His First Time with Strap-on

[amylin456]

The first time is not easy... women have not developed those thrusting muscles very well. Your ass and thighs will ache for days afterward. I found that having him on his back with legs over my shoulders is a lot better... gives me several ways to thrust and something to lean against. Plus, you can give his cock and balls a some attention while you do it.

That sounds so very sweet and sexy......

 

[allurs4thenight]

I wish I could find a girl to do this to me. This is my number 1 fantasy Ever!

 

[allurs4thenight]

oops double post!

 

[Mr. Briggs]

Having a woman do me with a strap on is like one of my biggest fantasies. I would love to find a woman and give her my ass.

It's so enjoyable

 

[amylin456]

Just go dominant on him. When he sees you naked and you're in charge I doubt he'll resist. Don't say anything but "lay down" and then do your thing.

I love your attitude !!!

 

[Hexachord]

One of my favorite times with a strapped lady was coming home from work to find the wife wearing it under her skirt. Dragged me to the bedroom and bent me over, then let me ride her 'til I came on her tits and belly. Immense fun, hope to do it again sometime.

 

[lets_experiment]

The wife and I tried it a few times with a "normal" strap on. Harness with a dildo. She looked absolutely exquisite wearing it. She was willing to tolerate it for me but it didn't really do much for her. Then we changed to a "feel doe" style. Something to be inside of her while she was using it on me. BIG Difference. Now she asks to use it on me. Big change in the experience for her. And if she is happy, then I am happy. It has since become a fairly regular part of our sex life.

 

[Mr. Briggs]

The wife and I tried it a few times with a "normal" strap on. Harness with a dildo. She looked absolutely exquisite wearing it. She was willing to tolerate it for me but it didn't really do much for her. Then we changed to a "feel doe" style. Something to be inside of her while she was using it on me. BIG Difference. Now she asks to use it on me. Big change in the experience for her. And if she is happy, then I am happy. It has since become a fairly regular part of our sex life.

Wow that's good to know

 

[oxfordsea]

Love to have my wife, or other woman, if she'd be willing to pop my back door cherry.

 

[Rigger287]

Having tried a small stainless steel butt plug, a larger glass butt plug and a solid metal dildo on myself, I would love to try a strap-on with a lady who would be prepared to be slow and gentle as she screws me until we are both satiated.

 

[preacher72]

I fucked him one time. Hot crazy romp in the sack, but neither of us came. He blamed it fucking all night with his gf. He wasn't patient with me. Then his real estate agent was scheduled to walk in any minute. He's a big player, and is really into young, beautiful girls - I am mature - MILK - and attractive, but not his type. Maybe it will happen again.

Im sorry to hear that you sound like my type id take that strap on any day

 

[Mr Bob]

A lady friend and I went to an adult store today and purchased a strap on together. I found the shopping to be rather exciting. We settled on one that she liked and would not be to big for me to handle. She has had strap on sex with other women before so her expertese came in handy. I have never had anything bigger than a finger or two in my ass befjore so am looking forward to her taking me. Any tips anyone can give me to make this very enjoyable would be appreciated. getting together next Wednesday and I can hardly wait

 

[Mr Bob]

My lady friend and I went to a motel yesterday and had first time strap on sex. It was fantastic. She started by giving me a nice massage which relaxed me as I was nervous. She massaged her way to my ass and got it all hot and loose, plenty of lube. She then began to fuck my ass with the strap on and it felf great. I had no discomfort and she fucked me very good. Next time she is bringing a larger phallus, I can hardly wait. Will be after first of year so stay tuned

 

[Brent106]

I have had the pleasure of having a woman use a strap-on with me. It is an incredible feeling and one that every man should feel at least once. If only more men knew how good it felt to have their prostate massaged. Having her peg my ass hits the right spot and I have the biggest orgasms.

 

[laurencedarabie]

Like the cock piercing

 

[nfrrdscnnr1]

sorry

I fucked him one time. Hot crazy romp in the sack, but neither of us came. He blamed it fucking all night with his gf. He wasn't patient with me. Then his real estate agent was scheduled to walk in any minute. He's a big player, and is really into young, beautiful girls - I am mature - MILK - and attractive, but not his type. Maybe it will happen again.

Sorry neither of you, especially you, didn't get off. Better luck next time.
Did you get close? Did your shyness get in the way? Had you fucked him longer could you have been sufficiently stimulated to get to the big O??

 

[Bi_Siamese]

I called an agency that specialized in Femdom. I was forty they sent a cute black lady around 19. I gave her the money she went with me to the bedroom strapped on my own harness and dildo screwing me for the entire half hour without talking. She drove me crazy and was very skilled. She pulled out removed the dildo said goodbye and left. Both my ass and head were spinning.

 

[Bi_Siamese]

Screwed by an Amazon

My wife was a six foot tall atheletic German Amazon butch. I was a handsome six foot tall brunette atheletic with a seven cut inch cock. I was her slave from day one when she surprised me one night on the couch unzipping my jeans and went down on me giving me a suck of a lifetime. Unafraid of letting me come in her mouth I gave her one heck of a blast. That was the best suck of my life and she definitely had me hooked. The next afternoon she invited me over to her place inviting me up to her bedroom. I thought I was going to get lucky when she started talking about spanking. Sharing that she had been spanked bare bottom all the way up to age 18 I told her that I had been spanked but not at a later age. I was about 31 years old and she suggested I was long overdue to get another spanking. In a stern voice she told me to pull my pants down to my knees and give her my belt. She then pulled me over her lap and gave me one hell of a whipping. It hurt my ego more than my ass but it was surprisingly a turn on as well. A year ago and old girlfriend gave me a bare bottom spanking that burned my curiosity into trying to find another dominant woman. Finding this gem of a lady was a one in 1 million chance. That was the beginning of our female dominant relationship.
We married in the early 80’s when BDSM was taboo and strapon sex was underground. There was not much available for how to dominate books and there was no internet. We had seen the erotic movie the opening of misty Beethoven where a guy got screwed in the ass with a dildo while screwing his girlfriend at the same time. My wife/mistress demanded we find a harness and dildo and do the very same thing to me. We had to experiment ourselves. We both had nasty imaginations and acted them out. I went to an adult store in town and found a cheap harness and dildo that would work that only had a 6 inch dildo but perfect for taking my cherry. My wife was quite excited and that Saturday afternoon I was naked in bed over pillows about to lose my virginity. Truthfully I didn’t know if she had used a dildo before or a vibrator but she knew exactly how to skewer me on the dildo and pop my cherry. She took her time using lots of lube. It hurt at first getting past my sphincter muscle but once I relaxed some she aggressively started fucking me. I couldn’t believe that for the first time I was on the receiving end instead of being the one that was doing the screwing. My wife actually preferred oral sex over intercourse and now having her own dildo she was in another glorious world experimenting with 21st century female domination. I looked over my shoulder while she was fucking me and asked if I could play with my cock at the same time and she gave her permission. I wanted to reassure my sexuality that I was still in charge in someway by masturbating while I got fucked. In about 15 minutes I filled my hand with come and tried to get up but my wife pushed me back down and started fucking me even harder. She was actually enjoying herself and watching my body wiggle, squirm, and listening to my cries and it was turning her on. She even held still to have me fuck myself sliding back and forth on the dildo. I learned a hard lesson that dildoes never gone soft and can last as long as your mistress wants to continue fucking you. With some pain my wife pulled of the grand opening taking my virginity with much success. Getting fucked was more than I expected and very desirable to repeat again. When my wife finally pulled the dildo out of my gaping ass she decided to give me a good strapping to take care of my homophobic guilt. Lecturing me during the strapping she reassured me that getting fucked in the ass by a dominant woman has nothing to do with Homoerotic feelings. It is all about dominance and serving your lady and being a obedient to her wishes. She made me pledge to find better harnesses and dildos because she wanted to be the fuckee in our relationship from now on.

 

[saintcero]

Bi_Siamese Posts above

Thanks for the two posts Bi_S, they will fuel many Lit fantasies.

 

[hasabrain2]

I am a bi gal and love to be dominment, although I am Shy.... I am fucking a guy with a strap-on for his first time today. I want to be as "professional" as possible. We met on a chat line. I like the idea of being dominant. I look sweet, but play hard. I don't want to talk about our families, etc. Just business. Any thoughts? Advice? I want him to cum back again for more. He says he's straight, but I think he's up for some real cock.....

I will let you practice on me if you want.

 

[NateBiDude]

I'm basiically a top but I've been ass fucked a couple of times by two different guys. Enjoyed it but just not my thing. I've had a burning fantasy to be strap fucked by a smoking hot woman. Feels awkward bringing it up for some reason when I meet a woman. Most women are ok with me beiing bi, but maybe I could explain that I'm a top but would love a woman to use a strap on. Still feels like an awkward conversation. Any suggestions?