Using a Strap-On?

[cynical_bitch]

So my boyfriend and I have been together about a year, and have sex on a fairly regular basis. He's got a nice sized package, never complains about wearing a condom/not getting enough from me, always offers to get me off before he finishes, and stays to cuddle afterwords. He's the first guy to ever finish me and genuinely enjoys getting me off...Basically, what I'm saying is that the sex is awesome.

I knew going into our relationship that he was bi-sexual and had no problem with it, and he has brought up liking to masturbate with a toy in his ass. This is fine with me, and I have told him that the thought of using a strap-on to have sex with him wouldn't be something I was opposed to. He confessed that this was one of his fantasies, so we went out and bought one. The first night we tried to use it, I got the harness on and put the dildo in the right place...and then started to laugh. For some reason, I couldn't be serious with it on, so much so that we decided to forgo it for the night.

I felt/feel terrible, because he does so much for me and I really want to be able to do this for him. He'd like to be dominated while I do this, and I'm thinking maybe if I get in that mindset it would help, but I'm kind of stumped as to how to get there.

I guess, bottom line: Does anyone out there have suggestions for how to emotionally "set the scene" to use a strapon on a submissive male partner?

 

[Roc_crawl]

While I'm not sub and can't speak for your boyfriend, I would suggest that you use some build-up to a night of fun that involves sexting and sexy chat to set the stage for your role reversal. Keep it suggestive initially to test your comfort level. At this point you don't know what you or he like, so use innuendo to work toward a scenario that makes you both comfortable. I would think a first sext of, "I'm gonna fuck your ass you dirty little boy" may be too much...it may NOT be, but start light and work toward what works for both of you.

From that base you can tailor the play to take him where he wants to go and slowly get used to your role as the Dominant. It may be that he wants to be "taken" or just have his lover take the lead to help him explore or something in the middle...it'll be great fun to learn together.

As far as the laughing/giggling is concerned...worry not. My Mrs. giggled a good bit as well and it took a time or two for her to get used to the sensation and visual. After that, she came to a point where she enjoyed the role reversal and the pleasure it brought her, her female lovers and myself.

Have fun and report back regularly.

 

[kodos9000]

Now this is just an idea, my GF and I use toys on me including a strap on!
I think you jumped to the strap on to quickly, try moving to it a little slower, use a dildo on him hold it against your pelvic bone like its your cock and try fucking him with it! this was how friends of mine eased into it!

I also agree that you need to set the mood, lots of talking and have fun with it! sex is supposed to be fun after all!


Let me know how it works!

 

[hotrochnywife]

Not sure which strap on you are using but I have 2 that are double ended so I get the benefit of enjoying it as much as he does

One has a strap and is called "Double Delight Strap-On". The other is strapless and is really amazing as it almost makes you feel like it's actually part of you called the "Tantus Feeldo" There are a few different sizes of the Tantus. I have the medium one. But the tantus is much harder to keep inside of you. It will take you some getting used to. Also it comes with a very small but very strong vibe Lastly if you decide you like the Tantus but it's still tough to keep in you can use most straps with it or even a pair of his underwear!

Both work great and maybe with the added dimension of you getting pleasured it will make it easier for you and keep your mind properly occupied

Hope it helps!

 

[Handoveryourgoo]

My suggestion?

So my boyfriend and I have been together about a year, and have sex on a fairly regular basis. He's got a nice sized package, never complains about wearing a condom/not getting enough from me, always offers to get me off before he finishes, and stays to cuddle afterwords. He's the first guy to ever finish me and genuinely enjoys getting me off...Basically, what I'm saying is that the sex is awesome.

I knew going into our relationship that he was bi-sexual and had no problem with it, and he has brought up liking to masturbate with a toy in his ass. This is fine with me, and I have told him that the thought of using a strap-on to have sex with him wouldn't be something I was opposed to. He confessed that this was one of his fantasies, so we went out and bought one. The first night we tried to use it, I got the harness on and put the dildo in the right place...and then started to laugh. For some reason, I couldn't be serious with it on, so much so that we decided to forgo it for the night.

I felt/feel terrible, because he does so much for me and I really want to be able to do this for him. He'd like to be dominated while I do this, and I'm thinking maybe if I get in that mindset it would help, but I'm kind of stumped as to how to get there.

I guess, bottom line: Does anyone out there have suggestions for how to emotionally "set the scene" to use a strapon on a submissive male partner?

Your boyfriend's story could be my story. I have not quite gotten to that point with my wife, but the drem would be this: plan a role reversal night. He picks out your outfit and you pick out his. Then play the role. Be confident, gentle, and relaxed about figuring it all out. Whisper to him how hot it makes you to dominate him. Reward him for good behavior. And make him suck it before you take him.

 

[starider07]

How about trying

this, when you have plenty of time for just you, you put on the strap-on and play. You lube it and rub it like it's your own. Get used to it so it isn't so funny but a turn on. Realize that this turns him on. You must want to please him. As my friend kodos said, this is supposed to be fun so make it so. I've not done this, but if my wife would, I would. This is a special time for you so don't humiliate him by laughing at him. Enjoy it with him. Let us know how it goes.

 

[SweetErika]

Honestly, it CAN look really funny!

I'm sure you reassured your bf that you weren't laughing at him in any way, and hopefully you two can take comfort in the thought that some of the best sexual moments include/are based on laughter. Don't worry about it and move on.

Regarding getting in the right headspace, I like to think about what having a "cock" and anal sex really mean. For me, they both can mean power and responsibility. Anal penetration in particular, if done improperly, can cause immense pain and serious physical and emotional damage. There's nothing funny about that! On the flip side, when it's done properly, it can lead to very intense emotions and pleasure. It can be transformative - the toughest people can feel submissive, vulnerable, an incredible release, etc. Part of it is also being the doer/giver instead of the receiver in new ways, which is pretty cool.

So, while the look might be silly, when I put that strap-on on, I feel a great sense of power, which is something I take quite seriously and get a lot of pleasure from myself. Plus, I can do a bunch of different things with my "cock" (e.g. making my partner perform oral on it, "worship" it, slap it against his cheeks, use it as the focus of talking dirty), which is pretty awesome.

Basically, look it all you can do with your strap-on and what it really means to both of you, then use those things to set the mood and help you decide what to do. I'm guessing once you see what really using it is like, it'll become a lot more cool and a lot less funny to you, too. But, hey, if you're playing the dominant role and you feel like laughing, there's nothing wrong with that, either!

 

[sterculius]

I agree with SweetErika, I enjoy switching roles with my wife. I love being made to deepthroat her cock!! And she likes being in charge sexually. Check out these sites for inspiration.
http://isissandosiriss.tumblr.com/ http://ferrre.tumblr.com/ http://bendoverboyfriend.tumblr.com/
http://gender-bender.tumblr.com/

 

[canadianpenny]

Redacted

 

[hotrochnywife]

We did some more of this last night and to be honest there were moments when we both had to laugh a little. It is a little clumsy and odd at first since we both are in positions we are not used to if that makes any sense.

But we both had a lot of fun and really enjoyed ourselves!

 

[dotmbl1415]

Thanks for the advice

i was reading the comments and they are very helpful. I guess it happened to my lover and I also. That awkward moment right before you take the plunge. So we stepped back and had to figure out how to be comfortable in role reversal. We still haven't gone all the way yet but getting closer. I think the anticipation makes it so much hotter...

 

[mattastic100]

comfort

................

 

[BeAGoodBoy]

It seems like he's ready to give in and you need some convincing. I'd say dress the part, wear the strap-on, when youre alone and try to feel your dominant side. You need to see if it's really you or not.

 

[ButtAnalMan]

So my boyfriend and I have been together about a year, and have sex on a fairly regular basis. He's got a nice sized package, never complains about wearing a condom/not getting enough from me, always offers to get me off before he finishes, and stays to cuddle afterwords. He's the first guy to ever finish me and genuinely enjoys getting me off...Basically, what I'm saying is that the sex is awesome.

I knew going into our relationship that he was bi-sexual and had no problem with it, and he has brought up liking to masturbate with a toy in his ass. This is fine with me, and I have told him that the thought of using a strap-on to have sex with him wouldn't be something I was opposed to. He confessed that this was one of his fantasies, so we went out and bought one. The first night we tried to use it, I got the harness on and put the dildo in the right place...and then started to laugh. For some reason, I couldn't be serious with it on, so much so that we decided to forgo it for the night.

I felt/feel terrible, because he does so much for me and I really want to be able to do this for him. He'd like to be dominated while I do this, and I'm thinking maybe if I get in that mindset it would help, but I'm kind of stumped as to how to get there.

I guess, bottom line: Does anyone out there have suggestions for how to emotionally "set the scene" to use a strapon on a submissive male partner?

for me, you can spank my butt while i am on your knee before you do

 

[psecond_psyght]

in my experience it's easier to work up to it like everyone is talking about in the post. i think they're still putting the cart before the horse though.

bring it up during sex. after he's made you cum and it's his turn to get off talk about how would like to bend him over the bed and make him take it. get him really worked up and the positive reinforcement will literally cum. you'll both get your reward from the dirty fantasy talk.

if you haven't tried it yet also use a hand held toy on him while he's masturbating. however since you are trying to find your dominant feet in the situation make him wait till you tell him he can touch himself. every time he tries to slap his hand away. tell him you decide when he gets to stroke it.

after you feel a little more confident in the new role tell him to suck your "cock". whether you're in bed or you're on the couch watching tv or what ever have him get in front of you and give you a blow job. hopefully by the time you get to that point you'll be able to put him in "his place".

i hope i've been helpful. take care and happy pegging.

 

[mattastic100]

just right

i dont recommend this one. it is too ridged and hard. Not enough flexability

 

[cynical_bitch]

Hey guys,

I just wanted to say THANK YOU to everyone who responded. We've been slowly working our way up with dirty-talk, a small bullet, and then the dildo without the strap-on. He's really appreciated taking it slow.

Your advice was totally what i needed to figure out the right direction. Thanks again!