead straight, masculine lives. They have their regular friends who probably are unaware. The straight population doesn’t suddenly see you with a scarlet letter on you. If you don’t tell, they wont is what I’ve found.

Relax and enjoy.

 

[Jada59]

You have nothing to be embarrassed about. If it feels good, do it!

 

[Sissy_Trish]

Maybe you should ask to wear some of her lingerie next time she wants to take your ass....and I can tell you once you try her stuff on your going to be hooked. Lingerie and nylons are sensual, even more so when you are wearing it.. she willhave fun with it as well...trust me

 

[Silvery65]

Many years ago I was dating a girl that did basically the same thing when she had me tied up and like you the pleasure was intense. We unfortunately didn’t date long and it was never repeated. All these years later I still regret not pursuing her kinky desires more. I have recently started using my wife’s dildo in my ass when masturbating and it is wonderful. I’m hoping to find a real cock soon but am terrified that I would get caught as it would end my marriage.

 

[MichelleD55]

I've cross dressed since I was about 8 years old (now 66).
It was always a turn on, but did not share it with my first wife.
I told my second wife before we got serious so I wouldn't wimp out for fear of losing her.
My wife is good with my dressing and it is somewhat of a turn on for her too.
So there was no problem with me shaving everything below my ears as the saying goes.
I can't tell you how much more sensual the lingerie and nylons feel when you shave.

Once you try that you will be hooked.

Get dressed and logon to Literotic for an hour or two. You will be ready to explode after that.

 

[cubbyfire04]

A few months ago, a girl I’ve been dating/fooling around with introduced me to a whole new world and ever since I’ve been wondering about it and hopefully this is somewhere I can find some help.

As someone in my mid twenties, I’ve always been more of a stereotypical guy who likes girls and has an intense sex drive. I’ve always been up to trying some of the kinkier things, and my sexual friend and I enjoy a little tying up from time to time. Like I said, a few months ago, she tied me up spread eagle and started her usual game of lick and tease until she reached my thighs and started to lick further and further towards my ass. I was really nervous and unsure, kind of pulling away, but I was pretty aroused and it felt wonderful. After not to long, her tongue was penetrating me and the way it wiggled and squirmed inside me, made me lose my mind...

After she had been teasing my ass and stroking my now extremely hard cock, I started to moan for more and she started pumping her fingers in and out of me. It was a feeling I had never even imagined and I was going wild. After seeing how much I was enjoying it, she pulled out her favorite toy, which is a long phallic vibrator and she started to slowly play with it around my asshole while her tongue played. I have to admit, after a while I was begging for more and my deviant fuck buddy began to work lube and the toy into me. After not to long she was working the vibrator in and out of me while she went back and forth from teasing me about how much I was enjoying it, to licking or kissing me in a myriad of ways. I eventually started to lose it, and while panting uncontrollably I came unlike anything I’ve ever felt.

Afterwards, I felt really self conscious and she teased me about it at work the next day. So I set that off limits... I said I’d enjoyed it, but it’s not for me... For the next while, trying to keep it a secret, I couldn’t stop making every masturbation session I had turn into me finding something to help me feel the same unreal experience via something in my ass. Not to mention I found this site and read story after story involving pegging or being bottomed.

I then started to try and figure out how to get my partner to do it to me again without hurting my pride... Because I’m still a little embarrassed about how much I really enjoy the experience. So... I started to try and get caught playing with my ass when my friend was going to come over. I did things like try and leave the little egg vibrator I got to use in my regular solo times, or lift my ass off the bed while she went down on me... But eventually I just made it so I couldn’t help but be caught and started using the vibrator on my ass while she slept next to me...

When she woke up to me doing it, she kind of just chuckled and started helping after admonishing me a bit for trying to hide or deny how good our first session was. It was horrifying, but so arousing... Since then, our sex has gotten even kinkier and she keeps talking about how bad she wishes she could teach me how good a real cock feels cumming inside you. Little by little, I’ve come to really want to know what it’s like.

I’ve come to enjoy sucking on her toys, being pegged, and cleaning up my own cum both inside her and off myself or whatever I end up making a mess on. In our fantasy talk, she’s gone so far as suggested bringing another cock into our regular sex games. I really love our friendship and damn, is the sex the best I’ve ever had, so I want to try and make it even better.

All of the above, said... I am incredibly aroused by a good looking (I really don’t want to offend anyone) transsexual woman with a nice cock... I can’t stop watching videos of guys being bottomed by a sexy woman with a cock... And I love when I can find the occasional video of a guy being drilled by another guy while he makes out with or stares into the eyes of his female partner... That being said, I fully understand I’m a masculine bisexual guy now, but I’m needing a little help to work through the thought before we finally make it real.

I’m kind of hoping this forum can help me through either some good role play and good advice to help me get more comfortable faster... I admit, the fact that I’m kind of safe from too much ridicule on here as the internet keeps me a little more anonymous, as I don’t know how I’d take coming out just yet, as I’m still working through it. But I have to say, Everything my partner and I have done has really made me more aroused than I ever have known, and the climaxes are beyond all explanation, I’m addicted. I can’t stop thinking about it, but it’s just to myself... I’m hoping I can get more confidence through interactions with all of you.

Hopefully I haven’t upset or disrespected anyone through this story, it’s not my intention... I’m just trying to grow in all of my new experiences.

DMs and posts here are both appreciated, thank you beforehand for sharing.

Chris

So it sounds like she's on board with really anything you are feeling sexually right now. Have you tried having the conversation outside of the bedroom? Something like, "when you mentioned seeing me get fucked by another man... Is that something you're truly interested in?"

No is a fine answer. You're exactly where you are now. Great, kinky sex with someone you love. Yes is an opportunity to let her know how you feel. And while I don't think your interest in a trans woman with a cock is going to scare her away, the issue is more about finding that unicorn. They aren't as abundant as porn would have you believe, however they are out there. Are you open to another masculine man? Anyone worth bringing in to your bedroom will be respectful of your boundaries.

Don't settle for a quick online arrangement. Make sure you're all 3 on the same page in the "get to know you" phase. Perhaps swinging or something is worth looking into as well. I find that swinger bi couples tend to be open to fulfilling other couple's fantasies. They often lead to realizing new ones as well!