Need Advice - BF into Tranny Porn and Strap Ons

[CherryNetherlan]

Help please - my boyfriend is fascinated with Trannys and would like me to use a strap-on on him.

We had great sex recently while watching Tranny porn, the ladies were all incredibly beautiful and sexy, and he loved it when the camera panned down them to reveal hard cocks being stroked, sucked.

He just shared with me that one of his deepest, private fantasies is for me to use a strap on that he could suck and I could fuck him with.

He is extremely sexual and is much more sexually advanced than me. He's had more female partners in his past than he could probably remember, hosted swinging parties, and has had group sex numerous times. He attracts and loves being surrounded by beautiful women.

I'm not sure what to think - is he bi, gay, tranny, or because he has tried all that a 'straight' male can try, is this something new and hot for him to experiment with? I am not sure that I can ask him without him thinking I'm being judgemental, he has trusted me with a very private fantasy that personally would be fun to act out. My concern is that ultimately I may not be able to give him what he really is looking for.

Any advice would be much appreciated!

 

[human_male]

What's the problem? Are you worried that because he wants you to use a dildo on him he's actually gay? Or are you just intimidated because he's way more experienced than you?

I don't know him but I can tell you that having bi or gay fantasies, liking trannies, wanting you to do him with a dildo and even sucking it like a dick doesn't mean he's gay, or that he wishes you were a man, or wants a man or is going to leave you for a man or whatever else your mind has come up with. Trust me, it's common for straight (or straight-ish) men to have all sorts of desires and fantasies for cock and stuff like this. It doesn't necessarily mean they actually want a real cock, or want to have sex with a man. Really.

If I were you I'd stop being so insecure, rush out and buy a stap on and enjoy this side of your partner with him.

 

[scmale2000]

He is a lucky man!

You sound like a GREAT girl and he is lucky to have you. A lot of guys (and girls) simply read things in books (or Penthouse or Lit) or see something in movies and, once they do, realize that it could be a turn-on. I'm very open about trying new things and your bf's fantasy is one of my own as well. He obviously trusts you and, since you are cool enough to be open to it (and turned on by it), go for it. Buy the strap-on without telling him and surprise him with an evening of fantasy fulfillment. I would love to know how it turns out.

Help please - my boyfriend is fascinated with Trannys and would like me to use a strap-on on him.

We had great sex recently while watching Tranny porn, the ladies were all incredibly beautiful and sexy, and he loved it when the camera panned down them to reveal hard cocks being stroked, sucked.

He just shared with me that one of his deepest, private fantasies is for me to use a strap on that he could suck and I could fuck him with.

He is extremely sexual and is much more sexually advanced than me. He's had more female partners in his past than he could probably remember, hosted swinging parties, and has had group sex numerous times. He attracts and loves being surrounded by beautiful women.

I'm not sure what to think - is he bi, gay, tranny, or because he has tried all that a 'straight' male can try, is this something new and hot for him to experiment with? I am not sure that I can ask him without him thinking I'm being judgemental, he has trusted me with a very private fantasy that personally would be fun to act out. My concern is that ultimately I may not be able to give him what he really is looking for.

Any advice would be much appreciated!

 

[sunandshadow]

All men have prostate gland, which apparently feel wonderful if massaged with fingers or a cock/dildo. Feels just as good to straight men as gay ones. The straightness is who he wants that feeling from: you, a female. Trannies or hermaphrodites are sort of a special case because people usually think of them as either male or female, depending on which gender they are attracted to. He probably sees them as female. Thus sex with one would be more or less straight. But people fantasize about a lot of things they don't actually want to do.

If you do buy a strap-on, a Feeldoe is the best because both the woman and the man feel the sensation from them, unlike the archetypal strap-on which does nothing for the person wearing it.

 

[CherryNetherlan]

Thanks for all the great advice! I am feeling a lot better, it really does help having other people's POV. And yes, a lot less insecure

I live in LA and there is a fabulous adult toy store. I took him there a while back, it was the first time I ever saw him speechless, it was great. He loves going there, he's like a kid in a candy shop. I think I may surprise him by taking him there after a night out so we can shop together.

Scmale2000, I will post back to let you know how it goes. He's out of town for a few weeks tho I think it's an incredible gift you can give someone to fulfill a fantasy.

Sunandshadow, thanks a bunch for the tip on the Feeldoe. I have heard that a leather harness is best, but other than that, this is new territory for me.

Heh, I think I had my fingers in his ass when he started talking about the strap-on. It was so hot, in that single exhale of breath right before he came, he strained out 'oh god, yougottamakethishappen'. Pretty hard to refuse that!

 

[Etoile]

Leather is best unless you don't mind your harness sounding like backpack straps.

Seriously, sunandshadow is right. Just because a guy wants to experience anal sex doesn't mean he's gay. If he wanted a MAN to do it, then maybe he would be bisexual, but he wants you to do it, so he's just interested in the sensation...what it feels like.

I prefer the Nexus to the Feeldoe - the end the woman wears is shaped more like your own insides, so it gives you a more "natural" feeling. The egg end of the Feeldoe is going to feel like you have something foreign in you - I'm sure it feels good, but I would think it feels more like you're wearing a strap on rather than using an extension of your own body.

 

[Tymeless]

good responses and very interesting

 

[sunandshadow]

Leather is best unless you don't mind your harness sounding like backpack straps.

Seriously, sunandshadow is right. Just because a guy wants to experience anal sex doesn't mean he's gay. If he wanted a MAN to do it, then maybe he would be bisexual, but he wants you to do it, so he's just interested in the sensation...what it feels like.

I prefer the Nexus to the Feeldoe - the end the woman wears is shaped more like your own insides, so it gives you a more "natural" feeling. The egg end of the Feeldoe is going to feel like you have something foreign in you - I'm sure it feels good, but I would think it feels more like you're wearing a strap on rather than using an extension of your own body.

Oh interesting, I haven't tried the Nexus. *googles it*

Leather - mine tends to soak up my sweat and consequently reek, and you can't just throw it in the washing machine. But other that that, yeah, leather's great.

 

[CherryNetherlan]

I totally understand what you are saying, and you all are right - He does see the trannies as female. And while he has had MFM, I'm pretty sure he has not had MMF. Plus fantasy #2 is to bring in another woman (lol, men - you gotta love em).

Ahhh - you don't need a harness for either the Feeldoe or Nexus! Would you still recommend using one?

Haha, I can be squeaky or stinky, eh?

The Feeldoe has the bullet vibrator, hmmm. Then the Nexus looks like he would enjoy it better during double penetration.

Decisions, decisions...

 

[uptoplay2]

feeldoe option

He can use the short end of the feeldoe... and then use both his cock and the longer part of the feeldoe on you. Or ... you could just ride the long end, that would be good for him too. With either of these options.... definitely no harness problem.

Expect to need something for the nexus and feeldoe at the start... unless you have great kegals and a lot of confindence.

No clue which feels better for a woman inside... but I'd love to hear!

 

[RowanMist]

Just a random statistic for you, only about 5% of 'Straight' people are 100% straight, everyone one else has some fantasies/acts that are considered homosexual. This doesn't make him any less straight, not even bi, it makes him normal!

Oh, and for anal first timers, start small. If it hurts it can ruin the moment. Here are my tips; go slow use lots of lube, and make sure everyone is nice and horny! This way things will turn out for the best. Have fun!

 

[CherryNetherlan]

The boyfriend is coming back in town on Monday.

We've had some pretty hot phone chats over the past couple of weeks that I'm glad we had cause I have a better idea about what he would like.

Sadly the feeldoe and nexus will have to wait a little longer. He would like to try a realistic big cock. I said, 'Big? Big as in thick or big as in long?' He said both would be nice, and I chuckled and replied he would have to finish everything that was on his plate. His answer - Bring it on!

Has anyone used the leather Terra Firma?

I read some previous Lit posts on strap-ons, and got some good tips. Is there anything I should make sure I avoid doing?

 

[Etoile]

Wow, he must have some experience, if he's asking for the big stuff! If you can, try to get silicone rather than vinyl. Most of the big realistic ones are vinyl, but silicone is SO much easier to clean and for that reason also safer! Get vinyl if you must, but wherever you're shopping, ask about silicone.

The Terra Firma is my 2nd most recommended harness behind the Texas 2-Strap.

My tips on strap-ons are here: http://snipurl.com/straponadvice

 

[Missouribiguy]

I could always be your strap-on test buddy, Cherry.

 

[CherryNetherlan]

Etoile, I am sure you hear this all the time, you are the best Your tips are really helpful, plus I now have another cool site. Silicone - yes - cleaning will be very important. I forgot that I need a harness that can take a dildo with balls, and both harnesses can. I can't wait to tell him to lick my balls.

This will be his first time with a strap on, I was originally thinking something on the smaller side as well. I have fisted him (or at least up to my knuckles, I think that counts) so he's got some experience. I told him he was not allowed to touch his dick until he took all of my cock in, and he said he was not afraid

Aw thanks for the offer Missouri We're a little too far away!

 

[RowanMist]

Silicone is definitely the best, but I would suggest using a condom too, it just makes it 100 times easier to clean! Not only that, but it can fit in better with the fantasy that it's a 'real' cock...

 

[Resonate717]

Wow - the world is fun!

What a find. I love what you have all written so far. After having experimented with two men, (only penetrated by one - was waaaay too tense) I finally got up the courage to ask my girlfriend about a strap-on. She barely even blinked...she's so great. The whole experience has been one of the most challenging and rewarding things to happen in my sex life. I feel so vulnerable when I let her inside me, such a totally different set of emotions that come with the sex. It makes me feel so whole, though. Being receptive like that seems to access a totally different part of one's sexuality, and is such an adventure! Of course, I felt a little bit of guilt after the first time, was it right, was I gay, etc. but refused to let myself think the thoughts of society. I call myself straight with a twist or bi, but know that I am sexual. And I'm thrilled to explore any part of myself that is sexual, included being mounted by my woman. Enjoy the trip, CherryNetherlan, don't take it too seriously. Sex is to be played with, enjoyed! I'd be curious to hear a woman's perspective on using a stap-on for the first time; how does it feel to change roles and to be penetrating someone if you haven't before?

Thanks to all for listening!

 

[janetcd]

I agree with Resonate, 1000% !

 

[CherryNetherlan]

What a find. I love what you have all written so far. After having experimented with two men, (only penetrated by one - was waaaay too tense) I finally got up the courage to ask my girlfriend about a strap-on. She barely even blinked...she's so great. The whole experience has been one of the most challenging and rewarding things to happen in my sex life. I feel so vulnerable when I let her inside me, such a totally different set of emotions that come with the sex. It makes me feel so whole, though. Being receptive like that seems to access a totally different part of one's sexuality, and is such an adventure! Of course, I felt a little bit of guilt after the first time, was it right, was I gay, etc. but refused to let myself think the thoughts of society. I call myself straight with a twist or bi, but know that I am sexual. And I'm thrilled to explore any part of myself that is sexual, included being mounted by my woman. Enjoy the trip, CherryNetherlan, don't take it too seriously. Sex is to be played with, enjoyed! I'd be curious to hear a woman's perspective on using a stap-on for the first time; how does it feel to change roles and to be penetrating someone if you haven't before?

Thanks to all for listening!

Thank you for such a personal and thoughtful post Resonate717. You have reminded me to be extra sensitive to BF's state of mind over the next few days. Part of him is feeling very subconscious about the social stigma attached. When I told him about the research I was doing and the help I've received, his response was, 'So I'm not crazy.' And I said not at all!!!

I think I'm going to wear a corset with the strap on. Contrasting the curves and feminity of the corset with a big hard cock I hope will blow his mind. There's also something so sexually dominant about a corset too.

Tomorrow night it is - wish me luck

 

[RowanMist]

Good luck!

 

[MasterMischief]

I think I'm going to wear a corset with the strap on. Contrasting the curves and feminity of the corset with a big hard cock I hope will blow his mind. There's also something so sexually dominant about a corset too.

That mental image is very arousing.

To anyone who may be lurking with the same question CherryNetherlan had, allow me to offer the following advice. If your partner initiated conversation about a fantasy it is because they want to talk about it and quite likely, try it. Do not be shy about asking questions and continuing the conversation they started.

Do not worry about feeling inadequte or some other hidden meaning. Find out more before jumping to conclusions.

 

[PantyLisa18]

Is it just me, or is it to obvious to tell you to simply ask him what his intentions are? Admitadly I am probably the most logical female you will ever meet, but I don't understand why if you have a question about your lovers intent you don't just ask them?

He has already risked a lot to admit he likes tranny porn and wants a dildo up his ass. So you taking that next step and asking point blank "Is this where it ends or do you fantasize about male-male sex" is not going to risk anything in the relationship.

He either answers "No" and you continue down the path you seem to be headed which includes you strapping one on for him on occassion, or he answers "Yes" and you then can decide where the relationship heads from there.

 

[sister76]

I wish I had a strap on. I would love to fuck my husband up the ass. He would probably like it, too. I don't know where to get a good strap on. I don't want to waste my money. Any suggestions?

 

[Mr. Briggs]

I wish I had a strap on. I would love to fuck my husband up the ass. He would probably like it, too. I don't know where to get a good strap on. I don't want to waste my money. Any suggestions?

The one we have is great. It feels good and looks real. It's the doc johnson realistic one.

 

[Etoile]

I wish I had a strap on. I would love to fuck my husband up the ass. He would probably like it, too. I don't know where to get a good strap on. I don't want to waste my money. Any suggestions?

Here's my advice, I wrote this a while back: http://snipurl.com/straponadvice