Taking /u/highavailability’s anal virginity. Lots of pictures. [f/m] xposted from /r/hastories

It’s no secret that I’m kindof obsessed with HA’s ass. It truly is a thing of beauty. I’ve never been particularly interested in exploring the male-gspot with anybody else, but HA’s ass is just begging to be played with. I initially approached that line awhile back when we were both pretty heavily under the influence. There was only light external massage on that occasion (mostly bc I have long fingernails), but I couldn’t stop thinking about it thereafter. HA was, understandably, apprehensive about the possibility, but somewhere along the way his curiosity got the best of him and he gave me carte blanche to do whatever I wanted…with the stipulation that anything I did to him, he could also do to me. Well, seeing as how he has fucked me in the ass on multiple occasions, this fine print didn’t dissuade me in the least.

At the time, I didn’t think I’d be seeing HA until mid-January, so I leisurely started reading up on prostate massage, watching tutorial videos, and consulting with my gay bestie. I ordered some things online and continued with my “education” because I approach sex like I do everything else….all or nothing, and if I’m going to do it, I’m going to do it right.

Our next meetup suddenly got much closer last week when we planned a last minute New Year’s weekend in HA’s neck of the woods. Naturally, I immediately tracked my orders and realized they wouldn’t be here on time. Dammit. So I did the only logical thing and the night before leaving to see HA, I ventured to a local sex/lingerie shop after work. This is actually really out of the ordinary for me. I don’t think I’ve been to a sex shop since high school. The things I saw…I’m still trying to process a few of them. I was equal parts intrigued and mortified to be there, but the former quickly won out. I ended up purchasing several different types of butt plugs, a prostate massager, some fancy lubes, and a black leather strappy get-up. When I got home, I tested out a couple of my purchases and sent these pics to HA with the message “these are what I got for me, but you’ll have to wait to see what I picked out for you.” Pleased with my purchases, I packed them in my bag and prayed TSA didn’t decide to go through my stuff.

Fast forward to this past Thursday, and I had to work a half day (which felt like about 3 years) before leaving for the airport. After 2 flights and a layover in ATL, I arrived at DCA and was immediately greeted by HA wrapping his arms around me and picking me up. Our sweet time quickly turned carnal when road head turned into road sex.

I woke up early on day 2 and decided to take a quick shower. By the time I was done, HA was awake and went to do the same. While he was in the bathroom, I dug my assortment of toys out of my bag but then decided to put them back up until the moment was right…and so that he’d have less opportunity to back out (pun intended). So he comes out of the bathroom with just a towel around his waist and has started to ask if I need my morning coffee. I’m wearing the strappy black contraption which pretty successfully stops him mid-sentence. I can see easily through the towel that his erection is growing at record speed. I pull the towel off and lead him to the bed by his cock. I think he’s figured out by this point that I’m planning to be in charge, so he lays back without much resistance. I began as I usually do with his cock in my mouth. I love giving head and love taking it slowly and feeling him throbbing in my throat. After a few minutes and when I don’t think he can possibly get any harder, I start massaging his balls and then gradually go lower until my finger is right on the edge of his ass. Slowly, I slide my finger in and find the prostate. He gasps. We’re both a little apprehensive about this. I have a habit of cutting tension with humor, so without thinking I looked up at him and say “you like that…you fucking retard!” What can I say, we bond over reddit. He laughs then grabs the back of my head and pushes it back down onto his cock. I can tell he’s starting to enjoy this double stimulation by the copious pre-cum that’s coating my mouth. I stop briefly to get my “tools” out of my bag. This time, he’s too close to cumming to seem particularly apprehensive. I put plenty of lube on one of the plugs, and with his cock in my mouth again, I ease it in and turn it on. He jumps, and I ask if he wants me to turn it off or take it out. He says no….that it actually feels really nice. I insert a plug of my own and then climb on top of HA. The combination of the vibrating and his huge cock inside of me is an unreal sensation. I knew it wouldn’t take me long to cum, so when he told him he was close, I didn’t let up but rode him even harder. He started exploding in me which always puts me over the edge. His hands were gripping my ass and forcing himself so far into me. After riding out the waves of complete euphoria, I rolled off of him and onto the bed beside him. Immediately we both started laughing when we realized our asses were still vibrating. We pulled ourselves together, went for coffee, then continued our weekend of sexcapades.

I played with his ass, he came in mine. Yesterday, for maybe the first time ever, we had to stop before completion because my pussy was too sore. Big dick problems.

2016 couldn’t have gotten off to a better start. We have so many plans for this year…travel, debauchery, and most importantly, plans to spend more time together than we spend apart. Happy New Year, Reddit!

Source: reddit.com/r/gonewildstories/comments/3zft29/taking_uhighavailabilitys_anal_virginity_lots_of