Strap On Sex – For Beginners

adventure-strapon

Following the same format as the “How to choose a Strap on guide”, I thought it would be more interesting to educate a little about strap on sex by sharing my own personal experience. It is my hope that this is not only helpful, but entertaining as well. So what follows, is my personal story, including all the pitfalls and some helpful tips that I have learned since…

I mentioned in the previous article that my main reason for using a strap-on was because I had a serious desire to find out what it was like to fuck a woman. So, we’re talking about woman fucking woman here (just want to make sure we’re all on the same page.) I also thought it might be kind of fun with our g/f because she’s usually up for anything, and to that I’m extremely grateful.

Over a year after buying the harness, the three of us (my b/f, my g/f and I) were finally able to make some real plans to meet and ring in the New Year with total filth. She lives a few states away, so getting together is not always easy. What a great way to start the New Year, the anticipation after all this time was just killing me!

I showed my g/f the harness and dildo earlier in the day because it was going to be a highlight of our time together. I also wanted to really confirm that she would be cool with that kind of play; you know making sure things didn’t look too scary or seem too weird. Its one thing to talk fantasy and filth with someone over the phone and online, but it’s quite another when you actually start to bring out the toys and things start getting real.

Just as I had hoped, she was totally digging it. She loved the look of the harness (See, I’m glad I was so finicky when purchasing one!) and she was really excited about feeling the dildo inside her. So, we have initial success, now we’ll fast forward to actually the next morning. I never got to the strap-on that night; I just wasn’t feeling it for some reason. Besides the fact that I was way too busy with my head in her pussy all night. The next morning she inquired about the strap-on…that’a girl!

Not wanting to disappoint and still really wanting to do it, I decided to get naked and don my strap-on. Once I got it set, my b/f pulled on those friction buckles making it nice and secure, as I giggled over thought of what was I was going to do. Somehow, I knew the giggles were going to happen, I get them during sex, but hey, it’s all in good fun right? So why not? One of the deals I made with my g/f was if she wanted me to fuck her, she was going to have to suck my cock first.

Hey, I’ve seen it in porn and think it looks hot, so I’d like to experience what it’s like. As she lay on her stomach across the bed, I propped my right leg up on the bed, real porno style (as my boyfriend put it) and told her, “You know what you have to do…Suck my cock, beeatch!” Sure enough, she did it. I giggled, she giggled, but it was pretty hot. I mean here I am standing over her telling her to suck my cock and she does it. I’m feeling rather powerful at the moment and starting to wonder if this feeling is going to get any stronger…

It’s Time for Penetration…Houston We Have a Problem

After the brief, yet sexy and fun cock sucking, I got her naked and laid her on the Ramp Liberator Shape on my bedroom floor. As she lay on her back with the Wedge Ramp under her booty, I thought, wow, this is pretty cool, this really going to happen. So I gave her some manual and oral pleasuring to get her all worked up, which got me all worked up and then it happened…

I learned about a problem that I hear about a lot on Allsexadvice.com…finding the hole! I know that many men, first timers or pros, experience this problem, but it was really funny to be kneeling down between her legs, laughing and saying…”Shit, I can’t find the hole!” Thankfully, we don’t take ourselves too seriously and have no problem laughing at ourselves, so this was really no big deal. I took my own advice, along with my boyfriends coaching (which he had no problem offering) and found the actual hole with my fingers then slid the dildo right in. Success, I was in!

Uh-Oh, Houston, We Have Another Unforeseen Dilemma

Next step is to thrust…not too fast though. I didn’t want to bang the bajeezus out of her, so I took it slowly, but realized that thrusting is a lot different than grinding. When I’m having sex with my b/f and I’m on top, well actually wherever I am positioned, I do a lot of grinding and moving my hips. It feels really good to me and looks hot for him. Anyway, those are two totally different actions.

I realized that my awesome grinding skills were really not going to help me here. So that was a little awkward at first, but I must say, it didn’t kill the mood. I looked up at my b/f and said with a giggle, “Damn this is difficult!” As he responded, “Keep going…it’s hot!” He loved it. After I realized that I shouldn’t concentrate so much on the thrusting, I decided to bend over and kiss my g/f, really get into the moment. Now we were in classic missionary position and she wrapped her legs around my hips. That was fuckin’hot! I checked in with her to make sure everything was okay and she was, as always, very supportive and very aroused. All I have to say is that I have the most rockin’ chick!

We did the missionary for a little while longer, I didn’t bring her to orgasm, but we did decide to turn the Ramp around and have her bend over it, so her beautiful behind was nice and exposed. I  added some more lube, although she was rather wet herself, but safety first.

And the hole was still difficult to find! No worries though, I got my hand involved and was again successful. This time I started to get all porn star on her and started to smack her ass a little as I was thrusting. There’s also this move I always see and I know my b/f has done it to me in the past; you’re banging doggy style and you put both hands on the woman’s butt cheeks and spread. This exposes the asshole more for your viewing pleasure and it also just feels really naughty to do.

I must say that I did really enjoy that! It was very hot!!! In fact, if I didn’t tire out due to the fact that I just didn’t have the muscles strength for the thrusting action, I probably could’ve done that all day. WooHoo!!

Holy Shit…My Girlfriend Wants to Try It Too!

After she reached orgasm, my g/f decided that she wanted to try fucking me…Holy Awesome! I wasn’t sure if she was going to because she had mentioned earlier that she probably wouldn’t fuck me and wanted to know if that was okay, which it absolutely was!

She saw how much fun I was having, thought it was really sexy and needed to give it a try. So we cleaned off the dildo, remember safety, and she put it on, while my b/f now strapped her in securely. I could tell right away that she was digging it from that very moment and so was I because now I also got to experience what it would be like to have a girl fuck me! I felt like the luckiest girl in the world!

So we started out the same as when I was wearing the strap-on. As I lay on my back, she gave me some wonderfully soft oral and manual pleasures and then she slowly found my hole with her fingers, and slowly penetrated me. I think she’s a little more muscular than me; she’s a dancer, so her thrusting experience went a little more smoothly. She didn’t seem to tire out as quickly, and to that I say…good for her!

I could tell she was getting totally lost in what was happening. She was really enjoying this and then she looked at me and said something like, “Holy Shit, this is hot!!! I feel very powerful right now!” Seeing her so involved was really sexy for me and my b/f totally loved it as well. Then she also bent over and kissed me and penetrated me pretty deeply, I was totally aroused by this and almost had an orgasm right there.

Then it was time to turn over, she used my Hitachi Magic Wand on me, which had great potential to send me through the roof. I really had to concentrate so I would be able to hold out because I really wanted her to fuck me from behind. It was nice to see she had to find my hole with her fingers again, and as well, and BAMM she was in. This time I could tell she was more comfortable with the experience because she got right to the thrusting and she was pretty fast about it too. It was awesome!

My Overall Thoughts

Using a strap-on is a lot of fun and I think we did pretty good our first time around. It’s really great to be able to switch roles in the bedroom and do the banging for a change. I wasn’t sure if I’d be able to feel anything physically because I did choose a harness and a dildo without the ability to add vibration, but using the strap-on wasn’t so much about a physical fuck, but a mental one.

Yes, I could physically feel the strap of the harness between my legs and moving a little as I thrust. However, it was the entire situation that I got off on; having someone that I could experience this with, having a b/f that was more than willing to just sit back, watch, coach a little and really enjoy. Knowing all of this was set, made me very comfortable and that’s when the mind fuck can really happen.

I was able to get lost in, not the just the action, but the visuals of it all. My g/f egging me on, telling me to fuck her and my b/f cheering me on with comments here and there and knowing that he was hard and hot over it, made the whole experience exciting. So, I guess it’s safe to say that I enjoyed the actual act of using a strap-on; the penetration, the thrusting and most of all, the power!

Speaking of power, that power can be very addicting. I have learned that there’s something very different about penetrating a woman with fingers, a dildo or a vibrator and penetrating her with something that has actually become a part of you. Even though that wasn’t actually my penis with real feeling and sensitivity, it felt like my penis and I could actually feel something. Maybe it was all in my mind but that doesn’t really matter to me. What matters is that it made the experience very, very real physically and very hot.

Should We Do It Again?

This is absolutely going to be part of the activities next time I see my g/f! In fact, I’ve been doing my research so I can improve my technique and give her a much better experience. Look out girl!

Some Tips

In looking back, here are some things I learned and, hopefully, some tips for you to take with you that you can apply to your own Female/Female strap-on experience:

Finding the Hole

The vaginal opening is not so easy to find and slide right into, even when you’re looking right down at it! I have really developed a special appreciation for what men have to do. But I did learn a way to overcome that, don’t be afraid to get your fingers involved.

Find the hole with the fingers of one hand, even gently spread it open a little, pay attention to what you’re doing, and with your other hand hold onto to the dildo and guide it between your fingers. You’ll be in with no problem and you won’t be poking at the wrong hole, which was another fear I had.

Another tip is to make sure you have some decent lighting. I did this during the day, with the sunlight coming in through the windows. If I had done it the night before in the dark candle light, it probably would have been more difficult or taken a little more time to accomplish.

The issue of feeling too masculine

That was a big fear that I had and I know a fear that many other women have as well. Some of us want to remain very girly during the whole ‘donning a penis’ experience. I can say that the concern didn’t even cross my mind. I didn’t feel self-conscious for a moment, but I really think it’s because I spent a lot of time picking out a harness and a dildo that I felt very comfortable with and that I felt looked good on me.

Some may feel that my vanity issues during my search were a little extreme, but I believe that because I was so extreme at that time, I was even surer of myself at the time of play. Besides, I’m a woman, there’s nothing manly about me normally, so adding a strap-on can’t possibly turn me into a man in my boyfriends or girlfriends mind.

Thrusting vs. Gyrating

The thrusting part was difficult, specifically, keeping a rhythm going, and that’s for both of us. I think the key is to take your time at first and try different positions. Our playtime got cut off abruptly, but if we had more time, trying even more positions would have been a way to go to see if things got easier. But then again, I’m a woman and don’t naturally fuck that way, but I’ve been watching lots of porn and taking note of what positions the girls are in when using a strap-on, so I have more positions to try. They say practice makes perfect.

So What About My Boyfriend Who Wasn’t Physically Involved

Luckily, my b/f and I have a very secure relationship. If you read my “How to have a Threesome” you’ll see that things are very open with our girlfriend. As long as she consents, he can do whatever he wants and the same applies with me. With that deal being totally understood and in total agreement, he had no complaints.

If for some reason he was bothered by the two of us being so intimate together without his involvement, he probably would have gotten himself involved in some way, there’s always room for his lovin’ too. It was actually his decision to step back, watch and cheer us on. He always has an open invitation to join, but his desire was to watch the show. In fact, he loved it so much that he can’t wait to see the follow-up performance.

I hope this article contained enough tips for strap on sex so that your experience will be as enjoyable as mine…even if I did have a few pitfalls.

Ann Andriani
My name is Ann Andriani. Since 1999, I've helped millions of folks sort through their questions and curiosities about sex. I hope that you enjoy your stay with me and benefit from my thoughts and sex advice.

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