So three days had passed since Greg, (the guy that "stalked" me to the park) had thoroughly stretched and filled my sissy ass. I was still wearing my chastity cage, panties, had on a pair of comfy leggings, bra stuffed with my inserts with an oversized T shirt. Doing housework and going about my day. My phone dinged and it was a message from Greg, "How's that sissy ass feel today?" I replied with, "empty, lol" He asked if I would like to fix that problem.  I told him I hadn't really done any preparing for a hookup tonight and sent him a picture of what I had on. I felt rather slouchy, but he replied with how hot he found the leggings. "Ok then" I texted, we agreed on a quiet park halfway between us and a time after dark.

I rushed to grab a quick douche and then slipped the big plug in my lubed hole. Quickly put on my girdle and some soft knee high boots with a short dress. Grab my short hair brunette wig and purse, threw a small blanket in the car just in case. I made it to the park just as the sun was setting. Drove around until I found what looked like a good spot. I grabbed the purse and blanket, headed down a pathway towards a picnic table. Placing the folded blanket on the wooden bench for some padding, I sat down and waited.

Dark settled in and I began to relax a bit, nobody could see me which always helps with the jitters. Greg texted he was close and I sent directions to the spot. A few minutes later and he was standing in front of me in a pair of baggy sweatpants and t shirt. A huge smile on his face told me he liked what I was wearing. He grabbed my ass as I stood up and gave it a hard squeeze. I reached for his crotch and began rubbing his half swollen cock through the sweats. I tugged at his waistband and he sat on the blanket as I pulled his pants down to his ankles.

Immediately I take the head of his magnificent cock in my smooth mouth and started licking and sucking it. Only taking it out of my mouth to lick and suck his gigantic balls, I worked his cock until it was rock hard and pre-cum was oozing nonstop. I could only take about half of his length in my mouth and throat, but I stroked the other half with my hand.

His moaning and squirming told me he was enjoying my efforts. Suddenly he tensed and grabbed the back of my head to hold me in place as his cock erupted in my throat. I swallow a lot, but my mouth is full of his salty sweet baby batter. Not losing a drop, I finally managed to get it all down. "Oh damn, I wasn't expecting that" he says to me. I just smile and tell him it's quite ok, that I enjoy it. I was about to ask if he was going to stay long enough to get some of my ass, when he got a phone call. His work was calling him in and he had to leave. Apologizing profusely, he promised to make it up to me. I nod in understanding and we part ways.

I sat down at the table, clicked on the vibrating plug. Happy with having swallowed a huge load of sperm, the taste still lingering in my mouth. But a little frustrated from not getting fucked. I decided to check Reddit to see if I could find some more fun, no luck tonight however. So I logged on to Grindr with very low expectations. After a minute or two a message pops up from a guy close to my area. He was 19 and looking for an ass to fill. He sent me a pic of his dick, about 8 inches, but very slender. A few more messages were exchanged along with pictures and he is very horny! I sent my location and told him I would wait for an hour, no longer.

I set there a few minutes and heard a vehicle pull up and park. Thinking that he arrived quicker than expected, I put the blanket on the ground and got to my knees. Footsteps approached and suddenly there was an older chubby guy in jogging shorts standing in front of me. I feel my face flush red, but the guy just grinned and stepped closer. Dropped his shorts and simply says, "suck"! In no position to argue much, as he shoved his dick in my face, I opened my smooth mouth and took it to the hilt. He was only about 4 inches, cut and kind of a wedge shape, thin at the head and wide at the base. He wasted no time grabbing my head and started thrusting in and out of my mouth. Usually I don't enjoy this, but his short dick made it fun. I grasp his legs as he pumps my mouth, keeping suction until he shot his semen down my throat. Pulling his shorts up quickly, he left without a word.

I go back to sitting at the table, checking the time, I see only a few minutes have passed. I heard that guys vehicle leave and smile to myself. Sipping on some water, I hear another vehicle approach and park. This time the footsteps brought the young man to me. I could tell he was extremely nervous, and I assured him it was fine. I got back to my knees and urged him to stick his cock in my mouth. He obliged me and soon I could feel him starting to relax. His long thin uncut cock, slid effortlessly down my throat, growing harder with each moment.

He moaned a few times and pulled his now throbbing hard cock from my mouth. Tells me he wants to bury it in my chubby ass. I throw the blanket on the wooden bench and kneel on it, bent over the table with my ass stuck out. I pull down my leggings and panties, pull the still vibrating plug and click it off. Handing him the lube as he stepped between my legs, he quickly lubed and shoved his entire length inside in one thrust. Not wasting any time, he grabbed my hips and begins pounding away at my hole. It didn't really hurt when he entered me, but it felt like a hard snake deep in my guts. His balls were making loud slapping noises against my ass and he was telling me what a good little slut I was. Surprisingly he held out for about 10 minutes before flooding my guts with his seed. He slammed it deep and held it there as scalding hot baby batter flooded my insides. He pulls out, and walks away quickly. I shoved the plug in and pulled up my panties and leggings.