That Time My Man Taught Me How To Do Another Woman With A Strap-On

Let me start with a language warning.  

This story is about sex. Down, dirty, hot, intense, raw sex. So I'm using sexual slang because that is the way I tell a story.

If the words dick, pussy and fuck offend you, you probably don’t want to keep reading.

I've been bisexual as long as I can remember. I love both boys and girls. In fact, I love all the different gender permutations. For me, attraction is about energy and connection, so gender becomes secondary.

Over the years I've had lots of female friends who have confessed that at various times they wished they had a dick. Some of these friends are lesbians, others are transgender, others are bisexual and quite a few are straight. 

My straight friends were interested in pegging, and talked about how hot it was to have a guy suck their dicks.     

I have never wanted a dick, even for a short time. I have always loved my lady parts, and I've always been very happy to be the receptive partner, the "fuck-ee," if you will. 

I never felt a need to be the fuck-er. In times when it was useful to be the more active partner, I always found my mouth, tongue, fingers and toys to be perfectly sufficient.

I also never played with a man who wanted me to fuck him, so I never got into pegging.

For the longest time, the women I played with were either happy to fuck me, or happy to have me fuck them using my fingers, tongue or a vibrator. 

The, about 5 years ago, I was playing with a couple of women who told me they would enjoy it if I fucked them. I’m usually game to try most things so I thought, why not?  

I'm a firm believer that the right tool for the job makes a big difference in how a job turns out.

So I set about finding the right tool for the job. I remembered that a guy I dated had given me a strap-on harness as a gift in the late 90’s (I suppose that was a hint but I completely missed it!). The harness was a gorgeous, made of leather and python with gold on one side, but when I tried it on it was too tight, so back into the toy box it went.

Time for a shopping trip! 

I was in Los Angeles visiting my then-fiancé, and we headed out to the Pleasure Chest in search of a good dick. 

We went to the counter and started looking at strap-on harnesses. You might be surprised by how many different kinds there are out there. Not just different brands, but entirely different types.

There are harnesses that go around your thigh. Ones that are thongs. Some that are very girly, or attached to panties, or sporty, or simple and made from leather. 

I was, quite simply, overwhelmed.

I called a queer friend of mine who said, "Just try a few and see what is most comfortable." She told me that, as with other things, you get what you pay for, so I should make sure I was getting one that was well made.  

I decided on a semi-sporty harness. Now I had to find a dick.

Picking a dick was even harder than picking a harness. The number of shapes and sizes and colors available is staggering. I never liked multi-colored, phosphorescent dildos very much. I prefer the natural look, so I immediately ruled out anything purple, pink, or neon yellow.

I knew that if I looked down and saw that I would not be able to stop laughing, and thought that this was likely to ruin the mood. 

I decided that it would be good to have a dick that was at least somewhat reflective of my skin tone. My fiancé started pulling out the white dicks and holding them up against my arm. He quickly put aside anything that was too dark and eventually found a couple that matched my skin tone perfectly. I was 12 shades of red by the time I settled on the medium size and gleefully took my purchases up to the counter.  

Now that I had purchased the right tools, I needed to figure out how to put them on so I wouldn’t fumble on my play date. I tried to put on the rig myself, but eventually had to ask my fiancé to help me figure out how to fasten everything. After a bit, I was all set.

I looked down and went into shock.

I have a round belly so when I looked down, instead of seeing harness, all I could see was this pale dick jutting out from between my legs. The color match is so good that it looks like the dick belongs to me. It was the most bizarre feeling.  

Having the right tool is only a small part of success, however. For complete success, you need to use the tool expertly. This was a problem. 

I had no idea how to fuck someone.  

Remember the first time you were with a new lover who couldn’t quite find the right place? I can’t count the number of times I've to say, "Sorry, but, wrong hole!" 

I experimented with various movements, only to continuously falling down in a heap of laughter.    

I didn’t want to be an awful fuck, or worse yet, a boring one, so I decided to ask an expert for help.

I turned to my fiancé and asked him to teach me how to fuck a woman.

First he helped me get into the right position. We started with missionary position. He got in position next to me and told me to watch how he moves.

"It’s all in the hips," he told me.  

More peals of laughter. I kept looking down, seeing "my" dick bobbing up and down, and I just couldn't keep a straight face.    

My second try was better. He put his hands on my hips and moved them for me until I was able to relax. After about 30 minutes, I was moving smoothly.  

Now for my play date.

It was with a friend I had been flirting with for some time. I arrived and things quickly heated up. There was hot kissing, a bit of biting and I settled down for some sweet oral.

When we were both warmed up, I put on my dildo, a condom and some lube, and I was ready to go.  

I started slow and easy, and then picked up the pace. My date bucked and moaned underneath me. Sweat rolled down my body as I pushed harder and faster. Her orgasm caught me by surprise. She wailed, dug her nails into me and almost upended me as she pressed up and tried to mash our bodies closer together.

Another orgasm followed, and by the time her breathing returned to normal, I was drenched in sweat — and lube.

When my date returned to earth, I withdrew slowly (because withdrawal is always the worst part!). I collapsed next to her on the bed. We cuddled and talked for a bit, all the while my dick still hard and ready to go. 

Every time I caught a glimpse of "myself," I did a double take.

After a while, I took off the harness and we went back to cuddling until it was time for me to go home.

My fiancé greeted me with, "Well ... ?," as I walked through the door.  

I grinned from ear to ear and said, "I made her cum more than once, and she was screaming. She asked when we can do it again."

His deep chuckle warmed me.  

"What was it like for you?" he asked.  

"I loved watching her. I loved that I was making her feel so good. It made me so fucking high. I got hot and wet — but I didn’t cum," I said.

"Do you think that's because there wasn’t enough pressure on your clit?" he asked.  

"Maybe," I conceded, "But I don’t think so. I just think I prefer to be the bottom."     

He pulled me to him and growled in my ear, "Good, because I prefer to be the top."   

The conversation stopped and my own moans began ...

If you want to talk to me about my sexual adventures and how you can create more of your own, email me at drbisbey@the-intimacy-coach.com. To learn more about my Intimacy Coaching practice, visit me online at www.the-intimacy-coach.com, and sign up to take the free Ultimate Passion Test to learn how to light your fire today!