What was your best strap-on experience, and what made it great?

[gergyorgergyor]

Gents, ladies, whether you were the wielder or recipient of said harnessed dong, which time was the ne plus ultra of strappin’?

For me, it was the very first time. I won’t rhapsodize overly here because I’m hoping to get off my non-Literotica story writing butt and make a story of this glorious event.

However, some of the things that were particularly wonderful:

• She and I had talked about it and watched some female on male strap-on porn along the way.
• I was her 2nd sexual relationship ever. The dipshit before me never helped her come, never really tried.
• She wasn’t sure if she wanted to go black leather quasi femdom- until the night of and got dressed. My normally _very_ conservative girl looked NICE sporting that cock.
• She came several times. Thank you, bullet-vibe!
• It all just worked. Everything either of us wanted to do, the other was really ready for.

greg

 

[SouthernAlberta]

1st time

We’d talked about ass play during sex and we both enjoyed it. Tongues, fingers...

So I stopped at an adult toy store on the way home from work and bought a small 5” dildo and harness setup took it home and hid it in the closet. Man I was nervous. We hadn’t specifically talked about me taking a dildo in the ass. I didn’t want her to think that I was into guys {25 years later and I’m definitely bi. Lol. And comfortable with it).

So a day or so later we’re hot and heavy in the bedroom. Ass play is happening. I start talking dirty. I’m nervous. I ask he if she’d like to fuck me with a strap on. Oh yes she’d love that, thinking I’m just fantasizing with her.

Then I get up and go to the closet, pull out the strap on and cock. As soon as she sees it her eyes light up and she gets this shit eating grin on her face. She is down!

From there we bought a feeldo. We broke it. Lol. Now we have a selection of cocks and a nice soft leather harness for her. Life is grand.

 

[bobb_sledd]

Likely not what the OP had in mind...when ED made penetrative sex all but impossible for me, I took to wearing a strap-on to service the wife. Between the strap-on and oral, I was able to keep the wife satisfied until her desires waned when lady issues neutralized her needs.

 

[bjlatx]

My wife and I were on our last night in Venice. We were in a fairly small hotel with only a few rooms. The room we were in was huge. It was one of the suites and had a balcony that overlooked the Grand Canal. There was a rooftop deck that we would sit at and drink wine with other people we would meet. This night we had drank a lot and it was getting late. It began to rain so we ran down to our room. While I was in the bathroom, my wife put on her strap on. I came out to her just standing there stroking it. I got naked as quickly as I could as she sat down on an oversized chair in the room. I got down on my knees and proceeded to suck her cock while she would take it out a playfully slap my face and tongue with it. She fucked my face for a while and then told me to stand up and turn around. She told me to sit down on her dick and she began to fuck me and stroke my cock while every once in a while playfully slapping my ass. After a while she told me to go out on the balcony. It was still raining and she bent me over the railing and proceeding to fuck me hard until I came. It was awesome.

 

[Smoothshavendad]

My wife and I were on our last night in Venice. We were in a fairly small hotel with only a few rooms. The room we were in was huge. It was one of the suites and had a balcony that overlooked the Grand Canal. There was a rooftop deck that we would sit at and drink wine with other people we would meet. This night we had drank a lot and it was getting late. It began to rain so we ran down to our room. While I was in the bathroom, my wife put on her strap on. I came out to her just standing there stroking it. I got naked as quickly as I could as she sat down on an oversized chair in the room. I got down on my knees and proceeded to suck her cock while she would take it out a playfully slap my face and tongue with it. She fucked my face for a while and then told me to stand up and turn around. She told me to sit down on her dick and she began to fuck me and stroke my cock while every once in a while playfully slapping my ass. After a while she told me to go out on the balcony. It was still raining and she bent me over the railing and proceeding to fuck me hard until I came. It was awesome.

Wowza!!!!!

 

[Goldenfinger]

Not the best but still a good story.

We were at some sort of medical convention for my wife’s work. Her work sent maybe a hundred or so people and put us up at a nice hotel. One evening we maybe drank a little too much. When we got to the room my wife unpacked our strap on. We made out, fooled around and then she aggressively fucked me. We were pretty loud the whole floor heard us. So I must sound like a girl when she fucks me cause the topic of the next day was my wife’s a screamer.

 

[gergyorgergyor]

Very glad to hear your wife is so good at it!

Wondering if I'd want my wife's work colleagues to think she was a screamer or know I was. Society's expectations and how we meet them or don't impacts the way they treat us, including on the job are so complicated (and generally somewhere between wrong/ stupid and totally fucked up.)
One one hand, her coworkers think they know a sexual secret about her, but an "acceptable" one. On the other hand, perhaps it would be "worse" (whatever that would mean) if they saw her and thought, "she's the one whose husband cries out like a virgin bride for god knows what reason!"

I've become totally obnoxious about that stuff if/ when work people choose to inquire TMI'ily. Perhaps, "how do you know all that screaming was either one of US?"

greg

 

[TallOne]

The first time my wife managed to trigger a prostate orgasm. Quick version. One of our "Sinful Sundays" where we tend to have our kinkier sex sessions. Me laying on my stomach on the bed, hips propped up by a pillow. Wife on top of me thrusting into me with all her strength and body weight. Was hitting just the right spot and love the feel of someone on top of me rather than doggy or me on top. I started feeling an orgasm building but it felt different, with more of a tingle sensation accompanying it and feeling like I had to pee. It just kept going to the point I yelled out "How am I still cumming?!?!?!?" And that was the biggest load I've ever produced, accompanied with a seemingly constant stream of pre-cum.

Also, me using the strap-on on her either for some double penetration or while I am locked up and she chooses the stunt cock for a hot mindfuck and total focus on her.

 

[Goldenfinger]

Very glad to hear your wife is so good at it!

Wondering if I'd want my wife's work colleagues to think she was a screamer or know I was. Society's expectations and how we meet them or don't impacts the way they treat us, including on the job are so complicated (and generally somewhere between wrong/ stupid and totally fucked up.)
One one hand, her coworkers think they know a sexual secret about her, but an "acceptable" one. On the other hand, perhaps it would be "worse" (whatever that would mean) if they saw her and thought, "she's the one whose husband cries out like a virgin bride for god knows what reason!"

I've become totally obnoxious about that stuff if/ when work people choose to inquire TMI'ily. Perhaps, "how do you know all that screaming was either one of US?"

greg

I’m glad she’s good at it also.

I do know some of her colleagues know the truth about who it was. It’s not a well guarded secret.

 

[Mason9653]

We talked about a strap on and when she agreed she insisted that I go into Lou der local sex shop to buy it in person.

The first few times was a learning experience for both of us. Then we got good at it, then she told her friends.

They all know and they are at our place often with their sly smiles.

I wasn't surprised when one of her friends asked in front of everyone if we had considered the real thing.

With that they suggested a few different guys and began discussing the guys and all the details.

While that hasn't happened I did agree to let them watch. That was the best!

 

[lowcollar]

After she pegged me with the big black dildo, she fisted me for the first time. Unbelievable!

 

[Goldenfinger]

I’ve had a lot of great experiences. It’s hard to choose one.

 

[Britva415]

One time my girlfriend got me off with pegging, then we cleaned the dildo off and put a new condom over it and I wore the strap-on and pegged her. I got hard again and one-man double penetrated her! Fun times.

 

[BiGuy999]

In a city centre hotel with floor to ceiling windows. Bent over with my hands on the window watching the people below walking around the city whilst my wife fucked me with our largest strap-on telling me how much she loves fucking ass. She came several times that night. I didn't cum at all. Such delicious agony!