(or, Strap-On Sex + IRC FTW)

Note: This story contains graphic descriptions of my own sexual experiences. If reading about my sex life might be TMI for you, then you’ll want to skip this post.

Technology and pleasure can intersect in a variety of ways (especially when you have a very broad definition of technology. Many of us decide to add dildos, vibrators, rope or other toys to our play because we want new physical experiences. What we don’t often consider is how using technology can change how you think about those physical experiences. (Not to mention the fact that bringing a new piece of technology into the bedroom can be extremely funny.)

Case in point: The first time I tried to fuck another person with a strap-on. It’s common for that experience to be awkward, but in my case, there was an additional piece of technology at play: the Internet. In a wonderfully geeky twist, while I (Vortacist) was trying to fuck partner Alpha, partner Bravo was relaying the whole hilarious situation to an IRC channel of our friends.

The story below includes some excerpts from the log file of that conversation. Anything that was said out loud, in real life, is shown in bold. Please note: My friends’ nicknames have been changed to protect their privacy. I received consent from everyone mentioned in the log before posting these excerpts.

Alpha, Bravo, and I had been watching porn in my basement for a while when Alpha and I decided that it would be a great time for me to try out my new cock, a feeldoe, in his ass. The feeldoe is not so much of a strap-on as a slide-in: it has a bulb which is inserted into the body and holds the cock in place so that you don’t need to wear a harness…at least in theory.

Bravo wasn’t particularly interested in playing with Alpha, so he moved over to a chair and pulled out his laptop. He watched Alpha and I with some amusement and relayed what was happening to an IRC channel of our friends.

“What was happening” was our amusing attempts to overcome a number of logistical challenges, including my lack of experience having a cock and the size difference between Alpha and me. (Alpha was 8″ taller than me and outweighed me by about 70 pounds.)

After a good amount of warm-up and stretching, Alpha and I were ready to try for penetration.

22:16:06 < Bravo> Vortacist is having the tables turned O_o 22:16:13 < Charlie> :O 22:16:14 < Delta> oh? 22:16:14 < Charlie> oh? 22:16:20 < Delta> hehe 22:16:22 < Bravo> she is using the feeldoe on Alpha 22:16:26 < Delta> ! 22:16:29 < Delta> ^_^ 22:16:31 < Charlie> :O 22:16:33 < Charlie> hawt

This wasn’t just the tables being turned; this was the tables being hoisted into the air and thrown at me. There were so many things to concentrate on at the same time! I had to figure out where his entrance actually was, gently push my cock into it at a comfortable angle, and keep from sliding out whenever either of us moved (or squirmed).

Those were just the physical challenges. Mentally, I was also experiencing a kind of inside-out deja vu. The previous July, I became Alpha’s first sexual partner, and the memory of the first time we had vaginal intercourse came rushing back to my mind. We were in the missionary position, and he struggled to get his cock inside me and keep it there. I did my best to be patient — I really wanted him to have a better first time than I had.

Everything had seemed so obvious when I was on the receiving end of his cock. Now, it was surreal to hear myself saying:

22:21:07 < Vortacist> Holy crap, how do people figure this out?

22:23:41 < Vortacist> Damn, this is hard work.

22:25:50 < Vortacist> Am I even in?

I clenched tightly to the feeldoe and somehow eventually managed to work all of it into Alpha’s ass. The triumph was short-lived because my arms were getting tired from holding myself up.

22:23:18 < Alpha> hey Delta :) 22:23:21 < Delta> Alpha: ... XD 22:23:26 < Delta> Alpha: why are you on IRC??? :-P 22:23:35 * Delta facepalm ... 22:24:21 < Bravo> is there a [purity] point for "irc while assfucked" :p 22:24:26 < Delta> hehehehehehe 22:24:28 < Delta> there better be 22:24:31 < Delta> if not we should add one

Yes, you read that correctly: Alpha logged on to IRC (via his smartphone) while I was fucking him. (As if the fact that this log even exists isn’t enough to convince you that I like kinky geeks. ;) Generally, I would have preferred for him be paying attention to me, not his phone…but the whole situation was too hilarious for me to care.

At the time, a bunch of my friends were obsessed with “purity tests”, which mainly involve checking off different activities you’ve done, most of them relating to sex or drugs. Each activity you check off reduces your overall purity score by one point. We had a list of complaints about a common test (including the fact that a disturbing number of the items seemed to involve animals or dead people), to which we could now add the fact that there wasn’t a point for “IRC while assfucked”.

The issue of localization (figuring out what body parts are where) continued to be a problem for us: Alpha was having a difficult time directing me, and while I could easily find his asshole with my fingers, trying to replace them with my cock was really tricky. A friend of mine once told me that trying to have sex while on shrooms is surprisingly difficult because the shrooms interfere with sensory processing. I have to wonder if it feels similar to my strap-on experience: you can’t feel your body, and where everything is located, in the way that you normally can.

I just couldn’t keep the feeldoe in for very long at one time–one squirm from either of us, and it was out again–and Alpha tended to squirm a lot. I was getting pretty frustrated at this point: I really wanted to get my cock inside him and keep it in him long enough to get a rhythm going.

22:47:56 < Vortacist> How much is it to ask, to be able to fuck you in the ass and reach around and grab your cock? That's all I wanna know.

We finally decided that this approach was just not going to work, so we adopted a slightly different tactic: I would wear a harness so the feeldoe would be more firmly attached to me. That was another logistical puzzle, as I didn’t have much experience getting into the harness. Thankfully Bravo stepped in to help me sort out which straps went around which legs. Using the harness meant that the effective length of my cock was a little shorter, but Alpha and I struggled and squirmed on.

23:07:06 < Bravo> yay success 23:07:23 < Delta> *g* yay! 23:07:40 < Bravo> Alpha getting more fucked than previously 23:07:40 < Delta> man who knew this was so complicated ... 23:11:56 < Bravo> also i gotta say one dildo advantage here -- if it were my cock, i'd be all -_- at this point due to repeated starts & stops :p 23:12:30 < Delta> heh yeah, dildo advantage indeed

We had moved from the couch, to missionary position on the floor, and then back up onto the couch. Finally, we found something that worked: Alpha kneeling on the couch, bent over the back of it, and me standing behind him. I leaned over him, holding myself up with one arm. I could fuck Alpha’s ass consistently, and I was able to reach around and jack him off at the same time!

23:25:28 < Bravo> success 23:25:43 < Delta> ^_^ 23:25:44 < Bravo> Alpha.orgasm++ 23:25:50 < Delta> heheee 23:25:53 < Delta> \o/ 23:26:21 < Vortacist> I have so much more respect for you guys now. 23:26:28 < Delta> *G*! 23:31:45 < Alpha> wheeeeeeeeeeeeeeeeeeeeee!

I was thrilled that I was finally able to help Alpha come. The strap-on had enabled me to have a new physical experience, and it also changed how I think about play. I gained a whole new level of respect for people who use cocks on other people (regardless of whether the cock is made of flesh or strapped on). The logistics of using a cock were much more difficult than they seemed in the books I read growing up — “insert tab A into slot B” didn’t even begin to do justice to the process. It seemed to me like a miracle that anyone ever managed to have penetrative intercourse at all.

The fact that my experience was being relayed to IRC was empowering, too:

Even though Bravo wasn’t particularly interested in joining in physically, IRC kept him engaged. I was very happy that he was involved.

What could have been a very embarrassing experience turned into a really fun time–rather than just Alpha and I struggling on our own, our friends laughed together with us and cheered us on.

I’m not necessarily advocating that everyone should try strap-on sex or ask a friend to watch and give running commentary . What I’ve found is that using technology when you play can change not only what you experience physically, but also the way you think about that experience.