Author: BigCrankJack

Discovering My Love of Pegging [M29/F29] [Married] [Pegging] [Anal] [DP] [Toys]

I never thought much of anal sex for the longest time, in any form. I’m a cis-male who was generally always into your standard, run of the mill porn. Heterosexual, lesbian at times, some other different fetishes but nothing ever involving anal and definitely not pegging.

I didn’t even really know it was a thing until I watched a video of my favorite pornstar at the time where she was pegging a guy. The description of the video had nothing to do with pegging and the thumbnail images never showed it either, but it made up a good portion of the video. Anyways, it was Remy Lacroix pegging a guy with a pink strap-on dildo (a bit of a deep cut for you porn fanatics).

When it first started showing the pegging scenes, I was obviously confused. But I found that as I was watching, I never lost my erection and was actually sort of turned on by it. Remy taking control of the situation and fucking the guy in the ass was super hot to watch, and it made me question for a brief moment what I really wanted to see. The rest of the video was back to standard stuff (at least as far as I remember), so I kind of forgot about it for a few years. Read more »

Fucking My College Best Friend [M19/F18] [BigTits]

I didn’t lose my virginity until my freshman year of college. I obviously felt very subconscious about the whole situation, understandably. All anyone talks about in high school and college is who is fucking who, and I hadn’t fucked anyone, so I was anxious about it.

It wasn’t for lack of chances. I’m a tall, athletic guy, not overly ripped or anything but toned and relatively well-hung (not that it was public knowledge). But overall, there wasn’t a reason why I was still a virgin, other than just not taking advantage of opportunities I had when I was younger.

Shortly after I arrived at school, I became good friends with a buddy of mine who had attended high school at a rival school close by but was a couple years older than me. I had played against him in sports and knew who he was, but once we got to college we realized we got along pretty well and ended up renting a house along with a couple other buddies to get out of the dorms. A few months later, I finally started hanging out with his sister who was my age. Read more »

First Trans Experience Part 2 [M30/T24] [Anal]

As I laid there on the bed, slowly waking up from last night’s excursions, my mind was still wildly active. I guess I was only able to sleep from sheer exhaustion because I soon as I awoke, I was still
I’m utter disbelief of the night I’d just had. I had never had an attraction to or anticipated myself having any sexual interactions with a trans person before but last night was one of the most pleasure-filled and exhilarating nights of my life! I could wait to talk to Jennifer when she woke up.

Wait…..where was she??

I turned over on the hotel bed and didn’t see Jennifer anywhere. I listened for a moment to try and see if I had heard her in the bathroom, but there was nothing. She was gone….

I sullenly sat up on the bed, still naked, my cock resting on my thigh, soft and defeated.

*she couldn’t have even said goodbye? I thought we had really connected….* I thought to myself.

As I got off the bed to go to the bathroom, I realized that the bathroom light was still on. When I opened the door, there was a note attached to the bathroom mirror. It read: Read more »

First Trans Experience [M30/T24] [First Time] [Anal]

I was sitting at the hotel bar enjoying a beer, wasting some time before heading back to my room for the night. I was out of town for a work conference and since I was the only person from my company who went, I didn’t really have anyone to hang out with at the hotel, so I was drinking alone.

The bar was a pretty popular spot in town it seemed like, not like a normal hotel bar with a few stragglers hanging around. This place had live music, packed dance floor, a really good environment to hang out in for a little bit.

As I sat and enjoyed my drink, I noticed a group of girls walk into the bar, appearing to celebrate some sort of bachelorette party. They had on the usual sashes with all of their nicknames and catchy phrases written on them, dressed skimpily to boot. The bride-to-be was obviously over-served already but still seemed to have her senses about her. About 8-9 of them made their way through the door and towards the bar.

One of the sashes ended up catching my eye. I had to read it 3-4 times to really make sure I was reading it right. Her sash said “The One with the Big Dick.” Read more »