Now, I am a straight guy and am married to a beautiful woman. However, I have loved anal stimulation for a long time and my wife is totally supportive and loving!
When I was about 19 I went to a local sex shop and, I admit, I was super horny. I browsed around for about an hour checking out the lingerie and porn movies. I finally made my way to the dildo aisle and I was faced with a hard decision. Up until that point I had only ever used my fingers and a hair brush to pleasure my booty hole with, so I was still rather tight. Eventually I landed on this particular one. It was jet black, 12 inches long and had a girth of about 3.5 inches. It was huge!!! I instantly tried to talk myself out of buying it. “What if it never fits? Then you’ve wasted like 30 bucks!” But I bought it anyway.
I walked up to the counter to purchase this monster and the gorgeous lady behind the counter looked at me through he pretty pink hair and grinned at me. She knew what was up! “Thanks and enjoy, big boy.” She said with a knowing grin as I walked away, blushing both from her and the fact that I had just bought a dildo that looked like it belonged on a horse.
As I walked out the door, I realized something; I didn’t have a way to hide this from my parents when I walked in with it. I kinda panicked and walked back inside the store. The lady giggled and said “forget to buy lube?” Then, it dawned me, what if I just wear it in? I hurried and bought some lube and asked if they had a bathroom I could use. The lady looked a bit taken aback but just laughed and pointed towards the back wall. I walked into the men’s restroom and unpacked this thing. It smelled kinda funny, but I just washed it off in the sink and took out the lube. Slowly I pulled down my thong (I wear men’s thongs) and applied a generous amount of lube to my puckered butt hole. The lube was a little cold but that only added to the sensation. I placed the dildo on the toilet lid and applied a heaping helping of lube to it as well. I noticed my nipples were erect and I was oozing a crazy amount of pre-cum. I slowly massaged and pinched my nipples and let my half erect dick drizzle pre-cum on the head of the dildo. After having worked up the courage, I turned around and felt around until the head pressed against my anus. My heart was pounding and I was sweating a little. I started rubbing the head between my ass cheeks and against my balls. It felt so intimidating but so exhilarating at the same time.
I pushed a little. The tip of it barely pressing into my ass and I felt the first twinge of pain. It wasn’t enough to make me stop but I slowed down. Little by little, I eased the full head into me. I felt so full and so slutty. My dick started throbbing and slinging pre-cum all over my thighs. During that moment, a loud knock on the bathroom door and a female voice rang out: “You okay in there?!” I flipped! In my panic, I sat straight down. The whole dildo went into me. All 12 Insertable inches of it. The my tight ball sack slammed into the balls of the dildo and the toilet lid. The mix of pain and pleasure was almost too much to handle. To this day I don’t know what kind of resolve came over me, but I just responded: “Yea I’ll be out soon!”
I sat there, breathing heavy and feeling my prostate being squeezed against this massive dong in my ass. Slowly, I pulled my purple and red thong up my freshly shaven legs and into position. I was relying on it to keep this monster inside me. I pulled up my jeans and with what little focus I could manage. I cleaned up the lube from the floor and toilet. I placed the lube in my pocket and walked out the door. I waddled a good bit. Just taking steps was enough to send waves of pleasure down my body. I could feel it bouncing around in my thong and rubbing my prostate. I could feel the pre-cum building up like a puddle in my undies. My nipples erect and at attention gently sliding across my t-shirt.
The lady behind the counter looked up at me and asked “Where is your …?” Before the could finish her sentence she realized exactly where it was. She blushed and glanced down at my crotch and nipples. “You gonna be alright, chief?” She said with a grin. “Yea, thanks….” I said with a hint of wanting in my voice.
Eventually, I made it to my truck. Let me tell ya, never had I been so happy for bumpy roads! I hit a big pothole just around the corner from home and I had to pull over. My erection was about to explode. “Just get home and get inside?” I kept telling myself.
When I got into the house, my Mom and Dad where not home so I quickly waddled to my room and bathroom. I spent the next hour showering and riding this dildo. My ass was gaped and raw but it felt great. I played with the inside of my ass with my fingers for a while before I slide the monster back where it belonged; my gaping, awaiting asshole. I put on a pretty pink and white, lace frilled g-string I had bought online from a sight that specializes in panties for guys. Then, I took a nap with the dildo still in my butt.
Source: reddit.com/r/eroticliterature/comments/e28z5i/taking_a_big_one_m_true_story